Methyl 2-(thiophene-2-carboxamido)benzoate

The title compound, C13H11NO3S, was synthesized from methyl anthranilate, triethylamine and 2-thiophenoyl chloride in benzene. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. The dihedral angle between the rings is 2.74 (12)°. In the crystal, C—H⋯O interactions link neighbouring molecules into a three-dimensional network.

The title compound, C 13 H 11 NO 3 S, was synthesized from methyl anthranilate, triethylamine and 2-thiophenoyl chloride in benzene. The molecular conformation is stabilized by an intramolecular N-HÁ Á ÁO hydrogen bond. The dihedral angle between the rings is 2.74 (12) . In the crystal, C-HÁ Á ÁO interactions link neighbouring molecules into a three-dimensional network.
DPS and SP are grateful to Banaras Hindu University, Varanasi, for financial support. RJB acknowledges the NSF-MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to acknowledge the USIEF for the award of a Fulbright-Nehru Senior Research Fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5852). -O3 show partial double bond character with bond lengths of 1.365 (4), 1.401 (4), and 1.329 (3) Å respectively. All bond length and bond angles confirm the sp 2 hybridization for all C and N atoms except C 13 , indicating that the whole molecule is planar.

Experimental
The title compound was synthesized using the literature procedure (Sladowska et al., 1980). To a solution of methyl anthranilate (10 mmol) and triethyl amine(10mmol) in benzene(30 ml) was added 2-thiophenoyl chloride (10 mmol) in benzene(10 ml) with stirring at room temperature. After stirring for three hour, the reaction mixture was washed successively with water, dilute HCl and aqueous Na 2 CO 3 and the organic layer was dried over dry Na 2 SO 4 . After removal of the solvent, the residue was recrystallized from ethanol. Colorless, needles type crystal suitable for X-ray diffraction were obtained after few days. Yield 78%.

Refinement
H atoms were placed in calculated positions with C-H = 0.95-0.98 Å with isotropic displacement parameters fixed to U iso (H) = 1.2 U eq (C). The H attached to N was isotropically refined but with the N-H distance restrained to 0.88 Å.

Computing details
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).   Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.25886 (