2,4,6-Trinitro­phenyl benzoate

Moreno-Fuquen, R.; Mosquera, F.; Kennedy, A.R.; Morrison, C.A.; De Almeida Santos, R.H.

doi:10.1107/S1600536812048362

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.073
Data-to-parameter ratio = 12.7
Details

2,4,6-Trinitrophenyl benzoate

Rodolfo Moreno-Fuquen,^a ^* Fabricio Mosquera,^a Alan R. Kennedy,^b Catriona A. Morrison ^b and Regina H. De Almeida Santos ^c

^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-HO interactions, forming helical chains along [010].

Related literature

For theoretical and spectroscopic properties of nitrophenyl esters, see: Ibrahim et al. (2011); Kirkien-Konasievicz & Maccoll (1964). For the structures of similar esters, see: Moreno-Fuquen et al. (2012a,b); Shibakami & Sekiya (1995); Gowda et al. (2007). For structural properties of nitrophenyl compounds, see: Domenicano et al. (1990); Glidewell et al. (2005). For hydrogen-bonding information, see: Nardelli (1995). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₁₃H₇N₃O₈
M_r = 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 radiation
= 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(I)'
R_int = 0.019
Standard reflections: 0

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.073
S = 1.05
2758 reflections
217 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O8ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Domenicano, A., Schultz, G., Hargittai, I., Colapietro, M., Portalone, G., George, P. & Bock, C. (1990). Struct. Chem. 1, 107-122.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2005). Acta Cryst. B61, 227-237.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3756.
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, 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.
Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187.
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.

organic compounds