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Volume 68 
Part 12 
Pages o3444-o3445  
December 2012  

Received 5 November 2012
Accepted 20 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.131
Data-to-parameter ratio = 21.0
Details
Open access

2,3-Diaminopyridinium 4-methoxyquinoline-2-carboxylate

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the 4-methoxyquinoline-2-carboxylate anion of the title salt, C5H8N3+·C11H8NO3-, the dihedral angle between the quinoline ring system and the carboxylate group is 16.54 (15)°. In the crystal, the cations and anions are linked via N-H...O and N-H...N hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(9) and R42(8) ring motifs. These units are further connected via N-H...O hydrogen bonds into a layer parallel to the bc plane. The crystal structure is also stabilized by weak C-H...O hydrogen bonds and [pi]-[pi] interactions between pyridine rings [centroid-centroid distance = 3.5886 (8) Å] and between pyridine and benzene rings [centroid-centroid distance = 3.6328 (8) Å].

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997[Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.]); Katritzky et al. (1996[Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.]). For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991[Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.]); Markees et al. (1970[Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.]). For a related structure, see: Hemamalini & Fun (2011[Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o435-o436.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8N3+·C11H8NO3-

  • Mr = 312.33

  • Monoclinic, P 21 /c

  • a = 12.4338 (12) Å

  • b = 7.7462 (7) Å

  • c = 19.4626 (14) Å

  • [beta] = 128.806 (4)°

  • V = 1460.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.24 × 0.21 × 0.11 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.989

  • 17919 measured reflections

  • 4820 independent reflections

  • 3806 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.131

  • S = 1.02

  • 4820 reflections

  • 229 parameters

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

  • [Delta][rho]max = 0.54 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
N3-H2...O3 0.91 (2) 1.890 (19) 2.7670 (18) 162.8 (19)
N2-H3...N1 0.94 (2) 1.94 (3) 2.843 (2) 162.5 (19)
N3-H1...O3i 0.89 (2) 1.94 (2) 2.812 (2) 163.4 (16)
N4-H4...O2ii 0.893 (18) 1.978 (19) 2.8617 (15) 169.8 (17)
N4-H5...O2i 0.88 (2) 2.17 (3) 2.9419 (18) 146 (3)
C4-H4A...O2iii 0.95 2.45 3.3529 (15) 158
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS5215 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o435-o436.  [CSD] [CrossRef] [details]
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.  [CrossRef] [ChemPort] [PubMed] [ISI]
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.  [CrossRef]
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
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 (2012). E68, o3444-o3445   [ doi:10.1107/S1600536812047642 ]

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