trans-2-(2-Bromo-4-methyl­phenyl­oxy)­cyclo­hexanol

The crystal structure of the title mol­ecule, C₁₃H₁₇BrO₂, contains two crystallographically independent mol­ecules in the asymmetric unit. The cyclo­hexane rings of these two mol­ecules adopt chair conformations. In the solid state, the mol­ecules are aggregated around the cell corners to form a four-membered cooperative O—H...O—H...O—H... hydrogen-bonded ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.122
• Data-to-parameter ratio = 21.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

Trans-2-(2-bromo-4-methylphenyloxy)-cyclohexanol

Crystal data

C13H17BrO2	Z = 4
Mr = 285.18	F(000) = 584
Triclinic, P1	Dx = 1.462 Mg m^−3
a = 9.7151 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6911 (3) Å	Cell parameters from 4186 reflections
c = 12.4332 (3) Å	θ = 1.7–28.3°
α = 77.401 (1)°	µ = 3.16 mm^−1
β = 80.521 (1)°	T = 293 K
γ = 70.905 (1)°	Plate, colourless
V = 1295.65 (5) Å^3	0.24 × 0.20 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer	6185 independent reflections
Radiation source: fine-focus sealed tube	3937 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.7°
ω scans	h = −9→12
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −14→15
Tmin = 0.518, Tmax = 0.743	l = −16→15
9000 measured 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0513P)^2] where P = (Fo^2 + 2Fc^2)/3
6185 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
Br1B	0.40645 (7)	0.54211 (4)	0.83119 (4)	0.0871 (2)
O1B	0.5970 (3)	0.2753 (2)	0.89449 (19)	0.0444 (6)
O2B	0.7840 (3)	0.0502 (2)	1.0026 (3)	0.0609 (7)
H2B	0.8249	0.0926	0.9554	0.091*
C1B	0.4001 (4)	0.4328 (3)	0.6496 (3)	0.0553 (10)
H1B	0.3410	0.5109	0.6221	0.066*
C2B	0.4541 (4)	0.4114 (3)	0.7516 (3)	0.0473 (9)
C3B	0.5414 (3)	0.2960 (3)	0.7950 (3)	0.0387 (7)
C4B	0.5759 (4)	0.2041 (3)	0.7332 (3)	0.0491 (9)
H4B	0.6359	0.1262	0.7601	0.059*
C5B	0.5227 (4)	0.2256 (4)	0.6316 (3)	0.0533 (10)
H5B	0.5477	0.1621	0.5915	0.064*
C6B	0.4326 (4)	0.3406 (3)	0.5887 (3)	0.0487 (9)
C7B	0.3728 (5)	0.3633 (4)	0.4780 (4)	0.0711 (13)
H7D	0.4469	0.3203	0.4273	0.107*
H7E	0.3445	0.4498	0.4487	0.107*
H7F	0.2891	0.3341	0.4881	0.107*
C8B	0.5419 (4)	0.1928 (3)	0.9816 (3)	0.0395 (8)
H8B	0.5236	0.1311	0.9484	0.047*
C9B	0.6596 (4)	0.1283 (3)	1.0587 (3)	0.0442 (8)
H9B	0.6897	0.1898	1.0834	0.053*
C10B	0.6065 (4)	0.0485 (4)	1.1584 (3)	0.0522 (9)
H10C	0.6816	0.0144	1.2091	0.063*
H10D	0.5900	−0.0194	1.1348	0.063*
C11B	0.4663 (5)	0.1194 (4)	1.2182 (3)	0.0628 (11)
H11C	0.4846	0.1827	1.2479	0.075*
H11D	0.4336	0.0642	1.2797	0.075*
C12B	0.3467 (4)	0.1789 (4)	1.1396 (4)	0.0643 (11)
H12C	0.3226	0.1154	1.1145	0.077*
H12D	0.2591	0.2267	1.1784	0.077*
C13B	0.3988 (4)	0.2618 (4)	1.0407 (3)	0.0551 (10)
H13C	0.4122	0.3302	1.0654	0.066*
H13D	0.3245	0.2949	0.9892	0.066*
Br1A	1.31470 (4)	0.03705 (4)	0.54404 (3)	0.05096 (14)
O1A	1.0635 (2)	0.2016 (2)	0.6593 (2)	0.0499 (6)
O2A	1.0011 (3)	0.1388 (2)	0.8876 (3)	0.0614 (7)
H2A	1.0757	0.0903	0.9127	0.092*
C1A	1.0964 (4)	0.1000 (3)	0.3978 (3)	0.0423 (8)
H1A	1.1694	0.0494	0.3557	0.051*
C2A	1.1258 (3)	0.1180 (3)	0.4968 (3)	0.0374 (7)
C3A	1.0212 (4)	0.1932 (3)	0.5629 (3)	0.0401 (8)
C4A	0.8835 (4)	0.2493 (3)	0.5263 (3)	0.0501 (9)
H4A	0.8101	0.2997	0.5683	0.060*
C5A	0.8551 (4)	0.2301 (3)	0.4262 (3)	0.0525 (10)
H5A	0.7621	0.2685	0.4031	0.063*
C6A	0.9588 (4)	0.1570 (3)	0.3606 (3)	0.0466 (9)
C7A	0.9280 (5)	0.1377 (4)	0.2512 (3)	0.0666 (12)
H7A	0.9484	0.0514	0.2524	0.100*
H7B	0.9891	0.1702	0.1919	0.100*
H7C	0.8270	0.1794	0.2401	0.100*
C8A	0.9723 (4)	0.2935 (3)	0.7234 (3)	0.0404 (8)
H8A	0.8701	0.2942	0.7296	0.049*
C9A	1.0275 (4)	0.2524 (3)	0.8374 (3)	0.0435 (8)
H9A	1.1330	0.2410	0.8295	0.052*
C10A	0.9490 (5)	0.3496 (4)	0.9095 (3)	0.0618 (11)
H10A	0.8464	0.3540	0.9243	0.074*
H10B	0.9904	0.3251	0.9799	0.074*
C11A	0.9612 (6)	0.4761 (4)	0.8557 (4)	0.0763 (14)
H11A	0.9056	0.5354	0.9027	0.092*
H11B	1.0628	0.4745	0.8476	0.092*
C12A	0.9036 (6)	0.5152 (4)	0.7428 (4)	0.0710 (13)
H12A	0.9174	0.5939	0.7077	0.085*
H12B	0.7996	0.5248	0.7515	0.085*
C13A	0.9844 (4)	0.4187 (3)	0.6695 (3)	0.0526 (9)
H13A	0.9435	0.4430	0.5989	0.063*
H13B	1.0869	0.4150	0.6553	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1B	0.1400 (5)	0.0404 (2)	0.0823 (4)	−0.0088 (3)	−0.0410 (3)	−0.0198 (2)
O1B	0.0502 (14)	0.0453 (13)	0.0408 (14)	−0.0203 (11)	−0.0170 (11)	0.0041 (11)
O2B	0.0455 (15)	0.0494 (15)	0.071 (2)	−0.0043 (12)	−0.0040 (13)	0.0080 (14)
C1B	0.068 (3)	0.040 (2)	0.055 (3)	−0.0107 (18)	−0.026 (2)	0.0029 (18)
C2B	0.059 (2)	0.0319 (17)	0.052 (2)	−0.0120 (16)	−0.0144 (17)	−0.0062 (16)
C3B	0.0375 (18)	0.0406 (18)	0.0392 (19)	−0.0134 (14)	−0.0092 (14)	−0.0033 (15)
C4B	0.052 (2)	0.0389 (18)	0.047 (2)	−0.0012 (16)	−0.0064 (16)	−0.0072 (17)
C5B	0.066 (2)	0.050 (2)	0.043 (2)	−0.0111 (19)	−0.0067 (18)	−0.0157 (18)
C6B	0.054 (2)	0.053 (2)	0.043 (2)	−0.0226 (18)	−0.0112 (17)	−0.0023 (18)
C7B	0.088 (3)	0.080 (3)	0.053 (3)	−0.033 (3)	−0.026 (2)	−0.003 (2)
C8B	0.0449 (19)	0.0374 (17)	0.0386 (19)	−0.0128 (15)	−0.0129 (14)	−0.0044 (15)
C9B	0.0442 (19)	0.0459 (19)	0.045 (2)	−0.0143 (16)	−0.0160 (15)	−0.0035 (17)
C10B	0.061 (2)	0.058 (2)	0.039 (2)	−0.0220 (19)	−0.0166 (17)	0.0034 (18)
C11B	0.082 (3)	0.069 (3)	0.043 (2)	−0.034 (2)	−0.003 (2)	−0.008 (2)
C12B	0.054 (2)	0.067 (3)	0.066 (3)	−0.017 (2)	0.004 (2)	−0.009 (2)
C13B	0.050 (2)	0.050 (2)	0.057 (3)	−0.0045 (18)	−0.0105 (18)	−0.0041 (19)
Br1A	0.03262 (19)	0.0676 (3)	0.0494 (2)	−0.00139 (16)	−0.00783 (14)	−0.02205 (19)
O1A	0.0397 (13)	0.0566 (14)	0.0477 (15)	0.0073 (11)	−0.0134 (11)	−0.0249 (12)
O2A	0.0547 (16)	0.0500 (15)	0.0672 (19)	−0.0117 (13)	−0.0094 (14)	0.0114 (14)
C1A	0.0416 (19)	0.0454 (19)	0.041 (2)	−0.0115 (16)	−0.0053 (14)	−0.0109 (16)
C2A	0.0323 (16)	0.0413 (17)	0.0377 (19)	−0.0100 (14)	−0.0033 (13)	−0.0074 (15)
C3A	0.0412 (18)	0.0386 (18)	0.041 (2)	−0.0087 (15)	−0.0090 (15)	−0.0089 (15)
C4A	0.0391 (19)	0.047 (2)	0.060 (2)	0.0015 (16)	−0.0114 (16)	−0.0183 (19)
C5A	0.049 (2)	0.047 (2)	0.062 (3)	−0.0077 (17)	−0.0273 (19)	−0.0044 (19)
C6A	0.053 (2)	0.047 (2)	0.043 (2)	−0.0169 (17)	−0.0159 (16)	−0.0043 (17)
C7A	0.078 (3)	0.074 (3)	0.055 (3)	−0.022 (2)	−0.031 (2)	−0.011 (2)
C8A	0.0351 (17)	0.0410 (18)	0.0408 (19)	−0.0018 (14)	−0.0044 (14)	−0.0126 (16)
C9A	0.0385 (18)	0.045 (2)	0.041 (2)	−0.0057 (15)	−0.0046 (14)	−0.0064 (16)
C10A	0.073 (3)	0.064 (3)	0.041 (2)	−0.004 (2)	−0.0094 (19)	−0.018 (2)
C11A	0.093 (3)	0.063 (3)	0.078 (3)	−0.010 (2)	−0.018 (3)	−0.038 (3)
C12A	0.093 (3)	0.043 (2)	0.073 (3)	−0.010 (2)	−0.020 (3)	−0.010 (2)
C13A	0.058 (2)	0.050 (2)	0.048 (2)	−0.0157 (18)	−0.0053 (17)	−0.0064 (18)

Geometric parameters (Å, º)

Br1B—C2B	1.891 (3)	Br1A—C2A	1.894 (3)
O1B—C3B	1.373 (4)	O1A—C3A	1.362 (4)
O1B—C8B	1.443 (4)	O1A—C8A	1.447 (4)
O2B—C9B	1.435 (4)	O2A—C9A	1.424 (4)
O2B—H2B	0.82	O2A—H2A	0.82
C1B—C6B	1.374 (5)	C1A—C2A	1.382 (4)
C1B—C2B	1.393 (5)	C1A—C6A	1.390 (4)
C1B—H1B	0.93	C1A—H1A	0.93
C2B—C3B	1.385 (5)	C2A—C3A	1.391 (4)
C3B—C4B	1.377 (5)	C3A—C4A	1.387 (4)
C4B—C5B	1.384 (5)	C4A—C5A	1.396 (5)
C4B—H4B	0.93	C4A—H4A	0.93
C5B—C6B	1.389 (5)	C5A—C6A	1.372 (5)
C5B—H5B	0.93	C5A—H5A	0.93
C6B—C7B	1.518 (5)	C6A—C7A	1.516 (5)
C7B—H7D	0.96	C7A—H7A	0.96
C7B—H7E	0.96	C7A—H7B	0.96
C7B—H7F	0.96	C7A—H7C	0.96
C8B—C9B	1.509 (4)	C8A—C13A	1.505 (5)
C8B—C13B	1.521 (5)	C8A—C9A	1.520 (5)
C8B—H8B	0.98	C8A—H8A	0.98
C9B—C10B	1.507 (5)	C9A—C10A	1.527 (5)
C9B—H9B	0.98	C9A—H9A	0.98
C10B—C11B	1.514 (6)	C10A—C11A	1.519 (6)
C10B—H10C	0.97	C10A—H10A	0.97
C10B—H10D	0.97	C10A—H10B	0.97
C11B—C12B	1.528 (6)	C11A—C12A	1.517 (6)
C11B—H11C	0.97	C11A—H11A	0.97
C11B—H11D	0.97	C11A—H11B	0.97
C12B—C13B	1.518 (6)	C12A—C13A	1.534 (5)
C12B—H12C	0.97	C12A—H12A	0.97
C12B—H12D	0.97	C12A—H12B	0.97
C13B—H13C	0.97	C13A—H13A	0.97
C13B—H13D	0.97	C13A—H13B	0.97
C3B—O1B—C8B	114.6 (2)	C3A—O1A—C8A	120.1 (2)
C9B—O2B—H2B	109.5	C9A—O2A—H2A	109.5
C6B—C1B—C2B	121.2 (3)	C2A—C1A—C6A	120.5 (3)
C6B—C1B—H1B	119.4	C2A—C1A—H1A	119.7
C2B—C1B—H1B	119.4	C6A—C1A—H1A	119.7
C3B—C2B—C1B	120.8 (3)	C1A—C2A—C3A	122.2 (3)
C3B—C2B—Br1B	119.9 (3)	C1A—C2A—Br1A	118.7 (2)
C1B—C2B—Br1B	119.3 (3)	C3A—C2A—Br1A	119.1 (2)
O1B—C3B—C4B	121.1 (3)	O1A—C3A—C4A	126.3 (3)
O1B—C3B—C2B	120.9 (3)	O1A—C3A—C2A	116.3 (3)
C4B—C3B—C2B	118.0 (3)	C4A—C3A—C2A	117.3 (3)
C3B—C4B—C5B	121.1 (3)	C3A—C4A—C5A	119.9 (3)
C3B—C4B—H4B	119.4	C3A—C4A—H4A	120.0
C5B—C4B—H4B	119.4	C5A—C4A—H4A	120.0
C4B—C5B—C6B	121.1 (3)	C6A—C5A—C4A	122.7 (3)
C4B—C5B—H5B	119.4	C6A—C5A—H5A	118.6
C6B—C5B—H5B	119.4	C4A—C5A—H5A	118.6
C1B—C6B—C5B	117.7 (3)	C5A—C6A—C1A	117.3 (3)
C1B—C6B—C7B	121.3 (3)	C5A—C6A—C7A	122.5 (3)
C5B—C6B—C7B	120.9 (4)	C1A—C6A—C7A	120.2 (3)
C6B—C7B—H7D	109.5	C6A—C7A—H7A	109.5
C6B—C7B—H7E	109.5	C6A—C7A—H7B	109.5
H7D—C7B—H7E	109.5	H7A—C7A—H7B	109.5
C6B—C7B—H7F	109.5	C6A—C7A—H7C	109.5
H7D—C7B—H7F	109.5	H7A—C7A—H7C	109.5
H7E—C7B—H7F	109.5	H7B—C7A—H7C	109.5
O1B—C8B—C9B	107.8 (3)	O1A—C8A—C13A	110.5 (3)
O1B—C8B—C13B	110.9 (3)	O1A—C8A—C9A	105.3 (2)
C9B—C8B—C13B	112.6 (3)	C13A—C8A—C9A	112.1 (3)
O1B—C8B—H8B	108.5	O1A—C8A—H8A	109.7
C9B—C8B—H8B	108.5	C13A—C8A—H8A	109.7
C13B—C8B—H8B	108.5	C9A—C8A—H8A	109.7
O2B—C9B—C10B	107.5 (3)	O2A—C9A—C8A	109.2 (3)
O2B—C9B—C8B	110.1 (3)	O2A—C9A—C10A	109.8 (3)
C10B—C9B—C8B	111.5 (3)	C8A—C9A—C10A	110.0 (3)
O2B—C9B—H9B	109.2	O2A—C9A—H9A	109.3
C10B—C9B—H9B	109.2	C8A—C9A—H9A	109.3
C8B—C9B—H9B	109.2	C10A—C9A—H9A	109.3
C9B—C10B—C11B	112.1 (3)	C11A—C10A—C9A	112.5 (4)
C9B—C10B—H10C	109.2	C11A—C10A—H10A	109.1
C11B—C10B—H10C	109.2	C9A—C10A—H10A	109.1
C9B—C10B—H10D	109.2	C11A—C10A—H10B	109.1
C11B—C10B—H10D	109.2	C9A—C10A—H10B	109.1
H10C—C10B—H10D	107.9	H10A—C10A—H10B	107.8
C10B—C11B—C12B	110.7 (3)	C12A—C11A—C10A	110.6 (4)
C10B—C11B—H11C	109.5	C12A—C11A—H11A	109.5
C12B—C11B—H11C	109.5	C10A—C11A—H11A	109.5
C10B—C11B—H11D	109.5	C12A—C11A—H11B	109.5
C12B—C11B—H11D	109.5	C10A—C11A—H11B	109.5
H11C—C11B—H11D	108.1	H11A—C11A—H11B	108.1
C13B—C12B—C11B	110.1 (4)	C11A—C12A—C13A	110.2 (3)
C13B—C12B—H12C	109.7	C11A—C12A—H12A	109.6
C11B—C12B—H12C	109.7	C13A—C12A—H12A	109.6
C13B—C12B—H12D	109.7	C11A—C12A—H12B	109.6
C11B—C12B—H12D	109.7	C13A—C12A—H12B	109.6
H12C—C12B—H12D	108.2	H12A—C12A—H12B	108.1
C12B—C13B—C8B	111.7 (3)	C8A—C13A—C12A	111.5 (3)
C12B—C13B—H13C	109.3	C8A—C13A—H13A	109.3
C8B—C13B—H13C	109.3	C12A—C13A—H13A	109.3
C12B—C13B—H13D	109.3	C8A—C13A—H13B	109.3
C8B—C13B—H13D	109.3	C12A—C13A—H13B	109.3
H13C—C13B—H13D	108.0	H13A—C13A—H13B	108.0
C6B—C1B—C2B—C3B	−0.5 (6)	C6A—C1A—C2A—C3A	−0.3 (6)
C6B—C1B—C2B—Br1B	179.7 (3)	C6A—C1A—C2A—Br1A	179.5 (3)
C8B—O1B—C3B—C4B	−68.4 (4)	C8A—O1A—C3A—C4A	−13.0 (6)
C8B—O1B—C3B—C2B	114.5 (4)	C8A—O1A—C3A—C2A	169.0 (3)
C1B—C2B—C3B—O1B	178.8 (3)	C1A—C2A—C3A—O1A	179.0 (3)
Br1B—C2B—C3B—O1B	−1.5 (5)	Br1A—C2A—C3A—O1A	−0.8 (4)
C1B—C2B—C3B—C4B	1.5 (6)	C1A—C2A—C3A—C4A	0.8 (5)
Br1B—C2B—C3B—C4B	−178.7 (3)	Br1A—C2A—C3A—C4A	−179.0 (3)
O1B—C3B—C4B—C5B	−178.5 (3)	O1A—C3A—C4A—C5A	−178.6 (4)
C2B—C3B—C4B—C5B	−1.2 (6)	C2A—C3A—C4A—C5A	−0.6 (6)
C3B—C4B—C5B—C6B	−0.1 (6)	C3A—C4A—C5A—C6A	0.0 (6)
C2B—C1B—C6B—C5B	−0.8 (6)	C4A—C5A—C6A—C1A	0.5 (6)
C2B—C1B—C6B—C7B	179.5 (4)	C4A—C5A—C6A—C7A	−179.2 (4)
C4B—C5B—C6B—C1B	1.1 (6)	C2A—C1A—C6A—C5A	−0.3 (5)
C4B—C5B—C6B—C7B	−179.2 (4)	C2A—C1A—C6A—C7A	179.4 (4)
C3B—O1B—C8B—C9B	150.6 (3)	C3A—O1A—C8A—C13A	−75.2 (4)
C3B—O1B—C8B—C13B	−85.7 (3)	C3A—O1A—C8A—C9A	163.7 (3)
O1B—C8B—C9B—O2B	−66.0 (3)	O1A—C8A—C9A—O2A	−65.0 (3)
C13B—C8B—C9B—O2B	171.3 (3)	C13A—C8A—C9A—O2A	174.9 (3)
O1B—C8B—C9B—C10B	174.8 (3)	O1A—C8A—C9A—C10A	174.4 (3)
C13B—C8B—C9B—C10B	52.1 (4)	C13A—C8A—C9A—C10A	54.3 (4)
O2B—C9B—C10B—C11B	−174.6 (3)	O2A—C9A—C10A—C11A	−174.8 (3)
C8B—C9B—C10B—C11B	−53.8 (4)	C8A—C9A—C10A—C11A	−54.6 (4)
C9B—C10B—C11B—C12B	56.7 (4)	C9A—C10A—C11A—C12A	56.3 (5)
C10B—C11B—C12B—C13B	−56.9 (5)	C10A—C11A—C12A—C13A	−56.0 (5)
C11B—C12B—C13B—C8B	55.4 (5)	O1A—C8A—C13A—C12A	−173.1 (3)
O1B—C8B—C13B—C12B	−174.5 (3)	C9A—C8A—C13A—C12A	−56.1 (4)
C9B—C8B—C13B—C12B	−53.6 (4)	C11A—C12A—C13A—C8A	56.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2B—H2B···O2A	0.82	1.97	2.712 (4)	151
O2A—H2A···O2B^i	0.82	1.98	2.777 (4)	164
C4A—H4A···CgB	0.93	3.21	3.968 (4)	140
C12A—H12A···CgA^ii	0.97	3.32	4.272 (5)	166

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