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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 [sigma](C-C) = 0.001 Å
R = 0.028
wR = 0.092
Data-to-parameter ratio = 19.9
Details
Open access

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

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-H...O, N-H...O, O-H...Cl and weak C-H...O 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[Balasubramanian, T. P. & Thomas Muthiah, P. (1996a). Acta Cryst. C52, 1017-1019.],b[Balasubramanian, T. & Muthiah, P. T. (1996b). Acta Cryst. C52, 2072-2073.]); 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 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 the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12NO+·Cl-·2H2O

  • Mr = 245.70

  • Triclinic, [P \overline 1]

  • a = 6.7990 (5) Å

  • b = 9.2215 (6) Å

  • c = 10.2123 (7) Å

  • [alpha] = 103.820 (1)°

  • [beta] = 95.629 (1)°

  • [gamma] = 105.517 (1)°

  • V = 590.04 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.889, Tmax = 0.958

  • 9368 measured reflections

  • 3410 independent reflections

  • 3153 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...O2W 0.95 2.55 3.2871 (13) 134
O2W-H2W2...Cl1 0.858 (19) 2.274 (19) 3.1306 (10) 177.4 (18)
O1-H1O1...O1W 0.874 (19) 1.811 (19) 2.6718 (10) 167.9 (18)
N1-H1N1...O1Wi 0.826 (18) 1.977 (18) 2.7516 (11) 155.9 (17)
O1W-H2W1...Cl1i 0.83 (2) 2.27 (2) 3.0758 (9) 164.0 (18)
O2W-H1W2...Cl1ii 0.76 (2) 2.36 (2) 3.1187 (10) 177.7 (18)
O1W-H1W1...O2Wiii 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[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: 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.  [CSD] [CrossRef] [details]
Balasubramanian, T. & Muthiah, P. T. (1996b). Acta Cryst. C52, 2072-2073.  [CSD] [CrossRef] [details]
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]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o44  [ doi:10.1107/S1600536812049495 ]

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