8-Hy­droxy-5,7-dimethyl­quinolin-1-ium chloride dihydrate

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

doi:10.1107/S1600536812049495

Volume 69
Part 1
Page o44
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) = 0.001 Å
R = 0.028
wR = 0.092
Data-to-parameter ratio = 19.9
Details

8-Hydroxy-5,7-dimethylquinolin-1-ium chloride dihydrate

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 title hydrated salt, C₁₁H₁₂NO⁺·Cl^-·2H₂O, the quinoline ring system is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the crystal, the three components are linked by O-HO, N-HO, O-HCl and weak C-HO hydrogen bonds, forming a layer structure parallel to the ac plane. The crystal structure is further stabilized by [pi] - [pi] stacking interactions, with centroid-centroid distances of 3.5213 (6) and 3.7176 (6) Å.

Related literature

For background to and the biological activity of quinoline derivatives, see: Balasubramanian & Muthiah (1996a,b); Morimoto et al. (1991); Markees et al. (1970). 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⁺·Cl^-·2H₂O
M_r = 245.70
Triclinic, $[P \overline 1]$
a = 6.7990 (5) Å
b = 9.2215 (6) Å
c = 10.2123 (7) Å
= 103.820 (1)°
= 95.629 (1)°
= 105.517 (1)°
V = 590.04 (7) Å³
Z = 2
Mo K radiation
= 0.32 mm^-1
T = 100 K
0.38 × 0.20 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.889, T_max = 0.958
9368 measured reflections
3410 independent reflections
3153 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.092
S = 1.08
3410 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1AO2W	0.95	2.55	3.2871 (13)	134
O2W-H2W2Cl1	0.858 (19)	2.274 (19)	3.1306 (10)	177.4 (18)
O1-H1O1O1W	0.874 (19)	1.811 (19)	2.6718 (10)	167.9 (18)
N1-H1N1O1Wⁱ	0.826 (18)	1.977 (18)	2.7516 (11)	155.9 (17)
O1W-H2W1Cl1ⁱ	0.83 (2)	2.27 (2)	3.0758 (9)	164.0 (18)
O2W-H1W2Cl1ⁱⁱ	0.76 (2)	2.36 (2)	3.1187 (10)	177.7 (18)
O1W-H1W1O2Wⁱⁱⁱ	0.805 (19)	1.86 (2)	2.6690 (11)	177.2 (19)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+2; (iii) x, y, z-1.

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: IS5226 ).

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.
Balasubramanian, T. P. & Thomas Muthiah, P. (1996a). Acta Cryst. C52, 1017-1019.
Balasubramanian, T. & Muthiah, P. T. (1996b). Acta Cryst. C52, 2072-2073.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds