Methyl 4-bromo-3-hy-droxy-benzoate.

In the title compound, C(8)H(7)BrO(3), the meth-oxy-carbonyl group is twisted at a dihedral angle of 8.06 (4)° with respect to the benzene ring. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds into helical chains running along the b axis.

Related literature

For applications of methyl 3-hy­droxy­benzoate derivatives in the synthesis of various broad-spectrum anti­microbials, see: Zhong et al. (2001 ▶). For the synthesis of the title compound, see: Nie et al. (2005 ▶).

Experimental

Crystal data

C8H7BrO3

M = 231.05

Monoclinic,

a = 10.812 (4) Å

b = 6.317 (2) Å

c = 12.490 (5) Å

β = 100.164 (6)°

V = 839.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.86 mm−1

T = 293 K

0.27 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.354, T max = 0.511

4755 measured reflections

1831 independent reflections

1129 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.172

S = 1.08

1831 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051445/xu5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051445/xu5110Isup2.hkl

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

C8H7BrO3	F(000) = 456
Mr = 231.05	Dx = 1.828 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1334 reflections
a = 10.812 (4) Å	θ = 2.3–24.2°
b = 6.317 (2) Å	µ = 4.86 mm−1
c = 12.490 (5) Å	T = 293 K
β = 100.164 (6)°	Plate, colorless
V = 839.7 (5) Å3	0.27 × 0.24 × 0.16 mm
Z = 4

Bruker SMART CCD 1000 diffractometer	1831 independent reflections
Radiation source: fine-focus sealed tube	1129 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 10.0 pixels mm-1	θmax = 27.2°, θmin = 1.9°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→3
Tmin = 0.354, Tmax = 0.511	l = −15→16
4755 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)] = 0.058	Hydrogen site location: difference Fourier map
wR(F2) = 0.172	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0685P)2 + 2.8188P] where P = (Fo2 + 2Fc2)/3
1831 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.92070 (8)	1.12616 (14)	0.78430 (7)	0.0617 (4)
C1	0.8397 (6)	0.8935 (11)	0.8349 (5)	0.0392 (15)
C2	0.7180 (6)	0.8391 (11)	0.7823 (5)	0.0382 (15)
C3	0.6621 (5)	0.6667 (10)	0.8204 (5)	0.0357 (15)
H3	0.5809	0.6296	0.7877	0.043*
C4	0.7238 (6)	0.5454 (10)	0.9072 (5)	0.0331 (14)
C5	0.8426 (6)	0.6045 (11)	0.9592 (5)	0.0425 (16)
H5	0.8837	0.5274	1.0183	0.051*
C6	0.8996 (6)	0.7797 (12)	0.9223 (6)	0.0449 (17)
H6	0.9792	0.8206	0.9571	0.054*
C7	0.6617 (6)	0.3570 (10)	0.9440 (5)	0.0396 (15)
C8	0.6834 (8)	0.0661 (13)	1.0640 (6)	0.057 (2)
H8A	0.6194	0.1164	1.1020	0.086*
H8B	0.7478	−0.0043	1.1142	0.086*
H8C	0.6471	−0.0314	1.0082	0.086*
O1	0.6635 (5)	0.9620 (9)	0.6988 (4)	0.0565 (14)
H1	0.5947	0.9128	0.6724	0.085*
O2	0.5536 (5)	0.3093 (9)	0.9112 (4)	0.0589 (15)
O3	0.7379 (4)	0.2443 (7)	1.0147 (4)	0.0432 (11)

	U11	U22	U33	U12	U13	U23
Br1	0.0603 (5)	0.0604 (6)	0.0619 (5)	−0.0167 (4)	0.0043 (4)	0.0095 (4)
C1	0.037 (3)	0.039 (4)	0.041 (3)	−0.006 (3)	0.006 (3)	−0.002 (3)
C2	0.037 (3)	0.043 (4)	0.033 (3)	0.003 (3)	0.003 (3)	−0.001 (3)
C3	0.026 (3)	0.043 (4)	0.037 (3)	−0.004 (3)	−0.001 (2)	−0.006 (3)
C4	0.033 (3)	0.035 (3)	0.030 (3)	−0.002 (3)	0.001 (3)	−0.003 (3)
C5	0.041 (4)	0.038 (4)	0.044 (4)	0.004 (3)	−0.008 (3)	−0.004 (3)
C6	0.037 (4)	0.043 (4)	0.050 (4)	−0.009 (3)	−0.003 (3)	−0.005 (3)
C7	0.045 (4)	0.036 (4)	0.037 (3)	−0.002 (3)	0.006 (3)	−0.005 (3)
C8	0.072 (5)	0.051 (5)	0.049 (4)	0.003 (4)	0.009 (4)	0.006 (4)
O1	0.050 (3)	0.057 (3)	0.055 (3)	−0.008 (3)	−0.011 (2)	0.022 (3)
O2	0.040 (3)	0.057 (3)	0.072 (3)	−0.014 (2)	−0.011 (2)	0.014 (3)
O3	0.044 (3)	0.037 (3)	0.044 (3)	−0.005 (2)	−0.003 (2)	0.009 (2)

Br1—C1	1.876 (7)	C5—H5	0.9300
C1—C6	1.370 (10)	C6—H6	0.9300
C1—C2	1.406 (9)	C7—O2	1.206 (8)
C2—O1	1.349 (8)	C7—O3	1.307 (8)
C2—C3	1.371 (9)	C8—O3	1.457 (9)
C3—C4	1.397 (9)	C8—H8A	0.9600
C3—H3	0.9300	C8—H8B	0.9600
C4—C5	1.384 (9)	C8—H8C	0.9600
C4—C7	1.480 (9)	O1—H1	0.8200
C5—C6	1.385 (10)
C6—C1—C2	121.0 (6)	C1—C6—C5	120.6 (6)
C6—C1—Br1	119.8 (5)	C1—C6—H6	119.7
C2—C1—Br1	119.2 (5)	C5—C6—H6	119.7
O1—C2—C3	124.5 (6)	O2—C7—O3	123.5 (6)
O1—C2—C1	117.7 (6)	O2—C7—C4	124.1 (6)
C3—C2—C1	117.7 (6)	O3—C7—C4	112.4 (5)
C2—C3—C4	121.7 (6)	O3—C8—H8A	109.5
C2—C3—H3	119.1	O3—C8—H8B	109.5
C4—C3—H3	119.1	H8A—C8—H8B	109.5
C5—C4—C3	119.5 (6)	O3—C8—H8C	109.5
C5—C4—C7	120.4 (6)	H8A—C8—H8C	109.5
C3—C4—C7	120.1 (5)	H8B—C8—H8C	109.5
C4—C5—C6	119.3 (6)	C2—O1—H1	109.5
C4—C5—H5	120.3	C7—O3—C8	116.9 (6)
C6—C5—H5	120.3
C6—C1—C2—O1	178.1 (6)	C2—C1—C6—C5	1.7 (11)
Br1—C1—C2—O1	−1.8 (8)	Br1—C1—C6—C5	−178.5 (5)
C6—C1—C2—C3	−0.9 (10)	C4—C5—C6—C1	−0.3 (10)
Br1—C1—C2—C3	179.2 (5)	C5—C4—C7—O2	171.3 (7)
O1—C2—C3—C4	179.8 (6)	C3—C4—C7—O2	−7.8 (10)
C1—C2—C3—C4	−1.2 (9)	C5—C4—C7—O3	−10.2 (9)
C2—C3—C4—C5	2.6 (10)	C3—C4—C7—O3	170.7 (6)
C2—C3—C4—C7	−178.3 (6)	O2—C7—O3—C8	−7.1 (10)
C3—C4—C5—C6	−1.8 (10)	C4—C7—O3—C8	174.4 (5)
C7—C4—C5—C6	179.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.87	2.681 (7)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.87	2.681 (7)	170

Symmetry code: (i) .