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5-Propyl-6-(p-tolyl-sulfan-yl)pyrimidine-2,4(1H,3H)-dione.

ABSTRACT: In the title pymiridine-2,4-dione derivative, C14H16N2O2S, the dihedral angle between the six-membered rings is 66.69?(10)°. The mol-ecule is twisted about the Cp-S (p = pyrimidine) bond, with a C-S-C-N torsion angle of -19.57?(16)°. In the crystal, adjacent mol-ecules form inversion dimers through pairs of strong N-H?O hydrogen bonds, generating an R 2 (2)(8) ring motif. The dimers are connected into chains extending along the c-axis direction through additional N-H?O hydrogen bonds.

SUBMITTER: Al-Omary FA

PROVIDER: S-EPMC3998333 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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5-Propyl-6-(p-tolyl-sulfan-yl)pyrimidine-2,4(1H,3H)-dione.

Al-Omary Fatmah A M FA Ghabbour Hazem A HA El-Emam Ali A AA Chidan Kumar C S CS Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20140122 Pt 2

In the title pymiridine-2,4-dione derivative, C14H16N2O2S, the dihedral angle between the six-membered rings is 66.69 (10)°. The mol-ecule is twisted about the Cp-S (p = pyrimidine) bond, with a C-S-C-N torsion angle of -19.57 (16)°. In the crystal, adjacent mol-ecules form inversion dimers through pairs of strong N-H⋯O hydrogen bonds, generating an R 2 (2)(8) ring motif. The dimers are connected into chains extending along the c-axis direction through additional N-H⋯O hydrogen bonds. ...[more]

PMID: 24764894

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6-[(2-Methyl-phen-yl)sulfan-yl]-5-propyl-pyrimidine-2,4(1H,3H)-dione.

Project description:In the title pyrimidine-2,4-dione derivative, C14H16N2O2S, the dihedral angle between the six-membered rings is 77.81?(10)°. The mol-ecule is twisted about the Cp-S (p = pyrimidine) bond, with a C-S-C-N torsion angle of -59.01?(17)°. An intramolecular C-H?S hydrogen bond generates an S(5) ring motif. In the crystal, bifurcated acceptor N-H?O and C-H?O hydrogen bonds generate inversion-related dimers incorporating R 2 (1)(9) and R 2 (2)(8) loops. These dimers are connected into a chain extending along the a-axis direction by a second pair of inversion-related N-H?O hydrogen bonds, forming another R 2 (2)(8) loop. The crystal structure is further stabilized by weak inter-molecular C-H?? inter-actions, generating a three-dimensional network.

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6-(Trifluoro-meth-yl)pyrimidine-2,4(1H,3H)-dione monohydrate.

Project description:The title compound, C(5)H(3)F(3)N(2)O(2)·H(2)O, was prepared by the reaction of ethyl 4,4,4-trifluoro-3-oxobutano-ate with urea. In the crystal, the 6-(trifluoro-meth-yl)pyrimidine-2,4(1H,3H)-dione and water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds. A ring dimer structure is formed by additional inter-molecular N-H⋯O hydrogen bonds.

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Crystal structure of 6-chloro-5-iso-propyl-pyrimidine-2,4(1H,3H)-dione.

Project description:In the mol-ecule of the title compound, C7H9ClN2O2, the conformation is determined by intra-molecular C-H?O and C-H?Cl hydrogen bonds, which generate S(6) and S(5) ring motifs. The isopropyl group is almost perpendicular to the pyrimidine ring with torsion angles of -70.8?(3) and 56.0?(3)°. In the crystal, two inversion-related mol-ecules are linked via a pair of N-H?O hydrogen bonds into R 2 (2)(8) dimers; these dimers are connected into chains extending along the bc plane via an additional N-H?O hydrogen bond and weaker C-H?O hydrogen bonds. The crystal structure is further stabilized by a weak ?-? inter-action [3.6465?(10)?Å] between adjacent pyrimidine-dione rings arranged in a head-to-tail fashion, producing a three-dimensional network.

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5-Fluoro-1-(3-metylbutano-yl)pyrimidine-2,4(1H,3H)-dione.

Project description:The 3-methyl-butanoyl group and the 5-fluoro-uracil unit of the title compound, C(9)H(11)FN(2)O(3), are essentially coplanar, with the carbonyl group oriented towards the ring CH group and away from the nearer ring carbonyl group. The 3-methyl-butanoyl (C=)C-N-C=O torsion angle of 9.6?(2)° is comparable to that in structurally related compounds. In the solid state, two inversion-related mol-ecules form N-H?O hydrogen bonds to generate an inter-molecular R(2) (2)(8) ring. The crystal structure also diplays intra- and inter-molecular C-H?O inter-actions.

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Project description:The title compound, C(14)H(16)N(4)O(2)S, is a Schiff base derivative of 2-(methyl-sulfan-yl)benzaldehyde. The configuration about the C=N double bond is E. The heterocyclic ring is essentially planar (τ = 3.1°) and makes a dihedral angle of 12.24 (7)° with the benzene ring. An intra-molecular N-H⋯S hydrogen bond is observed. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link mol-ecules into layers perpendicular to [101]. The closest distance between the centroids of two heterocyclic rings was found to be 3.5268 (8) Å.

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7-(Benzyl-sulfan-yl)-5-(2-methoxy-phen-yl)-1,3-dimethyl-5,6-dihydro-pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione.

Project description:In the mol-ecule of the title compound, C(22)H(22)N(4)O(3)S, the benzene and phenyl rings are oriented at a dihedral angle of 88.72?(4)°. The other two rings have flattened-boat conformations. In the crystal structure, inter-molecular N-H?O hydrogen bonds link the mol-ecules.

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5-Fluoro-1-(penta-noyl)pyrimidine-2,4(1H,3H)-dione.

Project description:The penta-noyl group and the 5-fluoro-uracil moiety of the title compound, C(9)H(11)FN(2)O(3), are essentially coplanar, with the penta-noyl carbonyl group oriented towards the ring CH group and away from the nearer ring carbonyl group. In the crystal structure, two inversion-related mol-ecules form a dimer structure, in which two N-H?O hydrogen bonds generate an inter-molecular R(2) (2)(8) ring. In addition, there are intra- and inter-molecular C-H?O inter-actions.

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A second monoclinic polymorph of 6-amino-1,3-dimethyl-5-[(E)-2-(methyl-sulfan-yl)benzyl-idene-amino]-pyrimidine-2,4(1H,3H)-dione.

Project description:A new monoclinic form of the title compound, C(14)H(16)N(4)O(2)S, has been identified unexpectedly during an attempt to synthesize a coordination compound. The heterocyclic ring is essentially planar (r.m.s. deviation = 0.005?Å) and makes a dihedral angle of 8.77?(5)° with the benzene ring. This is in contrast to 12.24?(7)° reported for the first monoclinic polymorph [Booysen et al. (2011 ?). Acta Cryst. E67, o1592]. An intra-molecular N-H?S hydrogen bond is observed. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into zigzag chains along the b axis. The closest distance between the centroids of symmetry-related heterocyclic rings is 3.5161?(6)?Å.

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1,3-Bis(4-methyl-benz-yl)pyrimidine-2,4(1H,3H)-dione.

Project description:In the title mol-ecule, C(20)H(20)N(2)O(2), the central pyrimidine ring forms dihedral angles of 71.9?(1) and 69.8?(1)° with the two benzene rings. In the crystal, weak inter-molecular C-H?O hydrogen bonds link mol-ecules into centrosymmetric dimers. The crystal packing exhibits also ?-? inter-actions as indicated by short distances of 3.674?(2)?Å between the centroids of the pyrimidine rings of neighbouring mol-ecules.

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1-(4-tert-Butyl-benz-yl)pyrimidine-2,4(1H,3H)-dione.

Project description:The asymmetric unit of the title compound, C(15)H(18)N(2)O(2), contains two independent mol-ecules with essentially identical geometries and conformations. The dihedral angles between the benzene and pyrimidine rings in the two mol-ecules are 89.96?(11) and 73.91?(11)°. The six methyl groups are disordered over two sets of sites, with site occupancies of 0.545?(4):0.455?(4) and 0.542?(7):0.458?(7) in the two mol-ecules. The crystal structure is stabilized by N-H?O hydrogen bonds.

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