5-Amino-6-methyl­quinolin-1-ium hydrogen malonate–malonic acid (2/1)

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

doi:10.1107/S1600536813002547

Volume 69
Part 3
Pages o319-o320
March 2013

Received 20 December 2012
Accepted 25 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.130
Data-to-parameter ratio = 17.0
Details

5-Amino-6-methylquinolin-1-ium hydrogen malonate-malonic acid (2/1)

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

The asymmetric unit of the title compound, 2C₁₀H₁₁N₂⁺·2C₃H₃O₄^-·C₃H₄O₄, consists of one 5-amino-6-methylquinolin-1-ium cation, one hydrogen malonate (2-carboxyacetate) anion and one-half molecule of malonic acid which lies on a twofold rotation axis. The quinoline ring system is essentially planar, with a maximum deviation of 0.062 (2) Å for all non-H atoms. In the anion, an intramolecular O-HO hydrogen bond generates an S(6) ring. In the crystal, the components are linked via N-HO and O-HO hydrogen bonds into layers parallel to the ac plane. The crystal structure also features weak C-HO hydrogen bonds and a [pi] - [pi] stacking interaction with a centroid-centroid distance of 3.8189 (10) Å.

Related literature

For background to and the biological activity of quinoline derivatives, see: Sasaki et al. (1998); Reux et al. (2009); Morimoto et al. (1991); Markees et al. (1970). For related structures, see: Thanigaimani et al. (2013a,b); Loh et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

2C₁₀H₁₁N₂⁺·2C₃H₃O₄^-·C₃H₄O₄
M_r = 628.59
Monoclinic, C 2/c
a = 24.701 (2) Å
b = 4.8530 (4) Å
c = 25.063 (2) Å
= 95.321 (3)°
V = 2991.4 (4) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 297 K
0.35 × 0.24 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.962, T_max = 0.990
25870 measured reflections
3835 independent reflections
2644 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.130
S = 1.03
3835 reflections
225 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O3	1.00 (2)	1.76 (2)	2.7450 (17)	172.3 (18)
O2-H1O2O4	0.86 (1)	1.64 (1)	2.4630 (18)	159 (2)
C1-H1AO4	0.93	2.44	3.095 (2)	127
N2-H1N2O1ⁱ	0.91 (2)	2.11 (2)	3.012 (2)	173.4 (18)
N2-H2N2O5ⁱⁱ	0.90 (2)	2.20 (2)	3.076 (2)	166 (2)
O6-H106O3ⁱⁱⁱ	1.02 (3)	1.60 (3)	2.5927 (19)	164 (2)
C1-H1AO2^iv	0.93	2.28	3.106 (2)	148
C3-H3AO1ⁱ	0.93	2.34	3.2648 (19)	174
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) x, y-1, z; (iv) -x, -y+1, -z.

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: IS5233 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant No. 304/PFIZIK/6312078 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.
Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2357.
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.
Reux, B., Nevalainen, T., Raitio, K. H. & Koskinen, A. M. P. (2009). Bioorg. Med. Chem. 17, 4441-4447.
Sasaki, K., Tsurumori, A. & Hirota, T. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3851-3856.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013a). Acta Cryst. E69, o42-o43.
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013b). Acta Cryst. E69, o44.

organic compounds