tert-Butyl (7R)-7-[(4S)-2,2-di­methyl-[1,3]­dioxolan-4-yl]-1,4-dioxa-8-aza­spiro­[4.5]­decane-8-carboxyl­ate

The title compound, C₁₇H₂₉NO₆, crystallizes with two mol­ecules in the asymmetric unit. The independent mol­ecules differ in the conformation of the side chain attached to nitro­gen. The piperidine ring adopts a chair conformation, with the 1,3-dioxolane ring occupying an axial position.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.049
• wR factor = 0.119
• Data-to-parameter ratio = 7.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.01
         From the CIF: _reflns_number_total               3277
         Count of symmetry unique reflns         3288
         Completeness (_total/calc)             99.67%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

Computing details

Data collection: XSCANS (Siemens, 1993); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1989); software used to prepare material for publication: SHELXL97.

tert-Butyl (7R)-7-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1,4-dioxa-8- azaspiro[4.5]decane-8-carboxylate

Crystal data

C17H29NO6	Z = 2
Mr = 343.41	F(000) = 372
Triclinic, P1	Dx = 1.220 Mg m^−3
a = 9.641 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.997 (1) Å	Cell parameters from 38 reflections
c = 11.042 (1) Å	θ = 7.2–12.5°
α = 84.77 (1)°	µ = 0.09 mm^−1
β = 69.72 (1)°	T = 293 K
γ = 69.59 (1)°	Block, colourless
V = 935.1 (2) Å^3	0.44 × 0.32 × 0.28 mm

Data collection

Siemens P4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
Graphite monochromator	h = −1→11
ω–2θ scans	k = −11→11
3913 measured reflections	l = −12→13
3277 independent reflections	3 standard reflections every 97 reflections
2068 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.1664P] where P = (Fo^2 + 2Fc^2)/3
3277 reflections	(Δ/σ)max < 0.001
433 parameters	Δρmax = 0.28 e Å^−3
3 restraints	Δρmin = −0.15 e Å^−3

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
O12	0.7843 (4)	0.0217 (3)	0.4476 (3)	0.0510 (9)
O9	0.6570 (4)	0.1932 (3)	0.8085 (3)	0.0578 (10)
O11	0.5675 (4)	0.2178 (4)	0.5191 (3)	0.0552 (9)
O6	0.5119 (4)	0.7777 (4)	1.1066 (3)	0.0557 (10)
O5	0.4772 (4)	0.7878 (4)	0.9121 (4)	0.0607 (10)
O8	1.0340 (4)	0.3510 (4)	0.6366 (3)	0.0591 (10)
O10	0.4529 (4)	0.3990 (4)	0.8835 (3)	0.0586 (10)
O3	0.8208 (4)	0.4724 (4)	1.0300 (4)	0.0650 (11)
O1	1.1256 (4)	0.6881 (4)	0.7640 (3)	0.0608 (10)
N2	0.7967 (4)	0.2017 (4)	0.5434 (4)	0.0446 (10)
N1	0.7187 (4)	0.7437 (4)	0.9261 (4)	0.0415 (10)
O2	1.0625 (5)	0.9282 (4)	0.7885 (4)	0.0722 (12)
O7	1.0679 (5)	0.4641 (4)	0.4481 (4)	0.0764 (12)
O4	1.0285 (5)	0.3622 (4)	1.0990 (4)	0.0826 (13)
C13	0.5622 (6)	0.7698 (5)	0.9752 (5)	0.0449 (13)
C30	0.7037 (6)	0.1536 (5)	0.5055 (4)	0.0426 (12)
C24	0.7273 (6)	0.3347 (5)	0.6198 (5)	0.0439 (12)
H24	0.6201	0.3806	0.6182	0.053*
C7	0.8252 (5)	0.7108 (5)	1.0001 (4)	0.0404 (12)
H7	0.7611	0.7317	1.0915	0.048*
C20	0.9941 (6)	0.3691 (5)	0.5228 (5)	0.0512 (13)
C18	0.9646 (6)	0.1287 (5)	0.5193 (5)	0.0491 (13)
H18A	1.0009	0.0421	0.4674	0.059*
H18B	0.9828	0.1023	0.6007	0.059*
C1	0.7936 (6)	0.7380 (5)	0.7851 (4)	0.0473 (13)
H1A	0.7140	0.7620	0.7443	0.057*
H1B	0.8653	0.6420	0.7563	0.057*
C6	0.9238 (6)	0.8088 (5)	0.9606 (5)	0.0481 (13)
H6A	1.0070	0.7748	0.9978	0.058*
H6B	0.8577	0.9040	0.9967	0.058*
C3	0.9975 (6)	0.8177 (5)	0.8144 (5)	0.0484 (13)
C31	0.7032 (6)	−0.0572 (6)	0.4082 (5)	0.0506 (13)
C25	0.7166 (6)	0.3069 (5)	0.7604 (5)	0.0467 (13)
H25	0.8195	0.2861	0.7697	0.056*
C23	0.8204 (6)	0.4349 (5)	0.5562 (5)	0.0507 (14)
H23A	0.7976	0.4697	0.4779	0.061*
H23B	0.7835	0.5168	0.6142	0.061*
C19	1.0561 (6)	0.2269 (5)	0.4486 (5)	0.0545 (14)
H19A	1.1665	0.1804	0.4382	0.065*
H19B	1.0472	0.2442	0.3633	0.065*
C2	0.8826 (6)	0.8416 (5)	0.7458 (5)	0.0498 (14)
H2A	0.9382	0.8313	0.6534	0.060*
H2B	0.8086	0.9384	0.7648	0.060*
C8	0.9246 (6)	0.5521 (5)	0.9850 (5)	0.0448 (12)
H8	0.9899	0.5262	0.8944	0.054*
C9	1.0245 (6)	0.5048 (5)	1.0713 (5)	0.0557 (14)
H9A	1.1294	0.5082	1.0269	0.067*
H9B	0.9769	0.5642	1.1497	0.067*
C27	0.4982 (6)	0.2480 (6)	0.8954 (5)	0.0538 (14)
C26	0.5925 (6)	0.4325 (5)	0.8513 (5)	0.0564 (15)
H26A	0.6186	0.4378	0.9277	0.068*
H26B	0.5825	0.5225	0.8079	0.068*
C10	0.8896 (7)	0.3483 (6)	1.0901 (6)	0.0622 (16)
C32	0.6442 (9)	0.0172 (6)	0.3020 (5)	0.0764 (19)
H32A	0.5643	0.1077	0.3345	0.115*
H32B	0.6008	−0.0407	0.2718	0.115*
H32C	0.7296	0.0320	0.2320	0.115*
C14	0.3486 (6)	0.7874 (6)	1.1817 (5)	0.0563 (15)
C33	0.5702 (7)	−0.0770 (7)	0.5246 (5)	0.0689 (17)
H33A	0.4909	0.0143	0.5551	0.103*
H33B	0.6109	−0.1204	0.5921	0.103*
H33C	0.5252	−0.1374	0.5000	0.103*
C28	0.3971 (7)	0.1943 (6)	0.8502 (6)	0.0695 (17)
H28A	0.4266	0.0926	0.8582	0.104*
H28B	0.4108	0.2174	0.7615	0.104*
H28C	0.2889	0.2385	0.9021	0.104*
C34	0.8286 (8)	−0.1985 (6)	0.3602 (7)	0.085 (2)
H34A	0.8649	−0.2441	0.4292	0.128*
H34B	0.9148	−0.1842	0.2906	0.128*
H34C	0.7866	−0.2577	0.3301	0.128*
C22	1.1862 (7)	0.3637 (7)	0.6017 (6)	0.0718 (18)
H22A	1.2682	0.2708	0.5820	0.086*
H22B	1.1947	0.4110	0.6705	0.086*
C15	0.2347 (7)	0.9240 (6)	1.1580 (7)	0.086 (2)
H15A	0.2375	0.9236	1.0703	0.128*
H15B	0.2627	1.0027	1.1729	0.128*
H15C	0.1307	0.9337	1.2156	0.128*
C29	0.4928 (8)	0.2072 (7)	1.0303 (6)	0.082 (2)
H29A	0.5235	0.1052	1.0359	0.123*
H29B	0.3879	0.2503	1.0890	0.123*
H29C	0.5637	0.2399	1.0526	0.123*
C16	0.3503 (8)	0.7822 (8)	1.3187 (6)	0.084 (2)
H16A	0.4253	0.6933	1.3300	0.126*
H16B	0.2477	0.7900	1.3782	0.126*
H16C	0.3792	0.8599	1.3348	0.126*
C11	0.9386 (9)	0.2180 (7)	1.0082 (8)	0.099 (2)
H11A	0.9848	0.1351	1.0507	0.149*
H11B	1.0141	0.2250	0.9263	0.149*
H11C	0.8483	0.2102	0.9951	0.149*
C17	0.3209 (8)	0.6550 (6)	1.1503 (6)	0.0774 (19)
H17A	0.3976	0.5707	1.1669	0.116*
H17B	0.3301	0.6542	1.0610	0.116*
H17C	0.2174	0.6570	1.2035	0.116*
C4	1.2642 (8)	0.7155 (9)	0.7451 (8)	0.095 (2)
H4A	1.3426	0.6738	0.6629	0.114*
H4B	1.3064	0.6752	0.8134	0.114*
C5	1.2233 (9)	0.8694 (9)	0.7465 (9)	0.107 (3)
H5A	1.2646	0.8989	0.8041	0.129*
H5B	1.2676	0.9008	0.6605	0.129*
C12	0.7706 (11)	0.3471 (10)	1.2206 (6)	0.122 (3)
H12A	0.8124	0.2639	1.2649	0.183*
H12B	0.6764	0.3452	1.2103	0.183*
H12C	0.7469	0.4313	1.2699	0.183*
C21	1.1963 (9)	0.4528 (9)	0.4837 (8)	0.100 (2)
H21A	1.1935	0.5467	0.5029	0.121*
H21B	1.2936	0.4076	0.4142	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O12	0.045 (2)	0.055 (2)	0.057 (2)	−0.0210 (18)	−0.0134 (18)	−0.0167 (17)
O9	0.048 (2)	0.0395 (19)	0.068 (3)	−0.0086 (18)	−0.005 (2)	0.0018 (17)
O11	0.040 (2)	0.064 (2)	0.065 (2)	−0.0135 (19)	−0.0227 (19)	−0.0115 (18)
O6	0.041 (2)	0.077 (2)	0.051 (2)	−0.0262 (19)	−0.0089 (18)	−0.0065 (18)
O5	0.045 (2)	0.076 (3)	0.066 (3)	−0.019 (2)	−0.025 (2)	−0.004 (2)
O8	0.056 (2)	0.071 (2)	0.064 (2)	−0.032 (2)	−0.027 (2)	0.006 (2)
O10	0.045 (2)	0.048 (2)	0.069 (3)	−0.0058 (19)	−0.0097 (19)	−0.0113 (18)
O3	0.072 (3)	0.060 (2)	0.093 (3)	−0.038 (2)	−0.056 (2)	0.034 (2)
O1	0.043 (2)	0.060 (2)	0.068 (2)	−0.014 (2)	−0.0074 (19)	−0.0001 (19)
N2	0.035 (2)	0.041 (2)	0.056 (3)	−0.010 (2)	−0.014 (2)	−0.012 (2)
N1	0.032 (2)	0.051 (2)	0.041 (2)	−0.014 (2)	−0.011 (2)	0.0019 (19)
O2	0.064 (3)	0.060 (2)	0.098 (3)	−0.039 (2)	−0.020 (2)	0.016 (2)
O7	0.084 (3)	0.077 (3)	0.084 (3)	−0.050 (3)	−0.034 (3)	0.037 (2)
O4	0.087 (3)	0.080 (3)	0.116 (4)	−0.042 (3)	−0.072 (3)	0.039 (3)
C13	0.046 (3)	0.036 (3)	0.052 (4)	−0.017 (3)	−0.012 (3)	−0.004 (2)
C30	0.045 (3)	0.046 (3)	0.036 (3)	−0.021 (3)	−0.005 (2)	−0.004 (2)
C24	0.035 (3)	0.035 (3)	0.059 (3)	−0.006 (2)	−0.017 (3)	−0.007 (2)
C7	0.036 (3)	0.053 (3)	0.034 (3)	−0.020 (3)	−0.009 (2)	−0.001 (2)
C20	0.056 (4)	0.049 (3)	0.060 (3)	−0.029 (3)	−0.025 (3)	0.012 (3)
C18	0.041 (3)	0.041 (3)	0.064 (3)	−0.012 (3)	−0.015 (3)	−0.008 (3)
C1	0.052 (3)	0.053 (3)	0.038 (3)	−0.016 (3)	−0.019 (3)	0.007 (2)
C6	0.039 (3)	0.044 (3)	0.058 (3)	−0.015 (2)	−0.010 (3)	−0.005 (2)
C3	0.050 (3)	0.037 (3)	0.059 (4)	−0.021 (3)	−0.013 (3)	0.002 (2)
C31	0.054 (3)	0.056 (3)	0.049 (3)	−0.030 (3)	−0.013 (3)	−0.006 (3)
C25	0.040 (3)	0.047 (3)	0.053 (3)	−0.012 (3)	−0.016 (3)	−0.003 (2)
C23	0.059 (4)	0.039 (3)	0.059 (3)	−0.015 (3)	−0.029 (3)	0.005 (2)
C19	0.044 (3)	0.062 (3)	0.059 (3)	−0.021 (3)	−0.018 (3)	0.004 (3)
C2	0.050 (3)	0.046 (3)	0.051 (3)	−0.016 (3)	−0.015 (3)	0.007 (2)
C8	0.049 (3)	0.044 (3)	0.050 (3)	−0.024 (3)	−0.019 (3)	0.006 (2)
C9	0.054 (3)	0.053 (3)	0.070 (4)	−0.022 (3)	−0.029 (3)	0.005 (3)
C27	0.043 (3)	0.053 (3)	0.057 (4)	−0.009 (3)	−0.012 (3)	−0.004 (3)
C26	0.054 (4)	0.048 (3)	0.064 (4)	−0.013 (3)	−0.016 (3)	−0.015 (3)
C10	0.074 (4)	0.066 (4)	0.070 (4)	−0.040 (3)	−0.042 (4)	0.025 (3)
C32	0.117 (6)	0.083 (4)	0.058 (4)	−0.060 (4)	−0.041 (4)	0.015 (3)
C14	0.039 (3)	0.063 (4)	0.062 (4)	−0.022 (3)	−0.001 (3)	−0.015 (3)
C33	0.090 (5)	0.078 (4)	0.052 (4)	−0.048 (4)	−0.022 (3)	0.009 (3)
C28	0.060 (4)	0.076 (4)	0.073 (4)	−0.026 (3)	−0.018 (3)	−0.006 (3)
C34	0.077 (5)	0.065 (4)	0.106 (5)	−0.022 (4)	−0.015 (4)	−0.036 (4)
C22	0.050 (4)	0.089 (5)	0.087 (5)	−0.031 (4)	−0.027 (3)	−0.006 (4)
C15	0.050 (4)	0.071 (4)	0.106 (5)	−0.002 (4)	−0.006 (4)	−0.012 (4)
C29	0.084 (5)	0.088 (5)	0.064 (4)	−0.022 (4)	−0.021 (4)	0.008 (3)
C16	0.072 (4)	0.126 (5)	0.056 (4)	−0.050 (4)	−0.003 (3)	−0.017 (4)
C11	0.104 (6)	0.061 (4)	0.146 (7)	−0.013 (4)	−0.073 (5)	0.004 (4)
C17	0.074 (4)	0.082 (4)	0.077 (4)	−0.042 (4)	−0.005 (4)	−0.018 (3)
C4	0.052 (4)	0.115 (6)	0.117 (6)	−0.031 (4)	−0.028 (4)	0.012 (5)
C5	0.068 (5)	0.118 (7)	0.150 (7)	−0.051 (5)	−0.040 (5)	0.031 (6)
C12	0.148 (8)	0.186 (9)	0.067 (5)	−0.112 (7)	−0.030 (5)	0.035 (5)
C21	0.090 (6)	0.122 (6)	0.110 (6)	−0.070 (5)	−0.028 (5)	0.025 (5)

Geometric parameters (Å, º)

O12—C30	1.358 (5)	C2—H2A	0.9700
O12—C31	1.467 (6)	C2—H2B	0.9700
O9—C25	1.427 (6)	C8—C9	1.515 (7)
O9—C27	1.434 (6)	C8—H8	0.9800
O11—C30	1.205 (6)	C9—H9A	0.9700
O6—C13	1.362 (6)	C9—H9B	0.9700
O6—C14	1.476 (6)	C27—C29	1.496 (8)
O5—C13	1.207 (6)	C27—C28	1.496 (8)
O8—C20	1.416 (6)	C26—H26A	0.9700
O8—C22	1.431 (6)	C26—H26B	0.9700
O10—C26	1.418 (6)	C10—C11	1.492 (8)
O10—C27	1.426 (6)	C10—C12	1.500 (9)
O3—C10	1.415 (6)	C32—H32A	0.9600
O3—C8	1.422 (6)	C32—H32B	0.9600
O1—C4	1.399 (7)	C32—H32C	0.9600
O1—C3	1.433 (6)	C14—C15	1.493 (8)
N2—C30	1.345 (6)	C14—C16	1.515 (8)
N2—C24	1.456 (5)	C14—C17	1.529 (7)
N2—C18	1.462 (6)	C33—H33A	0.9600
N1—C13	1.350 (6)	C33—H33B	0.9600
N1—C7	1.458 (6)	C33—H33C	0.9600
N1—C1	1.469 (6)	C28—H28A	0.9600
O2—C5	1.371 (7)	C28—H28B	0.9600
O2—C3	1.413 (6)	C28—H28C	0.9600
O7—C21	1.390 (8)	C34—H34A	0.9600
O7—C20	1.417 (6)	C34—H34B	0.9600
O4—C9	1.421 (6)	C34—H34C	0.9600
O4—C10	1.429 (7)	C22—C21	1.504 (9)
C24—C25	1.526 (7)	C22—H22A	0.9700
C24—C23	1.538 (7)	C22—H22B	0.9700
C24—H24	0.9800	C15—H15A	0.9600
C7—C6	1.528 (6)	C15—H15B	0.9600
C7—C8	1.530 (6)	C15—H15C	0.9600
C7—H7	0.9800	C29—H29A	0.9600
C20—C23	1.490 (7)	C29—H29B	0.9600
C20—C19	1.526 (7)	C29—H29C	0.9600
C18—C19	1.529 (7)	C16—H16A	0.9600
C18—H18A	0.9700	C16—H16B	0.9600
C18—H18B	0.9700	C16—H16C	0.9600
C1—C2	1.509 (6)	C11—H11A	0.9600
C1—H1A	0.9700	C11—H11B	0.9600
C1—H1B	0.9700	C11—H11C	0.9600
C6—C3	1.531 (7)	C17—H17A	0.9600
C6—H6A	0.9700	C17—H17B	0.9600
C6—H6B	0.9700	C17—H17C	0.9600
C3—C2	1.490 (7)	C4—C5	1.449 (10)
C31—C34	1.496 (7)	C4—H4A	0.9700
C31—C32	1.503 (7)	C4—H4B	0.9700
C31—C33	1.525 (7)	C5—H5A	0.9700
C25—C26	1.538 (7)	C5—H5B	0.9700
C25—H25	0.9800	C12—H12A	0.9600
C23—H23A	0.9700	C12—H12B	0.9600
C23—H23B	0.9700	C12—H12C	0.9600
C19—H19A	0.9700	C21—H21A	0.9700
C19—H19B	0.9700	C21—H21B	0.9700
C30—O12—C31	120.5 (4)	O10—C27—C29	111.1 (4)
C25—O9—C27	110.6 (4)	O9—C27—C29	109.8 (5)
C13—O6—C14	119.9 (4)	O10—C27—C28	108.9 (5)
C20—O8—C22	106.9 (4)	O9—C27—C28	108.7 (4)
C26—O10—C27	106.1 (4)	C29—C27—C28	113.0 (5)
C10—O3—C8	109.8 (4)	O10—C26—C25	103.0 (4)
C4—O1—C3	107.1 (5)	O10—C26—H26A	111.2
C30—N2—C24	119.0 (4)	C25—C26—H26A	111.2
C30—N2—C18	125.6 (4)	O10—C26—H26B	111.2
C24—N2—C18	115.3 (4)	C25—C26—H26B	111.2
C13—N1—C7	126.0 (4)	H26A—C26—H26B	109.1
C13—N1—C1	118.3 (4)	O3—C10—O4	106.1 (4)
C7—N1—C1	115.5 (4)	O3—C10—C11	110.7 (5)
C5—O2—C3	109.2 (5)	O4—C10—C11	107.7 (6)
C21—O7—C20	108.2 (5)	O3—C10—C12	106.6 (6)
C9—O4—C10	108.6 (4)	O4—C10—C12	112.2 (5)
O5—C13—N1	125.2 (5)	C11—C10—C12	113.3 (6)
O5—C13—O6	124.3 (5)	C31—C32—H32A	109.5
N1—C13—O6	110.4 (4)	C31—C32—H32B	109.5
O11—C30—N2	125.4 (4)	H32A—C32—H32B	109.5
O11—C30—O12	123.7 (5)	C31—C32—H32C	109.5
N2—C30—O12	110.9 (4)	H32A—C32—H32C	109.5
N2—C24—C25	111.2 (4)	H32B—C32—H32C	109.5
N2—C24—C23	109.2 (4)	O6—C14—C15	110.9 (4)
C25—C24—C23	113.0 (4)	O6—C14—C16	101.4 (4)
N2—C24—H24	107.7	C15—C14—C16	111.9 (5)
C25—C24—H24	107.7	O6—C14—C17	108.9 (4)
C23—C24—H24	107.7	C15—C14—C17	113.2 (5)
N1—C7—C6	109.4 (4)	C16—C14—C17	109.8 (5)
N1—C7—C8	110.7 (4)	C31—C33—H33A	109.5
C6—C7—C8	113.2 (4)	C31—C33—H33B	109.5
N1—C7—H7	107.8	H33A—C33—H33B	109.5
C6—C7—H7	107.8	C31—C33—H33C	109.5
C8—C7—H7	107.8	H33A—C33—H33C	109.5
O8—C20—O7	105.3 (4)	H33B—C33—H33C	109.5
O8—C20—C23	109.9 (4)	C27—C28—H28A	109.5
O7—C20—C23	109.6 (4)	C27—C28—H28B	109.5
O8—C20—C19	110.9 (4)	H28A—C28—H28B	109.5
O7—C20—C19	110.0 (4)	C27—C28—H28C	109.5
C23—C20—C19	111.0 (4)	H28A—C28—H28C	109.5
N2—C18—C19	109.8 (4)	H28B—C28—H28C	109.5
N2—C18—H18A	109.7	C31—C34—H34A	109.5
C19—C18—H18A	109.7	C31—C34—H34B	109.5
N2—C18—H18B	109.7	H34A—C34—H34B	109.5
C19—C18—H18B	109.7	C31—C34—H34C	109.5
H18A—C18—H18B	108.2	H34A—C34—H34C	109.5
N1—C1—C2	110.1 (4)	H34B—C34—H34C	109.5
N1—C1—H1A	109.6	O8—C22—C21	103.4 (5)
C2—C1—H1A	109.6	O8—C22—H22A	111.1
N1—C1—H1B	109.6	C21—C22—H22A	111.1
C2—C1—H1B	109.6	O8—C22—H22B	111.1
H1A—C1—H1B	108.1	C21—C22—H22B	111.1
C7—C6—C3	114.0 (4)	H22A—C22—H22B	109.1
C7—C6—H6A	108.7	C14—C15—H15A	109.5
C3—C6—H6A	108.7	C14—C15—H15B	109.5
C7—C6—H6B	108.7	H15A—C15—H15B	109.5
C3—C6—H6B	108.7	C14—C15—H15C	109.5
H6A—C6—H6B	107.6	H15A—C15—H15C	109.5
O2—C3—O1	106.4 (4)	H15B—C15—H15C	109.5
O2—C3—C2	110.1 (4)	C27—C29—H29A	109.5
O1—C3—C2	108.8 (4)	C27—C29—H29B	109.5
O2—C3—C6	109.2 (4)	H29A—C29—H29B	109.5
O1—C3—C6	109.6 (4)	C27—C29—H29C	109.5
C2—C3—C6	112.5 (4)	H29A—C29—H29C	109.5
O12—C31—C34	103.4 (4)	H29B—C29—H29C	109.5
O12—C31—C32	110.8 (4)	C14—C16—H16A	109.5
C34—C31—C32	110.7 (5)	C14—C16—H16B	109.5
O12—C31—C33	110.0 (4)	H16A—C16—H16B	109.5
C34—C31—C33	110.1 (5)	C14—C16—H16C	109.5
C32—C31—C33	111.6 (5)	H16A—C16—H16C	109.5
O9—C25—C24	111.4 (4)	H16B—C16—H16C	109.5
O9—C25—C26	101.8 (4)	C10—C11—H11A	109.5
C24—C25—C26	111.9 (4)	C10—C11—H11B	109.5
O9—C25—H25	110.5	H11A—C11—H11B	109.5
C24—C25—H25	110.5	C10—C11—H11C	109.5
C26—C25—H25	110.5	H11A—C11—H11C	109.5
C20—C23—C24	115.0 (4)	H11B—C11—H11C	109.5
C20—C23—H23A	108.5	C14—C17—H17A	109.5
C24—C23—H23A	108.5	C14—C17—H17B	109.5
C20—C23—H23B	108.5	H17A—C17—H17B	109.5
C24—C23—H23B	108.5	C14—C17—H17C	109.5
H23A—C23—H23B	107.5	H17A—C17—H17C	109.5
C20—C19—C18	111.3 (4)	H17B—C17—H17C	109.5
C20—C19—H19A	109.4	O1—C4—C5	106.5 (6)
C18—C19—H19A	109.4	O1—C4—H4A	110.4
C20—C19—H19B	109.4	C5—C4—H4A	110.4
C18—C19—H19B	109.4	O1—C4—H4B	110.4
H19A—C19—H19B	108.0	C5—C4—H4B	110.4
C3—C2—C1	112.0 (4)	H4A—C4—H4B	108.6
C3—C2—H2A	109.2	O2—C5—C4	107.7 (6)
C1—C2—H2A	109.2	O2—C5—H5A	110.2
C3—C2—H2B	109.2	C4—C5—H5A	110.2
C1—C2—H2B	109.2	O2—C5—H5B	110.2
H2A—C2—H2B	107.9	C4—C5—H5B	110.2
O3—C8—C9	102.6 (4)	H5A—C5—H5B	108.5
O3—C8—C7	108.0 (4)	C10—C12—H12A	109.5
C9—C8—C7	114.3 (4)	C10—C12—H12B	109.5
O3—C8—H8	110.5	H12A—C12—H12B	109.5
C9—C8—H8	110.5	C10—C12—H12C	109.5
C7—C8—H8	110.5	H12A—C12—H12C	109.5
O4—C9—C8	103.3 (4)	H12B—C12—H12C	109.5
O4—C9—H9A	111.1	O7—C21—C22	107.0 (5)
C8—C9—H9A	111.1	O7—C21—H21A	110.3
O4—C9—H9B	111.1	C22—C21—H21A	110.3
C8—C9—H9B	111.1	O7—C21—H21B	110.3
H9A—C9—H9B	109.1	C22—C21—H21B	110.3
O10—C27—O9	105.0 (4)	H21A—C21—H21B	108.6
C7—N1—C13—O5	−174.9 (5)	N2—C24—C25—C26	−158.5 (4)
C1—N1—C13—O5	0.9 (7)	C23—C24—C25—C26	78.2 (5)
C7—N1—C13—O6	7.0 (6)	O8—C20—C23—C24	−73.4 (5)
C1—N1—C13—O6	−177.3 (4)	O7—C20—C23—C24	171.3 (4)
C14—O6—C13—O5	9.6 (7)	C19—C20—C23—C24	49.6 (6)
C14—O6—C13—N1	−172.3 (4)	N2—C24—C23—C20	−49.8 (6)
C24—N2—C30—O11	7.3 (7)	C25—C24—C23—C20	74.5 (5)
C18—N2—C30—O11	−175.5 (5)	O8—C20—C19—C18	70.9 (6)
C24—N2—C30—O12	−173.4 (4)	O7—C20—C19—C18	−173.0 (4)
C18—N2—C30—O12	3.8 (7)	C23—C20—C19—C18	−51.5 (6)
C31—O12—C30—O11	−5.8 (7)	N2—C18—C19—C20	55.2 (6)
C31—O12—C30—N2	174.9 (4)	O2—C3—C2—C1	−172.1 (4)
C30—N2—C24—C25	106.8 (5)	O1—C3—C2—C1	71.7 (5)
C18—N2—C24—C25	−70.7 (5)	C6—C3—C2—C1	−49.9 (6)
C30—N2—C24—C23	−127.8 (5)	N1—C1—C2—C3	54.4 (5)
C18—N2—C24—C23	54.7 (5)	C10—O3—C8—C9	−24.2 (6)
C13—N1—C7—C6	−129.2 (5)	C10—O3—C8—C7	−145.2 (4)
C1—N1—C7—C6	54.9 (5)	N1—C7—C8—O3	−59.5 (5)
C13—N1—C7—C8	105.4 (5)	C6—C7—C8—O3	177.3 (4)
C1—N1—C7—C8	−70.5 (5)	N1—C7—C8—C9	−173.0 (4)
C22—O8—C20—O7	−31.4 (5)	C6—C7—C8—C9	63.8 (6)
C22—O8—C20—C23	−149.3 (4)	C10—O4—C9—C8	−26.8 (6)
C22—O8—C20—C19	87.6 (5)	O3—C8—C9—O4	30.6 (5)
C21—O7—C20—O8	25.2 (6)	C7—C8—C9—O4	147.2 (4)
C21—O7—C20—C23	143.3 (6)	C26—O10—C27—O9	−29.8 (5)
C21—O7—C20—C19	−94.4 (6)	C26—O10—C27—C29	88.8 (5)
C30—N2—C18—C19	123.8 (5)	C26—O10—C27—C28	−146.1 (4)
C24—N2—C18—C19	−58.9 (6)	C25—O9—C27—O10	9.2 (5)
C13—N1—C1—C2	124.9 (5)	C25—O9—C27—C29	−110.3 (5)
C7—N1—C1—C2	−58.9 (5)	C25—O9—C27—C28	125.7 (5)
N1—C7—C6—C3	−48.0 (5)	C27—O10—C26—C25	37.5 (5)
C8—C7—C6—C3	76.0 (5)	O9—C25—C26—O10	−30.4 (5)
C5—O2—C3—O1	−10.4 (6)	C24—C25—C26—O10	88.6 (5)
C5—O2—C3—C2	−128.1 (6)	C8—O3—C10—O4	8.4 (6)
C5—O2—C3—C6	107.8 (6)	C8—O3—C10—C11	−108.3 (6)
C4—O1—C3—O2	17.0 (6)	C8—O3—C10—C12	128.1 (5)
C4—O1—C3—C2	135.6 (5)	C9—O4—C10—O3	12.5 (6)
C4—O1—C3—C6	−101.0 (5)	C9—O4—C10—C11	131.2 (5)
C7—C6—C3—O2	170.0 (4)	C9—O4—C10—C12	−103.5 (6)
C7—C6—C3—O1	−73.8 (5)	C13—O6—C14—C15	−65.2 (6)
C7—C6—C3—C2	47.4 (5)	C13—O6—C14—C16	175.9 (4)
C30—O12—C31—C34	−175.4 (4)	C13—O6—C14—C17	60.1 (6)
C30—O12—C31—C32	66.0 (6)	C20—O8—C22—C21	24.9 (6)
C30—O12—C31—C33	−57.8 (6)	C3—O1—C4—C5	−16.9 (8)
C27—O9—C25—C24	−106.4 (4)	C3—O2—C5—C4	0.0 (8)
C27—O9—C25—C26	12.9 (5)	O1—C4—C5—O2	10.6 (9)
N2—C24—C25—O9	−45.4 (5)	C20—O7—C21—C22	−9.5 (8)
C23—C24—C25—O9	−168.7 (4)	O8—C22—C21—O7	−9.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O9^i	0.97	2.45	3.409 (6)	171
C5—H5A···O5^ii	0.97	2.59	3.383 (10)	139
C18—H18B···O2^iii	0.97	2.72	3.643 (7)	158
C22—H22A···O11^ii	0.97	2.59	3.266 (7)	127
C26—H26A···O3	0.97	2.70	3.558 (7)	148

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z.