(1S,3R,4R,4aS,8aS)-4-[(3S)-3-Hydro­xy-3-methyl-4-pentenyl]-3,4a,8,8-tetra­methyl­deca­hydro-1,3-naphthalene­diol

The title compound, C₂₀H₃₆O₃, forms clusters of mol­ecules connected by a co-operative hydrogen-bond chain of five members. The direction of the chain is disordered due to the presence of a crystallographic twofold rotation axis. The clusters are linked via hydrogen bonds in an infinite two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.107
• Data-to-parameter ratio = 11.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O(1)   -  *H(12)             ?

Author response: As a consequnce of the arrangement of the hydroxyl groups, the structure contains some D-H moieties without acceptors. In the comment section we describe this situation as follows: "The packing of the crystal displays clusters of four molecules, connected by hydrogen bonds (see Figure 2). Due to the arrangement of acceptor/donor atoms in a linear chain, it is not possible for each donor to be involved in a hydrogen bond; also some acceptor atoms will remain free. Since a co-operative hydrogen bond chain is normally preferred for this arrangement of donor/acceptor atoms, the hydrogen atoms of the hydroxyl groups were placed in positions enabling such a pattern."

General Notes



HYDTR_01  Extra text has been found in the _refine_ls_hydrogen_treatment field.
          Explanatory text should be in the _publ_section_refinement field.
          Hydrogen treatment given as H atoms: see text
          Hydrogen treatment identified as  see text

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.52
         From the CIF: _reflns_number_total               2367
         Count of symmetry unique reflns         2374
         Completeness (_total/calc)             99.71%
         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.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: COLLECT (Nonius, 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, 2001); software used to prepare material for publication: PLATON.

(I)

Crystal data

C20H36O3	F(000) = 720
Mr = 324.49	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 (29301 reflections wih 0.81 < θ < 27.48 deg).
Monoclinic, C2	Dx = 1.140 Mg m^−3
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 24.767 (3) Å	Cell parameters from 293 reflections
b = 6.2051 (10) Å	θ = 2.0–25.0°
c = 14.1446 (15) Å	µ = 0.07 mm^−1
β = 119.55 (5)°	T = 150 K
V = 1891.0 (10) Å^3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2271 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.042
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
Detector resolution: 18.4 pixels mm^-1	h = −32→32
φ scans and ω scans with κ offset	k = −8→8
28559 measured reflections	l = −18→18
2367 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms: see text
S = 1.04	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 3P] where P = (Fo^2 + 2Fc^2)/3
2367 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.40 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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	Occ. (<1)
O1	0.65690 (9)	0.6465 (6)	0.85744 (18)	0.0618 (11)
O2	0.86882 (11)	0.4182 (5)	1.01009 (19)	0.0639 (9)
O3	1.00606 (9)	0.4387 (5)	0.91019 (16)	0.0526 (8)
C1	0.74437 (12)	0.4908 (5)	0.6138 (2)	0.0380 (9)
C2	0.68265 (13)	0.5396 (7)	0.5136 (2)	0.0478 (10)
C3	0.62939 (13)	0.4829 (6)	0.5339 (2)	0.0443 (10)
C4	0.63101 (12)	0.5976 (5)	0.6316 (2)	0.0353 (8)
C5	0.69670 (10)	0.5652 (5)	0.7325 (2)	0.0302 (7)
C6	0.70876 (12)	0.6688 (6)	0.8393 (2)	0.0425 (9)
C7	0.76458 (12)	0.5561 (8)	0.9333 (2)	0.0515 (12)
C8	0.82497 (13)	0.5771 (7)	0.9296 (3)	0.0486 (12)
C9	0.81305 (11)	0.5102 (5)	0.8160 (2)	0.0350 (8)
C10	0.75444 (11)	0.6111 (4)	0.7166 (2)	0.0295 (8)
C11	0.87329 (12)	0.5223 (6)	0.8069 (3)	0.0409 (10)
C12	0.90117 (12)	0.3047 (5)	0.8124 (2)	0.0361 (8)
C13	0.96500 (12)	0.3102 (6)	0.8185 (2)	0.0367 (9)
C14	0.95973 (13)	0.4059 (6)	0.7159 (2)	0.0389 (9)
C15	0.99272 (14)	0.5639 (6)	0.7098 (3)	0.0486 (10)
C16	0.99002 (17)	0.0800 (7)	0.8315 (3)	0.0583 (12)
C17	0.85497 (17)	0.7939 (8)	0.9710 (3)	0.0626 (13)
C18	0.58075 (12)	0.4843 (7)	0.6489 (3)	0.0511 (12)
C19	0.61240 (15)	0.8358 (6)	0.6059 (3)	0.0525 (11)
C20	0.76417 (15)	0.8518 (5)	0.7029 (3)	0.0440 (10)
H1A	0.77820	0.52980	0.59890	0.0460*
H1B	0.74710	0.33380	0.62790	0.0460*
H2A	0.67890	0.45520	0.45120	0.0580*
H2B	0.68060	0.69450	0.49540	0.0580*
H3A	0.62980	0.32530	0.54520	0.0530*
H3B	0.58980	0.51870	0.46790	0.0530*
H5	0.69900	0.40690	0.74720	0.0360*
H6	0.71840	0.82520	0.83890	0.0510*
H7A	0.77100	0.61720	1.00270	0.0620*
H7B	0.75480	0.40120	0.93230	0.0620*
H9	0.80350	0.35280	0.81150	0.0420*
H11	0.64690	0.78370	0.87630	0.0930*	0.500
H11A	0.86340	0.59210	0.73730	0.0490*
H11B	0.90420	0.61330	0.86660	0.0490*
H12	0.66750	0.54640	0.91580	0.0930*	0.500
H12A	0.87210	0.22090	0.74750	0.0430*
H12B	0.90550	0.22770	0.87710	0.0430*
H14	0.92930	0.34490	0.64910	0.0470*
H15A	1.02380	0.63050	0.77420	0.0580*
H15B	0.98560	0.61210	0.64080	0.0580*
H16A	1.03020	0.08260	0.83390	0.0880*
H16B	0.96070	−0.00770	0.76980	0.0880*
H16C	0.99510	0.01800	0.89910	0.0880*
H17A	0.86470	0.81160	1.04660	0.0940*
H17B	0.82640	0.90800	0.92630	0.0940*
H17C	0.89330	0.80280	0.96700	0.0940*
H18A	0.57040	0.57510	0.69450	0.0760*
H18B	0.59660	0.34520	0.68480	0.0760*
H18C	0.54340	0.46100	0.57840	0.0760*
H19A	0.56940	0.84540	0.54650	0.0780*
H19B	0.64000	0.90700	0.58430	0.0780*
H19C	0.61590	0.90680	0.67070	0.0780*
H20A	0.80770	0.87690	0.72400	0.0660*
H20B	0.75330	0.93790	0.74920	0.0660*
H20C	0.73760	0.89360	0.62680	0.0660*
H21	0.90820	0.48510	1.05610	0.0960*	0.500
H22	0.85180	0.36570	1.05370	0.0960*	0.500
H31	1.01610	0.36450	0.97640	0.0790*	0.500
H32	1.04340	0.46550	0.90720	0.0790*	0.500

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0303 (10)	0.116 (3)	0.0499 (12)	0.0123 (14)	0.0281 (10)	0.0122 (16)
O2	0.0391 (12)	0.098 (2)	0.0463 (13)	0.0158 (15)	0.0146 (10)	0.0223 (16)
O3	0.0260 (9)	0.086 (2)	0.0347 (10)	0.0037 (12)	0.0064 (8)	−0.0124 (13)
C1	0.0358 (14)	0.0416 (17)	0.0443 (15)	0.0054 (13)	0.0257 (12)	0.0001 (14)
C2	0.0447 (16)	0.063 (2)	0.0396 (15)	0.0082 (17)	0.0237 (13)	0.0012 (17)
C3	0.0343 (14)	0.054 (2)	0.0387 (15)	0.0013 (15)	0.0135 (12)	−0.0019 (15)
C4	0.0234 (11)	0.0441 (18)	0.0366 (14)	0.0033 (12)	0.0135 (11)	0.0073 (13)
C5	0.0211 (10)	0.0360 (15)	0.0369 (13)	−0.0018 (11)	0.0168 (10)	0.0022 (12)
C6	0.0265 (12)	0.064 (2)	0.0435 (15)	0.0046 (15)	0.0222 (12)	0.0000 (16)
C7	0.0283 (13)	0.090 (3)	0.0383 (15)	0.0045 (18)	0.0180 (12)	0.0056 (19)
C8	0.0258 (13)	0.071 (3)	0.0474 (17)	0.0024 (16)	0.0169 (12)	0.0036 (18)
C9	0.0201 (11)	0.0416 (17)	0.0455 (15)	−0.0024 (12)	0.0178 (11)	−0.0021 (14)
C10	0.0268 (11)	0.0264 (14)	0.0431 (14)	0.0000 (11)	0.0232 (11)	0.0016 (12)
C11	0.0236 (12)	0.0443 (19)	0.0590 (18)	−0.0048 (13)	0.0237 (13)	−0.0074 (15)
C12	0.0258 (12)	0.0481 (18)	0.0345 (13)	−0.0016 (13)	0.0149 (11)	0.0000 (14)
C13	0.0278 (12)	0.0488 (19)	0.0347 (13)	0.0043 (13)	0.0164 (11)	−0.0006 (14)
C14	0.0321 (13)	0.0515 (19)	0.0351 (13)	−0.0009 (14)	0.0181 (11)	−0.0062 (14)
C15	0.0428 (16)	0.055 (2)	0.0494 (17)	0.0006 (17)	0.0238 (14)	0.0015 (17)
C16	0.056 (2)	0.056 (2)	0.077 (2)	0.0179 (19)	0.0436 (19)	0.011 (2)
C17	0.0438 (18)	0.083 (3)	0.059 (2)	−0.010 (2)	0.0239 (17)	−0.024 (2)
C18	0.0214 (12)	0.078 (3)	0.0487 (17)	−0.0061 (16)	0.0134 (12)	0.0062 (18)
C19	0.0461 (17)	0.056 (2)	0.059 (2)	0.0245 (17)	0.0287 (16)	0.0178 (19)
C20	0.0429 (16)	0.0316 (16)	0.072 (2)	−0.0007 (13)	0.0395 (16)	0.0040 (15)

Geometric parameters (Å, º)

O1—C6	1.435 (4)	C2—H2A	0.9905
O2—C8	1.493 (5)	C2—H2B	0.9899
O3—C13	1.432 (4)	C3—H3A	0.9901
O1—H12	0.9604	C3—H3B	0.9896
O1—H11	0.9604	C5—H5	0.9998
O2—H21	0.9597	C6—H6	1.0001
O2—H22	0.9596	C7—H7A	0.9893
O3—H32	0.9609	C7—H7B	0.9896
O3—H31	0.9598	C9—H9	0.9995
C1—C10	1.541 (4)	C11—H11A	0.9894
C1—C2	1.517 (4)	C11—H11B	0.9901
C2—C3	1.523 (5)	C12—H12A	0.9897
C3—C4	1.537 (4)	C12—H12B	0.9902
C4—C18	1.551 (5)	C14—H14	0.9495
C4—C5	1.560 (4)	C15—H15A	0.9494
C4—C19	1.538 (5)	C15—H15B	0.9504
C5—C6	1.530 (4)	C16—H16A	0.9790
C5—C10	1.579 (4)	C16—H16B	0.9798
C6—C7	1.535 (4)	C16—H16C	0.9795
C7—C8	1.528 (5)	C17—H17A	0.9795
C8—C9	1.541 (5)	C17—H17B	0.9800
C8—C17	1.508 (6)	C17—H17C	0.9800
C9—C10	1.569 (4)	C18—H18A	0.9809
C9—C11	1.561 (5)	C18—H18B	0.9800
C10—C20	1.540 (4)	C18—H18C	0.9804
C11—C12	1.501 (5)	C19—H19A	0.9803
C12—C13	1.541 (5)	C19—H19B	0.9807
C13—C16	1.532 (6)	C19—H19C	0.9815
C13—C14	1.513 (4)	C20—H20A	0.9789
C14—C15	1.306 (5)	C20—H20B	0.9802
C1—H1A	0.9895	C20—H20C	0.9799
C1—H1B	0.9900
O1···C18	2.790 (5)	H9···H5	2.3058
O1···C19	3.374 (4)	H9···H7B	2.5490
O1···O2^i	2.817 (4)	H9···H12A	2.4276
O1···C17^ii	3.386 (5)	H9···H12B	2.3523
O2···C12	3.342 (4)	H11···O2^i	2.0119
O2···O3^iii	2.728 (4)	H11···C7^i	3.0154
O2···O1^ii	2.817 (4)	H11···C8^i	3.0742
O3···O3^iii	2.701 (3)	H11A···C1	2.6567
O3···O2^iii	2.728 (4)	H11A···C14	2.7984
O1···H18B	2.8446	H11A···C20	2.7738
O1···H19C	2.8233	H11A···H1A	2.0880
O1···H17A^ii	2.6764	H11A···H20A	2.1922
O1···H18A	2.2864	H11B···O2	2.8473
O1···H22^i	1.9348	H11B···O3	2.5267
O2···H11B	2.8473	H11B···C17	2.5883
O2···H12B	2.7289	H11B···H17C	1.9622
O2···H11^ii	2.0119	H12···H7A	2.2731
O2···H12^ii	2.8567	H12···H7B	2.2458
O2···H32^iii	1.9164	H12···O2^i	2.8567
O2···H31^iii	2.7810	H12···C17^ii	2.4914
O3···H15A	2.4785	H12···H17A^ii	1.8601
O3···H11B	2.5267	H12···H17B^ii	2.3272
O3···H21^iii	1.9547	H12A···H9	2.4276
O3···H31^iii	1.9887	H12A···H14	2.5458
C12···O2	3.342 (4)	H12A···H16B	2.4988
C17···O1^i	3.386 (5)	H12A···H20A^vi	2.5861
C17···C20	3.340 (5)	H12B···O2	2.7289
C18···O1	2.790 (5)	H12B···H9	2.3523
C19···C20	3.307 (6)	H12B···H16C	2.4563
C19···O1	3.374 (4)	H12B···H31	2.5302
C20···C17	3.340 (5)	H12B···H31^iii	2.1946
C20···C19	3.307 (6)	H14···H12A	2.5458
C1···H11A	2.6567	H14···H3B^vii	2.5075
C2···H20C	2.6630	H15A···O3	2.4785
C2···H19B	2.8905	H15A···H32	1.9804
C6···H20B	2.6488	H15A···H21^iii	2.3291
C6···H22^i	2.8761	H16A···H32	2.5480
C6···H19C	2.7835	H16B···C15^vi	3.0132
C6···H17B	2.9445	H16B···H12A	2.4988
C6···H18A	3.0582	H16C···H12B	2.4563
C7···H11^ii	3.0154	H16C···H31	2.3511
C7···H7B^i	3.0545	H17A···H7A	2.4093
C8···H11^ii	3.0742	H17A···H21	2.2673
C8···H5	3.0929	H17A···O1^i	2.6764
C8···H32^iii	3.0022	H17A···H12^i	1.8601
C11···H17C	2.7012	H17B···C6	2.9445
C11···H1A	2.7148	H17B···C20	2.7710
C11···H31^iii	3.0945	H17B···H6	2.3844
C11···H20A	2.6413	H17B···H20B	2.2614
C12···H31^iii	2.6875	H17B···H12^i	2.3272
C13···H21^iii	2.9482	H17C···C11	2.7012
C13···H31^iii	2.7220	H17C···H11B	1.9622
C14···H11A	2.7984	H17C···H21	2.2698
C15···H16B^iv	3.0132	H18A···O1	2.2864
C15···H32	2.5075	H18A···C6	3.0582
C15···H21^iii	3.0349	H18A···H19C	2.4482
C17···H20B	3.0314	H18B···O1	2.8446
C17···H32^iii	3.0297	H18B···H3A	2.4883
C17···H11B	2.5883	H18B···H5	2.2693
C17···H12^i	2.4914	H18C···H3A	2.5495
C17···H6	2.9557	H18C···H3B	2.3798
C19···H20C	2.9878	H18C···H19A	2.5679
C19···H2B	2.9443	H18C···H18C^viii	2.1994
C19···H6	3.0371	H19A···H3B	2.4809
C20···H2B	2.8034	H19A···H18C	2.5679
C20···H6	2.6765	H19B···C2	2.8905
C20···H11A	2.7738	H19B···C20	2.7019
C20···H17B	2.7710	H19B···H2B	2.3618
C20···H19B	2.7019	H19B···H20C	2.1859
H1A···C11	2.7148	H19C···O1	2.8233
H1A···H11A	2.0880	H19C···C6	2.7835
H1A···H20C	2.5796	H19C···H6	2.5306
H1B···H3A	2.5415	H19C···H18A	2.4482
H1B···H5	2.5407	H20A···C11	2.6413
H1B···H9	2.2652	H20A···H11A	2.1922
H2B···C19	2.9443	H20A···H12A^iv	2.5861
H2B···C20	2.8034	H20B···C6	2.6488
H2B···H19B	2.3618	H20B···C17	3.0314
H2B···H20C	2.0942	H20B···H6	1.9818
H3A···H1B	2.5415	H20B···H17B	2.2614
H3A···H5	2.5548	H20C···C2	2.6630
H3A···H18B	2.4883	H20C···C19	2.9878
H3A···H18C	2.5495	H20C···H1A	2.5796
H3B···H18C	2.3798	H20C···H2B	2.0942
H3B···H19A	2.4809	H20C···H19B	2.1859
H3B···H14^v	2.5075	H21···H17A	2.2673
H5···C8	3.0929	H21···H17C	2.2698
H5···H1B	2.5407	H21···O3^iii	1.9547
H5···H3A	2.5548	H21···C13^iii	2.9482
H5···H7B	2.2797	H21···C15^iii	3.0349
H5···H9	2.3058	H21···H15A^iii	2.3291
H5···H18B	2.2693	H22···H7A	2.3530
H6···C17	2.9557	H22···H7B	2.1679
H6···C19	3.0371	H22···O1^ii	1.9348
H6···C20	2.6765	H22···C6^ii	2.8761
H6···H17B	2.3844	H31···H12B	2.5302
H6···H19C	2.5306	H31···H16C	2.3511
H6···H20B	1.9818	H31···O2^iii	2.7810
H7A···H12	2.2731	H31···O3^iii	1.9887
H7A···H17A	2.4093	H31···C11^iii	3.0945
H7A···H22	2.3530	H31···C12^iii	2.6875
H7A···H7B^i	2.2223	H31···C13^iii	2.7220
H7B···H5	2.2797	H31···H12B^iii	2.1946
H7B···H9	2.5490	H32···C15	2.5075
H7B···H12	2.2458	H32···H15A	1.9804
H7B···H22	2.1679	H32···H16A	2.5480
H7B···C7^ii	3.0545	H32···O2^iii	1.9164
H7B···H7A^ii	2.2223	H32···C8^iii	3.0022
H9···H1B	2.2652	H32···C17^iii	3.0297
C6—O1—H12	109.07	C4—C3—H3B	108.57
H11—O1—H12	109.46	H3A—C3—H3B	107.49
C6—O1—H11	109.90	C4—C5—H5	104.10
H21—O2—H22	109.43	C6—C5—H5	104.13
C8—O2—H21	110.20	C10—C5—H5	104.13
C8—O2—H22	109.24	O1—C6—H6	109.38
C13—O3—H32	108.99	C5—C6—H6	109.46
C13—O3—H31	110.07	C7—C6—H6	109.36
H31—O3—H32	109.52	C6—C7—H7A	108.68
C2—C1—C10	113.9 (3)	C6—C7—H7B	108.70
C1—C2—C3	110.2 (2)	C8—C7—H7A	108.68
C2—C3—C4	114.9 (3)	C8—C7—H7B	108.62
C3—C4—C18	105.4 (3)	H7A—C7—H7B	107.75
C3—C4—C19	111.1 (3)	C8—C9—H9	104.32
C5—C4—C19	113.3 (3)	C10—C9—H9	104.33
C18—C4—C19	107.6 (3)	C11—C9—H9	104.33
C5—C4—C18	110.7 (2)	C9—C11—H11A	108.99
C3—C4—C5	108.4 (3)	C9—C11—H11B	108.99
C4—C5—C6	117.2 (3)	C12—C11—H11A	109.10
C4—C5—C10	117.1 (2)	C12—C11—H11B	109.05
C6—C5—C10	108.4 (2)	H11A—C11—H11B	107.87
O1—C6—C5	112.3 (3)	C11—C12—H12A	108.60
O1—C6—C7	107.7 (3)	C11—C12—H12B	108.62
C5—C6—C7	108.5 (3)	C13—C12—H12A	108.70
C6—C7—C8	114.2 (3)	C13—C12—H12B	108.57
O2—C8—C17	105.0 (3)	H12A—C12—H12B	107.54
C7—C8—C9	109.0 (3)	C13—C14—H14	116.66
C7—C8—C17	111.5 (4)	C15—C14—H14	116.67
C9—C8—C17	116.7 (3)	C14—C15—H15A	120.06
O2—C8—C7	105.9 (3)	C14—C15—H15B	119.92
O2—C8—C9	108.1 (3)	H15A—C15—H15B	120.02
C10—C9—C11	114.0 (2)	C13—C16—H16A	109.45
C8—C9—C10	116.3 (3)	C13—C16—H16B	109.44
C8—C9—C11	111.9 (3)	C13—C16—H16C	109.46
C1—C10—C9	107.4 (2)	H16A—C16—H16B	109.52
C1—C10—C20	108.3 (2)	H16A—C16—H16C	109.49
C5—C10—C9	107.6 (2)	H16B—C16—H16C	109.47
C5—C10—C20	113.7 (3)	C8—C17—H17A	109.43
C9—C10—C20	111.5 (3)	C8—C17—H17B	109.46
C1—C10—C5	108.1 (2)	C8—C17—H17C	109.48
C9—C11—C12	112.7 (3)	H17A—C17—H17B	109.51
C11—C12—C13	114.6 (3)	H17A—C17—H17C	109.45
O3—C13—C16	110.2 (3)	H17B—C17—H17C	109.50
C12—C13—C14	110.7 (2)	C4—C18—H18A	109.50
O3—C13—C14	109.7 (3)	C4—C18—H18B	109.48
C14—C13—C16	108.6 (3)	C4—C18—H18C	109.55
C12—C13—C16	109.2 (3)	H18A—C18—H18B	109.45
O3—C13—C12	108.3 (2)	H18A—C18—H18C	109.39
C13—C14—C15	126.7 (3)	H18B—C18—H18C	109.46
C2—C1—H1A	108.74	C4—C19—H19A	109.47
C2—C1—H1B	108.78	C4—C19—H19B	109.45
C10—C1—H1A	108.81	C4—C19—H19C	109.43
C10—C1—H1B	108.86	H19A—C19—H19B	109.58
H1A—C1—H1B	107.62	H19A—C19—H19C	109.35
C1—C2—H2A	109.60	H19B—C19—H19C	109.55
C1—C2—H2B	109.61	C10—C20—H20A	109.45
C3—C2—H2A	109.67	C10—C20—H20B	109.45
C3—C2—H2B	109.59	C10—C20—H20C	109.44
H2A—C2—H2B	108.15	H20A—C20—H20B	109.49
C2—C3—H3A	108.52	H20A—C20—H20C	109.56
C2—C3—H3B	108.52	H20B—C20—H20C	109.43
C4—C3—H3A	108.57
C10—C1—C2—C3	−58.1 (4)	C5—C6—C7—C8	61.6 (4)
C2—C1—C10—C5	53.1 (3)	C6—C7—C8—O2	−167.2 (3)
C2—C1—C10—C20	−70.5 (4)	C6—C7—C8—C17	79.2 (4)
C2—C1—C10—C9	168.9 (3)	C6—C7—C8—C9	−51.1 (5)
C1—C2—C3—C4	57.2 (4)	O2—C8—C9—C11	−64.0 (4)
C2—C3—C4—C19	74.1 (4)	O2—C8—C9—C10	162.5 (3)
C2—C3—C4—C5	−51.1 (4)	C17—C8—C9—C10	−79.4 (4)
C2—C3—C4—C18	−169.6 (3)	C7—C8—C9—C10	47.9 (4)
C3—C4—C5—C6	179.5 (3)	C7—C8—C9—C11	−178.6 (3)
C3—C4—C5—C10	48.1 (3)	C17—C8—C9—C11	54.0 (4)
C18—C4—C5—C6	−65.4 (4)	C11—C9—C10—C1	58.2 (3)
C18—C4—C5—C10	163.2 (3)	C11—C9—C10—C5	174.4 (2)
C19—C4—C5—C6	55.6 (4)	C8—C9—C10—C20	72.3 (4)
C19—C4—C5—C10	−75.8 (3)	C8—C9—C11—C12	103.3 (3)
C4—C5—C6—C7	160.2 (3)	C10—C9—C11—C12	−122.0 (3)
C4—C5—C10—C1	−49.2 (3)	C11—C9—C10—C20	−60.3 (3)
C10—C5—C6—O1	176.5 (3)	C8—C9—C10—C1	−169.3 (3)
C10—C5—C6—C7	−64.5 (3)	C8—C9—C10—C5	−53.1 (3)
C4—C5—C6—O1	41.2 (4)	C9—C11—C12—C13	−172.6 (2)
C6—C5—C10—C1	175.4 (2)	C11—C12—C13—C16	176.2 (3)
C6—C5—C10—C9	59.7 (3)	C11—C12—C13—O3	56.1 (3)
C6—C5—C10—C20	−64.3 (3)	C11—C12—C13—C14	−64.2 (3)
C4—C5—C10—C9	−165.0 (2)	O3—C13—C14—C15	8.3 (5)
C4—C5—C10—C20	71.0 (3)	C12—C13—C14—C15	127.8 (4)
O1—C6—C7—C8	−176.5 (3)	C16—C13—C14—C15	−112.3 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2^i	0.96	2.01	2.817 (4)	140
O2—H21···O3^iii	0.96	1.95	2.728 (4)	136
O2—H22···O1^ii	0.96	1.93	2.817 (4)	152
O3—H31···O3^iii	0.96	1.99	2.701 (3)	129
O3—H32···O2^iii	0.96	1.92	2.728 (4)	141
C11—H11B···O3	0.99	2.53	2.912 (4)	103
C18—H18A···O1	0.98	2.29	2.790 (5)	111

Symmetry codes: (i) −x+3/2, y+1/2, −z+2; (ii) −x+3/2, y−1/2, −z+2; (iii) −x+2, y, −z+2.