Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031960/is2182sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031960/is2182Isup2.hkl |
CCDC reference: 657688
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.002 Å
- R factor = 0.044
- wR factor = 0.151
- Data-to-parameter ratio = 23.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For related literature, see: Gibson et al. (2006); Parker & Braden (1989); Ren et al. (2006). A similar acetophenone compound with methylbenzoyl has been reported (Kazak et al., 2002).
2-Hydroxy-5-methylacetophenone (4.0 g, 26.65 mmol), K2CO3 (3.69 g, 26.69 mmol) and 100 ml of dry acetone were taken in a 250 ml round bottom flask and the temperature was maintained at 273 K. Then the solution of methacryloylchloride (2.7 ml, 27.63 mmol) in 20 ml of dry acetone was added dropwise to the mixture with constant stirring for 30 min. After the addition was over, the reaction mixture was stirred for 6 h. The salt formed during the reaction was filtered and the filtrate was washed with water and dried over anhydrous MgSO4. The obtained compound was dissolved in hexane and ethyl acetate (9:1). Single crystals suitable for X-ray analysis were grown by slow evaporation of the solution.
H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Methacrylate compounds have figured prominently in the development of soft-tissue-compatible materials, orthopedic and dental cements. Methacrylate activated vinyl esters are readily polymerized by free-radical polymerization to form linear, branched or network polymers (Parker & Braden, 1989).
The geometric parameters in the title compound, (I), are comparable with those observed in similar structures (Gibson et al., 2006; Kazak et al., 2002; Ren et al., 2006). A similar acetophenone compound with methylbenzoyl moiety has been reported (Kazak et al., 2002). The torsion angles O2—C10—C11—C12 and O3—C10—C11—C13 [18.37 (17)° and 18.45 (19)°, respectively] indicate syn-periplanar conformations and the torsion angle O2—C10—C11—C13 [-163.64 (13)°], shows anti-periplanar conformation. The molecule is stabilized by a weak C—H···O intramolecular interaction (Table 1) and the crystal packing is stabilized by a weak C—H···π interaction and a π-π interaction; the centroid-centroid separation, Cg···Cgi [symmetry code: (i) -x, 1 - y, -z; Cg is the centroid of the benzene C2—C7 ring], is 5.048 (2) Å.
For related literature, see: Gibson et al. (2006); Parker & Braden (1989); Ren et al. (2006). A similar acetophenone compound with methylbenzoyl has been reported (Kazak et al., 2002).
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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C13H14O3 | Z = 2 |
Mr = 218.24 | F(000) = 232 |
Triclinic, P1 | Dx = 1.230 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4619 (3) Å | Cell parameters from 6575 reflections |
b = 8.4810 (4) Å | θ = 2.5–29.4° |
c = 8.4929 (3) Å | µ = 0.09 mm−1 |
α = 89.899 (2)° | T = 295 K |
β = 85.111 (3)° | Needle, colourless |
γ = 76.090 (2)° | 0.25 × 0.16 × 0.15 mm |
V = 589.36 (4) Å3 |
Bruker APEX II diffractometer | 3427 independent reflections |
Radiation source: fine-focus sealed tube | 2434 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 30.1°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.922, Tmax = 0.987 | k = −11→11 |
14784 measured reflections | l = −11→11 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0751P)2 + 0.0589P] where P = (Fo2 + 2Fc2)/3 |
3427 reflections | (Δ/σ)max < 0.001 |
148 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C13H14O3 | γ = 76.090 (2)° |
Mr = 218.24 | V = 589.36 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4619 (3) Å | Mo Kα radiation |
b = 8.4810 (4) Å | µ = 0.09 mm−1 |
c = 8.4929 (3) Å | T = 295 K |
α = 89.899 (2)° | 0.25 × 0.16 × 0.15 mm |
β = 85.111 (3)° |
Bruker APEX II diffractometer | 3427 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2434 reflections with I > 2σ(I) |
Tmin = 0.922, Tmax = 0.987 | Rint = 0.022 |
14784 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.23 e Å−3 |
3427 reflections | Δρmin = −0.15 e Å−3 |
148 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | −0.44662 (18) | 0.6979 (2) | 1.13671 (19) | 0.0725 (4) | |
H1A | −0.4721 | 0.5987 | 1.1055 | 0.109* | |
H1B | −0.5421 | 0.7859 | 1.1352 | 0.109* | |
H1C | −0.4113 | 0.6877 | 1.2415 | 0.109* | |
C2 | −0.31230 (14) | 0.73148 (16) | 1.02360 (15) | 0.0522 (3) | |
C3 | −0.21210 (14) | 0.60821 (14) | 0.92885 (14) | 0.0477 (3) | |
H3 | −0.2296 | 0.5043 | 0.9373 | 0.057* | |
C4 | −0.08662 (13) | 0.63235 (13) | 0.82175 (13) | 0.0449 (3) | |
C5 | −0.06243 (14) | 0.78974 (14) | 0.81322 (14) | 0.0478 (3) | |
C6 | −0.16081 (16) | 0.91501 (15) | 0.90530 (17) | 0.0568 (3) | |
H6 | −0.1440 | 1.0192 | 0.8973 | 0.068* | |
C7 | −0.28434 (16) | 0.88544 (16) | 1.00941 (16) | 0.0585 (3) | |
H7 | −0.3501 | 0.9706 | 1.0712 | 0.070* | |
C8 | 0.01559 (15) | 0.49421 (15) | 0.72077 (14) | 0.0516 (3) | |
C9 | −0.0391 (2) | 0.33884 (18) | 0.7179 (2) | 0.0766 (4) | |
H9A | 0.0345 | 0.2624 | 0.6462 | 0.115* | |
H9B | −0.1473 | 0.3599 | 0.6837 | 0.115* | |
H9C | −0.0395 | 0.2947 | 0.8220 | 0.115* | |
C10 | 0.21145 (15) | 0.78578 (13) | 0.74115 (14) | 0.0491 (3) | |
C11 | 0.32843 (16) | 0.81776 (16) | 0.61168 (15) | 0.0559 (3) | |
C12 | 0.2755 (2) | 0.9218 (2) | 0.49656 (18) | 0.0742 (4) | |
H12A | 0.3497 | 0.9443 | 0.4177 | 0.089* | |
H12B | 0.1647 | 0.9710 | 0.4960 | 0.089* | |
C13 | 0.4994 (2) | 0.7343 (3) | 0.6232 (2) | 0.0878 (5) | |
H13A | 0.5653 | 0.7611 | 0.5342 | 0.132* | |
H13B | 0.5100 | 0.6190 | 0.6239 | 0.132* | |
H13C | 0.5354 | 0.7679 | 0.7191 | 0.132* | |
O1 | 0.13873 (12) | 0.50525 (13) | 0.64342 (12) | 0.0701 (3) | |
O2 | 0.05429 (10) | 0.82955 (11) | 0.70451 (11) | 0.0565 (2) | |
O3 | 0.24860 (11) | 0.73175 (12) | 0.86701 (10) | 0.0609 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0567 (8) | 0.0888 (10) | 0.0656 (9) | −0.0089 (7) | 0.0051 (6) | 0.0065 (7) |
C2 | 0.0456 (6) | 0.0597 (7) | 0.0491 (6) | −0.0069 (5) | −0.0085 (5) | 0.0057 (5) |
C3 | 0.0475 (6) | 0.0458 (6) | 0.0509 (6) | −0.0114 (4) | −0.0102 (5) | 0.0061 (5) |
C4 | 0.0466 (6) | 0.0435 (6) | 0.0441 (6) | −0.0075 (4) | −0.0109 (4) | 0.0044 (4) |
C5 | 0.0473 (6) | 0.0480 (6) | 0.0488 (6) | −0.0110 (5) | −0.0104 (5) | 0.0109 (5) |
C6 | 0.0587 (7) | 0.0417 (6) | 0.0693 (8) | −0.0088 (5) | −0.0116 (6) | 0.0035 (5) |
C7 | 0.0541 (7) | 0.0534 (7) | 0.0623 (7) | −0.0009 (5) | −0.0073 (6) | −0.0059 (6) |
C8 | 0.0542 (7) | 0.0516 (6) | 0.0469 (6) | −0.0071 (5) | −0.0097 (5) | −0.0008 (5) |
C9 | 0.0955 (11) | 0.0539 (8) | 0.0798 (10) | −0.0197 (7) | 0.0012 (8) | −0.0135 (7) |
C10 | 0.0552 (7) | 0.0428 (6) | 0.0517 (6) | −0.0148 (5) | −0.0089 (5) | 0.0032 (5) |
C11 | 0.0593 (7) | 0.0576 (7) | 0.0531 (7) | −0.0195 (5) | −0.0027 (5) | −0.0004 (5) |
C12 | 0.0772 (10) | 0.0811 (10) | 0.0633 (8) | −0.0207 (8) | 0.0037 (7) | 0.0166 (7) |
C13 | 0.0616 (9) | 0.1160 (14) | 0.0836 (11) | −0.0185 (9) | −0.0028 (8) | 0.0156 (10) |
O1 | 0.0634 (6) | 0.0728 (6) | 0.0699 (6) | −0.0125 (5) | 0.0063 (5) | −0.0137 (5) |
O2 | 0.0539 (5) | 0.0589 (5) | 0.0584 (5) | −0.0158 (4) | −0.0088 (4) | 0.0195 (4) |
O3 | 0.0626 (5) | 0.0705 (6) | 0.0543 (5) | −0.0221 (4) | −0.0146 (4) | 0.0115 (4) |
C1—C2 | 1.5048 (19) | C8—O1 | 1.2067 (16) |
C1—H1A | 0.9600 | C8—C9 | 1.4988 (19) |
C1—H1B | 0.9600 | C9—H9A | 0.9600 |
C1—H1C | 0.9600 | C9—H9B | 0.9600 |
C2—C7 | 1.3851 (19) | C9—H9C | 0.9600 |
C2—C3 | 1.3856 (17) | C10—O3 | 1.1990 (14) |
C3—C4 | 1.3913 (16) | C10—O2 | 1.3550 (14) |
C3—H3 | 0.9300 | C10—C11 | 1.4849 (18) |
C4—C5 | 1.3991 (16) | C11—C12 | 1.348 (2) |
C4—C8 | 1.4986 (16) | C11—C13 | 1.462 (2) |
C5—C6 | 1.3784 (18) | C12—H12A | 0.9300 |
C5—O2 | 1.3948 (14) | C12—H12B | 0.9300 |
C6—C7 | 1.3802 (19) | C13—H13A | 0.9600 |
C6—H6 | 0.9300 | C13—H13B | 0.9600 |
C7—H7 | 0.9300 | C13—H13C | 0.9600 |
C2—C1—H1A | 109.5 | O1—C8—C9 | 120.02 (12) |
C2—C1—H1B | 109.5 | C4—C8—C9 | 118.01 (12) |
H1A—C1—H1B | 109.5 | C8—C9—H9A | 109.5 |
C2—C1—H1C | 109.5 | C8—C9—H9B | 109.5 |
H1A—C1—H1C | 109.5 | H9A—C9—H9B | 109.5 |
H1B—C1—H1C | 109.5 | C8—C9—H9C | 109.5 |
C7—C2—C3 | 117.54 (12) | H9A—C9—H9C | 109.5 |
C7—C2—C1 | 121.73 (12) | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 120.73 (12) | O3—C10—O2 | 122.57 (11) |
C2—C3—C4 | 123.21 (11) | O3—C10—C11 | 124.75 (11) |
C2—C3—H3 | 118.4 | O2—C10—C11 | 112.64 (10) |
C4—C3—H3 | 118.4 | C12—C11—C13 | 124.25 (13) |
C3—C4—C5 | 116.97 (10) | C12—C11—C10 | 120.27 (13) |
C3—C4—C8 | 120.52 (10) | C13—C11—C10 | 115.45 (12) |
C5—C4—C8 | 122.51 (11) | C11—C12—H12A | 120.0 |
C6—C5—O2 | 116.93 (10) | C11—C12—H12B | 120.0 |
C6—C5—C4 | 121.12 (11) | H12A—C12—H12B | 120.0 |
O2—C5—C4 | 121.82 (10) | C11—C13—H13A | 109.5 |
C5—C6—C7 | 119.87 (11) | C11—C13—H13B | 109.5 |
C5—C6—H6 | 120.1 | H13A—C13—H13B | 109.5 |
C7—C6—H6 | 120.1 | C11—C13—H13C | 109.5 |
C6—C7—C2 | 121.29 (11) | H13A—C13—H13C | 109.5 |
C6—C7—H7 | 119.4 | H13B—C13—H13C | 109.5 |
C2—C7—H7 | 119.4 | C10—O2—C5 | 116.49 (9) |
O1—C8—C4 | 121.97 (11) | ||
C7—C2—C3—C4 | −0.01 (18) | C3—C4—C8—O1 | −169.44 (11) |
C1—C2—C3—C4 | 179.70 (11) | C5—C4—C8—O1 | 10.93 (18) |
C2—C3—C4—C5 | 0.67 (17) | C3—C4—C8—C9 | 10.45 (17) |
C2—C3—C4—C8 | −178.98 (10) | C5—C4—C8—C9 | −169.18 (12) |
C3—C4—C5—C6 | −1.06 (17) | O3—C10—C11—C12 | −159.54 (14) |
C8—C4—C5—C6 | 178.59 (10) | O2—C10—C11—C12 | 18.37 (17) |
C3—C4—C5—O2 | −176.70 (9) | O3—C10—C11—C13 | 18.45 (19) |
C8—C4—C5—O2 | 2.94 (17) | O2—C10—C11—C13 | −163.65 (13) |
O2—C5—C6—C7 | 176.65 (11) | O3—C10—O2—C5 | −7.91 (17) |
C4—C5—C6—C7 | 0.80 (19) | C11—C10—O2—C5 | 174.13 (10) |
C5—C6—C7—C2 | −0.10 (19) | C6—C5—O2—C10 | 105.59 (12) |
C3—C2—C7—C6 | −0.29 (19) | C4—C5—O2—C10 | −78.59 (14) |
C1—C2—C7—C6 | 180.00 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O2 | 0.93 | 2.39 | 2.7147 (17) | 101 |
C13—H13C···Cgi | 0.96 | 3.00 | 3.8415 (19) | 148 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H14O3 |
Mr | 218.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.4619 (3), 8.4810 (4), 8.4929 (3) |
α, β, γ (°) | 89.899 (2), 85.111 (3), 76.090 (2) |
V (Å3) | 589.36 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.16 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX II |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.922, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14784, 3427, 2434 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.706 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.151, 1.05 |
No. of reflections | 3427 |
No. of parameters | 148 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.15 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O2 | 0.93 | 2.39 | 2.7147 (17) | 101 |
C13—H13C···Cgi | 0.96 | 3.00 | 3.8415 (19) | 148 |
Symmetry code: (i) x−1, y, z. |
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Methacrylate compounds have figured prominently in the development of soft-tissue-compatible materials, orthopedic and dental cements. Methacrylate activated vinyl esters are readily polymerized by free-radical polymerization to form linear, branched or network polymers (Parker & Braden, 1989).
The geometric parameters in the title compound, (I), are comparable with those observed in similar structures (Gibson et al., 2006; Kazak et al., 2002; Ren et al., 2006). A similar acetophenone compound with methylbenzoyl moiety has been reported (Kazak et al., 2002). The torsion angles O2—C10—C11—C12 and O3—C10—C11—C13 [18.37 (17)° and 18.45 (19)°, respectively] indicate syn-periplanar conformations and the torsion angle O2—C10—C11—C13 [-163.64 (13)°], shows anti-periplanar conformation. The molecule is stabilized by a weak C—H···O intramolecular interaction (Table 1) and the crystal packing is stabilized by a weak C—H···π interaction and a π-π interaction; the centroid-centroid separation, Cg···Cgi [symmetry code: (i) -x, 1 - y, -z; Cg is the centroid of the benzene C2—C7 ring], is 5.048 (2) Å.