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Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-chloro-acetamide.

ABSTRACT: In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83?(12)°. The O=C-C-Cl torsion angle is 46.4?(3)° and an intra-molecular C-H?O inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by N-H?O, N-H?N and C-H?N hydrogen bonds, generating sheets lying parallel to (120).

SUBMITTER: Mohamed SK

PROVIDER: S-EPMC4350726 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-chloro-acetamide.

Mohamed Shaaban K SK Knight Kyle S KS Akkurt Mehmet M Hussein Bahgat R M BR Albayati Mustafa R MR

Acta crystallographica. Section E, Crystallographic communications 20150213 Pt 3

In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83 (12)°. The O=C-C-Cl torsion angle is 46.4 (3)° and an intra-molecular C-H⋯O inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O, N-H⋯N and C-H⋯N hydrogen bonds, generating sheets lying parallel to (120). ...[more]

PMID: 25844231

Similar Datasets

Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]acetamide hemihydrate.

Project description:The title compound, C9H10N4OS·0.5H2O, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit, together with a water mol-ecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95?(16)° in mol-ecule A and by 1.77?(16)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked by two N-H?Ocarbon-yl hydrogen bonds, forming a dimer. The dimers are linked via N-H?N hydrogen bonds, forming ribbons that are linked by N-H?Owater hydrogen bonds to form sheets parallel to (110). The sheets are linked by O-H?N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel ?-? inter-actions [inter-centroid distance = 3.734?(2)?Å, inter-planar distance = 3.3505?(11)?Å and slippage = 1.648?Å], forming a three-dimensional structure.

| S-EPMC4350750 | biostudies-literature

Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-(cyclo-hexyl-sulfan-yl)acetamide.

Project description:In the title mol-ecule, C15H20N4OS2, the acetamido fragment is nearly coplanar with the pyridyl ring [C-N-C-C torsion angle = -4.1?(2)°], while the cyclo-hexyl-sulfanyl portion protrudes from this plane [N-C-C-S torsion angle = -40.8?(6)°]. In the crystal, alternating pairwise N-H?O and N-H?N hydrogen bonds across inversion centres form chains along [101], which are associated into stepped layers via offset ?-? stacking between pyridyl rings [centroid-centroid distance = 3.566?(1)?Å]. The cyclo-hexyl group and the two atoms of the S-C bond attached to it are disordered over two sets of sites with site-occupancy factors of 0.8845?(18) and 0.1155?(18).

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Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methyl-sulfan-yl)phen-yl]acetamide.

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Crystal structures of <i>N</i>-(4-chloro-phen-yl)-2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]acetamide and <i>N</i>-(3-chloro-phen-yl)-2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]acetamide.

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| S-EPMC5382600 | biostudies-literature

Crystal structures and Hirshfeld surface analyses of 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]-N-(pyrazin-2-yl)acetamide.

Project description:In the title compounds, C11H12N6OS (I) and C10H11N7OS (II), the di-amino-pyrimidine ring makes dihedral angles of 71.10?(9)° with the pyridine ring in (I) and 62.93?(15)° with the pyrazine ring in (II). The ethanamine group, -CH2-C(=O)-NH- lies in the plane of the pyridine and pyrazine rings in compounds (I) and (II), respectively. In both compounds, there is an intra-molecular N-H?N hydrogen bond forming an S(7) ring motif and a short C-H?O inter-action forming an S(6) loop. In the crystals of both compounds, mol-ecules are linked by pairs of N-H?N hydrogen bonds, forming inversion dimers with R22(8) ring motifs. In (I), the dimers are linked by N-H?O and N-H?N hydrogen bonds, forming layers parallel to (1[Formula: see text] [Formula: see text]). The layers are linked by offset ?-? inter-actions [inter-centroid distance = 3.777?(1)?Å], forming a three-dimensional supra-molecular structure. In (II), the dimers are linked by N-H?O, N-H?N and C-H?O hydrogen bonds, also forming a three-dimensional supra-molecular structure.

| S-EPMC5947495 | biostudies-literature

Crystal structure of (2-chloro-eth-yl)[2-(methyl-sulfan-yl)benz-yl]ammonium chloride.

Project description:In the title mol-ecular salt, C10H15ClNS(+)·Cl(-), the cation is [R'R"NH2](+), where R' is 2-MeS-C6H4CH2- and R" is -CH2CH2Cl, and the anion is Cl(-). In the cation, the N atom is protonated with sp (3)-hybridization and with a tetra-hedral geometry. In the crystal, the anions are connected to the cations through two pairs of N-H?Cl hydrogen bonds, generating a four-centred inversion dimer with an R 4 (2)(8) ring motif.

| S-EPMC4459316 | biostudies-literature

N-(4-Chloro-pyridin-2-yl)-N-(4-methyl-phenyl-sulfon-yl)acetamide.

Project description:The crystal structure of the title compound, C(14)H(13)ClN(2)O(3)S, features a three-dimensional network stabilized by inter-molecular C-H?O hydrogen bonds between the mol-ecules. The 4-methyl-phenyl-sulfonyl ring forms a dihedral angle of 30.6?(1)° with the 4-chloro-pyridine ring.

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2-Chloro-N-methyl-N-[2-(methyl-amino)-phen-yl]acetamide.

Project description:The title compound, C(10)H(13)ClN(2)O, was obtained as a by-product in the reaction of 2-chloro-methyl-1H-benzimidazole, dimethyl sulfate and toluene to synthesise 2-chloro-methyl-1-methyl-benzimidazole. The dihedral angle between the benzene ring and the acetamide group is 89.72 ?(6)° while that between the aromatic ring and the chloracetyl group is 84.40?(4)°. In the crystal, adjacent mol-ecules are linked by pairs of N-H?O hydrogen bonds into inversion dimers.

| S-EPMC3569763 | biostudies-literature

Ethyl 2-[({[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]carbamo-yl}meth-yl)sulfan-yl]acetate monohydrate.

Project description:The title compound, C13H16N4O3S2·H2O, crystallizes in a 'folded' conformation with the ester group lying over the carbamoyl moiety, with one solvent water mol-ecule. The mol-ecular conformation is stabilized by an intra-molecular C-H?O hydrogen bond, and an N-H?O hydrogen-bonding inter-action involving the lattice water mol-ecule. The packing involves N-H?N, N-H?O, O-H?N and O-H?O hydrogen bonds and consists of tilted layers running approximately parallel to the c axis, with the ester groups on the outer sides of the layers and with channels running parallel to (101).

| S-EPMC4120541 | biostudies-other

2-[(4,6-Di-amino-pyrimidin-2-yl)sulfan-yl]-N-(2-methyl-phen-yl)acetamide.

Project description:In the title compound, C13H15NOS, the plane of the pyrimidine ring makes a dihedral angle of 54.73?(9)° with that of the o-tolyl ring. The mol-ecule adopts an extended conformation, which is evident from the C-C(=O)-N-Car (ar = aromatic) torsion angle of 178.42?(15)°. In the crystal, mol-ecules are linked via pairs of N-H?N hydrogen bonds, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked by N-H?O and C-H?O hydrogen bonds, with the O atom accepting three such interactions, forming sheets parallel to (100).

| S-EPMC4158502 | biostudies-literature

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