2-Chloro-N-(2,6-dimethyl­phen­yl)benzamide

Rodrigues, V.Z.; Gowda, B.T.; Sivý, J.; Vrábel, V.; Kožíšek, J.

doi:10.1107/S1600536812015607

Volume 68
Part 5
Page o1408
May 2012

Received 29 March 2012
Accepted 10 April 2012
Online 18 April 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.008 Å
R = 0.092
wR = 0.248
Data-to-parameter ratio = 14.7
Details

2-Chloro-N-(2,6-dimethylphenyl)benzamide

Vinola Z. Rodrigues,^a B. Thimme Gowda,^a ^* Július Sivý,^b Viktor Vrábel ^c and Jozef Kozísek ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,^bInstitute of Mathematics and Physics, Faculty of Mechanical Engineering STU, Námestie Slobody 17, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₅H₁₄ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N-HO hydrogen bonds link the molecules into chains running along the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000, 2007, 2008); Saeed et al. (2010), on N-chloroarylsulfonamides, see: Jyothi & Gowda (2004) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental

Crystal data

C₁₅H₁₄ClNO
M_r = 259.72
Monoclinic, P 2₁ /n
a = 4.8322 (3) Å
b = 12.7817 (10) Å
c = 21.8544 (12) Å
= 90.778 (5)°
V = 1349.69 (15) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 295 K
0.51 × 0.30 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995)] T_min = 0.907, T_max = 0.971
18665 measured reflections
2469 independent reflections
1735 reflections with I > 2(I)
R_int = 0.081

Refinement

R[F² > 2(F²)] = 0.092
wR(F²) = 0.248
S = 1.12
2469 reflections
168 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.50 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86 (2)	1.96 (2)	2.818 (4)	172 (4)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: SHELXL97, PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5865 ).

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi for award of an RFSMS research fellowship. JS, VV and JK thank the Grant Agencies for their financial support (VEGA Grant Agency of Slovak Ministry of Education 1/0679/11; Research and Development Agency of Slovakia (APVV-0202-10) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o1975-o1976.
Gowda, B. T., Svoboda, I. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 779-790.
Gowda, B. T., Tokarcík, M., Kozísek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1493.
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.

organic compounds