3-Acetyl-4-hydroxy-phenyl acrylate.

In the title compound, C(12)H(12)O(4), the hydr-oxy O and the C and O atoms of the acetyl group are almost coplanar [maximum deviation = 0.0356 (1) Å] with the benzene ring. The dihedral angle between the benzene ring and the plane through the non-H atoms of the methacrylo-yloxy group is 86.1 (1)°. In the crystal structure, mol-ecules are linked by two C-H⋯O hydrogen bonds, forming dimers with graph-set descriptor R(2) (2)(16). A strong intra-molecular O-H⋯O hydrogen bond is also observed.

Related literature

For reference bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see Bernstein et al. (1995 ▶). For the biological properties of acetophenone derivatives, see Favier et al. (1998 ▶); Sala et al. (2001 ▶); Suksamrarn et al. (1997 ▶). Acetophenones are useful synthons for the preparation of a wide variety of polyphenolic compounds such as chalcones and flavones, see Parmar et al. (1996 ▶).

Experimental

Crystal data

C12H12O4

M = 220.22

Monoclinic,

a = 8.8335 (3) Å

b = 11.9320 (3) Å

c = 11.3295 (3) Å

β = 111.277 (2)°

V = 1112.75 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.17 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.976, T max = 0.983

14184 measured reflections

3437 independent reflections

2080 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.161

S = 1.05

3437 reflections

155 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032176/wn2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032176/wn2339Isup2.hkl

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

C12H12O4	F(000) = 464
Mr = 220.22	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3437 reflections
a = 8.8335 (3) Å	θ = 2.5–30.6°
b = 11.9320 (3) Å	µ = 0.10 mm−1
c = 11.3295 (3) Å	T = 293 K
β = 111.277 (2)°	Block, colourless
V = 1112.75 (6) Å3	0.25 × 0.17 × 0.17 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3437 independent reflections
Radiation source: fine-focus sealed tube	2080 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 30.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.976, Tmax = 0.983	k = −17→12
14184 measured reflections	l = −15→16

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.1247P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3437 reflections	Δρmax = 0.21 e Å−3
155 parameters	Δρmin = −0.17 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: 0.007 (4)

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	0.79745 (16)	0.06020 (12)	1.12189 (13)	0.0535 (3)
C2	0.82796 (18)	−0.01422 (13)	1.03977 (15)	0.0636 (4)
H2A	0.9148	−0.0638	1.0702	0.076*
C3	0.73129 (18)	−0.01579 (13)	0.91355 (14)	0.0610 (4)
H3A	0.7534	−0.0653	0.8584	0.073*
C4	0.60112 (16)	0.05669 (12)	0.86937 (12)	0.0508 (3)
C5	0.56645 (15)	0.12991 (10)	0.94908 (12)	0.0468 (3)
H5A	0.4769	0.1771	0.9177	0.056*
C6	0.66479 (15)	0.13418 (10)	1.07749 (11)	0.0455 (3)
C7	0.63168 (17)	0.21260 (12)	1.16503 (13)	0.0563 (4)
C8	0.4888 (2)	0.28945 (14)	1.11997 (18)	0.0747 (5)
H8A	0.4860	0.3344	1.1894	0.112*
H8B	0.3908	0.2461	1.0869	0.112*
H8C	0.4977	0.3372	1.0546	0.112*
C9	0.51842 (17)	0.12501 (12)	0.66068 (12)	0.0539 (3)
C10	0.39516 (16)	0.11754 (12)	0.53150 (12)	0.0524 (3)
C11	0.4200 (2)	0.19460 (15)	0.43794 (15)	0.0741 (5)
H11A	0.4197	0.2706	0.4657	0.111*
H11B	0.3341	0.1846	0.3573	0.111*
H11C	0.5225	0.1786	0.4301	0.111*
C12	0.2721 (2)	0.04683 (17)	0.50538 (18)	0.0744 (5)
O1	0.72227 (16)	0.21560 (11)	1.27744 (10)	0.0806 (4)
O2	0.89890 (14)	0.05916 (12)	1.24440 (10)	0.0777 (4)
H2	0.8702	0.1069	1.2839	0.131 (11)*
O3	0.49615 (13)	0.05008 (9)	0.74249 (9)	0.0621 (3)
O4	0.62770 (17)	0.18962 (14)	0.69180 (11)	0.1046 (5)
H12A	0.195 (3)	0.0427 (17)	0.420 (2)	0.101 (6)*
H12B	0.257 (3)	−0.0033 (19)	0.569 (2)	0.107 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0459 (7)	0.0615 (8)	0.0460 (7)	−0.0046 (6)	0.0081 (6)	0.0116 (6)
C2	0.0517 (8)	0.0687 (9)	0.0676 (9)	0.0109 (7)	0.0184 (7)	0.0115 (7)
C3	0.0638 (9)	0.0606 (9)	0.0632 (9)	0.0001 (7)	0.0287 (7)	−0.0031 (7)
C4	0.0518 (7)	0.0558 (7)	0.0411 (6)	−0.0130 (6)	0.0123 (6)	−0.0005 (5)
C5	0.0423 (6)	0.0496 (7)	0.0429 (6)	−0.0039 (5)	0.0090 (5)	0.0045 (5)
C6	0.0446 (6)	0.0482 (7)	0.0405 (6)	−0.0071 (5)	0.0114 (5)	0.0037 (5)
C7	0.0626 (8)	0.0581 (8)	0.0460 (7)	−0.0127 (6)	0.0171 (6)	−0.0022 (6)
C8	0.0814 (11)	0.0673 (10)	0.0778 (11)	0.0019 (8)	0.0316 (9)	−0.0141 (8)
C9	0.0565 (8)	0.0608 (8)	0.0429 (7)	−0.0084 (6)	0.0165 (6)	−0.0062 (6)
C10	0.0540 (7)	0.0572 (8)	0.0427 (7)	0.0101 (6)	0.0137 (6)	−0.0055 (5)
C11	0.0910 (12)	0.0762 (10)	0.0522 (9)	0.0150 (9)	0.0222 (8)	0.0069 (7)
C12	0.0591 (9)	0.0910 (13)	0.0576 (9)	−0.0046 (9)	0.0027 (8)	−0.0060 (9)
O1	0.0927 (9)	0.0936 (9)	0.0455 (6)	−0.0097 (7)	0.0130 (6)	−0.0124 (5)
O2	0.0672 (7)	0.0942 (9)	0.0505 (6)	0.0060 (6)	−0.0040 (5)	0.0160 (6)
O3	0.0678 (6)	0.0697 (7)	0.0405 (5)	−0.0222 (5)	0.0098 (4)	−0.0036 (4)
O4	0.1082 (10)	0.1330 (12)	0.0555 (7)	−0.0691 (9)	0.0092 (7)	0.0069 (7)

C1—O2	1.352 (2)	C8—H8A	0.9600
C1—C2	1.382 (2)	C8—H8B	0.9600
C1—C6	1.4062 (19)	C8—H8C	0.9600
C2—C3	1.374 (2)	C9—O4	1.185 (2)
C2—H2A	0.9300	C9—O3	1.353 (2)
C3—C4	1.379 (2)	C9—C10	1.476 (2)
C3—H3A	0.9300	C10—C12	1.322 (2)
C4—C5	1.3688 (19)	C10—C11	1.479 (2)
C4—O3	1.402 (2)	C11—H11A	0.9600
C5—C6	1.3987 (17)	C11—H11B	0.9600
C5—H5A	0.9300	C11—H11C	0.9600
C6—C7	1.4681 (19)	C12—H12A	0.96 (2)
C7—O1	1.235 (2)	C12—H12B	0.98 (2)
C7—C8	1.492 (2)	O2—H2	0.8200
O2—C1—C2	117.83 (13)	C7—C8—H8B	109.5
O2—C1—C6	121.95 (14)	H8A—C8—H8B	109.5
C2—C1—C6	120.22 (12)	C7—C8—H8C	109.5
C3—C2—C1	120.68 (13)	H8A—C8—H8C	109.5
C3—C2—H2A	119.7	H8B—C8—H8C	109.5
C1—C2—H2A	119.7	O4—C9—O3	122.11 (13)
C2—C3—C4	119.37 (14)	O4—C9—C10	124.24 (13)
C2—C3—H3A	120.3	O3—C9—C10	113.65 (12)
C4—C3—H3A	120.3	C12—C10—C9	120.75 (14)
C5—C4—C3	121.16 (12)	C12—C10—C11	124.09 (15)
C5—C4—O3	119.30 (12)	C9—C10—C11	115.16 (13)
C3—C4—O3	119.41 (12)	C10—C11—H11A	109.5
C4—C5—C6	120.41 (12)	C10—C11—H11B	109.5
C4—C5—H5A	119.8	H11A—C11—H11B	109.5
C6—C5—H5A	119.8	C10—C11—H11C	109.5
C5—C6—C1	118.14 (12)	H11A—C11—H11C	109.5
C5—C6—C7	121.67 (12)	H11B—C11—H11C	109.5
C1—C6—C7	120.19 (12)	C10—C12—H12A	118.7 (13)
O1—C7—C6	120.13 (14)	C10—C12—H12B	123.1 (13)
O1—C7—C8	119.10 (14)	H12A—C12—H12B	118.2 (19)
C6—C7—C8	120.78 (13)	C1—O2—H2	109.5
C7—C8—H8A	109.5	C9—O3—C4	117.32 (10)
O2—C1—C2—C3	−178.7 (1)	C5—C6—C7—O1	−178.84 (13)
C6—C1—C2—C3	1.1 (2)	C1—C6—C7—O1	1.6 (2)
C1—C2—C3—C4	−1.0 (2)	C5—C6—C7—C8	1.2 (2)
C2—C3—C4—C5	−0.1 (2)	C1—C6—C7—C8	−178.37 (13)
C2—C3—C4—O3	−175.79 (12)	O4—C9—C10—C12	−176.71 (18)
C3—C4—C5—C6	1.18 (19)	O3—C9—C10—C12	3.5 (2)
O3—C4—C5—C6	176.83 (11)	O4—C9—C10—C11	2.6 (2)
C4—C5—C6—C1	−1.04 (18)	O3—C9—C10—C11	−177.24 (12)
C4—C5—C6—C7	179.36 (11)	O4—C9—O3—C4	4.5 (2)
O2—C1—C6—C5	179.7 (1)	C10—C9—O3—C4	−175.63 (11)
C2—C1—C6—C5	−0.10 (19)	C5—C4—O3—C9	84.7 (2)
O2—C1—C6—C7	−0.69 (19)	C3—C4—O3—C9	−99.6 (2)
C2—C1—C6—C7	179.50 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.546 (2)	146
C5—H5A···O1i	0.93	2.57	3.483 (2)	166
C11—H11B···O4i	0.96	2.57	3.336 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.82	2.546 (2)	146
C5—H5A⋯O1i	0.93	2.57	3.483 (2)	166
C11—H11B⋯O4i	0.96	2.57	3.336 (2)	137

Symmetry code: (i) .