Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

Abstract

In the title mol­ecule, C16H14O4S, the dihydro­cyclo­penta­thio­phenone ring system is almost planar, with an r.m.s. deviation of 0.060 Å from the best fit plane through all nine non-H atoms. The cyclo­penta­none ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185 (3) Å from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37 (5)° to the dihydro­cyclo­penta­thio­phenone mean plane. In the crystal, mol­ecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers with R 2 2(10) ring motifs. Weak C—H⋯O hydrogen bonds also link mol­ecules into chains along c, while an approximately orthogonal set of C—H⋯O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R 2 2(12) C—H⋯S contacts, which combine with C—H⋯O contacts to form stacks along b.