3,4-Di-methyl-phenyl benzoate.

In the title compound, C15H14O2, the terminal rings form a dihedral angle of 52.39 (4)°. The mean plane of the central ester group [r.m.s. deviation = 0.0488 Å] is twisted away from the benzene and phenyl rings by 60.10 (4) and 8.67 (9)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming C(6) chains which run along [100].

Related literature

For similar structures, see: Gowda et al. (2008a ▶,b ▶). For hydrogen-bonding information, see: Nardelli (1995 ▶) and for hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C15H14O2

M = 226.26

Triclinic,

a = 6.0293 (4) Å

b = 7.8506 (3) Å

c = 13.1163 (9) Å

α = 88.592 (4)°

β = 77.020 (5)°

γ = 77.680 (4)°

V = 590.87 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.33 × 0.25 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.977, T max = 1.000

5782 measured reflections

2965 independent reflections

2196 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.112

S = 1.04

2965 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELX97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814001299/tk5288sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001299/tk5288Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001299/tk5288Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14O2	Z = 2
Mr = 226.26	F(000) = 240
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Melting point: 322(1) K
a = 6.0293 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8506 (3) Å	Cell parameters from 2013 reflections
c = 13.1163 (9) Å	θ = 3.1–29.6°
α = 88.592 (4)°	µ = 0.08 mm−1
β = 77.020 (5)°	T = 123 K
γ = 77.680 (4)°	Plate, colourless
V = 590.87 (6) Å3	0.33 × 0.25 × 0.06 mm

Oxford Diffraction Xcalibur E diffractometer	2965 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 29.8°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −8→8
Tmin = 0.977, Tmax = 1.000	k = −10→10
5782 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1253P] where P = (Fo2 + 2Fc2)/3
2965 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O7	0.50750 (18)	0.19314 (11)	0.74671 (8)	0.0239 (2)
O8	0.74671 (18)	0.27031 (12)	0.83880 (8)	0.0262 (3)
C1	0.4447 (2)	0.36566 (16)	0.71295 (11)	0.0202 (3)
C2	0.2126 (2)	0.44540 (17)	0.74124 (11)	0.0227 (3)
H2	0.1032	0.3888	0.7848	0.027*
C3	0.1425 (3)	0.61121 (18)	0.70426 (11)	0.0236 (3)
H3	−0.0171	0.6682	0.7231	0.028*
C4	0.3009 (3)	0.69544 (17)	0.64030 (11)	0.0218 (3)
C5	0.5366 (2)	0.61144 (17)	0.61281 (11)	0.0213 (3)
C6	0.6075 (2)	0.44503 (17)	0.64949 (11)	0.0211 (3)
H6	0.7665	0.3865	0.6310	0.025*
C7	0.6508 (2)	0.16320 (16)	0.81492 (10)	0.0184 (3)
C8	0.6695 (2)	−0.01620 (16)	0.85620 (10)	0.0182 (3)
C9	0.8327 (2)	−0.07177 (17)	0.91616 (11)	0.0226 (3)
H9	0.9322	0.0019	0.9267	0.027*
C10	0.8508 (3)	−0.23504 (18)	0.96080 (12)	0.0257 (3)
H10	0.9613	−0.2727	1.0025	0.031*
C11	0.7073 (3)	−0.34264 (17)	0.94426 (11)	0.0252 (3)
H11	0.7192	−0.4542	0.9748	0.030*
C12	0.5461 (3)	−0.28836 (17)	0.88330 (11)	0.0241 (3)
H12	0.4495	−0.3635	0.8716	0.029*
C13	0.5251 (2)	−0.12484 (16)	0.83937 (11)	0.0205 (3)
H13	0.4135	−0.0872	0.7982	0.025*
C14	0.2186 (3)	0.87556 (18)	0.60106 (13)	0.0314 (4)
H14A	0.0507	0.9147	0.6291	0.047*
H14B	0.2509	0.8716	0.5244	0.047*
H14C	0.3010	0.9570	0.6242	0.047*
C15	0.7122 (3)	0.6999 (2)	0.54453 (12)	0.0292 (3)
H15A	0.8692	0.6291	0.5400	0.044*
H15B	0.7010	0.8151	0.5748	0.044*
H15C	0.6807	0.7130	0.4743	0.044*

	U11	U22	U33	U12	U13	U23
O7	0.0319 (6)	0.0159 (4)	0.0298 (6)	−0.0087 (4)	−0.0163 (5)	0.0063 (4)
O8	0.0332 (6)	0.0197 (5)	0.0327 (6)	−0.0133 (4)	−0.0150 (5)	0.0059 (4)
C1	0.0273 (8)	0.0157 (6)	0.0211 (7)	−0.0066 (5)	−0.0112 (6)	0.0045 (5)
C2	0.0236 (7)	0.0247 (7)	0.0220 (7)	−0.0100 (6)	−0.0057 (6)	0.0049 (6)
C3	0.0222 (7)	0.0248 (7)	0.0240 (7)	−0.0035 (6)	−0.0071 (6)	0.0014 (6)
C4	0.0283 (8)	0.0189 (6)	0.0206 (7)	−0.0050 (6)	−0.0111 (6)	0.0028 (5)
C5	0.0256 (8)	0.0232 (7)	0.0181 (7)	−0.0097 (6)	−0.0074 (6)	0.0033 (5)
C6	0.0204 (7)	0.0226 (7)	0.0207 (7)	−0.0041 (5)	−0.0058 (6)	0.0001 (5)
C7	0.0194 (7)	0.0174 (6)	0.0188 (7)	−0.0051 (5)	−0.0043 (5)	0.0016 (5)
C8	0.0216 (7)	0.0147 (6)	0.0175 (7)	−0.0042 (5)	−0.0025 (5)	−0.0001 (5)
C9	0.0261 (8)	0.0196 (6)	0.0249 (7)	−0.0067 (5)	−0.0097 (6)	0.0012 (6)
C10	0.0303 (8)	0.0225 (7)	0.0241 (7)	−0.0013 (6)	−0.0098 (6)	0.0030 (6)
C11	0.0322 (8)	0.0147 (6)	0.0251 (8)	−0.0034 (6)	−0.0012 (6)	0.0034 (5)
C12	0.0278 (8)	0.0183 (6)	0.0264 (8)	−0.0094 (6)	−0.0024 (6)	−0.0003 (6)
C13	0.0217 (7)	0.0182 (6)	0.0225 (7)	−0.0053 (5)	−0.0056 (6)	0.0002 (5)
C14	0.0376 (9)	0.0237 (7)	0.0361 (9)	−0.0062 (6)	−0.0161 (7)	0.0080 (6)
C15	0.0323 (9)	0.0324 (8)	0.0270 (8)	−0.0145 (7)	−0.0087 (7)	0.0101 (6)

O7—C7	1.3609 (16)	C8—C13	1.3950 (18)
O7—C1	1.4145 (15)	C9—C10	1.3892 (19)
O8—C7	1.2008 (16)	C9—H9	0.9500
C1—C2	1.3755 (19)	C10—C11	1.384 (2)
C1—C6	1.383 (2)	C10—H10	0.9500
C2—C3	1.3909 (19)	C11—C12	1.386 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.391 (2)	C12—C13	1.3867 (18)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.402 (2)	C13—H13	0.9500
C4—C14	1.5133 (18)	C14—H14A	0.9800
C5—C6	1.3943 (19)	C14—H14B	0.9800
C5—C15	1.504 (2)	C14—H14C	0.9800
C6—H6	0.9500	C15—H15A	0.9800
C7—C8	1.4871 (17)	C15—H15B	0.9800
C8—C9	1.3872 (19)	C15—H15C	0.9800
C7—O7—C1	117.97 (10)	C8—C9—H9	120.0
C2—C1—C6	122.09 (13)	C10—C9—H9	120.0
C2—C1—O7	116.62 (12)	C11—C10—C9	119.75 (14)
C6—C1—O7	121.17 (12)	C11—C10—H10	120.1
C1—C2—C3	118.16 (13)	C9—C10—H10	120.1
C1—C2—H2	120.9	C10—C11—C12	120.31 (13)
C3—C2—H2	120.9	C10—C11—H11	119.8
C2—C3—C4	121.48 (14)	C12—C11—H11	119.8
C2—C3—H3	119.3	C11—C12—C13	120.32 (13)
C4—C3—H3	119.3	C11—C12—H12	119.8
C3—C4—C5	119.23 (12)	C13—C12—H12	119.8
C3—C4—C14	120.13 (13)	C12—C13—C8	119.38 (13)
C5—C4—C14	120.64 (13)	C12—C13—H13	120.3
C6—C5—C4	119.46 (13)	C8—C13—H13	120.3
C6—C5—C15	120.11 (13)	C4—C14—H14A	109.5
C4—C5—C15	120.43 (13)	C4—C14—H14B	109.5
C1—C6—C5	119.57 (13)	H14A—C14—H14B	109.5
C1—C6—H6	120.2	C4—C14—H14C	109.5
C5—C6—H6	120.2	H14A—C14—H14C	109.5
O8—C7—O7	123.50 (12)	H14B—C14—H14C	109.5
O8—C7—C8	125.00 (13)	C5—C15—H15A	109.5
O7—C7—C8	111.50 (11)	C5—C15—H15B	109.5
C9—C8—C13	120.17 (12)	H15A—C15—H15B	109.5
C9—C8—C7	117.48 (12)	C5—C15—H15C	109.5
C13—C8—C7	122.32 (12)	H15A—C15—H15C	109.5
C8—C9—C10	120.06 (13)	H15B—C15—H15C	109.5
C7—O7—C1—C2	−115.77 (14)	C1—O7—C7—O8	−8.5 (2)
C7—O7—C1—C6	67.97 (17)	C1—O7—C7—C8	170.72 (11)
C6—C1—C2—C3	−0.1 (2)	O8—C7—C8—C9	−8.7 (2)
O7—C1—C2—C3	−176.31 (12)	O7—C7—C8—C9	172.01 (12)
C1—C2—C3—C4	0.1 (2)	O8—C7—C8—C13	169.10 (14)
C2—C3—C4—C5	−0.2 (2)	O7—C7—C8—C13	−10.15 (18)
C2—C3—C4—C14	179.75 (13)	C13—C8—C9—C10	−0.8 (2)
C3—C4—C5—C6	0.4 (2)	C7—C8—C9—C10	177.06 (13)
C14—C4—C5—C6	−179.59 (13)	C8—C9—C10—C11	0.7 (2)
C3—C4—C5—C15	−179.47 (13)	C9—C10—C11—C12	0.1 (2)
C14—C4—C5—C15	0.6 (2)	C10—C11—C12—C13	−0.8 (2)
C2—C1—C6—C5	0.3 (2)	C11—C12—C13—C8	0.7 (2)
O7—C1—C6—C5	176.31 (12)	C9—C8—C13—C12	0.1 (2)
C4—C5—C6—C1	−0.4 (2)	C7—C8—C13—C12	−177.65 (12)
C15—C5—C6—C1	179.46 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O8i	0.95	2.47	3.3710 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O8i	0.95	2.47	3.3710 (18)	157

Symmetry code: (i) .