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N-[2-(4-Chloro-phen-yl)-5-methyl-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide.

ABSTRACT: The title compound, C(16)H(14)ClN(3)O(2)S, crystallizes with two mol-ecules in the asymmetric unit. In the 1,3-thia-zolidine rings, the carbonyl O atoms, the S atoms, the methyl groups and the ring carbon attached to the methyl groups are disordered with occupancy ratios of 0.509?(7):0.491?(7) in one mol-ecule and 0.464?(14):0.536?(14) in the other. The crystal structure is stabilized by inter-molecular N-H?N, C-H?O hydrogen bonds and C-H?Cl inter-actions. In addition, there is a ?-? stacking inter-action [centroid-centroid distance = 3.794?(3)?Å] between the benzene and pyridine rings.

SUBMITTER: Akkurt M

PROVIDER: S-EPMC3099898 | biostudies-other | 2011 Apr

REPOSITORIES: biostudies-other

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N-[2-(4-Chloro-phen-yl)-5-methyl-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide.

Akkurt Mehmet M Celik Ismail I Demir Hale H Ozkırımlı Sumru S Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20110302 Pt 4

The title compound, C(16)H(14)ClN(3)O(2)S, crystallizes with two mol-ecules in the asymmetric unit. In the 1,3-thia-zolidine rings, the carbonyl O atoms, the S atoms, the methyl groups and the ring carbon attached to the methyl groups are disordered with occupancy ratios of 0.509 (7):0.491 (7) in one mol-ecule and 0.464 (14):0.536 (14) in the other. The crystal structure is stabilized by inter-molecular N-H⋯N, C-H⋯O hydrogen bonds and C-H⋯Cl inter-actions. In addition, there is a π-π stacking in ...[more]

PMID: 21754043

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N-[2-(4-Bromo-phen-yl)-5-methyl-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide.

Project description:In the title compound, C(16)H(14)BrN(3)O(2)S, the atoms of the 1,3-thia-zolidine group, except for the N and the C atoms attached to the bromo-benzene ring, are disordered over two sets of sites with occupancies of 0.605?(13) and 0.395?(13). The benzene and pyridine rings make a dihedral angle of 86.2?(2)°. In the crystal, mol-ecules are linked by inter-molecular N-H?N and C-H?O hydrogen bonds, forming a three-dimensional network. Furthermore, there is a ?-? stacking inter-action [centroid-centroid distance = 3.758?(2)?Å] between the pyridine and benzene rings.

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N-[5-Methyl-2-(2-nitro-phen-yl)-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide monohydrate.

Project description:In the title compound, C(16)H(14)N(4)O(4)S·H(2)O, the benzene and pyridine rings make a dihedral angle of 85.8 (1)°. Both enanti-omers of the chiral title compound are statistically disordered over the same position in the unit cell. The methyl and carbonyl group attached to the stereogenic center (C(5) of the thia-zolidine ring) were therefore refined with common site-occupation factors of 0.531 (9) and 0.469 (9), respectively, for each stereoisomer. In the crystal, inter-molecular N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules, forming a three-dimensional supra-molecular network. The crystal structure further shows π-π stacking inter-actions [centroid-centroid distance = 3.5063 (13) Å] between the pyridine rings.

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5-Chloro-N-{4-oxo-2-[4-(trifluoro-meth-yl)phen-yl]-1,3-thia-zolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide.

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Project description:The title pesticide, C(17)H(21)ClN(2)O(2)S, has a trans arrangement of the 4-chloro-phenyl and 4-methyl substituents of the thia-zolidine ring; the structure features an intra-molecular amide-ring carbonyl N-H⋯O hydrogen bond. The thia-zolidine ring is almost planar, the largest deviation being 0.199 (1) Å for the methyl-substitued C atom, and the cyclohexane ring has a chair conformation.

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Crystal structures of 2,3-bis-(4-chloro-phen-yl)-1,3-thia-zolidin-4-one and trans-2,3-bis-(4-chloro-phen-yl)-1,3-thia-zolidin-4-one 1-oxide.

Project description:In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thia-zolidine ring is attached to two chloro-phenyl rings. The chloro-phenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chloro-phenyl ring on the 2-carbon. The chloro-phenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thia-zolidine ring has a twisted conformation on the S-Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), mol-ecules are linked by C-H⋯O hydrogen bonds, as well as by slipped parallel π-π inter-actions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), mol-ecules are linked via C-H⋯O and C-H⋯Cl hydrogen bonds, forming slabs parallel to (001).

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4-Methyl-N-[(2-oxo-1,3-thia-zolidin-3-yl)carbon-yl]benzene-sulfonamide.

Project description:The asymmetric unit of the title compound, C(11)H(12)N(2)O(4)S(2), contains two independent mol-ecules with similar dihedral angles of 76.7?(1) and 77.3?(1)° between the mean planes of the five- and six-membered rings. In both mol-ecules, the amino groups are involved in intra-molecular N-H?O hydrogen bonds. In the crystal structure, weak inter-molecular C-H?O hydrogen bonds link mol-ecules into ribbons extended along the a axis.

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3-(4-Methyl-phen-yl)-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(10)H(9)NOS(2), the toluene group and the 2-thioxo-1,3-thia-zolidin-4-one unit are planar with r.m.s. deviations of 0.0082 and 0.0136?Å, respectively. The dihedral angle between them is 71.20?(9)°. In the crystal, the mol-ecules are stabilized through inter-molecular C-H?O contacts, forming polymeric sheets extending parallel to the (01) plane. C-H?? contacts also occur.

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3-(3-Methyl-phen-yl)-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(10)H(9)NOS(2), the dihedral angle between the rhodanine (2-thioxo-1,3-thia-zolidin-4-one) and 3-methyl-phenyl rings is 83.30?(3)°. The H atoms of the methyl group are disordered over two set of sites with an occupancy ratio of 0.58?(3):0.42?(3). In the crystal, the mol-ecules inter-act by way of C-H?? and C=O?? inter-actions.

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2-(4-Chloro-phen-yl)-3-p-tolyl-1,3-thia-zolidin-4-one.

Project description:The title compound, C(16)H(14)ClNOS, a potent anti-bacterial chemical, features a dihedral angle of 49.4 (1)° between the 4-tolyl and thia-zolidinone rings, and a dihedral angle of 87.2 (5)° between the thia-zolidinone and 4-chloro-phenyl rings.

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