2,4,6-Trinitro­phenyl 4-methyl­benzoate

Moreno-Fuquen, R.; Mosquera, F.; Ellena, J.; Tenorio, J.C.; Corrêa, R.S.

doi:10.1107/S1600536812041773

Volume 68
Part 11
Page o3107
November 2012

Received 15 September 2012
Accepted 5 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 13.4
Details

2,4,6-Trinitrophenyl 4-methylbenzoate

Rodolfo Moreno-Fuquen,^a ^* Fabricio Mosquera,^a Javier Ellena,^b Juan C. Tenorio ^b and Rodrigo S. Corrêa ^c

^aDepartamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,^bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil, and ^cDepartamento de Química, Universidade Federal de São Carlos, CEP 13565-905, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C₁₄H₉N₃O₈, the benzene rings form a dihedral angle of 69.02 (5)°. The central ester group is rotated by 25.86 (9)° relative to the p-tolyl group. In the crystal, the molecules are linked by C-HO interactions into helical chains along [010].

Related literature

For optical, pharmacological and crystalline properties of picric acid, see: Khan et al. (2010); Zaderenko et al. (1997). For picric acid derivatives, see: Bertolasi et al. (2011). For bond-length data, see: Allen et al. (1987). For similar structures, see: Moreno-Fuquen et al. (2012); Bibi et al. (2009); Shibakami et al. (1994); Shibakami & Sekiya (1995); For hydrogen bonding, see: Nardelli (1995) and for supramolecular aggregation behaviour of isomers, see: Glidewell et al. (2005).

Experimental

Crystal data

C₁₄H₉N₃O₈
M_r = 347.24
Monoclinic, P 2₁ /c
a = 7.6126 (2) Å
b = 8.2124 (2) Å
c = 23.9893 (7) Å
= 94.448 (1)°
V = 1495.24 (7) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 295 K
0.27 × 0.22 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
5494 measured reflections
3044 independent reflections
2296 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.123
S = 1.02
3044 reflections
227 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O8ⁱ	0.93	2.50	3.4286 (19)	175
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2074 ).

Acknowledgements

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

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.
Bertolasi, V., Gilli, P. & Gilli, G. (2011). Cryst. Growth Des. 11, 2724-2735.
Bibi, U., Siddiqi, H. M., Bolte, M. & Akhter, Z. (2009). Acta Cryst. E65, o3038.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Glidewell, C., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2005). Acta Cryst. B61, 227-237.
Khan, I. M., Ahmad, A. & Oves, M. (2010). Spectrochim. Acta Part A, 77, 1059-1064.
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. (2012). Acta Cryst. E68, o2187.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, 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.
Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.
Shibakami, M., Tamura, M., Arimura, T., Kurosawa, S. & Sekiya, A. (1994). Acta Cryst. C50, 592-594.
Zaderenko, P., Gil, M. S., López, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997). Acta Cryst. B53, 961-967.

organic compounds