1(5),6(7)-Di­epoxy-4-guaiol hemihydrate

The title compound, C₁₅H₂₄O₃·0.5H₂O, crystallizes in the space group P2₁ with two mol­ecules in the asymmetric unit, both with the same conformation. In the crystal structure, O—H...O hydrogen bonds link the two independent mol­ecules, A and B, into an infinite chain along the a axis. These chains are further interlinked by water mol­ecules through O—H...O hydrogen bonds in different directions into supramolecular arrays.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.134
• Data-to-parameter ratio = 9.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.197
          Weighting scheme identified as calc

PLAT_320  Alert C Check Hybridisation of  C8A    in Main Residue          ?

PLAT_320  Alert C Check Hybridisation of  C8B    in Main Residue          ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.00
         From the CIF: _reflns_number_total               3127
         Count of symmetry unique reflns         3140
         Completeness (_total/calc)             99.59%
         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

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

S1. Comment

1(5),6(7)-diepoxy-4-guaiol, also known as as singuaiol, was isolated from the soft coral sinularia sp., collected from Sanya bay, Hainan Province, China. In this sesquiterpenoid, besides the ordinary epoxy group between atoms C6 and C7, there is a rare epoxy group between atoms C1 and C5. It is a new guaiane sesquiterpenoid. Its structure was elucidated on the basis of spectroscopic analysis (Rao et al.2000). We undertook an X-ray study of 1(5),6(7)-diepoxy-4-guaiol to confirm the relative stereochemistry and present here the structure of its hemihydrate, (I).

The X-ray study of (I) confirms the previously proposed structure based on spectroscopic data. The asymmetric unit of (I) consists of two independent molecules, A and B (Fig. 1), linked by hydrogen bonds O1A—H1A···O2B and O1B—H1B···O3A (Table 1). Its crystal structure shows that the two epoxy rings are approximately equilateral triangles. The C—O and C—C bond lengths are in the range 1.447 (3)–1.476 Å, and the angles are in the range 58.95 (15)–60.85 (15)°. [There is no bond length 1.476 and no angles as given, please check]

In the solid-state structure, O1A—H1A···O2B and O1B—H1B···O3A hydrogen bonds link the two independent molecules into an infinite chain along the a axis. These chains are further interlinked by the water molecules through O1W—H1WA···O1B and O1W—H1WB···O1A hydrogen bonds into supramolecular arrays (Fig. 2).

S2. Experimental

Freshly collected soft coral sinularia sp. was cut into pieces and extracted with EtOH three times. The combined extracts were concentrated under reduced pressure and the crude extract was partitioned between H₂O and EtOAc. The EtOAc-soluble portion was subjected to silica-gel column chromatography, eluting with EtOAc–hexane, and afforded the product 1(5),6(7)-diepoxy-4-guaiol according to NMR and two-dimensional NMR spectra. Crystals of (I) were obtained from hexane/EtOAc by solvent diffusion. ¹H NMR (500 MHz; CDCl₃): δ 1.73 (m, H2a), 2.01 (m, H2b), 1.56 (m, H3a), 1.62 (m, H3b), 3.15 (s, H6), 1.76 (m, H8a), 2.05 (m, H8b), 1.17 (m, H9a), 1.53 (m, H9b), 1.98 (m, H10), 1.07 (d, J = 7.0 Hz, H11), 1.54 (m, H12), 0.98 (d, J = 6.5 Hz, H13), 0.95 (d, J = 6.5 Hz, H14), 1.45 (s, H15).

S3. Refinement

The H atoms were positioned geometrically and were treated as riding on their parent C and O atoms, with C—H distances of 0.96 Å and O—H distances of 0.85 Å. The Friedel opposites were merged during the refinement.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. View of the title molecule, showing 30% probability displacement ellipsoids.
	Fig. 2. Perspective views showing the molecular packing of (I), viewed along the b axis direction. All H atoms on C atoms have been omitted for clarity.

1(5),6(7)-diepoxy-4-guaiol hemihydrate

Crystal data

C15H24O3·0.5H2O	F(000) = 572
Mr = 261.35	Dx = 1.155 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.3492 (13) Å	Cell parameters from 25 reflections
b = 9.9790 (13) Å	θ = 25–31°
c = 14.6493 (18) Å	µ = 0.08 mm^−1
β = 96.382 (2)°	T = 293 K
V = 1503.5 (3) Å^3	Rod, colorless
Z = 4	0.50 × 0.41 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer	2858 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
ω scans	h = −12→12
8011 measured reflections	k = −12→11
3127 independent reflections	l = −18→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.08	Calculated w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.1971P] where P = (Fo^2 + 2Fc^2)/3
3127 reflections	(Δ/σ)max = 0.001
335 parameters	Δρmax = 0.26 e Å^−3
1 restraint	Δρmin = −0.23 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
O1A	0.70920 (18)	0.0826 (2)	0.19439 (13)	0.0557 (5)
H1A	0.7783	0.0466	0.2201	0.080*
O2A	0.48219 (16)	−0.0122 (2)	0.35926 (13)	0.0491 (4)
O3A	0.38221 (16)	−0.1801 (2)	0.20371 (13)	0.0510 (5)
C1A	0.7130 (3)	0.0245 (4)	0.4115 (2)	0.0656 (9)
H1AA	0.7037	0.0429	0.4748	0.080*
H1AB	0.7986	−0.0103	0.4074	0.080*
C2A	0.6903 (3)	0.1507 (4)	0.3541 (2)	0.0664 (9)
H2AA	0.7716	0.1928	0.3459	0.080*
H2AB	0.6381	0.2132	0.3838	0.080*
C3A	0.6211 (3)	0.1082 (3)	0.2614 (2)	0.0503 (6)
C4A	0.5562 (2)	−0.0254 (3)	0.28154 (17)	0.0416 (5)
C5A	0.6115 (2)	−0.0740 (3)	0.37257 (17)	0.0473 (6)
C6A	0.6167 (3)	−0.2147 (4)	0.40948 (19)	0.0562 (7)
H6AA	0.7040	−0.2468	0.4086	0.080*
C7A	0.5271 (3)	−0.3137 (4)	0.3563 (3)	0.0660 (9)
H7AA	0.4399	−0.2799	0.3533	0.080*
H7AB	0.5298	−0.3964	0.3899	0.080*
C8A	0.5579 (3)	−0.3431 (3)	0.2587 (2)	0.0623 (8)
H8AA	0.6094	−0.4191	0.2452	0.080*
H8AB	0.4806	−0.3967	0.2487	0.080*
C9A	0.5015 (2)	−0.2475 (3)	0.1838 (2)	0.0484 (6)
C10A	0.4992 (2)	−0.1029 (3)	0.19948 (18)	0.0442 (5)
H10A	0.4977	−0.0526	0.1435	0.080*
C11A	0.5257 (3)	0.2133 (4)	0.2200 (3)	0.0709 (10)
H11A	0.5717	0.2942	0.2090	0.080*
H11B	0.4824	0.1805	0.1630	0.080*
H11C	0.4625	0.2314	0.2617	0.080*
C12A	0.5886 (4)	−0.2103 (6)	0.5107 (3)	0.0930 (14)
H12A	0.6462	−0.1472	0.5436	0.080*
H12B	0.5002	−0.1829	0.5136	0.080*
H12C	0.6019	−0.2975	0.5378	0.080*
C13A	0.5004 (3)	−0.2928 (4)	0.0849 (2)	0.0616 (8)
H13A	0.4615	−0.2215	0.0474	0.080*
C14A	0.6379 (4)	−0.3082 (7)	0.0607 (3)	0.1008 (17)
H14A	0.6354	−0.3369	−0.0021	0.080*
H14B	0.6823	−0.2238	0.0683	0.080*
H14C	0.6832	−0.3738	0.1002	0.080*
C15A	0.4162 (4)	−0.4159 (5)	0.0621 (3)	0.0881 (12)
H15A	0.4189	−0.4404	−0.0011	0.080*
H15B	0.4483	−0.4888	0.1010	0.080*
H15C	0.3282	−0.3963	0.0724	0.080*
O1B	1.15198 (18)	−0.1477 (3)	0.08521 (13)	0.0591 (6)
O2B	0.95868 (17)	−0.0122 (2)	0.25933 (13)	0.0513 (5)
H1B	1.2215	−0.1428	0.1216	0.080*
O3B	0.89470 (19)	−0.2958 (3)	0.27388 (16)	0.0626 (6)
C1B	1.1761 (3)	0.0758 (3)	0.2399 (2)	0.0550 (7)
H1BA	1.1690	0.1608	0.2696	0.080*
H1BB	1.2662	0.0513	0.2435	0.080*
C2B	1.1160 (3)	0.0812 (4)	0.1387 (2)	0.0645 (8)
H2BA	1.1808	0.1031	0.0990	0.080*
H2BB	1.0488	0.1478	0.1313	0.080*
C3B	1.0592 (3)	−0.0579 (3)	0.11682 (18)	0.0514 (7)
C4B	1.0271 (2)	−0.1108 (3)	0.21055 (16)	0.0408 (5)
C5B	1.0991 (2)	−0.0305 (3)	0.28343 (17)	0.0417 (5)
C6B	1.1434 (3)	−0.0689 (3)	0.38171 (18)	0.0506 (6)
H6BA	1.2354	−0.0847	0.3858	0.080*
C7B	1.0820 (3)	−0.1945 (4)	0.41605 (18)	0.0554 (7)
H7BA	0.9895	−0.1817	0.4105	0.080*
H7BB	1.1112	−0.2052	0.4801	0.080*
C8B	1.1106 (3)	−0.3220 (3)	0.3663 (2)	0.0590 (7)
H8BA	1.1811	−0.3796	0.3891	0.080*
H8BB	1.0534	−0.3702	0.4018	0.080*
C9B	1.0226 (3)	−0.3559 (3)	0.27959 (19)	0.0499 (6)
C10B	0.9826 (2)	−0.2537 (3)	0.21096 (19)	0.0483 (6)
H10B	0.9616	−0.2898	0.1504	0.080*
C11B	0.9447 (3)	−0.0539 (4)	0.0422 (2)	0.0696 (10)
H11D	0.9730	−0.0197	−0.0135	0.080*
H11E	0.9105	−0.1426	0.0317	0.080*
H11F	0.8783	0.0035	0.0614	0.080*
C12B	1.1224 (4)	0.0499 (4)	0.4450 (3)	0.0790 (11)
H12D	1.1619	0.1287	0.4228	0.080*
H12E	1.0308	0.0648	0.4456	0.080*
H12F	1.1611	0.0304	0.5062	0.080*
C13B	1.0234 (4)	−0.4995 (3)	0.2462 (2)	0.0664 (8)
H13B	0.9660	−0.5034	0.1901	0.080*
C14B	1.1578 (4)	−0.5380 (4)	0.2229 (3)	0.0838 (12)
H14D	1.1569	−0.6291	0.2017	0.080*
H14E	1.1818	−0.4798	0.1754	0.080*
H14F	1.2195	−0.5290	0.2765	0.080*
C15B	0.9711 (5)	−0.5981 (5)	0.3111 (3)	0.0942 (14)
H15D	0.9739	−0.6872	0.2866	0.080*
H15E	1.0236	−0.5940	0.3693	0.080*
H15F	0.8829	−0.5754	0.3191	0.080*
O1W	1.2145 (5)	−0.1662 (5)	−0.1012 (3)	0.160 (2)
H1WA	1.1963	−0.1621	−0.0454	0.150*
H1WB	1.2364	−0.2389	−0.1271	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0437 (9)	0.0702 (13)	0.0550 (10)	0.0048 (9)	0.0140 (8)	0.0112 (10)
O2A	0.0383 (9)	0.0605 (11)	0.0501 (10)	0.0000 (8)	0.0115 (7)	−0.0045 (9)
O3A	0.0337 (8)	0.0604 (11)	0.0579 (10)	0.0013 (8)	0.0004 (7)	−0.0085 (9)
C1A	0.0515 (16)	0.093 (3)	0.0517 (16)	−0.0161 (16)	0.0049 (12)	−0.0124 (16)
C2A	0.0583 (17)	0.070 (2)	0.073 (2)	−0.0209 (16)	0.0199 (15)	−0.0186 (18)
C3A	0.0420 (13)	0.0496 (15)	0.0612 (16)	−0.0007 (11)	0.0140 (11)	−0.0005 (13)
C4A	0.0332 (11)	0.0480 (14)	0.0444 (12)	0.0025 (11)	0.0072 (9)	0.0008 (11)
C5A	0.0353 (11)	0.0663 (17)	0.0408 (12)	−0.0012 (12)	0.0070 (9)	−0.0006 (12)
C6A	0.0468 (14)	0.073 (2)	0.0490 (15)	0.0065 (13)	0.0066 (11)	0.0159 (14)
C7A	0.0531 (16)	0.065 (2)	0.079 (2)	−0.0044 (15)	0.0046 (14)	0.0285 (17)
C8A	0.0612 (18)	0.0455 (15)	0.078 (2)	0.0058 (14)	−0.0026 (15)	−0.0025 (15)
C9A	0.0338 (11)	0.0524 (15)	0.0586 (16)	0.0005 (11)	0.0026 (11)	−0.0063 (13)
C10A	0.0385 (12)	0.0499 (14)	0.0437 (12)	0.0029 (11)	0.0033 (9)	0.0035 (11)
C11A	0.0545 (17)	0.0518 (18)	0.109 (3)	0.0077 (14)	0.0217 (18)	0.0119 (18)
C12A	0.105 (3)	0.120 (4)	0.0568 (19)	0.004 (3)	0.0212 (19)	0.028 (2)
C13A	0.0489 (15)	0.072 (2)	0.0635 (17)	−0.0039 (14)	0.0070 (13)	−0.0188 (15)
C14A	0.061 (2)	0.154 (5)	0.090 (3)	−0.005 (3)	0.0208 (19)	−0.039 (3)
C15A	0.098 (3)	0.089 (3)	0.078 (2)	−0.022 (2)	0.011 (2)	−0.031 (2)
O1B	0.0438 (10)	0.0900 (17)	0.0441 (9)	0.0126 (10)	0.0070 (8)	−0.0081 (10)
O2B	0.0364 (9)	0.0658 (12)	0.0524 (10)	0.0129 (9)	0.0076 (7)	−0.0024 (9)
O3B	0.0392 (9)	0.0775 (14)	0.0719 (13)	−0.0096 (10)	0.0095 (9)	0.0069 (11)
C1B	0.0545 (15)	0.0459 (15)	0.0658 (17)	−0.0024 (13)	0.0127 (13)	0.0017 (13)
C2B	0.0695 (19)	0.0629 (19)	0.0629 (18)	0.0045 (16)	0.0146 (15)	0.0203 (16)
C3B	0.0464 (13)	0.0659 (17)	0.0425 (13)	0.0117 (13)	0.0079 (10)	0.0075 (12)
C4B	0.0325 (10)	0.0499 (13)	0.0401 (12)	0.0075 (10)	0.0044 (9)	0.0018 (11)
C5B	0.0339 (11)	0.0461 (14)	0.0456 (12)	0.0047 (10)	0.0069 (9)	−0.0011 (11)
C6B	0.0426 (13)	0.0656 (18)	0.0425 (13)	−0.0053 (12)	−0.0007 (10)	−0.0041 (12)
C7B	0.0602 (16)	0.0686 (19)	0.0367 (12)	−0.0045 (14)	0.0014 (11)	0.0020 (12)
C8B	0.0580 (16)	0.0597 (18)	0.0564 (16)	0.0034 (14)	−0.0059 (13)	0.0096 (14)
C9B	0.0467 (13)	0.0543 (15)	0.0497 (14)	−0.0084 (12)	0.0101 (11)	0.0017 (12)
C10B	0.0405 (12)	0.0605 (16)	0.0427 (13)	−0.0075 (12)	−0.0006 (10)	−0.0019 (12)
C11B	0.0580 (17)	0.102 (3)	0.0470 (15)	0.0172 (18)	0.0000 (12)	0.0169 (17)
C12B	0.099 (3)	0.079 (2)	0.0585 (19)	−0.023 (2)	0.0093 (18)	−0.0213 (18)
C13B	0.083 (2)	0.0536 (17)	0.0640 (18)	−0.0177 (16)	0.0155 (16)	−0.0003 (15)
C14B	0.106 (3)	0.054 (2)	0.097 (3)	−0.0022 (19)	0.039 (2)	−0.0026 (19)
C15B	0.120 (4)	0.066 (2)	0.103 (3)	−0.031 (2)	0.045 (3)	0.000 (2)
O1W	0.268 (6)	0.134 (4)	0.085 (2)	0.082 (4)	0.052 (3)	0.008 (2)

Geometric parameters (Å, º)

O1A—C3A	1.435 (3)	O1B—H1B	0.8481
O1A—H1A	0.8500	O2B—C4B	1.447 (3)
O2A—C4A	1.447 (3)	O2B—C5B	1.468 (3)
O2A—C5A	1.467 (3)	O3B—C10B	1.429 (3)
O3A—C10A	1.442 (3)	O3B—C9B	1.448 (4)
O3A—C9A	1.463 (3)	C1B—C5B	1.510 (4)
C1A—C5A	1.503 (4)	C1B—C2B	1.543 (5)
C1A—C2A	1.518 (6)	C1B—H1BA	0.9600
C1A—H1AA	0.9601	C1B—H1BB	0.9597
C1A—H1AB	0.9600	C2B—C3B	1.528 (5)
C2A—C3A	1.524 (5)	C2B—H2BA	0.9601
C2A—H2AA	0.9598	C2B—H2BB	0.9601
C2A—H2AB	0.9601	C3B—C11B	1.520 (4)
C3A—C11A	1.520 (4)	C3B—C4B	1.541 (4)
C3A—C4A	1.536 (4)	C4B—C5B	1.469 (4)
C4A—C5A	1.473 (4)	C4B—C10B	1.499 (4)
C4A—C10A	1.495 (4)	C5B—C6B	1.511 (4)
C5A—C6A	1.504 (5)	C6B—C7B	1.516 (4)
C6A—C7A	1.511 (5)	C6B—C12B	1.536 (5)
C6A—C12A	1.543 (4)	C6B—H6BA	0.9600
C6A—H6AA	0.9600	C7B—C8B	1.512 (5)
C7A—C8A	1.527 (5)	C7B—H7BA	0.9600
C7A—H7AA	0.9600	C7B—H7BB	0.9599
C7A—H7AB	0.9600	C8B—C9B	1.516 (4)
C8A—C9A	1.520 (4)	C8B—H8BA	0.9600
C8A—H8AA	0.9600	C8B—H8BB	0.9600
C8A—H8AB	0.9599	C9B—C10B	1.460 (4)
C9A—C10A	1.462 (4)	C9B—C13B	1.514 (5)
C9A—C13A	1.517 (4)	C10B—H10B	0.9600
C10A—H10A	0.9600	C11B—H11D	0.9601
C11A—H11A	0.9601	C11B—H11E	0.9600
C11A—H11B	0.9603	C11B—H11F	0.9600
C11A—H11C	0.9597	C12B—H12D	0.9600
C12A—H12A	0.9600	C12B—H12E	0.9602
C12A—H12B	0.9600	C12B—H12F	0.9600
C12A—H12C	0.9600	C13B—C15B	1.510 (5)
C13A—C14A	1.513 (5)	C13B—C14B	1.518 (5)
C13A—C15A	1.522 (5)	C13B—H13B	0.9599
C13A—H13A	0.9600	C14B—H14D	0.9600
C14A—H14A	0.9601	C14B—H14E	0.9601
C14A—H14B	0.9600	C14B—H14F	0.9601
C14A—H14C	0.9600	C15B—H15D	0.9601
C15A—H15A	0.9601	C15B—H15E	0.9599
C15A—H15B	0.9601	C15B—H15F	0.9600
C15A—H15C	0.9600	O1W—H1WA	0.8600
O1B—C3B	1.428 (3)	O1W—H1WB	0.8606
C3A—O1A—H1A	109.9	C4B—O2B—C5B	60.55 (15)
C4A—O2A—C5A	60.74 (15)	C10B—O3B—C9B	61.00 (17)
C10A—O3A—C9A	60.42 (17)	C5B—C1B—C2B	104.8 (2)
C5A—C1A—C2A	105.9 (2)	C5B—C1B—H1BA	111.0
C5A—C1A—H1AA	110.6	C2B—C1B—H1BA	111.2
C2A—C1A—H1AA	110.5	C5B—C1B—H1BB	110.7
C5A—C1A—H1AB	110.5	C2B—C1B—H1BB	110.3
C2A—C1A—H1AB	110.6	H1BA—C1B—H1BB	108.9
H1AA—C1A—H1AB	108.8	C3B—C2B—C1B	105.9 (2)
C1A—C2A—C3A	106.9 (3)	C3B—C2B—H2BA	111.0
C1A—C2A—H2AA	110.4	C1B—C2B—H2BA	110.9
C3A—C2A—H2AA	110.0	C3B—C2B—H2BB	110.4
C1A—C2A—H2AB	110.4	C1B—C2B—H2BB	110.0
C3A—C2A—H2AB	110.6	H2BA—C2B—H2BB	108.7
H2AA—C2A—H2AB	108.6	O1B—C3B—C11B	106.4 (2)
O1A—C3A—C11A	106.5 (3)	O1B—C3B—C2B	112.4 (2)
O1A—C3A—C2A	112.8 (2)	C11B—C3B—C2B	112.2 (3)
C11A—C3A—C2A	112.5 (3)	O1B—C3B—C4B	107.1 (2)
O1A—C3A—C4A	107.6 (2)	C11B—C3B—C4B	114.9 (2)
C11A—C3A—C4A	113.4 (2)	C2B—C3B—C4B	103.9 (2)
C2A—C3A—C4A	104.0 (2)	O2B—C4B—C5B	60.45 (16)
O2A—C4A—C5A	60.28 (16)	O2B—C4B—C10B	118.5 (2)
O2A—C4A—C10A	118.9 (2)	C5B—C4B—C10B	130.3 (2)
C5A—C4A—C10A	129.6 (3)	O2B—C4B—C3B	111.9 (2)
O2A—C4A—C3A	110.7 (2)	C5B—C4B—C3B	108.6 (2)
C5A—C4A—C3A	109.0 (2)	C10B—C4B—C3B	115.2 (2)
C10A—C4A—C3A	115.9 (2)	O2B—C5B—C4B	59.00 (15)
O2A—C5A—C4A	58.98 (15)	O2B—C5B—C1B	111.5 (2)
O2A—C5A—C1A	111.4 (3)	C4B—C5B—C1B	109.0 (2)
C4A—C5A—C1A	108.3 (3)	O2B—C5B—C6B	116.6 (2)
O2A—C5A—C6A	115.8 (2)	C4B—C5B—C6B	129.0 (2)
C4A—C5A—C6A	128.8 (3)	C1B—C5B—C6B	117.5 (2)
C1A—C5A—C6A	118.6 (3)	C5B—C6B—C7B	115.6 (2)
C5A—C6A—C7A	115.5 (2)	C5B—C6B—C12B	109.3 (3)
C5A—C6A—C12A	108.4 (3)	C7B—C6B—C12B	110.2 (2)
C7A—C6A—C12A	110.1 (3)	C5B—C6B—H6BA	107.1
C5A—C6A—H6AA	107.6	C7B—C6B—H6BA	107.1
C7A—C6A—H6AA	107.4	C12B—C6B—H6BA	107.2
C12A—C6A—H6AA	107.5	C8B—C7B—C6B	115.1 (2)
C6A—C7A—C8A	115.4 (3)	C8B—C7B—H7BA	108.5
C6A—C7A—H7AA	108.2	C6B—C7B—H7BA	108.3
C8A—C7A—H7AA	108.5	C8B—C7B—H7BB	108.7
C6A—C7A—H7AB	108.4	C6B—C7B—H7BB	108.6
C8A—C7A—H7AB	108.6	H7BA—C7B—H7BB	107.5
H7AA—C7A—H7AB	107.4	C7B—C8B—C9B	117.4 (3)
C9A—C8A—C7A	116.8 (3)	C7B—C8B—H8BA	121.2
C9A—C8A—H8AA	121.6	C9B—C8B—H8BA	121.3
C7A—C8A—H8AA	121.5	C7B—C8B—H8BB	89.7
C9A—C8A—H8AB	89.5	C9B—C8B—H8BB	89.6
C7A—C8A—H8AB	89.6	H8BA—C8B—H8BB	90.1
H8AA—C8A—H8AB	90.0	O3B—C9B—C10B	58.87 (18)
C10A—C9A—O3A	59.06 (17)	O3B—C9B—C13B	114.3 (3)
C10A—C9A—C13A	116.4 (3)	C10B—C9B—C13B	116.8 (3)
O3A—C9A—C13A	114.2 (2)	O3B—C9B—C8B	114.6 (2)
C10A—C9A—C8A	121.2 (3)	C10B—C9B—C8B	121.2 (3)
O3A—C9A—C8A	114.2 (2)	C13B—C9B—C8B	117.2 (3)
C13A—C9A—C8A	117.6 (3)	O3B—C10B—C9B	60.13 (18)
O3A—C10A—C9A	60.52 (17)	O3B—C10B—C4B	120.0 (2)
O3A—C10A—C4A	120.0 (2)	C9B—C10B—C4B	127.2 (2)
C9A—C10A—C4A	128.7 (2)	O3B—C10B—H10B	113.0
O3A—C10A—H10A	112.5	C9B—C10B—H10B	113.0
C9A—C10A—H10A	112.4	C4B—C10B—H10B	113.1
C4A—C10A—H10A	112.6	C3B—C11B—H11D	109.5
C3A—C11A—H11A	109.6	C3B—C11B—H11E	109.6
C3A—C11A—H11B	109.3	H11D—C11B—H11E	109.5
H11A—C11A—H11B	109.4	C3B—C11B—H11F	109.3
C3A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11E—C11B—H11F	109.5
H11B—C11A—H11C	109.5	C6B—C12B—H12D	109.5
C6A—C12A—H12A	109.2	C6B—C12B—H12E	109.4
C6A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
H12A—C12A—H12B	109.5	C6B—C12B—H12F	109.5
C6A—C12A—H12C	109.8	H12D—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12E—C12B—H12F	109.5
H12B—C12A—H12C	109.5	C15B—C13B—C9B	113.5 (3)
C14A—C13A—C9A	110.3 (3)	C15B—C13B—C14B	112.3 (4)
C14A—C13A—C15A	113.4 (4)	C9B—C13B—C14B	110.5 (3)
C9A—C13A—C15A	113.2 (3)	C15B—C13B—H13B	106.3
C14A—C13A—H13A	106.7	C9B—C13B—H13B	106.9
C9A—C13A—H13A	106.5	C14B—C13B—H13B	107.0
C15A—C13A—H13A	106.2	C13B—C14B—H14D	109.7
C13A—C14A—H14A	109.2	C13B—C14B—H14E	109.1
C13A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14B	109.5	C13B—C14B—H14F	109.6
C13A—C14A—H14C	109.7	H14D—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14E—C14B—H14F	109.5
H14B—C14A—H14C	109.5	C13B—C15B—H15D	109.9
C13A—C15A—H15A	109.9	C13B—C15B—H15E	108.9
C13A—C15A—H15B	109.2	H15D—C15B—H15E	109.5
H15A—C15A—H15B	109.5	C13B—C15B—H15F	109.6
C13A—C15A—H15C	109.3	H15D—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15E—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H1WA—O1W—H1WB	123.7
C3B—O1B—H1B	108.3
C5A—C1A—C2A—C3A	−24.2 (3)	C5B—C1B—C2B—C3B	−27.0 (3)
C1A—C2A—C3A—O1A	−93.1 (3)	C1B—C2B—C3B—O1B	−88.1 (3)
C1A—C2A—C3A—C11A	146.3 (3)	C1B—C2B—C3B—C11B	152.0 (3)
C1A—C2A—C3A—C4A	23.1 (3)	C1B—C2B—C3B—C4B	27.3 (3)
C5A—O2A—C4A—C10A	121.5 (3)	C5B—O2B—C4B—C10B	122.6 (3)
C5A—O2A—C4A—C3A	−100.7 (2)	C5B—O2B—C4B—C3B	−99.6 (2)
O1A—C3A—C4A—O2A	170.6 (2)	O1B—C3B—C4B—O2B	166.2 (2)
C11A—C3A—C4A—O2A	−71.9 (3)	C11B—C3B—C4B—O2B	−75.9 (3)
C2A—C3A—C4A—O2A	50.7 (3)	C2B—C3B—C4B—O2B	47.1 (3)
O1A—C3A—C4A—C5A	106.1 (2)	O1B—C3B—C4B—C5B	101.4 (3)
C11A—C3A—C4A—C5A	−136.4 (3)	C11B—C3B—C4B—C5B	−140.7 (3)
C2A—C3A—C4A—C5A	−13.8 (3)	C2B—C3B—C4B—C5B	−17.7 (3)
O1A—C3A—C4A—C10A	−50.2 (3)	O1B—C3B—C4B—C10B	−54.4 (3)
C11A—C3A—C4A—C10A	67.3 (3)	C11B—C3B—C4B—C10B	63.4 (3)
C2A—C3A—C4A—C10A	−170.1 (2)	C2B—C3B—C4B—C10B	−173.6 (2)
C4A—O2A—C5A—C1A	99.1 (3)	C4B—O2B—C5B—C1B	99.8 (2)
C4A—O2A—C5A—C6A	−121.5 (3)	C4B—O2B—C5B—C6B	−121.3 (3)
C10A—C4A—C5A—O2A	−104.5 (3)	C10B—C4B—C5B—O2B	−103.8 (3)
C3A—C4A—C5A—O2A	103.5 (2)	C3B—C4B—C5B—O2B	105.2 (2)
O2A—C4A—C5A—C1A	−104.4 (3)	O2B—C4B—C5B—C1B	−104.2 (2)
C10A—C4A—C5A—C1A	151.1 (3)	C10B—C4B—C5B—C1B	152.0 (3)
C3A—C4A—C5A—C1A	−0.9 (3)	C3B—C4B—C5B—C1B	1.0 (3)
O2A—C4A—C5A—C6A	99.7 (3)	O2B—C4B—C5B—C6B	100.8 (3)
C10A—C4A—C5A—C6A	−4.8 (4)	C10B—C4B—C5B—C6B	−3.1 (4)
C3A—C4A—C5A—C6A	−156.8 (2)	C3B—C4B—C5B—C6B	−154.1 (2)
C2A—C1A—C5A—O2A	−47.6 (3)	C2B—C1B—C5B—O2B	−47.2 (3)
C2A—C1A—C5A—C4A	15.4 (3)	C2B—C1B—C5B—C4B	16.0 (3)
C2A—C1A—C5A—C6A	174.2 (2)	C2B—C1B—C5B—C6B	174.3 (2)
O2A—C5A—C6A—C7A	53.8 (3)	O2B—C5B—C6B—C7B	55.9 (3)
C4A—C5A—C6A—C7A	−16.0 (4)	C4B—C5B—C6B—C7B	−14.5 (4)
C1A—C5A—C6A—C7A	−169.7 (3)	C1B—C5B—C6B—C7B	−167.7 (2)
O2A—C5A—C6A—C12A	−70.2 (3)	O2B—C5B—C6B—C12B	−69.0 (3)
C4A—C5A—C6A—C12A	−140.0 (3)	C4B—C5B—C6B—C12B	−139.4 (3)
C1A—C5A—C6A—C12A	66.2 (3)	C1B—C5B—C6B—C12B	67.3 (3)
C5A—C6A—C7A—C8A	65.5 (4)	C5B—C6B—C7B—C8B	62.8 (3)
C12A—C6A—C7A—C8A	−171.4 (3)	C12B—C6B—C7B—C8B	−172.7 (3)
C6A—C7A—C8A—C9A	−85.2 (4)	C6B—C7B—C8B—C9B	−86.2 (3)
C10A—O3A—C9A—C13A	−107.4 (3)	C10B—O3B—C9B—C13B	−107.7 (3)
C10A—O3A—C9A—C8A	113.1 (3)	C10B—O3B—C9B—C8B	112.9 (3)
C7A—C8A—C9A—C10A	40.7 (4)	C7B—C8B—C9B—O3B	−23.7 (4)
C7A—C8A—C9A—O3A	−26.5 (4)	C7B—C8B—C9B—C10B	43.5 (4)
C7A—C8A—C9A—C13A	−164.5 (3)	C7B—C8B—C9B—C13B	−161.8 (3)
C9A—O3A—C10A—C4A	−120.2 (3)	C9B—O3B—C10B—C4B	−118.2 (3)
C13A—C9A—C10A—O3A	103.6 (2)	C13B—C9B—C10B—O3B	103.5 (3)
C8A—C9A—C10A—O3A	−101.3 (3)	C8B—C9B—C10B—O3B	−101.6 (3)
O3A—C9A—C10A—C4A	106.5 (3)	O3B—C9B—C10B—C4B	106.8 (3)
C13A—C9A—C10A—C4A	−149.9 (2)	C13B—C9B—C10B—C4B	−149.7 (3)
C8A—C9A—C10A—C4A	5.2 (4)	C8B—C9B—C10B—C4B	5.2 (4)
O2A—C4A—C10A—O3A	−9.6 (4)	O2B—C4B—C10B—O3B	−13.5 (3)
C5A—C4A—C10A—O3A	64.3 (3)	C5B—C4B—C10B—O3B	60.6 (4)
C3A—C4A—C10A—O3A	−145.3 (2)	C3B—C4B—C10B—O3B	−150.0 (2)
O2A—C4A—C10A—C9A	−84.2 (3)	O2B—C4B—C10B—C9B	−87.0 (3)
C5A—C4A—C10A—C9A	−10.3 (4)	C5B—C4B—C10B—C9B	−13.0 (4)
C3A—C4A—C10A—C9A	140.1 (3)	C3B—C4B—C10B—C9B	136.5 (3)
C10A—C9A—C13A—C14A	91.0 (4)	O3B—C9B—C13B—C15B	−72.8 (4)
O3A—C9A—C13A—C14A	157.1 (4)	C10B—C9B—C13B—C15B	−138.7 (3)
C8A—C9A—C13A—C14A	−64.9 (5)	C8B—C9B—C13B—C15B	65.4 (4)
C10A—C9A—C13A—C15A	−140.7 (3)	O3B—C9B—C13B—C14B	160.1 (3)
O3A—C9A—C13A—C15A	−74.7 (4)	C10B—C9B—C13B—C14B	94.2 (4)
C8A—C9A—C13A—C15A	63.3 (4)	C8B—C9B—C13B—C14B	−61.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B	0.85	1.98	2.814 (3)	167
O1B—H1B···O3A^i	0.85	1.98	2.806 (3)	166
O1W—H1WA···O1B	0.86	2.02	2.882 (4)	179
O1W—H1WB···O1A^ii	0.86	2.14	3.002 (5)	179

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