Acta Cryst. (2008). E64, o821 [ doi:10.1107/S1600536808008738 ]
The structure of the title compound, C9H10O2, is related to that of 4-methylphenyl 4-methylbenzoate and ethylene di-4-methylbenzoate showing similar bond parameters. The molecule is planar, the dihedral angle between the aromatic ring and the -COOMe group being 0.95 (6)°. The cystal structure exhibits intermolecular C-H
O contacts that link molecules into infinite chains extended in the [001] direction.
The title ester was prepared from commercial p-toluic acid according to standard procedure.
Hydrogen atoms were located in difference syntheses, refined at idealized positions riding on the carbon or nitrogen atoms (C–H = 0.88–0.99 Å) with isotropic displacement parameters Uiso(H) = 1.2U(Ceq).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./sg2231fig1thm.gif)
| Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./sg2231fig2thm.gif)
| Fig. 2. Crystal packing viewed along [100] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted. |
| C9H10O2 | F000 = 320 |
| Mr = 150.17 | Dx = 1.280 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 806 reflections |
| a = 5.9134 (11) Å | θ = 2.4–27.8º |
| b = 7.6048 (14) Å | µ = 0.09 mm−1 |
| c = 17.484 (3) Å | T = 120 (2) K |
| β = 97.783 (4)º | Block, colourless |
| V = 779.0 (2) Å3 | 0.45 × 0.43 × 0.39 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 1855 independent reflections |
| Radiation source: sealed tube | 1482 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.039 |
| T = 120(2) K | θmax = 27.9º |
| φ and ω scans | θmin = 2.4º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −7→7 |
| Tmin = 0.961, Tmax = 0.967 | k = −10→9 |
| 6617 measured reflections | l = −23→23 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0752P)2 + 0.0208P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 1855 reflections | Δρmax = 0.31 e Å−3 |
| 102 parameters | Δρmin = −0.20 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C9H10O2 | V = 779.0 (2) Å3 |
| Mr = 150.17 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 5.9134 (11) Å | µ = 0.09 mm−1 |
| b = 7.6048 (14) Å | T = 120 (2) K |
| c = 17.484 (3) Å | 0.45 × 0.43 × 0.39 mm |
| β = 97.783 (4)º |
| Bruker SMART APEX diffractometer | 1855 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1482 reflections with I > 2σ(I) |
| Tmin = 0.961, Tmax = 0.967 | Rint = 0.039 |
| 6617 measured reflections |
| R[F2 > 2σ(F2)] = 0.042 | 102 parameters |
| wR(F2) = 0.124 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.31 e Å−3 |
| 1855 reflections | Δρmin = −0.20 e Å−3 |
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 | ||
| O1 | 0.39091 (14) | 0.28701 (11) | 0.44793 (5) | 0.0280 (2) | |
| O2 | 0.68910 (15) | 0.15425 (13) | 0.51751 (5) | 0.0325 (3) | |
| C1 | 0.2956 (2) | 0.31740 (17) | 0.51874 (7) | 0.0320 (3) | |
| H1A | 0.2793 | 0.2050 | 0.5448 | 0.048* | |
| H1B | 0.1456 | 0.3732 | 0.5068 | 0.048* | |
| H1C | 0.3974 | 0.3946 | 0.5526 | 0.048* | |
| C2 | 0.59091 (19) | 0.20144 (15) | 0.45593 (6) | 0.0234 (3) | |
| C3 | 0.67753 (18) | 0.17434 (15) | 0.38071 (6) | 0.0223 (3) | |
| C4 | 0.55841 (19) | 0.23124 (15) | 0.31083 (7) | 0.0247 (3) | |
| H4A | 0.4154 | 0.2888 | 0.3098 | 0.030* | |
| C5 | 0.6496 (2) | 0.20350 (15) | 0.24261 (7) | 0.0262 (3) | |
| H5A | 0.5675 | 0.2426 | 0.1952 | 0.031* | |
| C6 | 0.8588 (2) | 0.11953 (15) | 0.24239 (7) | 0.0244 (3) | |
| C7 | 0.97615 (19) | 0.06389 (15) | 0.31291 (7) | 0.0253 (3) | |
| H7A | 1.1195 | 0.0068 | 0.3140 | 0.030* | |
| C8 | 0.88716 (19) | 0.09050 (15) | 0.38126 (7) | 0.0242 (3) | |
| H8A | 0.9693 | 0.0515 | 0.4287 | 0.029* | |
| C9 | 0.9593 (2) | 0.08897 (17) | 0.16858 (7) | 0.0312 (3) | |
| H9A | 1.1213 | 0.1213 | 0.1764 | 0.047* | |
| H9B | 0.8782 | 0.1613 | 0.1273 | 0.047* | |
| H9C | 0.9438 | −0.0355 | 0.1542 | 0.047* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0268 (5) | 0.0322 (5) | 0.0260 (4) | 0.0042 (3) | 0.0071 (3) | 0.0018 (3) |
| O2 | 0.0343 (5) | 0.0389 (5) | 0.0234 (5) | 0.0042 (4) | 0.0004 (4) | 0.0016 (3) |
| C1 | 0.0340 (7) | 0.0342 (7) | 0.0299 (7) | 0.0024 (5) | 0.0121 (5) | −0.0009 (5) |
| C2 | 0.0249 (6) | 0.0201 (6) | 0.0248 (6) | −0.0033 (4) | 0.0022 (5) | 0.0003 (4) |
| C3 | 0.0236 (6) | 0.0203 (6) | 0.0232 (6) | −0.0031 (4) | 0.0031 (4) | 0.0006 (4) |
| C4 | 0.0214 (5) | 0.0252 (6) | 0.0271 (6) | 0.0008 (4) | 0.0022 (4) | 0.0024 (4) |
| C5 | 0.0271 (6) | 0.0281 (6) | 0.0222 (6) | −0.0019 (5) | −0.0006 (5) | 0.0029 (4) |
| C6 | 0.0275 (6) | 0.0210 (6) | 0.0251 (6) | −0.0058 (4) | 0.0049 (4) | −0.0010 (4) |
| C7 | 0.0231 (6) | 0.0215 (6) | 0.0316 (6) | 0.0008 (4) | 0.0042 (5) | 0.0002 (4) |
| C8 | 0.0245 (6) | 0.0221 (6) | 0.0251 (6) | −0.0017 (4) | 0.0000 (4) | 0.0032 (4) |
| C9 | 0.0355 (7) | 0.0320 (7) | 0.0271 (6) | −0.0005 (5) | 0.0079 (5) | −0.0018 (5) |
| O1—C2 | 1.3405 (14) | C5—C6 | 1.3927 (17) |
| O1—C1 | 1.4468 (14) | C5—H5A | 0.9500 |
| O2—C2 | 1.2065 (14) | C6—C7 | 1.3962 (17) |
| C1—H1A | 0.9800 | C6—C9 | 1.5101 (16) |
| C1—H1B | 0.9800 | C7—C8 | 1.3843 (16) |
| C1—H1C | 0.9800 | C7—H7A | 0.9500 |
| C2—C3 | 1.4890 (16) | C8—H8A | 0.9500 |
| C3—C8 | 1.3929 (16) | C9—H9A | 0.9800 |
| C3—C4 | 1.3940 (16) | C9—H9B | 0.9800 |
| C4—C5 | 1.3899 (16) | C9—H9C | 0.9800 |
| C4—H4A | 0.9500 | ||
| C2—O1—C1 | 115.38 (9) | C4—C5—H5A | 119.3 |
| O1—C1—H1A | 109.5 | C6—C5—H5A | 119.3 |
| O1—C1—H1B | 109.5 | C5—C6—C7 | 118.16 (10) |
| H1A—C1—H1B | 109.5 | C5—C6—C9 | 121.71 (11) |
| O1—C1—H1C | 109.5 | C7—C6—C9 | 120.13 (11) |
| H1A—C1—H1C | 109.5 | C8—C7—C6 | 121.10 (10) |
| H1B—C1—H1C | 109.5 | C8—C7—H7A | 119.5 |
| O2—C2—O1 | 123.28 (10) | C6—C7—H7A | 119.5 |
| O2—C2—C3 | 124.43 (11) | C7—C8—C3 | 120.20 (10) |
| O1—C2—C3 | 112.28 (9) | C7—C8—H8A | 119.9 |
| C8—C3—C4 | 119.46 (10) | C3—C8—H8A | 119.9 |
| C8—C3—C2 | 118.00 (10) | C6—C9—H9A | 109.5 |
| C4—C3—C2 | 122.54 (10) | C6—C9—H9B | 109.5 |
| C5—C4—C3 | 119.76 (11) | H9A—C9—H9B | 109.5 |
| C5—C4—H4A | 120.1 | C6—C9—H9C | 109.5 |
| C3—C4—H4A | 120.1 | H9A—C9—H9C | 109.5 |
| C4—C5—C6 | 121.33 (10) | H9B—C9—H9C | 109.5 |
| C1—O1—C2—O2 | −1.07 (16) | C3—C4—C5—C6 | 0.00 (17) |
| C1—O1—C2—C3 | 179.72 (9) | C4—C5—C6—C7 | −0.20 (17) |
| O2—C2—C3—C8 | −0.70 (18) | C4—C5—C6—C9 | −179.94 (10) |
| O1—C2—C3—C8 | 178.50 (10) | C5—C6—C7—C8 | 0.28 (17) |
| O2—C2—C3—C4 | −179.94 (11) | C9—C6—C7—C8 | −179.98 (10) |
| O1—C2—C3—C4 | −0.74 (16) | C6—C7—C8—C3 | −0.16 (17) |
| C8—C3—C4—C5 | 0.12 (17) | C4—C3—C8—C7 | −0.05 (17) |
| C2—C3—C4—C5 | 179.36 (10) | C2—C3—C8—C7 | −179.32 (10) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9B···O2i | 0.98 | 2.51 | 3.4930 (16) | 177 |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
| O1—C2 | 1.3405 (14) | C2—C3 | 1.4890 (16) |
| O1—C1 | 1.4468 (14) | C6—C9 | 1.5101 (16) |
| O2—C2 | 1.2065 (14) | ||
| C2—O1—C1 | 115.38 (9) | O2—C2—C3 | 124.43 (11) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9B···O2i | 0.98 | 2.51 | 3.4930 (16) | 177 |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.
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The title ester is an important intermediate in the synthesis of a variety of natural products. These include the sclerotiorin group of fungal metabolites (Gray & Whalley, 1971), isochromans related to sclerotiorin pigments (Saeed & Rama, 1994) and isocoumarins like the 7-methylmellein (Harris & Mantle, 2001) and stellatin (Simpson, 1978).