organic compounds
2,3-Dimethylphenyl benzoate
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
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); Gowda et al. (2007a,b); Nayak & Gowda (2008).
Experimental
Crystal data
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Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell CAD-4-PC; 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.
Supporting information
10.1107/S160053680800963X/om2224sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680800963X/om2224Isup2.hkl
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.
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).
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell
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).C15H14O2 | F(000) = 960 |
Mr = 226.26 | Dx = 1.232 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 15.190 (2) Å | θ = 6.1–21.6° |
b = 8.417 (1) Å | µ = 0.65 mm−1 |
c = 20.604 (2) Å | T = 299 K |
β = 112.20 (1)° | Prism, colourless |
V = 2439.0 (5) Å3 | 0.50 × 0.44 × 0.36 mm |
Z = 8 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.083 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 4.6° |
Graphite monochromator | h = −18→1 |
ω/2θ scans | k = −10→0 |
2328 measured reflections | l = −23→24 |
2173 independent reflections | 3 standard reflections every 120 min |
1886 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0825P)2 + 1.2712P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.037 |
2173 reflections | Δρmax = 0.17 e Å−3 |
181 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0061 (5) |
C15H14O2 | V = 2439.0 (5) Å3 |
Mr = 226.26 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 15.190 (2) Å | µ = 0.65 mm−1 |
b = 8.417 (1) Å | T = 299 K |
c = 20.604 (2) Å | 0.50 × 0.44 × 0.36 mm |
β = 112.20 (1)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.083 |
2328 measured reflections | 3 standard reflections every 120 min |
2173 independent reflections | intensity decay: none |
1886 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.17 e Å−3 |
2173 reflections | Δρmin = −0.17 e Å−3 |
181 parameters |
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 | ||
C1 | 0.11995 (13) | 0.7351 (2) | 0.40638 (10) | 0.0564 (5) | |
C2 | 0.11817 (13) | 0.6814 (2) | 0.46975 (10) | 0.0595 (5) | |
C3 | 0.17181 (15) | 0.5454 (2) | 0.49885 (10) | 0.0642 (5) | |
C4 | 0.22248 (16) | 0.4726 (3) | 0.46390 (12) | 0.0704 (6) | |
H4 | 0.2630 (18) | 0.381 (3) | 0.4882 (13) | 0.085* | |
C5 | 0.22058 (17) | 0.5274 (3) | 0.40080 (12) | 0.0715 (6) | |
H5 | 0.2588 (18) | 0.475 (3) | 0.3809 (14) | 0.086* | |
C6 | 0.16888 (15) | 0.6605 (3) | 0.37155 (11) | 0.0649 (5) | |
H6 | 0.1671 (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) | |
C9 | 0.00808 (13) | 1.1812 (2) | 0.34477 (10) | 0.0564 (5) | |
H9 | 0.0723 (16) | 1.168 (3) | 0.3779 (11) | 0.068* | |
C10 | −0.02700 (15) | 1.3317 (2) | 0.32619 (11) | 0.0623 (5) | |
H10 | 0.0154 (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* | |
C14 | 0.06335 (18) | 0.7675 (4) | 0.50556 (15) | 0.0871 (8) | |
H14A | 0.0134 | 0.7002 | 0.5076 | 0.105* | |
H14B | 0.0362 | 0.8622 | 0.4798 | 0.105* | |
H14C | 0.1051 | 0.7954 | 0.5522 | 0.105* | |
C15 | 0.1773 (2) | 0.4813 (3) | 0.56843 (13) | 0.0935 (8) | |
H15A | 0.1143 | 0.4629 | 0.5670 | 0.112* | |
H15B | 0.2091 | 0.5568 | 0.6046 | 0.112* | |
H15C | 0.2121 | 0.3831 | 0.5780 | 0.112* | |
O1 | 0.07702 (9) | 0.88173 (15) | 0.37981 (8) | 0.0675 (4) | |
O2 | −0.06258 (11) | 0.76695 (18) | 0.31914 (10) | 0.0883 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0502 (9) | 0.0455 (9) | 0.0609 (10) | −0.0046 (7) | 0.0065 (8) | −0.0017 (8) |
C2 | 0.0535 (10) | 0.0564 (11) | 0.0610 (11) | −0.0095 (8) | 0.0129 (8) | −0.0072 (8) |
C3 | 0.0677 (11) | 0.0563 (11) | 0.0564 (10) | −0.0138 (9) | 0.0095 (9) | 0.0000 (8) |
C4 | 0.0738 (13) | 0.0501 (11) | 0.0703 (13) | 0.0013 (10) | 0.0079 (10) | −0.0009 (9) |
C5 | 0.0752 (13) | 0.0619 (12) | 0.0719 (13) | 0.0045 (10) | 0.0217 (11) | −0.0120 (10) |
C6 | 0.0691 (12) | 0.0617 (12) | 0.0573 (11) | −0.0039 (9) | 0.0164 (9) | −0.0044 (9) |
C7 | 0.0490 (9) | 0.0546 (11) | 0.0584 (10) | −0.0054 (8) | 0.0112 (8) | −0.0043 (8) |
C8 | 0.0471 (9) | 0.0549 (10) | 0.0493 (9) | −0.0032 (7) | 0.0182 (7) | −0.0015 (7) |
C9 | 0.0490 (9) | 0.0566 (11) | 0.0596 (10) | −0.0050 (8) | 0.0158 (8) | −0.0020 (8) |
C10 | 0.0629 (11) | 0.0524 (11) | 0.0707 (12) | −0.0060 (9) | 0.0244 (9) | −0.0003 (9) |
C11 | 0.0648 (12) | 0.0569 (11) | 0.0691 (12) | 0.0077 (9) | 0.0271 (10) | 0.0086 (9) |
C12 | 0.0511 (10) | 0.0692 (12) | 0.0668 (12) | 0.0066 (9) | 0.0148 (9) | 0.0069 (9) |
C13 | 0.0471 (9) | 0.0610 (11) | 0.0645 (11) | −0.0054 (8) | 0.0157 (8) | −0.0020 (9) |
C14 | 0.0745 (14) | 0.0993 (19) | 0.0908 (17) | −0.0057 (13) | 0.0348 (13) | −0.0173 (14) |
C15 | 0.111 (2) | 0.0891 (17) | 0.0706 (14) | −0.0173 (15) | 0.0230 (13) | 0.0152 (13) |
O1 | 0.0532 (7) | 0.0483 (8) | 0.0808 (9) | −0.0021 (5) | 0.0025 (6) | 0.0035 (6) |
O2 | 0.0634 (9) | 0.0556 (9) | 0.1143 (13) | −0.0099 (7) | −0.0022 (8) | −0.0049 (8) |
C1—C6 | 1.365 (3) | C8—C9 | 1.390 (2) |
C1—C2 | 1.391 (3) | C9—C10 | 1.372 (3) |
C1—O1 | 1.407 (2) | C9—H9 | 0.96 (2) |
C2—C3 | 1.402 (3) | C10—C11 | 1.381 (3) |
C2—C14 | 1.492 (3) | C10—H10 | 1.04 (2) |
C3—C4 | 1.380 (3) | C11—C12 | 1.383 (3) |
C3—C15 | 1.504 (3) | C11—H11 | 0.96 (2) |
C4—C5 | 1.369 (3) | C12—C13 | 1.370 (3) |
C4—H4 | 1.00 (3) | C12—H12 | 1.01 (3) |
C5—C6 | 1.370 (3) | C13—H13 | 0.91 (2) |
C5—H5 | 0.94 (3) | C14—H14A | 0.9600 |
C6—H6 | 0.92 (2) | C14—H14B | 0.9600 |
C7—O2 | 1.203 (2) | C14—H14C | 0.9600 |
C7—O1 | 1.344 (2) | C15—H15A | 0.9600 |
C7—C8 | 1.475 (3) | C15—H15B | 0.9600 |
C8—C13 | 1.387 (3) | C15—H15C | 0.9600 |
C6—C1—C2 | 123.46 (19) | C8—C9—H9 | 120.3 (14) |
C6—C1—O1 | 117.59 (18) | C9—C10—C11 | 120.18 (19) |
C2—C1—O1 | 118.66 (18) | C9—C10—H10 | 119.9 (13) |
C1—C2—C3 | 116.89 (19) | C11—C10—H10 | 119.9 (13) |
C1—C2—C14 | 121.2 (2) | C10—C11—C12 | 119.76 (19) |
C3—C2—C14 | 121.9 (2) | C10—C11—H11 | 121.1 (15) |
C4—C3—C2 | 119.20 (19) | C12—C11—H11 | 119.1 (15) |
C4—C3—C15 | 119.8 (2) | C13—C12—C11 | 120.09 (18) |
C2—C3—C15 | 121.0 (2) | C13—C12—H12 | 118.8 (14) |
C5—C4—C3 | 122.0 (2) | C11—C12—H12 | 121.0 (14) |
C5—C4—H4 | 121.7 (14) | C12—C13—C8 | 120.62 (19) |
C3—C4—H4 | 116.3 (14) | C12—C13—H13 | 120.3 (14) |
C4—C5—C6 | 119.7 (2) | C8—C13—H13 | 119.0 (15) |
C4—C5—H5 | 117.5 (16) | C2—C14—H14A | 109.5 |
C6—C5—H5 | 122.7 (16) | C2—C14—H14B | 109.5 |
C1—C6—C5 | 118.7 (2) | H14A—C14—H14B | 109.5 |
C1—C6—H6 | 120.0 (15) | C2—C14—H14C | 109.5 |
C5—C6—H6 | 121.3 (15) | H14A—C14—H14C | 109.5 |
O2—C7—O1 | 122.50 (17) | H14B—C14—H14C | 109.5 |
O2—C7—C8 | 125.80 (16) | C3—C15—H15A | 109.5 |
O1—C7—C8 | 111.70 (15) | C3—C15—H15B | 109.5 |
C13—C8—C9 | 118.88 (18) | H15A—C15—H15B | 109.5 |
C13—C8—C7 | 118.69 (16) | C3—C15—H15C | 109.5 |
C9—C8—C7 | 122.43 (16) | H15A—C15—H15C | 109.5 |
C10—C9—C8 | 120.46 (17) | H15B—C15—H15C | 109.5 |
C10—C9—H9 | 119.2 (14) | C7—O1—C1 | 119.33 (14) |
C6—C1—C2—C3 | 1.5 (3) | O1—C7—C8—C13 | 176.36 (16) |
O1—C1—C2—C3 | −172.15 (15) | O2—C7—C8—C9 | 175.1 (2) |
C6—C1—C2—C14 | −179.93 (19) | O1—C7—C8—C9 | −4.1 (3) |
O1—C1—C2—C14 | 6.5 (3) | C13—C8—C9—C10 | 1.0 (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—C15 | 177.84 (19) | C9—C10—C11—C12 | −0.6 (3) |
C14—C2—C3—C15 | −0.8 (3) | C10—C11—C12—C13 | 0.6 (3) |
C2—C3—C4—C5 | −1.3 (3) | C11—C12—C13—C8 | 0.3 (3) |
C15—C3—C4—C5 | −179.3 (2) | C9—C8—C13—C12 | −1.0 (3) |
C3—C4—C5—C6 | 1.5 (3) | C7—C8—C13—C12 | 178.55 (18) |
C2—C1—C6—C5 | −1.2 (3) | O2—C7—O1—C1 | −2.1 (3) |
O1—C1—C6—C5 | 172.43 (17) | C8—C7—O1—C1 | 177.08 (16) |
C4—C5—C6—C1 | −0.3 (3) | C6—C1—O1—C7 | 96.1 (2) |
O2—C7—C8—C13 | −4.5 (3) | C2—C1—O1—C7 | −90.0 (2) |
Experimental details
Crystal data | |
Chemical formula | C15H14O2 |
Mr | 226.26 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 299 |
a, b, c (Å) | 15.190 (2), 8.417 (1), 20.604 (2) |
β (°) | 112.20 (1) |
V (Å3) | 2439.0 (5) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.50 × 0.44 × 0.36 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2328, 2173, 1886 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.157, 1.07 |
No. of reflections | 2173 |
No. of parameters | 181 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
Acknowledgements
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
References
Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Enraf–Nonius (1996). CAD-4-PC. Version 1.2. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3756. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007b). Acta Cryst. E63, o4286. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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).