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2-Amino-6-methyl-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile.

ABSTRACT: In the title compound, C(10)H(12)N(2)S, one of the C atoms of the cyclo-hexene ring (at position 6) and the methyl group attached to it are disordered over two sets of sites in a 0.650 (3):0.350 (3) ratio. The cyclo-hexene ring in both the major and minor occupancy conformers adopts a half-chair conformation. The thio-phene ring is essentially planar (r.m.s. deviation = 0.05 Å). In the crystal, N-H⋯N hydrogen bonds involving the amino groups result in inversion dimers with R(2) (2)(12) graph-set motif. Further N-H⋯N hydrogen bonds involving the amino and carbonitrile groups generate zigzag chains along the a axis.

SUBMITTER: Ziaulla M

PROVIDER: S-EPMC3051984 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The mol-ecule of the title compound, C(18)H(19)NO(3)S, adopts an approximately planar conformation: the thio-phene and phenyl rings form a dihedral angle of 8.13?(11)° while the ethyl ester group (r.m.s. deviation = 0.0217?Å) is inclined at 1.25?(14) and 8.61?(13)°, respectively, to the thio-phene and phenyl rings. An intra-molecular N-H?O hydrogen bond with an S(6) ring motif occurs as well as an intra-molecular S?O hypervalent inter-action [S?O = 2.7369?(18)?Å]. The cyclo-hexene ring adopts a half-chair conformation and is disordered over two positions with site occupation factors of 0.641?(6) and 0.359?(6). In the crystal, inversion dimers linked by pairs of O-H?O hydrogen bonds generate R(2) (2)(10) loops.

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