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Volume 69 
Part 6 
Page o990  
June 2013  

Received 22 April 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.093
Data-to-parameter ratio = 13.0
Details
Open access

Methyl 2-[(2-chloroquinolin-3-yl)(hydroxy)methyl]acrylate

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

There are two independent molecules (A and B) in the asymmetric unit of the title compound, C14H12ClNO3. The mean planes of the methyl ester unit (Cmethyl-O-C=O; r.m.s. deviation = 0.051 Å for molecule A and 0.016 Å for molecule B) and the chloroquilonine ring system (r.m.s. deviation = 0.023 Å for molecule A and 0.014 Å for molecule B) form dihedral angles of 63.5 (1)° in molecule A and 78.1 (1)° in molecule B. The main difference between the two independent molecules is reflected in the (H)O-C-C=C(H2) torsion angle which is -109.7 (2)° in molecule A and 10.6 (2)° in molecule B. An intramolecular O-H...O hydrogen bond is observed in molecule A. In the crystal, molecules A and B are linked into pairs via bifurcated O-H...(N,Cl) hydrogen bonds and a weak C-H...O hydrogen bond links pairs of molecules into chains along [100].

Related literature

For the biological activity of quilonine compounds, see: Biavatti et al. (2002[Biavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66-70.]); Towers et al. (1981[Towers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136-142.]); Shen et al. (1999[Shen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543-548.]). For their luminescent properties, see: Montes et al. (2006[Montes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523-4535.]). For applications of acrylate compounds, see: Bhatia et al. (2007[Bhatia, S. P., Wellington, G. A., Cocchiara, J., Lalko, J., Letizia, C. S. & Api, A. M. (2007). J. Food Chem. Toxicol. 45, S113-S119.]); Sharma (2011[Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.]). For conformational aspects of methyl esters, see: Dunitz & Schweizer (1982[Dunitz, J. D. & Schweizer, B. W. (1982). Helv. Chim. Acta, 65, 1547-1554.]). For resonance effects in acrylates, see: Merlino (1971[Merlino, S. (1971). Acta Cryst. B27, 2491-2492.]); Varghese et al. (1986[Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544-1546.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO3

  • Mr = 277.70

  • Triclinic, [P \overline 1]

  • a = 9.2614 (4) Å

  • b = 11.0309 (4) Å

  • c = 13.8161 (6) Å

  • [alpha] = 102.557 (2)°

  • [beta] = 100.646 (2)°

  • [gamma] = 103.704 (2)°

  • V = 1296.29 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • 14402 measured reflections

  • 4466 independent reflections

  • 3767 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.093

  • S = 1.03

  • 4466 reflections

  • 344 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1A...O2A 0.82 2.24 2.8372 (19) 130
O1B-H1B...Cl1Ai 0.82 2.79 3.5040 (12) 147
O1B-H1B...N1Ai 0.82 2.16 2.8609 (17) 144
C5A-H5A...O1Bii 0.93 2.56 3.451 (2) 162
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON 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: LH5607 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, India, for the data collection.

References

Bhatia, S. P., Wellington, G. A., Cocchiara, J., Lalko, J., Letizia, C. S. & Api, A. M. (2007). J. Food Chem. Toxicol. 45, S113-S119.  [CrossRef]
Biavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66-70.  [CSD] [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
Dunitz, J. D. & Schweizer, B. W. (1982). Helv. Chim. Acta, 65, 1547-1554.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Merlino, S. (1971). Acta Cryst. B27, 2491-2492.  [CrossRef] [ChemPort] [details] [ISI]
Montes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523-4535.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543-548.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Towers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136-142.  [CrossRef] [ChemPort] [PubMed] [ISI]
Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544-1546.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o990  [ doi:10.1107/S1600536813014050 ]

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