Abstract
The title heterocyclic compound, C20H17NO3S, was synthesized by condensation of ethyl cyanoacetate with (Z)-2-benzylidenebenzo[b]thiophen-3(2H)-one in the presence of a basic catalyst in ethanol. The phenyl and ester groups make dihedral angles of 77.67 (6) and 8.52 (6)°, respectively, with the benzothienopyran ring system [maximum r.m.s. deviation = 0.1177 (13) Å]. In the crystal, centrosymmetric dimers are formed through pairs of N—H⋯O hydrogen bonds between the amine and ester groups. Intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions involving the thiophene ring are also observed.
Highlights
The title heterocyclic compound, C20H17NO3S, was synthesized by condensation of ethyl cyanoacetate with (Z)-2benzylidenebenzo[b]thiophen-3(2H)-one in the presence of a basic catalyst in ethanol
Centrosymmetric dimers are formed through pairs of N—HÁ Á ÁO hydrogen bonds between the amine and ester groups
H atoms treated by a mixture of independent and constrained refinement
Summary
Adil Boughaleb,a Hafid Zouihri,b Said Gmouh,c Abdelali Kerbala and Mohamed El yazidia*. Key indicators: single-crystal X-ray study; T = 296 K, P = 0.0 kPa; mean (C–C) = 0.002 A; R factor = 0.034; wR factor = 0.086; data-to-parameter ratio = 15.5. The title heterocyclic compound, C20H17NO3S, was synthesized by condensation of ethyl cyanoacetate with (Z)-2benzylidenebenzo[b]thiophen-3(2H)-one in the presence of a basic catalyst in ethanol. The phenyl and ester groups make dihedral angles of 77.67 (6) and 8.52 (6), respectively, with the benzothienopyran ring system [maximum r.m.s. deviation = 0.1177 (13) A ]. Centrosymmetric dimers are formed through pairs of N—HÁ Á ÁO hydrogen bonds between the amine and ester groups. Intermolecular C—HÁ Á ÁN hydrogen bonds and C—HÁ Á Á interactions involving the thiophene ring are observed.
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