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Volume 68 
Part 1 
Page o202  
January 2012  

Received 30 November 2011
Accepted 10 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.145
Data-to-parameter ratio = 16.9
Details
Open access

4-Chloro-N-(2,3-dimethylphenyl)benzamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,bDepartment of Inorganic Chemistry, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech 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 ortho- and meta-methyl substituents in the aniline ring are anti to the N-H bond. The dihedral angle between the benzoyl and aniline benzene rings is 95.0 (1)°. N-H...O hydrogen bonds and C-H...[pi] interactions link the molecules in the crystal structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (1996[Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.], 2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.]). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.]); Rodrigues et al. (2011[Rodrigues, V. Z., Herich, P., Gowda, B. T. & Kozísek, J. (2011). Acta Cryst. E67, o2463.]), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]) and on N-chloroarylamides, see: Gowda et al. (1996[Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14ClNO

  • Mr = 259.72

  • Monoclinic, P 21 /c

  • a = 8.1082 (8) Å

  • b = 19.5189 (17) Å

  • c = 9.2943 (9) Å

  • [beta] = 111.957 (11)°

  • V = 1364.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.90 × 0.15 × 0.09 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[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.953, Tmax = 0.976

  • 22574 measured reflections

  • 2793 independent reflections

  • 1923 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.145

  • S = 1.04

  • 2793 reflections

  • 165 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C2-C7 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.18 2.904 (2) 141
C14-H14A...Cg1ii 0.96 2.94 3.653 (2) 132
C7-H7...Cg2i 0.93 2.76 3.612 (2) 154
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2325 ).


Acknowledgements

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

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.  [CSD] [CrossRef] [details]
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.  [ChemPort]
Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.  [ChemPort]
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.  [ChemPort]
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Rodrigues, V. Z., Herich, P., Gowda, B. T. & Kozísek, J. (2011). Acta Cryst. E67, o2463.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o202  [ doi:10.1107/S1600536811053256 ]

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