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

In the title compound, C18H15BrClNO2, the indole ring system forms a dihedral angle of 86.9 (2)° with the 3-chloro-benzyl ring. In the crystal, mol-ecules 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 ▶). For details of the synthesis, see: Maguire et al. (2001 ▶).

Experimental

Crystal data

C18H15BrClNO2

M = 392.67

Triclinic,

a = 8.5386 (11) Å

b = 10.0157 (10) Å

c = 11.0821 (12) Å

α = 109.221 (8)°

β = 106.229 (9)°

γ = 101.886 (9)°

V = 811.52 (16) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.150

S = 1.02

4400 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.69 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046740/bt6855sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046740/bt6855Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046740/bt6855Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H15BrClNO2	Z = 2
Mr = 392.67	F(000) = 396
Triclinic, P1	Dx = 1.607 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5386 (11) Å	Cell parameters from 6836 reflections
b = 10.0157 (10) Å	θ = 2.4–29.3°
c = 11.0821 (12) Å	µ = 2.71 mm−1
α = 109.221 (8)°	T = 298 K
β = 106.229 (9)°	Block, colourless
γ = 101.886 (9)°	0.44 × 0.15 × 0.12 mm
V = 811.52 (16) Å3

Stoe IPDS 2T diffractometer	4400 independent reflections
Radiation source: sealed Tube	2791 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 6.67 pixels mm-1	θmax = 29.3°, θmin = 2.4°
rotation method scans	h = −11→11
Absorption correction: integration (X-RED; Stoe & Cie, 2010)	k = −13→12
Tmin = 0.388, Tmax = 0.785	l = −15→15
9139 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.069P)2 + 0.4677P] where P = (Fo2 + 2Fc2)/3
4400 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.98960 (7)	0.99173 (4)	0.68263 (5)	0.0811 (2)
Cl1	0.82521 (16)	0.14242 (15)	−0.02826 (13)	0.0943 (4)
N1	0.5804 (3)	0.3419 (3)	0.3758 (2)	0.0436 (5)
C1A	0.6557 (4)	0.4936 (3)	0.4301 (3)	0.0398 (6)
C2	0.6079 (4)	0.5993 (4)	0.3871 (3)	0.0478 (7)
H2	0.5097	0.5714	0.3094	0.057*
C3	0.7091 (5)	0.7457 (4)	0.4622 (3)	0.0520 (8)
H3	0.6801	0.8188	0.4351	0.062*
C4	0.8553 (5)	0.7865 (4)	0.5788 (3)	0.0516 (7)
C5	0.9056 (4)	0.6835 (4)	0.6232 (3)	0.0465 (7)
H5	1.0037	0.7130	0.7015	0.056*
C5A	0.8048 (4)	0.5337 (3)	0.5472 (3)	0.0396 (6)
C6	0.8162 (4)	0.3989 (3)	0.5604 (3)	0.0426 (6)
C7	0.6776 (4)	0.2843 (3)	0.4540 (3)	0.0458 (7)
C8	0.4319 (4)	0.2570 (4)	0.2463 (3)	0.0527 (7)
H8A	0.3432	0.3038	0.2471	0.063*
H8B	0.3848	0.1564	0.2387	0.063*
C9	0.4776 (4)	0.2482 (4)	0.1228 (3)	0.0476 (7)
C10	0.6134 (4)	0.2012 (4)	0.1056 (3)	0.0521 (7)
H10	0.6778	0.1724	0.1692	0.063*
C11	0.6520 (5)	0.1976 (4)	−0.0080 (3)	0.0602 (9)
C12	0.5554 (6)	0.2388 (5)	−0.1038 (3)	0.0733 (12)
H12	0.5833	0.2366	−0.1797	0.088*
C13	0.4217 (6)	0.2818 (5)	−0.0869 (4)	0.0765 (12)
H13	0.3560	0.3083	−0.1519	0.092*
C14	0.3804 (5)	0.2871 (5)	0.0259 (3)	0.0644 (9)
H14	0.2871	0.3169	0.0367	0.077*
C15	0.9604 (5)	0.3856 (4)	0.6627 (3)	0.0514 (7)
H15A	1.0681	0.4430	0.6646	0.062*
H15B	0.9548	0.2816	0.6302	0.062*
C16	0.9669 (4)	0.4356 (3)	0.8074 (3)	0.0436 (6)
O17	0.8593 (3)	0.4791 (3)	0.8448 (2)	0.0632 (7)
O18	1.1017 (3)	0.4268 (4)	0.8893 (2)	0.0717 (8)
H18	1.1012	0.4549	0.9675	0.108*
C19	0.6253 (6)	0.1216 (4)	0.4211 (4)	0.0663 (10)
H19A	0.7000	0.1043	0.4928	0.099*
H19B	0.6339	0.0682	0.3349	0.099*
H19C	0.5083	0.0871	0.4141	0.099*

	U11	U22	U33	U12	U13	U23
Br1	0.1083 (4)	0.0471 (2)	0.0743 (3)	0.0105 (2)	0.0368 (3)	0.01569 (18)
Cl1	0.0830 (8)	0.0973 (8)	0.0888 (8)	0.0194 (6)	0.0543 (7)	0.0096 (6)
N1	0.0509 (14)	0.0486 (13)	0.0299 (10)	0.0130 (11)	0.0149 (10)	0.0167 (10)
C1A	0.0468 (15)	0.0489 (15)	0.0299 (11)	0.0190 (12)	0.0183 (11)	0.0185 (11)
C2	0.0545 (18)	0.0626 (18)	0.0394 (14)	0.0274 (15)	0.0207 (13)	0.0289 (14)
C3	0.071 (2)	0.0532 (17)	0.0516 (17)	0.0312 (16)	0.0327 (17)	0.0310 (15)
C4	0.067 (2)	0.0444 (15)	0.0469 (16)	0.0165 (14)	0.0307 (15)	0.0172 (13)
C5	0.0494 (17)	0.0543 (17)	0.0339 (13)	0.0152 (14)	0.0171 (12)	0.0160 (12)
C5A	0.0476 (16)	0.0494 (15)	0.0287 (11)	0.0198 (12)	0.0188 (11)	0.0184 (11)
C6	0.0575 (18)	0.0530 (16)	0.0280 (12)	0.0266 (14)	0.0198 (12)	0.0213 (11)
C7	0.0638 (19)	0.0467 (15)	0.0363 (13)	0.0209 (14)	0.0264 (13)	0.0201 (12)
C8	0.0466 (17)	0.0630 (19)	0.0382 (14)	0.0075 (15)	0.0134 (13)	0.0171 (14)
C9	0.0476 (17)	0.0497 (16)	0.0304 (12)	0.0046 (13)	0.0091 (12)	0.0103 (11)
C10	0.0514 (18)	0.0563 (18)	0.0382 (14)	0.0070 (14)	0.0151 (13)	0.0149 (13)
C11	0.061 (2)	0.0509 (17)	0.0470 (17)	−0.0009 (15)	0.0243 (16)	0.0027 (14)
C12	0.092 (3)	0.074 (2)	0.0359 (16)	0.000 (2)	0.0260 (19)	0.0160 (16)
C13	0.091 (3)	0.094 (3)	0.0468 (19)	0.026 (3)	0.023 (2)	0.037 (2)
C14	0.072 (2)	0.076 (2)	0.0431 (17)	0.0236 (19)	0.0166 (16)	0.0258 (16)
C15	0.064 (2)	0.068 (2)	0.0361 (14)	0.0342 (17)	0.0225 (14)	0.0267 (14)
C16	0.0503 (17)	0.0512 (16)	0.0351 (13)	0.0191 (13)	0.0156 (12)	0.0235 (12)
O17	0.0651 (15)	0.104 (2)	0.0362 (11)	0.0458 (15)	0.0230 (11)	0.0328 (12)
O18	0.0711 (17)	0.121 (2)	0.0421 (12)	0.0550 (17)	0.0221 (12)	0.0410 (14)
C19	0.096 (3)	0.0489 (18)	0.059 (2)	0.0244 (19)	0.032 (2)	0.0248 (16)

Br1—C4	1.897 (3)	C8—H8B	0.9700
Cl1—C11	1.727 (4)	C9—C10	1.376 (5)
N1—C1A	1.365 (4)	C9—C14	1.380 (5)
N1—C7	1.378 (4)	C10—C11	1.379 (5)
N1—C8	1.458 (4)	C10—H10	0.9300
C1A—C2	1.384 (4)	C11—C12	1.384 (6)
C1A—C5A	1.411 (4)	C12—C13	1.340 (7)
C2—C3	1.364 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.379 (5)
C3—C4	1.391 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.375 (5)	C15—C16	1.495 (4)
C5—C5A	1.390 (4)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C5A—C6	1.425 (4)	C16—O17	1.210 (4)
C6—C7	1.370 (4)	C16—O18	1.291 (4)
C6—C15	1.485 (4)	O18—H18	0.8200
C7—C19	1.485 (4)	C19—H19A	0.9600
C8—C9	1.506 (4)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C1A—N1—C7	109.2 (2)	C10—C9—C8	120.8 (3)
C1A—N1—C8	123.7 (3)	C14—C9—C8	119.1 (3)
C7—N1—C8	126.7 (3)	C9—C10—C11	118.6 (3)
N1—C1A—C2	130.6 (3)	C9—C10—H10	120.7
N1—C1A—C5A	107.6 (2)	C11—C10—H10	120.7
C2—C1A—C5A	121.8 (3)	C10—C11—C12	121.0 (4)
C3—C2—C1A	118.1 (3)	C10—C11—Cl1	118.8 (3)
C3—C2—H2	121.0	C12—C11—Cl1	120.2 (3)
C1A—C2—H2	121.0	C13—C12—C11	119.7 (3)
C2—C3—C4	120.6 (3)	C13—C12—H12	120.1
C2—C3—H3	119.7	C11—C12—H12	120.1
C4—C3—H3	119.7	C12—C13—C14	120.6 (4)
C5—C4—C3	122.4 (3)	C12—C13—H13	119.7
C5—C4—Br1	118.3 (3)	C14—C13—H13	119.7
C3—C4—Br1	119.3 (2)	C13—C14—C9	119.9 (4)
C4—C5—C5A	117.8 (3)	C13—C14—H14	120.0
C4—C5—H5	121.1	C9—C14—H14	120.0
C5A—C5—H5	121.1	C6—C15—C16	117.1 (3)
C5—C5A—C1A	119.4 (3)	C6—C15—H15A	108.0
C5—C5A—C6	133.6 (3)	C16—C15—H15A	108.0
C1A—C5A—C6	107.0 (3)	C6—C15—H15B	108.0
C7—C6—C5A	106.9 (2)	C16—C15—H15B	108.0
C7—C6—C15	127.0 (3)	H15A—C15—H15B	107.3
C5A—C6—C15	125.8 (3)	O17—C16—O18	123.3 (3)
C6—C7—N1	109.2 (3)	O17—C16—C15	124.6 (3)
C6—C7—C19	129.3 (3)	O18—C16—C15	112.0 (3)
N1—C7—C19	121.4 (3)	C16—O18—H18	109.5
N1—C8—C9	112.4 (3)	C7—C19—H19A	109.5
N1—C8—H8A	109.1	C7—C19—H19B	109.5
C9—C8—H8A	109.1	H19A—C19—H19B	109.5
N1—C8—H8B	109.1	C7—C19—H19C	109.5
C9—C8—H8B	109.1	H19A—C19—H19C	109.5
H8A—C8—H8B	107.9	H19B—C19—H19C	109.5
C10—C9—C14	120.1 (3)
C7—N1—C1A—C2	179.0 (3)	C15—C6—C7—C19	6.7 (5)
C8—N1—C1A—C2	5.5 (5)	C1A—N1—C7—C6	0.5 (3)
C7—N1—C1A—C5A	−0.5 (3)	C8—N1—C7—C6	173.8 (3)
C8—N1—C1A—C5A	−174.1 (3)	C1A—N1—C7—C19	178.9 (3)
N1—C1A—C2—C3	−179.9 (3)	C8—N1—C7—C19	−7.8 (5)
C5A—C1A—C2—C3	−0.4 (4)	C1A—N1—C8—C9	71.6 (4)
C1A—C2—C3—C4	−0.3 (5)	C7—N1—C8—C9	−100.8 (4)
C2—C3—C4—C5	0.5 (5)	N1—C8—C9—C10	51.7 (4)
C2—C3—C4—Br1	−178.6 (2)	N1—C8—C9—C14	−128.7 (3)
C3—C4—C5—C5A	0.1 (5)	C14—C9—C10—C11	1.6 (5)
Br1—C4—C5—C5A	179.2 (2)	C8—C9—C10—C11	−178.8 (3)
C4—C5—C5A—C1A	−0.8 (4)	C9—C10—C11—C12	−0.7 (5)
C4—C5—C5A—C6	179.5 (3)	C9—C10—C11—Cl1	178.7 (3)
N1—C1A—C5A—C5	−179.4 (2)	C10—C11—C12—C13	−0.5 (6)
C2—C1A—C5A—C5	1.0 (4)	Cl1—C11—C12—C13	−179.8 (3)
N1—C1A—C5A—C6	0.3 (3)	C11—C12—C13—C14	0.7 (7)
C2—C1A—C5A—C6	−179.2 (3)	C12—C13—C14—C9	0.1 (7)
C5—C5A—C6—C7	179.6 (3)	C10—C9—C14—C13	−1.3 (6)
C1A—C5A—C6—C7	−0.1 (3)	C8—C9—C14—C13	179.1 (4)
C5—C5A—C6—C15	−5.5 (5)	C7—C6—C15—C16	−109.5 (4)
C1A—C5A—C6—C15	174.9 (3)	C5A—C6—C15—C16	76.6 (4)
C5A—C6—C7—N1	−0.2 (3)	C6—C15—C16—O17	3.5 (5)
C15—C6—C7—N1	−175.1 (3)	C6—C15—C16—O18	−176.6 (3)
C5A—C6—C7—C19	−178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O17i	0.82	1.87	2.679 (3)	170

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) .