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Volume 69 
Part 3 
Page o345  
March 2013  

Received 21 January 2013
Accepted 29 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.126
Data-to-parameter ratio = 13.1
Details
Open access

3-(4-Methoxybenzoyl)-6-nitrocoumarin

aDepartment of Organic Chemistry, University of Santiago de Compostela, Santiago de Compostela, A Coruna, Spain
Correspondence e-mail: svre77@gmail.com

In the title coumarin derivative (also known as 2H-chromen-2-one or 2H-1-benzopyran-2-one), C17H11NO6, the coumarin ring system is nearly planar, with a dihedral angle of 3.35 (9)° between the pyrone and the benzene rings. The dihedral angle between the planes formed by the coumarin ring system and the benzene substituent is 54.60 (7)°, clearly showing the non-coplanarity of the whole aromatic system. The crystal studied was a non-merohedral twin; the minor component refined to approximately 0.44.

Related literature

For the synthesis of the title compound, see: Raju et al. (2010[Raju, B. C., Tiwari, A. K., Kumar, J. A., Ali, A. Z., Agawane, S. B., Saidachary, G. & Madhusudana, K. (2010). Bioorg. Med. Chem. 18, 358-365.]). For examples of the biological activity of coumarin derivatives, see: Borges et al. (2009[Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.]), Matos et al. (2011a[Matos, M. J., Terán, C., Pérez-Castillo, Y., Uriarte, E., Santana, L. & Viña, D. (2011a). J. Med. Chem. 54, 7127-7137.],b[Matos, M. J., Vazquez-Rodriguez, S., Santan, L., Uriarte, E. & Viña, D. (2011b). Bioorg. Med. Chem. Lett. 21, 4224-4227.],c[Matos, M. J., Santana, L., Uriarte, E., Delogu, G., Corda, M., Fadda, M. B., Era, B. & Fais, A. (2011c). Bioorg. Med. Chem. Lett. 21, 3342-3345.]), Viña et al. (2012a[Viña, D., Matos, M. J., Yáñez, M., Santana, L. & Uriarte, E. (2012a). Med. Chem. Commun. 3, 213-218.],b[Viña, D., Matos, M. J., Ferino, G., Cadoni, E., Laguna, R., Borges, F., Uriarte, E. & Santana, L. (2012b). Chem. Med. Chem. 7, 464-470.]); Vazquez-Rodriguez et al. (2013[Vazquez-Rodriguez, S., Matos, M. J., Santana, L., Uriarte, E., Borges, F., Kachler, S. & Klotz, K.-N. (2013). J. Pharm. Pharmacol. DOI: 10.1111/jphp.12028.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11NO6

  • Mr = 325.27

  • Monoclinic, P 21 /n

  • a = 8.875 (3) Å

  • b = 17.266 (5) Å

  • c = 9.174 (3) Å

  • [beta] = 95.401 (15)°

  • V = 1399.6 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.67 × 0.14 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.604, Tmax = 0.745

  • 30736 measured reflections

  • 2864 independent reflections

  • 2200 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.126

  • S = 0.91

  • 2864 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: 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: GO2080 ).


Acknowledgements

This work was partially supported by the funds of the Xunta da Galicia (09CSA030203PR) and the Ministerio de Sanidad y Consumo (PS09/00501). SVR thanks the FPU program for her PhD grant AP2008-04263.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Matos, M. J., Santana, L., Uriarte, E., Delogu, G., Corda, M., Fadda, M. B., Era, B. & Fais, A. (2011c). Bioorg. Med. Chem. Lett. 21, 3342-3345.  [CrossRef] [ChemPort] [PubMed]
Matos, M. J., Terán, C., Pérez-Castillo, Y., Uriarte, E., Santana, L. & Viña, D. (2011a). J. Med. Chem. 54, 7127-7137.  [ISI] [CrossRef] [ChemPort] [PubMed]
Matos, M. J., Vazquez-Rodriguez, S., Santan, L., Uriarte, E. & Viña, D. (2011b). Bioorg. Med. Chem. Lett. 21, 4224-4227.  [CrossRef] [ChemPort] [PubMed]
Raju, B. C., Tiwari, A. K., Kumar, J. A., Ali, A. Z., Agawane, S. B., Saidachary, G. & Madhusudana, K. (2010). Bioorg. Med. Chem. 18, 358-365.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vazquez-Rodriguez, S., Matos, M. J., Santana, L., Uriarte, E., Borges, F., Kachler, S. & Klotz, K.-N. (2013). J. Pharm. Pharmacol. DOI: 10.1111/jphp.12028.
Viña, D., Matos, M. J., Ferino, G., Cadoni, E., Laguna, R., Borges, F., Uriarte, E. & Santana, L. (2012b). Chem. Med. Chem. 7, 464-470.  [PubMed]
Viña, D., Matos, M. J., Yáñez, M., Santana, L. & Uriarte, E. (2012a). Med. Chem. Commun. 3, 213-218.


Acta Cryst (2013). E69, o345  [ doi:10.1107/S1600536813002948 ]

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