Ethyl N-(2-benzoyl-4-chlorophenyl)ethanecarboximidate

In the title compound, C17H16ClNO2, the N=C—O—C—C fragment is planar within 0.029 (1) Å, and makes dihedral angles of 66.71 (8) and 59.61 (8)° with the planes of the chlorophenyl and benzoyl rings, respectively. The carbonyl C=O bond is not coplanar with either of the aromatic rings; it makes angles of 42.5 and 23.5° with the normals to the ring planes. In the crystal, very weak C—H⋯O, C—H⋯Cl, C—H⋯π and π–π [interplanar distance = 3.53 (1) Å] interactions are observed.

In the title compound, C 17 H 16 ClNO 2 , the N C-O-C-C fragment is planar within 0.029 (1) Å , and makes dihedral angles of 66.71 (8) and 59.61 (8) with the planes of the chlorophenyl and benzoyl rings, respectively. The carbonyl C O bond is not coplanar with either of the aromatic rings; it makes angles of 42.5 and 23.5 with the normals to the ring planes. In the crystal, very weak C-HÁ Á ÁO, C-HÁ Á ÁCl, C-HÁ Á Á and -[interplanar distance = 3.53 (1) Å ] interactions are observed.
ASD thanks the University of Mysore for research facilities. HSY thanks R. L. Fine Chem, Bengaluru, India, for the gift sample of the title compound. Benzophenone and related analogues have been reported to act as antiallergic, anti-inflammatory, antiasthamatic, antimalarial, anti-microbial and antianaphylactic agents (Evans et al., 1987;Wiesner et al., 2002). The competence of benzophenones as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer and inflammation, is well established and their chemistry has been studied extensively (Revesz et al., 2004, Zeng et al., 2010. The title compound -N-(2-Benzoyl-4-chloro-phenyl)-acetimidic acid ethyl ester (1, Scheme 1) -is an intermediate in the synthesis of certain anxiolytic, anticonvulsant and sedative drugs.
In the crystal only some weak but directional C-H···O, C-H···Cl and C-H···π interaction can be found (cf. Table), and they to some extent influence the packing together with van der Waals interactions. Also the phenyl rings B from molecules related by the center of symmetry stack to some extent with the interplanar distance of ca 3.53 Å.

Experimental
The title compound was obtained as a gift sample from R. L. Fine Chem., Bengaluru, India. The compound was recrystallized from dichloromethane by slow evaporation (m.p: 323 K).

Refinement
Hydrogen atoms were put in the idealized positions, and refined as riding model. Their isotropic thermal parameters were set at 1.2 times U eq 's of appropriate carrier atoms.

Computing details
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008   The crystal packing as seen approximately along the a-axis direction. Weak C-H···Cl hydrogen bonds are depicted as dashed lines.  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.