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Volume 69 
Part 7 
Pages o1081-o1082  
July 2013  

Received 23 May 2013
Accepted 5 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.071
wR = 0.193
Data-to-parameter ratio = 18.1
Details
Open access

2-Oxo-2H-chromen-4-yl 4-methylbenzoate

aLaboratoire d'Instrumentation Image et Spectroscopie, DFR-GEE, Institut National Polytechnique Félix Houphouët-Boigny, BP 1093 Yamoussoukro, Côte d'Ivoire,bLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université Félix Houphouët-Boigny de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, and cLaboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03, Burkina Faso
Correspondence e-mail: abou_akoun@yahoo.fr

The asymmetric unit of the title compound, C17H12O4, consists of two independent molecules. The chromen-2-one ring and the 4-methylbenzoate side chain are inclined to one another at a dihedral angle of 64.79 (10)° in one molecule and 88.3 (1)° in the other. In the crystal, molecules form R22(8) centrosymmetric dimers via C-H...O hydrogen bonds. These dimers are stacked by C-H...O hydrogen bonds, resulting in R22(18) and R32(16) ring motifs. [pi]-[pi] stacking interactions between two parallel chromen-2-one rings, with centroid-centroid distances of 3.743 (1) and 3.771 (1) Å, are also present.

Related literature

For related structures and background to coumarin derivatives, see: Abou et al. (2011[Abou, A., Djandé, A., Sessouma, B., Saba, A. & Kakou-Yao, R. (2011). Acta Cryst. E67, o2269-o2270.], 2012a[Abou, A., Sessouma, B., Djandé, A., Saba, A. & Kakou-Yao, R. (2012a). Acta Cryst. E68, o537-o538.],b[Abou, A., Djandé, A., Danger, G., Saba, A. & Kakou-Yao, R. (2012b). Acta Cryst. E68, o3438-o3439.]). For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009[Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.]); Vukovic et al. (2010[Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.]); Emmanuel-Giota et al. (2001[Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For [pi]-[pi] stacking interactions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O4

  • Mr = 280.27

  • Triclinic, [P \overline 1]

  • a = 9.2790 (5) Å

  • b = 10.7696 (5) Å

  • c = 14.5758 (9) Å

  • [alpha] = 95.274 (2)°

  • [beta] = 97.875 (2)°

  • [gamma] = 104.788 (5)°

  • V = 1382.75 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.35 × 0.20 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 16045 measured reflections

  • 6907 independent reflections

  • 3981 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.193

  • S = 1.02

  • 6907 reflections

  • 381 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5A-H5A...O4B 0.93 2.55 3.389 (3) 151
C8A-H8A...O2Bi 0.93 2.52 3.453 (3) 177
C8B-H8B...O2Ai 0.93 2.50 3.425 (3) 176
C12A-H12A...O2Ai 0.93 2.59 3.498 (3) 167
Symmetry code: (i) -x, -y, -z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallograhy, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5325 ).


Acknowledgements

The authors thank the Spectropôle Service of the Faculty of Sciences and Techniques of Saint Jérôme (France) for the use of the diffractometer.

References

Abou, A., Djandé, A., Danger, G., Saba, A. & Kakou-Yao, R. (2012b). Acta Cryst. E68, o3438-o3439.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Abou, A., Djandé, A., Sessouma, B., Saba, A. & Kakou-Yao, R. (2011). Acta Cryst. E67, o2269-o2270.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Abou, A., Sessouma, B., Djandé, A., Saba, A. & Kakou-Yao, R. (2012a). Acta Cryst. E68, o537-o538.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.  [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.  [CrossRef]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallograhy, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1081-o1082   [ doi:10.1107/S1600536813015717 ]

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