2-Chloro-N-(3,5-dichloro­phenyl)­benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808018072

Volume 64
Part 7
Page o1294
July 2008

Received 11 June 2008
Accepted 13 June 2008
Online 19 June 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.007 Å
R = 0.056
wR = 0.231
Data-to-parameter ratio = 16.2
Details

2-Chloro-N-(3,5-dichlorophenyl)benzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^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 amide group in the structure of the title compound (N35DCP2CBA), C₁₃H₈Cl₃NO, is trans-planar, similar to that observed in N-(3-chlorophenyl)benzamide, N-(3,5-dichlorophenyl)benzamide, 2-chloro-N-phenylbenzamide and other benzanilides. The C=O bond in N35DCP2CBA is anti to the ortho-chloro substituent in the benzoyl ring. The amide group makes dihedral angles of 63.1 (12) and 31.1 (17)°, respectively, with the benzoyl and aniline benzene rings, while the dihedral angle between the two benzene rings is 32.1 (2)°. The molecules are linked into chains along the b axis by N-HO hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003); Gowda, Foro et al. (2008); Gowda, Tokarcík et al. (2008).

Experimental

Crystal data

C₁₃H₈Cl₃NO
M_r = 300.55
Orthorhombic, P b c a
a = 14.699 (1) Å
b = 8.736 (1) Å
c = 20.445 (2) Å
V = 2625.4 (4) Å³
Z = 8
Mo K radiation
= 0.68 mm^-1
T = 299 (2) K
0.38 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.781, T_max = 0.960
12954 measured reflections
2686 independent reflections
1288 reflections with I > 2(I)
R_int = 0.094

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.230
S = 1.08
2686 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.81 (5)	2.14 (5)	2.913 (5)	160 (5)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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: CI2616 ).

Acknowledgements

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

References

Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1243.
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.
Gowda, B. T., Tokarcík, M., Kozísek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds