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

ABSTRACT: 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.

SUBMITTER: Shahwar D

PROVIDER: S-EPMC2971093 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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

Shahwar Durre D Tahir M Nawaz MN Raza Muhammad Asam MA Iqbal Bushra B

Acta crystallographica. Section E, Structure reports online 20091028 Pt 11

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. ...[more]

PMID: 21578485

Similar Datasets

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

Project description:In the title compound, C(10)H(7)NO(2)S(2)·0.5CH(3)OH, the dihedral angle between the aromatic rings is 11.43 (11)° and a short intra-molecular C-H⋯S contact occurs. The methanol solvent mol-ecule is equally disordered over two sets of sites. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. The methanol solvent mol-ecule connects the dimers through O-H⋯S and O-H⋯O inter-molecular hydrogen bonds. Further stability is afforded by C-H⋯π and π-π inter-actions [centroid-centroid separation = 3.5948 (13) Å].

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

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⋯π inter-actions and possible very weak aromatic π-π stacking [centroid-centroid separation = 4.025 (1) Å].

| S-EPMC2971373 | biostudies-literature

3-Phenyl-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the mol-ecule of the title compound, C(9)H(7)NOS(2), the heterocycle and the phenyl ring are oriented at a dihedral angle of 72.3 (1)°. Adjacent mol-ecules are connected through C-H⋯O inter-actions.

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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⋯π inter-actions and slipped π-π stacking between one of the phenyl rings and a neighboring ethylene π 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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3-Benzyl-2-phenyl-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(16)H(15)NOS, the thia-zolidine ring, which is essentially planar [maximum deviation = 0.071 (2) Å], makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45 (5)°. In the crystal, mol-ecules are linked by a weak inter-molecular C-H⋯O hydrogen bond, forming a supra-molecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C-H⋯π inter-action.

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(5Z)-5-(2-Hy-droxy-benzyl-idene)-3-(4-methyl-phen-yl)-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(17)H(13)NO(2)S(2), the dihedral angles between the 2-sulfanyl-idene-1,3-thia-zolidin-4-one group and the pendant toluene and 2-hy-droxy-benzene rings are 74.62 (6) and 8.73 (12)°, respectively. An intra-molecular C-H⋯S inter-action occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(16) loops. This link is reinforced by a pair of C-H⋯O hydrogen bonds. The dimers are connected by weak C-H⋯S inter-actions.

| S-EPMC3379392 | biostudies-literature

3-Benzyl-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(10)H(9)NOS(2), the five-membered heterocyclic ring and the benzyl moiety are oriented at a dihedral angle of 77.25 (4)°. In the crystal, infinite polymeric C(6) chains extending along [001] are formed due to C-H⋯O hydrogen bonds. C-H⋯π inter-actions link the chains, building up a three-dimensional network.

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(5E)-5-(4-Hydr-oxy-3-methoxy-benzyl-idene)-2-thioxo-1,3-thia-zolidin-4-one methanol monosolvate.

Project description:In the title compound, C(11)H(9)NO(3)S(2)·CH(4)O, the dihedral angle between the aromatic rings is 3.57 (16)° and intra-molecular O-H⋯O and C-H⋯S inter-actions occur. In the crystal, the thia-zolidin-4-one mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains. The hydrogen-bond motifs lead to S(5), S(6) and R(3) (3)(8) ring motifs. There exist C=O⋯π inter-actions between the heterocyclic rings and π-π inter-actions between the heterocyclic and benzene rings at distances of 3.455 (2) and 3.602 (2) Å, respectively. The methanol solvent mol-ecule is disordered over two sets of sites in a 0.542 (9):0.458 (9) ratio.

| S-EPMC2971307 | biostudies-literature

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)°.

| S-EPMC3213525 | biostudies-literature

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.

| S-EPMC2971948 | biostudies-literature

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