Crystal structure of (E)-3-(5-bromo-2-hydroxy­phen­yl)acryl­aldehyde

Kim, S.-G.

doi:10.1107/S1600536814023708

organic compounds

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Volume 70| Part 11| November 2014| Pages o1219-o1220

doi:10.1107/S1600536814023708

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Crystal structure of (E)-3-(5-bromo-2-hydroxyphenyl)acrylaldehyde

Sung-Gon Kim ^a ^*

^aDepartment of Chemistry, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon 443-760, Republic of Korea
^*Correspondence e-mail: sgkim123@kyonggi.ac.kr

Edited by T. N. Guru Row, Indian Institute of Science, India (Received 27 August 2014; accepted 28 October 2014; online 31 October 2014)

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 vinylaldehyde group adopts an extended conformation wih a C—C—C—C torsion angle of 179.7 (4)°. In the crystal, molecules are linked by classical O—H⋯O and weak C—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Keywords: crystal structure; trans configuration; vinylaldehyde group; hydrogen bonding; three-dimensional supramolecular network 2-hydroxycinnamaldehydes.

CCDC reference: 1031276

1. 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 ).

2. Experimental

2.1. Crystal data

C₉H₇BrO₂
M_r = 227.06
Orthorhombic, P n a 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.086
S = 1.16
2052 reflections
110 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.58 e Å⁻³
Absolute structure: Flack (1983 )
Absolute structure parameter: 0.021 (19)

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{3\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 1031276

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814023708/gw2149sup1.cif

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

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

checkCIF report

Structural commentary top

For related structures, see: Kang et al. (2013). 2-Hydroxycinnamaldehyde, isolated from the stern bark of cinnamonum cassia, and its synthetic derivatives have been shown to inhibit on farnesyl protein transferase in vitro as well as angiogenesis. (Kwon et al. 1996; Lee et al. 1999; Ka et al. 2003). Andrecently they also have been reported to have antitumor effects against various human tumor cells in vitro and in vivo (Gan et al. 2009; Han et al. 2011).In view of these potential applications and in continuation of our work, the structure of the title compound has been carried out and the results are presented here.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The title compound is essentially planar. The C==C double bond is in an E conformation and the vinylaldehyde groups adopt extended conformations as can be seen from the torsion angles C2—C7—C8—C9 = 179.7 (4)°. In the crystal, the molecules are linked by classic O—H···O hydrogen bond and weak C—H···O hydrogen bonds (Table 1).

Synthesis and crystallization top

5-Bromo-2-hydroxybenzaldehyde (5.0 mmol, 1.01 g) and (triphenylphosphoranylidene)acetaldehyde (6.0 mmol, 1.83 g) were dissolved in benzene (50 ml). After stirring for 6 h, solvent was evaporated. Purification by silica gel chromatography was afforded the title compound. Crystals suitable for X-ray analysis were obtained by recryatallization from an n-hexane/CH₂Cl₂ solution..

Refinement top

All H atoms were positioned geometrically, (O—H = 0.84 A ° and C—H = 0.95–0.96 Å) and constrained to ride on their parent atoms, with U_iso(H) = xUeq(C), where x = 1.2 for all other H atoms.

Related literature top

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).

Computing details top

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

Figures top

Fig. 1. A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 2. A partial view of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity.

(E)-3-(5-Bromo-2-hydroxyphenyl)acrylaldehyde top

Crystal data top

C₉H₇BrO₂	F(000) = 448
M_r = 227.06	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.P)² + 1.2584P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.001
2052 reflections	Δρ_max = 0.48 e Å⁻³
110 parameters	Δρ_min = −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)

Crystal data top

C₉H₇BrO₂	V = 892.06 (14) Å³
M_r = 227.06	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.1230 (11) Å	µ = 4.56 mm⁻¹
b = 15.0901 (14) Å	T = 200 K
c = 4.8763 (4) Å	0.41 × 0.35 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2052 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1683 reflections with I > 2σ(I)
T_min = 0.256, T_max = 0.548	R_int = 0.024
6031 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.48 e Å⁻³
S = 1.16	Δρ_min = −0.58 e Å⁻³
2052 reflections	Absolute structure: Flack (1983)
110 parameters	Absolute structure parameter: 0.021 (19)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1/2, −y+1/2, z+1; (ii) −x+3/2, y+1/2, z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.89	2.693 (5)	160.0
C5—H5···O2ⁱⁱ	0.95	2.35	3.267 (6)	162.0

Symmetry codes: (i) x−1/2, −y+1/2, z+1; (ii) −x+3/2, y+1/2, z+3/2.

Acknowledgements

This work was supported by Kyonggi University Research Grant 2013.

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1219-o1220

doi:10.1107/S1600536814023708

Open

access