[Journal logo]

Volume 69 
Part 12 
Page o1825  
December 2013  

Received 8 November 2013
Accepted 9 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.084
wR = 0.206
Data-to-parameter ratio = 11.2
Details
Open access

5-[(2-Methyl-4-nitro-1H-imidazol-1-yl)meth­yl]-1,3,4-thia­diazol-2-amine

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

In the title compound, C7H8N6O2S, the dihedral angle between the imidazole and thia­diazole rings is 70.86 (15)°. In the crystal, mol­ecules are linked into [10-1] chains by N-H...N hydrogen bonds, which incorporate centrosymmetric R22(8) and R22(18) loops. The chains are linked by C-H...O and C-H...N inter­actions, generating a three-dimensional network. Very weak [pi]-[pi] stacking [centroid-centroid distance = 3.901 (17) Å] is also observed.

Related literature

For biological background, see: Dogan et al. (2002[Dogan, H. N., Duran, A., Rollas, S., Sener, G., Uysal, M. K. & Gülen, D. (2002). Bioorg. Med. Chem. 10, 2893-2898.]); Frank & Kalluraya (2005[Frank, P. V. & Kalluraya, B. (2005). J. Indian J. Chem. Sect. B, 44, 1456-1459.]); Mullican et al. (1993[Mullican, M. D., Wilson, M. W., Conner, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.]). For related structures, see: Zama et al. (2013[Zama, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2013). Acta Cryst. E69, o837-o838.]); Yin et al. (2012[Yin, W., Wang, Z. & Yang, Z.-W. (2012). Acta Cryst. E68, o769.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N6O2S

  • Mr = 240.26

  • Triclinic, [P \overline 1]

  • a = 7.8030 (15) Å

  • b = 8.2750 (16) Å

  • c = 8.3596 (16) Å

  • [alpha] = 100.945 (8)°

  • [beta] = 92.379 (8)°

  • [gamma] = 105.911 (7)°

  • V = 507.15 (17) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.86 mm-1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.559, Tmax = 0.585

  • 5433 measured reflections

  • 1640 independent reflections

  • 1560 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.206

  • S = 1.10

  • 1640 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.80 e Å-3

  • [Delta][rho]min = -0.65 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...N1i 0.86 2.15 2.996 (4) 169
N3-H3B...N5ii 0.86 2.26 3.033 (4) 150
C3-H3D...O1iii 0.97 2.46 3.100 (4) 123
C4-H4...N2iv 0.93 2.51 3.296 (4) 142
C7-H7C...O2v 0.96 2.57 3.445 (4) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+2; (iii) x, y, z-1; (iv) -x, -y, -z+1; (v) x, y+1, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7159 ).


Acknowledgements

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. MKU is grateful to the DST, New Delhi, for the award of an INSPIRE Fellowship. DR acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [No. F.41-882/2012 (SR)].

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dogan, H. N., Duran, A., Rollas, S., Sener, G., Uysal, M. K. & Gülen, D. (2002). Bioorg. Med. Chem. 10, 2893-2898.  [CrossRef] [PubMed] [ChemPort]
Frank, P. V. & Kalluraya, B. (2005). J. Indian J. Chem. Sect. B, 44, 1456-1459.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mullican, M. D., Wilson, M. W., Conner, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yin, W., Wang, Z. & Yang, Z.-W. (2012). Acta Cryst. E68, o769.  [CSD] [CrossRef] [IUCr Journals]
Zama, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2013). Acta Cryst. E69, o837-o838.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1825  [ doi:10.1107/S1600536813030821 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.