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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o777.
Published online 2008 April 2. doi:  10.1107/S1600536808008428
PMCID: PMC2961125

2,4-Bis(4-chloro­benzo­yl)-1-(4-chloro­phen­yl)-3,5-di-2-thienylcyclo­hexa­nol methanol hemisolvate

Abstract

The title compound, C34H25Cl3O3S2·0.5CH3OH, was synthesized by the reaction of thio­phene-2-carbaldehyde with acetophenone and NaOH under solvent-free conditions, using tetra­butylammonium bromide as a phase-transfer catalyst. The central six-membered ring adopts a chair conformation with the bulky thio­phene, 4-chloro­phenyl and 4-chloro­benzoyl substituents in equatorial positions. The hydroxyl group is in an axial position and forms an intra­molecular O—H(...)O hydrogen bond to the carbonyl group of an adjacent 4-chloro­benzoyl substituent. The methanol solvent mol­ecules are disordered equally over two positions within one-dimensional channels, with site occupancy factors of 0.25.

Related literature

For related structures, see: Luo & Shan (2006 [triangle]); Huang & Wang (2007 [triangle]).

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Object name is e-64-0o777-scheme1.jpg

Experimental

Crystal data

  • C34H25Cl3O3S2·0.5CH4O
  • M r = 668.03
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o777-efi1.jpg
  • a = 22.5660 (16) Å
  • b = 12.1356 (12) Å
  • c = 26.030 (2) Å
  • V = 7128.4 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 298 (2) K
  • 0.67 × 0.16 × 0.13 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.772, T max = 0.949
  • 27584 measured reflections
  • 4502 independent reflections
  • 2357 reflections with I > 2σ(I)
  • R int = 0.096
  • θmax = 22.5°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.080
  • wR(F 2) = 0.290
  • S = 1.09
  • 4502 reflections
  • 415 parameters
  • 50 restraints
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle])); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008428/bi2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008428/bi2281Isup2.hkl

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

Acknowledgments

The authors acknowledge support from the National Natural Science Foundation of Liaocheng University (No. X051040).

supplementary crystallographic information

Comment

The title compound (Fig. 1) was synthesized by condensation and Michael addition of thiophene-2-carbaldehyde with 4-chloroacetophenone under solvent-free conditions, using tetrabutyl ammonium bromide as a phase-transfer catalyst. The bond lengths and angles are comparable to those observed in the related compounds 2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol (Luo & Shan, 2006) and 2,4-dibenzoyl-3,5-bis(2-thienyl)-1-phenylcyclohexanol (Huang & Wang, 2007). The hydroxyl group in the axial position forms an intramolecular O—H···O hydrogen bond to the carbonyl group of an adjacent para-chlorobenzoyl substituent (Table 1). The methanol solvent molecules lie within channels running along the crystallogaphic b axis, and are modelled as disordered along those channels.

Experimental

4-Chloroacetophenone (6.25 mmol), freshly distilled thiophene-2-carbaldehyde (3.125 mmol), NaOH (6.25 mmol) and tetrabutyl ammonium bromide (1 mmol) were mixed with a glass paddle in an open flask. The resulting mixture was washed several times with water to remove NaOH and recrystallized from methanol to give the title compound as a crystalline solid. Elemental analysis calculated: C 62.03, H 4.07%; found: C 62.08, H 4.02%.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5Ueq(C). The H atoms of hydroxyl groups were placed in idealized positions with O—H = 0.82 Å and refined as riding with Uiso(H) = 1.5Ueq(O). The crystal diffracted relatively weakly and the data are therefore limited to θmax = 22.5°, with ca 50% data observed at the 2σ(I) level. The resulting structure is therefore of relatively low precision. The methanol solvent molecule was refined as disordered over two orientations, each with 25% site occupancy to give reasonable displacement parameters. The C—O bonds were restrained to 1.45 (2) Å and the anisotropic displacement parameters of all atoms were restrained to have approximately equal components.

Figures

Fig. 1.
Molecular stucture showing displacement ellipsoids at 20% probability. H atoms and the disordered methanol molecule is omitted.

Crystal data

C34H25Cl3O3S2·0.5CH4OF000 = 2760
Mr = 668.03Dx = 1.245 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3877 reflections
a = 22.5660 (16) Åθ = 2.4–19.6º
b = 12.1356 (12) ŵ = 0.41 mm1
c = 26.030 (2) ÅT = 298 (2) K
V = 7128.4 (11) Å3Block, colourless
Z = 80.67 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer4502 independent reflections
Radiation source: fine-focus sealed tube2357 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.096
T = 298(2) Kθmax = 22.5º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −24→21
Tmin = 0.772, Tmax = 0.949k = −13→12
27584 measured reflectionsl = −28→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080H-atom parameters constrained
wR(F2) = 0.290  w = 1/[σ2(Fo2) + (0.1474P)2 + 3.8778P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.004
4502 reflectionsΔρmax = 0.64 e Å3
415 parametersΔρmin = −0.40 e Å3
50 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/UeqOcc. (<1)
Cl10.95396 (12)0.3492 (3)−0.16180 (9)0.1142 (10)
Cl21.09441 (11)0.3656 (2)0.12369 (13)0.1225 (11)
Cl30.53719 (14)0.0925 (3)0.28831 (11)0.1374 (13)
O10.8096 (2)−0.0250 (4)−0.02208 (17)0.0638 (13)
H10.8436−0.0488−0.02310.096*
O20.9156 (2)−0.0200 (4)0.0317 (2)0.0713 (14)
O30.7060 (2)−0.1231 (5)0.1052 (2)0.0798 (16)
O40.769 (2)0.641 (7)0.351 (3)0.26 (2)0.25
H40.78630.67940.33050.395*0.25
O50.747 (2)0.302 (6)0.304 (3)0.27 (2)0.25
H50.77350.28000.28560.401*0.25
S10.86979 (15)−0.0641 (3)0.16254 (12)0.1253 (11)
S20.62891 (9)0.23441 (18)0.03888 (10)0.0801 (7)
C10.8106 (3)0.0886 (5)−0.0078 (2)0.0512 (17)
C20.8364 (3)0.1015 (5)0.0474 (2)0.0486 (16)
H20.83210.17840.05830.058*
C30.8012 (3)0.0259 (6)0.0853 (3)0.0547 (18)
H30.8045−0.05020.07310.066*
C40.7355 (3)0.0580 (6)0.0849 (2)0.0506 (17)
H4A0.73080.13110.10040.061*
C50.7092 (3)0.0585 (6)0.0302 (3)0.0531 (17)
H5A0.7086−0.01770.01770.064*
C60.7465 (3)0.1268 (6)−0.0074 (3)0.0565 (18)
H6A0.73010.1202−0.04170.068*
H6B0.74490.20390.00240.068*
C70.8479 (3)0.1562 (6)−0.0462 (2)0.0551 (18)
C80.8786 (3)0.1061 (7)−0.0853 (3)0.073 (2)
H80.87700.0298−0.08840.088*
C90.9118 (4)0.1661 (9)−0.1201 (3)0.084 (3)
H90.93270.1301−0.14590.101*
C100.9137 (3)0.2763 (8)−0.1166 (3)0.071 (2)
C110.8847 (4)0.3293 (8)−0.0774 (3)0.080 (2)
H110.88710.4055−0.07420.096*
C120.8519 (4)0.2680 (7)−0.0428 (3)0.069 (2)
H120.83210.3041−0.01640.083*
C130.9012 (3)0.0708 (6)0.0487 (3)0.0547 (18)
C140.9471 (3)0.1467 (6)0.0680 (3)0.0529 (17)
C150.9353 (3)0.2480 (6)0.0891 (3)0.078 (2)
H150.89620.27100.09240.093*
C160.9803 (4)0.3164 (7)0.1056 (4)0.090 (3)
H160.97170.38590.11870.108*
C171.0372 (3)0.2813 (8)0.1023 (3)0.072 (2)
C181.0507 (4)0.1813 (8)0.0824 (3)0.079 (2)
H181.09000.15880.08020.095*
C191.0067 (3)0.1142 (7)0.0655 (3)0.070 (2)
H191.01620.04540.05200.084*
C200.8272 (3)0.0314 (6)0.1381 (3)0.0601 (19)
C210.8207 (3)0.1219 (6)0.1774 (2)0.0587 (18)
H210.79720.18440.17400.070*
C220.8565 (5)0.0956 (10)0.2202 (4)0.112 (3)
H220.86140.14300.24790.135*
C230.8815 (5)0.0013 (12)0.2177 (4)0.120 (4)
H230.9041−0.02800.24420.144*
C240.7011 (3)−0.0268 (7)0.1167 (3)0.0565 (18)
C250.6618 (3)0.0078 (7)0.1602 (3)0.0610 (19)
C260.6492 (4)0.1131 (8)0.1721 (3)0.083 (2)
H260.66730.16910.15340.100*
C270.6109 (4)0.1411 (9)0.2108 (4)0.096 (3)
H270.60270.21460.21800.115*
C280.5848 (4)0.0586 (10)0.2387 (3)0.085 (3)
C290.5948 (5)−0.0444 (10)0.2273 (4)0.109 (3)
H290.5755−0.09990.24540.131*
C300.6346 (4)−0.0719 (8)0.1880 (3)0.090 (3)
H300.6424−0.14560.18090.108*
C310.6455 (3)0.0992 (6)0.0322 (3)0.0537 (17)
C320.5939 (3)0.0334 (6)0.0320 (3)0.0607 (19)
H320.5929−0.04270.02800.073*
C330.5433 (3)0.1036 (8)0.0389 (3)0.080 (2)
H330.50480.07660.04020.095*
C340.5559 (3)0.2092 (8)0.0432 (3)0.078 (2)
H340.52740.26370.04810.094*
C350.756 (4)0.534 (7)0.328 (4)0.26 (2)0.25
H35A0.78550.51810.30270.394*0.25
H35B0.71770.53590.31260.394*0.25
H35C0.75700.47830.35440.394*0.25
C360.752 (3)0.420 (7)0.311 (4)0.26 (2)0.25
H36A0.73770.45770.28140.394*0.25
H36B0.79310.43910.31680.394*0.25
H36C0.72940.44260.34080.394*0.25

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1111 (19)0.148 (3)0.0834 (16)−0.0190 (16)0.0260 (13)0.0327 (16)
Cl20.0846 (17)0.096 (2)0.186 (3)−0.0247 (14)−0.0361 (17)−0.0093 (18)
Cl30.131 (2)0.192 (3)0.0885 (19)0.017 (2)0.0507 (16)0.0001 (19)
O10.074 (3)0.047 (3)0.071 (3)0.001 (2)0.006 (2)−0.013 (2)
O20.064 (3)0.053 (3)0.097 (4)0.008 (3)0.006 (3)−0.017 (3)
O30.085 (4)0.056 (4)0.099 (4)−0.012 (3)0.028 (3)−0.003 (3)
O40.14 (3)0.34 (7)0.31 (5)0.05 (4)−0.03 (2)0.05 (5)
O50.15 (2)0.34 (7)0.31 (5)0.05 (4)−0.02 (2)0.04 (5)
S10.145 (3)0.110 (2)0.121 (2)0.0275 (19)−0.0365 (18)0.0112 (18)
S20.0612 (12)0.0590 (14)0.1201 (18)0.0011 (10)−0.0021 (11)−0.0019 (12)
C10.055 (4)0.043 (4)0.056 (4)0.003 (3)0.007 (3)−0.003 (3)
C20.048 (4)0.044 (4)0.055 (4)−0.001 (3)0.010 (3)0.000 (3)
C30.054 (4)0.053 (4)0.057 (4)0.002 (3)0.008 (3)−0.001 (3)
C40.045 (4)0.049 (4)0.058 (4)−0.004 (3)0.003 (3)0.001 (3)
C50.049 (4)0.044 (4)0.066 (4)−0.006 (3)0.000 (3)−0.007 (3)
C60.049 (4)0.060 (5)0.060 (4)−0.006 (3)0.004 (3)0.000 (4)
C70.053 (4)0.065 (5)0.048 (4)−0.003 (3)0.004 (3)0.002 (4)
C80.084 (5)0.073 (6)0.062 (5)0.009 (4)0.021 (4)0.002 (4)
C90.089 (6)0.100 (8)0.063 (5)0.014 (5)0.025 (4)0.002 (5)
C100.060 (5)0.090 (7)0.061 (5)−0.002 (5)0.008 (4)0.010 (5)
C110.084 (5)0.080 (6)0.076 (6)−0.011 (5)0.013 (5)0.011 (5)
C120.088 (5)0.055 (5)0.063 (5)−0.007 (4)0.021 (4)0.001 (4)
C130.057 (4)0.047 (5)0.060 (4)0.008 (4)0.009 (3)0.001 (4)
C140.046 (4)0.053 (5)0.059 (4)−0.002 (3)0.001 (3)0.002 (3)
C150.052 (4)0.056 (5)0.125 (7)0.006 (4)−0.010 (4)−0.018 (5)
C160.082 (6)0.054 (5)0.136 (8)0.010 (5)−0.018 (5)−0.021 (5)
C170.053 (5)0.084 (7)0.079 (5)−0.009 (4)−0.013 (4)0.015 (5)
C180.057 (5)0.080 (6)0.101 (6)0.005 (5)0.002 (4)−0.007 (5)
C190.048 (4)0.078 (6)0.084 (6)0.009 (4)0.006 (4)−0.017 (4)
C200.060 (4)0.060 (5)0.060 (4)−0.006 (4)−0.002 (3)0.009 (4)
C210.072 (4)0.051 (4)0.053 (4)0.006 (3)−0.028 (3)−0.013 (3)
C220.128 (6)0.113 (6)0.097 (5)−0.001 (5)−0.023 (5)−0.013 (5)
C230.118 (8)0.160 (12)0.082 (7)−0.006 (8)−0.037 (6)0.036 (7)
C240.065 (5)0.047 (5)0.057 (4)−0.009 (4)0.005 (3)−0.003 (4)
C250.051 (4)0.073 (6)0.059 (4)−0.012 (4)0.001 (3)0.006 (4)
C260.091 (6)0.073 (7)0.085 (6)0.006 (5)0.024 (5)0.008 (5)
C270.109 (7)0.094 (7)0.085 (6)0.028 (6)0.033 (6)0.005 (6)
C280.077 (6)0.126 (9)0.052 (5)0.007 (6)0.010 (4)−0.007 (6)
C290.156 (10)0.093 (8)0.078 (6)−0.028 (7)0.036 (7)0.000 (6)
C300.116 (7)0.071 (6)0.082 (6)−0.017 (5)0.021 (5)0.005 (5)
C310.048 (4)0.052 (4)0.061 (4)−0.002 (3)0.000 (3)−0.004 (3)
C320.033 (4)0.059 (5)0.090 (5)−0.011 (3)0.006 (3)−0.013 (4)
C330.041 (4)0.104 (8)0.094 (6)−0.014 (4)−0.002 (4)−0.008 (5)
C340.060 (5)0.077 (7)0.097 (6)0.002 (4)−0.002 (4)0.002 (5)
C350.15 (2)0.34 (7)0.31 (5)0.06 (4)−0.04 (2)0.05 (5)
C360.14 (2)0.34 (7)0.31 (5)0.06 (4)−0.04 (2)0.05 (5)

Geometric parameters (Å, °)

Cl1—C101.729 (8)C12—H120.930
Cl2—C171.739 (8)C13—C141.475 (10)
Cl3—C281.730 (9)C14—C151.374 (10)
O1—C11.428 (7)C14—C191.402 (9)
O1—H10.820C15—C161.380 (11)
O2—C131.230 (8)C15—H150.930
O3—C241.211 (8)C16—C171.355 (11)
O4—C351.45 (2)C16—H160.930
O4—H40.820C17—C181.354 (11)
O5—C361.45 (2)C18—C191.358 (11)
O5—H50.820C18—H180.930
S1—C201.633 (8)C19—H190.930
S1—C231.661 (12)C20—C211.508 (10)
S2—C341.681 (8)C21—C221.411 (13)
S2—C311.692 (7)C21—H210.930
C1—C61.519 (9)C22—C231.279 (15)
C1—C71.543 (9)C22—H220.930
C1—C21.560 (9)C23—H230.930
C2—C131.509 (9)C24—C251.498 (10)
C2—C31.564 (9)C25—C261.346 (11)
C2—H20.980C25—C301.355 (11)
C3—C201.497 (10)C26—C271.371 (11)
C3—C41.533 (9)C26—H260.930
C3—H30.980C27—C281.369 (13)
C4—C241.531 (9)C27—H270.930
C4—C51.544 (9)C28—C291.304 (13)
C4—H4A0.980C29—C301.400 (13)
C5—C311.520 (9)C29—H290.930
C5—C61.535 (9)C30—H300.930
C5—H5A0.980C31—C321.411 (9)
C6—H6A0.970C32—C331.436 (11)
C6—H6B0.970C32—H320.930
C7—C121.363 (10)C33—C341.317 (11)
C7—C81.372 (10)C33—H330.930
C8—C91.383 (11)C34—H340.930
C8—H80.930C35—H35A0.960
C9—C101.341 (12)C35—H35B0.960
C9—H90.930C35—H35C0.960
C10—C111.372 (11)C36—H36A0.960
C11—C121.383 (10)C36—H36B0.960
C11—H110.930C36—H36C0.960
C1—O1—H1109.5C17—C16—H16120.4
C35—O4—H4109.5C15—C16—H16120.4
C36—O5—H5109.5C18—C17—C16121.3 (7)
C20—S1—C2395.2 (5)C18—C17—Cl2118.8 (6)
C34—S2—C3192.7 (4)C16—C17—Cl2119.9 (7)
O1—C1—C6106.3 (5)C17—C18—C19119.8 (7)
O1—C1—C7110.7 (5)C17—C18—H18120.1
C6—C1—C7111.2 (5)C19—C18—H18120.1
O1—C1—C2110.0 (5)C18—C19—C14121.2 (8)
C6—C1—C2108.6 (5)C18—C19—H19119.4
C7—C1—C2109.9 (5)C14—C19—H19119.4
C13—C2—C1110.9 (5)C3—C20—C21128.1 (6)
C13—C2—C3109.5 (5)C3—C20—S1123.8 (6)
C1—C2—C3109.4 (5)C21—C20—S1108.1 (5)
C13—C2—H2109.0C22—C21—C20108.3 (7)
C1—C2—H2109.0C22—C21—H21125.8
C3—C2—H2109.0C20—C21—H21125.8
C20—C3—C4111.9 (5)C23—C22—C21114.5 (10)
C20—C3—C2110.8 (5)C23—C22—H22122.7
C4—C3—C2109.8 (5)C21—C22—H22122.7
C20—C3—H3108.1C22—C23—S1113.7 (8)
C4—C3—H3108.1C22—C23—H23123.2
C2—C3—H3108.1S1—C23—H23123.2
C24—C4—C3108.4 (6)O3—C24—C25120.6 (6)
C24—C4—C5107.8 (5)O3—C24—C4118.0 (6)
C3—C4—C5112.3 (5)C25—C24—C4121.3 (7)
C24—C4—H4A109.4C26—C25—C30117.3 (8)
C3—C4—H4A109.4C26—C25—C24124.5 (7)
C5—C4—H4A109.4C30—C25—C24118.2 (8)
C31—C5—C6111.5 (6)C25—C26—C27122.6 (8)
C31—C5—C4109.5 (5)C25—C26—H26118.7
C6—C5—C4112.3 (5)C27—C26—H26118.7
C31—C5—H5A107.8C28—C27—C26118.6 (9)
C6—C5—H5A107.8C28—C27—H27120.7
C4—C5—H5A107.8C26—C27—H27120.7
C1—C6—C5111.3 (6)C29—C28—C27120.4 (8)
C1—C6—H6A109.4C29—C28—Cl3120.4 (9)
C5—C6—H6A109.4C27—C28—Cl3119.2 (9)
C1—C6—H6B109.4C28—C29—C30120.4 (9)
C5—C6—H6B109.4C28—C29—H29119.8
H6A—C6—H6B108.0C30—C29—H29119.8
C12—C7—C8117.2 (7)C25—C30—C29120.7 (9)
C12—C7—C1121.5 (6)C25—C30—H30119.6
C8—C7—C1121.3 (7)C29—C30—H30119.6
C7—C8—C9121.7 (8)C32—C31—C5126.6 (6)
C7—C8—H8119.2C32—C31—S2111.5 (5)
C9—C8—H8119.2C5—C31—S2121.8 (5)
C10—C9—C8119.9 (8)C31—C32—C33108.7 (7)
C10—C9—H9120.0C31—C32—H32125.7
C8—C9—H9120.0C33—C32—H32125.7
C9—C10—C11120.1 (7)C34—C33—C32114.7 (7)
C9—C10—Cl1118.8 (7)C34—C33—H33122.7
C11—C10—Cl1121.1 (7)C32—C33—H33122.7
C10—C11—C12119.2 (8)C33—C34—S2112.4 (6)
C10—C11—H11120.4C33—C34—H34123.8
C12—C11—H11120.4S2—C34—H34123.8
C7—C12—C11121.9 (7)O4—C35—H35A109.5
C7—C12—H12119.1O4—C35—H35B109.5
C11—C12—H12119.1H35A—C35—H35B109.5
O2—C13—C14119.8 (6)O4—C35—H35C109.5
O2—C13—C2117.9 (6)H35A—C35—H35C109.5
C14—C13—C2122.2 (6)H35B—C35—H35C109.5
C15—C14—C19117.2 (7)O5—C36—H36A109.5
C15—C14—C13124.0 (6)O5—C36—H36B109.5
C19—C14—C13118.8 (7)H36A—C36—H36B109.5
C14—C15—C16121.3 (7)O5—C36—H36C109.5
C14—C15—H15119.4H36A—C36—H36C109.5
C16—C15—H15119.4H36B—C36—H36C109.5
C17—C16—C15119.2 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.192.772 (7)128

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2281).

References

  • Bruker (2001). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Huang, X.-Q. & Wang, J.-X. (2007). Acta Cryst. E63, o4168.
  • Luo, X. & Shan, Z. (2006). Acta Cryst. E62, o1631–o1632.
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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