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The title compound, C13H14O3, was synthesized by the reaction of 2-hydr­oxy-5-methyl­acetophenone with methacryl­oyl chloride. The mol­ecular structure is stabilized by a weak C—H...O intra­molecular inter­action and the crystal packing is stabilized by a weak C—H...π inter­action and a π–π inter­action; the centroid–centroid separation and the inter­planar distance are 5.048 (2) and 3.421 Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031960/is2182sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031960/is2182Isup2.hkl
Contains datablock I

CCDC reference: 657688

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.044
  • wR factor = 0.151
  • Data-to-parameter ratio = 23.2

checkCIF/PLATON results

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No errors found in this datablock

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing diagram of (I), viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
2-Acetyl-4-methylphenyl methacrylate top
Crystal data top
C13H14O3Z = 2
Mr = 218.24F(000) = 232
Triclinic, P1Dx = 1.230 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4619 (3) ÅCell parameters from 6575 reflections
b = 8.4810 (4) Åθ = 2.5–29.4°
c = 8.4929 (3) ŵ = 0.09 mm1
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
Data collection top
Bruker APEX II
diffractometer
3427 independent reflections
Radiation source: fine-focus sealed tube2434 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.922, Tmax = 0.987k = 1111
14784 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C13H14O3γ = 76.090 (2)°
Mr = 218.24V = 589.36 (4) Å3
Triclinic, P1Z = 2
a = 8.4619 (3) ÅMo Kα radiation
b = 8.4810 (4) ŵ = 0.09 mm1
c = 8.4929 (3) ÅT = 295 K
α = 89.899 (2)°0.25 × 0.16 × 0.15 mm
β = 85.111 (3)°
Data collection top
Bruker APEX II
diffractometer
3427 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2434 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.987Rint = 0.022
14784 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.05Δρmax = 0.23 e Å3
3427 reflectionsΔρmin = 0.15 e Å3
148 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.44662 (18)0.6979 (2)1.13671 (19)0.0725 (4)
H1A0.47210.59871.10550.109*
H1B0.54210.78591.13520.109*
H1C0.41130.68771.24150.109*
C20.31230 (14)0.73148 (16)1.02360 (15)0.0522 (3)
C30.21210 (14)0.60821 (14)0.92885 (14)0.0477 (3)
H30.22960.50430.93730.057*
C40.08662 (13)0.63235 (13)0.82175 (13)0.0449 (3)
C50.06243 (14)0.78974 (14)0.81322 (14)0.0478 (3)
C60.16081 (16)0.91501 (15)0.90530 (17)0.0568 (3)
H60.14401.01920.89730.068*
C70.28434 (16)0.88544 (16)1.00941 (16)0.0585 (3)
H70.35010.97061.07120.070*
C80.01559 (15)0.49421 (15)0.72077 (14)0.0516 (3)
C90.0391 (2)0.33884 (18)0.7179 (2)0.0766 (4)
H9A0.03450.26240.64620.115*
H9B0.14730.35990.68370.115*
H9C0.03950.29470.82200.115*
C100.21145 (15)0.78578 (13)0.74115 (14)0.0491 (3)
C110.32843 (16)0.81776 (16)0.61168 (15)0.0559 (3)
C120.2755 (2)0.9218 (2)0.49656 (18)0.0742 (4)
H12A0.34970.94430.41770.089*
H12B0.16470.97100.49600.089*
C130.4994 (2)0.7343 (3)0.6232 (2)0.0878 (5)
H13A0.56530.76110.53420.132*
H13B0.51000.61900.62390.132*
H13C0.53540.76790.71910.132*
O10.13873 (12)0.50525 (13)0.64342 (12)0.0701 (3)
O20.05429 (10)0.82955 (11)0.70451 (11)0.0565 (2)
O30.24860 (11)0.73175 (12)0.86701 (10)0.0609 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0567 (8)0.0888 (10)0.0656 (9)0.0089 (7)0.0051 (6)0.0065 (7)
C20.0456 (6)0.0597 (7)0.0491 (6)0.0069 (5)0.0085 (5)0.0057 (5)
C30.0475 (6)0.0458 (6)0.0509 (6)0.0114 (4)0.0102 (5)0.0061 (5)
C40.0466 (6)0.0435 (6)0.0441 (6)0.0075 (4)0.0109 (4)0.0044 (4)
C50.0473 (6)0.0480 (6)0.0488 (6)0.0110 (5)0.0104 (5)0.0109 (5)
C60.0587 (7)0.0417 (6)0.0693 (8)0.0088 (5)0.0116 (6)0.0035 (5)
C70.0541 (7)0.0534 (7)0.0623 (7)0.0009 (5)0.0073 (6)0.0059 (6)
C80.0542 (7)0.0516 (6)0.0469 (6)0.0071 (5)0.0097 (5)0.0008 (5)
C90.0955 (11)0.0539 (8)0.0798 (10)0.0197 (7)0.0012 (8)0.0135 (7)
C100.0552 (7)0.0428 (6)0.0517 (6)0.0148 (5)0.0089 (5)0.0032 (5)
C110.0593 (7)0.0576 (7)0.0531 (7)0.0195 (5)0.0027 (5)0.0004 (5)
C120.0772 (10)0.0811 (10)0.0633 (8)0.0207 (8)0.0037 (7)0.0166 (7)
C130.0616 (9)0.1160 (14)0.0836 (11)0.0185 (9)0.0028 (8)0.0156 (10)
O10.0634 (6)0.0728 (6)0.0699 (6)0.0125 (5)0.0063 (5)0.0137 (5)
O20.0539 (5)0.0589 (5)0.0584 (5)0.0158 (4)0.0088 (4)0.0195 (4)
O30.0626 (5)0.0705 (6)0.0543 (5)0.0221 (4)0.0146 (4)0.0115 (4)
Geometric parameters (Å, º) top
C1—C21.5048 (19)C8—O11.2067 (16)
C1—H1A0.9600C8—C91.4988 (19)
C1—H1B0.9600C9—H9A0.9600
C1—H1C0.9600C9—H9B0.9600
C2—C71.3851 (19)C9—H9C0.9600
C2—C31.3856 (17)C10—O31.1990 (14)
C3—C41.3913 (16)C10—O21.3550 (14)
C3—H30.9300C10—C111.4849 (18)
C4—C51.3991 (16)C11—C121.348 (2)
C4—C81.4986 (16)C11—C131.462 (2)
C5—C61.3784 (18)C12—H12A0.9300
C5—O21.3948 (14)C12—H12B0.9300
C6—C71.3802 (19)C13—H13A0.9600
C6—H60.9300C13—H13B0.9600
C7—H70.9300C13—H13C0.9600
C2—C1—H1A109.5O1—C8—C9120.02 (12)
C2—C1—H1B109.5C4—C8—C9118.01 (12)
H1A—C1—H1B109.5C8—C9—H9A109.5
C2—C1—H1C109.5C8—C9—H9B109.5
H1A—C1—H1C109.5H9A—C9—H9B109.5
H1B—C1—H1C109.5C8—C9—H9C109.5
C7—C2—C3117.54 (12)H9A—C9—H9C109.5
C7—C2—C1121.73 (12)H9B—C9—H9C109.5
C3—C2—C1120.73 (12)O3—C10—O2122.57 (11)
C2—C3—C4123.21 (11)O3—C10—C11124.75 (11)
C2—C3—H3118.4O2—C10—C11112.64 (10)
C4—C3—H3118.4C12—C11—C13124.25 (13)
C3—C4—C5116.97 (10)C12—C11—C10120.27 (13)
C3—C4—C8120.52 (10)C13—C11—C10115.45 (12)
C5—C4—C8122.51 (11)C11—C12—H12A120.0
C6—C5—O2116.93 (10)C11—C12—H12B120.0
C6—C5—C4121.12 (11)H12A—C12—H12B120.0
O2—C5—C4121.82 (10)C11—C13—H13A109.5
C5—C6—C7119.87 (11)C11—C13—H13B109.5
C5—C6—H6120.1H13A—C13—H13B109.5
C7—C6—H6120.1C11—C13—H13C109.5
C6—C7—C2121.29 (11)H13A—C13—H13C109.5
C6—C7—H7119.4H13B—C13—H13C109.5
C2—C7—H7119.4C10—O2—C5116.49 (9)
O1—C8—C4121.97 (11)
C7—C2—C3—C40.01 (18)C3—C4—C8—O1169.44 (11)
C1—C2—C3—C4179.70 (11)C5—C4—C8—O110.93 (18)
C2—C3—C4—C50.67 (17)C3—C4—C8—C910.45 (17)
C2—C3—C4—C8178.98 (10)C5—C4—C8—C9169.18 (12)
C3—C4—C5—C61.06 (17)O3—C10—C11—C12159.54 (14)
C8—C4—C5—C6178.59 (10)O2—C10—C11—C1218.37 (17)
C3—C4—C5—O2176.70 (9)O3—C10—C11—C1318.45 (19)
C8—C4—C5—O22.94 (17)O2—C10—C11—C13163.65 (13)
O2—C5—C6—C7176.65 (11)O3—C10—O2—C57.91 (17)
C4—C5—C6—C70.80 (19)C11—C10—O2—C5174.13 (10)
C5—C6—C7—C20.10 (19)C6—C5—O2—C10105.59 (12)
C3—C2—C7—C60.29 (19)C4—C5—O2—C1078.59 (14)
C1—C2—C7—C6180.00 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O20.932.392.7147 (17)101
C13—H13C···Cgi0.963.003.8415 (19)148
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC13H14O3
Mr218.24
Crystal system, space groupTriclinic, 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)
V3)589.36 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.16 × 0.15
Data collection
DiffractometerBruker APEX II
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.922, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
14784, 3427, 2434
Rint0.022
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.151, 1.05
No. of reflections3427
No. of parameters148
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.15

Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O20.932.392.7147 (17)101
C13—H13C···Cgi0.963.003.8415 (19)148
Symmetry code: (i) x1, y, z.
 

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