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

Elkady, M.; Keck, P.R.W.E.F.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536812046740

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 (C-C) = 0.005 Å
R = 0.052
wR = 0.150
Data-to-parameter ratio = 21.1
Details

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

Mahmoud Elkady,^a Peter R. W. E. F. Keck,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^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-HO 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). For details of the synthesis, see: Maguire et al. (2001).

Experimental

Crystal data

C₁₈H₁₅BrClNO₂
M_r = 392.67
Triclinic, $[P \overline 1]$
a = 8.5386 (11) Å
b = 10.0157 (10) Å
c = 11.0821 (12) Å
= 109.221 (8)°
= 106.229 (9)°
= 101.886 (9)°
V = 811.52 (16) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.388, T_max = 0.785
9139 measured reflections
4400 independent reflections
2791 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.150
S = 1.02
4400 reflections
209 parameters
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.69 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O18-H18O17ⁱ	0.82	1.87	2.679 (3)	170
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
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.
Maguire, A. R., Plunkett, S. J., Papot, S., Clynes, M., O'Connor, R. & Touhey, S. (2001). Bioorg. Med. Chem. 9, 745-762.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds