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Volume 69 
Part 6 
Page o966  
June 2013  

Received 16 May 2013
Accepted 19 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.162
Data-to-parameter ratio = 14.9
Details
Open access

2,4,6-Trinitrophenyl 3-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 73.59 (7)°. The central ester unit forms an angle of 20.38 (12)° with the chloro-substituted benzene ring. In the crystal, molecules are linked by weak C-H...O interactions, forming helical chains along [101] and [100].

Related literature

For investigations on reaction kinetics, see: Kirkien-Konasiewicz & Maccoll (1964[Kirkien-Konasiewicz, A. & Maccoll, A. (1964). J. Chem. Soc. pp. 1267-1274.]); Belousova et al. (2000[Belousova, I. A., Simanenko, Yu. S., Savelova, V. A. & Suprun, I. P. (2000). Russ. J. Org. Chem. 36, 1656-1664.]). For spectroscopic and theoretical studies, 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.]). 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. (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.],c[Moreno-Fuquen, R., Mosquera, F., Kennedy, A. R., Morrison, C. A. & De Almeida Santos, R. H. (2012c). Acta Cryst. E68, o3493.], 2013[Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & De Simone, C. A. (2013). Acta Cryst. E69, o570.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and for hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]). 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
  • C13H6ClN3O8

  • Mr = 367.66

  • Monoclinic, P 21 /c

  • a = 11.0633 (4) Å

  • b = 9.6560 (4) Å

  • c = 14.0251 (6) Å

  • [beta] = 94.009 (2)°

  • V = 1494.60 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 295 K

  • 0.24 × 0.24 × 0.17 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 16939 measured reflections

  • 3383 independent reflections

  • 2015 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.162

  • S = 1.00

  • 3383 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O3i 0.93 2.50 3.167 (3) 128
C11-H11...O1ii 0.93 2.46 3.263 (3) 145
C13-H13...O4iii 0.93 2.41 3.312 (3) 165
C10-H10...O2iv 0.93 2.60 3.278 (3) 131
C5-H5...O8v 0.93 2.48 3.404 (3) 174
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y, -z+1; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 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: HG5316 ).


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]
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.
Belousova, I. A., Simanenko, Yu. S., Savelova, V. A. & Suprun, I. P. (2000). Russ. J. Org. Chem. 36, 1656-1664.  [ChemPort]
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [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.  [ISI] [CrossRef] [ChemPort]
Kirkien-Konasiewicz, 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.  [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., Ellena, J., Tenorio, J. C. & De Simone, C. A. (2013). Acta Cryst. E69, o570.  [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] [ChemPort] [details]


Acta Cryst (2013). E69, o966  [ doi:10.1107/S1600536813013792 ]

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