Monitoring structural transformations in crystals. 11. Yang photocyclizations – one type of reaction, but diversity of structural changes

Structural changes proceeding in a crystal during the Yang photocyclization of the salt 6,6-diethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate with (1S)-1-(4-methylphenyl)­ethylamine were monitored by means of X-ray structure analysis. The course of the photoreaction was evaluated on the basis of the geometrical parameters for the pure reactant crystal. Variations in the cell constants, the product content, the geometry of the reaction centre, the orientation of molecular fragments and the geometry of hydrogen bonds were described and analyzed. It was found that the cell volume increased until 56% product content and decreased thereafter. The distance between the directly reacting C atoms was constant, ∼ 3.0 Å, until ∼ 75% reaction progress. Analysis of the distance between atoms that would participate in the formation of the second (unobserved) enantiomorph excluded the formation of such an isomer. Molecular fragments varied their orientation during the photoreaction, and the largest change was observed for the carboxylate group despite its participation in strong hydrogen bonds. The geometry of the hydrogen bonds changed during the photoreaction. The largest change was 0.17 Å for the D...A distance and 13° for the D—H...A angle. A comparison of the intra- and intermolecular parameters for the studied salt with data for other compounds undergoing the Yang photocyclization in crystals revealed a diversity of structural changes brought about by this type of photochemical reaction.

Computing details

For all compounds, data collection: CRYSALIS (Oxford Diffraction, 2003); cell refinement: CRYSALIS (Oxford Diffraction, 2003); data reduction: CRYSALIS (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SXELXL97 (Sheldrick, 1997).

Figures

(0.0P)

Crystal data

C24H31NO3	Dx = 1.175 Mg m^−3
Mr = 381.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1000 reflections
a = 6.7448 (18) Å	θ = 3–16°
b = 11.849 (3) Å	µ = 0.08 mm^−1
c = 26.976 (6) Å	T = 299 K
V = 2155.9 (9) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 824

Data collection

Kuma KM4CCD diffractometer	2324 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 25.0°, θmin = 3.4°
ω scans	h = −8→3
11662 measured reflections	k = −14→13
3696 independent reflections	l = −32→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)] = 0.062	w = 1/[σ^2(Fo^2) + (0.121P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.194	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.37 e Å^−3
3696 reflections	Δρmin = −0.20 e Å^−3
255 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.025 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute structure was assigned on the basis of known absolute configuration of the cation.
Secondary atom site location: inferred from neighbouring sites

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1R	1.1519 (11)	−0.3058 (7)	0.2921 (2)	0.156 (3)
H1AR	1.2217	−0.3447	0.3180	0.234*
H1BR	1.0612	−0.2526	0.3065	0.234*
H1CR	1.2452	−0.2664	0.2715	0.234*
C2R	1.0395 (7)	−0.3890 (4)	0.26154 (18)	0.0988 (15)
H2AR	0.9495	−0.4291	0.2834	0.119*
H2BR	1.1335	−0.4439	0.2489	0.119*
C3R	0.9187 (6)	−0.3447 (3)	0.21758 (13)	0.0674 (10)
C4R	1.0673 (6)	−0.2930 (3)	0.18223 (15)	0.0722 (11)
C5R	1.0080 (5)	−0.1922 (3)	0.15224 (12)	0.0546 (9)
C6R	1.1434 (5)	−0.1411 (3)	0.12113 (15)	0.0657 (10)
H6R	1.2732	−0.1674	0.1202	0.079*
C7R	1.0891 (5)	−0.0513 (3)	0.09127 (14)	0.0604 (9)
H7R	1.1827	−0.0172	0.0709	0.072*
C8R	0.8962 (4)	−0.0125 (3)	0.09175 (12)	0.0507 (8)
C9R	0.7622 (5)	−0.0643 (3)	0.12247 (13)	0.0577 (9)
H9R	0.6312	−0.0398	0.1222	0.069*
C10R	0.8144 (5)	−0.1516 (3)	0.15389 (13)	0.0568 (9)
C11R	0.6660 (6)	−0.2022 (4)	0.18945 (16)	0.0777 (12)
H11A	0.5785	−0.1434	0.2016	0.093*
H11B	0.5858	−0.2576	0.1721	0.093*
C12R	0.7681 (6)	−0.2577 (4)	0.23264 (15)	0.0776 (11)
H12A	0.8335	−0.2001	0.2523	0.093*
H12B	0.6690	−0.2934	0.2534	0.093*
C13R	0.8230 (9)	−0.4433 (4)	0.19020 (19)	0.1025 (16)
H13A	0.7692	−0.4158	0.1591	0.123*
H13B	0.9249	−0.4982	0.1824	0.123*
C14R	0.6626 (8)	−0.5007 (5)	0.2180 (3)	0.134 (2)
H14A	0.6106	−0.5616	0.1985	0.201*
H14B	0.5586	−0.4478	0.2251	0.201*
H14C	0.7146	−0.5300	0.2486	0.201*
C15R	0.8318 (5)	0.0830 (3)	0.05987 (13)	0.0573 (9)
O1R	0.9604 (3)	0.1512 (2)	0.04422 (9)	0.0669 (7)
O2R	0.6530 (4)	0.0917 (2)	0.04934 (12)	0.0859 (9)
O3R	1.2306 (5)	−0.3360 (3)	0.17344 (15)	0.1248 (14)
C16R	0.3379 (6)	0.3220 (4)	0.08510 (15)	0.0789 (12)
H16R	0.2061	0.3566	0.0867	0.095*
C17R	0.3747 (9)	0.2576 (5)	0.13370 (16)	0.134 (2)
H17A	0.2754	0.2002	0.1376	0.202*
H17B	0.3681	0.3091	0.1611	0.202*
H17C	0.5035	0.2231	0.1327	0.202*
C18R	0.4898 (6)	0.4144 (4)	0.07504 (14)	0.0688 (10)
C19R	0.6824 (6)	0.3898 (3)	0.06422 (15)	0.0705 (11)
H19R	0.7271	0.3158	0.0668	0.085*
C20R	0.8098 (6)	0.4722 (4)	0.04965 (17)	0.0800 (12)
H20R	0.9392	0.4529	0.0412	0.096*
C21R	0.7518 (7)	0.5839 (4)	0.04703 (16)	0.0790 (12)
C22R	0.5641 (9)	0.6062 (4)	0.06066 (19)	0.0985 (15)
H22R	0.5220	0.6809	0.0610	0.118*
C23R	0.4350 (7)	0.5256 (4)	0.07378 (17)	0.0889 (14)
H23R	0.3059	0.5456	0.0822	0.107*
C24R	0.8911 (9)	0.6725 (5)	0.0291 (2)	0.128 (2)
H24A	0.8412	0.7046	−0.0011	0.192*
H24B	1.0189	0.6395	0.0231	0.192*
H24C	0.9030	0.7306	0.0537	0.192*
N1R	0.3405 (4)	0.2392 (2)	0.04344 (11)	0.0624 (8)
H1DR	0.2528	0.1848	0.0494	0.094*
H1ER	0.4611	0.2093	0.0408	0.094*
H1FR	0.3093	0.2742	0.0153	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.173 (6)	0.179 (6)	0.117 (4)	−0.044 (6)	−0.054 (5)	0.039 (5)
C2R	0.094 (3)	0.114 (4)	0.088 (3)	−0.024 (3)	−0.030 (3)	0.033 (3)
C3R	0.086 (2)	0.059 (2)	0.058 (2)	−0.001 (2)	−0.0068 (19)	0.0159 (18)
C4R	0.065 (2)	0.070 (2)	0.081 (3)	0.018 (2)	−0.002 (2)	0.019 (2)
C5R	0.0526 (18)	0.054 (2)	0.057 (2)	0.0085 (16)	0.0034 (16)	0.0139 (16)
C6R	0.0484 (18)	0.065 (2)	0.083 (3)	0.0088 (17)	0.0040 (18)	0.016 (2)
C7R	0.0512 (19)	0.064 (2)	0.066 (2)	0.0033 (17)	0.0075 (17)	0.0208 (18)
C8R	0.0485 (18)	0.0468 (18)	0.0569 (19)	0.0011 (15)	−0.0055 (15)	0.0068 (15)
C9R	0.0415 (16)	0.054 (2)	0.078 (2)	0.0030 (16)	0.0050 (16)	0.0165 (18)
C10R	0.0537 (19)	0.055 (2)	0.062 (2)	0.0033 (16)	0.0014 (16)	0.0095 (17)
C11R	0.065 (2)	0.073 (2)	0.095 (3)	0.009 (2)	0.026 (2)	0.033 (2)
C12R	0.091 (3)	0.072 (3)	0.069 (2)	−0.001 (2)	0.014 (2)	0.014 (2)
C13R	0.137 (4)	0.067 (3)	0.104 (4)	−0.003 (3)	−0.039 (3)	0.000 (3)
C14R	0.111 (4)	0.093 (4)	0.198 (6)	−0.029 (4)	−0.028 (5)	−0.001 (4)
C15R	0.0535 (19)	0.055 (2)	0.064 (2)	−0.0022 (18)	−0.0035 (17)	0.0142 (17)
O1R	0.0607 (14)	0.0616 (15)	0.0784 (17)	−0.0018 (12)	0.0024 (12)	0.0288 (14)
O2R	0.0549 (14)	0.0745 (17)	0.128 (2)	0.0048 (13)	−0.0216 (15)	0.0423 (18)
O3R	0.104 (2)	0.120 (3)	0.151 (3)	0.049 (2)	0.034 (2)	0.064 (2)
C16R	0.067 (2)	0.094 (3)	0.076 (3)	−0.003 (2)	0.011 (2)	0.003 (2)
C17R	0.154 (5)	0.185 (6)	0.064 (3)	−0.078 (5)	0.005 (3)	0.030 (3)
C18R	0.072 (2)	0.073 (3)	0.061 (2)	0.005 (2)	0.0021 (19)	−0.0003 (19)
C19R	0.064 (2)	0.062 (2)	0.086 (3)	−0.003 (2)	0.004 (2)	0.000 (2)
C20R	0.070 (2)	0.080 (3)	0.090 (3)	−0.004 (2)	−0.001 (2)	−0.008 (2)
C21R	0.098 (3)	0.070 (3)	0.068 (3)	−0.008 (3)	−0.012 (2)	0.003 (2)
C22R	0.129 (4)	0.063 (3)	0.104 (4)	0.016 (3)	−0.020 (3)	0.006 (3)
C23R	0.086 (3)	0.086 (3)	0.095 (3)	0.020 (3)	0.001 (3)	−0.006 (3)
C24R	0.174 (6)	0.094 (4)	0.117 (4)	−0.058 (4)	−0.019 (4)	0.010 (3)
N1R	0.0547 (15)	0.0680 (19)	0.0644 (18)	−0.0007 (15)	−0.0007 (14)	0.0219 (15)

Geometric parameters (Å, º)

C1R—C2R	1.493 (8)	C11R—C12R	1.505 (6)
C2R—C3R	1.532 (5)	C13R—C14R	1.483 (7)
C3R—C12R	1.503 (5)	C15R—O2R	1.243 (4)
C3R—C4R	1.513 (5)	C15R—O1R	1.259 (4)
C3R—C13R	1.526 (6)	C16R—N1R	1.492 (5)
C4R—O3R	1.237 (4)	C16R—C18R	1.523 (6)
C4R—C5R	1.497 (5)	C16R—C17R	1.537 (6)
C5R—C6R	1.380 (5)	C18R—C19R	1.363 (5)
C5R—C10R	1.392 (4)	C18R—C23R	1.370 (6)
C6R—C7R	1.384 (5)	C19R—C20R	1.359 (5)
C7R—C8R	1.381 (4)	C20R—C21R	1.383 (6)
C8R—C9R	1.371 (4)	C21R—C22R	1.345 (7)
C8R—C15R	1.486 (5)	C21R—C24R	1.489 (6)
C9R—C10R	1.383 (5)	C22R—C23R	1.340 (7)
C10R—C11R	1.510 (5)
C1R—C2R—C3R	118.1 (4)	C5R—C10R—C11R	120.3 (3)
C12R—C3R—C4R	109.9 (3)	C12R—C11R—C10R	111.2 (3)
C12R—C3R—C13R	111.7 (4)	C3R—C12R—C11R	113.6 (3)
C4R—C3R—C13R	106.6 (4)	C14R—C13R—C3R	114.5 (4)
C12R—C3R—C2R	112.7 (4)	O2R—C15R—O1R	122.6 (3)
C4R—C3R—C2R	105.9 (3)	O2R—C15R—C8R	118.6 (3)
C13R—C3R—C2R	109.7 (3)	O1R—C15R—C8R	118.8 (3)
O3R—C4R—C5R	117.6 (4)	N1R—C16R—C18R	109.3 (3)
O3R—C4R—C3R	122.9 (4)	N1R—C16R—C17R	108.3 (4)
C5R—C4R—C3R	119.1 (3)	C18R—C16R—C17R	113.6 (4)
C6R—C5R—C10R	119.2 (3)	C19R—C18R—C23R	117.3 (4)
C6R—C5R—C4R	120.1 (3)	C19R—C18R—C16R	121.7 (4)
C10R—C5R—C4R	120.6 (3)	C23R—C18R—C16R	120.9 (4)
C5R—C6R—C7R	121.1 (3)	C20R—C19R—C18R	120.7 (4)
C8R—C7R—C6R	120.0 (3)	C19R—C20R—C21R	121.6 (4)
C9R—C8R—C7R	118.5 (3)	C22R—C21R—C20R	116.1 (4)
C9R—C8R—C15R	119.9 (3)	C22R—C21R—C24R	123.0 (5)
C7R—C8R—C15R	121.6 (3)	C20R—C21R—C24R	120.9 (5)
C8R—C9R—C10R	122.5 (3)	C23R—C22R—C21R	123.0 (5)
C9R—C10R—C5R	118.5 (3)	C22R—C23R—C18R	121.1 (4)
C9R—C10R—C11R	121.1 (3)

(28.6P)

Crystal data

C24H31NO3	Dx = 1.174 Mg m^−3
Mr = 381.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1000 reflections
a = 6.7891 (12) Å	θ = 3–20°
b = 11.852 (2) Å	µ = 0.08 mm^−1
c = 26.822 (5) Å	T = 299 K
V = 2158.2 (7) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 824

Data collection

Kuma KM4CCD diffractometer	1914 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
ω scans	h = −8→3
11658 measured reflections	k = −14→14
3750 independent reflections	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)] = 0.059	w = 1/[σ^2(Fo^2) + (0.0993P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.175	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.20 e Å^−3
3750 reflections	Δρmin = −0.17 e Å^−3
327 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
215 restraints	Extinction coefficient: 0.019 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute structure was assigned on the basis of known absolute configuration of the cation.
Secondary atom site location: inferred from neighbouring sites

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1R	1.1496 (14)	−0.3078 (8)	0.2931 (3)	0.141 (4)	0.714 (6)
H1AR	1.2195	−0.3463	0.3192	0.211*	0.714 (6)
H1BR	1.0596	−0.2546	0.3076	0.211*	0.714 (6)
H1CR	1.2417	−0.2688	0.2722	0.211*	0.714 (6)
C2R	1.0364 (13)	−0.3925 (7)	0.2625 (3)	0.092 (3)	0.714 (6)
H2AR	0.9432	−0.4303	0.2842	0.111*	0.714 (6)
H2BR	1.1282	−0.4490	0.2505	0.111*	0.714 (6)
C3R	0.9239 (10)	−0.3459 (6)	0.2178 (3)	0.0650 (19)	0.714 (6)
C4R	1.0741 (14)	−0.2925 (7)	0.1835 (3)	0.072 (4)	0.714 (6)
C5R	1.0160 (12)	−0.1904 (8)	0.1544 (4)	0.052 (3)	0.714 (6)
C6R	1.1500 (11)	−0.1389 (8)	0.1233 (4)	0.060 (3)	0.714 (6)
H6R	1.2777	−0.1670	0.1218	0.071*	0.714 (6)
C7R	1.1011 (11)	−0.0473 (8)	0.0943 (3)	0.054 (2)	0.714 (6)
H7R	1.1961	−0.0117	0.0749	0.065*	0.714 (6)
C8R	0.9091 (12)	−0.0088 (8)	0.0943 (4)	0.050 (3)	0.714 (6)
C9R	0.7737 (10)	−0.0599 (6)	0.1253 (3)	0.050 (2)	0.714 (6)
H9R	0.6447	−0.0335	0.1256	0.060*	0.714 (6)
C10R	0.8238 (10)	−0.1490 (7)	0.1560 (3)	0.052 (3)	0.714 (6)
C11R	0.6741 (11)	−0.2014 (10)	0.1904 (4)	0.071 (3)	0.714 (6)
H11A	0.5860	−0.1434	0.2028	0.085*	0.714 (6)
H11B	0.5961	−0.2561	0.1722	0.085*	0.714 (6)
C12R	0.7741 (15)	−0.2588 (9)	0.2337 (3)	0.079 (3)	0.714 (6)
H12A	0.6749	−0.2951	0.2543	0.095*	0.714 (6)
H12B	0.8392	−0.2022	0.2540	0.095*	0.714 (6)
C13R	0.8316 (14)	−0.4443 (8)	0.1896 (3)	0.103 (3)	0.714 (6)
H13A	0.7857	−0.4168	0.1576	0.123*	0.714 (6)
H13B	0.9336	−0.4998	0.1832	0.123*	0.714 (6)
C14R	0.6626 (13)	−0.5028 (8)	0.2153 (4)	0.128 (3)	0.714 (6)
H14A	0.6150	−0.5629	0.1946	0.192*	0.714 (6)
H14B	0.5584	−0.4496	0.2211	0.192*	0.714 (6)
H14C	0.7066	−0.5330	0.2466	0.192*	0.714 (6)
C15R	0.8482 (11)	0.0876 (9)	0.0627 (5)	0.058 (3)	0.714 (6)
O1R	0.9764 (10)	0.1573 (6)	0.0481 (3)	0.0613 (17)	0.714 (6)
O2R	0.6730 (12)	0.0953 (11)	0.0496 (5)	0.099 (5)	0.714 (6)
O3R	1.2338 (7)	−0.3372 (4)	0.1746 (2)	0.102 (2)	0.714 (6)
C17R	0.3691 (17)	0.2657 (10)	0.1340 (3)	0.122 (4)	0.714 (6)
H17A	0.2703	0.2084	0.1379	0.184*	0.714 (6)
H17B	0.3531	0.3218	0.1595	0.184*	0.714 (6)
H17C	0.4974	0.2323	0.1368	0.184*	0.714 (6)
N1R	0.3590 (12)	0.2338 (7)	0.0422 (3)	0.0579 (18)	0.714 (6)
H1DR	0.2716	0.1794	0.0480	0.087*	0.714 (6)
H1ER	0.4796	0.2043	0.0413	0.087*	0.714 (6)
H1FR	0.3327	0.2663	0.0130	0.087*	0.714 (6)
C16R	0.3478 (8)	0.3205 (5)	0.08306 (17)	0.072 (2)	0.714 (6)
H16R	0.2166	0.3548	0.0816	0.087*	0.714 (6)
C18R	0.4961 (8)	0.4120 (5)	0.07168 (17)	0.0660 (17)	0.714 (6)
C19R	0.6863 (8)	0.3872 (5)	0.05975 (17)	0.0738 (19)	0.714 (6)
H19R	0.7283	0.3125	0.0610	0.089*	0.714 (6)
C20R	0.8179 (8)	0.4697 (5)	0.04600 (17)	0.083 (2)	0.714 (6)
H20R	0.9455	0.4495	0.0370	0.100*	0.714 (6)
C21R	0.7637 (8)	0.5820 (5)	0.04525 (17)	0.086 (4)	0.714 (6)
C22R	0.5776 (8)	0.6071 (5)	0.06137 (17)	0.099 (3)	0.714 (6)
H22R	0.5388	0.6822	0.0639	0.119*	0.714 (6)
C23R	0.4470 (8)	0.5230 (5)	0.07388 (17)	0.085 (3)	0.714 (6)
H23R	0.3209	0.5428	0.0842	0.101*	0.714 (6)
C24R	0.9023 (8)	0.6720 (5)	0.02646 (17)	0.133 (4)	0.714 (6)
H24A	0.8862	0.6805	−0.0089	0.200*	0.714 (6)
H24B	1.0356	0.6505	0.0336	0.200*	0.714 (6)
H24C	0.8731	0.7422	0.0427	0.200*	0.714 (6)
C1P	1.178 (2)	−0.2896 (16)	0.2243 (6)	0.109 (6)*	0.286 (6)
H1AP	1.2024	−0.2118	0.2337	0.130*	0.286 (6)
H1BP	1.3011	−0.3299	0.2199	0.130*	0.286 (6)
C2P	1.031 (3)	−0.351 (2)	0.2596 (7)	0.100 (8)*	0.286 (6)
H2AP	1.0668	−0.4283	0.2675	0.121*	0.286 (6)
H2BP	0.9964	−0.3089	0.2893	0.121*	0.286 (6)
C3P	0.884 (2)	−0.3399 (17)	0.2172 (9)	0.069 (4)*	0.286 (6)
C4P	1.040 (3)	−0.3014 (14)	0.1806 (5)	0.065 (10)*	0.286 (6)
C5P	0.990 (3)	−0.2008 (18)	0.1467 (10)	0.053 (10)*	0.286 (6)
C6P	1.130 (3)	−0.1558 (19)	0.1156 (10)	0.079 (12)*	0.286 (6)
H6P	1.2566	−0.1852	0.1160	0.095*	0.286 (6)
C7P	1.087 (3)	−0.0682 (18)	0.0838 (8)	0.051 (8)*	0.286 (6)
H7P	1.1826	−0.0402	0.0624	0.062*	0.286 (6)
C8P	0.900 (3)	−0.0224 (18)	0.0842 (9)	0.037 (8)*	0.286 (6)
C9P	0.759 (2)	−0.0756 (14)	0.1116 (6)	0.041 (6)*	0.286 (6)
H9P	0.6285	−0.0535	0.1074	0.049*	0.286 (6)
C10P	0.799 (2)	−0.1601 (17)	0.1450 (7)	0.043 (7)*	0.286 (6)
C11P	0.644 (2)	−0.204 (3)	0.1793 (9)	0.064 (6)*	0.286 (6)
H11C	0.5716	−0.2640	0.1631	0.077*	0.286 (6)
H11D	0.5517	−0.1437	0.1872	0.077*	0.286 (6)
C12P	0.736 (4)	−0.247 (2)	0.2267 (7)	0.073 (7)*	0.286 (6)
H12C	0.6335	−0.2755	0.2485	0.088*	0.286 (6)
H12D	0.8013	−0.1852	0.2437	0.088*	0.286 (6)
C13P	0.785 (4)	−0.451 (2)	0.2039 (9)	0.130 (9)*	0.286 (6)
H13C	0.8861	−0.5070	0.1967	0.156*	0.286 (6)
H13D	0.7073	−0.4410	0.1739	0.156*	0.286 (6)
C14P	0.649 (4)	−0.497 (2)	0.2465 (9)	0.145 (11)*	0.286 (6)
H14D	0.5790	−0.5621	0.2349	0.217*	0.286 (6)
H14E	0.5569	−0.4394	0.2560	0.217*	0.286 (6)
H14F	0.7284	−0.5171	0.2748	0.217*	0.286 (6)
C15P	0.842 (3)	0.075 (2)	0.0515 (10)	0.042 (8)*	0.286 (6)
O1P	0.978 (3)	0.1363 (14)	0.0354 (6)	0.049 (5)*	0.286 (6)
O2P	0.663 (3)	0.089 (2)	0.0441 (10)	0.064 (7)*	0.286 (6)
O3P	1.102 (2)	−0.3920 (10)	0.1502 (5)	0.115 (4)*	0.286 (6)
C17P	0.437 (4)	0.239 (2)	0.1338 (9)	0.105 (8)*	0.286 (6)
H17D	0.3330	0.1848	0.1376	0.157*	0.286 (6)
H17E	0.4593	0.2767	0.1649	0.157*	0.286 (6)
H17F	0.5552	0.2012	0.1235	0.157*	0.286 (6)
N1P	0.346 (4)	0.258 (2)	0.0485 (7)	0.074 (7)*	0.286 (6)
H1DP	0.2610	0.2024	0.0549	0.112*	0.286 (6)
H1EP	0.4599	0.2281	0.0385	0.112*	0.286 (6)
H1FP	0.2979	0.3019	0.0247	0.112*	0.286 (6)
C16P	0.379 (2)	0.3251 (12)	0.0945 (5)	0.082 (7)*	0.286 (6)
H16P	0.2539	0.3601	0.1043	0.098*	0.286 (6)
C18P	0.518 (2)	0.4131 (12)	0.0820 (5)	0.056 (4)*	0.286 (6)
C19P	0.712 (2)	0.3900 (12)	0.0727 (5)	0.047 (3)*	0.286 (6)
H19P	0.7586	0.3174	0.0783	0.056*	0.286 (6)
C20P	0.839 (2)	0.4713 (12)	0.0554 (5)	0.063 (4)*	0.286 (6)
H20P	0.9686	0.4520	0.0484	0.076*	0.286 (6)
C21P	0.777 (2)	0.5811 (12)	0.0481 (5)	0.069 (7)*	0.286 (6)
C22P	0.587 (2)	0.6058 (12)	0.0615 (5)	0.113 (9)*	0.286 (6)
H22P	0.5427	0.6799	0.0597	0.136*	0.286 (6)
C23P	0.461 (2)	0.5225 (12)	0.0778 (5)	0.118 (8)*	0.286 (6)
H23P	0.3326	0.5418	0.0861	0.141*	0.286 (6)
C24P	0.911 (2)	0.6685 (12)	0.0254 (5)	0.137 (9)*	0.286 (6)
H24D	0.8984	0.6666	−0.0103	0.206*	0.286 (6)
H24E	1.0447	0.6526	0.0345	0.206*	0.286 (6)
H24F	0.8749	0.7419	0.0374	0.206*	0.286 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.158 (7)	0.150 (8)	0.115 (6)	−0.055 (6)	−0.053 (6)	0.016 (6)
C2R	0.097 (5)	0.085 (6)	0.095 (5)	−0.021 (5)	−0.024 (4)	0.042 (5)
C3R	0.075 (4)	0.054 (3)	0.066 (4)	0.005 (3)	−0.011 (4)	0.020 (3)
C4R	0.070 (5)	0.067 (5)	0.080 (6)	0.004 (4)	−0.008 (4)	0.028 (4)
C5R	0.044 (4)	0.056 (4)	0.055 (4)	0.008 (3)	−0.005 (4)	0.009 (4)
C6R	0.034 (3)	0.071 (5)	0.074 (5)	0.006 (3)	−0.001 (3)	0.022 (4)
C7R	0.057 (4)	0.052 (4)	0.054 (5)	−0.005 (3)	0.002 (3)	0.009 (5)
C8R	0.057 (5)	0.045 (4)	0.048 (5)	−0.003 (3)	−0.006 (3)	0.005 (4)
C9R	0.054 (4)	0.047 (4)	0.051 (4)	0.005 (3)	−0.010 (3)	0.003 (4)
C10R	0.056 (4)	0.054 (4)	0.047 (4)	0.000 (3)	−0.008 (3)	−0.002 (4)
C11R	0.059 (4)	0.077 (5)	0.076 (6)	0.004 (4)	0.014 (4)	0.035 (5)
C12R	0.090 (6)	0.072 (5)	0.075 (5)	0.000 (5)	0.011 (4)	0.026 (4)
C13R	0.135 (7)	0.085 (5)	0.089 (6)	−0.008 (5)	−0.017 (6)	−0.001 (4)
C14R	0.131 (7)	0.106 (6)	0.146 (9)	−0.045 (6)	−0.028 (7)	0.000 (6)
C15R	0.060 (5)	0.054 (5)	0.058 (7)	0.007 (3)	−0.009 (3)	0.002 (5)
O1R	0.069 (3)	0.052 (3)	0.064 (4)	−0.002 (3)	0.008 (3)	0.011 (3)
O2R	0.059 (4)	0.086 (6)	0.152 (9)	0.002 (2)	−0.033 (3)	0.047 (5)
O3R	0.075 (3)	0.096 (3)	0.135 (4)	0.039 (3)	0.020 (3)	0.053 (3)
C17R	0.133 (9)	0.168 (9)	0.066 (4)	−0.038 (8)	0.022 (5)	0.043 (5)
N1R	0.045 (3)	0.055 (4)	0.074 (4)	0.001 (3)	0.005 (3)	0.017 (3)
C16R	0.063 (4)	0.112 (6)	0.042 (3)	−0.010 (4)	−0.001 (3)	−0.004 (4)
C18R	0.071 (4)	0.080 (4)	0.047 (4)	0.009 (3)	−0.006 (3)	0.004 (3)
C19R	0.077 (4)	0.066 (4)	0.079 (5)	−0.009 (3)	−0.015 (4)	0.001 (4)
C20R	0.080 (4)	0.083 (4)	0.088 (5)	−0.005 (4)	−0.007 (4)	−0.008 (4)
C21R	0.116 (6)	0.079 (5)	0.064 (5)	−0.017 (4)	−0.003 (4)	−0.002 (4)
C22R	0.137 (7)	0.061 (4)	0.100 (6)	0.016 (5)	−0.023 (5)	0.006 (4)
C23R	0.076 (4)	0.092 (5)	0.086 (5)	0.029 (4)	−0.004 (3)	−0.012 (4)
C24R	0.197 (9)	0.083 (5)	0.120 (6)	−0.077 (6)	−0.016 (6)	0.014 (4)

Geometric parameters (Å, º)

C1R—C2R	1.508 (8)	C1P—C2P	1.558 (10)
C2R—C3R	1.523 (6)	C2P—C3P	1.516 (10)
C3R—C12R	1.511 (7)	C3P—C12P	1.510 (9)
C3R—C4R	1.513 (7)	C3P—C4P	1.513 (9)
C3R—C13R	1.525 (7)	C3P—C13P	1.524 (9)
C4R—O3R	1.231 (7)	C4P—O3P	1.414 (10)
C4R—C5R	1.493 (6)	C4P—C5P	1.538 (9)
C5R—C6R	1.377 (6)	C5P—C6P	1.372 (9)
C5R—C10R	1.394 (6)	C5P—C10P	1.379 (9)
C6R—C7R	1.377 (6)	C6P—C7P	1.373 (9)
C7R—C8R	1.381 (6)	C7P—C8P	1.383 (9)
C8R—C9R	1.379 (6)	C8P—C9P	1.359 (9)
C8R—C15R	1.482 (6)	C8P—C15P	1.506 (9)
C9R—C10R	1.381 (6)	C9P—C10P	1.372 (9)
C10R—C11R	1.508 (6)	C10P—C11P	1.495 (9)
C11R—C12R	1.507 (7)	C11P—C12P	1.508 (10)
C13R—C14R	1.507 (8)	C13P—C14P	1.566 (10)
C15R—O2R	1.243 (6)	C15P—O2P	1.243 (9)
C15R—O1R	1.262 (6)	C15P—O1P	1.250 (9)
C17R—C16R	1.519 (6)	C17P—C16P	1.518 (9)
N1R—C16R	1.506 (6)	N1P—C16P	1.486 (9)
C16R—C18R	1.5104	C16P—C18P	1.4486
C18R—C23R	1.3586	C18P—C23P	1.3586
C18R—C19R	1.3626	C18P—C19P	1.3626
C19R—C20R	1.3749	C19P—C20P	1.3748
C20R—C21R	1.3816	C20P—C21P	1.3815
C21R—C22R	1.3680	C21P—C22P	1.3680
C21R—C24R	1.5085	C21P—C24P	1.5085
C22R—C23R	1.3761	C22P—C23P	1.3761
C1P—C4P	1.509 (10)
C1R—C2R—C3R	116.3 (7)	C12P—C3P—C4P	110.7 (10)
C12R—C3R—C4R	109.8 (5)	C12P—C3P—C2P	112.0 (19)
C12R—C3R—C2R	111.3 (7)	C4P—C3P—C2P	93.1 (8)
C4R—C3R—C2R	107.0 (5)	C12P—C3P—C13P	112.2 (12)
C12R—C3R—C13R	112.7 (6)	C4P—C3P—C13P	114.5 (19)
C4R—C3R—C13R	107.2 (7)	C2P—C3P—C13P	112.9 (12)
C2R—C3R—C13R	108.6 (5)	O3P—C4P—C1P	109.3 (11)
O3R—C4R—C5R	118.7 (6)	O3P—C4P—C3P	110.9 (17)
O3R—C4R—C3R	122.1 (5)	C1P—C4P—C3P	87.6 (8)
C5R—C4R—C3R	118.7 (5)	O3P—C4P—C5P	108.3 (12)
C6R—C5R—C10R	118.7 (5)	C1P—C4P—C5P	121.7 (18)
C6R—C5R—C4R	120.1 (5)	C3P—C4P—C5P	117.7 (9)
C10R—C5R—C4R	121.1 (5)	C6P—C5P—C10P	119.5 (10)
C5R—C6R—C7R	122.2 (5)	C6P—C5P—C4P	120.6 (10)
C6R—C7R—C8R	119.2 (5)	C10P—C5P—C4P	119.8 (9)
C9R—C8R—C7R	119.0 (5)	C5P—C6P—C7P	121.6 (12)
C9R—C8R—C15R	119.8 (5)	C6P—C7P—C8P	119.1 (11)
C7R—C8R—C15R	121.2 (5)	C9P—C8P—C7P	117.9 (10)
C8R—C9R—C10R	122.0 (5)	C9P—C8P—C15P	119.2 (10)
C9R—C10R—C5R	118.8 (5)	C7P—C8P—C15P	122.6 (10)
C9R—C10R—C11R	120.9 (5)	C8P—C9P—C10P	123.4 (11)
C5R—C10R—C11R	120.3 (5)	C9P—C10P—C5P	117.7 (10)
C12R—C11R—C10R	110.8 (6)	C9P—C10P—C11P	120.9 (10)
C11R—C12R—C3R	113.2 (6)	C5P—C10P—C11P	121.4 (10)
C14R—C13R—C3R	116.0 (6)	C10P—C11P—C12P	110.1 (12)
O2R—C15R—O1R	121.6 (7)	C11P—C12P—C3P	112.5 (13)
O2R—C15R—C8R	119.0 (7)	C3P—C13P—C14P	112.7 (13)
O1R—C15R—C8R	119.3 (6)	O2P—C15P—O1P	126.2 (14)
N1R—C16R—C18R	108.0 (3)	O2P—C15P—C8P	116.9 (12)
N1R—C16R—C17R	111.0 (5)	O1P—C15P—C8P	116.9 (11)
C18R—C16R—C17R	115.1 (4)	C18P—C16P—N1P	107.1 (10)
C23R—C18R—C19R	116.8	C18P—C16P—C17P	118.3 (10)
C23R—C18R—C16R	121.5	N1P—C16P—C17P	104.6 (11)
C19R—C18R—C16R	121.7	C23P—C18P—C19P	116.8
C18R—C19R—C20R	121.7	C23P—C18P—C16P	121.3
C19R—C20R—C21R	121.1	C19P—C18P—C16P	121.8
C22R—C21R—C20R	116.8	C18P—C19P—C20P	121.7
C22R—C21R—C24R	121.9	C19P—C20P—C21P	121.1
C20R—C21R—C24R	121.3	C22P—C21P—C20P	116.8
C21R—C22R—C23R	121.0	C22P—C21P—C24P	121.9
C18R—C23R—C22R	122.2	C20P—C21P—C24P	121.3
C4P—C1P—C2P	91.6 (8)	C21P—C22P—C23P	121.0
C3P—C2P—C1P	85.8 (8)	C18P—C23P—C22P	122.2

(56.5P)

Crystal data

C24H31NO3	Dx = 1.172 Mg m^−3
Mr = 381.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1000 reflections
a = 6.8320 (7) Å	θ = 3–12°
b = 11.8970 (15) Å	µ = 0.08 mm^−1
c = 26.609 (3) Å	T = 299 K
V = 2162.8 (4) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 824

Data collection

Kuma KM4CCD diffractometer	1869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −8→3
11741 measured reflections	k = −14→14
3780 independent reflections	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) + (0.108P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.203	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.21 e Å^−3
3780 reflections	Δρmin = −0.18 e Å^−3
327 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
179 restraints	Extinction coefficient: 0.027 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute structure was assigned on the basis of known absolute configuration of the cation.
Secondary atom site location: inferred from neighbouring sites

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1R	1.134 (3)	−0.3025 (16)	0.2974 (6)	0.151 (8)*	0.435 (9)
H1AR	1.2054	−0.3396	0.3238	0.226*	0.435 (9)
H1BR	1.0428	−0.2505	0.3119	0.226*	0.435 (9)
H1CR	1.2242	−0.2626	0.2762	0.226*	0.435 (9)
C2R	1.026 (4)	−0.3884 (15)	0.2669 (6)	0.112 (4)*	0.435 (9)
H2AR	0.9277	−0.4228	0.2883	0.134*	0.435 (9)
H2BR	1.1173	−0.4468	0.2573	0.134*	0.435 (9)
C3R	0.923 (2)	−0.3466 (12)	0.2189 (6)	0.078 (10)*	0.435 (9)
C4R	1.071 (2)	−0.2974 (13)	0.1835 (6)	0.085 (7)*	0.435 (9)
C5R	1.024 (2)	−0.1907 (16)	0.1567 (9)	0.049 (6)*	0.435 (9)
C6R	1.163 (2)	−0.1382 (17)	0.1268 (9)	0.068 (6)*	0.435 (9)
H6R	1.2903	−0.1661	0.1260	0.081*	0.435 (9)
C7R	1.116 (2)	−0.0451 (17)	0.0982 (9)	0.062 (8)*	0.435 (9)
H7R	1.2116	−0.0098	0.0789	0.074*	0.435 (9)
C8R	0.926 (2)	−0.0043 (13)	0.0982 (6)	0.048 (7)*	0.435 (9)
C9R	0.788 (2)	−0.0569 (14)	0.1274 (7)	0.050 (6)*	0.435 (9)
H9R	0.6601	−0.0308	0.1269	0.060*	0.435 (9)
C10R	0.835 (2)	−0.1476 (16)	0.1574 (7)	0.049 (7)*	0.435 (9)
C11R	0.6861 (19)	−0.1939 (13)	0.1940 (5)	0.058 (5)*	0.435 (9)
H11A	0.6134	−0.1319	0.2085	0.069*	0.435 (9)
H11B	0.5941	−0.2408	0.1758	0.069*	0.435 (9)
C12R	0.776 (3)	−0.2613 (16)	0.2353 (5)	0.074 (5)*	0.435 (9)
H12A	0.8395	−0.2100	0.2586	0.089*	0.435 (9)
H12B	0.6728	−0.2994	0.2535	0.089*	0.435 (9)
C13R	0.844 (3)	−0.4461 (18)	0.1895 (7)	0.119 (7)*	0.435 (9)
H13A	0.8017	−0.4203	0.1566	0.143*	0.435 (9)
H13B	0.9481	−0.5001	0.1845	0.143*	0.435 (9)
C14R	0.676 (3)	−0.503 (2)	0.2146 (8)	0.132 (8)*	0.435 (9)
H14A	0.6297	−0.5631	0.1937	0.198*	0.435 (9)
H14B	0.5729	−0.4500	0.2201	0.198*	0.435 (9)
H14C	0.7188	−0.5332	0.2463	0.198*	0.435 (9)
C15R	0.8695 (19)	0.0910 (14)	0.0654 (7)	0.054 (7)*	0.435 (9)
O1R	1.001 (3)	0.159 (2)	0.0510 (13)	0.075 (9)*	0.435 (9)
O2R	0.6922 (17)	0.1071 (11)	0.0563 (4)	0.070 (5)*	0.435 (9)
O3R	1.2371 (14)	−0.3357 (10)	0.1768 (5)	0.100 (4)*	0.435 (9)
C17R	0.374 (2)	0.2793 (15)	0.1342 (5)	0.101 (6)*	0.435 (9)
H17A	0.2742	0.2228	0.1368	0.151*	0.435 (9)
H17B	0.3479	0.3385	0.1578	0.151*	0.435 (9)
H17C	0.4992	0.2464	0.1414	0.151*	0.435 (9)
N1R	0.391 (4)	0.2363 (16)	0.0420 (6)	0.058 (4)*	0.435 (9)
H1DR	0.3028	0.1829	0.0483	0.086*	0.435 (9)
H1ER	0.5103	0.2068	0.0426	0.086*	0.435 (9)
H1FR	0.3679	0.2658	0.0118	0.086*	0.435 (9)
C16R	0.3752 (16)	0.3269 (9)	0.0813 (4)	0.078 (3)*	0.435 (9)
H16R	0.2464	0.3615	0.0765	0.094*	0.435 (9)
C18R	0.5245 (16)	0.4188 (9)	0.0698 (4)	0.055 (4)*	0.435 (9)
C19R	0.7137 (16)	0.3941 (9)	0.0579 (4)	0.089 (6)*	0.435 (9)
H19R	0.7554	0.3198	0.0592	0.107*	0.435 (9)
C20R	0.8447 (16)	0.4764 (9)	0.0443 (4)	0.094 (7)*	0.435 (9)
H20R	0.9716	0.4563	0.0354	0.113*	0.435 (9)
C21R	0.7909 (16)	0.5883 (9)	0.0435 (4)	0.085 (8)*	0.435 (9)
C22R	0.6057 (16)	0.6133 (9)	0.0596 (4)	0.111 (7)*	0.435 (9)
H22R	0.5671	0.6880	0.0621	0.133*	0.435 (9)
C23R	0.4757 (16)	0.5294 (9)	0.0720 (4)	0.089 (6)*	0.435 (9)
H23R	0.3502	0.5491	0.0823	0.107*	0.435 (9)
C24R	0.9289 (16)	0.6779 (9)	0.0247 (4)	0.139 (10)*	0.435 (9)
H24A	0.9135	0.6865	−0.0109	0.208*	0.435 (9)
H24B	1.0613	0.6565	0.0321	0.208*	0.435 (9)
H24C	0.8997	0.7479	0.0411	0.208*	0.435 (9)
C1P	1.1881 (16)	−0.2909 (12)	0.2280 (5)	0.155 (7)	0.565 (9)
H1AP	1.1975	−0.2149	0.2410	0.187*	0.565 (9)
H1BP	1.3172	−0.3229	0.2228	0.187*	0.565 (9)
C2P	1.046 (2)	−0.3695 (15)	0.2595 (5)	0.136 (4)	0.565 (9)
H2AP	1.0857	−0.4476	0.2612	0.164*	0.565 (9)
H2BP	1.0110	−0.3405	0.2924	0.164*	0.565 (9)
C3P	0.8967 (15)	−0.3436 (9)	0.2182 (5)	0.070 (7)	0.565 (9)
C4P	1.0560 (15)	−0.3013 (9)	0.1830 (4)	0.084 (5)	0.565 (9)
C5P	1.0078 (17)	−0.2022 (12)	0.1487 (7)	0.065 (6)	0.565 (9)
C6P	1.1525 (16)	−0.1540 (13)	0.1190 (6)	0.065 (4)	0.565 (9)
H6P	1.2785	−0.1835	0.1199	0.078*	0.565 (9)
C7P	1.1141 (15)	−0.0641 (14)	0.0884 (7)	0.056 (4)	0.565 (9)
H7P	1.2132	−0.0327	0.0690	0.067*	0.565 (9)
C8P	0.9262 (14)	−0.0203 (9)	0.0866 (5)	0.044 (3)	0.565 (9)
C9P	0.7836 (16)	−0.0716 (11)	0.1144 (6)	0.055 (4)	0.565 (9)
H9P	0.6554	−0.0467	0.1109	0.067*	0.565 (9)
C10P	0.8199 (15)	−0.1580 (13)	0.1473 (6)	0.055 (5)	0.565 (9)
C11P	0.6588 (13)	−0.2112 (10)	0.1783 (4)	0.062 (3)	0.565 (9)
H11C	0.5563	−0.1567	0.1847	0.074*	0.565 (9)
H11D	0.6022	−0.2740	0.1601	0.074*	0.565 (9)
C12P	0.745 (2)	−0.2515 (12)	0.2274 (4)	0.092 (5)	0.565 (9)
H12C	0.6420	−0.2804	0.2488	0.110*	0.565 (9)
H12D	0.8069	−0.1889	0.2446	0.110*	0.565 (9)
C13P	0.784 (2)	−0.4489 (10)	0.2015 (5)	0.120 (5)	0.565 (9)
H13C	0.8771	−0.5061	0.1912	0.143*	0.565 (9)
H13D	0.7040	−0.4303	0.1726	0.143*	0.565 (9)
C14P	0.650 (2)	−0.4975 (12)	0.2440 (6)	0.166 (7)	0.565 (9)
H14D	0.5814	−0.5622	0.2316	0.249*	0.565 (9)
H14E	0.5575	−0.4414	0.2543	0.249*	0.565 (9)
H14F	0.7293	−0.5189	0.2723	0.249*	0.565 (9)
C15P	0.8758 (15)	0.0791 (11)	0.0537 (6)	0.059 (5)	0.565 (9)
O1P	1.0103 (19)	0.1458 (16)	0.0414 (10)	0.068 (4)	0.565 (9)
O2P	0.7054 (12)	0.0885 (7)	0.0382 (4)	0.064 (2)	0.565 (9)
O3P	1.1341 (17)	−0.3900 (7)	0.1530 (4)	0.144 (5)	0.565 (9)
C17P	0.453 (2)	0.2391 (10)	0.1350 (4)	0.108 (4)	0.565 (9)
H17D	0.3513	0.1844	0.1394	0.162*	0.565 (9)
H17E	0.4689	0.2815	0.1654	0.162*	0.565 (9)
H17F	0.5737	0.2016	0.1271	0.162*	0.565 (9)
N1P	0.377 (4)	0.2439 (15)	0.0475 (5)	0.092 (5)	0.565 (9)
H1DP	0.2924	0.1893	0.0542	0.137*	0.565 (9)
H1EP	0.4930	0.2141	0.0398	0.137*	0.565 (9)
H1FP	0.3340	0.2843	0.0216	0.137*	0.565 (9)
C16P	0.3986 (12)	0.3180 (6)	0.0923 (3)	0.100 (3)	0.565 (9)
H16P	0.2717	0.3526	0.0998	0.119*	0.565 (9)
C18P	0.5391 (12)	0.4064 (6)	0.0797 (3)	0.077 (4)	0.565 (9)
C19P	0.7312 (12)	0.3834 (6)	0.0705 (3)	0.061 (3)	0.565 (9)
H19P	0.7779	0.3110	0.0761	0.074*	0.565 (9)
C20P	0.8578 (12)	0.4645 (6)	0.0532 (3)	0.074 (4)	0.565 (9)
H20P	0.9870	0.4453	0.0463	0.089*	0.565 (9)
C21P	0.7963 (12)	0.5739 (6)	0.0460 (3)	0.080 (6)	0.565 (9)
C22P	0.6078 (12)	0.5984 (6)	0.0594 (3)	0.104 (5)	0.565 (9)
H22P	0.5637	0.6722	0.0575	0.125*	0.565 (9)
C23P	0.4824 (12)	0.5154 (6)	0.0755 (3)	0.105 (5)	0.565 (9)
H23P	0.3545	0.5346	0.0838	0.126*	0.565 (9)
C24P	0.9300 (12)	0.6611 (6)	0.0233 (3)	0.120 (7)	0.565 (9)
H24D	0.9182	0.6594	−0.0127	0.180*	0.565 (9)
H24E	1.0629	0.6452	0.0326	0.180*	0.565 (9)
H24F	0.8941	0.7342	0.0354	0.180*	0.565 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.107 (9)	0.163 (13)	0.196 (16)	−0.024 (9)	−0.067 (10)	0.110 (13)
C2P	0.107 (7)	0.170 (9)	0.132 (8)	0.025 (7)	0.038 (7)	0.085 (7)
C3P	0.090 (9)	0.054 (8)	0.065 (8)	−0.001 (5)	−0.019 (6)	0.028 (5)
C4P	0.058 (6)	0.091 (8)	0.104 (9)	0.036 (5)	0.011 (5)	0.055 (6)
C5P	0.070 (8)	0.058 (7)	0.068 (9)	−0.001 (5)	−0.024 (6)	0.015 (7)
C6P	0.040 (5)	0.070 (7)	0.084 (9)	0.006 (5)	−0.002 (5)	0.017 (8)
C7P	0.050 (7)	0.059 (7)	0.058 (8)	0.009 (4)	−0.002 (5)	0.007 (8)
C8P	0.059 (7)	0.038 (5)	0.036 (6)	−0.004 (4)	0.000 (4)	−0.009 (5)
C9P	0.045 (6)	0.059 (7)	0.062 (9)	0.004 (4)	−0.006 (5)	0.002 (7)
C10P	0.043 (6)	0.067 (8)	0.054 (7)	−0.007 (4)	−0.008 (5)	0.003 (7)
C11P	0.057 (5)	0.069 (7)	0.059 (6)	−0.005 (5)	−0.004 (5)	0.004 (6)
C12P	0.078 (8)	0.115 (9)	0.082 (8)	0.016 (7)	0.013 (6)	0.054 (7)
C13P	0.138 (12)	0.093 (9)	0.128 (10)	0.031 (9)	0.021 (9)	0.040 (8)
C14P	0.187 (13)	0.103 (10)	0.207 (19)	−0.041 (10)	0.096 (13)	0.020 (11)
C15P	0.081 (10)	0.055 (7)	0.041 (7)	0.004 (5)	−0.003 (5)	−0.008 (6)
O1P	0.065 (6)	0.051 (5)	0.088 (11)	0.002 (4)	0.010 (5)	0.029 (9)
O2P	0.068 (4)	0.062 (5)	0.064 (6)	0.024 (3)	−0.027 (4)	0.000 (4)
O3P	0.200 (10)	0.092 (6)	0.140 (9)	0.093 (7)	0.068 (8)	0.047 (6)
C17P	0.143 (12)	0.106 (9)	0.075 (7)	0.005 (9)	0.031 (7)	0.040 (7)
N1P	0.061 (6)	0.101 (8)	0.113 (9)	−0.004 (5)	0.010 (6)	0.064 (6)
C16P	0.109 (7)	0.114 (7)	0.075 (7)	0.013 (6)	0.041 (6)	0.014 (6)
C18P	0.098 (8)	0.085 (8)	0.048 (6)	0.027 (6)	0.008 (5)	0.023 (5)
C19P	0.068 (6)	0.038 (5)	0.078 (7)	−0.003 (4)	0.000 (5)	0.009 (4)
C20P	0.059 (5)	0.069 (7)	0.094 (8)	0.006 (5)	0.002 (5)	0.013 (6)
C21P	0.134 (13)	0.054 (6)	0.052 (7)	−0.011 (6)	−0.006 (6)	0.003 (5)
C22P	0.142 (10)	0.065 (6)	0.107 (9)	0.057 (7)	−0.003 (7)	0.023 (6)
C23P	0.106 (8)	0.091 (9)	0.119 (10)	0.020 (7)	0.023 (7)	0.006 (7)
C24P	0.179 (14)	0.081 (8)	0.101 (10)	−0.075 (9)	−0.039 (8)	0.031 (6)

Geometric parameters (Å, º)

C1R—C2R	1.502 (10)	C1P—C2P	1.590 (10)
C2R—C3R	1.538 (10)	C2P—C3P	1.529 (9)
C3R—C12R	1.490 (9)	C3P—C4P	1.521 (8)
C3R—C4R	1.502 (9)	C3P—C12P	1.526 (9)
C3R—C13R	1.519 (10)	C3P—C13P	1.535 (9)
C4R—O3R	1.237 (9)	C4P—O3P	1.426 (9)
C4R—C5R	1.491 (9)	C4P—C5P	1.528 (8)
C5R—C6R	1.387 (9)	C5P—C10P	1.387 (8)
C5R—C10R	1.392 (9)	C5P—C6P	1.389 (8)
C6R—C7R	1.382 (9)	C6P—C7P	1.370 (8)
C7R—C8R	1.382 (9)	C7P—C8P	1.386 (7)
C8R—C9R	1.372 (9)	C8P—C9P	1.367 (8)
C8R—C15R	1.483 (9)	C8P—C15P	1.511 (8)
C9R—C10R	1.380 (9)	C9P—C10P	1.372 (8)
C10R—C11R	1.511 (9)	C10P—C11P	1.513 (8)
C11R—C12R	1.494 (9)	C11P—C12P	1.513 (9)
C13R—C14R	1.487 (10)	C13P—C14P	1.567 (10)
C15R—O2R	1.251 (9)	C15P—O2P	1.241 (7)
C15R—O1R	1.268 (9)	C15P—O1P	1.257 (7)
C17R—C16R	1.517 (9)	C17P—C16P	1.519 (8)
N1R—C16R	1.505 (9)	N1P—C16P	1.490 (8)
C16R—C18R	1.5265	C16P—C18P	1.4628
C18R—C23R	1.3586	C18P—C23P	1.3586
C18R—C19R	1.3626	C18P—C19P	1.3626
C19R—C20R	1.3748	C19P—C20P	1.3749
C20R—C21R	1.3815	C20P—C21P	1.3816
C21R—C22R	1.3680	C21P—C22P	1.3680
C21R—C24R	1.5085	C21P—C24P	1.5085
C22R—C23R	1.3761	C22P—C23P	1.3761
C1P—C4P	1.505 (9)
C1R—C2R—C3R	117.1 (12)	C4P—C3P—C12P	110.2 (7)
C12R—C3R—C4R	111.7 (9)	C4P—C3P—C2P	91.9 (7)
C12R—C3R—C13R	116.3 (11)	C12P—C3P—C2P	118.6 (12)
C4R—C3R—C13R	102.7 (14)	C4P—C3P—C13P	116.8 (11)
C12R—C3R—C2R	106.5 (15)	C12P—C3P—C13P	107.0 (9)
C4R—C3R—C2R	109.8 (11)	C2P—C3P—C13P	112.1 (8)
C13R—C3R—C2R	109.8 (11)	O3P—C4P—C1P	106.3 (8)
O3R—C4R—C5R	116.2 (10)	O3P—C4P—C3P	111.5 (10)
O3R—C4R—C3R	124.5 (10)	C1P—C4P—C3P	88.1 (6)
C5R—C4R—C3R	119.2 (9)	O3P—C4P—C5P	108.5 (9)
C6R—C5R—C10R	118.5 (9)	C1P—C4P—C5P	122.8 (12)
C6R—C5R—C4R	120.8 (9)	C3P—C4P—C5P	118.0 (6)
C10R—C5R—C4R	120.4 (9)	C10P—C5P—C6P	119.2 (7)
C7R—C6R—C5R	121.2 (11)	C10P—C5P—C4P	120.5 (7)
C6R—C7R—C8R	119.9 (11)	C6P—C5P—C4P	120.3 (7)
C9R—C8R—C7R	119.0 (9)	C7P—C6P—C5P	121.6 (8)
C9R—C8R—C15R	120.1 (9)	C6P—C7P—C8P	119.4 (8)
C7R—C8R—C15R	120.9 (10)	C9P—C8P—C7P	118.3 (7)
C8R—C9R—C10R	121.7 (10)	C9P—C8P—C15P	120.1 (7)
C9R—C10R—C5R	119.6 (9)	C7P—C8P—C15P	121.6 (8)
C9R—C10R—C11R	120.2 (9)	C8P—C9P—C10P	123.4 (7)
C5R—C10R—C11R	120.0 (9)	C9P—C10P—C5P	117.9 (7)
C12R—C11R—C10R	113.1 (10)	C9P—C10P—C11P	121.9 (7)
C3R—C12R—C11R	115.3 (9)	C5P—C10P—C11P	120.0 (7)
C14R—C13R—C3R	113.4 (13)	C12P—C11P—C10P	108.6 (8)
O2R—C15R—O1R	121.8 (13)	C11P—C12P—C3P	110.7 (7)
O2R—C15R—C8R	119.0 (10)	C3P—C13P—C14P	112.7 (9)
O1R—C15R—C8R	118.9 (12)	O2P—C15P—O1P	122.8 (9)
N1R—C16R—C17R	112.2 (10)	O2P—C15P—C8P	118.5 (8)
N1R—C16R—C18R	109.1 (9)	O1P—C15P—C8P	118.6 (8)
C17R—C16R—C18R	117.2 (7)	C18P—C16P—N1P	107.8 (7)
C23R—C18R—C19R	116.8	C18P—C16P—C17P	117.0 (6)
C23R—C18R—C16R	121.4	N1P—C16P—C17P	104.9 (8)
C19R—C18R—C16R	121.7	C23P—C18P—C19P	116.8
C18R—C19R—C20R	121.7	C23P—C18P—C16P	121.2
C19R—C20R—C21R	121.1	C19P—C18P—C16P	122.0
C22R—C21R—C20R	116.8	C18P—C19P—C20P	121.7
C22R—C21R—C24R	121.9	C19P—C20P—C21P	121.1
C20R—C21R—C24R	121.3	C22P—C21P—C20P	116.8
C21R—C22R—C23R	121.0	C22P—C21P—C24P	121.9
C18R—C23R—C22R	122.2	C20P—C21P—C24P	121.3
C4P—C1P—C2P	90.2 (6)	C21P—C22P—C23P	121.0
C3P—C2P—C1P	84.8 (6)	C18P—C23P—C22P	122.2

(72.6P)

Crystal data

C24H31NO3	Dx = 1.175 Mg m^−3
Mr = 381.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1000 reflections
a = 6.8632 (8) Å	θ = 3–12°
b = 11.9445 (17) Å	µ = 0.08 mm^−1
c = 26.305 (4) Å	T = 299 K
V = 2156.4 (5) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 824

Data collection

Kuma KM4CCD diffractometer	1767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −3→8
11703 measured reflections	k = −14→14
3760 independent reflections	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)] = 0.068	w = 1/[σ^2(Fo^2) + (0.1113P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.212	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.16 e Å^−3
3760 reflections	Δρmin = −0.15 e Å^−3
327 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
191 restraints	Extinction coefficient: 0.037 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute structure was assigned on the basis of known absolute configuration of the cation.
Secondary atom site location: inferred from neighbouring sites

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1R	1.142 (5)	−0.291 (3)	0.2985 (12)	0.177 (10)*	0.274 (9)
H1AR	1.2084	−0.3302	0.3251	0.265*	0.274 (9)
H1BR	1.0637	−0.2321	0.3131	0.265*	0.274 (9)
H1CR	1.2357	−0.2583	0.2757	0.265*	0.274 (9)
C2R	1.014 (6)	−0.370 (3)	0.2700 (9)	0.116 (9)*	0.274 (9)
H2AR	0.9001	−0.3825	0.2908	0.140*	0.274 (9)
H2BR	1.0836	−0.4403	0.2681	0.140*	0.274 (9)
C3R	0.942 (3)	−0.343 (2)	0.2167 (10)	0.092 (15)*	0.274 (9)
C4R	1.098 (3)	−0.2895 (18)	0.1853 (10)	0.069 (12)*	0.274 (9)
C5R	1.054 (3)	−0.1824 (15)	0.1580 (9)	0.047 (7)*	0.274 (9)
C6R	1.195 (3)	−0.1309 (17)	0.1290 (8)	0.056 (9)*	0.274 (9)
H6R	1.3217	−0.1589	0.1299	0.067*	0.274 (9)
C7R	1.156 (3)	−0.0391 (19)	0.0985 (10)	0.057 (10)*	0.274 (9)
H7R	1.2552	−0.0045	0.0802	0.069*	0.274 (9)
C8R	0.966 (3)	0.000 (2)	0.0958 (11)	0.045 (10)*	0.274 (9)
C9R	0.830 (3)	−0.048 (2)	0.1272 (11)	0.067 (14)*	0.274 (9)
H9R	0.7091	−0.0133	0.1298	0.081*	0.274 (9)
C10R	0.863 (3)	−0.143 (3)	0.1553 (17)	0.068 (18)*	0.274 (9)
C11R	0.702 (3)	−0.202 (3)	0.1840 (16)	0.077 (8)*	0.274 (9)
H11A	0.6049	−0.1482	0.1949	0.093*	0.274 (9)
H11B	0.6382	−0.2560	0.1618	0.093*	0.274 (9)
C12R	0.783 (5)	−0.262 (3)	0.2300 (12)	0.091 (9)*	0.274 (9)
H12A	0.8337	−0.2074	0.2537	0.110*	0.274 (9)
H12B	0.6785	−0.3025	0.2468	0.110*	0.274 (9)
C13R	0.869 (5)	−0.449 (3)	0.1900 (11)	0.136 (10)*	0.274 (9)
H13A	0.8469	−0.4314	0.1545	0.163*	0.274 (9)
H13B	0.9697	−0.5055	0.1917	0.163*	0.274 (9)
C14R	0.686 (4)	−0.494 (3)	0.2122 (14)	0.133 (13)*	0.274 (9)
H14A	0.6404	−0.5553	0.1915	0.200*	0.274 (9)
H14B	0.5890	−0.4368	0.2133	0.200*	0.274 (9)
H14C	0.7114	−0.5211	0.2460	0.200*	0.274 (9)
C15R	0.909 (3)	0.091 (3)	0.0599 (19)	0.078 (10)*	0.274 (9)
O1R	1.038 (4)	0.161 (3)	0.0475 (14)	0.063 (10)*	0.274 (9)
O2R	0.733 (3)	0.115 (2)	0.0574 (8)	0.079 (9)*	0.274 (9)
O3R	1.252 (3)	−0.3374 (15)	0.1724 (7)	0.107 (6)*	0.274 (9)
C17R	0.409 (5)	0.283 (3)	0.1336 (8)	0.109 (12)*	0.274 (9)
H17A	0.3106	0.2267	0.1374	0.164*	0.274 (9)
H17B	0.3869	0.3418	0.1580	0.164*	0.274 (9)
H17C	0.5350	0.2509	0.1391	0.164*	0.274 (9)
N1R	0.423 (7)	0.240 (3)	0.0417 (11)	0.058 (10)*	0.274 (9)
H1DR	0.3363	0.1864	0.0478	0.087*	0.274 (9)
H1ER	0.5429	0.2118	0.0441	0.087*	0.274 (9)
H1FR	0.4049	0.2674	0.0106	0.087*	0.274 (9)
C16R	0.399 (3)	0.3320 (15)	0.0801 (6)	0.078 (5)*	0.274 (9)
H16R	0.2688	0.3641	0.0755	0.094*	0.274 (9)
C18R	0.549 (3)	0.4244 (15)	0.0685 (6)	0.056 (4)*	0.274 (9)
C19R	0.738 (3)	0.3998 (15)	0.0567 (6)	0.092 (10)*	0.274 (9)
H19R	0.7790	0.3258	0.0579	0.111*	0.274 (9)
C20R	0.868 (3)	0.4818 (15)	0.0431 (6)	0.090 (10)*	0.274 (9)
H20R	0.9946	0.4618	0.0342	0.108*	0.274 (9)
C21R	0.815 (3)	0.5933 (15)	0.0423 (6)	0.088 (11)*	0.274 (9)
C22R	0.630 (3)	0.6181 (15)	0.0584 (6)	0.097 (8)*	0.274 (9)
H22R	0.5915	0.6925	0.0610	0.117*	0.274 (9)
C23R	0.500 (3)	0.5345 (15)	0.0708 (6)	0.076 (7)*	0.274 (9)
H23R	0.3753	0.5541	0.0810	0.091*	0.274 (9)
C24R	0.952 (3)	0.6826 (15)	0.0236 (6)	0.162 (15)*	0.274 (9)
H24A	0.9375	0.6913	−0.0125	0.243*	0.274 (9)
H24B	1.0839	0.6613	0.0312	0.243*	0.274 (9)
H24C	0.9229	0.7523	0.0401	0.243*	0.274 (9)
C1P	1.1995 (14)	−0.2949 (9)	0.2279 (4)	0.162 (5)	0.726 (9)
H1AP	1.2098	−0.2192	0.2410	0.195*	0.726 (9)
H1BP	1.3272	−0.3268	0.2217	0.195*	0.726 (9)
C2P	1.0617 (17)	−0.3724 (13)	0.2598 (4)	0.141 (5)	0.726 (9)
H2AP	1.0995	−0.4507	0.2602	0.169*	0.726 (9)
H2BP	1.0342	−0.3452	0.2938	0.169*	0.726 (9)
C3P	0.9064 (14)	−0.3434 (7)	0.2205 (4)	0.075 (4)	0.726 (9)
C4P	1.0584 (14)	−0.3066 (8)	0.1830 (3)	0.076 (4)	0.726 (9)
C5P	1.0205 (11)	−0.2046 (7)	0.1499 (3)	0.059 (3)	0.726 (9)
C6P	1.1666 (11)	−0.1583 (8)	0.1206 (4)	0.065 (3)	0.726 (9)
H6P	1.2900	−0.1905	0.1211	0.078*	0.726 (9)
C7P	1.1338 (13)	−0.0653 (9)	0.0905 (4)	0.065 (3)	0.726 (9)
H7P	1.2348	−0.0337	0.0718	0.077*	0.726 (9)
C8P	0.9478 (14)	−0.0198 (9)	0.0887 (5)	0.059 (4)	0.726 (9)
C9P	0.8032 (12)	−0.0685 (8)	0.1169 (4)	0.056 (3)	0.726 (9)
H9P	0.6767	−0.0415	0.1137	0.067*	0.726 (9)
C10P	0.8374 (15)	−0.1555 (12)	0.1498 (6)	0.058 (4)	0.726 (9)
C11P	0.6770 (15)	−0.2007 (14)	0.1835 (7)	0.091 (4)	0.726 (9)
H11C	0.5877	−0.1408	0.1923	0.109*	0.726 (9)
H11D	0.6044	−0.2579	0.1654	0.109*	0.726 (9)
C12P	0.763 (2)	−0.2500 (11)	0.2313 (5)	0.100 (4)	0.726 (9)
H12C	0.6586	−0.2787	0.2525	0.119*	0.726 (9)
H12D	0.8287	−0.1913	0.2502	0.119*	0.726 (9)
C13P	0.7914 (17)	−0.4478 (8)	0.2041 (4)	0.118 (3)	0.726 (9)
H13C	0.8823	−0.5049	0.1929	0.141*	0.726 (9)
H13D	0.7091	−0.4285	0.1754	0.141*	0.726 (9)
C14P	0.6621 (18)	−0.4967 (10)	0.2473 (6)	0.167 (6)	0.726 (9)
H14D	0.5936	−0.5613	0.2350	0.251*	0.726 (9)
H14E	0.5699	−0.4411	0.2582	0.251*	0.726 (9)
H14F	0.7430	−0.5179	0.2755	0.251*	0.726 (9)
C15P	0.9060 (14)	0.0844 (12)	0.0578 (7)	0.073 (4)	0.726 (9)
O1P	1.0480 (18)	0.1456 (12)	0.0454 (7)	0.091 (6)	0.726 (9)
O2P	0.7406 (11)	0.0951 (7)	0.0395 (4)	0.077 (2)	0.726 (9)
O3P	1.1383 (11)	−0.3940 (6)	0.1520 (3)	0.124 (3)	0.726 (9)
C17P	0.483 (2)	0.2452 (10)	0.1370 (4)	0.129 (5)	0.726 (9)
H17D	0.3822	0.1903	0.1418	0.194*	0.726 (9)
H17E	0.4918	0.2914	0.1668	0.194*	0.726 (9)
H17F	0.6049	0.2082	0.1314	0.194*	0.726 (9)
N1P	0.417 (3)	0.2402 (12)	0.0472 (5)	0.091 (6)	0.726 (9)
H1DP	0.3324	0.1861	0.0543	0.136*	0.726 (9)
H1EP	0.5332	0.2102	0.0406	0.136*	0.726 (9)
H1FP	0.3763	0.2782	0.0201	0.136*	0.726 (9)
C16P	0.4336 (9)	0.3173 (4)	0.0914 (2)	0.095 (3)	0.726 (9)
H16P	0.3062	0.3521	0.0972	0.114*	0.726 (9)
C18P	0.5747 (9)	0.4060 (4)	0.0787 (2)	0.071 (2)	0.726 (9)
C19P	0.7660 (9)	0.3832 (4)	0.0696 (2)	0.078 (3)	0.726 (9)
H19P	0.8124	0.3111	0.0752	0.094*	0.726 (9)
C20P	0.8923 (9)	0.4641 (4)	0.0523 (2)	0.082 (3)	0.726 (9)
H20P	1.0210	0.4451	0.0454	0.098*	0.726 (9)
C21P	0.8312 (9)	0.5731 (4)	0.0451 (2)	0.086 (4)	0.726 (9)
C22P	0.6433 (9)	0.5975 (4)	0.0584 (2)	0.098 (3)	0.726 (9)
H22P	0.5994	0.6710	0.0566	0.118*	0.726 (9)
C23P	0.5182 (9)	0.5147 (4)	0.0745 (2)	0.099 (3)	0.726 (9)
H23P	0.3908	0.5337	0.0829	0.118*	0.726 (9)
C24P	0.9646 (9)	0.6601 (4)	0.0224 (2)	0.124 (5)	0.726 (9)
H24D	0.9534	0.6587	−0.0140	0.186*	0.726 (9)
H24E	1.0967	0.6442	0.0319	0.186*	0.726 (9)
H24F	0.9287	0.7329	0.0347	0.186*	0.726 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.130 (8)	0.168 (10)	0.190 (11)	0.006 (7)	−0.074 (8)	0.118 (9)
C2P	0.100 (8)	0.197 (11)	0.126 (9)	0.009 (8)	0.013 (7)	0.084 (9)
C3P	0.097 (7)	0.057 (6)	0.071 (6)	−0.002 (5)	−0.015 (5)	0.028 (4)
C4P	0.047 (4)	0.077 (7)	0.105 (9)	0.000 (5)	−0.004 (5)	0.033 (5)
C5P	0.048 (4)	0.052 (5)	0.076 (6)	−0.010 (4)	−0.010 (4)	0.000 (4)
C6P	0.038 (4)	0.063 (5)	0.095 (7)	0.006 (4)	−0.017 (4)	−0.001 (5)
C7P	0.062 (5)	0.060 (6)	0.072 (6)	0.002 (5)	0.003 (4)	0.006 (6)
C8P	0.060 (6)	0.046 (5)	0.072 (7)	−0.012 (4)	−0.015 (4)	0.000 (5)
C9P	0.040 (4)	0.049 (5)	0.078 (7)	−0.001 (4)	−0.009 (4)	0.005 (5)
C10P	0.054 (5)	0.056 (6)	0.066 (7)	0.003 (4)	−0.006 (5)	0.010 (5)
C11P	0.067 (5)	0.101 (7)	0.104 (7)	0.023 (5)	0.041 (5)	0.041 (5)
C12P	0.101 (7)	0.095 (7)	0.103 (7)	0.008 (6)	0.044 (6)	0.033 (6)
C13P	0.110 (8)	0.088 (7)	0.156 (9)	−0.022 (6)	0.013 (7)	0.021 (7)
C14P	0.168 (11)	0.108 (8)	0.227 (17)	−0.023 (8)	0.098 (11)	0.058 (10)
C15P	0.082 (6)	0.063 (6)	0.074 (6)	0.008 (4)	0.013 (5)	0.010 (4)
O1P	0.072 (5)	0.065 (6)	0.136 (9)	−0.006 (4)	0.012 (4)	0.035 (6)
O2P	0.072 (4)	0.067 (4)	0.092 (6)	0.013 (3)	−0.034 (4)	0.005 (5)
O3P	0.127 (6)	0.089 (5)	0.157 (7)	0.053 (5)	0.051 (5)	0.045 (4)
C17P	0.174 (13)	0.131 (10)	0.082 (7)	−0.026 (10)	0.025 (7)	0.041 (7)
N1P	0.064 (5)	0.100 (8)	0.108 (9)	−0.004 (4)	0.010 (5)	0.047 (5)
C16P	0.097 (6)	0.107 (6)	0.080 (6)	0.014 (5)	0.029 (5)	0.012 (5)
C18P	0.072 (5)	0.071 (5)	0.068 (5)	0.008 (4)	0.008 (4)	0.020 (4)
C19P	0.079 (5)	0.050 (5)	0.105 (7)	0.001 (4)	−0.010 (5)	0.005 (4)
C20P	0.054 (4)	0.081 (6)	0.110 (8)	−0.003 (4)	−0.010 (5)	0.008 (5)
C21P	0.135 (9)	0.056 (5)	0.068 (6)	−0.015 (6)	−0.004 (5)	0.001 (4)
C22P	0.117 (7)	0.060 (5)	0.117 (8)	0.032 (5)	−0.008 (6)	0.017 (5)
C23P	0.095 (6)	0.085 (7)	0.115 (8)	0.016 (5)	0.002 (5)	−0.002 (6)
C24P	0.186 (11)	0.083 (6)	0.104 (8)	−0.068 (7)	−0.025 (7)	0.017 (5)

Geometric parameters (Å, º)

C1R—C2R	1.490 (11)	C1P—C2P	1.567 (9)
C2R—C3R	1.519 (11)	C2P—C3P	1.524 (8)
C3R—C4R	1.497 (10)	C3P—C4P	1.501 (8)
C3R—C12R	1.501 (10)	C3P—C12P	1.515 (8)
C3R—C13R	1.522 (11)	C3P—C13P	1.537 (8)
C4R—O3R	1.248 (10)	C4P—O3P	1.434 (8)
C4R—C5R	1.498 (9)	C4P—C5P	1.519 (7)
C5R—C6R	1.381 (10)	C5P—C6P	1.381 (7)
C5R—C10R	1.392 (10)	C5P—C10P	1.386 (7)
C6R—C7R	1.385 (10)	C6P—C7P	1.382 (7)
C7R—C8R	1.385 (10)	C7P—C8P	1.388 (7)
C8R—C9R	1.372 (10)	C8P—C9P	1.369 (7)
C8R—C15R	1.489 (10)	C8P—C15P	1.514 (7)
C9R—C10R	1.377 (10)	C9P—C10P	1.372 (7)
C10R—C11R	1.517 (10)	C10P—C11P	1.514 (7)
C11R—C12R	1.512 (11)	C11P—C12P	1.508 (9)
C13R—C14R	1.489 (11)	C13P—C14P	1.557 (9)
C15R—O2R	1.247 (11)	C15P—O2P	1.240 (8)
C15R—O1R	1.268 (11)	C15P—O1P	1.261 (7)
C17R—C16R	1.524 (10)	C17P—C16P	1.515 (8)
N1R—C16R	1.500 (11)	N1P—C16P	1.488 (7)
C16R—C18R	1.5395	C16P—C18P	1.4738
C18R—C23R	1.3586	C18P—C23P	1.3586
C18R—C19R	1.3626	C18P—C19P	1.3626
C19R—C20R	1.3748	C19P—C20P	1.3749
C20R—C21R	1.3816	C20P—C21P	1.3816
C21R—C22R	1.3681	C21P—C22P	1.3681
C21R—C24R	1.5085	C21P—C24P	1.5085
C22R—C23R	1.3761	C22P—C23P	1.3761
C1P—C4P	1.533 (9)
C1R—C2R—C3R	121.8 (16)	C4P—C3P—C12P	111.0 (6)
C4R—C3R—C12R	111.7 (12)	C4P—C3P—C2P	91.5 (6)
C4R—C3R—C2R	111.3 (14)	C12P—C3P—C2P	119.6 (10)
C12R—C3R—C2R	99 (3)	C4P—C3P—C13P	114.2 (9)
C4R—C3R—C13R	110 (2)	C12P—C3P—C13P	108.5 (8)
C12R—C3R—C13R	113.6 (14)	C2P—C3P—C13P	111.4 (7)
C2R—C3R—C13R	111.3 (14)	O3P—C4P—C3P	115.2 (9)
O3R—C4R—C3R	123.9 (14)	O3P—C4P—C5P	108.9 (6)
O3R—C4R—C5R	115.5 (12)	C3P—C4P—C5P	119.5 (6)
C3R—C4R—C5R	119.2 (10)	O3P—C4P—C1P	105.2 (7)
C6R—C5R—C10R	118.9 (10)	C3P—C4P—C1P	87.7 (6)
C6R—C5R—C4R	120.2 (11)	C5P—C4P—C1P	118.4 (9)
C10R—C5R—C4R	120.2 (10)	C6P—C5P—C10P	119.1 (6)
C5R—C6R—C7R	122.4 (12)	C6P—C5P—C4P	121.1 (6)
C6R—C7R—C8R	118.7 (12)	C10P—C5P—C4P	119.8 (6)
C9R—C8R—C7R	118.0 (11)	C5P—C6P—C7P	121.5 (6)
C9R—C8R—C15R	120.2 (12)	C6P—C7P—C8P	119.0 (7)
C7R—C8R—C15R	121.8 (12)	C9P—C8P—C7P	118.8 (6)
C8R—C9R—C10R	123.8 (13)	C9P—C8P—C15P	120.2 (6)
C9R—C10R—C5R	117.4 (11)	C7P—C8P—C15P	121.0 (7)
C9R—C10R—C11R	122.4 (12)	C8P—C9P—C10P	122.6 (6)
C5R—C10R—C11R	120.2 (11)	C9P—C10P—C5P	118.6 (6)
C12R—C11R—C10R	110.5 (14)	C9P—C10P—C11P	121.0 (6)
C3R—C12R—C11R	112.9 (14)	C5P—C10P—C11P	120.4 (6)
C14R—C13R—C3R	113.6 (15)	C12P—C11P—C10P	110.1 (8)
O2R—C15R—O1R	121 (2)	C11P—C12P—C3P	112.7 (8)
O2R—C15R—C8R	117.4 (15)	C3P—C13P—C14P	113.0 (8)
O1R—C15R—C8R	117.6 (17)	O2P—C15P—O1P	123.2 (8)
N1R—C16R—C17R	109.7 (14)	O2P—C15P—C8P	117.9 (8)
N1R—C16R—C18R	108.5 (12)	O1P—C15P—C8P	118.0 (8)
C17R—C16R—C18R	115.3 (12)	C18P—C16P—N1P	108.5 (5)
C23R—C18R—C19R	116.8	C18P—C16P—C17P	116.3 (5)
C23R—C18R—C16R	121.4	N1P—C16P—C17P	106.5 (7)
C19R—C18R—C16R	121.7	C23P—C18P—C19P	116.8
C18R—C19R—C20R	121.7	C23P—C18P—C16P	121.2
C19R—C20R—C21R	121.1	C19P—C18P—C16P	122.0
C22R—C21R—C20R	116.8	C18P—C19P—C20P	121.7
C22R—C21R—C24R	121.9	C19P—C20P—C21P	121.1
C20R—C21R—C24R	121.3	C22P—C21P—C20P	116.8
C21R—C22R—C23R	121.0	C22P—C21P—C24P	121.9
C18R—C23R—C22R	122.2	C20P—C21P—C24P	121.3
C4P—C1P—C2P	88.7 (6)	C21P—C22P—C23P	121.0
C3P—C2P—C1P	85.7 (6)	C18P—C23P—C22P	122.2

(100P)

Crystal data

C24H31NO3	Dx = 1.177 Mg m^−3
Mr = 381.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1000 reflections
a = 6.8834 (7) Å	θ = 3–12°
b = 12.0641 (15) Å	µ = 0.08 mm^−1
c = 25.924 (3) Å	T = 299 K
V = 2152.8 (4) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 824

Data collection

Kuma KM4CCD diffractometer	1344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.096
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −8→3
11650 measured reflections	k = −14→14
3741 independent reflections	l = −30→30

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0813P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max < 0.001
3741 reflections	Δρmax = 0.16 e Å^−3
254 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Absolute structure: The absolute structure was assigned on the basis of known absolute configuration of the cation.
Primary atom site location: structure-invariant direct methods

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1P	1.2109 (11)	−0.2905 (7)	0.2299 (4)	0.171 (4)
H1AP	1.2248	−0.2141	0.2409	0.205*
H1BP	1.3370	−0.3251	0.2255	0.205*
C2P	1.0690 (12)	−0.3590 (8)	0.2639 (3)	0.165 (4)
H2AP	1.1067	−0.4358	0.2687	0.198*
H2BP	1.0355	−0.3241	0.2965	0.198*
C3P	0.9215 (9)	−0.3403 (5)	0.2210 (2)	0.0838 (18)
C4P	1.0791 (9)	−0.3044 (5)	0.1838 (2)	0.0834 (17)
C5P	1.0461 (8)	−0.1992 (4)	0.1517 (2)	0.0738 (15)
C6P	1.1927 (7)	−0.1550 (5)	0.1222 (2)	0.0849 (17)
H6P	1.3132	−0.1898	0.1214	0.102*
C7P	1.1641 (8)	−0.0603 (5)	0.0939 (2)	0.0785 (16)
H7P	1.2676	−0.0281	0.0764	0.094*
C8P	0.9815 (7)	−0.0126 (4)	0.09136 (18)	0.0554 (13)
C9P	0.8368 (7)	−0.0592 (4)	0.1197 (2)	0.0702 (15)
H9P	0.7128	−0.0290	0.1174	0.084*
C10P	0.8654 (7)	−0.1490 (5)	0.1514 (2)	0.0697 (15)
C11P	0.7041 (8)	−0.1936 (5)	0.1839 (2)	0.101 (2)
H11A	0.6317	−0.2487	0.1646	0.121*
H11B	0.6158	−0.1340	0.1930	0.121*
C12P	0.7855 (10)	−0.2452 (7)	0.2322 (3)	0.123 (2)
H12A	0.6791	−0.2717	0.2534	0.148*
H12B	0.8547	−0.1890	0.2517	0.148*
C13P	0.8085 (12)	−0.4452 (7)	0.2067 (3)	0.143 (3)
H13A	0.9000	−0.5029	0.1973	0.171*
H13B	0.7283	−0.4298	0.1768	0.171*
C14P	0.6759 (13)	−0.4887 (6)	0.2513 (4)	0.193 (5)
H14A	0.6068	−0.5533	0.2399	0.290*
H14B	0.5848	−0.4321	0.2609	0.290*
H14C	0.7549	−0.5075	0.2806	0.290*
C15P	0.9436 (9)	0.0889 (4)	0.0589 (2)	0.0702 (15)
O1P	1.0846 (5)	0.1502 (3)	0.04827 (15)	0.0852 (11)
O2P	0.7763 (5)	0.1053 (3)	0.04271 (16)	0.0926 (13)
O3P	1.1520 (7)	−0.3910 (4)	0.1523 (2)	0.145 (2)
C16P	0.4649 (9)	0.3204 (5)	0.0902 (3)	0.0898 (18)
H16P	0.3366	0.3547	0.0939	0.108*
C17P	0.5053 (11)	0.2554 (6)	0.1386 (2)	0.141 (3)
H17A	0.4051	0.2010	0.1435	0.211*
H17B	0.5079	0.3048	0.1676	0.211*
H17C	0.6287	0.2188	0.1355	0.211*
C18P	0.6063 (7)	0.4101 (6)	0.0774 (2)	0.0723 (15)
C19P	0.7972 (8)	0.3877 (5)	0.0682 (2)	0.0826 (17)
H19P	0.8435	0.3163	0.0738	0.099*
C20P	0.9234 (8)	0.4680 (6)	0.0511 (2)	0.0913 (18)
H20P	1.0518	0.4493	0.0441	0.110*
C21P	0.8624 (11)	0.5760 (6)	0.0439 (2)	0.0882 (17)
C22P	0.6748 (11)	0.5999 (5)	0.0573 (3)	0.106 (2)
H22P	0.6310	0.6727	0.0556	0.127*
C23P	0.5500 (9)	0.5177 (7)	0.0733 (2)	0.0956 (19)
H23P	0.4227	0.5364	0.0817	0.115*
C24P	0.9957 (11)	0.6625 (6)	0.0212 (3)	0.145 (3)
H24A	0.9850	0.6614	−0.0157	0.217*
H24B	1.1273	0.6466	0.0310	0.217*
H24C	0.9595	0.7343	0.0339	0.217*
N1P	0.4542 (5)	0.2414 (4)	0.04694 (17)	0.0790 (14)
H1CP	0.3695	0.1880	0.0545	0.118*
H1DP	0.5708	0.2117	0.0416	0.118*
H1EP	0.4158	0.2767	0.0186	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.133 (7)	0.187 (10)	0.193 (9)	−0.043 (6)	−0.049 (7)	0.104 (7)
C2P	0.140 (7)	0.236 (10)	0.120 (7)	−0.039 (7)	−0.042 (6)	0.079 (7)
C3P	0.095 (4)	0.066 (4)	0.090 (5)	0.000 (4)	−0.002 (4)	0.025 (4)
C4P	0.082 (4)	0.080 (4)	0.088 (4)	0.014 (4)	−0.008 (4)	0.020 (4)
C5P	0.067 (3)	0.074 (4)	0.080 (4)	0.008 (3)	0.004 (3)	0.006 (3)
C6P	0.056 (3)	0.101 (5)	0.098 (5)	0.017 (3)	0.012 (4)	0.027 (4)
C7P	0.072 (4)	0.086 (4)	0.077 (4)	0.003 (3)	−0.005 (3)	0.022 (3)
C8P	0.054 (3)	0.053 (3)	0.059 (3)	0.004 (3)	−0.006 (3)	0.011 (3)
C9P	0.055 (3)	0.061 (4)	0.094 (4)	0.005 (3)	0.002 (3)	0.023 (3)
C10P	0.057 (3)	0.069 (4)	0.083 (4)	−0.007 (3)	0.009 (3)	0.010 (3)
C11P	0.076 (4)	0.121 (5)	0.105 (5)	0.007 (4)	0.017 (4)	0.034 (4)
C12P	0.125 (6)	0.126 (6)	0.120 (6)	−0.002 (5)	0.047 (5)	0.028 (5)
C13P	0.165 (7)	0.128 (7)	0.135 (7)	−0.017 (6)	0.003 (6)	0.021 (5)
C14P	0.186 (9)	0.118 (7)	0.275 (12)	−0.007 (7)	0.093 (8)	0.067 (8)
C15P	0.071 (4)	0.062 (4)	0.077 (4)	0.002 (3)	0.013 (4)	0.001 (3)
O1P	0.073 (2)	0.082 (3)	0.101 (3)	−0.008 (2)	0.014 (2)	0.024 (2)
O2P	0.068 (2)	0.083 (3)	0.127 (3)	0.015 (2)	−0.024 (2)	0.024 (2)
O3P	0.165 (4)	0.111 (4)	0.158 (4)	0.072 (3)	0.055 (4)	0.044 (3)
C16P	0.079 (4)	0.101 (5)	0.089 (5)	−0.017 (4)	0.007 (4)	−0.011 (4)
C17P	0.176 (7)	0.177 (8)	0.070 (5)	−0.055 (6)	0.005 (5)	0.035 (5)
C18P	0.064 (4)	0.080 (5)	0.073 (4)	0.007 (4)	0.007 (3)	−0.005 (3)
C19P	0.079 (4)	0.058 (4)	0.111 (5)	−0.003 (3)	0.001 (4)	−0.002 (3)
C20P	0.072 (4)	0.090 (5)	0.111 (5)	−0.010 (4)	−0.008 (4)	−0.002 (4)
C21P	0.105 (5)	0.082 (5)	0.078 (4)	−0.022 (4)	−0.019 (4)	0.004 (4)
C22P	0.119 (6)	0.078 (5)	0.121 (6)	0.014 (5)	−0.024 (5)	0.022 (4)
C23P	0.073 (4)	0.106 (6)	0.108 (5)	0.016 (4)	0.007 (4)	0.005 (4)
C24P	0.181 (7)	0.118 (6)	0.135 (7)	−0.062 (6)	−0.008 (6)	0.013 (5)
N1P	0.053 (2)	0.093 (4)	0.091 (3)	−0.006 (2)	−0.005 (3)	0.041 (3)

Geometric parameters (Å, º)

C1P—C4P	1.509 (9)	C10P—C11P	1.494 (7)
C1P—C2P	1.555 (9)	C11P—C12P	1.507 (8)
C2P—C3P	1.524 (8)	C13P—C14P	1.564 (9)
C3P—C12P	1.510 (8)	C15P—O2P	1.242 (6)
C3P—C4P	1.514 (7)	C15P—O1P	1.251 (6)
C3P—C13P	1.530 (9)	C16P—N1P	1.473 (7)
C4P—O3P	1.418 (6)	C16P—C18P	1.493 (7)
C4P—C5P	1.535 (7)	C16P—C17P	1.506 (8)
C5P—C6P	1.374 (7)	C18P—C23P	1.359 (7)
C5P—C10P	1.383 (6)	C18P—C19P	1.363 (6)
C6P—C7P	1.372 (7)	C19P—C20P	1.375 (7)
C7P—C8P	1.384 (6)	C20P—C21P	1.382 (7)
C8P—C9P	1.359 (6)	C21P—C22P	1.368 (8)
C8P—C15P	1.508 (7)	C21P—C24P	1.508 (8)
C9P—C10P	1.375 (7)	C22P—C23P	1.376 (8)
C4P—C1P—C2P	90.7 (6)	C9P—C10P—C5P	118.5 (5)
C3P—C2P—C1P	85.7 (5)	C9P—C10P—C11P	121.0 (5)
C12P—C3P—C4P	110.5 (5)	C5P—C10P—C11P	120.5 (5)
C12P—C3P—C2P	112.6 (7)	C10P—C11P—C12P	109.9 (5)
C4P—C3P—C2P	91.7 (5)	C11P—C12P—C3P	112.6 (6)
C12P—C3P—C13P	111.1 (6)	C3P—C13P—C14P	113.3 (7)
C4P—C3P—C13P	116.5 (6)	O2P—C15P—O1P	123.4 (5)
C2P—C3P—C13P	113.2 (6)	O2P—C15P—C8P	118.6 (5)
O3P—C4P—C1P	109.0 (6)	O1P—C15P—C8P	118.0 (5)
O3P—C4P—C3P	114.2 (5)	N1P—C16P—C18P	109.4 (5)
C1P—C4P—C3P	87.6 (5)	N1P—C16P—C17P	107.8 (5)
O3P—C4P—C5P	110.5 (5)	C18P—C16P—C17P	116.3 (5)
C1P—C4P—C5P	115.2 (6)	C23P—C18P—C19P	116.8 (6)
C3P—C4P—C5P	118.4 (5)	C23P—C18P—C16P	121.6 (5)
C6P—C5P—C10P	119.2 (5)	C19P—C18P—C16P	121.6 (6)
C6P—C5P—C4P	120.9 (5)	C18P—C19P—C20P	121.7 (6)
C10P—C5P—C4P	119.9 (5)	C19P—C20P—C21P	121.1 (5)
C7P—C6P—C5P	121.0 (5)	C22P—C21P—C20P	116.8 (6)
C6P—C7P—C8P	120.2 (5)	C22P—C21P—C24P	121.9 (7)
C9P—C8P—C7P	117.9 (4)	C20P—C21P—C24P	121.3 (7)
C9P—C8P—C15P	120.7 (4)	C21P—C22P—C23P	121.0 (6)
C7P—C8P—C15P	121.5 (5)	C18P—C23P—C22P	122.2 (6)
C8P—C9P—C10P	123.0 (5)