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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 [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 13.4
Details
Open access

2,4,6-Trinitrophenyl 4-methylbenzoate

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-H...O interactions into helical chains along [010].

Related literature

For optical, pharmacological and crystalline properties of picric acid, see: Khan et al. (2010[Khan, I. M., Ahmad, A. & Oves, M. (2010). Spectrochim. Acta Part A, 77, 1059-1064.]); Zaderenko et al. (1997[Zaderenko, P., Gil, M. S., López, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997). Acta Cryst. B53, 961-967.]). For picric acid derivatives, see: Bertolasi et al. (2011[Bertolasi, V., Gilli, P. & Gilli, G. (2011). Cryst. Growth Des. 11, 2724-2735.]). For bond-length data, see: Allen et al. (1987[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.]). For similar structures, see: Moreno-Fuquen et al. (2012[Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012). Acta Cryst. E68, o2187.]); Bibi et al. (2009[Bibi, U., Siddiqi, H. M., Bolte, M. & Akhter, Z. (2009). Acta Cryst. E65, o3038.]); Shibakami et al. (1994[Shibakami, M., Tamura, M., Arimura, T., Kurosawa, S. & Sekiya, A. (1994). Acta Cryst. C50, 592-594.]); Shibakami & Sekiya (1995[Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.]); For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and for supramolecular aggregation behaviour of isomers, see: 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.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9N3O8

  • Mr = 347.24

  • Monoclinic, P 21 /c

  • a = 7.6126 (2) Å

  • b = 8.2124 (2) Å

  • c = 23.9893 (7) Å

  • [beta] = 94.448 (1)°

  • V = 1495.24 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.017

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

  • wR(F2) = 0.123

  • S = 1.02

  • 3044 reflections

  • 227 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O8i 0.93 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[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: HKL DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [ChemPort]
Bibi, U., Siddiqi, H. M., Bolte, M. & Akhter, Z. (2009). Acta Cryst. E65, o3038.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [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]
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.  [ISI] [CrossRef] [ChemPort] [details]
Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012). Acta Cryst. E68, o2187.  [CSD] [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
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.  [CrossRef] [details]
Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.  [CrossRef] [details]
Shibakami, M., Tamura, M., Arimura, T., Kurosawa, S. & Sekiya, A. (1994). Acta Cryst. C50, 592-594.  [CrossRef] [details]
Zaderenko, P., Gil, M. S., López, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997). Acta Cryst. B53, 961-967.  [ISI] [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3107  [ doi:10.1107/S1600536812041773 ]

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