Pentyl (E)-3-(3,4-dihy­droxy­phen­yl)acrylate

Wang, J.; Gu, S.; Zhang, L.; Wu, F.; Guo, X.

doi:10.1107/S1600536811040499

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2871

doi:10.1107/S1600536811040499

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access

Pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Jun Wang,^a ^* Shuangshuang Gu,^a Leixia Zhang,^a Fuan Wu ^a,^b and Xijie Guo ^a,^b

^aSchool of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China, and ^bSericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, People's Republic of China
^*Correspondence e-mail: jimwang_js@hotmail.com

(Received 31 August 2011; accepted 2 October 2011; online 8 October 2011)

In the molecule of the title compound, C₁₄H₁₈O₄, the C=C double bond is in an E configuration. The molecule is almost planar (r.m.s. deviation of all non-H atoms = 0.04 Å). An intramolecular O—H⋯O hydrogen bond occurs. In the crystal, intermolecular O—H⋯O interactions link the molecules 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_r = 250.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.169
S = 1.00
2419 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x, -y+3, -z; (ii) -x+1, -y+2, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040499/gw2109sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040499/gw2109Isup3.cml

checkCIF report

Comment top

Caffeic acid and its esters have been a research hot spot for a long time. These compounds are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities (Uwai et al., 2008; Buzzi et al., 2009). As a part of our studies into the synthesis of caffeic acid derivatives, the title compound (1) pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate was synthesized (Xia et al. (2006); Son et al. (2011)). We report herein the crystal structure of the title compound.

The molecule of (I) has an E configuration (Fig. 1); All non-H atoms of (I) are almost coplanar, with a root mean square deviating from the least-squares plane of 0.04 A°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, hydroxy groups contribute to intermolecular O—H···O interactions (Table 1) link the molecules into ribbons extended in the [110] direction (Fig. 2), in which they may be effective in the stabilization of thestructure. On the other hand, the intramolecular O—H···O H-bond also contribute to the stability of the molecular configuration (Fig. 1 and Table 1).

Related literature top

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 top

Esterification of caffeic acid with amyl alcohol was performed in a column (inner diameter= 15 mm, length = 200 mm). Caffeic acid (8.95 g, 0.05 mol) was dissolved in amyl alcohol (100 ml). The mixture was stirred at 80°C for 60 minutes and fed from the top of the reactor with syringe pumps. The feed rate of the mixture was fixed at 10.0 ml/h. Cation exchange resin CD-552 particles(5 g) and molecular sieve(5 g) were packed into the middle of the reactor and glass beads of 2 mm in diameter were loaded into the rest of the column. The reaction temperature continued at 90°C for 20 h. The mixture was evaporated to dryness and followed by the addition of ethanol and extracted with chloroform three times. The chloroform extract was dried over evaporated to give a solid residue, and dissolved in ethanol/petroleum ether (1:1) to crystal. The solution was filtered and concentrated to yield a brown crystalline product (5.3 g, 59.2%). Recrystallization from ethanol gave colourless crystal.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

Pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate top

Crystal data top

C₁₄H₁₈O₄	Z = 2
M_r = 250.28	F(000) = 268
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)² + 0.040P] where P = (F_o² + 2F_c²)/3
2419 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₈O₄	γ = 98.60 (3)°
M_r = 250.28	V = 654.7 (2) Å³
Triclinic, P1	Z = 2
a = 5.3070 (11) Å	Mo Kα radiation
b = 10.567 (2) Å	µ = 0.09 mm⁻¹
c = 11.816 (2) Å	T = 293 K
α = 90.96 (3)°	0.30 × 0.20 × 0.10 mm
β = 91.84 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1627 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
2703 measured reflections	intensity decay: 1%
2419 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
2419 reflections	Δρ_min = −0.19 e Å⁻³
163 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+3, −z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈O₄
M_r	250.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.3070 (11), 10.567 (2), 11.816 (2)
α, β, γ (°)	90.96 (3), 91.84 (3), 98.60 (3)
V (Å³)	654.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2703, 2419, 1627
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.169, 1.00
No. of reflections	2419
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+3, −z; (ii) −x+1, −y+2, −z.

Acknowledgements

This work was sponsored by the Qing Lan Project of Jiangsu Province, the Natural Science Foundation of Jiangsu Province (BK2009213), the College Natural Science Research Project of Jiangsu Province (08KJB530002), the Science and Technology Support Program of Jiangsu Province (BE2010419), the Start Project for Introducing Talent of Jiangsu University of Science and Technology (35211002), the Pre-research for NSFC Project of Jiangsu University of Science and Technology (33201002) and the earmarked fund for Modern Agro-industry Technology Research Systems.

References

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Volume 67| Part 11| November 2011| Page o2871

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