Ethyl 4-hydroxy-6-(4-hydroxyphenyl)-4-trifluoromethyl-2-sulfanylidene-1,3-diazinane-5-carboxylate ethanol monosolvate

Feng-Ling Yang,Wen-Jun Fa

doi:10.1107/s1600536811015376

Abstract

The title compound, C14H15F3N2O4S·C2H5OH, was prepared by reaction of 4-hydroxybenzaldehyde, ethyl 4,4,4-trifluoro-3-oxobutanoate and thiourea. The hexahydropyrimidine ring adopts a half-chair conformation, the mean plane formed by the ring atoms excluding the C atom bonded to the ethoxycarbonyl group has an r.m.s. deviation of 0.0333 Å, and the dihedral angle between this plane and the benzene ring is 56.76 (5)°. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) ring. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds. The ethyl group of the ester unit is disordered over two positions, with an occupancy ratio of 0.757 (10):0.243 (10).

Highlights

The title compound, C14H15F3N2O4SÁC2H5OH, was prepared by reaction of 4-hydroxybenzaldehyde, ethyl 4,4,4-trifluoro-3oxobutanoate and thiourea
The hexahydropyrimidine ring adopts a half-chair conformation, the mean plane formed by the ring atoms excluding the C atom bonded to the ethoxycarbonyl group has an r.m.s. deviation of 0.0333 A, and the dihedral angle between this plane and the benzene ring is 56.76 (5)
The molecular conformation is stabilized by an intramolecular O—HÁ Á ÁO hydrogen bond, generating an S(6) ring

Summary

Structure Reports Online

Key indicators: single-crystal X-ray study; T = 113 K; mean (C–C) = 0.002 A; disorder in main residue; R factor = 0.036; wR factor = 0.092; data-to-parameter ratio = 16.0. The hexahydropyrimidine ring adopts a half-chair conformation, the mean plane formed by the ring atoms excluding the C atom bonded to the ethoxycarbonyl group has an r.m.s. deviation of 0.0333 A , and the dihedral angle between this plane and the benzene ring is 56.76 (5). The molecular conformation is stabilized by an intramolecular O—HÁ Á ÁO hydrogen bond, generating an S(6) ring. The crystal structure is stabilized by intermolecular O— HÁ Á ÁO, O—HÁ Á ÁS, N—HÁ Á ÁO and N—HÁ Á ÁS hydrogen bonds. The ethyl group of the ester unit is disordered over two positions, with an occupancy ratio of 0.757 (10):0.243 (10)

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