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1-(3-Cyano-phen-yl)-3-(2-furo-yl)thio-urea.

ABSTRACT: The title compound, C(13)H(9)N(3)O(2)S, was synthesized from furoyl isothio-cyanate and 3-amino-benzonitrile in dry acetone. The thio-urea group is in the thio-amide form. The thio-urea fragment makes dihedral angles of 3.91?(16) and 37.83?(12)° with the ketofuran group and the benzene ring, respectively. The mol-ecular geometry is stabilized by N-H?O hydrogen bonds. In the crystal structure, centrosymmetrically related mol-ecules are linked by two inter-molecular N-H?S hydrogen bonds to form dimers.

SUBMITTER: Theodoro JE

PROVIDER: S-EPMC2961779 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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1-(3-Cyano-phen-yl)-3-(2-furo-yl)thio-urea.

Theodoro Jahyr E JE Mascarenhas Yvonne Y Ellena Javier J Estévez-Hernández Osvaldo O Duque Julio J

Acta crystallographica. Section E, Structure reports online 20080607 Pt 7

The title compound, C(13)H(9)N(3)O(2)S, was synthesized from furoyl isothio-cyanate and 3-amino-benzonitrile in dry acetone. The thio-urea group is in the thio-amide form. The thio-urea fragment makes dihedral angles of 3.91 (16) and 37.83 (12)° with the ketofuran group and the benzene ring, respectively. The mol-ecular geometry is stabilized by N-H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related mol-ecules are linked by two inter-molecular N-H⋯S hydrogen bonds to form di ...[more]

PMID: 21202835

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1-(2-Furo-yl)-3-(2-meth-oxy-4-nitro-phen-yl)thio-urea.

Project description:The asymmetric unit of the title compound, C13H11N3O5S, contains two independent mol-ecules, which are linked by a pair of inter-molecular N-H⋯S hydrogen bonds, forming an R2(2)(8) ring motif. The central thio-urea core forms dihedral angles of 3.02 (12) and 14.00 (10)° with the essentially planar furoyl groups [maximum deviations = 0.030 (2) and 0.057 (2) Å] in the two mol-ecules and dihedral angles of 2.43 (13) and 8.03 (12)° with the benzene rings. The dihedral angles between the furoyl and benzene rings in the two mol-ecules are 3.97 (10) and 5.98 (9)°. The trans-cis geometry of the thio-urea group is stabilized by three intra-molecular N-H⋯O hydrogen bonds involving carbonyl and meth-oxy O atoms with the H atom of the cis-thio-amide group and between furan O atom and the other thio-amide H atom. There is also a weak intra-molecular C-H⋯S inter-action in each mol-ecule.

| S-EPMC3588461 | biostudies-literature

1-Benzyl-3-(2-furo-yl)thio-urea.

Project description:In the title compound, C(13)H(12)N(2)O(2)S, the dihedral angle between the two aromatic ring planes is 87.52 (12)°. The mol-ecule shows an intra-molecular N-H⋯O hydrogen bond. The crystal structure is stabilized by inter-molecular N-H⋯S and C-H⋯O hydrogen bonding.

| S-EPMC2960941 | biostudies-literature

N-(2-Furo-yl)-N'-(2-pyrid-yl)thio-urea.

Project description:The title compound, C(11)H(9)N(3)O(2)S, crystallizes with two independent mol-ecules in the asymmetric unit. The central thio-urea core makes dihedral angles of -3.3 (3) and 0.6 (3)° with the furan carbonyl groups in each mol-ecule, whereas the pyridine ring is inclined by 4.63 (2) and 11.28 (7)°, respectively. The trans-cis geometry of the thio-urea fragment is stabilized by an intra-molecular N-H⋯N hydrogen bond between the H atom of the cis-thio-amide group and the pyridine N atom. In the crystal structure, inter-molecular bifurcated N-H⋯S and N-H⋯O hydrogen bonds form centrosymmetric tetra-mers extending along the b axis.

| S-EPMC2968930 | biostudies-literature

1-(2-Furo-yl)-3-(1-naphth-yl)thio-urea.

Project description:In the title compound, C(16)H(12)N(2)O(2)S, the carbonyl-thio-urea group forms dihedral angles of 75.4 (1) and 13.1 (2)°, respectively, with the naphthalene ring system and furan ring. The mol-ecule adopts a trans-cis configuration with respect to the positions of the furoyl and naphthyl groups relative to the S atom across the thio-urea C-N bonds. This geometry is stabilized by an N-H⋯·O intra-molecular hydrogen bond. In the crystal structure, mol-ecules are linked by N-H⋯S hydrogen bonds, forming centrosymmetric dimers which are inter-linked through C-H⋯π inter-actions.

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1-(2-Furo-yl)-3-(o-tol-yl)thio-urea.

Project description:The title compound, C(13)H(12)N(2)O(2)S, was synthesized from furoyl isothio-cyanate and o-toluidine in dry acetone. The thio-urea group is in the thio-amide form. The central thio-urea fragment makes dihedral angles of 2.6 (1) and 22.4 (1)° with the ketofuran group and the benzene ring, respectively. The mol-ecular structure is stabilized by N-H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related mol-ecules are linked by a pair of N-H⋯S hydrogen bonds to form a dimer with an R(2) (2)(6) ring motif.

| S-EPMC2962048 | biostudies-literature

Redetermination of 1-cyclo-hexyl-3-(2-furo-yl)thio-urea.

Project description:The title compound, C(12)H(16)N(2)O(2)S, was synthesized from furoyl isothio-cyanate and cyclo-hexyl-amine in dry acetone, and the crystal structure redetermined. The thio-urea group is in the thio-amide form. The structure [Otazo-Sánchez et al. (2001 ?). J. Chem. Soc. Perkin Trans. 2, pp. 2211-2218] has been redetermined in order to establish the intra- and inter-molecular inter-actions. The trans-cis geometry of the thio-urea group is stabilized by intra-molecular hydrogen bonding between the carbonyl and cis-thio-amide groups, resulting in a pseudo-S(6) planar ring which makes a dihedral angle of 3.24?(6)° with the 2-furoyl group and a torsion angle of -84.3?(2)° with the cyclo-hexyl group. There is also an intra-molecular hydrogen bond between the furan O atom and the other thio-amide H atom. In the crystal structure, mol-ecules are linked by inter-molecular N-H?O hydrogen bonds, forming chains along [010].

| S-EPMC2979067 | biostudies-literature

N-(2-Bromo-phen-yl)thio-urea.

Project description:In the title compound, C(7)H(7)BrN(2)S, the thio-urea unit is almost perpendicular to the bromo-benzene fragment, making a dihedral angle of 80.82?(16)°. The crystal structure is stabilized by N-H?S inter-molecular hydrogen bonds, which form linear chains along the ab diagonal.

| S-EPMC2983840 | biostudies-literature

1-(3-Chloro-phen-yl)thio-urea.

Project description:In the title compound, C(7)H(7)ClN(2)S, the thio-urea N-C(=S)-N plane forms a dihedral angle of 64.80?(6)° with the benzene ring. In the crystal, mol-ecules are linked via inter-molecular N-H?S and N-H?Cl hydrogen bonds into a sheet extending parallel to the (101) plane.

| S-EPMC3414341 | biostudies-literature

N-(3,4-Dichloro-phen-yl)thio-urea.

Project description:In the title compound, C(7)H(6)Cl(2)N(2)S, the benzene ring and the mean plane of the thio-urea fragment [-N-C(=S)-N] make a dihedral angle of 66.77?(3)°. Inter-molecular N-H?S and N-H?Cl hydrogen bonds link the mol-ecules into a three-dimensional network.

| S-EPMC2970483 | biostudies-literature

1-(2,4-Difluoro-phen-yl)thio-urea.

Project description:The asymmetric unit of the title compound, C(7)H(6)F(2)N(2)S, consists of two independent mol-ecules, with comparable geometries. In one mol-ecule, the thio-urea moiety is essentially planar (r.m.s. deviation = 0.014 Å) and it forms a dihedral angle of 78.67 (9)° with the benzene ring. The corresponding r.m.s. deviation and dihedral angle for the other mol-ecule are 0.011 Å and 81.71 (8)°, respectively. In both mol-ecules, one of the F atoms is disordered over two positions with refined site occupancies of 0.572 (3):0.428 (3) and 0.909 (2):0.091 (2), respectively. In the crystal, mol-ecules are linked via N-H⋯S and C-H⋯F hydrogen bonds into two-dimensional networks parallel to (010).

| S-EPMC3414916 | biostudies-literature

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