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

Thanigaimani, K.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812047642

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 (C-C) = 0.002 Å
R = 0.047
wR = 0.131
Data-to-parameter ratio = 21.0
Details

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

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

^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-HO and N-HN hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R₂²(9) and R₄²(8) ring motifs. These units are further connected via N-HO hydrogen bonds into a layer parallel to the bc plane. The crystal structure is also stabilized by weak C-HO 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); Katritzky et al. (1996). For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991); Markees et al. (1970). For a related structure, see: Hemamalini & Fun (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₈N₃⁺·C₁₁H₈NO₃^-
M_r = 312.33
Monoclinic, P 2₁ /c
a = 12.4338 (12) Å
b = 7.7462 (7) Å
c = 19.4626 (14) Å
= 128.806 (4)°
V = 1460.8 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.976, T_max = 0.989
17919 measured reflections
4820 independent reflections
3806 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(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
_max = 0.54 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H2O3	0.91 (2)	1.890 (19)	2.7670 (18)	162.8 (19)
N2-H3N1	0.94 (2)	1.94 (3)	2.843 (2)	162.5 (19)
N3-H1O3ⁱ	0.89 (2)	1.94 (2)	2.812 (2)	163.4 (16)
N4-H4O2ⁱⁱ	0.893 (18)	1.978 (19)	2.8617 (15)	169.8 (17)
N4-H5O2ⁱ	0.88 (2)	2.17 (3)	2.9419 (18)	146 (3)
C4-H4AO2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o435-o436.
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.
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds