Structural reasons for the formation of multicom­ponent products and the influence of high pressure

(S)-(−)-1-Phenyl­ethan­aminium 4-(2,4,6-tri­iso­propyl­benzoyl)­benzoate (S-PEAT­PBB) undergoes a photochemical reaction in its crystalline form upon UV irradiation and forms three different products: the first product is the result of a Yang cyclization with the participation of the δ-H atom of o-iso­propyl (product D) and the second and third products are obtained via a Norrish–Yang reaction with the involvement of the γ-H atom of 2-iso­propyl (product P) and 6-iso­propyl (product Z). These products are formed in different proportions (D > P >> Z). The path and kinetics of the reaction were monitored step-by-step using crystallographic methods, both under ambient and high-pressure conditions. The reactivity of S-PEATPBB depends strongly on the geometry of the reaction centre and the volume of the reaction cavity. Due to the geometrical preferences making the cyclization reaction easier to proceed, product D dominates over the other products, while the formation of product Z becomes difficult or almost impossible at high pressure. The reaction proceeds with an increase of the unit-cell volume, which, suppressed by high pressure, results in a significant decrease of the reaction rate. The crystal lattice of S-PEATPBB shows high elasticity. The quality of the partially reacted crystal remains the same after decom­pression from 0.75 GPa to 0.1 MPa.

Computing details

Data collection: CrysAlis PRO (Agilent Technologies, 2014) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Bruker APEX2 for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa; Diamond Light Source, beamline I-19 for 1_5gpa_144huv. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; Bruker SAINT for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; Bruker SAINT for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; SHELXS2013/1 (Sheldrick, 2008) for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Program(s) used to refine structure: SHELXL 2014/7 (Sheldrick, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; SHELXL (Sheldrick, 2015) for 1_5gpa_144huv. Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Olex2 (Dolomanov et al., 2009) for 1_5gpa_144huv. Software used to prepare material for publication: SHELXL 2014/7 (Sheldrick, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Olex2 (Dolomanov et al., 2009) for 1_5gpa_144huv.

1-Phenylethanaminium 4-(2,4,6-triisopropylbenzoyl)benzoate (0minUV)

Crystal data

C8H12N^+·C23H27O3^−	Dx = 1.123 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4608 reflections
a = 6.2484 (3) Å	θ = 1.6–22.2°
b = 13.7976 (5) Å	µ = 0.07 mm^−1
c = 32.4874 (12) Å	T = 299 K
V = 2800.8 (2) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5414 independent reflections
Radiation source: fine-focus sealed tube	3235 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −17→14
Tmin = 0.921, Tmax = 1.000	l = −40→39
25399 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0489P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5414 reflections	Δρmax = 0.12 e Å^−3
324 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.8 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0310 (6)	0.2437 (2)	0.62912 (9)	0.0820 (11)
O2	0.6173 (4)	0.63153 (17)	0.51657 (8)	0.0518 (7)
O3	0.3168 (5)	0.6207 (2)	0.55225 (8)	0.0634 (8)
N1	0.0337 (5)	0.6701 (2)	0.49106 (8)	0.0439 (8)
H1A	0.1341	0.6488	0.5083	0.053*
H1B	−0.0948	0.6531	0.5004	0.053*
H1C	0.0411	0.7344	0.4892	0.053*
C1	0.8135 (6)	0.2762 (3)	0.68701 (10)	0.0402 (9)
C2	0.8888 (6)	0.3406 (3)	0.71687 (12)	0.0461 (10)
C3	0.8311 (7)	0.3242 (3)	0.75783 (12)	0.0495 (10)
H3	0.8794	0.3669	0.7779	0.059*
C4	0.7050 (6)	0.2470 (3)	0.76942 (11)	0.0475 (10)
C5	0.6316 (6)	0.1855 (3)	0.73881 (11)	0.0472 (10)
H5	0.5441	0.1338	0.7462	0.057*
C6	0.6834 (6)	0.1981 (2)	0.69771 (11)	0.0409 (9)
C7	0.8843 (7)	0.2910 (3)	0.64286 (11)	0.0468 (10)
C8	0.7773 (6)	0.3659 (2)	0.61708 (10)	0.0377 (9)
C9	0.8780 (7)	0.3976 (3)	0.58169 (11)	0.0489 (10)
H9	1.0067	0.3696	0.5736	0.059*
C10	0.7894 (7)	0.4702 (3)	0.55835 (11)	0.0509 (11)
H10	0.8602	0.4916	0.5349	0.061*
C11	0.5965 (6)	0.5120 (2)	0.56925 (11)	0.0389 (9)
C12	0.4919 (7)	0.4779 (3)	0.60349 (12)	0.0542 (11)
H12	0.3590	0.5032	0.6106	0.065*
C13	0.5829 (7)	0.4061 (3)	0.62750 (12)	0.0551 (11)
H13	0.5120	0.3847	0.6510	0.066*
C14	0.5027 (7)	0.5943 (3)	0.54432 (12)	0.0454 (10)
C15	1.0303 (7)	0.4257 (3)	0.70584 (12)	0.0570 (12)
H15	1.0504	0.4252	0.6759	0.068*
C16	1.2499 (7)	0.4164 (3)	0.72572 (14)	0.0713 (13)
H16A	1.3103	0.3544	0.7190	0.107*
H16B	1.2360	0.4219	0.7551	0.107*
H16C	1.3417	0.4669	0.7157	0.107*
C17	0.9255 (8)	0.5224 (3)	0.71743 (18)	0.0974 (18)
H17A	0.9084	0.5257	0.7468	0.146*
H17B	0.7879	0.5271	0.7044	0.146*
H17C	1.0146	0.5749	0.7084	0.146*
C18	0.6424 (8)	0.2263 (4)	0.81398 (12)	0.0659 (13)
H18	0.6455	0.1555	0.8165	0.079*
C19	0.7978 (9)	0.2619 (4)	0.84530 (14)	0.103 (2)
H19A	0.8030	0.3314	0.8445	0.155*
H19B	0.9372	0.2361	0.8394	0.155*
H19C	0.7533	0.2410	0.8722	0.155*
C20	0.4171 (9)	0.2539 (5)	0.82246 (16)	0.108 (2)
H20A	0.3270	0.2306	0.8007	0.162*
H20B	0.4062	0.3232	0.8241	0.162*
H20C	0.3724	0.2259	0.8481	0.162*
C21	0.6044 (7)	0.1270 (3)	0.66513 (12)	0.0558 (12)
H21	0.5881	0.1632	0.6394	0.067*
C22	0.7685 (9)	0.0474 (3)	0.65759 (15)	0.0792 (15)
H22A	0.7881	0.0105	0.6824	0.119*
H22B	0.9023	0.0760	0.6496	0.119*
H22C	0.7187	0.0055	0.6360	0.119*
C23	0.3890 (8)	0.0825 (4)	0.67528 (14)	0.0815 (15)
H23A	0.2879	0.1330	0.6812	0.122*
H23B	0.4031	0.0410	0.6989	0.122*
H23C	0.3394	0.0453	0.6522	0.122*
C24	0.2781 (8)	0.6620 (3)	0.43207 (13)	0.0658 (13)
H24A	0.3923	0.6441	0.4503	0.099*
H24B	0.2736	0.7313	0.4294	0.099*
H24C	0.3019	0.6334	0.4055	0.099*
C25	0.0684 (7)	0.6263 (3)	0.44928 (11)	0.0497 (11)
H25	−0.0456	0.6504	0.4312	0.060*
C26	0.0456 (7)	0.5176 (3)	0.45174 (11)	0.0496 (11)
C27	−0.1409 (8)	0.4731 (3)	0.43944 (13)	0.0693 (13)
H27	−0.2546	0.5107	0.4301	0.083*
C28	−0.1618 (11)	0.3731 (4)	0.44078 (17)	0.0918 (19)
H28	−0.2884	0.3442	0.4322	0.110*
C29	0.0010 (15)	0.3178 (4)	0.45456 (18)	0.101 (2)
H29	−0.0142	0.2508	0.4556	0.121*
C30	0.1882 (12)	0.3598 (4)	0.46706 (16)	0.0931 (18)
H30	0.3005	0.3214	0.4764	0.112*
C31	0.2104 (8)	0.4601 (3)	0.46584 (13)	0.0683 (13)
H31	0.3375	0.4885	0.4746	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.100 (3)	0.084 (2)	0.061 (2)	0.051 (2)	0.0339 (19)	0.0261 (17)
O2	0.0509 (17)	0.0491 (15)	0.0555 (16)	0.0022 (14)	0.0013 (15)	0.0209 (13)
O3	0.0474 (19)	0.086 (2)	0.0564 (18)	0.0215 (17)	0.0051 (16)	0.0227 (15)
N1	0.045 (2)	0.0415 (17)	0.0453 (19)	0.0014 (15)	−0.0010 (16)	0.0094 (15)
C1	0.046 (2)	0.039 (2)	0.036 (2)	0.0121 (19)	0.003 (2)	0.0074 (18)
C2	0.051 (3)	0.042 (2)	0.045 (2)	0.002 (2)	0.002 (2)	0.0060 (19)
C3	0.056 (3)	0.052 (2)	0.041 (2)	0.000 (2)	0.002 (2)	−0.0038 (19)
C4	0.049 (3)	0.057 (3)	0.037 (2)	0.005 (2)	0.004 (2)	0.005 (2)
C5	0.053 (3)	0.047 (2)	0.042 (2)	−0.001 (2)	0.001 (2)	0.0119 (19)
C6	0.046 (2)	0.040 (2)	0.037 (2)	0.005 (2)	−0.003 (2)	0.0095 (17)
C7	0.057 (3)	0.040 (2)	0.043 (2)	0.006 (2)	0.006 (2)	0.0064 (18)
C8	0.044 (2)	0.036 (2)	0.032 (2)	0.0041 (18)	0.0029 (18)	0.0038 (16)
C9	0.050 (3)	0.051 (2)	0.046 (2)	0.013 (2)	0.015 (2)	0.0113 (19)
C10	0.053 (3)	0.055 (2)	0.045 (2)	0.008 (2)	0.012 (2)	0.021 (2)
C11	0.040 (2)	0.039 (2)	0.038 (2)	0.0002 (19)	−0.0048 (19)	0.0063 (17)
C12	0.045 (3)	0.065 (3)	0.053 (2)	0.009 (2)	0.014 (2)	0.018 (2)
C13	0.056 (3)	0.064 (3)	0.045 (2)	0.010 (2)	0.014 (2)	0.022 (2)
C14	0.047 (3)	0.047 (2)	0.042 (2)	0.001 (2)	−0.006 (2)	0.005 (2)
C15	0.064 (3)	0.054 (3)	0.054 (3)	−0.009 (2)	0.002 (2)	0.004 (2)
C16	0.064 (3)	0.074 (3)	0.075 (3)	−0.002 (3)	0.010 (3)	−0.001 (3)
C17	0.074 (3)	0.049 (3)	0.169 (6)	−0.001 (3)	0.011 (4)	0.009 (3)
C18	0.068 (3)	0.089 (3)	0.041 (3)	0.002 (3)	0.012 (3)	0.000 (2)
C19	0.100 (4)	0.168 (6)	0.042 (3)	−0.014 (4)	0.000 (3)	0.000 (3)
C20	0.091 (5)	0.163 (6)	0.070 (4)	0.004 (4)	0.033 (3)	−0.001 (4)
C21	0.071 (3)	0.052 (2)	0.044 (2)	−0.004 (3)	−0.010 (2)	0.002 (2)
C22	0.099 (4)	0.063 (3)	0.075 (3)	0.008 (3)	−0.004 (3)	−0.019 (3)
C23	0.077 (4)	0.087 (3)	0.081 (3)	−0.024 (3)	−0.012 (3)	−0.001 (3)
C24	0.080 (4)	0.068 (3)	0.049 (2)	−0.010 (3)	0.018 (2)	−0.001 (2)
C25	0.055 (3)	0.054 (2)	0.039 (2)	−0.001 (2)	−0.007 (2)	0.0066 (19)
C26	0.059 (3)	0.055 (3)	0.035 (2)	−0.002 (2)	0.001 (2)	−0.0023 (19)
C27	0.071 (4)	0.080 (3)	0.057 (3)	−0.017 (3)	0.007 (3)	−0.014 (3)
C28	0.112 (5)	0.085 (4)	0.079 (4)	−0.042 (4)	0.025 (4)	−0.028 (3)
C29	0.158 (7)	0.060 (4)	0.084 (4)	−0.022 (5)	0.040 (5)	−0.009 (3)
C30	0.130 (6)	0.063 (4)	0.086 (4)	0.016 (4)	0.019 (4)	0.003 (3)
C31	0.076 (4)	0.057 (3)	0.072 (3)	−0.002 (3)	−0.001 (3)	0.000 (2)

Geometric parameters (Å, º)

O1—C7	1.210 (4)	C17—H17B	0.9600
O2—C14	1.261 (4)	C17—H17C	0.9600
O3—C14	1.244 (5)	C18—C20	1.484 (7)
N1—C25	1.502 (4)	C18—C19	1.489 (6)
N1—H1A	0.8900	C18—H18	0.9800
N1—H1B	0.8900	C19—H19A	0.9600
N1—H1C	0.8900	C19—H19B	0.9600
C1—C6	1.395 (5)	C19—H19C	0.9600
C1—C2	1.396 (5)	C20—H20A	0.9600
C1—C7	1.514 (5)	C20—H20B	0.9600
C2—C3	1.397 (5)	C20—H20C	0.9600
C2—C15	1.514 (5)	C21—C23	1.516 (6)
C3—C4	1.378 (5)	C21—C22	1.522 (6)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.385 (5)	C22—H22A	0.9600
C4—C18	1.526 (5)	C22—H22B	0.9600
C5—C6	1.385 (5)	C22—H22C	0.9600
C5—H5	0.9300	C23—H23A	0.9600
C6—C21	1.524 (5)	C23—H23B	0.9600
C7—C8	1.489 (5)	C23—H23C	0.9600
C8—C13	1.378 (5)	C24—C25	1.507 (6)
C8—C9	1.382 (5)	C24—H24A	0.9600
C9—C10	1.373 (5)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C10—C11	1.382 (5)	C25—C26	1.510 (5)
C10—H10	0.9300	C25—H25	0.9800
C11—C12	1.373 (5)	C26—C27	1.377 (6)
C11—C14	1.513 (5)	C26—C31	1.378 (6)
C12—C13	1.383 (5)	C27—C28	1.386 (7)
C12—H12	0.9300	C27—H27	0.9300
C13—H13	0.9300	C28—C29	1.348 (9)
C15—C16	1.522 (6)	C28—H28	0.9300
C15—C17	1.532 (6)	C29—C30	1.368 (8)
C15—H15	0.9800	C29—H29	0.9300
C16—H16A	0.9600	C30—C31	1.391 (7)
C16—H16B	0.9600	C30—H30	0.9300
C16—H16C	0.9600	C31—H31	0.9300
C17—H17A	0.9600
C25—N1—H1A	109.5	C20—C18—C19	114.0 (4)
C25—N1—H1B	109.5	C20—C18—C4	111.8 (4)
H1A—N1—H1B	109.5	C19—C18—C4	114.8 (4)
C25—N1—H1C	109.5	C20—C18—H18	105.0
H1A—N1—H1C	109.5	C19—C18—H18	105.0
H1B—N1—H1C	109.5	C4—C18—H18	105.0
C6—C1—C2	121.0 (3)	C18—C19—H19A	109.5
C6—C1—C7	120.7 (3)	C18—C19—H19B	109.5
C2—C1—C7	118.3 (3)	H19A—C19—H19B	109.5
C1—C2—C3	118.2 (3)	C18—C19—H19C	109.5
C1—C2—C15	121.7 (3)	H19A—C19—H19C	109.5
C3—C2—C15	120.1 (4)	H19B—C19—H19C	109.5
C4—C3—C2	122.2 (4)	C18—C20—H20A	109.5
C4—C3—H3	118.9	C18—C20—H20B	109.5
C2—C3—H3	118.9	H20A—C20—H20B	109.5
C3—C4—C5	117.8 (3)	C18—C20—H20C	109.5
C3—C4—C18	123.4 (4)	H20A—C20—H20C	109.5
C5—C4—C18	118.8 (4)	H20B—C20—H20C	109.5
C4—C5—C6	122.6 (4)	C23—C21—C22	109.9 (4)
C4—C5—H5	118.7	C23—C21—C6	113.4 (4)
C6—C5—H5	118.7	C22—C21—C6	110.9 (3)
C5—C6—C1	118.2 (3)	C23—C21—H21	107.4
C5—C6—C21	120.9 (3)	C22—C21—H21	107.4
C1—C6—C21	120.8 (3)	C6—C21—H21	107.4
O1—C7—C8	120.4 (3)	C21—C22—H22A	109.5
O1—C7—C1	119.9 (3)	C21—C22—H22B	109.5
C8—C7—C1	119.7 (3)	H22A—C22—H22B	109.5
C13—C8—C9	118.6 (3)	C21—C22—H22C	109.5
C13—C8—C7	122.5 (3)	H22A—C22—H22C	109.5
C9—C8—C7	118.9 (3)	H22B—C22—H22C	109.5
C10—C9—C8	120.5 (4)	C21—C23—H23A	109.5
C10—C9—H9	119.8	C21—C23—H23B	109.5
C8—C9—H9	119.8	H23A—C23—H23B	109.5
C9—C10—C11	121.0 (3)	C21—C23—H23C	109.5
C9—C10—H10	119.5	H23A—C23—H23C	109.5
C11—C10—H10	119.5	H23B—C23—H23C	109.5
C12—C11—C10	118.6 (3)	C25—C24—H24A	109.5
C12—C11—C14	120.4 (4)	C25—C24—H24B	109.5
C10—C11—C14	120.9 (3)	H24A—C24—H24B	109.5
C11—C12—C13	120.5 (4)	C25—C24—H24C	109.5
C11—C12—H12	119.8	H24A—C24—H24C	109.5
C13—C12—H12	119.8	H24B—C24—H24C	109.5
C8—C13—C12	120.8 (4)	N1—C25—C24	109.2 (3)
C8—C13—H13	119.6	N1—C25—C26	109.8 (3)
C12—C13—H13	119.6	C24—C25—C26	115.2 (4)
O3—C14—O2	124.0 (4)	N1—C25—H25	107.4
O3—C14—C11	118.1 (4)	C24—C25—H25	107.4
O2—C14—C11	117.9 (4)	C26—C25—H25	107.4
C2—C15—C16	111.1 (3)	C27—C26—C31	118.2 (4)
C2—C15—C17	111.6 (4)	C27—C26—C25	120.5 (4)
C16—C15—C17	110.8 (4)	C31—C26—C25	121.3 (4)
C2—C15—H15	107.7	C26—C27—C28	120.9 (5)
C16—C15—H15	107.7	C26—C27—H27	119.5
C17—C15—H15	107.7	C28—C27—H27	119.5
C15—C16—H16A	109.5	C29—C28—C27	120.2 (6)
C15—C16—H16B	109.5	C29—C28—H28	119.9
H16A—C16—H16B	109.5	C27—C28—H28	119.9
C15—C16—H16C	109.5	C28—C29—C30	120.2 (6)
H16A—C16—H16C	109.5	C28—C29—H29	119.9
H16B—C16—H16C	109.5	C30—C29—H29	119.9
C15—C17—H17A	109.5	C29—C30—C31	119.9 (6)
C15—C17—H17B	109.5	C29—C30—H30	120.0
H17A—C17—H17B	109.5	C31—C30—H30	120.0
C15—C17—H17C	109.5	C26—C31—C30	120.5 (5)
H17A—C17—H17C	109.5	C26—C31—H31	119.8
H17B—C17—H17C	109.5	C30—C31—H31	119.8

(140minUV)

Crystal data

C31H39NO3	Dx = 1.123 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3644 reflections
a = 6.2711 (3) Å	θ = 1.6–21.1°
b = 13.7242 (7) Å	µ = 0.07 mm^−1
c = 32.5405 (13) Å	T = 299 K
V = 2800.6 (2) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5416 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→16
Tmin = 0.882, Tmax = 1.000	l = −39→40
25271 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0392P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5416 reflections	Δρmax = 0.13 e Å^−3
411 parameters	Δρmin = −0.15 e Å^−3
300 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.8 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.0366 (10)	0.2455 (4)	0.63034 (15)	0.087 (2)	0.882 (7)
O2	0.6209 (5)	0.6313 (2)	0.51675 (10)	0.0590 (9)	0.882 (7)
O3	0.3198 (6)	0.6195 (3)	0.55168 (9)	0.0712 (10)	0.882 (7)
C1	0.8156 (14)	0.2773 (6)	0.6880 (2)	0.049 (2)	0.882 (7)
C2	0.8830 (19)	0.3425 (7)	0.7181 (3)	0.057 (2)	0.882 (7)
C3	0.8223 (17)	0.3265 (8)	0.7587 (3)	0.060 (3)	0.882 (7)
H3	0.8685	0.3697	0.7788	0.072*	0.882 (7)
C4	0.6963 (17)	0.2491 (8)	0.7699 (2)	0.056 (3)	0.882 (7)
C5	0.629 (2)	0.1865 (9)	0.7393 (2)	0.056 (2)	0.882 (7)
H5	0.5431	0.1339	0.7463	0.067*	0.882 (7)
C6	0.6859 (15)	0.1989 (6)	0.6984 (2)	0.048 (2)	0.882 (7)
C7	0.8878 (14)	0.2922 (6)	0.6441 (2)	0.063 (2)	0.882 (7)
C8	0.7793 (13)	0.3662 (5)	0.6180 (2)	0.049 (2)	0.882 (7)
C9	0.8772 (10)	0.3958 (4)	0.58193 (19)	0.0530 (16)	0.882 (7)
H9	1.0029	0.3660	0.5735	0.064*	0.882 (7)
C10	0.7896 (10)	0.4688 (4)	0.55864 (18)	0.0534 (16)	0.882 (7)
H10	0.8594	0.4895	0.5350	0.064*	0.882 (7)
C11	0.6000 (11)	0.5119 (4)	0.56974 (17)	0.047 (2)	0.882 (7)
C12	0.4961 (12)	0.4805 (5)	0.6050 (2)	0.055 (2)	0.882 (7)
H12	0.3646	0.5068	0.6122	0.066*	0.882 (7)
C13	0.5898 (12)	0.4098 (5)	0.6293 (2)	0.058 (2)	0.882 (7)
H13	0.5240	0.3914	0.6537	0.070*	0.882 (7)
C14	0.5063 (9)	0.5945 (3)	0.54446 (14)	0.0510 (12)	0.882 (7)
C15	1.0217 (16)	0.4284 (7)	0.7071 (4)	0.067 (3)	0.882 (7)
H15	1.0354	0.4293	0.6771	0.080*	0.882 (7)
C16	1.2454 (16)	0.4171 (8)	0.7248 (4)	0.077 (3)	0.882 (7)
H16A	1.3301	0.4726	0.7173	0.116*	0.882 (7)
H16B	1.2371	0.4126	0.7542	0.116*	0.882 (7)
H16C	1.3099	0.3591	0.7140	0.116*	0.882 (7)
C17	0.9233 (17)	0.5251 (6)	0.7199 (3)	0.098 (3)	0.882 (7)
H17A	1.0169	0.5774	0.7123	0.147*	0.882 (7)
H17B	0.7884	0.5333	0.7064	0.147*	0.882 (7)
H17C	0.9025	0.5256	0.7491	0.147*	0.882 (7)
C18	0.6349 (17)	0.2282 (8)	0.8144 (2)	0.080 (3)	0.882 (7)
H18	0.6422	0.1571	0.8167	0.096*	0.882 (7)
C19	0.7880 (13)	0.2640 (6)	0.8460 (2)	0.101 (3)	0.882 (7)
H19A	0.9303	0.2459	0.8383	0.152*	0.882 (7)
H19B	0.7783	0.3337	0.8479	0.152*	0.882 (7)
H19C	0.7540	0.2355	0.8721	0.152*	0.882 (7)
C20	0.4083 (12)	0.2516 (6)	0.8229 (2)	0.099 (3)	0.882 (7)
H20A	0.3206	0.2261	0.8012	0.149*	0.882 (7)
H20B	0.3666	0.2229	0.8486	0.149*	0.882 (7)
H20C	0.3909	0.3210	0.8244	0.149*	0.882 (7)
C21	0.6085 (12)	0.1281 (5)	0.66565 (19)	0.067 (2)	0.882 (7)
H21	0.5917	0.1651	0.6401	0.080*	0.882 (7)
C22	0.7733 (12)	0.0497 (5)	0.65774 (19)	0.091 (3)	0.882 (7)
H22A	0.7215	0.0059	0.6370	0.136*	0.882 (7)
H22B	0.9035	0.0793	0.6485	0.136*	0.882 (7)
H22C	0.7995	0.0143	0.6827	0.136*	0.882 (7)
C23	0.3921 (12)	0.0815 (5)	0.6755 (2)	0.094 (3)	0.882 (7)
H23A	0.2887	0.1317	0.6804	0.140*	0.882 (7)
H23B	0.3470	0.0423	0.6526	0.140*	0.882 (7)
H23C	0.4053	0.0413	0.6995	0.140*	0.882 (7)
O1D	1.094 (6)	0.286 (3)	0.6418 (13)	0.080 (12)*	0.118 (7)
O2D	0.6209 (5)	0.6313 (2)	0.51675 (10)	0.0590 (9)	0.118 (7)
O3D	0.3198 (6)	0.6195 (3)	0.55168 (9)	0.0712 (10)	0.118 (7)
C1D	0.803 (10)	0.289 (4)	0.6902 (12)	0.049 (14)*	0.118 (7)
C2D	0.910 (13)	0.344 (5)	0.7192 (15)	0.047 (14)*	0.118 (7)
C3D	0.866 (12)	0.321 (5)	0.7605 (15)	0.040 (13)*	0.118 (7)
H3D	0.9282	0.3576	0.7813	0.049*	0.118 (7)
C4D	0.728 (11)	0.242 (5)	0.7706 (13)	0.043 (13)*	0.118 (7)
C5D	0.618 (16)	0.193 (7)	0.7397 (13)	0.060 (14)*	0.118 (7)
H5D	0.5176	0.1459	0.7464	0.072*	0.118 (7)
C6D	0.660 (12)	0.215 (5)	0.6992 (13)	0.049 (14)*	0.118 (7)
C7D	0.866 (7)	0.282 (3)	0.6436 (12)	0.061 (14)*	0.118 (7)
C8D	0.776 (7)	0.370 (3)	0.6204 (11)	0.051 (14)*	0.118 (7)
C9D	0.905 (7)	0.424 (2)	0.5942 (10)	0.054 (13)*	0.118 (7)
H9D	1.0504	0.4106	0.5933	0.065*	0.118 (7)
C10D	0.823 (6)	0.497 (2)	0.5693 (10)	0.061 (13)*	0.118 (7)
H10D	0.9121	0.5318	0.5520	0.073*	0.118 (7)
C11D	0.603 (6)	0.5174 (15)	0.5704 (7)	0.048 (14)*	0.118 (7)
C12D	0.479 (7)	0.463 (3)	0.5968 (12)	0.050 (13)*	0.118 (7)
H12D	0.3330	0.4754	0.5980	0.060*	0.118 (7)
C13D	0.560 (7)	0.390 (3)	0.6216 (15)	0.040 (13)*	0.118 (7)
H13D	0.4711	0.3549	0.6390	0.049*	0.118 (7)
C14D	0.5063 (9)	0.5945 (3)	0.54446 (14)	0.0510 (12)	0.118 (7)
C15D	1.058 (11)	0.426 (4)	0.708 (2)	0.055 (14)*	0.118 (7)
H15D	1.1137	0.4094	0.6810	0.066*	0.118 (7)
C16D	1.248 (12)	0.431 (6)	0.736 (3)	0.07 (2)*	0.118 (7)
H16D	1.3372	0.4843	0.7274	0.099*	0.118 (7)
H16E	1.2031	0.4399	0.7635	0.099*	0.118 (7)
H16F	1.3273	0.3710	0.7334	0.099*	0.118 (7)
C17D	0.937 (15)	0.523 (5)	0.702 (2)	0.09 (2)*	0.118 (7)
H17D	0.8172	0.5123	0.6842	0.142*	0.118 (7)
H17E	0.8866	0.5460	0.7283	0.142*	0.118 (7)
H17F	1.0306	0.5702	0.6902	0.142*	0.118 (7)
C18D	0.654 (10)	0.219 (5)	0.8157 (13)	0.064 (14)*	0.118 (7)
H18D	0.5753	0.1573	0.8154	0.076*	0.118 (7)
C19D	0.834 (10)	0.210 (5)	0.8464 (18)	0.099 (14)*	0.118 (7)
H19D	0.9273	0.1580	0.8383	0.149*	0.118 (7)
H19E	0.9123	0.2699	0.8474	0.149*	0.118 (7)
H19F	0.7762	0.1961	0.8731	0.149*	0.118 (7)
C20D	0.498 (10)	0.301 (4)	0.8271 (18)	0.12 (2)*	0.118 (7)
H20D	0.3869	0.3047	0.8069	0.173*	0.118 (7)
H20E	0.4374	0.2884	0.8536	0.173*	0.118 (7)
H20F	0.5736	0.3622	0.8279	0.173*	0.118 (7)
C21D	0.587 (8)	0.160 (4)	0.6602 (14)	0.081 (14)*	0.118 (7)
H21D	0.4634	0.1941	0.6489	0.097*	0.118 (7)
C22D	0.778 (7)	0.181 (3)	0.6324 (12)	0.107 (17)*	0.118 (7)
H22D	0.8874	0.1321	0.6362	0.128*	0.118 (7)
H22E	0.7341	0.1804	0.6038	0.128*	0.118 (7)
C23D	0.523 (12)	0.056 (4)	0.668 (2)	0.14 (2)*	0.118 (7)
H23D	0.4011	0.0551	0.6857	0.213*	0.118 (7)
H23E	0.4867	0.0259	0.6422	0.213*	0.118 (7)
H23F	0.6387	0.0219	0.6804	0.213*	0.118 (7)
N1	0.0361 (5)	0.6693 (2)	0.49147 (9)	0.0489 (10)
H1A	0.1369	0.6477	0.5084	0.059*
H1B	−0.0915	0.6528	0.5012	0.059*
H1C	0.0447	0.7339	0.4895	0.059*
C24	0.2792 (9)	0.6599 (4)	0.43248 (15)	0.0773 (17)
H24A	0.3917	0.6437	0.4513	0.116*
H24B	0.2744	0.7292	0.4288	0.116*
H24C	0.3053	0.6289	0.4065	0.116*
C25	0.0671 (8)	0.6247 (3)	0.44975 (13)	0.0563 (13)
H25	−0.0462	0.6494	0.4318	0.068*
C26	0.0433 (9)	0.5164 (4)	0.45214 (14)	0.0577 (14)
C27	−0.1433 (10)	0.4726 (4)	0.43978 (15)	0.0780 (17)
H27	−0.2555	0.5110	0.4305	0.094*
C28	−0.1667 (14)	0.3726 (6)	0.4410 (2)	0.109 (3)
H28	−0.2936	0.3440	0.4324	0.130*
C29	−0.0051 (18)	0.3166 (6)	0.4546 (2)	0.122 (3)
H29	−0.0214	0.2493	0.4553	0.146*
C30	0.1813 (15)	0.3570 (5)	0.4672 (2)	0.109 (2)
H30	0.2923	0.3177	0.4763	0.130*
C31	0.2052 (11)	0.4583 (4)	0.46630 (16)	0.0831 (18)
H31	0.3317	0.4863	0.4754	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.104 (4)	0.085 (4)	0.071 (3)	0.049 (4)	0.036 (3)	0.025 (3)
O2	0.057 (2)	0.060 (2)	0.0600 (19)	0.0005 (18)	0.0036 (18)	0.0233 (17)
O3	0.055 (2)	0.100 (3)	0.059 (2)	0.023 (2)	0.003 (2)	0.0250 (19)
C1	0.056 (4)	0.044 (4)	0.047 (4)	0.016 (3)	0.002 (3)	0.013 (3)
C2	0.061 (5)	0.049 (4)	0.059 (4)	0.005 (3)	0.004 (4)	0.012 (3)
C3	0.064 (7)	0.058 (4)	0.057 (4)	0.001 (5)	−0.004 (4)	−0.002 (3)
C4	0.056 (5)	0.065 (5)	0.046 (4)	0.008 (4)	0.005 (3)	0.010 (3)
C5	0.062 (4)	0.055 (4)	0.051 (4)	0.000 (4)	0.000 (3)	0.013 (3)
C6	0.051 (4)	0.045 (4)	0.047 (4)	0.009 (4)	−0.007 (3)	0.010 (3)
C7	0.075 (5)	0.057 (4)	0.056 (4)	0.005 (4)	0.005 (4)	0.011 (3)
C8	0.059 (4)	0.048 (4)	0.039 (3)	0.007 (3)	0.006 (3)	0.010 (3)
C9	0.054 (4)	0.054 (4)	0.051 (4)	0.009 (3)	0.011 (3)	0.003 (3)
C10	0.060 (4)	0.056 (4)	0.045 (3)	0.007 (3)	0.005 (3)	0.013 (3)
C11	0.050 (4)	0.045 (3)	0.045 (3)	0.004 (3)	−0.005 (3)	0.009 (2)
C12	0.052 (4)	0.067 (4)	0.046 (4)	0.005 (3)	0.008 (3)	0.014 (4)
C13	0.061 (5)	0.072 (5)	0.043 (4)	0.007 (4)	0.010 (4)	0.020 (4)
C14	0.054 (3)	0.055 (3)	0.044 (3)	0.002 (3)	−0.007 (3)	0.005 (2)
C15	0.068 (6)	0.068 (5)	0.065 (4)	−0.006 (4)	−0.005 (4)	0.008 (3)
C16	0.074 (5)	0.084 (6)	0.074 (8)	−0.003 (4)	0.007 (5)	−0.008 (5)
C17	0.076 (5)	0.059 (4)	0.159 (10)	−0.003 (4)	0.010 (7)	0.005 (6)
C18	0.082 (6)	0.105 (6)	0.052 (4)	0.010 (5)	0.011 (4)	−0.005 (4)
C19	0.103 (6)	0.150 (8)	0.051 (4)	0.005 (6)	−0.002 (4)	−0.002 (5)
C20	0.091 (6)	0.138 (7)	0.070 (5)	−0.014 (6)	0.033 (4)	−0.009 (4)
C21	0.092 (6)	0.057 (4)	0.050 (4)	−0.008 (4)	−0.014 (4)	0.008 (3)
C22	0.126 (7)	0.080 (5)	0.067 (4)	0.017 (5)	−0.001 (4)	−0.022 (4)
C23	0.095 (6)	0.101 (5)	0.084 (5)	−0.034 (5)	−0.016 (5)	−0.003 (4)
O2D	0.057 (2)	0.060 (2)	0.0600 (19)	0.0005 (18)	0.0036 (18)	0.0233 (17)
O3D	0.055 (2)	0.100 (3)	0.059 (2)	0.023 (2)	0.003 (2)	0.0250 (19)
C14D	0.054 (3)	0.055 (3)	0.044 (3)	0.002 (3)	−0.007 (3)	0.005 (2)
N1	0.049 (2)	0.053 (2)	0.045 (2)	0.0009 (18)	0.000 (2)	0.0095 (18)
C24	0.097 (5)	0.086 (4)	0.050 (3)	−0.006 (3)	0.020 (3)	−0.002 (3)
C25	0.059 (4)	0.070 (3)	0.040 (3)	0.002 (3)	−0.008 (3)	0.006 (3)
C26	0.069 (4)	0.064 (3)	0.040 (3)	−0.001 (3)	0.000 (3)	−0.005 (3)
C27	0.080 (5)	0.089 (5)	0.065 (4)	−0.011 (4)	0.002 (3)	−0.014 (3)
C28	0.128 (7)	0.101 (6)	0.097 (5)	−0.042 (5)	0.028 (5)	−0.034 (5)
C29	0.180 (11)	0.075 (6)	0.112 (6)	−0.028 (6)	0.043 (7)	−0.011 (5)
C30	0.145 (8)	0.075 (5)	0.106 (5)	0.016 (5)	0.007 (5)	0.002 (4)
C31	0.092 (5)	0.074 (4)	0.083 (4)	−0.001 (4)	−0.007 (4)	−0.003 (3)

Geometric parameters (Å, º)

O1—C7	1.218 (7)	C4D—C18D	1.57 (2)
O2—C14	1.259 (5)	C5D—C6D	1.38 (2)
O3—C14	1.241 (5)	C5D—H5D	0.9300
C1—C2	1.391 (8)	C6D—C21D	1.55 (2)
C1—C6	1.391 (7)	C7D—C22D	1.53 (2)
C1—C7	1.513 (7)	C7D—C8D	1.53 (2)
C2—C3	1.392 (7)	C8D—C13D	1.38 (2)
C2—C15	1.508 (8)	C8D—C9D	1.39 (2)
C3—C4	1.375 (7)	C9D—C10D	1.39 (2)
C3—H3	0.9300	C9D—H9D	0.9300
C4—C5	1.382 (8)	C10D—C11D	1.41 (2)
C4—C18	1.526 (8)	C10D—H10D	0.9300
C5—C6	1.387 (7)	C11D—C12D	1.38 (2)
C5—H5	0.9300	C11D—C14D	1.48 (2)
C6—C21	1.521 (7)	C12D—C13D	1.38 (2)
C7—C8	1.489 (7)	C12D—H12D	0.9300
C8—C13	1.381 (7)	C13D—H13D	0.9300
C8—C9	1.386 (7)	C15D—C16D	1.49 (3)
C9—C10	1.371 (6)	C15D—C17D	1.54 (3)
C9—H9	0.9300	C15D—H15D	0.9800
C10—C11	1.376 (7)	C16D—H16D	0.9600
C10—H10	0.9300	C16D—H16E	0.9600
C11—C12	1.387 (7)	C16D—H16F	0.9600
C11—C14	1.519 (7)	C17D—H17D	0.9600
C12—C13	1.383 (7)	C17D—H17E	0.9600
C12—H12	0.9300	C17D—H17F	0.9600
C13—H13	0.9300	C18D—C19D	1.51 (3)
C15—C17	1.523 (9)	C18D—C20D	1.54 (3)
C15—C16	1.524 (9)	C18D—H18D	0.9800
C15—H15	0.9800	C19D—H19D	0.9600
C16—H16A	0.9600	C19D—H19E	0.9600
C16—H16B	0.9600	C19D—H19F	0.9600
C16—H16C	0.9600	C20D—H20D	0.9600
C17—H17A	0.9600	C20D—H20E	0.9600
C17—H17B	0.9600	C20D—H20F	0.9600
C17—H17C	0.9600	C21D—C23D	1.50 (3)
C18—C20	1.483 (10)	C21D—C22D	1.53 (3)
C18—C19	1.489 (10)	C21D—H21D	0.9800
C18—H18	0.9800	C22D—H22D	0.9700
C19—H19A	0.9600	C22D—H22E	0.9700
C19—H19B	0.9600	C23D—H23D	0.9600
C19—H19C	0.9600	C23D—H23E	0.9600
C20—H20A	0.9600	C23D—H23F	0.9600
C20—H20B	0.9600	N1—C25	1.502 (5)
C20—H20C	0.9600	N1—H1A	0.8900
C21—C22	1.513 (9)	N1—H1B	0.8900
C21—C23	1.534 (9)	N1—H1C	0.8900
C21—H21	0.9800	C24—C25	1.523 (7)
C22—H22A	0.9600	C24—H24A	0.9600
C22—H22B	0.9600	C24—H24B	0.9600
C22—H22C	0.9600	C24—H24C	0.9600
C23—H23A	0.9600	C25—C26	1.495 (6)
C23—H23B	0.9600	C25—H25	0.9800
C23—H23C	0.9600	C26—C31	1.371 (7)
O1D—C7D	1.43 (2)	C26—C27	1.375 (7)
O2D—C14D	1.259 (5)	C27—C28	1.381 (8)
O3D—C14D	1.241 (5)	C27—H27	0.9300
C1D—C2D	1.38 (2)	C28—C29	1.347 (10)
C1D—C6D	1.39 (2)	C28—H28	0.9300
C1D—C7D	1.57 (2)	C29—C30	1.357 (10)
C2D—C3D	1.41 (2)	C29—H29	0.9300
C2D—C15D	1.51 (2)	C30—C31	1.397 (8)
C3D—C4D	1.42 (2)	C30—H30	0.9300
C3D—H3D	0.9300	C31—H31	0.9300
C4D—C5D	1.39 (2)
C2—C1—C6	120.4 (5)	C22D—C7D—C8D	118 (3)
C2—C1—C7	119.1 (6)	O1D—C7D—C1D	107 (3)
C6—C1—C7	120.5 (6)	C22D—C7D—C1D	101 (2)
C1—C2—C3	118.8 (6)	C8D—C7D—C1D	110 (3)
C1—C2—C15	120.7 (7)	C13D—C8D—C9D	119 (3)
C3—C2—C15	120.4 (7)	C13D—C8D—C7D	120 (3)
C4—C3—C2	122.2 (7)	C9D—C8D—C7D	121 (3)
C4—C3—H3	118.9	C8D—C9D—C10D	122 (3)
C2—C3—H3	118.9	C8D—C9D—H9D	119.1
C3—C4—C5	117.6 (6)	C10D—C9D—H9D	119.1
C3—C4—C18	122.9 (7)	C9D—C10D—C11D	120 (3)
C5—C4—C18	119.5 (7)	C9D—C10D—H10D	120.1
C4—C5—C6	122.6 (6)	C11D—C10D—H10D	120.1
C4—C5—H5	118.7	C12D—C11D—C10D	117 (2)
C6—C5—H5	118.7	C12D—C11D—C14D	121 (2)
C5—C6—C1	118.5 (6)	C10D—C11D—C14D	122 (2)
C5—C6—C21	120.8 (6)	C11D—C12D—C13D	123 (3)
C1—C6—C21	120.8 (5)	C11D—C12D—H12D	118.4
O1—C7—C8	119.9 (6)	C13D—C12D—H12D	118.4
O1—C7—C1	120.4 (6)	C12D—C13D—C8D	119 (3)
C8—C7—C1	119.7 (6)	C12D—C13D—H13D	120.3
C13—C8—C9	118.6 (5)	C8D—C13D—H13D	120.3
C13—C8—C7	122.5 (6)	O3D—C14D—O2D	124.2 (4)
C9—C8—C7	118.8 (6)	O3D—C14D—C11D	118.3 (15)
C10—C9—C8	120.3 (5)	O2D—C14D—C11D	117.5 (15)
C10—C9—H9	119.8	C16D—C15D—C2D	113 (4)
C8—C9—H9	119.8	C16D—C15D—C17D	116 (4)
C9—C10—C11	121.0 (5)	C2D—C15D—C17D	112 (4)
C9—C10—H10	119.5	C16D—C15D—H15D	105.1
C11—C10—H10	119.5	C2D—C15D—H15D	105.1
C10—C11—C12	119.3 (5)	C17D—C15D—H15D	105.1
C10—C11—C14	120.9 (5)	C15D—C16D—H16D	109.5
C12—C11—C14	119.8 (6)	C15D—C16D—H16E	109.5
C13—C12—C11	119.4 (6)	H16D—C16D—H16E	109.5
C13—C12—H12	120.3	C15D—C16D—H16F	109.5
C11—C12—H12	120.3	H16D—C16D—H16F	109.5
C8—C13—C12	121.2 (6)	H16E—C16D—H16F	109.5
C8—C13—H13	119.4	C15D—C17D—H17D	109.5
C12—C13—H13	119.4	C15D—C17D—H17E	109.5
O3—C14—O2	124.2 (4)	H17D—C17D—H17E	109.5
O3—C14—C11	118.0 (5)	C15D—C17D—H17F	109.5
O2—C14—C11	117.8 (5)	H17D—C17D—H17F	109.5
C2—C15—C17	112.5 (7)	H17E—C17D—H17F	109.5
C2—C15—C16	111.2 (6)	C19D—C18D—C20D	112 (4)
C17—C15—C16	110.9 (7)	C19D—C18D—C4D	115 (3)
C2—C15—H15	107.3	C20D—C18D—C4D	105 (3)
C17—C15—H15	107.3	C19D—C18D—H18D	108.3
C16—C15—H15	107.3	C20D—C18D—H18D	108.3
C15—C16—H16A	109.5	C4D—C18D—H18D	108.3
C15—C16—H16B	109.5	C18D—C19D—H19D	109.5
H16A—C16—H16B	109.5	C18D—C19D—H19E	109.5
C15—C16—H16C	109.5	H19D—C19D—H19E	109.5
H16A—C16—H16C	109.5	C18D—C19D—H19F	109.5
H16B—C16—H16C	109.5	H19D—C19D—H19F	109.5
C15—C17—H17A	109.5	H19E—C19D—H19F	109.5
C15—C17—H17B	109.5	C18D—C20D—H20D	109.5
H17A—C17—H17B	109.5	C18D—C20D—H20E	109.5
C15—C17—H17C	109.5	H20D—C20D—H20E	109.5
H17A—C17—H17C	109.5	C18D—C20D—H20F	109.5
H17B—C17—H17C	109.5	H20D—C20D—H20F	109.5
C20—C18—C19	114.7 (7)	H20E—C20D—H20F	109.5
C20—C18—C4	112.2 (7)	C23D—C21D—C22D	120 (4)
C19—C18—C4	115.5 (7)	C23D—C21D—C6D	114 (3)
C20—C18—H18	104.3	C22D—C21D—C6D	99 (2)
C19—C18—H18	104.3	C23D—C21D—H21D	107.8
C4—C18—H18	104.3	C22D—C21D—H21D	107.8
C18—C19—H19A	109.5	C6D—C21D—H21D	107.8
C18—C19—H19B	109.5	C7D—C22D—C21D	108 (2)
H19A—C19—H19B	109.5	C7D—C22D—H22D	110.0
C18—C19—H19C	109.5	C21D—C22D—H22D	110.0
H19A—C19—H19C	109.5	C7D—C22D—H22E	110.0
H19B—C19—H19C	109.5	C21D—C22D—H22E	110.0
C18—C20—H20A	109.5	H22D—C22D—H22E	108.4
C18—C20—H20B	109.5	C21D—C23D—H23D	109.5
H20A—C20—H20B	109.5	C21D—C23D—H23E	109.5
C18—C20—H20C	109.5	H23D—C23D—H23E	109.5
H20A—C20—H20C	109.5	C21D—C23D—H23F	109.5
H20B—C20—H20C	109.5	H23D—C23D—H23F	109.5
C22—C21—C6	110.8 (6)	H23E—C23D—H23F	109.5
C22—C21—C23	110.1 (6)	C25—N1—H1A	109.5
C6—C21—C23	113.7 (6)	C25—N1—H1B	109.5
C22—C21—H21	107.3	H1A—N1—H1B	109.5
C6—C21—H21	107.3	C25—N1—H1C	109.5
C23—C21—H21	107.3	H1A—N1—H1C	109.5
C21—C22—H22A	109.5	H1B—N1—H1C	109.5
C21—C22—H22B	109.5	C25—C24—H24A	109.5
H22A—C22—H22B	109.5	C25—C24—H24B	109.5
C21—C22—H22C	109.5	H24A—C24—H24B	109.5
H22A—C22—H22C	109.5	C25—C24—H24C	109.5
H22B—C22—H22C	109.5	H24A—C24—H24C	109.5
C21—C23—H23A	109.5	H24B—C24—H24C	109.5
C21—C23—H23B	109.5	C26—C25—N1	110.2 (4)
H23A—C23—H23B	109.5	C26—C25—C24	114.9 (4)
C21—C23—H23C	109.5	N1—C25—C24	108.5 (4)
H23A—C23—H23C	109.5	C26—C25—H25	107.7
H23B—C23—H23C	109.5	N1—C25—H25	107.7
C2D—C1D—C6D	125 (3)	C24—C25—H25	107.7
C2D—C1D—C7D	125 (3)	C31—C26—C27	118.3 (5)
C6D—C1D—C7D	108 (2)	C31—C26—C25	121.5 (5)
C1D—C2D—C3D	116 (3)	C27—C26—C25	120.3 (5)
C1D—C2D—C15D	123 (3)	C26—C27—C28	121.1 (7)
C3D—C2D—C15D	121 (3)	C26—C27—H27	119.4
C2D—C3D—C4D	120 (3)	C28—C27—H27	119.4
C2D—C3D—H3D	119.8	C29—C28—C27	119.8 (8)
C4D—C3D—H3D	119.8	C29—C28—H28	120.1
C5D—C4D—C3D	120 (3)	C27—C28—H28	120.1
C5D—C4D—C18D	116 (3)	C28—C29—C30	120.9 (8)
C3D—C4D—C18D	123 (3)	C28—C29—H29	119.5
C6D—C5D—C4D	120 (3)	C30—C29—H29	119.5
C6D—C5D—H5D	120.2	C29—C30—C31	119.5 (8)
C4D—C5D—H5D	120.2	C29—C30—H30	120.2
C5D—C6D—C1D	119 (3)	C31—C30—H30	120.2
C5D—C6D—C21D	129 (3)	C26—C31—C30	120.4 (7)
C1D—C6D—C21D	112 (2)	C26—C31—H31	119.8
O1D—C7D—C22D	113 (3)	C30—C31—H31	119.8
O1D—C7D—C8D	108 (3)

(270minUV)

Crystal data

C31H39NO3	Dx = 1.121 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2672 reflections
a = 6.2975 (5) Å	θ = 1.6–19.9°
b = 13.6726 (12) Å	µ = 0.07 mm^−1
c = 32.5998 (19) Å	T = 299 K
V = 2806.9 (4) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5431 independent reflections
Radiation source: fine-focus sealed tube	2313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −16→14
Tmin = 0.783, Tmax = 1.000	l = −39→40
25077 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0388P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5431 reflections	Δρmax = 0.14 e Å^−3
505 parameters	Δρmin = −0.14 e Å^−3
571 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.9 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.0391 (18)	0.2455 (7)	0.6316 (3)	0.089 (3)	0.721 (4)
O2	0.6264 (7)	0.6312 (3)	0.51689 (13)	0.0704 (13)	0.721 (4)
O3	0.3267 (8)	0.6187 (4)	0.55118 (13)	0.0830 (15)	0.721 (4)
C1	0.817 (3)	0.2771 (10)	0.6886 (4)	0.059 (4)	0.721 (4)
C2	0.883 (4)	0.3431 (13)	0.7188 (5)	0.067 (4)	0.721 (4)
C3	0.821 (4)	0.3291 (16)	0.7595 (5)	0.069 (4)	0.721 (4)
H3	0.8676	0.3724	0.7795	0.083*	0.721 (4)
C4	0.692 (4)	0.2526 (16)	0.7705 (4)	0.062 (4)	0.721 (4)
C5	0.627 (5)	0.1879 (19)	0.7401 (4)	0.070 (4)	0.721 (4)
H5	0.5410	0.1353	0.7471	0.084*	0.721 (4)
C6	0.688 (4)	0.1999 (12)	0.6992 (4)	0.062 (4)	0.721 (4)
C7	0.893 (2)	0.2940 (9)	0.6457 (4)	0.066 (4)	0.721 (4)
C8	0.785 (2)	0.3672 (10)	0.6188 (4)	0.052 (4)	0.721 (4)
C9	0.881 (2)	0.3932 (8)	0.5820 (4)	0.060 (3)	0.721 (4)
H9	1.0043	0.3619	0.5735	0.072*	0.721 (4)
C10	0.7923 (19)	0.4654 (8)	0.5583 (3)	0.058 (3)	0.721 (4)
H10	0.8605	0.4842	0.5342	0.070*	0.721 (4)
C11	0.608 (2)	0.5100 (10)	0.5689 (4)	0.049 (3)	0.721 (4)
C12	0.503 (2)	0.4796 (11)	0.6049 (4)	0.061 (4)	0.721 (4)
H12	0.3714	0.5058	0.6119	0.073*	0.721 (4)
C13	0.598 (2)	0.4106 (8)	0.6298 (4)	0.057 (4)	0.721 (4)
H13	0.5332	0.3932	0.6544	0.069*	0.721 (4)
C14	0.5131 (13)	0.5941 (5)	0.54453 (19)	0.0617 (18)	0.721 (4)
C15	1.020 (3)	0.4314 (11)	0.7089 (7)	0.078 (4)	0.721 (4)
H15	1.0294	0.4354	0.6789	0.093*	0.721 (4)
C16	1.245 (3)	0.4183 (19)	0.7247 (7)	0.085 (6)	0.721 (4)
H16A	1.3014	0.3573	0.7149	0.127*	0.721 (4)
H16B	1.3324	0.4711	0.7150	0.127*	0.721 (4)
H16C	1.2442	0.4182	0.7541	0.127*	0.721 (4)
C17	0.925 (3)	0.5269 (10)	0.7236 (5)	0.099 (5)	0.721 (4)
H17A	1.0180	0.5800	0.7165	0.149*	0.721 (4)
H17B	0.7894	0.5367	0.7108	0.149*	0.721 (4)
H17C	0.9072	0.5247	0.7528	0.149*	0.721 (4)
C18	0.634 (3)	0.2298 (16)	0.8151 (4)	0.092 (5)	0.721 (4)
H18	0.6460	0.1585	0.8170	0.111*	0.721 (4)
C19	0.783 (2)	0.2664 (13)	0.8464 (4)	0.101 (5)	0.721 (4)
H19A	0.9258	0.2508	0.8384	0.152*	0.721 (4)
H19B	0.7684	0.3360	0.8490	0.152*	0.721 (4)
H19C	0.7524	0.2360	0.8723	0.152*	0.721 (4)
C20	0.405 (2)	0.2493 (16)	0.8240 (4)	0.094 (5)	0.721 (4)
H20A	0.3193	0.2233	0.8022	0.142*	0.721 (4)
H20B	0.3663	0.2186	0.8494	0.142*	0.721 (4)
H20C	0.3823	0.3186	0.8260	0.142*	0.721 (4)
C21	0.611 (2)	0.1297 (10)	0.6663 (4)	0.076 (4)	0.721 (4)
H21	0.5920	0.1677	0.6411	0.091*	0.721 (4)
C22	0.775 (2)	0.0522 (11)	0.6575 (5)	0.097 (5)	0.721 (4)
H22A	0.7223	0.0088	0.6367	0.145*	0.721 (4)
H22B	0.9034	0.0825	0.6482	0.145*	0.721 (4)
H22C	0.8031	0.0157	0.6821	0.145*	0.721 (4)
C23	0.393 (2)	0.0810 (10)	0.6764 (4)	0.103 (5)	0.721 (4)
H23A	0.2897	0.1308	0.6820	0.154*	0.721 (4)
H23B	0.3474	0.0424	0.6535	0.154*	0.721 (4)
H23C	0.4084	0.0397	0.7001	0.154*	0.721 (4)
O1D	1.090 (6)	0.278 (3)	0.6392 (15)	0.081 (11)*	0.201 (4)
O2D	0.6264 (7)	0.6312 (3)	0.51689 (13)	0.0704 (13)	0.201 (4)
O3D	0.3267 (8)	0.6187 (4)	0.55118 (13)	0.0830 (15)	0.201 (4)
C1D	0.799 (9)	0.287 (3)	0.6895 (11)	0.063 (12)*	0.201 (4)
C2D	0.897 (12)	0.344 (4)	0.7186 (14)	0.063 (12)*	0.201 (4)
C3D	0.852 (12)	0.323 (5)	0.7599 (14)	0.065 (12)*	0.201 (4)
H3D	0.9105	0.3617	0.7805	0.078*	0.201 (4)
C4D	0.718 (10)	0.243 (5)	0.7706 (12)	0.050 (11)*	0.201 (4)
C5D	0.615 (15)	0.191 (6)	0.7397 (12)	0.073 (12)*	0.201 (4)
H5D	0.5177	0.1424	0.7464	0.087*	0.201 (4)
C6D	0.659 (11)	0.212 (4)	0.6992 (12)	0.065 (12)*	0.201 (4)
C7D	0.863 (6)	0.277 (2)	0.6434 (11)	0.071 (12)*	0.201 (4)
C8D	0.767 (7)	0.361 (3)	0.6182 (13)	0.054 (11)*	0.201 (4)
C9D	0.892 (7)	0.412 (3)	0.5906 (13)	0.056 (11)*	0.201 (4)
H9D	1.0326	0.3928	0.5872	0.067*	0.201 (4)
C10D	0.816 (6)	0.490 (3)	0.5679 (12)	0.056 (11)*	0.201 (4)
H10D	0.9054	0.5224	0.5497	0.067*	0.201 (4)
C11D	0.605 (7)	0.520 (3)	0.5726 (13)	0.054 (11)*	0.201 (4)
C12D	0.481 (8)	0.468 (3)	0.6005 (14)	0.063 (12)*	0.201 (4)
H12D	0.3406	0.4863	0.6041	0.075*	0.201 (4)
C13D	0.559 (6)	0.390 (3)	0.6231 (13)	0.044 (11)*	0.201 (4)
H13D	0.4705	0.3568	0.6414	0.053*	0.201 (4)
C14D	0.5131 (13)	0.5941 (5)	0.54453 (19)	0.0617 (18)	0.201 (4)
C15D	1.051 (9)	0.425 (4)	0.708 (2)	0.070 (11)*	0.201 (4)
H15D	1.1014	0.4108	0.6800	0.084*	0.201 (4)
C16D	1.242 (12)	0.422 (7)	0.735 (3)	0.09 (2)*	0.201 (4)
H16D	1.3366	0.4745	0.7273	0.140*	0.201 (4)
H16E	1.1992	0.4306	0.7629	0.140*	0.201 (4)
H16F	1.3134	0.3608	0.7317	0.140*	0.201 (4)
C17D	0.935 (12)	0.524 (4)	0.706 (2)	0.081 (18)*	0.201 (4)
H17D	0.8153	0.5183	0.6877	0.121*	0.201 (4)
H17E	0.8881	0.5418	0.7326	0.121*	0.201 (4)
H17F	1.0309	0.5726	0.6954	0.121*	0.201 (4)
C18D	0.648 (8)	0.220 (5)	0.8160 (12)	0.082 (11)*	0.201 (4)
H18D	0.5815	0.1552	0.8160	0.099*	0.201 (4)
C19D	0.826 (8)	0.218 (3)	0.8469 (15)	0.097 (13)*	0.201 (4)
H19D	0.9295	0.1702	0.8389	0.145*	0.201 (4)
H19E	0.8925	0.2815	0.8480	0.145*	0.201 (4)
H19F	0.7707	0.2022	0.8735	0.145*	0.201 (4)
C20D	0.474 (8)	0.296 (4)	0.8263 (16)	0.122 (19)*	0.201 (4)
H20D	0.3652	0.2934	0.8057	0.184*	0.201 (4)
H20E	0.4134	0.2804	0.8526	0.184*	0.201 (4)
H20F	0.5353	0.3598	0.8271	0.184*	0.201 (4)
C21D	0.585 (7)	0.156 (3)	0.6603 (12)	0.097 (12)*	0.201 (4)
H21D	0.4603	0.1884	0.6486	0.116*	0.201 (4)
C22D	0.779 (6)	0.175 (2)	0.6334 (10)	0.106 (13)*	0.201 (4)
H22D	0.8873	0.1268	0.6386	0.127*	0.201 (4)
H22E	0.7392	0.1719	0.6046	0.127*	0.201 (4)
C23D	0.531 (10)	0.051 (3)	0.6700 (18)	0.15 (2)*	0.201 (4)
H23D	0.4071	0.0484	0.6871	0.224*	0.201 (4)
H23E	0.5045	0.0158	0.6450	0.224*	0.201 (4)
H23F	0.6483	0.0208	0.6842	0.224*	0.201 (4)
O1P	1.115 (9)	0.303 (5)	0.650 (2)	0.083 (13)*	0.078 (4)
O2P	0.6264 (7)	0.6312 (3)	0.51689 (13)	0.0704 (13)	0.078 (4)
O3P	0.3267 (8)	0.6187 (4)	0.55118 (13)	0.0830 (15)	0.078 (4)
C1P	0.803 (14)	0.293 (5)	0.6970 (16)	0.061 (13)*	0.078 (4)
C2P	0.846 (17)	0.350 (6)	0.7311 (16)	0.065 (14)*	0.078 (4)
C3P	0.779 (18)	0.321 (7)	0.7697 (17)	0.064 (13)*	0.078 (4)
H3P	0.8091	0.3590	0.7926	0.077*	0.078 (4)
C4P	0.67 (2)	0.235 (7)	0.774 (2)	0.047 (13)*	0.078 (4)
C5P	0.62 (3)	0.176 (8)	0.740 (2)	0.070 (13)*	0.078 (4)
H5P	0.5476	0.1183	0.7429	0.084*	0.078 (4)
C6P	0.70 (2)	0.205 (7)	0.702 (2)	0.064 (13)*	0.078 (4)
C7P	0.938 (8)	0.350 (3)	0.6675 (12)	0.064 (13)*	0.078 (4)
C8P	0.834 (7)	0.413 (2)	0.6345 (11)	0.045 (12)*	0.078 (4)
C9P	0.943 (7)	0.448 (3)	0.6006 (13)	0.060 (13)*	0.078 (4)
H9P	1.0855	0.4319	0.5974	0.072*	0.078 (4)
C10P	0.842 (7)	0.506 (3)	0.5713 (13)	0.059 (13)*	0.078 (4)
H10P	0.9179	0.5284	0.5487	0.071*	0.078 (4)
C11P	0.629 (6)	0.5307 (12)	0.5758 (9)	0.054 (13)*	0.078 (4)
C12P	0.519 (8)	0.497 (3)	0.6097 (13)	0.059 (13)*	0.078 (4)
H12P	0.3761	0.5127	0.6131	0.071*	0.078 (4)
C13P	0.620 (8)	0.439 (4)	0.6388 (14)	0.044 (14)*	0.078 (4)
H13P	0.5446	0.4164	0.6614	0.053*	0.078 (4)
C14P	0.5131 (13)	0.5941 (5)	0.54453 (19)	0.0617 (18)	0.078 (4)
C15P	0.982 (12)	0.421 (4)	0.7078 (15)	0.075 (13)*	0.078 (4)
C16P	1.217 (13)	0.428 (11)	0.717 (4)	0.09 (3)*	0.078 (4)
H16G	1.2809	0.4769	0.6997	0.128*	0.078 (4)
H16H	1.2368	0.4466	0.7453	0.128*	0.078 (4)
H16I	1.2832	0.3662	0.7121	0.128*	0.078 (4)
C17P	0.88 (2)	0.523 (4)	0.704 (4)	0.09 (3)*	0.078 (4)
H17G	0.9791	0.5645	0.6884	0.129*	0.078 (4)
H17H	0.7515	0.5182	0.6892	0.129*	0.078 (4)
H17I	0.8609	0.5502	0.7303	0.129*	0.078 (4)
C18P	0.568 (15)	0.207 (7)	0.815 (2)	0.088 (14)*	0.078 (4)
H18P	0.5541	0.1360	0.8176	0.106*	0.078 (4)
C19P	0.699 (18)	0.248 (12)	0.850 (3)	0.099 (15)*	0.078 (4)
H19G	0.6344	0.2297	0.8760	0.149*	0.078 (4)
H19H	0.8400	0.2214	0.8491	0.149*	0.078 (4)
H19I	0.7050	0.3177	0.8484	0.149*	0.078 (4)
C20P	0.349 (15)	0.255 (14)	0.813 (4)	0.08 (2)*	0.078 (4)
H20G	0.2731	0.2415	0.8379	0.113*	0.078 (4)
H20H	0.3652	0.3240	0.8096	0.113*	0.078 (4)
H20I	0.2724	0.2283	0.7901	0.113*	0.078 (4)
C21P	0.679 (15)	0.140 (6)	0.664 (2)	0.083 (14)*	0.078 (4)
H21P	0.6948	0.1837	0.6405	0.100*	0.078 (4)
C22P	0.863 (17)	0.068 (11)	0.661 (5)	0.10 (3)*	0.078 (4)
H22F	0.8462	0.0286	0.6371	0.147*	0.078 (4)
H22G	0.9940	0.1035	0.6597	0.147*	0.078 (4)
H22H	0.8634	0.0270	0.6851	0.147*	0.078 (4)
C23P	0.463 (15)	0.093 (9)	0.659 (4)	0.11 (3)*	0.078 (4)
H23G	0.4627	0.0526	0.6351	0.168*	0.078 (4)
H23H	0.4339	0.0529	0.6829	0.168*	0.078 (4)
H23I	0.3568	0.1425	0.6569	0.168*	0.078 (4)
N1	0.0407 (8)	0.6681 (3)	0.49166 (13)	0.0588 (14)
H1A	0.1439	0.6476	0.5082	0.071*
H1B	−0.0844	0.6499	0.5018	0.071*
H1C	0.0453	0.7330	0.4897	0.071*
C24	0.2820 (12)	0.6581 (5)	0.4326 (2)	0.090 (2)
H24A	0.3940	0.6412	0.4513	0.135*
H24B	0.2790	0.7277	0.4289	0.135*
H24C	0.3067	0.6268	0.4067	0.135*
C25	0.0698 (11)	0.6239 (5)	0.45005 (18)	0.0667 (19)
H25	−0.0428	0.6494	0.4323	0.080*
C26	0.0434 (13)	0.5159 (6)	0.45254 (19)	0.068 (2)
C27	−0.1423 (15)	0.4729 (7)	0.4402 (2)	0.092 (3)
H27	−0.2530	0.5122	0.4310	0.111*
C28	−0.170 (2)	0.3712 (9)	0.4409 (3)	0.125 (4)
H28	−0.2967	0.3430	0.4322	0.150*
C29	−0.008 (3)	0.3147 (9)	0.4547 (4)	0.147 (6)
H29	−0.0244	0.2471	0.4551	0.176*
C30	0.176 (2)	0.3542 (8)	0.4678 (3)	0.133 (4)
H30	0.2837	0.3140	0.4775	0.160*
C31	0.2042 (15)	0.4560 (6)	0.4668 (2)	0.095 (3)
H31	0.3314	0.4832	0.4757	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.111 (7)	0.083 (7)	0.075 (6)	0.041 (6)	0.037 (6)	0.022 (5)
O2	0.073 (3)	0.075 (3)	0.063 (3)	0.001 (3)	0.006 (3)	0.025 (2)
O3	0.071 (4)	0.114 (4)	0.064 (3)	0.028 (3)	0.002 (3)	0.028 (3)
C1	0.068 (7)	0.052 (6)	0.058 (6)	0.019 (6)	0.001 (6)	0.016 (5)
C2	0.073 (9)	0.055 (6)	0.072 (7)	0.009 (6)	0.008 (6)	0.020 (6)
C3	0.067 (10)	0.069 (7)	0.071 (7)	−0.004 (7)	−0.011 (6)	−0.007 (6)
C4	0.055 (9)	0.071 (9)	0.061 (7)	0.009 (7)	0.007 (6)	0.012 (6)
C5	0.074 (8)	0.074 (7)	0.063 (6)	−0.010 (7)	−0.005 (6)	0.021 (5)
C6	0.078 (9)	0.057 (7)	0.053 (6)	0.005 (7)	−0.014 (6)	0.020 (5)
C7	0.088 (9)	0.056 (6)	0.055 (6)	0.004 (7)	0.001 (6)	0.009 (5)
C8	0.061 (7)	0.050 (6)	0.047 (6)	0.004 (5)	0.002 (5)	0.010 (4)
C9	0.071 (7)	0.053 (6)	0.057 (7)	0.016 (6)	0.012 (6)	0.003 (6)
C10	0.064 (7)	0.059 (7)	0.051 (6)	0.006 (6)	0.008 (5)	0.002 (6)
C11	0.056 (7)	0.053 (6)	0.038 (5)	−0.002 (5)	0.000 (5)	0.001 (5)
C12	0.048 (6)	0.075 (7)	0.059 (7)	0.005 (6)	0.006 (6)	0.011 (6)
C13	0.066 (8)	0.066 (8)	0.040 (6)	−0.011 (7)	0.004 (6)	0.004 (6)
C14	0.078 (5)	0.062 (4)	0.046 (4)	0.015 (4)	−0.014 (4)	0.005 (3)
C15	0.073 (10)	0.080 (8)	0.079 (7)	0.003 (7)	−0.011 (7)	0.003 (6)
C16	0.088 (10)	0.088 (10)	0.079 (14)	−0.003 (7)	0.010 (9)	−0.001 (9)
C17	0.088 (10)	0.074 (8)	0.136 (15)	−0.014 (7)	0.008 (12)	0.008 (9)
C18	0.087 (9)	0.128 (11)	0.061 (7)	−0.001 (8)	0.018 (7)	−0.012 (6)
C19	0.106 (11)	0.135 (12)	0.063 (7)	−0.001 (10)	0.000 (7)	−0.002 (8)
C20	0.096 (11)	0.119 (11)	0.069 (9)	−0.020 (11)	0.018 (8)	−0.005 (9)
C21	0.103 (10)	0.078 (8)	0.048 (6)	−0.009 (8)	−0.020 (6)	0.006 (6)
C22	0.125 (12)	0.099 (9)	0.067 (7)	0.024 (11)	−0.009 (9)	−0.016 (6)
C23	0.112 (11)	0.116 (9)	0.080 (8)	−0.045 (10)	−0.010 (8)	0.000 (7)
O2D	0.073 (3)	0.075 (3)	0.063 (3)	0.001 (3)	0.006 (3)	0.025 (2)
O3D	0.071 (4)	0.114 (4)	0.064 (3)	0.028 (3)	0.002 (3)	0.028 (3)
C14D	0.078 (5)	0.062 (4)	0.046 (4)	0.015 (4)	−0.014 (4)	0.005 (3)
O2P	0.073 (3)	0.075 (3)	0.063 (3)	0.001 (3)	0.006 (3)	0.025 (2)
O3P	0.071 (4)	0.114 (4)	0.064 (3)	0.028 (3)	0.002 (3)	0.028 (3)
C14P	0.078 (5)	0.062 (4)	0.046 (4)	0.015 (4)	−0.014 (4)	0.005 (3)
N1	0.064 (4)	0.065 (3)	0.047 (3)	0.002 (3)	−0.001 (3)	0.010 (3)
C24	0.106 (7)	0.107 (6)	0.057 (4)	−0.012 (5)	0.023 (5)	0.001 (4)
C25	0.075 (5)	0.081 (5)	0.045 (4)	0.002 (4)	−0.010 (4)	0.003 (4)
C26	0.078 (6)	0.080 (5)	0.047 (4)	−0.002 (5)	0.004 (4)	−0.005 (4)
C27	0.098 (7)	0.106 (7)	0.073 (5)	−0.011 (6)	0.008 (5)	−0.018 (5)
C28	0.143 (11)	0.123 (10)	0.109 (8)	−0.039 (8)	0.027 (8)	−0.034 (7)
C29	0.215 (18)	0.097 (9)	0.128 (10)	−0.031 (10)	0.042 (11)	−0.024 (7)
C30	0.187 (13)	0.087 (8)	0.125 (9)	0.013 (8)	0.007 (9)	0.003 (6)
C31	0.108 (8)	0.084 (6)	0.092 (6)	0.000 (6)	−0.010 (6)	−0.007 (5)

Geometric parameters (Å, º)

O1—C7	1.223 (12)	C18D—C20D	1.54 (3)
O2—C14	1.256 (7)	C18D—H18D	0.9800
O3—C14	1.241 (8)	C19D—H19D	0.9600
C1—C6	1.376 (12)	C19D—H19E	0.9600
C1—C2	1.397 (12)	C19D—H19F	0.9600
C1—C7	1.497 (12)	C20D—H20D	0.9600
C2—C3	1.398 (13)	C20D—H20E	0.9600
C2—C15	1.518 (13)	C20D—H20F	0.9600
C3—C4	1.369 (12)	C21D—C23D	1.51 (3)
C3—H3	0.9300	C21D—C22D	1.53 (3)
C4—C5	1.391 (14)	C21D—H21D	0.9800
C4—C18	1.534 (13)	C22D—H22D	0.9700
C5—C6	1.396 (12)	C22D—H22E	0.9700
C5—H5	0.9300	C23D—H23D	0.9600
C6—C21	1.519 (12)	C23D—H23E	0.9600
C7—C8	1.494 (11)	C23D—H23F	0.9600
C8—C13	1.367 (12)	O1P—C7P	1.40 (2)
C8—C9	1.391 (11)	O2P—C14P	1.256 (7)
C9—C10	1.372 (10)	O3P—C14P	1.241 (8)
C9—H9	0.9300	C1P—C2P	1.39 (3)
C10—C11	1.355 (12)	C1P—C6P	1.39 (2)
C10—H10	0.9300	C1P—C7P	1.50 (2)
C11—C12	1.412 (11)	C2P—C3P	1.39 (2)
C11—C14	1.520 (10)	C2P—C15P	1.50 (2)
C12—C13	1.380 (11)	C3P—C4P	1.38 (3)
C12—H12	0.9300	C3P—H3P	0.9300
C13—H13	0.9300	C4P—C5P	1.40 (3)
C15—C17	1.516 (15)	C4P—C18P	1.52 (3)
C15—C16	1.518 (14)	C5P—C6P	1.39 (3)
C15—H15	0.9800	C5P—H5P	0.9300
C16—H16A	0.9600	C6P—C21P	1.51 (3)
C16—H16B	0.9600	C7P—C8P	1.53 (2)
C16—H16C	0.9600	C7P—C15P	1.66 (2)
C17—H17A	0.9600	C8P—C9P	1.38 (2)
C17—H17B	0.9600	C8P—C13P	1.39 (3)
C17—H17C	0.9600	C9P—C10P	1.40 (2)
C18—C19	1.476 (15)	C9P—H9P	0.9300
C18—C20	1.492 (15)	C10P—C11P	1.39 (3)
C18—H18	0.9800	C10P—H10P	0.9300
C19—H19A	0.9600	C11P—C12P	1.39 (3)
C19—H19B	0.9600	C11P—C14P	1.52 (2)
C19—H19C	0.9600	C12P—C13P	1.39 (3)
C20—H20A	0.9600	C12P—H12P	0.9300
C20—H20B	0.9600	C13P—H13P	0.9300
C20—H20C	0.9600	C15P—C16P	1.51 (3)
C21—C22	1.507 (14)	C15P—C17P	1.53 (3)
C21—C23	1.560 (14)	C16P—H16G	0.9600
C21—H21	0.9800	C16P—H16H	0.9600
C22—H22A	0.9600	C16P—H16I	0.9600
C22—H22B	0.9600	C17P—H17G	0.9600
C22—H22C	0.9600	C17P—H17H	0.9600
C23—H23A	0.9600	C17P—H17I	0.9600
C23—H23B	0.9600	C18P—C20P	1.52 (3)
C23—H23C	0.9600	C18P—C19P	1.52 (3)
O1D—C7D	1.44 (2)	C18P—H18P	0.9800
O2D—C14D	1.256 (7)	C19P—H19G	0.9600
O3D—C14D	1.241 (8)	C19P—H19H	0.9600
C1D—C2D	1.37 (2)	C19P—H19I	0.9600
C1D—C6D	1.39 (2)	C20P—H20G	0.9600
C1D—C7D	1.56 (2)	C20P—H20H	0.9600
C2D—C3D	1.41 (2)	C20P—H20I	0.9600
C2D—C15D	1.51 (2)	C21P—C23P	1.51 (3)
C3D—C4D	1.42 (2)	C21P—C22P	1.52 (3)
C3D—H3D	0.9300	C21P—H21P	0.9800
C4D—C5D	1.40 (2)	C22P—H22F	0.9600
C4D—C18D	1.58 (2)	C22P—H22G	0.9600
C5D—C6D	1.38 (2)	C22P—H22H	0.9600
C5D—H5D	0.9300	C23P—H23G	0.9600
C6D—C21D	1.55 (2)	C23P—H23H	0.9600
C7D—C22D	1.52 (2)	C23P—H23I	0.9600
C7D—C8D	1.53 (2)	N1—C25	1.496 (7)
C8D—C13D	1.38 (2)	N1—H1A	0.8900
C8D—C9D	1.38 (2)	N1—H1B	0.8900
C9D—C10D	1.38 (2)	N1—H1C	0.8900
C9D—H9D	0.9300	C24—C25	1.525 (9)
C10D—C11D	1.40 (2)	C24—H24A	0.9600
C10D—H10D	0.9300	C24—H24B	0.9600
C11D—C12D	1.39 (2)	C24—H24C	0.9600
C11D—C14D	1.48 (2)	C25—C26	1.489 (9)
C12D—C13D	1.39 (2)	C25—H25	0.9800
C12D—H12D	0.9300	C26—C27	1.370 (10)
C13D—H13D	0.9300	C26—C31	1.382 (10)
C15D—C16D	1.49 (3)	C27—C28	1.402 (11)
C15D—C17D	1.54 (3)	C27—H27	0.9300
C15D—H15D	0.9800	C28—C29	1.355 (15)
C16D—H16D	0.9600	C28—H28	0.9300
C16D—H16E	0.9600	C29—C30	1.347 (14)
C16D—H16F	0.9600	C29—H29	0.9300
C17D—H17D	0.9600	C30—C31	1.404 (11)
C17D—H17E	0.9600	C30—H30	0.9300
C17D—H17F	0.9600	C31—H31	0.9300
C18D—C19D	1.51 (3)
C6—C1—C2	119.6 (10)	C18D—C19D—H19D	109.5
C6—C1—C7	122.7 (10)	C18D—C19D—H19E	109.5
C2—C1—C7	117.6 (11)	H19D—C19D—H19E	109.5
C1—C2—C3	119.7 (11)	C18D—C19D—H19F	109.5
C1—C2—C15	122.2 (12)	H19D—C19D—H19F	109.5
C3—C2—C15	118.1 (12)	H19E—C19D—H19F	109.5
C4—C3—C2	121.3 (11)	C18D—C20D—H20D	109.5
C4—C3—H3	119.4	C18D—C20D—H20E	109.5
C2—C3—H3	119.4	H20D—C20D—H20E	109.5
C3—C4—C5	118.3 (11)	C18D—C20D—H20F	109.5
C3—C4—C18	123.0 (13)	H20D—C20D—H20F	109.5
C5—C4—C18	118.4 (12)	H20E—C20D—H20F	109.5
C4—C5—C6	121.6 (11)	C23D—C21D—C22D	118 (4)
C4—C5—H5	119.2	C23D—C21D—C6D	111 (3)
C6—C5—H5	119.2	C22D—C21D—C6D	98 (2)
C1—C6—C5	119.5 (11)	C23D—C21D—H21D	109.6
C1—C6—C21	119.8 (10)	C22D—C21D—H21D	109.6
C5—C6—C21	120.7 (11)	C6D—C21D—H21D	109.6
O1—C7—C8	119.1 (10)	C7D—C22D—C21D	108 (2)
O1—C7—C1	120.4 (10)	C7D—C22D—H22D	110.0
C8—C7—C1	120.4 (11)	C21D—C22D—H22D	110.0
C13—C8—C9	119.3 (9)	C7D—C22D—H22E	110.0
C13—C8—C7	122.1 (10)	C21D—C22D—H22E	110.0
C9—C8—C7	118.6 (10)	H22D—C22D—H22E	108.4
C10—C9—C8	119.6 (10)	C21D—C23D—H23D	109.5
C10—C9—H9	120.2	C21D—C23D—H23E	109.5
C8—C9—H9	120.2	H23D—C23D—H23E	109.5
C11—C10—C9	121.8 (9)	C21D—C23D—H23F	109.5
C11—C10—H10	119.1	H23D—C23D—H23F	109.5
C9—C10—H10	119.1	H23E—C23D—H23F	109.5
C10—C11—C12	118.9 (9)	C2P—C1P—C6P	120 (3)
C10—C11—C14	122.9 (9)	C2P—C1P—C7P	96 (2)
C12—C11—C14	118.1 (10)	C6P—C1P—C7P	143 (3)
C13—C12—C11	119.1 (11)	C1P—C2P—C3P	120 (3)
C13—C12—H12	120.5	C1P—C2P—C15P	94 (2)
C11—C12—H12	120.5	C3P—C2P—C15P	145 (4)
C8—C13—C12	121.1 (10)	C4P—C3P—C2P	120 (3)
C8—C13—H13	119.4	C4P—C3P—H3P	120.1
C12—C13—H13	119.4	C2P—C3P—H3P	120.1
O3—C14—O2	123.6 (6)	C3P—C4P—C5P	120 (3)
O3—C14—C11	119.1 (8)	C3P—C4P—C18P	121 (3)
O2—C14—C11	117.1 (8)	C5P—C4P—C18P	119 (3)
C17—C15—C2	113.1 (13)	C6P—C5P—C4P	120 (3)
C17—C15—C16	111.3 (13)	C6P—C5P—H5P	120.0
C2—C15—C16	111.4 (12)	C4P—C5P—H5P	120.0
C17—C15—H15	106.9	C5P—C6P—C1P	120 (3)
C2—C15—H15	106.9	C5P—C6P—C21P	123 (3)
C16—C15—H15	106.9	C1P—C6P—C21P	117 (3)
C15—C16—H16A	109.5	O1P—C7P—C1P	118 (3)
C15—C16—H16B	109.5	O1P—C7P—C8P	109 (3)
H16A—C16—H16B	109.5	C1P—C7P—C8P	120 (3)
C15—C16—H16C	109.5	O1P—C7P—C15P	117 (3)
H16A—C16—H16C	109.5	C1P—C7P—C15P	84 (2)
H16B—C16—H16C	109.5	C8P—C7P—C15P	107 (2)
C15—C17—H17A	109.5	C9P—C8P—C13P	118 (3)
C15—C17—H17B	109.5	C9P—C8P—C7P	123 (3)
H17A—C17—H17B	109.5	C13P—C8P—C7P	119 (3)
C15—C17—H17C	109.5	C8P—C9P—C10P	121 (3)
H17A—C17—H17C	109.5	C8P—C9P—H9P	119.5
H17B—C17—H17C	109.5	C10P—C9P—H9P	119.5
C19—C18—C20	114.9 (12)	C11P—C10P—C9P	120 (3)
C19—C18—C4	115.7 (13)	C11P—C10P—H10P	119.8
C20—C18—C4	112.3 (12)	C9P—C10P—H10P	119.8
C19—C18—H18	104.0	C10P—C11P—C12P	119 (3)
C20—C18—H18	104.0	C10P—C11P—C14P	122 (3)
C4—C18—H18	104.0	C12P—C11P—C14P	119 (3)
C18—C19—H19A	109.5	C11P—C12P—C13P	120 (3)
C18—C19—H19B	109.5	C11P—C12P—H12P	119.9
H19A—C19—H19B	109.5	C13P—C12P—H12P	119.9
C18—C19—H19C	109.5	C12P—C13P—C8P	121 (3)
H19A—C19—H19C	109.5	C12P—C13P—H13P	119.4
H19B—C19—H19C	109.5	C8P—C13P—H13P	119.4
C18—C20—H20A	109.5	O3P—C14P—O2P	123.6 (6)
C18—C20—H20B	109.5	O3P—C14P—C11P	119.5 (18)
H20A—C20—H20B	109.5	O2P—C14P—C11P	115.8 (18)
C18—C20—H20C	109.5	C2P—C15P—C16P	120 (4)
H20A—C20—H20C	109.5	C2P—C15P—C17P	114 (4)
H20B—C20—H20C	109.5	C16P—C15P—C17P	111 (3)
C22—C21—C6	111.0 (12)	C2P—C15P—C7P	86 (2)
C22—C21—C23	110.0 (10)	C16P—C15P—C7P	111 (4)
C6—C21—C23	113.8 (10)	C17P—C15P—C7P	114 (4)
C22—C21—H21	107.3	C15P—C16P—H16G	109.5
C6—C21—H21	107.3	C15P—C16P—H16H	109.5
C23—C21—H21	107.3	H16G—C16P—H16H	109.5
C21—C22—H22A	109.5	C15P—C16P—H16I	109.5
C21—C22—H22B	109.5	H16G—C16P—H16I	109.5
H22A—C22—H22B	109.5	H16H—C16P—H16I	109.5
C21—C22—H22C	109.5	C15P—C17P—H17G	109.5
H22A—C22—H22C	109.5	C15P—C17P—H17H	109.5
H22B—C22—H22C	109.5	H17G—C17P—H17H	109.5
C21—C23—H23A	109.5	C15P—C17P—H17I	109.5
C21—C23—H23B	109.5	H17G—C17P—H17I	109.5
H23A—C23—H23B	109.5	H17H—C17P—H17I	109.5
C21—C23—H23C	109.5	C4P—C18P—C20P	103 (4)
H23A—C23—H23C	109.5	C4P—C18P—C19P	111 (4)
H23B—C23—H23C	109.5	C20P—C18P—C19P	112 (4)
C2D—C1D—C6D	123 (3)	C4P—C18P—H18P	110.4
C2D—C1D—C7D	127 (3)	C20P—C18P—H18P	110.4
C6D—C1D—C7D	109 (2)	C19P—C18P—H18P	110.4
C1D—C2D—C3D	117 (3)	C18P—C19P—H19G	109.5
C1D—C2D—C15D	123 (3)	C18P—C19P—H19H	109.5
C3D—C2D—C15D	120 (3)	H19G—C19P—H19H	109.5
C2D—C3D—C4D	121 (3)	C18P—C19P—H19I	109.5
C2D—C3D—H3D	119.6	H19G—C19P—H19I	109.5
C4D—C3D—H3D	119.6	H19H—C19P—H19I	109.5
C5D—C4D—C3D	119 (3)	C18P—C20P—H20G	109.5
C5D—C4D—C18D	116 (3)	C18P—C20P—H20H	109.5
C3D—C4D—C18D	123 (3)	H20G—C20P—H20H	109.5
C6D—C5D—C4D	120 (3)	C18P—C20P—H20I	109.5
C6D—C5D—H5D	120.2	H20G—C20P—H20I	109.5
C4D—C5D—H5D	120.2	H20H—C20P—H20I	109.5
C5D—C6D—C1D	120 (3)	C6P—C21P—C23P	113 (4)
C5D—C6D—C21D	128 (3)	C6P—C21P—C22P	112 (4)
C1D—C6D—C21D	112 (2)	C23P—C21P—C22P	114 (4)
O1D—C7D—C22D	109 (3)	C6P—C21P—H21P	105.7
O1D—C7D—C8D	110 (3)	C23P—C21P—H21P	105.7
C22D—C7D—C8D	115 (3)	C22P—C21P—H21P	105.7
O1D—C7D—C1D	110 (3)	C21P—C22P—H22F	109.5
C22D—C7D—C1D	101 (2)	C21P—C22P—H22G	109.5
C8D—C7D—C1D	110 (3)	H22F—C22P—H22G	109.5
C13D—C8D—C9D	118 (2)	C21P—C22P—H22H	109.5
C13D—C8D—C7D	122 (3)	H22F—C22P—H22H	109.5
C9D—C8D—C7D	120 (3)	H22G—C22P—H22H	109.5
C10D—C9D—C8D	123 (3)	C21P—C23P—H23G	109.5
C10D—C9D—H9D	118.7	C21P—C23P—H23H	109.5
C8D—C9D—H9D	118.7	H23G—C23P—H23H	109.5
C9D—C10D—C11D	120 (3)	C21P—C23P—H23I	109.5
C9D—C10D—H10D	120.2	H23G—C23P—H23I	109.5
C11D—C10D—H10D	120.2	H23H—C23P—H23I	109.5
C12D—C11D—C10D	117 (2)	C25—N1—H1A	109.5
C12D—C11D—C14D	122 (3)	C25—N1—H1B	109.5
C10D—C11D—C14D	120 (3)	H1A—N1—H1B	109.5
C13D—C12D—C11D	123 (3)	C25—N1—H1C	109.5
C13D—C12D—H12D	118.5	H1A—N1—H1C	109.5
C11D—C12D—H12D	118.5	H1B—N1—H1C	109.5
C8D—C13D—C12D	120 (3)	C25—C24—H24A	109.5
C8D—C13D—H13D	120.2	C25—C24—H24B	109.5
C12D—C13D—H13D	120.2	H24A—C24—H24B	109.5
O3D—C14D—O2D	123.6 (6)	C25—C24—H24C	109.5
O3D—C14D—C11D	116.6 (17)	H24A—C24—H24C	109.5
O2D—C14D—C11D	119.8 (17)	H24B—C24—H24C	109.5
C16D—C15D—C2D	111 (4)	C26—C25—N1	109.7 (5)
C16D—C15D—C17D	115 (4)	C26—C25—C24	114.9 (6)
C2D—C15D—C17D	111 (4)	N1—C25—C24	108.8 (5)
C16D—C15D—H15D	106.4	C26—C25—H25	107.7
C2D—C15D—H15D	106.4	N1—C25—H25	107.7
C17D—C15D—H15D	106.4	C24—C25—H25	107.7
C15D—C16D—H16D	109.5	C27—C26—C31	118.1 (7)
C15D—C16D—H16E	109.5	C27—C26—C25	120.3 (8)
H16D—C16D—H16E	109.5	C31—C26—C25	121.6 (7)
C15D—C16D—H16F	109.5	C26—C27—C28	121.8 (10)
H16D—C16D—H16F	109.5	C26—C27—H27	119.1
H16E—C16D—H16F	109.5	C28—C27—H27	119.1
C15D—C17D—H17D	109.5	C29—C28—C27	118.5 (12)
C15D—C17D—H17E	109.5	C29—C28—H28	120.8
H17D—C17D—H17E	109.5	C27—C28—H28	120.8
C15D—C17D—H17F	109.5	C30—C29—C28	121.6 (13)
H17D—C17D—H17F	109.5	C30—C29—H29	119.2
H17E—C17D—H17F	109.5	C28—C29—H29	119.2
C19D—C18D—C20D	113 (3)	C29—C30—C31	120.0 (12)
C19D—C18D—C4D	115 (3)	C29—C30—H30	120.0
C20D—C18D—C4D	106 (3)	C31—C30—H30	120.0
C19D—C18D—H18D	107.6	C26—C31—C30	120.1 (10)
C20D—C18D—H18D	107.6	C26—C31—H31	120.0
C4D—C18D—H18D	107.6	C30—C31—H31	120.0

(530minUV)

Crystal data

C31H39NO3	Dx = 1.121 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2260 reflections
a = 6.3387 (5) Å	θ = 1.6–18.1°
b = 13.5668 (10) Å	µ = 0.07 mm^−1
c = 32.6429 (16) Å	T = 299 K
V = 2807.2 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5429 independent reflections
Radiation source: fine-focus sealed tube	1938 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.130
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→16
Tmin = 0.836, Tmax = 1.000	l = −40→39
24938 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.086	H-atom parameters constrained
wR(F^2) = 0.189	w = 1/[σ^2(Fo^2) + (0.0262P)^2 + 1.0565P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5429 reflections	Δρmax = 0.13 e Å^−3
484 parameters	Δρmin = −0.17 e Å^−3
565 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.1 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.0508 (10)	0.6678 (4)	0.49214 (16)	0.0657 (19)
H1A	0.0626	0.7330	0.4901	0.079*
H1B	0.1507	0.6449	0.5087	0.079*
H1C	−0.0755	0.6526	0.5023	0.079*
C24	0.2878 (14)	0.6540 (6)	0.4332 (3)	0.093 (3)*
H24A	0.2875	0.7240	0.4288	0.139*
H24B	0.3122	0.6210	0.4076	0.139*
H24C	0.3975	0.6371	0.4522	0.139*
C25	0.0753 (14)	0.6222 (6)	0.4505 (2)	0.074 (2)*
H25	−0.0354	0.6490	0.4327	0.089*
C26	0.0449 (19)	0.5142 (8)	0.4531 (3)	0.079 (3)
C27	−0.139 (2)	0.4716 (9)	0.4400 (3)	0.104 (3)
H27	−0.2459	0.5117	0.4300	0.125*
C28	−0.170 (3)	0.3683 (12)	0.4411 (4)	0.145 (6)
H28	−0.2973	0.3403	0.4329	0.173*
C29	−0.006 (4)	0.3110 (14)	0.4547 (6)	0.170 (9)
H29	−0.0201	0.2428	0.4543	0.204*
C30	0.176 (4)	0.3512 (12)	0.4688 (5)	0.169 (7)
H30	0.2827	0.3110	0.4791	0.203*
C31	0.203 (2)	0.4532 (9)	0.4678 (3)	0.110 (4)
H31	0.3287	0.4806	0.4771	0.132*
O1	1.050 (3)	0.2471 (13)	0.6341 (6)	0.097 (6)	0.560 (4)
O2	0.6403 (10)	0.6315 (4)	0.51753 (16)	0.0784 (17)	0.560 (4)
O3	0.3375 (11)	0.6177 (5)	0.55054 (17)	0.091 (2)	0.560 (4)
C1	0.817 (4)	0.2792 (17)	0.6903 (6)	0.064 (6)	0.560 (4)
C2	0.865 (5)	0.3438 (17)	0.7221 (7)	0.071 (6)	0.560 (4)
C3	0.809 (5)	0.325 (2)	0.7624 (7)	0.075 (6)	0.560 (4)
H3	0.8485	0.3678	0.7832	0.090*	0.560 (4)
C4	0.691 (5)	0.2413 (17)	0.7711 (5)	0.059 (5)	0.560 (4)
C5	0.620 (5)	0.1836 (18)	0.7396 (6)	0.064 (6)	0.560 (4)
H5	0.5288	0.1317	0.7453	0.076*	0.560 (4)
C6	0.683 (5)	0.2007 (18)	0.6993 (6)	0.066 (6)	0.560 (4)
C7	0.901 (4)	0.2936 (16)	0.6477 (6)	0.082 (6)	0.560 (4)
C8	0.798 (3)	0.3706 (16)	0.6212 (6)	0.053 (6)	0.560 (4)
C9	0.908 (3)	0.4047 (12)	0.5876 (5)	0.057 (5)	0.560 (4)
H9	1.0415	0.3805	0.5810	0.068*	0.560 (4)
C10	0.811 (3)	0.4769 (14)	0.5641 (6)	0.061 (6)	0.560 (4)
H10	0.8872	0.5028	0.5423	0.074*	0.560 (4)
C11	0.6143 (17)	0.5124 (7)	0.5705 (3)	0.057 (3)*	0.560 (4)
C12	0.498 (3)	0.4691 (14)	0.6025 (5)	0.063 (5)	0.560 (4)
H12	0.3584	0.4874	0.6069	0.076*	0.560 (4)
C13	0.592 (4)	0.3989 (18)	0.6275 (6)	0.069 (6)	0.560 (4)
H13	0.5152	0.3707	0.6488	0.083*	0.560 (4)
C14	0.5230 (16)	0.5931 (6)	0.5445 (2)	0.068 (2)	0.560 (4)
C15	1.007 (4)	0.4320 (16)	0.7137 (8)	0.084 (6)	0.560 (4)
H15	1.0145	0.4369	0.6838	0.101*	0.560 (4)
C16	1.229 (4)	0.415 (3)	0.7272 (16)	0.097 (9)	0.560 (4)
H16A	1.2761	0.3523	0.7174	0.146*	0.560 (4)
H16B	1.3174	0.4662	0.7163	0.146*	0.560 (4)
H16C	1.2350	0.4164	0.7566	0.146*	0.560 (4)
C17	0.919 (5)	0.5297 (17)	0.7277 (8)	0.109 (8)	0.560 (4)
H17A	0.7761	0.5363	0.7181	0.164*	0.560 (4)
H17B	0.9205	0.5325	0.7571	0.164*	0.560 (4)
H17C	1.0029	0.5823	0.7168	0.164*	0.560 (4)
C18	0.615 (4)	0.2174 (18)	0.8155 (6)	0.084 (6)	0.560 (4)
H18	0.6259	0.1460	0.8197	0.101*	0.560 (4)
C19	0.755 (4)	0.269 (2)	0.8475 (6)	0.121 (9)	0.560 (4)
H19A	0.8988	0.2491	0.8438	0.181*	0.560 (4)
H19B	0.7436	0.3390	0.8443	0.181*	0.560 (4)
H19C	0.7089	0.2507	0.8745	0.181*	0.560 (4)
C20	0.385 (4)	0.248 (3)	0.8208 (8)	0.112 (9)	0.560 (4)
H20A	0.3004	0.2148	0.8005	0.168*	0.560 (4)
H20B	0.3377	0.2293	0.8476	0.168*	0.560 (4)
H20C	0.3724	0.3176	0.8174	0.168*	0.560 (4)
C21	0.610 (4)	0.1339 (16)	0.6650 (7)	0.091 (6)	0.560 (4)
H21	0.5907	0.1725	0.6399	0.110*	0.560 (4)
C22	0.778 (3)	0.0547 (16)	0.6580 (6)	0.105 (7)	0.560 (4)
H22A	0.7335	0.0117	0.6363	0.157*	0.560 (4)
H22B	0.9089	0.0854	0.6506	0.157*	0.560 (4)
H22C	0.7966	0.0171	0.6826	0.157*	0.560 (4)
C23	0.394 (3)	0.0806 (16)	0.6767 (6)	0.114 (7)	0.560 (4)
H23A	0.3505	0.0386	0.6546	0.171*	0.560 (4)
H23B	0.4140	0.0417	0.7010	0.171*	0.560 (4)
H23C	0.2871	0.1293	0.6817	0.171*	0.560 (4)
O1D	1.092 (5)	0.279 (3)	0.6422 (15)	0.086 (15)*	0.299 (4)
O2D	0.6403 (10)	0.6315 (4)	0.51753 (16)	0.0784 (17)	0.299 (4)
O3D	0.3375 (11)	0.6177 (5)	0.55054 (17)	0.091 (2)	0.299 (4)
C1D	0.808 (8)	0.287 (3)	0.6916 (10)	0.069 (10)*	0.299 (4)
C2D	0.908 (7)	0.348 (3)	0.7192 (11)	0.070 (10)*	0.299 (4)
C3D	0.854 (7)	0.339 (3)	0.7605 (11)	0.075 (10)*	0.299 (4)
H3D	0.9240	0.3770	0.7798	0.090*	0.299 (4)
C4D	0.693 (7)	0.273 (3)	0.7737 (9)	0.065 (10)*	0.299 (4)
C5D	0.608 (8)	0.209 (3)	0.7443 (10)	0.070 (11)*	0.299 (4)
H5D	0.5114	0.1619	0.7525	0.084*	0.299 (4)
C6D	0.664 (9)	0.215 (3)	0.7031 (10)	0.063 (10)*	0.299 (4)
C7D	0.866 (5)	0.277 (2)	0.6455 (9)	0.079 (10)*	0.299 (4)
C8D	0.765 (7)	0.357 (3)	0.6187 (11)	0.049 (10)*	0.299 (4)
C9D	0.862 (6)	0.379 (2)	0.5817 (10)	0.064 (10)*	0.299 (4)
H9D	0.9770	0.3422	0.5728	0.077*	0.299 (4)
C10D	0.785 (5)	0.456 (3)	0.5581 (11)	0.058 (10)*	0.299 (4)
H10D	0.8501	0.4701	0.5332	0.070*	0.299 (4)
C11D	0.6143 (17)	0.5124 (7)	0.5705 (3)	0.057 (3)*	0.299 (4)
C12D	0.522 (6)	0.491 (3)	0.6086 (9)	0.053 (10)*	0.299 (4)
H12D	0.4081	0.5279	0.6179	0.064*	0.299 (4)
C13D	0.602 (7)	0.415 (3)	0.6321 (13)	0.064 (11)*	0.299 (4)
H13D	0.5424	0.4024	0.6577	0.077*	0.299 (4)
C14D	0.5230 (16)	0.5931 (6)	0.5445 (2)	0.068 (2)	0.299 (4)
C15D	1.057 (7)	0.429 (3)	0.7058 (15)	0.081 (10)*	0.299 (4)
H15D	1.0924	0.4200	0.6768	0.097*	0.299 (4)
C16D	1.254 (9)	0.429 (5)	0.730 (3)	0.091 (17)*	0.299 (4)
H16D	1.3447	0.4815	0.7212	0.136*	0.299 (4)
H16E	1.2205	0.4390	0.7588	0.136*	0.299 (4)
H16F	1.3252	0.3672	0.7271	0.136*	0.299 (4)
C17D	0.932 (11)	0.527 (3)	0.7108 (17)	0.078 (15)*	0.299 (4)
H17D	0.8063	0.5243	0.6945	0.118*	0.299 (4)
H17E	0.8953	0.5359	0.7391	0.118*	0.299 (4)
H17F	1.0183	0.5811	0.7019	0.118*	0.299 (4)
C18D	0.643 (6)	0.249 (4)	0.8194 (10)	0.093 (11)*	0.299 (4)
H18D	0.6338	0.1783	0.8145	0.112*	0.299 (4)
C19D	0.811 (8)	0.238 (4)	0.8509 (15)	0.108 (18)*	0.299 (4)
H19D	0.9462	0.2341	0.8377	0.163*	0.299 (4)
H19E	0.8089	0.2939	0.8690	0.163*	0.299 (4)
H19F	0.7865	0.1790	0.8664	0.163*	0.299 (4)
C20D	0.413 (6)	0.258 (6)	0.8318 (15)	0.089 (15)*	0.299 (4)
H20D	0.3273	0.2645	0.8077	0.133*	0.299 (4)
H20E	0.3718	0.1993	0.8464	0.133*	0.299 (4)
H20F	0.3943	0.3142	0.8490	0.133*	0.299 (4)
C21D	0.602 (7)	0.155 (3)	0.6648 (12)	0.108 (11)*	0.299 (4)
H21D	0.4797	0.1891	0.6530	0.129*	0.299 (4)
C22D	0.784 (5)	0.1739 (19)	0.6352 (9)	0.104 (11)*	0.299 (4)
H22D	0.8943	0.1251	0.6390	0.125*	0.299 (4)
H22E	0.7357	0.1711	0.6071	0.125*	0.299 (4)
C23D	0.535 (7)	0.049 (3)	0.6703 (13)	0.125 (12)*	0.299 (4)
H23D	0.4202	0.0460	0.6894	0.188*	0.299 (4)
H23E	0.4911	0.0227	0.6444	0.188*	0.299 (4)
H23F	0.6519	0.0115	0.6806	0.188*	0.299 (4)
O1P	1.125 (7)	0.302 (3)	0.6514 (14)	0.068 (15)*	0.141 (4)
O2P	0.6403 (10)	0.6315 (4)	0.51753 (16)	0.0784 (17)	0.141 (4)
O3P	0.3375 (11)	0.6177 (5)	0.55054 (17)	0.091 (2)	0.141 (4)
C1P	0.838 (9)	0.294 (4)	0.7007 (13)	0.061 (13)*	0.141 (4)
C2P	0.877 (12)	0.356 (4)	0.7332 (13)	0.066 (13)*	0.141 (4)
C3P	0.797 (16)	0.333 (6)	0.7719 (15)	0.075 (12)*	0.141 (4)
H3P	0.8260	0.3719	0.7946	0.090*	0.141 (4)
C4P	0.674 (15)	0.248 (6)	0.7752 (16)	0.063 (13)*	0.141 (4)
C5P	0.650 (17)	0.182 (6)	0.7431 (17)	0.061 (13)*	0.141 (4)
H5P	0.5869	0.1210	0.7474	0.074*	0.141 (4)
C6P	0.724 (9)	0.208 (4)	0.7047 (15)	0.068 (13)*	0.141 (4)
C7P	0.954 (6)	0.352 (3)	0.6688 (10)	0.082 (12)*	0.141 (4)
C8P	0.843 (6)	0.414 (2)	0.6367 (9)	0.051 (12)*	0.141 (4)
C9P	0.955 (6)	0.453 (3)	0.6043 (12)	0.061 (9)*	0.141 (4)
H9P	1.0975	0.4383	0.6018	0.073*	0.141 (4)
C10P	0.861 (6)	0.515 (3)	0.5751 (13)	0.056 (9)*	0.141 (4)
H10P	0.9432	0.5414	0.5542	0.067*	0.141 (4)
C11P	0.647 (6)	0.536 (3)	0.5769 (11)	0.050 (15)*	0.141 (4)
C12P	0.531 (7)	0.493 (5)	0.6088 (17)	0.056 (9)*	0.141 (4)
H12P	0.3863	0.5046	0.6106	0.067*	0.141 (4)
C13P	0.627 (7)	0.433 (4)	0.6378 (15)	0.061 (9)*	0.141 (4)
H13P	0.5453	0.4049	0.6584	0.073*	0.141 (4)
C14P	0.5230 (16)	0.5931 (6)	0.5445 (2)	0.068 (2)	0.141 (4)
C15P	1.008 (9)	0.426 (3)	0.7081 (13)	0.084 (13)*	0.141 (4)
C16P	1.244 (10)	0.436 (7)	0.712 (2)	0.12 (2)*	0.141 (4)
H16G	1.2950	0.4842	0.6933	0.176*	0.141 (4)
H16H	1.2784	0.4560	0.7398	0.176*	0.141 (4)
H16I	1.3101	0.3735	0.7067	0.176*	0.141 (4)
C17P	0.909 (17)	0.527 (4)	0.703 (3)	0.11 (2)*	0.141 (4)
H17G	0.9993	0.5684	0.6869	0.158*	0.141 (4)
H17H	0.7742	0.5210	0.6899	0.158*	0.141 (4)
H17I	0.8894	0.5568	0.7297	0.158*	0.141 (4)
C18P	0.585 (11)	0.222 (5)	0.8171 (16)	0.086 (13)*	0.141 (4)
H18P	0.4969	0.1627	0.8157	0.103*	0.141 (4)
C19P	0.767 (14)	0.209 (7)	0.847 (3)	0.11 (2)*	0.141 (4)
H19G	0.7126	0.1918	0.8736	0.172*	0.141 (4)
H19H	0.8582	0.1568	0.8376	0.172*	0.141 (4)
H19I	0.8461	0.2689	0.8489	0.172*	0.141 (4)
C20P	0.455 (11)	0.313 (5)	0.828 (2)	0.085 (19)*	0.141 (4)
H20G	0.3908	0.3043	0.8543	0.128*	0.141 (4)
H20H	0.5452	0.3700	0.8286	0.128*	0.141 (4)
H20I	0.3470	0.3227	0.8077	0.128*	0.141 (4)
C21P	0.700 (10)	0.148 (4)	0.6659 (17)	0.092 (13)*	0.141 (4)
H21P	0.7073	0.1945	0.6429	0.111*	0.141 (4)
C22P	0.887 (10)	0.079 (6)	0.662 (3)	0.11 (2)*	0.141 (4)
H22F	0.8731	0.0405	0.6374	0.166*	0.141 (4)
H22G	1.0153	0.1161	0.6610	0.166*	0.141 (4)
H22H	0.8905	0.0353	0.6853	0.166*	0.141 (4)
C23P	0.488 (10)	0.096 (7)	0.663 (3)	0.123 (15)*	0.141 (4)
H23G	0.4801	0.0592	0.6384	0.184*	0.141 (4)
H23H	0.4736	0.0520	0.6863	0.184*	0.141 (4)
H23I	0.3766	0.1440	0.6641	0.184*	0.141 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.071 (5)	0.082 (4)	0.044 (4)	0.007 (4)	−0.001 (4)	0.008 (3)
C26	0.089 (8)	0.103 (8)	0.045 (5)	−0.003 (8)	0.001 (5)	−0.009 (5)
C27	0.105 (11)	0.123 (10)	0.085 (8)	−0.009 (8)	0.008 (7)	−0.023 (7)
C28	0.171 (17)	0.139 (14)	0.124 (11)	−0.051 (13)	0.036 (11)	−0.041 (10)
C29	0.26 (3)	0.112 (14)	0.141 (15)	−0.019 (15)	0.032 (17)	−0.013 (11)
C30	0.26 (2)	0.108 (14)	0.137 (13)	0.028 (13)	−0.004 (14)	−0.008 (10)
C31	0.140 (12)	0.092 (9)	0.099 (8)	−0.001 (8)	−0.010 (8)	−0.007 (7)
O1	0.117 (13)	0.083 (13)	0.091 (11)	0.039 (11)	0.046 (10)	0.017 (10)
O2	0.081 (4)	0.087 (4)	0.068 (3)	−0.004 (4)	0.010 (3)	0.029 (3)
O3	0.072 (4)	0.135 (5)	0.066 (4)	0.031 (4)	0.000 (4)	0.029 (4)
C1	0.067 (11)	0.062 (10)	0.062 (10)	0.016 (9)	−0.004 (9)	0.016 (9)
C2	0.069 (13)	0.059 (10)	0.085 (12)	0.000 (9)	0.006 (11)	0.016 (10)
C3	0.073 (13)	0.066 (11)	0.087 (12)	−0.011 (10)	−0.017 (11)	−0.010 (10)
C4	0.069 (11)	0.053 (11)	0.054 (9)	0.005 (10)	0.003 (8)	0.008 (9)
C5	0.087 (13)	0.050 (11)	0.054 (9)	0.000 (11)	−0.006 (9)	0.005 (8)
C6	0.081 (13)	0.055 (10)	0.061 (10)	0.016 (10)	−0.006 (9)	0.010 (8)
C7	0.099 (14)	0.081 (12)	0.067 (11)	0.000 (11)	0.006 (10)	0.017 (10)
C8	0.048 (10)	0.051 (10)	0.062 (10)	−0.008 (9)	−0.006 (9)	0.004 (8)
C9	0.055 (10)	0.045 (9)	0.071 (10)	−0.011 (9)	0.009 (9)	0.007 (9)
C10	0.081 (12)	0.053 (11)	0.050 (9)	−0.011 (10)	−0.003 (9)	0.008 (9)
C12	0.054 (10)	0.070 (11)	0.065 (10)	−0.005 (10)	0.005 (9)	0.000 (10)
C13	0.083 (12)	0.083 (12)	0.040 (9)	−0.004 (11)	0.006 (9)	0.012 (9)
C14	0.100 (7)	0.061 (5)	0.042 (5)	0.011 (5)	−0.009 (5)	0.006 (4)
C15	0.061 (12)	0.101 (12)	0.090 (13)	0.008 (11)	−0.004 (11)	0.024 (10)
C16	0.105 (18)	0.098 (17)	0.088 (18)	−0.034 (13)	0.015 (15)	−0.015 (15)
C17	0.104 (16)	0.093 (14)	0.13 (2)	−0.021 (12)	0.009 (18)	0.007 (15)
C18	0.092 (13)	0.086 (12)	0.075 (10)	−0.002 (11)	−0.009 (10)	−0.023 (9)
C19	0.14 (2)	0.16 (2)	0.064 (12)	0.030 (18)	−0.034 (14)	0.003 (14)
C20	0.133 (19)	0.13 (2)	0.069 (14)	−0.003 (17)	0.028 (14)	−0.036 (14)
C21	0.113 (14)	0.081 (12)	0.080 (10)	−0.035 (12)	−0.016 (11)	−0.013 (10)
C22	0.123 (18)	0.122 (16)	0.070 (11)	0.011 (15)	−0.016 (13)	−0.029 (11)
C23	0.113 (15)	0.127 (13)	0.101 (12)	−0.029 (13)	−0.007 (12)	0.012 (11)
O2D	0.081 (4)	0.087 (4)	0.068 (3)	−0.004 (4)	0.010 (3)	0.029 (3)
O3D	0.072 (4)	0.135 (5)	0.066 (4)	0.031 (4)	0.000 (4)	0.029 (4)
C14D	0.100 (7)	0.061 (5)	0.042 (5)	0.011 (5)	−0.009 (5)	0.006 (4)
O2P	0.081 (4)	0.087 (4)	0.068 (3)	−0.004 (4)	0.010 (3)	0.029 (3)
O3P	0.072 (4)	0.135 (5)	0.066 (4)	0.031 (4)	0.000 (4)	0.029 (4)
C14P	0.100 (7)	0.061 (5)	0.042 (5)	0.011 (5)	−0.009 (5)	0.006 (4)

Geometric parameters (Å, º)

N1—C25	1.502 (9)	C8D—C13D	1.37 (2)
N1—H1A	0.8900	C8D—C9D	1.39 (2)
N1—H1B	0.8900	C9D—C10D	1.39 (2)
N1—H1C	0.8900	C9D—H9D	0.9300
C24—C25	1.523 (11)	C10D—C11D	1.39 (2)
C24—H24A	0.9600	C10D—H10D	0.9300
C24—H24B	0.9600	C11D—C12D	1.40 (2)
C24—H24C	0.9600	C11D—C14D	1.501 (10)
C25—C26	1.480 (12)	C12D—C13D	1.38 (2)
C25—H25	0.9800	C12D—H12D	0.9300
C26—C27	1.368 (14)	C13D—H13D	0.9300
C26—C31	1.386 (14)	C15D—C16D	1.49 (3)
C27—C28	1.416 (15)	C15D—C17D	1.55 (3)
C27—H27	0.9300	C15D—H15D	0.9800
C28—C29	1.37 (2)	C16D—H16D	0.9600
C28—H28	0.9300	C16D—H16E	0.9600
C29—C30	1.36 (2)	C16D—H16F	0.9600
C29—H29	0.9300	C17D—H17D	0.9600
C30—C31	1.394 (16)	C17D—H17E	0.9600
C30—H30	0.9300	C17D—H17F	0.9600
C31—H31	0.9300	C18D—C19D	1.49 (2)
O1—C7	1.221 (17)	C18D—C20D	1.52 (2)
O2—C14	1.265 (8)	C18D—H18D	0.9800
O3—C14	1.238 (9)	C19D—H19D	0.9600
C1—C6	1.391 (17)	C19D—H19E	0.9600
C1—C2	1.393 (17)	C19D—H19F	0.9600
C1—C7	1.503 (17)	C20D—H20D	0.9600
C2—C3	1.388 (17)	C20D—H20E	0.9600
C2—C15	1.521 (18)	C20D—H20F	0.9600
C3—C4	1.387 (18)	C21D—C23D	1.51 (3)
C3—H3	0.9300	C21D—C22D	1.53 (2)
C4—C5	1.368 (18)	C21D—H21D	0.9800
C4—C18	1.560 (17)	C22D—H22D	0.9700
C5—C6	1.396 (16)	C22D—H22E	0.9700
C5—H5	0.9300	C23D—H23D	0.9600
C6—C21	1.513 (17)	C23D—H23E	0.9600
C7—C8	1.504 (16)	C23D—H23F	0.9600
C8—C13	1.378 (18)	O1P—C7P	1.40 (2)
C8—C9	1.380 (16)	O2P—C14P	1.265 (8)
C9—C10	1.388 (15)	O3P—C14P	1.238 (9)
C9—H9	0.9300	C1P—C2P	1.38 (2)
C10—C11	1.354 (16)	C1P—C6P	1.38 (2)
C10—H10	0.9300	C1P—C7P	1.50 (2)
C11—C12	1.408 (15)	C2P—C3P	1.39 (2)
C11—C14	1.501 (10)	C2P—C15P	1.50 (2)
C12—C13	1.390 (16)	C3P—C4P	1.39 (3)
C12—H12	0.9300	C3P—H3P	0.9300
C13—H13	0.9300	C4P—C5P	1.39 (2)
C15—C16	1.488 (19)	C4P—C18P	1.52 (2)
C15—C17	1.510 (19)	C5P—C6P	1.38 (2)
C15—H15	0.9800	C5P—H5P	0.9300
C16—H16A	0.9600	C6P—C21P	1.51 (2)
C16—H16B	0.9600	C7P—C8P	1.52 (2)
C16—H16C	0.9600	C7P—C15P	1.67 (2)
C17—H17A	0.9600	C8P—C9P	1.38 (2)
C17—H17B	0.9600	C8P—C13P	1.39 (2)
C17—H17C	0.9600	C9P—C10P	1.40 (2)
C18—C20	1.53 (2)	C9P—H9P	0.9300
C18—C19	1.54 (2)	C10P—C11P	1.39 (2)
C18—H18	0.9800	C10P—H10P	0.9300
C19—H19A	0.9600	C11P—C12P	1.40 (2)
C19—H19B	0.9600	C11P—C14P	1.53 (2)
C19—H19C	0.9600	C12P—C13P	1.39 (2)
C20—H20A	0.9600	C12P—H12P	0.9300
C20—H20B	0.9600	C13P—H13P	0.9300
C20—H20C	0.9600	C15P—C16P	1.51 (3)
C21—C22	1.53 (2)	C15P—C17P	1.53 (3)
C21—C23	1.596 (19)	C16P—H16G	0.9600
C21—H21	0.9800	C16P—H16H	0.9600
C22—H22A	0.9600	C16P—H16I	0.9600
C22—H22B	0.9600	C17P—H17G	0.9600
C22—H22C	0.9600	C17P—H17H	0.9600
C23—H23A	0.9600	C17P—H17I	0.9600
C23—H23B	0.9600	C18P—C19P	1.52 (3)
C23—H23C	0.9600	C18P—C20P	1.53 (3)
O1D—C7D	1.44 (2)	C18P—H18P	0.9800
O2D—C14D	1.265 (8)	C19P—H19G	0.9600
O3D—C14D	1.238 (9)	C19P—H19H	0.9600
C1D—C2D	1.37 (2)	C19P—H19I	0.9600
C1D—C6D	1.40 (2)	C20P—H20G	0.9600
C1D—C7D	1.56 (2)	C20P—H20H	0.9600
C2D—C3D	1.40 (2)	C20P—H20I	0.9600
C2D—C15D	1.52 (2)	C21P—C22P	1.52 (3)
C3D—C4D	1.42 (2)	C21P—C23P	1.52 (3)
C3D—H3D	0.9300	C21P—H21P	0.9800
C4D—C5D	1.40 (2)	C22P—H22F	0.9600
C4D—C18D	1.56 (2)	C22P—H22G	0.9600
C5D—C6D	1.39 (2)	C22P—H22H	0.9600
C5D—H5D	0.9300	C23P—H23G	0.9600
C6D—C21D	1.54 (2)	C23P—H23H	0.9600
C7D—C22D	1.53 (2)	C23P—H23I	0.9600
C7D—C8D	1.54 (2)
C25—N1—H1A	109.5	C10D—C11D—C12D	118 (2)
C25—N1—H1B	109.5	C10D—C11D—C14D	122.7 (15)
H1A—N1—H1B	109.5	C12D—C11D—C14D	119.3 (16)
C25—N1—H1C	109.5	C13D—C12D—C11D	120 (3)
H1A—N1—H1C	109.5	C13D—C12D—H12D	120.2
H1B—N1—H1C	109.5	C11D—C12D—H12D	120.2
C25—C24—H24A	109.5	C8D—C13D—C12D	122 (3)
C25—C24—H24B	109.5	C8D—C13D—H13D	119.1
H24A—C24—H24B	109.5	C12D—C13D—H13D	119.1
C25—C24—H24C	109.5	O3D—C14D—O2D	123.9 (8)
H24A—C24—H24C	109.5	O3D—C14D—C11D	118.3 (8)
H24B—C24—H24C	109.5	O2D—C14D—C11D	117.8 (8)
C26—C25—N1	109.9 (7)	C16D—C15D—C2D	112 (3)
C26—C25—C24	114.6 (8)	C16D—C15D—C17D	112 (3)
N1—C25—C24	108.1 (7)	C2D—C15D—C17D	106 (3)
C26—C25—H25	108.0	C16D—C15D—H15D	109.1
N1—C25—H25	108.0	C2D—C15D—H15D	109.1
C24—C25—H25	108.0	C17D—C15D—H15D	109.1
C27—C26—C31	118.1 (10)	C15D—C16D—H16D	109.5
C27—C26—C25	120.7 (11)	C15D—C16D—H16E	109.5
C31—C26—C25	121.2 (10)	H16D—C16D—H16E	109.5
C26—C27—C28	122.0 (13)	C15D—C16D—H16F	109.5
C26—C27—H27	119.0	H16D—C16D—H16F	109.5
C28—C27—H27	119.0	H16E—C16D—H16F	109.5
C29—C28—C27	117.5 (18)	C15D—C17D—H17D	109.5
C29—C28—H28	121.3	C15D—C17D—H17E	109.5
C27—C28—H28	121.3	H17D—C17D—H17E	109.5
C30—C29—C28	122 (2)	C15D—C17D—H17F	109.5
C30—C29—H29	119.1	H17D—C17D—H17F	109.5
C28—C29—H29	119.1	H17E—C17D—H17F	109.5
C29—C30—C31	119.6 (19)	C19D—C18D—C20D	121 (3)
C29—C30—H30	120.2	C19D—C18D—C4D	123 (3)
C31—C30—H30	120.2	C20D—C18D—C4D	116 (3)
C26—C31—C30	120.9 (14)	C19D—C18D—H18D	93.2
C26—C31—H31	119.6	C20D—C18D—H18D	93.2
C30—C31—H31	119.6	C4D—C18D—H18D	93.2
C6—C1—C2	117.4 (14)	C18D—C19D—H19D	109.5
C6—C1—C7	120.7 (16)	C18D—C19D—H19E	109.5
C2—C1—C7	121.9 (17)	H19D—C19D—H19E	109.5
C3—C2—C1	122.1 (15)	C18D—C19D—H19F	109.5
C3—C2—C15	118.0 (17)	H19D—C19D—H19F	109.5
C1—C2—C15	119.5 (17)	H19E—C19D—H19F	109.5
C4—C3—C2	119.1 (16)	C18D—C20D—H20D	109.5
C4—C3—H3	120.5	C18D—C20D—H20E	109.5
C2—C3—H3	120.5	H20D—C20D—H20E	109.5
C5—C4—C3	119.3 (15)	C18D—C20D—H20F	109.5
C5—C4—C18	118.5 (15)	H20D—C20D—H20F	109.5
C3—C4—C18	121.8 (16)	H20E—C20D—H20F	109.5
C4—C5—C6	121.4 (16)	C23D—C21D—C22D	116 (3)
C4—C5—H5	119.3	C23D—C21D—C6D	118 (3)
C6—C5—H5	119.3	C22D—C21D—C6D	103 (2)
C1—C6—C5	119.9 (15)	C23D—C21D—H21D	105.8
C1—C6—C21	119.3 (15)	C22D—C21D—H21D	105.8
C5—C6—C21	120.8 (16)	C6D—C21D—H21D	105.8
O1—C7—C1	123.0 (17)	C7D—C22D—C21D	106 (2)
O1—C7—C8	119.0 (16)	C7D—C22D—H22D	110.6
C1—C7—C8	118.0 (17)	C21D—C22D—H22D	110.6
C13—C8—C9	120.5 (15)	C7D—C22D—H22E	110.6
C13—C8—C7	121.1 (16)	C21D—C22D—H22E	110.6
C9—C8—C7	118.1 (15)	H22D—C22D—H22E	108.7
C8—C9—C10	116.8 (15)	C21D—C23D—H23D	109.5
C8—C9—H9	121.6	C21D—C23D—H23E	109.5
C10—C9—H9	121.6	H23D—C23D—H23E	109.5
C11—C10—C9	125.2 (15)	C21D—C23D—H23F	109.5
C11—C10—H10	117.4	H23D—C23D—H23F	109.5
C9—C10—H10	117.4	H23E—C23D—H23F	109.5
C10—C11—C12	116.6 (12)	C2P—C1P—C6P	123 (3)
C10—C11—C14	121.9 (11)	C2P—C1P—C7P	97 (2)
C12—C11—C14	121.4 (11)	C6P—C1P—C7P	140 (3)
C13—C12—C11	119.8 (16)	C1P—C2P—C3P	119 (3)
C13—C12—H12	120.1	C1P—C2P—C15P	94 (2)
C11—C12—H12	120.1	C3P—C2P—C15P	147 (3)
C8—C13—C12	120.6 (17)	C4P—C3P—C2P	118 (3)
C8—C13—H13	119.7	C4P—C3P—H3P	121.2
C12—C13—H13	119.7	C2P—C3P—H3P	121.2
O3—C14—O2	123.9 (8)	C3P—C4P—C5P	122 (3)
O3—C14—C11	118.3 (8)	C3P—C4P—C18P	118 (3)
O2—C14—C11	117.8 (8)	C5P—C4P—C18P	119 (3)
C16—C15—C17	113 (2)	C6P—C5P—C4P	119 (3)
C16—C15—C2	112.5 (19)	C6P—C5P—H5P	120.6
C17—C15—C2	114.6 (18)	C4P—C5P—H5P	120.6
C16—C15—H15	105.1	C1P—C6P—C5P	118 (3)
C17—C15—H15	105.1	C1P—C6P—C21P	115 (3)
C2—C15—H15	105.1	C5P—C6P—C21P	126 (3)
C15—C16—H16A	109.5	O1P—C7P—C1P	114 (3)
C15—C16—H16B	109.5	O1P—C7P—C8P	110 (2)
H16A—C16—H16B	109.5	C1P—C7P—C8P	123 (3)
C15—C16—H16C	109.5	O1P—C7P—C15P	116 (3)
H16A—C16—H16C	109.5	C1P—C7P—C15P	83.1 (19)
H16B—C16—H16C	109.5	C8P—C7P—C15P	107 (2)
C15—C17—H17A	109.5	C9P—C8P—C13P	117 (2)
C15—C17—H17B	109.5	C9P—C8P—C7P	120 (3)
H17A—C17—H17B	109.5	C13P—C8P—C7P	123 (3)
C15—C17—H17C	109.5	C8P—C9P—C10P	122 (3)
H17A—C17—H17C	109.5	C8P—C9P—H9P	118.9
H17B—C17—H17C	109.5	C10P—C9P—H9P	118.9
C20—C18—C19	110.6 (19)	C11P—C10P—C9P	121 (3)
C20—C18—C4	110.1 (18)	C11P—C10P—H10P	119.7
C19—C18—C4	111.1 (16)	C9P—C10P—H10P	119.7
C20—C18—H18	108.3	C10P—C11P—C12P	117 (2)
C19—C18—H18	108.3	C10P—C11P—C14P	125 (3)
C4—C18—H18	108.3	C12P—C11P—C14P	117 (3)
C18—C19—H19A	109.5	C13P—C12P—C11P	121 (3)
C18—C19—H19B	109.5	C13P—C12P—H12P	119.4
H19A—C19—H19B	109.5	C11P—C12P—H12P	119.4
C18—C19—H19C	109.5	C12P—C13P—C8P	122 (3)
H19A—C19—H19C	109.5	C12P—C13P—H13P	119.2
H19B—C19—H19C	109.5	C8P—C13P—H13P	119.2
C18—C20—H20A	109.5	O3P—C14P—O2P	123.9 (8)
C18—C20—H20B	109.5	O3P—C14P—C11P	121.0 (16)
H20A—C20—H20B	109.5	O2P—C14P—C11P	112.9 (16)
C18—C20—H20C	109.5	C2P—C15P—C16P	124 (4)
H20A—C20—H20C	109.5	C2P—C15P—C17P	113 (3)
H20B—C20—H20C	109.5	C16P—C15P—C17P	110 (3)
C6—C21—C22	108.6 (19)	C2P—C15P—C7P	85.9 (19)
C6—C21—C23	110.9 (16)	C16P—C15P—C7P	109 (3)
C22—C21—C23	108.3 (16)	C17P—C15P—C7P	112 (3)
C6—C21—H21	109.7	C15P—C16P—H16G	109.5
C22—C21—H21	109.7	C15P—C16P—H16H	109.5
C23—C21—H21	109.7	H16G—C16P—H16H	109.5
C21—C22—H22A	109.5	C15P—C16P—H16I	109.5
C21—C22—H22B	109.5	H16G—C16P—H16I	109.5
H22A—C22—H22B	109.5	H16H—C16P—H16I	109.5
C21—C22—H22C	109.5	C15P—C17P—H17G	109.5
H22A—C22—H22C	109.5	C15P—C17P—H17H	109.5
H22B—C22—H22C	109.5	H17G—C17P—H17H	109.5
C21—C23—H23A	109.5	C15P—C17P—H17I	109.5
C21—C23—H23B	109.5	H17G—C17P—H17I	109.5
H23A—C23—H23B	109.5	H17H—C17P—H17I	109.5
C21—C23—H23C	109.5	C4P—C18P—C19P	109 (4)
H23A—C23—H23C	109.5	C4P—C18P—C20P	102 (3)
H23B—C23—H23C	109.5	C19P—C18P—C20P	111 (4)
C2D—C1D—C6D	123 (2)	C4P—C18P—H18P	111.4
C2D—C1D—C7D	126 (2)	C19P—C18P—H18P	111.4
C6D—C1D—C7D	110.4 (19)	C20P—C18P—H18P	111.4
C1D—C2D—C3D	118 (2)	C18P—C19P—H19G	109.5
C1D—C2D—C15D	122 (3)	C18P—C19P—H19H	109.5
C3D—C2D—C15D	120 (3)	H19G—C19P—H19H	109.5
C2D—C3D—C4D	122 (3)	C18P—C19P—H19I	109.5
C2D—C3D—H3D	119.2	H19G—C19P—H19I	109.5
C4D—C3D—H3D	119.2	H19H—C19P—H19I	109.5
C5D—C4D—C3D	117 (2)	C18P—C20P—H20G	109.5
C5D—C4D—C18D	117 (3)	C18P—C20P—H20H	109.5
C3D—C4D—C18D	124 (3)	H20G—C20P—H20H	109.5
C6D—C5D—C4D	122 (3)	C18P—C20P—H20I	109.5
C6D—C5D—H5D	118.9	H20G—C20P—H20I	109.5
C4D—C5D—H5D	118.9	H20H—C20P—H20I	109.5
C5D—C6D—C1D	118 (2)	C6P—C21P—C22P	109 (3)
C5D—C6D—C21D	134 (2)	C6P—C21P—C23P	112 (4)
C1D—C6D—C21D	109 (2)	C22P—C21P—C23P	113 (4)
O1D—C7D—C22D	110 (2)	C6P—C21P—H21P	107.3
O1D—C7D—C8D	111 (3)	C22P—C21P—H21P	107.3
C22D—C7D—C8D	112 (3)	C23P—C21P—H21P	107.3
O1D—C7D—C1D	108 (3)	C21P—C22P—H22F	109.5
C22D—C7D—C1D	102.5 (19)	C21P—C22P—H22G	109.5
C8D—C7D—C1D	113 (3)	H22F—C22P—H22G	109.5
C13D—C8D—C9D	119 (2)	C21P—C22P—H22H	109.5
C13D—C8D—C7D	123 (2)	H22F—C22P—H22H	109.5
C9D—C8D—C7D	118 (2)	H22G—C22P—H22H	109.5
C8D—C9D—C10D	119 (3)	C21P—C23P—H23G	109.5
C8D—C9D—H9D	120.3	C21P—C23P—H23H	109.5
C10D—C9D—H9D	120.3	H23G—C23P—H23H	109.5
C11D—C10D—C9D	122 (3)	C21P—C23P—H23I	109.5
C11D—C10D—H10D	119.1	H23G—C23P—H23I	109.5
C9D—C10D—H10D	119.1	H23H—C23P—H23I	109.5

(660minUV)

Crystal data

C31H39NO3	Dx = 1.118 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2213 reflections
a = 6.3595 (5) Å	θ = 1.6–18.8°
b = 13.5442 (11) Å	µ = 0.07 mm^−1
c = 32.6718 (16) Å	T = 299 K
V = 2814.2 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5439 independent reflections
Radiation source: fine-focus sealed tube	2046 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.124
ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	h = −7→7
Tmin = 0.812, Tmax = 1.000	k = −14→16
25010 measured reflections	l = −40→40

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.096	H-atom parameters constrained
wR(F^2) = 0.195	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 0.5481P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5439 reflections	Δρmax = 0.12 e Å^−3
498 parameters	Δρmin = −0.12 e Å^−3
583 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.0 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.044 (4)	0.2419 (17)	0.6336 (9)	0.079 (7)	0.399 (4)
O2	0.6471 (10)	0.6317 (4)	0.51770 (16)	0.0813 (17)	0.399 (4)
O3	0.3432 (11)	0.6162 (5)	0.55003 (16)	0.094 (2)	0.399 (4)
C1	0.818 (5)	0.279 (2)	0.6904 (6)	0.051 (9)*	0.399 (4)
C2	0.863 (5)	0.3448 (19)	0.7221 (7)	0.067 (9)*	0.399 (4)
C3	0.795 (5)	0.327 (2)	0.7624 (8)	0.069 (8)*	0.399 (4)
H3	0.8216	0.3733	0.7829	0.083*	0.399 (4)
C4	0.688 (5)	0.2391 (19)	0.7713 (6)	0.048 (7)*	0.399 (4)
C5	0.631 (5)	0.1791 (18)	0.7389 (6)	0.054 (7)*	0.399 (4)
H5	0.5466	0.1243	0.7439	0.065*	0.399 (4)
C6	0.697 (5)	0.1982 (18)	0.6988 (6)	0.063 (9)*	0.399 (4)
C7	0.910 (4)	0.2946 (17)	0.6481 (6)	0.069 (8)*	0.399 (4)
C8	0.806 (4)	0.3713 (14)	0.6221 (6)	0.053 (8)*	0.399 (4)
C9	0.920 (4)	0.4060 (16)	0.5898 (6)	0.050 (7)*	0.399 (4)
H9	1.0548	0.3825	0.5845	0.060*	0.399 (4)
C10	0.829 (4)	0.4772 (19)	0.5651 (8)	0.060 (8)*	0.399 (4)
H10	0.9065	0.5016	0.5432	0.072*	0.399 (4)
C11	0.631 (5)	0.514 (2)	0.5711 (9)	0.056 (10)*	0.399 (4)
C12	0.520 (6)	0.475 (3)	0.6045 (12)	0.058 (10)*	0.399 (4)
H12	0.3836	0.4957	0.6096	0.070*	0.399 (4)
C13	0.611 (5)	0.405 (2)	0.6298 (9)	0.060 (9)*	0.399 (4)
H13	0.5364	0.3818	0.6523	0.072*	0.399 (4)
C14	0.5291 (15)	0.5937 (6)	0.5448 (2)	0.070 (2)	0.399 (4)
C15	1.013 (4)	0.4317 (18)	0.7148 (10)	0.074 (9)*	0.399 (4)
H15	1.0186	0.4416	0.6851	0.089*	0.399 (4)
C16	1.233 (5)	0.413 (4)	0.729 (2)	0.087 (17)*	0.399 (4)
H16A	1.2827	0.3524	0.7165	0.130*	0.399 (4)
H16B	1.3215	0.4664	0.7200	0.130*	0.399 (4)
H16C	1.2364	0.4073	0.7578	0.130*	0.399 (4)
C17	0.926 (5)	0.527 (2)	0.7330 (10)	0.113 (11)*	0.399 (4)
H17A	0.7841	0.5368	0.7236	0.169*	0.399 (4)
H17B	0.9264	0.5224	0.7623	0.169*	0.399 (4)
H17C	1.0114	0.5815	0.7245	0.169*	0.399 (4)
C18	0.638 (4)	0.214 (2)	0.8168 (6)	0.073 (8)*	0.399 (4)
H18	0.6515	0.1417	0.8192	0.088*	0.399 (4)
C19	0.786 (4)	0.257 (2)	0.8481 (7)	0.064 (7)*	0.399 (4)
H19A	0.9283	0.2414	0.8408	0.096*	0.399 (4)
H19B	0.7687	0.3274	0.8489	0.096*	0.399 (4)
H19C	0.7548	0.2299	0.8746	0.096*	0.399 (4)
C20	0.419 (5)	0.237 (3)	0.8274 (13)	0.108 (14)*	0.399 (4)
H20A	0.3267	0.2087	0.8073	0.162*	0.399 (4)
H20B	0.3867	0.2095	0.8538	0.162*	0.399 (4)
H20C	0.4005	0.3070	0.8281	0.162*	0.399 (4)
C21	0.631 (4)	0.1283 (17)	0.6655 (7)	0.069 (8)*	0.399 (4)
H21	0.6181	0.1654	0.6399	0.083*	0.399 (4)
C22	0.793 (4)	0.0474 (18)	0.6596 (8)	0.091 (9)*	0.399 (4)
H22A	0.7476	0.0037	0.6382	0.137*	0.399 (4)
H22B	0.9256	0.0763	0.6523	0.137*	0.399 (4)
H22C	0.8085	0.0109	0.6846	0.137*	0.399 (4)
C23	0.419 (4)	0.076 (2)	0.6745 (11)	0.087 (10)*	0.399 (4)
H23A	0.3847	0.0327	0.6523	0.130*	0.399 (4)
H23B	0.4297	0.0391	0.6994	0.130*	0.399 (4)
H23C	0.3099	0.1250	0.6773	0.130*	0.399 (4)
O1D	1.093 (4)	0.273 (3)	0.6402 (12)	0.069 (9)	0.312 (4)
O2D	0.6471 (10)	0.6317 (4)	0.51770 (16)	0.0813 (17)	0.312 (4)
O3D	0.3432 (11)	0.6162 (5)	0.55003 (16)	0.094 (2)	0.312 (4)
C1D	0.800 (6)	0.282 (2)	0.6904 (8)	0.059 (12)*	0.312 (4)
C2D	0.898 (5)	0.344 (2)	0.7176 (8)	0.056 (9)*	0.312 (4)
C3D	0.847 (5)	0.331 (2)	0.7592 (8)	0.064 (9)*	0.312 (4)
H3D	0.9148	0.3703	0.7787	0.077*	0.312 (4)
C4D	0.696 (7)	0.261 (3)	0.7724 (8)	0.069 (11)*	0.312 (4)
C5D	0.605 (9)	0.198 (4)	0.7430 (8)	0.062 (10)*	0.312 (4)
H5D	0.5083	0.1508	0.7509	0.075*	0.312 (4)
C6D	0.661 (8)	0.208 (3)	0.7022 (8)	0.054 (10)*	0.312 (4)
C7D	0.865 (4)	0.2739 (17)	0.6441 (7)	0.073 (10)*	0.312 (4)
C8D	0.767 (4)	0.3568 (16)	0.6185 (7)	0.050 (9)*	0.312 (4)
C9D	0.866 (6)	0.387 (3)	0.5827 (10)	0.061 (9)*	0.312 (4)
H9D	0.9878	0.3542	0.5744	0.074*	0.312 (4)
C10D	0.790 (6)	0.462 (3)	0.5594 (11)	0.063 (10)*	0.312 (4)
H10D	0.8642	0.4823	0.5364	0.075*	0.312 (4)
C11D	0.602 (5)	0.509 (3)	0.5693 (11)	0.052 (10)*	0.312 (4)
C12D	0.494 (7)	0.472 (4)	0.6026 (15)	0.069 (11)*	0.312 (4)
H12D	0.3633	0.4988	0.6092	0.083*	0.312 (4)
C13D	0.574 (5)	0.397 (3)	0.6261 (11)	0.061 (10)*	0.312 (4)
H13D	0.4940	0.3721	0.6478	0.073*	0.312 (4)
C14D	0.5291 (15)	0.5937 (6)	0.5448 (2)	0.070 (2)	0.312 (4)
C15D	1.042 (5)	0.427 (2)	0.7041 (11)	0.070 (10)*	0.312 (4)
H15D	1.0709	0.4168	0.6749	0.084*	0.312 (4)
C16D	1.247 (7)	0.419 (5)	0.726 (3)	0.075 (19)*	0.312 (4)
H16D	1.3374	0.4717	0.7172	0.112*	0.312 (4)
H16E	1.2234	0.4239	0.7548	0.112*	0.312 (4)
H16F	1.3108	0.3568	0.7196	0.112*	0.312 (4)
C17D	0.936 (7)	0.528 (2)	0.7084 (12)	0.070 (12)*	0.312 (4)
H17D	0.8051	0.5274	0.6936	0.105*	0.312 (4)
H17E	0.9091	0.5410	0.7367	0.105*	0.312 (4)
H17F	1.0260	0.5779	0.6974	0.105*	0.312 (4)
C18D	0.621 (6)	0.238 (4)	0.8167 (8)	0.091 (12)*	0.312 (4)
H18D	0.5913	0.1688	0.8107	0.109*	0.312 (4)
C19D	0.767 (6)	0.214 (2)	0.8503 (9)	0.092 (12)*	0.312 (4)
H19D	0.9040	0.2009	0.8392	0.137*	0.312 (4)
H19E	0.7755	0.2695	0.8687	0.137*	0.312 (4)
H19F	0.7167	0.1575	0.8647	0.137*	0.312 (4)
C20D	0.399 (6)	0.262 (4)	0.8257 (16)	0.080 (14)*	0.312 (4)
H20D	0.3258	0.2758	0.8006	0.121*	0.312 (4)
H20E	0.3337	0.2071	0.8392	0.121*	0.312 (4)
H20F	0.3925	0.3191	0.8432	0.121*	0.312 (4)
C21D	0.595 (6)	0.150 (3)	0.6642 (10)	0.086 (11)*	0.312 (4)
H21D	0.4721	0.1829	0.6524	0.104*	0.312 (4)
C22D	0.785 (4)	0.1715 (17)	0.6358 (8)	0.095 (9)*	0.312 (4)
H22D	0.8959	0.1238	0.6408	0.114*	0.312 (4)
H22E	0.7422	0.1659	0.6074	0.114*	0.312 (4)
C23D	0.543 (6)	0.044 (2)	0.6696 (10)	0.110 (12)*	0.312 (4)
H23D	0.5042	0.0160	0.6437	0.165*	0.312 (4)
H23E	0.6625	0.0095	0.6804	0.165*	0.312 (4)
H23F	0.4270	0.0378	0.6884	0.165*	0.312 (4)
O1P	1.113 (7)	0.306 (3)	0.6514 (16)	0.075 (10)	0.169 (4)
O2P	0.6471 (10)	0.6317 (4)	0.51770 (16)	0.0813 (17)	0.169 (4)
O3P	0.3432 (11)	0.6162 (5)	0.55003 (16)	0.094 (2)	0.169 (4)
C1P	0.807 (7)	0.293 (3)	0.7006 (10)	0.053 (12)*	0.169 (4)
C2P	0.874 (7)	0.346 (3)	0.7350 (10)	0.062 (12)*	0.169 (4)
C3P	0.795 (8)	0.323 (4)	0.7737 (11)	0.063 (13)*	0.169 (4)
H3P	0.8416	0.3564	0.7969	0.075*	0.169 (4)
C4P	0.645 (8)	0.250 (4)	0.7764 (11)	0.066 (14)*	0.169 (4)
C5P	0.585 (13)	0.193 (6)	0.7434 (12)	0.060 (13)*	0.169 (4)
H5P	0.4929	0.1399	0.7468	0.072*	0.169 (4)
C6P	0.664 (11)	0.216 (4)	0.7047 (12)	0.056 (13)*	0.169 (4)
C7P	0.938 (5)	0.352 (2)	0.6700 (8)	0.059 (10)*	0.169 (4)
C8P	0.828 (5)	0.406 (3)	0.6351 (10)	0.054 (10)*	0.169 (4)
C9P	0.945 (5)	0.451 (3)	0.6048 (10)	0.065 (11)*	0.169 (4)
H9P	1.0900	0.4410	0.6040	0.078*	0.169 (4)
C10P	0.851 (6)	0.511 (3)	0.5752 (11)	0.069 (12)*	0.169 (4)
H10P	0.9321	0.5369	0.5543	0.082*	0.169 (4)
C11P	0.639 (6)	0.531 (3)	0.5767 (10)	0.065 (14)*	0.169 (4)
C12P	0.520 (7)	0.492 (5)	0.6087 (16)	0.063 (13)*	0.169 (4)
H12P	0.3778	0.5075	0.6111	0.076*	0.169 (4)
C13P	0.616 (6)	0.430 (4)	0.6370 (15)	0.056 (12)*	0.169 (4)
H13P	0.5349	0.4042	0.6581	0.067*	0.169 (4)
C14P	0.5291 (15)	0.5937 (6)	0.5448 (2)	0.070 (2)	0.169 (4)
C15P	0.989 (6)	0.422 (3)	0.7097 (11)	0.071 (14)*	0.169 (4)
C16P	1.224 (7)	0.438 (5)	0.7127 (18)	0.10 (2)*	0.169 (4)
H16G	1.2657	0.4891	0.6942	0.154*	0.169 (4)
H16H	1.2600	0.4563	0.7402	0.154*	0.169 (4)
H16I	1.2954	0.3776	0.7057	0.154*	0.169 (4)
C17P	0.884 (10)	0.523 (3)	0.713 (2)	0.061 (19)*	0.169 (4)
H17G	0.9604	0.5701	0.6968	0.092*	0.169 (4)
H17H	0.7419	0.5190	0.7036	0.092*	0.169 (4)
H17I	0.8850	0.5442	0.7412	0.092*	0.169 (4)
C18P	0.555 (7)	0.219 (4)	0.8176 (11)	0.074 (13)*	0.169 (4)
H18P	0.5577	0.1473	0.8212	0.089*	0.169 (4)
C19P	0.681 (8)	0.271 (5)	0.8508 (14)	0.087 (18)*	0.169 (4)
H19G	0.8216	0.2452	0.8512	0.130*	0.169 (4)
H19H	0.6858	0.3407	0.8451	0.130*	0.169 (4)
H19I	0.6157	0.2605	0.8769	0.130*	0.169 (4)
C20P	0.331 (6)	0.258 (5)	0.8157 (16)	0.065 (16)*	0.169 (4)
H20G	0.2553	0.2237	0.7946	0.097*	0.169 (4)
H20H	0.2629	0.2470	0.8416	0.097*	0.169 (4)
H20I	0.3330	0.3273	0.8098	0.097*	0.169 (4)
C21P	0.581 (8)	0.154 (4)	0.6698 (15)	0.080 (14)*	0.169 (4)
H21P	0.5461	0.1983	0.6471	0.096*	0.169 (4)
C22P	0.755 (9)	0.084 (4)	0.6548 (17)	0.077 (17)*	0.169 (4)
H22F	0.7026	0.0444	0.6327	0.115*	0.169 (4)
H22G	0.8732	0.1220	0.6455	0.115*	0.169 (4)
H22H	0.7984	0.0418	0.6769	0.115*	0.169 (4)
C23P	0.384 (9)	0.095 (5)	0.680 (3)	0.11 (3)*	0.169 (4)
H23G	0.3404	0.0574	0.6571	0.158*	0.169 (4)
H23H	0.4133	0.0515	0.7028	0.158*	0.169 (4)
H23I	0.2735	0.1399	0.6881	0.158*	0.169 (4)
O1Z	1.110 (8)	0.281 (6)	0.652 (2)	0.073 (11)*	0.121 (4)
O2Z	0.6471 (10)	0.6317 (4)	0.51770 (16)	0.0813 (17)	0.121 (4)
O3Z	0.3432 (11)	0.6162 (5)	0.55003 (16)	0.094 (2)	0.121 (4)
C1Z	0.876 (7)	0.303 (3)	0.6989 (11)	0.048 (13)*	0.121 (4)
C2Z	0.914 (6)	0.370 (3)	0.7300 (12)	0.061 (14)*	0.121 (4)
C3Z	0.836 (7)	0.359 (3)	0.7692 (13)	0.079 (15)*	0.121 (4)
H3Z	0.8604	0.4061	0.7893	0.095*	0.121 (4)
C4Z	0.721 (8)	0.275 (4)	0.7776 (11)	0.059 (14)*	0.121 (4)
C5Z	0.672 (9)	0.209 (4)	0.7464 (11)	0.061 (14)*	0.121 (4)
H5Z	0.5826	0.1561	0.7520	0.074*	0.121 (4)
C6Z	0.753 (8)	0.220 (3)	0.7067 (11)	0.055 (13)*	0.121 (4)
C7Z	0.887 (8)	0.288 (3)	0.6529 (11)	0.074 (15)*	0.121 (4)
C8Z	0.792 (10)	0.365 (4)	0.6237 (15)	0.054 (15)*	0.121 (4)
C9Z	0.884 (14)	0.384 (7)	0.586 (2)	0.060 (15)*	0.121 (4)
H9Z	1.0046	0.3498	0.5779	0.072*	0.121 (4)
C10Z	0.796 (14)	0.453 (6)	0.560 (2)	0.066 (15)*	0.121 (4)
H10Z	0.8494	0.4608	0.5333	0.079*	0.121 (4)
C11Z	0.630 (6)	0.5113 (18)	0.5723 (12)	0.057 (15)*	0.121 (4)
C12Z	0.542 (10)	0.496 (5)	0.6110 (16)	0.061 (14)*	0.121 (4)
H12Z	0.4274	0.5337	0.6195	0.073*	0.121 (4)
C13Z	0.629 (11)	0.425 (6)	0.6367 (18)	0.058 (14)*	0.121 (4)
H13Z	0.5758	0.4177	0.6630	0.069*	0.121 (4)
C14Z	0.5291 (15)	0.5937 (6)	0.5448 (2)	0.070 (2)	0.121 (4)
C15Z	1.045 (8)	0.458 (3)	0.7199 (19)	0.069 (14)*	0.121 (4)
H15Z	1.0766	0.4512	0.6907	0.083*	0.121 (4)
C16Z	1.253 (7)	0.453 (5)	0.740 (2)	0.11 (3)*	0.121 (4)
H16J	1.3128	0.3892	0.7361	0.164*	0.121 (4)
H16K	1.3441	0.5027	0.7288	0.164*	0.121 (4)
H16L	1.2359	0.4653	0.7690	0.164*	0.121 (4)
C17Z	0.925 (11)	0.552 (4)	0.723 (3)	0.07 (2)*	0.121 (4)
H17J	0.7943	0.5453	0.7082	0.105*	0.121 (4)
H17K	0.8975	0.5672	0.7508	0.105*	0.121 (4)
H17L	1.0057	0.6045	0.7106	0.105*	0.121 (4)
C18Z	0.628 (9)	0.267 (4)	0.8200 (12)	0.082 (15)*	0.121 (4)
H18Z	0.6132	0.1967	0.8273	0.098*	0.121 (4)
C19Z	0.808 (10)	0.311 (6)	0.8440 (17)	0.09 (2)*	0.121 (4)
H19J	0.7733	0.3120	0.8726	0.138*	0.121 (4)
H19K	0.9327	0.2730	0.8398	0.138*	0.121 (4)
H19L	0.8316	0.3779	0.8348	0.138*	0.121 (4)
C20Z	0.422 (10)	0.319 (6)	0.828 (2)	0.11 (2)*	0.121 (4)
H20J	0.3800	0.3081	0.8561	0.166*	0.121 (4)
H20K	0.4397	0.3889	0.8237	0.166*	0.121 (4)
H20L	0.3155	0.2944	0.8101	0.166*	0.121 (4)
C21Z	0.765 (7)	0.183 (3)	0.6633 (11)	0.085 (14)*	0.121 (4)
C22Z	0.908 (10)	0.093 (3)	0.6622 (18)	0.082 (19)*	0.121 (4)
H22I	0.9169	0.0686	0.6347	0.123*	0.121 (4)
H22J	1.0456	0.1109	0.6717	0.123*	0.121 (4)
H22K	0.8509	0.0425	0.6796	0.123*	0.121 (4)
C23Z	0.565 (10)	0.171 (5)	0.638 (2)	0.15 (3)*	0.121 (4)
H23J	0.6007	0.1473	0.6113	0.221*	0.121 (4)
H23K	0.4733	0.1251	0.6514	0.221*	0.121 (4)
H23L	0.4959	0.2340	0.6357	0.221*	0.121 (4)
N1	0.0554 (10)	0.6670 (4)	0.49226 (16)	0.0682 (19)
H1A	0.1547	0.6434	0.5088	0.082*
H1B	−0.0707	0.6521	0.5023	0.082*
H1C	0.0682	0.7323	0.4904	0.082*
C24	0.2920 (15)	0.6528 (7)	0.4332 (2)	0.102 (3)
H24A	0.4004	0.6372	0.4526	0.152*
H24B	0.2914	0.7226	0.4281	0.152*
H24C	0.3183	0.6182	0.4080	0.152*
C25	0.0792 (14)	0.6215 (7)	0.4503 (2)	0.074 (3)
H25	−0.0311	0.6482	0.4325	0.089*
C26	0.050 (2)	0.5132 (8)	0.4532 (3)	0.083 (3)
C27	−0.137 (2)	0.4721 (10)	0.4401 (3)	0.114 (4)
H27	−0.2436	0.5132	0.4305	0.137*
C28	−0.169 (3)	0.3705 (14)	0.4409 (4)	0.148 (6)
H28	−0.2955	0.3434	0.4319	0.178*
C29	−0.013 (4)	0.3122 (14)	0.4550 (6)	0.171 (8)
H29	−0.0350	0.2443	0.4554	0.205*
C30	0.173 (4)	0.3476 (12)	0.4685 (5)	0.172 (7)
H30	0.2776	0.3053	0.4777	0.206*
C31	0.202 (2)	0.4506 (10)	0.4681 (3)	0.120 (4)
H31	0.3269	0.4768	0.4782	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.095 (13)	0.063 (14)	0.080 (12)	0.028 (11)	0.026 (11)	0.015 (11)
O2	0.083 (4)	0.090 (4)	0.071 (3)	−0.001 (4)	0.010 (3)	0.030 (3)
O3	0.076 (4)	0.140 (5)	0.066 (4)	0.023 (4)	−0.007 (4)	0.034 (4)
C14	0.084 (6)	0.076 (5)	0.051 (5)	0.000 (5)	−0.021 (5)	0.008 (4)
O1D	0.071 (13)	0.062 (18)	0.074 (15)	0.011 (13)	0.011 (13)	−0.007 (14)
O2D	0.083 (4)	0.090 (4)	0.071 (3)	−0.001 (4)	0.010 (3)	0.030 (3)
O3D	0.076 (4)	0.140 (5)	0.066 (4)	0.023 (4)	−0.007 (4)	0.034 (4)
C14D	0.084 (6)	0.076 (5)	0.051 (5)	0.000 (5)	−0.021 (5)	0.008 (4)
O1P	0.077 (15)	0.073 (18)	0.074 (17)	0.012 (15)	0.018 (14)	0.008 (15)
O2P	0.083 (4)	0.090 (4)	0.071 (3)	−0.001 (4)	0.010 (3)	0.030 (3)
O3P	0.076 (4)	0.140 (5)	0.066 (4)	0.023 (4)	−0.007 (4)	0.034 (4)
C14P	0.084 (6)	0.076 (5)	0.051 (5)	0.000 (5)	−0.021 (5)	0.008 (4)
O2Z	0.083 (4)	0.090 (4)	0.071 (3)	−0.001 (4)	0.010 (3)	0.030 (3)
O3Z	0.076 (4)	0.140 (5)	0.066 (4)	0.023 (4)	−0.007 (4)	0.034 (4)
C14Z	0.084 (6)	0.076 (5)	0.051 (5)	0.000 (5)	−0.021 (5)	0.008 (4)
N1	0.073 (5)	0.081 (4)	0.051 (4)	0.006 (4)	−0.002 (4)	0.016 (3)
C24	0.109 (9)	0.127 (8)	0.068 (6)	−0.005 (7)	0.031 (6)	−0.002 (6)
C25	0.071 (7)	0.105 (8)	0.046 (5)	−0.002 (6)	−0.011 (5)	0.008 (5)
C26	0.106 (9)	0.093 (8)	0.050 (5)	−0.007 (8)	0.006 (6)	−0.006 (6)
C27	0.130 (13)	0.116 (11)	0.095 (8)	−0.004 (9)	0.024 (8)	−0.014 (7)
C28	0.155 (16)	0.156 (17)	0.133 (12)	−0.036 (13)	0.042 (11)	−0.035 (12)
C29	0.24 (3)	0.116 (15)	0.159 (16)	−0.037 (16)	0.036 (17)	−0.017 (11)
C30	0.24 (2)	0.103 (14)	0.171 (14)	0.033 (13)	−0.016 (14)	0.007 (10)
C31	0.165 (13)	0.105 (10)	0.091 (8)	0.010 (10)	−0.027 (8)	−0.006 (7)

Geometric parameters (Å, º)

O1—C7	1.21 (2)	C4P—C18P	1.52 (2)
O2—C14	1.269 (9)	C5P—C6P	1.40 (2)
O3—C14	1.232 (9)	C5P—H5P	0.9300
C1—C6	1.370 (19)	C6P—C21P	1.51 (2)
C1—C2	1.39 (2)	C7P—C8P	1.53 (2)
C1—C7	1.516 (19)	C7P—C15P	1.64 (2)
C2—C3	1.40 (2)	C8P—C9P	1.38 (2)
C2—C15	1.53 (2)	C8P—C13P	1.39 (2)
C3—C4	1.41 (2)	C9P—C10P	1.40 (2)
C3—H3	0.9300	C9P—H9P	0.9300
C4—C5	1.38 (2)	C10P—C11P	1.38 (2)
C4—C18	1.559 (19)	C10P—H10P	0.9300
C5—C6	1.400 (19)	C11P—C12P	1.40 (2)
C5—H5	0.9300	C11P—C14P	1.51 (2)
C6—C21	1.50 (2)	C12P—C13P	1.39 (2)
C7—C8	1.496 (18)	C12P—H12P	0.9300
C8—C13	1.35 (2)	C13P—H13P	0.9300
C8—C9	1.364 (18)	C15P—C16P	1.51 (3)
C9—C10	1.386 (18)	C15P—C17P	1.53 (2)
C9—H9	0.9300	C16P—H16G	0.9600
C10—C11	1.36 (2)	C16P—H16H	0.9600
C10—H10	0.9300	C16P—H16I	0.9600
C11—C12	1.40 (2)	C17P—H17G	0.9600
C11—C14	1.527 (17)	C17P—H17H	0.9600
C12—C13	1.38 (2)	C17P—H17I	0.9600
C12—H12	0.9300	C18P—C20P	1.52 (3)
C13—H13	0.9300	C18P—C19P	1.52 (3)
C15—C16	1.49 (2)	C18P—H18P	0.9800
C15—C17	1.52 (2)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C23P	1.53 (3)
C17—H17C	0.9600	C21P—C22P	1.53 (3)
C18—C20	1.47 (2)	C21P—H21P	0.9800
C18—C19	1.51 (2)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (3)
C20—H20C	0.9600	O2Z—C14Z	1.269 (9)
C21—C22	1.52 (2)	O3Z—C14Z	1.232 (9)
C21—C23	1.55 (2)	C1Z—C2Z	1.38 (2)
C21—H21	0.9800	C1Z—C6Z	1.40 (2)
C22—H22A	0.9600	C1Z—C7Z	1.52 (2)
C22—H22B	0.9600	C2Z—C3Z	1.38 (2)
C22—H22C	0.9600	C2Z—C15Z	1.50 (2)
C23—H23A	0.9600	C3Z—C4Z	1.38 (3)
C23—H23B	0.9600	C3Z—H3Z	0.9300
C23—H23C	0.9600	C4Z—C5Z	1.39 (2)
O1D—C7D	1.46 (2)	C4Z—C18Z	1.51 (2)
O2D—C14D	1.269 (9)	C5Z—C6Z	1.40 (2)
O3D—C14D	1.232 (9)	C5Z—H5Z	0.9300
C1D—C2D	1.37 (2)	C6Z—C21Z	1.51 (2)
C1D—C6D	1.39 (2)	C7Z—C8Z	1.54 (2)
C1D—C7D	1.57 (2)	C7Z—C21Z	1.65 (2)
C2D—C3D	1.41 (2)	C8Z—C13Z	1.39 (3)
C2D—C15D	1.52 (2)	C8Z—C9Z	1.39 (2)
C3D—C4D	1.42 (2)	C9Z—C10Z	1.39 (3)
C3D—H3D	0.9300	C9Z—H9Z	0.9300
C4D—C5D	1.40 (2)	C10Z—C11Z	1.38 (2)
C4D—C18D	1.55 (2)	C10Z—H10Z	0.9300
C5D—C6D	1.39 (2)	C11Z—C12Z	1.40 (2)
C5D—H5D	0.9300	C11Z—C14Z	1.57 (2)
C6D—C21D	1.53 (2)	C12Z—C13Z	1.39 (3)
C7D—C22D	1.50 (2)	C12Z—H12Z	0.9300
C7D—C8D	1.53 (2)	C13Z—H13Z	0.9300
C8D—C13D	1.36 (2)	C15Z—C16Z	1.48 (3)
C8D—C9D	1.39 (2)	C15Z—C17Z	1.48 (3)
C9D—C10D	1.36 (2)	C15Z—H15Z	0.9800
C9D—H9D	0.9300	C16Z—H16J	0.9600
C10D—C11D	1.39 (2)	C16Z—H16K	0.9600
C10D—H10D	0.9300	C16Z—H16L	0.9600
C11D—C12D	1.38 (2)	C17Z—H17J	0.9600
C11D—C14D	1.470 (18)	C17Z—H17K	0.9600
C12D—C13D	1.38 (2)	C17Z—H17L	0.9600
C12D—H12D	0.9300	C18Z—C20Z	1.51 (3)
C13D—H13D	0.9300	C18Z—C19Z	1.52 (3)
C15D—C16D	1.48 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.53 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C23Z	1.52 (2)
C17D—H17F	0.9600	C21Z—C22Z	1.53 (3)
C18D—C19D	1.47 (2)	C22Z—H22I	0.9600
C18D—C20D	1.48 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.510 (9)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.49 (2)	N1—H1C	0.8900
C21D—C22D	1.55 (2)	C24—C25	1.525 (11)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.482 (12)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C31	1.374 (14)
O1P—C7P	1.41 (2)	C26—C27	1.384 (15)
O2P—C14P	1.269 (9)	C27—C28	1.392 (16)
O3P—C14P	1.232 (9)	C27—H27	0.9300
C1P—C6P	1.39 (2)	C28—C29	1.35 (2)
C1P—C2P	1.40 (2)	C28—H28	0.9300
C1P—C7P	1.52 (2)	C29—C30	1.35 (2)
C2P—C3P	1.40 (2)	C29—H29	0.9300
C2P—C15P	1.51 (2)	C30—C31	1.408 (16)
C3P—C4P	1.38 (2)	C30—H30	0.9300
C3P—H3P	0.9300	C31—H31	0.9300
C4P—C5P	1.38 (2)
C6—C1—C2	118.5 (17)	C1P—C7P—C8P	119 (2)
C6—C1—C7	120.6 (19)	O1P—C7P—C15P	116 (3)
C2—C1—C7	120.8 (19)	C1P—C7P—C15P	83.6 (17)
C1—C2—C3	121.8 (19)	C8P—C7P—C15P	113 (2)
C1—C2—C15	120 (2)	C9P—C8P—C13P	117 (2)
C3—C2—C15	117.8 (19)	C9P—C8P—C7P	120 (2)
C2—C3—C4	119 (2)	C13P—C8P—C7P	122 (2)
C2—C3—H3	120.5	C8P—C9P—C10P	121 (3)
C4—C3—H3	120.5	C8P—C9P—H9P	119.5
C5—C4—C3	117.9 (18)	C10P—C9P—H9P	119.5
C5—C4—C18	123.1 (18)	C11P—C10P—C9P	121 (3)
C3—C4—C18	119.0 (18)	C11P—C10P—H10P	119.5
C4—C5—C6	122.0 (19)	C9P—C10P—H10P	119.5
C4—C5—H5	119.0	C10P—C11P—C12P	119 (2)
C6—C5—H5	119.0	C10P—C11P—C14P	123 (3)
C1—C6—C5	120.1 (18)	C12P—C11P—C14P	119 (3)
C1—C6—C21	121.2 (18)	C13P—C12P—C11P	119 (3)
C5—C6—C21	118.6 (18)	C13P—C12P—H12P	120.4
O1—C7—C8	120 (2)	C11P—C12P—H12P	120.4
O1—C7—C1	123 (2)	C12P—C13P—C8P	123 (3)
C8—C7—C1	116.2 (19)	C12P—C13P—H13P	118.7
C13—C8—C9	121.0 (18)	C8P—C13P—H13P	118.7
C13—C8—C7	122.6 (19)	O3P—C14P—O2P	124.3 (7)
C9—C8—C7	116.3 (18)	O3P—C14P—C11P	119.0 (16)
C8—C9—C10	117.9 (19)	O2P—C14P—C11P	115.7 (16)
C8—C9—H9	121.1	C2P—C15P—C16P	123 (3)
C10—C9—H9	121.1	C2P—C15P—C17P	111 (3)
C11—C10—C9	124 (2)	C16P—C15P—C17P	107 (3)
C11—C10—H10	118.1	C2P—C15P—C7P	86.6 (18)
C9—C10—H10	118.1	C16P—C15P—C7P	109 (3)
C10—C11—C12	115.9 (18)	C17P—C15P—C7P	120 (3)
C10—C11—C14	124.6 (19)	C15P—C16P—H16G	109.5
C12—C11—C14	119.5 (19)	C15P—C16P—H16H	109.5
C13—C12—C11	121 (2)	H16G—C16P—H16H	109.5
C13—C12—H12	119.5	C15P—C16P—H16I	109.5
C11—C12—H12	119.5	H16G—C16P—H16I	109.5
C8—C13—C12	120 (2)	H16H—C16P—H16I	109.5
C8—C13—H13	119.8	C15P—C17P—H17G	109.5
C12—C13—H13	119.8	C15P—C17P—H17H	109.5
O3—C14—O2	124.3 (7)	H17G—C17P—H17H	109.5
O3—C14—C11	120.3 (13)	C15P—C17P—H17I	109.5
O2—C14—C11	115.4 (13)	H17G—C17P—H17I	109.5
C16—C15—C17	112 (3)	H17H—C17P—H17I	109.5
C16—C15—C2	114 (2)	C20P—C18P—C19P	111 (3)
C17—C15—C2	111 (2)	C20P—C18P—C4P	103 (3)
C16—C15—H15	106.5	C19P—C18P—C4P	108 (3)
C17—C15—H15	106.5	C20P—C18P—H18P	111.4
C2—C15—H15	106.5	C19P—C18P—H18P	111.4
C15—C16—H16A	109.5	C4P—C18P—H18P	111.4
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C20—C18—C19	110 (2)	H20H—C20P—H20I	109.5
C20—C18—C4	112 (2)	C6P—C21P—C23P	114 (3)
C19—C18—C4	115.6 (19)	C6P—C21P—C22P	110 (3)
C20—C18—H18	106.1	C23P—C21P—C22P	110 (3)
C19—C18—H18	106.1	C6P—C21P—H21P	107.7
C4—C18—H18	106.1	C23P—C21P—H21P	107.7
C18—C19—H19A	109.5	C22P—C21P—H21P	107.7
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C6—C21—C22	111 (2)	H23H—C23P—H23I	109.5
C6—C21—C23	113 (2)	C2Z—C1Z—C6Z	119 (2)
C22—C21—C23	106.7 (19)	C2Z—C1Z—C7Z	144 (3)
C6—C21—H21	108.6	C6Z—C1Z—C7Z	95 (2)
C22—C21—H21	108.6	C1Z—C2Z—C3Z	123 (3)
C23—C21—H21	108.6	C1Z—C2Z—C15Z	117 (3)
C21—C22—H22A	109.5	C3Z—C2Z—C15Z	120 (3)
C21—C22—H22B	109.5	C4Z—C3Z—C2Z	118 (3)
H22A—C22—H22B	109.5	C4Z—C3Z—H3Z	121.2
C21—C22—H22C	109.5	C2Z—C3Z—H3Z	121.2
H22A—C22—H22C	109.5	C3Z—C4Z—C5Z	120 (3)
H22B—C22—H22C	109.5	C3Z—C4Z—C18Z	117 (3)
C21—C23—H23A	109.5	C5Z—C4Z—C18Z	122 (3)
C21—C23—H23B	109.5	C4Z—C5Z—C6Z	121 (3)
H23A—C23—H23B	109.5	C4Z—C5Z—H5Z	119.3
C21—C23—H23C	109.5	C6Z—C5Z—H5Z	119.3
H23A—C23—H23C	109.5	C1Z—C6Z—C5Z	118 (3)
H23B—C23—H23C	109.5	C1Z—C6Z—C21Z	94 (2)
C2D—C1D—C6D	123 (2)	C5Z—C6Z—C21Z	148 (3)
C2D—C1D—C7D	123 (2)	O1Z—C7Z—C1Z	95 (3)
C6D—C1D—C7D	112.6 (18)	O1Z—C7Z—C8Z	115 (3)
C1D—C2D—C3D	117 (2)	C1Z—C7Z—C8Z	120 (3)
C1D—C2D—C15D	123 (2)	O1Z—C7Z—C21Z	115 (3)
C3D—C2D—C15D	121 (2)	C1Z—C7Z—C21Z	83.9 (18)
C2D—C3D—C4D	122 (2)	C8Z—C7Z—C21Z	122 (3)
C2D—C3D—H3D	119.1	C13Z—C8Z—C9Z	119 (3)
C4D—C3D—H3D	119.1	C13Z—C8Z—C7Z	120 (3)
C5D—C4D—C3D	118 (2)	C9Z—C8Z—C7Z	121 (3)
C5D—C4D—C18D	113 (2)	C10Z—C9Z—C8Z	120 (3)
C3D—C4D—C18D	128 (2)	C10Z—C9Z—H9Z	120.0
C6D—C5D—C4D	120 (2)	C8Z—C9Z—H9Z	120.0
C6D—C5D—H5D	120.1	C11Z—C10Z—C9Z	121 (3)
C4D—C5D—H5D	120.1	C11Z—C10Z—H10Z	119.7
C5D—C6D—C1D	120 (2)	C9Z—C10Z—H10Z	119.7
C5D—C6D—C21D	131 (2)	C10Z—C11Z—C12Z	120 (3)
C1D—C6D—C21D	108.5 (18)	C10Z—C11Z—C14Z	123 (3)
O1D—C7D—C22D	108 (2)	C12Z—C11Z—C14Z	117 (3)
O1D—C7D—C8D	111 (2)	C13Z—C12Z—C11Z	119 (3)
C22D—C7D—C8D	116.1 (18)	C13Z—C12Z—H12Z	120.5
O1D—C7D—C1D	110 (2)	C11Z—C12Z—H12Z	120.5
C22D—C7D—C1D	98.7 (17)	C8Z—C13Z—C12Z	121 (3)
C8D—C7D—C1D	112 (2)	C8Z—C13Z—H13Z	119.3
C13D—C8D—C9D	117 (2)	C12Z—C13Z—H13Z	119.3
C13D—C8D—C7D	124 (2)	O3Z—C14Z—O2Z	124.3 (7)
C9D—C8D—C7D	119 (2)	O3Z—C14Z—C11Z	119.3 (17)
C10D—C9D—C8D	122 (2)	O2Z—C14Z—C11Z	116.4 (17)
C10D—C9D—H9D	119.2	C16Z—C15Z—C17Z	118 (4)
C8D—C9D—H9D	119.2	C16Z—C15Z—C2Z	111 (3)
C9D—C10D—C11D	121 (2)	C17Z—C15Z—C2Z	113 (3)
C9D—C10D—H10D	119.3	C16Z—C15Z—H15Z	104.5
C11D—C10D—H10D	119.3	C17Z—C15Z—H15Z	104.5
C12D—C11D—C10D	116 (2)	C2Z—C15Z—H15Z	104.5
C12D—C11D—C14D	124 (2)	C15Z—C16Z—H16J	109.5
C10D—C11D—C14D	120 (2)	C15Z—C16Z—H16K	109.5
C13D—C12D—C11D	122 (3)	H16J—C16Z—H16K	109.5
C13D—C12D—H12D	119.1	C15Z—C16Z—H16L	109.5
C11D—C12D—H12D	119.1	H16J—C16Z—H16L	109.5
C8D—C13D—C12D	122 (3)	H16K—C16Z—H16L	109.5
C8D—C13D—H13D	119.2	C15Z—C17Z—H17J	109.5
C12D—C13D—H13D	119.2	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	124.3 (7)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	114.8 (14)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	120.5 (14)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	110 (3)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	114 (3)	C4Z—C18Z—C20Z	118 (3)
C2D—C15D—C17D	111 (2)	C4Z—C18Z—C19Z	98 (3)
C16D—C15D—H15D	107.1	C20Z—C18Z—C19Z	112 (4)
C2D—C15D—H15D	107.1	C4Z—C18Z—H18Z	109.4
C17D—C15D—H15D	107.1	C20Z—C18Z—H18Z	109.4
C15D—C16D—H16D	109.5	C19Z—C18Z—H18Z	109.4
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C19D—C18D—C20D	120 (3)	H20K—C20Z—H20L	109.5
C19D—C18D—C4D	123 (3)	C6Z—C21Z—C23Z	120 (4)
C20D—C18D—C4D	116 (3)	C6Z—C21Z—C22Z	109 (3)
C19D—C18D—H18D	93.6	C23Z—C21Z—C22Z	114 (3)
C20D—C18D—H18D	93.6	C6Z—C21Z—C7Z	86.2 (19)
C4D—C18D—H18D	93.6	C23Z—C21Z—C7Z	112 (3)
C18D—C19D—H19D	109.5	C22Z—C21Z—C7Z	114 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	118 (3)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	115 (3)	C25—N1—H1A	109.5
C6D—C21D—C22D	100.3 (19)	C25—N1—H1B	109.5
C23D—C21D—H21D	107.7	H1A—N1—H1B	109.5
C6D—C21D—H21D	107.7	C25—N1—H1C	109.5
C22D—C21D—H21D	107.7	H1A—N1—H1C	109.5
C7D—C22D—C21D	109.0 (18)	H1B—N1—H1C	109.5
C7D—C22D—H22D	109.9	C25—C24—H24A	109.5
C21D—C22D—H22D	109.9	C25—C24—H24B	109.5
C7D—C22D—H22E	109.9	H24A—C24—H24B	109.5
C21D—C22D—H22E	109.9	C25—C24—H24C	109.5
H22D—C22D—H22E	108.3	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	109.5 (6)
H23D—C23D—H23E	109.5	C26—C25—C24	114.1 (9)
C21D—C23D—H23F	109.5	N1—C25—C24	108.0 (7)
H23D—C23D—H23F	109.5	C26—C25—H25	108.4
H23E—C23D—H23F	109.5	N1—C25—H25	108.4
C6P—C1P—C2P	120 (2)	C24—C25—H25	108.4
C6P—C1P—C7P	144 (3)	C31—C26—C27	117.9 (11)
C2P—C1P—C7P	95.6 (19)	C31—C26—C25	123.1 (12)
C3P—C2P—C1P	120 (2)	C27—C26—C25	119.0 (12)
C3P—C2P—C15P	145 (3)	C26—C27—C28	121.2 (14)
C1P—C2P—C15P	93 (2)	C26—C27—H27	119.4
C4P—C3P—C2P	118 (3)	C28—C27—H27	119.4
C4P—C3P—H3P	121.1	C29—C28—C27	118.5 (19)
C2P—C3P—H3P	121.1	C29—C28—H28	120.7
C5P—C4P—C3P	123 (3)	C27—C28—H28	120.7
C5P—C4P—C18P	116 (3)	C28—C29—C30	123 (2)
C3P—C4P—C18P	121 (3)	C28—C29—H29	118.4
C4P—C5P—C6P	119 (3)	C30—C29—H29	118.4
C4P—C5P—H5P	120.6	C29—C30—C31	117.8 (18)
C6P—C5P—H5P	120.6	C29—C30—H30	121.1
C1P—C6P—C5P	120 (3)	C31—C30—H30	121.1
C1P—C6P—C21P	125 (3)	C26—C31—C30	121.3 (14)
C5P—C6P—C21P	115 (3)	C26—C31—H31	119.3
O1P—C7P—C1P	119 (3)	C30—C31—H31	119.3
O1P—C7P—C8P	105 (2)

(790minUV)

Crystal data

C31H39NO3	Dx = 1.119 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2131 reflections
a = 6.3663 (6) Å	θ = 1.6–18.2°
b = 13.5168 (12) Å	µ = 0.07 mm^−1
c = 32.6694 (18) Å	T = 299 K
V = 2811.3 (4) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5436 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.128
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −16→14
Tmin = 0.856, Tmax = 1.000	l = −40→40
24990 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.090	H-atom parameters constrained
wR(F^2) = 0.211	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 0.5247P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5436 reflections	Δρmax = 0.13 e Å^−3
469 parameters	Δρmin = −0.15 e Å^−3
554 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.6 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.044 (4)	0.2420 (16)	0.6339 (8)	0.078 (7)	0.381 (4)
O2	0.6498 (10)	0.6314 (4)	0.51784 (16)	0.0842 (18)	0.381 (4)
O3	0.3469 (11)	0.6160 (5)	0.54992 (16)	0.094 (2)	0.381 (4)
C1	0.822 (6)	0.279 (2)	0.6917 (7)	0.060 (10)*	0.381 (4)
C2	0.862 (5)	0.346 (2)	0.7232 (8)	0.068 (9)*	0.381 (4)
C3	0.798 (5)	0.326 (2)	0.7633 (8)	0.067 (8)*	0.381 (4)
H3	0.8305	0.3688	0.7845	0.080*	0.381 (4)
C4	0.683 (4)	0.2390 (19)	0.7711 (6)	0.049 (7)*	0.381 (4)
C5	0.632 (5)	0.1776 (18)	0.7388 (6)	0.059 (8)*	0.381 (4)
H5	0.5535	0.1208	0.7437	0.071*	0.381 (4)
C6	0.695 (5)	0.1989 (19)	0.6986 (7)	0.057 (8)*	0.381 (4)
C7	0.913 (4)	0.2956 (18)	0.6493 (7)	0.077 (8)*	0.381 (4)
C8	0.808 (4)	0.3710 (14)	0.6225 (6)	0.053 (8)*	0.381 (4)
C9	0.924 (3)	0.4099 (14)	0.5912 (6)	0.047 (6)*	0.381 (4)
H9	1.0621	0.3903	0.5869	0.056*	0.381 (4)
C10	0.829 (4)	0.4793 (16)	0.5661 (7)	0.051 (7)*	0.381 (4)
H10	0.9071	0.5046	0.5444	0.061*	0.381 (4)
C11	0.631 (4)	0.512 (2)	0.5713 (8)	0.058 (10)*	0.381 (4)
C12	0.509 (5)	0.468 (2)	0.6021 (8)	0.060 (8)*	0.381 (4)
H12	0.3685	0.4841	0.6054	0.071*	0.381 (4)
C13	0.604 (5)	0.398 (2)	0.6277 (9)	0.064 (9)*	0.381 (4)
H13	0.5262	0.3688	0.6486	0.077*	0.381 (4)
C14	0.5333 (16)	0.5928 (6)	0.5445 (2)	0.072 (2)	0.381 (4)
C15	1.016 (5)	0.4321 (18)	0.7150 (11)	0.076 (9)*	0.381 (4)
H15	1.0227	0.4410	0.6853	0.091*	0.381 (4)
C16	1.235 (5)	0.407 (3)	0.7292 (18)	0.107 (18)*	0.381 (4)
H16A	1.2786	0.3457	0.7168	0.161*	0.381 (4)
H16B	1.3299	0.4586	0.7213	0.161*	0.381 (4)
H16C	1.2359	0.3998	0.7584	0.161*	0.381 (4)
C17	0.932 (5)	0.5274 (19)	0.7328 (9)	0.089 (8)*	0.381 (4)
H17A	0.7927	0.5391	0.7226	0.134*	0.381 (4)
H17B	0.9278	0.5224	0.7621	0.134*	0.381 (4)
H17C	1.0217	0.5813	0.7250	0.134*	0.381 (4)
C18	0.623 (5)	0.215 (3)	0.8166 (7)	0.082 (6)*	0.381 (4)
H18	0.6400	0.1438	0.8203	0.099*	0.381 (4)
C19	0.758 (5)	0.265 (2)	0.8485 (7)	0.066 (8)*	0.381 (4)
H19A	0.9027	0.2500	0.8434	0.099*	0.381 (4)
H19B	0.7377	0.3356	0.8470	0.099*	0.381 (4)
H19C	0.7188	0.2421	0.8752	0.099*	0.381 (4)
C20	0.397 (5)	0.238 (3)	0.8236 (13)	0.103 (11)*	0.381 (4)
H20A	0.3133	0.2054	0.8031	0.155*	0.381 (4)
H20B	0.3559	0.2145	0.8502	0.155*	0.381 (4)
H20C	0.3748	0.3080	0.8220	0.155*	0.381 (4)
C21	0.632 (4)	0.1291 (18)	0.6653 (8)	0.079 (9)*	0.381 (4)
H21	0.6186	0.1661	0.6396	0.094*	0.381 (4)
C22	0.793 (4)	0.0474 (19)	0.6594 (9)	0.093 (10)*	0.381 (4)
H22A	0.7473	0.0042	0.6378	0.140*	0.381 (4)
H22B	0.9259	0.0760	0.6523	0.140*	0.381 (4)
H22C	0.8065	0.0105	0.6843	0.140*	0.381 (4)
C23	0.420 (4)	0.076 (2)	0.6746 (11)	0.085 (9)*	0.381 (4)
H23A	0.3863	0.0322	0.6524	0.128*	0.381 (4)
H23B	0.4331	0.0389	0.6995	0.128*	0.381 (4)
H23C	0.3112	0.1245	0.6775	0.128*	0.381 (4)
O1D	1.092 (4)	0.275 (3)	0.6412 (10)	0.068 (8)	0.325 (4)
O2D	0.6498 (10)	0.6314 (4)	0.51784 (16)	0.0842 (18)	0.325 (4)
O3D	0.3469 (11)	0.6160 (5)	0.54992 (16)	0.094 (2)	0.325 (4)
C1D	0.802 (6)	0.280 (3)	0.6910 (7)	0.061 (11)*	0.325 (4)
C2D	0.899 (5)	0.342 (2)	0.7178 (8)	0.060 (9)*	0.325 (4)
C3D	0.850 (5)	0.331 (2)	0.7594 (8)	0.069 (9)*	0.325 (4)
H3D	0.9157	0.3721	0.7783	0.083*	0.325 (4)
C4D	0.703 (5)	0.260 (3)	0.7738 (8)	0.068 (10)*	0.325 (4)
C5D	0.609 (7)	0.198 (3)	0.7441 (8)	0.060 (10)*	0.325 (4)
H5D	0.5097	0.1513	0.7521	0.072*	0.325 (4)
C6D	0.664 (7)	0.206 (3)	0.7029 (8)	0.060 (10)*	0.325 (4)
C7D	0.862 (4)	0.2736 (17)	0.6446 (7)	0.072 (9)*	0.325 (4)
C8D	0.769 (4)	0.3565 (18)	0.6186 (7)	0.053 (8)*	0.325 (4)
C9D	0.872 (5)	0.385 (2)	0.5827 (8)	0.060 (8)*	0.325 (4)
H9D	0.9945	0.3536	0.5746	0.072*	0.325 (4)
C10D	0.791 (5)	0.461 (2)	0.5596 (9)	0.061 (9)*	0.325 (4)
H10D	0.8611	0.4794	0.5359	0.073*	0.325 (4)
C11D	0.610 (4)	0.5107 (19)	0.5702 (9)	0.057 (11)*	0.325 (4)
C12D	0.506 (6)	0.483 (3)	0.6059 (10)	0.069 (11)*	0.325 (4)
H12D	0.3835	0.5143	0.6140	0.082*	0.325 (4)
C13D	0.590 (5)	0.406 (3)	0.6290 (11)	0.064 (11)*	0.325 (4)
H13D	0.5204	0.3873	0.6528	0.077*	0.325 (4)
C14D	0.5333 (16)	0.5928 (6)	0.5445 (2)	0.072 (2)	0.325 (4)
C15D	1.041 (4)	0.426 (2)	0.7049 (11)	0.075 (10)*	0.325 (4)
H15D	1.0737	0.4141	0.6760	0.091*	0.325 (4)
C16D	1.245 (5)	0.424 (4)	0.7266 (17)	0.059 (12)*	0.325 (4)
H16D	1.3298	0.4782	0.7175	0.089*	0.325 (4)
H16E	1.2208	0.4295	0.7556	0.089*	0.325 (4)
H16F	1.3154	0.3627	0.7209	0.089*	0.325 (4)
C17D	0.931 (6)	0.526 (2)	0.7068 (12)	0.085 (10)*	0.325 (4)
H17D	0.8003	0.5225	0.6922	0.128*	0.325 (4)
H17E	0.9043	0.5432	0.7348	0.128*	0.325 (4)
H17F	1.0189	0.5755	0.6945	0.128*	0.325 (4)
C18D	0.640 (5)	0.232 (3)	0.8183 (8)	0.085 (7)*	0.325 (4)
H18D	0.6137	0.1615	0.8133	0.102*	0.325 (4)
C19D	0.805 (5)	0.219 (3)	0.8498 (8)	0.091 (9)*	0.325 (4)
H19D	0.9355	0.2022	0.8367	0.137*	0.325 (4)
H19E	0.8222	0.2795	0.8648	0.137*	0.325 (4)
H19F	0.7656	0.1669	0.8682	0.137*	0.325 (4)
C20D	0.422 (5)	0.258 (4)	0.8305 (13)	0.094 (11)*	0.325 (4)
H20D	0.3354	0.2638	0.8065	0.141*	0.325 (4)
H20E	0.3660	0.2080	0.8481	0.141*	0.325 (4)
H20F	0.4226	0.3205	0.8447	0.141*	0.325 (4)
C21D	0.602 (6)	0.148 (2)	0.6648 (10)	0.083 (11)*	0.325 (4)
H21D	0.4789	0.1824	0.6535	0.099*	0.325 (4)
C22D	0.785 (4)	0.1705 (16)	0.6352 (7)	0.089 (9)*	0.325 (4)
H22D	0.8968	0.1229	0.6390	0.107*	0.325 (4)
H22E	0.7365	0.1666	0.6071	0.107*	0.325 (4)
C23D	0.539 (6)	0.0440 (19)	0.6696 (9)	0.104 (11)*	0.325 (4)
H23D	0.5041	0.0169	0.6433	0.157*	0.325 (4)
H23E	0.6530	0.0071	0.6813	0.157*	0.325 (4)
H23F	0.4188	0.0400	0.6873	0.157*	0.325 (4)
O1P	1.123 (6)	0.308 (3)	0.6532 (14)	0.075 (10)*	0.162 (4)
O2P	0.6498 (10)	0.6314 (4)	0.51784 (16)	0.0842 (18)	0.162 (4)
O3P	0.3469 (11)	0.6160 (5)	0.54992 (16)	0.094 (2)	0.162 (4)
C1P	0.806 (7)	0.294 (3)	0.7011 (10)	0.059 (12)*	0.162 (4)
C2P	0.875 (7)	0.346 (3)	0.7361 (10)	0.057 (12)*	0.162 (4)
C3P	0.793 (8)	0.323 (4)	0.7747 (11)	0.066 (13)*	0.162 (4)
H3P	0.8362	0.3573	0.7979	0.080*	0.162 (4)
C4P	0.646 (8)	0.248 (4)	0.7777 (11)	0.075 (14)*	0.162 (4)
C5P	0.574 (10)	0.198 (5)	0.7436 (11)	0.062 (13)*	0.162 (4)
H5P	0.4700	0.1497	0.7464	0.074*	0.162 (4)
C6P	0.656 (10)	0.219 (4)	0.7052 (12)	0.058 (13)*	0.162 (4)
C7P	0.941 (5)	0.3505 (19)	0.6710 (8)	0.053 (10)*	0.162 (4)
C8P	0.839 (5)	0.4131 (16)	0.6378 (7)	0.049 (10)*	0.162 (4)
C9P	0.954 (5)	0.458 (2)	0.6074 (9)	0.071 (11)*	0.162 (4)
H9P	1.0989	0.4487	0.6072	0.086*	0.162 (4)
C10P	0.863 (5)	0.516 (2)	0.5768 (10)	0.065 (12)*	0.162 (4)
H10P	0.9473	0.5445	0.5568	0.078*	0.162 (4)
C11P	0.649 (5)	0.5312 (11)	0.5761 (7)	0.067 (14)*	0.162 (4)
C12P	0.526 (7)	0.487 (3)	0.6068 (10)	0.066 (14)*	0.162 (4)
H12P	0.3811	0.4961	0.6071	0.079*	0.162 (4)
C13P	0.624 (6)	0.430 (3)	0.6363 (11)	0.052 (12)*	0.162 (4)
H13P	0.5401	0.4016	0.6565	0.062*	0.162 (4)
C14P	0.5333 (16)	0.5928 (6)	0.5445 (2)	0.072 (2)	0.162 (4)
C15P	0.992 (7)	0.422 (3)	0.7111 (11)	0.076 (14)*	0.162 (4)
C16P	1.228 (7)	0.434 (5)	0.7136 (18)	0.090 (18)*	0.162 (4)
H16G	1.2712	0.4859	0.6953	0.135*	0.162 (4)
H16H	1.2671	0.4509	0.7411	0.135*	0.162 (4)
H16I	1.2954	0.3733	0.7058	0.135*	0.162 (4)
C17P	0.895 (12)	0.524 (3)	0.715 (2)	0.073 (13)*	0.162 (4)
H17G	0.9733	0.5697	0.6984	0.110*	0.162 (4)
H17H	0.7521	0.5214	0.7051	0.110*	0.162 (4)
H17I	0.8965	0.5443	0.7428	0.110*	0.162 (4)
C18P	0.549 (7)	0.213 (4)	0.8177 (11)	0.082 (8)*	0.162 (4)
H18P	0.5319	0.1411	0.8168	0.098*	0.162 (4)
C19P	0.686 (9)	0.240 (6)	0.8531 (14)	0.089 (14)*	0.162 (4)
H19G	0.6231	0.2175	0.8781	0.134*	0.162 (4)
H19H	0.8214	0.2093	0.8499	0.134*	0.162 (4)
H19I	0.7034	0.3106	0.8541	0.134*	0.162 (4)
C20P	0.333 (7)	0.262 (5)	0.8157 (18)	0.070 (13)*	0.162 (4)
H20G	0.2598	0.2389	0.7919	0.106*	0.162 (4)
H20H	0.2543	0.2448	0.8398	0.106*	0.162 (4)
H20I	0.3494	0.3323	0.8143	0.106*	0.162 (4)
C21P	0.573 (8)	0.154 (4)	0.6712 (15)	0.078 (14)*	0.162 (4)
H21P	0.5364	0.1977	0.6483	0.093*	0.162 (4)
C22P	0.749 (9)	0.086 (4)	0.6564 (18)	0.076 (16)*	0.162 (4)
H22F	0.6970	0.0443	0.6348	0.115*	0.162 (4)
H22G	0.8643	0.1247	0.6464	0.115*	0.162 (4)
H22H	0.7960	0.0452	0.6787	0.115*	0.162 (4)
C23P	0.380 (9)	0.093 (6)	0.681 (3)	0.12 (3)*	0.162 (4)
H23G	0.3398	0.0545	0.6579	0.185*	0.162 (4)
H23H	0.4105	0.0495	0.7038	0.185*	0.162 (4)
H23I	0.2662	0.1362	0.6888	0.185*	0.162 (4)
O1Z	1.112 (7)	0.278 (6)	0.651 (2)	0.069 (11)*	0.132 (4)
O2Z	0.6498 (10)	0.6314 (4)	0.51784 (16)	0.0842 (18)	0.132 (4)
O3Z	0.3469 (11)	0.6160 (5)	0.54992 (16)	0.094 (2)	0.132 (4)
C6Z	0.753 (7)	0.220 (2)	0.7065 (9)	0.050 (12)*	0.132 (4)
C1Z	0.875 (6)	0.303 (2)	0.6988 (8)	0.055 (13)*	0.132 (4)
C2Z	0.907 (7)	0.372 (2)	0.7296 (10)	0.067 (14)*	0.132 (4)
C3Z	0.819 (7)	0.358 (3)	0.7681 (9)	0.077 (14)*	0.132 (4)
H3Z	0.8422	0.4052	0.7892	0.092*	0.132 (4)
C4Z	0.698 (6)	0.275 (3)	0.7758 (8)	0.066 (14)*	0.132 (4)
C5Z	0.665 (7)	0.205 (3)	0.7450 (10)	0.059 (14)*	0.132 (4)
H5Z	0.5814	0.1484	0.7502	0.071*	0.132 (4)
C7Z	0.889 (7)	0.287 (2)	0.6529 (10)	0.076 (15)*	0.132 (4)
C8Z	0.801 (8)	0.367 (3)	0.6240 (12)	0.053 (15)*	0.132 (4)
C9Z	0.888 (10)	0.383 (5)	0.5855 (16)	0.063 (14)*	0.132 (4)
H9Z	1.0044	0.3446	0.5767	0.075*	0.132 (4)
C10Z	0.804 (9)	0.454 (4)	0.5597 (13)	0.066 (14)*	0.132 (4)
H10Z	0.8637	0.4654	0.5334	0.079*	0.132 (4)
C11Z	0.634 (5)	0.5107 (15)	0.5725 (10)	0.059 (15)*	0.132 (4)
C12Z	0.546 (7)	0.496 (3)	0.6109 (12)	0.064 (14)*	0.132 (4)
H12Z	0.4296	0.5339	0.6197	0.077*	0.132 (4)
C13Z	0.630 (8)	0.423 (4)	0.6367 (11)	0.057 (13)*	0.132 (4)
H13Z	0.5703	0.4130	0.6630	0.069*	0.132 (4)
C14Z	0.5333 (16)	0.5928 (6)	0.5445 (2)	0.072 (2)	0.132 (4)
C15Z	1.032 (8)	0.462 (3)	0.7198 (19)	0.075 (14)*	0.132 (4)
H15Z	1.0605	0.4559	0.6904	0.090*	0.132 (4)
C16Z	1.239 (7)	0.452 (5)	0.739 (2)	0.11 (3)*	0.132 (4)
H16J	1.2946	0.3870	0.7338	0.162*	0.132 (4)
H16K	1.3329	0.5008	0.7283	0.162*	0.132 (4)
H16L	1.2259	0.4609	0.7683	0.162*	0.132 (4)
C17Z	0.912 (11)	0.555 (3)	0.723 (3)	0.083 (15)*	0.132 (4)
H17J	0.7811	0.5484	0.7091	0.124*	0.132 (4)
H17K	0.8848	0.5681	0.7519	0.124*	0.132 (4)
H17L	0.9919	0.6080	0.7119	0.124*	0.132 (4)
C18Z	0.611 (8)	0.266 (4)	0.8183 (11)	0.080 (9)*	0.132 (4)
H18Z	0.6005	0.1959	0.8252	0.096*	0.132 (4)
C19Z	0.789 (9)	0.311 (6)	0.8431 (17)	0.097 (14)*	0.132 (4)
H19J	0.7525	0.3098	0.8716	0.145*	0.132 (4)
H19K	0.9145	0.2725	0.8390	0.145*	0.132 (4)
H19L	0.8129	0.3776	0.8345	0.145*	0.132 (4)
C20Z	0.403 (9)	0.315 (6)	0.829 (2)	0.102 (15)*	0.132 (4)
H20J	0.3698	0.3027	0.8570	0.153*	0.132 (4)
H20K	0.4132	0.3850	0.8242	0.153*	0.132 (4)
H20L	0.2942	0.2881	0.8117	0.153*	0.132 (4)
C21Z	0.762 (7)	0.184 (2)	0.6626 (10)	0.079 (13)*	0.132 (4)
C22Z	0.898 (9)	0.091 (3)	0.6614 (17)	0.078 (17)*	0.132 (4)
H22I	0.9057	0.0670	0.6338	0.118*	0.132 (4)
H22J	1.0364	0.1067	0.6710	0.118*	0.132 (4)
H22K	0.8371	0.0412	0.6787	0.118*	0.132 (4)
C23Z	0.560 (8)	0.172 (5)	0.6381 (19)	0.12 (2)*	0.132 (4)
H23J	0.5935	0.1489	0.6111	0.183*	0.132 (4)
H23K	0.4699	0.1254	0.6514	0.183*	0.132 (4)
H23L	0.4905	0.2350	0.6362	0.183*	0.132 (4)
N1	0.0572 (10)	0.6672 (4)	0.49239 (16)	0.0679 (19)
H1A	0.1557	0.6438	0.5091	0.082*
H1B	−0.0692	0.6524	0.5023	0.082*
H1C	0.0700	0.7326	0.4904	0.082*
C24	0.2954 (16)	0.6520 (7)	0.4331 (2)	0.104 (3)
H24A	0.4041	0.6353	0.4523	0.157*
H24B	0.2961	0.7221	0.4285	0.157*
H24C	0.3197	0.6181	0.4078	0.157*
C25	0.0826 (14)	0.6211 (6)	0.4505 (2)	0.074 (2)
H25	−0.0267	0.6485	0.4327	0.089*
C26	0.048 (2)	0.5121 (8)	0.4534 (3)	0.081 (3)
C27	−0.136 (2)	0.4713 (10)	0.4398 (3)	0.109 (3)
H27	−0.2409	0.5123	0.4295	0.131*
C28	−0.169 (3)	0.3692 (13)	0.4410 (4)	0.150 (6)
H28	−0.2960	0.3422	0.4327	0.180*
C29	−0.011 (4)	0.3101 (14)	0.4544 (6)	0.183 (10)
H29	−0.0274	0.2418	0.4534	0.219*
C30	0.171 (4)	0.3487 (13)	0.4693 (5)	0.181 (7)
H30	0.2740	0.3074	0.4800	0.218*
C31	0.202 (2)	0.4503 (10)	0.4683 (3)	0.127 (4)
H31	0.3274	0.4769	0.4777	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.092 (12)	0.067 (13)	0.074 (11)	0.026 (10)	0.024 (10)	0.007 (10)
O2	0.081 (4)	0.098 (4)	0.074 (3)	−0.004 (4)	0.013 (3)	0.033 (3)
O3	0.080 (4)	0.134 (5)	0.067 (4)	0.023 (4)	−0.006 (4)	0.037 (4)
C14	0.085 (6)	0.071 (5)	0.058 (5)	0.003 (5)	−0.015 (5)	−0.001 (4)
O1D	0.073 (12)	0.062 (14)	0.068 (14)	−0.002 (12)	0.006 (11)	−0.011 (12)
O2D	0.081 (4)	0.098 (4)	0.074 (3)	−0.004 (4)	0.013 (3)	0.033 (3)
O3D	0.080 (4)	0.134 (5)	0.067 (4)	0.023 (4)	−0.006 (4)	0.037 (4)
C14D	0.085 (6)	0.071 (5)	0.058 (5)	0.003 (5)	−0.015 (5)	−0.001 (4)
O2P	0.081 (4)	0.098 (4)	0.074 (3)	−0.004 (4)	0.013 (3)	0.033 (3)
O3P	0.080 (4)	0.134 (5)	0.067 (4)	0.023 (4)	−0.006 (4)	0.037 (4)
C14P	0.085 (6)	0.071 (5)	0.058 (5)	0.003 (5)	−0.015 (5)	−0.001 (4)
O2Z	0.081 (4)	0.098 (4)	0.074 (3)	−0.004 (4)	0.013 (3)	0.033 (3)
O3Z	0.080 (4)	0.134 (5)	0.067 (4)	0.023 (4)	−0.006 (4)	0.037 (4)
C14Z	0.085 (6)	0.071 (5)	0.058 (5)	0.003 (5)	−0.015 (5)	−0.001 (4)
N1	0.073 (5)	0.085 (4)	0.045 (4)	0.004 (4)	−0.002 (4)	0.014 (3)
C24	0.114 (9)	0.138 (8)	0.062 (5)	−0.004 (7)	0.029 (6)	0.002 (6)
C25	0.078 (7)	0.094 (7)	0.050 (5)	0.001 (6)	−0.011 (5)	0.011 (5)
C26	0.102 (9)	0.093 (8)	0.047 (5)	−0.004 (8)	−0.003 (6)	−0.004 (5)
C27	0.114 (11)	0.126 (11)	0.089 (8)	−0.004 (9)	0.015 (7)	−0.023 (7)
C28	0.168 (17)	0.133 (14)	0.150 (13)	−0.046 (12)	0.031 (12)	−0.039 (11)
C29	0.30 (3)	0.103 (13)	0.149 (15)	−0.019 (16)	0.033 (18)	−0.025 (11)
C30	0.28 (2)	0.113 (15)	0.154 (14)	0.029 (14)	−0.028 (15)	0.002 (10)
C31	0.172 (14)	0.101 (10)	0.109 (9)	0.008 (10)	−0.025 (9)	−0.003 (7)

Geometric parameters (Å, º)

O1—C7	1.22 (2)	C4P—C18P	1.52 (2)
O2—C14	1.258 (9)	C5P—C6P	1.39 (2)
O3—C14	1.240 (9)	C5P—H5P	0.9300
C1—C6	1.373 (19)	C6P—C21P	1.51 (2)
C1—C2	1.40 (2)	C7P—C8P	1.52 (2)
C1—C7	1.515 (19)	C7P—C15P	1.66 (2)
C2—C3	1.40 (2)	C8P—C9P	1.37 (2)
C2—C15	1.54 (2)	C8P—C13P	1.39 (2)
C3—C4	1.40 (2)	C9P—C10P	1.40 (2)
C3—H3	0.9300	C9P—H9P	0.9300
C4—C5	1.38 (2)	C10P—C11P	1.38 (2)
C4—C18	1.57 (2)	C10P—H10P	0.9300
C5—C6	1.402 (19)	C11P—C12P	1.40 (2)
C5—H5	0.9300	C11P—C14P	1.52 (2)
C6—C21	1.50 (2)	C12P—C13P	1.38 (2)
C7—C8	1.500 (19)	C12P—H12P	0.9300
C8—C13	1.36 (2)	C13P—H13P	0.9300
C8—C9	1.365 (18)	C15P—C16P	1.51 (3)
C9—C10	1.384 (18)	C15P—C17P	1.52 (2)
C9—H9	0.9300	C16P—H16G	0.9600
C10—C11	1.35 (2)	C16P—H16H	0.9600
C10—H10	0.9300	C16P—H16I	0.9600
C11—C12	1.41 (2)	C17P—H17G	0.9600
C11—C14	1.527 (18)	C17P—H17H	0.9600
C12—C13	1.40 (2)	C17P—H17I	0.9600
C12—H12	0.9300	C18P—C19P	1.50 (3)
C13—H13	0.9300	C18P—C20P	1.52 (3)
C15—C16	1.51 (2)	C18P—H18P	0.9800
C15—C17	1.51 (2)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C23P	1.52 (3)
C17—H17C	0.9600	C21P—C22P	1.53 (3)
C18—C20	1.49 (2)	C21P—H21P	0.9800
C18—C19	1.51 (2)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (3)
C20—H20C	0.9600	O2Z—C14Z	1.258 (9)
C21—C22	1.52 (2)	O3Z—C14Z	1.240 (9)
C21—C23	1.56 (2)	C6Z—C5Z	1.3894
C21—H21	0.9800	C6Z—C1Z	1.3922
C22—H22A	0.9600	C6Z—C21Z	1.51 (2)
C22—H22B	0.9600	C1Z—C2Z	1.3890
C22—H22C	0.9600	C1Z—C7Z	1.52 (2)
C23—H23A	0.9600	C2Z—C3Z	1.3895
C23—H23B	0.9600	C2Z—C15Z	1.48 (2)
C23—H23C	0.9600	C3Z—C4Z	1.3886
O1D—C7D	1.47 (2)	C3Z—H3Z	0.9503
O2D—C14D	1.258 (9)	C4Z—C5Z	1.3900
O3D—C14D	1.240 (9)	C4Z—C18Z	1.50 (2)
C1D—C2D	1.36 (2)	C5Z—H5Z	0.9508
C1D—C6D	1.38 (2)	C7Z—C8Z	1.55 (2)
C1D—C7D	1.57 (2)	C7Z—C21Z	1.65 (2)
C2D—C3D	1.40 (2)	C8Z—C13Z	1.3906
C2D—C15D	1.51 (2)	C8Z—C9Z	1.3919
C3D—C4D	1.42 (2)	C9Z—C10Z	1.3876
C3D—H3D	0.9300	C9Z—H9Z	0.9485
C4D—C5D	1.41 (2)	C10Z—C11Z	1.3920
C4D—C18D	1.56 (2)	C10Z—H10Z	0.9501
C5D—C6D	1.39 (2)	C11Z—C12Z	1.3870
C5D—H5D	0.9300	C11Z—C14Z	1.573 (19)
C6D—C21D	1.52 (2)	C12Z—C13Z	1.3947
C7D—C22D	1.51 (2)	C12Z—H12Z	0.9481
C7D—C8D	1.52 (2)	C13Z—H13Z	0.9480
C8D—C13D	1.36 (2)	C15Z—C16Z	1.47 (3)
C8D—C9D	1.40 (2)	C15Z—C17Z	1.47 (3)
C9D—C10D	1.37 (2)	C15Z—H15Z	0.9800
C9D—H9D	0.9300	C16Z—H16J	0.9600
C10D—C11D	1.38 (2)	C16Z—H16K	0.9600
C10D—H10D	0.9300	C16Z—H16L	0.9600
C11D—C12D	1.39 (2)	C17Z—H17J	0.9600
C11D—C14D	1.475 (18)	C17Z—H17K	0.9600
C12D—C13D	1.39 (2)	C17Z—H17L	0.9600
C12D—H12D	0.9300	C18Z—C20Z	1.52 (3)
C13D—H13D	0.9300	C18Z—C19Z	1.52 (3)
C15D—C16D	1.48 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.53 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C23Z	1.52 (2)
C17D—H17F	0.9600	C21Z—C22Z	1.52 (2)
C18D—C19D	1.48 (2)	C22Z—H22I	0.9600
C18D—C20D	1.49 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.513 (9)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.47 (2)	N1—H1C	0.8900
C21D—C22D	1.54 (2)	C24—C25	1.527 (11)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.493 (12)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C27	1.369 (14)
O1P—C7P	1.42 (2)	C26—C31	1.375 (14)
O2P—C14P	1.258 (9)	C27—C28	1.396 (15)
O3P—C14P	1.240 (9)	C27—H27	0.9300
C1P—C6P	1.40 (2)	C28—C29	1.36 (2)
C1P—C2P	1.41 (2)	C28—H28	0.9300
C1P—C7P	1.51 (2)	C29—C30	1.36 (2)
C2P—C3P	1.40 (2)	C29—H29	0.9300
C2P—C15P	1.51 (2)	C30—C31	1.387 (17)
C3P—C4P	1.38 (2)	C30—H30	0.9300
C3P—H3P	0.9300	C31—H31	0.9300
C4P—C5P	1.38 (2)
C6—C1—C2	119.9 (18)	C1P—C7P—C8P	120 (2)
C6—C1—C7	119.3 (19)	O1P—C7P—C15P	113 (3)
C2—C1—C7	120.8 (19)	C1P—C7P—C15P	83.6 (17)
C1—C2—C3	120.6 (19)	C8P—C7P—C15P	109.0 (17)
C1—C2—C15	118 (2)	C9P—C8P—C13P	115 (2)
C3—C2—C15	120 (2)	C9P—C8P—C7P	122 (2)
C2—C3—C4	119 (2)	C13P—C8P—C7P	123 (2)
C2—C3—H3	120.3	C8P—C9P—C10P	123 (3)
C4—C3—H3	120.3	C8P—C9P—H9P	118.6
C5—C4—C3	118.8 (18)	C10P—C9P—H9P	118.6
C5—C4—C18	123.1 (19)	C11P—C10P—C9P	120 (3)
C3—C4—C18	118.1 (19)	C11P—C10P—H10P	119.8
C4—C5—C6	121.7 (19)	C9P—C10P—H10P	119.8
C4—C5—H5	119.2	C10P—C11P—C12P	119 (2)
C6—C5—H5	119.2	C10P—C11P—C14P	125 (2)
C1—C6—C5	119.1 (18)	C12P—C11P—C14P	117 (2)
C1—C6—C21	122.5 (18)	C13P—C12P—C11P	119 (3)
C5—C6—C21	118.3 (18)	C13P—C12P—H12P	120.6
O1—C7—C8	117.9 (19)	C11P—C12P—H12P	120.6
O1—C7—C1	124 (2)	C12P—C13P—C8P	124 (3)
C8—C7—C1	118 (2)	C12P—C13P—H13P	118.0
C13—C8—C9	120.4 (18)	C8P—C13P—H13P	118.0
C13—C8—C7	122.1 (19)	O3P—C14P—O2P	123.9 (7)
C9—C8—C7	117.4 (18)	O3P—C14P—C11P	120.5 (16)
C8—C9—C10	118.1 (18)	O2P—C14P—C11P	114.4 (16)
C8—C9—H9	120.9	C2P—C15P—C16P	123 (3)
C10—C9—H9	120.9	C2P—C15P—C17P	112 (3)
C11—C10—C9	123.7 (19)	C16P—C15P—C17P	107 (3)
C11—C10—H10	118.1	C2P—C15P—C7P	86.3 (18)
C9—C10—H10	118.1	C16P—C15P—C7P	108 (3)
C10—C11—C12	117.6 (17)	C17P—C15P—C7P	120 (3)
C10—C11—C14	122.9 (18)	C15P—C16P—H16G	109.5
C12—C11—C14	119.5 (18)	C15P—C16P—H16H	109.5
C13—C12—C11	119 (2)	H16G—C16P—H16H	109.5
C13—C12—H12	120.7	C15P—C16P—H16I	109.5
C11—C12—H12	120.7	H16G—C16P—H16I	109.5
C8—C13—C12	121 (2)	H16H—C16P—H16I	109.5
C8—C13—H13	119.4	C15P—C17P—H17G	109.5
C12—C13—H13	119.4	C15P—C17P—H17H	109.5
O3—C14—O2	123.9 (7)	H17G—C17P—H17H	109.5
O3—C14—C11	119.2 (13)	C15P—C17P—H17I	109.5
O2—C14—C11	116.9 (13)	H17G—C17P—H17I	109.5
C16—C15—C17	114 (3)	H17H—C17P—H17I	109.5
C16—C15—C2	111 (2)	C19P—C18P—C4P	110 (3)
C17—C15—C2	110 (2)	C19P—C18P—C20P	117 (4)
C16—C15—H15	107.0	C4P—C18P—C20P	101 (3)
C17—C15—H15	107.0	C19P—C18P—H18P	109.2
C2—C15—H15	107.0	C4P—C18P—H18P	109.2
C15—C16—H16A	109.5	C20P—C18P—H18P	109.2
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C20—C18—C19	111 (3)	H20H—C20P—H20I	109.5
C20—C18—C4	110 (2)	C6P—C21P—C23P	116 (3)
C19—C18—C4	115 (2)	C6P—C21P—C22P	109 (3)
C20—C18—H18	106.9	C23P—C21P—C22P	109 (3)
C19—C18—H18	106.9	C6P—C21P—H21P	107.3
C4—C18—H18	106.9	C23P—C21P—H21P	107.3
C18—C19—H19A	109.5	C22P—C21P—H21P	107.3
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C6—C21—C22	112 (2)	H23H—C23P—H23I	109.5
C6—C21—C23	112 (2)	C5Z—C6Z—C1Z	120.0
C22—C21—C23	106 (2)	C5Z—C6Z—C21Z	145.8 (18)
C6—C21—H21	108.9	C1Z—C6Z—C21Z	93.9 (17)
C22—C21—H21	108.9	C2Z—C1Z—C6Z	119.8
C23—C21—H21	108.9	C2Z—C1Z—C7Z	143.4 (17)
C21—C22—H22A	109.5	C6Z—C1Z—C7Z	95.5 (17)
C21—C22—H22B	109.5	C1Z—C2Z—C3Z	120.20 (7)
H22A—C22—H22B	109.5	C1Z—C2Z—C15Z	118 (2)
C21—C22—H22C	109.5	C3Z—C2Z—C15Z	122 (2)
H22A—C22—H22C	109.5	C4Z—C3Z—C2Z	119.9
H22B—C22—H22C	109.5	C4Z—C3Z—H3Z	120.0
C21—C23—H23A	109.5	C2Z—C3Z—H3Z	120.0
C21—C23—H23B	109.5	C3Z—C4Z—C5Z	120.0
H23A—C23—H23B	109.5	C3Z—C4Z—C18Z	116 (2)
C21—C23—H23C	109.5	C5Z—C4Z—C18Z	124 (2)
H23A—C23—H23C	109.5	C6Z—C5Z—C4Z	120.05 (7)
H23B—C23—H23C	109.5	C6Z—C5Z—H5Z	120.0
C2D—C1D—C6D	123 (2)	C4Z—C5Z—H5Z	120.0
C2D—C1D—C7D	123 (2)	O1Z—C7Z—C1Z	97 (3)
C6D—C1D—C7D	112.9 (17)	O1Z—C7Z—C8Z	113 (3)
C1D—C2D—C3D	117 (2)	C1Z—C7Z—C8Z	119 (3)
C1D—C2D—C15D	124 (2)	O1Z—C7Z—C21Z	115 (3)
C3D—C2D—C15D	119 (2)	C1Z—C7Z—C21Z	84.3 (17)
C2D—C3D—C4D	122 (2)	C8Z—C7Z—C21Z	122 (2)
C2D—C3D—H3D	118.8	C13Z—C8Z—C9Z	120.1
C4D—C3D—H3D	118.8	C13Z—C8Z—C7Z	119 (2)
C5D—C4D—C3D	117 (2)	C9Z—C8Z—C7Z	121 (2)
C5D—C4D—C18D	113 (2)	C10Z—C9Z—C8Z	120.0
C3D—C4D—C18D	130 (2)	C10Z—C9Z—H9Z	119.8
C6D—C5D—C4D	120 (2)	C8Z—C9Z—H9Z	120.2
C6D—C5D—H5D	119.8	C9Z—C10Z—C11Z	119.9
C4D—C5D—H5D	119.8	C9Z—C10Z—H10Z	120.4
C1D—C6D—C5D	119 (2)	C11Z—C10Z—H10Z	119.8
C1D—C6D—C21D	107.7 (17)	C12Z—C11Z—C10Z	120.4
C5D—C6D—C21D	133 (2)	C12Z—C11Z—C14Z	118 (2)
O1D—C7D—C22D	109 (2)	C10Z—C11Z—C14Z	122 (2)
O1D—C7D—C8D	110 (2)	C11Z—C12Z—C13Z	119.8
C22D—C7D—C8D	116 (2)	C11Z—C12Z—H12Z	120.5
O1D—C7D—C1D	108 (2)	C13Z—C12Z—H12Z	119.7
C22D—C7D—C1D	99.6 (16)	C8Z—C13Z—C12Z	119.9
C8D—C7D—C1D	114 (2)	C8Z—C13Z—H13Z	120.1
C13D—C8D—C9D	117.5 (19)	C12Z—C13Z—H13Z	120.0
C13D—C8D—C7D	123 (2)	O3Z—C14Z—O2Z	123.9 (7)
C9D—C8D—C7D	119.4 (19)	O3Z—C14Z—C11Z	118.9 (16)
C10D—C9D—C8D	120 (2)	O2Z—C14Z—C11Z	117.2 (16)
C10D—C9D—H9D	120.2	C16Z—C15Z—C17Z	120 (4)
C8D—C9D—H9D	120.2	C16Z—C15Z—C2Z	108 (3)
C9D—C10D—C11D	123 (2)	C17Z—C15Z—C2Z	114 (3)
C9D—C10D—H10D	118.6	C16Z—C15Z—H15Z	104.2
C11D—C10D—H10D	118.6	C17Z—C15Z—H15Z	104.2
C10D—C11D—C12D	118 (2)	C2Z—C15Z—H15Z	104.2
C10D—C11D—C14D	120 (2)	C15Z—C16Z—H16J	109.5
C12D—C11D—C14D	122 (2)	C15Z—C16Z—H16K	109.5
C13D—C12D—C11D	118 (3)	H16J—C16Z—H16K	109.5
C13D—C12D—H12D	120.8	C15Z—C16Z—H16L	109.5
C11D—C12D—H12D	120.8	H16J—C16Z—H16L	109.5
C8D—C13D—C12D	124 (3)	H16K—C16Z—H16L	109.5
C8D—C13D—H13D	118.2	C15Z—C17Z—H17J	109.5
C12D—C13D—H13D	118.2	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	123.9 (7)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	115.3 (13)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	120.7 (13)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	112 (2)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	114 (3)	C4Z—C18Z—C20Z	120 (3)
C2D—C15D—C17D	112 (2)	C4Z—C18Z—C19Z	101 (3)
C16D—C15D—H15D	106.0	C20Z—C18Z—C19Z	111 (3)
C2D—C15D—H15D	106.0	C4Z—C18Z—H18Z	108.1
C17D—C15D—H15D	106.0	C20Z—C18Z—H18Z	108.1
C15D—C16D—H16D	109.5	C19Z—C18Z—H18Z	108.1
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C19D—C18D—C20D	120 (2)	H20K—C20Z—H20L	109.5
C19D—C18D—C4D	119 (2)	C6Z—C21Z—C23Z	120 (3)
C20D—C18D—C4D	116 (3)	C6Z—C21Z—C22Z	108 (3)
C19D—C18D—H18D	96.9	C23Z—C21Z—C22Z	112 (3)
C20D—C18D—H18D	96.9	C6Z—C21Z—C7Z	85.9 (17)
C4D—C18D—H18D	96.9	C23Z—C21Z—C7Z	114 (3)
C18D—C19D—H19D	109.5	C22Z—C21Z—C7Z	114 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	119 (3)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	117 (3)	C25—N1—H1A	109.5
C6D—C21D—C22D	102.5 (19)	C25—N1—H1B	109.5
C23D—C21D—H21D	105.9	H1A—N1—H1B	109.5
C6D—C21D—H21D	105.9	C25—N1—H1C	109.5
C22D—C21D—H21D	105.9	H1A—N1—H1C	109.5
C7D—C22D—C21D	107.3 (17)	H1B—N1—H1C	109.5
C7D—C22D—H22D	110.2	C25—C24—H24A	109.5
C21D—C22D—H22D	110.2	C25—C24—H24B	109.5
C7D—C22D—H22E	110.2	H24A—C24—H24B	109.5
C21D—C22D—H22E	110.2	C25—C24—H24C	109.5
H22D—C22D—H22E	108.5	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	109.4 (6)
H23D—C23D—H23E	109.5	C26—C25—C24	115.2 (8)
C21D—C23D—H23F	109.5	N1—C25—C24	108.5 (7)
H23D—C23D—H23F	109.5	C26—C25—H25	107.8
H23E—C23D—H23F	109.5	N1—C25—H25	107.8
C6P—C1P—C2P	120 (2)	C24—C25—H25	107.8
C6P—C1P—C7P	144 (3)	C27—C26—C31	118.6 (10)
C2P—C1P—C7P	95.8 (19)	C27—C26—C25	120.2 (11)
C3P—C2P—C1P	120 (2)	C31—C26—C25	121.2 (11)
C3P—C2P—C15P	145 (3)	C26—C27—C28	121.1 (13)
C1P—C2P—C15P	93 (2)	C26—C27—H27	119.5
C4P—C3P—C2P	119 (3)	C28—C27—H27	119.5
C4P—C3P—H3P	120.7	C29—C28—C27	118.8 (18)
C2P—C3P—H3P	120.7	C29—C28—H28	120.6
C3P—C4P—C5P	122 (3)	C27—C28—H28	120.6
C3P—C4P—C18P	124 (3)	C28—C29—C30	121 (2)
C5P—C4P—C18P	114 (3)	C28—C29—H29	119.3
C4P—C5P—C6P	120 (3)	C30—C29—H29	119.3
C4P—C5P—H5P	120.1	C29—C30—C31	119 (2)
C6P—C5P—H5P	120.1	C29—C30—H30	120.3
C5P—C6P—C1P	120 (3)	C31—C30—H30	120.3
C5P—C6P—C21P	114 (3)	C26—C31—C30	120.7 (15)
C1P—C6P—C21P	126 (3)	C26—C31—H31	119.7
O1P—C7P—C1P	122 (3)	C30—C31—H31	119.7
O1P—C7P—C8P	106 (2)

(920minUV)

Crystal data

C31H39NO3	Dx = 1.121 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2080 reflections
a = 6.3696 (5) Å	θ = 1.6–18.8°
b = 13.4941 (10) Å	µ = 0.07 mm^−1
c = 32.6553 (15) Å	T = 299 K
V = 2806.8 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5426 independent reflections
Radiation source: fine-focus sealed tube	1914 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→16
Tmin = 0.843, Tmax = 1.000	l = −40→40
25014 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.094	H-atom parameters constrained
wR(F^2) = 0.182	w = 1/[σ^2(Fo^2) + (0.0212P)^2 + 1.2062P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5426 reflections	Δρmax = 0.13 e Å^−3
476 parameters	Δρmin = −0.15 e Å^−3
557 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.2 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.043 (5)	0.243 (2)	0.6356 (12)	0.079 (8)	0.329 (4)
O2	0.6520 (10)	0.6320 (4)	0.51798 (16)	0.0819 (18)	0.329 (4)
O3	0.3506 (11)	0.6158 (5)	0.54976 (17)	0.096 (2)	0.329 (4)
C1	0.813 (8)	0.284 (3)	0.6915 (8)	0.065 (11)*	0.329 (4)
C2	0.853 (6)	0.348 (2)	0.7237 (9)	0.062 (10)*	0.329 (4)
C3	0.796 (6)	0.325 (3)	0.7640 (9)	0.076 (10)*	0.329 (4)
H3	0.8315	0.3675	0.7852	0.091*	0.329 (4)
C4	0.686 (5)	0.238 (2)	0.7722 (7)	0.054 (9)*	0.329 (4)
C5	0.637 (6)	0.178 (2)	0.7393 (7)	0.062 (9)*	0.329 (4)
H5	0.5605	0.1201	0.7441	0.075*	0.329 (4)
C6	0.696 (6)	0.200 (2)	0.6993 (8)	0.062 (10)*	0.329 (4)
C7	0.904 (5)	0.295 (2)	0.6488 (8)	0.072 (9)*	0.329 (4)
C8	0.801 (5)	0.368 (2)	0.6208 (8)	0.051 (10)*	0.329 (4)
C9	0.923 (4)	0.4083 (18)	0.5905 (7)	0.047 (7)*	0.329 (4)
H9	1.0613	0.3885	0.5864	0.057*	0.329 (4)
C10	0.830 (5)	0.4798 (19)	0.5666 (9)	0.055 (8)*	0.329 (4)
H10	0.9085	0.5070	0.5454	0.066*	0.329 (4)
C11	0.631 (5)	0.513 (2)	0.5717 (9)	0.059 (11)*	0.329 (4)
C12	0.509 (6)	0.467 (2)	0.6016 (9)	0.060 (9)*	0.329 (4)
H12	0.3689	0.4849	0.6049	0.072*	0.329 (4)
C13	0.597 (6)	0.394 (2)	0.6264 (10)	0.063 (10)*	0.329 (4)
H13	0.5175	0.3642	0.6467	0.076*	0.329 (4)
C14	0.5366 (16)	0.5933 (6)	0.5449 (2)	0.071 (2)	0.329 (4)
C15	1.010 (5)	0.434 (2)	0.7170 (12)	0.079 (10)*	0.329 (4)
H15	1.0164	0.4449	0.6874	0.094*	0.329 (4)
C16	1.230 (5)	0.406 (4)	0.730 (2)	0.11 (2)*	0.329 (4)
H16A	1.2699	0.3453	0.7171	0.164*	0.329 (4)
H16B	1.3250	0.4579	0.7221	0.164*	0.329 (4)
H16C	1.2337	0.3983	0.7592	0.164*	0.329 (4)
C17	0.932 (6)	0.529 (2)	0.7358 (11)	0.114 (13)*	0.329 (4)
H17A	0.7923	0.5419	0.7263	0.172*	0.329 (4)
H17B	0.9317	0.5227	0.7651	0.172*	0.329 (4)
H17C	1.0230	0.5823	0.7279	0.172*	0.329 (4)
C18	0.635 (5)	0.210 (3)	0.8175 (7)	0.077 (10)*	0.329 (4)
H18	0.6512	0.1376	0.8200	0.092*	0.329 (4)
C19	0.782 (6)	0.257 (3)	0.8484 (9)	0.072 (11)*	0.329 (4)
H19A	0.9249	0.2408	0.8414	0.108*	0.329 (4)
H19B	0.7644	0.3274	0.8480	0.108*	0.329 (4)
H19C	0.7517	0.2320	0.8753	0.108*	0.329 (4)
C20	0.414 (6)	0.233 (4)	0.8275 (16)	0.115 (17)*	0.329 (4)
H20A	0.3237	0.2022	0.8076	0.172*	0.329 (4)
H20B	0.3815	0.2078	0.8542	0.172*	0.329 (4)
H20C	0.3941	0.3032	0.8270	0.172*	0.329 (4)
C21	0.649 (5)	0.129 (2)	0.6646 (9)	0.074 (10)*	0.329 (4)
H21	0.6329	0.1661	0.6390	0.089*	0.329 (4)
C22	0.825 (5)	0.055 (2)	0.6603 (13)	0.109 (13)*	0.329 (4)
H22A	0.7944	0.0103	0.6382	0.164*	0.329 (4)
H22B	0.9537	0.0894	0.6547	0.164*	0.329 (4)
H22C	0.8392	0.0182	0.6853	0.164*	0.329 (4)
C23	0.439 (5)	0.073 (2)	0.6746 (12)	0.082 (11)*	0.329 (4)
H23A	0.3270	0.1200	0.6773	0.123*	0.329 (4)
H23B	0.4072	0.0275	0.6528	0.123*	0.329 (4)
H23C	0.4549	0.0369	0.6998	0.123*	0.329 (4)
O1D	1.096 (4)	0.271 (3)	0.6401 (12)	0.075 (9)	0.338 (4)
O2D	0.6520 (10)	0.6320 (4)	0.51798 (16)	0.0819 (18)	0.338 (4)
O3D	0.3506 (11)	0.6158 (5)	0.54976 (17)	0.096 (2)	0.338 (4)
C1D	0.807 (7)	0.279 (3)	0.6910 (7)	0.062 (10)*	0.338 (4)
C2D	0.897 (5)	0.342 (2)	0.7183 (7)	0.055 (8)*	0.338 (4)
C3D	0.843 (5)	0.333 (2)	0.7596 (8)	0.066 (8)*	0.338 (4)
H3D	0.9074	0.3739	0.7787	0.079*	0.338 (4)
C4D	0.692 (6)	0.262 (3)	0.7730 (8)	0.070 (10)*	0.338 (4)
C5D	0.601 (7)	0.200 (3)	0.7435 (8)	0.061 (10)*	0.338 (4)
H5D	0.5012	0.1534	0.7513	0.074*	0.338 (4)
C6D	0.662 (8)	0.208 (3)	0.7027 (8)	0.059 (10)*	0.338 (4)
C7D	0.869 (4)	0.2717 (18)	0.6448 (7)	0.079 (10)*	0.338 (4)
C8D	0.775 (5)	0.358 (2)	0.6202 (9)	0.061 (10)*	0.338 (4)
C9D	0.878 (5)	0.385 (2)	0.5842 (8)	0.061 (9)*	0.338 (4)
H9D	1.0027	0.3542	0.5767	0.073*	0.338 (4)
C10D	0.794 (4)	0.459 (2)	0.5602 (9)	0.059 (9)*	0.338 (4)
H10D	0.8642	0.4760	0.5363	0.071*	0.338 (4)
C11D	0.610 (4)	0.5079 (18)	0.5695 (9)	0.061 (10)*	0.338 (4)
C12D	0.510 (6)	0.479 (3)	0.6056 (10)	0.069 (11)*	0.338 (4)
H12D	0.3859	0.5100	0.6133	0.083*	0.338 (4)
C13D	0.594 (6)	0.405 (3)	0.6303 (11)	0.060 (10)*	0.338 (4)
H13D	0.5243	0.3872	0.6542	0.073*	0.338 (4)
C14D	0.5366 (16)	0.5933 (6)	0.5449 (2)	0.071 (2)	0.338 (4)
C15D	1.036 (5)	0.429 (2)	0.7057 (11)	0.080 (10)*	0.338 (4)
H15D	1.0603	0.4253	0.6761	0.096*	0.338 (4)
C16D	1.239 (4)	0.425 (3)	0.7269 (17)	0.058 (11)*	0.338 (4)
H16D	1.3238	0.4797	0.7186	0.087*	0.338 (4)
H16E	1.2161	0.4274	0.7560	0.087*	0.338 (4)
H16F	1.3090	0.3638	0.7201	0.087*	0.338 (4)
C17D	0.919 (5)	0.5273 (19)	0.7157 (12)	0.055 (9)*	0.338 (4)
H17D	0.7869	0.5287	0.7016	0.082*	0.338 (4)
H17E	0.8949	0.5314	0.7447	0.082*	0.338 (4)
H17F	1.0032	0.5825	0.7071	0.082*	0.338 (4)
C18D	0.625 (6)	0.240 (3)	0.8178 (8)	0.094 (11)*	0.338 (4)
H18D	0.5977	0.1701	0.8118	0.113*	0.338 (4)
C19D	0.776 (6)	0.216 (2)	0.8508 (9)	0.102 (13)*	0.338 (4)
H19D	0.9124	0.2049	0.8392	0.153*	0.338 (4)
H19E	0.7824	0.2698	0.8699	0.153*	0.338 (4)
H19F	0.7304	0.1570	0.8648	0.153*	0.338 (4)
C20D	0.402 (6)	0.260 (4)	0.8279 (15)	0.096 (16)*	0.338 (4)
H20D	0.3261	0.2746	0.8032	0.144*	0.338 (4)
H20E	0.3418	0.2032	0.8409	0.144*	0.338 (4)
H20F	0.3938	0.3161	0.8460	0.144*	0.338 (4)
C21D	0.597 (6)	0.151 (2)	0.6644 (9)	0.078 (10)*	0.338 (4)
H21D	0.4741	0.1845	0.6529	0.094*	0.338 (4)
C22D	0.783 (4)	0.1704 (16)	0.6351 (7)	0.080 (8)*	0.338 (4)
H22D	0.8903	0.1205	0.6388	0.096*	0.338 (4)
H22E	0.7352	0.1680	0.6069	0.096*	0.338 (4)
C23D	0.539 (6)	0.044 (2)	0.6699 (10)	0.126 (14)*	0.338 (4)
H23D	0.5007	0.0164	0.6438	0.189*	0.338 (4)
H23E	0.6558	0.0087	0.6810	0.189*	0.338 (4)
H23F	0.4215	0.0395	0.6883	0.189*	0.338 (4)
O1P	1.114 (7)	0.301 (3)	0.6508 (16)	0.078 (9)	0.204 (4)
O2P	0.6520 (10)	0.6320 (4)	0.51798 (16)	0.0819 (18)	0.204 (4)
O3P	0.3506 (11)	0.6158 (5)	0.54976 (17)	0.096 (2)	0.204 (4)
C1P	0.804 (7)	0.291 (3)	0.7004 (10)	0.054 (11)*	0.204 (4)
C2P	0.868 (7)	0.348 (3)	0.7344 (10)	0.060 (12)*	0.204 (4)
C3P	0.787 (8)	0.325 (4)	0.7732 (11)	0.073 (12)*	0.204 (4)
H3P	0.8258	0.3606	0.7963	0.088*	0.204 (4)
C4P	0.648 (7)	0.246 (4)	0.7758 (10)	0.064 (12)*	0.204 (4)
C5P	0.581 (10)	0.190 (5)	0.7428 (11)	0.057 (13)*	0.204 (4)
H5P	0.4857	0.1387	0.7462	0.068*	0.204 (4)
C6P	0.662 (10)	0.213 (4)	0.7042 (11)	0.057 (13)*	0.204 (4)
C7P	0.939 (5)	0.3451 (18)	0.6697 (7)	0.069 (10)*	0.204 (4)
C8P	0.838 (5)	0.4082 (17)	0.6362 (7)	0.056 (9)*	0.204 (4)
C9P	0.955 (5)	0.450 (2)	0.6055 (8)	0.072 (11)*	0.204 (4)
H9P	1.0992	0.4380	0.6046	0.086*	0.204 (4)
C10P	0.862 (5)	0.509 (2)	0.5755 (9)	0.072 (12)*	0.204 (4)
H10P	0.9453	0.5359	0.5548	0.086*	0.204 (4)
C11P	0.650 (5)	0.5292 (12)	0.5761 (7)	0.059 (12)*	0.204 (4)
C12P	0.529 (6)	0.488 (3)	0.6077 (10)	0.062 (12)*	0.204 (4)
H12P	0.3860	0.5011	0.6090	0.075*	0.204 (4)
C13P	0.624 (5)	0.429 (3)	0.6370 (10)	0.058 (11)*	0.204 (4)
H13P	0.5426	0.4020	0.6578	0.069*	0.204 (4)
C14P	0.5366 (16)	0.5933 (6)	0.5449 (2)	0.071 (2)	0.204 (4)
C15P	0.995 (6)	0.419 (2)	0.7091 (10)	0.072 (13)*	0.204 (4)
C16P	1.230 (6)	0.429 (5)	0.7125 (16)	0.11 (2)*	0.204 (4)
H16G	1.2785	0.4788	0.6936	0.163*	0.204 (4)
H16H	1.2666	0.4486	0.7399	0.163*	0.204 (4)
H16I	1.2958	0.3670	0.7062	0.163*	0.204 (4)
C17P	0.913 (10)	0.524 (3)	0.7024 (17)	0.12 (2)*	0.204 (4)
H17G	1.0105	0.5607	0.6857	0.177*	0.204 (4)
H17H	0.7790	0.5219	0.6889	0.177*	0.204 (4)
H17I	0.8979	0.5570	0.7284	0.177*	0.204 (4)
C18P	0.558 (6)	0.215 (4)	0.8171 (10)	0.078 (12)*	0.204 (4)
H18P	0.5581	0.1432	0.8203	0.094*	0.204 (4)
C19P	0.684 (7)	0.266 (4)	0.8511 (13)	0.081 (16)*	0.204 (4)
H19G	0.8234	0.2392	0.8517	0.122*	0.204 (4)
H19H	0.6894	0.3357	0.8461	0.122*	0.204 (4)
H19I	0.6164	0.2538	0.8770	0.122*	0.204 (4)
C20P	0.336 (5)	0.257 (4)	0.8159 (14)	0.065 (14)*	0.204 (4)
H20G	0.2655	0.2412	0.8410	0.097*	0.204 (4)
H20H	0.3418	0.3274	0.8125	0.097*	0.204 (4)
H20I	0.2615	0.2279	0.7933	0.097*	0.204 (4)
C21P	0.576 (7)	0.149 (3)	0.6701 (13)	0.070 (12)*	0.204 (4)
H21P	0.5544	0.1908	0.6459	0.084*	0.204 (4)
C22P	0.731 (8)	0.066 (4)	0.6584 (17)	0.088 (15)*	0.204 (4)
H22F	0.6719	0.0266	0.6368	0.132*	0.204 (4)
H22G	0.8606	0.0947	0.6494	0.132*	0.204 (4)
H22H	0.7567	0.0248	0.6819	0.132*	0.204 (4)
C23P	0.367 (7)	0.097 (4)	0.6801 (18)	0.107 (19)*	0.204 (4)
H23G	0.3238	0.0580	0.6570	0.161*	0.204 (4)
H23H	0.3853	0.0551	0.7035	0.161*	0.204 (4)
H23I	0.2620	0.1462	0.6859	0.161*	0.204 (4)
O1Z	1.117 (7)	0.281 (6)	0.653 (2)	0.077 (11)*	0.128 (4)
O2Z	0.6520 (10)	0.6320 (4)	0.51798 (16)	0.0819 (18)	0.128 (4)
O3Z	0.3506 (11)	0.6158 (5)	0.54976 (17)	0.096 (2)	0.128 (4)
C6Z	0.761 (7)	0.219 (3)	0.7070 (9)	0.051 (13)*	0.128 (4)
C1Z	0.881 (6)	0.303 (3)	0.6993 (9)	0.053 (13)*	0.128 (4)
C2Z	0.916 (7)	0.372 (3)	0.7302 (11)	0.069 (14)*	0.128 (4)
C3Z	0.831 (7)	0.357 (3)	0.7689 (10)	0.080 (14)*	0.128 (4)
H3Z	0.8554	0.4036	0.7901	0.096*	0.128 (4)
C4Z	0.712 (6)	0.273 (3)	0.7767 (9)	0.067 (14)*	0.128 (4)
C5Z	0.676 (7)	0.204 (3)	0.7458 (10)	0.061 (14)*	0.128 (4)
H5Z	0.5941	0.1469	0.7511	0.073*	0.128 (4)
C7Z	0.895 (7)	0.289 (3)	0.6533 (10)	0.077 (15)*	0.128 (4)
C8Z	0.809 (8)	0.370 (3)	0.6245 (13)	0.051 (14)*	0.128 (4)
C9Z	0.899 (10)	0.386 (5)	0.5862 (17)	0.059 (14)*	0.128 (4)
H9Z	1.0168	0.3483	0.5778	0.070*	0.128 (4)
C10Z	0.814 (10)	0.456 (5)	0.5601 (14)	0.064 (15)*	0.128 (4)
H10Z	0.8748	0.4678	0.5340	0.077*	0.128 (4)
C11Z	0.640 (5)	0.5115 (16)	0.5725 (10)	0.056 (14)*	0.128 (4)
C12Z	0.551 (7)	0.496 (3)	0.6106 (13)	0.055 (13)*	0.128 (4)
H12Z	0.4326	0.5333	0.6191	0.066*	0.128 (4)
C13Z	0.635 (8)	0.425 (4)	0.6367 (12)	0.058 (14)*	0.128 (4)
H13Z	0.5746	0.4138	0.6629	0.070*	0.128 (4)
C14Z	0.5366 (16)	0.5933 (6)	0.5449 (2)	0.071 (2)	0.128 (4)
C15Z	1.042 (8)	0.461 (3)	0.719 (2)	0.078 (14)*	0.128 (4)
H15Z	1.0703	0.4551	0.6901	0.094*	0.128 (4)
C16Z	1.249 (8)	0.452 (5)	0.739 (2)	0.11 (3)*	0.128 (4)
H16J	1.3064	0.3877	0.7337	0.165*	0.128 (4)
H16K	1.3413	0.5022	0.7292	0.165*	0.128 (4)
H16L	1.2327	0.4596	0.7685	0.165*	0.128 (4)
C17Z	0.919 (12)	0.553 (4)	0.724 (3)	0.10 (3)*	0.128 (4)
H17J	0.7892	0.5467	0.7088	0.147*	0.128 (4)
H17K	0.8889	0.5653	0.7520	0.147*	0.128 (4)
H17L	0.9975	0.6079	0.7126	0.147*	0.128 (4)
C18Z	0.624 (9)	0.261 (5)	0.8194 (12)	0.087 (15)*	0.128 (4)
H18Z	0.6096	0.1906	0.8262	0.105*	0.128 (4)
C19Z	0.800 (11)	0.307 (6)	0.8445 (17)	0.10 (2)*	0.128 (4)
H19J	0.7640	0.3048	0.8730	0.147*	0.128 (4)
H19K	0.9277	0.2714	0.8399	0.147*	0.128 (4)
H19L	0.8183	0.3751	0.8363	0.147*	0.128 (4)
C20Z	0.420 (9)	0.316 (6)	0.829 (2)	0.10 (2)*	0.128 (4)
H20J	0.3787	0.3032	0.8564	0.145*	0.128 (4)
H20K	0.4408	0.3857	0.8248	0.145*	0.128 (4)
H20L	0.3119	0.2931	0.8104	0.145*	0.128 (4)
C21Z	0.765 (7)	0.186 (3)	0.6629 (10)	0.077 (14)*	0.128 (4)
C22Z	0.903 (10)	0.095 (4)	0.659 (2)	0.10 (2)*	0.128 (4)
H22I	0.9061	0.0730	0.6312	0.154*	0.128 (4)
H22J	1.0427	0.1103	0.6681	0.154*	0.128 (4)
H22K	0.8469	0.0426	0.6761	0.154*	0.128 (4)
C23Z	0.562 (9)	0.174 (5)	0.639 (2)	0.14 (3)*	0.128 (4)
H23J	0.5931	0.1525	0.6117	0.206*	0.128 (4)
H23K	0.4742	0.1265	0.6523	0.206*	0.128 (4)
H23L	0.4911	0.2370	0.6379	0.206*	0.128 (4)
N1	0.0595 (9)	0.6667 (4)	0.49226 (17)	0.0657 (19)
H1A	0.1617	0.6456	0.5087	0.079*
H1B	−0.0643	0.6492	0.5026	0.079*
H1C	0.0657	0.7324	0.4901	0.079*
C24	0.2976 (16)	0.6512 (7)	0.4330 (2)	0.105 (4)
H24A	0.4066	0.6330	0.4518	0.158*
H24B	0.2997	0.7216	0.4288	0.158*
H24C	0.3201	0.6181	0.4073	0.158*
C25	0.0856 (15)	0.6207 (7)	0.4504 (2)	0.078 (3)
H25	−0.0237	0.6480	0.4325	0.094*
C26	0.051 (2)	0.5115 (9)	0.4535 (3)	0.087 (3)
C27	−0.136 (2)	0.4715 (11)	0.4395 (3)	0.112 (4)
H27	−0.2408	0.5127	0.4294	0.134*
C28	−0.167 (3)	0.3686 (14)	0.4408 (5)	0.155 (6)
H28	−0.2919	0.3414	0.4313	0.186*
C29	−0.014 (4)	0.3090 (15)	0.4558 (6)	0.187 (11)
H29	−0.0366	0.2410	0.4573	0.225*
C30	0.174 (4)	0.3480 (14)	0.4690 (5)	0.179 (8)
H30	0.2811	0.3066	0.4781	0.215*
C31	0.202 (2)	0.4499 (11)	0.4684 (3)	0.127 (5)
H31	0.3262	0.4767	0.4784	0.152*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.086 (15)	0.070 (15)	0.082 (12)	0.024 (13)	0.019 (12)	0.011 (12)
O2	0.078 (4)	0.095 (4)	0.072 (4)	0.004 (4)	0.009 (3)	0.031 (3)
O3	0.076 (5)	0.145 (6)	0.068 (4)	0.024 (5)	−0.006 (4)	0.031 (4)
C14	0.097 (7)	0.072 (5)	0.044 (5)	−0.004 (6)	−0.011 (6)	0.008 (4)
O1D	0.076 (13)	0.073 (18)	0.075 (14)	0.002 (13)	0.015 (13)	0.012 (14)
O2D	0.078 (4)	0.095 (4)	0.072 (4)	0.004 (4)	0.009 (3)	0.031 (3)
O3D	0.076 (5)	0.145 (6)	0.068 (4)	0.024 (5)	−0.006 (4)	0.031 (4)
C14D	0.097 (7)	0.072 (5)	0.044 (5)	−0.004 (6)	−0.011 (6)	0.008 (4)
O1P	0.076 (15)	0.078 (18)	0.079 (16)	0.006 (14)	0.020 (14)	0.014 (14)
O2P	0.078 (4)	0.095 (4)	0.072 (4)	0.004 (4)	0.009 (3)	0.031 (3)
O3P	0.076 (5)	0.145 (6)	0.068 (4)	0.024 (5)	−0.006 (4)	0.031 (4)
C14P	0.097 (7)	0.072 (5)	0.044 (5)	−0.004 (6)	−0.011 (6)	0.008 (4)
O2Z	0.078 (4)	0.095 (4)	0.072 (4)	0.004 (4)	0.009 (3)	0.031 (3)
O3Z	0.076 (5)	0.145 (6)	0.068 (4)	0.024 (5)	−0.006 (4)	0.031 (4)
C14Z	0.097 (7)	0.072 (5)	0.044 (5)	−0.004 (6)	−0.011 (6)	0.008 (4)
N1	0.064 (5)	0.080 (4)	0.053 (4)	0.010 (4)	0.001 (4)	0.014 (4)
C24	0.108 (9)	0.142 (9)	0.066 (6)	0.000 (8)	0.031 (6)	0.006 (6)
C25	0.084 (8)	0.098 (8)	0.053 (6)	0.011 (6)	−0.013 (5)	0.006 (5)
C26	0.110 (10)	0.105 (9)	0.046 (6)	0.004 (9)	−0.005 (6)	−0.010 (6)
C27	0.124 (12)	0.126 (12)	0.085 (8)	0.000 (10)	0.020 (8)	−0.018 (7)
C28	0.186 (19)	0.138 (15)	0.141 (13)	−0.049 (14)	0.030 (13)	−0.027 (12)
C29	0.29 (4)	0.112 (15)	0.155 (18)	−0.027 (18)	0.06 (2)	−0.006 (12)
C30	0.25 (3)	0.108 (15)	0.177 (15)	0.032 (14)	−0.011 (16)	0.001 (11)
C31	0.170 (15)	0.106 (10)	0.105 (9)	0.009 (11)	−0.024 (9)	−0.006 (8)

Geometric parameters (Å, º)

O1—C7	1.21 (2)	C4P—C18P	1.52 (2)
O2—C14	1.259 (9)	C5P—C6P	1.40 (2)
O3—C14	1.233 (10)	C5P—H5P	0.9300
C1—C2	1.38 (2)	C6P—C21P	1.51 (2)
C1—C6	1.39 (2)	C7P—C8P	1.53 (2)
C1—C7	1.52 (2)	C7P—C15P	1.66 (2)
C2—C3	1.40 (2)	C8P—C9P	1.37 (2)
C2—C15	1.54 (2)	C8P—C13P	1.39 (2)
C3—C4	1.39 (2)	C9P—C10P	1.40 (2)
C3—H3	0.9300	C9P—H9P	0.9300
C4—C5	1.38 (2)	C10P—C11P	1.38 (2)
C4—C18	1.56 (2)	C10P—H10P	0.9300
C5—C6	1.39 (2)	C11P—C12P	1.40 (2)
C5—H5	0.9300	C11P—C14P	1.52 (2)
C6—C21	1.51 (2)	C12P—C13P	1.39 (2)
C7—C8	1.50 (2)	C12P—H12P	0.9300
C8—C13	1.36 (2)	C13P—H13P	0.9300
C8—C9	1.37 (2)	C15P—C16P	1.51 (2)
C9—C10	1.38 (2)	C15P—C17P	1.53 (2)
C9—H9	0.9300	C16P—H16G	0.9600
C10—C11	1.35 (2)	C16P—H16H	0.9600
C10—H10	0.9300	C16P—H16I	0.9600
C11—C12	1.39 (2)	C17P—H17G	0.9600
C11—C14	1.515 (19)	C17P—H17H	0.9600
C12—C13	1.39 (2)	C17P—H17I	0.9600
C12—H12	0.9300	C18P—C20P	1.52 (3)
C13—H13	0.9300	C18P—C19P	1.53 (3)
C15—C16	1.50 (2)	C18P—H18P	0.9800
C15—C17	1.51 (2)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C23P	1.54 (3)
C17—H17C	0.9600	C21P—C22P	1.54 (3)
C18—C20	1.47 (2)	C21P—H21P	0.9800
C18—C19	1.52 (2)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (3)
C20—H20C	0.9600	O2Z—C14Z	1.259 (9)
C21—C22	1.51 (2)	O3Z—C14Z	1.233 (10)
C21—C23	1.57 (2)	C6Z—C5Z	1.3889
C21—H21	0.9800	C6Z—C1Z	1.3908
C22—H22A	0.9600	C6Z—C21Z	1.51 (2)
C22—H22B	0.9600	C1Z—C2Z	1.3877
C22—H22C	0.9600	C1Z—C7Z	1.52 (2)
C23—H23A	0.9600	C2Z—C3Z	1.3891
C23—H23B	0.9600	C2Z—C15Z	1.49 (2)
C23—H23C	0.9600	C3Z—C4Z	1.3873
O1D—C7D	1.45 (2)	C3Z—H3Z	0.9495
O2D—C14D	1.259 (9)	C4Z—C5Z	1.3887
O3D—C14D	1.233 (10)	C4Z—C18Z	1.51 (2)
C1D—C2D	1.36 (2)	C5Z—H5Z	0.9499
C1D—C6D	1.38 (2)	C7Z—C8Z	1.54 (2)
C1D—C7D	1.56 (2)	C7Z—C21Z	1.65 (2)
C2D—C3D	1.40 (2)	C8Z—C13Z	1.3903
C2D—C15D	1.53 (2)	C8Z—C9Z	1.3916
C3D—C4D	1.42 (2)	C9Z—C10Z	1.3863
C3D—H3D	0.9300	C9Z—H9Z	0.9482
C4D—C5D	1.40 (2)	C10Z—C11Z	1.3916
C4D—C18D	1.55 (2)	C10Z—H10Z	0.9500
C5D—C6D	1.39 (2)	C11Z—C12Z	1.3864
C5D—H5D	0.9300	C11Z—C14Z	1.571 (19)
C6D—C21D	1.53 (2)	C12Z—C13Z	1.3935
C7D—C22D	1.51 (2)	C12Z—H12Z	0.9479
C7D—C8D	1.54 (2)	C13Z—H13Z	0.9477
C8D—C13D	1.36 (2)	C15Z—C17Z	1.47 (3)
C8D—C9D	1.39 (2)	C15Z—C16Z	1.48 (3)
C9D—C10D	1.373 (19)	C15Z—H15Z	0.9800
C9D—H9D	0.9300	C16Z—H16J	0.9600
C10D—C11D	1.38 (2)	C16Z—H16K	0.9600
C10D—H10D	0.9300	C16Z—H16L	0.9600
C11D—C12D	1.39 (2)	C17Z—H17J	0.9600
C11D—C14D	1.481 (18)	C17Z—H17K	0.9600
C12D—C13D	1.39 (2)	C17Z—H17L	0.9600
C12D—H12D	0.9300	C18Z—C19Z	1.52 (3)
C13D—H13D	0.9300	C18Z—C20Z	1.53 (3)
C15D—C16D	1.47 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.56 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C22Z	1.51 (2)
C17D—H17F	0.9600	C21Z—C23Z	1.52 (2)
C18D—C19D	1.48 (2)	C22Z—H22I	0.9600
C18D—C20D	1.49 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.511 (9)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.49 (2)	N1—H1C	0.8900
C21D—C22D	1.54 (2)	C24—C25	1.522 (11)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.494 (12)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C31	1.361 (15)
O1P—C7P	1.40 (2)	C26—C27	1.384 (15)
O2P—C14P	1.259 (9)	C27—C28	1.403 (16)
O3P—C14P	1.233 (10)	C27—H27	0.9300
C1P—C6P	1.39 (2)	C28—C29	1.35 (2)
C1P—C2P	1.40 (2)	C28—H28	0.9300
C1P—C7P	1.51 (2)	C29—C30	1.38 (2)
C2P—C3P	1.40 (2)	C29—H29	0.9300
C2P—C15P	1.50 (2)	C30—C31	1.385 (17)
C3P—C4P	1.38 (2)	C30—H30	0.9300
C3P—H3P	0.9300	C31—H31	0.9300
C4P—C5P	1.38 (2)
C2—C1—C6	118.1 (19)	C1P—C7P—C8P	120 (2)
C2—C1—C7	125 (2)	O1P—C7P—C15P	115 (3)
C6—C1—C7	117 (2)	C1P—C7P—C15P	84.0 (16)
C1—C2—C3	122 (2)	C8P—C7P—C15P	108.1 (17)
C1—C2—C15	119 (2)	C9P—C8P—C13P	118 (2)
C3—C2—C15	118 (2)	C9P—C8P—C7P	121 (2)
C4—C3—C2	120 (2)	C13P—C8P—C7P	121 (2)
C4—C3—H3	120.0	C8P—C9P—C10P	121 (3)
C2—C3—H3	120.0	C8P—C9P—H9P	119.5
C5—C4—C3	117 (2)	C10P—C9P—H9P	119.5
C5—C4—C18	123 (2)	C11P—C10P—C9P	121 (3)
C3—C4—C18	120 (2)	C11P—C10P—H10P	119.4
C4—C5—C6	123 (2)	C9P—C10P—H10P	119.4
C4—C5—H5	118.5	C10P—C11P—C12P	118 (2)
C6—C5—H5	118.5	C10P—C11P—C14P	125 (2)
C1—C6—C5	120 (2)	C12P—C11P—C14P	117 (2)
C1—C6—C21	119 (2)	C13P—C12P—C11P	120 (3)
C5—C6—C21	121 (2)	C13P—C12P—H12P	120.2
O1—C7—C8	119 (2)	C11P—C12P—H12P	120.2
O1—C7—C1	124 (3)	C8P—C13P—C12P	122 (3)
C8—C7—C1	117 (2)	C8P—C13P—H13P	119.0
C13—C8—C9	122 (2)	C12P—C13P—H13P	119.0
C13—C8—C7	121 (2)	O3P—C14P—O2P	123.3 (8)
C9—C8—C7	117 (2)	O3P—C14P—C11P	120.7 (15)
C8—C9—C10	116 (2)	O2P—C14P—C11P	115.2 (15)
C8—C9—H9	121.8	C2P—C15P—C16P	123 (3)
C10—C9—H9	121.8	C2P—C15P—C17P	119 (3)
C11—C10—C9	125 (2)	C16P—C15P—C17P	105 (3)
C11—C10—H10	117.7	C2P—C15P—C7P	85.8 (17)
C9—C10—H10	117.7	C16P—C15P—C7P	109 (3)
C10—C11—C12	117.3 (19)	C17P—C15P—C7P	112 (3)
C10—C11—C14	122 (2)	C15P—C16P—H16G	109.5
C12—C11—C14	120 (2)	C15P—C16P—H16H	109.5
C13—C12—C11	120 (2)	H16G—C16P—H16H	109.5
C13—C12—H12	120.1	C15P—C16P—H16I	109.5
C11—C12—H12	120.1	H16G—C16P—H16I	109.5
C8—C13—C12	120 (2)	H16H—C16P—H16I	109.5
C8—C13—H13	120.2	C15P—C17P—H17G	109.5
C12—C13—H13	120.2	C15P—C17P—H17H	109.5
O3—C14—O2	123.3 (8)	H17G—C17P—H17H	109.5
O3—C14—C11	118.8 (14)	C15P—C17P—H17I	109.5
O2—C14—C11	117.9 (14)	H17G—C17P—H17I	109.5
C16—C15—C17	114 (3)	H17H—C17P—H17I	109.5
C16—C15—C2	112 (3)	C20P—C18P—C4P	103 (3)
C17—C15—C2	112 (2)	C20P—C18P—C19P	110 (3)
C16—C15—H15	106.3	C4P—C18P—C19P	109 (3)
C17—C15—H15	106.3	C20P—C18P—H18P	111.4
C2—C15—H15	106.3	C4P—C18P—H18P	111.4
C15—C16—H16A	109.5	C19P—C18P—H18P	111.4
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C20—C18—C19	111 (3)	H20H—C20P—H20I	109.5
C20—C18—C4	111 (2)	C6P—C21P—C23P	115 (3)
C19—C18—C4	113 (2)	C6P—C21P—C22P	112 (3)
C20—C18—H18	107.1	C23P—C21P—C22P	106 (3)
C19—C18—H18	107.1	C6P—C21P—H21P	108.1
C4—C18—H18	107.1	C23P—C21P—H21P	108.1
C18—C19—H19A	109.5	C22P—C21P—H21P	108.1
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C22—C21—C6	110 (2)	H23H—C23P—H23I	109.5
C22—C21—C23	110 (2)	C5Z—C6Z—C1Z	120.0
C6—C21—C23	108 (2)	C5Z—C6Z—C21Z	146.2 (18)
C22—C21—H21	109.7	C1Z—C6Z—C21Z	93.4 (18)
C6—C21—H21	109.7	C2Z—C1Z—C6Z	119.8
C23—C21—H21	109.7	C2Z—C1Z—C7Z	143.0 (18)
C21—C22—H22A	109.5	C6Z—C1Z—C7Z	96.1 (18)
C21—C22—H22B	109.5	C1Z—C2Z—C3Z	120.22 (8)
H22A—C22—H22B	109.5	C1Z—C2Z—C15Z	117 (2)
C21—C22—H22C	109.5	C3Z—C2Z—C15Z	123 (2)
H22A—C22—H22C	109.5	C4Z—C3Z—C2Z	120.0
H22B—C22—H22C	109.5	C4Z—C3Z—H3Z	120.0
C21—C23—H23A	109.5	C2Z—C3Z—H3Z	120.1
C21—C23—H23B	109.5	C3Z—C4Z—C5Z	120.0
H23A—C23—H23B	109.5	C3Z—C4Z—C18Z	117 (2)
C21—C23—H23C	109.5	C5Z—C4Z—C18Z	123 (2)
H23A—C23—H23C	109.5	C4Z—C5Z—C6Z	120.07 (8)
H23B—C23—H23C	109.5	C4Z—C5Z—H5Z	119.9
C2D—C1D—C6D	122.1 (19)	C6Z—C5Z—H5Z	120.0
C2D—C1D—C7D	125 (2)	O1Z—C7Z—C1Z	94 (3)
C6D—C1D—C7D	113.2 (17)	O1Z—C7Z—C8Z	114 (3)
C1D—C2D—C3D	118 (2)	C1Z—C7Z—C8Z	119 (3)
C1D—C2D—C15D	123 (2)	O1Z—C7Z—C21Z	116 (3)
C3D—C2D—C15D	118 (2)	C1Z—C7Z—C21Z	83.9 (17)
C2D—C3D—C4D	122 (2)	C8Z—C7Z—C21Z	123 (3)
C2D—C3D—H3D	119.2	C13Z—C8Z—C9Z	120.1
C4D—C3D—H3D	119.2	C13Z—C8Z—C7Z	119 (2)
C5D—C4D—C3D	118 (2)	C9Z—C8Z—C7Z	121 (2)
C5D—C4D—C18D	115 (2)	C10Z—C9Z—C8Z	120.0
C3D—C4D—C18D	127 (2)	C10Z—C9Z—H9Z	119.8
C6D—C5D—C4D	120 (2)	C8Z—C9Z—H9Z	120.2
C6D—C5D—H5D	120.2	C9Z—C10Z—C11Z	119.8
C4D—C5D—H5D	120.2	C9Z—C10Z—H10Z	120.3
C1D—C6D—C5D	120 (2)	C11Z—C10Z—H10Z	119.8
C1D—C6D—C21D	107.7 (17)	C12Z—C11Z—C10Z	120.4
C5D—C6D—C21D	132 (2)	C12Z—C11Z—C14Z	117 (2)
O1D—C7D—C22D	110 (2)	C10Z—C11Z—C14Z	123 (2)
O1D—C7D—C8D	110 (2)	C11Z—C12Z—C13Z	119.7
C22D—C7D—C8D	116 (2)	C11Z—C12Z—H12Z	120.5
O1D—C7D—C1D	111 (2)	C13Z—C12Z—H12Z	119.7
C22D—C7D—C1D	99.5 (16)	C8Z—C13Z—C12Z	119.9
C8D—C7D—C1D	111 (2)	C8Z—C13Z—H13Z	120.1
C13D—C8D—C9D	119 (2)	C12Z—C13Z—H13Z	120.0
C13D—C8D—C7D	124 (2)	O3Z—C14Z—O2Z	123.3 (8)
C9D—C8D—C7D	117 (2)	O3Z—C14Z—C11Z	120.2 (16)
C10D—C9D—C8D	119 (2)	O2Z—C14Z—C11Z	116.5 (16)
C10D—C9D—H9D	120.5	C17Z—C15Z—C16Z	121 (4)
C8D—C9D—H9D	120.5	C17Z—C15Z—C2Z	112 (3)
C9D—C10D—C11D	124 (2)	C16Z—C15Z—C2Z	108 (3)
C9D—C10D—H10D	118.2	C17Z—C15Z—H15Z	105.0
C11D—C10D—H10D	118.2	C16Z—C15Z—H15Z	105.0
C10D—C11D—C12D	116 (2)	C2Z—C15Z—H15Z	105.0
C10D—C11D—C14D	122 (2)	C15Z—C16Z—H16J	109.5
C12D—C11D—C14D	122 (2)	C15Z—C16Z—H16K	109.5
C13D—C12D—C11D	121 (3)	H16J—C16Z—H16K	109.5
C13D—C12D—H12D	119.4	C15Z—C16Z—H16L	109.5
C11D—C12D—H12D	119.4	H16J—C16Z—H16L	109.5
C8D—C13D—C12D	121 (3)	H16K—C16Z—H16L	109.5
C8D—C13D—H13D	119.4	C15Z—C17Z—H17J	109.5
C12D—C13D—H13D	119.4	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	123.3 (8)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	115.1 (14)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	121.2 (14)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	111 (2)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	111 (2)	C4Z—C18Z—C19Z	100 (3)
C2D—C15D—C17D	109 (2)	C4Z—C18Z—C20Z	116 (3)
C16D—C15D—H15D	108.9	C19Z—C18Z—C20Z	109 (4)
C2D—C15D—H15D	108.9	C4Z—C18Z—H18Z	110.3
C17D—C15D—H15D	108.9	C19Z—C18Z—H18Z	110.3
C15D—C16D—H16D	109.5	C20Z—C18Z—H18Z	110.3
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C19D—C18D—C20D	120 (3)	H20K—C20Z—H20L	109.5
C19D—C18D—C4D	123 (2)	C6Z—C21Z—C22Z	109 (3)
C20D—C18D—C4D	116 (2)	C6Z—C21Z—C23Z	120 (3)
C19D—C18D—H18D	92.8	C22Z—C21Z—C23Z	112 (3)
C20D—C18D—H18D	92.8	C6Z—C21Z—C7Z	86.4 (17)
C4D—C18D—H18D	92.8	C22Z—C21Z—C7Z	112 (3)
C18D—C19D—H19D	109.5	C23Z—C21Z—C7Z	114 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	117 (3)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	115 (3)	C25—N1—H1A	109.5
C6D—C21D—C22D	102.2 (19)	C25—N1—H1B	109.5
C23D—C21D—H21D	107.1	H1A—N1—H1B	109.5
C6D—C21D—H21D	107.1	C25—N1—H1C	109.5
C22D—C21D—H21D	107.1	H1A—N1—H1C	109.5
C7D—C22D—C21D	107.9 (17)	H1B—N1—H1C	109.5
C7D—C22D—H22D	110.1	C25—C24—H24A	109.5
C21D—C22D—H22D	110.1	C25—C24—H24B	109.5
C7D—C22D—H22E	110.1	H24A—C24—H24B	109.5
C21D—C22D—H22E	110.1	C25—C24—H24C	109.5
H22D—C22D—H22E	108.4	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	109.1 (7)
H23D—C23D—H23E	109.5	C26—C25—C24	115.0 (9)
C21D—C23D—H23F	109.5	N1—C25—C24	109.0 (7)
H23D—C23D—H23F	109.5	C26—C25—H25	107.8
H23E—C23D—H23F	109.5	N1—C25—H25	107.8
C6P—C1P—C2P	122 (2)	C24—C25—H25	107.8
C6P—C1P—C7P	142 (2)	C31—C26—C27	119.2 (12)
C2P—C1P—C7P	95.6 (19)	C31—C26—C25	121.5 (13)
C3P—C2P—C1P	119 (2)	C27—C26—C25	119.3 (13)
C3P—C2P—C15P	147 (3)	C26—C27—C28	119.8 (14)
C1P—C2P—C15P	93.9 (19)	C26—C27—H27	120.1
C4P—C3P—C2P	117 (3)	C28—C27—H27	120.1
C4P—C3P—H3P	121.3	C29—C28—C27	120 (2)
C2P—C3P—H3P	121.3	C29—C28—H28	120.1
C5P—C4P—C3P	125 (3)	C27—C28—H28	120.1
C5P—C4P—C18P	115 (3)	C28—C29—C30	121 (2)
C3P—C4P—C18P	120 (3)	C28—C29—H29	119.6
C4P—C5P—C6P	118 (3)	C30—C29—H29	119.6
C4P—C5P—H5P	121.0	C29—C30—C31	119 (2)
C6P—C5P—H5P	121.0	C29—C30—H30	120.5
C1P—C6P—C5P	119 (2)	C31—C30—H30	120.5
C1P—C6P—C21P	127 (3)	C26—C31—C30	121.3 (16)
C5P—C6P—C21P	114 (2)	C26—C31—H31	119.3
O1P—C7P—C1P	123 (3)	C30—C31—H31	119.3
O1P—C7P—C8P	105 (2)

(1050minUV)

Crystal data

C31H39NO3	Dx = 1.118 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1976 reflections
a = 6.3861 (5) Å	θ = 1.6–18.8°
b = 13.4799 (10) Å	µ = 0.07 mm^−1
c = 32.6933 (17) Å	T = 299 K
V = 2814.4 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5437 independent reflections
Radiation source: fine-focus sealed tube	1797 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.143
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→16
Tmin = 0.861, Tmax = 1.000	l = −40→40
25037 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.090	H-atom parameters constrained
wR(F^2) = 0.210	w = 1/[σ^2(Fo^2) + (0.0377P)^2 + 0.5056P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5437 reflections	Δρmax = 0.14 e Å^−3
426 parameters	Δρmin = −0.16 e Å^−3
511 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.2 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.046 (5)	0.242 (2)	0.6362 (13)	0.083 (8)	0.305 (4)
O2	0.6554 (10)	0.6319 (4)	0.51810 (16)	0.0869 (19)	0.305 (4)
O3	0.3544 (11)	0.6162 (5)	0.54967 (17)	0.099 (2)	0.305 (4)
C6	0.696 (5)	0.1990 (19)	0.6995 (6)	0.064 (10)*	0.305 (4)
C1	0.822 (6)	0.282 (2)	0.6932 (6)	0.064 (11)*	0.305 (4)
C2	0.881 (6)	0.343 (2)	0.7257 (8)	0.070 (11)*	0.305 (4)
C3	0.811 (6)	0.318 (2)	0.7649 (6)	0.078 (10)*	0.305 (4)
H3	0.8480	0.3589	0.7867	0.094*	0.305 (4)
C4	0.688 (5)	0.236 (2)	0.7722 (5)	0.053 (8)*	0.305 (4)
C5	0.631 (5)	0.1784 (17)	0.7391 (6)	0.067 (10)*	0.305 (4)
H5	0.5456	0.1235	0.7435	0.080*	0.305 (4)
C7	0.904 (4)	0.2922 (19)	0.6498 (7)	0.091 (11)*	0.305 (4)
C8	0.804 (4)	0.3673 (19)	0.6227 (8)	0.063 (11)*	0.305 (4)
C9	0.924 (3)	0.4103 (15)	0.5924 (7)	0.048 (7)*	0.305 (4)
H9	1.0615	0.3896	0.5885	0.057*	0.305 (4)
C10	0.842 (4)	0.4835 (13)	0.5680 (5)	0.058 (8)*	0.305 (4)
H10	0.9258	0.5125	0.5480	0.069*	0.305 (4)
C11	0.637 (4)	0.5145 (10)	0.5726 (5)	0.062 (11)*	0.305 (4)
C12	0.515 (4)	0.469 (2)	0.6016 (9)	0.067 (11)*	0.305 (4)
H12	0.3749	0.4870	0.6043	0.081*	0.305 (4)
C13	0.598 (4)	0.397 (3)	0.6268 (10)	0.066 (11)*	0.305 (4)
H13	0.5145	0.3677	0.6468	0.079*	0.305 (4)
C14	0.5391 (16)	0.5922 (6)	0.5448 (2)	0.071 (2)	0.305 (4)
C15	1.007 (5)	0.435 (2)	0.7160 (12)	0.066 (10)*	0.305 (4)
H15	1.0047	0.4381	0.6860	0.079*	0.305 (4)
C16	1.234 (5)	0.430 (4)	0.726 (2)	0.071 (15)*	0.305 (4)
H16A	1.2901	0.3680	0.7167	0.107*	0.305 (4)
H16B	1.3059	0.4836	0.7122	0.107*	0.305 (4)
H16C	1.2530	0.4364	0.7548	0.107*	0.305 (4)
C17	0.902 (7)	0.530 (2)	0.7287 (13)	0.084 (13)*	0.305 (4)
H17A	0.7561	0.5268	0.7213	0.126*	0.305 (4)
H17B	0.9139	0.5375	0.7578	0.126*	0.305 (4)
H17C	0.9668	0.5847	0.7152	0.126*	0.305 (4)
C18	0.628 (5)	0.209 (3)	0.8176 (7)	0.073 (10)*	0.305 (4)
H18	0.6462	0.1369	0.8203	0.087*	0.305 (4)
C19	0.771 (7)	0.257 (4)	0.8490 (10)	0.066 (11)*	0.305 (4)
H19A	0.9139	0.2426	0.8424	0.098*	0.305 (4)
H19B	0.7498	0.3278	0.8486	0.098*	0.305 (4)
H19C	0.7387	0.2321	0.8757	0.098*	0.305 (4)
C20	0.407 (6)	0.230 (4)	0.8269 (17)	0.124 (19)*	0.305 (4)
H20A	0.3188	0.1989	0.8069	0.186*	0.305 (4)
H20B	0.3730	0.2047	0.8536	0.186*	0.305 (4)
H20C	0.3841	0.3004	0.8264	0.186*	0.305 (4)
C21	0.647 (5)	0.130 (2)	0.6643 (9)	0.073 (10)*	0.305 (4)
H21	0.6336	0.1673	0.6388	0.087*	0.305 (4)
C22	0.815 (6)	0.051 (2)	0.6599 (12)	0.095 (13)*	0.305 (4)
H22A	0.7804	0.0077	0.6374	0.142*	0.305 (4)
H22B	0.9478	0.0816	0.6548	0.142*	0.305 (4)
H22C	0.8228	0.0122	0.6846	0.142*	0.305 (4)
C23	0.435 (5)	0.076 (3)	0.6748 (13)	0.084 (11)*	0.305 (4)
H23A	0.3994	0.0314	0.6531	0.126*	0.305 (4)
H23B	0.4504	0.0399	0.6999	0.126*	0.305 (4)
H23C	0.3266	0.1249	0.6778	0.126*	0.305 (4)
O1D	1.098 (4)	0.271 (2)	0.6404 (11)	0.074 (9)	0.356 (4)
O2D	0.6554 (10)	0.6319 (4)	0.51810 (16)	0.0869 (19)	0.356 (4)
O3D	0.3544 (11)	0.6162 (5)	0.54967 (17)	0.099 (2)	0.356 (4)
C1D	0.810 (5)	0.280 (2)	0.6910 (6)	0.067 (10)*	0.356 (4)
C2D	0.885 (5)	0.3469 (19)	0.7181 (7)	0.061 (8)*	0.356 (4)
C3D	0.839 (5)	0.337 (2)	0.7596 (7)	0.066 (8)*	0.356 (4)
H3D	0.9015	0.3793	0.7784	0.079*	0.356 (4)
C4D	0.698 (5)	0.263 (2)	0.7734 (7)	0.075 (9)*	0.356 (4)
C5D	0.612 (6)	0.200 (2)	0.7439 (7)	0.069 (9)*	0.356 (4)
H5D	0.5180	0.1510	0.7520	0.083*	0.356 (4)
C6D	0.665 (6)	0.208 (2)	0.7028 (7)	0.067 (10)*	0.356 (4)
C7D	0.871 (4)	0.2723 (16)	0.6448 (6)	0.077 (8)*	0.356 (4)
C9D	0.886 (5)	0.386 (2)	0.5836 (8)	0.071 (8)*	0.356 (4)
H9D	1.0109	0.3556	0.5759	0.085*	0.356 (4)
C8D	0.782 (4)	0.3576 (18)	0.6189 (8)	0.060 (9)*	0.356 (4)
C13D	0.600 (5)	0.403 (3)	0.6287 (11)	0.063 (10)*	0.356 (4)
H13D	0.5311	0.3837	0.6525	0.076*	0.356 (4)
C12D	0.511 (4)	0.477 (3)	0.6055 (10)	0.066 (10)*	0.356 (4)
H12D	0.3851	0.5060	0.6133	0.079*	0.356 (4)
C11D	0.614 (4)	0.5079 (14)	0.5694 (7)	0.057 (9)*	0.356 (4)
C10D	0.799 (4)	0.460 (2)	0.5602 (7)	0.055 (7)*	0.356 (4)
H10D	0.8692	0.4793	0.5366	0.066*	0.356 (4)
C14D	0.5391 (16)	0.5922 (6)	0.5448 (2)	0.071 (2)	0.356 (4)
C15D	1.043 (4)	0.4270 (19)	0.7059 (10)	0.077 (9)*	0.356 (4)
H15D	1.0703	0.4216	0.6764	0.093*	0.356 (4)
C16D	1.241 (5)	0.407 (3)	0.7282 (16)	0.094 (15)*	0.356 (4)
H16D	1.3431	0.4562	0.7211	0.141*	0.356 (4)
H16E	1.2151	0.4091	0.7571	0.141*	0.356 (4)
H16F	1.2923	0.3424	0.7209	0.141*	0.356 (4)
C17D	0.941 (7)	0.528 (2)	0.7144 (15)	0.087 (13)*	0.356 (4)
H17D	0.8144	0.5339	0.6986	0.131*	0.356 (4)
H17E	0.9075	0.5331	0.7430	0.131*	0.356 (4)
H17F	1.0355	0.5802	0.7069	0.131*	0.356 (4)
C18D	0.626 (5)	0.240 (3)	0.8175 (7)	0.101 (11)*	0.356 (4)
H18D	0.6017	0.1698	0.8117	0.121*	0.356 (4)
C19D	0.777 (6)	0.219 (2)	0.8508 (8)	0.095 (13)*	0.356 (4)
H19D	0.9135	0.2085	0.8394	0.142*	0.356 (4)
H19E	0.7811	0.2740	0.8694	0.142*	0.356 (4)
H19F	0.7337	0.1604	0.8653	0.142*	0.356 (4)
C20D	0.404 (5)	0.259 (4)	0.8272 (13)	0.087 (13)*	0.356 (4)
H20D	0.3276	0.2713	0.8024	0.131*	0.356 (4)
H20E	0.3455	0.2020	0.8407	0.131*	0.356 (4)
H20F	0.3929	0.3156	0.8449	0.131*	0.356 (4)
C21D	0.599 (5)	0.151 (2)	0.6647 (9)	0.083 (10)*	0.356 (4)
H21D	0.4774	0.1854	0.6532	0.099*	0.356 (4)
C22D	0.786 (4)	0.1709 (15)	0.6356 (7)	0.089 (8)*	0.356 (4)
H22D	0.8941	0.1213	0.6397	0.107*	0.356 (4)
H22E	0.7402	0.1676	0.6074	0.107*	0.356 (4)
C23D	0.538 (6)	0.0449 (19)	0.6698 (10)	0.122 (13)*	0.356 (4)
H23D	0.4995	0.0176	0.6437	0.184*	0.356 (4)
H23E	0.6532	0.0082	0.6809	0.184*	0.356 (4)
H23F	0.4203	0.0405	0.6881	0.184*	0.356 (4)
O1P	1.111 (7)	0.304 (3)	0.6505 (16)	0.076 (9)	0.193 (4)
O2P	0.6554 (10)	0.6319 (4)	0.51810 (16)	0.0869 (19)	0.193 (4)
O3P	0.3544 (11)	0.6162 (5)	0.54967 (17)	0.099 (2)	0.193 (4)
C6P	0.662 (6)	0.212 (2)	0.7040 (9)	0.065 (13)*	0.193 (4)
C1P	0.799 (6)	0.291 (2)	0.6993 (8)	0.058 (12)*	0.193 (4)
C2P	0.853 (7)	0.349 (3)	0.7329 (9)	0.072 (12)*	0.193 (4)
C3P	0.769 (6)	0.328 (3)	0.7712 (8)	0.064 (11)*	0.193 (4)
H3P	0.8065	0.3674	0.7941	0.077*	0.193 (4)
C4P	0.634 (6)	0.248 (3)	0.7759 (8)	0.080 (12)*	0.193 (4)
C5P	0.579 (6)	0.190 (3)	0.7424 (10)	0.068 (13)*	0.193 (4)
H5P	0.4859	0.1362	0.7456	0.082*	0.193 (4)
C7P	0.938 (4)	0.3479 (19)	0.6698 (7)	0.068 (10)*	0.193 (4)
C8P	0.831 (4)	0.4092 (15)	0.6363 (6)	0.047 (9)*	0.193 (4)
C9P	0.954 (3)	0.451 (2)	0.6056 (8)	0.070 (11)*	0.193 (4)
H9P	1.1002	0.4381	0.6051	0.083*	0.193 (4)
C10P	0.863 (4)	0.5099 (19)	0.5758 (7)	0.068 (11)*	0.193 (4)
H10P	0.9472	0.5381	0.5549	0.082*	0.193 (4)
C11P	0.649 (5)	0.5281 (15)	0.5766 (7)	0.066 (12)*	0.193 (4)
C12P	0.525 (4)	0.487 (3)	0.6071 (10)	0.063 (13)*	0.193 (4)
H12P	0.3790	0.4991	0.6077	0.076*	0.193 (4)
C13P	0.616 (4)	0.427 (3)	0.6370 (8)	0.062 (12)*	0.193 (4)
H13P	0.5320	0.3991	0.6579	0.075*	0.193 (4)
C14P	0.5391 (16)	0.5922 (6)	0.5448 (2)	0.071 (2)	0.193 (4)
C15P	0.987 (6)	0.421 (2)	0.7095 (10)	0.071 (13)*	0.193 (4)
C16P	1.221 (7)	0.433 (6)	0.715 (2)	0.12 (2)*	0.193 (4)
H16G	1.2710	0.4828	0.6964	0.177*	0.193 (4)
H16H	1.2510	0.4515	0.7424	0.177*	0.193 (4)
H16I	1.2886	0.3707	0.7087	0.177*	0.193 (4)
C17P	0.894 (11)	0.526 (3)	0.706 (2)	0.085 (19)*	0.193 (4)
H17G	0.9887	0.5670	0.6903	0.128*	0.193 (4)
H17H	0.7623	0.5221	0.6915	0.128*	0.193 (4)
H17I	0.8737	0.5534	0.7323	0.128*	0.193 (4)
C18P	0.559 (7)	0.215 (4)	0.8177 (10)	0.087 (13)*	0.193 (4)
H18P	0.5577	0.1422	0.8197	0.105*	0.193 (4)
C19P	0.686 (8)	0.260 (6)	0.8520 (14)	0.11 (2)*	0.193 (4)
H19G	0.6341	0.2373	0.8778	0.158*	0.193 (4)
H19H	0.8303	0.2415	0.8491	0.158*	0.193 (4)
H19I	0.6747	0.3314	0.8508	0.158*	0.193 (4)
C20P	0.336 (6)	0.256 (5)	0.8166 (16)	0.082 (17)*	0.193 (4)
H20G	0.2596	0.2261	0.7946	0.124*	0.193 (4)
H20H	0.2669	0.2426	0.8420	0.124*	0.193 (4)
H20I	0.3412	0.3269	0.8124	0.124*	0.193 (4)
C21P	0.578 (7)	0.147 (3)	0.6699 (13)	0.071 (13)*	0.193 (4)
H21P	0.5511	0.1894	0.6460	0.086*	0.193 (4)
C22P	0.735 (8)	0.067 (4)	0.6576 (17)	0.079 (15)*	0.193 (4)
H22F	0.6775	0.0270	0.6360	0.119*	0.193 (4)
H22G	0.8626	0.0972	0.6484	0.119*	0.193 (4)
H22H	0.7649	0.0252	0.6808	0.119*	0.193 (4)
C23P	0.373 (8)	0.093 (5)	0.681 (2)	0.13 (2)*	0.193 (4)
H23G	0.3283	0.0539	0.6582	0.194*	0.193 (4)
H23H	0.3968	0.0514	0.7043	0.194*	0.193 (4)
H23I	0.2672	0.1414	0.6875	0.194*	0.193 (4)
O1Z	1.108 (6)	0.283 (5)	0.6555 (17)	0.077 (10)*	0.146 (4)
O2Z	0.6554 (10)	0.6319 (4)	0.51810 (16)	0.0869 (19)	0.146 (4)
O3Z	0.3544 (11)	0.6162 (5)	0.54967 (17)	0.099 (2)	0.146 (4)
C6Z	0.749 (7)	0.220 (2)	0.7082 (8)	0.049 (11)*	0.146 (4)
C1Z	0.866 (6)	0.306 (2)	0.7023 (8)	0.056 (12)*	0.146 (4)
C2Z	0.896 (7)	0.371 (2)	0.7346 (9)	0.071 (13)*	0.146 (4)
C3Z	0.811 (7)	0.351 (3)	0.7728 (8)	0.081 (14)*	0.146 (4)
H3Z	0.8322	0.3953	0.7949	0.097*	0.146 (4)
C4Z	0.695 (6)	0.265 (3)	0.7787 (8)	0.074 (14)*	0.146 (4)
C5Z	0.664 (7)	0.199 (3)	0.7464 (9)	0.067 (13)*	0.146 (4)
H5Z	0.5845	0.1405	0.7504	0.080*	0.146 (4)
C7Z	0.887 (6)	0.292 (2)	0.6565 (9)	0.092 (14)*	0.146 (4)
C8Z	0.800 (7)	0.372 (3)	0.6273 (11)	0.057 (13)*	0.146 (4)
C9Z	0.892 (9)	0.385 (4)	0.5890 (15)	0.067 (14)*	0.146 (4)
H9Z	1.0089	0.3456	0.5813	0.080*	0.146 (4)
C10Z	0.812 (8)	0.454 (4)	0.5619 (12)	0.060 (14)*	0.146 (4)
H10Z	0.8737	0.4630	0.5357	0.072*	0.146 (4)
C11Z	0.640 (5)	0.5117 (15)	0.5731 (9)	0.061 (14)*	0.146 (4)
C12Z	0.548 (6)	0.500 (3)	0.6113 (11)	0.058 (13)*	0.146 (4)
H12Z	0.4314	0.5389	0.6190	0.069*	0.146 (4)
C13Z	0.628 (7)	0.430 (3)	0.6385 (10)	0.065 (13)*	0.146 (4)
H13Z	0.5665	0.4215	0.6646	0.078*	0.146 (4)
C14Z	0.5391 (16)	0.5922 (6)	0.5448 (2)	0.071 (2)	0.146 (4)
C15Z	1.033 (8)	0.460 (3)	0.7279 (16)	0.072 (13)*	0.146 (4)
H15Z	1.0463	0.4671	0.6982	0.086*	0.146 (4)
C16Z	1.243 (7)	0.428 (5)	0.743 (2)	0.13 (3)*	0.146 (4)
H16J	1.2788	0.3655	0.7313	0.194*	0.146 (4)
H16K	1.3451	0.4771	0.7353	0.194*	0.146 (4)
H16L	1.2391	0.4228	0.7723	0.194*	0.146 (4)
C17Z	0.955 (11)	0.555 (3)	0.743 (2)	0.12 (2)*	0.146 (4)
H17J	0.8198	0.5683	0.7317	0.185*	0.146 (4)
H17K	0.9446	0.5525	0.7725	0.185*	0.146 (4)
H17L	1.0506	0.6068	0.7355	0.185*	0.146 (4)
C18Z	0.610 (9)	0.253 (4)	0.8214 (11)	0.098 (15)*	0.146 (4)
H18Z	0.5902	0.1835	0.8293	0.118*	0.146 (4)
C19Z	0.792 (10)	0.303 (5)	0.8442 (16)	0.09 (2)*	0.146 (4)
H19J	0.7642	0.3025	0.8731	0.141*	0.146 (4)
H19K	0.9192	0.2673	0.8388	0.141*	0.146 (4)
H19L	0.8065	0.3702	0.8350	0.141*	0.146 (4)
C20Z	0.415 (9)	0.317 (6)	0.830 (2)	0.12 (2)*	0.146 (4)
H20J	0.3679	0.3062	0.8572	0.183*	0.146 (4)
H20K	0.4489	0.3855	0.8259	0.183*	0.146 (4)
H20L	0.3055	0.2983	0.8109	0.183*	0.146 (4)
C21Z	0.766 (6)	0.186 (2)	0.6641 (10)	0.086 (13)*	0.146 (4)
C22Z	0.908 (8)	0.096 (3)	0.6633 (15)	0.068 (16)*	0.146 (4)
H22I	0.9218	0.0722	0.6357	0.103*	0.146 (4)
H22J	1.0439	0.1137	0.6737	0.103*	0.146 (4)
H22K	0.8498	0.0442	0.6801	0.103*	0.146 (4)
C23Z	0.571 (9)	0.171 (5)	0.6382 (19)	0.15 (3)*	0.146 (4)
H23J	0.6103	0.1498	0.6114	0.220*	0.146 (4)
H23K	0.4821	0.1224	0.6507	0.220*	0.146 (4)
H23L	0.4963	0.2332	0.6363	0.220*	0.146 (4)
N1	0.0635 (10)	0.6667 (4)	0.49218 (17)	0.072 (2)
H1A	0.1650	0.6448	0.5085	0.086*
H1B	−0.0604	0.6504	0.5027	0.086*
H1C	0.0722	0.7324	0.4899	0.086*
C24	0.2982 (17)	0.6504 (7)	0.4331 (3)	0.112 (4)
H24A	0.4064	0.6359	0.4525	0.168*
H24B	0.2979	0.7202	0.4272	0.168*
H24C	0.3235	0.6140	0.4083	0.168*
C25	0.0862 (15)	0.6204 (7)	0.4507 (2)	0.080 (3)
H25	−0.0229	0.6481	0.4330	0.096*
C26	0.052 (2)	0.5106 (9)	0.4533 (3)	0.089 (3)
C27	−0.137 (3)	0.4718 (12)	0.4402 (3)	0.118 (4)
H27	−0.2434	0.5136	0.4311	0.141*
C28	−0.167 (3)	0.3681 (16)	0.4406 (5)	0.156 (7)
H28	−0.2905	0.3402	0.4308	0.187*
C29	−0.013 (5)	0.3101 (17)	0.4558 (7)	0.199 (12)
H29	−0.0343	0.2420	0.4569	0.239*
C30	0.172 (4)	0.3467 (16)	0.4694 (5)	0.183 (8)
H30	0.2774	0.3049	0.4790	0.220*
C31	0.199 (3)	0.4492 (12)	0.4686 (3)	0.136 (5)
H31	0.3220	0.4762	0.4790	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.084 (15)	0.076 (16)	0.089 (13)	0.019 (13)	0.019 (13)	0.013 (13)
O2	0.087 (5)	0.098 (4)	0.075 (4)	−0.001 (4)	0.010 (3)	0.036 (3)
O3	0.082 (5)	0.145 (6)	0.069 (4)	0.034 (5)	0.001 (4)	0.030 (4)
C14	0.093 (7)	0.071 (5)	0.048 (5)	0.003 (5)	−0.018 (5)	0.009 (4)
O1D	0.069 (12)	0.073 (17)	0.080 (14)	0.004 (13)	0.017 (12)	0.005 (13)
O2D	0.087 (5)	0.098 (4)	0.075 (4)	−0.001 (4)	0.010 (3)	0.036 (3)
O3D	0.082 (5)	0.145 (6)	0.069 (4)	0.034 (5)	0.001 (4)	0.030 (4)
C14D	0.093 (7)	0.071 (5)	0.048 (5)	0.003 (5)	−0.018 (5)	0.009 (4)
O1P	0.069 (14)	0.080 (18)	0.079 (16)	0.010 (15)	0.017 (14)	0.017 (14)
O2P	0.087 (5)	0.098 (4)	0.075 (4)	−0.001 (4)	0.010 (3)	0.036 (3)
O3P	0.082 (5)	0.145 (6)	0.069 (4)	0.034 (5)	0.001 (4)	0.030 (4)
C14P	0.093 (7)	0.071 (5)	0.048 (5)	0.003 (5)	−0.018 (5)	0.009 (4)
O2Z	0.087 (5)	0.098 (4)	0.075 (4)	−0.001 (4)	0.010 (3)	0.036 (3)
O3Z	0.082 (5)	0.145 (6)	0.069 (4)	0.034 (5)	0.001 (4)	0.030 (4)
C14Z	0.093 (7)	0.071 (5)	0.048 (5)	0.003 (5)	−0.018 (5)	0.009 (4)
N1	0.070 (5)	0.092 (5)	0.052 (4)	0.007 (4)	0.000 (4)	0.016 (4)
C24	0.123 (10)	0.145 (9)	0.068 (6)	0.003 (9)	0.030 (7)	0.005 (6)
C25	0.086 (8)	0.103 (8)	0.051 (6)	0.008 (6)	−0.014 (5)	0.005 (5)
C26	0.109 (10)	0.099 (9)	0.058 (6)	0.006 (9)	0.001 (7)	0.001 (6)
C27	0.114 (12)	0.135 (13)	0.104 (9)	−0.001 (10)	0.024 (8)	−0.019 (8)
C28	0.171 (19)	0.165 (18)	0.131 (13)	−0.068 (15)	0.032 (12)	−0.044 (12)
C29	0.29 (4)	0.129 (17)	0.17 (2)	−0.03 (2)	0.04 (2)	−0.001 (13)
C30	0.24 (3)	0.132 (18)	0.178 (16)	0.032 (15)	−0.020 (16)	0.017 (12)
C31	0.201 (17)	0.103 (10)	0.105 (9)	0.006 (11)	−0.031 (10)	0.002 (8)

Geometric parameters (Å, º)

O1—C7	1.21 (2)	C3P—H3P	0.9506
O2—C14	1.265 (9)	C4P—C5P	1.3902
O3—C14	1.233 (9)	C4P—C18P	1.52 (2)
C6—C5	1.3848	C5P—H5P	0.9502
C6—C1	1.3949	C7P—C8P	1.53 (2)
C6—C21	1.51 (2)	C7P—C15P	1.66 (2)
C1—C2	1.3963	C8P—C13P	1.3902
C1—C7	1.52 (2)	C8P—C9P	1.3908
C2—C3	1.3968	C9P—C10P	1.3882
C2—C15	1.51 (2)	C9P—H9P	0.9497
C3—C4	1.3776	C10P—C11P	1.3908
C3—H3	0.9300	C10P—H10P	0.9502
C4—C5	1.3849	C11P—C12P	1.3878
C4—C18	1.577 (19)	C11P—C14P	1.522 (15)
C5—H5	0.9300	C12P—C13P	1.3906
C7—C8	1.490 (19)	C12P—H12P	0.9500
C8—C13	1.3777	C13P—H13P	0.9501
C8—C9	1.3818	C15P—C16P	1.51 (2)
C9—C10	1.3730	C15P—C17P	1.54 (2)
C9—H9	0.9300	C16P—H16G	0.9600
C10—C11	1.3822	C16P—H16H	0.9600
C10—H10	0.9300	C16P—H16I	0.9600
C11—C12	1.3734	C17P—H17G	0.9600
C11—C14	1.521 (15)	C17P—H17H	0.9600
C12—C13	1.3828	C17P—H17I	0.9600
C12—H12	0.9300	C18P—C19P	1.51 (3)
C13—H13	0.9300	C18P—C20P	1.53 (3)
C15—C16	1.49 (2)	C18P—H18P	0.9800
C15—C17	1.50 (2)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C22P	1.54 (3)
C17—H17C	0.9600	C21P—C23P	1.54 (3)
C18—C20	1.47 (2)	C21P—H21P	0.9800
C18—C19	1.52 (2)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (2)
C20—H20C	0.9600	O2Z—C14Z	1.265 (9)
C21—C22	1.52 (2)	O3Z—C14Z	1.233 (9)
C21—C23	1.57 (2)	C6Z—C5Z	1.3894
C21—H21	0.9800	C6Z—C1Z	1.3921
C22—H22A	0.9600	C6Z—C21Z	1.51 (2)
C22—H22B	0.9600	C1Z—C2Z	1.3891
C22—H22C	0.9600	C1Z—C7Z	1.52 (2)
C23—H23A	0.9600	C2Z—C3Z	1.3894
C23—H23B	0.9600	C2Z—C15Z	1.49 (2)
C23—H23C	0.9600	C3Z—C4Z	1.3886
O1D—C7D	1.46 (2)	C3Z—H3Z	0.9504
O2D—C14D	1.265 (9)	C4Z—C5Z	1.3901
O3D—C14D	1.233 (9)	C4Z—C18Z	1.51 (2)
C1D—C2D	1.351 (19)	C5Z—H5Z	0.9508
C1D—C6D	1.403 (19)	C7Z—C8Z	1.54 (2)
C1D—C7D	1.56 (2)	C7Z—C21Z	1.65 (2)
C2D—C3D	1.39 (2)	C8Z—C13Z	1.3906
C2D—C15D	1.53 (2)	C8Z—C9Z	1.3920
C3D—C4D	1.41 (2)	C9Z—C10Z	1.3876
C3D—H3D	0.9300	C9Z—H9Z	0.9485
C4D—C5D	1.40 (2)	C10Z—C11Z	1.3920
C4D—C18D	1.55 (2)	C10Z—H10Z	0.9502
C5D—C6D	1.389 (18)	C11Z—C12Z	1.3869
C5D—H5D	0.9300	C11Z—C14Z	1.565 (18)
C6D—C21D	1.52 (2)	C12Z—C13Z	1.3948
C7D—C22D	1.50 (2)	C12Z—H12Z	0.9481
C7D—C8D	1.539 (19)	C13Z—H13Z	0.9480
C9D—C10D	1.377 (18)	C15Z—C17Z	1.47 (3)
C9D—C8D	1.387 (19)	C15Z—C16Z	1.49 (3)
C9D—H9D	0.9300	C15Z—H15Z	0.9800
C8D—C13D	1.354 (19)	C16Z—H16J	0.9600
C13D—C12D	1.373 (18)	C16Z—H16K	0.9600
C13D—H13D	0.9300	C16Z—H16L	0.9600
C12D—C11D	1.411 (19)	C17Z—H17J	0.9600
C12D—H12D	0.9300	C17Z—H17K	0.9600
C11D—C10D	1.379 (19)	C17Z—H17L	0.9600
C11D—C14D	1.472 (17)	C18Z—C20Z	1.54 (3)
C10D—H10D	0.9300	C18Z—C19Z	1.54 (3)
C15D—C16D	1.48 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.54 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C23Z	1.52 (2)
C17D—H17F	0.9600	C21Z—C22Z	1.52 (2)
C18D—C20D	1.48 (2)	C22Z—H22I	0.9600
C18D—C19D	1.48 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.499 (9)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.49 (2)	N1—H1C	0.8900
C21D—C22D	1.55 (2)	C24—C25	1.526 (12)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.499 (13)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C31	1.346 (15)
O1P—C7P	1.41 (2)	C26—C27	1.387 (16)
O2P—C14P	1.265 (9)	C27—C28	1.410 (17)
O3P—C14P	1.233 (9)	C27—H27	0.9300
C6P—C1P	1.3892	C28—C29	1.35 (2)
C6P—C5P	1.3911	C28—H28	0.9300
C6P—C21P	1.52 (2)	C29—C30	1.35 (2)
C1P—C2P	1.3907	C29—H29	0.9300
C1P—C7P	1.52 (2)	C30—C31	1.393 (18)
C2P—C3P	1.3909	C30—H30	0.9300
C2P—C15P	1.50 (2)	C31—H31	0.9300
C3P—C4P	1.3861
C5—C6—C1	118.2	C1P—C7P—C8P	118 (2)
C5—C6—C21	121.6 (15)	O1P—C7P—C15P	117 (3)
C1—C6—C21	119.9 (15)	C1P—C7P—C15P	85.0 (16)
C6—C1—C2	121.0	C8P—C7P—C15P	108.9 (18)
C6—C1—C7	114.4 (14)	C13P—C8P—C9P	119.9
C2—C1—C7	124.4 (15)	C13P—C8P—C7P	121.4 (17)
C1—C2—C3	118.19 (6)	C9P—C8P—C7P	118.6 (17)
C1—C2—C15	117.8 (18)	C10P—C9P—C8P	120.0
C3—C2—C15	123.9 (18)	C10P—C9P—H9P	120.1
C4—C3—C2	122.2	C8P—C9P—H9P	119.9
C4—C3—H3	118.9	C9P—C10P—C11P	120.1
C2—C3—H3	118.9	C9P—C10P—H10P	119.9
C3—C4—C5	117.8	C11P—C10P—H10P	120.0
C3—C4—C18	119.5 (16)	C12P—C11P—C10P	120.0
C5—C4—C18	122.6 (16)	C12P—C11P—C14P	117.3 (19)
C6—C5—C4	122.59 (5)	C10P—C11P—C14P	122.7 (19)
C6—C5—H5	118.7	C11P—C12P—C13P	120.0
C4—C5—H5	118.7	C11P—C12P—H12P	120.1
O1—C7—C8	119 (2)	C13P—C12P—H12P	119.9
O1—C7—C1	123 (3)	C8P—C13P—C12P	120.0
C8—C7—C1	118 (2)	C8P—C13P—H13P	120.0
C13—C8—C9	118.6	C12P—C13P—H13P	120.0
C13—C8—C7	123.3 (16)	O3P—C14P—O2P	122.6 (7)
C9—C8—C7	118.1 (16)	O3P—C14P—C11P	120.0 (14)
C10—C9—C8	120.5	O2P—C14P—C11P	116.2 (14)
C10—C9—H9	119.8	C2P—C15P—C16P	125 (3)
C8—C9—H9	119.8	C2P—C15P—C17P	114 (3)
C9—C10—C11	121.0	C16P—C15P—C17P	107 (3)
C9—C10—H10	119.5	C2P—C15P—C7P	84.7 (16)
C11—C10—H10	119.5	C16P—C15P—C7P	110 (3)
C12—C11—C10	118.6	C17P—C15P—C7P	114 (3)
C12—C11—C14	119.0 (16)	C15P—C16P—H16G	109.5
C10—C11—C14	122.2 (16)	C15P—C16P—H16H	109.5
C11—C12—C13	120.5	H16G—C16P—H16H	109.5
C11—C12—H12	119.8	C15P—C16P—H16I	109.5
C13—C12—H12	119.8	H16G—C16P—H16I	109.5
C8—C13—C12	120.8	H16H—C16P—H16I	109.5
C8—C13—H13	119.6	C15P—C17P—H17G	109.5
C12—C13—H13	119.6	C15P—C17P—H17H	109.5
O3—C14—O2	122.6 (7)	H17G—C17P—H17H	109.5
O3—C14—C11	119.8 (13)	C15P—C17P—H17I	109.5
O2—C14—C11	117.5 (13)	H17G—C17P—H17I	109.5
C16—C15—C17	115 (3)	H17H—C17P—H17I	109.5
C16—C15—C2	116 (3)	C19P—C18P—C4P	112 (3)
C17—C15—C2	113 (2)	C19P—C18P—C20P	112 (3)
C16—C15—H15	103.6	C4P—C18P—C20P	99 (3)
C17—C15—H15	103.6	C19P—C18P—H18P	111.1
C2—C15—H15	103.6	C4P—C18P—H18P	111.1
C15—C16—H16A	109.5	C20P—C18P—H18P	111.1
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C20—C18—C19	111 (3)	H20H—C20P—H20I	109.5
C20—C18—C4	112 (3)	C6P—C21P—C22P	111 (3)
C19—C18—C4	113 (2)	C6P—C21P—C23P	114 (3)
C20—C18—H18	106.9	C22P—C21P—C23P	107 (3)
C19—C18—H18	106.9	C6P—C21P—H21P	108.3
C4—C18—H18	106.9	C22P—C21P—H21P	108.3
C18—C19—H19A	109.5	C23P—C21P—H21P	108.3
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C6—C21—C22	111 (2)	H23H—C23P—H23I	109.5
C6—C21—C23	107 (2)	C5Z—C6Z—C1Z	120.0
C22—C21—C23	108 (2)	C5Z—C6Z—C21Z	145.1 (17)
C6—C21—H21	110.2	C1Z—C6Z—C21Z	94.9 (17)
C22—C21—H21	110.2	C2Z—C1Z—C6Z	119.8
C23—C21—H21	110.2	C2Z—C1Z—C7Z	144.9 (17)
C21—C22—H22A	109.5	C6Z—C1Z—C7Z	94.6 (17)
C21—C22—H22B	109.5	C1Z—C2Z—C3Z	120.20 (7)
H22A—C22—H22B	109.5	C1Z—C2Z—C15Z	118 (2)
C21—C22—H22C	109.5	C3Z—C2Z—C15Z	121 (2)
H22A—C22—H22C	109.5	C4Z—C3Z—C2Z	119.9
H22B—C22—H22C	109.5	C4Z—C3Z—H3Z	120.0
C21—C23—H23A	109.5	C2Z—C3Z—H3Z	120.0
C21—C23—H23B	109.5	C3Z—C4Z—C5Z	120.0
H23A—C23—H23B	109.5	C3Z—C4Z—C18Z	114 (2)
C21—C23—H23C	109.5	C5Z—C4Z—C18Z	126 (2)
H23A—C23—H23C	109.5	C6Z—C5Z—C4Z	120.05 (7)
H23B—C23—H23C	109.5	C6Z—C5Z—H5Z	120.0
C2D—C1D—C6D	121.3 (17)	C4Z—C5Z—H5Z	120.0
C2D—C1D—C7D	126.2 (18)	O1Z—C7Z—C1Z	97 (3)
C6D—C1D—C7D	112.5 (16)	O1Z—C7Z—C8Z	114 (3)
C1D—C2D—C3D	119.9 (17)	C1Z—C7Z—C8Z	120 (3)
C1D—C2D—C15D	122 (2)	O1Z—C7Z—C21Z	113 (3)
C3D—C2D—C15D	117.5 (19)	C1Z—C7Z—C21Z	85.2 (16)
C2D—C3D—C4D	120.9 (18)	C8Z—C7Z—C21Z	123 (2)
C2D—C3D—H3D	119.5	C13Z—C8Z—C9Z	120.1
C4D—C3D—H3D	119.5	C13Z—C8Z—C7Z	121 (2)
C5D—C4D—C3D	117.2 (17)	C9Z—C8Z—C7Z	119 (2)
C5D—C4D—C18D	114 (2)	C10Z—C9Z—C8Z	120.0
C3D—C4D—C18D	129 (2)	C10Z—C9Z—H9Z	119.8
C6D—C5D—C4D	121.7 (19)	C8Z—C9Z—H9Z	120.2
C6D—C5D—H5D	119.2	C9Z—C10Z—C11Z	119.9
C4D—C5D—H5D	119.2	C9Z—C10Z—H10Z	120.4
C5D—C6D—C1D	118.6 (17)	C11Z—C10Z—H10Z	119.8
C5D—C6D—C21D	133.4 (19)	C12Z—C11Z—C10Z	120.4
C1D—C6D—C21D	108.1 (16)	C12Z—C11Z—C14Z	116 (2)
O1D—C7D—C22D	109.2 (19)	C10Z—C11Z—C14Z	124 (2)
O1D—C7D—C8D	109.0 (19)	C11Z—C12Z—C13Z	119.8
C22D—C7D—C8D	116 (2)	C11Z—C12Z—H12Z	120.5
O1D—C7D—C1D	110 (2)	C13Z—C12Z—H12Z	119.7
C22D—C7D—C1D	99.6 (15)	C8Z—C13Z—C12Z	119.9
C8D—C7D—C1D	113 (2)	C8Z—C13Z—H13Z	120.1
C10D—C9D—C8D	117.8 (18)	C12Z—C13Z—H13Z	120.0
C10D—C9D—H9D	121.1	O3Z—C14Z—O2Z	122.6 (7)
C8D—C9D—H9D	121.1	O3Z—C14Z—C11Z	119.9 (15)
C13D—C8D—C9D	119.1 (16)	O2Z—C14Z—C11Z	117.4 (15)
C13D—C8D—C7D	121.9 (19)	C17Z—C15Z—C16Z	116 (4)
C9D—C8D—C7D	119.0 (18)	C17Z—C15Z—C2Z	117 (3)
C8D—C13D—C12D	123.4 (19)	C16Z—C15Z—C2Z	104 (2)
C8D—C13D—H13D	118.3	C17Z—C15Z—H15Z	106.2
C12D—C13D—H13D	118.3	C16Z—C15Z—H15Z	106.2
C13D—C12D—C11D	119.0 (18)	C2Z—C15Z—H15Z	106.2
C13D—C12D—H12D	120.5	C15Z—C16Z—H16J	109.5
C11D—C12D—H12D	120.5	C15Z—C16Z—H16K	109.5
C10D—C11D—C12D	116.3 (16)	H16J—C16Z—H16K	109.5
C10D—C11D—C14D	121.2 (18)	C15Z—C16Z—H16L	109.5
C12D—C11D—C14D	122.3 (18)	H16J—C16Z—H16L	109.5
C9D—C10D—C11D	124.5 (18)	H16K—C16Z—H16L	109.5
C9D—C10D—H10D	117.8	C15Z—C17Z—H17J	109.5
C11D—C10D—H10D	117.8	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	122.6 (7)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	116.2 (13)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	120.9 (12)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	108 (2)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	116 (3)	C4Z—C18Z—C20Z	113 (3)
C2D—C15D—C17D	107 (2)	C4Z—C18Z—C19Z	97 (3)
C16D—C15D—H15D	108.6	C20Z—C18Z—C19Z	107 (3)
C2D—C15D—H15D	108.6	C4Z—C18Z—H18Z	112.8
C17D—C15D—H15D	108.6	C20Z—C18Z—H18Z	112.8
C15D—C16D—H16D	109.5	C19Z—C18Z—H18Z	112.8
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C20D—C18D—C19D	120 (2)	H20K—C20Z—H20L	109.5
C20D—C18D—C4D	117 (2)	C6Z—C21Z—C23Z	121 (3)
C19D—C18D—C4D	122 (2)	C6Z—C21Z—C22Z	107 (3)
C20D—C18D—H18D	93.3	C23Z—C21Z—C22Z	112 (3)
C19D—C18D—H18D	93.3	C6Z—C21Z—C7Z	85.0 (17)
C4D—C18D—H18D	93.3	C23Z—C21Z—C7Z	114 (3)
C18D—C19D—H19D	109.5	C22Z—C21Z—C7Z	114 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	118 (2)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	116 (3)	C25—N1—H1A	109.5
C6D—C21D—C22D	101.5 (18)	C25—N1—H1B	109.5
C23D—C21D—H21D	107.0	H1A—N1—H1B	109.5
C6D—C21D—H21D	107.0	C25—N1—H1C	109.5
C22D—C21D—H21D	107.0	H1A—N1—H1C	109.5
C7D—C22D—C21D	108.4 (16)	H1B—N1—H1C	109.5
C7D—C22D—H22D	110.0	C25—C24—H24A	109.5
C21D—C22D—H22D	110.0	C25—C24—H24B	109.5
C7D—C22D—H22E	110.0	H24A—C24—H24B	109.5
C21D—C22D—H22E	110.0	C25—C24—H24C	109.5
H22D—C22D—H22E	108.4	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	110.3 (7)
H23D—C23D—H23E	109.5	C26—C25—C24	114.3 (9)
C21D—C23D—H23F	109.5	N1—C25—C24	108.5 (7)
H23D—C23D—H23F	109.5	C26—C25—H25	107.8
H23E—C23D—H23F	109.5	N1—C25—H25	107.8
C1P—C6P—C5P	120.0	C24—C25—H25	107.8
C1P—C6P—C21P	126 (2)	C31—C26—C27	119.4 (12)
C5P—C6P—C21P	114 (2)	C31—C26—C25	121.8 (13)
C6P—C1P—C2P	120.0	C27—C26—C25	118.8 (13)
C6P—C1P—C7P	145.6 (17)	C26—C27—C28	119.3 (15)
C2P—C1P—C7P	94.3 (17)	C26—C27—H27	120.4
C1P—C2P—C3P	119.91 (7)	C28—C27—H27	120.4
C1P—C2P—C15P	95.7 (17)	C29—C28—C27	118 (2)
C3P—C2P—C15P	144.3 (17)	C29—C28—H28	120.8
C4P—C3P—C2P	120.1	C27—C28—H28	120.8
C4P—C3P—H3P	120.1	C28—C29—C30	123 (3)
C2P—C3P—H3P	119.8	C28—C29—H29	118.4
C3P—C4P—C5P	120.1	C30—C29—H29	118.4
C3P—C4P—C18P	122 (2)	C29—C30—C31	117 (2)
C5P—C4P—C18P	118 (2)	C29—C30—H30	121.3
C4P—C5P—C6P	119.92 (6)	C31—C30—H30	121.3
C4P—C5P—H5P	120.1	C26—C31—C30	122.2 (16)
C6P—C5P—H5P	120.0	C26—C31—H31	118.9
O1P—C7P—C1P	122 (3)	C30—C31—H31	118.9
O1P—C7P—C8P	105 (2)

(1290minUV)

Crystal data

C31H39NO3	Dx = 1.120 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1909 reflections
a = 6.392 (1) Å	θ = 1.6–18.2°
b = 13.4462 (18) Å	µ = 0.07 mm^−1
c = 32.676 (3) Å	T = 299 K
V = 2808.4 (6) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5427 independent reflections
Radiation source: fine-focus sealed tube	1825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.138
ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	h = −7→7
Tmin = 0.878, Tmax = 1.000	k = −14→16
25062 measured reflections	l = −40→40

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.091	H-atom parameters constrained
wR(F^2) = 0.219	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.3835P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5427 reflections	Δρmax = 0.14 e Å^−3
450 parameters	Δρmin = −0.16 e Å^−3
537 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 2.6 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.052 (6)	0.241 (3)	0.6361 (14)	0.079 (9)	0.264 (4)
O2	0.6597 (10)	0.6317 (4)	0.51834 (17)	0.0885 (19)	0.264 (4)
O3	0.3579 (11)	0.6152 (5)	0.54952 (17)	0.098 (2)	0.264 (4)
C1	0.836 (8)	0.282 (3)	0.6944 (9)	0.065 (12)*	0.264 (4)
C6	0.703 (7)	0.202 (3)	0.6996 (9)	0.071 (11)*	0.264 (4)
C5	0.626 (8)	0.183 (3)	0.7388 (9)	0.077 (12)*	0.264 (4)
H5	0.5453	0.1266	0.7431	0.092*	0.264 (4)
C4	0.666 (6)	0.245 (3)	0.7714 (8)	0.065 (11)*	0.264 (4)
C3	0.789 (7)	0.328 (3)	0.7652 (11)	0.077 (11)*	0.264 (4)
H3	0.8160	0.3715	0.7868	0.092*	0.264 (4)
C2	0.875 (8)	0.348 (3)	0.7267 (10)	0.074 (12)*	0.264 (4)
C7	0.919 (5)	0.293 (2)	0.6511 (9)	0.079 (11)*	0.264 (4)
C8	0.822 (5)	0.373 (2)	0.6252 (9)	0.058 (10)*	0.264 (4)
C13	0.623 (6)	0.408 (3)	0.6308 (11)	0.056 (11)*	0.264 (4)
H13	0.5464	0.3827	0.6528	0.067*	0.264 (4)
C9	0.932 (5)	0.410 (2)	0.5930 (9)	0.054 (9)*	0.264 (4)
H9	1.0676	0.3888	0.5882	0.065*	0.264 (4)
C10	0.842 (5)	0.480 (2)	0.5672 (10)	0.072 (11)*	0.264 (4)
H10	0.9201	0.5044	0.5454	0.087*	0.264 (4)
C11	0.642 (5)	0.5152 (12)	0.5726 (8)	0.065 (12)*	0.264 (4)
C12	0.529 (6)	0.478 (2)	0.6057 (10)	0.069 (12)*	0.264 (4)
H12	0.3929	0.4989	0.6107	0.083*	0.264 (4)
C14	0.5418 (16)	0.5921 (6)	0.5448 (2)	0.073 (2)	0.264 (4)
C15	1.011 (6)	0.438 (2)	0.7203 (14)	0.078 (11)*	0.264 (4)
H15	0.9939	0.4517	0.6910	0.094*	0.264 (4)
C16	1.242 (6)	0.424 (5)	0.724 (2)	0.064 (16)*	0.264 (4)
H16A	1.2812	0.3619	0.7114	0.095*	0.264 (4)
H16B	1.3142	0.4774	0.7110	0.095*	0.264 (4)
H16C	1.2802	0.4216	0.7526	0.095*	0.264 (4)
C17	0.936 (7)	0.533 (3)	0.7395 (13)	0.104 (14)*	0.264 (4)
H17A	0.7868	0.5387	0.7361	0.156*	0.264 (4)
H17B	0.9688	0.5331	0.7682	0.156*	0.264 (4)
H17C	1.0027	0.5889	0.7266	0.156*	0.264 (4)
C18	0.576 (5)	0.233 (4)	0.8145 (9)	0.099 (12)*	0.264 (4)
H18	0.5679	0.1605	0.8169	0.119*	0.264 (4)
C19	0.699 (5)	0.259 (3)	0.8509 (9)	0.067 (11)*	0.264 (4)
H19A	0.8418	0.2383	0.8470	0.100*	0.264 (4)
H19B	0.6949	0.3296	0.8551	0.100*	0.264 (4)
H19C	0.6425	0.2258	0.8744	0.100*	0.264 (4)
C20	0.349 (4)	0.261 (3)	0.8166 (10)	0.059 (10)*	0.264 (4)
H20A	0.2804	0.2416	0.7917	0.089*	0.264 (4)
H20B	0.2841	0.2280	0.8393	0.089*	0.264 (4)
H20C	0.3365	0.3318	0.8200	0.089*	0.264 (4)
C21	0.648 (6)	0.133 (2)	0.6643 (11)	0.079 (12)*	0.264 (4)
H21	0.6352	0.1713	0.6388	0.095*	0.264 (4)
C22	0.816 (7)	0.053 (3)	0.6601 (15)	0.098 (15)*	0.264 (4)
H22A	0.7820	0.0102	0.6377	0.148*	0.264 (4)
H22B	0.9491	0.0845	0.6549	0.148*	0.264 (4)
H22C	0.8241	0.0155	0.6849	0.148*	0.264 (4)
C23	0.439 (6)	0.077 (4)	0.6738 (17)	0.088 (15)*	0.264 (4)
H23A	0.4046	0.0339	0.6514	0.131*	0.264 (4)
H23B	0.4553	0.0385	0.6983	0.131*	0.264 (4)
H23C	0.3283	0.1246	0.6776	0.131*	0.264 (4)
O1D	1.097 (3)	0.271 (2)	0.6419 (9)	0.078 (9)	0.400 (4)
O2D	0.6597 (10)	0.6317 (4)	0.51834 (17)	0.0885 (19)	0.400 (4)
O3D	0.3579 (11)	0.6152 (5)	0.54952 (17)	0.098 (2)	0.400 (4)
C1D	0.803 (5)	0.2802 (19)	0.6916 (6)	0.068 (9)*	0.400 (4)
C2D	0.887 (5)	0.3438 (18)	0.7196 (7)	0.067 (8)*	0.400 (4)
C3D	0.840 (4)	0.331 (2)	0.7614 (7)	0.080 (8)*	0.400 (4)
H3D	0.9044	0.3718	0.7807	0.097*	0.400 (4)
C4D	0.697 (4)	0.257 (2)	0.7747 (7)	0.077 (9)*	0.400 (4)
C5D	0.609 (6)	0.197 (2)	0.7440 (7)	0.074 (9)*	0.400 (4)
H5D	0.5112	0.1484	0.7513	0.089*	0.400 (4)
C6D	0.663 (6)	0.207 (2)	0.7033 (7)	0.074 (9)*	0.400 (4)
C7D	0.870 (3)	0.2715 (15)	0.6455 (6)	0.081 (8)*	0.400 (4)
C9D	0.896 (4)	0.3909 (18)	0.5857 (7)	0.066 (8)*	0.400 (4)
H9D	1.0276	0.3646	0.5798	0.079*	0.400 (4)
C8D	0.780 (3)	0.3549 (14)	0.6184 (6)	0.057 (7)*	0.400 (4)
C13D	0.590 (4)	0.3947 (18)	0.6269 (8)	0.072 (8)*	0.400 (4)
H13D	0.5132	0.3702	0.6488	0.087*	0.400 (4)
C12D	0.507 (4)	0.4717 (18)	0.6032 (7)	0.071 (9)*	0.400 (4)
H12D	0.3768	0.4982	0.6094	0.085*	0.400 (4)
C11D	0.622 (3)	0.5087 (10)	0.5702 (5)	0.055 (8)*	0.400 (4)
C10D	0.814 (4)	0.4663 (17)	0.5622 (7)	0.063 (8)*	0.400 (4)
H10D	0.8912	0.4896	0.5401	0.076*	0.400 (4)
C14D	0.5418 (16)	0.5921 (6)	0.5448 (2)	0.073 (2)	0.400 (4)
C15D	1.040 (4)	0.4245 (16)	0.7072 (8)	0.075 (8)*	0.400 (4)
H15D	1.0686	0.4188	0.6778	0.090*	0.400 (4)
C16D	1.241 (4)	0.409 (3)	0.7303 (14)	0.116 (17)*	0.400 (4)
H16D	1.3397	0.4590	0.7229	0.174*	0.400 (4)
H16E	1.2135	0.4121	0.7592	0.174*	0.400 (4)
H16F	1.2966	0.3442	0.7237	0.174*	0.400 (4)
C17D	0.934 (5)	0.5261 (16)	0.7157 (10)	0.072 (9)*	0.400 (4)
H17D	0.8080	0.5310	0.6999	0.107*	0.400 (4)
H17E	0.9018	0.5313	0.7443	0.107*	0.400 (4)
H17F	1.0279	0.5788	0.7081	0.107*	0.400 (4)
C18D	0.643 (4)	0.219 (3)	0.8195 (7)	0.094 (9)*	0.400 (4)
H18D	0.6602	0.1465	0.8180	0.112*	0.400 (4)
C19D	0.800 (4)	0.251 (2)	0.8505 (7)	0.081 (8)*	0.400 (4)
H19D	0.9386	0.2385	0.8403	0.121*	0.400 (4)
H19E	0.7845	0.3212	0.8556	0.121*	0.400 (4)
H19F	0.7793	0.2152	0.8755	0.121*	0.400 (4)
C20D	0.413 (4)	0.233 (3)	0.8301 (12)	0.106 (13)*	0.400 (4)
H20D	0.3281	0.2094	0.8079	0.159*	0.400 (4)
H20E	0.3804	0.1963	0.8545	0.159*	0.400 (4)
H20F	0.3856	0.3023	0.8346	0.159*	0.400 (4)
C21D	0.601 (5)	0.148 (2)	0.6652 (8)	0.085 (10)*	0.400 (4)
H21D	0.4775	0.1810	0.6536	0.103*	0.400 (4)
C22D	0.786 (3)	0.1701 (14)	0.6361 (6)	0.093 (7)*	0.400 (4)
H22D	0.8946	0.1207	0.6397	0.111*	0.400 (4)
H22E	0.7387	0.1675	0.6079	0.111*	0.400 (4)
C23D	0.546 (5)	0.0418 (17)	0.6708 (8)	0.122 (11)*	0.400 (4)
H23D	0.5101	0.0132	0.6448	0.183*	0.400 (4)
H23E	0.6635	0.0070	0.6822	0.183*	0.400 (4)
H23F	0.4288	0.0365	0.6891	0.183*	0.400 (4)
O1P	1.113 (6)	0.303 (3)	0.6526 (15)	0.075 (9)	0.199 (4)
O2P	0.6597 (10)	0.6317 (4)	0.51834 (17)	0.0885 (19)	0.199 (4)
O3P	0.3579 (11)	0.6152 (5)	0.54952 (17)	0.098 (2)	0.199 (4)
C6P	0.665 (6)	0.212 (3)	0.7049 (9)	0.069 (13)*	0.199 (4)
C1P	0.796 (6)	0.293 (2)	0.7003 (7)	0.059 (12)*	0.199 (4)
C2P	0.858 (7)	0.348 (3)	0.7343 (9)	0.061 (11)*	0.199 (4)
C3P	0.787 (7)	0.321 (3)	0.7730 (8)	0.074 (12)*	0.199 (4)
H3P	0.8291	0.3584	0.7963	0.089*	0.199 (4)
C4P	0.656 (6)	0.239 (3)	0.7777 (8)	0.077 (13)*	0.199 (4)
C5P	0.595 (7)	0.185 (3)	0.7436 (10)	0.079 (13)*	0.199 (4)
H5P	0.5049	0.1290	0.7468	0.095*	0.199 (4)
C7P	0.936 (4)	0.3476 (18)	0.6704 (7)	0.054 (9)*	0.199 (4)
C8P	0.832 (4)	0.4084 (15)	0.6363 (6)	0.051 (9)*	0.199 (4)
C9P	0.956 (3)	0.4520 (19)	0.6063 (8)	0.074 (11)*	0.199 (4)
H9P	1.1023	0.4411	0.6062	0.089*	0.199 (4)
C10P	0.864 (4)	0.5114 (18)	0.5765 (7)	0.070 (10)*	0.199 (4)
H10P	0.9491	0.5412	0.5559	0.084*	0.199 (4)
C11P	0.649 (5)	0.5274 (15)	0.5766 (7)	0.075 (12)*	0.199 (4)
C12P	0.526 (4)	0.484 (2)	0.6065 (10)	0.069 (13)*	0.199 (4)
H12P	0.3789	0.4947	0.6067	0.083*	0.199 (4)
C13P	0.617 (4)	0.424 (2)	0.6365 (8)	0.061 (12)*	0.199 (4)
H13P	0.5321	0.3946	0.6570	0.073*	0.199 (4)
C14P	0.5418 (16)	0.5921 (6)	0.5448 (2)	0.073 (2)	0.199 (4)
C15P	0.983 (6)	0.421 (2)	0.7097 (9)	0.068 (12)*	0.199 (4)
C16P	1.215 (6)	0.433 (5)	0.718 (2)	0.09 (2)*	0.199 (4)
H16G	1.2711	0.4826	0.6996	0.138*	0.199 (4)
H16H	1.2362	0.4536	0.7456	0.138*	0.199 (4)
H16I	1.2841	0.3709	0.7131	0.138*	0.199 (4)
C17P	0.891 (10)	0.525 (3)	0.7037 (18)	0.11 (2)*	0.199 (4)
H17G	0.9859	0.5646	0.6876	0.166*	0.199 (4)
H17H	0.7595	0.5201	0.6898	0.166*	0.199 (4)
H17I	0.8711	0.5562	0.7299	0.166*	0.199 (4)
C18P	0.581 (7)	0.206 (3)	0.8196 (10)	0.086 (13)*	0.199 (4)
H18P	0.5020	0.1442	0.8185	0.103*	0.199 (4)
C19P	0.761 (7)	0.201 (3)	0.8496 (12)	0.070 (13)*	0.199 (4)
H19G	0.7091	0.1801	0.8758	0.105*	0.199 (4)
H19H	0.8624	0.1542	0.8399	0.105*	0.199 (4)
H19I	0.8241	0.2655	0.8521	0.105*	0.199 (4)
C20P	0.440 (8)	0.297 (4)	0.8289 (17)	0.116 (19)*	0.199 (4)
H20G	0.3272	0.2986	0.8095	0.175*	0.199 (4)
H20H	0.3842	0.2906	0.8560	0.175*	0.199 (4)
H20I	0.5206	0.3566	0.8268	0.175*	0.199 (4)
C21P	0.583 (7)	0.148 (3)	0.6702 (14)	0.079 (13)*	0.199 (4)
H21P	0.5529	0.1919	0.6471	0.095*	0.199 (4)
C22P	0.752 (9)	0.074 (4)	0.6565 (19)	0.100 (17)*	0.199 (4)
H22F	0.6993	0.0336	0.6345	0.149*	0.199 (4)
H22G	0.8734	0.1097	0.6473	0.149*	0.199 (4)
H22H	0.7903	0.0318	0.6791	0.149*	0.199 (4)
C23P	0.385 (7)	0.088 (4)	0.679 (2)	0.088 (19)*	0.199 (4)
H23G	0.3468	0.0503	0.6552	0.131*	0.199 (4)
H23H	0.4104	0.0431	0.7014	0.131*	0.199 (4)
H23I	0.2730	0.1322	0.6861	0.131*	0.199 (4)
O1Z	1.110 (7)	0.283 (6)	0.655 (2)	0.075 (10)*	0.137 (4)
O2Z	0.6597 (10)	0.6317 (4)	0.51834 (17)	0.0885 (19)	0.137 (4)
O3Z	0.3579 (11)	0.6152 (5)	0.54952 (17)	0.098 (2)	0.137 (4)
C6Z	0.754 (8)	0.219 (3)	0.7084 (9)	0.060 (13)*	0.137 (4)
C1Z	0.871 (7)	0.304 (3)	0.7013 (9)	0.060 (13)*	0.137 (4)
C2Z	0.902 (7)	0.373 (3)	0.7326 (10)	0.073 (13)*	0.137 (4)
C3Z	0.818 (7)	0.355 (3)	0.7712 (10)	0.084 (14)*	0.137 (4)
H3Z	0.8393	0.4017	0.7926	0.100*	0.137 (4)
C4Z	0.702 (7)	0.269 (3)	0.7783 (9)	0.078 (14)*	0.137 (4)
C5Z	0.670 (7)	0.201 (3)	0.7470 (10)	0.072 (14)*	0.137 (4)
H5Z	0.5906	0.1427	0.7519	0.087*	0.137 (4)
C7Z	0.888 (7)	0.288 (2)	0.6554 (10)	0.083 (14)*	0.137 (4)
C8Z	0.796 (7)	0.367 (3)	0.6258 (11)	0.054 (14)*	0.137 (4)
C9Z	0.876 (7)	0.376 (3)	0.5864 (13)	0.070 (14)*	0.137 (4)
H9Z	0.9852	0.3336	0.5773	0.084*	0.137 (4)
C10Z	0.796 (7)	0.448 (3)	0.5601 (10)	0.064 (14)*	0.137 (4)
H10Z	0.8504	0.4548	0.5332	0.077*	0.137 (4)
C11Z	0.636 (4)	0.5102 (15)	0.5733 (9)	0.063 (14)*	0.137 (4)
C12Z	0.556 (6)	0.501 (3)	0.6126 (11)	0.063 (13)*	0.137 (4)
H12Z	0.4468	0.5435	0.6217	0.076*	0.137 (4)
C13Z	0.636 (7)	0.429 (3)	0.6389 (10)	0.064 (13)*	0.137 (4)
H13Z	0.5816	0.4223	0.6658	0.077*	0.137 (4)
C14Z	0.5418 (16)	0.5921 (6)	0.5448 (2)	0.073 (2)	0.137 (4)
C15Z	1.020 (8)	0.464 (3)	0.7222 (19)	0.080 (14)*	0.137 (4)
H15Z	1.0476	0.4586	0.6927	0.096*	0.137 (4)
C16Z	1.227 (7)	0.456 (5)	0.742 (2)	0.11 (2)*	0.137 (4)
H16J	1.2873	0.3926	0.7354	0.166*	0.137 (4)
H16K	1.3167	0.5079	0.7313	0.166*	0.137 (4)
H16L	1.2128	0.4631	0.7707	0.166*	0.137 (4)
C17Z	0.891 (10)	0.554 (3)	0.726 (2)	0.08 (2)*	0.137 (4)
H17J	0.7620	0.5453	0.7117	0.120*	0.137 (4)
H17K	0.8610	0.5654	0.7548	0.120*	0.137 (4)
H17L	0.9648	0.6102	0.7154	0.120*	0.137 (4)
C18Z	0.613 (10)	0.252 (5)	0.8202 (13)	0.088 (15)*	0.137 (4)
H18Z	0.6577	0.1850	0.8282	0.105*	0.137 (4)
C19Z	0.750 (11)	0.322 (6)	0.8437 (17)	0.12 (2)*	0.137 (4)
H19J	0.7123	0.3205	0.8721	0.178*	0.137 (4)
H19K	0.8934	0.3033	0.8405	0.178*	0.137 (4)
H19L	0.7305	0.3887	0.8334	0.178*	0.137 (4)
C20Z	0.383 (11)	0.259 (10)	0.831 (3)	0.10 (3)*	0.137 (4)
H20J	0.3051	0.2120	0.8150	0.143*	0.137 (4)
H20K	0.3643	0.2443	0.8596	0.143*	0.137 (4)
H20L	0.3331	0.3249	0.8255	0.143*	0.137 (4)
C21Z	0.767 (7)	0.183 (3)	0.6647 (10)	0.091 (14)*	0.137 (4)
C22Z	0.906 (9)	0.091 (3)	0.6633 (18)	0.087 (19)*	0.137 (4)
H22I	0.9151	0.0673	0.6356	0.131*	0.137 (4)
H22J	1.0432	0.1076	0.6730	0.131*	0.137 (4)
H22K	0.8472	0.0399	0.6803	0.131*	0.137 (4)
C23Z	0.570 (9)	0.169 (5)	0.639 (2)	0.15 (3)*	0.137 (4)
H23J	0.6069	0.1458	0.6124	0.221*	0.137 (4)
H23K	0.4797	0.1213	0.6521	0.221*	0.137 (4)
H23L	0.4977	0.2315	0.6369	0.221*	0.137 (4)
N1	0.0664 (9)	0.6673 (4)	0.49238 (17)	0.070 (2)
H1A	0.1673	0.6448	0.5087	0.084*
H1B	−0.0577	0.6521	0.5030	0.084*
H1C	0.0775	0.7330	0.4900	0.084*
C24	0.3019 (16)	0.6494 (7)	0.4333 (3)	0.111 (4)
H24A	0.4094	0.6319	0.4525	0.167*
H24B	0.3049	0.7199	0.4286	0.167*
H24C	0.3255	0.6151	0.4080	0.167*
C25	0.0869 (15)	0.6197 (7)	0.4507 (2)	0.079 (3)
H25	−0.0216	0.6475	0.4329	0.094*
C26	0.054 (2)	0.5098 (9)	0.4535 (3)	0.095 (3)
C27	−0.136 (2)	0.4703 (11)	0.4397 (3)	0.116 (4)
H27	−0.2407	0.5121	0.4300	0.139*
C28	−0.166 (3)	0.3671 (15)	0.4407 (5)	0.159 (6)
H28	−0.2907	0.3389	0.4317	0.191*
C29	−0.009 (5)	0.3094 (17)	0.4552 (7)	0.205 (13)
H29	−0.0262	0.2407	0.4547	0.246*
C30	0.171 (4)	0.3460 (16)	0.4703 (6)	0.195 (9)
H30	0.2720	0.3043	0.4815	0.234*
C31	0.201 (2)	0.4485 (11)	0.4686 (3)	0.133 (5)
H31	0.3258	0.4752	0.4782	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (15)	0.072 (17)	0.082 (14)	0.011 (14)	0.018 (13)	0.012 (13)
O2	0.080 (4)	0.107 (4)	0.079 (4)	0.005 (4)	0.011 (3)	0.034 (4)
O3	0.076 (4)	0.146 (5)	0.070 (4)	0.029 (5)	0.007 (4)	0.031 (4)
C14	0.099 (7)	0.072 (5)	0.049 (5)	0.012 (5)	−0.005 (6)	0.004 (4)
O1D	0.073 (11)	0.075 (17)	0.085 (14)	0.010 (13)	0.020 (11)	−0.001 (13)
O2D	0.080 (4)	0.107 (4)	0.079 (4)	0.005 (4)	0.011 (3)	0.034 (4)
O3D	0.076 (4)	0.146 (5)	0.070 (4)	0.029 (5)	0.007 (4)	0.031 (4)
C14D	0.099 (7)	0.072 (5)	0.049 (5)	0.012 (5)	−0.005 (6)	0.004 (4)
O1P	0.073 (14)	0.076 (18)	0.075 (16)	0.007 (14)	0.019 (14)	0.011 (14)
O2P	0.080 (4)	0.107 (4)	0.079 (4)	0.005 (4)	0.011 (3)	0.034 (4)
O3P	0.076 (4)	0.146 (5)	0.070 (4)	0.029 (5)	0.007 (4)	0.031 (4)
C14P	0.099 (7)	0.072 (5)	0.049 (5)	0.012 (5)	−0.005 (6)	0.004 (4)
O2Z	0.080 (4)	0.107 (4)	0.079 (4)	0.005 (4)	0.011 (3)	0.034 (4)
O3Z	0.076 (4)	0.146 (5)	0.070 (4)	0.029 (5)	0.007 (4)	0.031 (4)
C14Z	0.099 (7)	0.072 (5)	0.049 (5)	0.012 (5)	−0.005 (6)	0.004 (4)
N1	0.061 (5)	0.094 (5)	0.056 (4)	0.005 (4)	0.003 (4)	0.012 (4)
C24	0.116 (9)	0.141 (9)	0.077 (6)	−0.006 (8)	0.025 (6)	0.005 (6)
C25	0.076 (7)	0.102 (8)	0.058 (6)	0.017 (6)	−0.014 (5)	0.006 (5)
C26	0.120 (11)	0.112 (10)	0.053 (6)	0.011 (10)	−0.003 (7)	−0.005 (6)
C27	0.108 (11)	0.138 (12)	0.101 (9)	−0.007 (9)	0.018 (8)	−0.011 (8)
C28	0.174 (18)	0.143 (16)	0.160 (15)	−0.062 (14)	0.030 (13)	−0.037 (12)
C29	0.34 (4)	0.122 (17)	0.157 (18)	−0.02 (2)	0.03 (2)	−0.015 (13)
C30	0.29 (3)	0.134 (19)	0.161 (16)	0.052 (17)	−0.034 (16)	0.008 (12)
C31	0.176 (15)	0.105 (10)	0.118 (10)	0.016 (11)	−0.033 (10)	0.005 (8)

Geometric parameters (Å, º)

O1—C7	1.21 (2)	C3P—H3P	0.9506
O2—C14	1.266 (9)	C4P—C5P	1.3902
O3—C14	1.225 (9)	C4P—C18P	1.52 (2)
C1—C6	1.39 (2)	C5P—H5P	0.9502
C1—C2	1.40 (2)	C7P—C8P	1.533 (19)
C1—C7	1.52 (2)	C7P—C15P	1.65 (2)
C6—C5	1.39 (2)	C8P—C13P	1.3902
C6—C21	1.52 (2)	C8P—C9P	1.3909
C5—C4	1.38 (2)	C9P—C10P	1.3882
C5—H5	0.9300	C9P—H9P	0.9497
C4—C3	1.38 (2)	C10P—C11P	1.3908
C4—C18	1.53 (2)	C10P—H10P	0.9502
C3—C2	1.40 (2)	C11P—C12P	1.3877
C3—H3	0.9300	C11P—C14P	1.519 (15)
C2—C15	1.51 (2)	C12P—C13P	1.3906
C7—C8	1.50 (2)	C12P—H12P	0.9499
C8—C9	1.36 (2)	C13P—H13P	0.9501
C8—C13	1.37 (2)	C15P—C16P	1.51 (2)
C13—C12	1.39 (2)	C15P—C17P	1.53 (2)
C13—H13	0.9300	C16P—H16G	0.9600
C9—C10	1.39 (2)	C16P—H16H	0.9600
C9—H9	0.9300	C16P—H16I	0.9600
C10—C11	1.37 (2)	C17P—H17G	0.9600
C10—H10	0.9300	C17P—H17H	0.9600
C11—C12	1.39 (2)	C17P—H17I	0.9600
C11—C14	1.52 (2)	C18P—C19P	1.51 (3)
C12—H12	0.9300	C18P—C20P	1.54 (3)
C15—C16	1.50 (2)	C18P—H18P	0.9800
C15—C17	1.50 (2)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C23P	1.53 (3)
C17—H17C	0.9600	C21P—C22P	1.54 (3)
C18—C19	1.47 (2)	C21P—H21P	0.9800
C18—C20	1.50 (2)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (3)
C20—H20C	0.9600	O2Z—C14Z	1.266 (9)
C21—C22	1.53 (3)	O3Z—C14Z	1.225 (9)
C21—C23	1.57 (2)	C6Z—C5Z	1.3894
C21—H21	0.9800	C6Z—C1Z	1.3922
C22—H22A	0.9600	C6Z—C21Z	1.51 (2)
C22—H22B	0.9600	C1Z—C2Z	1.3891
C22—H22C	0.9600	C1Z—C7Z	1.52 (2)
C23—H23A	0.9600	C2Z—C3Z	1.3894
C23—H23B	0.9600	C2Z—C15Z	1.49 (2)
C23—H23C	0.9600	C3Z—C4Z	1.3887
O1D—C7D	1.46 (2)	C3Z—H3Z	0.9503
O2D—C14D	1.266 (9)	C4Z—C5Z	1.3901
O3D—C14D	1.225 (9)	C4Z—C18Z	1.50 (2)
C1D—C2D	1.362 (19)	C5Z—H5Z	0.9508
C1D—C6D	1.379 (19)	C7Z—C8Z	1.55 (2)
C1D—C7D	1.569 (19)	C7Z—C21Z	1.64 (2)
C2D—C3D	1.41 (2)	C8Z—C13Z	1.3906
C2D—C15D	1.52 (2)	C8Z—C9Z	1.3919
C3D—C4D	1.42 (2)	C9Z—C10Z	1.3876
C3D—H3D	0.9300	C9Z—H9Z	0.9484
C4D—C5D	1.41 (2)	C10Z—C11Z	1.3919
C4D—C18D	1.59 (2)	C10Z—H10Z	0.9502
C5D—C6D	1.384 (19)	C11Z—C12Z	1.3870
C5D—H5D	0.9300	C11Z—C14Z	1.564 (18)
C6D—C21D	1.53 (2)	C12Z—C13Z	1.3948
C7D—C22D	1.50 (2)	C12Z—H12Z	0.9481
C7D—C8D	1.541 (18)	C13Z—H13Z	0.9480
C9D—C10D	1.376 (18)	C15Z—C17Z	1.47 (3)
C9D—C8D	1.387 (18)	C15Z—C16Z	1.47 (3)
C9D—H9D	0.9300	C15Z—H15Z	0.9800
C8D—C13D	1.358 (19)	C16Z—H16J	0.9600
C13D—C12D	1.396 (19)	C16Z—H16K	0.9600
C13D—H13D	0.9300	C16Z—H16L	0.9600
C12D—C11D	1.396 (19)	C17Z—H17J	0.9600
C12D—H12D	0.9300	C17Z—H17K	0.9600
C11D—C10D	1.377 (19)	C17Z—H17L	0.9600
C11D—C14D	1.486 (16)	C18Z—C19Z	1.50 (3)
C10D—H10D	0.9300	C18Z—C20Z	1.52 (3)
C15D—C16D	1.50 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.55 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C22Z	1.52 (2)
C17D—H17F	0.9600	C21Z—C23Z	1.52 (2)
C18D—C19D	1.49 (2)	C22Z—H22I	0.9600
C18D—C20D	1.52 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.510 (9)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.48 (2)	N1—H1C	0.8900
C21D—C22D	1.55 (2)	C24—C25	1.540 (12)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.495 (13)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C31	1.344 (15)
O1P—C7P	1.41 (2)	C26—C27	1.399 (15)
O2P—C14P	1.266 (9)	C27—C28	1.402 (17)
O3P—C14P	1.225 (9)	C27—H27	0.9300
C6P—C1P	1.3892	C28—C29	1.36 (2)
C6P—C5P	1.3911	C28—H28	0.9300
C6P—C21P	1.51 (2)	C29—C30	1.34 (2)
C1P—C2P	1.3907	C29—H29	0.9300
C1P—C7P	1.51 (2)	C30—C31	1.393 (19)
C2P—C3P	1.3909	C30—H30	0.9300
C2P—C15P	1.50 (2)	C31—H31	0.9300
C3P—C4P	1.3861
C6—C1—C2	121 (2)	C1P—C7P—C8P	118 (2)
C6—C1—C7	114 (2)	O1P—C7P—C15P	116 (3)
C2—C1—C7	125 (2)	C1P—C7P—C15P	84.1 (15)
C1—C6—C5	118 (2)	C8P—C7P—C15P	108.9 (17)
C1—C6—C21	121 (2)	C13P—C8P—C9P	119.9
C5—C6—C21	121 (2)	C13P—C8P—C7P	120.6 (17)
C4—C5—C6	123 (3)	C9P—C8P—C7P	119.4 (17)
C4—C5—H5	118.7	C10P—C9P—C8P	120.0
C6—C5—H5	118.7	C10P—C9P—H9P	120.1
C5—C4—C3	119 (2)	C8P—C9P—H9P	119.9
C5—C4—C18	125 (3)	C9P—C10P—C11P	120.1
C3—C4—C18	116 (2)	C9P—C10P—H10P	119.9
C4—C3—C2	120 (3)	C11P—C10P—H10P	120.0
C4—C3—H3	119.8	C12P—C11P—C10P	120.0
C2—C3—H3	119.8	C12P—C11P—C14P	117.7 (18)
C1—C2—C3	120 (2)	C10P—C11P—C14P	122.3 (18)
C1—C2—C15	120 (2)	C11P—C12P—C13P	120.0
C3—C2—C15	120 (2)	C11P—C12P—H12P	120.1
O1—C7—C8	119 (3)	C13P—C12P—H12P	119.9
O1—C7—C1	124 (3)	C8P—C13P—C12P	120.0
C8—C7—C1	117 (2)	C8P—C13P—H13P	120.0
C9—C8—C13	117 (2)	C12P—C13P—H13P	120.0
C9—C8—C7	119 (2)	O3P—C14P—O2P	123.4 (7)
C13—C8—C7	123 (2)	O3P—C14P—C11P	119.6 (14)
C8—C13—C12	124 (3)	O2P—C14P—C11P	116.0 (14)
C8—C13—H13	118.2	C2P—C15P—C16P	120 (3)
C12—C13—H13	118.2	C2P—C15P—C17P	118 (3)
C8—C9—C10	121 (3)	C16P—C15P—C17P	108 (3)
C8—C9—H9	119.7	C2P—C15P—C7P	85.6 (16)
C10—C9—H9	119.7	C16P—C15P—C7P	112 (3)
C11—C10—C9	123 (3)	C17P—C15P—C7P	112 (3)
C11—C10—H10	118.7	C15P—C16P—H16G	109.5
C9—C10—H10	118.7	C15P—C16P—H16H	109.5
C10—C11—C12	117 (2)	H16G—C16P—H16H	109.5
C10—C11—C14	123 (2)	C15P—C16P—H16I	109.5
C12—C11—C14	119 (2)	H16G—C16P—H16I	109.5
C13—C12—C11	119 (3)	H16H—C16P—H16I	109.5
C13—C12—H12	120.6	C15P—C17P—H17G	109.5
C11—C12—H12	120.6	C15P—C17P—H17H	109.5
O3—C14—O2	123.4 (7)	H17G—C17P—H17H	109.5
O3—C14—C11	120.1 (16)	C15P—C17P—H17I	109.5
O2—C14—C11	116.4 (16)	H17G—C17P—H17I	109.5
C16—C15—C17	113 (3)	H17H—C17P—H17I	109.5
C16—C15—C2	117 (3)	C19P—C18P—C4P	111 (3)
C17—C15—C2	116 (3)	C19P—C18P—C20P	111 (3)
C16—C15—H15	102.5	C4P—C18P—C20P	98 (3)
C17—C15—H15	102.5	C19P—C18P—H18P	112.1
C2—C15—H15	102.5	C4P—C18P—H18P	112.1
C15—C16—H16A	109.5	C20P—C18P—H18P	112.1
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C19—C18—C20	115 (3)	H20H—C20P—H20I	109.5
C19—C18—C4	121 (3)	C6P—C21P—C23P	116 (3)
C20—C18—C4	112 (2)	C6P—C21P—C22P	110 (3)
C19—C18—H18	101.5	C23P—C21P—C22P	107 (3)
C20—C18—H18	101.5	C6P—C21P—H21P	107.6
C4—C18—H18	101.5	C23P—C21P—H21P	107.6
C18—C19—H19A	109.5	C22P—C21P—H21P	107.7
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C6—C21—C22	109 (3)	H23H—C23P—H23I	109.5
C6—C21—C23	110 (3)	C5Z—C6Z—C1Z	120.0
C22—C21—C23	106 (3)	C5Z—C6Z—C21Z	145.4 (18)
C6—C21—H21	110.4	C1Z—C6Z—C21Z	94.5 (17)
C22—C21—H21	110.4	C2Z—C1Z—C6Z	119.8
C23—C21—H21	110.4	C2Z—C1Z—C7Z	144.5 (17)
C21—C22—H22A	109.5	C6Z—C1Z—C7Z	94.8 (17)
C21—C22—H22B	109.5	C1Z—C2Z—C3Z	120.20 (8)
H22A—C22—H22B	109.5	C1Z—C2Z—C15Z	117 (2)
C21—C22—H22C	109.5	C3Z—C2Z—C15Z	123 (2)
H22A—C22—H22C	109.5	C4Z—C3Z—C2Z	119.9
H22B—C22—H22C	109.5	C4Z—C3Z—H3Z	120.0
C21—C23—H23A	109.5	C2Z—C3Z—H3Z	120.0
C21—C23—H23B	109.5	C3Z—C4Z—C5Z	120.0
H23A—C23—H23B	109.5	C3Z—C4Z—C18Z	119 (2)
C21—C23—H23C	109.5	C5Z—C4Z—C18Z	121 (2)
H23A—C23—H23C	109.5	C6Z—C5Z—C4Z	120.06 (7)
H23B—C23—H23C	109.5	C6Z—C5Z—H5Z	120.0
C2D—C1D—C6D	120.9 (17)	C4Z—C5Z—H5Z	120.0
C2D—C1D—C7D	125.7 (18)	O1Z—C7Z—C1Z	95 (3)
C6D—C1D—C7D	113.0 (16)	O1Z—C7Z—C8Z	114 (3)
C1D—C2D—C3D	119.5 (18)	C1Z—C7Z—C8Z	119 (3)
C1D—C2D—C15D	121.6 (19)	O1Z—C7Z—C21Z	115 (3)
C3D—C2D—C15D	118.8 (19)	C1Z—C7Z—C21Z	84.7 (17)
C2D—C3D—C4D	121.1 (19)	C8Z—C7Z—C21Z	122 (2)
C2D—C3D—H3D	119.5	C13Z—C8Z—C9Z	120.1
C4D—C3D—H3D	119.5	C13Z—C8Z—C7Z	120 (2)
C5D—C4D—C3D	116.5 (18)	C9Z—C8Z—C7Z	120 (2)
C5D—C4D—C18D	112.5 (19)	C10Z—C9Z—C8Z	120.0
C3D—C4D—C18D	130 (2)	C10Z—C9Z—H9Z	119.8
C6D—C5D—C4D	122 (2)	C8Z—C9Z—H9Z	120.2
C6D—C5D—H5D	119.2	C9Z—C10Z—C11Z	119.9
C4D—C5D—H5D	119.2	C9Z—C10Z—H10Z	120.4
C1D—C6D—C5D	120.3 (18)	C11Z—C10Z—H10Z	119.8
C1D—C6D—C21D	108.2 (16)	C12Z—C11Z—C10Z	120.4
C5D—C6D—C21D	131.5 (19)	C12Z—C11Z—C14Z	118 (2)
O1D—C7D—C22D	109.8 (18)	C10Z—C11Z—C14Z	122 (2)
O1D—C7D—C8D	109.0 (18)	C11Z—C12Z—C13Z	119.8
C22D—C7D—C8D	114.2 (18)	C11Z—C12Z—H12Z	120.5
O1D—C7D—C1D	110.5 (19)	C13Z—C12Z—H12Z	119.8
C22D—C7D—C1D	99.6 (14)	C8Z—C13Z—C12Z	119.9
C8D—C7D—C1D	113.4 (18)	C8Z—C13Z—H13Z	120.1
C10D—C9D—C8D	118.8 (19)	C12Z—C13Z—H13Z	120.0
C10D—C9D—H9D	120.6	O3Z—C14Z—O2Z	123.4 (7)
C8D—C9D—H9D	120.6	O3Z—C14Z—C11Z	118.3 (14)
C13D—C8D—C9D	120.0 (17)	O2Z—C14Z—C11Z	118.3 (14)
C13D—C8D—C7D	120.1 (17)	C17Z—C15Z—C16Z	122 (4)
C9D—C8D—C7D	119.9 (17)	C17Z—C15Z—C2Z	112 (3)
C8D—C13D—C12D	121 (2)	C16Z—C15Z—C2Z	107 (3)
C8D—C13D—H13D	119.4	C17Z—C15Z—H15Z	104.8
C12D—C13D—H13D	119.4	C16Z—C15Z—H15Z	104.8
C13D—C12D—C11D	120 (2)	C2Z—C15Z—H15Z	104.8
C13D—C12D—H12D	120.2	C15Z—C16Z—H16J	109.5
C11D—C12D—H12D	120.2	C15Z—C16Z—H16K	109.5
C10D—C11D—C12D	117.8 (17)	H16J—C16Z—H16K	109.5
C10D—C11D—C14D	121.0 (17)	C15Z—C16Z—H16L	109.5
C12D—C11D—C14D	121.2 (17)	H16J—C16Z—H16L	109.5
C9D—C10D—C11D	123 (2)	H16K—C16Z—H16L	109.5
C9D—C10D—H10D	118.6	C15Z—C17Z—H17J	109.5
C11D—C10D—H10D	118.6	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	123.4 (7)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	117.0 (12)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	119.5 (12)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	108 (2)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	114 (2)	C19Z—C18Z—C4Z	98 (3)
C2D—C15D—C17D	107 (2)	C19Z—C18Z—C20Z	114 (4)
C16D—C15D—H15D	108.9	C4Z—C18Z—C20Z	125 (4)
C2D—C15D—H15D	108.9	C19Z—C18Z—H18Z	106.0
C17D—C15D—H15D	108.9	C4Z—C18Z—H18Z	106.0
C15D—C16D—H16D	109.5	C20Z—C18Z—H18Z	106.0
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C19D—C18D—C20D	117 (2)	H20K—C20Z—H20L	109.5
C19D—C18D—C4D	112.5 (19)	C6Z—C21Z—C22Z	109 (3)
C20D—C18D—C4D	112 (2)	C6Z—C21Z—C23Z	121 (3)
C19D—C18D—H18D	104.3	C22Z—C21Z—C23Z	112 (3)
C20D—C18D—H18D	104.3	C6Z—C21Z—C7Z	85.6 (17)
C4D—C18D—H18D	104.3	C22Z—C21Z—C7Z	115 (3)
C18D—C19D—H19D	109.5	C23Z—C21Z—C7Z	113 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	118 (2)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	116 (2)	C25—N1—H1A	109.5
C6D—C21D—C22D	101.7 (17)	C25—N1—H1B	109.5
C23D—C21D—H21D	106.9	H1A—N1—H1B	109.5
C6D—C21D—H21D	106.9	C25—N1—H1C	109.5
C22D—C21D—H21D	106.9	H1A—N1—H1C	109.5
C7D—C22D—C21D	108.7 (16)	H1B—N1—H1C	109.5
C7D—C22D—H22D	109.9	C25—C24—H24A	109.5
C21D—C22D—H22D	109.9	C25—C24—H24B	109.5
C7D—C22D—H22E	109.9	H24A—C24—H24B	109.5
C21D—C22D—H22E	109.9	C25—C24—H24C	109.5
H22D—C22D—H22E	108.3	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	110.6 (7)
H23D—C23D—H23E	109.5	C26—C25—C24	113.9 (9)
C21D—C23D—H23F	109.5	N1—C25—C24	107.5 (7)
H23D—C23D—H23F	109.5	C26—C25—H25	108.2
H23E—C23D—H23F	109.5	N1—C25—H25	108.2
C1P—C6P—C5P	120.0	C24—C25—H25	108.2
C1P—C6P—C21P	125 (2)	C31—C26—C27	119.5 (12)
C5P—C6P—C21P	115 (2)	C31—C26—C25	122.0 (13)
C6P—C1P—C2P	120.0	C27—C26—C25	118.5 (12)
C6P—C1P—C7P	144.1 (17)	C26—C27—C28	119.2 (14)
C2P—C1P—C7P	95.4 (16)	C26—C27—H27	120.4
C1P—C2P—C3P	119.90 (7)	C28—C27—H27	120.4
C1P—C2P—C15P	94.0 (17)	C29—C28—C27	118 (2)
C3P—C2P—C15P	146.0 (17)	C29—C28—H28	120.9
C4P—C3P—C2P	120.1	C27—C28—H28	120.9
C4P—C3P—H3P	120.1	C30—C29—C28	124 (3)
C2P—C3P—H3P	119.8	C30—C29—H29	118.2
C3P—C4P—C5P	120.1	C28—C29—H29	118.2
C3P—C4P—C18P	121 (2)	C29—C30—C31	118 (2)
C5P—C4P—C18P	119 (2)	C29—C30—H30	121.1
C4P—C5P—C6P	119.92 (7)	C31—C30—H30	121.1
C4P—C5P—H5P	120.1	C26—C31—C30	121.7 (17)
C6P—C5P—H5P	120.0	C26—C31—H31	119.1
O1P—C7P—C1P	122 (3)	C30—C31—H31	119.1
O1P—C7P—C8P	106 (2)

(1950minUV)

Crystal data

C31H39NO3	Dx = 1.126 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1033 reflections
a = 6.401 (2) Å	θ = 1.6–16.7°
b = 13.422 (4) Å	µ = 0.07 mm^−1
c = 32.510 (9) Å	T = 299 K
V = 2793.1 (14) Å^3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5392 independent reflections
Radiation source: fine-focus sealed tube	1731 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.138
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→16
Tmin = 0.413, Tmax = 1.000	l = −40→40
24981 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.092	H-atom parameters constrained
wR(F^2) = 0.247	w = 1/[σ^2(Fo^2) + (0.0665P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5392 reflections	Δρmax = 0.14 e Å^−3
402 parameters	Δρmin = −0.15 e Å^−3
494 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.0 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.062 (7)	0.243 (4)	0.6402 (18)	0.084 (10)	0.209 (4)
O2	0.6682 (10)	0.6314 (4)	0.51864 (18)	0.094 (2)	0.209 (4)
O3	0.3655 (11)	0.6146 (5)	0.54890 (18)	0.102 (2)	0.209 (4)
C6	0.697 (7)	0.197 (2)	0.6997 (8)	0.068 (11)*	0.209 (4)
C1	0.826 (7)	0.280 (3)	0.6946 (8)	0.070 (13)*	0.209 (4)
C2	0.864 (7)	0.345 (3)	0.7271 (9)	0.074 (12)*	0.209 (4)
C3	0.771 (6)	0.325 (3)	0.7649 (8)	0.066 (10)*	0.209 (4)
H3	0.7944	0.3686	0.7867	0.079*	0.209 (4)
C4	0.645 (6)	0.244 (3)	0.7710 (7)	0.063 (10)*	0.209 (4)
C5	0.609 (6)	0.182 (2)	0.7379 (9)	0.079 (12)*	0.209 (4)
H5	0.5227	0.1269	0.7415	0.095*	0.209 (4)
C7	0.916 (5)	0.294 (2)	0.6521 (8)	0.081 (12)*	0.209 (4)
C8	0.820 (5)	0.3699 (17)	0.6245 (7)	0.059 (11)*	0.209 (4)
C9	0.940 (4)	0.412 (2)	0.5940 (9)	0.041 (9)*	0.209 (4)
H9	1.0777	0.3931	0.5908	0.049*	0.209 (4)
C10	0.857 (5)	0.483 (2)	0.5682 (9)	0.071 (12)*	0.209 (4)
H10	0.9400	0.5114	0.5481	0.085*	0.209 (4)
C11	0.652 (5)	0.511 (3)	0.5717 (12)	0.064 (13)*	0.209 (4)
C12	0.531 (5)	0.466 (4)	0.6010 (15)	0.071 (13)*	0.209 (4)
H12	0.3906	0.4826	0.6030	0.085*	0.209 (4)
C13	0.615 (5)	0.397 (3)	0.6275 (12)	0.068 (12)*	0.209 (4)
H13	0.5318	0.3682	0.6476	0.082*	0.209 (4)
C14	0.5514 (16)	0.5918 (6)	0.5446 (3)	0.078 (2)	0.209 (4)
C15	1.028 (6)	0.428 (3)	0.7224 (15)	0.081 (12)*	0.209 (4)
H15	1.0429	0.4429	0.6930	0.098*	0.209 (4)
C16	1.239 (7)	0.391 (4)	0.738 (2)	0.13 (2)*	0.209 (4)
H16A	1.2773	0.3312	0.7242	0.194*	0.209 (4)
H16B	1.3437	0.4413	0.7336	0.194*	0.209 (4)
H16C	1.2295	0.3782	0.7673	0.194*	0.209 (4)
C17	0.960 (7)	0.523 (3)	0.7438 (15)	0.094 (14)*	0.209 (4)
H17A	0.8271	0.5442	0.7330	0.141*	0.209 (4)
H17B	0.9474	0.5114	0.7728	0.141*	0.209 (4)
H17C	1.0617	0.5745	0.7390	0.141*	0.209 (4)
C18	0.555 (6)	0.221 (4)	0.8140 (9)	0.100 (13)*	0.209 (4)
H18	0.5359	0.1490	0.8155	0.119*	0.209 (4)
C19	0.694 (7)	0.249 (4)	0.8491 (11)	0.067 (13)*	0.209 (4)
H19A	0.8283	0.2183	0.8457	0.101*	0.209 (4)
H19B	0.7114	0.3204	0.8497	0.101*	0.209 (4)
H19C	0.6329	0.2275	0.8745	0.101*	0.209 (4)
C20	0.340 (6)	0.267 (4)	0.8168 (13)	0.068 (14)*	0.209 (4)
H20A	0.2583	0.2465	0.7936	0.102*	0.209 (4)
H20B	0.2736	0.2453	0.8417	0.102*	0.209 (4)
H20C	0.3521	0.3383	0.8170	0.102*	0.209 (4)
C21	0.643 (7)	0.129 (3)	0.6643 (12)	0.084 (13)*	0.209 (4)
H21	0.6275	0.1661	0.6385	0.100*	0.209 (4)
C22	0.814 (8)	0.049 (4)	0.6610 (17)	0.099 (17)*	0.209 (4)
H22A	0.7818	0.0052	0.6387	0.148*	0.209 (4)
H22B	0.9461	0.0809	0.6561	0.148*	0.209 (4)
H22C	0.8201	0.0122	0.6862	0.148*	0.209 (4)
C23	0.440 (7)	0.069 (4)	0.675 (2)	0.076 (15)*	0.209 (4)
H23A	0.4055	0.0259	0.6528	0.114*	0.209 (4)
H23B	0.4639	0.0307	0.6996	0.114*	0.209 (4)
H23C	0.3275	0.1151	0.6799	0.114*	0.209 (4)
O1D	1.099 (3)	0.269 (2)	0.6419 (10)	0.081 (8)	0.394 (4)
O2D	0.6682 (10)	0.6314 (4)	0.51864 (18)	0.094 (2)	0.394 (4)
O3D	0.3655 (11)	0.6146 (5)	0.54890 (18)	0.102 (2)	0.394 (4)
C6D	0.658 (4)	0.2093 (14)	0.7035 (5)	0.070 (8)*	0.394 (4)
C1D	0.807 (3)	0.2794 (14)	0.6921 (4)	0.071 (8)*	0.394 (4)
C2D	0.890 (3)	0.3452 (13)	0.7199 (5)	0.072 (7)*	0.394 (4)
C3D	0.834 (3)	0.3351 (15)	0.7614 (5)	0.082 (7)*	0.394 (4)
H3D	0.8927	0.3788	0.7811	0.098*	0.394 (4)
C4D	0.690 (3)	0.2612 (16)	0.7747 (4)	0.085 (9)*	0.394 (4)
C5D	0.601 (3)	0.2013 (14)	0.7444 (6)	0.068 (7)*	0.394 (4)
H5D	0.4997	0.1536	0.7520	0.081*	0.394 (4)
C7D	0.874 (3)	0.2713 (14)	0.6463 (6)	0.083 (8)*	0.394 (4)
C8D	0.783 (3)	0.3558 (11)	0.6206 (5)	0.068 (8)*	0.394 (4)
C9D	0.897 (3)	0.3904 (15)	0.5876 (6)	0.070 (8)*	0.394 (4)
H9D	1.0290	0.3618	0.5821	0.085*	0.394 (4)
C10D	0.824 (3)	0.4656 (17)	0.5626 (6)	0.072 (8)*	0.394 (4)
H10D	0.9052	0.4878	0.5399	0.087*	0.394 (4)
C11D	0.630 (3)	0.5094 (17)	0.5707 (7)	0.067 (9)*	0.394 (4)
C12D	0.516 (3)	0.472 (2)	0.6034 (9)	0.069 (9)*	0.394 (4)
H12D	0.3817	0.4986	0.6086	0.083*	0.394 (4)
C13D	0.593 (3)	0.3985 (19)	0.6286 (7)	0.079 (9)*	0.394 (4)
H13D	0.5145	0.3772	0.6517	0.095*	0.394 (4)
C14D	0.5514 (16)	0.5918 (6)	0.5446 (3)	0.078 (2)	0.394 (4)
C15D	1.037 (4)	0.4274 (18)	0.7071 (9)	0.089 (9)*	0.394 (4)
H15D	1.0536	0.4234	0.6772	0.107*	0.394 (4)
C16D	1.245 (4)	0.421 (3)	0.7257 (12)	0.070 (10)*	0.394 (4)
H16D	1.3299	0.4749	0.7162	0.105*	0.394 (4)
H16E	1.2333	0.4235	0.7551	0.105*	0.394 (4)
H16F	1.3093	0.3586	0.7178	0.105*	0.394 (4)
C17D	0.929 (6)	0.5280 (18)	0.7170 (11)	0.076 (10)*	0.394 (4)
H17D	0.7932	0.5296	0.7044	0.114*	0.394 (4)
H17E	0.9142	0.5349	0.7463	0.114*	0.394 (4)
H17F	1.0121	0.5817	0.7065	0.114*	0.394 (4)
C18D	0.627 (5)	0.237 (3)	0.8195 (7)	0.117 (10)*	0.394 (4)
H18D	0.6491	0.1650	0.8173	0.141*	0.394 (4)
C19D	0.777 (6)	0.252 (3)	0.8538 (8)	0.101 (11)*	0.394 (4)
H19D	0.9166	0.2552	0.8430	0.152*	0.394 (4)
H19E	0.7455	0.3139	0.8676	0.152*	0.394 (4)
H19F	0.7661	0.1982	0.8729	0.152*	0.394 (4)
C20D	0.399 (5)	0.230 (3)	0.8291 (12)	0.119 (15)*	0.394 (4)
H20D	0.3219	0.2206	0.8041	0.178*	0.394 (4)
H20E	0.3748	0.1755	0.8474	0.178*	0.394 (4)
H20F	0.3542	0.2911	0.8420	0.178*	0.394 (4)
C21D	0.603 (5)	0.149 (2)	0.6653 (8)	0.091 (10)*	0.394 (4)
H21D	0.4761	0.1791	0.6536	0.109*	0.394 (4)
C22D	0.784 (3)	0.1734 (14)	0.6354 (6)	0.082 (7)*	0.394 (4)
H22D	0.8910	0.1223	0.6373	0.098*	0.394 (4)
H22E	0.7328	0.1749	0.6073	0.098*	0.394 (4)
C23D	0.562 (5)	0.0415 (17)	0.6701 (8)	0.119 (10)*	0.394 (4)
H23D	0.5293	0.0132	0.6437	0.178*	0.394 (4)
H23E	0.6834	0.0095	0.6812	0.178*	0.394 (4)
H23F	0.4458	0.0319	0.6884	0.178*	0.394 (4)
O1P	1.122 (6)	0.304 (3)	0.6524 (14)	0.082 (9)	0.233 (4)
O2P	0.6682 (10)	0.6314 (4)	0.51864 (18)	0.094 (2)	0.233 (4)
O3P	0.3655 (11)	0.6146 (5)	0.54890 (18)	0.102 (2)	0.233 (4)
C6P	0.676 (5)	0.214 (2)	0.7053 (8)	0.072 (12)*	0.233 (4)
C1P	0.807 (5)	0.295 (2)	0.7009 (6)	0.065 (10)*	0.233 (4)
C2P	0.873 (5)	0.347 (2)	0.7353 (8)	0.059 (9)*	0.233 (4)
C3P	0.807 (5)	0.318 (2)	0.7741 (7)	0.083 (11)*	0.233 (4)
H3P	0.8527	0.3538	0.7976	0.100*	0.233 (4)
C4P	0.677 (5)	0.237 (2)	0.7786 (7)	0.071 (11)*	0.233 (4)
C5P	0.610 (5)	0.184 (2)	0.7442 (9)	0.081 (12)*	0.233 (4)
H5P	0.5203	0.1290	0.7472	0.097*	0.233 (4)
C7P	0.946 (4)	0.3482 (16)	0.6705 (6)	0.057 (8)*	0.233 (4)
C8P	0.836 (4)	0.4077 (13)	0.6366 (5)	0.050 (8)*	0.233 (4)
C9P	0.958 (3)	0.4502 (17)	0.6060 (7)	0.082 (10)*	0.233 (4)
H9P	1.1029	0.4380	0.6054	0.098*	0.233 (4)
C10P	0.867 (4)	0.5103 (17)	0.5764 (6)	0.072 (10)*	0.233 (4)
H10P	0.9501	0.5393	0.5555	0.086*	0.233 (4)
C11P	0.654 (4)	0.5281 (14)	0.5773 (6)	0.075 (11)*	0.233 (4)
C12P	0.533 (3)	0.486 (2)	0.6078 (8)	0.067 (12)*	0.233 (4)
H12P	0.3878	0.4978	0.6085	0.081*	0.233 (4)
C13P	0.624 (4)	0.426 (2)	0.6375 (7)	0.060 (10)*	0.233 (4)
H13P	0.5406	0.3965	0.6583	0.072*	0.233 (4)
C14P	0.5514 (16)	0.5918 (6)	0.5446 (3)	0.078 (2)	0.233 (4)
C15P	0.995 (5)	0.421 (2)	0.7106 (9)	0.065 (11)*	0.233 (4)
C16P	1.228 (6)	0.432 (4)	0.7166 (17)	0.089 (19)*	0.233 (4)
H16G	1.2802	0.4824	0.6984	0.134*	0.233 (4)
H16H	1.2556	0.4508	0.7446	0.134*	0.233 (4)
H16I	1.2952	0.3697	0.7108	0.134*	0.233 (4)
C17P	0.910 (10)	0.526 (2)	0.7056 (17)	0.11 (2)*	0.233 (4)
H17G	1.0052	0.5645	0.6891	0.167*	0.233 (4)
H17H	0.7763	0.5238	0.6924	0.167*	0.233 (4)
H17I	0.8966	0.5567	0.7322	0.167*	0.233 (4)
C18P	0.604 (6)	0.202 (3)	0.8207 (9)	0.084 (11)*	0.233 (4)
H18P	0.5336	0.1368	0.8205	0.101*	0.233 (4)
C19P	0.788 (8)	0.208 (4)	0.8500 (13)	0.113 (17)*	0.233 (4)
H19G	0.7453	0.1858	0.8769	0.170*	0.233 (4)
H19H	0.8985	0.1656	0.8402	0.170*	0.233 (4)
H19I	0.8364	0.2752	0.8515	0.170*	0.233 (4)
C20P	0.456 (8)	0.291 (4)	0.8305 (16)	0.14 (2)*	0.233 (4)
H20G	0.3378	0.2887	0.8123	0.217*	0.233 (4)
H20H	0.4092	0.2860	0.8584	0.217*	0.233 (4)
H20I	0.5303	0.3521	0.8266	0.217*	0.233 (4)
C21P	0.593 (6)	0.152 (3)	0.6700 (12)	0.084 (12)*	0.233 (4)
H21P	0.5575	0.1968	0.6473	0.100*	0.233 (4)
C22P	0.768 (8)	0.082 (4)	0.6554 (16)	0.114 (16)*	0.233 (4)
H22F	0.7187	0.0421	0.6330	0.171*	0.233 (4)
H22G	0.8856	0.1210	0.6465	0.171*	0.233 (4)
H22H	0.8100	0.0395	0.6777	0.171*	0.233 (4)
C23P	0.401 (7)	0.088 (4)	0.680 (2)	0.116 (19)*	0.233 (4)
H23G	0.3608	0.0518	0.6555	0.173*	0.233 (4)
H23H	0.4342	0.0421	0.7013	0.173*	0.233 (4)
H23I	0.2884	0.1304	0.6882	0.173*	0.233 (4)
O1Z	1.107 (6)	0.283 (5)	0.6572 (17)	0.083 (10)*	0.164 (4)
O2Z	0.6682 (10)	0.6314 (4)	0.51864 (18)	0.094 (2)	0.164 (4)
O3Z	0.3655 (11)	0.6146 (5)	0.54890 (18)	0.102 (2)	0.164 (4)
C6Z	0.754 (6)	0.217 (2)	0.7086 (8)	0.055 (10)*	0.164 (4)
C1Z	0.861 (6)	0.305 (2)	0.7019 (7)	0.061 (11)*	0.164 (4)
C2Z	0.888 (6)	0.372 (2)	0.7339 (9)	0.078 (12)*	0.164 (4)
C3Z	0.809 (6)	0.351 (2)	0.7726 (8)	0.084 (13)*	0.164 (4)
H3Z	0.8283	0.3969	0.7944	0.101*	0.164 (4)
C4Z	0.703 (6)	0.263 (3)	0.7793 (8)	0.080 (13)*	0.164 (4)
C5Z	0.676 (5)	0.196 (2)	0.7474 (9)	0.077 (12)*	0.164 (4)
H5Z	0.6029	0.1351	0.7520	0.093*	0.164 (4)
C7Z	0.885 (6)	0.287 (2)	0.6561 (9)	0.082 (13)*	0.164 (4)
C8Z	0.799 (6)	0.366 (2)	0.6264 (10)	0.064 (13)*	0.164 (4)
C9Z	0.883 (7)	0.376 (3)	0.5873 (11)	0.071 (13)*	0.164 (4)
H9Z	0.9930	0.3345	0.5787	0.085*	0.164 (4)
C10Z	0.805 (6)	0.448 (3)	0.5608 (9)	0.057 (12)*	0.164 (4)
H10Z	0.8622	0.4556	0.5341	0.069*	0.164 (4)
C11Z	0.643 (4)	0.5094 (14)	0.5735 (8)	0.070 (14)*	0.164 (4)
C12Z	0.559 (5)	0.499 (2)	0.6124 (10)	0.066 (12)*	0.164 (4)
H12Z	0.4491	0.5410	0.6211	0.079*	0.164 (4)
C13Z	0.637 (6)	0.427 (3)	0.6390 (9)	0.065 (13)*	0.164 (4)
H13Z	0.5799	0.4198	0.6657	0.078*	0.164 (4)
C14Z	0.5514 (16)	0.5918 (6)	0.5446 (3)	0.078 (2)	0.164 (4)
C15Z	1.006 (7)	0.464 (3)	0.7228 (15)	0.078 (13)*	0.164 (4)
H15Z	1.0228	0.4620	0.6928	0.094*	0.164 (4)
C16Z	1.218 (6)	0.448 (4)	0.7399 (19)	0.10 (2)*	0.164 (4)
H16J	1.2701	0.3845	0.7309	0.143*	0.164 (4)
H16K	1.3101	0.4997	0.7304	0.143*	0.164 (4)
H16L	1.2121	0.4493	0.7694	0.143*	0.164 (4)
C17Z	0.888 (8)	0.555 (3)	0.7312 (18)	0.074 (16)*	0.164 (4)
H17J	0.7549	0.5514	0.7175	0.110*	0.164 (4)
H17K	0.8659	0.5612	0.7603	0.110*	0.164 (4)
H17L	0.9638	0.6116	0.7213	0.110*	0.164 (4)
C18Z	0.616 (9)	0.238 (4)	0.8211 (11)	0.110 (14)*	0.164 (4)
H18Z	0.6510	0.1690	0.8288	0.132*	0.164 (4)
C19Z	0.748 (10)	0.311 (5)	0.8454 (15)	0.12 (2)*	0.164 (4)
H19J	0.7135	0.3068	0.8741	0.174*	0.164 (4)
H19K	0.8931	0.2964	0.8416	0.174*	0.164 (4)
H19L	0.7201	0.3778	0.8358	0.174*	0.164 (4)
C20Z	0.385 (8)	0.259 (7)	0.830 (2)	0.07 (2)*	0.164 (4)
H20J	0.3531	0.2392	0.8579	0.107*	0.164 (4)
H20K	0.3588	0.3292	0.8272	0.107*	0.164 (4)
H20L	0.2988	0.2226	0.8114	0.107*	0.164 (4)
C21Z	0.764 (6)	0.181 (2)	0.6646 (9)	0.092 (13)*	0.164 (4)
C22Z	0.913 (8)	0.093 (3)	0.6626 (16)	0.101 (18)*	0.164 (4)
H22I	0.9209	0.0691	0.6348	0.152*	0.164 (4)
H22J	1.0487	0.1134	0.6717	0.152*	0.164 (4)
H22K	0.8619	0.0407	0.6801	0.152*	0.164 (4)
C23Z	0.567 (7)	0.167 (4)	0.6392 (17)	0.12 (2)*	0.164 (4)
H23J	0.6043	0.1437	0.6122	0.184*	0.164 (4)
H23K	0.4787	0.1186	0.6523	0.184*	0.164 (4)
H23L	0.4949	0.2292	0.6370	0.184*	0.164 (4)
N1	0.0735 (10)	0.6664 (5)	0.49207 (18)	0.075 (2)
H1A	0.1778	0.6458	0.5080	0.090*
H1B	−0.0479	0.6494	0.5034	0.090*
H1C	0.0795	0.7324	0.4894	0.090*
C24	0.3064 (16)	0.6478 (8)	0.4332 (3)	0.114 (4)
H24A	0.4130	0.6303	0.4527	0.171*
H24B	0.3101	0.7183	0.4283	0.171*
H24C	0.3303	0.6129	0.4079	0.171*
C25	0.0920 (15)	0.6188 (8)	0.4505 (3)	0.084 (3)
H25	−0.0157	0.6473	0.4326	0.101*
C26	0.055 (2)	0.5087 (9)	0.4535 (3)	0.094 (3)
C27	−0.132 (2)	0.4714 (12)	0.4399 (4)	0.123 (4)
H27	−0.2352	0.5147	0.4305	0.148*
C28	−0.169 (3)	0.3688 (17)	0.4400 (5)	0.174 (7)
H28	−0.2924	0.3427	0.4296	0.208*
C29	−0.022 (5)	0.309 (2)	0.4555 (8)	0.221 (14)
H29	−0.0488	0.2413	0.4564	0.265*
C30	0.163 (4)	0.3410 (16)	0.4699 (6)	0.190 (8)
H30	0.2624	0.2967	0.4798	0.228*
C31	0.200 (3)	0.4460 (12)	0.4694 (4)	0.148 (5)
H31	0.3236	0.4713	0.4800	0.177*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.079 (15)	0.086 (17)	0.085 (14)	0.016 (15)	0.020 (14)	0.014 (14)
O2	0.084 (4)	0.116 (5)	0.083 (4)	0.005 (4)	0.019 (4)	0.038 (4)
O3	0.078 (4)	0.153 (5)	0.074 (4)	0.027 (5)	−0.002 (4)	0.035 (4)
C14	0.089 (6)	0.090 (6)	0.055 (5)	0.003 (6)	−0.013 (6)	0.008 (4)
O1D	0.071 (11)	0.089 (16)	0.082 (12)	0.015 (13)	0.017 (11)	0.008 (12)
O2D	0.084 (4)	0.116 (5)	0.083 (4)	0.005 (4)	0.019 (4)	0.038 (4)
O3D	0.078 (4)	0.153 (5)	0.074 (4)	0.027 (5)	−0.002 (4)	0.035 (4)
C14D	0.089 (6)	0.090 (6)	0.055 (5)	0.003 (6)	−0.013 (6)	0.008 (4)
O1P	0.075 (13)	0.088 (17)	0.083 (16)	0.008 (14)	0.019 (13)	0.023 (14)
O2P	0.084 (4)	0.116 (5)	0.083 (4)	0.005 (4)	0.019 (4)	0.038 (4)
O3P	0.078 (4)	0.153 (5)	0.074 (4)	0.027 (5)	−0.002 (4)	0.035 (4)
C14P	0.089 (6)	0.090 (6)	0.055 (5)	0.003 (6)	−0.013 (6)	0.008 (4)
O2Z	0.084 (4)	0.116 (5)	0.083 (4)	0.005 (4)	0.019 (4)	0.038 (4)
O3Z	0.078 (4)	0.153 (5)	0.074 (4)	0.027 (5)	−0.002 (4)	0.035 (4)
C14Z	0.089 (6)	0.090 (6)	0.055 (5)	0.003 (6)	−0.013 (6)	0.008 (4)
N1	0.058 (4)	0.098 (5)	0.069 (5)	0.005 (4)	0.003 (4)	0.011 (4)
C24	0.114 (9)	0.151 (9)	0.076 (6)	0.004 (8)	0.033 (6)	0.006 (6)
C25	0.082 (7)	0.115 (8)	0.056 (6)	0.018 (6)	0.000 (5)	0.006 (5)
C26	0.119 (11)	0.104 (9)	0.058 (6)	0.009 (9)	−0.005 (7)	−0.004 (6)
C27	0.106 (11)	0.153 (13)	0.111 (9)	−0.013 (10)	0.022 (9)	−0.018 (8)
C28	0.18 (2)	0.18 (2)	0.153 (15)	−0.078 (16)	0.030 (14)	−0.042 (14)
C29	0.32 (5)	0.16 (2)	0.19 (2)	−0.04 (2)	0.03 (3)	0.012 (15)
C30	0.26 (3)	0.134 (18)	0.175 (17)	0.048 (17)	0.012 (17)	0.023 (12)
C31	0.195 (16)	0.118 (11)	0.130 (11)	−0.001 (12)	−0.042 (11)	0.008 (8)

Geometric parameters (Å, º)

O1—C7	1.22 (2)	C3P—H3P	0.9480
O2—C14	1.247 (9)	C4P—C5P	1.3866
O3—C14	1.237 (10)	C4P—C18P	1.52 (2)
C6—C5	1.3806	C5P—H5P	0.9466
C6—C1	1.3900	C7P—C8P	1.535 (18)
C6—C21	1.51 (2)	C7P—C15P	1.66 (2)
C1—C2	1.3932	C8P—C13P	1.3809
C1—C7	1.51 (2)	C8P—C9P	1.3857
C2—C3	1.3925	C9P—C10P	1.3840
C2—C15	1.54 (2)	C9P—H9P	0.9434
C3—C4	1.3727	C10P—C11P	1.3816
C3—H3	0.9279	C10P—H10P	0.9467
C4—C5	1.3817	C11P—C12P	1.3826
C4—C18	1.54 (2)	C11P—C14P	1.514 (14)
C5—H5	0.9267	C12P—C13P	1.3864
C7—C8	1.49 (2)	C12P—H12P	0.9436
C8—C13	1.3688	C13P—H13P	0.9466
C8—C9	1.3767	C15P—C16P	1.51 (2)
C9—C10	1.3691	C15P—C17P	1.52 (2)
C9—H9	0.9241	C16P—H16G	0.9600
C10—C11	1.3733	C16P—H16H	0.9600
C10—H10	0.9265	C16P—H16I	0.9600
C11—C12	1.3682	C17P—H17G	0.9600
C11—C14	1.535 (17)	C17P—H17H	0.9600
C12—C13	1.3789	C17P—H17I	0.9600
C12—H12	0.9239	C18P—C19P	1.52 (3)
C13—H13	0.9265	C18P—C20P	1.55 (3)
C15—C17	1.52 (3)	C18P—H18P	0.9800
C15—C16	1.53 (3)	C19P—H19G	0.9600
C15—H15	0.9800	C19P—H19H	0.9600
C16—H16A	0.9600	C19P—H19I	0.9600
C16—H16B	0.9600	C20P—H20G	0.9600
C16—H16C	0.9600	C20P—H20H	0.9600
C17—H17A	0.9600	C20P—H20I	0.9600
C17—H17B	0.9600	C21P—C23P	1.53 (3)
C17—H17C	0.9600	C21P—C22P	1.54 (3)
C18—C19	1.50 (3)	C21P—H21P	0.9800
C18—C20	1.51 (3)	C22P—H22F	0.9600
C18—H18	0.9800	C22P—H22G	0.9600
C19—H19A	0.9600	C22P—H22H	0.9600
C19—H19B	0.9600	C23P—H23G	0.9600
C19—H19C	0.9600	C23P—H23H	0.9600
C20—H20A	0.9600	C23P—H23I	0.9600
C20—H20B	0.9600	O1Z—C7Z	1.42 (2)
C20—H20C	0.9600	O2Z—C14Z	1.247 (9)
C21—C22	1.53 (3)	O3Z—C14Z	1.237 (10)
C21—C23	1.57 (2)	C6Z—C5Z	1.3853
C21—H21	0.9800	C6Z—C1Z	1.3878
C22—H22A	0.9600	C6Z—C21Z	1.51 (2)
C22—H22B	0.9600	C1Z—C2Z	1.3860
C22—H22C	0.9600	C1Z—C7Z	1.52 (2)
C23—H23A	0.9600	C2Z—C3Z	1.3852
C23—H23B	0.9600	C2Z—C15Z	1.49 (2)
C23—H23C	0.9600	C3Z—C4Z	1.3843
O1D—C7D	1.45 (2)	C3Z—H3Z	0.9483
O2D—C14D	1.247 (9)	C4Z—C5Z	1.3870
O3D—C14D	1.237 (10)	C4Z—C18Z	1.51 (2)
C6D—C5D	1.3795	C5Z—H5Z	0.9478
C6D—C1D	1.3916	C7Z—C8Z	1.54 (2)
C6D—C21D	1.521 (19)	C7Z—C21Z	1.64 (2)
C1D—C2D	1.3719	C8Z—C13Z	1.3840
C1D—C7D	1.552 (17)	C8Z—C9Z	1.3877
C2D—C3D	1.4015	C9Z—C10Z	1.3838
C2D—C15D	1.506 (19)	C9Z—H9Z	0.9440
C3D—C4D	1.4202	C10Z—C11Z	1.3854
C3D—H3D	0.9477	C10Z—H10Z	0.9472
C4D—C5D	1.3935	C11Z—C12Z	1.3826
C4D—C18D	1.546 (19)	C11Z—C14Z	1.566 (17)
C5D—H5D	0.9459	C12Z—C13Z	1.3910
C7D—C22D	1.478 (19)	C12Z—H12Z	0.9436
C7D—C8D	1.525 (17)	C13Z—H13Z	0.9451
C8D—C13D	1.3687	C15Z—C17Z	1.46 (3)
C8D—C9D	1.3785	C15Z—C16Z	1.48 (3)
C9D—C10D	1.3774	C15Z—H15Z	0.9800
C9D—H9D	0.9442	C16Z—H16J	0.9600
C10D—C11D	1.4032	C16Z—H16K	0.9600
C10D—H10D	0.9477	C16Z—H16L	0.9600
C11D—C12D	1.3789	C17Z—H17J	0.9600
C11D—C14D	1.481 (13)	C17Z—H17K	0.9600
C12D—C13D	1.3795	C17Z—H17L	0.9600
C12D—H12D	0.9446	C18Z—C19Z	1.52 (3)
C13D—H13D	0.9472	C18Z—C20Z	1.53 (3)
C15D—C16D	1.47 (2)	C18Z—H18Z	0.9800
C15D—C17D	1.55 (2)	C19Z—H19J	0.9600
C15D—H15D	0.9800	C19Z—H19K	0.9600
C16D—H16D	0.9600	C19Z—H19L	0.9600
C16D—H16E	0.9600	C20Z—H20J	0.9600
C16D—H16F	0.9600	C20Z—H20K	0.9600
C17D—H17D	0.9600	C20Z—H20L	0.9600
C17D—H17E	0.9600	C21Z—C22Z	1.51 (2)
C17D—H17F	0.9600	C21Z—C23Z	1.52 (2)
C18D—C19D	1.49 (2)	C22Z—H22I	0.9600
C18D—C20D	1.49 (2)	C22Z—H22J	0.9600
C18D—H18D	0.9800	C22Z—H22K	0.9600
C19D—H19D	0.9600	C23Z—H23J	0.9600
C19D—H19E	0.9600	C23Z—H23K	0.9600
C19D—H19F	0.9600	C23Z—H23L	0.9600
C20D—H20D	0.9600	N1—C25	1.500 (10)
C20D—H20E	0.9600	N1—H1A	0.8900
C20D—H20F	0.9600	N1—H1B	0.8900
C21D—C23D	1.48 (2)	N1—H1C	0.8900
C21D—C22D	1.55 (2)	C24—C25	1.533 (12)
C21D—H21D	0.9800	C24—H24A	0.9600
C22D—H22D	0.9700	C24—H24B	0.9600
C22D—H22E	0.9700	C24—H24C	0.9600
C23D—H23D	0.9600	C25—C26	1.500 (13)
C23D—H23E	0.9600	C25—H25	0.9800
C23D—H23F	0.9600	C26—C31	1.353 (16)
O1P—C7P	1.40 (2)	C26—C27	1.373 (16)
O2P—C14P	1.247 (9)	C27—C28	1.397 (19)
O3P—C14P	1.237 (10)	C27—H27	0.9300
C6P—C1P	1.3840	C28—C29	1.33 (3)
C6P—C5P	1.3871	C28—H28	0.9300
C6P—C21P	1.51 (2)	C29—C30	1.34 (3)
C1P—C2P	1.3870	C29—H29	0.9300
C1P—C7P	1.511 (19)	C30—C31	1.43 (2)
C2P—C3P	1.3870	C30—H30	0.9300
C2P—C15P	1.50 (2)	C31—H31	0.9300
C3P—C4P	1.3809
C5—C6—C1	118.2	C1P—C7P—C8P	116.5 (19)
C5—C6—C21	119.8 (19)	O1P—C7P—C15P	116 (3)
C1—C6—C21	122.0 (19)	C1P—C7P—C15P	83.0 (14)
C6—C1—C2	121.0	C8P—C7P—C15P	110.1 (16)
C6—C1—C7	115.7 (17)	C13P—C8P—C9P	119.8
C2—C1—C7	123.3 (17)	C13P—C8P—C7P	121.8 (15)
C3—C2—C1	118.24 (7)	C9P—C8P—C7P	118.2 (15)
C3—C2—C15	121 (2)	C10P—C9P—C8P	120.2
C1—C2—C15	120 (2)	C10P—C9P—H9P	120.0
C4—C3—C2	122.2	C8P—C9P—H9P	119.8
C4—C3—H3	118.9	C11P—C10P—C9P	120.0
C2—C3—H3	118.9	C11P—C10P—H10P	119.8
C3—C4—C5	117.8	C9P—C10P—H10P	120.1
C3—C4—C18	120 (2)	C10P—C11P—C12P	119.8
C5—C4—C18	122 (2)	C10P—C11P—C14P	120.8 (16)
C6—C5—C4	122.64 (6)	C12P—C11P—C14P	119.4 (16)
C6—C5—H5	118.6	C11P—C12P—C13P	120.2
C4—C5—H5	118.7	C11P—C12P—H12P	120.0
O1—C7—C8	120 (3)	C13P—C12P—H12P	119.8
O1—C7—C1	121 (3)	C8P—C13P—C12P	119.9
C8—C7—C1	119 (2)	C8P—C13P—H13P	119.8
C13—C8—C9	118.4	C12P—C13P—H13P	120.2
C13—C8—C7	122.3 (19)	O3P—C14P—O2P	123.2 (7)
C9—C8—C7	119.3 (19)	O3P—C14P—C11P	118.7 (13)
C10—C9—C8	120.7	O2P—C14P—C11P	117.1 (13)
C10—C9—H9	119.7	C2P—C15P—C16P	121 (3)
C8—C9—H9	119.6	C2P—C15P—C17P	119 (3)
C9—C10—C11	120.9	C16P—C15P—C17P	106 (3)
C9—C10—H10	119.7	C2P—C15P—C7P	86.2 (15)
C11—C10—H10	119.4	C16P—C15P—C7P	110 (2)
C12—C11—C10	118.5	C17P—C15P—C7P	113 (3)
C12—C11—C14	118 (2)	C15P—C16P—H16G	109.5
C10—C11—C14	123.4 (19)	C15P—C16P—H16H	109.5
C11—C12—C13	120.7	H16G—C16P—H16H	109.5
C11—C12—H12	119.6	C15P—C16P—H16I	109.5
C13—C12—H12	119.7	H16G—C16P—H16I	109.5
C8—C13—C12	120.8	H16H—C16P—H16I	109.5
C8—C13—H13	119.4	C15P—C17P—H17G	109.5
C12—C13—H13	119.8	C15P—C17P—H17H	109.5
O3—C14—O2	123.2 (7)	H17G—C17P—H17H	109.5
O3—C14—C11	120.8 (15)	C15P—C17P—H17I	109.5
O2—C14—C11	116.0 (15)	H17G—C17P—H17I	109.5
C17—C15—C16	112 (3)	H17H—C17P—H17I	109.5
C17—C15—C2	112 (3)	C19P—C18P—C4P	108 (3)
C16—C15—C2	110 (3)	C19P—C18P—C20P	108 (3)
C17—C15—H15	107.9	C4P—C18P—C20P	98 (2)
C16—C15—H15	107.9	C19P—C18P—H18P	114.0
C2—C15—H15	107.9	C4P—C18P—H18P	114.0
C15—C16—H16A	109.5	C20P—C18P—H18P	114.0
C15—C16—H16B	109.5	C18P—C19P—H19G	109.5
H16A—C16—H16B	109.5	C18P—C19P—H19H	109.5
C15—C16—H16C	109.5	H19G—C19P—H19H	109.5
H16A—C16—H16C	109.5	C18P—C19P—H19I	109.5
H16B—C16—H16C	109.5	H19G—C19P—H19I	109.5
C15—C17—H17A	109.5	H19H—C19P—H19I	109.5
C15—C17—H17B	109.5	C18P—C20P—H20G	109.5
H17A—C17—H17B	109.5	C18P—C20P—H20H	109.5
C15—C17—H17C	109.5	H20G—C20P—H20H	109.5
H17A—C17—H17C	109.5	C18P—C20P—H20I	109.5
H17B—C17—H17C	109.5	H20G—C20P—H20I	109.5
C19—C18—C20	113 (3)	H20H—C20P—H20I	109.5
C19—C18—C4	115 (3)	C6P—C21P—C23P	116 (3)
C20—C18—C4	108 (3)	C6P—C21P—C22P	108 (3)
C19—C18—H18	106.6	C23P—C21P—C22P	108 (3)
C20—C18—H18	106.6	C6P—C21P—H21P	108.2
C4—C18—H18	106.6	C23P—C21P—H21P	108.2
C18—C19—H19A	109.5	C22P—C21P—H21P	108.2
C18—C19—H19B	109.5	C21P—C22P—H22F	109.5
H19A—C19—H19B	109.5	C21P—C22P—H22G	109.5
C18—C19—H19C	109.5	H22F—C22P—H22G	109.5
H19A—C19—H19C	109.5	C21P—C22P—H22H	109.5
H19B—C19—H19C	109.5	H22F—C22P—H22H	109.5
C18—C20—H20A	109.5	H22G—C22P—H22H	109.5
C18—C20—H20B	109.5	C21P—C23P—H23G	109.5
H20A—C20—H20B	109.5	C21P—C23P—H23H	109.5
C18—C20—H20C	109.5	H23G—C23P—H23H	109.5
H20A—C20—H20C	109.5	C21P—C23P—H23I	109.5
H20B—C20—H20C	109.5	H23G—C23P—H23I	109.5
C6—C21—C22	108 (3)	H23H—C23P—H23I	109.5
C6—C21—C23	109 (3)	C5Z—C6Z—C1Z	119.9
C22—C21—C23	104 (3)	C5Z—C6Z—C21Z	144.1 (16)
C6—C21—H21	111.5	C1Z—C6Z—C21Z	95.8 (16)
C22—C21—H21	111.5	C2Z—C1Z—C6Z	119.8
C23—C21—H21	111.5	C2Z—C1Z—C7Z	146.1 (16)
C21—C22—H22A	109.5	C6Z—C1Z—C7Z	93.8 (16)
C21—C22—H22B	109.5	C3Z—C2Z—C1Z	120.23 (6)
H22A—C22—H22B	109.5	C3Z—C2Z—C15Z	125 (2)
C21—C22—H22C	109.5	C1Z—C2Z—C15Z	115 (2)
H22A—C22—H22C	109.5	C4Z—C3Z—C2Z	119.9
H22B—C22—H22C	109.5	C4Z—C3Z—H3Z	120.0
C21—C23—H23A	109.5	C2Z—C3Z—H3Z	120.1
C21—C23—H23B	109.5	C3Z—C4Z—C5Z	120.0
H23A—C23—H23B	109.5	C3Z—C4Z—C18Z	121 (2)
C21—C23—H23C	109.5	C5Z—C4Z—C18Z	119 (2)
H23A—C23—H23C	109.5	C6Z—C5Z—C4Z	120.09 (6)
H23B—C23—H23C	109.5	C6Z—C5Z—H5Z	119.9
C5D—C6D—C1D	119.3	C4Z—C5Z—H5Z	120.0
C5D—C6D—C21D	133.2 (12)	O1Z—C7Z—C1Z	95 (3)
C1D—C6D—C21D	107.3 (12)	O1Z—C7Z—C8Z	114 (3)
C2D—C1D—C6D	121.7	C1Z—C7Z—C8Z	118 (2)
C2D—C1D—C7D	124.7 (12)	O1Z—C7Z—C21Z	116 (3)
C6D—C1D—C7D	113.5 (11)	C1Z—C7Z—C21Z	85.9 (16)
C1D—C2D—C3D	118.1	C8Z—C7Z—C21Z	122 (2)
C1D—C2D—C15D	122.1 (15)	C13Z—C8Z—C9Z	120.0
C3D—C2D—C15D	119.9 (15)	C13Z—C8Z—C7Z	120 (2)
C2D—C3D—C4D	122.0	C9Z—C8Z—C7Z	120 (2)
C2D—C3D—H3D	119.1	C10Z—C9Z—C8Z	120.1
C4D—C3D—H3D	118.9	C10Z—C9Z—H9Z	119.8
C5D—C4D—C3D	116.7	C8Z—C9Z—H9Z	120.1
C5D—C4D—C18D	116.1 (16)	C9Z—C10Z—C11Z	119.8
C3D—C4D—C18D	127.2 (16)	C9Z—C10Z—H10Z	120.5
C6D—C5D—C4D	122.0	C11Z—C10Z—H10Z	119.7
C6D—C5D—H5D	119.1	C12Z—C11Z—C10Z	120.3
C4D—C5D—H5D	119.0	C12Z—C11Z—C14Z	118.1 (19)
O1D—C7D—C22D	110.2 (18)	C10Z—C11Z—C14Z	121.6 (19)
O1D—C7D—C8D	109.8 (17)	C11Z—C12Z—C13Z	119.9
C22D—C7D—C8D	112.4 (14)	C11Z—C12Z—H12Z	120.4
O1D—C7D—C1D	111.8 (18)	C13Z—C12Z—H12Z	119.7
C22D—C7D—C1D	100.8 (14)	C8Z—C13Z—C12Z	119.9
C8D—C7D—C1D	111.6 (15)	C8Z—C13Z—H13Z	120.0
C13D—C8D—C9D	118.6	C12Z—C13Z—H13Z	120.2
C13D—C8D—C7D	123.0 (13)	O3Z—C14Z—O2Z	123.2 (7)
C9D—C8D—C7D	118.4 (13)	O3Z—C14Z—C11Z	118.0 (14)
C10D—C9D—C8D	121.8	O2Z—C14Z—C11Z	118.8 (13)
C10D—C9D—H9D	119.2	C17Z—C15Z—C16Z	122 (4)
C8D—C9D—H9D	119.0	C17Z—C15Z—C2Z	112 (2)
C9D—C10D—C11D	119.8	C16Z—C15Z—C2Z	105 (2)
C9D—C10D—H10D	120.3	C17Z—C15Z—H15Z	105.6
C11D—C10D—H10D	119.9	C16Z—C15Z—H15Z	105.6
C12D—C11D—C10D	117.5	C2Z—C15Z—H15Z	105.6
C12D—C11D—C14D	122.1 (13)	C15Z—C16Z—H16J	109.5
C10D—C11D—C14D	120.4 (13)	C15Z—C16Z—H16K	109.5
C11D—C12D—C13D	122.0	H16J—C16Z—H16K	109.5
C11D—C12D—H12D	119.0	C15Z—C16Z—H16L	109.5
C13D—C12D—H12D	119.0	H16J—C16Z—H16L	109.5
C8D—C13D—C12D	120.3	H16K—C16Z—H16L	109.5
C8D—C13D—H13D	119.7	C15Z—C17Z—H17J	109.5
C12D—C13D—H13D	120.0	C15Z—C17Z—H17K	109.5
O3D—C14D—O2D	123.2 (7)	H17J—C17Z—H17K	109.5
O3D—C14D—C11D	116.5 (12)	C15Z—C17Z—H17L	109.5
O2D—C14D—C11D	120.2 (12)	H17J—C17Z—H17L	109.5
C16D—C15D—C2D	114.0 (19)	H17K—C17Z—H17L	109.5
C16D—C15D—C17D	112 (2)	C4Z—C18Z—C19Z	97 (3)
C2D—C15D—C17D	107.7 (18)	C4Z—C18Z—C20Z	119 (3)
C16D—C15D—H15D	107.7	C19Z—C18Z—C20Z	108 (3)
C2D—C15D—H15D	107.7	C4Z—C18Z—H18Z	110.6
C17D—C15D—H15D	107.7	C19Z—C18Z—H18Z	110.6
C15D—C16D—H16D	109.5	C20Z—C18Z—H18Z	110.6
C15D—C16D—H16E	109.5	C18Z—C19Z—H19J	109.5
H16D—C16D—H16E	109.5	C18Z—C19Z—H19K	109.5
C15D—C16D—H16F	109.5	H19J—C19Z—H19K	109.5
H16D—C16D—H16F	109.5	C18Z—C19Z—H19L	109.5
H16E—C16D—H16F	109.5	H19J—C19Z—H19L	109.5
C15D—C17D—H17D	109.5	H19K—C19Z—H19L	109.5
C15D—C17D—H17E	109.5	C18Z—C20Z—H20J	109.5
H17D—C17D—H17E	109.5	C18Z—C20Z—H20K	109.5
C15D—C17D—H17F	109.5	H20J—C20Z—H20K	109.5
H17D—C17D—H17F	109.5	C18Z—C20Z—H20L	109.5
H17E—C17D—H17F	109.5	H20J—C20Z—H20L	109.5
C19D—C18D—C20D	119 (2)	H20K—C20Z—H20L	109.5
C19D—C18D—C4D	121 (2)	C6Z—C21Z—C22Z	108 (3)
C20D—C18D—C4D	118 (2)	C6Z—C21Z—C23Z	121 (3)
C19D—C18D—H18D	95.7	C22Z—C21Z—C23Z	114 (3)
C20D—C18D—H18D	95.7	C6Z—C21Z—C7Z	84.4 (16)
C4D—C18D—H18D	95.7	C22Z—C21Z—C7Z	112 (3)
C18D—C19D—H19D	109.5	C23Z—C21Z—C7Z	114 (3)
C18D—C19D—H19E	109.5	C21Z—C22Z—H22I	109.5
H19D—C19D—H19E	109.5	C21Z—C22Z—H22J	109.5
C18D—C19D—H19F	109.5	H22I—C22Z—H22J	109.5
H19D—C19D—H19F	109.5	C21Z—C22Z—H22K	109.5
H19E—C19D—H19F	109.5	H22I—C22Z—H22K	109.5
C18D—C20D—H20D	109.5	H22J—C22Z—H22K	109.5
C18D—C20D—H20E	109.5	C21Z—C23Z—H23J	109.5
H20D—C20D—H20E	109.5	C21Z—C23Z—H23K	109.5
C18D—C20D—H20F	109.5	H23J—C23Z—H23K	109.5
H20D—C20D—H20F	109.5	C21Z—C23Z—H23L	109.5
H20E—C20D—H20F	109.5	H23J—C23Z—H23L	109.5
C23D—C21D—C6D	118 (2)	H23K—C23Z—H23L	109.5
C23D—C21D—C22D	114 (2)	C25—N1—H1A	109.5
C6D—C21D—C22D	103.3 (16)	C25—N1—H1B	109.5
C23D—C21D—H21D	107.0	H1A—N1—H1B	109.5
C6D—C21D—H21D	107.0	C25—N1—H1C	109.5
C22D—C21D—H21D	107.0	H1A—N1—H1C	109.5
C7D—C22D—C21D	108.9 (15)	H1B—N1—H1C	109.5
C7D—C22D—H22D	109.9	C25—C24—H24A	109.5
C21D—C22D—H22D	109.9	C25—C24—H24B	109.5
C7D—C22D—H22E	109.9	H24A—C24—H24B	109.5
C21D—C22D—H22E	109.9	C25—C24—H24C	109.5
H22D—C22D—H22E	108.3	H24A—C24—H24C	109.5
C21D—C23D—H23D	109.5	H24B—C24—H24C	109.5
C21D—C23D—H23E	109.5	C26—C25—N1	110.4 (7)
H23D—C23D—H23E	109.5	C26—C25—C24	114.5 (9)
C21D—C23D—H23F	109.5	N1—C25—C24	107.0 (8)
H23D—C23D—H23F	109.5	C26—C25—H25	108.3
H23E—C23D—H23F	109.5	N1—C25—H25	108.3
C1P—C6P—C5P	120.0	C24—C25—H25	108.3
C1P—C6P—C21P	124.4 (19)	C31—C26—C27	119.5 (12)
C5P—C6P—C21P	115.6 (19)	C31—C26—C25	122.1 (13)
C6P—C1P—C2P	120.0	C27—C26—C25	118.4 (13)
C6P—C1P—C7P	143.2 (16)	C26—C27—C28	120.3 (15)
C2P—C1P—C7P	96.1 (15)	C26—C27—H27	119.8
C3P—C2P—C1P	119.97 (6)	C28—C27—H27	119.8
C3P—C2P—C15P	146.5 (16)	C29—C28—C27	118 (2)
C1P—C2P—C15P	93.5 (16)	C29—C28—H28	120.9
C4P—C3P—C2P	120.0	C27—C28—H28	120.9
C4P—C3P—H3P	120.1	C28—C29—C30	124 (3)
C2P—C3P—H3P	119.8	C28—C29—H29	117.8
C3P—C4P—C5P	120.1	C30—C29—H29	117.8
C3P—C4P—C18P	121.6 (19)	C29—C30—C31	117 (3)
C5P—C4P—C18P	118.4 (19)	C29—C30—H30	121.5
C4P—C5P—C6P	119.99 (6)	C31—C30—H30	121.5
C4P—C5P—H5P	120.0	C26—C31—C30	120.4 (16)
C6P—C5P—H5P	120.0	C26—C31—H31	119.8
O1P—C7P—C1P	123 (2)	C30—C31—H31	119.8
O1P—C7P—C8P	107 (2)

(0minUV_01GPa)

Crystal data

C31H39NO3	Dx = 1.141 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 900 reflections
a = 6.1975 (8) Å	θ = 5.6–18.6°
b = 13.744 (3) Å	µ = 0.07 mm^−1
c = 32.378 (17) Å	T = 299 K
V = 2757.9 (16) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.6°, θmin = 5.7°
φ– and ω scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→15
Tmin = 0.343, Tmax = 1.000	l = −21→18
5657 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.085	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 1.251P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.15 e Å^−3
2184 reflections	Δρmin = −0.12 e Å^−3
254 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
36 restraints	Absolute structure parameter: −1.4 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0381 (15)	0.7615 (7)	0.3714 (5)	0.092 (7)
O2	0.6129 (13)	0.3695 (6)	0.4832 (5)	0.080 (6)
O3	0.3123 (13)	0.3799 (6)	0.4464 (4)	0.076 (6)
C1	0.814 (2)	0.7291 (11)	0.3138 (10)	0.047 (9)
C2	0.679 (2)	0.8071 (11)	0.3023 (10)	0.048 (10)
C3	0.633 (2)	0.8181 (11)	0.2618 (12)	0.056 (10)
H3	0.5449	0.8702	0.2546	0.067*
C4	0.707 (2)	0.7570 (11)	0.2291 (9)	0.057 (8)
C5	0.840 (2)	0.6787 (10)	0.2406 (9)	0.052 (9)
H5	0.8915	0.6360	0.2206	0.062*
C6	0.895 (2)	0.6651 (11)	0.2823 (10)	0.047 (9)
C7	0.889 (3)	0.7137 (10)	0.3554 (10)	0.074 (12)
C8	0.7789 (17)	0.6386 (8)	0.3841 (7)	0.043 (3)*
C9	0.5776 (18)	0.5985 (9)	0.3715 (6)	0.063 (4)*
H9	0.5072	0.6210	0.3480	0.076*
C10	0.4899 (18)	0.5246 (9)	0.3956 (7)	0.060 (4)*
H10	0.3578	0.4978	0.3881	0.072*
C11	0.5947 (18)	0.4900 (9)	0.4305 (7)	0.050 (4)*
C12	0.7921 (18)	0.5322 (9)	0.4413 (7)	0.068 (4)*
H12	0.8649	0.5104	0.4646	0.082*
C13	0.881 (2)	0.6062 (9)	0.4177 (6)	0.057 (4)*
H13	1.0122	0.6334	0.4253	0.069*
C14	0.499 (3)	0.4078 (9)	0.4567 (8)	0.066 (9)
C15	1.0418 (17)	0.5779 (9)	0.2929 (7)	0.081 (11)
H15	1.0630	0.5777	0.3229	0.097*
C16	1.2596 (17)	0.5872 (9)	0.2732 (7)	0.079 (10)
H16A	1.3199	0.6497	0.2796	0.118*
H16B	1.2455	0.5808	0.2438	0.118*
H16C	1.3529	0.5370	0.2834	0.118*
C17	0.925 (2)	0.4818 (9)	0.2812 (7)	0.106 (11)
H17A	0.9272	0.4739	0.2517	0.160*
H17B	0.7787	0.4841	0.2907	0.160*
H17C	0.9982	0.4279	0.2939	0.160*
C18	0.642 (3)	0.7791 (11)	0.1856 (11)	0.076 (6)*
H18	0.6464	0.8502	0.1835	0.091*
C19	0.4132 (19)	0.7514 (12)	0.1733 (9)	0.124 (12)
H19A	0.3650	0.7933	0.1514	0.186*
H19B	0.3192	0.7584	0.1967	0.186*
H19C	0.4111	0.6851	0.1640	0.186*
C20	0.795 (2)	0.7427 (13)	0.1526 (10)	0.122 (15)
H20A	0.7812	0.6735	0.1499	0.184*
H20B	0.9409	0.7585	0.1602	0.184*
H20C	0.7615	0.7732	0.1267	0.184*
C21	0.602 (2)	0.8790 (10)	0.3335 (7)	0.068 (10)
H21	0.5847	0.8431	0.3594	0.082*
C22	0.776 (2)	0.9586 (10)	0.3416 (10)	0.098 (12)
H22A	0.7897	0.9991	0.3176	0.148*
H22B	0.9119	0.9280	0.3474	0.148*
H22C	0.7332	0.9976	0.3648	0.148*
C23	0.3839 (18)	0.9262 (10)	0.3243 (10)	0.096 (10)
H23A	0.2747	0.8768	0.3227	0.145*
H23B	0.3916	0.9602	0.2984	0.145*
H23C	0.3485	0.9712	0.3459	0.145*
N1	0.0364 (13)	0.3303 (7)	0.5092 (6)	0.067 (8)
H1A	0.0292	0.2659	0.5116	0.080*
H1B	0.1445	0.3461	0.4924	0.080*
H1C	−0.0870	0.3528	0.4989	0.080*
C24	0.2877 (18)	0.3373 (8)	0.5666 (8)	0.095 (10)
H24A	0.4019	0.3637	0.5500	0.142*
H24B	0.2893	0.2676	0.5648	0.142*
H24C	0.3079	0.3566	0.5949	0.142*
C25	0.0751 (19)	0.3750 (10)	0.5514 (8)	0.052 (4)*
H25	−0.0373	0.3507	0.5700	0.062*
C26	0.0535 (17)	0.4829 (9)	0.5492 (7)	0.057 (4)*
C27	−0.138 (2)	0.5270 (10)	0.5596 (7)	0.085 (5)*
H27	−0.2546	0.4890	0.5679	0.102*
C28	−0.160 (2)	0.6307 (11)	0.5578 (8)	0.096 (5)*
H28	−0.2863	0.6617	0.5663	0.115*
C29	0.010 (2)	0.6813 (10)	0.5433 (7)	0.087 (5)*
H29	−0.0087	0.7480	0.5400	0.105*
C30	0.204 (2)	0.6443 (11)	0.5332 (8)	0.097 (6)*
H30	0.3195	0.6830	0.5252	0.116*
C31	0.2180 (19)	0.5399 (10)	0.5359 (7)	0.071 (5)*
H31	0.3464	0.5101	0.5281	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.102 (7)	0.080 (8)	0.09 (2)	−0.046 (6)	−0.044 (9)	0.021 (7)
O2	0.053 (5)	0.040 (7)	0.15 (2)	0.005 (4)	0.006 (8)	0.024 (7)
O3	0.055 (5)	0.087 (7)	0.09 (2)	−0.028 (5)	−0.006 (7)	0.021 (7)
C1	0.048 (9)	0.053 (12)	0.04 (3)	−0.005 (8)	−0.001 (13)	−0.004 (12)
C2	0.056 (9)	0.042 (11)	0.05 (3)	0.003 (7)	−0.009 (14)	0.012 (12)
C3	0.059 (9)	0.038 (10)	0.07 (3)	0.011 (7)	0.002 (13)	0.018 (13)
C4	0.060 (8)	0.054 (12)	0.06 (3)	−0.013 (8)	−0.005 (14)	−0.006 (12)
C5	0.058 (8)	0.043 (10)	0.05 (3)	−0.006 (7)	−0.003 (13)	−0.004 (11)
C6	0.075 (10)	0.049 (11)	0.02 (3)	−0.016 (8)	−0.003 (14)	0.003 (12)
C7	0.056 (10)	0.039 (11)	0.13 (4)	0.012 (7)	−0.030 (15)	0.006 (12)
C14	0.077 (10)	0.026 (10)	0.09 (3)	0.006 (8)	0.020 (13)	0.006 (10)
C15	0.056 (7)	0.038 (10)	0.15 (4)	0.011 (7)	−0.009 (11)	0.022 (10)
C16	0.074 (8)	0.072 (12)	0.09 (4)	0.010 (7)	−0.004 (12)	−0.003 (11)
C17	0.094 (9)	0.036 (10)	0.19 (4)	0.001 (8)	−0.012 (13)	0.004 (10)
C19	0.070 (9)	0.153 (18)	0.15 (4)	−0.029 (10)	−0.009 (15)	0.010 (14)
C20	0.102 (12)	0.148 (18)	0.12 (6)	0.022 (12)	−0.008 (16)	−0.014 (15)
C21	0.077 (9)	0.044 (11)	0.08 (3)	0.003 (8)	−0.012 (12)	0.004 (10)
C22	0.095 (9)	0.081 (13)	0.12 (4)	−0.010 (9)	0.016 (13)	−0.037 (13)
C23	0.080 (9)	0.081 (13)	0.13 (4)	0.022 (9)	−0.011 (13)	0.012 (11)
N1	0.060 (6)	0.036 (7)	0.11 (3)	−0.001 (5)	0.003 (9)	0.012 (8)
C24	0.081 (8)	0.054 (10)	0.15 (3)	0.011 (7)	−0.029 (13)	0.011 (10)

Geometric parameters (Å, º)

O1—C7	1.245 (19)	C18—H18	0.9800
O2—C14	1.23 (2)	C19—H19A	0.9600
O3—C14	1.265 (17)	C19—H19B	0.9600
C1—C2	1.41 (2)	C19—H19C	0.9600
C1—C6	1.44 (3)	C20—H20A	0.9600
C1—C7	1.44 (3)	C20—H20B	0.9600
C2—C3	1.35 (4)	C20—H20C	0.9600
C2—C21	1.49 (3)	C21—C23	1.529 (16)
C3—C4	1.43 (4)	C21—C22	1.558 (16)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.41 (2)	C22—H22A	0.9600
C4—C18	1.50 (4)	C22—H22B	0.9600
C5—C6	1.41 (3)	C22—H22C	0.9600
C5—H5	0.9300	C23—H23A	0.9600
C6—C15	1.54 (2)	C23—H23B	0.9600
C7—C8	1.55 (3)	C23—H23C	0.9600
C8—C13	1.33 (2)	N1—C25	1.52 (2)
C8—C9	1.424 (17)	N1—H1A	0.8900
C9—C10	1.391 (19)	N1—H1B	0.8900
C9—H9	0.9300	N1—H1C	0.8900
C10—C11	1.39 (2)	C24—C25	1.499 (16)
C10—H10	0.9300	C24—H24A	0.9600
C11—C12	1.399 (15)	C24—H24B	0.9600
C11—C14	1.53 (2)	C24—H24C	0.9600
C12—C13	1.38 (2)	C25—C26	1.491 (16)
C12—H12	0.9300	C25—H25	0.9800
C13—H13	0.9300	C26—C31	1.356 (16)
C15—C16	1.499 (18)	C26—C27	1.376 (15)
C15—C17	1.553 (16)	C27—C28	1.434 (16)
C15—H15	0.9800	C27—H27	0.9300
C16—H16A	0.9600	C28—C29	1.347 (19)
C16—H16B	0.9600	C28—H28	0.9300
C16—H16C	0.9600	C29—C30	1.347 (17)
C17—H17A	0.9600	C29—H29	0.9300
C17—H17B	0.9600	C30—C31	1.440 (16)
C17—H17C	0.9600	C30—H30	0.9300
C18—C20	1.52 (3)	C31—H31	0.9300
C18—C19	1.52 (2)
C2—C1—C6	119 (3)	C18—C19—H19A	109.5
C2—C1—C7	123 (2)	C18—C19—H19B	109.5
C6—C1—C7	117.5 (19)	H19A—C19—H19B	109.5
C3—C2—C1	118 (3)	C18—C19—H19C	109.5
C3—C2—C21	121.0 (18)	H19A—C19—H19C	109.5
C1—C2—C21	121 (3)	H19B—C19—H19C	109.5
C2—C3—C4	126 (2)	C18—C20—H20A	109.5
C2—C3—H3	117.1	C18—C20—H20B	109.5
C4—C3—H3	117.1	H20A—C20—H20B	109.5
C5—C4—C3	116 (3)	C18—C20—H20C	109.5
C5—C4—C18	124 (2)	H20A—C20—H20C	109.5
C3—C4—C18	119.4 (19)	H20B—C20—H20C	109.5
C4—C5—C6	120 (2)	C2—C21—C23	115.6 (18)
C4—C5—H5	120.0	C2—C21—C22	110.9 (14)
C6—C5—H5	120.0	C23—C21—C22	110.3 (11)
C5—C6—C1	121 (2)	C2—C21—H21	106.5
C5—C6—C15	117 (2)	C23—C21—H21	106.5
C1—C6—C15	121 (3)	C22—C21—H21	106.5
O1—C7—C1	123 (2)	C21—C22—H22A	109.5
O1—C7—C8	115 (3)	C21—C22—H22B	109.5
C1—C7—C8	121.2 (16)	H22A—C22—H22B	109.5
C13—C8—C9	121.3 (15)	C21—C22—H22C	109.5
C13—C8—C7	120.3 (14)	H22A—C22—H22C	109.5
C9—C8—C7	118.1 (19)	H22B—C22—H22C	109.5
C10—C9—C8	117.6 (17)	C21—C23—H23A	109.5
C10—C9—H9	121.2	C21—C23—H23B	109.5
C8—C9—H9	121.2	H23A—C23—H23B	109.5
C11—C10—C9	121.6 (13)	C21—C23—H23C	109.5
C11—C10—H10	119.2	H23A—C23—H23C	109.5
C9—C10—H10	119.2	H23B—C23—H23C	109.5
C10—C11—C12	118.1 (16)	C25—N1—H1A	109.5
C10—C11—C14	121.6 (13)	C25—N1—H1B	109.5
C12—C11—C14	120.3 (18)	H1A—N1—H1B	109.5
C13—C12—C11	120.9 (19)	C25—N1—H1C	109.5
C13—C12—H12	119.5	H1A—N1—H1C	109.5
C11—C12—H12	119.5	H1B—N1—H1C	109.5
C8—C13—C12	120.5 (14)	C25—C24—H24A	109.5
C8—C13—H13	119.8	C25—C24—H24B	109.5
C12—C13—H13	119.8	H24A—C24—H24B	109.5
O2—C14—O3	125.5 (15)	C25—C24—H24C	109.5
O2—C14—C11	118.8 (14)	H24A—C24—H24C	109.5
O3—C14—C11	115.5 (18)	H24B—C24—H24C	109.5
C16—C15—C6	111.7 (13)	C26—C25—C24	116.0 (10)
C16—C15—C17	112.7 (14)	C26—C25—N1	110.2 (17)
C6—C15—C17	109.5 (11)	C24—C25—N1	107.2 (13)
C16—C15—H15	107.6	C26—C25—H25	107.7
C6—C15—H15	107.6	C24—C25—H25	107.7
C17—C15—H15	107.6	N1—C25—H25	107.7
C15—C16—H16A	109.5	C31—C26—C27	118.3 (13)
C15—C16—H16B	109.5	C31—C26—C25	121.5 (11)
H16A—C16—H16B	109.5	C27—C26—C25	120.2 (12)
C15—C16—H16C	109.5	C26—C27—C28	120.7 (15)
H16A—C16—H16C	109.5	C26—C27—H27	119.7
H16B—C16—H16C	109.5	C28—C27—H27	119.7
C15—C17—H17A	109.5	C29—C28—C27	116.9 (15)
C15—C17—H17B	109.5	C29—C28—H28	121.5
H17A—C17—H17B	109.5	C27—C28—H28	121.5
C15—C17—H17C	109.5	C28—C29—C30	126.1 (15)
H17A—C17—H17C	109.5	C28—C29—H29	117.0
H17B—C17—H17C	109.5	C30—C29—H29	117.0
C4—C18—C20	115.2 (17)	C29—C30—C31	114.6 (14)
C4—C18—C19	117 (2)	C29—C30—H30	122.7
C20—C18—C19	109 (2)	C31—C30—H30	122.7
C4—C18—H18	105.1	C26—C31—C30	123.3 (13)
C20—C18—H18	105.1	C26—C31—H31	118.4
C19—C18—H18	105.1	C30—C31—H31	118.4

(0minUV_075GPa)

Crystal data

C31H39NO3	Dx = 1.238 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.70932 Å
Orthorhombic, P212121	Cell parameters from 2405 reflections
a = 5.9706 (10) Å	θ = 2.4–23.7°
b = 13.368 (4) Å	µ = 0.08 mm^−1
c = 31.832 (8) Å	T = 299 K
V = 2540.7 (11) Å^3	Block, colourless
Z = 4	0.40 × 0.18 × 0.14 mm
F(000) = 1024

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.125
φ– and ω scans	θmax = 25.0°, θmin = 1.7°
13548 measured reflections	h = −7→7
2324 independent reflections	k = −12→12
1279 reflections with I > 2σ(I)	l = −31→31

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[σ^2(Fo^2) + (0.0772P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.165	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
2324 reflections	Δρmin = −0.15 e Å^−3
294 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
0 restraints	Absolute structure parameter: 1.2 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0504 (13)	0.2264 (6)	0.6293 (2)	0.070 (3)
O3	0.3045 (11)	0.6173 (6)	0.5556 (2)	0.058 (2)
O2	0.6120 (11)	0.6260 (5)	0.5170 (2)	0.047 (2)
C1	0.8206 (16)	0.2585 (9)	0.6886 (3)	0.037 (3)
C2	0.9036 (14)	0.3231 (8)	0.7191 (4)	0.036 (3)
C3	0.8433 (15)	0.3078 (8)	0.7606 (4)	0.041 (3)
H3	0.8998	0.3509	0.7809	0.049*
C4	0.7036 (15)	0.2315 (9)	0.7731 (3)	0.039 (3)
C5	0.6222 (14)	0.1688 (8)	0.7411 (3)	0.035 (3)
H5	0.5271	0.1165	0.7485	0.042*
C6	0.6772 (15)	0.1811 (8)	0.6991 (4)	0.036 (3)
C7	0.8952 (17)	0.2726 (9)	0.6440 (4)	0.041 (3)
C8	0.7852 (14)	0.3498 (8)	0.6175 (3)	0.035 (3)*
C9	0.8946 (15)	0.3863 (8)	0.5827 (3)	0.039 (3)*
H9	1.0329	0.3600	0.5751	0.046*
C10	0.8002 (15)	0.4618 (8)	0.5591 (3)	0.043 (3)*
H10	0.8748	0.4851	0.5354	0.051*
C11	0.5938 (14)	0.5039 (7)	0.5703 (3)	0.033 (2)*
C12	0.4837 (15)	0.4651 (8)	0.6047 (3)	0.040 (3)*
H12	0.3446	0.4905	0.6124	0.048*
C13	0.5788 (15)	0.3884 (8)	0.6281 (3)	0.047 (3)*
H13	0.5024	0.3628	0.6512	0.057*
C14	0.4986 (18)	0.5892 (9)	0.5464 (3)	0.041 (3)
C15	1.0523 (15)	0.4091 (8)	0.7064 (3)	0.042 (3)
H15	1.0815	0.4035	0.6762	0.051*
C16	1.2788 (14)	0.4050 (9)	0.7294 (3)	0.053 (3)
H16A	1.3376	0.3383	0.7281	0.080*
H16B	1.2583	0.4239	0.7583	0.080*
H16C	1.3819	0.4504	0.7163	0.080*
C17	0.9363 (18)	0.5088 (9)	0.7142 (4)	0.072 (4)
H17A	0.9213	0.5196	0.7439	0.108*
H17B	0.7906	0.5080	0.7015	0.108*
H17C	1.0239	0.5618	0.7022	0.108*
C18	0.6388 (17)	0.2105 (10)	0.8184 (4)	0.055 (3)
H18	0.6513	0.1378	0.8215	0.066*
C19	0.7932 (17)	0.2533 (9)	0.8512 (4)	0.069 (4)
H19A	0.7776	0.3248	0.8518	0.103*
H19B	0.9451	0.2362	0.8444	0.103*
H19C	0.7552	0.2263	0.8782	0.103*
C20	0.3991 (17)	0.2334 (10)	0.8265 (4)	0.083 (5)
H20A	0.3546	0.2039	0.8527	0.124*
H20B	0.3091	0.2065	0.8042	0.124*
H20C	0.3789	0.3046	0.8279	0.124*
C21	0.5905 (16)	0.1083 (8)	0.6663 (3)	0.042 (3)
H21	0.5639	0.1472	0.6407	0.050*
C22	0.7669 (18)	0.0298 (9)	0.6555 (4)	0.063 (3)
H22A	0.7993	−0.0097	0.6799	0.095*
H22B	0.9011	0.0625	0.6461	0.095*
H22C	0.7112	−0.0127	0.6335	0.095*
C23	0.3696 (15)	0.0596 (9)	0.6778 (4)	0.064 (4)
H23A	0.2684	0.1095	0.6883	0.096*
H23B	0.3944	0.0100	0.6991	0.096*
H23C	0.3062	0.0285	0.6534	0.096*
N1	0.0383 (13)	0.6720 (6)	0.4902 (3)	0.042 (2)
H1A	0.1410	0.6507	0.5084	0.051*
H1B	−0.0969	0.6529	0.4988	0.051*
H1C	0.0432	0.7384	0.4886	0.051*
C24	0.3050 (15)	0.6681 (8)	0.4309 (4)	0.052 (3)
H24A	0.4236	0.6510	0.4500	0.077*
H24B	0.2958	0.7396	0.4284	0.077*
H24C	0.3348	0.6393	0.4039	0.077*
C25	0.0849 (16)	0.6279 (10)	0.4477 (3)	0.044 (3)
H25	−0.0332	0.6516	0.4288	0.053*
C26	0.0631 (17)	0.5163 (9)	0.4502 (3)	0.041 (3)
C27	−0.1340 (16)	0.4684 (10)	0.4401 (3)	0.048 (3)
H27	−0.2561	0.5062	0.4314	0.058*
C28	−0.154 (2)	0.3681 (13)	0.4425 (4)	0.068 (4)
H28	−0.2886	0.3379	0.4347	0.081*
C29	0.022 (3)	0.3094 (10)	0.4564 (4)	0.065 (4)
H29	0.0077	0.2403	0.4580	0.078*
C30	0.218 (2)	0.3556 (12)	0.4679 (4)	0.066 (4)
H30	0.3385	0.3177	0.4775	0.079*
C31	0.2369 (19)	0.4591 (11)	0.4652 (3)	0.052 (3)
H31	0.3689	0.4901	0.4736	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.082 (5)	0.066 (8)	0.062 (7)	0.043 (6)	0.027 (5)	0.024 (4)
O3	0.050 (4)	0.055 (7)	0.068 (7)	0.023 (4)	0.007 (4)	0.016 (4)
O2	0.056 (4)	0.036 (7)	0.048 (6)	−0.004 (4)	0.007 (4)	0.017 (3)
C1	0.045 (6)	0.028 (12)	0.037 (10)	0.007 (6)	0.009 (6)	0.011 (5)
C2	0.039 (6)	0.023 (11)	0.048 (11)	0.006 (6)	0.004 (6)	0.005 (5)
C3	0.040 (6)	0.044 (12)	0.039 (11)	−0.004 (6)	−0.004 (6)	−0.003 (5)
C4	0.041 (6)	0.042 (12)	0.032 (11)	0.004 (6)	−0.005 (6)	−0.003 (5)
C5	0.034 (5)	0.032 (12)	0.038 (11)	−0.005 (5)	0.003 (5)	0.007 (5)
C6	0.041 (6)	0.029 (11)	0.037 (11)	0.000 (6)	0.003 (6)	0.008 (4)
C7	0.047 (6)	0.020 (10)	0.057 (11)	0.000 (6)	−0.004 (6)	0.005 (5)
C14	0.055 (7)	0.033 (11)	0.033 (9)	0.001 (7)	−0.016 (6)	0.003 (5)
C15	0.043 (6)	0.037 (10)	0.047 (9)	−0.005 (6)	0.004 (5)	−0.002 (5)
C16	0.046 (6)	0.055 (12)	0.058 (11)	0.001 (6)	−0.003 (6)	0.002 (5)
C17	0.048 (6)	0.049 (14)	0.119 (14)	−0.007 (7)	0.006 (7)	0.013 (6)
C18	0.063 (7)	0.072 (12)	0.030 (11)	−0.002 (7)	0.010 (6)	0.003 (5)
C19	0.062 (7)	0.102 (14)	0.042 (11)	−0.017 (8)	−0.009 (7)	−0.004 (6)
C20	0.058 (8)	0.107 (16)	0.082 (14)	−0.014 (8)	0.016 (7)	−0.009 (7)
C21	0.064 (7)	0.048 (11)	0.013 (9)	−0.002 (7)	−0.004 (6)	−0.005 (4)
C22	0.079 (7)	0.049 (11)	0.063 (11)	0.007 (7)	0.005 (7)	−0.020 (5)
C23	0.057 (7)	0.053 (12)	0.081 (12)	−0.021 (7)	−0.017 (7)	0.003 (5)
N1	0.039 (4)	0.030 (8)	0.058 (9)	0.004 (4)	−0.005 (4)	0.002 (4)
C24	0.062 (7)	0.036 (10)	0.057 (10)	−0.008 (6)	0.015 (6)	0.002 (5)
C25	0.056 (7)	0.046 (12)	0.030 (10)	0.009 (7)	−0.008 (6)	0.000 (5)
C26	0.050 (7)	0.055 (12)	0.019 (9)	−0.008 (8)	0.002 (6)	0.000 (4)
C27	0.050 (7)	0.059 (12)	0.036 (11)	−0.017 (7)	0.004 (6)	−0.001 (5)
C28	0.079 (9)	0.065 (15)	0.060 (12)	−0.025 (10)	0.013 (7)	−0.017 (6)
C29	0.107 (11)	0.040 (13)	0.049 (11)	−0.015 (10)	0.032 (8)	−0.012 (6)
C30	0.071 (9)	0.056 (15)	0.072 (13)	0.005 (9)	0.009 (7)	0.007 (6)
C31	0.058 (7)	0.049 (13)	0.049 (12)	−0.006 (8)	0.002 (6)	0.002 (5)

Geometric parameters (Å, º)

O1—C7	1.208 (12)	C18—H18	0.9800
O3—C14	1.253 (12)	C19—H19A	0.9600
O2—C14	1.254 (11)	C19—H19B	0.9600
C1—C6	1.385 (14)	C19—H19C	0.9600
C1—C2	1.390 (15)	C20—H20A	0.9600
C1—C7	1.499 (14)	C20—H20B	0.9600
C2—C3	1.386 (13)	C20—H20C	0.9600
C2—C15	1.507 (14)	C21—C23	1.515 (13)
C3—C4	1.376 (14)	C21—C22	1.526 (13)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.406 (14)	C22—H22A	0.9600
C4—C18	1.518 (15)	C22—H22B	0.9600
C5—C6	1.386 (13)	C22—H22C	0.9600
C5—H5	0.9300	C23—H23A	0.9600
C6—C21	1.517 (14)	C23—H23B	0.9600
C7—C8	1.485 (15)	C23—H23C	0.9600
C8—C9	1.374 (12)	N1—C25	1.503 (13)
C8—C13	1.379 (13)	N1—H1A	0.8900
C9—C10	1.379 (13)	N1—H1B	0.8900
C9—H9	0.9300	N1—H1C	0.8900
C10—C11	1.401 (11)	C24—C25	1.516 (13)
C10—H10	0.9300	C24—H24A	0.9600
C11—C12	1.380 (12)	C24—H24B	0.9600
C11—C14	1.484 (13)	C24—H24C	0.9600
C12—C13	1.388 (13)	C25—C26	1.500 (14)
C12—H12	0.9300	C25—H25	0.9800
C13—H13	0.9300	C26—C31	1.374 (13)
C15—C17	1.522 (14)	C26—C27	1.378 (13)
C15—C16	1.539 (12)	C27—C28	1.349 (15)
C15—H15	0.9800	C27—H27	0.9300
C16—H16A	0.9600	C28—C29	1.386 (17)
C16—H16B	0.9600	C28—H28	0.9300
C16—H16C	0.9600	C29—C30	1.375 (16)
C17—H17A	0.9600	C29—H29	0.9300
C17—H17B	0.9600	C30—C31	1.390 (15)
C17—H17C	0.9600	C30—H30	0.9300
C18—C20	1.486 (13)	C31—H31	0.9300
C18—C19	1.506 (14)
C6—C1—C2	121.0 (11)	C18—C19—H19A	109.5
C6—C1—C7	120.5 (9)	C18—C19—H19B	109.5
C2—C1—C7	118.5 (11)	H19A—C19—H19B	109.5
C3—C2—C1	118.8 (11)	C18—C19—H19C	109.5
C3—C2—C15	121.3 (9)	H19A—C19—H19C	109.5
C1—C2—C15	119.8 (11)	H19B—C19—H19C	109.5
C4—C3—C2	122.9 (10)	C18—C20—H20A	109.5
C4—C3—H3	118.6	C18—C20—H20B	109.5
C2—C3—H3	118.6	H20A—C20—H20B	109.5
C3—C4—C5	116.2 (11)	C18—C20—H20C	109.5
C3—C4—C18	124.5 (10)	H20A—C20—H20C	109.5
C5—C4—C18	119.3 (11)	H20B—C20—H20C	109.5
C6—C5—C4	123.1 (11)	C23—C21—C6	113.9 (9)
C6—C5—H5	118.5	C23—C21—C22	111.1 (10)
C4—C5—H5	118.5	C6—C21—C22	111.2 (8)
C1—C6—C5	118.0 (10)	C23—C21—H21	106.7
C1—C6—C21	121.5 (11)	C6—C21—H21	106.7
C5—C6—C21	120.4 (10)	C22—C21—H21	106.7
O1—C7—C8	118.4 (11)	C21—C22—H22A	109.5
O1—C7—C1	121.9 (10)	C21—C22—H22B	109.5
C8—C7—C1	119.6 (10)	H22A—C22—H22B	109.5
C9—C8—C13	119.3 (10)	C21—C22—H22C	109.5
C9—C8—C7	119.6 (8)	H22A—C22—H22C	109.5
C13—C8—C7	121.1 (10)	H22B—C22—H22C	109.5
C8—C9—C10	120.3 (9)	C21—C23—H23A	109.5
C8—C9—H9	119.8	C21—C23—H23B	109.5
C10—C9—H9	119.8	H23A—C23—H23B	109.5
C9—C10—C11	121.0 (10)	C21—C23—H23C	109.5
C9—C10—H10	119.5	H23A—C23—H23C	109.5
C11—C10—H10	119.5	H23B—C23—H23C	109.5
C12—C11—C10	118.0 (9)	C25—N1—H1A	109.5
C12—C11—C14	120.9 (9)	C25—N1—H1B	109.5
C10—C11—C14	121.0 (10)	H1A—N1—H1B	109.5
C11—C12—C13	120.6 (9)	C25—N1—H1C	109.5
C11—C12—H12	119.7	H1A—N1—H1C	109.5
C13—C12—H12	119.7	H1B—N1—H1C	109.5
C8—C13—C12	120.7 (10)	C25—C24—H24A	109.5
C8—C13—H13	119.6	C25—C24—H24B	109.5
C12—C13—H13	119.6	H24A—C24—H24B	109.5
O3—C14—O2	123.8 (10)	C25—C24—H24C	109.5
O3—C14—C11	117.6 (10)	H24A—C24—H24C	109.5
O2—C14—C11	118.5 (9)	H24B—C24—H24C	109.5
C2—C15—C17	110.9 (8)	C26—C25—N1	109.0 (8)
C2—C15—C16	111.3 (8)	C26—C25—C24	116.6 (9)
C17—C15—C16	110.7 (9)	N1—C25—C24	109.7 (9)
C2—C15—H15	107.9	C26—C25—H25	107.0
C17—C15—H15	107.9	N1—C25—H25	107.0
C16—C15—H15	107.9	C24—C25—H25	107.0
C15—C16—H16A	109.5	C31—C26—C27	117.9 (12)
C15—C16—H16B	109.5	C31—C26—C25	120.5 (10)
H16A—C16—H16B	109.5	C27—C26—C25	121.6 (11)
C15—C16—H16C	109.5	C28—C27—C26	121.8 (12)
H16A—C16—H16C	109.5	C28—C27—H27	119.1
H16B—C16—H16C	109.5	C26—C27—H27	119.1
C15—C17—H17A	109.5	C27—C28—C29	120.8 (12)
C15—C17—H17B	109.5	C27—C28—H28	119.6
H17A—C17—H17B	109.5	C29—C28—H28	119.6
C15—C17—H17C	109.5	C30—C29—C28	118.6 (13)
H17A—C17—H17C	109.5	C30—C29—H29	120.7
H17B—C17—H17C	109.5	C28—C29—H29	120.7
C20—C18—C19	113.0 (10)	C29—C30—C31	119.9 (13)
C20—C18—C4	111.9 (10)	C29—C30—H30	120.1
C19—C18—C4	115.6 (9)	C31—C30—H30	120.1
C20—C18—H18	105.1	C26—C31—C30	121.0 (11)
C19—C18—H18	105.1	C26—C31—H31	119.5
C4—C18—H18	105.1	C30—C31—H31	119.5

(10hUV_075GPa)

Crystal data

C31H39NO3	Dx = 1.238 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.70932 Å
Orthorhombic, P212121	Cell parameters from 2531 reflections
a = 5.9793 (10) Å	θ = 2.4–23.8°
b = 13.334 (4) Å	µ = 0.08 mm^−1
c = 31.884 (8) Å	T = 299 K
V = 2542.0 (11) Å^3	Block, colourless
Z = 4	0.40 × 0.18 × 0.14 mm
F(000) = 1024

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.132
φ– and ω scans	θmax = 25.4°, θmin = 1.7°
13624 measured reflections	h = −7→7
2378 independent reflections	k = −13→12
1201 reflections with I > 2σ(I)	l = −31→31

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.069	w = 1/[σ^2(Fo^2) + (0.0914P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.189	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.17 e Å^−3
2378 reflections	Δρmin = −0.19 e Å^−3
278 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
74 restraints	Absolute structure parameter: −0.9 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3867 (11)	0.6251 (6)	0.4830 (2)	0.053 (2)
O3	0.6941 (13)	0.6172 (6)	0.4450 (3)	0.068 (2)
N1	0.9607 (14)	0.6719 (7)	0.5097 (3)	0.048 (3)
H1A	0.9639	0.7384	0.5122	0.058*
H1B	0.8527	0.6544	0.4919	0.058*
H1C	1.0917	0.6503	0.5000	0.058*
C1	0.1780 (16)	0.2605 (9)	0.3109 (3)	0.042 (3)*
C2	0.0987 (15)	0.3230 (9)	0.2798 (3)	0.043 (3)*
C3	0.1591 (15)	0.3072 (8)	0.2386 (4)	0.047 (3)*
H3	0.1021	0.3497	0.2181	0.056*
C4	0.2993 (15)	0.2317 (9)	0.2269 (3)	0.043 (3)*
C5	0.3816 (14)	0.1679 (8)	0.2585 (3)	0.041 (3)*
H5	0.4760	0.1152	0.2513	0.049*
C6	0.3248 (15)	0.1820 (8)	0.3002 (3)	0.038 (3)*
C8	0.2118 (16)	0.3497 (8)	0.3820 (3)	0.042 (3)*
C9	0.1047 (17)	0.3868 (8)	0.4162 (3)	0.045 (3)*
H9	−0.0344	0.3609	0.4234	0.054*
C10	0.1968 (17)	0.4620 (9)	0.4404 (3)	0.051 (3)*
H10	0.1215	0.4849	0.4641	0.061*
C11	0.4032 (16)	0.5036 (8)	0.4294 (3)	0.041 (3)*
C12	0.5145 (17)	0.4637 (8)	0.3952 (3)	0.044 (3)*
H12	0.6570	0.4867	0.3886	0.053*
C13	0.4178 (16)	0.3911 (9)	0.3711 (3)	0.051 (3)*
H13	0.4904	0.3690	0.3470	0.062*
C14	0.498 (2)	0.5878 (9)	0.4539 (4)	0.041 (3)
C15	−0.0501 (17)	0.4111 (8)	0.2922 (3)	0.047 (3)
H15	−0.0767	0.4060	0.3225	0.057*
C16	−0.2773 (15)	0.4039 (9)	0.2706 (3)	0.056 (3)
H16A	−0.3434	0.3398	0.2766	0.084*
H16B	−0.3734	0.4562	0.2808	0.084*
H16C	−0.2581	0.4110	0.2408	0.084*
C17	0.0656 (19)	0.5091 (9)	0.2846 (4)	0.073 (4)
H17A	−0.0312	0.5632	0.2926	0.109*
H17B	0.2005	0.5119	0.3009	0.109*
H17C	0.1018	0.5150	0.2554	0.109*
C18	0.3640 (18)	0.2084 (10)	0.1812 (4)	0.061 (4)
H18	0.3547	0.1354	0.1785	0.073*
C19	0.2069 (19)	0.2501 (10)	0.1488 (4)	0.077 (4)
H19A	0.0565	0.2304	0.1554	0.115*
H19B	0.2171	0.3219	0.1486	0.115*
H19C	0.2467	0.2244	0.1216	0.115*
C20	0.6052 (18)	0.2345 (12)	0.1740 (4)	0.090 (5)
H20A	0.6949	0.2055	0.1959	0.135*
H20B	0.6523	0.2085	0.1474	0.135*
H20C	0.6227	0.3060	0.1743	0.135*
C24	0.6962 (17)	0.6666 (8)	0.5685 (4)	0.058 (3)
H24A	0.7002	0.7385	0.5686	0.087*
H24B	0.5752	0.6439	0.5511	0.087*
H24C	0.6743	0.6427	0.5966	0.087*
C25	0.9166 (18)	0.6260 (11)	0.5515 (4)	0.056 (4)
H25	1.0346	0.6499	0.5703	0.067*
C26	0.939 (2)	0.5150 (10)	0.5492 (3)	0.045 (3)
C27	0.763 (2)	0.4569 (12)	0.5347 (4)	0.062 (4)
H27	0.6289	0.4870	0.5267	0.074*
C28	0.787 (3)	0.3547 (13)	0.5323 (4)	0.076 (4)
H28	0.6684	0.3155	0.5227	0.092*
C29	0.984 (3)	0.3100 (11)	0.5439 (5)	0.076 (4)
H29	0.9970	0.2407	0.5422	0.091*
C30	1.157 (2)	0.3644 (14)	0.5577 (4)	0.072 (4)
H30	1.2904	0.3333	0.5655	0.087*
C31	1.1351 (18)	0.4671 (12)	0.5602 (4)	0.058 (4)
H31	1.2556	0.5052	0.5695	0.070*
O1	−0.0561 (17)	0.2284 (8)	0.3694 (3)	0.079 (4)	0.931 (14)
C7	0.102 (2)	0.2744 (10)	0.3553 (3)	0.047 (3)	0.931 (14)
C21	0.4059 (19)	0.1084 (10)	0.3338 (4)	0.050 (4)	0.931 (14)
H21	0.4328	0.1476	0.3593	0.060*	0.931 (14)
C22	0.229 (2)	0.0306 (10)	0.3445 (4)	0.074 (4)	0.931 (14)
H22A	0.0916	0.0638	0.3516	0.110*	0.931 (14)
H22B	0.2052	−0.0124	0.3208	0.110*	0.931 (14)
H22C	0.2785	−0.0087	0.3680	0.110*	0.931 (14)
C23	0.6255 (19)	0.0578 (10)	0.3225 (4)	0.068 (4)	0.931 (14)
H23A	0.7350	0.1080	0.3158	0.102*	0.931 (14)
H23B	0.6767	0.0187	0.3458	0.102*	0.931 (14)
H23C	0.6034	0.0149	0.2987	0.102*	0.931 (14)
O1D	−0.120 (8)	0.259 (8)	0.364 (3)	0.076 (17)*	0.069 (14)
C7D	0.119 (8)	0.258 (3)	0.3585 (8)	0.051 (16)*	0.069 (14)
C21D	0.413 (15)	0.132 (6)	0.3406 (12)	0.052 (16)*	0.069 (14)
H21D	0.5498	0.1673	0.3489	0.063*	0.069 (14)
C22D	0.229 (17)	0.160 (4)	0.3720 (18)	0.06 (3)*	0.069 (14)
H22D	0.1183	0.1072	0.3731	0.076*	0.069 (14)
H22E	0.2935	0.1678	0.3997	0.076*	0.069 (14)
C23D	0.47 (3)	0.023 (7)	0.336 (3)	0.08 (3)*	0.069 (14)
H23E	0.5834	0.0146	0.3157	0.117*	0.069 (14)
H23D	0.5157	−0.0033	0.3626	0.117*	0.069 (14)
H23F	0.3357	−0.0128	0.3271	0.117*	0.069 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.058 (4)	0.048 (7)	0.052 (7)	0.004 (4)	0.003 (4)	−0.024 (4)
O3	0.054 (4)	0.070 (8)	0.081 (8)	−0.027 (5)	0.009 (5)	−0.014 (4)
N1	0.047 (5)	0.038 (9)	0.059 (9)	−0.011 (5)	−0.005 (5)	−0.003 (4)
C14	0.062 (7)	0.017 (10)	0.046 (10)	0.006 (7)	−0.016 (7)	−0.008 (5)
C15	0.055 (7)	0.033 (10)	0.055 (10)	0.011 (7)	0.009 (6)	0.000 (5)
C16	0.052 (6)	0.047 (12)	0.069 (11)	0.001 (6)	0.003 (7)	0.002 (5)
C17	0.058 (6)	0.029 (13)	0.132 (14)	−0.006 (7)	0.008 (7)	−0.013 (6)
C18	0.064 (8)	0.068 (12)	0.050 (12)	−0.007 (7)	0.009 (7)	−0.003 (6)
C19	0.074 (8)	0.115 (15)	0.042 (11)	0.021 (9)	−0.001 (8)	0.001 (6)
C20	0.069 (9)	0.147 (18)	0.054 (13)	0.019 (9)	0.023 (7)	0.009 (7)
C24	0.074 (8)	0.048 (11)	0.053 (11)	0.008 (7)	0.021 (7)	−0.002 (5)
C25	0.063 (8)	0.091 (15)	0.014 (11)	−0.009 (8)	−0.007 (6)	0.000 (6)
C26	0.065 (8)	0.052 (12)	0.018 (10)	0.003 (8)	0.010 (6)	0.001 (5)
C27	0.070 (9)	0.047 (14)	0.068 (14)	0.000 (9)	−0.005 (8)	0.002 (6)
C28	0.085 (11)	0.039 (16)	0.105 (16)	−0.016 (10)	0.000 (9)	−0.001 (7)
C29	0.111 (12)	0.037 (13)	0.080 (13)	0.010 (11)	0.036 (10)	0.011 (7)
C30	0.075 (10)	0.070 (17)	0.072 (14)	0.032 (11)	0.009 (8)	0.020 (7)
C31	0.045 (8)	0.078 (15)	0.052 (13)	0.023 (8)	0.008 (6)	0.007 (6)
O1	0.087 (6)	0.076 (10)	0.075 (9)	−0.041 (7)	0.033 (6)	−0.030 (5)
C7	0.057 (7)	0.034 (11)	0.050 (11)	−0.002 (7)	−0.001 (7)	−0.005 (5)
C21	0.061 (8)	0.063 (12)	0.025 (10)	0.013 (8)	−0.005 (6)	−0.001 (5)
C22	0.102 (10)	0.059 (13)	0.059 (12)	−0.017 (9)	−0.002 (8)	0.016 (6)
C23	0.069 (9)	0.067 (13)	0.068 (13)	0.011 (8)	−0.017 (8)	0.002 (6)

Geometric parameters (Å, º)

O2—C14	1.245 (11)	C18—H18	0.9800
O3—C14	1.269 (12)	C19—H19A	0.9600
N1—C25	1.489 (14)	C19—H19B	0.9600
N1—H1A	0.8900	C19—H19C	0.9600
N1—H1B	0.8900	C20—H20A	0.9600
N1—H1C	0.8900	C20—H20B	0.9600
C1—C2	1.377 (14)	C20—H20C	0.9600
C1—C6	1.408 (13)	C24—C25	1.525 (14)
C1—C7	1.498 (13)	C24—H24A	0.9600
C1—C7D	1.56 (2)	C24—H24B	0.9600
C2—C3	1.380 (13)	C24—H24C	0.9600
C2—C15	1.526 (14)	C25—C26	1.488 (15)
C3—C4	1.363 (13)	C25—H25	0.9800
C3—H3	0.9300	C26—C31	1.381 (15)
C4—C5	1.409 (14)	C26—C27	1.388 (15)
C4—C18	1.538 (15)	C27—C28	1.372 (17)
C5—C6	1.384 (13)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.371 (18)
C6—C21	1.531 (13)	C28—H28	0.9300
C6—C21D	1.54 (3)	C29—C30	1.342 (18)
C8—C9	1.356 (12)	C29—H29	0.9300
C8—C13	1.394 (13)	C30—C31	1.379 (16)
C8—C7	1.471 (14)	C30—H30	0.9300
C8—C7D	1.54 (2)	C31—H31	0.9300
C9—C10	1.381 (14)	O1—C7	1.215 (12)
C9—H9	0.9300	C21—C23	1.519 (14)
C10—C11	1.398 (12)	C21—C22	1.520 (14)
C10—H10	0.9300	C21—H21	0.9800
C11—C12	1.384 (13)	C22—H22A	0.9600
C11—C14	1.481 (14)	C22—H22B	0.9600
C12—C13	1.364 (14)	C22—H22C	0.9600
C12—H12	0.9300	C23—H23A	0.9600
C13—H13	0.9300	C23—H23B	0.9600
C15—C17	1.498 (15)	C23—H23C	0.9600
C15—C16	1.527 (13)	O1D—C7D	1.44 (3)
C15—H15	0.9800	C7D—C22D	1.53 (3)
C16—H16A	0.9600	C21D—C23D	1.50 (3)
C16—H16B	0.9600	C21D—C22D	1.53 (3)
C16—H16C	0.9600	C21D—H21D	0.9800
C17—H17A	0.9600	C22D—H22D	0.9700
C17—H17B	0.9600	C22D—H22E	0.9700
C17—H17C	0.9600	C23D—H23E	0.9600
C18—C20	1.501 (14)	C23D—H23D	0.9600
C18—C19	1.503 (15)	C23D—H23F	0.9600
C25—N1—H1A	109.5	C18—C20—H20A	109.5
C25—N1—H1B	109.5	C18—C20—H20B	109.5
H1A—N1—H1B	109.5	H20A—C20—H20B	109.5
C25—N1—H1C	109.5	C18—C20—H20C	109.5
H1A—N1—H1C	109.5	H20A—C20—H20C	109.5
H1B—N1—H1C	109.5	H20B—C20—H20C	109.5
C2—C1—C6	119.4 (10)	C25—C24—H24A	109.5
C2—C1—C7	120.0 (11)	C25—C24—H24B	109.5
C6—C1—C7	120.5 (9)	H24A—C24—H24B	109.5
C2—C1—C7D	129 (2)	C25—C24—H24C	109.5
C6—C1—C7D	111 (2)	H24A—C24—H24C	109.5
C1—C2—C3	120.2 (11)	H24B—C24—H24C	109.5
C1—C2—C15	118.7 (10)	C26—C25—N1	110.5 (9)
C3—C2—C15	121.1 (9)	C26—C25—C24	116.5 (10)
C4—C3—C2	122.3 (10)	N1—C25—C24	109.0 (10)
C4—C3—H3	118.8	C26—C25—H25	106.7
C2—C3—H3	118.8	N1—C25—H25	106.7
C3—C4—C5	117.7 (11)	C24—C25—H25	106.7
C3—C4—C18	124.3 (10)	C31—C26—C27	118.1 (13)
C5—C4—C18	118.0 (10)	C31—C26—C25	121.6 (12)
C6—C5—C4	121.4 (11)	C27—C26—C25	120.2 (12)
C6—C5—H5	119.3	C28—C27—C26	119.6 (13)
C4—C5—H5	119.3	C28—C27—H27	120.2
C5—C6—C1	119.0 (8)	C26—C27—H27	120.2
C5—C6—C21	120.5 (10)	C29—C28—C27	120.4 (14)
C1—C6—C21	120.3 (10)	C29—C28—H28	119.8
C5—C6—C21D	131 (2)	C27—C28—H28	119.8
C1—C6—C21D	109 (2)	C30—C29—C28	121.3 (15)
C9—C8—C13	118.2 (10)	C30—C29—H29	119.3
C9—C8—C7	120.3 (9)	C28—C29—H29	119.3
C13—C8—C7	121.2 (11)	C29—C30—C31	118.7 (13)
C9—C8—C7D	120.7 (16)	C29—C30—H30	120.7
C13—C8—C7D	120.8 (17)	C31—C30—H30	120.6
C8—C9—C10	121.7 (10)	C30—C31—C26	121.8 (13)
C8—C9—H9	119.1	C30—C31—H31	119.1
C10—C9—H9	119.1	C26—C31—H31	119.1
C9—C10—C11	120.0 (11)	O1—C7—C8	118.5 (11)
C9—C10—H10	120.0	O1—C7—C1	121.5 (10)
C11—C10—H10	120.0	C8—C7—C1	119.9 (10)
C12—C11—C10	118.0 (10)	C23—C21—C22	110.6 (11)
C12—C11—C14	121.6 (9)	C23—C21—C6	113.1 (10)
C10—C11—C14	120.4 (10)	C22—C21—C6	112.0 (9)
C13—C12—C11	120.8 (9)	C23—C21—H21	106.9
C13—C12—H12	119.6	C22—C21—H21	106.9
C11—C12—H12	119.6	C6—C21—H21	106.9
C12—C13—C8	121.0 (11)	C21—C22—H22A	109.5
C12—C13—H13	119.5	C21—C22—H22B	109.5
C8—C13—H13	119.5	H22A—C22—H22B	109.5
O2—C14—O3	122.6 (10)	C21—C22—H22C	109.5
O2—C14—C11	119.5 (10)	H22A—C22—H22C	109.5
O3—C14—C11	118.0 (10)	H22B—C22—H22C	109.5
C17—C15—C2	111.1 (8)	C21—C23—H23A	109.5
C17—C15—C16	113.1 (9)	C21—C23—H23B	109.5
C2—C15—C16	110.7 (9)	H23A—C23—H23B	109.5
C17—C15—H15	107.2	C21—C23—H23C	109.5
C2—C15—H15	107.2	H23A—C23—H23C	109.5
C16—C15—H15	107.2	H23B—C23—H23C	109.5
C15—C16—H16A	109.5	O1D—C7D—C22D	114 (4)
C15—C16—H16B	109.5	O1D—C7D—C8	107 (3)
H16A—C16—H16B	109.5	C22D—C7D—C8	113 (3)
C15—C16—H16C	109.5	O1D—C7D—C1	110 (4)
H16A—C16—H16C	109.5	C22D—C7D—C1	101 (3)
H16B—C16—H16C	109.5	C8—C7D—C1	112.2 (19)
C15—C17—H17A	109.5	C23D—C21D—C22D	117 (5)
C15—C17—H17B	109.5	C23D—C21D—C6	114 (4)
H17A—C17—H17B	109.5	C22D—C21D—C6	101 (3)
C15—C17—H17C	109.5	C23D—C21D—H21D	107.9
H17A—C17—H17C	109.5	C22D—C21D—H21D	107.9
H17B—C17—H17C	109.5	C6—C21D—H21D	107.9
C20—C18—C19	114.2 (11)	C7D—C22D—C21D	110 (3)
C20—C18—C4	109.8 (10)	C7D—C22D—H22D	109.8
C19—C18—C4	114.8 (10)	C21D—C22D—H22D	109.8
C20—C18—H18	105.7	C7D—C22D—H22E	109.8
C19—C18—H18	105.7	C21D—C22D—H22E	109.8
C4—C18—H18	105.7	H22D—C22D—H22E	108.2
C18—C19—H19A	109.5	C21D—C23D—H23E	109.5
C18—C19—H19B	109.5	C21D—C23D—H23D	109.5
H19A—C19—H19B	109.5	H23E—C23D—H23D	109.5
C18—C19—H19C	109.5	C21D—C23D—H23F	109.5
H19A—C19—H19C	109.5	H23E—C23D—H23F	109.5
H19B—C19—H19C	109.5	H23D—C23D—H23F	109.5

(44hUV_075GPa)

Crystal data

C31H39NO3	Dx = 1.237 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.70932 Å
Orthorhombic, P212121	Cell parameters from 1825 reflections
a = 5.9907 (12) Å	θ = 2.4–24.8°
b = 13.301 (5) Å	µ = 0.08 mm^−1
c = 31.928 (9) Å	T = 299 K
V = 2544.1 (13) Å^3	Block, colourless
Z = 4	0.40 × 0.18 × 0.14 mm
F(000) = 1024

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.182
φ– and ω scans	θmax = 25.0°, θmin = 1.7°
15004 measured reflections	h = −7→7
2311 independent reflections	k = −12→12
1039 reflections with I > 2σ(I)	l = −31→31

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0919P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.203	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.14 e Å^−3
2311 reflections	Δρmin = −0.15 e Å^−3
259 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
225 restraints	Absolute structure parameter: −2.8 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3828 (14)	0.6251 (7)	0.4829 (3)	0.068 (3)
O3	0.6937 (16)	0.6163 (7)	0.4452 (3)	0.076 (3)
C1	0.1806 (17)	0.2604 (9)	0.3102 (4)	0.0502 (14)*
C2	0.0991 (17)	0.3242 (10)	0.2787 (4)	0.0502 (14)*
C3	0.1630 (16)	0.3079 (9)	0.2375 (4)	0.0502 (14)*
H3	0.1072	0.3498	0.2167	0.060*
C4	0.3045 (17)	0.2325 (10)	0.2266 (4)	0.0502 (14)*
C5	0.3820 (16)	0.1694 (10)	0.2587 (4)	0.0502 (14)*
H5	0.4749	0.1160	0.2517	0.060*
C6	0.3253 (18)	0.1835 (9)	0.3005 (4)	0.0502 (14)*
C14	0.498 (2)	0.5866 (11)	0.4542 (4)	0.052 (4)
C18	0.3671 (19)	0.2074 (11)	0.1819 (4)	0.072 (4)*
H18	0.3572	0.1340	0.1799	0.087*
C19	0.6088 (19)	0.2326 (12)	0.1733 (4)	0.086 (5)*
H19A	0.7005	0.2056	0.1952	0.129*
H19B	0.6527	0.2038	0.1470	0.129*
H19C	0.6267	0.3042	0.1722	0.129*
C20	0.212 (2)	0.2473 (11)	0.1486 (5)	0.097 (5)*
H20A	0.0609	0.2295	0.1555	0.145*
H20B	0.2248	0.3192	0.1472	0.145*
H20C	0.2509	0.2187	0.1220	0.145*
C26	0.940 (2)	0.5155 (11)	0.5497 (4)	0.059 (4)*
N1	0.9601 (15)	0.6715 (7)	0.5092 (3)	0.057 (3)
H1A	0.8506	0.6534	0.4920	0.068*
H1B	1.0898	0.6490	0.4994	0.068*
H1C	0.9646	0.7383	0.5111	0.068*
C24	0.6970 (18)	0.6664 (10)	0.5690 (4)	0.077 (4)*
H24A	0.6717	0.6379	0.5963	0.115*
H24B	0.7019	0.7383	0.5712	0.115*
H24C	0.5779	0.6470	0.5506	0.115*
C25	0.919 (2)	0.6278 (12)	0.5517 (4)	0.066 (4)*
H25	1.0371	0.6524	0.5702	0.079*
C27	1.139 (2)	0.4687 (11)	0.5595 (4)	0.070 (4)*
H27	1.2617	0.5070	0.5675	0.084*
C28	1.156 (2)	0.3657 (12)	0.5576 (5)	0.085 (5)*
H28	1.2891	0.3354	0.5659	0.102*
C29	0.993 (2)	0.3091 (13)	0.5444 (5)	0.090 (5)*
H29	1.0115	0.2398	0.5435	0.107*
C30	0.795 (2)	0.3501 (12)	0.5321 (5)	0.088 (5)*
H30	0.6803	0.3095	0.5224	0.106*
C31	0.768 (2)	0.4569 (11)	0.5343 (4)	0.070 (4)*
H31	0.6352	0.4866	0.5255	0.083*
O1	−0.054 (3)	0.2269 (12)	0.3690 (5)	0.074 (5)	0.745 (4)
C7	0.104 (3)	0.2733 (14)	0.3552 (5)	0.061 (6)*	0.745 (4)
C8	0.2140 (19)	0.3494 (9)	0.3820 (4)	0.041 (3)*	0.745 (4)
C9	0.105 (2)	0.3856 (11)	0.4161 (4)	0.049 (4)*	0.745 (4)
H9	−0.0342	0.3594	0.4233	0.058*	0.745 (4)
C10	0.198 (2)	0.4604 (11)	0.4400 (4)	0.054 (4)*	0.745 (4)
H10	0.1241	0.4823	0.4640	0.065*	0.745 (4)
C11	0.398 (2)	0.5035 (11)	0.4290 (4)	0.049 (4)*	0.745 (4)
C12	0.514 (2)	0.4629 (11)	0.3958 (4)	0.053 (4)*	0.745 (4)
H12	0.6574	0.4854	0.3898	0.063*	0.745 (4)
C13	0.418 (2)	0.3894 (11)	0.3715 (4)	0.052 (4)*	0.745 (4)
H13	0.4924	0.3664	0.3478	0.062*	0.745 (4)
C15	−0.047 (2)	0.4137 (11)	0.2906 (4)	0.056 (4)	0.745 (4)
H15	−0.0710	0.4096	0.3209	0.067*	0.745 (4)
C16	−0.2744 (19)	0.4058 (11)	0.2702 (4)	0.057 (4)	0.745 (4)
H16A	−0.3389	0.3415	0.2766	0.085*	0.745 (4)
H16B	−0.3695	0.4582	0.2807	0.085*	0.745 (4)
H16C	−0.2592	0.4128	0.2404	0.085*	0.745 (4)
C17	0.068 (2)	0.5109 (11)	0.2827 (5)	0.073 (5)	0.745 (4)
H17A	0.2105	0.5109	0.2964	0.110*	0.745 (4)
H17B	0.0888	0.5196	0.2531	0.110*	0.745 (4)
H17C	−0.0215	0.5650	0.2934	0.110*	0.745 (4)
C21	0.399 (3)	0.1082 (12)	0.3330 (5)	0.056 (5)	0.745 (4)
H21	0.4259	0.1472	0.3586	0.067*	0.745 (4)
C22	0.220 (3)	0.0320 (13)	0.3443 (5)	0.086 (6)	0.745 (4)
H22A	0.2774	−0.0136	0.3650	0.129*	0.745 (4)
H22B	0.0922	0.0664	0.3554	0.129*	0.745 (4)
H22C	0.1779	−0.0050	0.3198	0.129*	0.745 (4)
C23	0.619 (2)	0.0567 (14)	0.3232 (5)	0.075 (6)	0.745 (4)
H23A	0.6541	0.0102	0.3452	0.113*	0.745 (4)
H23B	0.6061	0.0211	0.2972	0.113*	0.745 (4)
H23C	0.7348	0.1061	0.3211	0.113*	0.745 (4)
O1D	−0.124 (5)	0.263 (4)	0.3578 (17)	0.057 (19)*	0.176 (4)
C7D	0.117 (6)	0.260 (2)	0.3576 (8)	0.07 (2)*	0.176 (4)
C8D	0.2140 (19)	0.3494 (9)	0.3820 (4)	0.041 (3)*	0.176 (4)
C9D	0.105 (2)	0.3856 (11)	0.4161 (4)	0.049 (4)*	0.176 (4)
H9D	−0.0342	0.3594	0.4233	0.058*	0.176 (4)
C10D	0.198 (2)	0.4604 (11)	0.4400 (4)	0.054 (4)*	0.176 (4)
H10D	0.1241	0.4823	0.4640	0.065*	0.176 (4)
C11D	0.398 (2)	0.5035 (11)	0.4290 (4)	0.049 (4)*	0.176 (4)
C12D	0.514 (2)	0.4629 (11)	0.3958 (4)	0.053 (4)*	0.176 (4)
H12D	0.6574	0.4854	0.3898	0.063*	0.176 (4)
C13D	0.418 (2)	0.3894 (11)	0.3715 (4)	0.052 (4)*	0.176 (4)
H13D	0.4924	0.3664	0.3478	0.062*	0.176 (4)
C15D	−0.047 (2)	0.4137 (11)	0.2906 (4)	0.056 (4)	0.176 (4)
H15D	−0.0710	0.4096	0.3209	0.067*	0.176 (4)
C16D	−0.2744 (19)	0.4058 (11)	0.2702 (4)	0.057 (4)	0.176 (4)
H16D	−0.3389	0.3415	0.2766	0.085*	0.176 (4)
H16E	−0.3695	0.4582	0.2807	0.085*	0.176 (4)
H16F	−0.2592	0.4128	0.2404	0.085*	0.176 (4)
C17D	0.068 (2)	0.5109 (11)	0.2827 (5)	0.073 (5)	0.176 (4)
H17D	0.2105	0.5109	0.2964	0.110*	0.176 (4)
H17E	0.0888	0.5196	0.2531	0.110*	0.176 (4)
H17F	−0.0215	0.5650	0.2934	0.110*	0.176 (4)
C21D	0.418 (9)	0.135 (4)	0.3402 (10)	0.060 (11)*	0.176 (4)
H21D	0.5520	0.1713	0.3491	0.073*	0.176 (4)
C22D	0.225 (9)	0.160 (3)	0.3699 (14)	0.078 (18)*	0.176 (4)
H22D	0.1148	0.1069	0.3690	0.094*	0.176 (4)
H22E	0.2812	0.1647	0.3984	0.094*	0.176 (4)
C23D	0.478 (14)	0.027 (4)	0.333 (2)	0.09 (2)*	0.176 (4)
H23D	0.5353	−0.0018	0.3582	0.130*	0.176 (4)
H23E	0.3469	−0.0094	0.3243	0.130*	0.176 (4)
H23F	0.5888	0.0228	0.3112	0.130*	0.176 (4)
O1P	−0.082 (16)	0.256 (7)	0.371 (2)	0.08 (3)*	0.079 (4)
C7P	0.038 (7)	0.314 (3)	0.3428 (8)	0.07 (2)*	0.079 (4)
C8P	0.163 (9)	0.391 (5)	0.3699 (15)	0.023 (18)*	0.079 (4)
C9P	0.050 (9)	0.425 (6)	0.4051 (19)	0.030 (18)*	0.079 (4)
H9P	−0.0965	0.4055	0.4104	0.036*	0.079 (4)
C10P	0.162 (9)	0.489 (5)	0.4320 (18)	0.038 (19)*	0.079 (4)
H10P	0.0911	0.5126	0.4559	0.046*	0.079 (4)
C11P	0.381 (7)	0.517 (2)	0.4237 (11)	0.049 (19)*	0.079 (4)
C12P	0.493 (10)	0.483 (5)	0.3884 (18)	0.046 (19)*	0.079 (4)
H12P	0.6390	0.5026	0.3831	0.055*	0.079 (4)
C13P	0.381 (11)	0.419 (6)	0.361 (2)	0.048 (19)*	0.079 (4)
H13P	0.4512	0.3948	0.3369	0.058*	0.079 (4)
C15P	−0.076 (8)	0.378 (5)	0.3045 (12)	0.058 (12)*	0.079 (4)
C16P	−0.318 (8)	0.356 (11)	0.295 (3)	0.08 (2)*	0.079 (4)
H16G	−0.4107	0.3945	0.3135	0.117*	0.079 (4)
H16H	−0.3495	0.3739	0.2665	0.117*	0.079 (4)
H16I	−0.3466	0.2856	0.2991	0.117*	0.079 (4)
C17P	−0.03 (2)	0.491 (4)	0.305 (3)	0.07 (2)*	0.079 (4)
H17G	0.1267	0.5017	0.3114	0.107*	0.079 (4)
H17H	−0.0638	0.5193	0.2785	0.107*	0.079 (4)
H17I	−0.1182	0.5219	0.3265	0.107*	0.079 (4)
C21P	0.399 (3)	0.1082 (12)	0.3330 (5)	0.056 (5)	0.079 (4)
H21P	0.4259	0.1472	0.3586	0.067*	0.079 (4)
C22P	0.220 (3)	0.0320 (13)	0.3443 (5)	0.086 (6)	0.079 (4)
H22F	0.2774	−0.0136	0.3650	0.129*	0.079 (4)
H22G	0.0922	0.0664	0.3554	0.129*	0.079 (4)
H22H	0.1779	−0.0050	0.3198	0.129*	0.079 (4)
C23P	0.619 (2)	0.0567 (14)	0.3232 (5)	0.075 (6)	0.079 (4)
H23G	0.6541	0.0102	0.3452	0.113*	0.079 (4)
H23H	0.6061	0.0211	0.2972	0.113*	0.079 (4)
H23I	0.7348	0.1061	0.3211	0.113*	0.079 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.074 (6)	0.056 (9)	0.075 (9)	0.007 (5)	0.007 (5)	−0.028 (5)
O3	0.072 (5)	0.069 (9)	0.086 (9)	−0.035 (6)	0.005 (6)	−0.014 (5)
C14	0.071 (9)	0.029 (13)	0.056 (13)	0.011 (9)	−0.022 (9)	−0.004 (7)
N1	0.060 (6)	0.037 (10)	0.073 (10)	−0.014 (6)	−0.006 (6)	0.002 (5)
O1	0.105 (10)	0.059 (13)	0.059 (11)	−0.017 (10)	0.017 (9)	−0.024 (7)
C15	0.072 (8)	0.043 (11)	0.053 (10)	0.005 (8)	−0.001 (7)	0.002 (6)
C16	0.065 (8)	0.041 (13)	0.065 (12)	−0.005 (8)	0.007 (8)	0.006 (6)
C17	0.056 (8)	0.041 (14)	0.123 (15)	0.005 (8)	0.014 (9)	−0.016 (8)
C21	0.078 (10)	0.052 (12)	0.036 (10)	0.020 (9)	−0.004 (8)	0.003 (7)
C22	0.109 (13)	0.056 (15)	0.093 (15)	−0.008 (12)	−0.009 (11)	0.038 (9)
C23	0.094 (12)	0.078 (15)	0.055 (14)	0.027 (11)	−0.010 (10)	0.009 (8)
C15D	0.072 (8)	0.043 (11)	0.053 (10)	0.005 (8)	−0.001 (7)	0.002 (6)
C16D	0.065 (8)	0.041 (13)	0.065 (12)	−0.005 (8)	0.007 (8)	0.006 (6)
C17D	0.056 (8)	0.041 (14)	0.123 (15)	0.005 (8)	0.014 (9)	−0.016 (8)
C21P	0.078 (10)	0.052 (12)	0.036 (10)	0.020 (9)	−0.004 (8)	0.003 (7)
C22P	0.109 (13)	0.056 (15)	0.093 (15)	−0.008 (12)	−0.009 (11)	0.038 (9)
C23P	0.094 (12)	0.078 (15)	0.055 (14)	0.027 (11)	−0.010 (10)	0.009 (8)

Geometric parameters (Å, º)

O2—C14	1.257 (14)	C8—C13	1.376 (15)
O3—C14	1.268 (14)	C9—C10	1.372 (16)
C1—C6	1.376 (14)	C10—C11	1.375 (15)
C1—C2	1.401 (15)	C11—C12	1.379 (16)
C1—C7	1.517 (16)	C12—C13	1.373 (17)
C1—C7P	1.53 (2)	C15—C17	1.485 (18)
C1—C7D	1.56 (2)	C15—C16	1.515 (16)
C2—C3	1.389 (14)	C21—C23	1.515 (17)
C2—C15P	1.51 (2)	C21—C22	1.520 (17)
C2—C15	1.525 (17)	O1D—C7D	1.44 (3)
C2—C15D	1.525 (17)	C7D—C22D	1.53 (3)
C3—C4	1.358 (14)	C7D—C8D	1.54 (2)
C4—C5	1.404 (15)	C8D—C9D	1.360 (14)
C4—C18	1.513 (16)	C8D—C13D	1.376 (15)
C5—C6	1.392 (14)	C9D—C10D	1.372 (16)
C6—C21P	1.508 (16)	C10D—C11D	1.375 (15)
C6—C21	1.508 (16)	C11D—C12D	1.379 (16)
C6—C21D	1.53 (2)	C12D—C13D	1.373 (17)
C14—C11D	1.493 (18)	C15D—C17D	1.485 (18)
C14—C11	1.493 (18)	C15D—C16D	1.515 (16)
C14—C11P	1.52 (2)	C21D—C23D	1.50 (3)
C18—C20	1.509 (16)	C21D—C22D	1.53 (3)
C18—C19	1.511 (15)	O1P—C7P	1.39 (3)
C26—C27	1.381 (15)	C7P—C8P	1.54 (2)
C26—C31	1.382 (15)	C7P—C15P	1.64 (3)
C26—C25	1.501 (17)	C8P—C13P	1.38 (3)
N1—C25	1.495 (15)	C8P—C9P	1.39 (3)
C24—C25	1.529 (15)	C9P—C10P	1.38 (3)
C27—C28	1.375 (16)	C10P—C11P	1.39 (3)
C28—C29	1.304 (17)	C11P—C12P	1.39 (3)
C29—C30	1.361 (17)	C12P—C13P	1.40 (3)
C30—C31	1.432 (18)	C15P—C16P	1.51 (3)
O1—C7	1.214 (15)	C15P—C17P	1.53 (3)
C7—C8	1.480 (17)	C21P—C23P	1.515 (17)
C8—C9	1.360 (14)	C21P—C22P	1.520 (17)
C6—C1—C2	120.6 (11)	C12—C11—C14	120.1 (12)
C6—C1—C7	119.1 (11)	C13—C12—C11	120.2 (12)
C2—C1—C7	120.3 (12)	C12—C13—C8	120.6 (12)
C6—C1—C7P	148.6 (17)	C17—C15—C16	113.8 (12)
C2—C1—C7P	90.7 (15)	C17—C15—C2	111.9 (11)
C6—C1—C7D	111.5 (16)	C16—C15—C2	110.8 (11)
C2—C1—C7D	127.8 (17)	C6—C21—C23	114.5 (13)
C3—C2—C1	119.2 (12)	C6—C21—C22	113.5 (11)
C3—C2—C15P	141.4 (18)	C23—C21—C22	111.0 (14)
C1—C2—C15P	97.8 (16)	O1D—C7D—C22D	116 (3)
C3—C2—C15	121.0 (10)	O1D—C7D—C8D	111 (3)
C1—C2—C15	119.6 (11)	C22D—C7D—C8D	112 (3)
C3—C2—C15D	121.0 (10)	O1D—C7D—C1	104 (3)
C1—C2—C15D	119.6 (11)	C22D—C7D—C1	99 (2)
C4—C3—C2	122.1 (12)	C8D—C7D—C1	113.3 (19)
C3—C4—C5	117.4 (12)	C9D—C8D—C13D	119.1 (11)
C3—C4—C18	124.0 (11)	C9D—C8D—C7D	119.9 (14)
C5—C4—C18	118.3 (12)	C13D—C8D—C7D	120.8 (15)
C6—C5—C4	122.7 (12)	C8D—C9D—C10D	120.4 (11)
C1—C6—C5	118.0 (10)	C9D—C10D—C11D	121.0 (13)
C1—C6—C21P	121.7 (12)	C10D—C11D—C12D	118.2 (13)
C5—C6—C21P	119.9 (12)	C10D—C11D—C14	121.5 (14)
C1—C6—C21	121.7 (12)	C12D—C11D—C14	120.1 (12)
C5—C6—C21	119.9 (12)	C13D—C12D—C11D	120.2 (12)
C1—C6—C21D	111.1 (17)	C12D—C13D—C8D	120.6 (12)
C5—C6—C21D	130.5 (17)	C17D—C15D—C16D	113.8 (12)
O2—C14—O3	123.1 (12)	C17D—C15D—C2	111.9 (11)
O2—C14—C11D	118.2 (13)	C16D—C15D—C2	110.8 (11)
O3—C14—C11D	118.7 (13)	C23D—C21D—C6	111 (4)
O2—C14—C11	118.2 (13)	C23D—C21D—C22D	119 (4)
O3—C14—C11	118.7 (13)	C6—C21D—C22D	98 (2)
O2—C14—C11P	118 (2)	C7D—C22D—C21D	111 (3)
O3—C14—C11P	118 (2)	O1P—C7P—C1	118 (4)
C20—C18—C19	112.6 (12)	O1P—C7P—C8P	105 (3)
C20—C18—C4	115.7 (11)	C1—C7P—C8P	115 (3)
C19—C18—C4	111.1 (11)	O1P—C7P—C15P	124 (4)
C27—C26—C31	118.1 (14)	C1—C7P—C15P	87.9 (15)
C27—C26—C25	120.8 (13)	C8P—C7P—C15P	106 (3)
C31—C26—C25	120.8 (11)	C13P—C8P—C9P	123 (3)
N1—C25—C26	109.6 (10)	C13P—C8P—C7P	121 (3)
N1—C25—C24	110.0 (11)	C9P—C8P—C7P	116 (3)
C26—C25—C24	115.0 (11)	C10P—C9P—C8P	118 (3)
C28—C27—C26	120.3 (14)	C9P—C10P—C11P	121 (3)
C29—C28—C27	122.1 (15)	C12P—C11P—C10P	121 (3)
C28—C29—C30	121.0 (17)	C12P—C11P—C14	120 (3)
C29—C30—C31	119.0 (15)	C10P—C11P—C14	119 (3)
C26—C31—C30	119.3 (13)	C11P—C12P—C13P	119 (3)
O1—C7—C8	118.9 (15)	C8P—C13P—C12P	119 (3)
O1—C7—C1	121.5 (14)	C16P—C15P—C2	118 (4)
C8—C7—C1	119.4 (13)	C16P—C15P—C17P	112 (3)
C9—C8—C13	119.1 (11)	C2—C15P—C17P	110 (4)
C9—C8—C7	119.4 (11)	C16P—C15P—C7P	117 (4)
C13—C8—C7	121.3 (13)	C2—C15P—C7P	82.9 (15)
C8—C9—C10	120.4 (11)	C17P—C15P—C7P	115 (4)
C9—C10—C11	121.0 (13)	C6—C21P—C23P	114.5 (13)
C10—C11—C12	118.2 (13)	C6—C21P—C22P	113.5 (11)
C10—C11—C14	121.5 (14)	C23P—C21P—C22P	111.0 (14)

(44hUV_01MPa)

Crystal data

C31H39NO3	Dx = 1.112 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 6751 reflections
a = 6.2884 (3) Å	θ = 1.9–23.1°
b = 13.7572 (5) Å	µ = 0.07 mm^−1
c = 32.7030 (13) Å	T = 299 K
V = 2829.2 (2) Å^3	Block, colourless
Z = 4	0.40 × 0.18 × 0.14 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	5496 independent reflections
Radiation source: fine-focus sealed tube	4027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 15.9718 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −7→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −16→16
Tmin = 0.995, Tmax = 1.000	l = −38→39
25524 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.3002P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.11 e Å^−3
5496 reflections	Δρmin = −0.13 e Å^−3
505 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
560 restraints	Absolute structure parameter: 2.0 (6)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.0340 (11)	0.2438 (4)	0.63069 (18)	0.0815 (18)	0.740 (4)
O2	0.6228 (3)	0.63113 (15)	0.51713 (7)	0.0599 (6)	0.740 (4)
O3	0.3222 (4)	0.61925 (18)	0.55187 (7)	0.0703 (7)	0.740 (4)
C1	0.8160 (18)	0.2758 (7)	0.6882 (2)	0.043 (2)	0.740 (4)
C2	0.886 (2)	0.3407 (9)	0.7181 (3)	0.049 (3)	0.740 (4)
C3	0.826 (3)	0.3252 (12)	0.7589 (4)	0.053 (3)	0.740 (4)
H3	0.8760	0.3676	0.7788	0.064*	0.740 (4)
C4	0.696 (3)	0.2500 (12)	0.7704 (3)	0.054 (3)	0.740 (4)
C5	0.624 (3)	0.1886 (11)	0.7396 (3)	0.053 (3)	0.740 (4)
H5	0.5316	0.1387	0.7466	0.064*	0.740 (4)
C6	0.684 (3)	0.1976 (9)	0.6984 (3)	0.048 (3)	0.740 (4)
C7	0.8893 (13)	0.2920 (5)	0.6447 (2)	0.0490 (18)	0.740 (4)
C8	0.7790 (12)	0.3667 (5)	0.6195 (2)	0.042 (2)	0.740 (4)
C9	0.8710 (12)	0.3944 (6)	0.5826 (2)	0.053 (2)	0.740 (4)
H9	0.9944	0.3631	0.5741	0.064*	0.740 (4)
C10	0.7867 (13)	0.4661 (5)	0.5582 (3)	0.0510 (19)	0.740 (4)
H10	0.8548	0.4842	0.5342	0.061*	0.740 (4)
C11	0.6017 (14)	0.5105 (6)	0.5698 (3)	0.042 (3)	0.740 (4)
C12	0.4974 (13)	0.4797 (6)	0.6050 (2)	0.052 (2)	0.740 (4)
H12	0.3671	0.5067	0.6122	0.063*	0.740 (4)
C13	0.5885 (9)	0.4085 (5)	0.62934 (19)	0.0476 (17)	0.740 (4)
H13	0.5185	0.3887	0.6530	0.057*	0.740 (4)
C14	0.5081 (5)	0.5932 (2)	0.54472 (9)	0.0488 (7)	0.740 (4)
C15	1.0251 (19)	0.4284 (8)	0.7076 (5)	0.060 (3)	0.740 (4)
H15	1.0372	0.4318	0.6778	0.072*	0.740 (4)
C16	1.2494 (15)	0.4172 (8)	0.7252 (3)	0.066 (2)	0.740 (4)
H16A	1.3329	0.4731	0.7181	0.099*	0.740 (4)
H16B	1.2415	0.4114	0.7544	0.099*	0.740 (4)
H16C	1.3146	0.3599	0.7140	0.099*	0.740 (4)
C17	0.9222 (17)	0.5240 (6)	0.7226 (4)	0.086 (3)	0.740 (4)
H17A	1.0125	0.5778	0.7156	0.129*	0.740 (4)
H17B	0.7861	0.5322	0.7098	0.129*	0.740 (4)
H17C	0.9042	0.5215	0.7517	0.129*	0.740 (4)
C18	0.6363 (17)	0.2290 (10)	0.8147 (3)	0.069 (2)	0.740 (4)
H18	0.6471	0.1581	0.8168	0.083*	0.740 (4)
C19	0.7875 (13)	0.2648 (10)	0.8466 (2)	0.092 (3)	0.740 (4)
H19A	0.9305	0.2493	0.8387	0.137*	0.740 (4)
H19B	0.7733	0.3340	0.8494	0.137*	0.740 (4)
H19C	0.7556	0.2343	0.8723	0.137*	0.740 (4)
C20	0.4076 (10)	0.2489 (8)	0.8235 (2)	0.085 (2)	0.740 (4)
H20A	0.3216	0.2238	0.8017	0.128*	0.740 (4)
H20B	0.3682	0.2180	0.8487	0.128*	0.740 (4)
H20C	0.3859	0.3178	0.8258	0.128*	0.740 (4)
C21	0.6113 (17)	0.1268 (7)	0.6657 (2)	0.065 (3)	0.740 (4)
H21	0.5914	0.1643	0.6405	0.078*	0.740 (4)
C22	0.7803 (13)	0.0504 (5)	0.6569 (2)	0.083 (2)	0.740 (4)
H22A	0.7299	0.0068	0.6362	0.124*	0.740 (4)
H22B	0.9079	0.0817	0.6477	0.124*	0.740 (4)
H22C	0.8098	0.0145	0.6815	0.124*	0.740 (4)
C23	0.3986 (11)	0.0784 (5)	0.6755 (2)	0.077 (2)	0.740 (4)
H23A	0.3610	0.0347	0.6538	0.115*	0.740 (4)
H23B	0.4107	0.0429	0.7006	0.115*	0.740 (4)
H23C	0.2906	0.1273	0.6782	0.115*	0.740 (4)
O1D	1.088 (4)	0.2710 (19)	0.6371 (9)	0.055 (6)*	0.184 (4)
O2D	0.6228 (3)	0.63113 (15)	0.51713 (7)	0.0599 (6)	0.184 (4)
O3D	0.3222 (4)	0.61925 (18)	0.55187 (7)	0.0703 (7)	0.184 (4)
C1D	0.810 (8)	0.286 (3)	0.6888 (9)	0.049 (11)*	0.184 (4)
C2D	0.892 (10)	0.346 (4)	0.7188 (12)	0.047 (11)*	0.184 (4)
C3D	0.843 (10)	0.323 (4)	0.7599 (13)	0.047 (11)*	0.184 (4)
H3D	0.8933	0.3640	0.7805	0.056*	0.184 (4)
C4D	0.720 (8)	0.241 (4)	0.7708 (10)	0.032 (8)*	0.184 (4)
C5D	0.647 (11)	0.181 (4)	0.7398 (10)	0.043 (9)*	0.184 (4)
H5D	0.5794	0.1224	0.7460	0.052*	0.184 (4)
C6D	0.677 (11)	0.208 (4)	0.6995 (10)	0.051 (11)*	0.184 (4)
C7D	0.862 (5)	0.277 (2)	0.6423 (9)	0.063 (10)*	0.184 (4)
C8D	0.787 (4)	0.3581 (19)	0.6138 (9)	0.034 (8)*	0.184 (4)
C9D	0.919 (4)	0.4048 (18)	0.5854 (8)	0.026 (6)*	0.184 (4)
H9D	1.0601	0.3866	0.5813	0.031*	0.184 (4)
C10D	0.822 (4)	0.482 (2)	0.5637 (10)	0.032 (7)*	0.184 (4)
H10D	0.9051	0.5142	0.5446	0.039*	0.184 (4)
C11D	0.610 (5)	0.513 (2)	0.5684 (10)	0.043 (11)*	0.184 (4)
C12D	0.491 (5)	0.4623 (19)	0.5972 (8)	0.046 (9)*	0.184 (4)
H12D	0.3503	0.4797	0.6017	0.055*	0.184 (4)
C13D	0.579 (4)	0.3865 (18)	0.6194 (8)	0.048 (8)*	0.184 (4)
H13D	0.4952	0.3540	0.6385	0.058*	0.184 (4)
C14D	0.5081 (5)	0.5932 (2)	0.54472 (9)	0.0488 (7)	0.184 (4)
C15D	1.047 (7)	0.427 (3)	0.7099 (17)	0.049 (10)*	0.184 (4)
H15D	1.0955	0.4155	0.6819	0.059*	0.184 (4)
C16D	1.243 (7)	0.421 (4)	0.7359 (13)	0.063 (9)*	0.184 (4)
H16D	1.3357	0.4743	0.7290	0.094*	0.184 (4)
H16E	1.2038	0.4258	0.7642	0.094*	0.184 (4)
H16F	1.3144	0.3609	0.7310	0.094*	0.184 (4)
C17D	0.937 (9)	0.527 (3)	0.7094 (17)	0.080 (13)*	0.184 (4)
H17D	0.8134	0.5240	0.6922	0.120*	0.184 (4)
H17E	0.8951	0.5441	0.7367	0.120*	0.184 (4)
H17F	1.0338	0.5747	0.6990	0.120*	0.184 (4)
C18D	0.644 (6)	0.214 (3)	0.8152 (11)	0.055 (6)*	0.184 (4)
H18D	0.5911	0.1469	0.8155	0.066*	0.184 (4)
C19D	0.825 (6)	0.224 (3)	0.8457 (11)	0.097 (11)*	0.184 (4)
H19D	0.9382	0.1809	0.8384	0.145*	0.184 (4)
H19E	0.8760	0.2899	0.8455	0.145*	0.184 (4)
H19F	0.7741	0.2084	0.8726	0.145*	0.184 (4)
C20D	0.465 (5)	0.284 (3)	0.8277 (11)	0.104 (10)*	0.184 (4)
H20D	0.3493	0.2787	0.8087	0.157*	0.184 (4)
H20E	0.4161	0.2681	0.8547	0.157*	0.184 (4)
H20F	0.5180	0.3496	0.8275	0.157*	0.184 (4)
C21D	0.602 (6)	0.148 (2)	0.6624 (9)	0.068 (10)*	0.184 (4)
H21D	0.4717	0.1790	0.6526	0.082*	0.184 (4)
C22D	0.777 (3)	0.1761 (14)	0.6325 (6)	0.080 (6)*	0.184 (4)
H22D	0.7205	0.1753	0.6049	0.096*	0.184 (4)
H22E	0.8914	0.1292	0.6340	0.096*	0.184 (4)
C23D	0.547 (7)	0.0450 (19)	0.6712 (9)	0.109 (10)*	0.184 (4)
H23D	0.4332	0.0428	0.6908	0.164*	0.184 (4)
H23E	0.5021	0.0137	0.6463	0.164*	0.184 (4)
H23F	0.6689	0.0120	0.6820	0.164*	0.184 (4)
O1P	1.113 (5)	0.299 (2)	0.6508 (11)	0.063 (9)*	0.076 (3)
O2P	0.6228 (3)	0.63113 (15)	0.51713 (7)	0.0599 (6)	0.076 (3)
O3P	0.3222 (4)	0.61925 (18)	0.55187 (7)	0.0703 (7)	0.076 (3)
C1P	0.779 (8)	0.284 (3)	0.6949 (11)	0.044 (12)*	0.076 (3)
C2P	0.835 (7)	0.342 (3)	0.7280 (12)	0.039 (11)*	0.076 (3)
C3P	0.765 (8)	0.314 (4)	0.7661 (12)	0.055 (12)*	0.076 (3)
H3P	0.7958	0.3528	0.7885	0.066*	0.076 (3)
C4P	0.651 (8)	0.230 (4)	0.7724 (12)	0.025 (10)*	0.076 (3)
C5P	0.581 (11)	0.174 (4)	0.7397 (13)	0.033 (11)*	0.076 (3)
H5P	0.4895	0.1215	0.7433	0.040*	0.076 (3)
C6P	0.655 (13)	0.201 (4)	0.7010 (14)	0.044 (13)*	0.076 (3)
C7P	0.925 (4)	0.339 (2)	0.6666 (8)	0.063 (10)*	0.076 (3)
C8P	0.814 (5)	0.4040 (17)	0.6350 (8)	0.047 (9)*	0.076 (3)
C9P	0.919 (5)	0.442 (2)	0.6020 (9)	0.052 (9)*	0.076 (3)
H9P	1.0618	0.4278	0.5983	0.062*	0.076 (3)
C10P	0.818 (5)	0.5020 (19)	0.5737 (10)	0.050 (10)*	0.076 (3)
H10P	0.8956	0.5258	0.5518	0.060*	0.076 (3)
C11P	0.607 (6)	0.5273 (11)	0.5770 (8)	0.048 (12)*	0.076 (3)
C12P	0.499 (7)	0.490 (3)	0.6104 (11)	0.051 (13)*	0.076 (3)
H12P	0.3555	0.5045	0.6139	0.062*	0.076 (3)
C13P	0.600 (5)	0.429 (3)	0.6389 (12)	0.050 (12)*	0.076 (3)
H13P	0.5230	0.4057	0.6610	0.060*	0.076 (3)
C14P	0.5081 (5)	0.5932 (2)	0.54472 (9)	0.0488 (7)	0.076 (3)
C15P	0.983 (7)	0.409 (3)	0.7069 (11)	0.054 (12)*	0.076 (3)
C16P	1.220 (7)	0.401 (6)	0.715 (2)	0.078 (13)*	0.076 (3)
H16G	1.2941	0.4488	0.6989	0.116*	0.076 (3)
H16H	1.2479	0.4115	0.7433	0.116*	0.076 (3)
H16I	1.2685	0.3372	0.7072	0.116*	0.076 (3)
C17P	0.923 (15)	0.515 (3)	0.701 (3)	0.10 (2)*	0.076 (3)
H17G	1.0350	0.5483	0.6867	0.150*	0.076 (3)
H17H	0.7941	0.5193	0.6851	0.150*	0.076 (3)
H17I	0.9005	0.5452	0.7270	0.150*	0.076 (3)
C18P	0.563 (8)	0.207 (4)	0.8150 (12)	0.060 (7)*	0.076 (3)
H18P	0.5514	0.1364	0.8187	0.072*	0.076 (3)
C19P	0.717 (11)	0.249 (8)	0.846 (2)	0.100 (14)*	0.076 (3)
H19G	0.8515	0.2162	0.8445	0.149*	0.076 (3)
H19H	0.7376	0.3172	0.8411	0.149*	0.076 (3)
H19I	0.6600	0.2408	0.8734	0.149*	0.076 (3)
C20P	0.345 (9)	0.253 (8)	0.815 (2)	0.086 (13)*	0.076 (3)
H20G	0.2586	0.2218	0.7942	0.129*	0.076 (3)
H20H	0.2794	0.2443	0.8410	0.129*	0.076 (3)
H20I	0.3570	0.3207	0.8087	0.129*	0.076 (3)
C21P	0.583 (12)	0.136 (5)	0.6664 (18)	0.063 (13)*	0.076 (3)
H21P	0.6059	0.1680	0.6401	0.076*	0.076 (3)
C22P	0.712 (13)	0.041 (5)	0.668 (3)	0.09 (2)*	0.076 (3)
H22F	0.6680	−0.0011	0.6463	0.133*	0.076 (3)
H22G	0.8607	0.0557	0.6652	0.133*	0.076 (3)
H22H	0.6884	0.0096	0.6939	0.133*	0.076 (3)
C23P	0.349 (11)	0.107 (7)	0.671 (3)	0.12 (3)*	0.076 (3)
H23G	0.3083	0.0655	0.6488	0.173*	0.076 (3)
H23H	0.3292	0.0732	0.6964	0.173*	0.076 (3)
H23I	0.2624	0.1645	0.6708	0.173*	0.076 (3)
N1	0.0382 (4)	0.66931 (17)	0.49138 (7)	0.0480 (6)
H1A	0.1377	0.6473	0.5084	0.058*
H1B	−0.0897	0.6532	0.5009	0.058*
H1C	0.0478	0.7337	0.4895	0.058*
C24	0.2811 (6)	0.6596 (3)	0.43250 (11)	0.0765 (11)
H24A	0.3946	0.6395	0.4502	0.115*
H24B	0.2801	0.7292	0.4305	0.115*
H24C	0.3019	0.6320	0.4058	0.115*
C25	0.0699 (5)	0.6249 (2)	0.44984 (9)	0.0573 (9)
H25	−0.0428	0.6498	0.4320	0.069*
C26	0.0442 (6)	0.5159 (3)	0.45217 (9)	0.0592 (9)
C27	−0.1422 (7)	0.4721 (3)	0.43977 (11)	0.0784 (11)
H27	−0.2541	0.5104	0.4305	0.094*
C28	−0.1653 (10)	0.3718 (4)	0.44096 (15)	0.1092 (18)
H28	−0.2922	0.3436	0.4325	0.131*
C29	−0.0032 (14)	0.3147 (4)	0.45440 (17)	0.120 (2)
H29	−0.0182	0.2474	0.4546	0.144*
C30	0.1810 (12)	0.3563 (4)	0.46759 (15)	0.1155 (17)
H30	0.2902	0.3172	0.4775	0.139*
C31	0.2073 (7)	0.4567 (3)	0.46639 (12)	0.0825 (12)
H31	0.3344	0.4843	0.4751	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.100 (4)	0.074 (4)	0.071 (3)	0.043 (4)	0.030 (3)	0.023 (3)
O2	0.0587 (13)	0.0590 (13)	0.0620 (14)	0.0031 (12)	0.0025 (11)	0.0263 (11)
O3	0.0548 (14)	0.0958 (18)	0.0603 (14)	0.0213 (13)	0.0022 (11)	0.0255 (13)
C1	0.049 (4)	0.036 (3)	0.044 (4)	0.016 (3)	0.003 (2)	0.011 (2)
C2	0.050 (4)	0.043 (4)	0.055 (4)	0.005 (3)	0.010 (3)	0.013 (2)
C3	0.053 (5)	0.055 (4)	0.052 (4)	0.002 (3)	−0.003 (3)	−0.008 (2)
C4	0.048 (6)	0.060 (6)	0.053 (4)	0.002 (5)	0.006 (3)	0.008 (3)
C5	0.051 (6)	0.051 (5)	0.057 (4)	−0.006 (4)	−0.002 (3)	0.016 (2)
C6	0.059 (4)	0.043 (4)	0.041 (4)	0.007 (3)	−0.005 (2)	0.011 (2)
C7	0.060 (4)	0.043 (3)	0.043 (3)	0.009 (3)	0.004 (2)	0.007 (2)
C8	0.058 (4)	0.040 (3)	0.026 (3)	0.005 (2)	0.004 (2)	0.000 (2)
C9	0.042 (4)	0.059 (4)	0.059 (4)	0.009 (3)	0.007 (3)	0.009 (3)
C10	0.057 (4)	0.051 (4)	0.045 (4)	−0.003 (3)	0.006 (3)	0.011 (3)
C11	0.047 (4)	0.043 (4)	0.036 (3)	−0.002 (2)	−0.005 (2)	0.0076 (18)
C12	0.049 (4)	0.067 (4)	0.041 (4)	0.012 (3)	0.009 (3)	0.012 (4)
C13	0.062 (4)	0.055 (4)	0.026 (3)	0.008 (3)	0.011 (2)	0.006 (3)
C14	0.0512 (19)	0.0512 (18)	0.0440 (18)	−0.0017 (16)	−0.0051 (15)	0.0074 (14)
C15	0.062 (5)	0.053 (4)	0.065 (5)	−0.011 (3)	−0.003 (3)	0.004 (2)
C16	0.066 (4)	0.076 (5)	0.056 (7)	−0.010 (3)	0.008 (4)	−0.010 (4)
C17	0.067 (4)	0.041 (3)	0.151 (10)	−0.004 (3)	0.016 (6)	0.014 (5)
C18	0.068 (4)	0.089 (6)	0.051 (3)	0.006 (4)	0.011 (3)	0.003 (3)
C19	0.087 (6)	0.146 (9)	0.042 (3)	0.007 (6)	0.003 (3)	0.000 (4)
C20	0.069 (5)	0.116 (6)	0.070 (5)	−0.011 (5)	0.024 (4)	−0.010 (4)
C21	0.095 (5)	0.058 (4)	0.043 (3)	−0.015 (4)	−0.018 (3)	0.013 (3)
C22	0.120 (6)	0.067 (4)	0.062 (4)	0.013 (4)	0.004 (4)	−0.023 (3)
C23	0.082 (5)	0.075 (4)	0.074 (4)	−0.022 (4)	−0.021 (3)	0.007 (3)
O2D	0.0587 (13)	0.0590 (13)	0.0620 (14)	0.0031 (12)	0.0025 (11)	0.0263 (11)
O3D	0.0548 (14)	0.0958 (18)	0.0603 (14)	0.0213 (13)	0.0022 (11)	0.0255 (13)
C14D	0.0512 (19)	0.0512 (18)	0.0440 (18)	−0.0017 (16)	−0.0051 (15)	0.0074 (14)
O2P	0.0587 (13)	0.0590 (13)	0.0620 (14)	0.0031 (12)	0.0025 (11)	0.0263 (11)
O3P	0.0548 (14)	0.0958 (18)	0.0603 (14)	0.0213 (13)	0.0022 (11)	0.0255 (13)
C14P	0.0512 (19)	0.0512 (18)	0.0440 (18)	−0.0017 (16)	−0.0051 (15)	0.0074 (14)
N1	0.0450 (14)	0.0505 (14)	0.0486 (16)	0.0030 (12)	−0.0007 (12)	0.0113 (12)
C24	0.091 (3)	0.084 (3)	0.054 (2)	−0.007 (2)	0.022 (2)	0.0034 (19)
C25	0.063 (2)	0.067 (2)	0.0412 (19)	−0.0001 (18)	−0.0079 (15)	0.0087 (15)
C26	0.069 (2)	0.068 (2)	0.0410 (18)	−0.004 (2)	0.0005 (16)	−0.0031 (16)
C27	0.078 (3)	0.093 (3)	0.064 (2)	−0.015 (2)	0.006 (2)	−0.013 (2)
C28	0.121 (4)	0.104 (4)	0.103 (4)	−0.049 (4)	0.031 (3)	−0.040 (3)
C29	0.183 (7)	0.071 (3)	0.106 (4)	−0.019 (4)	0.038 (4)	−0.013 (3)
C30	0.160 (5)	0.072 (3)	0.115 (4)	0.021 (4)	0.004 (4)	0.000 (3)
C31	0.098 (3)	0.067 (3)	0.083 (3)	0.001 (2)	−0.008 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C7	1.214 (7)	C18D—C20D	1.54 (3)
O2—C14	1.267 (3)	C18D—H18D	0.9800
O3—C14	1.245 (4)	C19D—H19D	0.9600
C1—C2	1.397 (8)	C19D—H19E	0.9600
C1—C6	1.399 (8)	C19D—H19F	0.9600
C1—C7	1.512 (8)	C20D—H20D	0.9600
C2—C3	1.402 (9)	C20D—H20E	0.9600
C2—C15	1.527 (9)	C20D—H20F	0.9600
C3—C4	1.371 (9)	C21D—C23D	1.49 (2)
C3—H3	0.9300	C21D—C22D	1.52 (2)
C4—C5	1.391 (9)	C21D—H21D	0.9800
C4—C18	1.525 (9)	C22D—H22D	0.9700
C5—C6	1.403 (9)	C22D—H22E	0.9700
C5—H5	0.9300	C23D—H23D	0.9600
C6—C21	1.518 (8)	C23D—H23E	0.9600
C7—C8	1.489 (7)	C23D—H23F	0.9600
C8—C13	1.367 (8)	O1P—C7P	1.40 (2)
C8—C9	1.391 (8)	O2P—C14P	1.267 (3)
C9—C10	1.374 (7)	O3P—C14P	1.245 (4)
C9—H9	0.9300	C1P—C6P	1.39 (2)
C10—C11	1.368 (8)	C1P—C2P	1.40 (3)
C10—H10	0.9300	C1P—C7P	1.51 (2)
C11—C12	1.391 (8)	C2P—C3P	1.38 (2)
C11—C14	1.521 (7)	C2P—C15P	1.48 (2)
C12—C13	1.386 (7)	C3P—C4P	1.37 (2)
C12—H12	0.9300	C3P—H3P	0.9300
C13—H13	0.9300	C4P—C5P	1.39 (3)
C15—C16	1.531 (10)	C4P—C18P	1.53 (2)
C15—C17	1.546 (11)	C5P—C6P	1.40 (3)
C15—H15	0.9800	C5P—H5P	0.9300
C16—H16A	0.9600	C6P—C21P	1.52 (3)
C16—H16B	0.9600	C7P—C8P	1.54 (2)
C16—H16C	0.9600	C7P—C15P	1.67 (2)
C17—H17A	0.9600	C8P—C9P	1.37 (2)
C17—H17B	0.9600	C8P—C13P	1.39 (2)
C17—H17C	0.9600	C9P—C10P	1.39 (2)
C18—C20	1.492 (10)	C9P—H9P	0.9300
C18—C19	1.496 (10)	C10P—C11P	1.38 (2)
C18—H18	0.9800	C10P—H10P	0.9300
C19—H19A	0.9600	C11P—C12P	1.39 (3)
C19—H19B	0.9600	C11P—C14P	1.52 (2)
C19—H19C	0.9600	C12P—C13P	1.40 (3)
C20—H20A	0.9600	C12P—H12P	0.9300
C20—H20B	0.9600	C13P—H13P	0.9300
C20—H20C	0.9600	C15P—C16P	1.52 (3)
C21—C22	1.522 (11)	C15P—C17P	1.52 (3)
C21—C23	1.528 (10)	C16P—H16G	0.9600
C21—H21	0.9800	C16P—H16H	0.9600
C22—H22A	0.9600	C16P—H16I	0.9600
C22—H22B	0.9600	C17P—H17G	0.9600
C22—H22C	0.9600	C17P—H17H	0.9600
C23—H23A	0.9600	C17P—H17I	0.9600
C23—H23B	0.9600	C18P—C20P	1.51 (3)
C23—H23C	0.9600	C18P—C19P	1.53 (3)
O1D—C7D	1.44 (2)	C18P—H18P	0.9800
O2D—C14D	1.267 (3)	C19P—H19G	0.9600
O3D—C14D	1.245 (4)	C19P—H19H	0.9600
C1D—C2D	1.38 (2)	C19P—H19I	0.9600
C1D—C6D	1.40 (2)	C20P—H20G	0.9600
C1D—C7D	1.56 (2)	C20P—H20H	0.9600
C2D—C3D	1.41 (2)	C20P—H20I	0.9600
C2D—C15D	1.51 (2)	C21P—C22P	1.53 (3)
C3D—C4D	1.42 (2)	C21P—C23P	1.53 (3)
C3D—H3D	0.9300	C21P—H21P	0.9800
C4D—C5D	1.39 (2)	C22P—H22F	0.9600
C4D—C18D	1.57 (2)	C22P—H22G	0.9600
C5D—C6D	1.38 (2)	C22P—H22H	0.9600
C5D—H5D	0.9300	C23P—H23G	0.9600
C6D—C21D	1.54 (2)	C23P—H23H	0.9600
C7D—C22D	1.52 (2)	C23P—H23I	0.9600
C7D—C8D	1.53 (2)	N1—C25	1.503 (4)
C8D—C13D	1.38 (2)	N1—H1A	0.8900
C8D—C9D	1.40 (2)	N1—H1B	0.8900
C9D—C10D	1.41 (2)	N1—H1C	0.8900
C9D—H9D	0.9300	C24—C25	1.521 (5)
C10D—C11D	1.41 (2)	C24—H24A	0.9600
C10D—H10D	0.9300	C24—H24B	0.9600
C11D—C12D	1.39 (2)	C24—H24C	0.9600
C11D—C14D	1.49 (2)	C25—C26	1.510 (5)
C12D—C13D	1.38 (2)	C25—H25	0.9800
C12D—H12D	0.9300	C26—C27	1.378 (5)
C13D—H13D	0.9300	C26—C31	1.390 (5)
C15D—C16D	1.50 (3)	C27—C28	1.388 (6)
C15D—C17D	1.54 (3)	C27—H27	0.9300
C15D—H15D	0.9800	C28—C29	1.360 (8)
C16D—H16D	0.9600	C28—H28	0.9300
C16D—H16E	0.9600	C29—C30	1.362 (8)
C16D—H16F	0.9600	C29—H29	0.9300
C17D—H17D	0.9600	C30—C31	1.392 (6)
C17D—H17E	0.9600	C30—H30	0.9300
C17D—H17F	0.9600	C31—H31	0.9300
C18D—C19D	1.52 (3)
C2—C1—C6	120.8 (7)	C18D—C19D—H19D	109.5
C2—C1—C7	118.0 (7)	C18D—C19D—H19E	109.5
C6—C1—C7	121.3 (7)	H19D—C19D—H19E	109.5
C1—C2—C3	118.9 (8)	C18D—C19D—H19F	109.5
C1—C2—C15	121.9 (8)	H19D—C19D—H19F	109.5
C3—C2—C15	119.2 (9)	H19E—C19D—H19F	109.5
C4—C3—C2	122.5 (9)	C18D—C20D—H20D	109.5
C4—C3—H3	118.7	C18D—C20D—H20E	109.5
C2—C3—H3	118.7	H20D—C20D—H20E	109.5
C3—C4—C5	116.9 (8)	C18D—C20D—H20F	109.5
C3—C4—C18	123.5 (10)	H20D—C20D—H20F	109.5
C5—C4—C18	119.6 (9)	H20E—C20D—H20F	109.5
C4—C5—C6	123.7 (9)	C23D—C21D—C22D	122 (3)
C4—C5—H5	118.1	C23D—C21D—C6D	116 (3)
C6—C5—H5	118.1	C22D—C21D—C6D	99 (2)
C1—C6—C5	117.1 (8)	C23D—C21D—H21D	106.4
C1—C6—C21	120.2 (7)	C22D—C21D—H21D	106.4
C5—C6—C21	122.6 (8)	C6D—C21D—H21D	106.4
O1—C7—C8	121.2 (6)	C21D—C22D—C7D	110.5 (18)
O1—C7—C1	120.1 (6)	C21D—C22D—H22D	109.5
C8—C7—C1	118.7 (6)	C7D—C22D—H22D	109.5
C13—C8—C9	117.0 (6)	C21D—C22D—H22E	109.5
C13—C8—C7	124.6 (6)	C7D—C22D—H22E	109.5
C9—C8—C7	118.3 (6)	H22D—C22D—H22E	108.1
C10—C9—C8	122.6 (7)	C21D—C23D—H23D	109.5
C10—C9—H9	118.7	C21D—C23D—H23E	109.5
C8—C9—H9	118.7	H23D—C23D—H23E	109.5
C11—C10—C9	119.3 (6)	C21D—C23D—H23F	109.5
C11—C10—H10	120.4	H23D—C23D—H23F	109.5
C9—C10—H10	120.4	H23E—C23D—H23F	109.5
C10—C11—C12	119.6 (6)	C6P—C1P—C2P	120 (2)
C10—C11—C14	121.0 (6)	C6P—C1P—C7P	147 (3)
C12—C11—C14	119.5 (7)	C2P—C1P—C7P	92 (2)
C13—C12—C11	119.7 (6)	C3P—C2P—C1P	117 (3)
C13—C12—H12	120.1	C3P—C2P—C15P	143 (3)
C11—C12—H12	120.1	C1P—C2P—C15P	99 (2)
C8—C13—C12	121.6 (6)	C4P—C3P—C2P	123 (3)
C8—C13—H13	119.2	C4P—C3P—H3P	118.6
C12—C13—H13	119.2	C2P—C3P—H3P	118.6
O3—C14—O2	123.3 (3)	C3P—C4P—C5P	121 (3)
O3—C14—C11	118.5 (4)	C3P—C4P—C18P	120 (3)
O2—C14—C11	118.2 (4)	C5P—C4P—C18P	118 (3)
C2—C15—C16	111.3 (9)	C4P—C5P—C6P	116 (3)
C2—C15—C17	111.2 (9)	C4P—C5P—H5P	122.0
C16—C15—C17	110.6 (9)	C6P—C5P—H5P	122.0
C2—C15—H15	107.9	C1P—C6P—C5P	122 (3)
C16—C15—H15	107.9	C1P—C6P—C21P	123 (3)
C17—C15—H15	107.9	C5P—C6P—C21P	114 (3)
C15—C16—H16A	109.5	O1P—C7P—C1P	123 (3)
C15—C16—H16B	109.5	O1P—C7P—C8P	111 (2)
H16A—C16—H16B	109.5	C1P—C7P—C8P	115 (3)
C15—C16—H16C	109.5	O1P—C7P—C15P	109 (2)
H16A—C16—H16C	109.5	C1P—C7P—C15P	86.4 (18)
H16B—C16—H16C	109.5	C8P—C7P—C15P	106.7 (18)
C15—C17—H17A	109.5	C9P—C8P—C13P	116 (2)
C15—C17—H17B	109.5	C9P—C8P—C7P	122 (2)
H17A—C17—H17B	109.5	C13P—C8P—C7P	122 (2)
C15—C17—H17C	109.5	C8P—C9P—C10P	122 (3)
H17A—C17—H17C	109.5	C8P—C9P—H9P	119.0
H17B—C17—H17C	109.5	C10P—C9P—H9P	119.0
C20—C18—C19	114.7 (7)	C11P—C10P—C9P	123 (3)
C20—C18—C4	112.8 (8)	C11P—C10P—H10P	118.7
C19—C18—C4	116.3 (8)	C9P—C10P—H10P	118.7
C20—C18—H18	103.7	C10P—C11P—C12P	116 (2)
C19—C18—H18	103.7	C10P—C11P—C14P	119 (2)
C4—C18—H18	103.7	C12P—C11P—C14P	125 (3)
C18—C19—H19A	109.5	C11P—C12P—C13P	121 (3)
C18—C19—H19B	109.5	C11P—C12P—H12P	119.3
H19A—C19—H19B	109.5	C13P—C12P—H12P	119.3
C18—C19—H19C	109.5	C8P—C13P—C12P	122 (3)
H19A—C19—H19C	109.5	C8P—C13P—H13P	119.1
H19B—C19—H19C	109.5	C12P—C13P—H13P	119.1
C18—C20—H20A	109.5	O3P—C14P—O2P	123.3 (3)
C18—C20—H20B	109.5	O3P—C14P—C11P	115.0 (15)
H20A—C20—H20B	109.5	O2P—C14P—C11P	120.5 (15)
C18—C20—H20C	109.5	C2P—C15P—C16P	120 (3)
H20A—C20—H20C	109.5	C2P—C15P—C17P	120 (4)
H20B—C20—H20C	109.5	C16P—C15P—C17P	110 (3)
C6—C21—C22	111.4 (9)	C2P—C15P—C7P	82.8 (18)
C6—C21—C23	113.3 (8)	C16P—C15P—C7P	108 (3)
C22—C21—C23	110.5 (6)	C17P—C15P—C7P	114 (3)
C6—C21—H21	107.1	C15P—C16P—H16G	109.5
C22—C21—H21	107.1	C15P—C16P—H16H	109.5
C23—C21—H21	107.1	H16G—C16P—H16H	109.5
C21—C22—H22A	109.5	C15P—C16P—H16I	109.5
C21—C22—H22B	109.5	H16G—C16P—H16I	109.5
H22A—C22—H22B	109.5	H16H—C16P—H16I	109.5
C21—C22—H22C	109.5	C15P—C17P—H17G	109.5
H22A—C22—H22C	109.5	C15P—C17P—H17H	109.5
H22B—C22—H22C	109.5	H17G—C17P—H17H	109.5
C21—C23—H23A	109.5	C15P—C17P—H17I	109.5
C21—C23—H23B	109.5	H17G—C17P—H17I	109.5
H23A—C23—H23B	109.5	H17H—C17P—H17I	109.5
C21—C23—H23C	109.5	C20P—C18P—C19P	115 (4)
H23A—C23—H23C	109.5	C20P—C18P—C4P	104 (3)
H23B—C23—H23C	109.5	C19P—C18P—C4P	108 (3)
C2D—C1D—C6D	120 (2)	C20P—C18P—H18P	110.1
C2D—C1D—C7D	131 (2)	C19P—C18P—H18P	110.1
C6D—C1D—C7D	108 (2)	C4P—C18P—H18P	110.1
C1D—C2D—C3D	118 (3)	C18P—C19P—H19G	109.5
C1D—C2D—C15D	123 (3)	C18P—C19P—H19H	109.5
C3D—C2D—C15D	119 (3)	H19G—C19P—H19H	109.5
C2D—C3D—C4D	122 (3)	C18P—C19P—H19I	109.5
C2D—C3D—H3D	119.0	H19G—C19P—H19I	109.5
C4D—C3D—H3D	119.0	H19H—C19P—H19I	109.5
C5D—C4D—C3D	118 (3)	C18P—C20P—H20G	109.5
C5D—C4D—C18D	116 (3)	C18P—C20P—H20H	109.5
C3D—C4D—C18D	126 (3)	H20G—C20P—H20H	109.5
C6D—C5D—C4D	119 (3)	C18P—C20P—H20I	109.5
C6D—C5D—H5D	120.4	H20G—C20P—H20I	109.5
C4D—C5D—H5D	120.4	H20H—C20P—H20I	109.5
C5D—C6D—C1D	122 (3)	C6P—C21P—C22P	109 (4)
C5D—C6D—C21D	124 (2)	C6P—C21P—C23P	111 (4)
C1D—C6D—C21D	113 (2)	C22P—C21P—C23P	107 (4)
O1D—C7D—C22D	106 (2)	C6P—C21P—H21P	110.0
O1D—C7D—C8D	106 (2)	C22P—C21P—H21P	110.0
C22D—C7D—C8D	115 (2)	C23P—C21P—H21P	110.0
O1D—C7D—C1D	109 (3)	C21P—C22P—H22F	109.5
C22D—C7D—C1D	101.5 (18)	C21P—C22P—H22G	109.5
C8D—C7D—C1D	118 (3)	H22F—C22P—H22G	109.5
C13D—C8D—C9D	121 (2)	C21P—C22P—H22H	109.5
C13D—C8D—C7D	115 (2)	H22F—C22P—H22H	109.5
C9D—C8D—C7D	124 (2)	H22G—C22P—H22H	109.5
C8D—C9D—C10D	115 (2)	C21P—C23P—H23G	109.5
C8D—C9D—H9D	122.6	C21P—C23P—H23H	109.5
C10D—C9D—H9D	122.6	H23G—C23P—H23H	109.5
C11D—C10D—C9D	126 (2)	C21P—C23P—H23I	109.5
C11D—C10D—H10D	117.1	H23G—C23P—H23I	109.5
C9D—C10D—H10D	117.1	H23H—C23P—H23I	109.5
C12D—C11D—C10D	115 (2)	C25—N1—H1A	109.5
C12D—C11D—C14D	119 (2)	C25—N1—H1B	109.5
C10D—C11D—C14D	125 (2)	H1A—N1—H1B	109.5
C13D—C12D—C11D	121 (3)	C25—N1—H1C	109.5
C13D—C12D—H12D	119.3	H1A—N1—H1C	109.5
C11D—C12D—H12D	119.3	H1B—N1—H1C	109.5
C8D—C13D—C12D	121 (2)	C25—C24—H24A	109.5
C8D—C13D—H13D	119.3	C25—C24—H24B	109.5
C12D—C13D—H13D	119.3	H24A—C24—H24B	109.5
O3D—C14D—O2D	123.3 (3)	C25—C24—H24C	109.5
O3D—C14D—C11D	121.2 (13)	H24A—C24—H24C	109.5
O2D—C14D—C11D	115.4 (13)	H24B—C24—H24C	109.5
C16D—C15D—C2D	113 (3)	N1—C25—C26	110.1 (2)
C16D—C15D—C17D	115 (3)	N1—C25—C24	109.0 (3)
C2D—C15D—C17D	112 (3)	C26—C25—C24	115.1 (3)
C16D—C15D—H15D	105.5	N1—C25—H25	107.4
C2D—C15D—H15D	105.5	C26—C25—H25	107.4
C17D—C15D—H15D	105.5	C24—C25—H25	107.4
C15D—C16D—H16D	109.5	C27—C26—C31	118.0 (4)
C15D—C16D—H16E	109.5	C27—C26—C25	120.7 (3)
H16D—C16D—H16E	109.5	C31—C26—C25	121.3 (3)
C15D—C16D—H16F	109.5	C26—C27—C28	121.0 (5)
H16D—C16D—H16F	109.5	C26—C27—H27	119.5
H16E—C16D—H16F	109.5	C28—C27—H27	119.5
C15D—C17D—H17D	109.5	C29—C28—C27	120.4 (5)
C15D—C17D—H17E	109.5	C29—C28—H28	119.8
H17D—C17D—H17E	109.5	C27—C28—H28	119.8
C15D—C17D—H17F	109.5	C28—C29—C30	119.8 (5)
H17D—C17D—H17F	109.5	C28—C29—H29	120.1
H17E—C17D—H17F	109.5	C30—C29—H29	120.1
C19D—C18D—C20D	108 (3)	C29—C30—C31	120.6 (5)
C19D—C18D—C4D	111 (3)	C29—C30—H30	119.7
C20D—C18D—C4D	109 (3)	C31—C30—H30	119.7
C19D—C18D—H18D	109.6	C26—C31—C30	120.2 (5)
C20D—C18D—H18D	109.6	C26—C31—H31	119.9
C4D—C18D—H18D	109.6	C30—C31—H31	119.9

(0minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.250 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1031 reflections
a = 5.9414 (8) Å	θ = 5.6–21.7°
b = 13.381 (3) Å	µ = 0.08 mm^−1
c = 31.662 (18) Å	T = 299 K
V = 2517.2 (16) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2091 independent reflections
Radiation source: fine-focus sealed tube	1073 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.6°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→15
Tmin = 0.334, Tmax = 1.000	l = −19→22
5484 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.0585P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.164	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.16 e Å^−3
2091 reflections	Δρmin = −0.19 e Å^−3
264 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
0 restraints	Absolute structure parameter: 1.6 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0568 (13)	0.2206 (6)	0.6295 (4)	0.083 (5)
O2	0.6131 (11)	0.6246 (6)	0.5177 (4)	0.055 (5)
O3	0.3025 (11)	0.6156 (6)	0.5557 (4)	0.069 (5)
N1	0.0415 (13)	0.6715 (7)	0.4901 (6)	0.054 (7)
H1A	0.1554	0.6577	0.5074	0.065*
H1B	−0.0846	0.6449	0.5003	0.065*
H1C	0.0255	0.7375	0.4880	0.065*
C1	0.8226 (17)	0.2537 (9)	0.6880 (7)	0.043 (3)*
C2	0.9051 (16)	0.3186 (8)	0.7206 (6)	0.044 (3)*
C3	0.8454 (15)	0.3033 (8)	0.7613 (7)	0.049 (4)*
H3	0.9019	0.3459	0.7819	0.059*
C4	0.7033 (18)	0.2268 (9)	0.7732 (7)	0.049 (4)*
C5	0.6178 (15)	0.1643 (8)	0.7414 (6)	0.042 (3)*
H5	0.5181	0.1138	0.7490	0.050*
C6	0.6745 (16)	0.1744 (8)	0.6998 (7)	0.042 (3)*
C7	0.900 (2)	0.2662 (9)	0.6435 (8)	0.069 (9)
C8	0.7878 (15)	0.3448 (8)	0.6163 (6)	0.040 (3)*
C9	0.8961 (17)	0.3826 (8)	0.5832 (5)	0.046 (3)*
H9	1.0368	0.3575	0.5759	0.055*
C10	0.8020 (15)	0.4588 (8)	0.5596 (6)	0.052 (3)*
H10	0.8766	0.4829	0.5358	0.063*
C11	0.5966 (16)	0.4992 (8)	0.5713 (6)	0.048 (3)*
C12	0.4828 (16)	0.4611 (8)	0.6057 (6)	0.047 (3)*
H12	0.3430	0.4869	0.6132	0.057*
C13	0.5769 (16)	0.3841 (8)	0.6294 (5)	0.053 (3)*
H13	0.5038	0.3591	0.6531	0.064*
C14	0.4959 (19)	0.5854 (9)	0.5459 (7)	0.054 (8)
C15	1.0590 (14)	0.4053 (7)	0.7077 (6)	0.067 (8)
H15	1.0866	0.3989	0.6773	0.080*
C16	1.2839 (15)	0.4023 (9)	0.7293 (7)	0.059 (7)
H16A	1.3493	0.3372	0.7258	0.089*
H16B	1.2651	0.4163	0.7588	0.089*
H16C	1.3812	0.4515	0.7169	0.089*
C17	0.936 (2)	0.5046 (8)	0.7146 (6)	0.071 (8)
H17A	0.9217	0.5171	0.7444	0.107*
H17B	0.7889	0.5011	0.7021	0.107*
H17C	1.0199	0.5577	0.7017	0.107*
C18	0.6375 (19)	0.2073 (10)	0.8187 (8)	0.071 (8)
H18	0.6542	0.1349	0.8222	0.085*
C19	0.7912 (18)	0.2526 (10)	0.8525 (7)	0.070 (8)
H19A	0.7617	0.3229	0.8549	0.104*
H19B	0.9457	0.2425	0.8447	0.104*
H19C	0.7627	0.2208	0.8792	0.104*
C20	0.3938 (17)	0.2273 (11)	0.8281 (9)	0.100 (9)
H20A	0.3524	0.1941	0.8539	0.149*
H20B	0.3026	0.2027	0.8054	0.149*
H20C	0.3708	0.2980	0.8312	0.149*
C21	0.5820 (16)	0.1039 (8)	0.6665 (6)	0.050 (6)
H21	0.5543	0.1428	0.6408	0.060*
C22	0.760 (2)	0.0241 (9)	0.6562 (7)	0.070 (8)
H22A	0.7951	−0.0132	0.6812	0.104*
H22B	0.8940	0.0560	0.6458	0.104*
H22C	0.7024	−0.0204	0.6350	0.104*
C23	0.3647 (17)	0.0525 (9)	0.6786 (8)	0.070 (8)
H23A	0.2567	0.1016	0.6874	0.105*
H23B	0.3925	0.0067	0.7013	0.105*
H23C	0.3070	0.0165	0.6547	0.105*
C24	0.3130 (16)	0.6686 (9)	0.4299 (8)	0.076 (8)
H24A	0.4330	0.6480	0.4482	0.113*
H24B	0.3068	0.7402	0.4290	0.113*
H24C	0.3394	0.6431	0.4020	0.113*
C25	0.0897 (18)	0.6278 (11)	0.4465 (7)	0.046 (8)
H25	−0.0292	0.6510	0.4275	0.056*
C26	0.0690 (18)	0.5160 (9)	0.4499 (6)	0.062 (8)
C27	−0.1310 (17)	0.4689 (11)	0.4405 (7)	0.080 (9)
H27	−0.2537	0.5064	0.4314	0.096*
C28	−0.151 (2)	0.3659 (13)	0.4443 (7)	0.091 (10)
H28	−0.2861	0.3351	0.4376	0.109*
C29	0.027 (3)	0.3091 (11)	0.4580 (7)	0.073 (8)
H29	0.0115	0.2402	0.4603	0.088*
C30	0.223 (2)	0.3531 (12)	0.4680 (7)	0.070 (8)
H30	0.3435	0.3146	0.4774	0.085*
C31	0.2455 (18)	0.4556 (12)	0.4644 (7)	0.062 (8)
H31	0.3814	0.4853	0.4719	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.084 (5)	0.088 (8)	0.076 (18)	0.048 (5)	0.028 (7)	0.029 (6)
O2	0.051 (4)	0.051 (6)	0.064 (16)	−0.002 (4)	−0.007 (6)	0.009 (6)
O3	0.055 (4)	0.075 (6)	0.077 (16)	0.023 (4)	0.004 (6)	0.014 (6)
N1	0.040 (5)	0.048 (8)	0.07 (3)	0.002 (4)	0.000 (8)	0.014 (8)
C7	0.053 (7)	0.052 (10)	0.10 (3)	−0.001 (7)	−0.001 (11)	0.016 (9)
C14	0.043 (6)	0.039 (9)	0.08 (3)	−0.002 (6)	−0.004 (9)	0.006 (8)
C15	0.039 (5)	0.035 (8)	0.13 (3)	−0.001 (5)	0.003 (8)	−0.010 (8)
C16	0.059 (6)	0.052 (9)	0.07 (2)	0.002 (5)	−0.005 (9)	−0.002 (8)
C17	0.059 (6)	0.056 (10)	0.10 (3)	0.001 (6)	0.021 (9)	0.003 (9)
C18	0.051 (7)	0.069 (11)	0.09 (3)	0.006 (6)	−0.001 (11)	−0.010 (10)
C19	0.068 (7)	0.096 (12)	0.04 (3)	−0.002 (7)	−0.012 (11)	0.009 (10)
C20	0.057 (7)	0.114 (14)	0.13 (3)	0.000 (7)	0.007 (11)	−0.004 (11)
C21	0.052 (6)	0.049 (9)	0.05 (2)	−0.006 (6)	−0.002 (9)	−0.007 (7)
C22	0.077 (7)	0.053 (11)	0.08 (3)	−0.006 (6)	0.003 (10)	−0.014 (9)
C23	0.069 (7)	0.057 (10)	0.08 (3)	−0.023 (6)	−0.011 (10)	0.004 (9)
C24	0.067 (7)	0.060 (10)	0.10 (3)	−0.015 (6)	0.017 (10)	−0.002 (9)
C25	0.047 (6)	0.074 (13)	0.02 (3)	−0.007 (6)	0.002 (9)	0.010 (10)
C26	0.057 (7)	0.045 (10)	0.09 (3)	−0.004 (6)	0.016 (9)	0.003 (8)
C27	0.053 (7)	0.066 (12)	0.12 (3)	−0.011 (7)	0.009 (9)	−0.016 (11)
C28	0.080 (9)	0.072 (13)	0.12 (3)	−0.034 (9)	0.030 (12)	−0.020 (12)
C29	0.105 (11)	0.064 (11)	0.05 (3)	−0.008 (10)	0.028 (11)	−0.012 (9)
C30	0.086 (9)	0.052 (13)	0.07 (3)	−0.001 (8)	0.010 (10)	−0.001 (9)
C31	0.055 (7)	0.076 (13)	0.06 (3)	−0.006 (7)	−0.003 (9)	−0.002 (9)

Geometric parameters (Å, º)

O1—C7	1.198 (16)	C17—H17B	0.9600
O2—C14	1.247 (18)	C17—H17C	0.9600
O3—C14	1.257 (13)	C18—C20	1.502 (16)
N1—C25	1.53 (2)	C18—C19	1.53 (2)
N1—H1A	0.8900	C18—H18	0.9800
N1—H1B	0.8900	C19—H19A	0.9600
N1—H1C	0.8900	C19—H19B	0.9600
C1—C6	1.429 (17)	C19—H19C	0.9600
C1—C2	1.43 (2)	C20—H20A	0.9600
C1—C7	1.49 (3)	C20—H20B	0.9600
C2—C3	1.35 (2)	C20—H20C	0.9600
C2—C15	1.531 (15)	C21—C23	1.512 (15)
C3—C4	1.381 (16)	C21—C22	1.539 (14)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.40 (2)	C22—H22A	0.9600
C4—C18	1.51 (3)	C22—H22B	0.9600
C5—C6	1.37 (2)	C22—H22C	0.9600
C5—H5	0.9300	C23—H23A	0.9600
C6—C21	1.52 (2)	C23—H23B	0.9600
C7—C8	1.51 (2)	C23—H23C	0.9600
C8—C9	1.328 (19)	C24—C25	1.528 (16)
C8—C13	1.421 (15)	C24—H24A	0.9600
C9—C10	1.384 (17)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C10—C11	1.385 (14)	C25—C26	1.506 (17)
C10—H10	0.9300	C25—H25	0.9800
C11—C12	1.38 (2)	C26—C27	1.378 (16)
C11—C14	1.528 (19)	C26—C31	1.401 (15)
C12—C13	1.389 (17)	C27—C28	1.388 (17)
C12—H12	0.9300	C27—H27	0.9300
C13—H13	0.9300	C28—C29	1.37 (2)
C15—C16	1.500 (16)	C28—H28	0.9300
C15—C17	1.532 (13)	C29—C30	1.343 (18)
C15—H15	0.9800	C29—H29	0.9300
C16—H16A	0.9600	C30—C31	1.383 (16)
C16—H16B	0.9600	C30—H30	0.9300
C16—H16C	0.9600	C31—H31	0.9300
C17—H17A	0.9600
C25—N1—H1A	109.5	C20—C18—C4	114.0 (18)
C25—N1—H1B	109.5	C20—C18—C19	111.4 (17)
H1A—N1—H1B	109.5	C4—C18—C19	116.2 (13)
C25—N1—H1C	109.5	C20—C18—H18	104.6
H1A—N1—H1C	109.5	C4—C18—H18	104.6
H1B—N1—H1C	109.5	C19—C18—H18	104.6
C6—C1—C2	118.2 (18)	C18—C19—H19A	109.5
C6—C1—C7	121.3 (15)	C18—C19—H19B	109.5
C2—C1—C7	120.4 (13)	H19A—C19—H19B	109.5
C3—C2—C1	120.2 (13)	C18—C19—H19C	109.5
C3—C2—C15	121.6 (14)	H19A—C19—H19C	109.5
C1—C2—C15	118.1 (16)	H19B—C19—H19C	109.5
C2—C3—C4	122.3 (16)	C18—C20—H20A	109.5
C2—C3—H3	118.8	C18—C20—H20B	109.5
C4—C3—H3	118.8	H20A—C20—H20B	109.5
C3—C4—C5	117.8 (19)	C18—C20—H20C	109.5
C3—C4—C18	123.1 (16)	H20A—C20—H20C	109.5
C5—C4—C18	119.1 (13)	H20B—C20—H20C	109.5
C6—C5—C4	122.9 (14)	C23—C21—C6	114.6 (15)
C6—C5—H5	118.6	C23—C21—C22	109.0 (9)
C4—C5—H5	118.6	C6—C21—C22	109.3 (11)
C5—C6—C1	118.5 (15)	C23—C21—H21	107.9
C5—C6—C21	121.3 (12)	C6—C21—H21	107.9
C1—C6—C21	120.2 (18)	C22—C21—H21	107.9
O1—C7—C1	122.2 (14)	C21—C22—H22A	109.5
O1—C7—C8	119 (2)	C21—C22—H22B	109.5
C1—C7—C8	118.6 (14)	H22A—C22—H22B	109.5
C9—C8—C13	121.1 (13)	C21—C22—H22C	109.5
C9—C8—C7	119.9 (11)	H22A—C22—H22C	109.5
C13—C8—C7	118.7 (16)	H22B—C22—H22C	109.5
C8—C9—C10	120.7 (11)	C21—C23—H23A	109.5
C8—C9—H9	119.6	C21—C23—H23B	109.5
C10—C9—H9	119.6	H23A—C23—H23B	109.5
C9—C10—C11	119.9 (15)	C21—C23—H23C	109.5
C9—C10—H10	120.0	H23A—C23—H23C	109.5
C11—C10—H10	120.0	H23B—C23—H23C	109.5
C12—C11—C10	119.9 (13)	C25—C24—H24A	109.5
C12—C11—C14	120.2 (11)	C25—C24—H24B	109.5
C10—C11—C14	119.9 (15)	H24A—C24—H24B	109.5
C11—C12—C13	120.1 (10)	C25—C24—H24C	109.5
C11—C12—H12	119.9	H24A—C24—H24C	109.5
C13—C12—H12	119.9	H24B—C24—H24C	109.5
C12—C13—C8	118.2 (14)	C26—C25—N1	107.5 (15)
C12—C13—H13	120.9	C26—C25—C24	116.8 (11)
C8—C13—H13	120.9	N1—C25—C24	109.8 (13)
O2—C14—O3	123.5 (13)	C26—C25—H25	107.5
O2—C14—C11	118.3 (10)	N1—C25—H25	107.5
O3—C14—C11	118.1 (15)	C24—C25—H25	107.5
C16—C15—C2	113.0 (12)	C27—C26—C31	116.9 (12)
C16—C15—C17	112.5 (10)	C27—C26—C25	120.6 (12)
C2—C15—C17	109.5 (9)	C31—C26—C25	122.4 (11)
C16—C15—H15	107.1	C26—C27—C28	120.5 (13)
C2—C15—H15	107.1	C26—C27—H27	119.8
C17—C15—H15	107.1	C28—C27—H27	119.8
C15—C16—H16A	109.5	C29—C28—C27	120.9 (13)
C15—C16—H16B	109.5	C29—C28—H28	119.5
H16A—C16—H16B	109.5	C27—C28—H28	119.5
C15—C16—H16C	109.5	C30—C29—C28	120.0 (14)
H16A—C16—H16C	109.5	C30—C29—H29	120.0
H16B—C16—H16C	109.5	C28—C29—H29	120.0
C15—C17—H17A	109.5	C29—C30—C31	119.9 (13)
C15—C17—H17B	109.5	C29—C30—H30	120.0
H17A—C17—H17B	109.5	C31—C30—H30	120.0
C15—C17—H17C	109.5	C30—C31—C26	121.8 (12)
H17A—C17—H17C	109.5	C30—C31—H31	119.1
H17B—C17—H17C	109.5	C26—C31—H31	119.1

(140minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.247 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 957 reflections
a = 5.9654 (10) Å	θ = 5.6–22.5°
b = 13.321 (4) Å	µ = 0.08 mm^−1
c = 31.75 (2) Å	T = 299 K
V = 2523.0 (18) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2098 independent reflections
Radiation source: fine-focus sealed tube	1029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→15
Tmin = 0.379, Tmax = 1.000	l = −19→22
5503 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.075	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.6534P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.160	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.17 e Å^−3
2098 reflections	Δρmin = −0.15 e Å^−3
248 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
86 restraints	Absolute structure parameter: 0.6 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3851 (12)	0.6241 (6)	0.4833 (4)	0.060 (5)
O3	0.6953 (13)	0.6142 (6)	0.4448 (4)	0.078 (5)
N1	0.9576 (13)	0.6708 (7)	0.5102 (6)	0.056 (7)
H1A	0.9602	0.7374	0.5121	0.068*
H1B	0.8497	0.6522	0.4925	0.068*
H1C	1.0892	0.6490	0.5007	0.068*
C1	0.1769 (16)	0.2562 (8)	0.3091 (5)	0.046 (4)*
C2	0.0937 (16)	0.3196 (8)	0.2787 (6)	0.042 (3)*
C3	0.1570 (15)	0.3039 (8)	0.2381 (6)	0.047 (3)*
H3	0.1023	0.3472	0.2176	0.056*
C4	0.2989 (19)	0.2268 (9)	0.2256 (7)	0.049 (4)*
C5	0.3819 (15)	0.1653 (8)	0.2582 (6)	0.040 (3)*
H5	0.4814	0.1144	0.2510	0.048*
C6	0.3256 (16)	0.1758 (8)	0.3000 (6)	0.041 (3)*
C8	0.2084 (16)	0.3475 (8)	0.3812 (6)	0.048 (3)*
C9	0.1002 (18)	0.3835 (8)	0.4165 (5)	0.052 (3)*
H9	−0.0366	0.3561	0.4246	0.062*
C10	0.1945 (16)	0.4598 (8)	0.4399 (6)	0.053 (3)*
H10	0.1207	0.4845	0.4635	0.064*
C11	0.4016 (17)	0.5000 (8)	0.4279 (6)	0.048 (3)*
C12	0.5132 (17)	0.4616 (8)	0.3935 (6)	0.051 (4)*
H12	0.6526	0.4875	0.3862	0.062*
C13	0.4211 (16)	0.3855 (8)	0.3700 (5)	0.054 (3)*
H13	0.4979	0.3594	0.3470	0.064*
C14	0.502 (2)	0.5857 (9)	0.4549 (7)	0.056 (7)
C15	−0.0554 (15)	0.4074 (8)	0.2920 (6)	0.065 (8)
H15	−0.0815	0.4014	0.3224	0.078*
C16	−0.2815 (14)	0.4026 (8)	0.2703 (6)	0.054 (6)
H16A	−0.3502	0.3388	0.2759	0.081*
H16B	−0.3759	0.4553	0.2808	0.081*
H16C	−0.2617	0.4106	0.2405	0.081*
C17	0.0623 (17)	0.5070 (8)	0.2843 (6)	0.077 (8)
H17A	0.2044	0.5071	0.2985	0.116*
H17B	0.0855	0.5161	0.2546	0.116*
H17C	−0.0287	0.5608	0.2950	0.116*
C18	0.3680 (19)	0.2055 (10)	0.1820 (8)	0.068 (8)
H18	0.3549	0.1325	0.1792	0.081*
C19	0.2133 (19)	0.2488 (11)	0.1468 (7)	0.076 (8)
H19A	0.2724	0.2309	0.1197	0.115*
H19B	0.0652	0.2216	0.1498	0.115*
H19C	0.2072	0.3206	0.1492	0.115*
C20	0.6126 (17)	0.2278 (10)	0.1730 (7)	0.091 (8)
H20A	0.6454	0.2122	0.1441	0.136*
H20B	0.6419	0.2976	0.1781	0.136*
H20C	0.7054	0.1877	0.1911	0.136*
C24	0.6889 (16)	0.6674 (9)	0.5695 (6)	0.072 (7)
H24A	0.6968	0.7393	0.5706	0.108*
H24B	0.5714	0.6475	0.5506	0.108*
H24C	0.6579	0.6416	0.5972	0.108*
C25	0.9121 (19)	0.6255 (11)	0.5540 (8)	0.054 (8)
H25	1.0298	0.6489	0.5731	0.065*
C26	0.9327 (16)	0.5144 (9)	0.5502 (6)	0.054 (3)*
C27	0.7592 (17)	0.4567 (10)	0.5358 (6)	0.064 (4)*
H27	0.6257	0.4868	0.5275	0.077*
C28	0.7822 (19)	0.3524 (10)	0.5337 (7)	0.076 (5)*
H28	0.6601	0.3132	0.5258	0.091*
C29	0.978 (2)	0.3084 (11)	0.5427 (7)	0.085 (5)*
H29	0.9953	0.2393	0.5398	0.102*
C30	1.151 (2)	0.3660 (10)	0.5563 (7)	0.081 (4)*
H30	1.2853	0.3354	0.5638	0.097*
C31	1.1319 (18)	0.4695 (9)	0.5592 (7)	0.068 (4)*
H31	1.2546	0.5081	0.5673	0.082*
O1	−0.0640 (19)	0.2233 (9)	0.3686 (5)	0.087 (6)	0.909 (17)
C7	0.099 (2)	0.2680 (10)	0.3550 (6)	0.071 (7)	0.909 (17)
C21	0.4095 (17)	0.1044 (10)	0.3342 (6)	0.052 (5)	0.909 (17)
H21	0.4371	0.1437	0.3598	0.062*	0.909 (17)
C22	0.230 (2)	0.0242 (10)	0.3445 (7)	0.079 (8)	0.909 (17)
H22A	0.2856	−0.0199	0.3660	0.118*	0.909 (17)
H22B	0.0960	0.0566	0.3542	0.118*	0.909 (17)
H22C	0.1972	−0.0139	0.3196	0.118*	0.909 (17)
C23	0.629 (2)	0.0513 (10)	0.3220 (8)	0.087 (9)	0.909 (17)
H23A	0.6742	0.0075	0.3445	0.130*	0.909 (17)
H23B	0.6055	0.0128	0.2969	0.130*	0.909 (17)
H23C	0.7434	0.1005	0.3171	0.130*	0.909 (17)
O1D	−0.130 (7)	0.261 (7)	0.360 (3)	0.085 (18)*	0.091 (17)
C7D	0.111 (7)	0.257 (3)	0.3571 (9)	0.070 (17)*	0.091 (17)
C21D	0.426 (12)	0.141 (7)	0.3420 (12)	0.052 (17)*	0.091 (17)
H21D	0.5399	0.1908	0.3499	0.063*	0.091 (17)
C22D	0.223 (13)	0.160 (4)	0.3705 (18)	0.060 (15)*	0.091 (17)
H22D	0.1180	0.1043	0.3679	0.072*	0.091 (17)
H22E	0.2708	0.1640	0.3996	0.072*	0.091 (17)
C23D	0.54 (2)	0.042 (9)	0.342 (3)	0.09 (2)*	0.091 (17)
H23E	0.6625	0.0433	0.3222	0.136*	0.091 (17)
H23D	0.5944	0.0268	0.3694	0.136*	0.091 (17)
H23F	0.4345	−0.0090	0.3332	0.136*	0.091 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.053 (4)	0.055 (6)	0.072 (17)	0.006 (4)	−0.002 (6)	−0.012 (6)
O3	0.060 (4)	0.077 (7)	0.097 (16)	−0.024 (5)	0.008 (7)	−0.018 (7)
N1	0.046 (5)	0.043 (8)	0.08 (3)	0.003 (5)	−0.007 (8)	−0.014 (8)
C14	0.058 (8)	0.036 (10)	0.08 (3)	0.001 (6)	−0.007 (10)	−0.008 (8)
C15	0.054 (6)	0.028 (9)	0.11 (3)	0.002 (6)	−0.002 (9)	0.001 (8)
C16	0.053 (6)	0.054 (9)	0.06 (2)	0.002 (5)	−0.005 (9)	0.005 (8)
C17	0.059 (6)	0.047 (10)	0.13 (3)	−0.004 (6)	0.003 (9)	−0.005 (9)
C18	0.055 (8)	0.067 (11)	0.08 (3)	−0.003 (6)	0.013 (11)	0.019 (10)
C19	0.080 (8)	0.118 (13)	0.03 (3)	−0.002 (9)	−0.002 (11)	0.001 (10)
C20	0.060 (8)	0.110 (13)	0.10 (3)	−0.010 (7)	−0.003 (10)	0.002 (10)
C24	0.071 (7)	0.059 (10)	0.09 (3)	0.004 (6)	0.021 (10)	−0.004 (8)
C25	0.057 (7)	0.087 (14)	0.02 (3)	0.003 (7)	0.001 (10)	−0.012 (11)
O1	0.099 (7)	0.084 (9)	0.077 (17)	−0.046 (7)	0.022 (9)	−0.036 (8)
C7	0.054 (7)	0.064 (11)	0.09 (2)	−0.006 (7)	0.011 (11)	−0.011 (10)
C21	0.057 (7)	0.036 (9)	0.063 (16)	0.010 (7)	−0.013 (9)	0.003 (8)
C22	0.082 (9)	0.069 (12)	0.08 (3)	−0.008 (8)	0.007 (12)	0.009 (10)
C23	0.071 (9)	0.046 (11)	0.14 (3)	0.034 (8)	0.014 (12)	0.005 (10)

Geometric parameters (Å, º)

O2—C14	1.250 (18)	C18—H18	0.9800
O3—C14	1.255 (14)	C19—H19A	0.9600
N1—C25	1.54 (3)	C19—H19B	0.9600
N1—H1A	0.8900	C19—H19C	0.9600
N1—H1B	0.8900	C20—H20A	0.9600
N1—H1C	0.8900	C20—H20B	0.9600
C1—C2	1.375 (17)	C20—H20C	0.9600
C1—C6	1.420 (14)	C24—C25	1.526 (16)
C1—C7	1.536 (18)	C24—H24A	0.9600
C1—C7D	1.57 (3)	C24—H24B	0.9600
C2—C3	1.36 (2)	C24—H24C	0.9600
C2—C15	1.528 (15)	C25—C26	1.490 (18)
C3—C4	1.388 (15)	C25—H25	0.9800
C3—H3	0.9300	C26—C31	1.361 (15)
C4—C5	1.41 (2)	C26—C27	1.367 (15)
C4—C18	1.47 (3)	C27—C28	1.397 (14)
C5—C6	1.37 (2)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.340 (15)
C6—C21	1.528 (16)	C28—H28	0.9300
C6—C21D	1.53 (3)	C29—C30	1.355 (17)
C8—C9	1.380 (19)	C29—H29	0.9300
C8—C13	1.411 (15)	C30—C31	1.387 (15)
C8—C7	1.496 (16)	C30—H30	0.9300
C8—C7D	1.54 (2)	C31—H31	0.9300
C9—C10	1.379 (16)	O1—C7	1.221 (13)
C9—H9	0.9300	C21—C23	1.536 (14)
C10—C11	1.399 (14)	C21—C22	1.547 (15)
C10—H10	0.9300	C21—H21	0.9800
C11—C12	1.38 (2)	C22—H22A	0.9600
C11—C14	1.548 (19)	C22—H22B	0.9600
C12—C13	1.374 (16)	C22—H22C	0.9600
C12—H12	0.9300	C23—H23A	0.9600
C13—H13	0.9300	C23—H23B	0.9600
C15—C16	1.515 (15)	C23—H23C	0.9600
C15—C17	1.521 (13)	O1D—C7D	1.44 (3)
C15—H15	0.9800	C7D—C22D	1.53 (3)
C16—H16A	0.9600	C21D—C23D	1.49 (3)
C16—H16B	0.9600	C21D—C22D	1.53 (3)
C16—H16C	0.9600	C21D—H21D	0.9800
C17—H17A	0.9600	C22D—H22D	0.9700
C17—H17B	0.9600	C22D—H22E	0.9700
C17—H17C	0.9600	C23D—H23E	0.9600
C18—C20	1.516 (15)	C23D—H23D	0.9600
C18—C19	1.56 (2)	C23D—H23F	0.9600
C25—N1—H1A	109.5	C18—C20—H20A	109.5
C25—N1—H1B	109.5	C18—C20—H20B	109.5
H1A—N1—H1B	109.5	H20A—C20—H20B	109.5
C25—N1—H1C	109.5	C18—C20—H20C	109.5
H1A—N1—H1C	109.5	H20A—C20—H20C	109.5
H1B—N1—H1C	109.5	H20B—C20—H20C	109.5
C2—C1—C6	123.1 (15)	C25—C24—H24A	109.5
C2—C1—C7	119.5 (12)	C25—C24—H24B	109.5
C6—C1—C7	117.3 (12)	H24A—C24—H24B	109.5
C2—C1—C7D	126 (2)	C25—C24—H24C	109.5
C6—C1—C7D	111 (2)	H24A—C24—H24C	109.5
C3—C2—C1	118.0 (12)	H24B—C24—H24C	109.5
C3—C2—C15	122.8 (13)	C26—C25—C24	117.5 (11)
C1—C2—C15	119.1 (15)	C26—C25—N1	107.6 (16)
C2—C3—C4	123.7 (16)	C24—C25—N1	107.6 (13)
C2—C3—H3	118.2	C26—C25—H25	107.9
C4—C3—H3	118.2	C24—C25—H25	107.9
C3—C4—C5	115.7 (19)	N1—C25—H25	107.9
C3—C4—C18	125.6 (16)	C31—C26—C27	119.0 (12)
C5—C4—C18	118.7 (13)	C31—C26—C25	119.4 (11)
C6—C5—C4	124.3 (13)	C27—C26—C25	121.5 (11)
C6—C5—H5	117.9	C26—C27—C28	120.1 (12)
C4—C5—H5	117.9	C26—C27—H27	120.0
C5—C6—C1	115.2 (12)	C28—C27—H27	120.0
C5—C6—C21	122.9 (12)	C29—C28—C27	120.7 (13)
C1—C6—C21	121.9 (15)	C29—C28—H28	119.6
C5—C6—C21D	135 (2)	C27—C28—H28	119.6
C1—C6—C21D	107 (2)	C28—C29—C30	119.0 (14)
C9—C8—C13	120.0 (13)	C28—C29—H29	120.5
C9—C8—C7	119.6 (10)	C30—C29—H29	120.5
C13—C8—C7	120.3 (14)	C29—C30—C31	121.5 (13)
C9—C8—C7D	119.9 (15)	C29—C30—H30	119.3
C13—C8—C7D	119.6 (18)	C31—C30—H30	119.3
C10—C9—C8	120.2 (11)	C26—C31—C30	119.6 (13)
C10—C9—H9	119.9	C26—C31—H31	120.2
C8—C9—H9	119.9	C30—C31—H31	120.2
C9—C10—C11	119.8 (15)	O1—C7—C8	119.7 (15)
C9—C10—H10	120.1	O1—C7—C1	121.7 (13)
C11—C10—H10	120.1	C8—C7—C1	118.0 (12)
C12—C11—C10	120.0 (13)	C6—C21—C23	112.7 (14)
C12—C11—C14	121.6 (11)	C6—C21—C22	110.7 (11)
C10—C11—C14	118.3 (15)	C23—C21—C22	108.9 (11)
C13—C12—C11	120.8 (11)	C6—C21—H21	108.1
C13—C12—H12	119.6	C23—C21—H21	108.1
C11—C12—H12	119.6	C22—C21—H21	108.1
C12—C13—C8	119.2 (14)	C21—C22—H22A	109.5
C12—C13—H13	120.4	C21—C22—H22B	109.5
C8—C13—H13	120.4	H22A—C22—H22B	109.5
O2—C14—O3	125.0 (13)	C21—C22—H22C	109.5
O2—C14—C11	119.0 (11)	H22A—C22—H22C	109.5
O3—C14—C11	116.0 (15)	H22B—C22—H22C	109.5
C16—C15—C17	112.0 (10)	C21—C23—H23A	109.5
C16—C15—C2	111.1 (11)	C21—C23—H23B	109.5
C17—C15—C2	110.8 (9)	H23A—C23—H23B	109.5
C16—C15—H15	107.6	C21—C23—H23C	109.5
C17—C15—H15	107.6	H23A—C23—H23C	109.5
C2—C15—H15	107.6	H23B—C23—H23C	109.5
C15—C16—H16A	109.5	O1D—C7D—C22D	116 (4)
C15—C16—H16B	109.5	O1D—C7D—C8	109 (3)
H16A—C16—H16B	109.5	C22D—C7D—C8	111 (3)
C15—C16—H16C	109.5	O1D—C7D—C1	109 (4)
H16A—C16—H16C	109.5	C22D—C7D—C1	99 (3)
H16B—C16—H16C	109.5	C8—C7D—C1	113 (2)
C15—C17—H17A	109.5	C23D—C21D—C22D	120 (5)
C15—C17—H17B	109.5	C23D—C21D—C6	116 (5)
H17A—C17—H17B	109.5	C22D—C21D—C6	99 (3)
C15—C17—H17C	109.5	C23D—C21D—H21D	106.8
H17A—C17—H17C	109.5	C22D—C21D—H21D	106.8
H17B—C17—H17C	109.5	C6—C21D—H21D	106.8
C4—C18—C20	114.1 (17)	C7D—C22D—C21D	109 (3)
C4—C18—C19	115.9 (12)	C7D—C22D—H22D	110.0
C20—C18—C19	111.2 (16)	C21D—C22D—H22D	110.0
C4—C18—H18	104.7	C7D—C22D—H22E	110.0
C20—C18—H18	104.7	C21D—C22D—H22E	110.0
C19—C18—H18	104.7	H22D—C22D—H22E	108.3
C18—C19—H19A	109.5	C21D—C23D—H23E	109.5
C18—C19—H19B	109.5	C21D—C23D—H23D	109.5
H19A—C19—H19B	109.5	H23E—C23D—H23D	109.5
C18—C19—H19C	109.5	C21D—C23D—H23F	109.5
H19A—C19—H19C	109.5	H23E—C23D—H23F	109.5
H19B—C19—H19C	109.5	H23D—C23D—H23F	109.5

(270minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.245 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 806 reflections
a = 5.9717 (12) Å	θ = 5.6–21.7°
b = 13.299 (5) Å	µ = 0.08 mm^−1
c = 31.81 (3) Å	T = 299 K
V = 2526 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	1901 independent reflections
Radiation source: fine-focus sealed tube	778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→14
Tmin = 0.272, Tmax = 1.000	l = −20→22
4915 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.088	w = 1/[σ^2(Fo^2) + (0.0814P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.247	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.15 e Å^−3
1901 reflections	Δρmin = −0.16 e Å^−3
192 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
65 restraints	Absolute structure parameter: 0.8 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3842 (15)	0.6234 (8)	0.4827 (5)	0.072 (6)
O3	0.6931 (16)	0.6128 (8)	0.4443 (6)	0.094 (7)
N1	0.9553 (17)	0.6719 (9)	0.5106 (7)	0.076 (9)
H1A	0.9766	0.7377	0.5137	0.091*
H1B	0.8381	0.6614	0.4939	0.091*
H1C	1.0768	0.6443	0.4992	0.091*
C1	0.179 (2)	0.2566 (11)	0.3094 (7)	0.057 (4)*
C2	0.097 (2)	0.3181 (10)	0.2784 (8)	0.053 (4)*
C3	0.160 (2)	0.3028 (11)	0.2367 (8)	0.058 (3)*
H3	0.1041	0.3462	0.2164	0.069*
C4	0.304 (2)	0.2254 (11)	0.2239 (9)	0.062 (4)*
C5	0.380 (2)	0.1675 (11)	0.2594 (8)	0.058 (3)*
H5	0.4816	0.1167	0.2530	0.069*
C6	0.327 (2)	0.1755 (11)	0.3002 (7)	0.064 (5)*
C8	0.207 (2)	0.3482 (12)	0.3810 (8)	0.065 (2)*
C9	0.100 (2)	0.3833 (11)	0.4163 (7)	0.065 (2)*
H9	−0.0356	0.3551	0.4245	0.078*
C10	0.192 (2)	0.4595 (11)	0.4395 (8)	0.065 (2)*
H10	0.1170	0.4848	0.4628	0.078*
C11	0.400 (2)	0.4989 (11)	0.4281 (8)	0.065 (2)*
C12	0.513 (2)	0.4604 (12)	0.3937 (8)	0.065 (2)*
H12	0.6547	0.4847	0.3870	0.078*
C13	0.418 (2)	0.3864 (12)	0.3691 (7)	0.065 (2)*
H13	0.4909	0.3624	0.3453	0.078*
C14	0.500 (3)	0.5840 (13)	0.4558 (9)	0.065 (5)*
C15	−0.055 (2)	0.4064 (10)	0.2910 (8)	0.079 (10)
H15	−0.0796	0.4009	0.3213	0.095*
C16	−0.2818 (19)	0.4024 (12)	0.2705 (8)	0.069 (5)*
H16A	−0.3494	0.3381	0.2759	0.104*
H16B	−0.3749	0.4546	0.2818	0.104*
H16C	−0.2659	0.4118	0.2407	0.104*
C17	0.060 (2)	0.5057 (11)	0.2836 (8)	0.074 (5)*
H17A	0.2035	0.5054	0.2971	0.111*
H17B	0.0788	0.5160	0.2539	0.111*
H17C	−0.0301	0.5589	0.2950	0.111*
C18	0.368 (2)	0.2043 (13)	0.1814 (9)	0.075 (5)*
H18	0.3550	0.1311	0.1786	0.090*
C19	0.213 (2)	0.2478 (15)	0.1465 (9)	0.102 (7)*
H19A	0.2706	0.2294	0.1194	0.153*
H19B	0.0646	0.2212	0.1497	0.153*
H19C	0.2084	0.3198	0.1488	0.153*
C20	0.613 (2)	0.2277 (13)	0.1721 (9)	0.096 (6)*
H20A	0.6458	0.2121	0.1433	0.143*
H20B	0.6415	0.2978	0.1771	0.143*
H20C	0.7073	0.1880	0.1902	0.143*
C24	0.687 (2)	0.6678 (12)	0.5689 (8)	0.083 (6)*
H24A	0.6943	0.7399	0.5688	0.125*
H24B	0.5689	0.6458	0.5506	0.125*
H24C	0.6590	0.6445	0.5969	0.125*
C25	0.911 (3)	0.6247 (16)	0.5533 (11)	0.086 (6)*
H25	1.0278	0.6494	0.5724	0.103*
C26	0.936 (2)	0.5121 (11)	0.5510 (9)	0.070 (5)*
C27	0.760 (2)	0.4537 (14)	0.5353 (9)	0.082 (6)*
H27	0.6287	0.4835	0.5256	0.099*
C28	0.786 (2)	0.3501 (14)	0.5346 (9)	0.080 (6)*
H28	0.6652	0.3098	0.5274	0.097*
C29	0.983 (3)	0.3067 (15)	0.5442 (9)	0.095 (6)*
H29	0.9997	0.2372	0.5424	0.114*
C30	1.154 (3)	0.3637 (15)	0.5561 (10)	0.097 (6)*
H30	1.2909	0.3330	0.5620	0.117*
C31	1.137 (2)	0.4677 (13)	0.5603 (9)	0.083 (6)*
H31	1.2584	0.5060	0.5691	0.099*
O1	−0.066 (3)	0.2249 (13)	0.3681 (7)	0.103 (8)	0.87 (2)
C7	0.098 (3)	0.2700 (15)	0.3545 (7)	0.083 (9)	0.87 (2)
C21	0.408 (2)	0.1038 (15)	0.3343 (8)	0.070 (7)	0.87 (2)
H21	0.4369	0.1440	0.3595	0.083*	0.87 (2)
C22	0.230 (3)	0.0275 (15)	0.3456 (10)	0.099 (8)*	0.87 (2)
H22A	0.2862	−0.0164	0.3671	0.148*	0.87 (2)
H22B	0.0992	0.0617	0.3557	0.148*	0.87 (2)
H22C	0.1921	−0.0112	0.3211	0.148*	0.87 (2)
C23	0.626 (3)	0.0507 (15)	0.3227 (10)	0.085 (8)*	0.87 (2)
H23A	0.7371	0.0999	0.3156	0.127*	0.87 (2)
H23B	0.6766	0.0115	0.3461	0.127*	0.87 (2)
H23C	0.6005	0.0074	0.2990	0.127*	0.87 (2)
O1D	−0.134 (7)	0.262 (7)	0.359 (3)	0.098 (18)*	0.13 (2)
C7D	0.108 (7)	0.258 (3)	0.3570 (9)	0.082 (17)*	0.13 (2)
C21D	0.411 (13)	0.134 (6)	0.3424 (12)	0.075 (17)*	0.13 (2)
H21D	0.5324	0.1786	0.3513	0.090*	0.13 (2)
C22D	0.212 (13)	0.158 (4)	0.3708 (19)	0.082 (16)*	0.13 (2)
H22D	0.1009	0.1053	0.3690	0.098*	0.13 (2)
H22E	0.2611	0.1633	0.3998	0.098*	0.13 (2)
C23D	0.51 (2)	0.031 (6)	0.341 (3)	0.09 (3)*	0.13 (2)
H23E	0.6311	0.0293	0.3218	0.133*	0.13 (2)
H23D	0.5606	0.0129	0.3688	0.133*	0.13 (2)
H23F	0.3956	−0.0162	0.3324	0.133*	0.13 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.067 (6)	0.069 (9)	0.08 (2)	−0.002 (5)	−0.004 (8)	−0.016 (7)
O3	0.079 (6)	0.092 (10)	0.11 (2)	−0.027 (6)	0.008 (9)	−0.005 (9)
N1	0.054 (6)	0.050 (10)	0.12 (3)	−0.005 (6)	−0.023 (10)	−0.010 (9)
C15	0.065 (7)	0.033 (11)	0.14 (4)	−0.013 (7)	−0.017 (11)	0.000 (10)
O1	0.108 (9)	0.106 (13)	0.09 (2)	−0.042 (10)	0.031 (12)	−0.041 (11)
C7	0.066 (10)	0.098 (15)	0.08 (3)	−0.005 (11)	0.005 (14)	−0.026 (14)
C21	0.064 (9)	0.063 (12)	0.081 (19)	−0.001 (9)	−0.015 (11)	0.021 (11)

Geometric parameters (Å, º)

O2—C14	1.22 (2)	C18—H18	0.9800
O3—C14	1.267 (18)	C19—H19A	0.9600
N1—C25	1.52 (3)	C19—H19B	0.9600
N1—H1A	0.8900	C19—H19C	0.9600
N1—H1B	0.8900	C20—H20A	0.9600
N1—H1C	0.8900	C20—H20B	0.9600
C1—C2	1.37 (2)	C20—H20C	0.9600
C1—C6	1.425 (19)	C24—C25	1.54 (2)
C1—C7	1.53 (2)	C24—H24A	0.9600
C1—C7D	1.57 (2)	C24—H24B	0.9600
C2—C3	1.39 (3)	C24—H24C	0.9600
C2—C15	1.534 (19)	C25—C26	1.51 (2)
C3—C4	1.40 (2)	C25—H25	0.9800
C3—H3	0.9300	C26—C31	1.37 (2)
C4—C18	1.43 (3)	C26—C27	1.40 (2)
C4—C5	1.44 (3)	C27—C28	1.387 (19)
C5—C6	1.34 (3)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.35 (2)
C6—C21	1.521 (19)	C28—H28	0.9300
C6—C21D	1.53 (3)	C29—C30	1.33 (2)
C8—C9	1.37 (2)	C29—H29	0.9300
C8—C13	1.41 (2)	C30—C31	1.39 (2)
C8—C7	1.486 (19)	C30—H30	0.9300
C8—C7D	1.54 (2)	C31—H31	0.9300
C9—C10	1.37 (2)	O1—C7	1.227 (17)
C9—H9	0.9300	C21—C22	1.510 (18)
C10—C11	1.397 (18)	C21—C23	1.527 (19)
C10—H10	0.9300	C21—H21	0.9800
C11—C12	1.38 (3)	C22—H22A	0.9600
C11—C14	1.55 (3)	C22—H22B	0.9600
C12—C13	1.38 (2)	C22—H22C	0.9600
C12—H12	0.9300	C23—H23A	0.9600
C13—H13	0.9300	C23—H23B	0.9600
C15—C16	1.50 (2)	C23—H23C	0.9600
C15—C17	1.505 (18)	O1D—C7D	1.45 (3)
C15—H15	0.9800	C7D—C22D	1.53 (3)
C16—H16A	0.9600	C21D—C23D	1.49 (3)
C16—H16B	0.9600	C21D—C22D	1.53 (3)
C16—H16C	0.9600	C21D—H21D	0.9800
C17—H17A	0.9600	C22D—H22D	0.9700
C17—H17B	0.9600	C22D—H22E	0.9700
C17—H17C	0.9600	C23D—H23E	0.9600
C18—C20	1.53 (2)	C23D—H23D	0.9600
C18—C19	1.56 (3)	C23D—H23F	0.9600
C25—N1—H1A	109.5	C18—C20—H20A	109.5
C25—N1—H1B	109.5	C18—C20—H20B	109.5
H1A—N1—H1B	109.5	H20A—C20—H20B	109.5
C25—N1—H1C	109.5	C18—C20—H20C	109.5
H1A—N1—H1C	109.5	H20A—C20—H20C	109.5
H1B—N1—H1C	109.5	H20B—C20—H20C	109.5
C2—C1—C6	121.8 (18)	C25—C24—H24A	109.5
C2—C1—C7	119.5 (15)	C25—C24—H24B	109.5
C6—C1—C7	118.5 (16)	H24A—C24—H24B	109.5
C2—C1—C7D	126 (2)	C25—C24—H24C	109.5
C6—C1—C7D	112 (2)	H24A—C24—H24C	109.5
C1—C2—C3	119.9 (16)	H24B—C24—H24C	109.5
C1—C2—C15	118.8 (19)	C26—C25—N1	111 (2)
C3—C2—C15	121.3 (17)	C26—C25—C24	118.1 (15)
C2—C3—C4	123 (2)	N1—C25—C24	106.5 (17)
C2—C3—H3	118.3	C26—C25—H25	107.0
C4—C3—H3	118.3	N1—C25—H25	107.0
C3—C4—C18	126 (2)	C24—C25—H25	107.0
C3—C4—C5	111 (2)	C31—C26—C27	119.8 (16)
C18—C4—C5	123.4 (16)	C31—C26—C25	120.3 (16)
C6—C5—C4	130.0 (18)	C27—C26—C25	119.6 (16)
C6—C5—H5	115.0	C28—C27—C26	118.0 (16)
C4—C5—H5	115.0	C28—C27—H27	121.0
C5—C6—C1	113.8 (16)	C26—C27—H27	121.0
C5—C6—C21	124.4 (17)	C29—C28—C27	121.6 (17)
C1—C6—C21	121.7 (19)	C29—C28—H28	119.2
C5—C6—C21D	138 (2)	C27—C28—H28	119.2
C1—C6—C21D	107 (2)	C30—C29—C28	119.4 (19)
C9—C8—C13	120.7 (16)	C30—C29—H29	120.3
C9—C8—C7	119.8 (13)	C28—C29—H29	120.3
C13—C8—C7	119.4 (18)	C29—C30—C31	122.4 (19)
C9—C8—C7D	119.5 (17)	C29—C30—H30	118.8
C13—C8—C7D	119 (2)	C31—C30—H30	118.8
C10—C9—C8	120.4 (14)	C26—C31—C30	118.3 (17)
C10—C9—H9	119.8	C26—C31—H31	120.9
C8—C9—H9	119.8	C30—C31—H31	120.9
C9—C10—C11	119.7 (19)	O1—C7—C8	119.5 (18)
C9—C10—H10	120.2	O1—C7—C1	121.7 (16)
C11—C10—H10	120.2	C8—C7—C1	118.4 (15)
C12—C11—C10	119.9 (17)	C22—C21—C6	111.6 (15)
C12—C11—C14	122.2 (14)	C22—C21—C23	110.2 (16)
C10—C11—C14	118 (2)	C6—C21—C23	112.8 (18)
C13—C12—C11	120.9 (14)	C22—C21—H21	107.3
C13—C12—H12	119.6	C6—C21—H21	107.3
C11—C12—H12	119.6	C23—C21—H21	107.3
C12—C13—C8	118.2 (19)	C21—C22—H22A	109.5
C12—C13—H13	120.9	C21—C22—H22B	109.5
C8—C13—H13	120.9	H22A—C22—H22B	109.5
O2—C14—O3	126.1 (19)	C21—C22—H22C	109.5
O2—C14—C11	119.6 (14)	H22A—C22—H22C	109.5
O3—C14—C11	114 (2)	H22B—C22—H22C	109.5
C16—C15—C17	111.9 (14)	C21—C23—H23A	109.5
C16—C15—C2	113.0 (14)	C21—C23—H23B	109.5
C17—C15—C2	111.3 (11)	H23A—C23—H23B	109.5
C16—C15—H15	106.7	C21—C23—H23C	109.5
C17—C15—H15	106.7	H23A—C23—H23C	109.5
C2—C15—H15	106.7	H23B—C23—H23C	109.5
C15—C16—H16A	109.5	O1D—C7D—C22D	115 (4)
C15—C16—H16B	109.5	O1D—C7D—C8	109 (3)
H16A—C16—H16B	109.5	C22D—C7D—C8	112 (3)
C15—C16—H16C	109.5	O1D—C7D—C1	108 (3)
H16A—C16—H16C	109.5	C22D—C7D—C1	99 (3)
H16B—C16—H16C	109.5	C8—C7D—C1	113 (2)
C15—C17—H17A	109.5	C23D—C21D—C22D	121 (5)
C15—C17—H17B	109.5	C23D—C21D—C6	116 (4)
H17A—C17—H17B	109.5	C22D—C21D—C6	101 (3)
C15—C17—H17C	109.5	C23D—C21D—H21D	106.0
H17A—C17—H17C	109.5	C22D—C21D—H21D	106.0
H17B—C17—H17C	109.5	C6—C21D—H21D	106.0
C4—C18—C20	113 (2)	C7D—C22D—C21D	109 (3)
C4—C18—C19	116.3 (15)	C7D—C22D—H22D	109.8
C20—C18—C19	111 (2)	C21D—C22D—H22D	109.8
C4—C18—H18	105.0	C7D—C22D—H22E	109.8
C20—C18—H18	105.0	C21D—C22D—H22E	109.8
C19—C18—H18	105.0	H22D—C22D—H22E	108.3
C18—C19—H19A	109.5	C21D—C23D—H23E	109.5
C18—C19—H19B	109.5	C21D—C23D—H23D	109.5
H19A—C19—H19B	109.5	H23E—C23D—H23D	109.5
C18—C19—H19C	109.5	C21D—C23D—H23F	109.5
H19A—C19—H19C	109.5	H23E—C23D—H23F	109.5
H19B—C19—H19C	109.5	H23D—C23D—H23F	109.5

(400minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.244 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 822 reflections
a = 5.9814 (12) Å	θ = 5.6–23.4°
b = 13.288 (5) Å	µ = 0.08 mm^−1
c = 31.81 (3) Å	T = 299 K
V = 2528 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	1913 independent reflections
Radiation source: fine-focus sealed tube	843 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→14
Tmin = 0.244, Tmax = 1.000	l = −20→22
4926 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.084	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 2.360P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.182	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.18 e Å^−3
1913 reflections	Δρmin = −0.14 e Å^−3
193 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
65 restraints	Absolute structure parameter: 4.1 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3819 (14)	0.6228 (6)	0.4827 (4)	0.063 (5)
O3	0.6909 (15)	0.6124 (8)	0.4445 (5)	0.087 (6)
N1	0.9551 (15)	0.6714 (7)	0.5106 (6)	0.066 (7)
H1A	0.9665	0.7377	0.5139	0.080*
H1B	0.8420	0.6576	0.4933	0.080*
H1C	1.0816	0.6475	0.4998	0.080*
C1	0.1794 (19)	0.2577 (9)	0.3089 (6)	0.049 (4)*
C2	0.0951 (19)	0.3205 (9)	0.2787 (7)	0.048 (4)*
C3	0.1597 (18)	0.3039 (9)	0.2374 (7)	0.047 (4)*
H3	0.1026	0.3464	0.2168	0.056*
C4	0.3049 (19)	0.2275 (10)	0.2249 (7)	0.051 (4)*
C5	0.3838 (18)	0.1652 (9)	0.2584 (7)	0.045 (4)*
H5	0.4803	0.1128	0.2516	0.054*
C6	0.327 (2)	0.1772 (10)	0.3002 (7)	0.053 (4)*
C8	0.206 (2)	0.3486 (10)	0.3805 (7)	0.0576 (19)*
C9	0.097 (2)	0.3840 (10)	0.4164 (6)	0.0576 (19)*
H9	−0.0380	0.3557	0.4246	0.069*
C10	0.190 (2)	0.4608 (9)	0.4398 (7)	0.0576 (19)*
H10	0.1150	0.4868	0.4629	0.069*
C11	0.399 (2)	0.4991 (10)	0.4282 (7)	0.0576 (19)*
C12	0.511 (2)	0.4614 (10)	0.3935 (7)	0.0576 (19)*
H12	0.6510	0.4865	0.3866	0.069*
C13	0.417 (2)	0.3873 (10)	0.3691 (6)	0.0576 (19)*
H13	0.4909	0.3632	0.3455	0.069*
C14	0.498 (3)	0.5848 (12)	0.4551 (8)	0.058 (5)*
C15	−0.0540 (19)	0.4075 (9)	0.2910 (7)	0.061 (8)
H15	−0.0807	0.4012	0.3213	0.074*
C16	−0.2796 (17)	0.4027 (10)	0.2700 (7)	0.060 (4)*
H16A	−0.3458	0.3380	0.2751	0.090*
H16B	−0.3745	0.4543	0.2813	0.090*
H16C	−0.2622	0.4126	0.2403	0.090*
C17	0.061 (2)	0.5076 (9)	0.2844 (7)	0.066 (5)*
H17A	0.2035	0.5070	0.2983	0.100*
H17B	0.0825	0.5188	0.2549	0.100*
H17C	−0.0298	0.5605	0.2959	0.100*
C18	0.368 (2)	0.2015 (12)	0.1814 (8)	0.071 (5)*
H18	0.3562	0.1281	0.1790	0.085*
C19	0.215 (2)	0.2464 (13)	0.1466 (9)	0.103 (7)*
H19A	0.2687	0.2256	0.1195	0.155*
H19B	0.0649	0.2230	0.1505	0.155*
H19C	0.2181	0.3186	0.1483	0.155*
C20	0.615 (2)	0.2287 (11)	0.1731 (8)	0.085 (5)*
H20A	0.6531	0.2114	0.1447	0.127*
H20B	0.6359	0.2996	0.1773	0.127*
H20C	0.7084	0.1920	0.1922	0.127*
C24	0.6908 (19)	0.6669 (10)	0.5687 (7)	0.075 (5)*
H24A	0.7008	0.7390	0.5692	0.112*
H24B	0.5718	0.6469	0.5503	0.112*
H24C	0.6613	0.6425	0.5966	0.112*
C25	0.913 (2)	0.6226 (13)	0.5528 (9)	0.074 (5)*
H25	1.0308	0.6457	0.5719	0.089*
C26	0.932 (2)	0.5136 (10)	0.5497 (7)	0.061 (4)*
C27	0.759 (2)	0.4538 (11)	0.5352 (8)	0.066 (5)*
H27	0.6257	0.4830	0.5265	0.079*
C28	0.786 (2)	0.3501 (12)	0.5338 (8)	0.079 (5)*
H28	0.6661	0.3098	0.5259	0.095*
C29	0.986 (3)	0.3061 (13)	0.5438 (8)	0.092 (6)*
H29	1.0036	0.2368	0.5415	0.110*
C30	1.157 (3)	0.3645 (13)	0.5570 (8)	0.090 (6)*
H30	1.2923	0.3348	0.5641	0.107*
C31	1.134 (2)	0.4689 (12)	0.5601 (8)	0.076 (5)*
H31	1.2529	0.5081	0.5692	0.091*
O1	−0.068 (3)	0.2251 (11)	0.3676 (6)	0.091 (7)	0.842 (19)
C7	0.095 (3)	0.2704 (14)	0.3541 (7)	0.072 (8)	0.842 (19)
C21	0.407 (3)	0.1055 (13)	0.3341 (7)	0.062 (6)	0.842 (19)
H21	0.4318	0.1451	0.3597	0.074*	0.842 (19)
C22	0.225 (3)	0.0277 (14)	0.3440 (10)	0.103 (9)*	0.842 (19)
H22A	0.2769	−0.0172	0.3655	0.155*	0.842 (19)
H22B	0.0925	0.0617	0.3537	0.155*	0.842 (19)
H22C	0.1904	−0.0100	0.3191	0.155*	0.842 (19)
C23	0.624 (3)	0.0511 (12)	0.3240 (8)	0.072 (7)*	0.842 (19)
H23A	0.6624	0.0074	0.3469	0.108*	0.842 (19)
H23B	0.6047	0.0120	0.2989	0.108*	0.842 (19)
H23C	0.7407	0.0995	0.3198	0.108*	0.842 (19)
O1D	−0.129 (6)	0.263 (6)	0.359 (2)	0.095 (18)*	0.158 (19)
C7D	0.112 (7)	0.257 (2)	0.3568 (9)	0.074 (16)*	0.158 (19)
C21D	0.409 (11)	0.129 (5)	0.3410 (12)	0.064 (16)*	0.158 (19)
H21D	0.5408	0.1667	0.3505	0.077*	0.158 (19)
C22D	0.215 (11)	0.157 (3)	0.3699 (17)	0.072 (15)*	0.158 (19)
H22D	0.1017	0.1044	0.3687	0.086*	0.158 (19)
H22E	0.2677	0.1612	0.3987	0.086*	0.158 (19)
C23D	0.480 (16)	0.021 (5)	0.335 (3)	0.09 (3)*	0.158 (19)
H23D	0.6037	0.0179	0.3163	0.128*	0.158 (19)
H23E	0.5234	−0.0064	0.3621	0.128*	0.158 (19)
H23F	0.3570	−0.0171	0.3243	0.128*	0.158 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.061 (5)	0.059 (7)	0.069 (18)	0.011 (5)	−0.003 (7)	−0.012 (6)
O3	0.071 (6)	0.090 (9)	0.10 (2)	−0.026 (6)	0.015 (8)	−0.014 (8)
N1	0.052 (6)	0.035 (8)	0.11 (3)	0.000 (5)	−0.020 (9)	−0.010 (8)
C15	0.063 (7)	0.037 (10)	0.08 (3)	−0.009 (7)	−0.022 (11)	−0.002 (9)
O1	0.107 (10)	0.089 (12)	0.08 (2)	−0.044 (10)	0.037 (11)	−0.036 (10)
C7	0.066 (11)	0.085 (14)	0.06 (2)	−0.008 (11)	0.001 (14)	−0.011 (13)
C21	0.066 (9)	0.053 (12)	0.066 (18)	−0.004 (9)	−0.001 (11)	−0.003 (10)

Geometric parameters (Å, º)

O2—C14	1.23 (2)	C18—H18	0.9800
O3—C14	1.255 (16)	C19—H19A	0.9600
N1—C25	1.51 (3)	C19—H19B	0.9600
N1—H1A	0.8900	C19—H19C	0.9600
N1—H1B	0.8900	C20—H20A	0.9600
N1—H1C	0.8900	C20—H20B	0.9600
C1—C2	1.37 (2)	C20—H20C	0.9600
C1—C6	1.415 (17)	C24—C25	1.539 (19)
C1—C7	1.531 (19)	C24—H24A	0.9600
C1—C7D	1.57 (2)	C24—H24B	0.9600
C2—C3	1.38 (2)	C24—H24C	0.9600
C2—C15	1.513 (17)	C25—C26	1.457 (19)
C3—C4	1.395 (16)	C25—H25	0.9800
C3—H3	0.9300	C26—C27	1.382 (18)
C4—C5	1.43 (2)	C26—C31	1.384 (19)
C4—C18	1.48 (3)	C27—C28	1.388 (16)
C5—C6	1.38 (2)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.367 (18)
C6—C21	1.516 (19)	C28—H28	0.9300
C6—C21D	1.53 (3)	C29—C30	1.35 (2)
C8—C9	1.40 (2)	C29—H29	0.9300
C8—C13	1.407 (18)	C30—C31	1.397 (17)
C8—C7	1.494 (18)	C30—H30	0.9300
C8—C7D	1.54 (2)	C31—H31	0.9300
C9—C10	1.378 (18)	O1—C7	1.223 (16)
C9—H9	0.9300	C21—C23	1.520 (17)
C10—C11	1.400 (17)	C21—C22	1.534 (18)
C10—H10	0.9300	C21—H21	0.9800
C11—C12	1.38 (2)	C22—H22A	0.9600
C11—C14	1.54 (2)	C22—H22B	0.9600
C12—C13	1.37 (2)	C22—H22C	0.9600
C12—H12	0.9300	C23—H23A	0.9600
C13—H13	0.9300	C23—H23B	0.9600
C15—C16	1.507 (17)	C23—H23C	0.9600
C15—C17	1.511 (16)	O1D—C7D	1.45 (3)
C15—H15	0.9800	C7D—C22D	1.53 (3)
C16—H16A	0.9600	C21D—C23D	1.50 (3)
C16—H16B	0.9600	C21D—C22D	1.53 (3)
C16—H16C	0.9600	C21D—H21D	0.9800
C17—H17A	0.9600	C22D—H22D	0.9700
C17—H17B	0.9600	C22D—H22E	0.9700
C17—H17C	0.9600	C23D—H23D	0.9600
C18—C20	1.543 (17)	C23D—H23E	0.9600
C18—C19	1.55 (3)	C23D—H23F	0.9600
C25—N1—H1A	109.5	C18—C20—H20A	109.5
C25—N1—H1B	109.5	C18—C20—H20B	109.5
H1A—N1—H1B	109.5	H20A—C20—H20B	109.5
C25—N1—H1C	109.5	C18—C20—H20C	109.5
H1A—N1—H1C	109.5	H20A—C20—H20C	109.5
H1B—N1—H1C	109.5	H20B—C20—H20C	109.5
C2—C1—C6	123.5 (17)	C25—C24—H24A	109.5
C2—C1—C7	118.1 (14)	C25—C24—H24B	109.5
C6—C1—C7	118.2 (14)	H24A—C24—H24B	109.5
C2—C1—C7D	126.2 (19)	C25—C24—H24C	109.5
C6—C1—C7D	110.1 (19)	H24A—C24—H24C	109.5
C1—C2—C3	117.8 (14)	H24B—C24—H24C	109.5
C1—C2—C15	120.0 (18)	C26—C25—N1	110.6 (19)
C3—C2—C15	122.2 (15)	C26—C25—C24	118.1 (13)
C2—C3—C4	124.1 (17)	N1—C25—C24	105.8 (14)
C2—C3—H3	117.9	C26—C25—H25	107.3
C4—C3—H3	117.9	N1—C25—H25	107.3
C3—C4—C5	114 (2)	C24—C25—H25	107.3
C3—C4—C18	126.7 (18)	C27—C26—C31	119.0 (14)
C5—C4—C18	118.7 (14)	C27—C26—C25	122.4 (14)
C6—C5—C4	124.8 (15)	C31—C26—C25	118.6 (14)
C6—C5—H5	117.6	C26—C27—C28	119.6 (14)
C4—C5—H5	117.6	C26—C27—H27	120.2
C5—C6—C1	115.4 (14)	C28—C27—H27	120.2
C5—C6—C21	122.4 (15)	C29—C28—C27	121.2 (15)
C1—C6—C21	122.1 (18)	C29—C28—H28	119.4
C5—C6—C21D	133.6 (19)	C27—C28—H28	119.4
C1—C6—C21D	111 (2)	C30—C29—C28	119.2 (16)
C9—C8—C13	120.3 (15)	C30—C29—H29	120.4
C9—C8—C7	119.2 (12)	C28—C29—H29	120.4
C13—C8—C7	120.5 (16)	C29—C30—C31	121.2 (16)
C9—C8—C7D	119.8 (16)	C29—C30—H30	119.4
C13—C8—C7D	119.3 (19)	C31—C30—H30	119.4
C10—C9—C8	120.1 (13)	C26—C31—C30	119.7 (16)
C10—C9—H9	120.0	C26—C31—H31	120.2
C8—C9—H9	120.0	C30—C31—H31	120.2
C9—C10—C11	119.2 (17)	O1—C7—C8	119.9 (17)
C9—C10—H10	120.4	O1—C7—C1	122.6 (15)
C11—C10—H10	120.4	C8—C7—C1	117.3 (14)
C12—C11—C10	120.6 (16)	C6—C21—C23	114.6 (17)
C12—C11—C14	121.8 (14)	C6—C21—C22	110.3 (15)
C10—C11—C14	117.7 (18)	C23—C21—C22	109.2 (14)
C13—C12—C11	120.9 (13)	C6—C21—H21	107.5
C13—C12—H12	119.5	C23—C21—H21	107.5
C11—C12—H12	119.5	C22—C21—H21	107.5
C12—C13—C8	118.8 (17)	C21—C22—H22A	109.5
C12—C13—H13	120.6	C21—C22—H22B	109.5
C8—C13—H13	120.6	H22A—C22—H22B	109.5
O2—C14—O3	126.3 (17)	C21—C22—H22C	109.5
O2—C14—C11	118.9 (13)	H22A—C22—H22C	109.5
O3—C14—C11	114.7 (19)	H22B—C22—H22C	109.5
C16—C15—C17	112.5 (12)	C21—C23—H23A	109.5
C16—C15—C2	112.3 (12)	C21—C23—H23B	109.5
C17—C15—C2	111.6 (10)	H23A—C23—H23B	109.5
C16—C15—H15	106.6	C21—C23—H23C	109.5
C17—C15—H15	106.6	H23A—C23—H23C	109.5
C2—C15—H15	106.6	H23B—C23—H23C	109.5
C15—C16—H16A	109.5	O1D—C7D—C22D	116 (3)
C15—C16—H16B	109.5	O1D—C7D—C8	107 (3)
H16A—C16—H16B	109.5	C22D—C7D—C8	114 (3)
C15—C16—H16C	109.5	O1D—C7D—C1	107 (3)
H16A—C16—H16C	109.5	C22D—C7D—C1	100 (3)
H16B—C16—H16C	109.5	C8—C7D—C1	112 (2)
C15—C17—H17A	109.5	C23D—C21D—C22D	121 (5)
C15—C17—H17B	109.5	C23D—C21D—C6	113 (4)
H17A—C17—H17B	109.5	C22D—C21D—C6	99 (3)
C15—C17—H17C	109.5	C23D—C21D—H21D	107.6
H17A—C17—H17C	109.5	C22D—C21D—H21D	107.6
H17B—C17—H17C	109.5	C6—C21D—H21D	107.6
C4—C18—C20	110.3 (16)	C7D—C22D—C21D	111 (3)
C4—C18—C19	115.4 (14)	C7D—C22D—H22D	109.5
C20—C18—C19	110.6 (17)	C21D—C22D—H22D	109.5
C4—C18—H18	106.7	C7D—C22D—H22E	109.5
C20—C18—H18	106.7	C21D—C22D—H22E	109.5
C19—C18—H18	106.7	H22D—C22D—H22E	108.1
C18—C19—H19A	109.5	C21D—C23D—H23D	109.5
C18—C19—H19B	109.5	C21D—C23D—H23E	109.5
H19A—C19—H19B	109.5	H23D—C23D—H23E	109.5
C18—C19—H19C	109.5	C21D—C23D—H23F	109.5
H19A—C19—H19C	109.5	H23D—C23D—H23F	109.5
H19B—C19—H19C	109.5	H23E—C23D—H23F	109.5

(580minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.242 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1102 reflections
a = 5.9850 (11) Å	θ = 5.6–23.4°
b = 13.301 (4) Å	µ = 0.08 mm^−1
c = 31.82 (3) Å	T = 299 K
V = 2533 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2240 independent reflections
Radiation source: fine-focus sealed tube	931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.111
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.5°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→14
Tmin = 0.256, Tmax = 1.000	l = −20→22
7190 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.087	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 2.3251P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.234	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.17 e Å^−3
2240 reflections	Δρmin = −0.15 e Å^−3
233 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
80 restraints	Absolute structure parameter: 2.7 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3821 (15)	0.6236 (7)	0.4825 (5)	0.078 (5)
O3	0.6913 (17)	0.6135 (8)	0.4448 (5)	0.095 (6)
N1	0.9558 (17)	0.6702 (7)	0.5101 (6)	0.076 (7)
H1A	0.9474	0.7370	0.5114	0.091*
H1B	0.8533	0.6473	0.4922	0.091*
H1C	1.0911	0.6523	0.5012	0.091*
C1	0.175 (2)	0.2573 (11)	0.3084 (7)	0.075 (5)*
C2	0.097 (2)	0.3214 (10)	0.2774 (7)	0.059 (4)*
C3	0.162 (2)	0.3039 (9)	0.2372 (8)	0.063 (4)*
H3	0.1062	0.3465	0.2165	0.076*
C4	0.307 (2)	0.2259 (10)	0.2243 (9)	0.062 (5)*
C5	0.384 (2)	0.1660 (10)	0.2586 (7)	0.059 (4)*
H5	0.4846	0.1149	0.2522	0.071*
C6	0.326 (2)	0.1757 (10)	0.2993 (7)	0.061 (4)*
C8	0.204 (2)	0.3473 (10)	0.3801 (7)	0.062 (4)*
C9	0.098 (3)	0.3836 (10)	0.4156 (7)	0.072 (5)*
H9	−0.0388	0.3561	0.4236	0.087*
C10	0.191 (2)	0.4602 (9)	0.4397 (7)	0.067 (4)*
H10	0.1161	0.4846	0.4632	0.080*
C11	0.395 (2)	0.4996 (9)	0.4282 (8)	0.065 (4)*
C12	0.512 (2)	0.4632 (10)	0.3943 (8)	0.070 (5)*
H12	0.6526	0.4885	0.3878	0.084*
C13	0.416 (2)	0.3872 (10)	0.3697 (7)	0.074 (5)*
H13	0.4915	0.3630	0.3463	0.089*
C14	0.499 (3)	0.5845 (12)	0.4544 (8)	0.066 (5)*
C15	−0.054 (2)	0.4078 (9)	0.2913 (8)	0.085 (10)
H15	−0.0780	0.4009	0.3217	0.101*
C16	−0.278 (2)	0.4030 (10)	0.2707 (7)	0.070 (8)
H16A	−0.3683	0.4582	0.2802	0.104*
H16B	−0.2601	0.4069	0.2408	0.104*
H16C	−0.3499	0.3408	0.2779	0.104*
C17	0.065 (2)	0.5091 (9)	0.2838 (8)	0.091 (9)
H17A	0.2075	0.5086	0.2976	0.136*
H17B	0.0862	0.5190	0.2542	0.136*
H17C	−0.0246	0.5628	0.2949	0.136*
C18	0.370 (3)	0.2031 (12)	0.1802 (9)	0.067 (8)
H18	0.3574	0.1299	0.1775	0.080*
C19	0.216 (3)	0.2474 (14)	0.1458 (9)	0.096 (11)
H19A	0.2705	0.2283	0.1186	0.144*
H19B	0.0667	0.2219	0.1494	0.144*
H19C	0.2138	0.3193	0.1480	0.144*
C20	0.616 (2)	0.2278 (13)	0.1717 (9)	0.110 (11)
H20A	0.6518	0.2122	0.1430	0.165*
H20B	0.6422	0.2980	0.1768	0.165*
H20C	0.7092	0.1886	0.1901	0.165*
C24	0.692 (2)	0.6668 (10)	0.5699 (8)	0.090 (5)*
H24A	0.6997	0.7388	0.5715	0.135*
H24B	0.5741	0.6476	0.5510	0.135*
H24C	0.6615	0.6401	0.5974	0.135*
C25	0.914 (3)	0.6254 (12)	0.5539 (9)	0.086 (5)*
H25	1.0323	0.6486	0.5728	0.103*
C26	0.933 (2)	0.5134 (10)	0.5494 (8)	0.072 (5)*
C27	0.762 (2)	0.4537 (11)	0.5349 (8)	0.080 (5)*
H27	0.6279	0.4829	0.5264	0.096*
C28	0.788 (3)	0.3497 (13)	0.5330 (9)	0.095 (6)*
H28	0.6692	0.3091	0.5246	0.114*
C29	0.986 (3)	0.3081 (13)	0.5435 (8)	0.098 (6)*
H29	1.0041	0.2389	0.5414	0.118*
C30	1.157 (3)	0.3641 (13)	0.5567 (9)	0.105 (6)*
H30	1.2916	0.3339	0.5638	0.126*
C31	1.133 (3)	0.4675 (12)	0.5599 (9)	0.093 (6)*
H31	1.2522	0.5063	0.5691	0.111*
O1	−0.069 (3)	0.2256 (12)	0.3677 (6)	0.088 (7)	0.81 (2)
C7	0.097 (3)	0.2687 (15)	0.3538 (7)	0.090 (8)	0.81 (2)
C21	0.406 (3)	0.1050 (15)	0.3344 (8)	0.074 (7)	0.81 (2)
H21	0.4337	0.1448	0.3598	0.088*	0.81 (2)
C22	0.223 (3)	0.0273 (15)	0.3440 (10)	0.103 (10)	0.81 (2)
H22A	0.0878	0.0614	0.3517	0.155*	0.81 (2)
H22B	0.1972	−0.0133	0.3196	0.155*	0.81 (2)
H22C	0.2706	−0.0148	0.3668	0.155*	0.81 (2)
C23	0.621 (3)	0.0501 (14)	0.3223 (10)	0.097 (11)	0.81 (2)
H23A	0.7358	0.0985	0.3162	0.145*	0.81 (2)
H23B	0.6680	0.0080	0.3451	0.145*	0.81 (2)
H23C	0.5945	0.0095	0.2978	0.145*	0.81 (2)
O1D	−0.140 (6)	0.268 (4)	0.355 (2)	0.077 (16)*	0.19 (2)
C7D	0.101 (6)	0.259 (2)	0.3557 (9)	0.090 (16)*	0.19 (2)
C21D	0.402 (10)	0.132 (5)	0.3417 (12)	0.075 (16)*	0.19 (2)
H21D	0.5236	0.1754	0.3519	0.090*	0.19 (2)
C22D	0.197 (10)	0.157 (3)	0.3683 (17)	0.084 (14)*	0.19 (2)
H22D	0.2378	0.1581	0.3978	0.101*	0.19 (2)
H22E	0.0842	0.1055	0.3643	0.101*	0.19 (2)
C23D	0.494 (16)	0.028 (5)	0.338 (3)	0.11 (2)*	0.19 (2)
H23D	0.6220	0.0287	0.3204	0.162*	0.19 (2)
H23E	0.5360	0.0051	0.3659	0.162*	0.19 (2)
H23F	0.3816	−0.0154	0.3270	0.162*	0.19 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.068 (6)	0.075 (7)	0.091 (19)	0.002 (5)	0.001 (8)	−0.010 (7)
O3	0.079 (6)	0.102 (8)	0.10 (2)	−0.030 (6)	0.016 (9)	−0.016 (8)
N1	0.061 (6)	0.057 (8)	0.11 (3)	0.002 (6)	−0.014 (10)	−0.011 (8)
C15	0.053 (8)	0.055 (10)	0.14 (3)	0.005 (8)	−0.017 (12)	−0.005 (10)
C16	0.068 (9)	0.074 (11)	0.07 (3)	0.010 (7)	−0.008 (12)	0.010 (10)
C17	0.060 (8)	0.066 (11)	0.15 (3)	−0.007 (8)	−0.001 (12)	−0.008 (11)
C18	0.078 (11)	0.085 (13)	0.04 (3)	−0.018 (9)	0.023 (14)	0.007 (10)
C19	0.104 (13)	0.141 (17)	0.04 (4)	0.007 (12)	−0.020 (17)	0.018 (13)
C20	0.082 (11)	0.126 (17)	0.12 (4)	−0.021 (11)	0.017 (15)	0.027 (13)
O1	0.108 (10)	0.092 (12)	0.065 (19)	−0.035 (10)	0.017 (12)	−0.036 (10)
C7	0.081 (12)	0.086 (14)	0.10 (3)	−0.024 (12)	−0.019 (16)	−0.012 (14)
C21	0.081 (11)	0.066 (12)	0.073 (18)	0.011 (10)	−0.017 (13)	0.007 (11)
C22	0.116 (16)	0.088 (15)	0.11 (3)	−0.022 (12)	−0.019 (18)	0.033 (14)
C23	0.087 (14)	0.075 (14)	0.13 (3)	0.042 (12)	0.024 (18)	0.012 (13)

Geometric parameters (Å, º)

O2—C14	1.25 (2)	C11—C14	1.54 (2)
O3—C14	1.250 (18)	C12—C13	1.40 (2)
N1—C25	1.54 (3)	C15—C16	1.49 (2)
C1—C2	1.38 (2)	C15—C17	1.544 (17)
C1—C6	1.439 (18)	C18—C20	1.54 (2)
C1—C7	1.53 (2)	C18—C19	1.55 (3)
C1—C7D	1.57 (2)	C24—C25	1.52 (2)
C2—C3	1.36 (3)	C25—C26	1.50 (2)
C2—C15	1.529 (19)	C26—C27	1.377 (19)
C3—C4	1.414 (19)	C26—C31	1.38 (2)
C4—C5	1.43 (3)	C27—C28	1.393 (18)
C4—C18	1.48 (3)	C28—C29	1.35 (2)
C5—C6	1.35 (2)	C29—C30	1.33 (2)
C6—C21	1.54 (2)	C30—C31	1.386 (18)
C6—C21D	1.54 (3)	O1—C7	1.231 (17)
C8—C9	1.39 (2)	C21—C23	1.531 (19)
C8—C13	1.412 (19)	C21—C22	1.534 (19)
C8—C7	1.482 (18)	O1D—C7D	1.45 (3)
C8—C7D	1.53 (2)	C7D—C22D	1.53 (3)
C9—C10	1.39 (2)	C21D—C23D	1.49 (3)
C10—C11	1.380 (18)	C21D—C22D	1.53 (3)
C11—C12	1.38 (3)
C2—C1—C6	122.3 (18)	C16—C15—C2	111.9 (14)
C2—C1—C7	120.6 (16)	C16—C15—C17	112.6 (13)
C6—C1—C7	117.1 (16)	C2—C15—C17	109.6 (11)
C2—C1—C7D	125.2 (19)	C4—C18—C20	111.5 (19)
C6—C1—C7D	112.4 (19)	C4—C18—C19	116.1 (17)
C3—C2—C1	117.9 (15)	C20—C18—C19	111.5 (18)
C3—C2—C15	124.8 (17)	C26—C25—C24	117.2 (14)
C1—C2—C15	117.3 (18)	C26—C25—N1	106.6 (18)
C2—C3—C4	125 (2)	C24—C25—N1	107.8 (16)
C3—C4—C5	113 (2)	C27—C26—C31	118.0 (14)
C3—C4—C18	125.5 (19)	C27—C26—C25	123.1 (14)
C5—C4—C18	121.8 (16)	C31—C26—C25	118.8 (15)
C6—C5—C4	126.7 (17)	C26—C27—C28	120.3 (15)
C5—C6—C1	115.3 (15)	C29—C28—C27	119.5 (17)
C5—C6—C21	124.0 (15)	C30—C29—C28	121.5 (18)
C1—C6—C21	120.7 (18)	C29—C30—C31	119.9 (18)
C5—C6—C21D	137 (2)	C26—C31—C30	120.7 (17)
C1—C6—C21D	107 (2)	O1—C7—C8	118.2 (18)
C9—C8—C13	118.2 (15)	O1—C7—C1	122.8 (16)
C9—C8—C7	120.6 (14)	C8—C7—C1	118.2 (15)
C13—C8—C7	121.2 (17)	C23—C21—C22	109.2 (16)
C9—C8—C7D	119.7 (16)	C23—C21—C6	111.7 (18)
C13—C8—C7D	121.9 (19)	C22—C21—C6	109.6 (16)
C8—C9—C10	121.4 (14)	O1D—C7D—C22D	117 (3)
C11—C10—C9	119.2 (18)	O1D—C7D—C8	110 (3)
C12—C11—C10	121.7 (16)	C22D—C7D—C8	113 (3)
C12—C11—C14	118.6 (14)	O1D—C7D—C1	105 (3)
C10—C11—C14	119.7 (19)	C22D—C7D—C1	98 (3)
C11—C12—C13	118.9 (14)	C8—C7D—C1	113 (2)
C12—C13—C8	120.6 (18)	C23D—C21D—C22D	122 (5)
O2—C14—O3	124.3 (18)	C23D—C21D—C6	113 (4)
O2—C14—C11	117.8 (15)	C22D—C21D—C6	100 (3)
O3—C14—C11	118 (2)	C21D—C22D—C7D	110 (3)

(760minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.242 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 836 reflections
a = 5.9831 (15) Å	θ = 5.6–23.4°
b = 13.294 (4) Å	µ = 0.08 mm^−1
c = 31.84 (3) Å	T = 299 K
V = 2533 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2210 independent reflections
Radiation source: fine-focus sealed tube	808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.118
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→15
Tmin = 0.171, Tmax = 1.000	l = −20→22
6242 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.086	w = 1/[σ^2(Fo^2) + (0.1115P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.262	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.16 e Å^−3
2210 reflections	Δρmin = −0.15 e Å^−3
198 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
65 restraints	Absolute structure parameter: −1.4 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3823 (16)	0.6240 (7)	0.4826 (5)	0.082 (5)
O3	0.6898 (18)	0.6130 (7)	0.4451 (5)	0.096 (6)
N1	0.9559 (17)	0.6703 (7)	0.5092 (6)	0.084 (8)
H1A	0.9652	0.7370	0.5109	0.101*
H1B	0.8438	0.6536	0.4922	0.101*
H1C	1.0833	0.6458	0.4990	0.101*
C1	0.176 (2)	0.2581 (10)	0.3083 (7)	0.068 (5)*
C2	0.097 (2)	0.3220 (10)	0.2780 (7)	0.060 (4)*
C3	0.163 (2)	0.3048 (10)	0.2373 (8)	0.066 (5)*
H3	0.1072	0.3472	0.2166	0.079*
C4	0.308 (2)	0.2279 (10)	0.2249 (8)	0.067 (5)*
C5	0.385 (2)	0.1664 (9)	0.2583 (7)	0.059 (4)*
H5	0.4827	0.1145	0.2515	0.071*
C6	0.327 (2)	0.1769 (9)	0.2996 (7)	0.059 (4)*
C8	0.205 (2)	0.3470 (10)	0.3805 (7)	0.062 (4)*
C9	0.098 (3)	0.3848 (10)	0.4151 (7)	0.075 (5)*
H9	−0.0400	0.3584	0.4228	0.090*
C10	0.190 (2)	0.4608 (10)	0.4388 (7)	0.075 (5)*
H10	0.1137	0.4860	0.4620	0.090*
C11	0.396 (3)	0.4993 (10)	0.4277 (8)	0.070 (5)*
C12	0.511 (3)	0.4626 (10)	0.3943 (8)	0.074 (5)*
H12	0.6523	0.4873	0.3878	0.089*
C13	0.413 (2)	0.3860 (10)	0.3693 (7)	0.075 (5)*
H13	0.4869	0.3620	0.3457	0.090*
C14	0.498 (3)	0.5836 (12)	0.4550 (8)	0.069 (5)*
C15	−0.052 (2)	0.4080 (10)	0.2904 (8)	0.083 (10)
H15	−0.0765	0.4011	0.3207	0.100*
C16	−0.277 (2)	0.4033 (10)	0.2707 (7)	0.071 (5)*
H16A	−0.3642	0.4600	0.2797	0.106*
H16B	−0.2618	0.4049	0.2407	0.106*
H16C	−0.3503	0.3422	0.2789	0.106*
C17	0.065 (3)	0.5097 (9)	0.2842 (8)	0.086 (5)*
H17A	0.2092	0.5080	0.2976	0.130*
H17B	0.0840	0.5225	0.2548	0.130*
H17C	−0.0236	0.5621	0.2965	0.130*
C18	0.372 (3)	0.2031 (12)	0.1819 (9)	0.083 (5)*
H18	0.3605	0.1298	0.1796	0.100*
C19	0.219 (3)	0.2462 (13)	0.1470 (9)	0.125 (8)*
H19A	0.2746	0.2258	0.1200	0.188*
H19B	0.0698	0.2213	0.1507	0.188*
H19C	0.2182	0.3183	0.1487	0.188*
C20	0.617 (3)	0.2294 (12)	0.1724 (9)	0.108 (7)*
H20A	0.6511	0.2119	0.1438	0.161*
H20B	0.6400	0.3002	0.1764	0.161*
H20C	0.7131	0.1925	0.1910	0.161*
C24	0.691 (2)	0.6654 (10)	0.5692 (8)	0.093 (6)*
H24A	0.6958	0.7375	0.5707	0.140*
H24B	0.5739	0.6453	0.5503	0.140*
H24C	0.6618	0.6384	0.5966	0.140*
C25	0.913 (3)	0.6261 (12)	0.5533 (9)	0.088 (6)*
H25	1.0311	0.6499	0.5722	0.105*
C26	0.933 (2)	0.5138 (10)	0.5490 (8)	0.076 (5)*
C27	0.762 (2)	0.4525 (12)	0.5340 (8)	0.085 (6)*
H27	0.6293	0.4813	0.5246	0.102*
C28	0.789 (3)	0.3487 (13)	0.5330 (9)	0.096 (6)*
H28	0.6699	0.3078	0.5250	0.115*
C29	0.987 (3)	0.3072 (13)	0.5436 (8)	0.101 (6)*
H29	1.0039	0.2378	0.5422	0.121*
C30	1.158 (3)	0.3641 (12)	0.5559 (9)	0.102 (6)*
H30	1.2947	0.3344	0.5625	0.122*
C31	1.133 (3)	0.4676 (11)	0.5590 (9)	0.093 (6)*
H31	1.2525	0.5066	0.5680	0.112*
O1	−0.066 (3)	0.2244 (13)	0.3673 (7)	0.092 (8)	0.77 (2)
C7	0.096 (4)	0.2690 (16)	0.3539 (7)	0.097 (9)	0.77 (2)
C21	0.405 (3)	0.1057 (15)	0.3340 (8)	0.073 (7)	0.77 (2)
H21	0.4257	0.1457	0.3595	0.087*	0.77 (2)
C22	0.224 (4)	0.0280 (15)	0.3432 (11)	0.108 (9)*	0.77 (2)
H22A	0.0853	0.0618	0.3487	0.162*	0.77 (2)
H22B	0.2067	−0.0156	0.3194	0.162*	0.77 (2)
H22C	0.2661	−0.0110	0.3673	0.162*	0.77 (2)
C23	0.624 (3)	0.0523 (15)	0.3253 (9)	0.083 (8)*	0.77 (2)
H23A	0.6604	0.0092	0.3485	0.124*	0.77 (2)
H23B	0.6103	0.0128	0.3002	0.124*	0.77 (2)
H23C	0.7408	0.1012	0.3216	0.124*	0.77 (2)
O1D	−0.138 (5)	0.264 (4)	0.3565 (19)	0.076 (15)*	0.23 (2)
C7D	0.104 (6)	0.258 (2)	0.3560 (9)	0.094 (15)*	0.23 (2)
C21D	0.398 (10)	0.128 (4)	0.3410 (11)	0.075 (15)*	0.23 (2)
H21D	0.5252	0.1671	0.3515	0.090*	0.23 (2)
C22D	0.199 (9)	0.155 (3)	0.3685 (16)	0.083 (14)*	0.23 (2)
H22D	0.2453	0.1573	0.3977	0.099*	0.23 (2)
H22E	0.0840	0.1045	0.3656	0.099*	0.23 (2)
C23D	0.482 (13)	0.023 (4)	0.335 (2)	0.09 (2)*	0.23 (2)
H23D	0.6081	0.0231	0.3167	0.141*	0.23 (2)
H23E	0.5250	−0.0045	0.3620	0.141*	0.23 (2)
H23F	0.3650	−0.0180	0.3234	0.141*	0.23 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.077 (7)	0.084 (8)	0.084 (19)	0.002 (6)	0.002 (9)	−0.012 (7)
O3	0.083 (7)	0.110 (9)	0.09 (2)	−0.028 (7)	0.016 (9)	−0.016 (8)
N1	0.061 (7)	0.059 (8)	0.13 (3)	−0.007 (6)	−0.010 (10)	−0.013 (8)
C15	0.056 (8)	0.072 (11)	0.12 (3)	−0.003 (8)	−0.016 (12)	−0.007 (10)
O1	0.119 (12)	0.095 (13)	0.063 (19)	−0.040 (11)	0.026 (13)	−0.027 (10)
C7	0.092 (15)	0.103 (15)	0.10 (3)	−0.023 (14)	0.005 (18)	−0.006 (15)
C21	0.078 (11)	0.064 (12)	0.075 (18)	0.009 (10)	−0.005 (13)	−0.010 (10)

Geometric parameters (Å, º)

O2—C14	1.24 (2)	C11—C14	1.54 (3)
O3—C14	1.254 (19)	C12—C13	1.42 (2)
N1—C25	1.54 (3)	C15—C16	1.487 (19)
C1—C2	1.37 (2)	C15—C17	1.536 (17)
C1—C6	1.433 (18)	C18—C20	1.54 (2)
C1—C7	1.54 (2)	C18—C19	1.55 (3)
C1—C7D	1.58 (2)	C24—C25	1.52 (2)
C2—C3	1.37 (3)	C25—C26	1.51 (2)
C2—C15	1.503 (18)	C26—C31	1.38 (2)
C3—C4	1.399 (18)	C26—C27	1.39 (2)
C4—C5	1.42 (2)	C27—C28	1.390 (18)
C4—C18	1.46 (3)	C28—C29	1.35 (2)
C5—C6	1.37 (2)	C29—C30	1.33 (2)
C6—C21	1.52 (2)	C30—C31	1.388 (18)
C6—C21D	1.53 (2)	O1—C7	1.213 (17)
C8—C9	1.37 (2)	C21—C23	1.516 (19)
C8—C13	1.397 (19)	C21—C22	1.52 (2)
C8—C7	1.490 (19)	O1D—C7D	1.45 (3)
C8—C7D	1.54 (2)	C7D—C22D	1.53 (3)
C9—C10	1.375 (19)	C21D—C23D	1.49 (3)
C10—C11	1.382 (19)	C21D—C22D	1.52 (3)
C11—C12	1.36 (3)
C2—C1—C6	123.2 (18)	C16—C15—C2	113.3 (14)
C2—C1—C7	119.9 (16)	C16—C15—C17	113.4 (13)
C6—C1—C7	116.8 (16)	C2—C15—C17	111.4 (11)
C2—C1—C7D	125.7 (18)	C4—C18—C20	112.4 (19)
C6—C1—C7D	110.9 (18)	C4—C18—C19	115.9 (16)
C1—C2—C3	117.5 (15)	C20—C18—C19	109.7 (19)
C1—C2—C15	119.5 (18)	C26—C25—C24	116.3 (14)
C3—C2—C15	123.0 (16)	C26—C25—N1	106.3 (18)
C2—C3—C4	124.5 (19)	C24—C25—N1	108.6 (16)
C3—C4—C5	114 (2)	C31—C26—C27	117.1 (15)
C3—C4—C18	126.3 (19)	C31—C26—C25	119.4 (16)
C5—C4—C18	119.3 (15)	C27—C26—C25	123.4 (14)
C6—C5—C4	125.4 (16)	C28—C27—C26	120.2 (16)
C5—C6—C1	115.0 (14)	C29—C28—C27	120.0 (17)
C5—C6—C21	123.4 (15)	C30—C29—C28	121.2 (18)
C1—C6—C21	121.5 (18)	C29—C30—C31	119.9 (18)
C5—C6—C21D	135.5 (18)	C26—C31—C30	121.4 (18)
C1—C6—C21D	109.3 (19)	O1—C7—C8	119.1 (19)
C9—C8—C13	119.0 (15)	O1—C7—C1	122.5 (17)
C9—C8—C7	120.7 (14)	C8—C7—C1	117.9 (16)
C13—C8—C7	120.2 (17)	C23—C21—C6	115.2 (19)
C9—C8—C7D	120.5 (16)	C23—C21—C22	109.5 (15)
C13—C8—C7D	120.3 (18)	C6—C21—C22	109.9 (17)
C8—C9—C10	121.6 (14)	O1D—C7D—C22D	115 (3)
C9—C10—C11	119.3 (19)	O1D—C7D—C8	110 (3)
C12—C11—C10	121.3 (17)	C22D—C7D—C8	114 (3)
C12—C11—C14	120.1 (15)	O1D—C7D—C1	107 (3)
C10—C11—C14	119 (2)	C22D—C7D—C1	99 (2)
C11—C12—C13	119.2 (15)	C8—C7D—C1	112 (2)
C8—C13—C12	119.5 (18)	C23D—C21D—C22D	124 (4)
O2—C14—O3	123.7 (18)	C23D—C21D—C6	113 (4)
O2—C14—C11	119.6 (16)	C22D—C21D—C6	100 (3)
O3—C14—C11	116 (2)	C21D—C22D—C7D	111 (3)

(940minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.243 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 926 reflections
a = 5.9808 (13) Å	θ = 5.6–21.7°
b = 13.293 (4) Å	µ = 0.08 mm^−1
c = 31.84 (3) Å	T = 299 K
V = 2531 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2248 independent reflections
Radiation source: fine-focus sealed tube	852 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.144
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −11→15
Tmin = 0.337, Tmax = 1.000	l = −20→23
7206 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.085	w = 1/[σ^2(Fo^2) + (0.0916P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.236	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.16 e Å^−3
2248 reflections	Δρmin = −0.15 e Å^−3
200 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
154 restraints	Absolute structure parameter: −2.4 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3799 (14)	0.6235 (6)	0.4828 (4)	0.078 (5)
O3	0.6898 (15)	0.6126 (7)	0.4450 (5)	0.098 (6)
C1	0.1780 (19)	0.2568 (9)	0.3082 (5)	0.0582 (18)*
C2	0.1001 (19)	0.3211 (9)	0.2775 (6)	0.0582 (18)*
C3	0.1636 (19)	0.3056 (9)	0.2360 (7)	0.0582 (18)*
H3	0.1091	0.3484	0.2154	0.070*
C4	0.3067 (19)	0.2276 (9)	0.2246 (7)	0.0582 (18)*
C5	0.3877 (18)	0.1657 (9)	0.2580 (6)	0.0582 (18)*
H5	0.4876	0.1145	0.2513	0.070*
C6	0.328 (2)	0.1768 (9)	0.2984 (6)	0.0582 (18)*
C14	0.498 (3)	0.5852 (11)	0.4543 (7)	0.070 (5)*
C18	0.372 (2)	0.2038 (10)	0.1818 (8)	0.075 (5)*
H18	0.3604	0.1304	0.1795	0.091*
C19	0.619 (2)	0.2286 (11)	0.1729 (8)	0.107 (6)*
H19A	0.6540	0.2117	0.1443	0.161*
H19B	0.6442	0.2991	0.1773	0.161*
H19C	0.7126	0.1905	0.1915	0.161*
C20	0.218 (2)	0.2456 (12)	0.1471 (8)	0.118 (7)*
H20A	0.2748	0.2260	0.1201	0.177*
H20B	0.0700	0.2192	0.1507	0.177*
H20C	0.2140	0.3177	0.1489	0.177*
C26	0.9382 (8)	0.5130 (4)	0.5487 (3)	0.070 (4)*
N1	0.9529 (13)	0.6722 (4)	0.5093 (4)	0.077 (6)
H1A	0.8485	0.6506	0.4915	0.092*
H1B	1.0873	0.6546	0.4998	0.092*
H1C	0.9454	0.7389	0.5114	0.092*
C24	0.6956 (15)	0.6627 (5)	0.5691 (4)	0.087 (5)*
H24A	0.5767	0.6447	0.5503	0.130*
H24B	0.7005	0.7345	0.5722	0.130*
H24C	0.6696	0.6324	0.5961	0.130*
C25	0.9150 (10)	0.6259 (4)	0.5517 (3)	0.088 (5)*
H25	1.0336	0.6502	0.5703	0.106*
C27	1.1324 (10)	0.4663 (5)	0.5613 (4)	0.089 (5)*
H27	1.2510	0.5050	0.5711	0.107*
C28	1.1537 (13)	0.3626 (5)	0.5595 (4)	0.101 (5)*
H28	1.2855	0.3321	0.5684	0.121*
C29	0.9837 (15)	0.3056 (4)	0.5451 (4)	0.105 (6)*
H29	0.9992	0.2361	0.5438	0.126*
C30	0.7889 (14)	0.3498 (4)	0.5323 (4)	0.095 (5)*
H30	0.6716	0.3103	0.5225	0.114*
C31	0.7661 (9)	0.4538 (4)	0.5339 (4)	0.084 (5)*
H31	0.6339	0.4837	0.5249	0.101*
O1	−0.062 (3)	0.2221 (12)	0.3676 (7)	0.080 (7)	0.675 (4)
C7	0.097 (3)	0.2686 (15)	0.3535 (7)	0.075 (8)*	0.675 (4)
C8	0.204 (2)	0.3460 (10)	0.3801 (6)	0.055 (4)*	0.675 (4)
C9	0.096 (2)	0.3806 (10)	0.4164 (6)	0.062 (5)*	0.675 (4)
H9	−0.0383	0.3518	0.4250	0.074*	0.675 (4)
C10	0.190 (2)	0.4574 (10)	0.4390 (7)	0.064 (5)*	0.675 (4)
H10	0.1137	0.4829	0.4621	0.076*	0.675 (4)
C11	0.395 (2)	0.4981 (11)	0.4283 (8)	0.058 (5)*	0.675 (4)
C12	0.510 (2)	0.4611 (11)	0.3951 (8)	0.063 (5)*	0.675 (4)
H12	0.6514	0.4860	0.3887	0.075*	0.675 (4)
C13	0.415 (2)	0.3852 (10)	0.3706 (7)	0.067 (5)*	0.675 (4)
H13	0.4928	0.3604	0.3476	0.081*	0.675 (4)
C15	−0.053 (2)	0.4098 (9)	0.2899 (7)	0.068 (5)	0.675 (4)
H15	−0.0801	0.4043	0.3202	0.082*	0.675 (4)
C16	−0.279 (2)	0.4033 (10)	0.2685 (8)	0.065 (5)*	0.675 (4)
H16A	−0.3452	0.3389	0.2742	0.098*	0.675 (4)
H16B	−0.3748	0.4555	0.2791	0.098*	0.675 (4)
H16C	−0.2603	0.4115	0.2388	0.098*	0.675 (4)
C17	0.064 (3)	0.5108 (10)	0.2824 (9)	0.075 (5)*	0.675 (4)
H17A	0.2053	0.5111	0.2965	0.113*	0.675 (4)
H17B	0.0866	0.5203	0.2528	0.113*	0.675 (4)
H17C	−0.0279	0.5643	0.2931	0.113*	0.675 (4)
C21	0.405 (3)	0.1061 (14)	0.3334 (7)	0.073 (6)	0.675 (4)
H21	0.4277	0.1468	0.3587	0.087*	0.675 (4)
C22	0.222 (3)	0.0284 (15)	0.3434 (11)	0.120 (8)*	0.675 (4)
H22A	0.0836	0.0626	0.3491	0.179*	0.675 (4)
H22B	0.2024	−0.0157	0.3198	0.179*	0.675 (4)
H22C	0.2651	−0.0102	0.3676	0.179*	0.675 (4)
C23	0.621 (3)	0.0509 (13)	0.3245 (9)	0.080 (7)*	0.675 (4)
H23A	0.6566	0.0082	0.3479	0.120*	0.675 (4)
H23B	0.6035	0.0106	0.2997	0.120*	0.675 (4)
H23C	0.7387	0.0987	0.3203	0.120*	0.675 (4)
O1D	−0.137 (5)	0.264 (4)	0.3545 (18)	0.079 (19)*	0.230 (4)
C7D	0.106 (6)	0.257 (2)	0.3557 (8)	0.076 (18)*	0.230 (4)
C8D	0.204 (2)	0.3460 (10)	0.3801 (6)	0.055 (4)*	0.230 (4)
C9D	0.096 (2)	0.3806 (10)	0.4164 (6)	0.062 (5)*	0.230 (4)
H9D	−0.0383	0.3518	0.4250	0.074*	0.230 (4)
C10D	0.190 (2)	0.4574 (10)	0.4390 (7)	0.064 (5)*	0.230 (4)
H10D	0.1137	0.4829	0.4621	0.076*	0.230 (4)
C11D	0.395 (2)	0.4981 (11)	0.4283 (8)	0.058 (5)*	0.230 (4)
C12D	0.510 (2)	0.4611 (11)	0.3951 (8)	0.063 (5)*	0.230 (4)
H12D	0.6514	0.4860	0.3887	0.075*	0.230 (4)
C13D	0.415 (2)	0.3852 (10)	0.3706 (7)	0.067 (5)*	0.230 (4)
H13D	0.4928	0.3604	0.3476	0.081*	0.230 (4)
C15D	−0.053 (2)	0.4098 (9)	0.2899 (7)	0.068 (5)	0.230 (4)
H15D	−0.0801	0.4043	0.3202	0.082*	0.230 (4)
C16D	−0.279 (2)	0.4033 (10)	0.2685 (8)	0.065 (5)*	0.230 (4)
H16D	−0.3452	0.3389	0.2742	0.098*	0.230 (4)
H16E	−0.3748	0.4555	0.2791	0.098*	0.230 (4)
H16F	−0.2603	0.4115	0.2388	0.098*	0.230 (4)
C17D	0.064 (3)	0.5108 (10)	0.2824 (9)	0.075 (5)*	0.230 (4)
H17D	0.2053	0.5111	0.2965	0.113*	0.230 (4)
H17E	0.0866	0.5203	0.2528	0.113*	0.230 (4)
H17F	−0.0279	0.5643	0.2931	0.113*	0.230 (4)
C21D	0.402 (9)	0.128 (4)	0.3397 (10)	0.076 (11)*	0.230 (4)
H21D	0.5289	0.1676	0.3498	0.091*	0.230 (4)
C22D	0.206 (8)	0.155 (3)	0.3679 (15)	0.10 (2)*	0.230 (4)
H22D	0.2554	0.1573	0.3969	0.122*	0.230 (4)
H22E	0.0915	0.1034	0.3657	0.122*	0.230 (4)
C23D	0.486 (12)	0.023 (4)	0.334 (2)	0.10 (2)*	0.230 (4)
H23D	0.6098	0.0229	0.3153	0.149*	0.230 (4)
H23E	0.5328	−0.0028	0.3612	0.149*	0.230 (4)
H23F	0.3682	−0.0186	0.3234	0.149*	0.230 (4)
O1P	−0.110 (14)	0.258 (7)	0.365 (2)	0.09 (3)*	0.096 (4)
C7P	0.044 (7)	0.312 (3)	0.3410 (11)	0.07 (2)*	0.096 (4)
C8P	0.164 (7)	0.384 (2)	0.3709 (11)	0.056 (19)*	0.096 (4)
C9P	0.056 (7)	0.422 (5)	0.4038 (17)	0.069 (19)*	0.096 (4)
H9P	−0.0914	0.4027	0.4089	0.082*	0.096 (4)
C10P	0.160 (9)	0.489 (7)	0.430 (2)	0.049 (19)*	0.096 (4)
H10P	0.0846	0.5137	0.4539	0.059*	0.096 (4)
C11P	0.376 (9)	0.521 (7)	0.422 (2)	0.061 (19)*	0.096 (4)
C12P	0.489 (9)	0.483 (7)	0.388 (2)	0.055 (19)*	0.096 (4)
H12P	0.6359	0.5025	0.3826	0.067*	0.096 (4)
C13P	0.385 (9)	0.414 (6)	0.3612 (17)	0.067 (19)*	0.096 (4)
H13P	0.4587	0.3892	0.3377	0.081*	0.096 (4)
C15P	−0.047 (8)	0.388 (4)	0.3036 (14)	0.071 (12)*	0.096 (4)
C16P	−0.296 (8)	0.383 (8)	0.297 (3)	0.09 (3)*	0.096 (4)
H16G	−0.3683	0.4293	0.3156	0.135*	0.096 (4)
H16H	−0.3293	0.4010	0.2683	0.135*	0.096 (4)
H16I	−0.3478	0.3161	0.3023	0.135*	0.096 (4)
C17P	0.043 (17)	0.495 (3)	0.306 (3)	0.05 (3)*	0.096 (4)
H17G	−0.0561	0.5349	0.3234	0.076*	0.096 (4)
H17H	0.1889	0.4944	0.3189	0.076*	0.096 (4)
H17I	0.0516	0.5236	0.2788	0.076*	0.096 (4)
C21P	0.405 (3)	0.1061 (14)	0.3334 (7)	0.073 (6)	0.096 (4)
H21P	0.4277	0.1468	0.3587	0.087*	0.096 (4)
C22P	0.222 (3)	0.0284 (15)	0.3434 (11)	0.120 (8)*	0.096 (4)
H22F	0.0836	0.0626	0.3491	0.179*	0.096 (4)
H22G	0.2024	−0.0157	0.3198	0.179*	0.096 (4)
H22H	0.2651	−0.0102	0.3676	0.179*	0.096 (4)
C23P	0.621 (3)	0.0509 (13)	0.3245 (9)	0.080 (7)*	0.096 (4)
H23G	0.6566	0.0082	0.3479	0.120*	0.096 (4)
H23H	0.6035	0.0106	0.2997	0.120*	0.096 (4)
H23I	0.7387	0.0987	0.3203	0.120*	0.096 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.077 (6)	0.073 (7)	0.084 (17)	0.001 (5)	0.010 (8)	−0.019 (6)
O3	0.075 (6)	0.105 (8)	0.11 (2)	−0.029 (6)	0.011 (8)	−0.025 (8)
N1	0.078 (7)	0.054 (7)	0.10 (2)	0.001 (5)	−0.009 (9)	−0.005 (7)
O1	0.104 (12)	0.084 (13)	0.05 (2)	−0.031 (11)	0.028 (13)	−0.020 (11)
C15	0.074 (8)	0.047 (8)	0.085 (15)	0.002 (7)	−0.010 (10)	0.004 (8)
C21	0.080 (10)	0.065 (11)	0.072 (15)	0.013 (9)	0.001 (11)	0.003 (10)
C15D	0.074 (8)	0.047 (8)	0.085 (15)	0.002 (7)	−0.010 (10)	0.004 (8)
C21P	0.080 (10)	0.065 (11)	0.072 (15)	0.013 (9)	0.001 (11)	0.003 (10)

Geometric parameters (Å, º)

O2—C14	1.26 (2)	C8—C9	1.40 (2)
O3—C14	1.239 (16)	C9—C10	1.369 (18)
C1—C2	1.380 (18)	C10—C11	1.386 (18)
C1—C6	1.427 (15)	C11—C12	1.35 (3)
C1—C7P	1.50 (2)	C12—C13	1.40 (2)
C1—C7	1.53 (2)	C15—C16	1.515 (19)
C1—C7D	1.57 (2)	C15—C17	1.533 (17)
C2—C3	1.39 (2)	C21—C23	1.512 (18)
C2—C15P	1.50 (2)	C21—C22	1.54 (2)
C2—C15	1.545 (18)	O1D—C7D	1.45 (3)
C2—C15D	1.545 (18)	C7D—C22D	1.53 (3)
C3—C4	1.393 (15)	C7D—C8D	1.54 (2)
C4—C5	1.43 (2)	C8D—C13D	1.394 (18)
C4—C18	1.45 (3)	C8D—C9D	1.40 (2)
C5—C6	1.34 (2)	C9D—C10D	1.369 (18)
C6—C21P	1.526 (19)	C10D—C11D	1.386 (18)
C6—C21	1.526 (19)	C11D—C12D	1.35 (3)
C6—C21D	1.53 (2)	C12D—C13D	1.40 (2)
C14—C11P	1.52 (2)	C15D—C16D	1.515 (19)
C14—C11	1.55 (2)	C15D—C17D	1.533 (17)
C14—C11D	1.55 (2)	C21D—C23D	1.49 (3)
C18—C20	1.54 (2)	C21D—C22D	1.52 (3)
C18—C19	1.541 (18)	O1P—C7P	1.40 (3)
C26—C27	1.3764	C7P—C8P	1.53 (2)
C26—C31	1.3785	C7P—C15P	1.65 (3)
C26—C25	1.5097	C8P—C9P	1.3282
N1—C25	1.5013	C8P—C13P	1.4209
C24—C25	1.5071	C9P—C10P	1.3841
C27—C28	1.3864	C10P—C11P	1.3855
C28—C29	1.3481	C11P—C12P	1.3815
C29—C30	1.3674	C12P—C13P	1.3894
C30—C31	1.3911	C15P—C16P	1.51 (3)
O1—C7	1.220 (17)	C15P—C17P	1.53 (3)
C7—C8	1.479 (18)	C21P—C23P	1.512 (18)
C8—C13	1.394 (18)	C21P—C22P	1.54 (2)
C2—C1—C6	121.4 (15)	C10—C11—C14	120.8 (19)
C2—C1—C7P	90.7 (19)	C11—C12—C13	119.4 (14)
C6—C1—C7P	148 (2)	C8—C13—C12	121.2 (18)
C2—C1—C7	119.9 (14)	C16—C15—C17	112.7 (13)
C6—C1—C7	118.7 (14)	C16—C15—C2	111.8 (13)
C2—C1—C7D	126.1 (17)	C17—C15—C2	110.9 (11)
C6—C1—C7D	112.4 (17)	C23—C21—C6	114.7 (18)
C1—C2—C3	119.3 (13)	C23—C21—C22	108.7 (14)
C1—C2—C15P	100 (2)	C6—C21—C22	110.7 (16)
C3—C2—C15P	141 (2)	O1D—C7D—C22D	117 (3)
C1—C2—C15	119.4 (16)	O1D—C7D—C8D	110 (3)
C3—C2—C15	121.3 (14)	C22D—C7D—C8D	114 (3)
C1—C2—C15D	119.4 (16)	O1D—C7D—C1	104 (3)
C3—C2—C15D	121.3 (14)	C22D—C7D—C1	98 (2)
C2—C3—C4	121.9 (17)	C8D—C7D—C1	112.3 (19)
C3—C4—C5	116.2 (19)	C13D—C8D—C9D	118.2 (15)
C3—C4—C18	124.9 (17)	C13D—C8D—C7D	121.8 (18)
C5—C4—C18	118.8 (14)	C9D—C8D—C7D	119.4 (15)
C6—C5—C4	124.1 (14)	C10D—C9D—C8D	119.1 (13)
C5—C6—C1	117.2 (13)	C9D—C10D—C11D	121.8 (17)
C5—C6—C21P	123.5 (14)	C12D—C11D—C10D	120.0 (16)
C1—C6—C21P	119.2 (16)	C12D—C11D—C14	119.2 (14)
C5—C6—C21	123.5 (14)	C10D—C11D—C14	120.8 (19)
C1—C6—C21	119.2 (16)	C11D—C12D—C13D	119.4 (14)
C5—C6—C21D	134.5 (17)	C8D—C13D—C12D	121.2 (18)
C1—C6—C21D	108.0 (18)	C16D—C15D—C17D	112.7 (13)
O3—C14—O2	125.0 (16)	C16D—C15D—C2	111.8 (13)
O3—C14—C11P	117 (2)	C17D—C15D—C2	110.9 (11)
O2—C14—C11P	116 (2)	C23D—C21D—C22D	123 (4)
O3—C14—C11	117.3 (18)	C23D—C21D—C6	113 (4)
O2—C14—C11	117.7 (15)	C22D—C21D—C6	101 (3)
O3—C14—C11D	117.3 (18)	C21D—C22D—C7D	111 (3)
O2—C14—C11D	117.7 (15)	O1P—C7P—C1	119 (4)
C4—C18—C20	115.7 (14)	O1P—C7P—C8P	107 (3)
C4—C18—C19	112.5 (17)	C1—C7P—C8P	119 (2)
C20—C18—C19	111.3 (17)	O1P—C7P—C15P	120 (4)
C27—C26—C31	118.2	C1—C7P—C15P	88.3 (18)
C27—C26—C25	120.5	C8P—C7P—C15P	103 (2)
C31—C26—C25	121.3	C9P—C8P—C13P	121.1
N1—C25—C24	109.3	C9P—C8P—C7P	120 (2)
N1—C25—C26	109.8	C13P—C8P—C7P	119 (2)
C24—C25—C26	115.2	C8P—C9P—C10P	120.75 (8)
C26—C27—C28	120.9	C9P—C10P—C11P	119.9
C29—C28—C27	120.2	C12P—C11P—C10P	119.88 (6)
C28—C29—C30	120.2	C12P—C11P—C14	120 (3)
C29—C30—C31	119.9	C10P—C11P—C14	119 (3)
C26—C31—C30	120.5	C11P—C12P—C13P	120.14 (9)
O1—C7—C8	118.8 (19)	C12P—C13P—C8P	118.2
O1—C7—C1	122.7 (17)	C2—C15P—C16P	118 (4)
C8—C7—C1	118.2 (15)	C2—C15P—C17P	112 (4)
C13—C8—C9	118.2 (15)	C16P—C15P—C17P	113 (3)
C13—C8—C7	121.9 (17)	C2—C15P—C7P	81.2 (18)
C9—C8—C7	119.9 (13)	C16P—C15P—C7P	114 (4)
C10—C9—C8	119.1 (13)	C17P—C15P—C7P	114 (4)
C9—C10—C11	121.8 (17)	C23P—C21P—C6	114.7 (18)
C12—C11—C10	120.0 (16)	C23P—C21P—C22P	108.7 (14)
C12—C11—C14	119.2 (14)	C6—C21P—C22P	110.7 (16)

(1120minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.245 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 601 reflections
a = 5.9870 (15) Å	θ = 5.7–21.7°
b = 13.257 (5) Å	µ = 0.08 mm^−1
c = 31.84 (3) Å	T = 299 K
V = 2527 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2199 independent reflections
Radiation source: fine-focus sealed tube	741 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.142
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.7°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→11
Tmin = 0.352, Tmax = 1.000	l = −20→23
5410 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.100	w = 1/[σ^2(Fo^2) + (0.1008P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.280	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.16 e Å^−3
2199 reflections	Δρmin = −0.16 e Å^−3
177 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
154 restraints	Absolute structure parameter: 0.2 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C26	0.9387 (10)	0.5134 (5)	0.5485 (4)	0.088 (6)*
N1	0.9532 (15)	0.6731 (5)	0.5090 (4)	0.076 (4)*
H1A	0.8494	0.6514	0.4912	0.092*
H1B	1.0878	0.6556	0.4996	0.092*
H1C	0.9452	0.7400	0.5111	0.092*
C24	0.6948 (18)	0.6632 (6)	0.5686 (5)	0.096 (6)*
H24A	0.5766	0.6450	0.5497	0.144*
H24B	0.6991	0.7353	0.5717	0.144*
H24C	0.6684	0.6327	0.5956	0.144*
C25	0.9147 (12)	0.6266 (5)	0.5514 (4)	0.097 (6)*
H25	1.0325	0.6511	0.5701	0.117*
C27	1.1327 (13)	0.4669 (6)	0.5612 (5)	0.099 (6)*
H27	1.2507	0.5058	0.5711	0.119*
C28	1.1547 (16)	0.3629 (6)	0.5594 (5)	0.107 (7)*
H28	1.2864	0.3325	0.5684	0.129*
C29	0.9857 (19)	0.3056 (5)	0.5448 (5)	0.112 (7)*
H29	1.0017	0.2358	0.5436	0.134*
C30	0.7910 (17)	0.3496 (5)	0.5318 (5)	0.107 (7)*
H30	0.6744	0.3098	0.5220	0.129*
C31	0.7676 (11)	0.4539 (5)	0.5335 (4)	0.092 (6)*
H31	0.6355	0.4837	0.5244	0.111*
C1	0.177 (2)	0.2577 (10)	0.3085 (6)	0.064 (2)*
O2	0.3776 (18)	0.6236 (8)	0.4834 (5)	0.086 (6)
C2	0.104 (2)	0.3206 (11)	0.2764 (7)	0.064 (2)*
O3	0.689 (2)	0.6127 (8)	0.4459 (5)	0.109 (7)
C3	0.165 (2)	0.3060 (10)	0.2342 (8)	0.064 (2)*
H3	0.1079	0.3474	0.2131	0.077*
C4	0.313 (2)	0.2282 (11)	0.2246 (9)	0.064 (2)*
C5	0.387 (2)	0.1663 (11)	0.2580 (7)	0.064 (2)*
H5	0.4834	0.1137	0.2515	0.077*
C6	0.327 (2)	0.1776 (10)	0.2992 (6)	0.064 (2)*
C14	0.495 (3)	0.5849 (13)	0.4546 (8)	0.076 (6)*
C18	0.370 (3)	0.2022 (13)	0.1814 (9)	0.087 (6)*
H18	0.3577	0.1286	0.1792	0.104*
C19	0.616 (3)	0.2291 (13)	0.1724 (9)	0.110 (7)*
H19A	0.6521	0.2117	0.1440	0.165*
H19B	0.6384	0.3001	0.1766	0.165*
H19C	0.7112	0.1921	0.1912	0.165*
C20	0.220 (3)	0.2460 (15)	0.1475 (10)	0.134 (9)*
H20A	0.2716	0.2244	0.1204	0.201*
H20B	0.0694	0.2230	0.1517	0.201*
H20C	0.2238	0.3183	0.1489	0.201*
O1	−0.060 (4)	0.2216 (16)	0.3673 (8)	0.084 (9)	0.633 (4)
C7	0.100 (4)	0.2691 (19)	0.3537 (7)	0.090 (10)*	0.633 (4)
C8	0.2035 (18)	0.3460 (8)	0.3813 (4)	0.054 (5)*	0.633 (4)
C9	0.0955 (15)	0.3816 (8)	0.4146 (5)	0.073 (3)*	0.633 (4)
H9	−0.0452	0.3565	0.4212	0.087*	0.633 (4)
C10	0.190 (2)	0.4558 (9)	0.4395 (4)	0.073 (3)*	0.633 (4)
H10	0.1153	0.4783	0.4634	0.087*	0.633 (4)
C11	0.395 (2)	0.4964 (9)	0.4289 (5)	0.068 (6)*	0.633 (4)
C12	0.5090 (16)	0.4605 (9)	0.3942 (5)	0.073 (3)*	0.633 (4)
H12	0.6488	0.4864	0.3875	0.087*	0.633 (4)
C13	0.4146 (19)	0.3857 (9)	0.3693 (4)	0.073 (3)*	0.633 (4)
H13	0.4876	0.3622	0.3455	0.087*	0.633 (4)
C15	−0.054 (3)	0.4104 (12)	0.2900 (9)	0.079 (6)	0.633 (4)
H15	−0.0784	0.4057	0.3203	0.095*	0.633 (4)
C16	−0.281 (3)	0.4031 (13)	0.2679 (9)	0.073 (6)*	0.633 (4)
H16A	−0.3488	0.3394	0.2744	0.109*	0.633 (4)
H16B	−0.3756	0.4568	0.2774	0.109*	0.633 (4)
H16C	−0.2600	0.4084	0.2381	0.109*	0.633 (4)
C17	0.064 (3)	0.5106 (12)	0.2808 (10)	0.079 (7)*	0.633 (4)
H17A	0.2050	0.5123	0.2951	0.119*	0.633 (4)
H17B	0.0879	0.5170	0.2511	0.119*	0.633 (4)
H17C	−0.0277	0.5654	0.2904	0.119*	0.633 (4)
C21	0.403 (4)	0.1060 (16)	0.3338 (9)	0.081 (7)	0.633 (4)
H21	0.4263	0.1467	0.3592	0.097*	0.633 (4)
C22	0.221 (4)	0.0286 (17)	0.3440 (12)	0.109 (9)*	0.633 (4)
H22A	0.0832	0.0630	0.3498	0.164*	0.633 (4)
H22B	0.2006	−0.0156	0.3204	0.164*	0.633 (4)
H22C	0.2645	−0.0102	0.3681	0.164*	0.633 (4)
C23	0.622 (4)	0.0524 (16)	0.3245 (11)	0.095 (9)*	0.633 (4)
H23A	0.6589	0.0089	0.3476	0.142*	0.633 (4)
H23B	0.6060	0.0130	0.2994	0.142*	0.633 (4)
H23C	0.7379	0.1014	0.3208	0.142*	0.633 (4)
O1D	−0.132 (6)	0.259 (4)	0.358 (2)	0.08 (2)*	0.253 (4)
C7D	0.110 (6)	0.256 (2)	0.3561 (9)	0.084 (18)*	0.253 (4)
C8D	0.2035 (18)	0.3460 (8)	0.3813 (4)	0.054 (5)*	0.253 (4)
C9D	0.0955 (15)	0.3816 (8)	0.4146 (5)	0.073 (3)*	0.253 (4)
H9D	−0.0452	0.3565	0.4212	0.087*	0.253 (4)
C10D	0.190 (2)	0.4558 (9)	0.4395 (4)	0.073 (3)*	0.253 (4)
H10D	0.1153	0.4783	0.4634	0.087*	0.253 (4)
C11D	0.395 (2)	0.4964 (9)	0.4289 (5)	0.068 (6)*	0.253 (4)
C12D	0.5090 (16)	0.4605 (9)	0.3942 (5)	0.073 (3)*	0.253 (4)
H12D	0.6488	0.4864	0.3875	0.087*	0.253 (4)
C13D	0.4146 (19)	0.3857 (9)	0.3693 (4)	0.073 (3)*	0.253 (4)
H13D	0.4876	0.3622	0.3455	0.087*	0.253 (4)
C15D	−0.054 (3)	0.4104 (12)	0.2900 (9)	0.079 (6)	0.253 (4)
H15D	−0.0784	0.4057	0.3203	0.095*	0.253 (4)
C16D	−0.281 (3)	0.4031 (13)	0.2679 (9)	0.073 (6)*	0.253 (4)
H16D	−0.3488	0.3394	0.2744	0.109*	0.253 (4)
H16E	−0.3756	0.4568	0.2774	0.109*	0.253 (4)
H16F	−0.2600	0.4084	0.2381	0.109*	0.253 (4)
C17D	0.064 (3)	0.5106 (12)	0.2808 (10)	0.079 (7)*	0.253 (4)
H17D	0.2050	0.5123	0.2951	0.119*	0.253 (4)
H17E	0.0879	0.5170	0.2511	0.119*	0.253 (4)
H17F	−0.0277	0.5654	0.2904	0.119*	0.253 (4)
C21D	0.401 (10)	0.126 (4)	0.3398 (11)	0.084 (11)*	0.253 (4)
H21D	0.5309	0.1647	0.3496	0.101*	0.253 (4)
C22D	0.212 (9)	0.155 (3)	0.3693 (15)	0.11 (2)*	0.253 (4)
H22D	0.2683	0.1596	0.3978	0.127*	0.253 (4)
H22E	0.0978	0.1028	0.3687	0.127*	0.253 (4)
C23D	0.481 (12)	0.021 (4)	0.334 (2)	0.10 (2)*	0.253 (4)
H23D	0.6011	0.0202	0.3142	0.145*	0.253 (4)
H23E	0.5334	−0.0047	0.3606	0.145*	0.253 (4)
H23F	0.3608	−0.0202	0.3241	0.145*	0.253 (4)
O1P	−0.126 (12)	0.266 (7)	0.363 (2)	0.09 (3)*	0.114 (4)
C7P	0.039 (6)	0.315 (3)	0.3399 (11)	0.08 (2)*	0.114 (4)
C8P	0.155 (8)	0.387 (2)	0.3708 (11)	0.060 (19)*	0.114 (4)
C9P	0.050 (7)	0.425 (4)	0.4039 (15)	0.070 (10)*	0.114 (4)
H9P	−0.0984	0.4077	0.4088	0.084*	0.114 (4)
C10P	0.159 (8)	0.489 (6)	0.4314 (19)	0.070 (10)*	0.114 (4)
H10P	0.0860	0.5127	0.4551	0.084*	0.114 (4)
C11P	0.378 (9)	0.517 (7)	0.423 (2)	0.071 (19)*	0.114 (4)
C12P	0.489 (8)	0.479 (6)	0.389 (2)	0.070 (10)*	0.114 (4)
H12P	0.6370	0.4963	0.3841	0.084*	0.114 (4)
C13P	0.380 (8)	0.414 (5)	0.3615 (15)	0.070 (10)*	0.114 (4)
H13P	0.4512	0.3890	0.3378	0.084*	0.114 (4)
C15P	−0.037 (8)	0.392 (3)	0.3015 (14)	0.079 (12)*	0.114 (4)
C16P	−0.284 (9)	0.398 (8)	0.294 (3)	0.07 (3)*	0.114 (4)
H16G	−0.3484	0.4474	0.3126	0.100*	0.114 (4)
H16H	−0.3118	0.4177	0.2654	0.100*	0.114 (4)
H16I	−0.3510	0.3336	0.2992	0.100*	0.114 (4)
C17P	0.067 (17)	0.497 (3)	0.304 (3)	0.07 (3)*	0.114 (4)
H17G	−0.0277	0.5404	0.3202	0.101*	0.114 (4)
H17H	0.2112	0.4926	0.3171	0.101*	0.114 (4)
H17I	0.0833	0.5240	0.2761	0.101*	0.114 (4)
C21P	0.403 (4)	0.1060 (16)	0.3338 (9)	0.081 (7)	0.114 (4)
H21P	0.4263	0.1467	0.3592	0.097*	0.114 (4)
C22P	0.221 (4)	0.0286 (17)	0.3440 (12)	0.109 (9)*	0.114 (4)
H22F	0.0832	0.0630	0.3498	0.164*	0.114 (4)
H22G	0.2006	−0.0156	0.3204	0.164*	0.114 (4)
H22H	0.2645	−0.0102	0.3681	0.164*	0.114 (4)
C23P	0.622 (4)	0.0524 (16)	0.3245 (11)	0.095 (9)*	0.114 (4)
H23G	0.6589	0.0089	0.3476	0.142*	0.114 (4)
H23H	0.6060	0.0130	0.2994	0.142*	0.114 (4)
H23I	0.7379	0.1014	0.3208	0.142*	0.114 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.087 (8)	0.081 (9)	0.09 (2)	−0.001 (6)	0.005 (10)	−0.012 (7)
O3	0.092 (8)	0.110 (10)	0.13 (2)	−0.024 (8)	−0.001 (10)	−0.022 (9)
O1	0.125 (16)	0.095 (17)	0.03 (2)	−0.020 (15)	0.032 (16)	−0.026 (13)
C15	0.076 (10)	0.068 (10)	0.093 (16)	0.009 (9)	−0.009 (11)	0.003 (10)
C21	0.093 (12)	0.073 (12)	0.075 (16)	0.020 (11)	0.011 (13)	0.011 (11)
C15D	0.076 (10)	0.068 (10)	0.093 (16)	0.009 (9)	−0.009 (11)	0.003 (10)
C21P	0.093 (12)	0.073 (12)	0.075 (16)	0.020 (11)	0.011 (13)	0.011 (11)

Geometric parameters (Å, º)

C26—C27	1.3765	C8—C13	1.4209
C26—C31	1.3784	C9—C10	1.3841
C26—C25	1.5095	C10—C11	1.3855
N1—C25	1.5014	C11—C12	1.3815
C24—C25	1.5074	C12—C13	1.3894
C27—C28	1.3861	C15—C17	1.53 (2)
C28—C29	1.3484	C15—C16	1.53 (2)
C29—C30	1.3675	C21—C23	1.52 (2)
C30—C31	1.3909	C21—C22	1.53 (2)
C1—C2	1.39 (2)	O1D—C7D	1.45 (3)
C1—C6	1.422 (17)	C7D—C22D	1.53 (3)
C1—C7P	1.50 (2)	C7D—C8D	1.54 (2)
C1—C7	1.52 (2)	C8D—C9D	1.3283
C1—C7D	1.57 (2)	C8D—C13D	1.4209
O2—C14	1.26 (2)	C9D—C10D	1.3841
C2—C3	1.41 (3)	C10D—C11D	1.3855
C2—C15P	1.50 (2)	C11D—C12D	1.3815
C2—C15	1.58 (2)	C12D—C13D	1.3894
C2—C15D	1.58 (2)	C15D—C17D	1.53 (2)
O3—C14	1.250 (19)	C15D—C16D	1.53 (2)
C3—C4	1.395 (18)	C21D—C23D	1.49 (3)
C4—C5	1.41 (3)	C21D—C22D	1.52 (3)
C4—C18	1.46 (3)	O1P—C7P	1.40 (3)
C5—C6	1.37 (3)	C7P—C8P	1.53 (2)
C6—C21P	1.53 (2)	C7P—C15P	1.66 (2)
C6—C21	1.53 (2)	C8P—C9P	1.3283
C6—C21D	1.53 (2)	C8P—C13P	1.4209
C14—C11P	1.51 (2)	C9P—C10P	1.3841
C14—C11	1.55 (2)	C10P—C11P	1.3855
C14—C11D	1.55 (2)	C11P—C12P	1.3815
C18—C20	1.52 (3)	C12P—C13P	1.3894
C18—C19	1.54 (2)	C15P—C16P	1.50 (3)
O1—C7	1.226 (19)	C15P—C17P	1.53 (3)
C7—C8	1.482 (19)	C21P—C23P	1.52 (2)
C8—C9	1.3283	C21P—C22P	1.53 (2)
C27—C26—C31	118.2	C10—C11—C14	120.4 (13)
C27—C26—C25	120.5	C11—C12—C13	120.1
C31—C26—C25	121.3	C12—C13—C8	118.2
N1—C25—C24	109.2	C17—C15—C16	112.0 (17)
N1—C25—C26	109.8	C17—C15—C2	109.1 (14)
C24—C25—C26	115.2	C16—C15—C2	110.9 (16)
C26—C27—C28	120.9	C23—C21—C6	114 (2)
C29—C28—C27	120.2	C23—C21—C22	109.9 (16)
C28—C29—C30	120.2	C6—C21—C22	110.9 (19)
C29—C30—C31	119.9	O1D—C7D—C22D	114 (3)
C26—C31—C30	120.5	O1D—C7D—C8D	108 (3)
C2—C1—C6	119.5 (16)	C22D—C7D—C8D	113 (3)
C2—C1—C7P	90.6 (19)	O1D—C7D—C1	107 (3)
C6—C1—C7P	150 (2)	C22D—C7D—C1	100 (2)
C2—C1—C7	122.8 (16)	C8D—C7D—C1	113.5 (19)
C6—C1—C7	117.7 (17)	C9D—C8D—C13D	121.1
C2—C1—C7D	129.8 (19)	C9D—C8D—C7D	120.9 (13)
C6—C1—C7D	110.6 (18)	C13D—C8D—C7D	117.9 (13)
C1—C2—C3	122.6 (16)	C8D—C9D—C10D	120.7
C1—C2—C15P	99 (2)	C9D—C10D—C11D	119.9
C3—C2—C15P	138 (2)	C12D—C11D—C10D	119.9
C1—C2—C15	116.1 (18)	C12D—C11D—C14	119.6 (13)
C3—C2—C15	121.4 (17)	C10D—C11D—C14	120.4 (13)
C1—C2—C15D	116.1 (18)	C11D—C12D—C13D	120.1
C3—C2—C15D	121.4 (17)	C12D—C13D—C8D	118.2
C4—C3—C2	118 (2)	C17D—C15D—C16D	112.0 (17)
C3—C4—C5	118 (2)	C17D—C15D—C2	109.1 (14)
C3—C4—C18	122 (2)	C16D—C15D—C2	110.9 (16)
C5—C4—C18	120.1 (17)	C23D—C21D—C22D	123 (4)
C6—C5—C4	125.2 (18)	C23D—C21D—C6	114 (4)
C5—C6—C1	116.6 (15)	C22D—C21D—C6	101 (3)
C5—C6—C21P	123.2 (16)	C21D—C22D—C7D	110 (3)
C1—C6—C21P	120.1 (18)	O1P—C7P—C1	120 (4)
C5—C6—C21	123.2 (16)	O1P—C7P—C8P	106 (3)
C1—C6—C21	120.1 (18)	C1—C7P—C8P	119 (2)
C5—C6—C21D	133.5 (19)	O1P—C7P—C15P	119 (4)
C1—C6—C21D	109.7 (19)	C1—C7P—C15P	88.4 (18)
O3—C14—O2	124.0 (19)	C8P—C7P—C15P	103 (2)
O3—C14—C11P	117 (3)	C9P—C8P—C13P	121.1
O2—C14—C11P	117 (2)	C9P—C8P—C7P	122 (2)
O3—C14—C11	118 (2)	C13P—C8P—C7P	117 (2)
O2—C14—C11	118.5 (17)	C8P—C9P—C10P	120.75 (8)
O3—C14—C11D	118 (2)	C9P—C10P—C11P	119.9
O2—C14—C11D	118.5 (17)	C12P—C11P—C10P	119.88 (5)
C4—C18—C20	116.3 (18)	C12P—C11P—C14	121 (3)
C4—C18—C19	110 (2)	C10P—C11P—C14	119 (3)
C20—C18—C19	110 (2)	C11P—C12P—C13P	120.14 (8)
O1—C7—C8	118 (2)	C12P—C13P—C8P	118.2
O1—C7—C1	121.4 (19)	C2—C15P—C16P	120 (4)
C8—C7—C1	120.1 (16)	C2—C15P—C17P	112 (4)
C9—C8—C13	121.1	C16P—C15P—C17P	111 (3)
C9—C8—C7	120.8 (12)	C2—C15P—C7P	81.4 (18)
C13—C8—C7	117.9 (12)	C16P—C15P—C7P	115 (4)
C8—C9—C10	120.7	C17P—C15P—C7P	114 (4)
C9—C10—C11	119.9	C23P—C21P—C6	114 (2)
C12—C11—C10	119.9	C23P—C21P—C22P	109.9 (16)
C12—C11—C14	119.6 (13)	C6—C21P—C22P	110.9 (19)

(1300minUV_1GPa)

Crystal data

C31H39NO3	Dx = 1.244 Mg m^−3
Mr = 473.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 453 reflections
a = 5.997 (2) Å	θ = 5.7–22.7°
b = 13.267 (7) Å	µ = 0.08 mm^−1
c = 31.79 (5) Å	T = 299 K
V = 2529 (4) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

KM4 with Eos CCD diffractometer	2189 independent reflections
Radiation source: fine-focus sealed tube	653 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.186
Detector resolution: 15.9718 pixels mm^-1	θmax = 24.5°, θmin = 5.6°
φ– and ω scans	h = −6→6
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −14→11
Tmin = 0.324, Tmax = 1.000	l = −22→20
5382 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.099	w = 1/[σ^2(Fo^2) + (0.0778P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.284	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.13 e Å^−3
2189 reflections	Δρmin = −0.13 e Å^−3
164 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
154 restraints	Absolute structure parameter: −6.7 (10)
Primary atom site location: isomorphous structure methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3784 (19)	0.6239 (9)	0.4829 (6)	0.102 (7)
O3	0.687 (2)	0.6141 (9)	0.4456 (6)	0.120 (8)
C6	0.3263 (18)	0.1785 (7)	0.2991 (4)	0.069 (5)*
C1	0.1776 (18)	0.2580 (8)	0.3074 (4)	0.075 (3)*
C2	0.0986 (14)	0.3213 (6)	0.2758 (5)	0.075 (3)*
C3	0.1683 (17)	0.3033 (7)	0.2348 (4)	0.075 (3)*
H3	0.1141	0.3443	0.2134	0.090*
C4	0.3133 (18)	0.2276 (8)	0.2247 (4)	0.075 (3)*
C5	0.3912 (13)	0.1657 (6)	0.2574 (5)	0.075 (3)*
H5	0.4902	0.1140	0.2509	0.090*
C14	0.499 (4)	0.5840 (14)	0.4550 (9)	0.088 (7)*
C18	0.371 (3)	0.2031 (14)	0.1800 (9)	0.095 (6)*
H18	0.3586	0.1296	0.1776	0.115*
C19	0.617 (3)	0.2280 (14)	0.1723 (9)	0.128 (8)*
H19A	0.6547	0.2124	0.1437	0.192*
H19B	0.6419	0.2984	0.1774	0.192*
H19C	0.7083	0.1889	0.1909	0.192*
C20	0.218 (3)	0.2463 (15)	0.1468 (10)	0.132 (8)*
H20A	0.2687	0.2263	0.1195	0.197*
H20B	0.0690	0.2215	0.1512	0.197*
H20C	0.2177	0.3185	0.1488	0.197*
C26	0.9376 (10)	0.5132 (5)	0.5487 (4)	0.088 (6)*
N1	0.9533 (16)	0.6725 (6)	0.5090 (5)	0.098 (5)*
H1A	0.8500	0.6507	0.4911	0.118*
H1B	1.0878	0.6549	0.4998	0.118*
H1C	0.9454	0.7393	0.5111	0.118*
C24	0.6941 (19)	0.6632 (7)	0.5686 (5)	0.104 (7)*
H24A	0.5765	0.6449	0.5496	0.156*
H24B	0.6986	0.7351	0.5716	0.156*
H24C	0.6672	0.6329	0.5956	0.156*
C25	0.9139 (13)	0.6263 (5)	0.5515 (4)	0.114 (7)*
H25	1.0313	0.6510	0.5703	0.137*
C27	1.1310 (13)	0.4667 (6)	0.5617 (5)	0.107 (7)*
H27	1.2488	0.5056	0.5716	0.128*
C28	1.1527 (17)	0.3628 (7)	0.5601 (6)	0.120 (7)*
H28	1.2840	0.3325	0.5691	0.143*
C29	0.984 (2)	0.3055 (5)	0.5453 (6)	0.121 (8)*
H29	0.9999	0.2358	0.5442	0.145*
C30	0.7901 (18)	0.3495 (5)	0.5322 (6)	0.114 (7)*
H30	0.6738	0.3097	0.5223	0.137*
C31	0.7669 (12)	0.4537 (5)	0.5337 (5)	0.106 (7)*
H31	0.6353	0.4835	0.5245	0.127*
O1	−0.058 (4)	0.2222 (17)	0.3674 (9)	0.102 (11)	0.595 (4)
C7	0.099 (5)	0.271 (2)	0.3529 (7)	0.113 (12)*	0.595 (4)
C8	0.206 (2)	0.3452 (8)	0.3817 (5)	0.067 (6)*	0.595 (4)
C9	0.0969 (17)	0.3811 (9)	0.4148 (5)	0.085 (4)*	0.595 (4)
H9	−0.0426	0.3552	0.4216	0.102*	0.595 (4)
C10	0.188 (2)	0.4568 (11)	0.4394 (4)	0.085 (4)*	0.595 (4)
H10	0.1133	0.4795	0.4631	0.102*	0.595 (4)
C11	0.392 (3)	0.4985 (12)	0.4284 (6)	0.083 (7)*	0.595 (4)
C12	0.507 (2)	0.4622 (12)	0.3939 (6)	0.085 (4)*	0.595 (4)
H12	0.6453	0.4890	0.3870	0.102*	0.595 (4)
C13	0.415 (2)	0.3860 (11)	0.3694 (4)	0.085 (4)*	0.595 (4)
H13	0.4888	0.3622	0.3457	0.102*	0.595 (4)
C15	−0.051 (3)	0.4115 (12)	0.2897 (9)	0.084 (7)	0.595 (4)
H15	−0.0756	0.4065	0.3200	0.101*	0.595 (4)
C16	−0.276 (3)	0.4035 (14)	0.2676 (11)	0.088 (5)*	0.595 (4)
H16A	−0.3438	0.3399	0.2743	0.132*	0.595 (4)
H16B	−0.3713	0.4572	0.2769	0.132*	0.595 (4)
H16C	−0.2552	0.4083	0.2377	0.132*	0.595 (4)
C17	0.069 (3)	0.5110 (13)	0.2807 (11)	0.088 (5)*	0.595 (4)
H17A	0.2096	0.5119	0.2953	0.132*	0.595 (4)
H17B	0.0951	0.5173	0.2510	0.132*	0.595 (4)
H17C	−0.0210	0.5662	0.2902	0.132*	0.595 (4)
C21	0.401 (4)	0.1067 (19)	0.3335 (9)	0.097 (7)	0.595 (4)
H21	0.4222	0.1459	0.3593	0.117*	0.595 (4)
C22	0.222 (4)	0.0273 (18)	0.3420 (12)	0.108 (8)*	0.595 (4)
H22A	0.2726	−0.0173	0.3638	0.161*	0.595 (4)
H22B	0.0872	0.0599	0.3507	0.161*	0.595 (4)
H22C	0.1952	−0.0105	0.3168	0.161*	0.595 (4)
C23	0.620 (4)	0.0531 (18)	0.3236 (12)	0.108 (8)*	0.595 (4)
H23A	0.6578	0.0090	0.3464	0.161*	0.595 (4)
H23B	0.6030	0.0145	0.2983	0.161*	0.595 (4)
H23C	0.7357	0.1021	0.3199	0.161*	0.595 (4)
O1D	−0.134 (6)	0.265 (4)	0.3577 (19)	0.11 (2)*	0.285 (4)
C7D	0.109 (6)	0.258 (2)	0.3552 (8)	0.109 (18)*	0.285 (4)
C8D	0.206 (2)	0.3452 (8)	0.3817 (5)	0.067 (6)*	0.285 (4)
C9D	0.0969 (17)	0.3811 (9)	0.4148 (5)	0.085 (4)*	0.285 (4)
H9D	−0.0426	0.3552	0.4216	0.102*	0.285 (4)
C10D	0.188 (2)	0.4568 (11)	0.4394 (4)	0.085 (4)*	0.285 (4)
H10D	0.1133	0.4795	0.4631	0.102*	0.285 (4)
C11D	0.392 (3)	0.4985 (12)	0.4284 (6)	0.083 (7)*	0.285 (4)
C12D	0.507 (2)	0.4622 (12)	0.3939 (6)	0.085 (4)*	0.285 (4)
H12D	0.6453	0.4890	0.3870	0.102*	0.285 (4)
C13D	0.415 (2)	0.3860 (11)	0.3694 (4)	0.085 (4)*	0.285 (4)
H13D	0.4888	0.3622	0.3457	0.102*	0.285 (4)
C15D	−0.051 (3)	0.4115 (12)	0.2897 (9)	0.084 (7)	0.285 (4)
H15D	−0.0756	0.4065	0.3200	0.101*	0.285 (4)
C16D	−0.276 (3)	0.4035 (14)	0.2676 (11)	0.088 (5)*	0.285 (4)
H16D	−0.3438	0.3399	0.2743	0.132*	0.285 (4)
H16E	−0.3713	0.4572	0.2769	0.132*	0.285 (4)
H16F	−0.2552	0.4083	0.2377	0.132*	0.285 (4)
C17D	0.069 (3)	0.5110 (13)	0.2807 (11)	0.088 (5)*	0.285 (4)
H17D	0.2096	0.5119	0.2953	0.132*	0.285 (4)
H17E	0.0951	0.5173	0.2510	0.132*	0.285 (4)
H17F	−0.0210	0.5662	0.2902	0.132*	0.285 (4)
C21D	0.394 (9)	0.126 (4)	0.3397 (11)	0.098 (11)*	0.285 (4)
H21D	0.5172	0.1663	0.3507	0.118*	0.285 (4)
C22D	0.197 (10)	0.153 (3)	0.3672 (16)	0.16 (3)*	0.285 (4)
H22D	0.2418	0.1532	0.3965	0.188*	0.285 (4)
H22E	0.0792	0.1037	0.3637	0.188*	0.285 (4)
C23D	0.493 (12)	0.025 (4)	0.332 (2)	0.12 (2)*	0.285 (4)
H23D	0.6163	0.0303	0.3134	0.174*	0.285 (4)
H23E	0.5435	−0.0027	0.3588	0.174*	0.285 (4)
H23F	0.3822	−0.0194	0.3206	0.174*	0.285 (4)
O1P	−0.110 (13)	0.258 (6)	0.365 (2)	0.11 (3)*	0.121 (4)
C7P	0.042 (6)	0.313 (3)	0.3402 (11)	0.11 (2)*	0.121 (4)
C8P	0.159 (8)	0.385 (2)	0.3710 (11)	0.075 (19)*	0.121 (4)
C9P	0.055 (8)	0.420 (4)	0.4048 (15)	0.082 (10)*	0.121 (4)
H9P	−0.0935	0.4037	0.4095	0.098*	0.121 (4)
C10P	0.165 (10)	0.482 (7)	0.4331 (19)	0.082 (10)*	0.121 (4)
H10P	0.0930	0.5042	0.4572	0.098*	0.121 (4)
C11P	0.384 (11)	0.510 (8)	0.425 (2)	0.079 (19)*	0.121 (4)
C12P	0.494 (10)	0.474 (7)	0.390 (2)	0.082 (10)*	0.121 (4)
H12P	0.6418	0.4916	0.3856	0.098*	0.121 (4)
C13P	0.383 (9)	0.412 (5)	0.3620 (16)	0.082 (10)*	0.121 (4)
H13P	0.4538	0.3887	0.3379	0.098*	0.121 (4)
C15P	−0.048 (8)	0.387 (4)	0.3022 (13)	0.085 (13)*	0.121 (4)
C16P	−0.295 (8)	0.384 (8)	0.294 (3)	0.11 (3)*	0.121 (4)
H16G	−0.3702	0.4290	0.3127	0.166*	0.121 (4)
H16H	−0.3232	0.4038	0.2653	0.166*	0.121 (4)
H16I	−0.3490	0.3165	0.2981	0.166*	0.121 (4)
C17P	0.036 (17)	0.495 (3)	0.306 (3)	0.05 (3)*	0.121 (4)
H17G	−0.0657	0.5331	0.3234	0.082*	0.121 (4)
H17H	0.1806	0.4950	0.3190	0.082*	0.121 (4)
H17I	0.0444	0.5252	0.2788	0.082*	0.121 (4)
C21P	0.401 (4)	0.1067 (19)	0.3335 (9)	0.097 (7)	0.121 (4)
H21P	0.4222	0.1459	0.3593	0.117*	0.121 (4)
C22P	0.222 (4)	0.0273 (18)	0.3420 (12)	0.108 (8)*	0.121 (4)
H22F	0.2726	−0.0173	0.3638	0.161*	0.121 (4)
H22G	0.0872	0.0599	0.3507	0.161*	0.121 (4)
H22H	0.1952	−0.0105	0.3168	0.161*	0.121 (4)
C23P	0.620 (4)	0.0531 (18)	0.3236 (12)	0.108 (8)*	0.121 (4)
H23G	0.6578	0.0090	0.3464	0.161*	0.121 (4)
H23H	0.6030	0.0145	0.2983	0.161*	0.121 (4)
H23I	0.7357	0.1021	0.3199	0.161*	0.121 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.096 (8)	0.088 (10)	0.12 (2)	0.001 (7)	0.021 (11)	−0.020 (8)
O3	0.092 (8)	0.137 (12)	0.13 (3)	−0.028 (8)	0.019 (11)	−0.004 (10)
O1	0.140 (18)	0.084 (17)	0.08 (3)	−0.007 (16)	0.030 (18)	−0.021 (15)
C15	0.101 (11)	0.063 (10)	0.088 (16)	0.006 (9)	−0.014 (12)	−0.010 (10)
C21	0.097 (12)	0.098 (13)	0.098 (16)	0.032 (12)	0.021 (13)	0.012 (12)
C15D	0.101 (11)	0.063 (10)	0.088 (16)	0.006 (9)	−0.014 (12)	−0.010 (10)
C21P	0.097 (12)	0.098 (13)	0.098 (16)	0.032 (12)	0.021 (13)	0.012 (12)

Geometric parameters (Å, º)

O2—C14	1.26 (3)	C8—C13	1.4209
O3—C14	1.23 (2)	C9—C10	1.3841
C6—C5	1.3947	C10—C11	1.3855
C6—C1	1.4060	C11—C12	1.3814
C6—C21P	1.517 (19)	C12—C13	1.3894
C6—C21	1.517 (19)	C15—C16	1.53 (3)
C6—C21D	1.52 (2)	C15—C17	1.53 (2)
C1—C2	1.3900	C21—C23	1.52 (2)
C1—C7P	1.51 (2)	C21—C22	1.53 (2)
C1—C7	1.53 (2)	O1D—C7D	1.46 (2)
C1—C7D	1.58 (2)	C7D—C22D	1.53 (3)
C2—C3	1.3901	C7D—C8D	1.55 (2)
C2—C15P	1.50 (2)	C8D—C9D	1.3283
C2—C15	1.558 (19)	C8D—C13D	1.4209
C2—C15D	1.558 (19)	C9D—C10D	1.3841
C3—C4	1.3667	C10D—C11D	1.3855
C4—C5	1.4051	C11D—C12D	1.3814
C4—C18	1.50 (3)	C12D—C13D	1.3894
C14—C11P	1.52 (2)	C15D—C16D	1.53 (3)
C14—C11	1.55 (2)	C15D—C17D	1.53 (2)
C14—C11D	1.55 (2)	C21D—C23D	1.49 (3)
C18—C20	1.51 (3)	C21D—C22D	1.52 (3)
C18—C19	1.53 (2)	O1P—C7P	1.40 (2)
C26—C27	1.3765	C7P—C8P	1.53 (2)
C26—C31	1.3784	C7P—C15P	1.65 (2)
C26—C25	1.5095	C8P—C9P	1.3283
N1—C25	1.5015	C8P—C13P	1.4208
C24—C25	1.5074	C9P—C10P	1.3842
C27—C28	1.3862	C10P—C11P	1.3855
C28—C29	1.3487	C11P—C12P	1.3816
C29—C30	1.3677	C12P—C13P	1.3894
C30—C31	1.3909	C15P—C16P	1.50 (3)
O1—C7	1.24 (2)	C15P—C17P	1.52 (3)
C7—C8	1.490 (19)	C21P—C23P	1.52 (2)
C8—C9	1.3283	C21P—C22P	1.53 (2)
C5—C6—C1	116.5	C10—C11—C14	121.4 (15)
C5—C6—C21P	121.8 (13)	C11—C12—C13	120.1
C1—C6—C21P	121.7 (12)	C12—C13—C8	118.2
C5—C6—C21	121.8 (13)	C16—C15—C17	113.1 (18)
C1—C6—C21	121.7 (12)	C16—C15—C2	109.1 (16)
C5—C6—C21D	132.5 (16)	C17—C15—C2	109.8 (14)
C1—C6—C21D	110.9 (16)	C6—C21—C23	113 (2)
C2—C1—C6	122.4	C6—C21—C22	111 (2)
C2—C1—C7P	91.3 (17)	C23—C21—C22	108.5 (18)
C6—C1—C7P	146.3 (17)	O1D—C7D—C22D	113 (3)
C2—C1—C7	120.6 (15)	O1D—C7D—C8D	107 (3)
C6—C1—C7	116.9 (15)	C22D—C7D—C8D	114 (3)
C2—C1—C7D	127.3 (16)	O1D—C7D—C1	108 (3)
C6—C1—C7D	110.2 (16)	C22D—C7D—C1	99 (2)
C1—C2—C3	118.0	C8D—C7D—C1	115.2 (19)
C1—C2—C15P	98.6 (18)	C9D—C8D—C13D	121.1
C3—C2—C15P	143.4 (18)	C9D—C8D—C7D	121.0 (14)
C1—C2—C15	117.2 (14)	C13D—C8D—C7D	117.9 (13)
C3—C2—C15	124.7 (14)	C8D—C9D—C10D	120.7
C1—C2—C15D	117.2 (14)	C9D—C10D—C11D	119.9
C3—C2—C15D	124.7 (14)	C12D—C11D—C10D	119.9
C4—C3—C2	122.6	C12D—C11D—C14	118.7 (16)
C3—C4—C5	117.8	C10D—C11D—C14	121.4 (15)
C3—C4—C18	122.1 (13)	C11D—C12D—C13D	120.1
C5—C4—C18	119.8 (13)	C12D—C13D—C8D	118.2
C6—C5—C4	122.7	C16D—C15D—C17D	113.1 (18)
O3—C14—O2	124 (2)	C16D—C15D—C2	109.1 (16)
O3—C14—C11P	118 (3)	C17D—C15D—C2	109.8 (14)
O2—C14—C11P	116 (2)	C23D—C21D—C22D	128 (4)
O3—C14—C11	119 (2)	C23D—C21D—C6	113 (3)
O2—C14—C11	116.8 (19)	C22D—C21D—C6	100 (3)
O3—C14—C11D	119 (2)	C21D—C22D—C7D	110 (3)
O2—C14—C11D	116.8 (19)	O1P—C7P—C1	119 (4)
C4—C18—C20	116.0 (17)	O1P—C7P—C8P	105 (3)
C4—C18—C19	109.2 (19)	C1—C7P—C8P	120 (2)
C20—C18—C19	113 (2)	O1P—C7P—C15P	120 (4)
C27—C26—C31	118.2	C1—C7P—C15P	87.6 (17)
C27—C26—C25	120.5	C8P—C7P—C15P	104 (2)
C31—C26—C25	121.3	C9P—C8P—C13P	121.06 (5)
N1—C25—C24	109.2	C9P—C8P—C7P	121 (2)
N1—C25—C26	109.8	C13P—C8P—C7P	117 (2)
C24—C25—C26	115.2	C8P—C9P—C10P	120.75 (10)
C26—C27—C28	120.9	C9P—C10P—C11P	119.9
C29—C28—C27	120.2	C12P—C11P—C10P	119.88 (5)
C28—C29—C30	120.2	C12P—C11P—C14	120 (3)
C29—C30—C31	119.9	C10P—C11P—C14	120 (3)
C26—C31—C30	120.5	C11P—C12P—C13P	120.14 (11)
O1—C7—C8	116 (2)	C12P—C13P—C8P	118.2
O1—C7—C1	122 (2)	C2—C15P—C16P	118 (4)
C8—C7—C1	121.6 (17)	C2—C15P—C17P	114 (4)
C9—C8—C13	121.1	C16P—C15P—C17P	112 (3)
C9—C8—C7	120.9 (13)	C2—C15P—C7P	82.5 (17)
C13—C8—C7	117.5 (12)	C16P—C15P—C7P	116 (4)
C8—C9—C10	120.7	C17P—C15P—C7P	113 (3)
C9—C10—C11	119.9	C6—C21P—C23P	113 (2)
C12—C11—C10	119.9	C6—C21P—C22P	111 (2)
C12—C11—C14	118.7 (16)	C23P—C21P—C22P	108.5 (18)

(1_5gpa_144huv)

Crystal data

C23H26.67O3·C8H12N	Dx = 1.243 Mg m^−3
Mr = 473.63	Synchrotron radiation, λ = 0.6889 Å
Orthorhombic, P212121	Cell parameters from 2230 reflections
a = 5.9560 (5) Å	θ = 3.0–25.8°
b = 13.3207 (11) Å	µ = 0.07 mm^−1
c = 31.89 (3) Å	T = 295 K
V = 2530 (2) Å^3	Block, colourless
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1024

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	1824 independent reflections
Radiation source: synchrotron	1070 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.060
Detector resolution: 5.8140 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω and φ scans	h = −7→7
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015)	k = −16→16
Tmin = 0.600, Tmax = 1.000	l = −10→11
8166 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.1888P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.256	(Δ/σ)max = 0.002
S = 0.98	Δρmax = 0.14 e Å^−3
1824 reflections	Δρmin = −0.16 e Å^−3
263 parameters	Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
356 restraints	Absolute structure parameter: 1.1 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.3828 (12)	0.6234 (5)	0.4826 (6)	0.085 (13)
O3	0.6870 (13)	0.6146 (6)	0.4455 (7)	0.133 (15)
C6	0.3211 (11)	0.1811 (4)	0.2994 (4)	0.073 (8)
C1	0.1764 (11)	0.2613 (5)	0.3087 (4)	0.071 (8)
C2	0.0984 (9)	0.3271 (3)	0.2780 (4)	0.069 (8)
C3	0.1649 (10)	0.3108 (4)	0.2367 (4)	0.072 (8)
H3	0.1113	0.3536	0.2158	0.086*
C4	0.3059 (12)	0.2345 (5)	0.2255 (4)	0.073 (8)
C5	0.3831 (9)	0.1701 (3)	0.2573 (4)	0.069 (8)
H5	0.4794	0.1180	0.2501	0.083*
C14	0.4974 (19)	0.5864 (8)	0.4544 (9)	0.090 (3)*
C18	0.377 (2)	0.2073 (9)	0.1843 (11)	0.103 (4)*
H18	0.3610	0.1343	0.1819	0.123*
C19	0.626 (2)	0.2335 (9)	0.1741 (11)	0.115 (4)*
H19A	0.6603	0.2129	0.1460	0.172*
H19B	0.6480	0.3046	0.1767	0.172*
H19C	0.7229	0.1990	0.1934	0.172*
C20	0.231 (3)	0.2520 (11)	0.1526 (16)	0.149 (6)*
H20A	0.2822	0.2326	0.1252	0.224*
H20B	0.0801	0.2291	0.1567	0.224*
H20C	0.2360	0.3238	0.1551	0.224*
C26	0.9435 (8)	0.5141 (3)	0.5492 (4)	0.097 (3)*
N1	0.9570 (12)	0.6719 (4)	0.5084 (4)	0.079 (14)
H1A	0.8528	0.6494	0.4908	0.095*
H1B	1.0910	0.6540	0.4990	0.095*
H1C	0.9490	0.7388	0.5100	0.095*
C24	0.7006 (15)	0.6647 (5)	0.5685 (5)	0.134 (5)*
H24A	0.5821	0.6456	0.5498	0.201*
H24B	0.7051	0.7367	0.5710	0.201*
H24C	0.6751	0.6354	0.5957	0.201*
C25	0.9196 (10)	0.6272 (3)	0.5512 (4)	0.112 (4)*
H25	1.0379	0.6526	0.5697	0.134*
C27	1.1376 (10)	0.4682 (4)	0.5621 (5)	0.118 (4)*
H27	1.2556	0.5074	0.5716	0.141*
C28	1.1594 (12)	0.3641 (4)	0.5611 (6)	0.142 (5)*
H28	1.2911	0.3342	0.5701	0.171*
C29	0.9903 (14)	0.3062 (3)	0.5470 (6)	0.135 (5)*
H29	1.0062	0.2365	0.5463	0.162*
C30	0.7956 (13)	0.3497 (3)	0.5339 (6)	0.124 (4)*
H30	0.6788	0.3095	0.5244	0.148*
C31	0.7722 (9)	0.4540 (4)	0.5348 (5)	0.101 (4)*
H31	0.6401	0.4833	0.5256	0.121*
O1	−0.087 (3)	0.2362 (14)	0.3636 (11)	0.145 (13)	0.666 (4)
C7	0.088 (3)	0.2759 (13)	0.3534 (7)	0.084 (8)	0.666 (4)
C8	0.2072 (13)	0.3479 (6)	0.3813 (5)	0.070 (6)	0.666 (4)
C9	0.0998 (11)	0.3821 (6)	0.4150 (5)	0.088 (6)	0.666 (4)
H9	−0.0397	0.3562	0.4217	0.106*	0.666 (4)
C10	0.1935 (14)	0.4560 (6)	0.4402 (4)	0.085 (6)	0.666 (4)
H10	0.1196	0.4776	0.4642	0.102*	0.666 (4)
C11	0.3973 (14)	0.4978 (6)	0.4294 (5)	0.074 (6)	0.666 (4)
C12	0.5101 (11)	0.4633 (7)	0.3943 (5)	0.085 (6)	0.666 (4)
H12	0.6488	0.4901	0.3875	0.102*	0.666 (4)
C13	0.4165 (14)	0.3888 (7)	0.3692 (5)	0.090 (6)	0.666 (4)
H13	0.4890	0.3662	0.3451	0.107*	0.666 (4)
C15	−0.0534 (16)	0.4145 (6)	0.2898 (8)	0.081 (6)	0.666 (4)
H15	−0.0728	0.4115	0.3203	0.097*	0.666 (4)
C16	−0.2812 (15)	0.4079 (8)	0.2712 (10)	0.075 (10)	0.666 (4)
H16A	−0.3682	0.4649	0.2798	0.112*	0.666 (4)
H16B	−0.2697	0.4069	0.2412	0.112*	0.666 (4)
H16C	−0.3531	0.3475	0.2807	0.112*	0.666 (4)
C17	0.0673 (15)	0.5145 (7)	0.2802 (10)	0.085 (10)	0.666 (4)
H17A	0.2132	0.5142	0.2930	0.128*	0.666 (4)
H17B	0.0829	0.5223	0.2504	0.128*	0.666 (4)
H17C	−0.0192	0.5693	0.2913	0.128*	0.666 (4)
C21	0.399 (3)	0.1088 (11)	0.3330 (8)	0.090 (6)	0.666 (4)
H21	0.4225	0.1488	0.3584	0.108*	0.666 (4)
C22	0.217 (3)	0.0297 (11)	0.3438 (15)	0.134 (11)	0.666 (4)
H22A	0.2727	−0.0145	0.3652	0.200*	0.666 (4)
H22B	0.0845	0.0632	0.3538	0.200*	0.666 (4)
H22C	0.1809	−0.0084	0.3192	0.200*	0.666 (4)
C23	0.618 (3)	0.0535 (11)	0.3247 (11)	0.103 (11)	0.666 (4)
H23A	0.6506	0.0100	0.3480	0.155*	0.666 (4)
H23B	0.6038	0.0142	0.2996	0.155*	0.666 (4)
H23C	0.7374	0.1012	0.3214	0.155*	0.666 (4)
O1D	−0.135 (6)	0.266 (4)	0.357 (2)	0.16 (2)*	0.260 (4)
C7D	0.108 (6)	0.259 (2)	0.3564 (8)	0.070 (11)*	0.260 (4)
C8D	0.2072 (13)	0.3479 (6)	0.3813 (5)	0.070 (6)	0.260 (4)
C9D	0.0998 (11)	0.3821 (6)	0.4150 (5)	0.088 (6)	0.260 (4)
H9D	−0.0404	0.3561	0.4217	0.106*	0.260 (4)
C10D	0.1935 (14)	0.4560 (6)	0.4402 (4)	0.085 (6)	0.260 (4)
H10D	0.1191	0.4773	0.4643	0.102*	0.260 (4)
C11D	0.3973 (14)	0.4978 (6)	0.4294 (5)	0.074 (6)	0.260 (4)
C12D	0.5101 (11)	0.4633 (7)	0.3943 (5)	0.085 (6)	0.260 (4)
H12D	0.6494	0.4901	0.3875	0.102*	0.260 (4)
C13D	0.4165 (14)	0.3888 (7)	0.3692 (5)	0.090 (6)	0.260 (4)
H13D	0.4895	0.3665	0.3451	0.107*	0.260 (4)
C15D	−0.0534 (16)	0.4145 (6)	0.2898 (8)	0.081 (6)	0.260 (4)
H15D	−0.0728	0.4115	0.3203	0.097*	0.260 (4)
C16D	−0.2812 (15)	0.4079 (8)	0.2712 (10)	0.075 (10)	0.260 (4)
H16D	−0.3682	0.4649	0.2798	0.112*	0.260 (4)
H16E	−0.2697	0.4069	0.2412	0.112*	0.260 (4)
H16F	−0.3531	0.3475	0.2807	0.112*	0.260 (4)
C17D	0.0673 (15)	0.5145 (7)	0.2802 (10)	0.085 (10)	0.260 (4)
H17D	0.2132	0.5142	0.2930	0.128*	0.260 (4)
H17E	0.0829	0.5223	0.2504	0.128*	0.260 (4)
H17F	−0.0192	0.5693	0.2913	0.128*	0.260 (4)
C21D	0.391 (7)	0.128 (3)	0.3399 (10)	0.085 (10)*	0.260 (4)
H21D	0.5134	0.1691	0.3513	0.101*	0.260 (4)
C22D	0.186 (7)	0.152 (2)	0.3672 (16)	0.120 (14)*	0.260 (4)
H22D	0.0666	0.1047	0.3618	0.144*	0.260 (4)
H22E	0.2260	0.1485	0.3967	0.144*	0.260 (4)
C23D	0.484 (10)	0.026 (3)	0.337 (3)	0.132 (18)*	0.260 (4)
H23D	0.5213	0.0015	0.3641	0.198*	0.260 (4)
H23E	0.3753	−0.0178	0.3240	0.198*	0.260 (4)
H23F	0.6175	0.0271	0.3196	0.198*	0.260 (4)
O1P	−0.099 (15)	0.253 (7)	0.368 (2)	0.15 (3)*	0.075 (4)
C7P	0.037 (6)	0.311 (3)	0.3424 (11)	0.080 (16)*	0.075 (4)
C8P	0.165 (8)	0.383 (2)	0.3716 (11)	0.060 (13)*	0.075 (4)
C9P	0.047 (7)	0.438 (6)	0.399 (3)	0.085 (7)*	0.075 (4)
H9P	−0.1074	0.4324	0.3990	0.102*	0.075 (4)
C10P	0.153 (8)	0.503 (6)	0.426 (2)	0.085 (7)*	0.075 (4)
H10P	0.0693	0.5387	0.4458	0.102*	0.075 (4)
C11P	0.382 (7)	0.5136 (19)	0.4248 (10)	0.071 (13)*	0.075 (4)
C12P	0.507 (7)	0.457 (7)	0.397 (3)	0.085 (7)*	0.075 (4)
H12P	0.6611	0.4634	0.3961	0.102*	0.075 (4)
C13P	0.401 (9)	0.392 (7)	0.369 (3)	0.085 (7)*	0.075 (4)
H13P	0.4821	0.3550	0.3494	0.102*	0.075 (4)
C15P	−0.062 (7)	0.384 (4)	0.3053 (14)	0.083 (13)*	0.075 (4)
C16P	−0.311 (7)	0.375 (8)	0.299 (4)	0.08 (2)*	0.075 (4)
H16G	−0.3886	0.4164	0.3187	0.122*	0.075 (4)
H16H	−0.3483	0.3970	0.2708	0.122*	0.075 (4)
H16I	−0.3560	0.3065	0.3022	0.122*	0.075 (4)
C17P	0.008 (18)	0.494 (3)	0.310 (4)	0.09 (2)*	0.075 (4)
H17G	−0.0978	0.5283	0.3277	0.131*	0.075 (4)
H17H	0.1547	0.4976	0.3224	0.131*	0.075 (4)
H17I	0.0110	0.5255	0.2829	0.131*	0.075 (4)
C21P	0.399 (3)	0.1088 (11)	0.3330 (8)	0.090 (6)	0.075 (4)
H21P	0.4225	0.1488	0.3584	0.108*	0.075 (4)
C22P	0.217 (3)	0.0297 (11)	0.3438 (15)	0.134 (11)	0.075 (4)
H22F	0.2727	−0.0145	0.3652	0.200*	0.075 (4)
H22G	0.0845	0.0632	0.3538	0.200*	0.075 (4)
H22H	0.1809	−0.0084	0.3192	0.200*	0.075 (4)
C23P	0.618 (3)	0.0535 (11)	0.3247 (11)	0.103 (11)	0.075 (4)
H23G	0.6506	0.0100	0.3480	0.155*	0.075 (4)
H23H	0.6038	0.0142	0.2996	0.155*	0.075 (4)
H23I	0.7374	0.1012	0.3214	0.155*	0.075 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.101 (5)	0.101 (4)	0.05 (4)	0.009 (4)	0.000 (8)	−0.037 (7)
O3	0.107 (5)	0.133 (6)	0.16 (5)	−0.029 (4)	0.000 (9)	−0.034 (10)
C6	0.081 (5)	0.071 (4)	0.07 (3)	−0.009 (4)	−0.012 (9)	−0.008 (7)
C1	0.068 (4)	0.073 (4)	0.07 (3)	−0.007 (4)	−0.006 (8)	−0.009 (8)
C2	0.070 (5)	0.066 (4)	0.07 (3)	0.002 (3)	−0.011 (8)	−0.007 (8)
C3	0.071 (4)	0.076 (4)	0.07 (3)	−0.007 (4)	−0.007 (8)	−0.005 (8)
C4	0.073 (4)	0.079 (5)	0.07 (3)	0.000 (4)	−0.012 (8)	−0.005 (8)
C5	0.073 (4)	0.072 (4)	0.06 (3)	0.001 (4)	−0.012 (8)	0.002 (8)
N1	0.100 (5)	0.089 (5)	0.05 (4)	0.007 (4)	−0.009 (9)	−0.020 (8)
O1	0.158 (11)	0.125 (11)	0.15 (4)	−0.078 (10)	0.107 (17)	−0.072 (16)
C7	0.078 (9)	0.095 (10)	0.08 (2)	−0.018 (9)	−0.002 (13)	0.002 (14)
C8	0.081 (5)	0.073 (5)	0.056 (18)	0.003 (5)	0.002 (9)	0.011 (8)
C9	0.087 (6)	0.078 (5)	0.100 (17)	−0.011 (5)	0.000 (10)	−0.006 (9)
C10	0.090 (6)	0.091 (5)	0.074 (17)	−0.003 (5)	−0.012 (9)	−0.001 (10)
C11	0.079 (5)	0.080 (5)	0.063 (18)	0.005 (5)	−0.009 (9)	0.000 (8)
C12	0.073 (5)	0.104 (6)	0.079 (17)	−0.010 (5)	0.005 (10)	0.005 (10)
C13	0.088 (6)	0.095 (6)	0.086 (17)	−0.006 (5)	0.014 (10)	−0.005 (10)
C15	0.079 (5)	0.067 (4)	0.096 (18)	0.001 (4)	0.003 (9)	0.005 (8)
C16	0.068 (5)	0.099 (6)	0.06 (3)	−0.009 (4)	0.007 (9)	0.006 (11)
C17	0.069 (5)	0.083 (5)	0.10 (3)	0.000 (4)	0.019 (9)	−0.021 (9)
C21	0.116 (9)	0.075 (7)	0.077 (18)	0.031 (7)	−0.001 (12)	−0.020 (10)
C22	0.171 (14)	0.099 (8)	0.13 (3)	−0.014 (10)	0.02 (2)	0.027 (16)
C23	0.101 (10)	0.095 (7)	0.11 (3)	0.024 (7)	−0.047 (14)	−0.020 (14)
C8D	0.081 (5)	0.073 (5)	0.056 (18)	0.003 (5)	0.002 (9)	0.011 (8)
C9D	0.087 (6)	0.078 (5)	0.100 (17)	−0.011 (5)	0.000 (10)	−0.006 (9)
C10D	0.090 (6)	0.091 (5)	0.074 (17)	−0.003 (5)	−0.012 (9)	−0.001 (10)
C11D	0.079 (5)	0.080 (5)	0.063 (18)	0.005 (5)	−0.009 (9)	0.000 (8)
C12D	0.073 (5)	0.104 (6)	0.079 (17)	−0.010 (5)	0.005 (10)	0.005 (10)
C13D	0.088 (6)	0.095 (6)	0.086 (17)	−0.006 (5)	0.014 (10)	−0.005 (10)
C15D	0.079 (5)	0.067 (4)	0.096 (18)	0.001 (4)	0.003 (9)	0.005 (8)
C16D	0.068 (5)	0.099 (6)	0.06 (3)	−0.009 (4)	0.007 (9)	0.006 (11)
C17D	0.069 (5)	0.083 (5)	0.10 (3)	0.000 (4)	0.019 (9)	−0.021 (9)
C21P	0.116 (9)	0.075 (7)	0.077 (18)	0.031 (7)	−0.001 (12)	−0.020 (10)
C22P	0.171 (14)	0.099 (8)	0.13 (3)	−0.014 (10)	0.02 (2)	0.027 (16)
C23P	0.101 (10)	0.095 (7)	0.11 (3)	0.024 (7)	−0.047 (14)	−0.020 (14)

Geometric parameters (Å, º)

O2—C14	1.23 (3)	C8—C13	1.4147
O3—C14	1.223 (16)	C9—C10	1.3885
C6—C1	1.4049	C10—C11	1.3792
C6—C5	1.3986	C11—C12	1.3841
C6—C21	1.513 (19)	C12—C13	1.3922
C6—C21D	1.53 (2)	C15—C16	1.48 (2)
C6—C21P	1.513 (19)	C15—C17	1.545 (15)
C1—C2	1.3943	C21—C22	1.55 (2)
C1—C7	1.53 (2)	C21—C23	1.521 (18)
C1—C7D	1.58 (2)	O1D—C7D	1.45 (3)
C1—C7P	1.51 (2)	C7D—C8D	1.55 (2)
C2—C3	1.3923	C7D—C22D	1.53 (3)
C2—C15	1.521 (12)	C8D—C9D	1.3297
C2—C15D	1.521 (12)	C8D—C13D	1.4147
C2—C15P	1.50 (2)	C9D—C10D	1.3885
C3—C4	1.3661	C10D—C11D	1.3792
C4—C5	1.4075	C11D—C12D	1.3841
C4—C18	1.43 (3)	C12D—C13D	1.3922
C14—C11	1.54 (2)	C15D—C16D	1.48 (2)
C14—C11D	1.54 (2)	C15D—C17D	1.545 (15)
C14—C11P	1.52 (2)	C21D—C22D	1.54 (3)
C18—C19	1.56 (2)	C21D—C23D	1.48 (3)
C18—C20	1.46 (4)	O1P—C7P	1.39 (3)
C26—C25	1.5154	C7P—C8P	1.54 (2)
C26—C27	1.3713	C7P—C15P	1.65 (3)
C26—C31	1.3757	C8P—C9P	1.3285
N1—C25	1.5058	C8P—C13P	1.4129
C24—C25	1.5008	C9P—C10P	1.3858
C27—C28	1.3925	C10P—C11P	1.3774
C28—C29	1.3453	C11P—C12P	1.3842
C29—C30	1.3623	C12P—C13P	1.3904
C30—C31	1.3962	C15P—C16P	1.51 (3)
O1—C7	1.212 (17)	C15P—C17P	1.53 (3)
C7—C8	1.489 (17)	C21P—C22P	1.55 (2)
C8—C9	1.3297	C21P—C23P	1.521 (18)
C1—C6—C21	121.5 (10)	C12—C11—C14	119.0 (11)
C1—C6—C21D	109.9 (14)	C11—C12—C13	120.6
C1—C6—C21P	121.5 (10)	C12—C13—C8	118.0
C5—C6—C1	116.4	C2—C15—C17	109.6 (10)
C5—C6—C21	122.1 (10)	C16—C15—C2	113.6 (13)
C5—C6—C21D	133.6 (13)	C16—C15—C17	113.5 (14)
C5—C6—C21P	122.1 (10)	C6—C21—C22	112.1 (18)
C6—C1—C7	120.3 (9)	C6—C21—C23	116.7 (19)
C6—C1—C7D	110.1 (13)	C23—C21—C22	108.0 (12)
C6—C1—C7P	145.0 (19)	O1D—C7D—C1	105 (3)
C2—C1—C6	122.3	O1D—C7D—C8D	109 (3)
C2—C1—C7	117.4 (9)	O1D—C7D—C22D	111 (3)
C2—C1—C7D	127.5 (13)	C8D—C7D—C1	112.3 (17)
C2—C1—C7P	92.5 (19)	C22D—C7D—C1	99 (2)
C1—C2—C15	120.3 (11)	C22D—C7D—C8D	119 (3)
C1—C2—C15D	120.3 (11)	C9D—C8D—C7D	119.7 (12)
C1—C2—C15P	97.0 (19)	C9D—C8D—C13D	120.9
C3—C2—C1	118.2	C13D—C8D—C7D	119.4 (12)
C3—C2—C15	121.5 (11)	C8D—C9D—C10D	121.2
C3—C2—C15D	121.5 (11)	C11D—C10D—C9D	119.7
C3—C2—C15P	144.1 (18)	C10D—C11D—C14	121.3 (10)
C4—C3—C2	122.6	C10D—C11D—C12D	119.7
C3—C4—C5	117.7	C12D—C11D—C14	119.0 (11)
C3—C4—C18	127.7 (10)	C11D—C12D—C13D	120.6
C5—C4—C18	114.4 (10)	C12D—C13D—C8D	118.0
C6—C5—C4	122.8	C2—C15D—C17D	109.6 (10)
O2—C14—C11	117.9 (10)	C16D—C15D—C2	113.6 (13)
O2—C14—C11D	117.9 (10)	C16D—C15D—C17D	113.5 (14)
O2—C14—C11P	117 (2)	C6—C21D—C22D	100 (3)
O3—C14—O2	123.9 (16)	C23D—C21D—C6	118 (4)
O3—C14—C11	118.1 (19)	C23D—C21D—C22D	122 (4)
O3—C14—C11D	118.1 (19)	C7D—C22D—C21D	108 (3)
O3—C14—C11P	118 (2)	C1—C7P—C8P	115 (2)
C4—C18—C19	115 (2)	C1—C7P—C15P	86.7 (19)
C4—C18—C20	111.1 (17)	O1P—C7P—C1	120 (4)
C20—C18—C19	109 (2)	O1P—C7P—C8P	106 (3)
C27—C26—C25	120.6	O1P—C7P—C15P	123 (4)
C27—C26—C31	117.8	C8P—C7P—C15P	103.8 (18)
C31—C26—C25	121.6	C9P—C8P—C7P	118 (3)
N1—C25—C26	109.8	C9P—C8P—C13P	121.0
C24—C25—C26	115.4	C13P—C8P—C7P	121 (3)
C24—C25—N1	109.2	C8P—C9P—C10P	121.16 (8)
C26—C27—C28	121.0	C11P—C10P—C9P	119.7
C29—C28—C27	120.6	C10P—C11P—C14	120 (3)
C28—C29—C30	119.7	C10P—C11P—C12P	119.7
C29—C30—C31	120.1	C12P—C11P—C14	121 (3)
C26—C31—C30	120.8	C11P—C12P—C13P	120.60 (9)
O1—C7—C1	119.3 (18)	C12P—C13P—C8P	117.9
O1—C7—C8	122.0 (19)	C2—C15P—C7P	83.6 (18)
C8—C7—C1	118.3 (11)	C2—C15P—C16P	120 (4)
C9—C8—C7	118.3 (9)	C2—C15P—C17P	112 (4)
C9—C8—C13	120.9	C16P—C15P—C7P	114 (4)
C13—C8—C7	120.3 (9)	C16P—C15P—C17P	111 (3)
C8—C9—C10	121.2	C17P—C15P—C7P	114 (4)
C11—C10—C9	119.7	C6—C21P—C22P	112.1 (18)
C10—C11—C14	121.3 (10)	C6—C21P—C23P	116.7 (19)
C10—C11—C12	119.7	C23P—C21P—C22P	108.0 (12)