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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o507.
Published online 2008 January 23. doi:  10.1107/S1600536807066469
PMCID: PMC2960412

Benzoyl­methyl 4-chloro­benzoate

Abstract

The asymmetric unit of the title compound, C15H11ClO3, contains three mol­ecules, A, B, and C. Mol­ecules A and B are aligned edge-to-face, whereas mol­ecules B and C are aligned almost parallel to each other. The crystal structure displays C—H(...)π and π–π [centroid–centroid distances of 3.960 (4), 3.971 (4) and 3.971 (4) for mol­ecules A, B and C, respectively] parallel-displaced inter­actions, and C—H(...)O hydrogen bonds.

Related literature

For background literature, see: Kelly & Howard (1932 [triangle]). For the synthesis, see Hendrickson & Kandall (1970 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o507-scheme1.jpg

Experimental

Crystal data

  • C15H11ClO3
  • M r = 274.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o507-efi1.jpg
  • a = 14.7634 (6) Å
  • b = 16.4509 (6) Å
  • c = 15.8214 (5) Å
  • β = 92.105 (4)°
  • V = 3840.0 (2) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 293 (2) K
  • 0.18 × 0.15 × 0.10 mm

Data collection

  • Bruker APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.948, T max = 0.971
  • 18809 measured reflections
  • 6647 independent reflections
  • 3093 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.071
  • S = 0.79
  • 6647 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT (Bruker, 2001 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [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/S1600536807066469/ng2408sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066469/ng2408Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Key Foundation of Science & Technology Project of Fujian Province, China (Key grant No. 2002H011) and also thank Professor G. M. Blackburn and Mr Harry Adams of Sheffield University Chemistry Department for their helpful suggestions.

supplementary crystallographic information

Comment

An X-ray crystal structure determination of the molecule of the title compound, 2-oxo-2-phenylethyl 4-chlorobenzoate, (I) (Scheme. 1), was carried out to determine its conformation and the results are presented here. The bond lengths and angles are within their normal ranges (Allen et al., 1987).

The unit cell has four identical asymmetric units which contain three molecules of (I) each (Fig. 2). In each asymmetric unit, the benzene rings of molecules B and C stack in a parallel-displaced structure, while the benzene rings of molecules A and B form a displaced T-shaped structure (Fig. 1). The two benzene rings within molecule A make a dihedral angle of 61.68 (6)°, while the two benzene rings within molecules B and C make almost identical dihedral angles of 77.66 (6)° and 77.29 (6)° respectively.

Hydrogen bonds C—H···O which are found not only between molecules A and B in the asymmetric unit but also between molecule A and the symmetry- equivalent Ci in the next asymmetric unit (Fig. 3). These C—H···O interactions stabilize the formation of asymmetric units as well as of the whole unit cell (Table 2).

Meanwhile, π—π interactions in stacked, slipped benzene rings from two symmetry-equivalent molecules in adjacent asymmetric units also provide stability for the crystal structure. The distance between Cg1 A and Cg2 Aii is 3.960 (4) Å and the angles between the line through the centroids of these two benzene rings and the normal through Cg1 A is 26.6 (1)° and through Cg2 Aii is 25.0 (1)°. The corresponding values for benzene rings C1B/C6B and C10B/C15Biii are 3.971 (4) Å, 26.4 (1)° and 24.9 (1)°. For C1C/C6C and C10C/C15Ciii they are 3.971 (4) Å, 18.1 (1)° and 33.5 (1)°.Cg1X and Cg2X are the centroids of C1/C6 and C10/C15 benzene rings in molecule X (X=A, B, C) respectively [Symmetry code: (ii) x, -y - 1/2, z + 1/2; (iii) x, -y + 1/2, z - 1/2] (Fig. 2). The packing is further stabilized by weak C—H···π interactions(Table 1).The distances and angles correspond to their caculated ranges.

Experimental

Triethylamine (0.84 ml, 6 mmol) was slowly dropped into 2-bromo-1-phenylethanone (796 mg, 4 mmol) and 4-chlorobenzoic acid (630 mg, 4 mmol) dissolved in freshly distilled tetrahydrofuran (10 ml) at rt under nitrogen and stirred overnight. The precipitate was collected at the pump and washed with ethyl acetate. The filtrate and washings were combined and back-washed successively with 1/3 of the volume each of 10% citric acid, 10% sodium bicarbonate, and water and then dried. Solvent was distilled off in vacuo and the residue recrystallized repeatedly from ethyl acetate-petroleum ether giving 1.085 g (98%) as colourless needles, m.p.128°C. (Hendrickson & Kandall, 1970).

Refinement

The hydrogen atoms were generated geometrically (C—H = 0.93, 0.98, 0.97 or 0.96Å for phenyl, tertiary, methylene or methyl H atoms respectively, and N—H = 0.86 Å) and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5 times Ueq of the equivalent isotropic displacement parameters of their parent atoms, while those of other H atoms were set to 1.2 times.

Figures

Fig. 1.
The asymmetric unit of (I), drawn with 50% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radius.
Fig. 2.
The unit cell of (I). The same subscript means the molecules form one asymmetric unit and the symmetry-equivalent molecules have the same color.
Fig. 3.
The asymmetric unit of molecule (I) which is formed by three molecules A, B, and Ci—symmetry-equivalent of C in the next asymmetric unit. Hydrogen bonds are indicated by dashed lines.

Crystal data

C15H11ClO3F000 = 1704
Mr = 274.69Dx = 1.425 Mg m3
Monoclinic, P21/cMelting point: 128 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 14.7634 (6) ÅCell parameters from 3122 reflections
b = 16.4509 (6) Åθ = 2.5–32.7º
c = 15.8214 (5) ŵ = 0.30 mm1
β = 92.105 (4)ºT = 293 (2) K
V = 3840.0 (2) Å3Needle, colorless
Z = 120.18 × 0.15 × 0.10 mm

Data collection

Bruker APEX area-detector diffractometer6647 independent reflections
Radiation source: fine-focus sealed tube3093 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
T = 293(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −17→17
Tmin = 0.948, Tmax = 0.971k = −19→19
18809 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.071  w = 1/[σ2(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3
S = 0.79(Δ/σ)max = 0.001
6647 reflectionsΔρmax = 0.16 e Å3
514 parametersΔρmin = −0.18 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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*/Ueq
Cl1A0.03772 (5)−0.08212 (4)0.11747 (4)0.0556 (2)
Cl1B0.26822 (6)0.11374 (5)1.12967 (4)0.0633 (2)
Cl1C0.61726 (6)0.10917 (5)1.00742 (4)0.0683 (3)
O2A0.03489 (12)−0.10047 (10)0.53569 (9)0.0424 (5)
O1B0.19554 (12)0.18589 (10)0.65265 (10)0.0436 (5)
O2B0.32721 (12)0.09438 (10)0.71717 (9)0.0402 (5)
O1C0.50058 (12)0.18749 (10)0.51078 (10)0.0450 (5)
O3A0.16842 (13)−0.03651 (11)0.52509 (10)0.0499 (5)
O3B0.21291 (13)0.00485 (11)0.72245 (10)0.0488 (5)
O2C0.63757 (12)0.11032 (11)0.59116 (10)0.0447 (5)
O1A0.14699 (14)−0.20470 (10)0.62048 (10)0.0561 (6)
C8A0.04329 (18)−0.09541 (15)0.62601 (13)0.0385 (7)
H8AA−0.0167−0.09710.64910.046*
H8AB0.0707−0.04370.64170.046*
C7C0.55633 (18)0.15783 (14)0.46475 (15)0.0323 (6)
C1C0.55205 (18)0.17052 (14)0.37173 (14)0.0311 (6)
C10A0.08523 (17)−0.07507 (14)0.39938 (15)0.0309 (6)
C7B0.24177 (18)0.15393 (14)0.60005 (14)0.0308 (6)
C1A0.09642 (18)−0.17310 (14)0.75762 (14)0.0324 (6)
O3C0.53403 (16)0.01186 (11)0.60006 (11)0.0650 (6)
C8B0.31582 (17)0.09562 (15)0.62639 (13)0.0373 (7)
H8BA0.30060.04150.60600.045*
H8BB0.37210.11200.60160.045*
C10B0.27073 (18)0.06419 (14)0.85060 (14)0.0309 (6)
C3C0.6090 (2)0.15411 (15)0.23220 (16)0.0403 (7)
H3CA0.65250.13400.19670.048*
C10C0.59559 (18)0.07204 (15)0.72688 (14)0.0318 (6)
C7A0.09950 (18)−0.16285 (15)0.66412 (15)0.0366 (7)
C12A0.13340 (19)−0.04395 (15)0.25981 (16)0.0415 (7)
H12A0.1753−0.02130.22420.050*
C3B0.2621 (2)0.15140 (16)0.36190 (16)0.0459 (8)
H3BA0.29720.12700.32140.055*
C2C0.61796 (18)0.14046 (14)0.31906 (15)0.0357 (7)
H2CA0.66730.11160.34160.043*
C1B0.22630 (17)0.17034 (14)0.50769 (14)0.0282 (6)
C9B0.26507 (19)0.04978 (16)0.75790 (15)0.0357 (7)
C13B0.2710 (2)0.09279 (16)1.02189 (15)0.0417 (7)
C4A0.1008 (2)−0.19577 (16)0.93128 (17)0.0508 (8)
H4AA0.1021−0.20340.98960.061*
C12B0.2066 (2)0.04234 (16)0.98578 (16)0.0470 (8)
H12B0.16330.01831.01890.056*
C6A0.16530 (19)−0.21753 (15)0.79763 (16)0.0424 (7)
H6AA0.2105−0.24020.76570.051*
C12C0.5516 (2)0.03615 (17)0.86616 (17)0.0470 (8)
H12C0.51700.00490.90180.056*
C11A0.14801 (18)−0.04141 (14)0.34670 (15)0.0385 (7)
H11A0.2001−0.01700.36970.046*
C3A0.0322 (2)−0.15192 (16)0.89305 (17)0.0503 (8)
H3AA−0.0130−0.12970.92540.060*
C2B0.27901 (18)0.13470 (14)0.44678 (14)0.0390 (7)
H2BA0.32580.09960.46310.047*
C9C0.5839 (2)0.05997 (17)0.63423 (16)0.0391 (7)
C6B0.15735 (18)0.22224 (15)0.48194 (16)0.0404 (7)
H6BA0.12130.24610.52210.048*
C9A0.1030 (2)−0.06842 (16)0.49227 (16)0.0374 (7)
C11B0.20653 (18)0.02740 (15)0.89963 (15)0.0412 (7)
H11B0.1635−0.00720.87470.049*
C5C0.4711 (2)0.22617 (15)0.25039 (16)0.0481 (8)
H5CA0.42180.25490.22750.058*
C5B0.1412 (2)0.23927 (16)0.39721 (16)0.0514 (8)
H5BA0.09480.27480.38060.062*
C2A0.02969 (19)−0.14037 (15)0.80593 (15)0.0425 (7)
H2AA−0.0171−0.11050.78020.051*
C13A0.05596 (19)−0.08045 (15)0.22680 (14)0.0379 (7)
C13C0.61072 (19)0.09358 (16)0.89888 (15)0.0395 (7)
C6C0.47918 (19)0.21258 (15)0.33635 (16)0.0401 (7)
H6CA0.43470.23210.37120.048*
C15B0.33538 (18)0.11417 (15)0.88873 (14)0.0371 (7)
H15A0.37910.13830.85610.045*
C8C0.63088 (19)0.10529 (17)0.50074 (14)0.0498 (8)
H8CA0.61970.04930.48410.060*
H8CB0.68790.12200.47770.060*
C14C0.66371 (19)0.13928 (15)0.84783 (15)0.0408 (7)
H14A0.70460.17690.87090.049*
C14A−0.00688 (18)−0.11492 (14)0.27799 (14)0.0375 (7)
H14B−0.0586−0.13970.25470.045*
C15A0.00808 (17)−0.11202 (14)0.36445 (14)0.0351 (6)
H15B−0.0339−0.13510.39970.042*
C4C0.5369 (2)0.19671 (15)0.19875 (16)0.0481 (8)
H4CA0.53210.20600.14080.058*
C4B0.1938 (2)0.20361 (16)0.33722 (17)0.0507 (8)
H4BA0.18300.21500.28020.061*
C15C0.65510 (19)0.12822 (15)0.76153 (15)0.0381 (7)
H15C0.69020.15930.72610.046*
C14B0.33586 (19)0.12884 (15)0.97478 (14)0.0405 (7)
H14C0.37940.16261.00020.049*
C11C0.54441 (19)0.02561 (15)0.77951 (16)0.0436 (7)
H11C0.5047−0.01310.75660.052*
C5A0.1678 (2)−0.22867 (16)0.88403 (16)0.0498 (8)
H5AA0.2146−0.25830.91020.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.0629 (5)0.0707 (5)0.0334 (4)−0.0070 (4)0.0027 (4)−0.0032 (4)
Cl1B0.0917 (7)0.0693 (5)0.0292 (3)0.0110 (5)0.0060 (4)−0.0045 (4)
Cl1C0.0927 (7)0.0810 (6)0.0312 (3)0.0232 (5)0.0041 (4)−0.0038 (4)
O2A0.0411 (12)0.0550 (12)0.0309 (9)−0.0050 (10)−0.0012 (9)0.0031 (8)
O1B0.0521 (12)0.0455 (11)0.0337 (9)0.0056 (10)0.0100 (10)−0.0054 (9)
O2B0.0402 (11)0.0540 (12)0.0264 (9)−0.0049 (10)−0.0011 (8)0.0029 (8)
O1C0.0497 (13)0.0514 (12)0.0344 (10)0.0079 (10)0.0094 (10)−0.0046 (9)
O3A0.0404 (12)0.0647 (13)0.0440 (11)−0.0114 (11)−0.0084 (10)−0.0061 (10)
O3B0.0611 (14)0.0502 (12)0.0344 (10)−0.0144 (11)−0.0086 (10)−0.0042 (9)
O2C0.0411 (12)0.0656 (12)0.0269 (9)0.0029 (10)−0.0038 (9)0.0029 (9)
O1A0.0757 (15)0.0533 (12)0.0391 (10)0.0234 (11)0.0011 (11)−0.0099 (9)
C8A0.0394 (17)0.0472 (17)0.0287 (13)0.0009 (15)−0.0038 (13)−0.0007 (13)
C7C0.0325 (17)0.0310 (15)0.0336 (14)−0.0046 (13)0.0040 (14)−0.0043 (12)
C1C0.0373 (17)0.0277 (15)0.0287 (14)−0.0042 (13)0.0053 (14)−0.0016 (12)
C10A0.0257 (15)0.0293 (14)0.0375 (14)0.0051 (13)−0.0024 (13)0.0016 (12)
C7B0.0334 (16)0.0278 (14)0.0314 (14)−0.0074 (13)0.0030 (13)−0.0004 (12)
C1A0.0377 (17)0.0267 (14)0.0326 (14)0.0002 (13)−0.0017 (14)0.0009 (12)
O3C0.0987 (18)0.0496 (13)0.0450 (12)−0.0208 (13)−0.0213 (12)−0.0034 (10)
C8B0.0364 (16)0.0540 (18)0.0214 (13)−0.0004 (15)0.0004 (12)0.0017 (12)
C10B0.0350 (16)0.0291 (15)0.0283 (13)0.0026 (13)−0.0020 (13)0.0025 (12)
C3C0.054 (2)0.0368 (16)0.0307 (15)−0.0088 (15)0.0095 (15)−0.0034 (13)
C10C0.0322 (16)0.0310 (15)0.0321 (14)0.0005 (13)−0.0004 (13)0.0004 (12)
C7A0.0409 (18)0.0323 (16)0.0363 (15)0.0005 (14)−0.0044 (14)−0.0045 (13)
C12A0.0369 (18)0.0436 (17)0.0443 (17)−0.0007 (14)0.0064 (15)0.0054 (14)
C3B0.059 (2)0.0492 (18)0.0297 (15)−0.0075 (17)0.0031 (15)−0.0003 (13)
C2C0.0390 (17)0.0309 (16)0.0373 (15)−0.0013 (13)0.0019 (14)0.0006 (12)
C1B0.0305 (15)0.0269 (14)0.0275 (13)−0.0050 (13)0.0020 (13)0.0022 (11)
C9B0.0392 (18)0.0354 (17)0.0323 (15)0.0047 (14)−0.0011 (15)0.0024 (13)
C13B0.058 (2)0.0411 (17)0.0256 (13)0.0114 (16)0.0024 (15)0.0006 (13)
C4A0.076 (2)0.0398 (18)0.0366 (16)−0.0080 (17)0.0003 (18)0.0053 (14)
C12B0.051 (2)0.0533 (19)0.0371 (16)−0.0015 (16)0.0096 (15)0.0073 (14)
C6A0.0469 (19)0.0384 (16)0.0419 (16)0.0031 (15)0.0005 (15)0.0017 (13)
C12C0.0436 (19)0.0537 (19)0.0441 (17)−0.0007 (16)0.0084 (15)0.0184 (15)
C11A0.0258 (16)0.0411 (16)0.0481 (16)−0.0021 (13)−0.0058 (13)0.0046 (14)
C3A0.063 (2)0.0428 (18)0.0457 (17)0.0089 (17)0.0123 (17)0.0036 (14)
C2B0.0449 (18)0.0398 (17)0.0326 (14)−0.0033 (14)0.0066 (14)0.0011 (12)
C9C0.0426 (19)0.0356 (17)0.0384 (16)0.0087 (15)−0.0075 (15)0.0016 (14)
C6B0.0382 (17)0.0396 (17)0.0434 (16)0.0024 (14)0.0040 (14)0.0064 (13)
C9A0.0322 (17)0.0385 (17)0.0414 (16)0.0012 (15)−0.0026 (15)−0.0008 (13)
C11B0.0400 (18)0.0454 (17)0.0381 (15)−0.0085 (15)0.0006 (14)0.0010 (13)
C5C0.055 (2)0.0457 (18)0.0425 (16)0.0073 (16)−0.0039 (16)0.0080 (14)
C5B0.054 (2)0.0512 (19)0.0484 (17)−0.0018 (16)−0.0063 (16)0.0168 (15)
C2A0.0457 (19)0.0434 (17)0.0384 (15)0.0069 (15)0.0015 (14)0.0049 (13)
C13A0.0427 (18)0.0385 (16)0.0324 (14)0.0063 (15)0.0007 (14)−0.0045 (13)
C13C0.0446 (18)0.0431 (18)0.0309 (14)0.0148 (15)0.0026 (14)0.0005 (13)
C6C0.0440 (19)0.0391 (16)0.0373 (16)0.0023 (14)0.0027 (14)0.0036 (13)
C15B0.0392 (17)0.0418 (16)0.0305 (14)0.0018 (15)0.0032 (13)0.0033 (13)
C8C0.051 (2)0.073 (2)0.0256 (14)0.0195 (17)0.0028 (14)0.0040 (14)
C14C0.0473 (19)0.0351 (17)0.0395 (16)0.0008 (14)−0.0072 (15)−0.0062 (13)
C14A0.0362 (17)0.0408 (16)0.0357 (14)−0.0067 (14)0.0025 (13)−0.0046 (13)
C15A0.0331 (16)0.0378 (15)0.0343 (14)−0.0023 (14)0.0022 (13)0.0013 (12)
C4C0.070 (2)0.0449 (18)0.0295 (15)−0.0065 (17)0.0021 (17)0.0055 (14)
C4B0.069 (2)0.0494 (19)0.0327 (15)−0.0193 (17)−0.0060 (16)0.0113 (14)
C15C0.0439 (18)0.0345 (16)0.0361 (15)−0.0050 (14)0.0037 (14)0.0005 (13)
C14B0.0472 (19)0.0392 (17)0.0345 (15)0.0007 (15)−0.0062 (14)−0.0011 (13)
C11C0.0432 (19)0.0444 (17)0.0427 (16)−0.0075 (15)−0.0070 (14)0.0061 (14)
C5A0.057 (2)0.0438 (18)0.0473 (17)0.0044 (16)−0.0130 (16)0.0116 (14)

Geometric parameters (Å, °)

Cl1A—C13A1.741 (2)C5C—C6C1.379 (3)
O1A—C7A1.216 (2)C6A—H6AA0.9300
C1A—C2A1.378 (3)C6B—H6BA0.9300
C1A—C6A1.386 (3)C6C—H6CA0.9300
C1A—C7A1.491 (3)C7A—C8A1.499 (3)
Cl1B—C13B1.742 (2)C7B—C8B1.502 (3)
O1B—C7B1.215 (2)C7C—C8C1.495 (4)
C1B—C2B1.390 (3)C8A—H8AA0.9700
C1B—C6B1.379 (3)C8A—H8AB0.9700
C1B—C7B1.495 (3)C8B—H8BA0.9700
Cl1C—C13C1.736 (2)C8B—H8BB0.9700
O1C—C7C1.221 (2)C8C—H8CA0.9700
C1C—C2C1.395 (3)C8C—H8CB0.9700
C1C—C6C1.380 (3)C9A—C10A1.487 (3)
C1C—C7C1.486 (3)C9B—C10B1.485 (3)
O2A—C8A1.432 (3)C9C—C10C1.483 (3)
O2A—C9A1.346 (3)C10A—C11A1.385 (3)
C2A—H2AA0.9300C10A—C15A1.388 (3)
C2A—C3A1.391 (3)C10B—C11B1.386 (3)
O2B—C8B1.440 (3)C10B—C15B1.382 (3)
O2B—C9B1.356 (3)C10C—C11C1.376 (3)
C2B—H2BA0.9300C10C—C15C1.375 (3)
C2B—C3B1.384 (3)C11A—H11A0.9300
O2C—C8C1.433 (3)C11A—C12A1.384 (3)
O2C—C9C1.349 (3)C11B—H11B0.9300
C2C—H2CA0.9300C11B—C12B1.385 (3)
C2C—C3C1.394 (3)C11C—H11C0.9300
O3A—C9A1.200 (3)C11C—C12C1.382 (3)
C3A—H3AA0.9300C12A—H12A0.9300
C3A—C4A1.366 (4)C12A—C13A1.377 (4)
O3B—C9B1.193 (3)C12B—H12B0.9300
C3B—H3BA0.9300C12B—C13B1.370 (4)
C3B—C4B1.370 (4)C12C—H12C0.9300
O3C—C9C1.196 (3)C12C—C13C1.375 (4)
C3C—H3CA0.9300C13A—C14A1.376 (3)
C3C—C4C1.364 (4)C13B—C14B1.370 (3)
C4A—H4AA0.9300C13C—C14C1.370 (3)
C4A—C5A1.373 (3)C14A—H14B0.9300
C4B—H4BA0.9300C14A—C15A1.378 (3)
C4B—C5B1.379 (3)C14B—H14C0.9300
C4C—H4CA0.9300C14B—C15B1.382 (3)
C4C—C5C1.381 (3)C14C—H14A0.9300
C5A—H5AA0.9300C14C—C15C1.379 (3)
C5A—C6A1.378 (3)C15A—H15B0.9300
C5B—H5BA0.9300C15B—H15A0.9300
C5B—C6B1.382 (3)C15C—H15C0.9300
C5C—H5CA0.9300
Cl1A—C13A—C14A119.7 (2)C4C—C5C—C6C119.3 (3)
Cl1A—C13A—C12A118.7 (2)C5A—C4A—H4AA119.8
O1A—C7A—C1A122.6 (2)C5A—C6A—H6AA119.5
O1A—C7A—C8A120.9 (2)C5B—C4B—H4BA120.1
C1A—C2A—H2AA119.9C5B—C6B—H6BA119.6
C1A—C2A—C3A120.2 (3)C5C—C4C—H4CA119.8
C1A—C6A—H6AA119.5C5C—C6C—H6CA119.4
C1A—C6A—C5A121.0 (3)C6A—C1A—C7A117.7 (2)
C1A—C7A—C8A116.5 (2)C6A—C5A—H5AA120.2
Cl1B—C13B—C14B119.3 (2)C6B—C1B—C7B119.0 (2)
Cl1B—C13B—C12B119.2 (2)C6B—C5B—H5BA120.0
O1B—C7B—C1B121.4 (2)C6C—C1C—C7C118.5 (2)
O1B—C7B—C8B120.5 (2)C6C—C5C—H5CA120.4
C1B—C2B—H2BA119.9C7A—C8A—H8AA109.1
C1B—C2B—C3B120.2 (3)C7A—C8A—H8AB109.1
C1B—C6B—H6BA119.6C7B—C8B—H8BA109.7
C1B—C6B—C5B120.8 (2)C7B—C8B—H8BB109.7
C1B—C7B—C8B118.0 (2)C7C—C8C—H8CA109.3
Cl1C—C13C—C14C119.4 (2)C7C—C8C—H8CB109.3
Cl1C—C13C—C12C119.1 (2)C8A—O2A—C9A116.6 (2)
O1C—C7C—C1C122.0 (2)H8AA—C8A—H8AB107.8
O1C—C7C—C8C120.5 (2)C8B—O2B—C9B115.2 (2)
C1C—C2C—H2CA120.4H8BA—C8B—H8BB108.2
C1C—C2C—C3C119.3 (3)C8C—O2C—C9C116.7 (2)
C1C—C6C—H6CA119.4H8CA—C8C—H8CB107.9
C1C—C6C—C5C121.3 (2)C9A—C10A—C11A117.9 (3)
C1C—C7C—C8C117.5 (2)C9A—C10A—C15A122.6 (2)
O2A—C8A—H8AA109.1C9B—C10B—C11B117.9 (3)
O2A—C8A—H8AB109.1C9B—C10B—C15B122.6 (2)
O2A—C8A—C7A112.62 (19)C9C—C10C—C11C118.5 (3)
O2A—C9A—O3A123.7 (2)C9C—C10C—C15C122.3 (2)
O2A—C9A—C10A111.5 (3)C10A—C11A—H11A119.9
C2A—C1A—C6A118.7 (2)C10A—C11A—C12A120.2 (3)
C2A—C1A—C7A123.7 (3)C10A—C15A—H15B119.7
C2A—C3A—H3AA119.9C10A—C15A—C14A120.6 (2)
C2A—C3A—C4A120.2 (3)C10B—C11B—H11B120.1
O2B—C8B—H8BA109.7C10B—C11B—C12B119.8 (3)
O2B—C8B—H8BB109.7C10B—C15B—H15A119.6
O2B—C8B—C7B110.05 (18)C10B—C15B—C14B120.8 (2)
O2B—C9B—O3B123.3 (2)C10C—C11C—H11C119.8
O2B—C9B—C10B111.6 (2)C10C—C11C—C12C120.4 (3)
C2B—C1B—C6B118.8 (2)C10C—C15C—H15C119.4
C2B—C1B—C7B122.1 (2)C10C—C15C—C14C121.2 (2)
C2B—C3B—H3BA119.8C11A—C10A—C15A119.5 (2)
C2B—C3B—C4B120.4 (3)C11A—C12A—H12A120.4
O2C—C8C—H8CA109.3C11A—C12A—C13A119.1 (2)
O2C—C8C—H8CB109.3C11B—C10B—C15B119.4 (2)
O2C—C8C—C7C111.7 (2)C11B—C12B—H12B120.2
O2C—C9C—O3C122.8 (2)C11B—C12B—C13B119.6 (2)
O2C—C9C—C10C111.6 (3)C11C—C10C—C15C119.3 (2)
C2C—C1C—C6C119.1 (2)C11C—C12C—H12C120.5
C2C—C1C—C7C122.5 (3)C11C—C12C—C13C119.0 (2)
C2C—C3C—H3CA119.7C12A—C11A—H11A119.9
C2C—C3C—C4C120.6 (3)C12A—C13A—C14A121.6 (2)
O3A—C9A—C10A124.7 (2)C12B—C11B—H11B120.1
C3A—C2A—H2AA119.9C12B—C13B—C14B121.6 (2)
C3A—C4A—H4AA119.8C12C—C11C—H11C119.8
C3A—C4A—C5A120.3 (3)C12C—C13C—C14C121.6 (2)
O3B—C9B—C10B125.1 (2)C13A—C12A—H12A120.4
C3B—C2B—H2BA119.9C13A—C14A—H14B120.6
C3B—C4B—H4BA120.1C13A—C14A—C15A118.9 (3)
C3B—C4B—C5B119.8 (3)C13B—C12B—H12B120.2
O3C—C9C—C10C125.7 (3)C13B—C14B—H14C120.6
C3C—C2C—H2CA120.4C13B—C14B—C15B118.8 (3)
C3C—C4C—H4CA119.8C13C—C12C—H12C120.5
C3C—C4C—C5C120.5 (2)C13C—C14C—H14A120.7
C4A—C3A—H3AA119.9C13C—C14C—C15C118.5 (3)
C4A—C5A—H5AA120.2C14A—C15A—H15B119.7
C4A—C5A—C6A119.6 (3)C14B—C15B—H15A119.6
C4B—C3B—H3BA119.8C14C—C15C—H15C119.4
C4B—C5B—H5BA120.0C15A—C14A—H14B120.6
C4B—C5B—C6B120.0 (3)C15B—C14B—H14C120.6
C4C—C3C—H3CA119.7C15C—C14C—H14A120.7
C4C—C5C—H5CA120.4
Cl1A—C13A—C12A—C11A179.21 (19)O3B—C9B—C10B—C15B176.9 (3)
Cl1A—C13A—C14A—C15A−179.1 (2)C3B—C2B—C1B—C6B−0.0 (4)
O1A—C7A—C8A—O2A14.7 (3)C3B—C2B—C1B—C7B179.8 (2)
O1A—C7A—C1A—C2A−164.7 (2)C3B—C4B—C5B—C6B−0.1 (4)
O1A—C7A—C1A—C6A15.9 (4)C8C—O2C—C9C—O3C1.5 (4)
C1A—C2A—C3A—C4A−0.0 (4)O3C—C9C—C10C—C11C−1.2 (4)
C1A—C6A—C5A—C4A0.5 (4)O3C—C9C—C10C—C15C179.3 (3)
C1A—C7A—C8A—O2A−167.6 (2)C3C—C2C—C1C—C6C0.5 (4)
Cl1B—C13B—C12B—C11B177.9 (2)C3C—C2C—C1C—C7C179.4 (2)
Cl1B—C13B—C14B—C15B−177.6 (2)C3C—C4C—C5C—C6C0.5 (4)
O1B—C7B—C8B—O2B−7.1 (3)C5A—C6A—C1A—C7A179.1 (2)
O1B—C7B—C1B—C2B179.5 (2)C5B—C6B—C1B—C7B179.7 (2)
O1B—C7B—C1B—C6B−0.7 (4)C5C—C6C—C1C—C7C−179.8 (2)
C1B—C2B—C3B—C4B0.5 (4)C6A—C1A—C7A—C8A−161.8 (2)
C1B—C6B—C5B—C4B0.6 (4)C6B—C1B—C7B—C8B178.5 (2)
C1B—C7B—C8B—O2B173.7 (2)C6C—C1C—C7C—C8C174.2 (2)
Cl1C—C13C—C12C—C11C178.0 (2)C7A—C8A—O2A—C9A−83.8 (3)
Cl1C—C13C—C14C—C15C−177.6 (2)C7B—C8B—O2B—C9B78.7 (2)
O1C—C7C—C8C—O2C−12.2 (4)C7C—C8C—O2C—C9C86.1 (3)
O1C—C7C—C1C—C2C176.6 (2)C8A—O2A—C9A—C10A−178.2 (2)
O1C—C7C—C1C—C6C−4.5 (4)C8B—O2B—C9B—C10B−169.2 (2)
C1C—C2C—C3C—C4C0.3 (4)C8C—O2C—C9C—C10C−178.8 (2)
C1C—C6C—C5C—C4C0.4 (4)C9A—C10A—C11A—C12A−178.2 (2)
C1C—C7C—C8C—O2C169.1 (2)C9A—C10A—C15A—C14A178.2 (2)
O2A—C9A—C10A—C11A177.32 (19)C9B—C10B—C11B—C12B−176.9 (2)
O2A—C9A—C10A—C15A−1.5 (3)C9B—C10B—C15B—C14B177.1 (2)
C2A—C1A—C6A—C5A−0.4 (4)C9C—C10C—C11C—C12C−178.5 (3)
C2A—C1A—C7A—C8A17.6 (4)C9C—C10C—C15C—C14C178.9 (3)
C2A—C3A—C4A—C5A−0.1 (4)C10A—C11A—C12A—C13A0.2 (4)
O2B—C9B—C10B—C11B175.1 (2)C10A—C15A—C14A—C13A0.1 (4)
O2B—C9B—C10B—C15B−3.1 (3)C10B—C11B—C12B—C13B−0.7 (4)
C2B—C1B—C6B—C5B−0.6 (4)C10B—C15B—C14B—C13B0.1 (4)
C2B—C1B—C7B—C8B−1.2 (3)C10C—C11C—C12C—C13C0.1 (4)
C2B—C3B—C4B—C5B−0.5 (4)C10C—C15C—C14C—C13C−0.8 (4)
O2C—C9C—C10C—C11C179.2 (2)C11A—C10A—C15A—C14A−0.5 (4)
O2C—C9C—C10C—C15C−0.3 (4)C11A—C12A—C13A—C14A−0.4 (4)
C2C—C1C—C6C—C5C−0.8 (4)C11B—C10B—C15B—C14B−1.0 (4)
C2C—C1C—C7C—C8C−4.8 (4)C11B—C12B—C13B—C14B0.2 (4)
C2C—C3C—C4C—C5C−0.8 (4)C11C—C10C—C15C—C14C−0.6 (4)
O3A—C9A—O2A—C8A0.2 (4)C11C—C12C—C13C—C14C−1.3 (4)
O3A—C9A—C10A—C11A−0.7 (4)C12A—C11A—C10A—C15A0.6 (4)
O3A—C9A—C10A—C15A−179.5 (2)C12A—C13A—C14A—C15A0.6 (4)
C3A—C2A—C1A—C6A0.1 (4)C12B—C11B—C10B—C15B1.3 (4)
C3A—C2A—C1A—C7A−179.3 (3)C12B—C13B—C14B—C15B0.6 (4)
C3A—C4A—C5A—C6A−0.3 (4)C12C—C11C—C10C—C15C1.0 (4)
O3B—C9B—O2B—C8B10.9 (3)C12C—C13C—C14C—C15C1.7 (4)
O3B—C9B—C10B—C11B−4.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O3B0.972.553.322 (3)137
C8C—H8CB···O3Ai0.972.553.212 (3)126
C11A—H11A···Cg1B0.933.464.036 (4)123
C11B—H11B···Cg1A0.933.103.917 (4)137

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2408).

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 (2001). SAINT (Version 6.22), SMART (Version 5.625) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Hendrickson, J. B. & Kandall, C. (1970). Tetrahedron Lett.5, 343–344.
  • Kelly, T. L. & Howard, H. W. (1932). J. Am. Chem. Soc.54, 4383–4385.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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