2,4-Dimethyl-phenyl 4-methyl-benzoate.

In the title compound, C(16)H(16)O(2), the two aromatic rings form a dihedral angle of 49.1 (1)°. In the crystal structure, there are no classical hydrogen bonds. The long axes of the mol-ecules are directed along the c axis.

Related literature

For the preparation of the compound, see: Nayak & Gowda (2009 ▶). For background to our study of the effect of substituents on the crystal structures of aryl benzoates and for related structures, see: Gowda, Foro et al. (2007 ▶, 2008 ▶); Gowda, Tokarčík et al. (2008 ▶, 2009 ▶). For phenyl benzoate, see: Adams & Morsi (1976 ▶);

Experimental

Crystal data

C16H16O2

M = 240.29

Monoclinic,

a = 11.8022 (3) Å

b = 7.4959 (2) Å

c = 15.6288 (4) Å

β = 107.760 (3)°

V = 1316.75 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.52 × 0.38 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.96, T max = 0.991

15897 measured reflections

2497 independent reflections

1917 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.09

2497 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 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/S1600536809039397/bt5076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039397/bt5076Isup2.hkl

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

C16H16O2	F(000) = 512
Mr = 240.29	Dx = 1.212 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8238 reflections
a = 11.8022 (3) Å	θ = 2.6–29.1°
b = 7.4959 (2) Å	µ = 0.08 mm−1
c = 15.6288 (4) Å	T = 295 K
β = 107.760 (3)°	Block, colourless
V = 1316.75 (6) Å3	0.52 × 0.38 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector	2497 independent reflections
graphite	1917 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.018
ω scans	θmax = 25.7°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.96, Tmax = 0.991	k = −9→9
15897 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.1263P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2497 reflections	Δρmax = 0.15 e Å−3
167 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

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	Occ. (<1)
C1	0.40414 (14)	0.71817 (19)	−0.01638 (9)	0.0553 (4)
C2	0.51327 (13)	0.76241 (18)	−0.02574 (9)	0.0527 (4)
C3	0.51869 (13)	0.7825 (2)	−0.11255 (9)	0.0579 (4)
H3	0.5913	0.8118	−0.1207	0.069*
C4	0.42059 (14)	0.7608 (2)	−0.18776 (9)	0.0604 (4)
C5	0.31413 (15)	0.7133 (2)	−0.17447 (10)	0.0701 (5)
H5	0.2473	0.6958	−0.224	0.084*
C6	0.30490 (14)	0.6913 (2)	−0.08916 (10)	0.0670 (4)
H6	0.2328	0.6589	−0.081	0.08*
C7	0.33024 (12)	0.79735 (19)	0.10460 (10)	0.0550 (4)
C8	0.36066 (12)	0.78320 (18)	0.20315 (9)	0.0515 (4)
C9	0.45901 (12)	0.6895 (2)	0.25536 (9)	0.0563 (4)
H9	0.5079	0.6299	0.2281	0.068*
C10	0.48429 (13)	0.6843 (2)	0.34706 (9)	0.0602 (4)
H10	0.5504	0.6208	0.381	0.072*
C11	0.41410 (14)	0.77096 (19)	0.39020 (10)	0.0593 (4)
C12	0.31643 (14)	0.8645 (2)	0.33777 (11)	0.0669 (4)
H12	0.2677	0.9238	0.3653	0.08*
C13	0.28975 (13)	0.8717 (2)	0.24585 (10)	0.0632 (4)
H13	0.2239	0.9361	0.2121	0.076*
C14	0.62123 (14)	0.7885 (2)	0.05441 (10)	0.0680 (4)
H14A	0.6063	0.8821	0.0915	0.102*
H14B	0.6879	0.8203	0.0346	0.102*
H14C	0.6384	0.6798	0.0884	0.102*
C15	0.43107 (18)	0.7894 (3)	−0.28053 (10)	0.0820 (5)
H15A	0.5134	0.8025	−0.2767	0.123*	0.5
H15B	0.3884	0.8953	−0.3062	0.123*	0.5
H15C	0.3981	0.6886	−0.3177	0.123*	0.5
H15D	0.3532	0.7884	−0.3237	0.123*	0.5
H15E	0.4782	0.6957	−0.2942	0.123*	0.5
H15F	0.4685	0.9023	−0.2827	0.123*	0.5
C16	0.44110 (17)	0.7610 (2)	0.49069 (11)	0.0781 (5)
H16A	0.4014	0.6596	0.5059	0.117*
H16B	0.4138	0.8679	0.512	0.117*
H16C	0.5254	0.7492	0.5183	0.117*
O1	0.40148 (9)	0.69351 (15)	0.07226 (6)	0.0647 (3)
O2	0.25305 (10)	0.88935 (17)	0.05767 (7)	0.0784 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0661 (9)	0.0529 (8)	0.0450 (8)	0.0106 (7)	0.0143 (6)	0.0031 (6)
C2	0.0564 (8)	0.0514 (8)	0.0461 (8)	0.0135 (6)	0.0092 (6)	0.0001 (6)
C3	0.0614 (9)	0.0608 (9)	0.0507 (8)	0.0127 (7)	0.0157 (7)	0.0010 (6)
C4	0.0715 (10)	0.0599 (9)	0.0454 (8)	0.0123 (7)	0.0111 (7)	−0.0027 (6)
C5	0.0696 (10)	0.0784 (11)	0.0503 (9)	0.0004 (8)	0.0004 (7)	−0.0058 (7)
C6	0.0607 (9)	0.0752 (11)	0.0612 (10)	−0.0030 (7)	0.0125 (7)	−0.0009 (8)
C7	0.0523 (8)	0.0551 (9)	0.0580 (8)	0.0018 (6)	0.0176 (6)	0.0054 (6)
C8	0.0521 (7)	0.0507 (8)	0.0537 (8)	−0.0020 (6)	0.0191 (6)	0.0046 (6)
C9	0.0560 (8)	0.0596 (9)	0.0561 (8)	0.0043 (6)	0.0215 (6)	0.0064 (7)
C10	0.0592 (8)	0.0648 (9)	0.0568 (9)	0.0011 (7)	0.0179 (7)	0.0098 (7)
C11	0.0710 (9)	0.0559 (9)	0.0548 (8)	−0.0110 (7)	0.0247 (7)	0.0020 (7)
C12	0.0757 (10)	0.0668 (10)	0.0682 (10)	0.0058 (8)	0.0367 (8)	0.0008 (8)
C13	0.0616 (8)	0.0649 (10)	0.0663 (9)	0.0112 (7)	0.0245 (7)	0.0082 (7)
C14	0.0628 (9)	0.0794 (11)	0.0526 (9)	0.0122 (8)	0.0041 (7)	0.0054 (7)
C15	0.0993 (13)	0.0965 (14)	0.0477 (9)	0.0158 (10)	0.0185 (9)	0.0004 (8)
C16	0.1006 (13)	0.0819 (12)	0.0553 (9)	−0.0093 (10)	0.0287 (9)	0.0016 (8)
O1	0.0757 (7)	0.0698 (7)	0.0500 (6)	0.0191 (5)	0.0213 (5)	0.0094 (5)
O2	0.0729 (7)	0.0965 (9)	0.0624 (7)	0.0288 (6)	0.0154 (5)	0.0131 (6)

C1—C6	1.376 (2)	C10—C11	1.380 (2)
C1—C2	1.380 (2)	C10—H10	0.93
C1—O1	1.4075 (16)	C11—C12	1.384 (2)
C2—C3	1.3858 (19)	C11—C16	1.506 (2)
C2—C14	1.5023 (19)	C12—C13	1.375 (2)
C3—C4	1.385 (2)	C12—H12	0.93
C3—H3	0.93	C13—H13	0.93
C4—C5	1.381 (2)	C14—H14A	0.96
C4—C15	1.508 (2)	C14—H14B	0.96
C5—C6	1.380 (2)	C14—H14C	0.96
C5—H5	0.93	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—O2	1.1982 (16)	C15—H15C	0.96
C7—O1	1.3519 (17)	C15—H15D	0.96
C7—C8	1.475 (2)	C15—H15E	0.96
C8—C13	1.388 (2)	C15—H15F	0.96
C8—C9	1.3889 (19)	C16—H16A	0.96
C9—C10	1.373 (2)	C16—H16B	0.96
C9—H9	0.93	C16—H16C	0.96
C6—C1—C2	122.28 (14)	C12—C13—H13	119.9
C6—C1—O1	121.70 (14)	C8—C13—H13	119.9
C2—C1—O1	115.94 (13)	C2—C14—H14A	109.5
C1—C2—C3	116.94 (13)	C2—C14—H14B	109.5
C1—C2—C14	121.63 (13)	H14A—C14—H14B	109.5
C3—C2—C14	121.43 (14)	C2—C14—H14C	109.5
C4—C3—C2	122.82 (15)	H14A—C14—H14C	109.5
C4—C3—H3	118.6	H14B—C14—H14C	109.5
C2—C3—H3	118.6	C4—C15—H15A	109.5
C5—C4—C3	117.76 (14)	C4—C15—H15B	109.5
C5—C4—C15	121.77 (14)	H15A—C15—H15B	109.5
C3—C4—C15	120.46 (15)	C4—C15—H15C	109.5
C6—C5—C4	121.29 (14)	H15A—C15—H15C	109.5
C6—C5—H5	119.4	H15B—C15—H15C	109.5
C4—C5—H5	119.4	C4—C15—H15D	109.5
C1—C6—C5	118.88 (15)	H15A—C15—H15D	141.1
C1—C6—H6	120.6	H15B—C15—H15D	56.3
C5—C6—H6	120.6	H15C—C15—H15D	56.3
O2—C7—O1	123.10 (13)	C4—C15—H15E	109.5
O2—C7—C8	125.31 (13)	H15A—C15—H15E	56.3
O1—C7—C8	111.59 (12)	H15B—C15—H15E	141.1
C13—C8—C9	118.54 (13)	H15C—C15—H15E	56.3
C13—C8—C7	118.51 (13)	H15D—C15—H15E	109.5
C9—C8—C7	122.93 (13)	C4—C15—H15F	109.5
C10—C9—C8	120.28 (14)	H15A—C15—H15F	56.3
C10—C9—H9	119.9	H15B—C15—H15F	56.3
C8—C9—H9	119.9	H15C—C15—H15F	141.1
C9—C10—C11	121.70 (14)	H15D—C15—H15F	109.5
C9—C10—H10	119.1	H15E—C15—H15F	109.5
C11—C10—H10	119.1	C11—C16—H16A	109.5
C10—C11—C12	117.70 (14)	C11—C16—H16B	109.5
C10—C11—C16	121.25 (15)	H16A—C16—H16B	109.5
C12—C11—C16	121.04 (14)	C11—C16—H16C	109.5
C13—C12—C11	121.51 (14)	H16A—C16—H16C	109.5
C13—C12—H12	119.2	H16B—C16—H16C	109.5
C11—C12—H12	119.2	C7—O1—C1	119.70 (11)
C12—C13—C8	120.27 (14)
C6—C1—C2—C3	1.2 (2)	O1—C7—C8—C9	6.60 (19)
O1—C1—C2—C3	178.26 (12)	C13—C8—C9—C10	0.4 (2)
C6—C1—C2—C14	−179.04 (14)	C7—C8—C9—C10	178.54 (13)
O1—C1—C2—C14	−2.0 (2)	C8—C9—C10—C11	−0.1 (2)
C1—C2—C3—C4	0.3 (2)	C9—C10—C11—C12	−0.1 (2)
C14—C2—C3—C4	−179.44 (14)	C9—C10—C11—C16	178.61 (14)
C2—C3—C4—C5	−1.5 (2)	C10—C11—C12—C13	−0.1 (2)
C2—C3—C4—C15	178.28 (14)	C16—C11—C12—C13	−178.80 (15)
C3—C4—C5—C6	1.2 (2)	C11—C12—C13—C8	0.4 (2)
C15—C4—C5—C6	−178.55 (15)	C9—C8—C13—C12	−0.6 (2)
C2—C1—C6—C5	−1.5 (2)	C7—C8—C13—C12	−178.81 (14)
O1—C1—C6—C5	−178.35 (14)	O2—C7—O1—C1	13.5 (2)
C4—C5—C6—C1	0.2 (3)	C8—C7—O1—C1	−166.00 (12)
O2—C7—C8—C13	5.2 (2)	C6—C1—O1—C7	−62.88 (19)
O1—C7—C8—C13	−175.27 (13)	C2—C1—O1—C7	120.07 (15)
O2—C7—C8—C9	−172.89 (15)