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Volume 68 
Part 12 
Page o3493  
December 2012  

Received 17 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.073
Data-to-parameter ratio = 12.7
Details
Open access

2,4,6-Trinitrophenyl benzoate

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,bWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and cInstituto de Química de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title molecule, C13H7N3O8, the phenyl and benzene rings are rotated from the mean plane of the central ester group by 18.41 (9) and 81.80 (5)°, respectively. The dihedral angle between the rings is 80.12 (14)°. In the crystal, molecules are linked by weak C-H...O interactions, forming helical chains along [010].

Related literature

For theoretical and spectroscopic properties of nitrophenyl esters, see: Ibrahim et al. (2011[Ibrahim, M. F., Senior, S. A., El-atawy, M. A., El-Sadany, S. K. & Hamed, E. A. (2011). J. Mol. Struct. 1006, 303-311.]); Kirkien-Konasievicz & Maccoll (1964[Kirkien-Konasievicz, A. & Maccoll, A. (1964). J. Chem. Soc. pp. 1267-1274.]). For the structures of similar esters, see: Moreno-Fuquen et al. (2012a[Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187.],b[Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.]); Shibakami & Sekiya (1995[Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.]); Gowda et al. (2007[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3756.]). For structural properties of nitrophenyl compounds, see: Domenicano et al. (1990[Domenicano, A., Schultz, G., Hargittai, I., Colapietro, M., Portalone, G., George, P. & Bock, C. (1990). Struct. Chem. 1, 107-122.]); Glidewell et al. (2005[Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2005). Acta Cryst. B61, 227-237.]). For hydrogen-bonding information, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C13H7N3O8

  • Mr = 333.22

  • Orthorhombic, P 21 21 21

  • a = 7.5818 (3) Å

  • b = 8.3714 (2) Å

  • c = 21.0625 (10) Å

  • V = 1336.84 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 123 K

  • 0.31 × 0.21 × 0.12 mm

Data collection
  • Oxford Diffraction Xcalibur E diffractometer

  • 5179 measured reflections

  • 2758 independent reflections

  • 2563 reflections with I > 2[sigma](I)'

  • Rint = 0.019

  • Standard reflections: 0

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

  • wR(F2) = 0.073

  • S = 1.05

  • 2758 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O8i 0.95 2.44 3.388 (2) 177
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: LH5562 ).


Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database and also thanks the Universidad del Valle, Colombia, for partial financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Domenicano, A., Schultz, G., Hargittai, I., Colapietro, M., Portalone, G., George, P. & Bock, C. (1990). Struct. Chem. 1, 107-122.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2005). Acta Cryst. B61, 227-237.  [ISI] [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3756.  [CSD] [CrossRef] [details]
Ibrahim, M. F., Senior, S. A., El-atawy, M. A., El-Sadany, S. K. & Hamed, E. A. (2011). J. Mol. Struct. 1006, 303-311.  [CrossRef] [ChemPort]
Kirkien-Konasievicz, A. & Maccoll, A. (1964). J. Chem. Soc. pp. 1267-1274.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187.  [CrossRef] [details]
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.  [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.  [CrossRef] [details]


Acta Cryst (2012). E68, o3493  [ doi:10.1107/S1600536812048362 ]

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