Pentyl (E)-3-(3,4-dihy-droxy-phen-yl)acrylate.

In the mol-ecule of the title compound, C(14)H(18)O(4), the C=C double bond is in an E configuration. The mol-ecule is almost planar (r.m.s. deviation of all non-H atoms = 0.04 Å). An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, inter-molecular O-H⋯O inter-actions link the mol-ecules into ribbons extending in [110].

Related literature

For general background to the biological activity of caffeic acid and its esters, see: Uwai et al. (2008 ▶); Buzzi et al. (2009 ▶); For the preparation, see: Xia et al. (2006 ▶); Son et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H18O4

M = 250.28

Triclinic,

a = 5.3070 (11) Å

b = 10.567 (2) Å

c = 11.816 (2) Å

α = 90.96 (3)°

β = 91.84 (3)°

γ = 98.60 (3)°

V = 654.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

2703 measured reflections

2419 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.023

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.169

S = 1.00

2419 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040499/gw2109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040499/gw2109Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040499/gw2109Isup3.cml

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

C14H18O4	Z = 2
Mr = 250.28	F(000) = 268
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3070 (11) Å	Cell parameters from 25 reflections
b = 10.567 (2) Å	θ = 9–13°
c = 11.816 (2) Å	µ = 0.09 mm−1
α = 90.96 (3)°	T = 293 K
β = 91.84 (3)°	Block, colourless
γ = 98.60 (3)°	0.30 × 0.20 × 0.10 mm
V = 654.7 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1627 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.973, Tmax = 0.991	l = −14→14
2703 measured reflections	3 standard reflections every 200 reflections
2419 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.040P] where P = (Fo2 + 2Fc2)/3
2419 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 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
O1	−0.2441 (3)	1.39149 (14)	0.11914 (14)	0.0617 (5)
H1B	−0.1743	1.4410	0.0731	0.093*
C1	−0.1068 (4)	1.08131 (19)	0.20524 (17)	0.0469 (5)
H1A	−0.1712	1.0179	0.2547	0.056*
O2	0.1576 (3)	1.36636 (13)	−0.01491 (12)	0.0535 (4)
H2A	0.2656	1.3441	−0.0559	0.080*
C2	−0.2175 (4)	1.1903 (2)	0.19717 (18)	0.0506 (6)
H2B	−0.3549	1.2002	0.2416	0.061*
C3	−0.1266 (4)	1.28540 (18)	0.12364 (17)	0.0435 (5)
O3	0.4807 (3)	0.73067 (15)	0.14536 (14)	0.0699 (6)
O4	0.2176 (3)	0.65259 (13)	0.27822 (13)	0.0578 (5)
C4	0.0776 (4)	1.26997 (18)	0.05777 (16)	0.0408 (5)
C5	0.1902 (4)	1.16118 (18)	0.06704 (16)	0.0408 (5)
H5A	0.3293	1.1521	0.0233	0.049*
C6	0.0999 (4)	1.06446 (18)	0.14062 (16)	0.0396 (5)
C7	0.2247 (4)	0.95104 (18)	0.14637 (17)	0.0453 (5)
H7A	0.3589	0.9487	0.0980	0.054*
C8	0.1716 (4)	0.85117 (19)	0.21148 (17)	0.0493 (6)
H8A	0.0415	0.8506	0.2624	0.059*
C9	0.3082 (4)	0.74206 (19)	0.20677 (17)	0.0457 (5)
C10	0.3335 (4)	0.53739 (19)	0.28150 (19)	0.0519 (6)
H10A	0.5153	0.5582	0.2982	0.062*
H10B	0.3079	0.4919	0.2091	0.062*
C11	0.2072 (5)	0.4569 (2)	0.37279 (18)	0.0525 (6)
H11A	0.0261	0.4364	0.3542	0.063*
H11B	0.2270	0.5057	0.4437	0.063*
C12	0.3173 (4)	0.3342 (2)	0.38791 (18)	0.0512 (6)
H12A	0.2967	0.2858	0.3169	0.061*
H12B	0.4987	0.3553	0.4055	0.061*
C13	0.1962 (5)	0.2508 (2)	0.4799 (2)	0.0664 (7)
H13A	0.0162	0.2262	0.4609	0.080*
H13B	0.2109	0.2998	0.5506	0.080*
C14	0.3177 (7)	0.1313 (3)	0.4962 (3)	0.0930 (10)
H14A	0.2336	0.0813	0.5549	0.140*
H14B	0.4949	0.1551	0.5172	0.140*
H14C	0.3016	0.0818	0.4268	0.140*

	U11	U22	U33	U12	U13	U23
O1	0.0648 (10)	0.0488 (9)	0.0805 (11)	0.0307 (8)	0.0265 (8)	0.0173 (8)
C1	0.0505 (13)	0.0405 (11)	0.0512 (12)	0.0086 (9)	0.0125 (10)	0.0095 (9)
O2	0.0618 (10)	0.0405 (8)	0.0644 (9)	0.0217 (7)	0.0251 (8)	0.0162 (7)
C2	0.0468 (12)	0.0504 (13)	0.0587 (13)	0.0164 (10)	0.0180 (10)	0.0057 (10)
C3	0.0438 (12)	0.0371 (11)	0.0522 (12)	0.0139 (9)	0.0048 (9)	0.0010 (9)
O3	0.0806 (12)	0.0553 (10)	0.0841 (12)	0.0321 (8)	0.0460 (10)	0.0256 (8)
O4	0.0741 (11)	0.0403 (8)	0.0658 (10)	0.0227 (7)	0.0301 (8)	0.0172 (7)
C4	0.0456 (11)	0.0339 (10)	0.0439 (11)	0.0081 (9)	0.0059 (9)	0.0039 (8)
C5	0.0408 (11)	0.0383 (11)	0.0456 (11)	0.0116 (9)	0.0091 (9)	0.0025 (9)
C6	0.0427 (11)	0.0342 (10)	0.0430 (10)	0.0089 (8)	0.0040 (9)	0.0008 (8)
C7	0.0488 (12)	0.0400 (11)	0.0492 (11)	0.0114 (9)	0.0116 (10)	0.0039 (9)
C8	0.0573 (13)	0.0371 (11)	0.0569 (13)	0.0147 (10)	0.0189 (11)	0.0065 (10)
C9	0.0515 (13)	0.0392 (11)	0.0482 (11)	0.0099 (9)	0.0112 (10)	0.0048 (9)
C10	0.0640 (14)	0.0362 (11)	0.0601 (13)	0.0190 (10)	0.0157 (11)	0.0082 (10)
C11	0.0644 (15)	0.0430 (12)	0.0534 (12)	0.0151 (10)	0.0181 (11)	0.0072 (10)
C12	0.0580 (14)	0.0430 (12)	0.0555 (13)	0.0142 (10)	0.0090 (11)	0.0084 (10)
C13	0.0863 (19)	0.0551 (14)	0.0610 (14)	0.0161 (13)	0.0184 (13)	0.0158 (11)
C14	0.126 (3)	0.0666 (17)	0.095 (2)	0.0349 (17)	0.0191 (19)	0.0386 (15)

O1—C3	1.363 (2)	C7—H7A	0.9300
O1—H1B	0.8200	C8—C9	1.452 (3)
C1—C2	1.372 (3)	C8—H8A	0.9300
C1—C6	1.388 (3)	C10—C11	1.498 (3)
C1—H1A	0.9300	C10—H10A	0.9700
O2—C4	1.371 (2)	C10—H10B	0.9700
O2—H2A	0.8200	C11—C12	1.512 (3)
C2—C3	1.382 (3)	C11—H11A	0.9700
C2—H2B	0.9300	C11—H11B	0.9700
C3—C4	1.382 (3)	C12—C13	1.509 (3)
O3—C9	1.205 (2)	C12—H12A	0.9700
O4—C9	1.324 (2)	C12—H12B	0.9700
O4—C10	1.444 (2)	C13—C14	1.513 (3)
C4—C5	1.377 (3)	C13—H13A	0.9700
C5—C6	1.393 (3)	C13—H13B	0.9700
C5—H5A	0.9300	C14—H14A	0.9600
C6—C7	1.455 (3)	C14—H14B	0.9600
C7—C8	1.318 (3)	C14—H14C	0.9600
C3—O1—H1B	109.5	O4—C10—C11	106.74 (16)
C2—C1—C6	120.89 (18)	O4—C10—H10A	110.4
C2—C1—H1A	119.6	C11—C10—H10A	110.4
C6—C1—H1A	119.6	O4—C10—H10B	110.4
C4—O2—H2A	109.5	C11—C10—H10B	110.4
C1—C2—C3	120.64 (18)	H10A—C10—H10B	108.6
C1—C2—H2B	119.7	C10—C11—C12	112.26 (17)
C3—C2—H2B	119.7	C10—C11—H11A	109.2
O1—C3—C2	118.08 (17)	C12—C11—H11A	109.2
O1—C3—C4	122.54 (18)	C10—C11—H11B	109.2
C2—C3—C4	119.38 (18)	C12—C11—H11B	109.2
C9—O4—C10	117.71 (15)	H11A—C11—H11B	107.9
O2—C4—C5	123.18 (17)	C13—C12—C11	113.87 (18)
O2—C4—C3	116.98 (17)	C13—C12—H12A	108.8
C5—C4—C3	119.85 (18)	C11—C12—H12A	108.8
C4—C5—C6	121.30 (17)	C13—C12—H12B	108.8
C4—C5—H5A	119.4	C11—C12—H12B	108.8
C6—C5—H5A	119.4	H12A—C12—H12B	107.7
C1—C6—C5	117.94 (18)	C12—C13—C14	112.6 (2)
C1—C6—C7	123.06 (18)	C12—C13—H13A	109.1
C5—C6—C7	119.01 (17)	C14—C13—H13A	109.1
C8—C7—C6	128.16 (19)	C12—C13—H13B	109.1
C8—C7—H7A	115.9	C14—C13—H13B	109.1
C6—C7—H7A	115.9	H13A—C13—H13B	107.8
C7—C8—C9	122.58 (19)	C13—C14—H14A	109.5
C7—C8—H8A	118.7	C13—C14—H14B	109.5
C9—C8—H8A	118.7	H14A—C14—H14B	109.5
O3—C9—O4	122.77 (19)	C13—C14—H14C	109.5
O3—C9—C8	125.58 (19)	H14A—C14—H14C	109.5
O4—C9—C8	111.64 (17)	H14B—C14—H14C	109.5
C6—C1—C2—C3	0.5 (3)	C4—C5—C6—C7	179.50 (18)
C1—C2—C3—O1	179.97 (19)	C1—C6—C7—C8	−1.5 (4)
C1—C2—C3—C4	0.1 (3)	C5—C6—C7—C8	178.6 (2)
O1—C3—C4—O2	−0.8 (3)	C6—C7—C8—C9	178.43 (19)
C2—C3—C4—O2	179.06 (18)	C10—O4—C9—O3	0.1 (3)
O1—C3—C4—C5	179.26 (18)	C10—O4—C9—C8	179.17 (18)
C2—C3—C4—C5	−0.8 (3)	C7—C8—C9—O3	0.3 (4)
O2—C4—C5—C6	−178.85 (17)	C7—C8—C9—O4	−178.7 (2)
C3—C4—C5—C6	1.0 (3)	C9—O4—C10—C11	176.82 (18)
C2—C1—C6—C5	−0.4 (3)	O4—C10—C11—C12	−178.17 (18)
C2—C1—C6—C7	179.72 (19)	C10—C11—C12—C13	179.56 (19)
C4—C5—C6—C1	−0.4 (3)	C11—C12—C13—C14	−177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2	0.82	2.30	2.738 (2)	114
O1—H1B···O2i	0.82	2.15	2.840 (2)	142
O2—H2A···O3ii	0.82	1.98	2.800 (2)	173
C5—H5A···O3ii	0.93	2.52	3.230 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2	0.82	2.30	2.738 (2)	114
O1—H1B⋯O2i	0.82	2.15	2.840 (2)	142
O2—H2A⋯O3ii	0.82	1.98	2.800 (2)	173
C5—H5A⋯O3ii	0.93	2.52	3.230 (3)	133

Symmetry codes: (i) ; (ii) .