Crystal Structures of two Triazole Derivatives

Ambalavanan, P.; Palani, K.; Ponnuswamy, M. N.; Thirumuruhan, R.; Yathirajan, H. S.; Prabhuswamy, B.; Raju, C.; Nagaraja, Padmarajaiah; Mohana, K. N.

doi:10.1080/10587250307068

Cited by 9 publications

(7 citation statements)

References 3 publications

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“…The title molecule ( Fig.1) contains the rings 1,2,4-triazole and 4-chlorophenyl. All the bond lengths and bond angles are well agreed with previously reported structure (Ambalavanan et al, 2003;Natarajan and Mathews, 2011). The phenyl ring substituted on the atom C2 shows rotational disorder by the atoms of C4, C5, C7 & C8.…”

Section: Methodssupporting

confidence: 88%

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

Natarajan

Mathews

2012

Acta Cryst E

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In the title compound, C8H7ClN4S, the benzene ring is statistically disordered over two conformations rotated about the Cl—C⋯C—C axis, which subtend dihedral angles of 24.7 (3) and 9.9 (2) ° with respect to the triazole ring. An intramolecular C—H⋯N close contact occurs. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds link the molecules into (001) sheets: R 2 2(8) and R 2 2(10) graph-set motifs result. Weak C—H⋯N hydrogen bonds and aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.681 (7) Å] complete the structure.

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Section: Methodssupporting

confidence: 88%

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

Natarajan

Mathews

2012

Acta Cryst E

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“…The longer one (3.84 Å ) might correspond to a weak S-HÁ Á ÁN interaction (Zhu-Ohlbach et al, 1998). In the third compound (Ambalalavanan et al, 2003), 3-(p-tolyl)-4amino-5-mercapto-1,2,4-triazole (ILOQEF), the R factor is perhaps high (0.066) and there is a possibility of tautomerism so that instead of an S-HÁ Á ÁN bond, an N-HÁ Á ÁS bond could be formed instead. In the last compound, 1-formyl-3-thiosemicarbazide (SOJNAG; Saxena et al, 1991), a possible S-HÁ Á ÁN interaction (3.67 Å , 2.63 Å , 143 ) was identified in the CSD search, although the accepted structural formula does not contain an S-H group.…”

Section: Introductionmentioning

confidence: 98%

Five varieties of hydrogen bond in 1-formyl-3-thiosemicarbazide: an electron density study

Munshi

Thakur

Row

et al. 2006

Acta Crystallogr Sect B

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In an attempt to investigate the putative S-H...N hydrogen bond, we have studied the title compound, 1-formyl-3-thiosemicarbazide, which was revealed in a CSD search as a crystal structure which might show such an interaction. However, a redetermination of the structure at room temperature and careful analysis showed that the earlier study [Saxena et al. (1991). Acta Cryst. C47, 2374-2376] on which the CSD search was based was in error and that the possibility of an S-H...N hydrogen bond is negated. The presence of five other varieties of hydrogen bond (N-H...O, N-H...S, N-H...N, C-H...O, C-H...S) in the crystal packing prompted us to redirect our efforts and to undertake a study of the charge-density distribution at 90 K. The topological analysis of these five varieties of hydrogen bond was carried out with Bader's quantum theory of ;atoms in molecules' and by applying Koch-Popelier's criteria. The analysis reveals that the hydrogen-bond strength is highest for N-H...O and lowest for C-H...S with N-H...S, N-H...N and C-H...O forming the middle order.

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“…Imidazole derivatives have applications as pharmaceuticals, agrochemicals, dyes and high-temperature polymer products (Rasmussen, 1999;Ambalavanan et al, 2003). The title compound, (I), is used as an intermediate for the synthesis of biologically active novel heterocycles (Rai et al, 1992).…”

Section: Commentmentioning

confidence: 99%

4′-[2-Butyl-4-chloro-5-(hydroxyiminomethyl)-1H-imidazol-3-ylmethyl]biphenyl-2-carbonitrile

et al. 2005

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Key indicatorsSingle-crystal X-ray study T = 173 K Mean (C-C) = 0.003 Å Disorder in main residue R factor = 0.043 wR factor = 0.105 Data-to-parameter ratio = 13.8For details of how these key indicators were automatically derived from the article, seePerspective view of the title compound, with the atom numbering; displacement ellipsoids are drawn at the 50% probability level. The minor occupancy disordered atoms are shown with open bonds.

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Crystal Structures of two Triazole Derivatives

Cited by 9 publications

References 3 publications

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

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

Five varieties of hydrogen bond in 1-formyl-3-thiosemicarbazide: an electron density study

4′-[2-Butyl-4-chloro-5-(hydroxyiminomethyl)-1H-imidazol-3-ylmethyl]biphenyl-2-carbonitrile

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