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

The benzene ring in the title compound, C(10)H(10)O(4), makes an angle of 4.4 (1)° with the C-C-C-O linker. The hy-droxy groups are involved in both intra- and inter-molecular O-H⋯O hydrogen bonds. The crystal packing is stabilized by O-H⋯O hydrogen-bonding inter-actions. The mol-ecules of the caffeic acid ester form a dimeric structure in a head-to-head manner along the a axis through O-H⋯O hydrogen bonds. The dimers inter-act with one another through O-H⋯O hydrogen bonds, forming supermolecular chains. These chains are further extended through C-H⋯O hydrogen bonds as well as van der Waals inter-actions into the final three-dimensional architecture.

Related literature

For properties of caffeic acids and their esters, see: Altug et al. (2008 ▶); Ates et al. (2006 ▶); Atik et al. (2006 ▶); Chun et al. (2008 ▶); Huang et al. (2010 ▶); Hwang et al. (2001 ▶); Padinchare et al. (2001 ▶). For a polymorphic form of the title compound, see: Chen et al. (1979 ▶).

Experimental

Crystal data

C10H10O4

M = 194.18

Triclinic,

a = 5.129 (5) Å

b = 9.969 (8) Å

c = 10.586 (9) Å

α = 117.627 (7)°

β = 97.924 (11)°

γ = 94.322 (11)°

V = 468.9 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.33 × 0.24 × 0.18 mm

Data collection

Multiwire proportional diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.966, T max = 0.981

2494 measured reflections

1619 independent reflections

1337 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.05

1619 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054504/bg2376sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054504/bg2376Isup2.hkl

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

C10H10O4	Z = 2
Mr = 194.18	F(000) = 204
Triclinic, P1	Dx = 1.375 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.129 (5) Å	Cell parameters from 1619 reflections
b = 9.969 (8) Å	θ = 2.2–25.0°
c = 10.586 (9) Å	µ = 0.11 mm−1
α = 117.627 (7)°	T = 296 K
β = 97.924 (11)°	Block, colourless
γ = 94.322 (11)°	0.33 × 0.24 × 0.18 mm
V = 468.9 (7) Å3

Multiwire proportional diffractometer	1619 independent reflections
Radiation source: fine-focus sealed tube	1337 reflections with I > 2σ(I)
graphite	Rint = 0.013
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→5
Tmin = 0.966, Tmax = 0.981	k = −11→11
2494 measured reflections	l = −12→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.0896P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1619 reflections	Δρmax = 0.18 e Å−3
128 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (7)

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	0.3038 (3)	0.37534 (14)	−0.18804 (13)	0.0565 (4)
O2	0.5270 (3)	0.19675 (16)	−0.17913 (15)	0.0718 (5)
O3	0.1400 (2)	−0.02223 (14)	0.35179 (13)	0.0548 (4)
H3A	0.2389	−0.0773	0.3036	0.082*
O4	−0.2041 (3)	0.17229 (17)	0.47736 (15)	0.0696 (5)
H4A	−0.1537	0.1033	0.4914	0.104*
C1	0.4334 (5)	0.3652 (2)	−0.3048 (2)	0.0689 (6)
H1A	0.3752	0.4367	−0.3354	0.103*
H1B	0.3878	0.2631	−0.3853	0.103*
H1C	0.6232	0.3891	−0.2711	0.103*
C2	0.3676 (3)	0.28238 (18)	−0.13522 (17)	0.0436 (4)
C3	0.2244 (3)	0.29584 (18)	−0.02085 (17)	0.0445 (4)
H3B	0.1053	0.3654	0.0075	0.053*
C4	0.2628 (3)	0.20962 (19)	0.04297 (18)	0.0460 (4)
H4B	0.3849	0.1428	0.0100	0.055*
C5	0.1401 (3)	0.20498 (18)	0.15770 (17)	0.0424 (4)
C6	−0.0350 (3)	0.30272 (19)	0.22626 (19)	0.0513 (5)
H6A	−0.0774	0.3767	0.2001	0.062*
C7	−0.1459 (4)	0.2904 (2)	0.3326 (2)	0.0568 (5)
H7A	−0.2618	0.3568	0.3778	0.068*
C8	−0.0874 (3)	0.1811 (2)	0.37298 (18)	0.0476 (4)
C9	0.0889 (3)	0.08337 (18)	0.30649 (16)	0.0423 (4)
C10	0.2006 (3)	0.09637 (18)	0.20077 (17)	0.0442 (4)
H10A	0.3192	0.0312	0.1571	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0832 (9)	0.0569 (7)	0.0553 (7)	0.0308 (6)	0.0364 (6)	0.0392 (6)
O2	0.0865 (10)	0.0896 (10)	0.0850 (10)	0.0535 (8)	0.0538 (8)	0.0637 (8)
O3	0.0709 (8)	0.0646 (8)	0.0599 (7)	0.0330 (6)	0.0364 (6)	0.0458 (6)
O4	0.0859 (10)	0.0920 (10)	0.0775 (9)	0.0488 (8)	0.0561 (8)	0.0633 (8)
C1	0.1062 (17)	0.0689 (12)	0.0585 (11)	0.0311 (11)	0.0432 (11)	0.0430 (10)
C2	0.0502 (10)	0.0428 (8)	0.0462 (9)	0.0123 (7)	0.0160 (7)	0.0257 (7)
C3	0.0501 (10)	0.0474 (9)	0.0464 (9)	0.0156 (7)	0.0185 (7)	0.0275 (7)
C4	0.0511 (10)	0.0498 (9)	0.0487 (9)	0.0161 (7)	0.0205 (8)	0.0291 (8)
C5	0.0451 (9)	0.0463 (9)	0.0438 (8)	0.0104 (7)	0.0143 (7)	0.0263 (7)
C6	0.0596 (11)	0.0559 (10)	0.0588 (10)	0.0233 (8)	0.0246 (8)	0.0388 (9)
C7	0.0644 (12)	0.0650 (11)	0.0655 (11)	0.0341 (9)	0.0361 (9)	0.0418 (10)
C8	0.0520 (10)	0.0588 (10)	0.0467 (9)	0.0178 (8)	0.0233 (7)	0.0324 (8)
C9	0.0470 (9)	0.0475 (9)	0.0424 (8)	0.0121 (7)	0.0142 (7)	0.0278 (7)
C10	0.0490 (10)	0.0486 (9)	0.0456 (9)	0.0173 (7)	0.0209 (7)	0.0268 (7)

O1—C2	1.325 (2)	C3—H3B	0.9300
O1—C1	1.449 (2)	C4—C5	1.460 (2)
O2—C2	1.206 (2)	C4—H4B	0.9300
O3—C9	1.372 (2)	C5—C6	1.392 (2)
O3—H3A	0.8200	C5—C10	1.395 (2)
O4—C8	1.361 (2)	C6—C7	1.378 (2)
O4—H4A	0.8200	C6—H6A	0.9300
C1—H1A	0.9600	C7—C8	1.381 (2)
C1—H1B	0.9600	C7—H7A	0.9300
C1—H1C	0.9600	C8—C9	1.391 (2)
C2—C3	1.460 (2)	C9—C10	1.378 (2)
C3—C4	1.327 (2)	C10—H10A	0.9300
C2—O1—C1	115.65 (14)	C6—C5—C10	118.11 (15)
C9—O3—H3A	109.5	C6—C5—C4	123.59 (15)
C8—O4—H4A	109.5	C10—C5—C4	118.30 (14)
O1—C1—H1A	109.5	C7—C6—C5	120.39 (15)
O1—C1—H1B	109.5	C7—C6—H6A	119.8
H1A—C1—H1B	109.5	C5—C6—H6A	119.8
O1—C1—H1C	109.5	C6—C7—C8	121.02 (16)
H1A—C1—H1C	109.5	C6—C7—H7A	119.5
H1B—C1—H1C	109.5	C8—C7—H7A	119.5
O2—C2—O1	122.42 (15)	O4—C8—C7	118.86 (15)
O2—C2—C3	124.94 (14)	O4—C8—C9	121.79 (15)
O1—C2—C3	112.64 (14)	C7—C8—C9	119.35 (15)
C4—C3—C2	120.52 (15)	O3—C9—C10	123.84 (14)
C4—C3—H3B	119.7	O3—C9—C8	116.62 (14)
C2—C3—H3B	119.7	C10—C9—C8	119.54 (14)
C3—C4—C5	129.05 (16)	C9—C10—C5	121.59 (14)
C3—C4—H4B	115.5	C9—C10—H10A	119.2
C5—C4—H4B	115.5	C5—C10—H10A	119.2
C1—O1—C2—O2	1.4 (3)	C6—C7—C8—O4	−179.27 (17)
C1—O1—C2—C3	−178.44 (15)	C6—C7—C8—C9	0.9 (3)
O2—C2—C3—C4	−0.5 (3)	O4—C8—C9—O3	−0.2 (2)
O1—C2—C3—C4	179.32 (15)	C7—C8—C9—O3	179.66 (16)
C2—C3—C4—C5	−179.72 (15)	O4—C8—C9—C10	179.64 (16)
C3—C4—C5—C6	−3.9 (3)	C7—C8—C9—C10	−0.5 (3)
C3—C4—C5—C10	175.86 (16)	O3—C9—C10—C5	179.43 (14)
C10—C5—C6—C7	−0.6 (3)	C8—C9—C10—C5	−0.4 (3)
C4—C5—C6—C7	179.19 (17)	C6—C5—C10—C9	0.9 (2)
C5—C6—C7—C8	−0.3 (3)	C4—C5—C10—C9	−178.84 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.82	2.28	2.723 (2)	114.
C4—H4B···O2	0.93	2.48	2.829 (4)	102
O4—H4A···O3i	0.82	2.15	2.835 (2)	141.
O3—H3A···O2ii	0.82	1.95	2.764 (2)	175.
C10—H10A···O2ii	0.93	2.56	3.260 (4)	132

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	2.723 (2)	114
O4—H4A⋯O3i	0.82	2.15	2.835 (2)	141
O3—H3A⋯O2ii	0.82	1.95	2.764 (2)	175
C10—H10A⋯O2ii	0.93	2.56	3.260 (4)	132

Symmetry codes: (i) ; (ii) .