Crystal structure of (E)-3-(5-bromo-2-hydroxy-phen-yl)acryl-aldehyde.

The title compound, C9H7BrO2, displays a trans configuration with respect to the C=C double bond and is essentially planar [maximum deviation from the least-squares plane through all non-H atoms = 0.056 (4) Å]. The vinyl-aldehyde group adopts an extended conformation wih a C-C-C-C torsion angle of 179.7 (4)°. In the crystal, mol-ecules are linked by classical O-H⋯O and weak C-H⋯O hydrogen bonds into a three-dimensional supra-molecular network.

Related literature

For the synthesis of 2-hy­droxy­cinnamaldehydes, see: Kim et al. (2004 ▶); Zeiter & Rose (2009 ▶). For their biological activity, see: Kwon et al. (1996 ▶); Lee et al. (1999 ▶); Ka et al. (2003 ▶); Gan et al. (2009 ▶); Han et al. (2011 ▶). For their synthetic applications, see: Cabrera et al. (2008 ▶); Zu et al. (2009 ▶); Choi & Kim (2010 ▶); Lee & Kim (2011 ▶); Lee et al. (2011 ▶). For related structures, see: Kang & Kim (2013 ▶).

Experimental

Crystal data

C9H7BrO2

M = 227.06

Orthorhombic,

a = 12.1230 (11) Å

b = 15.0901 (14) Å

c = 4.8763 (4) Å

V = 892.06 (14) Å3

Z = 4

Mo Kα radiation

μ = 4.56 mm−1

T = 200 K

0.41 × 0.35 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.256, T max = 0.548

6031 measured reflections

2052 independent reflections

1683 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.086

S = 1.16

2052 reflections

110 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.58 e Å−3

Absolute structure: Flack (1983 ▶)

Absolute structure parameter: 0.021 (19)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814023708/gw2149sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023708/gw2149Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023708/gw2149Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023708/gw2149fig1.tif

A view of the mol­ecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814023708/gw2149fig2.tif

A partial view of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity.

CCDC reference: 1031276

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H7BrO2	F(000) = 448
Mr = 227.06	Dx = 1.691 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3701 reflections
a = 12.1230 (11) Å	θ = 2.7–28.2°
b = 15.0901 (14) Å	µ = 4.56 mm−1
c = 4.8763 (4) Å	T = 200 K
V = 892.06 (14) Å3	Block, pale yellow
Z = 4	0.41 × 0.35 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	2052 independent reflections
Radiation source: fine-focus sealed tube	1683 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→13
Tmin = 0.256, Tmax = 0.548	k = −20→19
6031 measured reflections	l = −6→5

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.P)2 + 1.2584P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
2052 reflections	Δρmax = 0.48 e Å−3
110 parameters	Δρmin = −0.58 e Å−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (19)

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
C1	0.5560 (4)	0.3452 (3)	0.1499 (9)	0.0325 (9)
O1	0.4596 (3)	0.3084 (2)	0.0686 (7)	0.0452 (8)
H1	0.4091	0.3236	0.1766	0.068*
C2	0.6537 (4)	0.3149 (3)	0.0237 (8)	0.0295 (9)
C3	0.7531 (3)	0.3521 (3)	0.1065 (9)	0.0305 (9)
H3	0.8200	0.3336	0.0229	0.037*
C4	0.7550 (3)	0.4153 (3)	0.3081 (10)	0.0352 (10)
Br1	0.89425 (3)	0.45978 (3)	0.4305 (2)	0.04971 (16)
C5	0.6611 (3)	0.4457 (2)	0.4299 (17)	0.0350 (8)
H5	0.6645	0.4905	0.5663	0.042*
C6	0.5603 (4)	0.4099 (3)	0.3509 (8)	0.0359 (11)
H6	0.4942	0.4299	0.4351	0.043*
C7	0.6470 (4)	0.2463 (3)	−0.1865 (9)	0.0350 (9)
H7	0.5764	0.2211	−0.2199	0.042*
C8	0.7312 (4)	0.2157 (3)	−0.3365 (10)	0.0339 (9)
H8	0.8032	0.2391	−0.3108	0.041*
C9	0.7127 (3)	0.1470 (3)	−0.5372 (13)	0.0368 (10)
H9	0.6403	0.1234	−0.5524	0.044*
O2	0.7830 (3)	0.1175 (2)	−0.6872 (7)	0.0426 (8)

	U11	U22	U33	U12	U13	U23
C1	0.022 (2)	0.038 (2)	0.038 (2)	−0.0013 (17)	0.0002 (17)	−0.0013 (19)
O1	0.0208 (16)	0.062 (2)	0.053 (2)	−0.0040 (15)	0.0017 (14)	−0.0239 (17)
C2	0.026 (2)	0.033 (2)	0.029 (2)	0.0007 (16)	0.0008 (15)	−0.0015 (16)
C3	0.021 (2)	0.032 (2)	0.039 (2)	0.0016 (16)	0.0024 (17)	0.0006 (18)
C4	0.026 (2)	0.035 (2)	0.045 (2)	−0.0046 (17)	−0.0061 (18)	−0.001 (2)
Br1	0.0290 (2)	0.0552 (3)	0.0649 (3)	−0.00854 (18)	−0.0047 (3)	−0.0132 (3)
C5	0.0267 (18)	0.0353 (18)	0.043 (2)	−0.0007 (14)	0.002 (4)	−0.007 (3)
C6	0.034 (2)	0.038 (2)	0.036 (3)	0.0056 (17)	0.0033 (17)	−0.0051 (18)
C7	0.031 (2)	0.035 (2)	0.039 (2)	−0.0026 (18)	0.0010 (19)	−0.0035 (19)
C8	0.028 (2)	0.035 (2)	0.039 (2)	0.0007 (18)	−0.0009 (19)	−0.0018 (18)
C9	0.029 (2)	0.0342 (19)	0.047 (3)	−0.0032 (15)	0.008 (2)	−0.002 (2)
O2	0.0374 (19)	0.0407 (17)	0.050 (2)	0.0004 (14)	0.0109 (14)	−0.0110 (15)

C1—O1	1.353 (5)	C5—C6	1.391 (6)
C1—C6	1.384 (6)	C5—H5	0.9500
C1—C2	1.411 (6)	C6—H6	0.9500
O1—H1	0.8400	C7—C8	1.339 (6)
C2—C3	1.389 (6)	C7—H7	0.9500
C2—C7	1.459 (6)	C8—C9	1.443 (7)
C3—C4	1.370 (6)	C8—H8	0.9500
C3—H3	0.9500	C9—O2	1.208 (6)
C4—C5	1.363 (6)	C9—H9	0.9500
C4—Br1	1.913 (4)
O1—C1—C6	122.0 (4)	C4—C5—H5	120.6
O1—C1—C2	117.6 (4)	C6—C5—H5	120.6
C6—C1—C2	120.4 (4)	C1—C6—C5	120.2 (4)
C1—O1—H1	109.5	C1—C6—H6	119.9
C3—C2—C1	118.1 (4)	C5—C6—H6	119.9
C3—C2—C7	122.6 (4)	C8—C7—C2	125.9 (4)
C1—C2—C7	119.3 (4)	C8—C7—H7	117.0
C4—C3—C2	120.3 (4)	C2—C7—H7	117.0
C4—C3—H3	119.9	C7—C8—C9	120.0 (4)
C2—C3—H3	119.9	C7—C8—H8	120.0
C5—C4—C3	122.2 (4)	C9—C8—H8	120.0
C5—C4—Br1	118.9 (4)	O2—C9—C8	124.5 (4)
C3—C4—Br1	118.9 (3)	O2—C9—H9	117.8
C4—C5—C6	118.9 (5)	C8—C9—H9	117.8
O1—C1—C2—C3	−179.8 (4)	Br1—C4—C5—C6	−176.7 (4)
C6—C1—C2—C3	−0.2 (6)	O1—C1—C6—C5	179.6 (5)
O1—C1—C2—C7	0.1 (6)	C2—C1—C6—C5	0.1 (7)
C6—C1—C2—C7	179.7 (4)	C4—C5—C6—C1	−0.7 (8)
C1—C2—C3—C4	1.0 (6)	C3—C2—C7—C8	−5.0 (7)
C7—C2—C3—C4	−178.9 (4)	C1—C2—C7—C8	175.1 (4)
C2—C3—C4—C5	−1.7 (7)	C2—C7—C8—C9	179.7 (4)
C2—C3—C4—Br1	176.5 (3)	C7—C8—C9—O2	177.5 (5)
C3—C4—C5—C6	1.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.89	2.693 (5)	160
C5—H5···O2ii	0.95	2.35	3.267 (6)	162

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O2i	0.84	1.89	2.693(5)	160
C5H5O2ii	0.95	2.35	3.267(6)	162

Symmetry codes: (i) ; (ii) .