3-Bromo-2-hy-droxy-benzaldehyde.

The mol-ecule of the title compound, C(7)H(5)BrO(2), is almost planar (r.m.s. deviation from the plane of all the non-H atoms = 0.0271 Å) and displays intra-molecular O-H⋯O hydrogen bonding between the phenol group and the aldehyde O atom. Packing is directed by weak inter-molecular C-H⋯Br inter-actions and π-stacking between nearly parallel mol-ecules [dihedral angle = 5.30 (6)° and centroid-centroid distance = 3.752 (1) Å].

Related literature

For information on the synthesis of the title compound, see: Hansen & Skattebol (2005 ▶). For recent uses of the title compound in the synthesis of biologically active compounds, see: Velázquez et al. (2012 ▶); Wang et al. (2012 ▶); Zhang et al. (2012 ▶). For use of the title compound to prepare Schiff base ligands for metal coordination chemistry, see: Escudero-Adán et al. (2010 ▶); McGarrigle et al. (2004 ▶); Tzubery & Tshuva (2012 ▶). For related crystal structures, see: Balasubramani et al. (2011 ▶); Fan, You, Liu, Qian & Huang (2008 ▶); Fan, You, Qian, Liu & Huang (2008 ▶) Iwasaki et al. (1976 ▶); Kirchner et al. (2011 ▶); Tang et al. (2010 ▶).

Experimental

Crystal data

C7H5BrO2

M = 201.02

Monoclinic,

a = 7.0282 (3) Å

b = 14.9715 (7) Å

c = 6.8472 (3) Å

β = 108.907 (1)°

V = 681.61 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.96 mm−1

T = 125 K

0.22 × 0.08 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.354, T max = 0.842

10788 measured reflections

2074 independent reflections

1815 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.048

S = 1.04

2074 reflections

95 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.25 e Å−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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031510/bg2472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031510/bg2472Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031510/bg2472Isup3.cml

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

C7H5BrO2	F(000) = 392
Mr = 201.02	Dx = 1.959 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6585 reflections
a = 7.0282 (3) Å	θ = 2.7–30.5°
b = 14.9715 (7) Å	µ = 5.96 mm−1
c = 6.8472 (3) Å	T = 125 K
β = 108.907 (1)°	Plate, colourless
V = 681.61 (5) Å3	0.22 × 0.08 × 0.03 mm
Z = 4

Bruker APEXII CCD diffractometer	2074 independent reflections
Radiation source: fine-focus sealed tube	1815 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −10→10
Tmin = 0.354, Tmax = 0.842	k = −21→21
10788 measured reflections	l = −9→9

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0249P)2 + 0.1779P] where P = (Fo2 + 2Fc2)/3
2074 reflections	(Δ/σ)max = 0.001
95 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.25 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	0.11374 (2)	0.567091 (9)	0.25208 (2)	0.02342 (6)
O2	0.12613 (15)	0.76969 (8)	0.28306 (17)	0.0236 (2)
H2	0.144 (4)	0.8217 (17)	0.294 (4)	0.055 (8)*
C1	0.4646 (2)	0.88799 (9)	0.3840 (2)	0.0228 (3)
H1	0.5839	0.9229	0.4229	0.027*
O1	0.30259 (19)	0.92736 (7)	0.33528 (18)	0.0284 (2)
C6	0.3410 (2)	0.64329 (9)	0.3299 (2)	0.0170 (2)
C7	0.3132 (2)	0.73579 (9)	0.3323 (2)	0.0166 (2)
C3	0.6776 (2)	0.75351 (10)	0.4401 (2)	0.0202 (3)
H3	0.7925	0.7913	0.4781	0.024*
C5	0.5322 (2)	0.60728 (9)	0.3814 (2)	0.0192 (3)
H5	0.5480	0.5443	0.3776	0.023*
C2	0.4853 (2)	0.79087 (9)	0.38599 (19)	0.0177 (2)
C4	0.7016 (2)	0.66178 (10)	0.4385 (2)	0.0219 (3)
H4	0.8323	0.6363	0.4760	0.026*

	U11	U22	U33	U12	U13	U23
Br1	0.01950 (8)	0.01875 (8)	0.03050 (9)	−0.00399 (5)	0.00602 (6)	−0.00323 (5)
O2	0.0177 (5)	0.0199 (5)	0.0302 (6)	0.0043 (4)	0.0037 (4)	−0.0004 (4)
C1	0.0317 (8)	0.0177 (6)	0.0188 (6)	−0.0035 (6)	0.0080 (6)	0.0005 (5)
O1	0.0383 (7)	0.0187 (5)	0.0275 (6)	0.0039 (4)	0.0095 (5)	0.0031 (4)
C6	0.0183 (6)	0.0165 (6)	0.0158 (6)	−0.0017 (5)	0.0049 (5)	−0.0020 (5)
C7	0.0168 (6)	0.0177 (6)	0.0144 (6)	0.0022 (5)	0.0040 (5)	−0.0002 (5)
C3	0.0190 (7)	0.0241 (7)	0.0175 (6)	−0.0041 (5)	0.0059 (5)	−0.0014 (5)
C5	0.0222 (7)	0.0172 (6)	0.0181 (6)	0.0027 (5)	0.0062 (5)	−0.0014 (5)
C2	0.0222 (6)	0.0169 (6)	0.0134 (6)	−0.0018 (5)	0.0050 (5)	−0.0005 (5)
C4	0.0174 (6)	0.0265 (7)	0.0208 (6)	0.0037 (5)	0.0048 (5)	−0.0009 (5)

Br1—C6	1.8933 (13)	C7—C2	1.4107 (19)
O2—C7	1.3466 (16)	C3—C4	1.384 (2)
O2—H2	0.79 (2)	C3—C2	1.397 (2)
C1—O1	1.2284 (19)	C3—H3	0.9500
C1—C2	1.4609 (19)	C5—C4	1.391 (2)
C1—H1	0.9500	C5—H5	0.9500
C6—C5	1.3836 (19)	C4—H4	0.9500
C6—C7	1.3993 (19)
C7—O2—H2	103.8 (18)	C4—C3—H3	119.8
O1—C1—C2	124.12 (14)	C2—C3—H3	119.8
O1—C1—H1	117.9	C6—C5—C4	121.02 (13)
C2—C1—H1	117.9	C6—C5—H5	119.5
C5—C6—C7	120.67 (13)	C4—C5—H5	119.5
C5—C6—Br1	119.87 (10)	C3—C2—C7	120.60 (13)
C7—C6—Br1	119.45 (10)	C3—C2—C1	119.08 (13)
O2—C7—C6	119.90 (12)	C7—C2—C1	120.32 (13)
O2—C7—C2	122.02 (12)	C3—C4—C5	119.28 (13)
C6—C7—C2	118.08 (12)	C3—C4—H4	120.4
C4—C3—C2	120.32 (13)	C5—C4—H4	120.4
C5—C6—C7—O2	−179.59 (12)	O2—C7—C2—C3	178.81 (12)
Br1—C6—C7—O2	1.18 (17)	C6—C7—C2—C3	−1.59 (19)
C5—C6—C7—C2	0.79 (19)	O2—C7—C2—C1	−1.71 (19)
Br1—C6—C7—C2	−178.43 (9)	C6—C7—C2—C1	177.89 (12)
C7—C6—C5—C4	0.6 (2)	O1—C1—C2—C3	178.64 (13)
Br1—C6—C5—C4	179.81 (11)	O1—C1—C2—C7	−0.9 (2)
C4—C3—C2—C7	1.0 (2)	C2—C3—C4—C5	0.4 (2)
C4—C3—C2—C1	−178.47 (13)	C6—C5—C4—C3	−1.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.79 (2)	1.90 (2)	2.6364 (16)	154 (2)
C4—H4···Br1i	0.95	3.05	3.798 (2)	137

Table 1

Hydrogen-bond and C—H⋯Br interaction geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.79 (2)	1.90 (2)	2.6364 (16)	154 (2)
C4—H4⋯Br1i	0.95	3.05	3.798 (2)	137

Symmetry code: (i) .