8-Hy­droxy-5,7-dimethyl­quinolin-1-ium hydrogen sulfate

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

doi:10.1107/S1600536812049483

Volume 69
Part 1
Pages o42-o43
January 2013

Received 27 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.103
Data-to-parameter ratio = 18.8
Details

8-Hydroxy-5,7-dimethylquinolin-1-ium hydrogen sulfate

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 quinoline ring system of the title salt, C₁₁H₁₂NO⁺·HSO₄^-, is essentially planar, with a maximum deviation of 0.054 (2) Å for all non H atoms. In the crystal, the cations and anions are linked via N-HO, O-HO and weak C-HO hydrogen bonds, and are stacked respectively in columns along the a axis. [pi] - [pi] stacking interactions, with centroid-centroid distances of 3.5473 (12) and 3.6926 (12) Å, are also observed. The crystal studied was an inversion twin with refined components of 0.43 (7):0.57 (7).

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: Loh et al. (2010a,b). 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

C₁₁H₁₂NO⁺·HSO₄^-
M_r = 271.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.6750 (9) Å
b = 11.6952 (14) Å
c = 14.7283 (18) Å
V = 1149.8 (3) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 100 K
0.41 × 0.17 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.889, T_max = 0.956
9735 measured reflections
3341 independent reflections
3142 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.103
S = 1.05
3341 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.84 e Å^-3
_min = -0.42 e Å^-3
Absolute structure: Flack (1983), 1410 Friedel pairs
Flack parameter: 0.43 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O3ⁱ	0.91 (2)	1.90 (2)	2.7753 (17)	161 (2)
O5-H1O5O2ⁱⁱ	0.79 (3)	1.91 (3)	2.698 (2)	172 (2)
O1-H1O1O4ⁱ	0.97 (4)	1.64 (4)	2.601 (2)	172 (3)
C3-H3AO5ⁱⁱⁱ	0.95	2.46	3.3448 (19)	154
C11-H11CO3ⁱⁱ	0.98	2.50	3.445 (3)	161
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5225 ).

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.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o2357.
Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o2396.
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.

organic compounds