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Volume 69 
Part 8 
Page o1246  
August 2013  

Received 5 July 2013
Accepted 7 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 125 K
Mean [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 22.5
Details
Open access

2-Bromo-5-fluorobenzaldehyde

aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
Correspondence e-mail: jotanski@vassar.edu

In the title compound, C7H4BrFO, the benzaldehyde O atom is found to be trans to the 2-bromo substituent. In the crystal, short Br...F interactions between the bromine and fluorine substituents are observed at distances of 3.1878 (14), 3.3641 (13) and 3.3675 (14) Å. Offset face-to-face [pi]-stacking interactions are also observed for both of the independent molecules in the asymmetric unit running parallel to the crystallographic b axis, characterized by centroid-centroid distances of 3.8699 (2) and 3.8699 (2) Å.

Related literature

For information on the synthesis of 2-bromo-5-fluorobenzaldehyde, see: Dubost et al. (2011[Dubost, E., Fossey, C., Cailly, T., Rault, S. & Fabis, F. (2011). J. Org. Chem. 76, 6414-6420.]). For vibrational spectroscopic analysis and ab initio structure calculations on 2-bromo-5-fluorobenzaldehyde, see: Hiremath & Sundius (2009[Hiremath, C. S. & Sundius, T. (2009). Spectrochim. Acta Part A, 74, 1260-1267.]). For the use of 2-bromo-5-fluorobenzaldehyde in organic synthesis of biologically active compounds, see: Chen et al. (2013[Chen, D. S., Dou, G. L., Li, Y. L., Liu, Y. & Wang, X. S. (2013). J. Org. Chem. 78, 5700-5704.]). For additional information on halogenated aromatic aldehydes in crystal structures, see: Byrn et al. (1993[Byrn, M. P., Curtis, C. J., Hsiou, Y., Khan, S. I., Sawin, P. A., Tendick, S. K., Terzis, A. & Strouse, C. E. (1993). J. Am. Chem. Soc. 115, 9480-9497.]); Moorthy et al. (2003[Moorthy, J. N., Venkatakrishnan, P., Mal, P., Dixit, S. & Venugopalan, P. (2003). Cryst. Growth Des. 3, 581-585.]). For information on halogen-halogen interactions in crystal structures, see: Pedireddi et al. (1994[Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.]).

[Scheme 1]

Experimental

Crystal data
  • C7H4BrFO

  • Mr = 203.01

  • Monoclinic, P 21 /c

  • a = 15.3593 (6) Å

  • b = 3.8699 (2) Å

  • c = 23.4189 (9) Å

  • [beta] = 106.330 (1)°

  • V = 1335.84 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 6.09 mm-1

  • T = 125 K

  • 0.36 × 0.16 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.218, Tmax = 0.838

  • 20203 measured reflections

  • 4080 independent reflections

  • 3468 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.068

  • S = 1.03

  • 4080 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.83 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2171 ).


Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.
Byrn, M. P., Curtis, C. J., Hsiou, Y., Khan, S. I., Sawin, P. A., Tendick, S. K., Terzis, A. & Strouse, C. E. (1993). J. Am. Chem. Soc. 115, 9480-9497.  [CrossRef] [ChemPort] [Web of Science]
Chen, D. S., Dou, G. L., Li, Y. L., Liu, Y. & Wang, X. S. (2013). J. Org. Chem. 78, 5700-5704.  [CrossRef] [ChemPort] [PubMed]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Dubost, E., Fossey, C., Cailly, T., Rault, S. & Fabis, F. (2011). J. Org. Chem. 76, 6414-6420.  [CSD] [CrossRef] [ChemPort] [PubMed]
Hiremath, C. S. & Sundius, T. (2009). Spectrochim. Acta Part A, 74, 1260-1267.  [ChemPort]
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]
Moorthy, J. N., Venkatakrishnan, P., Mal, P., Dixit, S. & Venugopalan, P. (2003). Cryst. Growth Des. 3, 581-585.  [CSD] [CrossRef] [ChemPort]
Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1246  [ doi:10.1107/S1600536813018783 ]

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