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Volume 68 
Part 12 
Page o3396  
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) = 0.005 Å
R = 0.052
wR = 0.150
Data-to-parameter ratio = 21.1
Details
Open access

2-[5-Bromo-1-(3-chlorobenzyl)-2-methyl-1H-indol-3-yl]acetic acid

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

In the title compound, C18H15BrClNO2, the indole ring system forms a dihedral angle of 86.9 (2)° with the 3-chlorobenzyl ring. In the crystal, molecules form inversion dimers connected via pairs of O-H...O hydrogen bonds.

Related literature

For 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: Maguire et al. (2001[Maguire, A. R., Plunkett, S. J., Papot, S., Clynes, M., O'Connor, R. & Touhey, S. (2001). Bioorg. Med. Chem. 9, 745-762.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15BrClNO2

  • Mr = 392.67

  • Triclinic, [P \overline 1]

  • a = 8.5386 (11) Å

  • b = 10.0157 (10) Å

  • c = 11.0821 (12) Å

  • [alpha] = 109.221 (8)°

  • [beta] = 106.229 (9)°

  • [gamma] = 101.886 (9)°

  • V = 811.52 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.71 mm-1

  • T = 298 K

  • 0.44 × 0.15 × 0.12 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • Absorption correction: integration (X-RED; Stoe & Cie, 2010[Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]) Tmin = 0.388, Tmax = 0.785

  • 9139 measured reflections

  • 4400 independent reflections

  • 2791 reflections with I > 2[sigma](I)

  • Rint = 0.040

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

  • wR(F2) = 0.150

  • S = 1.02

  • 4400 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.69 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O18-H18...O17i 0.82 1.87 2.679 (3) 170
Symmetry code: (i) -x+2, -y+1, -z+2.

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: BT6855 ).


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]
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]
Maguire, A. R., Plunkett, S. J., Papot, S., Clynes, M., O'Connor, R. & Touhey, S. (2001). Bioorg. Med. Chem. 9, 745-762.  [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, o3396  [ doi:10.1107/S1600536812046740 ]

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