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Ethyl 4-(4-chloro-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

ABSTRACT: In the title compound, C(14)H(15)ClN(2)O(2)S, the tetra-hydro-pyrimidine ring adopts a twisted boat conformation with the carbonyl group in an s-trans conformation with respect to the C=C double bond of the six-membered tetra-hydro-pyrimidine ring. The mol-ecular conformation is determined by an intra-molecular C-H?? inter-action. The crystal structure is further stabilized by inter-molecular N-H?O mol-ecular chains and centrosymmetric N-H?S dimers.

SUBMITTER: Nayak SK

PROVIDER: S-EPMC2970428 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Ethyl 4-(4-chloro-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Nayak Susanta K SK Venugopala K N KN Chopra Deepak D Govender Thavendran T Kruger Hendrik G HG Maguire Glenn E M GE Guru Row T N TN

Acta crystallographica. Section E, Structure reports online 20090926 Pt 10

In the title compound, C(14)H(15)ClN(2)O(2)S, the tetra-hydro-pyrimidine ring adopts a twisted boat conformation with the carbonyl group in an s-trans conformation with respect to the C=C double bond of the six-membered tetra-hydro-pyrimidine ring. The mol-ecular conformation is determined by an intra-molecular C-H⋯π inter-action. The crystal structure is further stabilized by inter-molecular N-H⋯O mol-ecular chains and centrosymmetric N-H⋯S dimers. ...[more]

PMID: 21577965

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Ethyl 4-(4-cyano-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(15)H(15)N(3)O(2)S, contains two independent mol-ecules corresponding to the R and S enanti-omers. The dihydro-pyrimidinone rings adopt a flattened boat conformation. One of the ethyl groups is disordered over two orientations with occupancy factors of 0.700 (7) and 0.300 (7). In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen-bonding inter-actions into one-dimensional chains along the c-axis direction. The chains are further connected by N-H⋯S hydrogen bonds, forming a three-dimensional network.

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Project description:In the title compound, C14H14Cl2N2O3, the chloro-phenyl ring makes a dihedral angle of 87.08?(9)° with the tetra-hydro-pyrimidine ring. There is a short intra-molecular C-H?O contact present. In the crystal, mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked via a second pair of N-H?O hydrogen bonds, this time enclosing an R (4) 4(20) ring motif, forming ribbons along [100]. The ribbons are linked via C-H?O hydrogen bonds, forming sheets lying parallel to (001). The terminal ethyl group is disordered over two positions with an occupancy ratio of 0.654?(17):0.346?(17).

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Project description:A new Biginelli compound, C(18)H(25)BN(2)O(4)S(2), containing a boronate ester group was synthesized from a lithium bromide-catalysed reaction. The compound crystallizes with two independent mol-ecules in the asymmetric unit that differ mainly in the conformation of the ester functionality. The crystal structure is stabilized by inter-molecular N-H⋯O and N-H⋯S hydrogen bonds involving the 3,4-dihydro-pyrimidine-2(1H)-thione NH groups as donors and the carbonyl O and thio-phene S atoms as acceptors.

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Ethyl 4-(3-bromo-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title compound, C(14)H(15)BrN(2)O(3), the dihydro-pyrimidin-one ring adopts a boat conformation. In the crystal, adjacent mol-ecules are linked through N-H?O hydrogen bonds forming an R(2) (2)(8) ring motif and generating a zigzag chain extending in [010].

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Ethyl 4-(2,4-difluoro-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title compound, C(14)H(14)F(2)N(2)O(3), the dihydro-pyrimidin-one ring adopts a flattened boat conformation. The difluoro-phenyl group is disordered over two orientations with occupancies of 0.544 (3) and 0.456 (3). The methoxy-carbonyl group is disordered over two positions with occupancies of 0.580 (8) and 0.420 (8). In the crystal, mol-ecules are linked into centrosymmetric dimers by paired N-H⋯O hydrogen bonds and the dimers are linked into a ribbon-like structure along [100] by further N-H⋯O hydrogen bonds.

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Ethyl 4-(4-hydroxy-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate monohydrate.

Project description:In the title compound, C(14)H(16)N(2)O(4)·H(2)O, the dihedral angles between the planes of the 4-hydroxy-phenyl and ester groups with the plane of the six-membered tetra-hydro-pyrimidine ring are 87.3?(1) and 75.9?(1)°, respectively. The crystal structure is stabilized by O-H?O and N-H?O hydrogen bonding between the water mol-ecule and the organic functionalities.

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