2′-(2-Hydroxy­ethoxy)-1,1′-biphen­yl-2-ol

The title compound, C₁₄H₁₄O₃, was obtained by the Williamson method using 2,2′-dihydr­oxy-1,1′-biphenyl with chloro­hydrin. The asymmetric unit contains two crystallographically independent mol­ecules which differ slightly in the orientations of the hydroxy­ethoxy side chains. In each independent mol­ecule, an intra­molecular O—H...O hydrogen bond is observed. In the solid state, each of the two independent mol­ecules forms an O—H...O hydrogen-bonded centrosymmetric dimer. The crystal packing is further stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.145
• Data-to-parameter ratio = 13.5

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S1. Comment

Biphenyl ethers are used extensively as important chemical materials in the field of liquid crystal chemistry and crown ether chemistry (Martinez-Gomez et al., 2006; Shishkina et al., 2007). We report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). These molecules differ slightly in the orientations of the hydroxyethoxy side chains (Table 1). In one of the independent molecules the two benzene rings (C3—C8 and C9—C14) are twisted away from one another by 59.02 (13)° while in the other molecule the rings are twisted by 63.24 (16)°.

The conformation of each independent molecule is influenced by an intramolecular O—H···O hydrogen bond (Table 2), similar to that observed by Dabrowska et al. (2007). In the solid state, each of the two independent molecules exists as an O—H···O hydrogen-bonded centrosymmetric dimer, and one such dimer is shown in Fig.2. In addition, the crystal packing is stabilized by C—H···π interactions (Table 2). In Table 2, Cg1, Cg2 and Cg3 denote the centroids of C23—C28, C17—C22 and C3—C8 rings, respectively.

Related literature

For the general role of biphenyl ethers, see: Martinez-Gomez et al. (2006); Shishkina et al. (2007). For related hydrogen bonds, see: Dabrowska et al. (2007). For the synthesis of related compounds, see: Niu et al. (2006).

Cg1, Cg2 and Cg3 denote the centroids of the C23–C28, C17–C22 and C3–C8 rings, respectively.

S2. Experimental

The reaction was carried out under nitrogen atmosphere (Niu et al., 2006). 2,2'-Dihydroxy-1,1'-biphenyl (7.44 g, 0.04 mol), sodium hydroxide (1.6 g, 0.04 mol) and chlorohydrin (2.68 ml, 0.04 mol) were added to a solution of ethanol (40 ml). The mixture was heated at reflux for 7 h to ensure completion of the reaction. After cooling to room temperature, the solid product obtained was filtered off and was recrystallized from n-heptane. Single crystals of the title compound suitable for X-ray analysis were grown from ethanol by slow evaporation at room temperature over a period of about one week. Analysis C₁₄H₁₄O₃: C 72.76, H 6.43%; found: C 72.71, H 6.53%.

S3. Refinement

All H atoms were placed in geometrically idealized positions (O—H = 0.82 Å and C—H 0.93 or 0.97 Å) and treated as riding on their parent atoms, with U_iso(H) = 1.5U_eq(O) or 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. H atoms have been omitted for clarity.
	Fig. 2. A view of an O—H···O hydrogen-bonded (dashed lines) dimer in the title compound.

2'-(2-Hydroxyethoxy)-1,1'-biphenyl-2-ol

Crystal data

C14H14O3	Z = 4
Mr = 230.25	F(000) = 488
Triclinic, P1	Dx = 1.284 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2804 (15) Å	Cell parameters from 1864 reflections
b = 12.8846 (18) Å	θ = 2.7–23.7°
c = 14.106 (2) Å	µ = 0.09 mm^−1
α = 108.870 (3)°	T = 298 K
β = 101.160 (2)°	Block, colourless
γ = 99.516 (2)°	0.59 × 0.53 × 0.44 mm
V = 1190.8 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4133 independent reflections
Radiation source: fine-focus sealed tube	2562 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.949, Tmax = 0.962	k = −15→14
6226 measured reflections	l = −16→12

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) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0645P)^2 + 0.2314P] where P = (Fo^2 + 2Fc^2)/3
4133 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.20 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
O1	0.0453 (3)	0.04937 (14)	0.14343 (14)	0.0736 (6)
H1	0.0755	0.0910	0.1127	0.110*
O2	0.2256 (2)	0.27719 (12)	0.22548 (12)	0.0469 (4)
O3	0.1344 (2)	0.15170 (13)	0.00340 (12)	0.0506 (4)
H3	0.0992	0.0844	−0.0338	0.076*
O4	0.7641 (3)	0.52204 (15)	0.45876 (17)	0.0794 (6)
H4	0.8674	0.5627	0.4634	0.119*
O5	0.7889 (3)	0.74097 (15)	0.46791 (14)	0.0628 (5)
O6	1.1385 (2)	0.64946 (13)	0.49509 (13)	0.0564 (5)
H6	1.1735	0.6069	0.5234	0.085*
C1	0.0777 (4)	0.1153 (2)	0.25096 (19)	0.0559 (7)
H1A	0.2016	0.1127	0.2895	0.067*
H1B	−0.0217	0.0834	0.2776	0.067*
C2	0.0755 (4)	0.2349 (2)	0.2665 (2)	0.0549 (7)
H2A	−0.0491	0.2389	0.2302	0.066*
H2B	0.0998	0.2793	0.3398	0.066*
C3	0.2114 (3)	0.36991 (18)	0.19976 (17)	0.0422 (6)
C4	0.1180 (4)	0.4490 (2)	0.24718 (19)	0.0525 (6)
H4A	0.0594	0.4395	0.2978	0.063*
C5	0.1116 (4)	0.5422 (2)	0.2196 (2)	0.0642 (8)
H5	0.0474	0.5949	0.2510	0.077*
C6	0.1997 (5)	0.5569 (2)	0.1459 (2)	0.0708 (8)
H6A	0.1954	0.6196	0.1272	0.085*
C7	0.2950 (4)	0.4788 (2)	0.0994 (2)	0.0599 (7)
H7	0.3545	0.4900	0.0496	0.072*
C8	0.3046 (3)	0.38399 (18)	0.12474 (17)	0.0419 (6)
C9	0.4140 (3)	0.30379 (19)	0.07534 (17)	0.0413 (6)
C10	0.6086 (4)	0.3426 (2)	0.08374 (19)	0.0550 (7)
H10	0.6697	0.4182	0.1229	0.066*
C11	0.7144 (4)	0.2715 (3)	0.0352 (2)	0.0614 (7)
H11	0.8441	0.2995	0.0413	0.074*
C12	0.6259 (4)	0.1602 (2)	−0.0215 (2)	0.0606 (7)
H12	0.6958	0.1120	−0.0540	0.073*
C13	0.4345 (4)	0.1191 (2)	−0.03062 (18)	0.0508 (6)
H13	0.3757	0.0429	−0.0685	0.061*
C14	0.3284 (3)	0.19018 (19)	0.01615 (17)	0.0410 (5)
C15	0.6137 (5)	0.5472 (3)	0.3989 (3)	0.0881 (11)
H15A	0.4921	0.4983	0.3930	0.106*
H15B	0.6307	0.5317	0.3296	0.106*
C16	0.6050 (4)	0.6646 (3)	0.4432 (3)	0.0827 (10)
H16A	0.5120	0.6807	0.3940	0.099*
H16B	0.5612	0.6762	0.5057	0.099*
C17	0.8592 (5)	0.7621 (2)	0.3902 (2)	0.0602 (7)
C18	0.7459 (6)	0.7352 (2)	0.2908 (2)	0.0853 (11)
H18	0.6161	0.6977	0.2717	0.102*
C19	0.8302 (8)	0.7657 (3)	0.2196 (3)	0.1014 (14)
H19	0.7558	0.7468	0.1522	0.122*
C20	1.0166 (8)	0.8217 (3)	0.2467 (3)	0.0997 (13)
H20	1.0695	0.8424	0.1986	0.120*
C21	1.1299 (6)	0.8487 (2)	0.3464 (3)	0.0802 (10)
H21	1.2583	0.8883	0.3648	0.096*
C22	1.0549 (4)	0.8175 (2)	0.4192 (2)	0.0568 (7)
C23	1.1798 (4)	0.84402 (19)	0.52450 (19)	0.0495 (6)
C24	1.2675 (4)	0.9555 (2)	0.5899 (2)	0.0637 (7)
H24	1.2429	1.0138	0.5680	0.076*
C25	1.3902 (4)	0.9814 (3)	0.6867 (3)	0.0731 (9)
H25	1.4473	1.0566	0.7292	0.088*
C26	1.4279 (4)	0.8967 (3)	0.7198 (2)	0.0700 (8)
H26	1.5103	0.9144	0.7851	0.084*
C27	1.3445 (4)	0.7853 (2)	0.6571 (2)	0.0588 (7)
H27	1.3703	0.7277	0.6798	0.071*
C28	1.2219 (3)	0.75958 (19)	0.56005 (19)	0.0471 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0995 (15)	0.0516 (11)	0.0570 (12)	−0.0078 (10)	0.0310 (11)	0.0106 (9)
O2	0.0470 (10)	0.0498 (9)	0.0476 (10)	0.0121 (7)	0.0190 (8)	0.0190 (8)
O3	0.0447 (10)	0.0479 (9)	0.0491 (10)	0.0026 (7)	0.0147 (8)	0.0079 (8)
O4	0.0594 (12)	0.0650 (12)	0.1080 (16)	0.0071 (10)	−0.0061 (12)	0.0444 (12)
O5	0.0576 (12)	0.0642 (11)	0.0653 (12)	0.0134 (9)	0.0122 (10)	0.0253 (10)
O6	0.0612 (11)	0.0449 (10)	0.0614 (11)	0.0136 (8)	0.0100 (9)	0.0205 (9)
C1	0.0592 (17)	0.0593 (16)	0.0518 (16)	0.0098 (13)	0.0225 (13)	0.0217 (13)
C2	0.0526 (16)	0.0650 (17)	0.0493 (15)	0.0121 (13)	0.0221 (13)	0.0200 (13)
C3	0.0383 (13)	0.0395 (13)	0.0392 (13)	0.0050 (10)	0.0036 (11)	0.0078 (10)
C4	0.0495 (15)	0.0521 (15)	0.0483 (15)	0.0118 (12)	0.0164 (12)	0.0069 (12)
C5	0.0654 (19)	0.0471 (15)	0.0738 (19)	0.0219 (13)	0.0188 (16)	0.0099 (14)
C6	0.087 (2)	0.0508 (16)	0.082 (2)	0.0236 (15)	0.0246 (18)	0.0288 (16)
C7	0.0723 (19)	0.0528 (16)	0.0603 (17)	0.0145 (14)	0.0246 (15)	0.0244 (14)
C8	0.0367 (13)	0.0420 (13)	0.0404 (13)	0.0040 (10)	0.0081 (11)	0.0106 (11)
C9	0.0410 (14)	0.0480 (14)	0.0347 (12)	0.0062 (11)	0.0108 (11)	0.0165 (11)
C10	0.0448 (16)	0.0615 (16)	0.0503 (15)	0.0009 (13)	0.0113 (13)	0.0164 (13)
C11	0.0361 (14)	0.091 (2)	0.0560 (17)	0.0121 (14)	0.0159 (13)	0.0244 (16)
C12	0.0534 (17)	0.077 (2)	0.0546 (16)	0.0274 (15)	0.0190 (14)	0.0200 (15)
C13	0.0548 (17)	0.0523 (14)	0.0456 (14)	0.0167 (12)	0.0168 (12)	0.0147 (12)
C14	0.0395 (14)	0.0501 (14)	0.0361 (12)	0.0105 (11)	0.0117 (11)	0.0184 (11)
C15	0.066 (2)	0.077 (2)	0.106 (3)	0.0042 (17)	−0.0099 (19)	0.038 (2)
C16	0.0533 (19)	0.083 (2)	0.110 (3)	0.0160 (16)	0.0113 (18)	0.038 (2)
C17	0.086 (2)	0.0436 (14)	0.0533 (17)	0.0297 (14)	0.0099 (16)	0.0193 (13)
C18	0.122 (3)	0.0630 (19)	0.066 (2)	0.0372 (19)	−0.003 (2)	0.0255 (17)
C19	0.167 (4)	0.080 (2)	0.058 (2)	0.054 (3)	0.003 (3)	0.031 (2)
C20	0.175 (4)	0.080 (2)	0.072 (3)	0.049 (3)	0.048 (3)	0.048 (2)
C21	0.129 (3)	0.0599 (18)	0.074 (2)	0.0314 (18)	0.047 (2)	0.0384 (16)
C22	0.084 (2)	0.0393 (13)	0.0572 (17)	0.0232 (14)	0.0291 (16)	0.0212 (13)
C23	0.0540 (15)	0.0460 (14)	0.0515 (15)	0.0119 (12)	0.0261 (13)	0.0150 (12)
C24	0.0678 (19)	0.0490 (16)	0.075 (2)	0.0118 (14)	0.0310 (17)	0.0173 (15)
C25	0.0573 (18)	0.0591 (18)	0.077 (2)	0.0004 (15)	0.0205 (17)	−0.0027 (16)
C26	0.0497 (17)	0.083 (2)	0.0596 (18)	0.0192 (15)	0.0131 (14)	0.0032 (17)
C27	0.0483 (16)	0.0710 (18)	0.0564 (17)	0.0211 (14)	0.0159 (14)	0.0179 (15)
C28	0.0430 (14)	0.0458 (14)	0.0515 (15)	0.0103 (11)	0.0201 (12)	0.0126 (12)

Geometric parameters (Å, º)

O1—C1	1.428 (3)	C11—C12	1.365 (4)
O1—H1	0.82	C11—H11	0.93
O2—C3	1.370 (3)	C12—C13	1.372 (3)
O2—C2	1.442 (3)	C12—H12	0.93
O3—C14	1.374 (3)	C13—C14	1.383 (3)
O3—H3	0.82	C13—H13	0.93
O4—C15	1.398 (3)	C15—C16	1.455 (4)
O4—H4	0.82	C15—H15A	0.97
O5—C17	1.378 (3)	C15—H15B	0.97
O5—C16	1.430 (3)	C16—H16A	0.97
O6—C28	1.371 (3)	C16—H16B	0.97
O6—H6	0.82	C17—C18	1.382 (4)
C1—C2	1.488 (3)	C17—C22	1.399 (4)
C1—H1A	0.97	C18—C19	1.397 (5)
C1—H1B	0.97	C18—H18	0.93
C2—H2A	0.97	C19—C20	1.344 (5)
C2—H2B	0.97	C19—H19	0.93
C3—C4	1.383 (3)	C20—C21	1.385 (5)
C3—C8	1.405 (3)	C20—H20	0.93
C4—C5	1.382 (4)	C21—C22	1.388 (4)
C4—H4A	0.93	C21—H21	0.93
C5—C6	1.368 (4)	C22—C23	1.482 (4)
C5—H5	0.93	C23—C28	1.390 (3)
C6—C7	1.381 (4)	C23—C24	1.390 (3)
C6—H6A	0.93	C24—C25	1.381 (4)
C7—C8	1.387 (3)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.366 (4)
C8—C9	1.486 (3)	C25—H25	0.93
C9—C10	1.391 (3)	C26—C27	1.376 (4)
C9—C14	1.391 (3)	C26—H26	0.93
C10—C11	1.390 (4)	C27—C28	1.385 (3)
C10—H10	0.93	C27—H27	0.93
C1—O1—H1	109.5	O3—C14—C13	121.1 (2)
C3—O2—C2	116.93 (18)	O3—C14—C9	117.9 (2)
C14—O3—H3	109.5	C13—C14—C9	120.9 (2)
C15—O4—H4	109.5	O4—C15—C16	112.6 (3)
C17—O5—C16	120.3 (2)	O4—C15—H15A	109.1
C28—O6—H6	109.5	C16—C15—H15A	109.1
O1—C1—C2	110.9 (2)	O4—C15—H15B	109.1
O1—C1—H1A	109.5	C16—C15—H15B	109.1
C2—C1—H1A	109.5	H15A—C15—H15B	107.8
O1—C1—H1B	109.5	O5—C16—C15	111.7 (3)
C2—C1—H1B	109.5	O5—C16—H16A	109.3
H1A—C1—H1B	108.0	C15—C16—H16A	109.3
O2—C2—C1	106.8 (2)	O5—C16—H16B	109.3
O2—C2—H2A	110.4	C15—C16—H16B	109.3
C1—C2—H2A	110.4	H16A—C16—H16B	107.9
O2—C2—H2B	110.4	O5—C17—C18	123.5 (3)
C1—C2—H2B	110.4	O5—C17—C22	115.5 (2)
H2A—C2—H2B	108.6	C18—C17—C22	121.0 (3)
O2—C3—C4	122.7 (2)	C17—C18—C19	118.7 (4)
O2—C3—C8	116.4 (2)	C17—C18—H18	120.7
C4—C3—C8	120.8 (2)	C19—C18—H18	120.7
C5—C4—C3	120.2 (2)	C20—C19—C18	121.3 (3)
C5—C4—H4A	119.9	C20—C19—H19	119.3
C3—C4—H4A	119.9	C18—C19—H19	119.3
C6—C5—C4	119.9 (3)	C19—C20—C21	120.0 (4)
C6—C5—H5	120.1	C19—C20—H20	120.0
C4—C5—H5	120.1	C21—C20—H20	120.0
C5—C6—C7	120.0 (2)	C20—C21—C22	121.1 (4)
C5—C6—H6A	120.0	C20—C21—H21	119.4
C7—C6—H6A	120.0	C22—C21—H21	119.4
C6—C7—C8	122.0 (2)	C21—C22—C17	117.9 (3)
C6—C7—H7	119.0	C21—C22—C23	120.4 (3)
C8—C7—H7	119.0	C17—C22—C23	121.7 (2)
C7—C8—C3	117.1 (2)	C28—C23—C24	117.3 (2)
C7—C8—C9	120.3 (2)	C28—C23—C22	121.9 (2)
C3—C8—C9	122.58 (19)	C24—C23—C22	120.7 (2)
C10—C9—C14	117.2 (2)	C25—C24—C23	121.4 (3)
C10—C9—C8	119.9 (2)	C25—C24—H24	119.3
C14—C9—C8	122.8 (2)	C23—C24—H24	119.3
C11—C10—C9	121.8 (2)	C26—C25—C24	120.0 (3)
C11—C10—H10	119.1	C26—C25—H25	120.0
C9—C10—H10	119.1	C24—C25—H25	120.0
C12—C11—C10	119.3 (2)	C25—C26—C27	120.3 (3)
C12—C11—H11	120.3	C25—C26—H26	119.8
C10—C11—H11	120.3	C27—C26—H26	119.8
C11—C12—C13	120.3 (3)	C26—C27—C28	119.5 (3)
C11—C12—H12	119.8	C26—C27—H27	120.2
C13—C12—H12	119.8	C28—C27—H27	120.2
C12—C13—C14	120.4 (2)	O6—C28—C27	121.0 (2)
C12—C13—H13	119.8	O6—C28—C23	117.6 (2)
C14—C13—H13	119.8	C27—C28—C23	121.4 (2)
C3—O2—C2—C1	159.09 (19)	C17—O5—C16—C15	75.7 (3)
O1—C1—C2—O2	−59.1 (3)	O4—C15—C16—O5	50.4 (4)
C2—O2—C3—C4	27.2 (3)	C16—O5—C17—C18	15.8 (3)
C2—O2—C3—C8	−155.41 (19)	C16—O5—C17—C22	−166.6 (2)
O2—C3—C4—C5	178.6 (2)	O5—C17—C18—C19	176.9 (3)
C8—C3—C4—C5	1.4 (3)	C22—C17—C18—C19	−0.5 (4)
C3—C4—C5—C6	−0.7 (4)	C17—C18—C19—C20	−1.6 (5)
C4—C5—C6—C7	−0.1 (4)	C18—C19—C20—C21	1.7 (6)
C5—C6—C7—C8	0.2 (4)	C19—C20—C21—C22	0.3 (5)
C6—C7—C8—C3	0.5 (4)	C20—C21—C22—C17	−2.4 (4)
C6—C7—C8—C9	−178.0 (2)	C20—C21—C22—C23	178.3 (3)
O2—C3—C8—C7	−178.7 (2)	O5—C17—C22—C21	−175.2 (2)
C4—C3—C8—C7	−1.3 (3)	C18—C17—C22—C21	2.4 (4)
O2—C3—C8—C9	−0.2 (3)	O5—C17—C22—C23	4.2 (3)
C4—C3—C8—C9	177.2 (2)	C18—C17—C22—C23	−178.2 (2)
C7—C8—C9—C10	57.1 (3)	C21—C22—C23—C28	−115.6 (3)
C3—C8—C9—C10	−121.3 (2)	C17—C22—C23—C28	65.0 (3)
C7—C8—C9—C14	−120.1 (2)	C21—C22—C23—C24	61.3 (3)
C3—C8—C9—C14	61.4 (3)	C17—C22—C23—C24	−118.1 (3)
C14—C9—C10—C11	0.0 (3)	C28—C23—C24—C25	−0.5 (4)
C8—C9—C10—C11	−177.4 (2)	C22—C23—C24—C25	−177.5 (2)
C9—C10—C11—C12	−0.7 (4)	C23—C24—C25—C26	0.1 (4)
C10—C11—C12—C13	0.2 (4)	C24—C25—C26—C27	0.2 (4)
C11—C12—C13—C14	0.9 (4)	C25—C26—C27—C28	−0.1 (4)
C12—C13—C14—O3	176.7 (2)	C26—C27—C28—O6	179.0 (2)
C12—C13—C14—C9	−1.5 (3)	C26—C27—C28—C23	−0.4 (4)
C10—C9—C14—O3	−177.20 (19)	C24—C23—C28—O6	−178.8 (2)
C8—C9—C14—O3	0.1 (3)	C22—C23—C28—O6	−1.8 (3)
C10—C9—C14—C13	1.1 (3)	C24—C23—C28—C27	0.6 (4)
C8—C9—C14—C13	178.4 (2)	C22—C23—C28—C27	177.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	2.02	2.821 (3)	164
O3—H3···O1^i	0.82	1.87	2.660 (3)	160
O4—H4···O6	0.82	1.99	2.797 (3)	169
O6—H6···O4^ii	0.82	1.87	2.661 (3)	161
C1—H1B···Cg1^iii	0.97	2.75	3.584 (3)	144
C5—H5···Cg2^iv	0.93	2.71	3.602 (3)	160
C11—H11···Cg3^v	0.93	2.93	3.742 (3)	146

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