4-(2-Hy-droxy-eth-oxy)phenol.

The asymmetric unit of the title compound, C8H10O3, contains four mol-ecules, which differ in the orientation of the hy--droxy-ethyl group [O-C-C-O torsion angles = -168.89 (17), 72.9 (2), -65.8 (2) and 71.8 (2)°], as well as the orientation of the hy-droxy H atoms. Furthermore, the crystal structure displays two different types of strong hydrogen bond. The first is between an alcohol O-H and another alcohol O atom, and the second between an alcohol O-H group and an ether O atom. Additional weak hydrogen bonds between C-H groups and ether O atoms stabilize the structure.

Related literature

For the synthesis of the title compound, see: Read & Miller (1932 ▶). For its biological activity, see: Smit et al. (1992 ▶). For its use in the synthesis of biologically active materials, see: Ding et al. (2009 ▶); Pitterna et al. (2004 ▶); Petrović & Brückner (2011 ▶). For its application in polymer synthesis, see: Nakano et al. (2000 ▶); Kaneda et al. (2004 ▶); Xi et al. (2010 ▶). For its use as a substrate for dye synthesis, see: Kelly (1996 ▶). For information about the cuprate, used for synthesis, see: Normant et al. (1980 ▶). For its reactivity, see: Semmelhack et al. (1985 ▶).

Experimental

Crystal data

C8H10O3

M = 154.16

Triclinic,

a = 10.0388 (10) Å

b = 10.2425 (8) Å

c = 15.0692 (11) Å

α = 83.916 (8)°

β = 86.470 (9)°

γ = 77.124 (8)°

V = 1500.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.16 × 0.08 × 0.04 mm

Data collection

Bruker Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.910, T max = 0.997

17940 measured reflections

5282 independent reflections

3204 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.110

S = 1.02

5282 reflections

421 parameters

48 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: EVALCCD (Duisenberg et al., 2003 ▶); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019818/mw2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019818/mw2112Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019818/mw2112Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H10O3	Z = 8
Mr = 154.16	F(000) = 656
Triclinic, P1	Dx = 1.365 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0388 (10) Å	Cell parameters from 109 reflections
b = 10.2425 (8) Å	θ = 1–25°
c = 15.0692 (11) Å	µ = 0.10 mm−1
α = 83.916 (8)°	T = 123 K
β = 86.470 (9)°	Plate, colourless
γ = 77.124 (8)°	0.16 × 0.08 × 0.04 mm
V = 1500.8 (2) Å3

Bruker Nonius KappaCCD diffractometer	5282 independent reflections
Radiation source: fine-focus sealed tube	3204 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
rotation in φ and ω, 2° scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
Tmin = 0.910, Tmax = 0.997	k = −12→12
17940 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.2157P] where P = (Fo2 + 2Fc2)/3
5282 reflections	(Δ/σ)max < 0.001
421 parameters	Δρmax = 0.21 e Å−3
48 restraints	Δρmin = −0.27 e Å−3

Experimental. NMR spectra were recorded on a Bruker AM 400 spectrometer as solutions. Chemical shifts are expressed in parts per million (p.p.m., δ) downfield from tetramethylsilane (TMS) and are referenced to residual solvent peaks. The descriptions of signals include: m = multiplet, mc = centered multiplet, bs = broad singlet. The spectra were analyzed as first order patterns. The signal structure in the 13C NMR was analyzed by DEPT and is described as follows: + = primary or tertiary C-atom (positive DEPT signal), – = secondary C-atom (negative DEPT signal) and Cq = quaternary C-atom (no DEPT signal). MS(EI) (electron impact mass spectrometry) was performed by using a FINNIGAN MAT 90 (70 eV). The mass peak [M]+ and characteristic fragment peaks are given as mass to charge ratio (m/z) and the intensity of the signals were indicated in percent, relative to the intensity of the base signal (100%). IR (infrared spectroscopy) was recorded on a FT–IR Bruker alpha and intensities of the signals are characterized as follows: vs (very strong, 0–10% transmission), s (strong, 11–30% transmission), m (medium, 31–70% transmission), w (weak, 71–90% transmission) and vw (very weak, 91–100% transmission). Solvents, reagents and chemicals were purchased from Aldrich, Acros and Merck. All solvents, reagents and chemicals were used as purchased. Rf (cyclohexane/ethyl acetate = 1:1) = 0.30. – 1H NMR (400 MHz, acetone-D6): δ/p.p.m. = 3.80–3.84 (m, 2H, 2 × CH2), 3.92–3.97 (m, 3H, OH, 2 × CH2), 6.76 (mc, 4H, 4 × CHAr), 7.89 (bs, 1H, OHAr). – 13C NMR (100 MHz, acetone-D6): δ /p.p.m. = 61.51 (–, CH2), 71.09 (–, CH2), 116.36 (+, 2 × CHAr), 116.59 (+, 2 × CHAr), 152.21 (Cq, CAr), 153.30 (Cq, CAr). – IR (ATR) ν/cm-1 = 3468 (vw), 3250 (w), 2927 (w), 1862 (vw), 1604 (vw), 1505 (m), 1448 (m), 1367 (w), 1298 (w), 1274 (vw), 1215 (m), 1173 (w), 1073 (w), 1051 (m), 900 (w), 884 (w), 824 (m), 766 (w), 750 (m), 708 (w), 660 (w), 638 (w), 565 (w), 525 (w). – MS (70 eV, EI): m/z (%) = 154 (42) [M]+, 126 (55) [M – C2H4]+, 110 (100) [M – C2H4O]+, 98 (29) [M – C3H4O]+, 43 (24) [C2H3O]+. – HR-EIMS (C8H10O3): calc. 154.0630; found 154.0631.

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.

	x	y	z	Uiso*/Ueq
O1A	0.18232 (16)	0.52473 (17)	0.64327 (11)	0.0282 (4)
H1A	0.216 (2)	0.551 (2)	0.6858 (11)	0.042*
C2A	0.1518 (2)	0.3973 (2)	0.67249 (16)	0.0259 (6)
H2A1	0.2346	0.3354	0.6968	0.031*
H2A2	0.1242	0.3581	0.6211	0.031*
C3A	0.0380 (2)	0.4116 (2)	0.74358 (16)	0.0203 (6)
H3A1	0.0568	0.4653	0.7904	0.024*
H3A2	−0.0503	0.4569	0.7172	0.024*
O4A	0.03354 (14)	0.27818 (15)	0.78052 (10)	0.0209 (4)
C5A	−0.0668 (2)	0.2645 (2)	0.84542 (15)	0.0163 (5)
C6A	−0.1655 (2)	0.3708 (2)	0.87354 (15)	0.0193 (6)
H6A	−0.1661	0.4602	0.8488	0.023*
C7A	−0.2637 (2)	0.3459 (2)	0.93823 (16)	0.0208 (6)
H7A	−0.3316	0.4186	0.9578	0.025*
C8A	−0.2632 (2)	0.2165 (2)	0.97428 (16)	0.0207 (6)
O8A	−0.36470 (16)	0.19848 (17)	1.03765 (12)	0.0330 (5)
H8A	−0.338 (2)	0.1330 (19)	1.0753 (13)	0.050*
C9A	−0.1640 (2)	0.1099 (2)	0.94606 (16)	0.0207 (6)
H9A	−0.1636	0.0206	0.9709	0.025*
C10A	−0.0659 (2)	0.1338 (2)	0.88185 (15)	0.0188 (6)
H10A	0.0022	0.0609	0.8626	0.023*
O1B	0.31123 (17)	−0.00352 (17)	0.83922 (11)	0.0301 (4)
H1B	0.279 (2)	0.009 (2)	0.7885 (9)	0.045*
C2B	0.3478 (2)	0.1151 (2)	0.86098 (16)	0.0226 (6)
H2B1	0.3557	0.1102	0.9265	0.027*
H2B2	0.2740	0.1937	0.8434	0.027*
C3B	0.4795 (2)	0.1358 (2)	0.81603 (15)	0.0214 (6)
H3B1	0.5118	0.2062	0.8435	0.026*
H3B2	0.5502	0.0513	0.8230	0.026*
O4B	0.45661 (14)	0.17600 (15)	0.72330 (10)	0.0218 (4)
C5B	0.5635 (2)	0.2121 (2)	0.67196 (15)	0.0177 (5)
C6B	0.5347 (2)	0.2712 (2)	0.58594 (15)	0.0191 (6)
H6B	0.4449	0.2840	0.5651	0.023*
C7B	0.6359 (2)	0.3114 (2)	0.53055 (16)	0.0199 (6)
H7B	0.6156	0.3520	0.4719	0.024*
C8B	0.7674 (2)	0.2924 (2)	0.56081 (15)	0.0175 (5)
O8B	0.87364 (15)	0.33208 (16)	0.50961 (11)	0.0225 (4)
H8B	0.8447 (19)	0.377 (2)	0.4622 (10)	0.034*
C9B	0.7968 (2)	0.2323 (2)	0.64565 (16)	0.0207 (6)
H9B	0.8870	0.2189	0.6660	0.025*
C10B	0.6956 (2)	0.1913 (2)	0.70164 (15)	0.0191 (6)
H10B	0.7166	0.1493	0.7599	0.023*
O1C	0.73642 (15)	0.41867 (16)	0.20251 (11)	0.0263 (4)
H1C	0.7721 (19)	0.3400 (12)	0.1917 (16)	0.040*
C2C	0.5993 (2)	0.4495 (3)	0.17389 (16)	0.0269 (6)
H2C1	0.5892	0.3843	0.1321	0.032*
H2C2	0.5800	0.5404	0.1412	0.032*
C3C	0.4975 (2)	0.4452 (2)	0.25053 (16)	0.0228 (6)
H3C1	0.5111	0.5047	0.2953	0.027*
H3C2	0.4033	0.4765	0.2291	0.027*
O4C	0.51734 (14)	0.30920 (15)	0.28973 (10)	0.0213 (4)
C5C	0.4156 (2)	0.2782 (2)	0.34923 (15)	0.0177 (5)
C6C	0.3025 (2)	0.3728 (2)	0.37613 (15)	0.0186 (6)
H6C	0.2935	0.4653	0.3560	0.022*
C7C	0.2028 (2)	0.3308 (2)	0.43256 (15)	0.0188 (6)
H7C	0.1246	0.3950	0.4505	0.023*
C8C	0.2159 (2)	0.1967 (2)	0.46305 (15)	0.0182 (6)
O8C	0.11772 (15)	0.15193 (16)	0.51912 (11)	0.0246 (4)
H8C	0.0441 (13)	0.2101 (17)	0.5174 (15)	0.037*
C9C	0.3306 (2)	0.1033 (2)	0.43747 (15)	0.0202 (6)
H9C	0.3405	0.0112	0.4590	0.024*
C10C	0.4306 (2)	0.1434 (2)	0.38082 (15)	0.0199 (6)
H10C	0.5092	0.0792	0.3636	0.024*
O1D	0.80068 (17)	0.00017 (16)	0.32015 (11)	0.0271 (4)
H1D	0.826 (2)	−0.0651 (14)	0.3584 (12)	0.041*
C2D	0.8360 (2)	0.1160 (2)	0.34876 (16)	0.0207 (6)
H2D1	0.8426	0.1046	0.4145	0.025*
H2D2	0.7626	0.1959	0.3333	0.025*
C3D	0.9696 (2)	0.1395 (2)	0.30650 (15)	0.0207 (6)
H3D1	1.0007	0.2075	0.3373	0.025*
H3D2	1.0403	0.0548	0.3121	0.025*
O4D	0.95064 (14)	0.18600 (15)	0.21384 (10)	0.0201 (4)
C5D	1.0629 (2)	0.2190 (2)	0.16558 (15)	0.0175 (5)
C6D	1.0385 (2)	0.2832 (2)	0.08097 (15)	0.0209 (6)
H6D	0.9484	0.3029	0.0596	0.025*
C7D	1.1431 (2)	0.3191 (2)	0.02700 (16)	0.0223 (6)
H7D	1.1251	0.3631	−0.0311	0.027*
C8D	1.2757 (2)	0.2905 (2)	0.05823 (15)	0.0176 (5)
O8D	1.37587 (15)	0.32883 (16)	0.00195 (11)	0.0257 (4)
H8D	1.4524 (11)	0.288 (2)	0.0213 (14)	0.039*
C9D	1.2997 (2)	0.2284 (2)	0.14293 (15)	0.0191 (6)
H9D	1.3896	0.2098	0.1646	0.023*
C10D	1.1939 (2)	0.1924 (2)	0.19739 (16)	0.0206 (6)
H10D	1.2114	0.1499	0.2560	0.025*

	U11	U22	U33	U12	U13	U23
O1A	0.0300 (10)	0.0323 (10)	0.0228 (11)	−0.0131 (8)	−0.0012 (8)	0.0089 (8)
C2A	0.0302 (14)	0.0234 (14)	0.0219 (15)	−0.0051 (11)	0.0016 (11)	0.0046 (11)
C3A	0.0208 (13)	0.0185 (13)	0.0206 (14)	−0.0037 (10)	−0.0015 (10)	0.0024 (11)
O4A	0.0198 (9)	0.0179 (9)	0.0233 (10)	−0.0031 (7)	0.0032 (7)	0.0018 (7)
C5A	0.0132 (12)	0.0233 (14)	0.0131 (14)	−0.0055 (10)	−0.0020 (10)	−0.0005 (11)
C6A	0.0186 (12)	0.0178 (13)	0.0212 (15)	−0.0036 (10)	−0.0059 (11)	0.0022 (11)
C7A	0.0155 (12)	0.0214 (13)	0.0235 (15)	0.0000 (10)	−0.0027 (11)	−0.0006 (11)
C8A	0.0148 (12)	0.0262 (14)	0.0196 (14)	−0.0042 (11)	0.0008 (10)	0.0041 (11)
O8A	0.0236 (9)	0.0325 (11)	0.0343 (12)	0.0017 (8)	0.0085 (8)	0.0140 (8)
C9A	0.0217 (13)	0.0180 (13)	0.0223 (15)	−0.0060 (11)	−0.0043 (11)	0.0036 (11)
C10A	0.0164 (12)	0.0175 (13)	0.0211 (15)	−0.0003 (10)	−0.0029 (10)	−0.0018 (11)
O1B	0.0397 (10)	0.0335 (10)	0.0218 (11)	−0.0192 (8)	−0.0083 (8)	0.0046 (8)
C2B	0.0277 (14)	0.0236 (14)	0.0178 (14)	−0.0088 (11)	−0.0004 (11)	−0.0008 (11)
C3B	0.0244 (13)	0.0253 (14)	0.0130 (14)	−0.0039 (11)	−0.0005 (10)	0.0015 (11)
O4B	0.0172 (8)	0.0294 (9)	0.0177 (10)	−0.0054 (7)	0.0008 (7)	0.0025 (8)
C5B	0.0191 (12)	0.0172 (12)	0.0171 (14)	−0.0043 (10)	0.0032 (10)	−0.0048 (10)
C6B	0.0160 (12)	0.0190 (13)	0.0214 (15)	−0.0007 (10)	−0.0036 (11)	−0.0025 (11)
C7B	0.0215 (13)	0.0210 (13)	0.0159 (14)	−0.0025 (11)	−0.0021 (11)	0.0007 (11)
C8B	0.0169 (12)	0.0164 (12)	0.0201 (15)	−0.0056 (10)	0.0019 (11)	−0.0037 (10)
O8B	0.0196 (9)	0.0256 (10)	0.0202 (10)	−0.0041 (7)	−0.0007 (7)	0.0066 (8)
C9B	0.0159 (12)	0.0194 (13)	0.0257 (16)	−0.0004 (10)	−0.0036 (11)	−0.0026 (11)
C10B	0.0221 (13)	0.0210 (13)	0.0132 (14)	−0.0044 (11)	−0.0021 (10)	0.0021 (10)
O1C	0.0190 (9)	0.0250 (10)	0.0335 (11)	−0.0036 (8)	0.0029 (7)	−0.0008 (8)
C2C	0.0246 (14)	0.0344 (15)	0.0221 (15)	−0.0097 (12)	−0.0024 (11)	0.0032 (12)
C3C	0.0200 (13)	0.0184 (13)	0.0279 (15)	−0.0028 (11)	−0.0039 (11)	0.0068 (11)
O4C	0.0173 (8)	0.0208 (9)	0.0245 (10)	−0.0045 (7)	0.0030 (7)	0.0017 (7)
C5C	0.0174 (12)	0.0211 (13)	0.0158 (14)	−0.0058 (10)	−0.0043 (10)	−0.0015 (10)
C6C	0.0210 (13)	0.0160 (13)	0.0187 (14)	−0.0038 (10)	−0.0019 (11)	−0.0004 (10)
C7C	0.0160 (12)	0.0210 (13)	0.0179 (14)	0.0002 (10)	−0.0010 (10)	−0.0036 (11)
C8C	0.0174 (12)	0.0225 (13)	0.0153 (14)	−0.0064 (11)	−0.0020 (10)	0.0010 (11)
O8C	0.0187 (9)	0.0259 (10)	0.0253 (10)	−0.0011 (7)	0.0024 (8)	0.0058 (8)
C9C	0.0212 (13)	0.0164 (13)	0.0218 (15)	−0.0026 (10)	−0.0045 (11)	0.0025 (11)
C10C	0.0168 (12)	0.0200 (13)	0.0214 (15)	0.0002 (10)	−0.0033 (10)	−0.0029 (11)
O1D	0.0384 (10)	0.0211 (9)	0.0242 (11)	−0.0129 (8)	−0.0085 (8)	0.0046 (8)
C2D	0.0239 (13)	0.0176 (13)	0.0206 (14)	−0.0040 (10)	−0.0029 (11)	−0.0012 (11)
C3D	0.0206 (13)	0.0225 (13)	0.0186 (15)	−0.0040 (11)	−0.0031 (10)	0.0002 (11)
O4D	0.0160 (8)	0.0276 (9)	0.0160 (10)	−0.0046 (7)	−0.0014 (7)	0.0013 (7)
C5D	0.0186 (12)	0.0168 (12)	0.0183 (14)	−0.0051 (10)	−0.0008 (10)	−0.0037 (11)
C6D	0.0141 (12)	0.0253 (14)	0.0218 (15)	−0.0008 (11)	−0.0031 (11)	−0.0021 (11)
C7D	0.0247 (13)	0.0247 (14)	0.0164 (14)	−0.0038 (11)	−0.0025 (11)	0.0012 (11)
C8D	0.0175 (12)	0.0164 (12)	0.0177 (14)	−0.0021 (10)	0.0036 (10)	−0.0021 (10)
O8D	0.0192 (9)	0.0295 (10)	0.0271 (11)	−0.0056 (8)	−0.0005 (8)	0.0027 (8)
C9D	0.0145 (12)	0.0203 (13)	0.0222 (15)	−0.0023 (10)	−0.0017 (10)	−0.0037 (11)
C10D	0.0198 (13)	0.0226 (13)	0.0193 (15)	−0.0037 (11)	−0.0042 (11)	−0.0014 (11)

O1A—C2A	1.425 (3)	O1C—C2C	1.425 (3)
O1A—H1A	0.840 (9)	O1C—H1C	0.835 (9)
C2A—C3A	1.511 (3)	C2C—C3C	1.498 (3)
C2A—H2A1	0.9900	C2C—H2C1	0.9900
C2A—H2A2	0.9900	C2C—H2C2	0.9900
C3A—O4A	1.429 (3)	C3C—O4C	1.431 (3)
C3A—H3A1	0.9900	C3C—H3C1	0.9900
C3A—H3A2	0.9900	C3C—H3C2	0.9900
O4A—C5A	1.379 (3)	O4C—C5C	1.385 (3)
C5A—C6A	1.383 (3)	C5C—C6C	1.389 (3)
C5A—C10A	1.391 (3)	C5C—C10C	1.390 (3)
C6A—C7A	1.388 (3)	C6C—C7C	1.385 (3)
C6A—H6A	0.9500	C6C—H6C	0.9500
C7A—C8A	1.377 (3)	C7C—C8C	1.382 (3)
C7A—H7A	0.9500	C7C—H7C	0.9500
C8A—O8A	1.382 (3)	C8C—O8C	1.382 (3)
C8A—C9A	1.388 (3)	C8C—C9C	1.387 (3)
O8A—H8A	0.838 (9)	O8C—H8C	0.840 (9)
C9A—C10A	1.381 (3)	C9C—C10C	1.382 (3)
C9A—H9A	0.9500	C9C—H9C	0.9500
C10A—H10A	0.9500	C10C—H10C	0.9500
O1B—C2B	1.420 (3)	O1D—C2D	1.426 (3)
O1B—H1B	0.836 (9)	O1D—H1D	0.840 (9)
C2B—C3B	1.495 (3)	C2D—C3D	1.506 (3)
C2B—H2B1	0.9900	C2D—H2D1	0.9900
C2B—H2B2	0.9900	C2D—H2D2	0.9900
C3B—O4B	1.432 (3)	C3D—O4D	1.437 (3)
C3B—H3B1	0.9900	C3D—H3D1	0.9900
C3B—H3B2	0.9900	C3D—H3D2	0.9900
O4B—C5B	1.379 (3)	O4D—C5D	1.389 (3)
C5B—C10B	1.390 (3)	C5D—C6D	1.381 (3)
C5B—C6B	1.390 (3)	C5D—C10D	1.387 (3)
C6B—C7B	1.381 (3)	C6D—C7D	1.379 (3)
C6B—H6B	0.9500	C6D—H6D	0.9500
C7B—C8B	1.389 (3)	C7D—C8D	1.398 (3)
C7B—H7B	0.9500	C7D—H7D	0.9500
C8B—C9B	1.378 (3)	C8D—O8D	1.373 (3)
C8B—O8B	1.387 (3)	C8D—C9D	1.374 (3)
O8B—H8B	0.839 (8)	O8D—H8D	0.841 (9)
C9B—C10B	1.389 (3)	C9D—C10D	1.393 (3)
C9B—H9B	0.9500	C9D—H9D	0.9500
C10B—H10B	0.9500	C10D—H10D	0.9500
C2A—O1A—H1A	108.1 (14)	C2C—O1C—H1C	108.1 (14)
O1A—C2A—C3A	110.68 (19)	O1C—C2C—C3C	112.20 (19)
O1A—C2A—H2A1	109.5	O1C—C2C—H2C1	109.2
C3A—C2A—H2A1	109.5	C3C—C2C—H2C1	109.2
O1A—C2A—H2A2	109.5	O1C—C2C—H2C2	109.2
C3A—C2A—H2A2	109.5	C3C—C2C—H2C2	109.2
H2A1—C2A—H2A2	108.1	H2C1—C2C—H2C2	107.9
O4A—C3A—C2A	106.28 (18)	O4C—C3C—C2C	107.90 (19)
O4A—C3A—H3A1	110.5	O4C—C3C—H3C1	110.1
C2A—C3A—H3A1	110.5	C2C—C3C—H3C1	110.1
O4A—C3A—H3A2	110.5	O4C—C3C—H3C2	110.1
C2A—C3A—H3A2	110.5	C2C—C3C—H3C2	110.1
H3A1—C3A—H3A2	108.7	H3C1—C3C—H3C2	108.4
C5A—O4A—C3A	117.24 (17)	C5C—O4C—C3C	116.79 (17)
O4A—C5A—C6A	124.0 (2)	O4C—C5C—C6C	123.7 (2)
O4A—C5A—C10A	115.83 (19)	O4C—C5C—C10C	116.1 (2)
C6A—C5A—C10A	120.2 (2)	C6C—C5C—C10C	120.3 (2)
C5A—C6A—C7A	119.5 (2)	C7C—C6C—C5C	119.3 (2)
C5A—C6A—H6A	120.3	C7C—C6C—H6C	120.3
C7A—C6A—H6A	120.3	C5C—C6C—H6C	120.3
C8A—C7A—C6A	120.5 (2)	C8C—C7C—C6C	120.7 (2)
C8A—C7A—H7A	119.8	C8C—C7C—H7C	119.7
C6A—C7A—H7A	119.8	C6C—C7C—H7C	119.7
C7A—C8A—O8A	117.6 (2)	C7C—C8C—O8C	121.9 (2)
C7A—C8A—C9A	120.0 (2)	C7C—C8C—C9C	119.6 (2)
O8A—C8A—C9A	122.4 (2)	O8C—C8C—C9C	118.4 (2)
C8A—O8A—H8A	111.9 (15)	C8C—O8C—H8C	109.9 (13)
C10A—C9A—C8A	119.9 (2)	C10C—C9C—C8C	120.4 (2)
C10A—C9A—H9A	120.0	C10C—C9C—H9C	119.8
C8A—C9A—H9A	120.0	C8C—C9C—H9C	119.8
C9A—C10A—C5A	120.0 (2)	C9C—C10C—C5C	119.7 (2)
C9A—C10A—H10A	120.0	C9C—C10C—H10C	120.2
C5A—C10A—H10A	120.0	C5C—C10C—H10C	120.2
C2B—O1B—H1B	110.2 (14)	C2D—O1D—H1D	108.4 (14)
O1B—C2B—C3B	112.92 (19)	O1D—C2D—C3D	112.26 (19)
O1B—C2B—H2B1	109.0	O1D—C2D—H2D1	109.2
C3B—C2B—H2B1	109.0	C3D—C2D—H2D1	109.2
O1B—C2B—H2B2	109.0	O1D—C2D—H2D2	109.2
C3B—C2B—H2B2	109.0	C3D—C2D—H2D2	109.2
H2B1—C2B—H2B2	107.8	H2D1—C2D—H2D2	107.9
O4B—C3B—C2B	108.39 (18)	O4D—C3D—C2D	109.02 (18)
O4B—C3B—H3B1	110.0	O4D—C3D—H3D1	109.9
C2B—C3B—H3B1	110.0	C2D—C3D—H3D1	109.9
O4B—C3B—H3B2	110.0	O4D—C3D—H3D2	109.9
C2B—C3B—H3B2	110.0	C2D—C3D—H3D2	109.9
H3B1—C3B—H3B2	108.4	H3D1—C3D—H3D2	108.3
C5B—O4B—C3B	117.01 (17)	C5D—O4D—C3D	116.55 (16)
O4B—C5B—C10B	123.5 (2)	C6D—C5D—C10D	119.6 (2)
O4B—C5B—C6B	116.82 (19)	C6D—C5D—O4D	116.18 (19)
C10B—C5B—C6B	119.6 (2)	C10D—C5D—O4D	124.3 (2)
C7B—C6B—C5B	120.4 (2)	C7D—C6D—C5D	120.9 (2)
C7B—C6B—H6B	119.8	C7D—C6D—H6D	119.5
C5B—C6B—H6B	119.8	C5D—C6D—H6D	119.5
C6B—C7B—C8B	119.9 (2)	C6D—C7D—C8D	119.7 (2)
C6B—C7B—H7B	120.1	C6D—C7D—H7D	120.2
C8B—C7B—H7B	120.1	C8D—C7D—H7D	120.2
C9B—C8B—O8B	116.93 (19)	O8D—C8D—C9D	123.2 (2)
C9B—C8B—C7B	119.9 (2)	O8D—C8D—C7D	117.3 (2)
O8B—C8B—C7B	123.1 (2)	C9D—C8D—C7D	119.4 (2)
C8B—O8B—H8B	110.6 (13)	C8D—O8D—H8D	108.3 (13)
C8B—C9B—C10B	120.5 (2)	C8D—C9D—C10D	120.8 (2)
C8B—C9B—H9B	119.7	C8D—C9D—H9D	119.6
C10B—C9B—H9B	119.7	C10D—C9D—H9D	119.6
C9B—C10B—C5B	119.6 (2)	C5D—C10D—C9D	119.6 (2)
C9B—C10B—H10B	120.2	C5D—C10D—H10D	120.2
C5B—C10B—H10B	120.2	C9D—C10D—H10D	120.2
O1A—C2A—C3A—O4A	−168.89 (17)	O1C—C2C—C3C—O4C	−65.8 (2)
C2A—C3A—O4A—C5A	−177.71 (18)	C2C—C3C—O4C—C5C	−166.76 (18)
C3A—O4A—C5A—C6A	2.9 (3)	C3C—O4C—C5C—C6C	−4.2 (3)
C3A—O4A—C5A—C10A	−178.20 (19)	C3C—O4C—C5C—C10C	174.66 (19)
O4A—C5A—C6A—C7A	178.77 (19)	O4C—C5C—C6C—C7C	176.9 (2)
C10A—C5A—C6A—C7A	−0.1 (3)	C10C—C5C—C6C—C7C	−1.9 (3)
C5A—C6A—C7A—C8A	0.0 (3)	C5C—C6C—C7C—C8C	0.8 (3)
C6A—C7A—C8A—O8A	−179.3 (2)	C6C—C7C—C8C—O8C	−179.7 (2)
C6A—C7A—C8A—C9A	0.1 (3)	C6C—C7C—C8C—C9C	0.6 (3)
C7A—C8A—C9A—C10A	0.0 (3)	C7C—C8C—C9C—C10C	−0.9 (3)
O8A—C8A—C9A—C10A	179.3 (2)	O8C—C8C—C9C—C10C	179.4 (2)
C8A—C9A—C10A—C5A	−0.1 (3)	C8C—C9C—C10C—C5C	−0.2 (3)
O4A—C5A—C10A—C9A	−178.77 (19)	O4C—C5C—C10C—C9C	−177.3 (2)
C6A—C5A—C10A—C9A	0.2 (3)	C6C—C5C—C10C—C9C	1.6 (3)
O1B—C2B—C3B—O4B	72.9 (2)	O1D—C2D—C3D—O4D	71.8 (2)
C2B—C3B—O4B—C5B	174.15 (18)	C2D—C3D—O4D—C5D	176.98 (18)
C3B—O4B—C5B—C10B	10.5 (3)	C3D—O4D—C5D—C6D	−170.15 (19)
C3B—O4B—C5B—C6B	−170.01 (19)	C3D—O4D—C5D—C10D	9.3 (3)
O4B—C5B—C6B—C7B	179.37 (19)	C10D—C5D—C6D—C7D	1.2 (3)
C10B—C5B—C6B—C7B	−1.1 (3)	O4D—C5D—C6D—C7D	−179.3 (2)
C5B—C6B—C7B—C8B	0.2 (3)	C5D—C6D—C7D—C8D	−0.1 (3)
C6B—C7B—C8B—C9B	0.6 (3)	C6D—C7D—C8D—O8D	−179.8 (2)
C6B—C7B—C8B—O8B	−178.9 (2)	C6D—C7D—C8D—C9D	−0.8 (3)
O8B—C8B—C9B—C10B	179.1 (2)	O8D—C8D—C9D—C10D	179.6 (2)
C7B—C8B—C9B—C10B	−0.4 (3)	C7D—C8D—C9D—C10D	0.7 (3)
C8B—C9B—C10B—C5B	−0.5 (3)	C6D—C5D—C10D—C9D	−1.3 (3)
O4B—C5B—C10B—C9B	−179.2 (2)	O4D—C5D—C10D—C9D	179.2 (2)
C6B—C5B—C10B—C9B	1.3 (3)	C8D—C9D—C10D—C5D	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1Ci	0.84 (1)	1.85 (1)	2.671 (2)	165 (2)
O8A—H8A···O1Bii	0.84 (1)	1.74 (1)	2.565 (2)	170 (2)
O1B—H1B···O1Diii	0.84 (1)	1.88 (1)	2.707 (2)	168 (2)
O8B—H8B···O1Ai	0.84 (1)	1.79 (1)	2.617 (2)	169 (2)
O1C—H1C···O4D	0.84 (1)	2.12 (1)	2.830 (2)	142 (2)
O8C—H8C···O8Biv	0.84 (1)	1.88 (1)	2.721 (2)	176 (2)
O1D—H1D···O8Ciii	0.84 (1)	2.02 (1)	2.800 (2)	155 (2)
O8D—H8D···O8Av	0.84 (1)	1.88 (1)	2.707 (2)	167 (2)
C2A—H2A1···O4B	0.99	2.48	3.452 (3)	168
C2B—H2B2···O4A	0.99	2.58	3.450 (3)	147
C2C—H2C1···O8Avi	0.99	2.44	3.402 (3)	163
C9B—H9B···O4Avii	0.95	2.54	3.361 (3)	145
C2C—H2C2···O8Dviii	0.99	2.49	3.337 (3)	144
C2D—H2D2···O4C	0.99	2.57	3.478 (3)	152

Table 1

Selected torsion angles (°)

O1A—C2A—C3A—O4A	−168.89 (17)
O1B—C2B—C3B—O4B	72.9 (2)
O1C—C2C—C3C—O4C	−65.8 (2)
O1D—C2D—C3D—O4D	71.8 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O1C i	0.84 (1)	1.85 (1)	2.671 (2)	165 (2)
O8A—H8A⋯O1B ii	0.84 (1)	1.74 (1)	2.565 (2)	170 (2)
O1B—H1B⋯O1D iii	0.84 (1)	1.88 (1)	2.707 (2)	168 (2)
O8B—H8B⋯O1A i	0.84 (1)	1.79 (1)	2.617 (2)	169 (2)
O1C—H1C⋯O4D	0.84 (1)	2.12 (1)	2.830 (2)	142 (2)
O8C—H8C⋯O8B iv	0.84 (1)	1.88 (1)	2.721 (2)	176 (2)
O1D—H1D⋯O8C iii	0.84 (1)	2.02 (1)	2.800 (2)	155 (2)
O8D—H8D⋯O8A v	0.84 (1)	1.88 (1)	2.707 (2)	167 (2)
C2A—H2A1⋯O4B	0.99	2.48	3.452 (3)	168
C2B—H2B2⋯O4A	0.99	2.58	3.450 (3)	147
C2C—H2C1⋯O8A vi	0.99	2.44	3.402 (3)	163
C9B—H9B⋯O4A vii	0.95	2.54	3.361 (3)	145
C2C—H2C2⋯O8D viii	0.99	2.49	3.337 (3)	144
C2D—H2D2⋯O4C	0.99	2.57	3.478 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .