4-Chloro­phenyl 4-chloro­benzoate

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536808022800

Volume 64
Part 8
Page o1582
August 2008

Received 18 July 2008
Accepted 20 July 2008
Online 23 July 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 11.8
Details

4-Chlorophenyl 4-chlorobenzoate

B. Thimme Gowda,^a ^* Sabine Foro,^b K. S. Babitha ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

The structure of the title compound (4CP4CBA), C₁₃H₈Cl₂O₂, resembles those of 4-methylphenyl 4-chlorobenzoate (4MP4CBA), 4-chlorophenyl 4-methylbenzoate (4CP4MBA) and 4-methylphenyl 4-methylbenzoate (4MP4MBA), with similar bond parameters. The dihedral angle between the two benzene rings in 4CP4CBA is 47.98 (7)°, compared with 51.86 (4)° in 4MP4CBA, 63.89 (8)° in 4CP4MBA and 63.57 (5)° in 4MP4MBA. In the crystal structure, molecules are linked into helical chains running along the b axis by C-H-O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2007); Gowda, Foro et al. (2008); Gowda, Svoboda et al. (2008); Nayak & Gowda (2008).

Experimental

Crystal data

C₁₃H₈Cl₂O₂
M_r = 267.09
Monoclinic, P 2₁ /n
a = 15.370 (2) Å
b = 3.9528 (4) Å
c = 19.465 (2) Å
= 91.804 (9)°
V = 1182.0 (2) Å³
Z = 4
Cu K radiation
= 4.83 mm^-1
T = 299 (2) K
0.45 × 0.23 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.194, T_max = 0.420
4211 measured reflections
2109 independent reflections
1724 reflections with I > 2(I)
R_int = 0.080
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.139
S = 1.05
2109 reflections
178 parameters
Only H-atom coordinates refined
_max = 0.39 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O2ⁱ	0.92 (3)	2.58 (3)	3.168 (3)	123 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2640 ).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3867.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1518.
Gowda, B. T., Svoboda, I., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o88.
Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63. In the press.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds