2,5-Dimethyl-phenyl benzoate.

In the title compound, C(15)H(14)O(2), the plane of the central -C(=O)-O- group is inclined at an angle of 3.7 (2)° with respect to the benzoate ring. The two benzene rings are almost perpendicular, making a dihedral angle of 87.4 (1)°. In the crystal, mol-ecules are packed into infinite chains through weak C-H⋯π inter-actions.

Related literature

For the preparation of the compound, see: Nayak & Gowda (2009 ▶); For related structures, see: Gowda et al. (2008 ▶).

Experimental

Crystal data

C15H14O2

M = 226.26

Monoclinic,

a = 8.1095 (4) Å

b = 9.8569 (4) Å

c = 15.8805 (10) Å

β = 105.617 (5)°

V = 1222.54 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.51 × 0.37 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.958, T max = 0.982

29473 measured reflections

2330 independent reflections

1890 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.07

2330 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.10 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010976/dn2434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010976/dn2434Isup2.hkl

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

C15H14O2	F(000) = 480
Mr = 226.26	Dx = 1.229 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15569 reflections
a = 8.1095 (4) Å	θ = 3.2–29.5°
b = 9.8569 (4) Å	µ = 0.08 mm−1
c = 15.8805 (10) Å	T = 295 K
β = 105.617 (5)°	Block, colourless
V = 1222.54 (11) Å3	0.51 × 0.37 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector	2330 independent reflections
graphite	1890 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.025
ω scans	θmax = 25.9°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.958, Tmax = 0.982	k = −12→12
29473 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.051P)2 + 0.1667P] where P = (Fo2 + 2Fc2)/3
2330 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.10 e Å−3

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
O1	0.08573 (11)	0.73415 (10)	0.37466 (6)	0.0590 (3)
O2	−0.16712 (13)	0.79648 (13)	0.28463 (7)	0.0766 (3)
C1	−0.08701 (16)	0.75141 (14)	0.35356 (8)	0.0522 (3)
C2	−0.16012 (16)	0.70922 (12)	0.42546 (8)	0.0478 (3)
C3	−0.33645 (17)	0.71460 (15)	0.41159 (9)	0.0586 (4)
H3	−0.4058	0.7447	0.3583	0.070*
C4	−0.40821 (19)	0.67532 (17)	0.47672 (10)	0.0671 (4)
H4	−0.5264	0.6778	0.4673	0.080*
C5	−0.30493 (19)	0.63207 (16)	0.55630 (10)	0.0669 (4)
H5	−0.3540	0.6058	0.6004	0.080*
C6	−0.13073 (18)	0.62763 (15)	0.57060 (9)	0.0606 (4)
H6	−0.0618	0.5993	0.6245	0.073*
C7	−0.05770 (17)	0.66498 (13)	0.50552 (8)	0.0520 (3)
H7	0.0605	0.6606	0.5151	0.062*
C8	0.16784 (16)	0.77386 (14)	0.31055 (8)	0.0529 (3)
C9	0.22655 (16)	0.90581 (15)	0.31172 (8)	0.0577 (3)
C10	0.30805 (18)	0.93723 (17)	0.24763 (9)	0.0665 (4)
H10	0.3487	1.0249	0.2449	0.080*
C11	0.33025 (18)	0.84237 (19)	0.18820 (9)	0.0681 (4)
H11	0.3845	0.8677	0.1460	0.082*
C12	0.27415 (17)	0.71068 (17)	0.18959 (9)	0.0626 (4)
C13	0.19194 (17)	0.67728 (15)	0.25320 (8)	0.0570 (3)
H13	0.1533	0.5892	0.2567	0.068*
C14	0.2076 (2)	1.00775 (18)	0.37817 (11)	0.0801 (5)
H14A	0.0973	0.9975	0.3890	0.120*
H14B	0.2175	1.0975	0.3566	0.120*
H14C	0.2956	0.9938	0.4316	0.120*
C15	0.2950 (2)	0.6074 (2)	0.12344 (11)	0.0871 (5)
H15A	0.1904	0.6008	0.0776	0.131*
H15B	0.3217	0.5207	0.1514	0.131*
H15C	0.3862	0.6348	0.0992	0.131*

	U11	U22	U33	U12	U13	U23
O1	0.0521 (5)	0.0796 (6)	0.0484 (5)	0.0000 (4)	0.0188 (4)	0.0125 (4)
O2	0.0609 (6)	0.1169 (9)	0.0518 (6)	0.0068 (6)	0.0147 (5)	0.0194 (6)
C1	0.0531 (7)	0.0587 (7)	0.0451 (7)	−0.0021 (6)	0.0138 (6)	−0.0006 (6)
C2	0.0517 (7)	0.0480 (7)	0.0454 (6)	−0.0037 (5)	0.0159 (5)	−0.0056 (5)
C3	0.0530 (7)	0.0680 (9)	0.0545 (8)	−0.0003 (6)	0.0137 (6)	−0.0014 (6)
C4	0.0521 (8)	0.0831 (10)	0.0720 (9)	−0.0040 (7)	0.0269 (7)	−0.0051 (8)
C5	0.0696 (9)	0.0770 (9)	0.0643 (9)	−0.0056 (7)	0.0357 (7)	0.0002 (7)
C6	0.0664 (9)	0.0697 (9)	0.0487 (7)	0.0003 (7)	0.0204 (6)	0.0034 (6)
C7	0.0517 (7)	0.0576 (7)	0.0484 (7)	−0.0025 (6)	0.0163 (5)	−0.0028 (6)
C8	0.0455 (7)	0.0698 (8)	0.0432 (6)	−0.0006 (6)	0.0116 (5)	0.0114 (6)
C9	0.0513 (7)	0.0689 (8)	0.0492 (7)	−0.0028 (6)	0.0070 (6)	0.0075 (6)
C10	0.0558 (8)	0.0794 (10)	0.0607 (8)	−0.0133 (7)	0.0096 (7)	0.0171 (7)
C11	0.0494 (8)	0.1034 (12)	0.0545 (8)	−0.0048 (8)	0.0190 (6)	0.0147 (8)
C12	0.0476 (7)	0.0890 (11)	0.0518 (7)	0.0099 (7)	0.0144 (6)	0.0083 (7)
C13	0.0521 (7)	0.0665 (8)	0.0527 (7)	0.0014 (6)	0.0146 (6)	0.0075 (6)
C14	0.0914 (12)	0.0787 (11)	0.0666 (9)	−0.0073 (9)	0.0153 (8)	−0.0050 (8)
C15	0.0837 (12)	0.1139 (14)	0.0708 (10)	0.0228 (10)	0.0329 (9)	−0.0025 (10)

O1—C1	1.3605 (16)	C8—C9	1.383 (2)
O1—C8	1.4136 (15)	C9—C10	1.3895 (19)
O2—C1	1.1977 (16)	C9—C14	1.495 (2)
C1—C2	1.4807 (17)	C10—C11	1.374 (2)
C2—C3	1.3880 (18)	C10—H10	0.9300
C2—C7	1.3885 (18)	C11—C12	1.378 (2)
C3—C4	1.372 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.3913 (19)
C4—C5	1.382 (2)	C12—C15	1.505 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.370 (2)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.3727 (18)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C13	1.367 (2)	C15—H15C	0.9600
C1—O1—C8	116.19 (10)	C8—C9—C14	122.75 (13)
O2—C1—O1	122.74 (12)	C10—C9—C14	121.80 (14)
O2—C1—C2	125.28 (12)	C11—C10—C9	121.83 (14)
O1—C1—C2	111.98 (10)	C11—C10—H10	119.1
C3—C2—C7	119.61 (12)	C9—C10—H10	119.1
C3—C2—C1	118.43 (11)	C10—C11—C12	121.67 (13)
C7—C2—C1	121.96 (11)	C10—C11—H11	119.2
C4—C3—C2	119.83 (13)	C12—C11—H11	119.2
C4—C3—H3	120.1	C11—C12—C13	117.36 (14)
C2—C3—H3	120.1	C11—C12—C15	121.77 (14)
C3—C4—C5	120.05 (13)	C13—C12—C15	120.84 (15)
C3—C4—H4	120.0	C8—C13—C12	120.07 (14)
C5—C4—H4	120.0	C8—C13—H13	120.0
C6—C5—C4	120.36 (13)	C12—C13—H13	120.0
C6—C5—H5	119.8	C9—C14—H14A	109.5
C4—C5—H5	119.8	C9—C14—H14B	109.5
C5—C6—C7	120.09 (13)	H14A—C14—H14B	109.5
C5—C6—H6	120.0	C9—C14—H14C	109.5
C7—C6—H6	120.0	H14A—C14—H14C	109.5
C6—C7—C2	120.05 (12)	H14B—C14—H14C	109.5
C6—C7—H7	120.0	C12—C15—H15A	109.5
C2—C7—H7	120.0	C12—C15—H15B	109.5
C13—C8—C9	123.58 (12)	H15A—C15—H15B	109.5
C13—C8—O1	117.80 (12)	C12—C15—H15C	109.5
C9—C8—O1	118.54 (12)	H15A—C15—H15C	109.5
C8—C9—C10	115.44 (14)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···CT1i	0.93	2.92	3.7477 (14)	148
C6—H6···CT1ii	0.93	2.91	3.6495 (14)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯CT1i	0.93	2.92	3.7477 (14)	148
C6—H6⋯CT1ii	0.93	2.91	3.6495 (14)	137

Symmetry codes: (i) ; (ii) . CT1 is the centroid of the benzoate ring C8–C13.