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Volume 69 
Part 6 
Pages o999-o1000  
June 2013  

Received 16 May 2013
Accepted 24 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.084
Data-to-parameter ratio = 14.4
Details
Open access

2-Benzoyl-4-chlorophenyl benzoate

aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and bPost-Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: shaukathara@yahoo.co.in

In the title compound, C20H13ClO3, the dihedral angles between the benzoate and the chlorobenzene and benzoyl rings are 68.82 (5) and 53.76 (6)°, respectively, while the dihedral angle between the benzoyl and benzoate rings is 81.17 (5)°. The eight atoms of the benzoyl residue are essentially planar with the exception of the O atom which lies 0.1860 (5) Å out of their mean plane (r.m.s. deviation = 0.97 Å). The nine atoms of benzoate residue are also essentially planar (r.m.s. deviation = 0.20 Å) with the ester O atom showing the greatest deviation [0.407 (12) Å] from their mean plane. In the crystal, molecules are connected into centrosymmetric dimers by pairs of C-H...O hydrogen bonds.

Related literature

For related structures, see: Sieron et al. (2004[Sieron, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889-o1891.]); Mahendra et al. (2005[Mahendra, M., Doreswamy, B. H., Sridhar, M. A., Prasad, J. S., Khanum, S. A., Shashikanth, S. & Venu, T. D. (2005). J. Chem. Crystallogr. 35, 463-467.]); Naveen et al. (2006[Naveen, S., Venu, T. D., Shashikanth, S., Sridhar, M. A. & Shashidhara Prasad, J. (2006). Acta Cryst. E62, o5896-o5898.]). For the biological activity of the title compound, see: Belluti et al. (2011[Belluti, F., Bartolini, M., Bottegoni, G., Bisi, A., Cavalli, A., Andrisano, V. & Rampa, A. (2011). Eur. J. Med. Chem. 46, 1682-1693.]); Revesz et al. (2004[Revesz, L., Blum, F. E., Di Padova, E. T., Buhl, R., Feifel, H., Gram, P., Hiestand, U., Manning, U. & Rucklin, G. (2004). Bioorg. Med. Chem. Lett. 14, 3595-3599.]); Khanum et al. (2004[Khanum, S. A., Shashikanth, S. & Deepak, A. V. (2004). Bioorg. Chem. 32, 211-222.], 2009[Khanum, S. A., Girish, V., Suparshwa, S. S. & Khanum, N. F. (2009). Bioorg. Med. Chem. Lett. 19, 1887-91.], 2010[Khanum, S. A., Begum, B. A., Girish, V. & Khanum, N. F. (2010). Int. J. Biomed. Sci. 6, 60-65.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Prpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C20H13ClO3

  • Mr = 336.75

  • Triclinic, [P \overline 1]

  • a = 9.1934 (2) Å

  • b = 9.8641 (3) Å

  • c = 10.0778 (3) Å

  • [alpha] = 94.033 (2)°

  • [beta] = 114.207 (2)°

  • [gamma] = 102.512 (2)°

  • V = 800.64 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.871, Tmax = 1.000

  • 18813 measured reflections

  • 3131 independent reflections

  • 2631 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.084

  • S = 1.03

  • 3131 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O7i 0.93 2.50 3.394 (2) 162
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2090 ).


Acknowledgements

SAK gratefully acknowledges financial support provided by the UGC, New Delhi, under the Major Research Project Scheme.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Prpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Belluti, F., Bartolini, M., Bottegoni, G., Bisi, A., Cavalli, A., Andrisano, V. & Rampa, A. (2011). Eur. J. Med. Chem. 46, 1682-1693.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khanum, S. A., Begum, B. A., Girish, V. & Khanum, N. F. (2010). Int. J. Biomed. Sci. 6, 60-65.  [ChemPort] [PubMed]
Khanum, S. A., Girish, V., Suparshwa, S. S. & Khanum, N. F. (2009). Bioorg. Med. Chem. Lett. 19, 1887-91.  [CrossRef] [PubMed] [ChemPort]
Khanum, S. A., Shashikanth, S. & Deepak, A. V. (2004). Bioorg. Chem. 32, 211-222.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mahendra, M., Doreswamy, B. H., Sridhar, M. A., Prasad, J. S., Khanum, S. A., Shashikanth, S. & Venu, T. D. (2005). J. Chem. Crystallogr. 35, 463-467.  [CrossRef] [ChemPort]
Naveen, S., Venu, T. D., Shashikanth, S., Sridhar, M. A. & Shashidhara Prasad, J. (2006). Acta Cryst. E62, o5896-o5898.  [CrossRef] [ChemPort] [details]
Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Revesz, L., Blum, F. E., Di Padova, E. T., Buhl, R., Feifel, H., Gram, P., Hiestand, U., Manning, U. & Rucklin, G. (2004). Bioorg. Med. Chem. Lett. 14, 3595-3599.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sieron, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889-o1891.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o999-o1000   [ doi:10.1107/S1600536813014396 ]

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