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2-Methyl-N-[(3-methyl-2-pyrid-yl)carbamothio-yl]benzamide.

ABSTRACT: In the title compound, C(15)H(15)N(3)OS, the thio-urea group is stabilized by an intra-molecular hydrogen bond between the carbonyl O atom and the thio-amide group. A C-H?N intramolecular hydrogen bond is also present. Mol-ecules are linked by inter-molecular N-H?O and C-H?S hydrogen bonds.

SUBMITTER: Yamin BM

PROVIDER: S-EPMC2961265 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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2-Methyl-N-[(3-methyl-2-pyrid-yl)carbamothio-yl]benzamide.

Yamin B M BM Yousuf S S Yusof M S M MS Jusoh R H RH

Acta crystallographica. Section E, Structure reports online 20080410 Pt 5

In the title compound, C(15)H(15)N(3)OS, the thio-urea group is stabilized by an intra-molecular hydrogen bond between the carbonyl O atom and the thio-amide group. A C-H⋯N intramolecular hydrogen bond is also present. Mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯S hydrogen bonds. ...[more]

PMID: 21202322

Similar Datasets

N-(Diphenyl-carbamothio-yl)-3-methyl-benzamide.

Project description:The synthesis of the title compound, C(21)H(18)N(2)OS, involves the reaction of 3-methyl-benzoyl chloride with potassium thio-cyanate in dry acetone followed by condensation of the 3-methyl-benzoyl isothio-cyanate with diphenyl-amine. The carbonyl [C-O = 1.215?(2)?Å] and thio-carbonyl [C-S = 1.6721?(17)?Å] distances indicate that these correspond to double bonds. The short C-N bonds at the center of the mol-ecule reveal the effects of resonance in this part of the mol-ecule. The conformation of the mol-ecule with respect to the thio-carbonyl and carbonyl groups is twisted. The 3-methyl-phenyl and two phenyl rings are also twisted, with dihedral angles of 75.67?(9) and 14.91?(9)°. The phenyl rings are rotated out of the mean plane of the N-C-S-N atoms by 66.87?(8) and 78.40?(9)°. Pairs of mol-ecules are linked into centrosymmetric dimers via inter-molecular N-H?S inter-actions and a C-H?O link also occurs. The dimers are stacked along the a axis.

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N-[(2,4-Dimethyl-phen-yl)carbamothio-yl]-2-methyl-benzamide.

Project description:The title compound, C(17)H(18)N(2)OS, adopts a trans-cis geometry of the thio-urea group which is stabilized by intra-molecular hydrogen bonds between the O atom of the carbonyl group and the H atom of the thio-amide group. A C-H⋯S intramolecular hydrogen bond is also present. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯S hydrogen bonds to form centrosymmetric dimers.

| S-EPMC2961187 | biostudies-literature

2-Iodo-N-(6-methyl-2-pyrid-yl)benzamide.

Project description:The asymmetric unit of the title compound, C(13)H(11)IN(2)O, comprises two crystallographically independent mol-ecules. The dihedral angles between the ring planes are 53.56?(9) and 72.14?(19)° in the two molecules. Pairs of inter-molecular N-H?N hydrogen bonds and I?O inter-actions link neighbouring mol-ecules into two different pairs of dimers, those involving N-H?N interactions having R(2) (2)(8) ring motifs. Short inter-molecular I?O [3.1458?(15)?Å] and I?N [3.4834?(16)?Å] contacts are present. The crystal structure is further stabilized by inter-molecular C-H?? inter-actions [3.565?(2) and 3.629?(2)?Å].

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3-Chloro-N-(diphenyl-carbamothio-yl)benzamide.

Project description:In the title compound, C(20)H(15)ClN(2)OS, the bond lengths and angles in the thio-urea group are typical of thio-urea derivatives. The C-N bond lengths in the center of the mol-ecule are shorter than the normal C-N single bond due to the resonance effects in this part of the mol-ecule. The conformation of the title mol-ecule with respect to the thio-carbonyl and carbonyl groups is twisted, as reflected by the C-N-C-O and C-N-C-N torsion angles of -4.4?(6) and -53.3?(5)°, respectively. Pairs of the mol-ecules are linked into centrosymmetric dimers, stacked along the c axis via inter-molecular N-H?S inter-actions. There are also weak inter-molecular C-H?O and C-H?S contacts in the structure.

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4-Bromo-N-(diethyl-carbamothio-yl)-benzamide.

Project description:The synthesis of the title compound, C(12)H(15)BrN(2)OS, involves the reaction of 4-bromo-benzoyl chloride with potassium thio-cyanate in dry acetone, followed by condensation of 4-bromo-benzoyl isothio-cyanate with diethyl-amine. The carbonyl and thio-carbonyl bond lengths indicate that these correspond to double bonds. The short C-N bond lengths reveal the effects of resonance in this part of the mol-ecule. The conformation of the mol-ecule with respect to the thio-carbonyl and carbonyl units is twisted, with torsion angles of -5.7?(3) and 87.2?(2)°. The N atom of the diethyl-amine group is sp(2)-hybridized: the sum of the angles around the N atom is 359.97?(14)°. The two diethyl groups are twisted in + and - anti-periplanar conformations with angles of -179.89 and 179.92°. In the crystal structure, the mol-ecules form infinite chains via an inter-molecular N-H?O inter-action.

| S-EPMC2968358 | biostudies-literature

N-(Diethyl-carbamothio-yl)-4-nitro-benzamide.

Project description:In the title compound, C(12)H(15)N(3)O(3)S, the 4-nitro and carbonyl groups are nearly coplanar with the benzene ring [C-C-N-O = -175.72 (14) and C-C-C-O = 172.75 (14)°]. The diethyl-carbamothioyl group is twisted significantly from the plane of the benzene ring [C-N-C-N = -89.79 (15)°] with the S atom pointing away from each of these groups [C-N-C-S = 91.12 (14)°]. In the crystal, an inter-molecular N-H⋯O hydrogen bond, which forms an infinite polymeric chain along the c axis, and weak C-H⋯O and C-H⋯S hydrogen bonds are observed.

| S-EPMC2983343 | biostudies-literature

2-Ferrocenyl-N-(2-ferrocenylbenzo-yl)-N-(4-methyl-2-pyrid-yl)benzamide.

Project description:The title compound, [Fe(2)(C(5)H(5))(2)(C(30)H(22)N(2)O(2))], a 2:1 product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-4-methyl-pyridine, forms a twisted mol-ecular structure in the solid state due to steric effects from the two benzene rings ortho-substituted with ferrocenyl and carbonyl-derived groups. A short intra-molecular C-H?? interaction is observed involving a substituted ?(5)-C(5)H(4) ring and an ortho H atom of the benzene ring on the opposite side of the mol-ecule. In the crystal structure, there are no classical hydrogen bonds: inter-actions comprise a short C(6)-H??(C(6)) inter-action involving substituted benzene rings and two C-H?O=C inter-actions per mol-ecule.

| S-EPMC2968647 | biostudies-literature

N-[(4-Carbamoylphen-yl)carbamothio-yl]-2,3,4,5-tetra-fluoro-benzamide.

Project description:In the title compound, C(15)H(9)F(4)N(3)O(2)S, the N,N'-disubstituted thio-urea fragment adopts a cis,trans geometry, stabilized by an intra-molecular N-H⋯O hydrogen bond to the carbonyl O atom of the tetra-fluoro-benzoyl group. The central thio-urea group makes dihedral angles of 47.79 (7) and 35.54 (8)° with the two aromatic rings. In the crystal, mol-ecules are linked via N-H⋯O and N-H⋯S hydrogen bonds into two-dimensional polymeric structures parallel to (100). In turn, π-π stacking inter-actions between tetra-fluoro-benzene and benzene units [centroid-centroid distance = 3.996 (10) Å; dihedral angle = 13.60 (8)°] organize these two-dimensional assemblies into a three-dimensional framework.

| S-EPMC3051937 | biostudies-literature

4-Chloro-N-[N-(6-methyl-2-pyrid-yl)car-bamo-thio-yl]benzamide.

Project description:In the title compound, C(14)H(12)ClN(3)OS, the short exocyclic N-C bond lengths indicate resonance in the thiourea part of the mol-ecule. The title compound is stabilized by an intra-molecular N-H⋯N hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thio-carbonyl group and the pyridine group. Inter-molecular N-H⋯S and C-H⋯O inter-actions are also present.

| S-EPMC2967990 | biostudies-literature

[(Methyl-carbamothio-yl)disulfan-yl]methyl N-methyl-carbamodithio-ate.

Project description:The title compound, C(5)H(10)N(2)S(5), was unintentionally obtained as the product of an attempted synthesis of a methyl-carbamodithioic acid using methyl-amine and carbon disulfide. In the mol-ecule, two dithio-carbamate groups are bridged by a -CH(2)S- unit. The C-S-S-C torsion angle is -90.13 (11)°. The crystal structure is stabilized by N-H⋯S inter-actions between neighbouring mol-ecules. An intra-molecular N-H⋯S hydrogen bond also occurs.

| S-EPMC2983331 | biostudies-literature

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