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Ethyl 2-acet-amido-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

ABSTRACT: In the title compound, C(13)H(17)NO(3)S, the dihedral angles between the thio-phene ring and the ethyl ester and acetamide groups are 5.21?(13) and 10.06?(16)°, respectively. The cyclo-hezene ring adopts a half-chair conformation. An S(6) ring is formed due to an intra-molecular N-H?O hydrogen bond. In the crystal, mol-ecules are linked by C-H?O inter-actions between the tetra-hydro-1-benzothio-phene unit and the ethyl ester group, forming C(7) chains propagating along the b-axis direction.

SUBMITTER: Mukhtar A

PROVIDER: S-EPMC3393310 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Ethyl 2-acet-amido-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

Mukhtar Asma A Tahir M Nawaz MN Khan Misbahul Ain MA Ather Abdul Qayyum AQ Khan Muhammad Naeem MN

Acta crystallographica. Section E, Structure reports online 20120613 Pt 7

In the title compound, C(13)H(17)NO(3)S, the dihedral angles between the thio-phene ring and the ethyl ester and acetamide groups are 5.21 (13) and 10.06 (16)°, respectively. The cyclo-hezene ring adopts a half-chair conformation. An S(6) ring is formed due to an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by C-H⋯O inter-actions between the tetra-hydro-1-benzothio-phene unit and the ethyl ester group, forming C(7) chains propagating along the b-axis direction. ...[more]

PMID: 22807867

Similar Datasets

Ethyl 2-benzamido-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

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.

| S-EPMC2983258 | biostudies-literature

Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

Project description:In the title compound, C(17)H(18)N(2)O(3)S, the dihedral angles between the thio-phene ring and the ethyl ester group and the pyridine-4-carboxamide unit are 7.1?(2) and 9.47?(11)°, respectively. An intra-molecular N-H?O hydrogen bond generates an S(6) ring. In the crystal, inversion dimers linked by pairs of C-H?O hydrogen bonds between the tetra-hydro-1-benzothio-phene and the pyridine-4-carboxamide residues generate R(2) (2)(16) loops. There exists positional disorder in three methelene groups of the cyclo-hexane ring and the terminal C atom of the ethyl ester side chain in a 0.691?(14):0.309?(14) occupancy ratio.

| S-EPMC3393309 | biostudies-literature

Methyl 2-(2-hydroxy-benzyl-ideneamino)-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

Project description:In the title compound, C(17)H(17)NO(3)S, the cyclohexene ring is essentially planar, with a maximum deviation of 0.006 (1) Å. The cyclo-hexene ring adopts a half-chair conformation. The dihedral angle between the thio-phene and benzene rings is 29.7 (1)°. The mol-ecular structure exhibits intra-molecular O-H⋯O, O-H⋯N and C-H⋯S hydrogen bonds, which generate one S(5) and two S(6) motifs. There is also a C-H⋯π inter-action between the cyclo-hexene ring system and the π-system of the benzene ring.

| S-EPMC2961328 | biostudies-literature

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

Project description: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.

| S-EPMC3051984 | biostudies-literature

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

Project description:In the title compound, C(9)H(8)N(2)OS, the benzothio-phene ring is substituted with amino, oxo and carbonitrile groups. The thio-phene ring is essentially planar (r.m.s. deviation = 0.0003 Å), while the cyclo-hexene ring is in a half-chair conformation. In the crystal, N-H⋯O hydrogen bonds generate chains of mol-ecules in a zigzag pattern along the b axis. Pairs of N-H⋯N hydrogen bonds form centrosymmetric head-to-head dimers about inversion centres, corresponding to an R(2) (2)(12) graph-set motif. In addition, rather weak N-H⋯S inter-actions are also present in the structure and the supra-molecular assembly is further consolidated by π-π stacking inter-actions between the benzothio-phene rings, disposed at a distance of 3.742 (3) Å.

| S-EPMC2983310 | biostudies-literature

Ethyl 2-(3,3-dibutyl-thio-ureido)-4,5,6,7-tetra-hydro-benzo[b]thio-phene-3-carboxyl-ate.

Project description:In the title compound, C(20)H(32)N(2)O(2)S(2), the cyclo-hexene ring is disordered over two half-boat conformations with occupancy factors of 0.71:0.29. One n-butyl chain is also disordered over two positions with occupancy factors of 0.83:0.17. The mol-ecular conformation is stabilized by an intra-molecular N-H?O hydrogen bond.

| S-EPMC2971811 | biostudies-other

2-[(4-Chloro-benzyl-idene)amino]-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile.

Project description:In the title compound, C(16)H(13)ClN(2)S, the dihedral angle between the 4-chloro-benzaldehyde moiety and the heterocyclic five-membered ring is 7.21?(17)°. In the crystal, mol-ecules are linked by weak C-H?? inter-actions, generating [100] chains.

| S-EPMC3200595 | biostudies-literature

2-[(2-Chloro-benzyl-idene)amino]-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile.

Project description:In the title compound, C(16)H(13)ClN(2)S, the mean planes fitted through all non-H atoms of the heterocyclic five-membered and the benzene rings are oriented at a dihedral angle of 5.19?(7)°. In the crystal, a weak C-H?? inter-action occurs, along with weak ?-? inter-actions [cenroid-centroid distance = 3.7698?(11)?Å].

| S-EPMC3200582 | biostudies-literature

Ethyl 2-amino-6-benzyl-4,5,6,7-tetra-hydro-thieno[2,3-c]pyridine-3-carboxyl-ate.

Project description:In the title compound, C(17)H(20)N(2)O(2)S, the tetra-hydro-pyridine ring adopts an envelope conformation with the N atom at the flap position; the phenyl ring makes a dihedral angle of 81.06?(10)° with the thio-phene ring. The amino group links with the carbonyl O atom via intra-molecular N-H?O hydrogen bonding, forming a six-membered ring. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into infinite chains running along the b axis.

| S-EPMC3050265 | biostudies-literature

2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyl-eneamino]-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile-benzene (2/1).

Project description:In the title compound, 2C(24)H(21)N(3)S·C(6)H(6), the two independent Schiff base mol-ecules (A and B) in the asymmetric unit differ in the orientation of the tetra-hydro-benzothio-phene ring system with respect to the carbazole ring system by 180° rotation about the C-C bond in the C-C=N-C linkage. The two mol-ecules also differ in the orientation of the ethyl groups [C-N-C-C torsion angle of 90.7?(3)° in mol-ecule A, and -79.4?(3)° in mol-ecule B]. In mol-ecule B, two methyl-ene C atoms of the cyclo-hexene ring are disordered over two sites with occupancies of 0.58?(1) and 0.42?(1). The cyclo-hexene rings in both mol-ecules adopt half-chair conformations. The dihedral angle between the thio-phene ring and the carbazole ring system is 8.07?(9)° in mol-ecule A [3.10?(9)° in mol-ecule B]. In the crystal structure, the independent mol-ecules are linked into dimers by inter-molecular C-H?N hydrogen bonds. In addition, C-H?? inter-actions are observed.

| S-EPMC2979233 | biostudies-literature

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