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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1256.
Published online 2008 June 13. doi:  10.1107/S1600536808017315
PMCID: PMC2961821

4,4′-Dimethoxy­benzophenone: a triclinic polymorph

Abstract

The title compound, C15H14O3, has been found to crystallize as a new triclinic polymorph. The asymmetric unit of the present structure, as in the previously reported monoclinic structure [Norment & Karle (1962 [triangle]). Acta Cryst. 15, 873–878], contains two independent mol­ecules, which differ slightly in the orientations of the two benzene rings. The crystal packing of the triclinic polymorph is stabilized by inter­molecular C—H(...)O hydrogen bonds and C—H(...)π inter­actions.

Related literature

For the monoclinic polymorph of 4,4′-dimethoxy­benzo­phenone, see: Norment & Karle (1962 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o1256-scheme1.jpg

Experimental

Crystal data

  • C15H14O3
  • M r = 242.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1256-efi1.jpg
  • a = 9.4296 (2) Å
  • b = 9.4569 (2) Å
  • c = 14.7963 (3) Å
  • α = 76.945 (1)°
  • β = 78.813 (1)°
  • γ = 70.670 (1)°
  • V = 1202.65 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100.0 (1) K
  • 0.50 × 0.19 × 0.16 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.955, T max = 0.985
  • 26162 measured reflections
  • 6478 independent reflections
  • 4651 reflections with I > 2σ(I))
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.170
  • S = 1.09
  • 6478 reflections
  • 329 parameters
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017315/ci2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017315/ci2608Isup2.hkl

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

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

The crystal structure of the title compound has previously been reported in the monoclinic space group P21/a (Norment & Karle, 1962). We report here the structure of a second polymorph which crystallizes in the triclinic space group P1.

The asymmetric unit of the triclinic polymporph contains two crystallographically independent molecules (Fig.1), similar to the monoclinic form. Bond lengths and angles of the molecules agree with each other and show normal values (Allen et al., 1987). The two independent molecules differ slightly in the orientations of the two benzene rings. The dihedral angle formed by C1A-C6A and C8A-C13A rings is 52.12 (8)° and that between C1B-C6B and C8B-C13B planes is 55.73 (7)°. These dihedral angles are comparable to those observed in the monoclinic polymorph.

The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds (Fig.2) and C—H···π interactions.

Experimental

The title compound was purchased from Merck and single crystals suitable for X-ray diffraction studies were obtained by slow evaporation of an ethanol solution.

Refinement

H atoms were positioned geometrically [C-H = 0.93 Å (aromatic) and 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C). A rotating group model was used for the methyl group.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C15H14O3Z = 4
Mr = 242.26F000 = 512
Triclinic, P1Dx = 1.338 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.4296 (2) ÅCell parameters from 5758 reflections
b = 9.4569 (2) Åθ = 2.3–28.8º
c = 14.7963 (3) ŵ = 0.09 mm1
α = 76.945 (1)ºT = 100.0 (1) K
β = 78.813 (1)ºNeedle, colourless
γ = 70.670 (1)º0.50 × 0.19 × 0.16 mm
V = 1202.65 (4) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer6478 independent reflections
Radiation source: fine-focus sealed tube4651 reflections with I > 2σ(I))
Monochromator: graphiteRint = 0.035
T = 100.0(1) Kθmax = 29.3º
[var phi] and ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −12→11
Tmin = 0.955, Tmax = 0.985k = −12→12
26162 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.170  w = 1/[σ2(Fo2) + (0.0952P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
6478 reflectionsΔρmax = 0.67 e Å3
329 parametersΔρmin = −0.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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
O1A−0.28278 (12)0.49910 (12)0.23294 (8)0.0249 (3)
O2A0.34179 (12)0.13120 (12)0.02987 (7)0.0214 (3)
O3A−0.28335 (13)0.14327 (12)0.64984 (7)0.0229 (3)
C1A0.08731 (17)0.22148 (16)0.23864 (10)0.0184 (3)
H1A0.09090.19870.30280.022*
C2A0.21523 (18)0.16537 (16)0.17906 (11)0.0194 (3)
H2A0.30480.10640.20300.023*
C3A0.21106 (17)0.19668 (15)0.08281 (10)0.0178 (3)
C4A0.07749 (17)0.28874 (16)0.04661 (10)0.0191 (3)
H4A0.07420.3113−0.01760.023*
C5A−0.04971 (18)0.34589 (16)0.10750 (10)0.0193 (3)
H5A−0.13820.40800.08340.023*
C6A−0.04823 (17)0.31234 (15)0.20434 (10)0.0174 (3)
C7A−0.18690 (17)0.38447 (16)0.26527 (10)0.0183 (3)
C8A−0.20800 (16)0.31981 (16)0.36677 (10)0.0173 (3)
C9A−0.28139 (17)0.41828 (16)0.43012 (11)0.0191 (3)
H9A−0.31350.52250.40810.023*
C10A−0.30776 (17)0.36486 (16)0.52506 (10)0.0196 (3)
H10A−0.35460.43280.56630.024*
C11A−0.26370 (17)0.20849 (16)0.55851 (10)0.0176 (3)
C12A−0.19281 (17)0.10750 (16)0.49558 (11)0.0193 (3)
H12A−0.16540.00310.51720.023*
C13A−0.16374 (17)0.16278 (16)0.40171 (10)0.0182 (3)
H13A−0.11400.09500.36070.022*
C14A0.3446 (2)0.1650 (2)−0.07020 (11)0.0283 (4)
H14A0.44200.1114−0.09910.042*
H14B0.32610.2725−0.09140.042*
H14C0.26750.1338−0.08690.042*
C15A−0.3511 (2)0.24333 (18)0.71693 (11)0.0272 (4)
H15A−0.35310.18430.77890.041*
H15B−0.45280.30080.70510.041*
H15C−0.29280.31170.71150.041*
O1B0.29024 (13)−0.00749 (12)0.75911 (8)0.0274 (3)
O2B0.28485 (12)0.35935 (12)0.34377 (7)0.0210 (3)
O3B−0.31914 (13)0.37626 (12)0.96641 (7)0.0235 (3)
C1B0.09869 (17)0.26402 (16)0.57589 (11)0.0186 (3)
H1B−0.00010.28270.60620.022*
C2B0.12419 (17)0.32062 (16)0.48158 (10)0.0182 (3)
H2B0.04260.37590.44870.022*
C3B0.27200 (17)0.29506 (15)0.43542 (10)0.0167 (3)
C4B0.39422 (17)0.20963 (16)0.48461 (10)0.0189 (3)
H4B0.49300.19200.45440.023*
C5B0.36678 (17)0.15134 (16)0.57903 (10)0.0189 (3)
H5B0.44810.09270.61130.023*
C6B0.21978 (17)0.17880 (15)0.62655 (10)0.0177 (3)
C7B0.19627 (17)0.10850 (16)0.72667 (10)0.0189 (3)
C8B0.05613 (17)0.17899 (16)0.78730 (10)0.0182 (3)
C9B−0.00698 (18)0.08532 (16)0.85877 (10)0.0199 (3)
H9B0.0361−0.01970.86570.024*
C10B−0.13333 (18)0.14621 (17)0.92001 (11)0.0205 (3)
H10B−0.17570.08240.96670.025*
C11B−0.19608 (17)0.30392 (16)0.91082 (10)0.0184 (3)
C12B−0.13197 (18)0.39894 (16)0.84036 (10)0.0192 (3)
H12B−0.17230.50400.83510.023*
C13B−0.00913 (17)0.33727 (16)0.77866 (10)0.0183 (3)
H13B0.03100.40120.73080.022*
C14B0.43412 (18)0.33423 (19)0.29271 (11)0.0255 (4)
H14D0.42770.38750.22950.038*
H14E0.48040.22730.29260.038*
H14F0.49420.37110.32190.038*
C15B−0.3891 (2)0.28448 (19)1.04042 (12)0.0302 (4)
H15D−0.47870.34871.07090.045*
H15E−0.31950.22991.08500.045*
H15F−0.41590.21341.01490.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0211 (6)0.0212 (5)0.0269 (6)−0.0024 (4)−0.0026 (5)0.0003 (5)
O2A0.0190 (6)0.0234 (5)0.0185 (5)−0.0032 (4)−0.0011 (4)−0.0030 (4)
O3A0.0277 (6)0.0198 (5)0.0190 (5)−0.0045 (4)−0.0032 (5)−0.0024 (4)
C1A0.0218 (8)0.0164 (7)0.0184 (7)−0.0070 (6)−0.0060 (6)−0.0011 (5)
C2A0.0189 (8)0.0160 (7)0.0230 (8)−0.0052 (6)−0.0072 (6)0.0007 (6)
C3A0.0181 (8)0.0146 (6)0.0219 (7)−0.0067 (6)−0.0022 (6)−0.0029 (6)
C4A0.0224 (8)0.0178 (7)0.0175 (7)−0.0070 (6)−0.0042 (6)−0.0009 (5)
C5A0.0205 (8)0.0171 (7)0.0213 (7)−0.0072 (6)−0.0054 (6)−0.0007 (6)
C6A0.0190 (8)0.0135 (6)0.0208 (7)−0.0067 (5)−0.0033 (6)−0.0021 (5)
C7A0.0180 (8)0.0159 (7)0.0224 (7)−0.0071 (6)−0.0038 (6)−0.0023 (6)
C8A0.0139 (7)0.0188 (7)0.0206 (7)−0.0066 (5)−0.0031 (6)−0.0030 (6)
C9A0.0162 (7)0.0159 (7)0.0246 (8)−0.0044 (5)−0.0030 (6)−0.0030 (6)
C10A0.0188 (8)0.0187 (7)0.0217 (7)−0.0048 (6)−0.0016 (6)−0.0064 (6)
C11A0.0159 (7)0.0198 (7)0.0183 (7)−0.0061 (6)−0.0049 (6)−0.0021 (6)
C12A0.0200 (8)0.0132 (6)0.0240 (8)−0.0047 (6)−0.0034 (6)−0.0014 (6)
C13A0.0158 (7)0.0157 (7)0.0241 (8)−0.0048 (5)−0.0021 (6)−0.0058 (6)
C14A0.0262 (9)0.0313 (9)0.0202 (8)−0.0025 (7)0.0004 (7)−0.0024 (6)
C15A0.0318 (9)0.0270 (8)0.0204 (8)−0.0048 (7)−0.0011 (7)−0.0072 (6)
O1B0.0300 (7)0.0210 (5)0.0235 (6)0.0013 (5)−0.0042 (5)−0.0016 (4)
O2B0.0181 (6)0.0246 (5)0.0178 (5)−0.0045 (4)−0.0018 (4)−0.0023 (4)
O3B0.0216 (6)0.0232 (5)0.0215 (6)−0.0039 (4)0.0014 (4)−0.0033 (4)
C1B0.0170 (7)0.0168 (7)0.0238 (8)−0.0065 (6)−0.0018 (6)−0.0058 (6)
C2B0.0158 (7)0.0174 (7)0.0216 (7)−0.0019 (6)−0.0072 (6)−0.0044 (6)
C3B0.0189 (8)0.0139 (6)0.0191 (7)−0.0056 (5)−0.0036 (6)−0.0041 (5)
C4B0.0162 (7)0.0192 (7)0.0220 (7)−0.0056 (6)−0.0008 (6)−0.0059 (6)
C5B0.0187 (8)0.0154 (7)0.0223 (7)−0.0032 (6)−0.0058 (6)−0.0029 (6)
C6B0.0197 (8)0.0136 (6)0.0202 (7)−0.0046 (5)−0.0029 (6)−0.0038 (5)
C7B0.0213 (8)0.0153 (7)0.0208 (7)−0.0056 (6)−0.0038 (6)−0.0033 (6)
C8B0.0198 (8)0.0181 (7)0.0172 (7)−0.0061 (6)−0.0036 (6)−0.0025 (5)
C9B0.0234 (8)0.0150 (7)0.0215 (7)−0.0063 (6)−0.0051 (6)−0.0013 (6)
C10B0.0235 (8)0.0196 (7)0.0198 (7)−0.0101 (6)−0.0040 (6)0.0006 (6)
C11B0.0175 (8)0.0205 (7)0.0177 (7)−0.0044 (6)−0.0060 (6)−0.0033 (6)
C12B0.0233 (8)0.0146 (6)0.0200 (7)−0.0049 (6)−0.0064 (6)−0.0020 (5)
C13B0.0221 (8)0.0162 (7)0.0179 (7)−0.0075 (6)−0.0060 (6)−0.0002 (5)
C14B0.0215 (8)0.0314 (8)0.0200 (8)−0.0050 (7)0.0012 (6)−0.0050 (6)
C15B0.0244 (9)0.0311 (9)0.0293 (9)−0.0089 (7)0.0048 (7)0.0002 (7)

Geometric parameters (Å, °)

O1A—C7A1.2272 (17)O1B—C7B1.2257 (17)
O2A—C3A1.3623 (17)O2B—C3B1.3550 (17)
O2A—C14A1.4394 (18)O2B—C14B1.4336 (18)
O3A—C11A1.3576 (17)O3B—C11B1.3599 (17)
O3A—C15A1.4377 (17)O3B—C15B1.4343 (19)
C1A—C2A1.374 (2)C1B—C2B1.382 (2)
C1A—C6A1.399 (2)C1B—C6B1.402 (2)
C1A—H1A0.93C1B—H1B0.93
C2A—C3A1.393 (2)C2B—C3B1.396 (2)
C2A—H2A0.93C2B—H2B0.93
C3A—C4A1.399 (2)C3B—C4B1.398 (2)
C4A—C5A1.383 (2)C4B—C5B1.389 (2)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.398 (2)C5B—C6B1.396 (2)
C5A—H5A0.93C5B—H5B0.93
C6A—C7A1.4893 (19)C6B—C7B1.487 (2)
C7A—C8A1.490 (2)C7B—C8B1.491 (2)
C8A—C9A1.3930 (19)C8B—C9B1.392 (2)
C8A—C13A1.405 (2)C8B—C13B1.4035 (19)
C9A—C10A1.385 (2)C9B—C10B1.391 (2)
C9A—H9A0.93C9B—H9B0.93
C10A—C11A1.395 (2)C10B—C11B1.396 (2)
C10A—H10A0.93C10B—H10B0.93
C11A—C12A1.4012 (19)C11B—C12B1.397 (2)
C12A—C13A1.377 (2)C12B—C13B1.378 (2)
C12A—H12A0.93C12B—H12B0.93
C13A—H13A0.93C13B—H13B0.93
C14A—H14A0.96C14B—H14D0.96
C14A—H14B0.96C14B—H14E0.96
C14A—H14C0.96C14B—H14F0.96
C15A—H15A0.96C15B—H15D0.96
C15A—H15B0.96C15B—H15E0.96
C15A—H15C0.96C15B—H15F0.96
C3A—O2A—C14A117.70 (12)C3B—O2B—C14B117.78 (12)
C11A—O3A—C15A117.33 (11)C11B—O3B—C15B117.90 (12)
C2A—C1A—C6A121.10 (14)C2B—C1B—C6B120.88 (14)
C2A—C1A—H1A119.5C2B—C1B—H1B119.6
C6A—C1A—H1A119.5C6B—C1B—H1B119.6
C1A—C2A—C3A120.14 (14)C1B—C2B—C3B120.21 (14)
C1A—C2A—H2A119.9C1B—C2B—H2B119.9
C3A—C2A—H2A119.9C3B—C2B—H2B119.9
O2A—C3A—C2A115.76 (13)O2B—C3B—C2B115.56 (13)
O2A—C3A—C4A124.33 (13)O2B—C3B—C4B124.67 (13)
C2A—C3A—C4A119.90 (13)C2B—C3B—C4B119.76 (14)
C5A—C4A—C3A119.20 (14)C5B—C4B—C3B119.40 (14)
C5A—C4A—H4A120.4C5B—C4B—H4B120.3
C3A—C4A—H4A120.4C3B—C4B—H4B120.3
C4A—C5A—C6A121.50 (14)C4B—C5B—C6B121.46 (14)
C4A—C5A—H5A119.2C4B—C5B—H5B119.3
C6A—C5A—H5A119.2C6B—C5B—H5B119.3
C5A—C6A—C1A118.13 (13)C5B—C6B—C1B118.27 (14)
C5A—C6A—C7A118.48 (13)C5B—C6B—C7B119.27 (13)
C1A—C6A—C7A123.22 (13)C1B—C6B—C7B122.33 (13)
O1A—C7A—C6A120.49 (13)O1B—C7B—C6B120.47 (13)
O1A—C7A—C8A119.53 (13)O1B—C7B—C8B120.05 (13)
C6A—C7A—C8A119.96 (12)C6B—C7B—C8B119.47 (12)
C9A—C8A—C13A117.96 (14)C9B—C8B—C13B118.68 (13)
C9A—C8A—C7A118.92 (12)C9B—C8B—C7B118.98 (13)
C13A—C8A—C7A123.05 (12)C13B—C8B—C7B122.22 (14)
C10A—C9A—C8A121.65 (13)C10B—C9B—C8B121.10 (13)
C10A—C9A—H9A119.2C10B—C9B—H9B119.5
C8A—C9A—H9A119.2C8B—C9B—H9B119.5
C9A—C10A—C11A119.62 (13)C9B—C10B—C11B119.45 (14)
C9A—C10A—H10A120.2C9B—C10B—H10B120.3
C11A—C10A—H10A120.2C11B—C10B—H10B120.3
O3A—C11A—C10A124.78 (13)O3B—C11B—C10B124.69 (14)
O3A—C11A—C12A115.67 (12)O3B—C11B—C12B115.42 (12)
C10A—C11A—C12A119.55 (14)C10B—C11B—C12B119.88 (13)
C13A—C12A—C11A120.05 (13)C13B—C12B—C11B120.14 (13)
C13A—C12A—H12A120.0C13B—C12B—H12B119.9
C11A—C12A—H12A120.0C11B—C12B—H12B119.9
C12A—C13A—C8A121.14 (13)C12B—C13B—C8B120.72 (14)
C12A—C13A—H13A119.4C12B—C13B—H13B119.6
C8A—C13A—H13A119.4C8B—C13B—H13B119.6
O2A—C14A—H14A109.5O2B—C14B—H14D109.5
O2A—C14A—H14B109.5O2B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
O2A—C14A—H14C109.5O2B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
O3A—C15A—H15A109.5O3B—C15B—H15D109.5
O3A—C15A—H15B109.5O3B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O3A—C15A—H15C109.5O3B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C6A—C1A—C2A—C3A−0.9 (2)C6B—C1B—C2B—C3B−0.8 (2)
C14A—O2A—C3A—C2A−177.69 (14)C14B—O2B—C3B—C2B−178.89 (13)
C14A—O2A—C3A—C4A3.1 (2)C14B—O2B—C3B—C4B2.0 (2)
C1A—C2A—C3A—O2A−177.55 (13)C1B—C2B—C3B—O2B−178.01 (12)
C1A—C2A—C3A—C4A1.7 (2)C1B—C2B—C3B—C4B1.1 (2)
O2A—C3A—C4A—C5A178.31 (13)O2B—C3B—C4B—C5B178.98 (13)
C2A—C3A—C4A—C5A−0.9 (2)C2B—C3B—C4B—C5B−0.1 (2)
C3A—C4A—C5A—C6A−0.7 (2)C3B—C4B—C5B—C6B−1.4 (2)
C4A—C5A—C6A—C1A1.5 (2)C4B—C5B—C6B—C1B1.7 (2)
C4A—C5A—C6A—C7A176.83 (14)C4B—C5B—C6B—C7B177.53 (13)
C2A—C1A—C6A—C5A−0.6 (2)C2B—C1B—C6B—C5B−0.6 (2)
C2A—C1A—C6A—C7A−175.76 (14)C2B—C1B—C6B—C7B−176.32 (13)
C5A—C6A—C7A—O1A−19.5 (2)C5B—C6B—C7B—O1B−24.1 (2)
C1A—C6A—C7A—O1A155.62 (15)C1B—C6B—C7B—O1B151.59 (15)
C5A—C6A—C7A—C8A162.10 (14)C5B—C6B—C7B—C8B156.77 (14)
C1A—C6A—C7A—C8A−22.8 (2)C1B—C6B—C7B—C8B−27.6 (2)
O1A—C7A—C8A—C9A−32.7 (2)O1B—C7B—C8B—C9B−32.4 (2)
C6A—C7A—C8A—C9A145.72 (15)C6B—C7B—C8B—C9B146.71 (15)
O1A—C7A—C8A—C13A144.16 (16)O1B—C7B—C8B—C13B143.46 (16)
C6A—C7A—C8A—C13A−37.4 (2)C6B—C7B—C8B—C13B−37.4 (2)
C13A—C8A—C9A—C10A1.4 (2)C13B—C8B—C9B—C10B0.8 (2)
C7A—C8A—C9A—C10A178.38 (14)C7B—C8B—C9B—C10B176.84 (15)
C8A—C9A—C10A—C11A−1.7 (2)C8B—C9B—C10B—C11B−1.3 (2)
C15A—O3A—C11A—C10A−1.6 (2)C15B—O3B—C11B—C10B0.6 (2)
C15A—O3A—C11A—C12A177.99 (14)C15B—O3B—C11B—C12B−179.56 (14)
C9A—C10A—C11A—O3A179.83 (14)C9B—C10B—C11B—O3B180.00 (15)
C9A—C10A—C11A—C12A0.2 (2)C9B—C10B—C11B—C12B0.1 (2)
O3A—C11A—C12A—C13A−178.09 (14)O3B—C11B—C12B—C13B−178.39 (14)
C10A—C11A—C12A—C13A1.6 (2)C10B—C11B—C12B—C13B1.5 (2)
C11A—C12A—C13A—C8A−1.9 (2)C11B—C12B—C13B—C8B−2.0 (2)
C9A—C8A—C13A—C12A0.4 (2)C9B—C8B—C13B—C12B0.8 (2)
C7A—C8A—C13A—C12A−176.43 (15)C7B—C8B—C13B—C12B−175.07 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14B—H14E···O1Bi0.962.593.446 (2)149
C9B—H9B···Cg1ii0.932.843.5252 (17)132
C12B—H12B···Cg1iii0.932.783.5223 (16)137
C4B—H4B···Cg2iv0.932.883.6301 (18)138
C9A—H9A···Cg3iii0.932.923.5723 (16)128
C12A—H12A···Cg3ii0.932.883.5651 (16)132
C4A—H4A···Cg4v0.932.903.6376 (17)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2608).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Norment, H. G. & Karle, I. L. (1962). Acta Cryst.15, 873–878.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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