(E)-2-Hy-droxy-cinnamaldehyde.

The asymmetric unit of the title compound, C9H8O2, contains two independent mol-ecules, 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 vinyl-aldehyde groups adopt extended conformations. In the crystal, mol-ecules 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 = 148.15

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.182

S = 0.97

3725 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006648/fy2086sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006648/fy2086Isup3.cml

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

C9H8O2	F(000) = 624
Mr = 148.15	Dx = 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

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

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(Fo2) + (0.0927P)2] where P = (Fo2 + 2Fc2)/3
3725 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.27 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
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)

	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)

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)

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

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) ; (ii) .