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Volume 66 
Part 11 
Page o2872  
November 2010  

Received 30 September 2010
Accepted 5 October 2010
Online 20 October 2010

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.072
wR = 0.230
Data-to-parameter ratio = 13.3
Details
Open access

3-(Pyridin-2-yl)coumarin

Yu-Xia Daa* and Zheng-Jun Quana

aGansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: dayuxia@nwnu.edu.cn

In the title compound, C14H9NO2, the dihedral angle between the pyridine ring and the lactone ring is 10.40 (3)°. The coumarin ring system is nearly planar, with a dihedral angle of 1.40 (2)° between the lactone and benzene rings. An intramolecular C-H...O hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of C-H...O interactions occur, generating R22(14) loops.

Related literature

For background to the structures and properties of coumarins, see: Fylaktakidou et al. (2004[Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2004). Curr. Pharm. Des. 10, 3813-3833.]); Griffiths et al. (1995[Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327-339.]); Moffett (1964[Moffett, R. B. (1964). J. Med. Chem. 7, 446-449.]); Ren & Huo (2008[Ren, X. F. & Huo, S. Q. (2008). WO Patent 2008/010915 A2.]); Ren et al. (2010[Ren, X. F., Kondakova, M. E., Giesen, D. J., Rajeswaran, M., Madaras, M. & Lenhart, W. C. (2010). Inorg. Chem. 49, 1301-1303.]); Trenor et al. (2004[Trenor, S. R., Shultz, A. R., Love, B. J. & Long, T. E. (2004). Chem. Rev. 104, 3059-3077.]); Walshe et al. (1997[Walshe, M., Howarth, J., Kelly, M. T., O'Kennedy, R. & Smyth, M. R. (1997). J. Pharm. Biomed. Anal. 16, 319-325.]); Yu et al. (2006[Yu, T. Z., Zhao, Y. L. & Fan, D. W. (2006). J. Mol. Struct. 791, 18-22.]); Yu, Yang et al. (2010[Yu, T. Z., Yang, S. D., Zhao, Y. L., Zhang, H., Han, X. Q., Fan, D. W., Qiu, Y. Q. & Chen, L. L. (2010). J. Photochem. Photobiol. A, 214, 92-99.]); Yu, Zhang et al. (2010[Yu, T. Z., Zhang, P., Zhao, Y. L., Zhang, H., Meng, J., Fan, D. W., Chen, L. L. & Qiu, Y. Q. (2010). Org. Electron. 11, 41-49.]). For reference bond lengths, 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.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9NO2

  • Mr = 223.22

  • Orthorhombic, P b c a

  • a = 7.1107 (3) Å

  • b = 13.9635 (5) Å

  • c = 21.2867 (9) Å

  • V = 2113.56 (15) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.77 mm-1

  • T = 293 K

  • 0.31 × 0.22 × 0.11 mm
Data collection

  • Siemens SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.795, Tmax = 0.920

  • 4495 measured reflections

  • 2055 independent reflections

  • 1581 reflections with I > 2[sigma](I)

  • Rint = 0.021
Refinement

  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.230

  • S = 1.09

  • 2055 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O2 0.93 2.25 2.875 (3) 124
C12-H12...O2i 0.93 2.50 3.318 (3) 147
Symmetry code: (i) -x-1, -y, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5667 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Gansu Province (3ZS061-A25-019).

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.
Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2004). Curr. Pharm. Des. 10, 3813-3833.  [ISI] [CrossRef] [PubMed] [ChemPort]
Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327-339.  [CrossRef] [ChemPort]
Moffett, R. B. (1964). J. Med. Chem. 7, 446-449.  [CrossRef] [PubMed] [ChemPort] [ISI]
Ren, X. F. & Huo, S. Q. (2008). WO Patent 2008/010915 A2.
Ren, X. F., Kondakova, M. E., Giesen, D. J., Rajeswaran, M., Madaras, M. & Lenhart, W. C. (2010). Inorg. Chem. 49, 1301-1303.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Trenor, S. R., Shultz, A. R., Love, B. J. & Long, T. E. (2004). Chem. Rev. 104, 3059-3077.  [ISI] [CrossRef] [PubMed] [ChemPort]
Walshe, M., Howarth, J., Kelly, M. T., O'Kennedy, R. & Smyth, M. R. (1997). J. Pharm. Biomed. Anal. 16, 319-325.  [CrossRef] [ChemPort] [PubMed] [ISI]
Yu, T. Z., Yang, S. D., Zhao, Y. L., Zhang, H., Han, X. Q., Fan, D. W., Qiu, Y. Q. & Chen, L. L. (2010). J. Photochem. Photobiol. A, 214, 92-99.  [CrossRef] [ChemPort]
Yu, T. Z., Zhang, P., Zhao, Y. L., Zhang, H., Meng, J., Fan, D. W., Chen, L. L. & Qiu, Y. Q. (2010). Org. Electron. 11, 41-49.  [ISI] [CrossRef] [ChemPort]
Yu, T. Z., Zhao, Y. L. & Fan, D. W. (2006). J. Mol. Struct. 791, 18-22.  [ISI] [CSD] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, o2872  [ doi:10.1107/S1600536810039796 ]

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