4-Chloro-N-(2-chloro­phen­yl)benzamide

Saeed, A.; Khera, R.A.; Gotoh, K.; Ishida, H.

doi:10.1107/S1600536808028882

Volume 64
Part 10
Page o1934
October 2008

Received 19 August 2008
Accepted 9 September 2008
Online 13 September 2008

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.155
Data-to-parameter ratio = 22.3
Details

4-Chloro-N-(2-chlorophenyl)benzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Kazuma Gotoh ^b and Hiroyuki Ishida ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
Correspondence e-mail: aamersaeed@yahoo.com

In the molecular structure of the title compound, C₁₃H₉Cl₂NO, the amide N-C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chlorophenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The molecules are stacked in columns along the b axis through intermolecular N-HO hydrogen bonds. The columns are further connected by weak C-HO hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

Related literature

For general background, see: Capdeville et al. (2002); Chopra & Row (2005); Ho et al. (2002); Igawa et al. (1999); Jackson et al. (1994); Makino et al. (2003); Zhichkin et al. (2007). For related structures, see: Chopra & Row (2005).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.13
Monoclinic, P 2₁ /n
a = 10.7913 (14) Å
b = 4.8078 (6) Å
c = 23.570 (3) Å
= 97.718 (3)°
V = 1211.8 (3) Å³
Z = 4
Mo- K radiation
= 0.52 mm^-1
T = 223 (1) K
0.35 × 0.31 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.884, T_max = 0.975
14924 measured reflections
3527 independent reflections
1847 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.154
S = 1.00
3527 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2-H2O1ⁱⁱ	0.94	2.59	3.456 (3)	153
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2189 ).

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

References

Capdeville, R., Buchdunger, E., Zimmermann, J. & Matter, A. (2002). Nat. Rev. Drug Discov. 1, 493-502.
Chopra, D. & Row, T. N. G. (2005). Cryst. Growth Des. 5, 1679-1681.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ho, T.-I., Chen, W.-S., Hsu, C.-W., Tsai, Y.-M. & Fang, J.-M. (2002). Heterocycles, 57, 1501-1506.
Igawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Jpn Patent Kokai Tokkyo Koho. JP 11 171 848.
Jackson, S., DeGrado, W., Dwivedi, A., Parthasarathy, A., Higley, A., Krywko, J., Rockwell, A., Markwalder, J., Wells, G., Wexler, R., Mousa, S. & Harlow, R. (1994). J. Am. Chem. Soc. 116, 3220-3230.
Makino, S., Nakanishi, E. & Tsuji, T. (2003). Bull. Korean Chem. Soc. 24, 389-392.
Rigaku/MSC (2004). CrystalStructure and PROCESS-AUTO. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415-1418.

organic compounds