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Volume 69 
Part 12 
Page o1806  
December 2013  

Received 3 October 2013
Accepted 15 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.044
wR = 0.120
Data-to-parameter ratio = 12.6
Details
Open access

4-Formyl-2-nitro­phenyl 2-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 compound, C14H8ClNO5, the benzene rings form a dihedral angle of 19.55 (9)°. The mean plane of the central ester group [r.m.s. deviation = 0.024 Å] forms dihedral angles of 53.28 (13) and 36.93 (16)°, respectively, with the nitro- and chloro-substituted rings. The nitro group forms a dihedral angle of 19.24 (19)° with the benzene ring to which it is attached. In the crystal, mol­ecules are linked by weak C-H...O hydrogen bonds, forming C(7) chains, which run along [100].

Related literature

For industrial applications of nitro­aromatic compounds, see: Ju & Parales (2010[Ju, K. S. & Parales, R. E. (2010). Microbiol. Mol. Biol. Rev. 74, 250-272.]). For similar structures, see: Moreno-Fuquen et al. (2013a[Moreno-Fuquen, R., Hernandez, G., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013a). Acta Cryst. E69, o793.],b[Moreno-Fuquen, R., Mosquera, F., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013b). Acta Cryst. E69, o966.]); For information on hydrogen bonds, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For hydrogen-bond graph-set motifs, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8ClNO5

  • Mr = 305.66

  • Orthorhombic, P n a 21

  • a = 16.2367 (7) Å

  • b = 7.1047 (2) Å

  • c = 11.4018 (3) Å

  • V = 1315.28 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 293 K

  • 0.22 × 0.19 × 0.03 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 4581 measured reflections

  • 2449 independent reflections

  • 1762 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.120

  • S = 1.03

  • 2449 reflections

  • 194 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack parameter determined using 664 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: -0.05 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14...O4i 1.10 (6) 2.48 (6) 3.381 (7) 138 (4)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z].

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: SHELXL2013 (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: LH5661 ).


Acknowledgements

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

References

Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ju, K. S. & Parales, R. E. (2010). Microbiol. Mol. Biol. Rev. 74, 250-272.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
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., Hernandez, G., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013a). Acta Cryst. E69, o793.  [CSD] [CrossRef] [IUCr Journals]
Moreno-Fuquen, R., Mosquera, F., Ellena, J., De Simone, C. A. & Tenorio, J. C. (2013b). 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.
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1806  [ doi:10.1107/S1600536813031346 ]

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