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Volume 69 
Part 4 
Pages o612-o613  
April 2013  

Received 18 March 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.148
Data-to-parameter ratio = 19.1
Details
Open access

N-tert-Butyl-2-[4-(dimethylamino)phenyl]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, C18H23N5, the imidazole ring makes a dihedral angles of 3.96 (8) and 19.02 (8)°, respectively, with the pyrazine and benzene rings while the dihedral angle between the pyrazine and benzene rings is 16.96 (7)°. In the crystal, molecules are linked via N-H...N hydrogen bonds, forming chains along [010]. These chains are linked by C-H...N hydrogen bonds, forming two-dimensional networks lying parallel to (001).

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 ongoing structural studies of heterocyclic N-containing derivatives, see: Nasir et al. (2010[Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.]). For background to the fluorescence properties of compounds related to the title compound, 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 a related structure, see: Ouzidan et al. (2011[Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1684.]).

[Scheme 1]

Experimental

Crystal data
  • C18H23N5

  • Mr = 309.41

  • Orthorhombic, P b c a

  • a = 12.1746 (11) Å

  • b = 13.9614 (13) Å

  • c = 20.2985 (19) Å

  • V = 3450.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 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 = 0.978, Tmax = 0.985

  • 18314 measured reflections

  • 4157 independent reflections

  • 2964 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.148

  • S = 1.03

  • 4157 reflections

  • 218 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...N1i 0.873 (18) 2.201 (18) 3.0361 (18) 160.0 (14)
C11-H11...N4ii 0.93 2.53 3.428 (2) 162
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, 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: SU2577 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for 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.  [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] [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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o612-o613   [ doi:10.1107/S1600536813007861 ]

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