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N-(2-Chloro-phen-yl)-2-(4,6-dimethyl-pyrimidin-2-ylsulfan-yl)acetamide.

ABSTRACT: In the title compound, C(14)H(14)ClN(3)OS, the 4,6-dimethyl-pyrimidine ring and the chloro-benzene ring subtend a dihedral angle of 80.0?(2)°. The length of the Csp(2)-S bond is significantly shorter than that of the Csp(3)-S bond. The crystal structure is stabilized by inter-molecular N-H?O, C-H?O and C-H?N hydrogen bonding, and C-H?? inter-actions.

SUBMITTER: Li Q

PROVIDER: S-EPMC2977659 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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N-(2-Chloro-phen-yl)-2-(4,6-dimethyl-pyrimidin-2-ylsulfan-yl)acetamide.

Li Qiang Q Wang Wei W Wang Hui H Gao Yan Y Qiu Hong H

Acta crystallographica. Section E, Structure reports online 20090402 Pt 5

In the title compound, C(14)H(14)ClN(3)OS, the 4,6-dimethyl-pyrimidine ring and the chloro-benzene ring subtend a dihedral angle of 80.0 (2)°. The length of the Csp(2)-S bond is significantly shorter than that of the Csp(3)-S bond. The crystal structure is stabilized by inter-molecular N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonding, and C-H⋯π inter-actions. ...[more]

PMID: 21584002

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2-(4,6-Dimethyl-pyrimidin-2-ylsulfan-yl)-N-phenyl-acetamide.

Project description:In the title compound, C(14)H(15)N(3)OS, the phenyl ring is almost perpendicular to the dimethyl-pyrimidine group, with a dihedral angle of 88.1 (3)°. The Csp(2)-S bond of 1.759 (3) Å is significantly shorter than the Csp(3)-S bond of 1.795 (3) Å due to the p-π conjugation.

| S-EPMC2960928 | biostudies-literature

2-(4,6-Dimethyl-pyrimidin-2-ylsulfan-yl)-N-(4-methyl-pyridin-2-yl)acetamide.

Project description:The non-H atoms of the title mol-ecule, C(14)H(16)N(4)OS, are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two aromatic rings is 2.4 (2)°. An intra-molecular C-H⋯O hydrogen bond is observed. The mol-ecules exist as N-H⋯N hydrogen-bonded centrosymmetric dimers.

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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.

Project description:The title compounds, C12H12ClN5OS, (I), and C12H12ClN5OS, (II), are 2-[(di-amino-pyrimidin-2-yl)sulfan-yl]acetamides. Compound (II), crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In each of the mol-ecules, in both (I) and (II), an intra-molecular N-H⋯N hydrogen bond forms an S(7) ring motif. The pyrimidine ring is inclined to the benzene ring by 42.25 (14)° in (I), and by 59.70 (16) and 62.18 (15)° in mol-ecules A and B, respectively, of compound (II). In the crystal of (I), mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via bifurcated N-H⋯O and C-H⋯O hydrogen bonds, forming corrugated layers parallel to the ac plane. In the crystal of (II), the A mol-ecules are linked through N-H⋯O and N-H⋯Cl hydrogen bonds, forming layers parallel to (100). The B mol-ecules are also linked by N-H⋯O and N-H⋯Cl hydrogen bonds, also forming layers parallel to (100). The parallel layers of A and B mol-ecules are linked via N-H⋯N hydrogen bonds, forming a three-dimensional structure.

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N-(4,6-Dimeth-oxy-pyrimidin-2-yl)-2-(3-methyl-phen-yl)acetamide.

Project description:In the title compound, C(15)H(17)N(3)O(3), the dihedral angle between the pyrimidine and benzene rings is 87.0?(7)°. In the crystal, mol-ecules are linked into inversion dimers with R(2) (2)(8) graph-set motifs by a pair of N-H?O hydrogen bonds. Weak C-H?O hydrogen bonds and inter-molecular ?-? inter-actions [centroid-centroid distance = 3.544?(1)?Å] are also observed.

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2-Chloro-N-(2,4-dimethyl-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the structure of the title compound, C(10)H(12)ClNO, is syn to the ortho methyl group, similar to that observed with respect to the meta methyl group in 2-chloro-N-(3-methyl-phen-yl)acetamide and the ortho-chloro group in 2-chloro-N-(2-chloro-phen-yl)acetamide. The geometric parameters are similar to those of other acetanilides. The mol-ecules are linked into chains through inter-molecular N-H?O hydrogen bonds.

| S-EPMC2915041 | biostudies-literature

2-Chloro-N-(3,5-dimethyl-phen-yl)acetamide.

Project description:The conformation of the C=O bond in the structure of the title compound, C(10)H(12)ClNO, is anti to the N-H bond and to the C-Cl bond in the side chain in all four independent mol-ecules comprising the asymmetric unit. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains.

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2-Chloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:The conformation of the C=O bond in the structure of the title compound, C(10)H(12)ClNO, is anti to the N-H bond and to the methyl-ene H atoms in the side chain in both the independent mol-ecules comprising the asymmetric unit. However, the conformation of the N-H bond is syn to the meta-methyl substituent in the aromatic ring of one of the mol-ecules and anti in the other mol-ecule. The two independent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonding into chains parallel to the b axis.

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2-Chloro-N-(2,6-dimethyl-phen-yl)acetamide.

Project description:The crystal structure of the title compound (26DMPCA), C(10)H(12)ClNO, is closely related to those of side-chain-unsubstituted N-(2,6-dimethyl-phen-yl)acetamide and side-chain-substituted 2,2,2-trichloro-N-(2,6-dimethyl-phen-yl)-acet-amide and N-(2,6-dimethyl-phen-yl)-2,2,2-trimethylacet-amide, with slightly different bond parameters. The mol-ecules in 26DMPCA are linked into chains through N-H⋯O hydrogen bonding.

| S-EPMC2915338 | biostudies-literature

N-[2-Chloro-6-(4-chloro-6-methoxy-pyrimidin-2-ylsulfan-yl)benz-yl]-3,4-dimethyl-aniline.

Project description:In the title mol-ecule, C(20)H(19)Cl(2)N(3)OS, the dihedral angle between the two benzene rings is 79.3?(7)°. The 4-chloro-6-methoxy-pyrimidine group is rotationally disordered over two sites by approximately 180°, the ratio of the refined occupancies being 0.6772?(15):0.3228?(15). Both disorder components of disorder are involved in intra-molecular N-H?N hydrogen bonds.

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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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