(E)-2-Hy­droxy­cinnamaldehyde

Kang, K.-T.; Kim, S.-G.

doi:10.1107/S1600536813006648

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o534

doi:10.1107/S1600536813006648

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(E)-2-Hydroxycinnamaldehyde

Ki-Tae Kang ^a and Sung-Gon Kim ^a ^*

^aDepartment of Chemistry, Kyonggi University, San 94-6, Iui-dong, Yeongtong-gu, Suwon 443-760, Republic of Korea
^*Correspondence e-mail: sgkim123@kyonggi.ac.kr

(Received 26 December 2012; accepted 8 March 2013; online 16 March 2013)

The asymmetric unit of the title compound, C₉H₈O₂, contains two independent molecules, both of which are essentially planar (r.m.s. deviations = 0.0294 and 0.0284 Å). The C=C double bond is in an E conformation and the vinylaldehyde groups adopt extended conformations. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming infinite chains parallel to [101].

Related literature

For the synthesis of the title compound, see: Kim et al. (2004 ); Zeiter & Rose (2009 ). For the biological activity of 2-hydroxycinnamaldehydes, see: Kwon et al. (1996 ); Lee et al. (1999 ); Ka et al. (2003 ). For applications of 2-hydroxycinnamaldehydes, see: Zu et al. (2009 ); Choi & Kim (2010 ); Lee & Kim (2011 ).

Experimental

Crystal data

C₉H₈O₂
M_r = 148.15
Monoclinic, P 2₁ /c
a = 10.1192 (15) Å
b = 13.7078 (19) Å
c = 10.9891 (15) Å
β = 102.537 (3)°
V = 1488.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.40 × 0.34 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer
10982 measured reflections
3725 independent reflections
1785 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.182
S = 0.97
3725 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.84	1.90	2.7260 (19)	166
O1—H1A⋯O4ⁱⁱ	0.84	1.90	2.7193 (19)	166
Symmetry codes: (i) x, y+1, z-1; (ii) x+1, y-1, z.

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006648/fy2086sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006648/fy2086Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006648/fy2086Isup3.cml

checkCIF report

Comment top

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, and tumor cell growth (Kwon et al. 1996; Lee et al. 1999; Ka et al. 2003). In view of these potential applications and in continuation of our work, the structure of the title compound has been determined and the results are presented here.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The asymmetric unit of the title compound contains two independent molecules, A and B, with similar conformations. Both molecules are essentially planar. The r.m.s deviations of the atoms from their mean plane in molecules A and B are 0.0294 Å and 0.0284 Å, respectively. The molecule displays a trans configuration with respect to the C═C double bond, and the vinylaldehyde groups adopt extended conformations as can be seen from the torsion angles C2—C7—C8—C9 = -177.1 (2)° and C11—C16—C17—C18 = 179.2 (2)°. In the crystal, the molecules are linked by intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For the synthesis of the title compound, see: Kim et al. (2004); Zeiter & Rose (2009). For the biological activity of 2-hydroxycinnamaldehydes, see: Kwon et al. (1996); Lee et al. (1999); Ka et al. (2003). For applications of 2-hydroxycinnamaldehydes, see: Zu et al. (2009); Choi & Kim (2010); Lee & Kim (2011).

Experimental top

A solution of 2-hydroxybenzaldehyde (10.0 mmol) and vinyl acetate (11.0 mmol) in CH₃CN (20 ml) was added to a stirred suspension of K₂CO₃ in CH₃CN (30 ml). After refluxing for 48 h, the reaction mixture was poured into cold water and diluted with EtOAc. The organic layer was washed with 10% NaOH solution, and the aqueous layer was separated, acidified with 10% HCl solution, and extracted with CH₂Cl₂. The resultant organic layer was dried over MgSO₄ and concentrated in vacuo. The dark residue was purified by silica gel chromatography to afford the title compound (Fig. 2). Crystals suitable for X-ray analysis were obtained by slow evaporation from an n-hexane/CH₂Cl₂ solution.

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. The preparation of the title compound.

(E)-2-Hydroxycinnamaldehyde top

Crystal data top

C₉H₈O₂	F(000) = 624
M_r = 148.15	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3327 reflections
a = 10.1192 (15) Å	θ = 2.4–28.3°
b = 13.7078 (19) Å	µ = 0.09 mm⁻¹
c = 10.9891 (15) Å	T = 200 K
β = 102.537 (3)°	Block, pale yellow
V = 1488.0 (4) Å³	0.40 × 0.34 × 0.29 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	1785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 28.4°, θ_min = 2.1°
ϕ and ω scans	h = −13→12
10982 measured reflections	k = −18→16
3725 independent reflections	l = −14→14

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0927P)²] where P = (F_o² + 2F_c²)/3
3725 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₉H₈O₂	V = 1488.0 (4) Å³
M_r = 148.15	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1192 (15) Å	µ = 0.09 mm⁻¹
b = 13.7078 (19) Å	T = 200 K
c = 10.9891 (15) Å	0.40 × 0.34 × 0.29 mm
β = 102.537 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	1785 reflections with I > 2σ(I)
10982 measured reflections	R_int = 0.041
3725 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 0.97	Δρ_max = 0.22 e Å⁻³
3725 reflections	Δρ_min = −0.27 e Å⁻³
201 parameters

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	1.0099 (2)	0.23356 (14)	0.6613 (2)	0.0446 (5)
O1	1.00066 (17)	0.13543 (10)	0.66051 (15)	0.0594 (5)
H1A	1.0513	0.1121	0.6166	0.089*
C2	0.9346 (2)	0.28553 (14)	0.73291 (19)	0.0407 (5)
C3	0.9417 (2)	0.38675 (15)	0.7331 (2)	0.0483 (6)
H3	0.8915	0.4230	0.7813	0.058*
C4	1.0197 (2)	0.43568 (16)	0.6651 (2)	0.0568 (7)
H4	1.0226	0.5049	0.6658	0.068*
C5	1.0941 (2)	0.38336 (16)	0.5954 (2)	0.0526 (6)
H5	1.1484	0.4169	0.5484	0.063*
C6	1.0897 (2)	0.28362 (15)	0.5939 (2)	0.0494 (6)
H6	1.1416	0.2483	0.5463	0.059*
C7	0.8519 (2)	0.23186 (15)	0.80343 (19)	0.0447 (5)
H7	0.8512	0.1629	0.7948	0.054*
C8	0.7771 (2)	0.26827 (15)	0.8786 (2)	0.0476 (6)
H8	0.7705	0.3369	0.8879	0.057*
C9	0.7067 (2)	0.20404 (16)	0.94542 (19)	0.0475 (6)
H9	0.7137	0.1361	0.9307	0.057*
O2	0.63875 (17)	0.22802 (11)	1.01920 (14)	0.0556 (5)
C10	0.5413 (2)	1.02655 (15)	0.18904 (19)	0.0449 (5)
O3	0.50581 (16)	1.12074 (10)	0.16394 (15)	0.0573 (5)
H3A	0.5548	1.1450	0.1191	0.086*
C11	0.4817 (2)	0.97679 (15)	0.27481 (19)	0.0437 (5)
C12	0.5162 (2)	0.87942 (15)	0.3007 (2)	0.0470 (6)
H12	0.4756	0.8449	0.3581	0.056*
C13	0.6071 (2)	0.83215 (16)	0.2456 (2)	0.0513 (6)
H13	0.6300	0.7659	0.2651	0.062*
C14	0.6654 (2)	0.88235 (16)	0.1606 (2)	0.0545 (6)
H14	0.7278	0.8500	0.1212	0.065*
C15	0.6336 (2)	0.97798 (16)	0.1334 (2)	0.0531 (6)
H15	0.6750	1.0116	0.0759	0.064*
C16	0.3859 (2)	1.02833 (15)	0.3339 (2)	0.0472 (6)
H16	0.3724	1.0955	0.3138	0.057*
C17	0.3155 (2)	0.99221 (15)	0.4125 (2)	0.0468 (6)
H17	0.3238	0.9253	0.4353	0.056*
C18	0.2269 (2)	1.05456 (15)	0.4629 (2)	0.0498 (6)
H18	0.2201	1.1204	0.4353	0.060*
O4	0.15958 (16)	1.03140 (10)	0.53740 (14)	0.0556 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (13)	0.0384 (11)	0.0525 (13)	0.0014 (9)	0.0243 (11)	0.0000 (9)
O1	0.0778 (13)	0.0387 (8)	0.0785 (12)	−0.0006 (7)	0.0535 (10)	−0.0030 (7)
C2	0.0439 (13)	0.0384 (11)	0.0440 (12)	0.0026 (9)	0.0189 (10)	−0.0009 (9)
C3	0.0536 (14)	0.0434 (12)	0.0535 (14)	0.0030 (10)	0.0238 (11)	−0.0019 (10)
C4	0.0662 (17)	0.0406 (12)	0.0712 (17)	−0.0037 (11)	0.0319 (14)	−0.0005 (11)
C5	0.0594 (15)	0.0488 (13)	0.0575 (14)	−0.0061 (11)	0.0298 (12)	0.0029 (11)
C6	0.0545 (15)	0.0462 (12)	0.0560 (14)	0.0022 (10)	0.0308 (12)	−0.0004 (10)
C7	0.0497 (14)	0.0414 (12)	0.0485 (13)	0.0010 (9)	0.0228 (11)	−0.0009 (9)
C8	0.0550 (15)	0.0433 (12)	0.0518 (13)	0.0000 (10)	0.0277 (12)	−0.0024 (10)
C9	0.0543 (15)	0.0467 (12)	0.0466 (13)	−0.0003 (10)	0.0223 (11)	−0.0026 (10)
O2	0.0639 (11)	0.0573 (10)	0.0565 (10)	−0.0011 (8)	0.0368 (9)	−0.0010 (7)
C10	0.0520 (14)	0.0390 (11)	0.0509 (13)	−0.0038 (9)	0.0274 (11)	−0.0050 (9)
O3	0.0728 (12)	0.0428 (9)	0.0708 (11)	0.0018 (7)	0.0470 (9)	0.0043 (7)
C11	0.0466 (13)	0.0416 (12)	0.0493 (13)	−0.0030 (9)	0.0245 (11)	−0.0044 (9)
C12	0.0517 (14)	0.0427 (12)	0.0533 (13)	−0.0029 (10)	0.0262 (11)	0.0003 (10)
C13	0.0572 (15)	0.0413 (12)	0.0614 (14)	0.0006 (10)	0.0260 (12)	−0.0028 (10)
C14	0.0565 (15)	0.0498 (13)	0.0667 (15)	0.0036 (11)	0.0343 (13)	−0.0058 (11)
C15	0.0561 (15)	0.0541 (14)	0.0594 (15)	−0.0032 (11)	0.0353 (13)	−0.0027 (11)
C16	0.0539 (15)	0.0408 (11)	0.0549 (13)	−0.0015 (10)	0.0292 (12)	−0.0018 (10)
C17	0.0531 (14)	0.0435 (12)	0.0519 (13)	−0.0001 (10)	0.0292 (11)	−0.0023 (10)
C18	0.0561 (15)	0.0458 (13)	0.0556 (14)	−0.0004 (10)	0.0299 (12)	−0.0014 (10)
O4	0.0619 (11)	0.0516 (9)	0.0663 (10)	−0.0048 (7)	0.0421 (9)	−0.0062 (8)

Geometric parameters (Å, º) top

C1—O1	1.348 (2)	C10—O3	1.352 (2)
C1—C6	1.390 (3)	C10—C15	1.392 (3)
C1—C2	1.403 (3)	C10—C11	1.401 (3)
O1—H1A	0.8400	O3—H3A	0.8400
C2—C3	1.389 (3)	C11—C12	1.393 (3)
C2—C7	1.457 (3)	C11—C16	1.460 (3)
C3—C4	1.374 (3)	C12—C13	1.369 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.385 (3)	C13—C14	1.390 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.368 (3)	C14—C15	1.367 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.333 (3)	C16—C17	1.330 (3)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.431 (3)	C17—C18	1.434 (3)
C8—H8	0.9500	C17—H17	0.9500
C9—O2	1.216 (2)	C18—O4	1.215 (2)
C9—H9	0.9500	C18—H18	0.9500

O1—C1—C6	122.46 (17)	O3—C10—C15	122.74 (18)
O1—C1—C2	117.70 (17)	O3—C10—C11	117.90 (17)
C6—C1—C2	119.84 (19)	C15—C10—C11	119.4 (2)
C1—O1—H1A	109.5	C10—O3—H3A	109.5
C3—C2—C1	118.24 (18)	C12—C11—C10	118.56 (18)
C3—C2—C7	122.64 (18)	C12—C11—C16	122.27 (18)
C1—C2—C7	119.12 (18)	C10—C11—C16	119.17 (19)
C4—C3—C2	121.5 (2)	C13—C12—C11	121.74 (19)
C4—C3—H3	119.2	C13—C12—H12	119.1
C2—C3—H3	119.2	C11—C12—H12	119.1
C3—C4—C5	119.6 (2)	C12—C13—C14	119.1 (2)
C3—C4—H4	120.2	C12—C13—H13	120.4
C5—C4—H4	120.2	C14—C13—H13	120.4
C6—C5—C4	120.3 (2)	C15—C14—C13	120.5 (2)
C6—C5—H5	119.9	C15—C14—H14	119.7
C4—C5—H5	119.9	C13—C14—H14	119.7
C5—C6—C1	120.53 (19)	C14—C15—C10	120.73 (19)
C5—C6—H6	119.7	C14—C15—H15	119.6
C1—C6—H6	119.7	C10—C15—H15	119.6
C8—C7—C2	127.6 (2)	C17—C16—C11	127.6 (2)
C8—C7—H7	116.2	C17—C16—H16	116.2
C2—C7—H7	116.2	C11—C16—H16	116.2
C7—C8—C9	120.0 (2)	C16—C17—C18	119.8 (2)
C7—C8—H8	120.0	C16—C17—H17	120.1
C9—C8—H8	120.0	C18—C17—H17	120.1
O2—C9—C8	126.3 (2)	O4—C18—C17	126.4 (2)
O2—C9—H9	116.9	O4—C18—H18	116.8
C8—C9—H9	116.9	C17—C18—H18	116.8

O1—C1—C2—C3	−179.1 (2)	O3—C10—C11—C12	179.4 (2)
C6—C1—C2—C3	0.5 (3)	C15—C10—C11—C12	−0.6 (3)
O1—C1—C2—C7	0.7 (3)	O3—C10—C11—C16	−0.6 (3)
C6—C1—C2—C7	−179.8 (2)	C15—C10—C11—C16	179.4 (2)
C1—C2—C3—C4	0.2 (3)	C10—C11—C12—C13	0.6 (3)
C7—C2—C3—C4	−179.5 (2)	C16—C11—C12—C13	−179.4 (2)
C2—C3—C4—C5	−0.6 (4)	C11—C12—C13—C14	−0.7 (4)
C3—C4—C5—C6	0.2 (4)	C12—C13—C14—C15	0.7 (4)
C4—C5—C6—C1	0.5 (4)	C13—C14—C15—C10	−0.7 (4)
O1—C1—C6—C5	178.7 (2)	O3—C10—C15—C14	−179.3 (2)
C2—C1—C6—C5	−0.8 (3)	C11—C10—C15—C14	0.7 (4)
C3—C2—C7—C8	−2.3 (4)	C12—C11—C16—C17	−3.3 (4)
C1—C2—C7—C8	178.0 (2)	C10—C11—C16—C17	176.7 (2)
C2—C7—C8—C9	−177.1 (2)	C11—C16—C17—C18	179.2 (2)
C7—C8—C9—O2	177.7 (2)	C16—C17—C18—O4	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.84	1.90	2.7260 (19)	166
O1—H1A···O4ⁱⁱ	0.84	1.90	2.7193 (19)	166

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

Experimental details

Crystal data
Chemical formula	C₉H₈O₂
M_r	148.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	10.1192 (15), 13.7078 (19), 10.9891 (15)
β (°)	102.537 (3)
V (Å³)	1488.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.34 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10982, 3725, 1785
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.182, 0.97
No. of reflections	3725
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.84	1.90	2.7260 (19)	165.7
O1—H1A···O4ⁱⁱ	0.84	1.90	2.7193 (19)	166.3

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

Acknowledgements

This work was supported by Kyonggi University Research Grant 2012.

References

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