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Volume 69 
Part 5 
Page o779  
May 2013  

Received 21 March 2013
Accepted 13 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 15.5
Details
Open access

2-[(2-Chloroquinolin-3-yl)(hydroxy)methyl]acrylonitrile

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, C13H9ClN2O, the dihedral angle between the acrylonitrile C=C-CN plane and the quilonine ring system is 71.3 (2)°. In the crystal, molecules are linked by O-H...N hydrogen bonds, forming chains along [01-1]. The chains are linked into a three-dimensional network through C-H...N interactions.

Related literature

For the biological activity of quinoline and arcylonitrile compounds, see: Dutta et al. (2002[Dutta, N. J., Khunt, R. C. & Parikh, A. R. (2002). Indian J. Chem. Sect. B, 41, 433-435.]); Ohsumi et al. (1998[Ohsumi, K., Nakagawa, R., Fukuda, Y., Hatanaka, T., Morinaga, Y., Nihei, Y., Ohishi, K., Suga, Y., Akiyama, Y. & Tsuji, T. (1998). J. Med. Chem. 41, 3022-3032.]); Saczewski et al. (2004[Saczewski, F., Reszka, P., Gdaniec, M., Grunert, R. & Bednarski, P. J. (2004). J. Med. Chem. 47, 3438-3449.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9ClN2O

  • Mr = 244.67

  • Orthorhombic, P n a 21

  • a = 12.2879 (12) Å

  • b = 9.6422 (11) Å

  • c = 10.3642 (12) Å

  • V = 1228.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]) Tmin = 0.943, Tmax = 0.971

  • 6334 measured reflections

  • 2423 independent reflections

  • 2144 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.02

  • 2423 reflections

  • 156 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 819 Friedel pairs

  • Flack parameter: 0.02 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.82 1.99 2.781 (2) 161
C10-H10...N2ii 0.98 2.57 3.385 (3) 140
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5260 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Bruker (2004). SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.
Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
Dutta, N. J., Khunt, R. C. & Parikh, A. R. (2002). Indian J. Chem. Sect. B, 41, 433-435.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ohsumi, K., Nakagawa, R., Fukuda, Y., Hatanaka, T., Morinaga, Y., Nihei, Y., Ohishi, K., Suga, Y., Akiyama, Y. & Tsuji, T. (1998). J. Med. Chem. 41, 3022-3032.  [ISI] [CrossRef] [ChemPort] [PubMed]
Saczewski, F., Reszka, P., Gdaniec, M., Grunert, R. & Bednarski, P. J. (2004). J. Med. Chem. 47, 3438-3449.  [ISI] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o779  [ doi:10.1107/S1600536813010155 ]

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