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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 [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.130
Data-to-parameter ratio = 17.0
Details
Open access

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

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-H...O hydrogen bond generates an S(6) ring. In the crystal, the components are linked via N-H...O and O-H...O hydrogen bonds into layers parallel to the ac plane. The crystal structure also features weak C-H...O 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[Sasaki, K., Tsurumori, A. & Hirota, T. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3851-3856.]); Reux et al. (2009[Reux, B., Nevalainen, T., Raitio, K. H. & Koskinen, A. M. P. (2009). Bioorg. Med. Chem. 17, 4441-4447.]); 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 related structures, see: Thanigaimani et al. (2013a[Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013a). Acta Cryst. E69, o42-o43.],b[Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013b). Acta Cryst. E69, o44.]); Loh et al. (2010[Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2357.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • 2C10H11N2+·2C3H3O4-·C3H4O4

  • Mr = 628.59

  • Monoclinic, C 2/c

  • a = 24.701 (2) Å

  • b = 4.8530 (4) Å

  • c = 25.063 (2) Å

  • [beta] = 95.321 (3)°

  • V = 2991.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.990

  • 25870 measured reflections

  • 3835 independent reflections

  • 2644 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O3 1.00 (2) 1.76 (2) 2.7450 (17) 172.3 (18)
O2-H1O2...O4 0.86 (1) 1.64 (1) 2.4630 (18) 159 (2)
C1-H1A...O4 0.93 2.44 3.095 (2) 127
N2-H1N2...O1i 0.91 (2) 2.11 (2) 3.012 (2) 173.4 (18)
N2-H2N2...O5ii 0.90 (2) 2.20 (2) 3.076 (2) 166 (2)
O6-H106...O3iii 1.02 (3) 1.60 (3) 2.5927 (19) 164 (2)
C1-H1A...O2iv 0.93 2.28 3.106 (2) 148
C3-H3A...O1i 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[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: 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.  [CrossRef] [ChemPort] [ISI]
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.  [CSD] [CrossRef] [details]
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]
Reux, B., Nevalainen, T., Raitio, K. H. & Koskinen, A. M. P. (2009). Bioorg. Med. Chem. 17, 4441-4447.  [CrossRef] [PubMed] [ChemPort]
Sasaki, K., Tsurumori, A. & Hirota, T. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3851-3856.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013a). Acta Cryst. E69, o42-o43.  [CSD] [CrossRef] [details]
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013b). Acta Cryst. E69, o44.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o319-o320   [ doi:10.1107/S1600536813002547 ]

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