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Volume 69 
Part 5 
Page o777  
May 2013  

Received 16 March 2013
Accepted 17 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.124
Data-to-parameter ratio = 14.6
Details
Open access

Methyl 3,5-bis[(3-chloropyrazin-2-yl)oxy]benzoate

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C16H10Cl2N4O4, the pyrazine rings make dihedral angles of 67.82 (9) and 75.91 (9)° with the benzene ring, while the dihedral angle between the pyrazine rings is 44.69 (10)°. The methoxycarbonyl group makes a dihedral angle of 16.82 (8)° with the benzene ring to which it is attached. In the crystal, C-H...O hydrogen bonds link the molecules, forming chains running along the ab plane.

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 a related structure, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10Cl2N4O4

  • Mr = 393.18

  • Triclinic, [P \overline 1]

  • a = 8.5437 (15) Å

  • b = 9.2984 (18) Å

  • c = 11.545 (2) Å

  • [alpha] = 88.592 (10)°

  • [beta] = 74.974 (9)°

  • [gamma] = 73.231 (9)°

  • V = 846.9 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.41 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 = 0.886, Tmax = 0.922

  • 12425 measured reflections

  • 3453 independent reflections

  • 3076 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.124

  • S = 1.04

  • 3453 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O2i 0.93 2.47 3.192 (3) 135
Symmetry code: (i) x, y-1, 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: PV2625 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship. The UGC (SAP-CAS) is acknowleged for departmental facilities.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
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]
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, o777  [ doi:10.1107/S1600536813010465 ]

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