2,3-Dimethyl-phenyl benzoate.

The structure of the title compound (23DMPBA), C(15)H(14)O(2), resembles those of phenyl benzoate (PBA), 3-methyl-phenyl benzoate (3MePBA), 2,6-dichloro-phenyl benzoate (26DC-PBA) 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 mol-ecules 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

C15H14O2

M = 226.26

Monoclinic,

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 ▶); cell refinement: 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.

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

Enhanced figure: interactive version of Fig. 3

C15H14O2	F000 = 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 = 6.1–21.6º
b = 8.417 (1) Å	µ = 0.65 mm−1
c = 20.604 (2) Å	T = 299 (2) K
β = 112.20 (1)º	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 = 66.9º
Monochromator: graphite	θmin = 4.6º
T = 299(2) K	h = −18→1
ω/2θ scans	k = −10→0
Absorption correction: none	l = −23→24
2328 measured reflections	3 standard reflections
2173 independent reflections	every 120 min
1886 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H 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 = 1.07	Δρmax = 0.17 e Å−3
2173 reflections	Δρmin = −0.17 e Å−3
181 parameters	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)
Secondary atom site location: difference Fourier map

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)