2-(2-Bromo-phen-yl)acetic acid.

In the title mol-ecule, C(8)H(7)BrO(2), the carboxyl group is twisted by 76.2 (3)° from the benzene ring plane. In the crystal, mol-ecules are linked into inversion dimers through pairs of O-H⋯O hydrogen bonds. The dimers are further linked into layers parallel to the bc plane by weak C-H⋯O hydrogen bonds.

Related literature

For applications of the title compound, see: Deshpande et al. (2008 ▶); Rodriguesa et al. (2002 ▶); Pratt et al. (2000 ▶). For related structures, see: Hodgson & Asplund (1991 ▶); Harris et al. (1994 ▶); Hartung et al. (2004 ▶); Yuan et al. (2008 ▶); Jasinski et al.(2010 ▶); Li et al. (2010 ▶).

Experimental

Crystal data

C8H7BrO2

M = 215.05

Monoclinic,

a = 8.9732 (5) Å

b = 5.9114 (3) Å

c = 15.8489 (7) Å

β = 99.529 (5)°

V = 829.09 (7) Å3

Z = 4

Mo Kα radiation

μ = 4.90 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.370, T max = 1.000

8471 measured reflections

1628 independent reflections

1248 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.096

S = 1.07

1628 reflections

105 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.69 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997) ▶; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020545/cv5295sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020545/cv5295Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020545/cv5295Isup3.cml

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

C8H7BrO2	F(000) = 424
Mr = 215.05	Dx = 1.723 Mg m−3
Monoclinic, P21/c	Melting point = 381–377 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9732 (5) Å	Cell parameters from 3025 reflections
b = 5.9114 (3) Å	θ = 3.4–29.1°
c = 15.8489 (7) Å	µ = 4.90 mm−1
β = 99.529 (5)°	T = 293 K
V = 829.09 (7) Å3	Prism, white
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1628 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.7°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.370, Tmax = 1.000	l = −19→19
8471 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0324P)2 + 1.055P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1628 reflections	Δρmax = 0.55 e Å−3
105 parameters	Δρmin = −0.69 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.071 (3)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.42140 (6)	0.23223 (8)	0.92648 (3)	0.0681 (3)
C1	0.2498 (4)	0.4863 (6)	0.7908 (2)	0.0427 (9)
C2	0.3352 (4)	0.2936 (6)	0.8109 (2)	0.0395 (8)
C3	0.3640 (4)	0.1404 (7)	0.7497 (3)	0.0498 (10)
H3	0.4208	0.0110	0.7654	0.060*
C4	0.3078 (6)	0.1819 (8)	0.6660 (3)	0.0627 (12)
H4	0.3275	0.0813	0.6241	0.075*
C5	0.2223 (6)	0.3715 (9)	0.6430 (3)	0.0689 (13)
H5	0.1839	0.3990	0.5857	0.083*
C6	0.1935 (5)	0.5208 (7)	0.7051 (3)	0.0599 (12)
H6	0.1347	0.6480	0.6890	0.072*
C7	0.2239 (5)	0.6574 (7)	0.8568 (3)	0.0570 (11)
H7A	0.3211	0.7023	0.8887	0.068*
H7B	0.1779	0.7906	0.8276	0.068*
O8	0.1337 (4)	0.7126 (6)	0.9850 (2)	0.0710 (10)
C8	0.1266 (4)	0.5795 (7)	0.9188 (3)	0.0520 (10)
O9	0.0457 (3)	0.4130 (5)	0.9081 (2)	0.0650 (9)
H8	0.072 (7)	0.678 (10)	1.020 (5)	0.11 (2)*

	U11	U22	U33	U12	U13	U23
Br1	0.0835 (4)	0.0712 (4)	0.0440 (3)	−0.0020 (2)	−0.0059 (2)	0.0091 (2)
C1	0.049 (2)	0.0354 (19)	0.047 (2)	−0.0069 (16)	0.0158 (18)	0.0034 (16)
C2	0.045 (2)	0.041 (2)	0.0330 (19)	−0.0082 (16)	0.0085 (16)	0.0050 (15)
C3	0.058 (2)	0.043 (2)	0.052 (3)	−0.0005 (18)	0.021 (2)	0.0007 (19)
C4	0.085 (3)	0.059 (3)	0.049 (3)	−0.015 (2)	0.026 (2)	−0.014 (2)
C5	0.088 (3)	0.079 (3)	0.038 (3)	−0.007 (3)	0.004 (2)	0.007 (2)
C6	0.070 (3)	0.053 (2)	0.055 (3)	0.007 (2)	0.006 (2)	0.016 (2)
C7	0.070 (3)	0.040 (2)	0.067 (3)	−0.005 (2)	0.029 (2)	−0.004 (2)
O8	0.080 (2)	0.069 (2)	0.071 (2)	−0.0264 (17)	0.0341 (19)	−0.0325 (17)
C8	0.053 (2)	0.048 (2)	0.058 (3)	−0.0015 (19)	0.019 (2)	−0.010 (2)
O9	0.0697 (19)	0.0631 (19)	0.069 (2)	−0.0253 (16)	0.0323 (16)	−0.0258 (16)

Br1—C2	1.901 (4)	C5—C6	1.378 (6)
C1—C2	1.380 (5)	C5—H5	0.9300
C1—C6	1.383 (5)	C6—H6	0.9300
C1—C7	1.502 (5)	C7—C8	1.491 (6)
C2—C3	1.383 (5)	C7—H7A	0.9700
C3—C4	1.361 (6)	C7—H7B	0.9700
C3—H3	0.9300	O8—C8	1.304 (5)
C4—C5	1.373 (7)	O8—H8	0.87 (7)
C4—H4	0.9300	C8—O9	1.218 (5)
C2—C1—C6	116.6 (4)	C6—C5—H5	120.2
C2—C1—C7	122.6 (4)	C5—C6—C1	121.7 (4)
C6—C1—C7	120.8 (4)	C5—C6—H6	119.1
C1—C2—C3	122.6 (4)	C1—C6—H6	119.1
C1—C2—Br1	120.1 (3)	C8—C7—C1	115.2 (3)
C3—C2—Br1	117.2 (3)	C8—C7—H7A	108.5
C4—C3—C2	118.9 (4)	C1—C7—H7A	108.5
C4—C3—H3	120.5	C8—C7—H7B	108.5
C2—C3—H3	120.5	C1—C7—H7B	108.5
C3—C4—C5	120.4 (4)	H7A—C7—H7B	107.5
C3—C4—H4	119.8	C8—O8—H8	115 (4)
C5—C4—H4	119.8	O9—C8—O8	123.3 (4)
C4—C5—C6	119.7 (4)	O9—C8—C7	123.9 (4)
C4—C5—H5	120.2	O8—C8—C7	112.8 (4)
C6—C1—C2—C3	−0.2 (5)	C4—C5—C6—C1	0.6 (7)
C7—C1—C2—C3	−177.4 (3)	C2—C1—C6—C5	−0.6 (6)
C6—C1—C2—Br1	178.8 (3)	C7—C1—C6—C5	176.8 (4)
C7—C1—C2—Br1	1.5 (5)	C2—C1—C7—C8	−68.9 (5)
C1—C2—C3—C4	0.9 (6)	C6—C1—C7—C8	114.0 (4)
Br1—C2—C3—C4	−178.1 (3)	C1—C7—C8—O9	−15.8 (6)
C2—C3—C4—C5	−0.9 (6)	C1—C7—C8—O8	166.1 (4)
C3—C4—C5—C6	0.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O9i	0.87 (7)	1.76 (7)	2.630 (4)	175 (3)
C6—H6···O9ii	0.93	2.57	3.453 (5)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O9i	0.87 (7)	1.76 (7)	2.630 (4)	175 (3)
C6—H6⋯O9ii	0.93	2.57	3.453 (5)	158

Symmetry codes: (i) ; (ii) .