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5-Acetyl-4-(2-chloro-phen-yl)-6-methyl-3,4-dihydro-pyrimidine-2(1H)-thione.

ABSTRACT: In the title mol-ecule, C(13)H(13)ClN(2)OS, the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 85.6?(1)° with the benzene ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Inter-molecular N-H?O, N-H?S and C-H?S hydrogen bonds are found in the crystal structure. A weak C-H?? inter-action involving the benzene ring also occurs.

SUBMITTER: Anuradha N

PROVIDER: S-EPMC2972027 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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5-Acetyl-4-(2-chloro-phen-yl)-6-methyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Anuradha N N Thiruvalluvar A A Pandiarajan K K Chitra S S Butcher R J RJ

Acta crystallographica. Section E, Structure reports online 20091114 Pt 12

In the title mol-ecule, C(13)H(13)ClN(2)OS, the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 85.6 (1)° with the benzene ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Inter-molecular N-H⋯O, N-H⋯S and C-H⋯S hydrogen bonds are found in the crystal structure. A weak C-H⋯π inter-action involving the benzene ring also occurs. ...[more]

PMID: 21578798

Similar Datasets

5-Acetyl-4-(4-chloro-phen-yl)-6-methyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:In the title mol-ecule, C(13)H(13)ClN(2)OS, the heterocyclic ring adopts a flattened boat conformation, and the plane through the four coplanar atoms makes a dihedral angle of 87.92?(10)° with the benzene ring. The thione, acetyl and methyl groups have equatorial orientations with respect to the attached heterocyclic ring. The chloro-phenyl group has an axial orientation. Inter-molecular N-H?O, N-H?S and C-H?O hydrogen bonds are found in the crystal structure.

| S-EPMC2968427 | biostudies-literature

1-(3-Chloro-phen-yl)-4,4,6-trimethyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:In the title compound, C(13)H(15)ClN(2)S, the dihydro-pyrimidine ring is essentially planar, with a maximum deviation from the least-squares plane of 0.122?(3)?Å for the unsubstitued olefinic C atom. The dihedral angle between the dihydro-pyrimidine and benzene rings is 86.62?(13)°. The crystal structure is stabilized by inter-molecular N-H?S hydrogen bonds, which form centrosymmetric dimers arranged along the c axis.

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1-(4-Chloro-phen-yl)-4,4,6-trimethyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:The dihydro-pyrimidine ring of the title compound, C(13)H(15)ClN(2)S, adopts an envelope conformation with five almost coplanar atoms (r.m.s. deviation = 0.054?Å) and the C atom bearing the two methyl substituents deviating from this plane by 0.441?(2)?Å. The best plane through the five almost coplanar atoms forms a dihedral angle of 89.56?(5)° with the benzene ring. The crystal packing is characterized by centrosymmetric dimers connected by pairs of N-H?S hydrogen bonds.

| S-EPMC2979773 | biostudies-literature

4,4,6-Trimethyl-1-(3-methyl-phen-yl)-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:The asymmetric unit of the title compound, C(14)H(18)N(2)S, contains two independent and conformationally similar mol-ecules, which form cyclic dimers via inter-molecular hydrogen bonds of the type N-H?S [graph set R(2) (2)(8)]. The structure is iso-morphous with that of one of the polymorphs of 4,4,6-tri-methyl-1-phenyl-3,4-dihydro-pyrimidine-2(1H)-thione [Yam-in et al. (2005 ?). Acta Cryst. E61, o55-o57].

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5-Acetyl-4-(4-methoxy-phen-yl)-6-methyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:In the title mol-ecule, C(14)H(16)N(2)O(2)S, the heterocyclic ring adopts an envelope conformation with the plane through the five coplanar atoms making a dihedral angle of 88.99?(4)° with the benzene ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Inter-molecular N-H?S, N-H?O, C-H?O and C-H?S hydrogen bonds are found in the crystal structure.

| S-EPMC2972144 | biostudies-other

1-(3-Fluoro-phen-yl)-4,4,6-trimethyl-3,4-dihydro-pyrimidine-2(1H)-thione.

Project description:In the title compound, C(13)H(15)FN(2)S, the dihydro-pyrimidine ring is essentially planar, with a maximum deviation of 0.086?(3)?Å from the mean plane of the rest of the ring for the dimethyl-ated C atom. The benzene ring is almost perpendicular to the dihydro-pyrimidine ring, with a dihedral angle of 83.97?(14)°. The crystal packing is characterized by centrosymmetric dimers resulting from pairs of inter-molecular N-H?S hydrogen bonds. There are also C-H?? inter-actions.

| S-EPMC3152063 | biostudies-literature

5-Acetyl-4-(2-chloro-phen-yl)-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one.

Project description:In the title mol-ecule, C(13)H(13)ClN(2)O(2), the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 89.16?(5)° with the benzene ring, which adopts an axial orientation. The carbonyl, acetyl and methyl groups each have an equatorial orientation. In the crystal structure, inter-molecular N-H?O hydrogen bonds lead to a tape motif. The H atoms of the methyl group at position 6 are disordered over two positions of opposite orientation.

| S-EPMC2960013 | biostudies-literature

5-Acetyl-4-(4-methoxy-phen-yl)-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one.

Project description:In the title mol-ecule, C(14)H(16)N(2)O(3), the heterocyclic ring adopts a flattened boat conformation, and the plane through its four coplanar atoms makes a dihedral angle of 89.65 (7)° with the benzene ring. The non-H atoms of the carbonyl, acetyl and methyl groups are nearly coplanar with the attached heterocyclic ring. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds are present in the crystal structure.

| S-EPMC2967942 | biostudies-literature

4-[3,4-Dimethyl-1-(4-methyl-phen-yl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methyl-phen-yl)-4,5-dihydro-1H-pyrazol-5-one.

Project description:In the title compound, C(24)H(26)N(4)O(2), the complete mol-ecule is generated by the application of twofold symmetry. The pyrazole ring is approximately planar [r.m.s. deviation = 0.026 Å] and the benzene ring is twisted out of this plane [dihedral angle = 21.94 (7)°]. A twist in the mol-ecule about the central C-C bond [1.566 (3) Å] is also evident [C-C-C-C torsion angle = 44.30 (14)°]. Supra-molecular layers in the bc plane are formed in the crystal packing via C-H⋯O and C-H⋯π inter-actions.

| S-EPMC3343962 | biostudies-literature

7-Chloro-5-(2-ethoxy-phen-yl)-1-methyl-3-propyl-2,6-dihydro-1H-pyrazolo[4,3-d]pyrimidine.

Project description:In the title compound, C(17)H(21)ClN(4)O, the benzene ring is oriented at dihedral angles of 1.59?(3) and 1.27?(3)° with respect to the pyrimidine and pyrazole rings, while the dihedral angle between the pyrimidine and pyrazole rings is 0.83?(3)°. An intra-molecular N-H?O hydrogen bond results in the formation of a planar (r.m.s. deviation 0.004?Å) six-membered ring.

| S-EPMC2970445 | biostudies-literature

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