2-Methyl-phenyl 4-methyl-benzoate.

The conformation of the C=O bond in the title compound 2MP4MBA, C(15)H(14)O(2), is anti to the ortho-methyl group in the phen-oxy ring. The bond parameters in 2MP4MBA are similar to those in 3-methyl-phenyl 4-methyl-benzoate (3MP4MBA), 4-methyl-phenyl 4-methyl-benzoate (4MP4MBA) and other aryl benzoates. The dihedral angle between the two aromatic rings in 2MP4MBA is 73.04 (8)°.

Related literature

For related literature, see Gowda et al. (2007 ▶, 2008 ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C15H14O2

M = 226.26

Monoclinic,

a = 11.690 (2) Å

b = 9.670 (1) Å

c = 11.478 (2) Å

β = 104.50 (2)°

V = 1256.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 299 (2) K

0.50 × 0.46 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.968, T max = 0.989

7861 measured reflections

2529 independent reflections

1385 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.200

S = 1.04

2529 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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/S1600536808022733/bx2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022733/bx2161Isup2.hkl

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

C15H14O2	F000 = 480
Mr = 226.26	Dx = 1.196 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1609 reflections
a = 11.690 (2) Å	θ = 2.8–27.9º
b = 9.670 (1) Å	µ = 0.08 mm−1
c = 11.478 (2) Å	T = 299 (2) K
β = 104.50 (2)º	Prism, colourless
V = 1256.2 (3) Å3	0.50 × 0.46 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2529 independent reflections
Radiation source: fine-focus sealed tube	1385 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.8º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −11→14
Tmin = 0.968, Tmax = 0.989	k = −12→9
7861 measured reflections	l = −13→14

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)] = 0.053	w = 1/[σ2(Fo2) + (0.092P)2 + 0.342P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.200	(Δ/σ)max = 0.006
S = 1.04	Δρmax = 0.21 e Å−3
2529 reflections	Δρmin = −0.15 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: 0.031 (6)
Secondary atom site location: difference Fourier map

Experimental. empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.5348 (2)	0.2164 (2)	0.4626 (2)	0.0639 (6)
C2	0.5493 (2)	0.1082 (2)	0.3892 (2)	0.0665 (6)
C3	0.4583 (3)	0.0849 (3)	0.2881 (2)	0.0818 (8)
H3	0.465 (2)	0.002 (3)	0.238 (3)	0.098*
C4	0.3581 (3)	0.1645 (4)	0.2630 (3)	0.0920 (9)
H4	0.293 (3)	0.134 (3)	0.192 (3)	0.110*
C5	0.3464 (3)	0.2706 (4)	0.3381 (3)	0.0929 (10)
H5	0.282 (3)	0.329 (3)	0.318 (3)	0.111*
C6	0.4355 (3)	0.2979 (3)	0.4402 (3)	0.0787 (8)
H6	0.436 (3)	0.363 (3)	0.493 (3)	0.094*
C7	0.7074 (2)	0.3305 (2)	0.5779 (2)	0.0642 (6)
C8	0.8038 (2)	0.3150 (2)	0.6887 (2)	0.0623 (6)
C9	0.8060 (2)	0.2066 (3)	0.7680 (2)	0.0713 (7)
H9	0.741 (2)	0.137 (3)	0.754 (2)	0.086*
C10	0.8988 (2)	0.1943 (3)	0.8698 (2)	0.0774 (7)
H10	0.901 (2)	0.116 (3)	0.926 (2)	0.093*
C11	0.9911 (2)	0.2878 (3)	0.8946 (2)	0.0786 (7)
C12	0.9879 (3)	0.3953 (3)	0.8146 (3)	0.0899 (9)
H12	1.052 (3)	0.462 (3)	0.823 (3)	0.108*
C13	0.8960 (2)	0.4098 (3)	0.7127 (3)	0.0802 (7)
H13	0.896 (2)	0.489 (3)	0.650 (2)	0.096*
C14	0.6588 (2)	0.0208 (3)	0.4190 (3)	0.0866 (8)
H14A	0.6673	−0.0210	0.4965	0.129*
H14B	0.7264	0.0777	0.4203	0.129*
H14C	0.6527	−0.0500	0.3592	0.129*
C15	1.0906 (3)	0.2722 (4)	1.0064 (3)	0.1079 (11)
H15A	1.1586	0.2344	0.9851	0.162*
H15B	1.0665	0.2111	1.0618	0.162*
H15C	1.1101	0.3610	1.0434	0.162*
O1	0.62322 (15)	0.23295 (16)	0.57090 (14)	0.0759 (5)
O2	0.70209 (16)	0.41780 (18)	0.50210 (17)	0.0858 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0637 (14)	0.0663 (13)	0.0593 (13)	−0.0023 (11)	0.0110 (11)	0.0084 (10)
C2	0.0723 (15)	0.0639 (13)	0.0640 (14)	0.0001 (11)	0.0183 (12)	0.0075 (11)
C3	0.097 (2)	0.0791 (17)	0.0654 (16)	−0.0007 (15)	0.0136 (14)	0.0045 (13)
C4	0.089 (2)	0.102 (2)	0.0721 (17)	−0.0112 (18)	−0.0030 (15)	0.0184 (17)
C5	0.0727 (19)	0.101 (2)	0.100 (2)	0.0197 (16)	0.0132 (17)	0.0367 (19)
C6	0.0850 (19)	0.0726 (15)	0.0808 (18)	0.0127 (14)	0.0252 (15)	0.0111 (13)
C7	0.0685 (15)	0.0544 (12)	0.0733 (15)	0.0050 (11)	0.0248 (12)	−0.0033 (11)
C8	0.0629 (13)	0.0598 (12)	0.0673 (14)	−0.0005 (10)	0.0220 (11)	−0.0064 (10)
C9	0.0678 (15)	0.0668 (14)	0.0770 (16)	−0.0082 (12)	0.0141 (13)	−0.0005 (12)
C10	0.0683 (16)	0.0829 (17)	0.0773 (17)	−0.0054 (13)	0.0115 (13)	0.0052 (13)
C11	0.0633 (15)	0.0930 (18)	0.0776 (17)	−0.0054 (13)	0.0140 (12)	−0.0117 (14)
C12	0.0740 (18)	0.0924 (19)	0.101 (2)	−0.0253 (15)	0.0165 (16)	−0.0105 (17)
C13	0.0813 (18)	0.0707 (15)	0.0899 (19)	−0.0129 (13)	0.0242 (15)	0.0009 (13)
C14	0.0866 (19)	0.0814 (17)	0.0954 (19)	0.0142 (14)	0.0294 (15)	0.0050 (14)
C15	0.0766 (19)	0.138 (3)	0.098 (2)	−0.0173 (18)	0.0013 (16)	−0.0083 (19)
O1	0.0790 (11)	0.0763 (11)	0.0667 (11)	−0.0141 (9)	0.0075 (8)	0.0060 (8)
O2	0.0901 (13)	0.0725 (11)	0.0936 (14)	0.0013 (9)	0.0205 (10)	0.0188 (9)

C1—C6	1.373 (3)	C8—C13	1.390 (3)
C1—C2	1.381 (3)	C9—C10	1.386 (4)
C1—O1	1.413 (3)	C9—H9	1.00 (3)
C2—C3	1.383 (4)	C10—C11	1.382 (4)
C2—C14	1.499 (3)	C10—H10	0.99 (3)
C3—C4	1.371 (4)	C11—C12	1.382 (4)
C3—H3	1.00 (3)	C11—C15	1.508 (4)
C4—C5	1.369 (4)	C12—C13	1.383 (4)
C4—H4	1.01 (3)	C12—H12	0.97 (3)
C5—C6	1.384 (4)	C13—H13	1.05 (3)
C5—H5	0.92 (3)	C14—H14A	0.9600
C6—H6	0.87 (3)	C14—H14B	0.9600
C7—O2	1.202 (3)	C14—H14C	0.9600
C7—O1	1.351 (3)	C15—H15A	0.9600
C7—C8	1.481 (3)	C15—H15B	0.9600
C8—C9	1.385 (3)	C15—H15C	0.9600
C6—C1—C2	123.3 (2)	C10—C9—H9	118.6 (15)
C6—C1—O1	119.9 (2)	C11—C10—C9	121.6 (3)
C2—C1—O1	116.6 (2)	C11—C10—H10	118.4 (16)
C1—C2—C3	116.7 (2)	C9—C10—H10	120.0 (16)
C1—C2—C14	121.1 (2)	C12—C11—C10	117.7 (3)
C3—C2—C14	122.2 (2)	C12—C11—C15	121.9 (3)
C4—C3—C2	121.5 (3)	C10—C11—C15	120.4 (3)
C4—C3—H3	121.1 (16)	C11—C12—C13	121.7 (3)
C2—C3—H3	117.2 (16)	C11—C12—H12	122.7 (18)
C5—C4—C3	120.2 (3)	C13—C12—H12	115.5 (18)
C5—C4—H4	123.4 (18)	C12—C13—C8	120.0 (3)
C3—C4—H4	116.1 (18)	C12—C13—H13	121.3 (15)
C4—C5—C6	120.2 (3)	C8—C13—H13	118.6 (15)
C4—C5—H5	120.5 (19)	C2—C14—H14A	109.5
C6—C5—H5	119 (2)	C2—C14—H14B	109.5
C1—C6—C5	118.1 (3)	H14A—C14—H14B	109.5
C1—C6—H6	115.4 (19)	C2—C14—H14C	109.5
C5—C6—H6	126.5 (19)	H14A—C14—H14C	109.5
O2—C7—O1	122.9 (2)	H14B—C14—H14C	109.5
O2—C7—C8	125.6 (2)	C11—C15—H15A	109.5
O1—C7—C8	111.49 (19)	C11—C15—H15B	109.5
C9—C8—C13	118.9 (2)	H15A—C15—H15B	109.5
C9—C8—C7	121.8 (2)	C11—C15—H15C	109.5
C13—C8—C7	119.3 (2)	H15A—C15—H15C	109.5
C8—C9—C10	120.1 (2)	H15B—C15—H15C	109.5
C8—C9—H9	121.4 (15)	C7—O1—C1	119.55 (17)
C6—C1—C2—C3	0.9 (4)	C13—C8—C9—C10	0.4 (4)
O1—C1—C2—C3	174.9 (2)	C7—C8—C9—C10	178.9 (2)
C6—C1—C2—C14	−179.0 (2)	C8—C9—C10—C11	−0.4 (4)
O1—C1—C2—C14	−4.9 (3)	C9—C10—C11—C12	0.3 (4)
C1—C2—C3—C4	−0.7 (4)	C9—C10—C11—C15	179.7 (3)
C14—C2—C3—C4	179.1 (2)	C10—C11—C12—C13	−0.1 (4)
C2—C3—C4—C5	0.4 (4)	C15—C11—C12—C13	−179.5 (3)
C3—C4—C5—C6	−0.3 (5)	C11—C12—C13—C8	0.1 (4)
C2—C1—C6—C5	−0.7 (4)	C9—C8—C13—C12	−0.2 (4)
O1—C1—C6—C5	−174.6 (2)	C7—C8—C13—C12	−178.8 (2)
C4—C5—C6—C1	0.4 (4)	O2—C7—O1—C1	10.7 (3)
O2—C7—C8—C9	−176.4 (2)	C8—C7—O1—C1	−169.31 (18)
O1—C7—C8—C9	3.7 (3)	C6—C1—O1—C7	−85.0 (3)
O2—C7—C8—C13	2.2 (4)	C2—C1—O1—C7	100.8 (2)
O1—C7—C8—C13	−177.7 (2)