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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o821.
Published online 2008 April 10. doi:  10.1107/S1600536808008738
PMCID: PMC2961182

Methyl 4-methyl­benzoate

Abstract

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.

Related literature

For related literature, see: Deguire & Brisse (1988 [triangle]); Gowda et al. (2007 [triangle]; Gray & Whalley (1971 [triangle]); Harris & Mantle (2001 [triangle]); Saeed & Rama (1994 [triangle]); Simpson (1978 [triangle]).

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Object name is e-64-0o821-scheme1.jpg

Experimental

Crystal data

  • C9H10O2
  • M r = 150.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o821-efi1.jpg
  • a = 5.9134 (11) Å
  • b = 7.6048 (14) Å
  • c = 17.484 (3) Å
  • β = 97.783 (4)°
  • V = 779.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 120 (2) K
  • 0.45 × 0.43 × 0.39 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.961, T max = 0.967
  • 6617 measured reflections
  • 1855 independent reflections
  • 1482 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.124
  • S = 1.06
  • 1855 reflections
  • 102 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008738/sg2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008738/sg2231Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

supplementary crystallographic information

Comment

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).

Experimental

The title ester was prepared from commercial p-toluic acid according to standard procedure.

Refinement

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).

Figures

Fig. 1.
Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
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.

Crystal data

C9H10O2F000 = 320
Mr = 150.17Dx = 1.280 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 806 reflections
a = 5.9134 (11) Åθ = 2.4–27.8º
b = 7.6048 (14) ŵ = 0.09 mm1
c = 17.484 (3) ÅT = 120 (2) K
β = 97.783 (4)ºBlock, colourless
V = 779.0 (2) Å30.45 × 0.43 × 0.39 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1855 independent reflections
Radiation source: sealed tube1482 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 120(2) Kθmax = 27.9º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −7→7
Tmin = 0.961, Tmax = 0.967k = −10→9
6617 measured reflectionsl = −23→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.31 e Å3
102 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.39091 (14)0.28701 (11)0.44793 (5)0.0280 (2)
O20.68910 (15)0.15425 (13)0.51751 (5)0.0325 (3)
C10.2956 (2)0.31740 (17)0.51874 (7)0.0320 (3)
H1A0.27930.20500.54480.048*
H1B0.14560.37320.50680.048*
H1C0.39740.39460.55260.048*
C20.59091 (19)0.20144 (15)0.45593 (6)0.0234 (3)
C30.67753 (18)0.17434 (15)0.38071 (6)0.0223 (3)
C40.55841 (19)0.23124 (15)0.31083 (7)0.0247 (3)
H4A0.41540.28880.30980.030*
C50.6496 (2)0.20350 (15)0.24261 (7)0.0262 (3)
H5A0.56750.24260.19520.031*
C60.8588 (2)0.11953 (15)0.24239 (7)0.0244 (3)
C70.97615 (19)0.06389 (15)0.31291 (7)0.0253 (3)
H7A1.11950.00680.31400.030*
C80.88716 (19)0.09050 (15)0.38126 (7)0.0242 (3)
H8A0.96930.05150.42870.029*
C90.9593 (2)0.08897 (17)0.16858 (7)0.0312 (3)
H9A1.12130.12130.17640.047*
H9B0.87820.16130.12730.047*
H9C0.9438−0.03550.15420.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0268 (5)0.0322 (5)0.0260 (4)0.0042 (3)0.0071 (3)0.0018 (3)
O20.0343 (5)0.0389 (5)0.0234 (5)0.0042 (4)0.0004 (4)0.0016 (3)
C10.0340 (7)0.0342 (7)0.0299 (7)0.0024 (5)0.0121 (5)−0.0009 (5)
C20.0249 (6)0.0201 (6)0.0248 (6)−0.0033 (4)0.0022 (5)0.0003 (4)
C30.0236 (6)0.0203 (6)0.0232 (6)−0.0031 (4)0.0031 (4)0.0006 (4)
C40.0214 (5)0.0252 (6)0.0271 (6)0.0008 (4)0.0022 (4)0.0024 (4)
C50.0271 (6)0.0281 (6)0.0222 (6)−0.0019 (5)−0.0006 (5)0.0029 (4)
C60.0275 (6)0.0210 (6)0.0251 (6)−0.0058 (4)0.0049 (4)−0.0010 (4)
C70.0231 (6)0.0215 (6)0.0316 (6)0.0008 (4)0.0042 (5)0.0002 (4)
C80.0245 (6)0.0221 (6)0.0251 (6)−0.0017 (4)0.0000 (4)0.0032 (4)
C90.0355 (7)0.0320 (7)0.0271 (6)−0.0005 (5)0.0079 (5)−0.0018 (5)

Geometric parameters (Å, °)

O1—C21.3405 (14)C5—C61.3927 (17)
O1—C11.4468 (14)C5—H5A0.9500
O2—C21.2065 (14)C6—C71.3962 (17)
C1—H1A0.9800C6—C91.5101 (16)
C1—H1B0.9800C7—C81.3843 (16)
C1—H1C0.9800C7—H7A0.9500
C2—C31.4890 (16)C8—H8A0.9500
C3—C81.3929 (16)C9—H9A0.9800
C3—C41.3940 (16)C9—H9B0.9800
C4—C51.3899 (16)C9—H9C0.9800
C4—H4A0.9500
C2—O1—C1115.38 (9)C4—C5—H5A119.3
O1—C1—H1A109.5C6—C5—H5A119.3
O1—C1—H1B109.5C5—C6—C7118.16 (10)
H1A—C1—H1B109.5C5—C6—C9121.71 (11)
O1—C1—H1C109.5C7—C6—C9120.13 (11)
H1A—C1—H1C109.5C8—C7—C6121.10 (10)
H1B—C1—H1C109.5C8—C7—H7A119.5
O2—C2—O1123.28 (10)C6—C7—H7A119.5
O2—C2—C3124.43 (11)C7—C8—C3120.20 (10)
O1—C2—C3112.28 (9)C7—C8—H8A119.9
C8—C3—C4119.46 (10)C3—C8—H8A119.9
C8—C3—C2118.00 (10)C6—C9—H9A109.5
C4—C3—C2122.54 (10)C6—C9—H9B109.5
C5—C4—C3119.76 (11)H9A—C9—H9B109.5
C5—C4—H4A120.1C6—C9—H9C109.5
C3—C4—H4A120.1H9A—C9—H9C109.5
C4—C5—C6121.33 (10)H9B—C9—H9C109.5
C1—O1—C2—O2−1.07 (16)C3—C4—C5—C60.00 (17)
C1—O1—C2—C3179.72 (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—C8178.50 (10)C5—C6—C7—C80.28 (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—C50.12 (17)C4—C3—C8—C7−0.05 (17)
C2—C3—C4—C5179.36 (10)C2—C3—C8—C7−179.32 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···O2i0.982.513.4930 (16)177

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2231).

References

  • Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Deguire, S. & Brisse, F. (1988). Can. J. Chem.66, 2545–2552.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3867.
  • Gray, R. W. & Whalley, W. B. (1971). J. Chem. Soc. C, pp. 3575–3577. [PubMed]
  • Harris, J. P. & Mantle, P. G. (2001). Phytochemistry, 58, 709–716. [PubMed]
  • Saeed, A. & Rama, N. H. (1994). J. Sci. I. R. Iran, 5, 173–175.
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Simpson, T. J. (1978). J. Chem. Soc. Chem. Commun. pp. 627–628.

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