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

The title mol-ecule, C(15)H(20)O(4), has an E conformation about its C=C bond and is almost planar (r.m.s. deviation of all non-H atoms = 0.04 Å). The crystal structurere features O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background to caffeic acid and its derivatives, see: Buzzi et al. (2009 ▶); Uwai et al. (2008 ▶). For details of the synthesis, see: Feng et al. (2011 ▶); Son et al. (2011 ▶). For related structures, see: Xia et al. (2004 ▶, 2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H20O4

M = 264.31

Triclinic,

a = 5.2920 (11) Å

b = 10.689 (2) Å

c = 12.732 (3) Å

α = 95.45 (3)°

β = 92.76 (3)°

γ = 96.84 (3)°

V = 710.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.983, T max = 0.991

2912 measured reflections

2608 independent reflections

1515 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.178

S = 1.00

2608 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 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/S1600536811051671/aa2034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051671/aa2034Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051671/aa2034Isup3.cml

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

C15H20O4	Z = 2
Mr = 264.31	F(000) = 284
Triclinic, P1	Dx = 1.235 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2920 (11) Å	Cell parameters from 25 reflections
b = 10.689 (2) Å	θ = 9–13°
c = 12.732 (3) Å	µ = 0.09 mm−1
α = 95.45 (3)°	T = 293 K
β = 92.76 (3)°	Block, brown
γ = 96.84 (3)°	0.20 × 0.10 × 0.10 mm
V = 710.6 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1515 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.983, Tmax = 0.991	l = −15→15
2912 measured reflections	3 standard reflections every 200 reflections
2608 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.085P)2 + 0.096P] where P = (Fo2 + 2Fc2)/3
2608 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.28 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	0.7392 (4)	0.09426 (17)	0.38828 (16)	0.0649 (6)
H1A	0.6881	0.0408	0.4304	0.078*
C1	0.5906 (5)	0.3938 (2)	0.3065 (2)	0.0504 (7)
H1B	0.6496	0.4508	0.2597	0.060*
O2	0.3463 (4)	0.13532 (16)	0.51361 (14)	0.0564 (6)
H2A	0.2394	0.1617	0.5516	0.085*
C2	0.7038 (5)	0.2853 (2)	0.3144 (2)	0.0528 (8)
H2B	0.8390	0.2700	0.2730	0.063*
C3	0.6192 (5)	0.1991 (2)	0.3832 (2)	0.0463 (7)
O3	0.0120 (4)	0.75695 (18)	0.36537 (16)	0.0685 (7)
O4	0.2768 (4)	0.81988 (16)	0.24479 (15)	0.0571 (6)
C4	0.4190 (5)	0.2232 (2)	0.4456 (2)	0.0434 (7)
C5	0.3053 (5)	0.3312 (2)	0.43703 (19)	0.0440 (7)
H5A	0.1696	0.3462	0.4783	0.053*
C6	0.3883 (5)	0.4188 (2)	0.36794 (19)	0.0420 (6)
C7	0.2635 (5)	0.5329 (2)	0.36356 (19)	0.0443 (7)
H7A	0.1264	0.5394	0.4059	0.053*
C8	0.3218 (5)	0.6278 (2)	0.3067 (2)	0.0505 (7)
H8A	0.4555	0.6237	0.2622	0.061*
C9	0.1864 (5)	0.7388 (2)	0.3105 (2)	0.0466 (7)
C10	0.1571 (6)	0.9344 (2)	0.2397 (2)	0.0518 (7)
H10A	0.1845	0.9868	0.3067	0.062*
H10B	−0.0249	0.9137	0.2235	0.062*
C11	0.2783 (6)	1.0026 (2)	0.1537 (2)	0.0525 (7)
H11A	0.2586	0.9468	0.0884	0.063*
H11B	0.4594	1.0242	0.1720	0.063*
C12	0.1614 (5)	1.1224 (2)	0.1367 (2)	0.0506 (7)
H12A	−0.0210	1.1008	0.1222	0.061*
H12B	0.1877	1.1792	0.2015	0.061*
C13	0.2692 (6)	1.1911 (3)	0.0477 (2)	0.0584 (8)
H13A	0.2456	1.1339	−0.0168	0.070*
H13B	0.4512	1.2140	0.0629	0.070*
C14	0.1498 (7)	1.3098 (3)	0.0292 (3)	0.0744 (10)
H14A	−0.0338	1.2884	0.0198	0.089*
H14B	0.1860	1.3702	0.0915	0.089*
C15	0.2443 (8)	1.3718 (3)	−0.0660 (3)	0.0952 (13)
H15A	0.1629	1.4464	−0.0732	0.143*
H15B	0.2044	1.3136	−0.1284	0.143*
H15C	0.4256	1.3947	−0.0569	0.143*

	U11	U22	U33	U12	U13	U23
O1	0.0696 (14)	0.0486 (12)	0.0879 (15)	0.0312 (10)	0.0301 (12)	0.0239 (10)
C1	0.0538 (17)	0.0444 (15)	0.0573 (17)	0.0095 (13)	0.0182 (14)	0.0156 (13)
O2	0.0697 (13)	0.0446 (11)	0.0651 (12)	0.0252 (10)	0.0277 (10)	0.0239 (9)
C2	0.0500 (17)	0.0478 (16)	0.0664 (19)	0.0191 (14)	0.0213 (15)	0.0108 (14)
C3	0.0475 (16)	0.0373 (14)	0.0569 (17)	0.0139 (12)	0.0091 (13)	0.0056 (12)
O3	0.0834 (16)	0.0585 (13)	0.0778 (14)	0.0343 (11)	0.0419 (12)	0.0294 (11)
O4	0.0708 (13)	0.0429 (11)	0.0678 (13)	0.0232 (10)	0.0280 (11)	0.0254 (10)
C4	0.0489 (16)	0.0362 (14)	0.0478 (15)	0.0100 (12)	0.0100 (13)	0.0085 (12)
C5	0.0484 (16)	0.0406 (15)	0.0470 (15)	0.0153 (12)	0.0148 (13)	0.0077 (12)
C6	0.0485 (16)	0.0359 (14)	0.0441 (14)	0.0104 (12)	0.0083 (12)	0.0084 (11)
C7	0.0486 (17)	0.0403 (15)	0.0477 (16)	0.0126 (13)	0.0137 (13)	0.0083 (12)
C8	0.0581 (18)	0.0464 (16)	0.0533 (17)	0.0174 (14)	0.0213 (14)	0.0150 (13)
C9	0.0539 (17)	0.0393 (15)	0.0509 (16)	0.0126 (13)	0.0110 (14)	0.0134 (12)
C10	0.0632 (19)	0.0366 (14)	0.0618 (18)	0.0199 (13)	0.0177 (15)	0.0136 (13)
C11	0.0647 (19)	0.0437 (15)	0.0538 (16)	0.0150 (14)	0.0165 (14)	0.0133 (13)
C12	0.0589 (18)	0.0412 (15)	0.0556 (17)	0.0119 (13)	0.0149 (14)	0.0124 (13)
C13	0.072 (2)	0.0495 (17)	0.0578 (18)	0.0131 (15)	0.0152 (16)	0.0156 (14)
C14	0.098 (3)	0.0557 (19)	0.077 (2)	0.0170 (18)	0.018 (2)	0.0281 (17)
C15	0.134 (4)	0.072 (2)	0.083 (3)	0.002 (2)	0.007 (2)	0.037 (2)

O1—C3	1.357 (3)	C8—H8A	0.9300
O1—H1A	0.8500	C10—C11	1.499 (3)
C1—C2	1.377 (4)	C10—H10A	0.9700
C1—C6	1.392 (3)	C10—H10B	0.9700
C1—H1B	0.9300	C11—C12	1.516 (3)
O2—C4	1.371 (3)	C11—H11A	0.9700
O2—H2A	0.8200	C11—H11B	0.9700
C2—C3	1.382 (3)	C12—C13	1.507 (3)
C2—H2B	0.9300	C12—H12A	0.9700
C3—C4	1.389 (3)	C12—H12B	0.9700
O3—C9	1.207 (3)	C13—C14	1.516 (4)
O4—C9	1.326 (3)	C13—H13A	0.9700
O4—C10	1.449 (3)	C13—H13B	0.9700
C4—C5	1.375 (3)	C14—C15	1.514 (4)
C5—C6	1.392 (3)	C14—H14A	0.9700
C5—H5A	0.9300	C14—H14B	0.9700
C6—C7	1.459 (3)	C15—H15A	0.9600
C7—C8	1.317 (3)	C15—H15B	0.9600
C7—H7A	0.9300	C15—H15C	0.9600
C8—C9	1.455 (3)
C3—O1—H1A	118.8	O4—C10—H10B	110.4
C2—C1—C6	120.5 (2)	C11—C10—H10B	110.4
C2—C1—H1B	119.8	H10A—C10—H10B	108.6
C6—C1—H1B	119.8	C10—C11—C12	112.0 (2)
C4—O2—H2A	109.5	C10—C11—H11A	109.2
C1—C2—C3	120.9 (2)	C12—C11—H11A	109.2
C1—C2—H2B	119.6	C10—C11—H11B	109.2
C3—C2—H2B	119.6	C12—C11—H11B	109.2
O1—C3—C2	118.3 (2)	H11A—C11—H11B	107.9
O1—C3—C4	122.3 (2)	C13—C12—C11	113.9 (2)
C2—C3—C4	119.3 (2)	C13—C12—H12A	108.8
C9—O4—C10	117.5 (2)	C11—C12—H12A	108.8
O2—C4—C5	123.6 (2)	C13—C12—H12B	108.8
O2—C4—C3	116.7 (2)	C11—C12—H12B	108.8
C5—C4—C3	119.7 (2)	H12A—C12—H12B	107.7
C4—C5—C6	121.6 (2)	C12—C13—C14	114.1 (3)
C4—C5—H5A	119.2	C12—C13—H13A	108.7
C6—C5—H5A	119.2	C14—C13—H13A	108.7
C5—C6—C1	118.1 (2)	C12—C13—H13B	108.7
C5—C6—C7	119.2 (2)	C14—C13—H13B	108.7
C1—C6—C7	122.7 (2)	H13A—C13—H13B	107.6
C8—C7—C6	127.7 (2)	C15—C14—C13	113.5 (3)
C8—C7—H7A	116.1	C15—C14—H14A	108.9
C6—C7—H7A	116.1	C13—C14—H14A	108.9
C7—C8—C9	122.9 (2)	C15—C14—H14B	108.9
C7—C8—H8A	118.5	C13—C14—H14B	108.9
C9—C8—H8A	118.5	H14A—C14—H14B	107.7
O3—C9—O4	122.9 (2)	C14—C15—H15A	109.5
O3—C9—C8	125.4 (2)	C14—C15—H15B	109.5
O4—C9—C8	111.7 (2)	H15A—C15—H15B	109.5
O4—C10—C11	106.6 (2)	C14—C15—H15C	109.5
O4—C10—H10A	110.4	H15A—C15—H15C	109.5
C11—C10—H10A	110.4	H15B—C15—H15C	109.5
C6—C1—C2—C3	0.1 (4)	C5—C6—C7—C8	177.1 (3)
C1—C2—C3—O1	−179.5 (3)	C1—C6—C7—C8	−2.1 (5)
C1—C2—C3—C4	−0.7 (4)	C6—C7—C8—C9	−178.6 (3)
O1—C3—C4—O2	−0.1 (4)	C10—O4—C9—O3	−0.3 (4)
C2—C3—C4—O2	−178.9 (2)	C10—O4—C9—C8	179.3 (2)
O1—C3—C4—C5	179.9 (3)	C7—C8—C9—O3	0.9 (5)
C2—C3—C4—C5	1.1 (4)	C7—C8—C9—O4	−178.8 (3)
O2—C4—C5—C6	179.0 (2)	C9—O4—C10—C11	−175.1 (2)
C3—C4—C5—C6	−0.9 (4)	O4—C10—C11—C12	177.5 (2)
C4—C5—C6—C1	0.4 (4)	C10—C11—C12—C13	−177.4 (2)
C4—C5—C6—C7	−178.9 (2)	C11—C12—C13—C14	179.0 (3)
C2—C1—C6—C5	0.0 (4)	C12—C13—C14—C15	−175.2 (3)
C2—C1—C6—C7	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.85	2.41	2.733 (2)	103
O1—H1A···O2i	0.85	2.07	2.857 (2)	154
O2—H2A···O3ii	0.82	1.97	2.786 (3)	173
C5—H5A···O3ii	0.93	2.54	3.243 (3)	133
C7—H7A···O3	0.93	2.56	2.874 (3)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.85	2.07	2.857 (2)	154
O2—H2A⋯O3ii	0.82	1.97	2.786 (3)	173
C5—H5A⋯O3ii	0.93	2.54	3.243 (3)	133

Symmetry codes: (i) ; (ii) .