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

The title compound, C(14)H(18)O(4), a derivative of caffeic acid, has an E configuration about the C=C bond. The benzene ring is almost coplanar with the C=C-C(O)-O-C linker [maximum deviation = 0.050 (2) Å], making a dihedral angle of only 4.53 (2)°. In the mol-ecule, the adjacent hy-droxy groups form an O-H⋯O inter-action. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating a chain propagating in the [110] direction.

Related literature

For the biological properties of caffeic acid esters, see: Buzzi et al. (2009 ▶); Uwai et al. (2008 ▶). For synthetic details, see: Feng et al. (2011 ▶); Wang et al. (2011 ▶). For related structures, see: Xia et al. (2004 ▶, 2006 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C14H18O4

M = 250.28

Triclinic,

a = 5.2790 (11) Å

b = 10.244 (2) Å

c = 13.834 (3) Å

α = 69.05 (3)°

β = 80.11 (3)°

γ = 78.79 (3)°

V = 681.0 (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 = 0.974, T max = 0.991

2507 measured reflections

2507 independent reflections

1300 reflections with I > 2σ(I)

3 standard reflections every 200 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.156

S = 1.00

2507 reflections

163 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 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/S1600536812003352/su2370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003352/su2370Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003352/su2370Isup3.cml

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

C14H18O4	Z = 2
Mr = 250.28	F(000) = 268
Triclinic, P1	Dx = 1.220 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2790 (11) Å	Cell parameters from 25 reflections
b = 10.244 (2) Å	θ = 9–13°
c = 13.834 (3) Å	µ = 0.09 mm−1
α = 69.05 (3)°	T = 293 K
β = 80.11 (3)°	Block, colourless
γ = 78.79 (3)°	0.30 × 0.20 × 0.10 mm
V = 681.0 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1300 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −11→12
Tmin = 0.974, Tmax = 0.991	l = 0→16
2507 measured reflections	3 standard reflections every 200 min
2507 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
2507 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.14 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	0.2966 (5)	0.6252 (2)	0.56768 (18)	0.0557 (7)
H1A	0.1700	0.6372	0.5248	0.067*
O1	−0.0024 (4)	0.16077 (18)	0.62733 (15)	0.0877 (7)
O2	0.1887 (4)	0.01321 (17)	0.76260 (13)	0.0743 (6)
C2	0.4057 (5)	0.7386 (2)	0.55959 (18)	0.0543 (7)
O3	0.3407 (3)	0.87217 (15)	0.49143 (12)	0.0658 (6)
H3A	0.2404	0.8698	0.4531	0.099*
C3	0.5921 (5)	0.7242 (2)	0.62374 (18)	0.0561 (7)
O4	0.7014 (4)	0.83462 (17)	0.62142 (14)	0.0793 (7)
H4A	0.6432	0.9064	0.5765	0.119*
C4	0.6631 (5)	0.5938 (2)	0.6955 (2)	0.0663 (8)
H4B	0.7863	0.5837	0.7393	0.080*
C5	0.5533 (5)	0.4770 (3)	0.70355 (19)	0.0666 (8)
H5A	0.6029	0.3894	0.7523	0.080*
C6	0.3678 (5)	0.4917 (2)	0.63792 (17)	0.0530 (7)
C7	0.2509 (5)	0.3738 (2)	0.63921 (18)	0.0570 (7)
H7A	0.1330	0.3959	0.5909	0.068*
C8	0.2875 (5)	0.2395 (2)	0.69908 (18)	0.0610 (7)
H8A	0.4077	0.2102	0.7472	0.073*
C9	0.1449 (5)	0.1375 (2)	0.69123 (18)	0.0541 (7)
C10	0.0528 (7)	−0.0973 (3)	0.7622 (2)	0.0821 (10)
H10A	0.1149	−0.1228	0.7003	0.099*
H10B	−0.1322	−0.0639	0.7620	0.099*
C11	0.1015 (8)	−0.2212 (3)	0.8563 (2)	0.1123 (13)
H11A	0.0061	−0.2928	0.8556	0.135*
H11B	0.2847	−0.2584	0.8493	0.135*
C12	0.0392 (9)	−0.2063 (4)	0.9575 (2)	0.1090 (13)
H12A	0.1470	−0.1399	0.9599	0.131*
C13	0.1016 (11)	−0.3421 (5)	1.0451 (3)	0.171 (2)
H13A	0.2824	−0.3785	1.0352	0.256*
H13B	−0.0021	−0.4098	1.0459	0.256*
H13C	0.0644	−0.3247	1.1102	0.256*
C14	−0.2487 (11)	−0.1421 (5)	0.9771 (4)	0.179 (2)
H14A	−0.2887	−0.0562	0.9206	0.268*
H14B	−0.2751	−0.1222	1.0411	0.268*
H14C	−0.3602	−0.2082	0.9815	0.268*

	U11	U22	U33	U12	U13	U23
C1	0.0686 (18)	0.0450 (14)	0.0592 (15)	−0.0190 (13)	−0.0249 (13)	−0.0107 (12)
O1	0.1255 (19)	0.0556 (11)	0.0918 (14)	−0.0350 (11)	−0.0638 (14)	−0.0015 (10)
O2	0.1147 (17)	0.0505 (11)	0.0639 (11)	−0.0347 (10)	−0.0391 (11)	−0.0014 (9)
C2	0.0689 (18)	0.0438 (14)	0.0547 (14)	−0.0209 (13)	−0.0223 (13)	−0.0083 (12)
O3	0.0876 (14)	0.0435 (10)	0.0711 (11)	−0.0261 (9)	−0.0368 (10)	−0.0037 (8)
C3	0.0700 (18)	0.0471 (14)	0.0576 (14)	−0.0250 (13)	−0.0186 (13)	−0.0116 (12)
O4	0.1004 (16)	0.0569 (11)	0.0944 (14)	−0.0368 (11)	−0.0507 (11)	−0.0107 (10)
C4	0.080 (2)	0.0540 (16)	0.0741 (17)	−0.0224 (14)	−0.0340 (15)	−0.0142 (14)
C5	0.087 (2)	0.0486 (15)	0.0666 (16)	−0.0247 (14)	−0.0390 (15)	−0.0004 (12)
C6	0.0623 (17)	0.0493 (14)	0.0529 (14)	−0.0235 (13)	−0.0112 (12)	−0.0135 (12)
C7	0.0710 (19)	0.0493 (15)	0.0549 (14)	−0.0226 (13)	−0.0237 (13)	−0.0076 (12)
C8	0.079 (2)	0.0495 (15)	0.0574 (15)	−0.0228 (14)	−0.0284 (14)	−0.0048 (12)
C9	0.0681 (19)	0.0418 (14)	0.0534 (14)	−0.0161 (13)	−0.0183 (13)	−0.0078 (12)
C10	0.143 (3)	0.0514 (16)	0.0632 (16)	−0.0484 (17)	−0.0326 (17)	−0.0050 (13)
C11	0.183 (4)	0.069 (2)	0.092 (2)	−0.058 (2)	−0.050 (2)	0.0008 (18)
C12	0.120 (3)	0.126 (3)	0.073 (2)	−0.055 (3)	−0.016 (2)	−0.0006 (19)
C13	0.223 (6)	0.145 (4)	0.123 (3)	−0.028 (4)	−0.040 (3)	−0.009 (3)
C14	0.171 (6)	0.200 (6)	0.160 (5)	−0.019 (4)	−0.014 (4)	−0.060 (4)

C1—C2	1.356 (3)	C7—H7A	0.9300
C1—C6	1.390 (3)	C8—C9	1.444 (3)
C1—H1A	0.9300	C8—H8A	0.9300
O1—C9	1.207 (3)	C10—C11	1.476 (3)
O2—C9	1.310 (3)	C10—H10A	0.9700
O2—C10	1.455 (3)	C10—H10B	0.9700
C2—O3	1.373 (3)	C11—C12	1.439 (5)
C2—C3	1.388 (3)	C11—H11A	0.9700
O3—H3A	0.8200	C11—H11B	0.9700
C3—O4	1.355 (3)	C12—C13	1.505 (5)
C3—C4	1.377 (3)	C12—C14	1.553 (6)
O4—H4A	0.8200	C12—H12A	0.9800
C4—C5	1.390 (3)	C13—H13A	0.9600
C4—H4B	0.9300	C13—H13B	0.9600
C5—C6	1.398 (3)	C13—H13C	0.9600
C5—H5A	0.9300	C14—H14A	0.9600
C6—C7	1.453 (3)	C14—H14B	0.9600
C7—C8	1.324 (3)	C14—H14C	0.9600
C2—C1—C6	122.1 (2)	O2—C10—C11	108.5 (2)
C2—C1—H1A	118.9	O2—C10—H10A	110.0
C6—C1—H1A	118.9	C11—C10—H10A	110.0
C9—O2—C10	117.5 (2)	O2—C10—H10B	110.0
C1—C2—O3	124.0 (2)	C11—C10—H10B	110.0
C1—C2—C3	120.1 (2)	H10A—C10—H10B	108.4
O3—C2—C3	115.9 (2)	C12—C11—C10	119.8 (3)
C2—O3—H3A	109.5	C12—C11—H11A	107.4
O4—C3—C4	118.2 (2)	C10—C11—H11A	107.4
O4—C3—C2	122.6 (2)	C12—C11—H11B	107.4
C4—C3—C2	119.1 (2)	C10—C11—H11B	107.4
C3—O4—H4A	109.5	H11A—C11—H11B	106.9
C3—C4—C5	121.0 (2)	C11—C12—C13	113.3 (4)
C3—C4—H4B	119.5	C11—C12—C14	112.5 (4)
C5—C4—H4B	119.5	C13—C12—C14	109.6 (3)
C4—C5—C6	119.7 (2)	C11—C12—H12A	107.0
C4—C5—H5A	120.1	C13—C12—H12A	107.0
C6—C5—H5A	120.1	C14—C12—H12A	107.0
C1—C6—C5	117.9 (2)	C12—C13—H13A	109.5
C1—C6—C7	119.1 (2)	C12—C13—H13B	109.5
C5—C6—C7	122.9 (2)	H13A—C13—H13B	109.5
C8—C7—C6	129.5 (2)	C12—C13—H13C	109.5
C8—C7—H7A	115.3	H13A—C13—H13C	109.5
C6—C7—H7A	115.3	H13B—C13—H13C	109.5
C7—C8—C9	121.4 (2)	C12—C14—H14A	109.5
C7—C8—H8A	119.3	C12—C14—H14B	109.5
C9—C8—H8A	119.3	H14A—C14—H14B	109.5
O1—C9—O2	121.8 (2)	C12—C14—H14C	109.5
O1—C9—C8	125.2 (2)	H14A—C14—H14C	109.5
O2—C9—C8	113.0 (2)	H14B—C14—H14C	109.5
C6—C1—C2—O3	−179.9 (2)	C4—C5—C6—C7	177.9 (3)
C6—C1—C2—C3	−1.0 (4)	C1—C6—C7—C8	−179.5 (3)
C1—C2—C3—O4	−177.8 (3)	C5—C6—C7—C8	1.5 (4)
O3—C2—C3—O4	1.2 (4)	C6—C7—C8—C9	177.8 (3)
C1—C2—C3—C4	−0.3 (4)	C10—O2—C9—O1	0.1 (4)
O3—C2—C3—C4	178.7 (2)	C10—O2—C9—C8	179.5 (2)
O4—C3—C4—C5	178.4 (3)	C7—C8—C9—O1	5.2 (4)
C2—C3—C4—C5	0.8 (4)	C7—C8—C9—O2	−174.1 (2)
C3—C4—C5—C6	0.0 (4)	C9—O2—C10—C11	−172.5 (3)
C2—C1—C6—C5	1.7 (4)	O2—C10—C11—C12	56.0 (4)
C2—C1—C6—C7	−177.4 (2)	C10—C11—C12—C13	−179.7 (3)
C4—C5—C6—C1	−1.2 (4)	C10—C11—C12—C14	55.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.82	2.28	2.721 (2)	114
O3—H3A···O1i	0.82	1.95	2.764 (2)	173
O4—H4A···O3ii	0.82	2.13	2.831 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3	0.82	2.28	2.721 (2)	114
O3—H3A⋯O1i	0.82	1.95	2.764 (2)	173
O4—H4A⋯O3ii	0.82	2.13	2.831 (2)	143

Symmetry codes: (i) ; (ii) .