2,3-Dimethyl­phenyl benzoate

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.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.157
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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S1. 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).

Related literature

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

S2. 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.

S3. 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 U_eq of the parent atom).

Computing details

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

	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.

2,3-Dimethylphenyl benzoate

Crystal data

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) Å^3	0.50 × 0.44 × 0.36 mm
Z = 8

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0825P)^2 + 1.2712P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (5)

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)