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Volume 70 
Part 1 
Pages o48-o49  
January 2014  

Received 8 December 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.102
Data-to-parameter ratio = 13.1
Details
Open access

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

aDepartment of Chemistry, P.A. College of Engineering, Nadupadavu 574 153, D.K., Mangalore, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C9H10N4OS, the dihedral angle between the benzene and 1H-1,2,4-triazole-5(4H)-thione rings is 67.51 (16)°. In the crystal, mol­ecules are liked via N-H...O hydrogen bonds, forming chains along the c-axis direction. The chains are linked via O-H...S hydrogen bonds, forming corrugated layers lying parallel to the bc plane. The layers are linked via N-H...N and N-H...S hydrogen bonds, forming a three-dimensional network.

Related literature

For biological properties of 1,2,4-triazole derivatives, see: Holla et al. (2001[Holla, B. S., Sarojini, B. K., Rao, B. S., Akberali, P. M. & Suchetha Kumari, N. (2001). Il Farmaco, 56, 565-570.], 2006[Holla, B. S., Rao, B. S., Sarojini, B. K., Akberali, P. M. & Suchetha Kumari, N. (2006). Eur. J. Med. Chem. 41, 657-663.]); Mullican et al. (1993[Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.]); Jones et al. (1965[Jones, D. H., Slack, R., Squires, S. & Wooldridge, K. R. H. (1965). J. Med. Chem. 8, 676-680.]); Shams El-Dine et al. (1974[Shams El-Dine, Sh. A. & Hazzaa, A. A. B. (1974). Pharmazie, 29, 761-768.]); Misato et al. (1977[Misato, T., Ko, K., Honma, Y., Konno, K. & Taniyama, E. (1977). Chem. Abstr. 87, 147054a.]); Kane et al. (1988[Kane, J. M., Dudley, M. W., Sorensen, S. M. & Miller, F. P. (1988). J. Med. Chem. 31, 1253-1258.]). For related structures, see: Puviarasan et al. (1999[Puviarasan, K., Govindasamy, L., Shanmuga Sundara Raj, S., Velmurugan, D., Jayanthi, G. & Fun, H.-K. (1999). Acta Cryst. C55, 951-953.]); Chen et al. (2007[Chen, X.-A., Huang, X.-B. & Wu, H.-Y. (2007). Acta Cryst. E63, o3191.]); Karczmarzyk et al. (2012[Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.]); Gao et al. (2011[Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10N4OS

  • Mr = 222.27

  • Triclinic, P 1

  • a = 4.2117 (5) Å

  • b = 6.1891 (7) Å

  • c = 10.0641 (11) Å

  • [alpha] = 100.590 (9)°

  • [beta] = 94.916 (9)°

  • [gamma] = 104.589 (10)°

  • V = 247.14 (5) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 173 K

  • 0.34 × 0.30 × 0.24 mm

Data collection
  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]). Tmin = 0.941, Tmax = 1.000

  • 2555 measured reflections

  • 1897 independent reflections

  • 1826 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.102

  • S = 1.10

  • 1897 reflections

  • 145 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 265 Friedel pairs (15% coverage)

  • Absolute structure parameter: -0.02 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.88 1.97 2.840 (3) 170
O1-H1...S1ii 0.95 (5) 2.27 (5) 3.180 (2) 159 (4)
N4-H4A...S1iii 0.86 2.74 3.435 (3) 138
N4-H4B...N1iv 0.91 (3) 2.32 (3) 3.149 (4) 153 (3)
Symmetry codes: (i) x, y, z-1; (ii) x+1, y+1, z+1; (iii) x-1, y, z; (iv) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2674 ).


Acknowledgements

BKS and PSM gratefully acknowledge the Department of Chemistry, P. A. College of Engineering, for providing research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Chen, X.-A., Huang, X.-B. & Wu, H.-Y. (2007). Acta Cryst. E63, o3191.  [CSD] [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.  [CSD] [CrossRef] [IUCr Journals]
Holla, B. S., Rao, B. S., Sarojini, B. K., Akberali, P. M. & Suchetha Kumari, N. (2006). Eur. J. Med. Chem. 41, 657-663.  [PubMed] [ChemPort]
Holla, B. S., Sarojini, B. K., Rao, B. S., Akberali, P. M. & Suchetha Kumari, N. (2001). Il Farmaco, 56, 565-570.  [CrossRef] [PubMed] [ChemPort]
Jones, D. H., Slack, R., Squires, S. & Wooldridge, K. R. H. (1965). J. Med. Chem. 8, 676-680.  [CrossRef] [ChemPort] [Web of Science]
Kane, J. M., Dudley, M. W., Sorensen, S. M. & Miller, F. P. (1988). J. Med. Chem. 31, 1253-1258.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Misato, T., Ko, K., Honma, Y., Konno, K. & Taniyama, E. (1977). Chem. Abstr. 87, 147054a.
Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Puviarasan, K., Govindasamy, L., Shanmuga Sundara Raj, S., Velmurugan, D., Jayanthi, G. & Fun, H.-K. (1999). Acta Cryst. C55, 951-953.  [CSD] [CrossRef] [IUCr Journals]
Shams El-Dine, Sh. A. & Hazzaa, A. A. B. (1974). Pharmazie, 29, 761-768.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o48-o49   [ doi:10.1107/S1600536813033370 ]

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