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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o844.
Published online 2008 April 16. doi:  10.1107/S160053680800963X
PMCID: PMC2961320

2,3-Dimethyl­phenyl benzoate

Abstract

The structure of the title compound (23DMPBA), C15H14O2, resembles those of phenyl benzoate (PBA), 3-methyl­phenyl benzoate (3MePBA), 2,6-dichloro­phenyl benzoate (26DC­PBA) and other aryl benzoates, with similar bond parameters. The dihedral angle between the benzene and benzoyl rings in 23DMPBA is 87.36 (6)°, compared with values of 55.7° in PBA, 79.61 (6)° in 3MePBA and 75.75 (10)° in 26DCPBA. The mol­ecules in 23DMPBA are packed into a chain-like structure in the direction of the a axis.

Related literature

For related literature, see: Adams & Morsi (1976 [triangle]); Gowda et al. (2007a [triangle],b [triangle]); Nayak & Gowda (2008 [triangle]).

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Object name is e-64-0o844-scheme1.jpg

Experimental

Crystal data

  • C15H14O2
  • M r = 226.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o844-efi1.jpg
  • a = 15.190 (2) Å
  • b = 8.417 (1) Å
  • c = 20.604 (2) Å
  • β = 112.20 (1)°
  • V = 2439.0 (5) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 0.65 mm−1
  • T = 299 (2) K
  • 0.50 × 0.44 × 0.36 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 2328 measured reflections
  • 2173 independent reflections
  • 1886 reflections with I > 2σ(I)
  • R int = 0.083
  • 3 standard reflections frequency: 120 min intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.157
  • S = 1.07
  • 2173 reflections
  • 181 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800963X/om2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800963X/om2224Isup2.hkl

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, as part of a study of the substituent effects on the structures of aryl benzoates (Gowda et al., 2007a,b), the structure of 2,3-dimethylphenyl benzoate (23DMPBA) has been determined. The structure of 23DMPBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976); 3-methylphenyl benzoate (3MePBA) (Gowda et al., 2007a), 2,3-dichlorophenyl benzoate (23DCPBA), 2,6-dichlorophenyl benzoate (26DCPBA) and other aryl benzoates (Gowda et al., 2007b). The bond parameters in 23DMPBA are similar to those in PBA, 3MePBA, 23DCPBA, 26DCPBA and other aryl benzoates. The dihedral angle between the benzene and benzoyl rings in 23DMPBA is 87.36 (6)°, compared to the values of 55.7° in PBA, 79.61 (6)° in 3MePBA and 75.75 (10)° in 26DCPBA. The molecules in the title compound are packed with the 2,3-dimethylphenyl and the benzoyl rings nearly orthogonal to each other, in the direction of the a axis (Fig. 2).

Experimental

The title compound was prepared according to a literature method (Nayak & Gowda, 2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2008). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution.

Refinement

The H atoms of the methyl groups were positioned with idealized geometry using a riding model with C—H = 0.96 Å The other H atoms were located in difference map, and their positional parameters were refined freely (C—H = 0.91 (2)–1.04 (2) Å). All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of the title compound as viewed down a axis.
Fig. 3.
View of the molecule in the unit cell.

Crystal data

C15H14O2F000 = 960
Mr = 226.26Dx = 1.232 Mg m3
Monoclinic, C2/cCu Kα radiation λ = 1.54180 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 15.190 (2) Åθ = 6.1–21.6º
b = 8.417 (1) ŵ = 0.65 mm1
c = 20.604 (2) ÅT = 299 (2) K
β = 112.20 (1)ºPrism, colourless
V = 2439.0 (5) Å30.50 × 0.44 × 0.36 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.083
Radiation source: fine-focus sealed tubeθmax = 66.9º
Monochromator: graphiteθmin = 4.6º
T = 299(2) Kh = −18→1
ω/2θ scansk = −10→0
Absorption correction: nonel = −23→24
2328 measured reflections3 standard reflections
2173 independent reflections every 120 min
1886 reflections with I > 2σ(I) intensity decay: none

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.048  w = 1/[σ2(Fo2) + (0.0825P)2 + 1.2712P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157(Δ/σ)max = 0.037
S = 1.07Δρmax = 0.17 e Å3
2173 reflectionsΔρmin = −0.17 e Å3
181 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (5)
Secondary atom site location: difference Fourier map

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
C10.11995 (13)0.7351 (2)0.40638 (10)0.0564 (5)
C20.11817 (13)0.6814 (2)0.46975 (10)0.0595 (5)
C30.17181 (15)0.5454 (2)0.49885 (10)0.0642 (5)
C40.22248 (16)0.4726 (3)0.46390 (12)0.0704 (6)
H40.2630 (18)0.381 (3)0.4882 (13)0.085*
C50.22058 (17)0.5274 (3)0.40080 (12)0.0715 (6)
H50.2588 (18)0.475 (3)0.3809 (14)0.086*
C60.16888 (15)0.6605 (3)0.37155 (11)0.0649 (5)
H60.1671 (17)0.701 (3)0.3293 (13)0.078*
C7−0.01527 (13)0.8854 (2)0.33725 (10)0.0567 (5)
C8−0.04911 (12)1.0494 (2)0.31758 (9)0.0504 (4)
C90.00808 (13)1.1812 (2)0.34477 (10)0.0564 (5)
H90.0723 (16)1.168 (3)0.3779 (11)0.068*
C10−0.02700 (15)1.3317 (2)0.32619 (11)0.0623 (5)
H100.0154 (16)1.430 (3)0.3487 (12)0.075*
C11−0.11960 (15)1.3535 (3)0.28000 (11)0.0631 (5)
H11−0.1449 (17)1.458 (3)0.2661 (13)0.076*
C12−0.17667 (14)1.2230 (3)0.25200 (11)0.0645 (5)
H12−0.2430 (17)1.236 (3)0.2159 (13)0.077*
C13−0.14166 (13)1.0727 (3)0.27052 (11)0.0591 (5)
H13−0.1795 (16)0.987 (3)0.2533 (12)0.071*
C140.06335 (18)0.7675 (4)0.50556 (15)0.0871 (8)
H14A0.01340.70020.50760.105*
H14B0.03620.86220.47980.105*
H14C0.10510.79540.55220.105*
C150.1773 (2)0.4813 (3)0.56843 (13)0.0935 (8)
H15A0.11430.46290.56700.112*
H15B0.20910.55680.60460.112*
H15C0.21210.38310.57800.112*
O10.07702 (9)0.88173 (15)0.37981 (8)0.0675 (4)
O2−0.06258 (11)0.76695 (18)0.31914 (10)0.0883 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0502 (9)0.0455 (9)0.0609 (10)−0.0046 (7)0.0065 (8)−0.0017 (8)
C20.0535 (10)0.0564 (11)0.0610 (11)−0.0095 (8)0.0129 (8)−0.0072 (8)
C30.0677 (11)0.0563 (11)0.0564 (10)−0.0138 (9)0.0095 (9)0.0000 (8)
C40.0738 (13)0.0501 (11)0.0703 (13)0.0013 (10)0.0079 (10)−0.0009 (9)
C50.0752 (13)0.0619 (12)0.0719 (13)0.0045 (10)0.0217 (11)−0.0120 (10)
C60.0691 (12)0.0617 (12)0.0573 (11)−0.0039 (9)0.0164 (9)−0.0044 (9)
C70.0490 (9)0.0546 (11)0.0584 (10)−0.0054 (8)0.0112 (8)−0.0043 (8)
C80.0471 (9)0.0549 (10)0.0493 (9)−0.0032 (7)0.0182 (7)−0.0015 (7)
C90.0490 (9)0.0566 (11)0.0596 (10)−0.0050 (8)0.0158 (8)−0.0020 (8)
C100.0629 (11)0.0524 (11)0.0707 (12)−0.0060 (9)0.0244 (9)−0.0003 (9)
C110.0648 (12)0.0569 (11)0.0691 (12)0.0077 (9)0.0271 (10)0.0086 (9)
C120.0511 (10)0.0692 (12)0.0668 (12)0.0066 (9)0.0148 (9)0.0069 (9)
C130.0471 (9)0.0610 (11)0.0645 (11)−0.0054 (8)0.0157 (8)−0.0020 (9)
C140.0745 (14)0.0993 (19)0.0908 (17)−0.0057 (13)0.0348 (13)−0.0173 (14)
C150.111 (2)0.0891 (17)0.0706 (14)−0.0173 (15)0.0230 (13)0.0152 (13)
O10.0532 (7)0.0483 (8)0.0808 (9)−0.0021 (5)0.0025 (6)0.0035 (6)
O20.0634 (9)0.0556 (9)0.1143 (13)−0.0099 (7)−0.0022 (8)−0.0049 (8)

Geometric parameters (Å, °)

C1—C61.365 (3)C8—C91.390 (2)
C1—C21.391 (3)C9—C101.372 (3)
C1—O11.407 (2)C9—H90.96 (2)
C2—C31.402 (3)C10—C111.381 (3)
C2—C141.492 (3)C10—H101.04 (2)
C3—C41.380 (3)C11—C121.383 (3)
C3—C151.504 (3)C11—H110.96 (2)
C4—C51.369 (3)C12—C131.370 (3)
C4—H41.00 (3)C12—H121.01 (3)
C5—C61.370 (3)C13—H130.91 (2)
C5—H50.94 (3)C14—H14A0.9600
C6—H60.92 (2)C14—H14B0.9600
C7—O21.203 (2)C14—H14C0.9600
C7—O11.344 (2)C15—H15A0.9600
C7—C81.475 (3)C15—H15B0.9600
C8—C131.387 (3)C15—H15C0.9600
C6—C1—C2123.46 (19)C8—C9—H9120.3 (14)
C6—C1—O1117.59 (18)C9—C10—C11120.18 (19)
C2—C1—O1118.66 (18)C9—C10—H10119.9 (13)
C1—C2—C3116.89 (19)C11—C10—H10119.9 (13)
C1—C2—C14121.2 (2)C10—C11—C12119.76 (19)
C3—C2—C14121.9 (2)C10—C11—H11121.1 (15)
C4—C3—C2119.20 (19)C12—C11—H11119.1 (15)
C4—C3—C15119.8 (2)C13—C12—C11120.09 (18)
C2—C3—C15121.0 (2)C13—C12—H12118.8 (14)
C5—C4—C3122.0 (2)C11—C12—H12121.0 (14)
C5—C4—H4121.7 (14)C12—C13—C8120.62 (19)
C3—C4—H4116.3 (14)C12—C13—H13120.3 (14)
C4—C5—C6119.7 (2)C8—C13—H13119.0 (15)
C4—C5—H5117.5 (16)C2—C14—H14A109.5
C6—C5—H5122.7 (16)C2—C14—H14B109.5
C1—C6—C5118.7 (2)H14A—C14—H14B109.5
C1—C6—H6120.0 (15)C2—C14—H14C109.5
C5—C6—H6121.3 (15)H14A—C14—H14C109.5
O2—C7—O1122.50 (17)H14B—C14—H14C109.5
O2—C7—C8125.80 (16)C3—C15—H15A109.5
O1—C7—C8111.70 (15)C3—C15—H15B109.5
C13—C8—C9118.88 (18)H15A—C15—H15B109.5
C13—C8—C7118.69 (16)C3—C15—H15C109.5
C9—C8—C7122.43 (16)H15A—C15—H15C109.5
C10—C9—C8120.46 (17)H15B—C15—H15C109.5
C10—C9—H9119.2 (14)C7—O1—C1119.33 (14)
C6—C1—C2—C31.5 (3)O1—C7—C8—C13176.36 (16)
O1—C1—C2—C3−172.15 (15)O2—C7—C8—C9175.1 (2)
C6—C1—C2—C14−179.93 (19)O1—C7—C8—C9−4.1 (3)
O1—C1—C2—C146.5 (3)C13—C8—C9—C101.0 (3)
C1—C2—C3—C4−0.2 (3)C7—C8—C9—C10−178.57 (18)
C14—C2—C3—C4−178.79 (19)C8—C9—C10—C11−0.2 (3)
C1—C2—C3—C15177.84 (19)C9—C10—C11—C12−0.6 (3)
C14—C2—C3—C15−0.8 (3)C10—C11—C12—C130.6 (3)
C2—C3—C4—C5−1.3 (3)C11—C12—C13—C80.3 (3)
C15—C3—C4—C5−179.3 (2)C9—C8—C13—C12−1.0 (3)
C3—C4—C5—C61.5 (3)C7—C8—C13—C12178.55 (18)
C2—C1—C6—C5−1.2 (3)O2—C7—O1—C1−2.1 (3)
O1—C1—C6—C5172.43 (17)C8—C7—O1—C1177.08 (16)
C4—C5—C6—C1−0.3 (3)C6—C1—O1—C796.1 (2)
O2—C7—C8—C13−4.5 (3)C2—C1—O1—C7−90.0 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2224).

References

  • Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347.
  • Enraf–Nonius (1996). CAD-4-PC Version 1.2. Enraf–Nonius, Delft, The Netherlands.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3756.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007b). Acta Cryst. E63, o4286.
  • Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63 In the press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stoe & Cie (1987). REDU4 Version 6.2c. Stoe & Cie, Darmstadt, Germany.

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