The title molecule, C12H12N2OS, is planar, with an r.m.s. deviation of 0.04 Å. In the crystal, the N atom adjacent to the carbonyl group is sp
2-hybridized. The crystal structure is stabilized by π–π stacking interactions observed between thiophene and pyrimidinone rings of c-glide-related molecules [centroid–centroid distance = 3.9554 (13) Å] and by C—H⋯π interactions, forming an infinite chain along the c-axis direction.
The new compounds (Z)-ethyl 2-cyano-2-(3H- and 2-methyl-3H-quinazoline- 4-ylidene) acetate (1 and 2, respectively) were synthesized by multi-step reactions. The structures in a solution have been determined by 1H-NMR spectroscopy and in the crystal form by X-ray analysis. Molecule 1 crystallized in a primitive monoclinic cell, space group Р21/c. The cell dimensions are a=7.970(6) Å, b=7.061(2) Å, c=20.537(7) Å, β=97.69(5)°, V=1145.3(10) Å3. Molecule 2 crystallized in a triclinic cell, space group P1, the cell dimensions are a=8.196(5) Å, b=8.997(6) Å, c=9.435(4) Å, α=74.22(4)°, β=89.75(4)°, γ=74.07(5)°, V=641.9(6) Å3. In both compounds the presence of intramolecular NH---O=C hydrogen bonding between the nitrogen atom in position 3 of the quinazoline ring and a carbonyl group of the ethyl cyanoacetate residue was proven by quantum-chemical, 1H-NMR and X-ray methods.
Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.007 Å; disorder in main residue; R factor = 0.063; wR factor = 0.169; data-to-parameter ratio = 9.9.There are two independent molecules in the asymmetric unit of the title compound, C 12 H 12 N 2 O 3 S. With the exception of the methylene groups, a mean plane fitted through all non-H atoms of each molecule has an r.m.s. deviation of 0.035 Å for one molecule and 0.120 Å for the second. In one of the independent molecules, the methylene groups was refined using a disorder model with an occupancy ratio of 0.53:0.47 (14). Each molecule features an intramolecular O-HÁ Á ÁO hydrogen bond, which generates an S(7) ring.
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