3,5-Dibromo-2-hydroxy-benzaldehyde.

The title compound, C(7)H(4)Br(2)O(2), exhibits a layer packing structure via weak π-π stacking inter-actions [centroid-centroid distances between adjacent aromatic rings are 4.040 (8) and 3.776 (7) Å]. Mol-ecules in each layer are linked by inter-molecular O-H⋯O hydrogen bonding and Br⋯Br inter-actions [3.772 (4) Å]. There are two mol-ecules in the asymmetric unit.

Related literature

For related compounds, see Harkat et al. (2008 ▶); Lu et al. (2006 ▶); Duan et al. (2007 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C7H4Br2O2

M = 279.92

Monoclinic,

a = 16.474 (8) Å

b = 14.025 (10) Å

c = 7.531 (7) Å

β = 103.212 (2)°

V = 1694 (2) Å3

Z = 8

Mo Kα radiation

μ = 9.52 mm−1

T = 291 (2) K

0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.450, T max = 0.450 (expected range = 0.386–0.386)

8777 measured reflections

3328 independent reflections

1670 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 0.79

3328 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008726/at2547sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008726/at2547Isup2.hkl

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

C7H4Br2O2	F000 = 1056
Mr = 279.92	Dx = 2.195 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1688 reflections
a = 16.474 (8) Å	θ = 2.9–22.8º
b = 14.025 (10) Å	µ = 9.52 mm−1
c = 7.531 (7) Å	T = 291 (2) K
β = 103.212 (2)º	Block, yellow
V = 1694 (2) Å3	0.10 × 0.10 × 0.10 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3328 independent reflections
Radiation source: fine-focus sealed tube	1670 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.109
T = 291(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −20→15
Tmin = 0.450, Tmax = 0.450	k = −17→16
8777 measured reflections	l = −7→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0451P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106	(Δ/σ)max < 0.001
S = 0.79	Δρmax = 0.67 e Å−3
3328 reflections	Δρmin = −0.55 e Å−3
202 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (3)
Secondary atom site location: difference Fourier map

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	0.33358 (5)	0.40384 (5)	0.34454 (11)	0.0666 (3)
Br2	0.32451 (4)	−0.00188 (5)	0.34528 (10)	0.0653 (3)
Br3	0.10268 (5)	0.96790 (5)	0.39100 (13)	0.0750 (3)
Br4	−0.12580 (4)	0.67358 (6)	0.46512 (11)	0.0727 (3)
C1	0.5095 (4)	0.1950 (4)	0.3046 (8)	0.0424 (15)
C2	0.4701 (4)	0.2838 (4)	0.3143 (8)	0.0455 (16)
C3	0.3876 (4)	0.2848 (5)	0.3376 (8)	0.0490 (17)
C4	0.3467 (4)	0.2004 (5)	0.3511 (9)	0.0539 (18)
H4	0.2925	0.2016	0.3681	0.065*
C5	0.3858 (4)	0.1130 (5)	0.3396 (8)	0.0504 (17)
C6	0.4670 (4)	0.1100 (5)	0.3151 (8)	0.0488 (17)
H6	0.4927	0.0518	0.3059	0.059*
C7	0.5945 (4)	0.1906 (5)	0.2718 (9)	0.0574 (19)
H7	0.6177	0.1306	0.2649	0.069*
C8	0.1215 (4)	0.6721 (5)	0.4036 (9)	0.0494 (17)
C9	0.1402 (4)	0.7692 (5)	0.3912 (8)	0.0456 (16)
C10	0.0787 (4)	0.8359 (4)	0.4063 (8)	0.0477 (17)
C11	0.0001 (4)	0.8089 (5)	0.4295 (9)	0.0542 (18)
H11	−0.0393	0.8548	0.4395	0.065*
C12	−0.0188 (4)	0.7110 (5)	0.4376 (9)	0.0510 (18)
C13	0.0415 (4)	0.6440 (5)	0.4260 (8)	0.0518 (17)
H13	0.0294	0.5795	0.4329	0.062*
C14	0.1838 (5)	0.5982 (5)	0.3899 (10)	0.066 (2)
H14	0.1689	0.5349	0.4011	0.079*
O1	0.6364 (3)	0.2604 (3)	0.2531 (7)	0.0702 (15)
O2	0.5114 (3)	0.3678 (3)	0.3080 (7)	0.0655 (13)
H2	0.5587	0.3568	0.2960	0.098*
O3	0.2528 (3)	0.6135 (3)	0.3652 (8)	0.0762 (15)
O4	0.2139 (2)	0.8015 (3)	0.3645 (7)	0.0563 (12)
H4A	0.2422	0.7563	0.3452	0.084*

	U11	U22	U33	U12	U13	U23
Br1	0.0687 (5)	0.0551 (5)	0.0819 (6)	0.0197 (4)	0.0292 (4)	0.0055 (4)
Br2	0.0571 (5)	0.0538 (5)	0.0879 (6)	−0.0152 (4)	0.0226 (4)	−0.0017 (4)
Br3	0.0666 (5)	0.0371 (5)	0.1317 (8)	0.0011 (4)	0.0441 (5)	−0.0014 (5)
Br4	0.0484 (5)	0.0764 (6)	0.0966 (6)	−0.0142 (4)	0.0233 (4)	0.0000 (5)
C1	0.041 (4)	0.039 (4)	0.048 (4)	−0.005 (3)	0.012 (3)	0.000 (3)
C2	0.054 (4)	0.034 (4)	0.049 (4)	−0.005 (3)	0.012 (3)	0.004 (3)
C3	0.048 (4)	0.051 (5)	0.047 (4)	0.010 (3)	0.010 (3)	−0.001 (4)
C4	0.043 (4)	0.060 (5)	0.060 (4)	−0.003 (4)	0.016 (3)	−0.004 (4)
C5	0.050 (4)	0.049 (5)	0.054 (4)	−0.007 (3)	0.015 (3)	−0.008 (4)
C6	0.040 (4)	0.046 (4)	0.060 (5)	−0.003 (3)	0.011 (3)	0.001 (4)
C7	0.050 (4)	0.046 (5)	0.078 (5)	0.008 (3)	0.018 (4)	0.006 (4)
C8	0.053 (4)	0.041 (4)	0.055 (4)	−0.004 (3)	0.014 (3)	0.003 (3)
C9	0.043 (4)	0.046 (4)	0.049 (4)	0.001 (3)	0.011 (3)	−0.001 (3)
C10	0.049 (4)	0.041 (4)	0.055 (4)	−0.002 (3)	0.015 (3)	−0.001 (3)
C11	0.049 (4)	0.056 (5)	0.059 (4)	0.002 (4)	0.016 (3)	−0.005 (4)
C12	0.041 (4)	0.063 (5)	0.052 (4)	0.001 (3)	0.018 (3)	0.007 (4)
C13	0.053 (4)	0.042 (4)	0.062 (5)	−0.010 (3)	0.017 (3)	0.005 (4)
C14	0.077 (6)	0.035 (4)	0.091 (6)	0.013 (4)	0.028 (5)	0.011 (4)
O1	0.049 (3)	0.052 (3)	0.116 (4)	−0.002 (3)	0.032 (3)	0.010 (3)
O2	0.057 (3)	0.045 (3)	0.098 (4)	0.001 (2)	0.026 (3)	0.004 (3)
O3	0.059 (3)	0.049 (3)	0.130 (5)	0.013 (3)	0.043 (3)	0.013 (3)
O4	0.037 (3)	0.041 (3)	0.097 (4)	0.001 (2)	0.029 (2)	−0.002 (3)

Br1—C3	1.898 (6)	C7—H7	0.9300
Br2—C5	1.906 (6)	C8—C9	1.404 (9)
Br3—C10	1.902 (6)	C8—C13	1.424 (8)
Br4—C12	1.895 (6)	C8—C14	1.479 (9)
C1—C6	1.394 (8)	C9—O4	1.355 (7)
C1—C2	1.413 (8)	C9—C10	1.402 (8)
C1—C7	1.477 (8)	C10—C11	1.398 (8)
C2—O2	1.368 (7)	C11—C12	1.412 (9)
C2—C3	1.410 (8)	C11—H11	0.9300
C3—C4	1.377 (8)	C12—C13	1.384 (8)
C4—C5	1.397 (8)	C13—H13	0.9300
C4—H4	0.9300	C14—O3	1.213 (8)
C5—C6	1.393 (8)	C14—H14	0.9300
C6—H6	0.9300	O2—H2	0.8200
C7—O1	1.225 (7)	O4—H4A	0.8200
C6—C1—C2	120.5 (6)	C9—C8—C14	120.7 (6)
C6—C1—C7	118.7 (6)	C13—C8—C14	119.4 (6)
C2—C1—C7	120.7 (6)	O4—C9—C10	118.6 (6)
O2—C2—C3	119.8 (6)	O4—C9—C8	123.5 (6)
O2—C2—C1	121.3 (6)	C10—C9—C8	118.0 (6)
C3—C2—C1	118.9 (6)	C11—C10—C9	122.4 (6)
C4—C3—C2	120.2 (6)	C11—C10—Br3	118.9 (5)
C4—C3—Br1	120.9 (5)	C9—C10—Br3	118.7 (5)
C2—C3—Br1	118.9 (5)	C10—C11—C12	119.3 (6)
C3—C4—C5	120.6 (6)	C10—C11—H11	120.4
C3—C4—H4	119.7	C12—C11—H11	120.4
C5—C4—H4	119.7	C13—C12—C11	119.3 (6)
C6—C5—C4	120.3 (6)	C13—C12—Br4	121.2 (5)
C6—C5—Br2	120.5 (5)	C11—C12—Br4	119.6 (5)
C4—C5—Br2	119.1 (5)	C12—C13—C8	121.1 (6)
C5—C6—C1	119.5 (6)	C12—C13—H13	119.4
C5—C6—H6	120.2	C8—C13—H13	119.4
C1—C6—H6	120.2	O3—C14—C8	125.1 (7)
O1—C7—C1	124.5 (6)	O3—C14—H14	117.4
O1—C7—H7	117.7	C8—C14—H14	117.4
C1—C7—H7	117.7	C2—O2—H2	109.5
C9—C8—C13	119.9 (6)	C9—O4—H4A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.94	2.660 (6)	146
O4—H4A···O3	0.82	2.01	2.713 (6)	143
O4—H4A···O1i	0.82	2.29	2.863 (6)	128
C7—H7···O3ii	0.93	2.55	3.122 (8)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.94	2.660 (6)	146
O4—H4A⋯O3	0.82	2.01	2.713 (6)	143
O4—H4A⋯O1i	0.82	2.29	2.863 (6)	128
C7—H7⋯O3ii	0.93	2.55	3.122 (8)	120

Symmetry codes: (i) ; (ii) .