Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057492/bg2126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057492/bg2126Isup2.hkl |
CCDC reference: 672950
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.150
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
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
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).
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.
H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H and CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3, O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O) for OH.
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.
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) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
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 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0614P)2 + 0.1779P] where P = (Fo2 + 2Fc2)/3 |
2561 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C11H10O4 | V = 1034.7 (2) Å3 |
Mr = 206.19 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.3214 (16) Å | µ = 0.10 mm−1 |
b = 6.1103 (8) Å | T = 295 K |
c = 14.1971 (19) Å | 0.30 × 0.20 × 0.20 mm |
β = 104.527 (3)° |
Bruker Kappa APEXII diffractometer | 2561 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1581 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.980 | Rint = 0.022 |
11880 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.16 e Å−3 |
2561 reflections | Δρmin = −0.18 e Å−3 |
138 parameters |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O3i | 0.93 | 2.59 | 3.440 (2) | 153 |
C10—H10···O2ii | 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. |
Experimental details
Crystal data | |
Chemical formula | C11H10O4 |
Mr | 206.19 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 12.3214 (16), 6.1103 (8), 14.1971 (19) |
β (°) | 104.527 (3) |
V (Å3) | 1034.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.923, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11880, 2561, 1581 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.150, 1.04 |
No. of reflections | 2561 |
No. of parameters | 138 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
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···O3i | 0.93 | 2.59 | 3.440 (2) | 153 |
C10—H10···O2ii | 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. |
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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).