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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3279.
Published online 2009 November 28. doi:  10.1107/S1600536809050016
PMCID: PMC2971848

Benzene-1,3,5-triyl triacetate

Abstract

The asymmetric unit of the title compound, C12H12O6, contains two essentially identical mol­ecules related by a pseudo-inversion centre. The three acet­oxy groups in each mol­ecule are essentially planar and are tilted, in a regular propeller-style arrangement, with their normals oriented between 56.72 (12) and 76.35 (9)° from the normal to the mean plane of the central C6 ring; in each mol­ecule the three carbonyl O atoms are on the same side of the C6 ring, with the Cring—O—C—Me bonds in a trans conformation. The principal inter­molecular contacts appear to be C—H(...)π-ring inter­actions; each C6 ring has such a contact to both faces of the ring; in addition, each mol­ecule has two inter­molecular C—H(...)O contacts with H(...)O distances less than 2.55 Å.

Related literature

For our previous studies in this area, see: Haines & Hughes (2007 [triangle]); Haines et al. (2008 [triangle], 2009 [triangle]). For a related structure, see: Haines & Hughes (2009 [triangle]).

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Object name is e-65-o3279-scheme1.jpg

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Experimental

Crystal data

  • C12H12O6
  • M r = 252.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3279-efi1.jpg
  • a = 6.20290 (16) Å
  • b = 24.6643 (6) Å
  • c = 15.3862 (4) Å
  • β = 95.297 (2)°
  • V = 2343.88 (11) Å3
  • Z = 8
  • Mo- Kα radiation
  • μ = 0.12 mm−1
  • T = 140 K
  • 0.38 × 0.18 × 0.17 mm

Data collection

  • Oxford Diffraction Xcalibur 3/CCD diffractometer
  • Absorption correction: multi-scan (CrysAlisPro RED; Oxford Diffraction, 2008 [triangle]) T min = 0.931, T max = 1.041
  • 40881 measured reflections
  • 4128 independent reflections
  • 2769 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.196
  • S = 1.08
  • 4128 reflections
  • 331 parameters
  • H-atom parameters constrained
  • Δρmax = 0.65 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlisPro RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlisPro RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050016/hb5176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050016/hb5176Isup2.hkl

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

supplementary crystallographic information

Comment

Structural factors which enhance the solubility of organic compounds in liquid carbon dioxide are difficult to identify, but a knowledge of these is important in view of the possibility of using liquid carbon dioxide as an environmentally acceptable, cheap, safe and readily available alternative to replace organic-based solvents in the development of so-called "green chemistry". Previous studies (Haines et al., 2008) have shown that certain types of acyl group promote the solubilities of per-acylated D-glucopyranose derivatives in liquid carbon dioxide; in particular trimethylacetyl groups promoted solubility, their effect being comparable to acetyl groups and superior to dimethylacetyl groups. In searching for an explanation for solubility differences in this series based on differing intermolecular forces in the solid state, we conducted crystal structure studies on the compounds (Haines & Hughes, 2007), but the results indicated no substantial difference in such intermolecular forces.

Measurement of solubilities in liquid carbon dioxide of the series of 1,3,5-triacetoxybenzene (1) and substituted derivatives, viz 1,3,5-tris-(dimethylacetoxy)benzene (2) and 1,3,5-tris-(trimethylacetoxy)benzene (3), chosen in an attempt to separate the effects on solubility of the number and structure of peripheral substituents in compounds of similar overall molecular dimensions to the carbohydrate derivatives, showed no major differences (Haines, et al., 2009, unpublished results) and prompted an investigation of their crystal structures in order to compare intermolecular interactions in these compounds.

The stucture of the first compound of the series, (1) is shown in Figure 1; other compounds of the series are described in the accompanying paper (Haines and Hughes, 2009). Dimensions are available in the archived CIFs.

Compound (1) was prepared by the acylation of 1,3,5-trihydroxybenzene with acetic anhydride and formed crystals having two essentially identical molecules with very similar orientations in the cell, related by a pseudo inversion centre. The three acetoxy groups in each molecule are essentially planar and are tilted, in a regular propeller-style arrangement, with their normals at 56.72 (12), 76.35 (9) and 60.73 (12)° from the normal to the mean-plane of the central C6 ring in one molecule and 58.44 (11), 75.11 (13) and 63.76 (11) ° in the second molecule. In each molecule the three carbonyl O-atoms are on the same side of the C6 ring, with the Cring—O—C—Me bonds in a trans conformation. The principal intermolecular contacts appear to be C—H···π-ring interactions: each C6 ring has such a contact to both faces of the ring – the ring C(1–6) has H(12Ca) and H(94b) on opposite sides of the ring at 3.25 and 2.63 Å from the ring mean-plane, and the ring of C(91–96) is bounded by H(4c) and H(91Bd) at 2.65 and 3.14 Å from the ring mean-plane (the superscripts ad indicate symmetry operations). Also, each molecule makes two intermolecular C—H···O contacts with H···O distances in the range 2.31–2.54 Å.

Experimental

The title compound was prepared by the conventional acylation of the parent 1,3,5-trihydroxybenzene and has been described previously (Hegetschweiler et al., 1990); the physical data (m.p., 1H and 13C NMR spectra) of our product agreed with those reported.

To a solution of anhydrous 1,3,5-trihydroxybenzene (phloroglucinol) (1.26 g) in pyridine (6 ml) was added acetic anhydride (5.6 ml) and after 12 h the solution was poured into iced water which led to formation of a white precipitate. After stirring for 2 h, the solid was collected by filtration, and recrystallized from ethanol to give compound 1 (1.67 g, 66%), m.p. 106–107 °C (lit. {Hegetschweiler et al., 1990} 106 °C); δH(CDCl3) 6.84, (s, 3H), 2.27 (s, 9H); δC(CDCl3) 168.65, 151.19, 112.76, 20.91. The NMR data are in full agreement with the reported literature values (Hegetschweiler et al., 1990).

Refinement

Hydrogen atoms were included in idealized positions and their Uiso values were set to ride on the Ueq values of the parent carbon atoms.

Figures

Fig. 1.
View of the two independent molecules in (I), related by a pseudo-inversion centre at ca 0, 1/4, 1/2. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C12H12O6Z = 8
Mr = 252.22F(000) = 1056
Monoclinic, P21/nDx = 1.429 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 6.20290 (16) ŵ = 0.12 mm1
b = 24.6643 (6) ÅT = 140 K
c = 15.3862 (4) ÅPrism, colourless
β = 95.297 (2)°0.38 × 0.18 × 0.17 mm
V = 2343.88 (11) Å3

Data collection

Oxford Diffraction Xcalibur 3/CCD diffractometer4128 independent reflections
Radiation source: Enhance (Mo) X-ray Source2769 reflections with I > 2σ(I)
graphiteRint = 0.054
Detector resolution: 16.0050 pixels mm-1θmax = 25.0°, θmin = 3.1°
Thin–slice [var phi] and ω scansh = −7→7
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2008)k = −29→29
Tmin = 0.931, Tmax = 1.041l = −18→18
40881 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1157P)2 + 0.643P] where P = (Fo2 + 2Fc2)/3
4128 reflections(Δ/σ)max = 0.001
331 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

Experimental. CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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 (Å2)

xyzUiso*/Ueq
C10.1644 (5)0.22484 (12)0.2555 (2)0.0171 (7)
C20.2182 (5)0.21091 (12)0.17203 (19)0.0171 (7)
H20.12960.22000.12210.020*
C30.4090 (5)0.18306 (12)0.16789 (19)0.0188 (7)
C40.5456 (5)0.16979 (12)0.24048 (19)0.0177 (7)
H40.67560.15180.23530.021*
C50.4830 (5)0.18408 (13)0.32137 (19)0.0191 (7)
C60.2907 (5)0.21159 (12)0.33028 (19)0.0176 (7)
H60.24930.22070.38500.021*
O1−0.0344 (3)0.24931 (9)0.26764 (13)0.0208 (5)
C11−0.0865 (5)0.29755 (13)0.2254 (2)0.0216 (7)
O110.0352 (4)0.32021 (9)0.18212 (16)0.0330 (6)
C12−0.3065 (5)0.31541 (14)0.2446 (2)0.0255 (8)
H12A−0.32710.35270.22810.038*
H12B−0.32060.31150.30590.038*
H12C−0.41370.29350.21220.038*
O30.4578 (3)0.16404 (8)0.08570 (13)0.0210 (5)
C310.6135 (5)0.19045 (13)0.0455 (2)0.0211 (7)
O310.7100 (4)0.22877 (10)0.07680 (15)0.0301 (6)
C320.6401 (5)0.16603 (14)−0.04125 (19)0.0255 (8)
H32A0.51920.1759−0.08160.038*
H32B0.64690.1273−0.03590.038*
H32C0.77140.1792−0.06220.038*
O50.6130 (3)0.16564 (9)0.39428 (13)0.0233 (5)
C510.7090 (5)0.20210 (14)0.4523 (2)0.0222 (7)
O510.6831 (4)0.25004 (10)0.44501 (15)0.0325 (6)
C520.8440 (5)0.17336 (15)0.5235 (2)0.0265 (8)
H52A0.98720.18850.52920.040*
H52B0.85180.13550.50960.040*
H52C0.77970.17760.57750.040*
C910.8316 (5)0.52607 (12)0.23650 (19)0.0169 (7)
C920.7795 (5)0.53882 (12)0.32051 (19)0.0155 (7)
H920.86990.52930.36970.019*
C930.5880 (5)0.56608 (12)0.32707 (19)0.0177 (7)
C940.4486 (5)0.58031 (12)0.25507 (19)0.0181 (7)
H940.31880.59810.26140.022*
C950.5094 (5)0.56707 (12)0.17385 (18)0.0170 (7)
C960.7021 (5)0.54049 (11)0.16326 (19)0.0162 (7)
H960.74230.53270.10790.019*
O911.0296 (3)0.50177 (9)0.22335 (13)0.0189 (5)
C9111.0768 (5)0.45224 (13)0.26152 (19)0.0184 (7)
O9110.9526 (4)0.42894 (9)0.30330 (16)0.0317 (6)
C9121.2938 (6)0.43354 (14)0.2422 (2)0.0240 (7)
H91A1.31710.39720.26350.036*
H91B1.40210.45710.27030.036*
H91C1.30300.43420.18030.036*
O930.5437 (3)0.58395 (9)0.41005 (13)0.0224 (5)
C9310.3854 (5)0.55818 (14)0.4494 (2)0.0211 (7)
O9310.2877 (4)0.52004 (11)0.41682 (15)0.0315 (6)
C9320.3602 (6)0.58228 (15)0.5361 (2)0.0290 (9)
H93A0.23550.56690.55940.043*
H93B0.34200.62080.53020.043*
H93C0.48700.57470.57490.043*
O950.3780 (3)0.58607 (9)0.10101 (13)0.0217 (5)
C9510.2842 (5)0.54966 (13)0.04289 (19)0.0196 (7)
O9510.3003 (3)0.50160 (9)0.05213 (13)0.0241 (5)
C9520.1636 (5)0.57803 (15)−0.0327 (2)0.0273 (8)
H95A0.24780.5771−0.08190.041*
H95B0.13800.6150−0.01710.041*
H95C0.02770.5601−0.04740.041*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0166 (16)0.0130 (15)0.0220 (16)−0.0003 (13)0.0030 (12)0.0001 (12)
C20.0153 (16)0.0180 (17)0.0176 (15)−0.0033 (14)−0.0001 (12)0.0030 (13)
C30.0249 (17)0.0158 (16)0.0158 (15)−0.0062 (14)0.0019 (13)−0.0008 (12)
C40.0195 (16)0.0127 (16)0.0208 (16)−0.0002 (13)0.0012 (13)−0.0017 (12)
C50.0215 (16)0.0151 (16)0.0195 (16)−0.0029 (13)−0.0047 (13)0.0001 (12)
C60.0208 (17)0.0176 (17)0.0150 (15)−0.0015 (14)0.0051 (12)−0.0013 (13)
O10.0186 (11)0.0217 (12)0.0225 (12)0.0032 (9)0.0034 (9)0.0036 (9)
C110.0286 (18)0.0173 (17)0.0186 (16)−0.0003 (14)0.0005 (14)−0.0033 (13)
O110.0367 (14)0.0195 (13)0.0459 (15)0.0016 (11)0.0193 (12)0.0053 (11)
C120.0261 (17)0.0234 (19)0.0261 (18)0.0035 (17)−0.0022 (14)−0.0001 (14)
O30.0263 (12)0.0209 (12)0.0159 (11)−0.0037 (10)0.0025 (9)−0.0021 (9)
C310.0166 (16)0.0240 (18)0.0227 (17)0.0027 (14)0.0020 (13)0.0025 (14)
O310.0279 (13)0.0334 (14)0.0294 (13)−0.0088 (11)0.0052 (10)−0.0059 (11)
C320.0285 (18)0.033 (2)0.0159 (16)0.0031 (15)0.0049 (14)0.0009 (14)
O50.0276 (12)0.0208 (12)0.0203 (11)0.0033 (10)−0.0051 (9)−0.0036 (9)
C510.0174 (16)0.0282 (19)0.0214 (17)0.0000 (14)0.0050 (13)−0.0055 (14)
O510.0434 (15)0.0262 (14)0.0262 (13)−0.0040 (12)−0.0056 (11)−0.0018 (11)
C520.0247 (18)0.036 (2)0.0184 (16)0.0039 (16)−0.0025 (14)−0.0049 (14)
C910.0150 (16)0.0148 (15)0.0210 (16)−0.0036 (13)0.0019 (13)0.0006 (12)
C920.0179 (16)0.0137 (16)0.0144 (15)−0.0037 (13)−0.0010 (12)0.0004 (12)
C930.0224 (16)0.0153 (16)0.0158 (15)−0.0030 (13)0.0031 (12)−0.0027 (12)
C940.0200 (16)0.0148 (16)0.0199 (16)−0.0029 (13)0.0035 (13)−0.0016 (12)
C950.0185 (15)0.0162 (16)0.0157 (15)−0.0002 (13)−0.0018 (12)0.0031 (12)
C960.0241 (17)0.0114 (16)0.0139 (14)−0.0019 (13)0.0053 (12)−0.0021 (12)
O910.0177 (11)0.0205 (12)0.0190 (11)0.0034 (9)0.0045 (9)0.0034 (9)
C9110.0241 (17)0.0168 (16)0.0142 (15)−0.0007 (14)0.0008 (13)−0.0021 (12)
O9110.0407 (14)0.0178 (12)0.0398 (14)0.0016 (11)0.0209 (12)0.0034 (11)
C9120.0276 (17)0.0188 (18)0.0255 (17)0.0052 (16)0.0015 (13)0.0004 (14)
O930.0275 (12)0.0262 (13)0.0143 (11)−0.0010 (10)0.0061 (9)−0.0055 (9)
C9310.0170 (16)0.0264 (19)0.0203 (16)0.0076 (14)0.0039 (13)0.0062 (14)
O9310.0282 (13)0.0416 (16)0.0249 (13)−0.0075 (12)0.0036 (10)−0.0011 (11)
C9320.0313 (19)0.039 (2)0.0177 (17)0.0069 (17)0.0072 (14)0.0040 (14)
O950.0251 (12)0.0194 (12)0.0192 (11)0.0044 (9)−0.0050 (9)−0.0028 (9)
C9510.0176 (16)0.0255 (18)0.0160 (16)−0.0011 (14)0.0040 (12)−0.0044 (14)
O9510.0297 (13)0.0219 (13)0.0205 (12)−0.0041 (10)0.0012 (9)−0.0015 (9)
C9520.0292 (19)0.030 (2)0.0210 (17)0.0029 (16)−0.0061 (14)0.0004 (14)

Geometric parameters (Å, °)

C1—C61.370 (4)C91—C961.369 (4)
C1—C21.399 (4)C91—C921.397 (4)
C1—O11.401 (3)C91—O911.398 (3)
C2—C31.375 (4)C92—C931.376 (4)
C2—H20.9300C92—H920.9300
C3—C41.378 (4)C93—C941.386 (4)
C3—O31.408 (4)C93—O931.402 (3)
C4—C51.383 (4)C94—C951.377 (4)
C4—H40.9300C94—H940.9300
C5—C61.390 (4)C95—C961.386 (4)
C5—O51.396 (3)C95—O951.404 (3)
C6—H60.9300C96—H960.9300
O1—C111.380 (4)O91—C9111.375 (4)
C11—O111.191 (4)C911—O9111.195 (4)
C11—C121.489 (4)C911—C9121.479 (4)
C12—H12A0.9600C912—H91A0.9600
C12—H12B0.9600C912—H91B0.9600
C12—H12C0.9600C912—H91C0.9600
O3—C311.360 (4)O93—C9311.359 (4)
C31—O311.196 (4)C931—O9311.203 (4)
C31—C321.488 (4)C931—C9321.481 (4)
C32—H32A0.9600C932—H93A0.9600
C32—H32B0.9600C932—H93B0.9600
C32—H32C0.9600C932—H93C0.9600
O5—C511.365 (4)O95—C9511.359 (4)
C51—O511.197 (4)C951—O9511.197 (4)
C51—C521.495 (4)C951—C9521.496 (4)
C52—H52A0.9600C952—H95A0.9600
C52—H52B0.9600C952—H95B0.9600
C52—H52C0.9600C952—H95C0.9600
C6—C1—C2123.1 (3)C96—C91—C92122.3 (3)
C6—C1—O1115.7 (3)C96—C91—O91116.7 (3)
C2—C1—O1121.0 (3)C92—C91—O91120.8 (3)
C3—C2—C1116.4 (3)C93—C92—C91116.9 (3)
C3—C2—H2121.8C93—C92—H92121.5
C1—C2—H2121.8C91—C92—H92121.5
C2—C3—C4123.3 (3)C92—C93—C94122.9 (3)
C2—C3—O3117.7 (3)C92—C93—O93117.6 (3)
C4—C3—O3118.8 (3)C94—C93—O93119.2 (3)
C3—C4—C5117.8 (3)C95—C94—C93117.5 (3)
C3—C4—H4121.1C95—C94—H94121.2
C5—C4—H4121.1C93—C94—H94121.2
C4—C5—C6121.9 (3)C94—C95—C96122.0 (3)
C4—C5—O5116.8 (3)C94—C95—O95117.2 (3)
C6—C5—O5121.1 (3)C96—C95—O95120.5 (3)
C1—C6—C5117.6 (3)C91—C96—C95118.2 (3)
C1—C6—H6121.2C91—C96—H96120.9
C5—C6—H6121.2C95—C96—H96120.9
C11—O1—C1118.7 (2)C911—O91—C91118.3 (2)
O11—C11—O1122.3 (3)O911—C911—O91122.3 (3)
O11—C11—C12127.7 (3)O911—C911—C912127.0 (3)
O1—C11—C12109.9 (3)O91—C911—C912110.7 (3)
C11—C12—H12A109.5C911—C912—H91A109.5
C11—C12—H12B109.5C911—C912—H91B109.5
H12A—C12—H12B109.5H91A—C912—H91B109.5
C11—C12—H12C109.5C911—C912—H91C109.5
H12A—C12—H12C109.5H91A—C912—H91C109.5
H12B—C12—H12C109.5H91B—C912—H91C109.5
C31—O3—C3118.0 (2)C931—O93—C93118.0 (2)
O31—C31—O3123.1 (3)O931—C931—O93122.5 (3)
O31—C31—C32126.0 (3)O931—C931—C932126.8 (3)
O3—C31—C32110.9 (3)O93—C931—C932110.7 (3)
C31—C32—H32A109.5C931—C932—H93A109.5
C31—C32—H32B109.5C931—C932—H93B109.5
H32A—C32—H32B109.5H93A—C932—H93B109.5
C31—C32—H32C109.5C931—C932—H93C109.5
H32A—C32—H32C109.5H93A—C932—H93C109.5
H32B—C32—H32C109.5H93B—C932—H93C109.5
C51—O5—C5119.7 (2)C951—O95—C95119.1 (2)
O51—C51—O5122.9 (3)O951—C951—O95123.4 (3)
O51—C51—C52126.8 (3)O951—C951—C952125.8 (3)
O5—C51—C52110.4 (3)O95—C951—C952110.8 (3)
C51—C52—H52A109.5C951—C952—H95A109.5
C51—C52—H52B109.5C951—C952—H95B109.5
H52A—C52—H52B109.5H95A—C952—H95B109.5
C51—C52—H52C109.5C951—C952—H95C109.5
H52A—C52—H52C109.5H95A—C952—H95C109.5
H52B—C52—H52C109.5H95B—C952—H95C109.5
C6—C1—C2—C3−0.6 (5)C96—C91—C92—C931.1 (4)
O1—C1—C2—C3−174.8 (3)O91—C91—C92—C93175.6 (3)
C1—C2—C3—C4−1.1 (4)C91—C92—C93—C940.7 (4)
C1—C2—C3—O3174.2 (2)C91—C92—C93—O93−173.7 (2)
C2—C3—C4—C51.9 (5)C92—C93—C94—C95−1.2 (5)
O3—C3—C4—C5−173.4 (3)O93—C93—C94—C95173.1 (3)
C3—C4—C5—C6−0.9 (5)C93—C94—C95—C960.0 (5)
C3—C4—C5—O5173.9 (3)C93—C94—C95—O95−174.1 (3)
C2—C1—C6—C51.5 (5)C92—C91—C96—C95−2.2 (4)
O1—C1—C6—C5175.9 (3)O91—C91—C96—C95−176.9 (3)
C4—C5—C6—C1−0.7 (5)C94—C95—C96—C911.6 (5)
O5—C5—C6—C1−175.3 (3)O95—C95—C96—C91175.6 (3)
C6—C1—O1—C11127.7 (3)C96—C91—O91—C911−125.3 (3)
C2—C1—O1—C11−57.7 (4)C92—C91—O91—C91159.9 (4)
C1—O1—C11—O11−3.2 (4)C91—O91—C911—O9111.9 (4)
C1—O1—C11—C12178.0 (2)C91—O91—C911—C912−178.7 (2)
C2—C3—O3—C31105.9 (3)C92—C93—O93—C931−108.7 (3)
C4—C3—O3—C31−78.6 (3)C94—C93—O93—C93176.7 (4)
C3—O3—C31—O310.1 (4)C93—O93—C931—O9312.1 (4)
C3—O3—C31—C32−178.5 (3)C93—O93—C931—C932−179.9 (3)
C4—C5—O5—C51120.3 (3)C94—C95—O95—C951−120.5 (3)
C6—C5—O5—C51−64.9 (4)C96—C95—O95—C95165.3 (4)
C5—O5—C51—O511.9 (4)C95—O95—C951—O9513.1 (4)
C5—O5—C51—C52−178.6 (3)C95—O95—C951—C952−176.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C52—H52A···O31i0.962.533.363 (4)145
C52—H52C···O11i0.962.313.242 (4)163
C932—H93A···O911ii0.962.513.292 (4)139
C952—H95C···O951iii0.962.543.474 (4)165
C4—H4···Cg2iv0.932.683.460 (3)141
C12—H12C···Cg1v0.962.863.604 (4)135
C912—H91B···Cg2vi0.962.843.658 (4)143
C94—H94···Cg1vii0.932.673.435 (3)140

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x+3/2, y−1/2, −z+1/2; (v) x−1, y, z; (vi) x+1, y, z; (vii) −x+1/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5176).

References

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  • Haines, A. H., Steytler, D. C. & Rivett, C. (2008). J. Supercrit. Fluids, 44, 21–24.
  • Haines, A. H., Steytler, D. C. & Rivett, C. (2009). Unpublished data.
  • Oxford Diffraction (2008). CrysAlisPro CCD and CrysAlisPro RED. Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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