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(Z)-3-Benzyl-2-[(2-phenyl-cyclo-hex-2-en-yl)imino]-1,3-thia-zolidin-4-one.

ABSTRACT: The title compound, C(22)H(22)N(2)OS, exists in a Z configuration with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar, with a maximum deviation of 0.030?(2)?Å, and forms dihedral angles of 76.66?(6) and 74.55?(6)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 71.55?(7)°. In the crystal, a C-H?? inter-action is observed.

SUBMITTER: Ooi CW

PROVIDER: S-EPMC3415005 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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(Z)-3-Benzyl-2-[(2-phenyl-cyclo-hex-2-en-yl)imino]-1,3-thia-zolidin-4-one.

Ooi Chin Wei CW Fun Hoong-Kun HK Quah Ching Kheng CK Sathishkumar Murugan M Ponnuswamy Alagusundaram A

Acta crystallographica. Section E, Structure reports online 20120728 Pt 8

The title compound, C(22)H(22)N(2)OS, exists in a Z configuration with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar, with a maximum deviation of 0.030 (2) Å, and forms dihedral angles of 76.66 (6) and 74.55 (6)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 71.55 (7)°. In the crystal, a C-H⋯π inter-action is observed. ...[more]

PMID: 22904992

Similar Datasets

5-Benzyl-idene-3-phenyl-2-phenyl-imino-1,3-thia-zolidin-4-one.

Project description:The title compound, C(22)H(16)N(2)OS, is a chalcone analog with a thia-zolidinone core that was synthesized as a potential cytotoxic and anti-cancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent mol-ecules are differerentiated by the dihedral angle between the mean planes of the benzyl-idene phenyl group against the thia-zolidin-4-one moiety, which is 5.01?(7)° in one mol-ecule, and 17.41?(6)° in the other. The two mol-ecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two mol-ecules are not planar but are slightly bent with the benzyl-idene and phenyl-imino substituents being bent upwards with respect to the center planes of the two mol-ecules. The degree of bending of the two halves of the thia-zolidin-4-one moieties (defined as the planes that inter-sect at the S atom) are 11.08?(7) and 15.88?(7)°. Packing of the mol-ecules is facilitated by C-H?? inter-actions and slipped ?-? stacking between one of the phenyl rings and a neighboring ethylene ? system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267?(2)?Å, Cg(phenyl)?Cg(ethylene) = 3.926?Å].

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(Z)-3-(4-Chloro-phen-yl)-2-(2-phenyl-cyclo-hex-2-en-1-yl-imino)-thia-zolidin-4-one.

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Project description:The title compound, C(22)H(22)N(2)OS, exists in a cis conformation with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar with a maximum deviation of 0.025?(2)?Å and forms dihedral angles of 63.50?(7) and 57.52?(6)° with the benzene rings. In the crystal, mol-ecules are linked by C-H?O and C-H?N hydrogen bonds, generating R(2) (2)(8) ring motifs, and forming infinite chains along the c axis. The crystal is further consolidated by C-H?? inter-actions.

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Project description:In the title compound, C(17)H(13)NOS(2), the heterocyclic ring is oriented at a dihedral angle of 74.43?(5)° with respect to the anilinic benzene ring and at a dihedral angle of 17.31?(9)° with respect to phenyl ring. An intra-molecular C-H?S inter-action occurs, resulting in an S(6) ring. In the crystal, the packing is consolidated by C-H?? inter-actions and possible very weak aromatic ?-? stacking [centroid-centroid separation = 4.025?(1)?Å].

| S-EPMC2971373 | biostudies-literature

(5Z)-5-(2-Hydroxy-benzyl-idene)-3-phenyl-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(16)H(11)NO(2)S(2), the dihedral angles between the heterocyclic ring and the phenyl and anilinic benzene rings are 9.68 (13) and 79.26 (6)°, respectively, and an intra-molecular C-H⋯S inter-action occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur, leading to R(2) (2)(10) loops, and C-H⋯O and weak C-H⋯π inter-actions further consolidate the packing.

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3-Cyclo-hexyl-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(9)H(13)NOS(2), the complete mol-ecule is generated by crystallographic mirror symmetry, with all the non-H atoms of the rhodanine (2-thioxo-1,3-thia-zolidin-4-one) system and two C atoms of the cyclo-hexyl ring lying on the reflecting plane. The conformation is stabilized by intra-molecular C-H⋯O and C-H⋯S inter-actions. In the crystal, weak π-π inter-actions at a distance of 3.8140 (5) Å between the centroids of the heterocyclic rings occur.

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(Z)-3-(4-Bromo-phen-yl)-2-[(2-phenyl-cyclo-hex-2-en-1-yl)imino]-1,3-thia-zol-idin-4-one.

Project description:The title compound, C(21)H(19)BrN(2)OS, exists in a cis conformation with respect to the N=C bond [1.2602?(14)?Å]. The cyclo-hexene ring adopts a distorted half-chair conformation and the C-N bond lies in an equatorial orientation. The thia-zolidine ring forms dihedral angles of 53.76?(7) and 57.22?(7)° with the benzene and bromo-substituted benzene rings, respectively. The dihedral angle between the benzene and bromo-substituted benzene rings is 76.06?(7)°. In the crystal, inversion dimers linked by pairs of C-H?O hydrogen bonds generate R(2) (2)(14) loops. The crystal is further consolidated by weak C-H?? inter-actions.

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3-Benzyl-5-benzyl-idene-2-sulfanylidene-1,3-thia-zolidin-4-one.

Project description:In the title mol-ecule, C(17)H(13)NOS(2), the essentially planar thia-zole ring (r.m.s deviation 0.005?Å) forms dihedral angles of 16.85?(8)° and 75.02?(8)° with the phenyl rings. The dihedral angle between the two phenyl rings is 61.95?(9)°.

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