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

ABSTRACT: 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.

SUBMITTER: Booysen I

PROVIDER: S-EPMC3151916 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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

Booysen Irvin I Muhammed Ismail I Soares Anna A Gerber Thomas T Hosten Eric E Betz Richard R

Acta crystallographica. Section E, Structure reports online 20110611 Pt 7

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 f ...[more]

PMID: 21837000

Similar Datasets

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.

| S-EPMC3213476 | biostudies-literature

(E)-6-Amino-1,3-dimethyl-5-[(pyridin-2-yl-methyl-idene)amino]-pyrimidine-2,4(1H,3H)-dione.

Project description:In the title compound, C(12)H(13)N(5)O(2), a Schiff-base-derived chelate ligand, the non-aromatic heterocycle and its substituents essentially occupy one common plane (r.m.s. of fitted non-H atoms = 0.0503 Å). The N=C bond is E-configured. Intra-cyclic angles in the pyridine moiety cover the range 117.6 (2)-124.1 (2)°. Intra- and inter-molecular N-H⋯N and N-H⋯O hydrogen bonds are observed in the crystal structure, as are intra- and inter-molecular C-H⋯O contacts which, in total, connect the mol-ecules into a three-dimensional network. The shortest ring-centroid-to-ring-centroid distance of 3.5831 (14) Å is between the two different types of six-membered rings.

| S-EPMC3200715 | biostudies-literature

6-[(Dimethyl-amino)methyl-ene-amino]-1,3-dimethyl-pyrimidine-2,4(1H,3H)-dione dihydrate.

Project description:Uracil, the pyrimidine nucleobase, which combined with adenine forms one of the major motifs present in the biopolymer RNA, is also involved in the self-assembly of RNA. In the title compound, C(9)H(14)N(4)O(2)·2H(2)O, the asymmetric unit contains one dimethyl-amino-uracil group and two water mol-ecules. The plane of the N=C-NMe(2) side chain is inclined at 27.6?(5)° to the plane of the uracil ring. Both water mol-ecules form O-H?O hydrogen bonds with the carbonyl O atoms of the uracil group. Additional water-water hydrogen-bond inter-actions are also observed in the crystal structure. The O-H?O hydrogen bonds lead to the formation of a two-dimensional hydrogen-bonded network cage consisting of two dimethyl-amino-uracil groups and six water mol-ecules.

| S-EPMC2960636 | biostudies-literature

6-Amino-1,3-dimethyl-5-[(E)-2-(methyl-sulfan-yl)benzyl-idene-amino]-pyrimidine-2,4(1H,3H)-dione-1,3,7,9-tetra-methyl-pyrimido[5,4-g]pteridine-2,4,6,8-tetrone (1/1).

Project description:In the title co-crystal, C(12)H(12)N(6)O(4)·C(14)H(16)N(4)O(2)S, both mol-ecules are essentially planar [maximum deviations = 0.129 (1) and 0.097 (1) Å, respectively]. The tricyclic and Schiff base mol-ecules are alternately stacked along the a axis and are linked by π-π inter-actions with centroid-centroid distances of 3.5170 (16) and 3.6576 (17) Å. An intra-molecular C-H⋯O hydrogen bond and a C-H⋯S contact occur in the Schiff base molecule. In the crystal, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

| S-EPMC3414272 | biostudies-literature

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.

| S-EPMC2960738 | biostudies-literature

2-[(E)-(2,4-Dichloro-benzyl-idene)amino]-isoindoline-1,3-dione.

Project description:In the title compound, C(15)H(8)Cl(2)N(2)O(2), the mol-ecule adopts an E configuration about the central C=N double bond. The isoindoline ring is essentially planar, with a maximum deviation of 0.019 (2) Å. The dihedral angle between the isoindoline ring and the dichloro-substituted benzene ring is 6.54 (9)°. An intra-molecular C-H⋯O hydrogen bond occurs. A short Cl⋯Cl contact of 3.4027 (9) Å is present in the crystal structure. The crystal packing is further stabilized by weak C-H⋯π inter-actions.

| S-EPMC3151809 | biostudies-literature

1,3-Dimethyl-5-(2-methyl-benzyl-idene)pyrimidine-2,4,6(1H,3H,5H)-trione.

Project description:In the title compound, C(14)H(14)N(2)O(3), the dihedral angle between the pyrimidine and benzene rings is 14.9 (1)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal structure exhibits a weak inter-molecular π-π inter-action [centroid-centroid distance = 3.575 (3) Å].

| S-EPMC2970469 | biostudies-literature

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

Project description: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.

| S-EPMC3998333 | biostudies-literature

6,6'-Diamino-1,1',3,3'-tetra-methyl-5,5'-(4-chloro-benzyl-idene)bis-[pyrimidine-2,4(1H,3H)-dione].

Project description:The title compound, C(19)H(21)ClN(6)O(4), is a 1:2 adduct of p-chloro-benzaldehyde and uracil. It crystallizes with two mol-ecules in the asymmetric unit. The two uracil units in the same mol-ecule are connected by a pair of strong N-H⋯O hydrogen bonds. The packing is stabilized by N-H⋯O, C-H⋯O and C-H⋯N inter-actions.

| S-EPMC2970351 | biostudies-literature

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 π-π inter-actions as indicated by short distances of 3.674 (2) Å between the centroids of the pyrimidine rings of neighbouring mol-ecules.

| S-EPMC2980275 | biostudies-literature

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