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

ABSTRACT: 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.

SUBMITTER: Yuan CX

PROVIDER: S-EPMC4158482 | biostudies-literature | 2014 Aug

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.

Yuan Cai-Xia CX Lan Shu-Fen SF Liu Xin-Yu XY Zhu Miao-Li ML

Acta crystallographica. Section E, Structure reports online 20140726 Pt 8

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. Ther ...[more]

PMID: 25249924

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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.

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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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