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Volume 69 
Part 12 
Page o1787  
December 2013  

Received 8 November 2013
Accepted 12 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.046
wR = 0.134
Data-to-parameter ratio = 14.2
Details
Open access

2,4,6-Tri­nitro­phenyl 4-bromo­benzoate

aDepartamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia
Correspondence e-mail: rodimo26@yahoo.es

In the title benzoate derivative, C13H6BrN3O8, the benzene rings form a dihedral angle of 80.90 (9)°. The ester moiety forms dihedral angles of 3.2 (2) and 82.8 4(10)° with the benzene and picryl rings, respectively. The Br atom is disordered over two positions, with the site occupancy for the minor component being 0.48 (4). The crystal structure features C-H...O inter­actions, which generate a three-dimensional network.

Related literature

For similar esters, see: Moreno-Fuquen et al. (2013[Moreno-Fuquen, R., Mosquera, F., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013). Acta Cryst. E69, o966.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

[Scheme 1]

Experimental

Crystal data
  • C13H6BrN3O8

  • Mr = 412.12

  • Monoclinic, P 21 /c

  • a = 10.8409 (5) Å

  • b = 10.0152 (7) Å

  • c = 13.9777 (7) Å

  • [beta] = 99.246 (3)°

  • V = 1497.89 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.80 mm-1

  • T = 295 K

  • 0.34 × 0.13 × 0.11 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.668, Tmax = 0.753

  • 10473 measured reflections

  • 3340 independent reflections

  • 2092 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.02

  • 3340 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O2i 0.93 2.48 3.169 (4) 131
C12-H12...O1ii 0.93 2.49 3.273 (4) 142
C5-H5...O8iii 0.93 2.46 3.384 (4) 173
C3-H3...O6iv 0.93 2.42 3.291 (4) 157
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x, -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: 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: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); 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: TK5272 ).


Acknowledgements

RMF thanks the Universidad del Valle, Colombia, for partial financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Moreno-Fuquen, R., Mosquera, F., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013). Acta Cryst. E69, o966.  [CSD] [CrossRef] [IUCr Journals]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
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] [IUCr Journals]


Acta Cryst (2013). E69, o1787  [ doi:10.1107/S1600536813031061 ]

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