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Volume 69 
Part 10 
Page o1568  
October 2013  

Received 4 September 2013
Accepted 16 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.105
Data-to-parameter ratio = 12.8
Details
Open access

4-Chloro-2-(2-chlorobenzoyl)phenol

aDepartment of Chemistry, Yuvaraja's College (Autonomous), University of Mysore, Mysore, 570 005, India, and bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India
Correspondence e-mail: shaukathara@yahoo.co.in

In the title molecule, C13H8Cl2O2, the dihedral angle between the benzene rings is 74.53 (9)°. An intramolecular O-H...O hydrogen bond leading to a S(6) ring is observed. In the crystal, the molecules are connected into a three-dimensional network by C-H...O and [pi]-[pi] [inter-centroid distance = 3.6254 (10) Å] interactions.

Related literature

For the biological activity of benzophenone derivatives, see: Khanum et al. (2005[Khanum, S. A., Shashikanth, S., Umesha, S. & Kavitha, R. (2005). Eur. J. Med. Chem. 40, 1156-1162.], 2010[Khanum, S. A., Begum, B. A., Girish, V. & Khanum, N. F. (2010). Int. J. Biomed. Sci. 6, 60-65.]). For a related structure, see: Devaiah et al. (2006[Devaiah, V. T., Naveen, S., Shashikanth, S., Anandalwar, S. M. & Prasad, J. S. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, x157-x158.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8Cl2O2

  • Mr = 267.09

  • Orthorhombic, P b c a

  • a = 16.0231 (4) Å

  • b = 7.4216 (2) Å

  • c = 19.6843 (5) Å

  • V = 2340.80 (10) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 4.87 mm-1

  • T = 295 K

  • 0.20 × 0.19 × 0.18 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madaison, Wisconsin, USA.]) Tmin = 0.442, Tmax = 0.474

  • 15868 measured reflections

  • 1972 independent reflections

  • 1712 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.105

  • S = 1.06

  • 1972 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 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
O16-H16...O9 0.82 1.88 2.598 (2) 146
C13-H13...O9i 0.93 2.50 3.413 (3) 168
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madaison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madaison, Wisconsin, USA.]); data reduction: SAINT; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5253 ).


Acknowledgements

The authors thank the IOE and the University of Mysore for providing the single crystal X-ray diffractometer facility.

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madaison, Wisconsin, USA.
Devaiah, V. T., Naveen, S., Shashikanth, S., Anandalwar, S. M. & Prasad, J. S. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, x157-x158.  [CSD] [CrossRef] [ChemPort]
Khanum, S. A., Begum, B. A., Girish, V. & Khanum, N. F. (2010). Int. J. Biomed. Sci. 6, 60-65.  [ChemPort] [PubMed]
Khanum, S. A., Shashikanth, S., Umesha, S. & Kavitha, R. (2005). Eur. J. Med. Chem. 40, 1156-1162.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1568  [ doi:10.1107/S1600536813025609 ]

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