7-Chloro-5-cyclopropyl-9-methyl-5H-4,5,6,10-tetraazadibenzo[a,d]cyclohepten-11(10H)-one

In the title compound, C15H13ClN4O, which is a chloro derivative of the drug Nevirapine, the diazepine ring is in a twisted boat conformation. The pyridine rings fused to the diazepine fragment form a dihedral angle of 58.44 (10)° and the molecule adopts a butterfly shape. The molecules are joined via N—H⋯N hydrogen bonding into polymeric chains down the b axis. All weaker C—H⋯O interactions involve the carbonyl O atom as acceptor.

In the title compound, C 15 H 13 ClN 4 O, which is a chloro derivative of the drug Nevirapine, the diazepine ring is in a twisted boat conformation. The pyridine rings fused to the diazepine fragment form a dihedral angle of 58.44 (10) and the molecule adopts a butterfly shape. The molecules are joined via N-HÁ Á ÁN hydrogen bonding into polymeric chains down the b axis. All weaker C-HÁ Á ÁO interactions involve the carbonyl O atom as acceptor.
The title diazepine compound is a chloro derivative of the well known anti-HIV drug Nevirapine. The drug Nevirapine is the first human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase (RT) inhibitor to reach regulatory approval. The title compound has been synthesized as a basic scaffold as reported earlier (Matsumoto et al., 1984). We have also synthesized its derivatives and tested for secretory phospholipase A 2 with anti-inflammatory activity (Thimmegowda et al., 2007). We have identified a few derivatives with good activity. In view of this we have crystallized the title compound and finally the structure was confirmed by the X-ray diffraction studies.
The structure exhibits intermolecular hydrogen bonds of the N-H···N and C-H···O type. The oxygen atom attatched to the diazepine ring accepts four intermolecular C-H···O hydrogen bonds.

Experimental
The title compound was synthesized as per the procedure reported earlier (Matsumoto et al., 1984). After synthesis and purification, the resultant pure product obtained was dissolved in ethyl acetate and was left undisturbed for slow evaporation of the solvent. Brown crystals grew after five days.
supplementary materials sup-2 Refinement H atoms were placed at idealized positions and allowed to ride on their parent atoms with C-H distances in the range 0.93-0.98 Å and N-H distance 0.86 Å; U iso (H) = 1.2U eq (carrier atom) for all H atoms. Fig. 1. A view of the title compound with 50% probability displacement ellipsoids.