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Volume 69 
Part 4 
Page o570  
April 2013  

Received 25 February 2013
Accepted 17 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.151
Data-to-parameter ratio = 13.4
Details
Open access

2,4,6-Trinitrophenyl 4-chlorobenzoate

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

In the title benzoate derivative, C13H6ClN3O8, the planes of the benzene rings form a dihedral angle of 63.46 (5)°. The dihedral angles between the benzene ring and its nitro groups are 12.78 (16)° for the first ortho, 28.4 (4) and 17.4 (4)° for the second (disordered) ortho and 3.58 (16)° for the para nitro group. The central ester moiety, -C-(C=O)-O-, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0229 Å) and forms dihedral angles of 7.37 (14)° with the chloro-substituted benzene ring and 69.85 (6)° with the trinitro-substituted benzene ring. One of the nitro groups was refined as disordered over two sets of sites with fixed site occupancies of 0.61 and 0.39. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For the industrial and synthetic applications of nitroaryl compounds, see: Moreno-Fuquen et al. (2012a[Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187.]) and references therein. For similar structures, see: Moreno-Fuquen et al. (2012b[Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.],c[Moreno-Fuquen, R., Mosquera, F., Kennedy, A. R., Morrison, C. A. & De Almeida Santos, R. H. (2012c). Acta Cryst. E68, o3493.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For a description of the Cambridge Structural Database (CSD), see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C13H6ClN3O8

  • Mr = 367.66

  • Monoclinic, P 21 /c

  • a = 9.3526 (3) Å

  • b = 11.4793 (3) Å

  • c = 13.6089 (4) Å

  • [beta] = 93.612 (2)°

  • V = 1458.17 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 295 K

  • 0.35 × 0.31 × 0.24 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 15908 measured reflections

  • 3288 independent reflections

  • 2424 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.151

  • S = 1.02

  • 3288 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 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
C13-H13...O4i 0.93 2.55 3.472 (3) 174
C5-H5...O8ii 0.93 2.53 3.457 (2) 174
C3-H3...O6Biii 0.93 2.36 3.188 (5) 147
C12-H12...O1iv 0.93 2.51 3.377 (2) 156
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+2.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: 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: 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, 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: LH5591 ).


Acknowledgements

RMF is grateful to the Universidad del Valle, Colombia, for partial financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CSD] [CrossRef] [details]
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.  [CSD] [CrossRef] [details]
Moreno-Fuquen, R., Mosquera, F., Kennedy, A. R., Morrison, C. A. & De Almeida Santos, R. H. (2012c). Acta Cryst. E68, o3493.  [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]


Acta Cryst (2013). E69, o570  [ doi:10.1107/S1600536813007332 ]

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