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Volume 69 
Part 6 
Pages o949-o950  
June 2013  

Received 13 May 2013
Accepted 17 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.120
Data-to-parameter ratio = 16.9
Details
Open access

N-tert-Butyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyrazin-3-amine

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C16H16Cl2N4, the imidazole ring mean plane makes a dihedral angle of 70.01 (1)° with the phenyl ring. The Cl atoms deviate by -0.0472 (6) and 0.0245 (8) Å from the plane of their attached benzene ring. In the crystal, molecules are linked via pairs of C-H...N hydrogen bonds, forming inversion dimers.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009[Du, X. H., Gustin, D. J., Chen, X. Q., Duquette, J., McGee, L. R., Wang, Z. L., Ebsworth, K., Henne, K., Lemon, B., Ma, J., Miao, S. C., Sabalan, E., Sullivan, T. J., Tonn, G., Collins, T. L. & Medina, J. C. (2009). Bioorg. Med. Chem. Lett. 19, 5200-5204.]); Dubinina et al. (2006[Dubinina, G. G., Platonov, M. O., Golovach, S. M., Borysko, P. O., Tolmachov, A. O. & Volovenko, Y. M. (2006). Eur. J. Med. Chem. 41, 727-737.]); Ellsworth et al. (2007[Ellsworth, B. A., Wang, Y., Zhu, Y. H., Pendri, A., Gerritz, S. W., Sun, C. Q., Carlson, K. E., Kang, L. Y., Baska, R. A., Yang, Y. F., Huang, Q., Burford, N. T., Cullen, M. J., Johnghar, S., Behnia, K., Pelleymounter, M. A., Washburn, W. N. & Ewing, W. R. (2007). Bioorg. Med. Chem. Lett. 17, 3978-3982.]); Mukaiyama et al. (2007[Mukaiyama, H., Nishimura, T., Kobayashi, S., Ozawa, T., Kamada, N., Komatsu, Y., Kikuchi, S., Oonota, H. & Kusama, H. (2007). Bioorg. Med. Chem. Lett. 15, 868-885.]). For background to the fluorescence properties of related compounds, see: Kawai et al. (2001[Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.]); Abdullah (2005[Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.]). For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992[Dooley, S. W., Jarvis, W. R., Marione, W. J. & Snider, D. E. Jr (1992). Ann. Intern. Med. 117, 257-259.]); Jackson et al. (2000[Jackson, C. J., Lamb, D. C., Kelly, D. E. & Kelly, S. L. (2000). FEMS Microbiol. Lett. 192, 159-162.]); Banfi et al. (2006[Banfi, E., Scialino, G., Zampieri, D., Mamolo, M. G., Vio, L., Ferrone, M., Fermeglia, M., Paneni, M. S. & Pricl, S. (2006). J. Antimicrob. Chemother. 58, 76-84.]). For related structures, see: Ouzidan et al. (2011[Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1684.]); Nasir et al. (2010[Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16Cl2N4

  • Mr = 335.23

  • Triclinic, [P \overline 1]

  • a = 8.1482 (4) Å

  • b = 9.8553 (5) Å

  • c = 11.5265 (6) Å

  • [alpha] = 93.218 (2)°

  • [beta] = 99.320 (3)°

  • [gamma] = 113.026 (2)°

  • V = 833.31 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.39 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.892, Tmax = 0.926

  • 12583 measured reflections

  • 3438 independent reflections

  • 2941 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.120

  • S = 1.05

  • 3438 reflections

  • 203 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...N2i 0.93 2.62 3.500 (3) 158
Symmetry code: (i) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and 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: SU2601 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF also thanks the UGC for a meritorious fellowship.

References

Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.  [ChemPort]
Banfi, E., Scialino, G., Zampieri, D., Mamolo, M. G., Vio, L., Ferrone, M., Fermeglia, M., Paneni, M. S. & Pricl, S. (2006). J. Antimicrob. Chemother. 58, 76-84.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dooley, S. W., Jarvis, W. R., Marione, W. J. & Snider, D. E. Jr (1992). Ann. Intern. Med. 117, 257-259.  [CrossRef] [PubMed] [ChemPort]
Du, X. H., Gustin, D. J., Chen, X. Q., Duquette, J., McGee, L. R., Wang, Z. L., Ebsworth, K., Henne, K., Lemon, B., Ma, J., Miao, S. C., Sabalan, E., Sullivan, T. J., Tonn, G., Collins, T. L. & Medina, J. C. (2009). Bioorg. Med. Chem. Lett. 19, 5200-5204.  [CrossRef] [PubMed] [ChemPort]
Dubinina, G. G., Platonov, M. O., Golovach, S. M., Borysko, P. O., Tolmachov, A. O. & Volovenko, Y. M. (2006). Eur. J. Med. Chem. 41, 727-737.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ellsworth, B. A., Wang, Y., Zhu, Y. H., Pendri, A., Gerritz, S. W., Sun, C. Q., Carlson, K. E., Kang, L. Y., Baska, R. A., Yang, Y. F., Huang, Q., Burford, N. T., Cullen, M. J., Johnghar, S., Behnia, K., Pelleymounter, M. A., Washburn, W. N. & Ewing, W. R. (2007). Bioorg. Med. Chem. Lett. 17, 3978-3982.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jackson, C. J., Lamb, D. C., Kelly, D. E. & Kelly, S. L. (2000). FEMS Microbiol. Lett. 192, 159-162.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.  [CrossRef] [ChemPort]
Mukaiyama, H., Nishimura, T., Kobayashi, S., Ozawa, T., Kamada, N., Komatsu, Y., Kikuchi, S., Oonota, H. & Kusama, H. (2007). Bioorg. Med. Chem. Lett. 15, 868-885.  [ChemPort]
Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.  [CSD] [CrossRef] [details]
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1684.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o949-o950   [ doi:10.1107/S1600536813013640 ]

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