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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.

Manjula PS, Sarojini BK, Yathirajan HS, Akkurt M, Ersanlı CC, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported.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)°.Comparisons are made with some related structures.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu 574 153, Mangaluru, D. K., India.

ABSTRACT
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.

No MeSH data available.


The mol­ecular structure of compound (I) showing the atom-labelling scheme. The non-H atoms all lie on a mirror plane and the H atom sites in the methyl group all have occupancy 0.5. Displacement ellipsoids are drawn at the 30% probability level.
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fig1: The mol­ecular structure of compound (I) showing the atom-labelling scheme. The non-H atoms all lie on a mirror plane and the H atom sites in the methyl group all have occupancy 0.5. Displacement ellipsoids are drawn at the 30% probability level.

Mentions: Heterocyclic compounds containing both nitro­gen and sulfur exhibit a wide variety of biological activities, including analgesic (Thieme et al., 1973a ▸,b ▸), anti­hypertensive (Wei & Bell, 1981a ▸,b ▸), and anti-inflammatory activity (Dornow et al., 1964 ▸), in addition to fungicidal (Malik et al., 2011 ▸) and sedative action (Barrera et al., 1985 ▸). Here we report the mol­ecular and crystal structures of three examples of 1,2,4-triazole-5-thio­nes, namely 4-amino-3-methyl-1H-1,2,4-triazole-5-thione, (I) (Fig. 1 ▸), 4-[(E)-(3,4-di­meth­oxy­benzyl­idene)amino]-3-methyl-1H-1,2,4-triazole-5-thione, (II) (Fig. 2 ▸), and 4-[(E)-(2-hy­droxy-5-bromo­benzyl­idene)amino]-3-methyl-1H-1,2,4-tri­azol-5-thione, (III) (Fig. 3 ▸).


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.

Manjula PS, Sarojini BK, Yathirajan HS, Akkurt M, Ersanlı CC, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of compound (I) showing the atom-labelling scheme. The non-H atoms all lie on a mirror plane and the H atom sites in the methyl group all have occupancy 0.5. Displacement ellipsoids are drawn at the 30% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555427&req=5

fig1: The mol­ecular structure of compound (I) showing the atom-labelling scheme. The non-H atoms all lie on a mirror plane and the H atom sites in the methyl group all have occupancy 0.5. Displacement ellipsoids are drawn at the 30% probability level.
Mentions: Heterocyclic compounds containing both nitro­gen and sulfur exhibit a wide variety of biological activities, including analgesic (Thieme et al., 1973a ▸,b ▸), anti­hypertensive (Wei & Bell, 1981a ▸,b ▸), and anti-inflammatory activity (Dornow et al., 1964 ▸), in addition to fungicidal (Malik et al., 2011 ▸) and sedative action (Barrera et al., 1985 ▸). Here we report the mol­ecular and crystal structures of three examples of 1,2,4-triazole-5-thio­nes, namely 4-amino-3-methyl-1H-1,2,4-triazole-5-thione, (I) (Fig. 1 ▸), 4-[(E)-(3,4-di­meth­oxy­benzyl­idene)amino]-3-methyl-1H-1,2,4-triazole-5-thione, (II) (Fig. 2 ▸), and 4-[(E)-(2-hy­droxy-5-bromo­benzyl­idene)amino]-3-methyl-1H-1,2,4-tri­azol-5-thione, (III) (Fig. 3 ▸).

Bottom Line: The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported.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)°.Comparisons are made with some related structures.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu 574 153, Mangaluru, D. K., India.

ABSTRACT
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.

No MeSH data available.