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Volume 68 
Part 12 
Pages o3400-o3401  
December 2012  

Received 6 November 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.144
Data-to-parameter ratio = 19.4
Details
Open access

Methyl 2-(3-chlorobenzamido)benzoate

aLaboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco,bUnité de Chimie Biomoléculaire et Médicinale, Faculté des Sciences Semlalia, Marrakech, Morocco,cLaboratoire de la Matière Condensée et des Nanostructures, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: a_ouahrouch@yahoo.fr

In the molecule of the title compound, C15H12ClNO3, the chlorobenzamide and benzoate units are almost co-planar, with a dihedral angle between the six-membered rings of 2.99 (10)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, each molecule is linked to a symmetry-equivalent counterpart across a twofold rotation axis by weak C-H...O and C-H...Cl hydrogen bonds, forming dimers. The packing is stabilized through weak [pi]-[pi] stacking along the b-axis direction, leading to [pi]-stacked columns of inversion-related molecules, with an interplanar distance of 3.46 (2) Å and a centroid-centroid vector of 3.897 (2) Å.

Related literature

For details of the synthesis, see: Shariat & Abdollahi (2004[Shariat, M. & Abdollahi, S. (2004). Molecules, 9, 705-712.]); Xingwen et al. (2007[Xingwen, G., Xuejian, C., Kai, Y., Baoan, S., Lili, G. & Zhuo, C. (2007). Molecules, 12, 2621-2642.]); Chandrika et al. (2008[Chandrika, P. M., Yakaiah, T., Raghu Ram Rao, A., Narsaiah, B., Chakra Reddy, N., Sridhar, V. & Venkateshwara Rao, J. (2008). Eur. J. Med. Chem. 43, 846-852.]). For background to the potential biological use of benzoxazinone derivatives, see: Kurosaki & Naishi (1983[Kurosaki, F. & Naishi, A. (1983). Phytochemistry, 22, 669-672.]); Ponchet et al. (1988[Ponchet, M., Favre-Bonvin, J., Hauteville, M. & Ricci, P. (1988). Phytochemistry, 27, 725-730.]); Hedsrom et al. (1984[Hedsrom, L., Moorman, A. R., Dobbs, J. & Abeles, R. H. (1984). Biochemistry, 23, 1753-1759.]); Krantz et al. (1990[Krantz, A., Spencer, R. W., Tam, T. F., Liak, T. J., Copp, L. J., Thomas, E. M. & Rafferty, S. P. (1990). J. Med. Chem. 33, 464-479.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12ClNO3

  • Mr = 289.71

  • Monoclinic, C 2/c

  • a = 25.7464 (10) Å

  • b = 6.9203 (2) Å

  • c = 16.9735 (6) Å

  • [beta] = 116.045 (2)°

  • V = 2717.10 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 296 K

  • 0.36 × 0.31 × 0.27 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.997

  • 20126 measured reflections

  • 3511 independent reflections

  • 2143 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.144

  • S = 1.02

  • 3511 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H2...O2 0.86 1.96 2.6506 (19) 137
C1-H1...O1i 0.93 2.67 3.573 (2) 163
C9-H9...Cl1i 0.93 2.87 3.617 (2) 139
Symmetry code: (i) [-x+2, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al. 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2515 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chandrika, P. M., Yakaiah, T., Raghu Ram Rao, A., Narsaiah, B., Chakra Reddy, N., Sridhar, V. & Venkateshwara Rao, J. (2008). Eur. J. Med. Chem. 43, 846-852.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hedsrom, L., Moorman, A. R., Dobbs, J. & Abeles, R. H. (1984). Biochemistry, 23, 1753-1759.  [PubMed] [ISI]
Krantz, A., Spencer, R. W., Tam, T. F., Liak, T. J., Copp, L. J., Thomas, E. M. & Rafferty, S. P. (1990). J. Med. Chem. 33, 464-479.  [CrossRef] [ChemPort] [PubMed] [ISI]
Kurosaki, F. & Naishi, A. (1983). Phytochemistry, 22, 669-672.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Ponchet, M., Favre-Bonvin, J., Hauteville, M. & Ricci, P. (1988). Phytochemistry, 27, 725-730.  [CrossRef] [ChemPort] [ISI]
Shariat, M. & Abdollahi, S. (2004). Molecules, 9, 705-712.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Xingwen, G., Xuejian, C., Kai, Y., Baoan, S., Lili, G. & Zhuo, C. (2007). Molecules, 12, 2621-2642.  [PubMed]


Acta Cryst (2012). E68, o3400-o3401   [ doi:10.1107/S1600536812046934 ]

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