Methyl 5-bromo-2-hy-droxy-benzoate.

The title compound, C(8)H(7)BrO(3), is almost planar (r.m.s. deviation for the non-H atoms = 0.055 Å). In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into C(6) chains propagating in [010]. Very weak aromatic π-π inter-actions [centroid-centroid distances = 3.984 (5) and 3.982 (5) Å] also occur.

Related literature

For the crystal structure of the methyl 4-bromo-3-hy­droxy­benzoate isomer, see: Huang et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H7BrO3

M = 231.04

Monoclinic,

a = 3.9829 (8) Å

b = 9.0950 (19) Å

c = 12.122 (3) Å

β = 95.162 (9)°

V = 437.33 (17) Å3

Z = 2

Mo Kα radiation

μ = 4.66 mm−1

T = 296 K

0.34 × 0.28 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.228, T max = 0.342

3242 measured reflections

1644 independent reflections

1186 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.142

S = 1.06

1644 reflections

112 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.31 e Å−3

Δρmin = −0.72 e Å−3

Absolute structure: Flack (1983 ▶), 687 Freidel pairs

Flack parameter: 0.07 (3)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016297/hb6740sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016297/hb6740Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016297/hb6740Isup3.cml

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

C8H7BrO3	F(000) = 228
Mr = 231.04	Dx = 1.755 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1516 reflections
a = 3.9829 (8) Å	θ = 2.8–24.2°
b = 9.0950 (19) Å	µ = 4.66 mm−1
c = 12.122 (3) Å	T = 296 K
β = 95.162 (9)°	Needle, yellow–brown
V = 437.33 (17) Å3	0.34 × 0.28 × 0.23 mm
Z = 2

Bruker APEXII CCD diffractometer	1644 independent reflections
Radiation source: sealed tube	1186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 26.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.228, Tmax = 0.342	k = −11→11
3242 measured reflections	l = −15→15

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1644 reflections	Δρmax = 1.31 e Å−3
112 parameters	Δρmin = −0.72 e Å−3
1 restraint	Absolute structure: Flack (1983), 687 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	1.1035 (2)	1.05024 (13)	0.06707 (7)	0.0606 (3)
O1	0.663 (2)	0.7888 (8)	0.4895 (6)	0.076 (3)
O2	0.4780 (15)	0.5536 (9)	0.3653 (4)	0.0601 (18)
O3	0.6181 (14)	0.5492 (9)	0.1924 (4)	0.0512 (18)
C1	0.759 (2)	0.8434 (8)	0.3920 (6)	0.035 (3)
C2	0.901 (2)	0.9860 (8)	0.3906 (7)	0.043 (3)
C3	0.9992 (16)	1.0454 (12)	0.2961 (6)	0.042 (2)
C4	0.966 (2)	0.9673 (8)	0.1995 (7)	0.039 (3)
C5	0.8380 (19)	0.8249 (8)	0.1976 (6)	0.037 (3)
C6	0.736 (2)	0.7643 (7)	0.2943 (6)	0.033 (2)
C7	0.594 (2)	0.6113 (8)	0.2910 (7)	0.039 (3)
C8	0.478 (3)	0.4012 (8)	0.1801 (8)	0.060 (4)
H1	0.64600	0.85650	0.53340	0.1140*
H2	0.92750	1.04020	0.45590	0.0520*
H3	1.08960	1.13970	0.29710	0.0510*
H5	0.82060	0.77090	0.13220	0.0440*
H8A	0.59580	0.33700	0.23330	0.0910*
H8B	0.50350	0.36590	0.10670	0.0910*
H8C	0.24340	0.40340	0.19220	0.0910*

	U11	U22	U33	U12	U13	U23
Br1	0.0692 (6)	0.0456 (4)	0.0687 (6)	−0.0185 (6)	0.0153 (4)	0.0107 (5)
O1	0.105 (6)	0.059 (4)	0.066 (4)	0.024 (4)	0.019 (4)	0.002 (3)
O2	0.096 (4)	0.034 (2)	0.054 (3)	−0.004 (5)	0.027 (3)	0.009 (4)
O3	0.070 (4)	0.030 (2)	0.055 (3)	−0.022 (4)	0.014 (2)	−0.006 (4)
C1	0.035 (5)	0.031 (4)	0.038 (4)	0.009 (3)	0.001 (3)	0.006 (3)
C2	0.051 (5)	0.031 (4)	0.047 (5)	0.005 (4)	−0.001 (4)	−0.009 (3)
C3	0.040 (4)	0.024 (3)	0.061 (5)	−0.004 (5)	−0.003 (3)	0.007 (6)
C4	0.035 (4)	0.029 (4)	0.052 (5)	0.000 (3)	0.003 (4)	0.009 (3)
C5	0.039 (5)	0.024 (3)	0.046 (5)	−0.001 (3)	−0.001 (3)	−0.001 (3)
C6	0.031 (4)	0.019 (3)	0.049 (5)	0.002 (3)	0.001 (3)	0.004 (3)
C7	0.039 (5)	0.028 (3)	0.050 (5)	0.003 (3)	−0.003 (4)	0.003 (4)
C8	0.078 (7)	0.016 (4)	0.087 (7)	−0.015 (4)	0.008 (5)	−0.005 (4)

Br1—C4	1.899 (8)	C4—C5	1.391 (10)
O1—C1	1.368 (10)	C5—C6	1.389 (10)
O2—C7	1.173 (10)	C6—C7	1.501 (10)
O3—C7	1.333 (10)	C2—H2	0.9300
O3—C8	1.460 (11)	C3—H3	0.9300
O1—H1	0.8200	C5—H5	0.9300
C1—C6	1.382 (10)	C8—H8A	0.9600
C1—C2	1.416 (10)	C8—H8B	0.9600
C2—C3	1.356 (11)	C8—H8C	0.9600
C3—C4	1.366 (12)
C7—O3—C8	115.1 (7)	O3—C7—C6	111.1 (7)
C1—O1—H1	109.00	O2—C7—O3	124.3 (8)
O1—C1—C6	123.3 (7)	C1—C2—H2	119.00
C2—C1—C6	117.6 (7)	C3—C2—H2	119.00
O1—C1—C2	119.1 (7)	C2—C3—H3	120.00
C1—C2—C3	121.4 (8)	C4—C3—H3	120.00
C2—C3—C4	120.3 (9)	C4—C5—H5	120.00
Br1—C4—C5	119.3 (6)	C6—C5—H5	120.00
C3—C4—C5	120.4 (8)	O3—C8—H8A	109.00
Br1—C4—C3	120.4 (6)	O3—C8—H8B	109.00
C4—C5—C6	119.3 (7)	O3—C8—H8C	110.00
C1—C6—C7	120.1 (7)	H8A—C8—H8B	109.00
C5—C6—C7	118.9 (7)	H8A—C8—H8C	110.00
C1—C6—C5	121.0 (6)	H8B—C8—H8C	110.00
O2—C7—C6	124.6 (8)
C8—O3—C7—C6	−178.4 (7)	C2—C3—C4—C5	−1.4 (12)
C8—O3—C7—O2	1.8 (12)	Br1—C4—C5—C6	−179.7 (6)
C6—C1—C2—C3	2.5 (12)	C3—C4—C5—C6	1.7 (12)
O1—C1—C2—C3	−179.8 (8)	C4—C5—C6—C7	179.2 (7)
C2—C1—C6—C5	−2.2 (12)	C4—C5—C6—C1	0.2 (12)
C2—C1—C6—C7	178.8 (7)	C1—C6—C7—O2	4.8 (13)
O1—C1—C6—C5	−179.8 (8)	C5—C6—C7—O3	6.0 (10)
O1—C1—C6—C7	1.2 (12)	C1—C6—C7—O3	−174.9 (7)
C1—C2—C3—C4	−0.7 (12)	C5—C6—C7—O2	−174.2 (8)
C2—C3—C4—Br1	−180.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	2.25	3.065 (10)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	2.25	3.065 (10)	170

Symmetry code: (i) .