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Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione.

ABSTRACT: In the title compound, C12H12N6S, the dihedral angles between the central pyrazole ring and the pendant triazole and benzene rings are 68.01?(4) and 59.83?(9)°, respectively. In the crystal, mol-ecules are linked by N-H?N and N-H?S hydrogen bonds, generating (10-1) sheets.

SUBMITTER: Mague JT

PROVIDER: S-EPMC4459321 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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

Project description:In the title compound, C(12)H(10)N(6)S, a weak intra-molecular C-H?S hydrogen bond stabilizes the mol-ecular conformation. The pyrazole and triazole rings form a dihedral angle of 17.82?(8)°. The mol-ecule adopts an E configuration with respect to the central C=N double bond. In the crystal, inter-molecular N-H?N and N-H?S hydrogen bonds link mol-ecules into chains propagating in [20[Formula: see text]].

| S-EPMC3212330 | biostudies-literature

4-Amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C(8)H(8)N(4)S, the planar triazole ring forms a dihedral angle of 13.7?(2)° with the phenyl ring. The crystal structure is stabilized by inter-molecular N-H?S hydrogen-bond inter-actions, linking the mol-ecules into chains along the a axis.

| S-EPMC2961480 | biostudies-literature

rac-4-Amino-1-(2-benzoyl-1-phenyl-eth-yl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C(18)H(18)N(4)OS, has an almost planar 1,2,4-triazole ring [r.m.s. deviation = 0.0036?(2)?Å], which makes dihedral angles of 78.5?(2) and 77.6?(11)° with the two phenyl rings. An intra-molecular N-H?S inter-action occurs. In the crystal, mol-ecules are linked by an inter-molecular three-centre N-H?(O,S) cyclic hydrogen-bonding inter-action.

| S-EPMC3051463 | 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)-3-thien-ylmethyl-idene-amino]-1H-1,2,4-triazole-5(4H)-thione.

Project description:The asymmetric unit of the title compound, C(8)H(8)N(4)S(2), contains two crystallographically independent mol-ecules. The thio-phene ring of one mol-ecule is disordered over two positions with refined site occupancies of 0.6375?(19) and 0.3625?(19). One mol-ecule is almost planar and the other one is twisted, the dihedral angles between the thio-phene and triazole rings being 7.28?(7) and 48.9?(2)° [48.5?(4)° for the minor component], respectively. An intra-molecular C-H?S hydrogen bond stabilizes the mol-ecular conformation of the planar molecule. In the crystal, the two mol-ecules are inter-connected by N-H?S hydrogen bonds into dimers, which are further consolidated into chains along the b axis by C-H?N hydrogen bonds. Weak C-H?? and ?-? inter-actions [centroid-centroid distance = 3.5149?(7)?Å] are also observed.

| S-EPMC3009062 | 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

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 π-π 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 π-π stacking in the crystal structure.

| S-EPMC2962033 | 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-[(E)-(4-Hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description: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.

| S-EPMC4051099 | biostudies-literature

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