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

ABSTRACT: 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).

SUBMITTER: Wang M

PROVIDER: S-EPMC2960248 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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

Wang Min M Cao Minna M Hu Bo B Cheng Cuixia C Song Xuegang X

Acta crystallographica. Section E, Structure reports online 20080104 Pt 2

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 π-π stacking of the triazole rings and of the benzene rings (centroid-centroid distances of 3.4109 and 3.569 Å, respectively). ...[more]

PMID: 21201405

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4-[(E)-4-Bromo-benzyl-ideneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title mol-ecule, C(10)H(9)BrN(4)S, the dihedral angle between the triazole and benzene rings is 12.32?(19)°. An intra-molecular C-H?S hydrogen bond generates an S(6) ring motif. In the crystal packing, centrosymmetrically related mol-ecules are linked into a dimer by N-H?S hydrogen bonds, and the dimers are linked into a chain running along [11] by Br?N short contacts [3.187?(3)?Å]. The crystal packing is further strengthened by ?-? inter-actions involving the triazole ring [centroid-centroid distance = 3.322?(2)?Å].

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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.

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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.

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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.

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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.

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3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77?(2):0.23?(2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002?(3)?Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94?(18) and 86.56?(49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55?(15)° and this conformation is stabilized by an intra-molecular C-H?S contact. In the crystal, pairs of N-H?S hydrogen bonds link mol-ecules into inversion dimers. ?-? inter-actions are observed between the triazole and benzene rings, with centroid-centroid separations of 3.547?(4) and 3.544?(12)?Å for components A and B, and slippages of 0.49?(6) and 0.58?(15)?Å, respectively.

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