17-Isopropyl-3-meth­oxy-13-methyl-7,8,9,11,12,13,14,15,16,17-deca­hydro-6H-cyclo­penta­[a]phenanthrene

The steroid ring B of the title compound, C₂₂H₃₂O, is in a half-chair conformation. The five-membered ring is in an inter­mediate form between the envelope and half-chair conformations.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.049
• wR factor = 0.131
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

17-isopropyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro- 6H-cyclopenta[a]phenanthrene

Crystal data

C22H32O	F(000) = 688
Mr = 312.48	Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set.
Monoclinic, P21/c	Dx = 1.168 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.260 (6) Å	Cell parameters from 457 reflections
b = 6.1189 (10) Å	θ = 2.0–20.0°
c = 13.662 (3) Å	µ = 0.07 mm^−1
β = 90.35 (1)°	T = 150 K
V = 1777.2 (7) Å^3	Plate, colourless
Z = 4	0.30 × 0.30 × 0.07 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2308 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.097
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
Detector resolution: 18.4 pixels mm^-1	h = −26→26
φ scans and ω scans with κ offset	k = −7→7
37859 measured reflections	l = −16→16
3508 independent reflections

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) = 0.131	Only H-atom coordinates refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.13P] where P = (Fo^2 + 2Fc^2)/3
3508 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O3	0.03148 (5)	0.44570 (18)	0.39750 (8)	0.0387 (4)
C1	0.15613 (8)	0.6826 (3)	0.25448 (12)	0.0349 (6)
C2	0.11231 (8)	0.6494 (3)	0.32635 (12)	0.0355 (6)
C3	0.07350 (8)	0.4669 (3)	0.32188 (12)	0.0328 (5)
C4	0.07901 (8)	0.3217 (3)	0.24508 (12)	0.0332 (6)
C5	0.12333 (7)	0.3567 (2)	0.17145 (11)	0.0312 (5)
C6	0.12619 (9)	0.1939 (3)	0.08869 (13)	0.0379 (6)
C7	0.16213 (9)	0.2740 (3)	0.00066 (13)	0.0402 (6)
C8	0.22270 (8)	0.3832 (3)	0.03118 (12)	0.0354 (5)
C9	0.21009 (8)	0.5834 (3)	0.09453 (12)	0.0331 (5)
C10	0.16321 (7)	0.5383 (3)	0.17555 (11)	0.0311 (5)
C11	0.27142 (8)	0.6908 (3)	0.12807 (13)	0.0382 (6)
C12	0.31603 (9)	0.7407 (3)	0.04348 (13)	0.0361 (6)
C13	0.32896 (8)	0.5406 (3)	−0.02089 (11)	0.0324 (5)
C14	0.26444 (8)	0.4495 (3)	−0.05349 (12)	0.0346 (5)
C15	0.27932 (10)	0.2851 (3)	−0.13368 (13)	0.0426 (6)
C16	0.33746 (9)	0.3820 (3)	−0.18388 (13)	0.0399 (6)
C17	0.35897 (8)	0.5827 (3)	−0.12255 (12)	0.0347 (6)
C18	0.36832 (10)	0.3723 (3)	0.03650 (14)	0.0423 (7)
C20	0.42979 (9)	0.6228 (3)	−0.13130 (13)	0.0404 (6)
C21	0.45357 (10)	0.8113 (3)	−0.06817 (16)	0.0463 (7)
C22	0.44717 (11)	0.6682 (4)	−0.23811 (15)	0.0500 (7)
C30	−0.00588 (9)	0.2510 (3)	0.39983 (15)	0.0411 (6)
H1	0.1816 (8)	0.814 (3)	0.2577 (12)	0.0420*
H2	0.1078 (8)	0.756 (3)	0.3802 (12)	0.0430*
H4	0.0524 (8)	0.191 (3)	0.2398 (12)	0.0400*
H6A	0.0834 (9)	0.148 (3)	0.0713 (12)	0.0460*
H6B	0.1468 (8)	0.057 (3)	0.1144 (12)	0.0460*
H7A	0.1705 (8)	0.152 (3)	−0.0473 (13)	0.0480*
H7B	0.1356 (8)	0.392 (3)	−0.0366 (13)	0.0480*
H8	0.2470 (8)	0.271 (3)	0.0744 (12)	0.0420*
H9	0.1892 (8)	0.688 (3)	0.0504 (12)	0.0400*
H11A	0.2917 (8)	0.595 (3)	0.1773 (13)	0.0460*
H11B	0.2617 (8)	0.829 (3)	0.1650 (13)	0.0460*
H12A	0.3545 (8)	0.809 (3)	0.0702 (12)	0.0430*
H12B	0.2955 (8)	0.859 (3)	−0.0007 (12)	0.0430*
H14	0.2422 (8)	0.577 (3)	−0.0859 (11)	0.0420*
H15A	0.2445 (9)	0.269 (3)	−0.1800 (14)	0.0510*
H15B	0.2888 (8)	0.131 (3)	−0.1051 (13)	0.0510*
H16A	0.3300 (8)	0.426 (3)	−0.2541 (13)	0.0480*
H16B	0.3733 (9)	0.273 (3)	−0.1878 (13)	0.0480*
H17	0.3365 (8)	0.712 (3)	−0.1478 (12)	0.0420*
H18A	0.3770 (9)	0.242 (4)	−0.0033 (14)	0.0630*
H18B	0.3452 (9)	0.327 (3)	0.0998 (16)	0.0630*
H18C	0.4115 (10)	0.435 (3)	0.0561 (14)	0.0630*
H20	0.4508 (8)	0.487 (3)	−0.1110 (12)	0.0480*
H21A	0.4302 (10)	0.953 (3)	−0.0834 (15)	0.0690*
H21B	0.4991 (11)	0.844 (3)	−0.0829 (14)	0.0690*
H21C	0.4485 (9)	0.784 (3)	0.0026 (17)	0.0690*
H22A	0.4332 (10)	0.551 (4)	−0.2809 (16)	0.0750*
H22B	0.4944 (11)	0.688 (3)	−0.2437 (15)	0.0750*
H22C	0.4248 (10)	0.815 (4)	−0.2614 (15)	0.0750*
H30A	−0.0359 (9)	0.250 (3)	0.3388 (15)	0.0620*
H30B	−0.0319 (9)	0.263 (3)	0.4600 (15)	0.0620*
H30C	0.0217 (9)	0.116 (3)	0.4014 (14)	0.0620*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0434 (7)	0.0378 (7)	0.0349 (7)	−0.0049 (5)	0.0020 (5)	−0.0029 (5)
C1	0.0405 (10)	0.0302 (9)	0.0340 (10)	−0.0025 (8)	−0.0046 (8)	−0.0033 (8)
C2	0.0441 (10)	0.0331 (10)	0.0292 (9)	0.0013 (8)	−0.0040 (8)	−0.0048 (8)
C3	0.0352 (9)	0.0337 (9)	0.0294 (9)	0.0033 (8)	−0.0032 (7)	0.0010 (7)
C4	0.0360 (10)	0.0284 (9)	0.0352 (10)	−0.0010 (8)	−0.0066 (8)	0.0004 (8)
C5	0.0354 (9)	0.0272 (9)	0.0308 (9)	0.0018 (7)	−0.0070 (7)	0.0002 (7)
C6	0.0438 (11)	0.0317 (10)	0.0383 (10)	−0.0074 (8)	−0.0019 (8)	−0.0062 (8)
C7	0.0475 (11)	0.0361 (10)	0.0369 (10)	−0.0054 (9)	−0.0021 (9)	−0.0083 (8)
C8	0.0436 (10)	0.0299 (9)	0.0327 (9)	−0.0027 (8)	−0.0027 (8)	−0.0034 (8)
C9	0.0392 (10)	0.0281 (9)	0.0320 (9)	0.0003 (7)	−0.0048 (8)	−0.0013 (7)
C10	0.0344 (9)	0.0279 (9)	0.0308 (9)	0.0015 (7)	−0.0062 (7)	−0.0003 (7)
C11	0.0436 (11)	0.0351 (10)	0.0358 (10)	−0.0039 (8)	−0.0008 (8)	−0.0074 (8)
C12	0.0399 (10)	0.0329 (10)	0.0354 (10)	−0.0039 (8)	−0.0015 (8)	−0.0053 (8)
C13	0.0396 (10)	0.0281 (9)	0.0294 (9)	0.0018 (7)	−0.0023 (7)	−0.0006 (7)
C14	0.0423 (10)	0.0300 (9)	0.0315 (9)	−0.0005 (8)	−0.0038 (8)	−0.0029 (7)
C15	0.0562 (12)	0.0373 (11)	0.0343 (10)	−0.0026 (9)	0.0003 (9)	−0.0066 (8)
C16	0.0505 (12)	0.0378 (10)	0.0314 (10)	0.0051 (9)	0.0002 (8)	−0.0019 (8)
C17	0.0408 (10)	0.0285 (9)	0.0349 (10)	0.0052 (8)	−0.0016 (8)	0.0012 (8)
C18	0.0486 (12)	0.0404 (11)	0.0378 (11)	0.0063 (9)	−0.0021 (9)	0.0049 (9)
C20	0.0444 (11)	0.0352 (10)	0.0416 (11)	0.0059 (8)	0.0016 (8)	0.0006 (8)
C21	0.0425 (12)	0.0466 (12)	0.0497 (12)	−0.0022 (9)	0.0028 (9)	−0.0040 (10)
C22	0.0540 (13)	0.0497 (13)	0.0464 (12)	−0.0005 (11)	0.0083 (10)	−0.0015 (10)
C30	0.0431 (11)	0.0388 (11)	0.0414 (11)	−0.0054 (9)	0.0023 (9)	−0.0010 (9)

Geometric parameters (Å, º)

O3—C3	1.376 (2)	C6—H6A	0.980 (19)
O3—C30	1.432 (2)	C6—H6B	1.008 (18)
C1—C2	1.373 (2)	C7—H7A	1.010 (18)
C1—C10	1.403 (2)	C7—H7B	1.047 (18)
C2—C3	1.390 (3)	C8—H8	1.041 (18)
C3—C4	1.380 (2)	C9—H9	0.983 (17)
C4—C5	1.399 (2)	C11—H11A	0.989 (18)
C5—C6	1.508 (2)	C11—H11B	1.007 (18)
C5—C10	1.399 (2)	C12—H12A	0.987 (17)
C6—C7	1.511 (3)	C12—H12B	1.037 (18)
C7—C8	1.507 (3)	C14—H14	1.013 (18)
C8—C9	1.525 (3)	C15—H15A	0.976 (19)
C8—C14	1.518 (2)	C15—H15B	1.040 (18)
C9—C10	1.519 (2)	C16—H16A	1.008 (18)
C9—C11	1.528 (2)	C16—H16B	1.014 (19)
C11—C12	1.530 (3)	C17—H17	0.986 (18)
C12—C13	1.533 (3)	C18—H18A	0.98 (2)
C13—C14	1.544 (2)	C18—H18B	1.04 (2)
C13—C17	1.554 (2)	C18—H18C	1.03 (2)
C13—C18	1.539 (3)	C20—H20	0.983 (18)
C14—C15	1.522 (3)	C21—H21A	1.020 (19)
C15—C16	1.536 (3)	C21—H21B	1.01 (2)
C16—C17	1.554 (3)	C21—H21C	0.99 (2)
C17—C20	1.531 (3)	C22—H22A	0.97 (2)
C20—C21	1.525 (3)	C22—H22B	1.02 (2)
C20—C22	1.533 (3)	C22—H22C	1.06 (2)
C1—H1	0.970 (18)	C30—H30A	1.05 (2)
C2—H2	0.988 (17)	C30—H30B	1.00 (2)
C4—H4	0.982 (18)	C30—H30C	1.013 (19)
O3···O3^i	3.1817 (18)	H8···H18B	2.14 (3)
O3···C30^i	3.380 (2)	H9···H6B^vi	2.59 (3)
O3···C6^ii	3.397 (2)	H9···H7B	2.44 (3)
O3···C7^ii	3.385 (2)	H9···H12B	2.59 (2)
O3···H6A^iii	2.773 (19)	H9···H14	2.29 (2)
O3···H30B^i	2.64 (2)	H11A···C18	2.872 (18)
O3···H6A^ii	2.675 (17)	H11A···H18B	2.26 (3)
C3···C7^ii	3.411 (3)	H11B···C1	2.714 (17)
C6···O3^iv	3.397 (2)	H11B···H1	2.13 (2)
C7···O3^iv	3.385 (2)	H11B···H16A^vii	2.36 (3)
C7···C3^iv	3.411 (3)	H12A···C21	2.839 (17)
C12···C21	3.334 (3)	H12A···H18C	2.60 (3)
C18···C21	3.546 (3)	H12A···H21C	2.21 (3)
C21···C18	3.546 (3)	H12B···H9	2.59 (2)
C21···C21^v	3.557 (3)	H12B···H14	2.37 (2)
C21···C12	3.334 (3)	H12B···H15B^vi	2.20 (3)
C30···O3^i	3.380 (2)	H12B···H17	2.37 (2)
C1···H30A^iii	2.879 (19)	H14···C11	3.065 (15)
C1···H11B	2.714 (17)	H14···H9	2.29 (2)
C1···H6B^vi	2.991 (18)	H14···H12B	2.37 (2)
C2···H30A^iii	2.84 (2)	H14···H17	2.33 (2)
C2···H7A^ii	2.808 (18)	H14···H1^x	2.58 (2)
C3···H30A^iii	2.91 (2)	H15A···C7	3.035 (19)
C3···H7A^ii	2.816 (18)	H15A···H7A	2.51 (3)
C4···H30A	2.80 (2)	H15B···C18	2.957 (18)
C4···H30A^iii	3.001 (19)	H15B···H12B^ix	2.20 (3)
C4···H30C	2.768 (19)	H15B···H18A	2.43 (3)
C5···H30A^iii	3.044 (19)	H16A···C22	2.906 (18)
C5···H8	2.998 (17)	H16A···H22A	2.35 (3)
C7···H15A	3.035 (19)	H16A···H11B^x	2.36 (3)
C8···H18B	2.78 (2)	H16A···H18B^iv	2.55 (3)
C10···H30A^iii	3.006 (19)	H16B···C22	2.966 (19)
C10···H7B	3.086 (18)	H16B···H18A	2.53 (3)
C11···H1	2.719 (17)	H16B···H20	2.35 (3)
C11···H14	3.065 (15)	H16B···H22A	2.48 (3)
C11···H18B	2.752 (19)	H17···H12B	2.37 (2)
C12···H21C	2.887 (19)	H17···H14	2.33 (2)
C13···H21C	2.961 (19)	H17···H22C	2.52 (3)
C15···H18A	2.740 (19)	H18A···C15	2.740 (19)
C15···H7A	2.728 (17)	H18A···C16	2.74 (2)
C16···H22A	2.65 (2)	H18A···H15B	2.43 (3)
C16···H18A	2.74 (2)	H18A···H16B	2.53 (3)
C18···H15B	2.957 (18)	H18A···H21A^ix	2.37 (3)
C18···H11A	2.872 (18)	H18B···C8	2.78 (2)
C18···H8	2.706 (17)	H18B···C11	2.752 (19)
C18···H21C	3.078 (19)	H18B···H8	2.14 (3)
C18···H20	2.770 (17)	H18B···H11A	2.26 (3)
C20···H18C	2.835 (19)	H18B···H16A^ii	2.55 (3)
C21···H18C	3.000 (19)	H18C···C20	2.835 (19)
C21···H12A	2.839 (17)	H18C···C21	3.000 (19)
C22···H16A	2.906 (18)	H18C···H12A	2.60 (3)
C22···H16B	2.966 (19)	H18C···H20	2.46 (3)
C30···H4	2.546 (17)	H18C···H21C	2.39 (3)
C30···H6A^iii	2.963 (19)	H18C···H21B^xi	2.58 (3)
C30···H6A^ii	3.069 (18)	H20···C18	2.770 (17)
H1···C11	2.719 (17)	H20···H16B	2.35 (3)
H1···H6B^vi	2.56 (2)	H20···H18C	2.46 (3)
H1···H11B	2.13 (2)	H21A···H18A^vi	2.37 (3)
H1···H14^vii	2.58 (2)	H21A···H22C	2.58 (3)
H2···H7B^vii	2.50 (3)	H21B···H22B	2.40 (3)
H4···C30	2.546 (17)	H21B···H18C^xi	2.58 (3)
H4···H6A	2.41 (2)	H21C···C12	2.887 (19)
H4···H30A	2.35 (3)	H21C···C13	2.961 (19)
H4···H30C	2.35 (3)	H21C···C18	3.078 (19)
H6A···H4	2.41 (2)	H21C···H12A	2.21 (3)
H6A···O3^viii	2.773 (19)	H21C···H18C	2.39 (3)
H6A···C30^viii	2.963 (19)	H22A···C16	2.65 (2)
H6A···O3^iv	2.675 (17)	H22A···H16A	2.35 (3)
H6A···C30^iv	3.069 (18)	H22A···H16B	2.48 (3)
H6B···C1^ix	2.991 (18)	H22B···H21B	2.40 (3)
H6B···H1^ix	2.56 (2)	H22C···H17	2.52 (3)
H6B···H8	2.56 (2)	H22C···H21A	2.58 (3)
H6B···H9^ix	2.59 (3)	H30A···C4	2.80 (2)
H7A···C15	2.728 (17)	H30A···H4	2.35 (3)
H7A···H15A	2.51 (3)	H30A···C1^viii	2.88 (2)
H7A···C2^iv	2.808 (18)	H30A···C2^viii	2.84 (2)
H7A···C3^iv	2.816 (18)	H30A···C3^viii	2.91 (2)
H7B···C10	3.086 (18)	H30A···C4^viii	3.001 (19)
H7B···H9	2.44 (3)	H30A···C5^viii	3.044 (19)
H7B···H2^x	2.50 (3)	H30A···C10^viii	3.006 (19)
H7B···H30C^iv	2.56 (3)	H30B···O3^i	2.64 (2)
H8···C5	2.998 (17)	H30C···C4	2.768 (19)
H8···C18	2.706 (17)	H30C···H4	2.35 (3)
H8···H6B	2.56 (2)	H30C···H7B^ii	2.56 (3)
C3—O3—C30	117.24 (13)	C14—C8—H8	108.6 (9)
C2—C1—C10	122.23 (16)	C8—C9—H9	104.8 (10)
C1—C2—C3	119.53 (16)	C10—C9—H9	105.6 (10)
O3—C3—C2	115.52 (15)	C11—C9—H9	106.6 (10)
O3—C3—C4	124.65 (16)	C9—C11—H11A	108.5 (10)
C2—C3—C4	119.84 (16)	C9—C11—H11B	109.5 (10)
C3—C4—C5	120.58 (16)	C12—C11—H11A	111.2 (10)
C4—C5—C6	117.92 (14)	C12—C11—H11B	109.9 (10)
C4—C5—C10	120.24 (14)	H11A—C11—H11B	104.3 (15)
C6—C5—C10	121.84 (14)	C11—C12—H12A	108.7 (10)
C5—C6—C7	113.92 (15)	C11—C12—H12B	108.6 (9)
C6—C7—C8	111.04 (15)	C13—C12—H12A	113.5 (10)
C7—C8—C9	111.12 (14)	C13—C12—H12B	107.5 (10)
C7—C8—C14	114.22 (14)	H12A—C12—H12B	105.4 (14)
C9—C8—C14	108.88 (15)	C8—C14—H14	105.4 (9)
C8—C9—C10	112.71 (15)	C13—C14—H14	105.1 (10)
C8—C9—C11	111.29 (14)	C15—C14—H14	107.0 (9)
C10—C9—C11	114.96 (14)	C14—C15—H15A	111.9 (11)
C1—C10—C5	117.59 (14)	C14—C15—H15B	111.7 (10)
C1—C10—C9	121.32 (15)	C16—C15—H15A	111.0 (11)
C5—C10—C9	121.02 (14)	C16—C15—H15B	111.3 (10)
C9—C11—C12	113.02 (14)	H15A—C15—H15B	107.3 (15)
C11—C12—C13	112.83 (15)	C15—C16—H16A	113.9 (10)
C12—C13—C14	106.96 (14)	C15—C16—H16B	112.1 (11)
C12—C13—C17	117.16 (15)	C17—C16—H16A	110.3 (10)
C12—C13—C18	109.94 (14)	C17—C16—H16B	109.2 (11)
C14—C13—C17	99.85 (12)	H16A—C16—H16B	103.8 (14)
C14—C13—C18	112.63 (15)	C13—C17—H17	104.2 (10)
C17—C13—C18	109.97 (14)	C16—C17—H17	107.8 (10)
C8—C14—C13	113.54 (13)	C20—C17—H17	108.6 (10)
C8—C14—C15	119.81 (15)	C13—C18—H18A	111.4 (12)
C13—C14—C15	104.96 (14)	C13—C18—H18B	110.2 (11)
C14—C15—C16	103.75 (15)	C13—C18—H18C	111.4 (10)
C15—C16—C17	107.41 (14)	H18A—C18—H18B	109.7 (16)
C13—C17—C16	103.29 (14)	H18A—C18—H18C	106.0 (16)
C13—C17—C20	120.39 (14)	H18B—C18—H18C	108.1 (15)
C16—C17—C20	111.77 (14)	C17—C20—H20	106.7 (10)
C17—C20—C21	113.58 (16)	C21—C20—H20	109.4 (10)
C17—C20—C22	110.26 (16)	C22—C20—H20	108.1 (10)
C21—C20—C22	108.69 (16)	C20—C21—H21A	111.6 (12)
C2—C1—H1	118.1 (10)	C20—C21—H21B	110.6 (11)
C10—C1—H1	119.6 (10)	C20—C21—H21C	112.8 (11)
C1—C2—H2	120.3 (10)	H21A—C21—H21B	104.9 (16)
C3—C2—H2	120.2 (10)	H21A—C21—H21C	106.7 (16)
C3—C4—H4	121.9 (10)	H21B—C21—H21C	109.8 (16)
C5—C4—H4	117.5 (10)	C20—C22—H22A	111.4 (14)
C5—C6—H6A	109.2 (10)	C20—C22—H22B	109.7 (12)
C5—C6—H6B	107.9 (10)	C20—C22—H22C	109.1 (11)
C7—C6—H6A	111.9 (10)	H22A—C22—H22B	110.0 (17)
C7—C6—H6B	109.0 (10)	H22A—C22—H22C	108.0 (18)
H6A—C6—H6B	104.3 (15)	H22B—C22—H22C	108.5 (16)
C6—C7—H7A	111.6 (10)	O3—C30—H30A	108.8 (10)
C6—C7—H7B	109.7 (10)	O3—C30—H30B	105.5 (11)
C8—C7—H7A	110.7 (10)	O3—C30—H30C	111.0 (11)
C8—C7—H7B	106.6 (10)	H30A—C30—H30B	108.6 (16)
H7A—C7—H7B	106.9 (14)	H30A—C30—H30C	111.2 (15)
C7—C8—H8	106.6 (10)	H30B—C30—H30C	111.5 (15)
C9—C8—H8	107.2 (10)
C30—O3—C3—C2	−175.14 (15)	C10—C9—C11—C12	−177.85 (15)
C30—O3—C3—C4	4.6 (2)	C8—C9—C10—C1	165.14 (15)
C10—C1—C2—C3	0.3 (3)	C8—C9—C10—C5	−18.1 (2)
C2—C1—C10—C5	0.5 (2)	C11—C9—C10—C1	36.2 (2)
C2—C1—C10—C9	177.33 (16)	C9—C11—C12—C13	−52.9 (2)
C1—C2—C3—O3	179.35 (15)	C11—C12—C13—C14	53.77 (18)
C1—C2—C3—C4	−0.5 (3)	C11—C12—C13—C17	164.71 (14)
C2—C3—C4—C5	−0.1 (3)	C11—C12—C13—C18	−68.82 (19)
O3—C3—C4—C5	−179.86 (15)	C17—C13—C14—C8	178.22 (15)
C3—C4—C5—C6	−178.98 (16)	C18—C13—C14—C8	61.61 (19)
C3—C4—C5—C10	0.8 (2)	C18—C13—C14—C15	−71.04 (17)
C4—C5—C6—C7	164.55 (15)	C17—C13—C14—C15	45.57 (17)
C10—C5—C6—C7	−15.3 (2)	C12—C13—C14—C8	−59.28 (19)
C6—C5—C10—C9	1.9 (2)	C12—C13—C14—C15	168.06 (14)
C6—C5—C10—C1	178.80 (15)	C14—C13—C17—C20	−165.13 (16)
C4—C5—C10—C1	−1.0 (2)	C18—C13—C17—C16	78.95 (17)
C4—C5—C10—C9	−177.87 (15)	C18—C13—C17—C20	−46.5 (2)
C5—C6—C7—C8	44.6 (2)	C12—C13—C17—C20	79.9 (2)
C6—C7—C8—C9	−61.74 (19)	C14—C13—C17—C16	−39.65 (16)
C6—C7—C8—C14	174.61 (15)	C12—C13—C17—C16	−154.60 (15)
C7—C8—C9—C10	47.51 (19)	C8—C14—C15—C16	−161.92 (15)
C7—C8—C14—C13	−174.42 (15)	C13—C14—C15—C16	−32.92 (17)
C7—C8—C14—C15	−49.4 (2)	C14—C15—C16—C17	7.08 (18)
C9—C8—C14—C13	60.73 (19)	C15—C16—C17—C20	151.69 (15)
C9—C8—C14—C15	−174.24 (15)	C15—C16—C17—C13	20.84 (18)
C7—C8—C9—C11	178.37 (14)	C13—C17—C20—C21	−55.7 (2)
C14—C8—C9—C10	174.16 (13)	C13—C17—C20—C22	−177.91 (17)
C14—C8—C9—C11	−54.99 (18)	C16—C17—C20—C21	−177.07 (15)
C11—C9—C10—C5	−147.09 (15)	C16—C17—C20—C22	60.7 (2)
C8—C9—C11—C12	52.5 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+2, −z; (vi) x, y+1, z; (vii) x, −y+3/2, z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) x, y−1, z; (x) x, −y+3/2, z−1/2; (xi) −x+1, −y+1, −z.