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Volume 68 
Part 12 
Page o3397  
December 2012  

Received 12 November 2012
Accepted 13 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.052
wR = 0.158
Data-to-parameter ratio = 18.7
Details
Open access

3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: stefan.laufer@uni-tuebingen.de

The asymmetric unit of the title compound, C16H11BrN2O, contains two independent molecules with slightly different geometries. The 4-bromobenzene ring forms dihedral angles of 26.0 (2) and 39.9 (7)° with the pyrazole ring in the two molecules while the phenyl ring is oriented at 19.7 (5) and 7.3 (0)° with respect to the pyrazole ring.

Related literature

For the biological activity of inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012[Elkady, M., Niess, R., Schaible, A. M., Bauer, J., Luderer, S., Ambrosi, G., Werz, O. & Laufer, S. A. (2012). J. Med. Chem. 55, 8958-8962.]). For details of the synthesis, see: Rathelot et al. (2002[Rathelot, P., Azas, N., El-Kashef, H., Delmas, F., Di Giorgio, C., Timon-David, P., Maldonado, J. & Vanelle, P. (2002). Eur. J. Med. Chem. 37, 671-679.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11BrN2O

  • Mr = 327.18

  • Triclinic, [P \overline 1]

  • a = 9.6716 (8) Å

  • b = 11.4617 (9) Å

  • c = 13.8257 (10) Å

  • [alpha] = 113.497 (5)°

  • [beta] = 92.753 (6)°

  • [gamma] = 93.753 (6)°

  • V = 1397.91 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.94 mm-1

  • T = 298 K

  • 0.34 × 0.18 × 0.06 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • Absorption correction: multi-scan (MULABS; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.477, Tmax = 0.660

  • 14312 measured reflections

  • 6740 independent reflections

  • 2856 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.158

  • S = 0.92

  • 6740 reflections

  • 361 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.73 e Å-3

Data collection: X-AREA (Stoe & Cie, 2010[Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2010[Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6856 ).


Acknowledgements

This research was supported financially by the Landesgraduiertenförderung program of the Ministry of Science, Research and Arts of the state of Baden-Württemberg, Germany.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Elkady, M., Niess, R., Schaible, A. M., Bauer, J., Luderer, S., Ambrosi, G., Werz, O. & Laufer, S. A. (2012). J. Med. Chem. 55, 8958-8962.  [CrossRef] [ChemPort] [PubMed]
Rathelot, P., Azas, N., El-Kashef, H., Delmas, F., Di Giorgio, C., Timon-David, P., Maldonado, J. & Vanelle, P. (2002). Eur. J. Med. Chem. 37, 671-679.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.


Acta Cryst (2012). E68, o3397  [ doi:10.1107/S1600536812046752 ]

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