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Acta Cryst. (2008). E64, o844    [ doi:10.1107/S160053680800963X ]

2,3-Dimethylphenyl benzoate

B. T. Gowda, S. Foro, K. S. Babitha and H. Fuess

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound as viewed down a axis.
[Figure 3] Fig. 3. View of the molecule in the unit cell.
2,3-Dimethylphenyl benzoate top
Crystal data top
C15H14O2F000 = 960
Mr = 226.26Dx = 1.232 Mg m−3
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 mm−1
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 top
Enraf–Nonius CAD-4
diffractometer		Rint = 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 top
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 Å−3
2173 reflectionsΔρmin = −0.17 e Å−3
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
Crystal data top
C15H14O2V = 2439.0 (5) Å3
Mr = 226.26Z = 8
Monoclinic, C2/cCu Kα
a = 15.190 (2) ŵ = 0.65 mm−1
b = 8.417 (1) ÅT = 299 (2) K
c = 20.604 (2) Å0.50 × 0.44 × 0.36 mm
β = 112.20 (1)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.083
Absorption correction: none3 standard reflections
2328 measured reflections every 120 min
2173 independent reflections intensity decay: none
1886 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.048181 parameters
wR(F2) = 0.157H atoms treated by a mixture of
independent and constrained refinement
S = 1.07Δρmax = 0.17 e Å−3
2173 reflectionsΔρmin = −0.17 e Å−3
Special details top

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) top
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) top
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, °) top
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)
Acknowledgements top

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

references
References top

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.

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Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Stoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany.