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Volume 69 
Part 4 
Pages o539-o540  
April 2013  

Received 1 March 2013
Accepted 8 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.066
wR = 0.200
Data-to-parameter ratio = 17.0
Details
Open access

5-Amino-6-methylquinolin-1-ium 3-carboxypropanoate

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

The asymmetric unit of the title salt, C10H11N2+·C4H5O4-, consists of two independent 5-amino-6-methylquinolin-1-ium cations and two 3-carboxypropanoate anions. Both cations are protonated at the pyridine N atoms and are essentially planar, with maximum deviations of 0.026 (3) and 0.016 (2) Å. In the crystal, the cations and anions are linked via N-H...O and O-H...O hydrogen bonds, forming a layer parallel to the ab plane. In the layer, weak C-H...O hydrogen bonds and [pi]-[pi] stacking interactions, with centroid-to-centroid distances of 3.7283 (15) and 3.8467 (15) Å, are observed. The crystal structure also features weak C-H...O hydrogen bonds between the layers.

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.],c[Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013c). Acta Cryst. E69, o319-o320.]); Loh et al. (2010[Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2357.]); Sauer et al. (2008[Sauer, M., Porro, D., Mattanovich, D. & Branduaradi, P. (2008). Trends Biotechnol. 26, 100-108.]). For reference 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 stability of the temperature controller used for data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11N2+·C4H5O4-

  • Mr = 276.29

  • Triclinic, [P \overline 1]

  • a = 8.0784 (3) Å

  • b = 10.8234 (4) Å

  • c = 16.4366 (6) Å

  • [alpha] = 91.608 (2)°

  • [beta] = 101.039 (2)°

  • [gamma] = 105.782 (2)°

  • V = 1352.49 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.31 × 0.17 × 0.16 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 = 0.970, Tmax = 0.984

  • 19941 measured reflections

  • 6733 independent reflections

  • 4669 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.200

  • S = 1.04

  • 6733 reflections

  • 395 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1NA...O4A 0.88 (1) 1.78 (1) 2.667 (3) 177 (4)
N1B-H1NB...O4B 0.97 (3) 1.71 (3) 2.664 (3) 170 (3)
O2A-H1OA...O4Ai 0.83 (2) 1.69 (2) 2.520 (2) 176 (3)
O2B-H1OB...O4Bi 0.93 (4) 1.60 (4) 2.525 (2) 179 (4)
N2A-H2NA...O3Aii 0.99 (5) 1.97 (5) 2.931 (3) 163 (4)
N2A-H3NA...O2Biii 0.93 (4) 2.11 (4) 2.937 (3) 149 (3)
N2B-H2NB...O2Aii 0.87 (3) 2.22 (3) 3.037 (3) 157 (3)
N2B-H3NB...O3Bii 0.87 (3) 2.14 (3) 3.001 (3) 172 (3)
C7A-H7AA...O3Aii 0.95 2.42 3.343 (3) 165
C9A-H9AA...O1Aiv 0.95 2.37 3.271 (3) 158
C7B-H7BA...O3Bii 0.95 2.31 3.253 (3) 169
C8B-H8BA...O3Bv 0.95 2.51 3.323 (3) 143
C9B-H9BA...O4Bv 0.95 2.52 3.388 (3) 153
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x-1, y+1, z; (iv) -x+1, -y+1, -z; (v) -x+1, -y+1, -z+1.

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: IS5252 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for research facilities and a 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 the 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.
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]
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]
Sauer, M., Porro, D., Mattanovich, D. & Branduaradi, P. (2008). Trends Biotechnol. 26, 100-108.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013c). Acta Cryst. E69, o319-o320.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o539-o540   [ doi:10.1107/S1600536813006673 ]

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