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Volume 68 
Part 1 
Pages o79-o80  
January 2012  

Received 15 November 2011
Accepted 5 December 2011
Online 10 December 2011

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Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.085
Data-to-parameter ratio = 13.4
Details
Open access

3-Carbamoylquinoxalin-1-ium chloride

James K. Harper,a* Gary Strobelb and Atta M. Arifc

aUniversity of Central Florida, Department of Chemistry, 4000 Central Florida Blvd., Orlando, FL 32816, USA,bMontana State University, Department of Plant Sciences and Plant Patology, Bozeman, MT 59717, USA, and cUniversity of Utah, Department of Chemistry, 315 S. 1400 E. Rm. 2020, Salt Lake City, UT 84112, USA
Correspondence e-mail: james.harper@ucf.edu

The title compound, C9H8N3O+·Cl-, was isolated from a liquid culture of streptomyces sp. In the cation, the ring system makes a dihedral angle of 0.2 (2)° with the amide group. The protonation creating the cation occurs at ome of the N atoms in the quinoxaline ring system. In the crystal, the ions are linked through N-H...O and N-H...Cl hydrogen bonds, forming a two-dimensional network parallel to (10[\overline{3}]).

Related literature

For a description of the bioactivity and mode of action of compounds containing the quinoxaline moiety, see: Bailly et al. (1999[Bailly, C., Echepare, S., Gago, F. & Waring, M. J. (1999). Anti-Cancer Drug Des. 14, 291-303.]); May et al. (2004[May, L. G., Madine, M. A. & Waring, M. J. (2004). Nucleic Acids Res. 32, 65-72.]); Mollegaard et al. (2000[Mollegaard, N. K., Bailly, C., Waring, M. J. & Nielsen, P. E. (2000). Biochemistry, 39, 9502-9507.]); Waring (1993[Waring, M. J. (1993). In Molecular aspects of anticancer drug-DNA interactions. Boca Raton, Florida, USA: CRC Press.]). For crystal structures of the molecules triostin A, echinomycin and their derivatives, which all contain two quinoxalines, see: Hossain et al. (1982[Hossain, M. B., van der Helm, D., Olsen, R. K., Jones, P. G., Sheldrick, G. M., Egert, E., Kennard, O., Waring, M. J. & Viswamitra, M. A. (1982). J. Am. Chem. Soc. 104, 3401-3408.]); Sheldrick et al. (1984[Sheldrick, G. M., Guy, J. J., Kennard, O., Rivera, U. & Waring, M. J. (1984). J. Chem. Soc. Perkin Trans. 2, pp. 1601-1605.], 1995[Sheldrick, G. M., Heine, A., Schmidt-Bäse, K., Pohl, E., Jones, P. G., Paulus, E. & Waring, M. J. (1995). Acta Cryst. B51, 987-999.]); Viswamitra et al. (1981[Viswamitra, M. A., Kennard, O., Cruse, W. B. T., Egert, E., Sheldrick, G. M., Jones, P. G., Waring, M. J., Wakelin, L. P. G. & Olsen, R. K. (1981). Nature (London), 289, 817-819.]); Wang et al. (1984[Wang, A. H.-J., Ughetto, G., Quigley, G. J., Hakoshima, T., van der Marel, G. A., van Boom, J. H., Rich, A. (1984). Science, 225, 1115-1121.]); Ughetto et al. (1985[Ughetto, G., Wang, A. H.-J., Quigley, G. J., van der Marel, G. A., van Boom, J. H., Rich, A. (1985). Nucleic Acids Res. 13, 2305-2323.]). For a description of the Streptomycete producing the title compound, see: Castillo et al. (2003[Castillo, U., Harper, J. K., Strobel, G. A., Sears, J., Alesi, K., Ford, E., Lin, J., Hunter, M., Maranta, M., Ge, H., Yaver, D., Jensen, J. B., Porter, H., Robison, R., Miller, D., Hess, W. M., Condron, M. & Teplow, D. (2003). FEMS Microbiol. Lett. 224, 183-190.]).

[Scheme 1]

Experimental

Crystal data

  • C9H8N3O+·Cl-

  • Mr = 209.63

  • Monoclinic, P 21 /n

  • a = 5.6476 (2) Å

  • b = 15.1045 (9) Å

  • c = 11.2556 (6) Å

  • [beta] = 99.993 (3)°

  • V = 945.58 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 150 K

  • 0.25 × 0.20 × 0.08 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.913, Tmax = 0.971

  • 3671 measured reflections

  • 2147 independent reflections

  • 1798 reflections with I > 2[sigma](I)

  • Rint = 0.018
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.085

  • S = 1.05

  • 2147 reflections

  • 160 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 (2) 2.04 (2) 2.9008 (17) 173.5 (17)
N1-H1B...Cl1 0.90 (2) 2.44 (2) 3.2590 (13) 152.0 (17)
N3-H3N...Cl1ii 0.94 (2) 2.02 (2) 2.9501 (13) 169.8 (15)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5381 ).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bailly, C., Echepare, S., Gago, F. & Waring, M. J. (1999). Anti-Cancer Drug Des. 14, 291-303.  [PubMed] [ChemPort]
Castillo, U., Harper, J. K., Strobel, G. A., Sears, J., Alesi, K., Ford, E., Lin, J., Hunter, M., Maranta, M., Ge, H., Yaver, D., Jensen, J. B., Porter, H., Robison, R., Miller, D., Hess, W. M., Condron, M. & Teplow, D. (2003). FEMS Microbiol. Lett. 224, 183-190.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hossain, M. B., van der Helm, D., Olsen, R. K., Jones, P. G., Sheldrick, G. M., Egert, E., Kennard, O., Waring, M. J. & Viswamitra, M. A. (1982). J. Am. Chem. Soc. 104, 3401-3408.  [CrossRef] [ChemPort] [ISI]
May, L. G., Madine, M. A. & Waring, M. J. (2004). Nucleic Acids Res. 32, 65-72.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mollegaard, N. K., Bailly, C., Waring, M. J. & Nielsen, P. E. (2000). Biochemistry, 39, 9502-9507.  [ISI] [PubMed] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sheldrick, G. M., Guy, J. J., Kennard, O., Rivera, U. & Waring, M. J. (1984). J. Chem. Soc. Perkin Trans. 2, pp. 1601-1605.
Sheldrick, G. M., Heine, A., Schmidt-Bäse, K., Pohl, E., Jones, P. G., Paulus, E. & Waring, M. J. (1995). Acta Cryst. B51, 987-999.  [CrossRef] [ISI] [details]
Ughetto, G., Wang, A. H.-J., Quigley, G. J., van der Marel, G. A., van Boom, J. H., Rich, A. (1985). Nucleic Acids Res. 13, 2305-2323.  [CrossRef] [ChemPort] [PubMed] [ISI]
Viswamitra, M. A., Kennard, O., Cruse, W. B. T., Egert, E., Sheldrick, G. M., Jones, P. G., Waring, M. J., Wakelin, L. P. G. & Olsen, R. K. (1981). Nature (London), 289, 817-819.  [CrossRef] [ChemPort] [PubMed] [ISI]
Wang, A. H.-J., Ughetto, G., Quigley, G. J., Hakoshima, T., van der Marel, G. A., van Boom, J. H., Rich, A. (1984). Science, 225, 1115-1121.  [CrossRef] [ChemPort] [PubMed] [ISI]
Waring, M. J. (1993). In Molecular aspects of anticancer drug-DNA interactions. Boca Raton, Florida, USA: CRC Press.

Acta Cryst (2012). E68, o79-o80   [ doi:10.1107/S1600536811052457 ]

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