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4-[(E)-(4-Hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

ABSTRACT: The title compound, C10H10N4OS, is nearly planar with the mean planes of the hy-droxy-benzyl and triazole rings inclined at an angle of only 3.2 (7)°. In the crystal, O-H⋯N hydrogen bonds between the hy-droxy group and the triazole ring in concert with weak N-H⋯S inter-molecular inter-actions between the triazole ring and thione group form chains along [-210] enclosing R 2 (2)(8) graph-set motifs. A weak intra-molecular C-H⋯S inter-action and inter-molecular π-π inter-actions [centroid-centroid distance = 3.5990 (15) Å] are also observed.

SUBMITTER: Sarojini BK

PROVIDER: S-EPMC4051099 | biostudies-literature |

REPOSITORIES: biostudies-literature

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4-[(5-Bromo-2-hy-droxy-benzyl-idene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C11H11BrN4OS, crystallized as a racemic twin with two symmetry-independent mol-ecules in the asymmetric unit. The dihedral angles between the benzene and triazole rings of the two independent mol-ecules are 56.41?(18) and 54.48?(18)°. An intra-molecular O-H?N hydrogen bond occurs in each mol-ecule. In the crystal, pairs of symmetry-independent mol-ecules are linked by pairs of almost linear N-H?S hydrogen bonds, forming cyclic dimers characterized by an R 2 (2)(8) motif. There are weak ?-? inter-actions between the benzene rings of symmetry-independent mol-ecules, with a centroid-centroid distance of 3.874?(3)?Å.

| S-EPMC4158482 | biostudies-literature

Crystal structure of (E)-3-(4-hy-droxy-benz-yl)-4-{[4-(methyl-sulfan-yl)benzyl-idene]amino}-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C17H16N4OS2, the triazole and methyl-thio-benzyl-idene rings are nearly coplanar, making a dihedral angle of 6.52 (12)°. An intra-molecular C-H⋯S hydrogen bond forms an S(6) ring motif. The hy-droxy-benzyl ring is almost normal to the triazole and methyl-thio-benzyl-idene rings, making dihedral angles of 78.56 (12) and 84.79 (11)°, respectively. In the crystal, mol-ecules are linked through O-H⋯N and N-H⋯O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked via C-H⋯N hydrogen bonds, forming a three-dimensional structure. In addition, a short π-π inter-action is observed [inter-centroid distance = 3.764 (3) Å], involving inversion-related methyl-thio-benzyl-idene rings.

| S-EPMC4719935 | biostudies-literature

4-[(E)-(4-Fluoro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the asymmetric unit of the title compound, C(10)H(9)FN(4)S, there are two independent mol-ecules in which the dihedral angles between the 1,2,4-triazole and benzene rings are 36.85?(10) and 7.81?(10)°. In the crystal, N-H?S inter-actions link pairs of independent mol-ecules into dimers. There are also ?-? inter-actions between the triazole and benzene rings of inversion-related pairs of the more planar mol-ecule [centroid-centroid distance = 3.6430?(13)?Å].

| S-EPMC3379215 | biostudies-literature

3-Ethyl-4-[(E)-2-methyl-benzyl-idene-amino]-1H-1,2,4-triazole-5(4H)-thione.

Project description:Crystals of the title compound, C(12)H(14)N(4)S, were obtained from a condensation reaction of 4-amino-3-ethyl-1H-1,2,4-triazole-5(4H)-thione and 2-methyl-benzaldehyde. In the mol-ecular structure, there is a short N=C double bond [1.255?(2)?Å], and the benzene and triazole rings are located on opposite sites of this double bond. The two rings are approximately parallel to each other, the dihedral angle being 1.75?(11)°. A partially overlapped arrangement is observed between the nearly parallel triazole and benzene rings of adjacent mol-ecules; the perpendicular distance of the centroid of the triazole ring from the benzene ring is 3.482?Å, indicating the existence of ?-? stacking in the crystal structure.

| S-EPMC2962033 | biostudies-literature

4-[(E)-(4-Chloro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C10H9ClN4S, the dihedral angle between the mean planes of the phenyl and 1H-1,2,4-triazole-5(4H)-thione rings is 25.3 (9)°. The latter ring is essentially planar, with maximum deviations of 0.010 and -0.010 Å for the ring N atom in the 4-position and ring C atom bearing the methyl group, respectively. An intra-molecular C-H⋯S contact occurs. In the crystal, pairs of weak N-H⋯S inter-actions link the mol-ecules into inversion dimers in the ac plane, forming R 2 (2)(8) graph-set motifs. In addition, weak π-π inter-actions [centroid-centroid distances = 3.3463 (14) and 3.6127 (13)Å] are observed.

| S-EPMC3914094 | biostudies-literature

The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thio-nes, including a second polymorph of 4-[(E)-(5-bromo-2-hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported. The structure of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C3H6N4S, (I), has been redetermined with an improved model for the H atoms: the non-H atoms of (I) all lie on mirror planes in space group Pbcm, and the H atoms of the methyl group are disordered over two sets of reflection-related atomic sites having occupancy 0.5: two independent N-H?S hydrogen bonds link the mol-ecules of compound (I) into complex sheets. The non-H atoms in the mol-ecules of 4-[(E)-(3,4-di-meth-oxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-tri-azol-5(4H)-thione, C12H14N4O2S, (II), despite lying in general positions are close to planar, with a dihedral angle between the two rings of 6.31?(10)°: the mol-ecules of compound (II) are linked by a three-centre N-H?(O)2 hydrogen bond into a C(10)C(11)[R 1 (2)(5)] chain of rings. A second polymorph of 4-[(E)-(5-bromo-2-hy-droxy-5-bromo-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C10H9BrN4OS, (III), has been identified; the non-H atoms are nearly co-planar with a dihedral angle between the two rings of 1.9?(4)°. There is an intra-molecular O-H?N hydrogen bond and the mol-ecules are linked by N-H?S hydrogen bonds, forming centrosymmetric R 2 (2)(8) dimers. Comparisons are made with some related structures.

| S-EPMC4555427 | biostudies-literature

3-Methyl-4-{(E)-[4-(methyl-sulfan-yl)benzyl-idene]amino}-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title mol-ecule, C11H12N4S2, the dihedral angle between the triazole and benzene rings is 21.31?(5)°. A weak intra-molecular C-H?S hydrogen bond generates an S(6) ring motif. In the crystal, pairs of N-H?S hydrogen bonds form inversion dimers. In addition, ?-? inter-actions are observed between the benzene rings, with a centroid-centroid separation of 3.7599?(11)?Å.

| S-EPMC3648251 | biostudies-literature

4-(5-Bromo-2-hydroxy-benzyl-idene-amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C(10)H(9)BrN(4)OS, the triazole ring forms a dihedral angle of 72.05?(14)° with the benzene ring. The conformation of the mol-ecule is stabilized by intra-molecular O-H?·N hydrogen bonding. The crystal packing is determined by inter-molecular N-H?S inter-actions, a short Br?S contact of 3.4464?(13)?Å and ?-? stacking of the triazole rings and of the benzene rings (centroid-centroid distances of 3.4109 and 3.569?Å, respectively).

| S-EPMC2960248 | biostudies-literature

4-[(5-Bromo-2-hy-droxy-benzyl-idene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The asymmetric unit of the title compound, C(12)H(13)BrN(4)OS, contains two independent mol-ecules in which the dihedral angles between the triazole and benzene rings are 2.9?(3) and 7.5?(3)°. The thione group is of the form R(2)C=S. An intra-molecular O-H?N hydrogen bond occurs in each mol-ecule. The crystal structure features weak N-H?S inter-actions and ?-? stacking of the benzene rings [centroid-centroid distance = 3.667?(3)?Å].

| S-EPMC3379270 | biostudies-other

4-[(5-Chloro-2-hy-droxy-benzyl-idene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C11H11ClN4OS, crystallizes with two mol-ecules, A and B, in the asymmetric unit in which the dihedral angles between the triazole and benzene rings are 54.6?(3) and 56.0?(3)°. Both mol-ecules feature an intra-molecular O-H?N hydrogen bond, which generates an S(6) ring. In the crystal, A-B dimers are linked by pairs of weak C-H?S hydrogen bonds along with ?-? stacking inter-actions between the triazole rings [centroid-centroid separations = 3.631?(3) and 3.981?(4)Å]. N-H?S hydrogen bonds link the dimers into [100] chains, which feature R 2 (2)(8) loops.

| S-EPMC4011212 | biostudies-other

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