Methyl 2-(3-chloro­benzamido)­benzoate

Ouahrouch, A.; Taourirte, M.; Lazrek, H.B.; El Azhari, M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812046934

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.144
Data-to-parameter ratio = 19.4
Details

Methyl 2-(3-chlorobenzamido)benzoate

Abdelaaziz Ouahrouch,^a ^* Moha Taourirte,^a Hassan B. Lazrek,^b Mohamed El Azhari,^c Mohamed Saadi ^d and Lahcen El Ammari ^d

^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-HO hydrogen bond occurs. In the crystal, each molecule is linked to a symmetry-equivalent counterpart across a twofold rotation axis by weak C-HO and C-HCl 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); Xingwen et al. (2007); Chandrika et al. (2008). For background to the potential biological use of benzoxazinone derivatives, see: Kurosaki & Naishi (1983); Ponchet et al. (1988); Hedsrom et al. (1984); Krantz et al. (1990).

Experimental

Crystal data

C₁₅H₁₂ClNO₃
M_r = 289.71
Monoclinic, C 2/c
a = 25.7464 (10) Å
b = 6.9203 (2) Å
c = 16.9735 (6) Å
= 116.045 (2)°
V = 2717.10 (16) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.957, T_max = 0.997
20126 measured reflections
3511 independent reflections
2143 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.144
S = 1.02
3511 reflections
181 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H2O2	0.86	1.96	2.6506 (19)	137
C1-H1O1ⁱ	0.93	2.67	3.573 (2)	163
C9-H9Cl1ⁱ	0.93	2.87	3.617 (2)	139
Symmetry code: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

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organic compounds