3-Acetyl-4-hydroxy­phenyl acrylate

In the title compound, C₁₁H₁₀O₄, the acetyl and acrylo­yloxy groups make dihedral angles of 3.93 (8) and 55.18 (6)°, respectively, with the benzene ring. The mol­ecular structure is, in turn, stabilized by a medium-strength intra­molecular O—H...O inter­action, while the crystal packing is in turn stabilized by weak inter­molecular C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.150
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

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Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The acrylic derivatives have been used in clinical applications and biomaterials because of their excellent biocompatibility and long-term stability (Williams, 1981). The geometric parameters in the title compound (I) (Fig. 1) agree with the reported values of similar structures (Chakkaravarthi et al. (2007); Ren et al. (2006); Xu et al. (2006)).

The acetyl and acryloyloxy groups make dihedral angles of 3.93 (8)° and 55.18 (6)°, respectively, with the benzene ring. The O3—C9—C10—C11 and C1—C2—C3—C8 torsion angles [-177.46 (18)° and 176.94 (16)°, respectively] indicate anti-periplanar conformation of the respective groups. The molecular structure is stabilized by medium strength intramolecular O—H···O interaction while the crystal packing is in turn stabilized by weak intermolecular C—H···O contacts defining columns along [010]. (Table 1 and Fig. 2).

Related literature

For related literature, see: Ren et al. (2006); Williams (1981); Xu et al. (2006). A similiar compound has been reported by Chakkaravarthi et al. (2007).

S2. Experimental

2,4-Dihydroxyacetophenone(4.2 g, 27.60 mmol), triethylamine (3.85 ml, 27.67 mmol) and 150 ml of dry 2-butanone were taken in a 250 ml round bottom flask and the temperature was maintained at 273 K. Then the solution of acryloylchloride (2.3 ml, 28.30 mmol) in 30 ml of 2-butanone was added dropwise to the mixture with constant stirring for 30 minutes. After the addition was over, the reaction mixture was stirred for another 6 h. The salt formed during the reaction was filtered and the filtrate was washed with water and dried over anhydrous MgSO₄. The filtrate was concentrated under reduced pressure and the product was obtained. This was dissolved in the hexane and ethyl acetate solution (9:1). Crystals suitable for X-ray analysis were grown by slow evaporation of an ethyl acetate solution.

S3. Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and U_iso(H) = 1.2Ueq(C) for aromatic C—H and CH₂, C—H = 0.96 Å and U_iso(H) = 1.5Ueq(C) for CH₃, O—H = 0.82 Å and U_iso(H) = 1.5Ueq(O) for OH.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The packing of (I), viewed down the columns direction, [010]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

3-Acetyl-4-hydroxyphenyl acrylate

Crystal data

C11H10O4	F(000) = 432
Mr = 206.19	Dx = 1.324 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2985 reflections
a = 12.3214 (16) Å	θ = 2.5–24.6°
b = 6.1103 (8) Å	µ = 0.10 mm^−1
c = 14.1971 (19) Å	T = 295 K
β = 104.527 (3)°	Needle, colourless
V = 1034.7 (2) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and ϕ scan	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.923, Tmax = 0.980	k = −8→8
11880 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0614P)^2 + 0.1779P] where P = (Fo^2 + 2Fc^2)/3
2561 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.17657 (16)	0.2923 (4)	0.09037 (15)	0.0900 (6)
H1A	1.2553	0.2798	0.0945	0.135*
H1B	1.1630	0.4231	0.1231	0.135*
H1C	1.1358	0.2991	0.0233	0.135*
C2	1.13892 (14)	0.0991 (3)	0.13712 (12)	0.0686 (5)
C3	1.02051 (12)	0.0754 (3)	0.13889 (10)	0.0573 (4)
C4	0.94110 (14)	0.2365 (3)	0.10348 (13)	0.0718 (5)
H4	0.9633	0.3637	0.0775	0.086*
C5	0.83090 (14)	0.2133 (3)	0.10566 (14)	0.0742 (5)
H5	0.7790	0.3229	0.0817	0.089*
C6	0.79906 (12)	0.0249 (3)	0.14395 (11)	0.0595 (4)
C7	0.87330 (13)	−0.1366 (3)	0.18126 (13)	0.0681 (4)
H7	0.8499	−0.2616	0.2080	0.082*
C8	0.98466 (12)	−0.1117 (3)	0.17884 (12)	0.0647 (4)
C9	0.62307 (12)	−0.1612 (3)	0.11041 (12)	0.0630 (4)
C10	0.50996 (13)	−0.1397 (3)	0.12550 (13)	0.0733 (5)
H10	0.4923	−0.0143	0.1556	0.088*
C11	0.43508 (15)	−0.2867 (4)	0.09882 (16)	0.0927 (6)
H11A	0.4512	−0.4133	0.0686	0.111*
H11B	0.3643	−0.2674	0.1096	0.111*
O1	1.20776 (10)	−0.0411 (3)	0.17501 (11)	0.0960 (5)
O2	1.05545 (10)	−0.2747 (2)	0.21735 (13)	0.1046 (5)
H2	1.1177	−0.2487	0.2092	0.157*
O3	0.68743 (8)	0.01363 (19)	0.14911 (9)	0.0732 (4)
O4	0.65694 (10)	−0.3061 (2)	0.07039 (11)	0.0929 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0714 (11)	0.1181 (16)	0.0850 (12)	−0.0226 (11)	0.0279 (10)	0.0082 (12)
C2	0.0542 (9)	0.0894 (12)	0.0628 (9)	−0.0094 (9)	0.0160 (7)	−0.0063 (9)
C3	0.0495 (8)	0.0684 (9)	0.0530 (8)	−0.0052 (7)	0.0108 (6)	−0.0020 (7)
C4	0.0593 (9)	0.0703 (10)	0.0822 (11)	−0.0062 (8)	0.0108 (8)	0.0139 (9)
C5	0.0560 (9)	0.0651 (10)	0.0944 (12)	0.0050 (8)	0.0054 (8)	0.0053 (9)
C6	0.0437 (7)	0.0659 (9)	0.0679 (9)	−0.0023 (7)	0.0122 (6)	−0.0101 (7)
C7	0.0524 (8)	0.0688 (10)	0.0826 (11)	−0.0050 (7)	0.0158 (8)	0.0106 (9)
C8	0.0471 (8)	0.0672 (10)	0.0767 (10)	0.0029 (7)	0.0098 (7)	0.0058 (8)
C9	0.0487 (8)	0.0726 (10)	0.0679 (9)	−0.0017 (7)	0.0148 (7)	−0.0072 (8)
C10	0.0493 (8)	0.0905 (12)	0.0814 (11)	−0.0011 (8)	0.0186 (8)	−0.0157 (10)
C11	0.0568 (10)	0.1180 (16)	0.1077 (15)	−0.0143 (11)	0.0289 (10)	−0.0223 (13)
O1	0.0515 (7)	0.1164 (11)	0.1217 (11)	0.0044 (7)	0.0248 (7)	0.0148 (9)
O2	0.0551 (7)	0.0884 (9)	0.1665 (15)	0.0122 (7)	0.0208 (8)	0.0429 (9)
O3	0.0468 (6)	0.0756 (8)	0.0988 (9)	−0.0033 (5)	0.0210 (5)	−0.0220 (6)
O4	0.0598 (7)	0.0952 (9)	0.1297 (11)	−0.0125 (6)	0.0352 (7)	−0.0440 (9)

Geometric parameters (Å, º)

C1—C2	1.485 (3)	C6—O3	1.3973 (17)
C1—H1A	0.9600	C7—C8	1.389 (2)
C1—H1B	0.9600	C7—H7	0.9300
C1—H1C	0.9600	C8—O2	1.3461 (19)
C2—O1	1.230 (2)	C9—O4	1.1831 (19)
C2—C3	1.473 (2)	C9—O3	1.3616 (19)
C3—C4	1.390 (2)	C9—C10	1.468 (2)
C3—C8	1.396 (2)	C10—C11	1.275 (2)
C4—C5	1.373 (2)	C10—H10	0.9300
C4—H4	0.9300	C11—H11A	0.9300
C5—C6	1.371 (2)	C11—H11B	0.9300
C5—H5	0.9300	O2—H2	0.8200
C6—C7	1.359 (2)
C2—C1—H1A	109.5	C7—C6—O3	121.24 (15)
C2—C1—H1B	109.5	C5—C6—O3	116.45 (14)
H1A—C1—H1B	109.5	C6—C7—C8	118.89 (15)
C2—C1—H1C	109.5	C6—C7—H7	120.6
H1A—C1—H1C	109.5	C8—C7—H7	120.6
H1B—C1—H1C	109.5	O2—C8—C7	116.90 (15)
O1—C2—C3	120.09 (16)	O2—C8—C3	122.13 (14)
O1—C2—C1	119.40 (16)	C7—C8—C3	120.97 (14)
C3—C2—C1	120.51 (16)	O4—C9—O3	122.76 (14)
C4—C3—C8	117.45 (14)	O4—C9—C10	126.82 (15)
C4—C3—C2	122.33 (15)	O3—C9—C10	110.42 (14)
C8—C3—C2	120.21 (15)	C11—C10—C9	122.42 (17)
C5—C4—C3	121.95 (16)	C11—C10—H10	118.8
C5—C4—H4	119.0	C9—C10—H10	118.8
C3—C4—H4	119.0	C10—C11—H11A	120.0
C6—C5—C4	118.57 (16)	C10—C11—H11B	120.0
C6—C5—H5	120.7	H11A—C11—H11B	120.0
C4—C5—H5	120.7	C8—O2—H2	109.5
C7—C6—C5	122.15 (14)	C9—O3—C6	119.93 (12)
O1—C2—C3—C4	175.22 (16)	C6—C7—C8—C3	0.0 (3)
C1—C2—C3—C4	−4.4 (2)	C4—C3—C8—O2	−178.28 (16)
O1—C2—C3—C8	−3.5 (2)	C2—C3—C8—O2	0.5 (3)
C1—C2—C3—C8	176.94 (16)	C4—C3—C8—C7	1.1 (2)
C8—C3—C4—C5	−1.1 (3)	C2—C3—C8—C7	179.89 (15)
C2—C3—C4—C5	−179.82 (17)	O4—C9—C10—C11	2.9 (3)
C3—C4—C5—C6	−0.1 (3)	O3—C9—C10—C11	−177.46 (18)
C4—C5—C6—C7	1.3 (3)	O4—C9—O3—C6	−1.2 (3)
C4—C5—C6—O3	176.86 (15)	C10—C9—O3—C6	179.16 (14)
C5—C6—C7—C8	−1.2 (3)	C7—C6—O3—C9	−56.9 (2)
O3—C6—C7—C8	−176.60 (15)	C5—C6—O3—C9	127.46 (17)
C6—C7—C8—O2	179.42 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.83	2.5467 (18)	145
C7—H7···O3^i	0.93	2.59	3.440 (2)	153
C10—H10···O2^ii	0.93	2.50	3.392 (2)	160

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.