N-(2-Chloro­phen­yl)-3-methyl­benzamide

Rodrigues, V.Z.; Tokarčík, M.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S160053681000992X

Volume 66
Part 4
Page o891
April 2010

Received 15 March 2010
Accepted 17 March 2010
Online 20 March 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 13.5
Details

N-(2-Chlorophenyl)-3-methylbenzamide

Vinola Zeena Rodrigues,^a Miroslav Tokarcík,^b B. Thimme Gowda ^a ^* and Jozef Kozísek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₄H₁₂ClNO, the N-H bond is anti to the carbonyl bond and the two aromatic rings make a dihedral angle of 5.4 (2)°. In the crystal, intermolecular N-HO hydrogen bonds connect the molecules into chains running along the b axis. The chains are interconnected through short ClCl contacts [3.279 (1) Å].

Related literature

For the preparation of the compound, see: Gowda et al. (2003). For related structures, see: Bowes et al. (2003); Gowda et al. (2008a,b).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.7
Monoclinic, P 2₁ /c
a = 9.9972 (3) Å
b = 4.9124 (1) Å
c = 24.6662 (7) Å
= 100.248 (3)°
V = 1192.04 (5) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 295 K
0.55 × 0.35 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.897, T_max = 0.978
25420 measured reflections
2119 independent reflections
1884 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.108
S = 1.05
2119 reflections
157 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.86	2.16	2.936 (2)	151
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5219 ).

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o770.
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o1421.
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds