Naphthalene-1,6-diol: a three-dimensional framework built from O-H...O, O-H...[pi] and C-H...O hydrogen bonds

The asymmetric unit of the title compound, C₁₀H₈O₂, contains two practically planar symmetry-independent mol­ecules linked by one O-H...O hydrogen bond. Mol­ecules are further linked into a three-dimensional network, which is built from R₆⁶(36), R₆⁶(18), R₆⁶(30) and R₄⁴(26) rings formed by the combined effect of three O-H...O and one C-H...O hydrogen bond. This network is additionally stabilized by an O-H...[pi] inter­action.

S1. Comment

This paper is a continuation of our structural studies of mono- and dihydroxynaphthalenes, which are a class of intermediates important for applications in the synthesis of dyes, tanning agents, antioxidants and antiseptics. In the previous papers, the structures of 1-hydroxynaphthalene (1-naphthol; Rozycka-Sokolowska et al., 2004), 2-hydroxynaphthalene (2-naphthol; Marciniak et al., 2003), 1,3-dihydroxynaphthalene (naphthalene-1,3-diol; Marciniak et al., 2006), 1,7-dihydroxynaphthalene (naphthalene-1,7-diol; Marciniak, 2007) and 2,7-dihydroxynaphthalene (naphthalene-2,7-diol; Rozycka-Sokolowska et al., 2005) have been reported, and the results of structural studies of naphthalene-1,6-diol, (I), are presented here.

As in the case of the other naphthalenediol isomers, such as naphthalene-1,7-diol (Marciniak, 2007), naphthalene-2,3-diol and naphthalene-2,6-diol (Belskii et al., 1990), in the structure of the title compound there are two symmetry-independent molecules, A and B, in the asymmetric unit, which are linked by an O—H···O hydrogen bond (Fig. 1 and Table 2). The C—C bond distances range from 1.351 (3) to 1.425 (3) Å in molecule A and 1.337 (3) to 1.413 (3) Å in molecule B (Table 1). In each molecule, four C—C bonds, viz. C1A—C2A, C3A—C4A, C6A—C7A and C8A—C9A, and C1B—C2B, C3B—C4B, C6B—C7B and C8B—C9B, are shorter than the typical aromatic bond length of 1.384 (13) Å (Allen et al., 1987), whereas all the other bonds are longer. The valence angles within the aromatic rings of these molecules lie in the ranges 118.4 (2)–122.6 (2)° and 118.8 (2)–122.4 (2)°, respectively (Table 1). The naphthalene C1A–C10A and C1B–C10B ring systems are practically planar, with largest out-of-plane deviations of 0.049 (2) and -0.027 (2) Å for atoms C1A and C1B, respectively. The O atoms attached to these rings at atoms C1A, C7A, C1B and C7B deviate from the planes of these rings by only 0.130 (2), 0.029 (2), -0.062 (2) and -0.056 (2) Å, respectively. The angle between the mean planes formed by the C atoms of molecules A and B is 81.46 (7)°. This value is in close agreement with that observed for the other naphthalenediol isomer containing two independent molecules, viz. naphthalene-1,7-diol [the dihedral angle between the mean planes formed by the C atoms of the two independent molecules is 78.97 ° (Marciniak, 2007)], and it is about 25° less than the value of this parameter observed for naphthalene-2,3-diol (Belskii et al., 1990). This noncoplanar orientation of two symmetry-independent molecules observed in (I) is in contrast with the nearly coplanar orientation of the independent molecules observed in naphthalene-2,6-diol [the dihedral angle between the mean planes formed by the C atoms of the two independent molecules is 4.6 (4)° (Belskii et al., 1990)].

Apart from the above-mentioned O1B—H11B···O1A hydrogen bond, in the crystal structure of (I), there are also two intermolecular O—H···O hydrogen bonds and one intermolecular C—H···O hydrogen bond (Table 2 and Figs. 2–4). The O1A—H11A···O2Aⁱ interactions [symmetry code: (i) -x, y - 1/2, -z + 1/2] link the A molecules into a C(8) chain (Bernstein et al., 1995) running parallel to the [010] direction (Fig. 2). The A molecules belonging to the C(8) chains are connected to B molecules by two O—H···O hydrogen bonds, viz. O1B—H11B···O1A and O2A—H12A···O2Bⁱⁱ [symmetry code: (ii) -x + 1, y + 1/2, -z + 1/2], which are classified as D on the first-level graph set (Bernstein et al., 1995). The combined effect of these three O—H···O hydrogen bonds is the formation of a puckered sheet parallel to the (001) plane containing R₆⁶(36) rings (Fig. 2). The non-H atoms belonging to the (001) sheets lie in the domains (-0.05 + z/2) < c < (0.55 + z/2) (where z is zero or an integer). Moreover, each such sheet is linked to two neighbouring sheets by a classical O—H···π hydrogen bond and a weak C—H···O hydrogen bond to form a continuous three-dimensional network (Fig. 4). Atom O2B in molecule B at (x, y, z), belonging to the sheet in domain -0.05 < c < 0.55, acts as a hydrogen-bond donor, via atom H12B, to the C1A–C5A/C10A benzene ring (centroid Cg1) of molecule A at (1 + x, 1/2 - y, 1/2 + z), which belongs to the adjacent sheet in domain 0.45 < c < 1.05. As mentioned above, in the structure of (I) there is also a C—H···O interaction, which links atom C9A atom of molecule A at (x, y, z), via H9A, with atom O1B at (x, -y + 1/2, z - 1/2), and this can be described by the graph-set notation D (Fig. 2 and Table 1). A detailed analysis of the three-dimensional network indicates that, apart from the above-mentioned R₆⁶(36) rings, this network contains also R₆⁶(18) and R₆⁶(30) rings formed by the combined effect of the O1B—H11B···O1A, O1A—H11A···O2Aⁱ and C9A—H9A···O1Bⁱⁱⁱ hydrogen bonds (Fig. 3), as well as R₄⁴(26) rings, being a combination of the C9A—H9A···O1Bⁱⁱⁱ and O2A—H12A···O2Bⁱⁱ hydrogen bonds [symmetry code: (iii) x, -y + 1/2, z - 1/2] (Fig. 4).

Related literature

For related literature, see: Allen et al. (1987); Belskii et al. (1990); Bernstein et al. (1995); Marciniak (2007); Marciniak et al. (2003, 2006); Rozycka-Sokolowska, Marciniak & Pavlyuk (2004, 2005); Sheldrick (1997).

S2. Experimental

The starting material was commercially available naphthalene-1,6-diol (Sigma Aldrich, purity 99%), which was purified by twofold crystallization from anhydrous ethanol. In such purified material, no impurities were detected by gas chromatography. Crystals of (I) were grown from solution in chloroform by slow evaporation of this solvent at a constant temperature of 293 K.

S3. Refinement

H atoms involved in hydrogen-bond formation (attached to atoms O1A, O2A, O1B, O2B and C9A) were located in a difference Fourier map and refined with isotropic displacement parameters. All O—H distances were restrained with a DFIX 0.83 (3) Å command (Sheldrick, 1997), while the C9A—H9A distance was restrained with a DFIX 0.93 (3) Å command. All other H atoms were included in the refinement at geometrically calculated positions and refined using a riding model with C—H distances of 0.93 Å and with U_iso(H) set at 1.2U_eq(C).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,2003) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Views of molecules A (left) and B (right) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line depicts the intermolecular hydrogen bond.
	Fig. 2. Part of the crystal structure of (I), showing the O—H···O hydrogen bonds (see Table 1 for details), shown as dashed lines, as well as the C(8) chains (atoms belonging to this chain are represented by spheres) and the R6^6(36) rings. All H atoms not involved in these hydrogen bonds have been omitted for clarity.
	Fig. 3. Part of the crystal structure of (I), showing the R6^6(18) and R6^6(30) rings formed by O—H···O and C—H···O hydrogen bonds (shown as dashed lines); symmetry codes are given in Table 1. In order to differentiate molecules A and B, all H atoms of molecules A are included, while the H atoms of molecules B, except for atoms H11B and H12B, have been omitted.
	Fig. 4. Part of the crystal structure of (I), showing the R4^4(26) rings formed by O—H···O and C—H···O hydrogen bonds (grey dashed lines), as well as the intermolecular O—H···π interactions (black dashed lines). Symmetry codes are given in Table 1; the centroid (Cg1) of the C1A–C5A/C10A benzene ring is denoted by a small sphere. In order to differentiate molecules A and B, all H atoms of molecules A are included, while the H atoms of molecules B, except for atoms H11B and H12B, have been omitted.

Naphthalene-1,6-diol

Crystal data

C10H8O2	F(000) = 672
Mr = 160.16	Dx = 1.382 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8646 reflections
a = 11.5109 (19) Å	θ = 4.4–25.0°
b = 16.882 (3) Å	µ = 0.10 mm^−1
c = 7.9362 (19) Å	T = 290 K
β = 93.034 (17)°	Tablet, red
V = 1540.1 (5) Å^3	0.39 × 0.33 × 0.06 mm
Z = 8

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer	2709 independent reflections
Radiation source: fine-focus sealed tube	2034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 25.0°, θmin = 4.4°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005)	h = −11→13
Tmin = 0.996, Tmax = 0.999	k = −20→18
8646 measured reflections	l = −7→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.0446P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
2709 reflections	Δρmax = 0.15 e Å^−3
238 parameters	Δρmin = −0.16 e Å^−3
5 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

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	−0.03689 (15)	0.21015 (11)	0.1858 (2)	0.0571 (5)
H11A	−0.071 (3)	0.1669 (14)	0.211 (4)	0.106 (13)*
O2A	0.11237 (17)	0.56926 (10)	0.1928 (2)	0.0590 (5)
H12A	0.1669 (19)	0.5703 (17)	0.129 (3)	0.069 (9)*
C1A	−0.09485 (19)	0.27314 (14)	0.2484 (3)	0.0476 (6)
C2A	−0.1980 (2)	0.26679 (15)	0.3231 (3)	0.0538 (6)
H2A	−0.2343	0.2177	0.3289	0.065*
C3A	−0.2499 (2)	0.33354 (15)	0.3912 (3)	0.0557 (7)
H3A	−0.3199	0.3283	0.4433	0.067*
C4A	−0.1994 (2)	0.40556 (16)	0.3821 (3)	0.0539 (7)
H4A	−0.2344	0.4492	0.4298	0.065*
C5A	−0.0938 (2)	0.41540 (14)	0.3009 (3)	0.0457 (6)
C6A	−0.0391 (2)	0.48944 (14)	0.2871 (3)	0.0492 (6)
H6A	−0.0712	0.5339	0.3358	0.059*
C7A	0.0608 (2)	0.49652 (13)	0.2029 (3)	0.0465 (6)
C8A	0.1097 (2)	0.43019 (13)	0.1279 (3)	0.0477 (6)
H8A	0.1766	0.4358	0.0681	0.057*
C9A	0.0602 (2)	0.35805 (14)	0.1420 (3)	0.0464 (6)
H9A	0.0944 (18)	0.3128 (11)	0.093 (2)	0.045 (6)*
C10A	−0.04136 (19)	0.34851 (13)	0.2297 (3)	0.0428 (6)
O1B	0.19124 (16)	0.19075 (12)	0.3131 (2)	0.0639 (5)
H11B	0.1257 (19)	0.194 (2)	0.263 (4)	0.102 (12)*
O2B	0.70072 (16)	0.07700 (13)	0.5059 (2)	0.0710 (6)
H12B	0.709 (3)	0.0891 (19)	0.609 (2)	0.101 (12)*
C1B	0.2706 (2)	0.16014 (14)	0.2106 (3)	0.0481 (6)
C2B	0.2486 (2)	0.14754 (14)	0.0447 (3)	0.0536 (6)
H2B	0.1762	0.1600	−0.0059	0.064*
C3B	0.3357 (2)	0.11558 (17)	−0.0511 (3)	0.0624 (7)
H3B	0.3204	0.1076	−0.1661	0.075*
C4B	0.4411 (2)	0.09603 (16)	0.0181 (3)	0.0597 (7)
H4B	0.4973	0.0748	−0.0487	0.072*
C5B	0.4660 (2)	0.10779 (14)	0.1909 (3)	0.0482 (6)
C6B	0.5733 (2)	0.08620 (15)	0.2702 (3)	0.0544 (6)
H6B	0.6299	0.0625	0.2077	0.065*
C7B	0.5945 (2)	0.09946 (15)	0.4351 (3)	0.0535 (6)
C8B	0.5110 (2)	0.13529 (17)	0.5319 (3)	0.0615 (7)
H8B	0.5276	0.1451	0.6460	0.074*
C9B	0.4064 (2)	0.15570 (15)	0.4599 (3)	0.0562 (7)
H9B	0.3512	0.1793	0.5251	0.067*
C10B	0.3801 (2)	0.14188 (14)	0.2890 (3)	0.0457 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0488 (10)	0.0457 (10)	0.0766 (12)	0.0033 (9)	0.0024 (9)	−0.0062 (9)
O2A	0.0595 (12)	0.0474 (10)	0.0708 (12)	−0.0086 (9)	0.0082 (10)	−0.0011 (9)
C1A	0.0414 (13)	0.0486 (14)	0.0522 (13)	0.0024 (12)	−0.0035 (11)	0.0013 (11)
C2A	0.0409 (14)	0.0554 (15)	0.0647 (15)	−0.0068 (12)	−0.0006 (12)	0.0060 (13)
C3A	0.0453 (15)	0.0652 (17)	0.0570 (15)	0.0021 (13)	0.0071 (11)	0.0067 (13)
C4A	0.0504 (15)	0.0587 (16)	0.0531 (14)	0.0110 (13)	0.0073 (11)	−0.0005 (12)
C5A	0.0439 (13)	0.0528 (14)	0.0398 (12)	0.0045 (11)	−0.0018 (10)	0.0028 (10)
C6A	0.0533 (15)	0.0449 (14)	0.0489 (13)	0.0045 (12)	0.0007 (11)	−0.0019 (11)
C7A	0.0458 (14)	0.0446 (14)	0.0480 (13)	−0.0014 (12)	−0.0071 (11)	0.0043 (10)
C8A	0.0432 (13)	0.0524 (15)	0.0472 (13)	0.0025 (12)	0.0006 (10)	0.0029 (11)
C9A	0.0447 (14)	0.0460 (14)	0.0483 (13)	0.0043 (12)	0.0014 (11)	−0.0021 (11)
C10A	0.0393 (12)	0.0488 (13)	0.0397 (12)	0.0050 (11)	−0.0036 (9)	0.0009 (10)
O1B	0.0462 (11)	0.0834 (13)	0.0619 (11)	0.0125 (10)	0.0006 (9)	−0.0043 (10)
O2B	0.0475 (11)	0.1068 (16)	0.0578 (12)	0.0135 (10)	−0.0068 (9)	−0.0041 (11)
C1B	0.0409 (13)	0.0508 (14)	0.0526 (15)	0.0008 (11)	0.0034 (11)	0.0051 (11)
C2B	0.0457 (14)	0.0618 (15)	0.0523 (15)	−0.0004 (13)	−0.0050 (11)	0.0064 (12)
C3B	0.0623 (17)	0.0794 (18)	0.0447 (13)	−0.0072 (15)	−0.0039 (12)	−0.0001 (13)
C4B	0.0510 (15)	0.0811 (19)	0.0473 (14)	−0.0008 (14)	0.0055 (12)	−0.0068 (13)
C5B	0.0433 (13)	0.0562 (14)	0.0451 (13)	−0.0048 (12)	0.0016 (10)	−0.0001 (11)
C6B	0.0408 (13)	0.0720 (17)	0.0508 (14)	0.0035 (12)	0.0063 (11)	−0.0056 (12)
C7B	0.0412 (14)	0.0672 (16)	0.0516 (14)	0.0048 (13)	−0.0010 (11)	0.0007 (12)
C8B	0.0531 (15)	0.0871 (19)	0.0439 (14)	0.0058 (15)	−0.0014 (12)	−0.0050 (13)
C9B	0.0492 (14)	0.0691 (16)	0.0509 (15)	0.0099 (13)	0.0079 (11)	−0.0048 (12)
C10B	0.0426 (13)	0.0497 (14)	0.0450 (13)	−0.0023 (11)	0.0021 (10)	0.0026 (10)

Geometric parameters (Å, º)

O1A—C1A	1.363 (3)	O1B—C1B	1.357 (3)
O1A—H11A	0.86 (2)	O1B—H11B	0.84 (2)
O2A—C7A	1.368 (3)	O2B—C7B	1.371 (3)
O2A—H12A	0.83 (2)	O2B—H12B	0.84 (2)
C1A—C2A	1.359 (3)	C1B—C2B	1.345 (3)
C1A—C10A	1.425 (3)	C1B—C10B	1.409 (3)
C2A—C3A	1.397 (3)	C2B—C3B	1.398 (4)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.351 (3)	C3B—C4B	1.346 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.415 (3)	C4B—C5B	1.400 (3)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.406 (3)	C5B—C6B	1.405 (3)
C5A—C10A	1.412 (3)	C5B—C10B	1.413 (3)
C6A—C7A	1.365 (3)	C6B—C7B	1.337 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.401 (3)	C7B—C8B	1.400 (3)
C8A—C9A	1.352 (3)	C8B—C9B	1.350 (3)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.402 (3)	C9B—C10B	1.394 (3)
C9A—H9A	0.95 (2)	C9B—H9B	0.9300
C1A—O1A—H11A	110 (2)	C1B—O1B—H11B	111 (2)
C7A—O2A—H12A	114 (2)	C7B—O2B—H12B	112 (2)
C2A—C1A—O1A	123.6 (2)	C2B—C1B—O1B	123.3 (2)
C2A—C1A—C10A	120.5 (2)	C2B—C1B—C10B	121.0 (2)
O1A—C1A—C10A	115.9 (2)	O1B—C1B—C10B	115.7 (2)
C1A—C2A—C3A	120.4 (2)	C1B—C2B—C3B	119.4 (2)
C1A—C2A—H2A	119.8	C1B—C2B—H2B	120.3
C3A—C2A—H2A	119.8	C3B—C2B—H2B	120.3
C4A—C3A—C2A	120.8 (2)	C4B—C3B—C2B	122.0 (2)
C4A—C3A—H3A	119.6	C4B—C3B—H3B	119.0
C2A—C3A—H3A	119.6	C2B—C3B—H3B	119.0
C3A—C4A—C5A	120.8 (2)	C3B—C4B—C5B	119.9 (2)
C3A—C4A—H4A	119.6	C3B—C4B—H4B	120.1
C5A—C4A—H4A	119.6	C5B—C4B—H4B	120.1
C6A—C5A—C10A	118.5 (2)	C4B—C5B—C6B	122.1 (2)
C6A—C5A—C4A	122.6 (2)	C4B—C5B—C10B	119.0 (2)
C10A—C5A—C4A	118.9 (2)	C6B—C5B—C10B	118.9 (2)
C7A—C6A—C5A	120.5 (2)	C7B—C6B—C5B	120.4 (2)
C7A—C6A—H6A	119.7	C7B—C6B—H6B	119.8
C5A—C6A—H6A	119.7	C5B—C6B—H6B	119.8
C6A—C7A—O2A	119.1 (2)	C6B—C7B—O2B	117.9 (2)
C6A—C7A—C8A	120.4 (2)	C6B—C7B—C8B	121.0 (2)
O2A—C7A—C8A	120.5 (2)	O2B—C7B—C8B	121.2 (2)
C9A—C8A—C7A	120.3 (2)	C9B—C8B—C7B	120.1 (2)
C9A—C8A—H8A	119.9	C9B—C8B—H8B	120.0
C7A—C8A—H8A	119.9	C7B—C8B—H8B	120.0
C8A—C9A—C10A	120.7 (2)	C8B—C9B—C10B	120.8 (2)
C8A—C9A—H9A	120.3 (13)	C8B—C9B—H9B	119.6
C10A—C9A—H9A	119.0 (13)	C10B—C9B—H9B	119.6
C9A—C10A—C5A	119.5 (2)	C9B—C10B—C1B	122.4 (2)
C9A—C10A—C1A	122.1 (2)	C9B—C10B—C5B	118.8 (2)
C5A—C10A—C1A	118.4 (2)	C1B—C10B—C5B	118.8 (2)
O1A—C1A—C2A—C3A	177.1 (2)	O1B—C1B—C2B—C3B	−179.9 (2)
C10A—C1A—C2A—C3A	−3.6 (4)	C10B—C1B—C2B—C3B	0.2 (4)
C1A—C2A—C3A—C4A	0.9 (4)	C1B—C2B—C3B—C4B	0.8 (4)
C2A—C3A—C4A—C5A	1.1 (4)	C2B—C3B—C4B—C5B	−0.1 (4)
C3A—C4A—C5A—C6A	179.3 (2)	C3B—C4B—C5B—C6B	178.0 (2)
C3A—C4A—C5A—C10A	−0.3 (3)	C3B—C4B—C5B—C10B	−1.4 (4)
C10A—C5A—C6A—C7A	1.7 (3)	C4B—C5B—C6B—C7B	179.0 (2)
C4A—C5A—C6A—C7A	−177.9 (2)	C10B—C5B—C6B—C7B	−1.5 (4)
C5A—C6A—C7A—O2A	−179.54 (18)	C5B—C6B—C7B—O2B	179.9 (2)
C5A—C6A—C7A—C8A	0.5 (3)	C5B—C6B—C7B—C8B	−0.3 (4)
C6A—C7A—C8A—C9A	−1.8 (3)	C6B—C7B—C8B—C9B	1.2 (4)
O2A—C7A—C8A—C9A	178.2 (2)	O2B—C7B—C8B—C9B	−178.9 (2)
C7A—C8A—C9A—C10A	0.8 (3)	C7B—C8B—C9B—C10B	−0.3 (4)
C8A—C9A—C10A—C5A	1.4 (3)	C8B—C9B—C10B—C1B	178.0 (2)
C8A—C9A—C10A—C1A	−179.3 (2)	C8B—C9B—C10B—C5B	−1.5 (4)
C6A—C5A—C10A—C9A	−2.6 (3)	C2B—C1B—C10B—C9B	178.7 (2)
C4A—C5A—C10A—C9A	177.0 (2)	O1B—C1B—C10B—C9B	−1.2 (3)
C6A—C5A—C10A—C1A	178.02 (19)	C2B—C1B—C10B—C5B	−1.8 (4)
C4A—C5A—C10A—C1A	−2.4 (3)	O1B—C1B—C10B—C5B	178.3 (2)
C2A—C1A—C10A—C9A	−175.0 (2)	C4B—C5B—C10B—C9B	−178.1 (2)
O1A—C1A—C10A—C9A	4.3 (3)	C6B—C5B—C10B—C9B	2.4 (3)
C2A—C1A—C10A—C5A	4.3 (3)	C4B—C5B—C10B—C1B	2.4 (3)
O1A—C1A—C10A—C5A	−176.35 (18)	C6B—C5B—C10B—C1B	−177.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H11A···O2A^i	0.86 (3)	1.89 (3)	2.726 (3)	165 (3)
O1B—H11B···O1A	0.84 (2)	1.96 (2)	2.783 (3)	169 (3)
O2A—H12A···O2B^ii	0.83 (2)	1.91 (2)	2.737 (3)	176 (2)
C9A—H9A···O1B^iii	0.95 (2)	2.54 (2)	3.191 (3)	126 (2)
O2B—H12B···Cg1^iv	0.84 (2)	2.55 (3)	3.243 (2)	140 (3)

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