Methyl 2-[(2-methyl-phen-oxy)meth-yl]benzoate.

In the title methyl-benzoate compound, C(16)H(16)O(3), the mol-ecule is essentially planar (r.m.s. of all fitted non-H atoms = 0.0370 Å); the dihedral angle between the phenyl rings is 2.30 (7)°. Apart from a C-H⋯π inter-action, no marked inter-molecular contacts are obvious.

Related literature

For the pharmaceutical background to methyl­benzoate derivatives, see: Orlek et al. (1991 ▶); Ankersen et al. (1997 ▶); Andersen et al. (1996 ▶).

Experimental

Crystal data

C16H16O3

M = 256.29

Monoclinic,

a = 31.6873 (13) Å

b = 6.5389 (2) Å

c = 13.8746 (6) Å

β = 111.716 (2)°

V = 2670.79 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.51 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.956, T max = 0.996

12273 measured reflections

3320 independent reflections

2295 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.108

S = 1.03

3320 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005995/tk5056sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812005995/tk5056Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005995/tk5056Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812005995/tk5056Isup4.cml

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

C16H16O3	F(000) = 1088
Mr = 256.29	Dx = 1.275 Mg m−3
Monoclinic, C2/c	Melting point = 412–414 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 31.6873 (13) Å	Cell parameters from 4067 reflections
b = 6.5389 (2) Å	θ = 2.8–28.1°
c = 13.8746 (6) Å	µ = 0.09 mm−1
β = 111.716 (2)°	T = 200 K
V = 2670.79 (18) Å3	Platelet, colourless
Z = 8	0.51 × 0.12 × 0.05 mm

Bruker APEXII CCD diffractometer	3320 independent reflections
Radiation source: fine-focus sealed tube	2295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −39→42
Tmin = 0.956, Tmax = 0.996	k = −8→7
12273 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0475P)2 + 1.0316P] where P = (Fo2 + 2Fc2)/3
3320 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.10397 (3)	0.81204 (14)	0.13302 (7)	0.0379 (2)
O2	0.18815 (3)	0.10731 (15)	0.06203 (7)	0.0413 (3)
O3	0.20550 (3)	0.42927 (15)	0.11449 (9)	0.0479 (3)
C1	0.04466 (5)	1.1075 (2)	0.14318 (12)	0.0452 (4)
H1A	0.0273	1.1996	0.1703	0.068*
H1B	0.0330	0.9679	0.1401	0.068*
H1C	0.0416	1.1517	0.0734	0.068*
C2	0.13423 (4)	0.6661 (2)	0.11746 (10)	0.0317 (3)
H2A	0.1505	0.5918	0.1830	0.038*
H2B	0.1570	0.7366	0.0962	0.038*
C3	0.17758 (4)	0.3033 (2)	0.06884 (9)	0.0305 (3)
C4	0.23538 (5)	0.0547 (3)	0.11380 (13)	0.0519 (4)
H4A	0.2394	−0.0923	0.1064	0.078*
H4B	0.2451	0.0893	0.1876	0.078*
H4C	0.2537	0.1312	0.0826	0.078*
C11	0.12341 (4)	0.96097 (19)	0.20588 (10)	0.0311 (3)
C12	0.09376 (5)	1.1127 (2)	0.21316 (10)	0.0331 (3)
C13	0.11164 (5)	1.2669 (2)	0.28589 (11)	0.0410 (3)
H13	0.0921	1.3722	0.2919	0.049*
C14	0.15703 (5)	1.2712 (2)	0.34969 (12)	0.0443 (4)
H14	0.1684	1.3778	0.3991	0.053*
C15	0.18555 (5)	1.1203 (2)	0.34109 (11)	0.0411 (3)
H15	0.2168	1.1230	0.3845	0.049*
C16	0.16901 (5)	0.9642 (2)	0.26944 (10)	0.0359 (3)
H16	0.1888	0.8597	0.2639	0.043*
C21	0.10746 (4)	0.51750 (19)	0.03453 (9)	0.0282 (3)
C22	0.06136 (4)	0.5484 (2)	−0.02189 (10)	0.0339 (3)
H22	0.0466	0.6644	−0.0074	0.041*
C23	0.03669 (5)	0.4130 (2)	−0.09866 (10)	0.0385 (3)
H23	0.0054	0.4375	−0.1368	0.046*
C24	0.05731 (5)	0.2426 (2)	−0.12015 (10)	0.0390 (3)
H24	0.0403	0.1505	−0.1733	0.047*
C25	0.10285 (4)	0.2062 (2)	−0.06413 (10)	0.0337 (3)
H25	0.1170	0.0877	−0.0781	0.040*
C26	0.12814 (4)	0.34252 (19)	0.01282 (9)	0.0277 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0334 (5)	0.0333 (5)	0.0417 (5)	0.0048 (4)	0.0079 (4)	−0.0104 (4)
O2	0.0333 (5)	0.0335 (5)	0.0489 (6)	0.0078 (4)	0.0056 (4)	−0.0051 (4)
O3	0.0302 (5)	0.0371 (6)	0.0677 (7)	−0.0025 (4)	0.0078 (5)	−0.0114 (5)
C1	0.0420 (8)	0.0468 (9)	0.0476 (9)	0.0138 (7)	0.0173 (7)	0.0052 (7)
C2	0.0307 (7)	0.0269 (7)	0.0362 (7)	0.0029 (5)	0.0110 (5)	−0.0033 (5)
C3	0.0329 (7)	0.0299 (7)	0.0300 (6)	0.0020 (6)	0.0130 (5)	0.0000 (5)
C4	0.0368 (8)	0.0470 (9)	0.0628 (10)	0.0142 (7)	0.0077 (7)	−0.0014 (8)
C11	0.0378 (7)	0.0256 (6)	0.0311 (7)	−0.0001 (5)	0.0143 (6)	−0.0008 (5)
C12	0.0406 (7)	0.0290 (7)	0.0353 (7)	0.0037 (6)	0.0205 (6)	0.0058 (5)
C13	0.0552 (9)	0.0293 (7)	0.0485 (8)	0.0044 (7)	0.0308 (7)	−0.0012 (6)
C14	0.0562 (9)	0.0367 (8)	0.0461 (8)	−0.0092 (7)	0.0259 (7)	−0.0124 (6)
C15	0.0407 (8)	0.0407 (8)	0.0426 (8)	−0.0100 (7)	0.0164 (6)	−0.0080 (6)
C16	0.0365 (7)	0.0319 (7)	0.0401 (7)	0.0007 (6)	0.0149 (6)	−0.0037 (6)
C21	0.0310 (6)	0.0264 (6)	0.0275 (6)	−0.0008 (5)	0.0111 (5)	0.0021 (5)
C22	0.0329 (7)	0.0340 (7)	0.0348 (7)	0.0043 (6)	0.0127 (6)	−0.0004 (6)
C23	0.0277 (7)	0.0465 (9)	0.0370 (7)	0.0007 (6)	0.0070 (6)	−0.0014 (6)
C24	0.0355 (7)	0.0434 (8)	0.0345 (7)	−0.0056 (6)	0.0088 (6)	−0.0103 (6)
C25	0.0354 (7)	0.0325 (7)	0.0341 (7)	−0.0006 (6)	0.0140 (6)	−0.0050 (6)
C26	0.0293 (6)	0.0275 (6)	0.0273 (6)	−0.0014 (5)	0.0113 (5)	0.0010 (5)

O1—C11	1.3744 (15)	C12—C13	1.3901 (19)
O1—C2	1.4251 (15)	C13—C14	1.382 (2)
O2—C3	1.3367 (16)	C13—H13	0.9500
O2—C4	1.4419 (16)	C14—C15	1.373 (2)
O3—C3	1.2034 (15)	C14—H14	0.9500
C1—C12	1.4988 (19)	C15—C16	1.3856 (19)
C1—H1A	0.9800	C15—H15	0.9500
C1—H1B	0.9800	C16—H16	0.9500
C1—H1C	0.9800	C21—C22	1.3933 (17)
C2—C21	1.5049 (17)	C21—C26	1.4054 (18)
C2—H2A	0.9900	C22—C23	1.3836 (19)
C2—H2B	0.9900	C22—H22	0.9500
C3—C26	1.4910 (17)	C23—C24	1.379 (2)
C4—H4A	0.9800	C23—H23	0.9500
C4—H4B	0.9800	C24—C25	1.3832 (19)
C4—H4C	0.9800	C24—H24	0.9500
C11—C16	1.3869 (18)	C25—C26	1.3940 (17)
C11—C12	1.3954 (18)	C25—H25	0.9500
C11—O1—C2	116.26 (10)	C14—C13—H13	119.1
C3—O2—C4	115.77 (11)	C12—C13—H13	119.1
C12—C1—H1A	109.5	C15—C14—C13	119.48 (13)
C12—C1—H1B	109.5	C15—C14—H14	120.3
H1A—C1—H1B	109.5	C13—C14—H14	120.3
C12—C1—H1C	109.5	C14—C15—C16	120.37 (14)
H1A—C1—H1C	109.5	C14—C15—H15	119.8
H1B—C1—H1C	109.5	C16—C15—H15	119.8
O1—C2—C21	109.13 (10)	C15—C16—C11	119.72 (13)
O1—C2—H2A	109.9	C15—C16—H16	120.1
C21—C2—H2A	109.9	C11—C16—H16	120.1
O1—C2—H2B	109.9	C22—C21—C26	118.21 (11)
C21—C2—H2B	109.9	C22—C21—C2	120.87 (12)
H2A—C2—H2B	108.3	C26—C21—C2	120.92 (11)
O3—C3—O2	122.60 (12)	C23—C22—C21	121.06 (13)
O3—C3—C26	125.65 (12)	C23—C22—H22	119.5
O2—C3—C26	111.75 (11)	C21—C22—H22	119.5
O2—C4—H4A	109.5	C24—C23—C22	120.37 (12)
O2—C4—H4B	109.5	C24—C23—H23	119.8
H4A—C4—H4B	109.5	C22—C23—H23	119.8
O2—C4—H4C	109.5	C23—C24—C25	119.80 (12)
H4A—C4—H4C	109.5	C23—C24—H24	120.1
H4B—C4—H4C	109.5	C25—C24—H24	120.1
O1—C11—C16	123.80 (12)	C24—C25—C26	120.31 (13)
O1—C11—C12	115.25 (12)	C24—C25—H25	119.8
C16—C11—C12	120.95 (12)	C26—C25—H25	119.8
C13—C12—C11	117.63 (13)	C25—C26—C21	120.22 (11)
C13—C12—C1	122.21 (13)	C25—C26—C3	118.98 (11)
C11—C12—C1	120.15 (12)	C21—C26—C3	120.77 (11)
C14—C13—C12	121.85 (13)
C11—O1—C2—C21	−179.15 (10)	O1—C2—C21—C26	−172.01 (11)
C4—O2—C3—O3	0.5 (2)	C26—C21—C22—C23	−1.23 (19)
C4—O2—C3—C26	179.87 (12)	C2—C21—C22—C23	179.57 (12)
C2—O1—C11—C16	−6.01 (19)	C21—C22—C23—C24	0.7 (2)
C2—O1—C11—C12	174.45 (11)	C22—C23—C24—C25	0.5 (2)
O1—C11—C12—C13	179.82 (11)	C23—C24—C25—C26	−1.0 (2)
C16—C11—C12—C13	0.3 (2)	C24—C25—C26—C21	0.4 (2)
O1—C11—C12—C1	−0.95 (18)	C24—C25—C26—C3	−177.54 (12)
C16—C11—C12—C1	179.49 (13)	C22—C21—C26—C25	0.69 (18)
C11—C12—C13—C14	−0.4 (2)	C2—C21—C26—C25	179.89 (12)
C1—C12—C13—C14	−179.57 (13)	C22—C21—C26—C3	178.60 (11)
C12—C13—C14—C15	0.4 (2)	C2—C21—C26—C3	−2.21 (18)
C13—C14—C15—C16	−0.3 (2)	O3—C3—C26—C25	158.37 (14)
C14—C15—C16—C11	0.2 (2)	O2—C3—C26—C25	−20.99 (16)
O1—C11—C16—C15	−179.72 (12)	O3—C3—C26—C21	−19.6 (2)
C12—C11—C16—C15	−0.2 (2)	O2—C3—C26—C21	161.08 (11)
O1—C2—C21—C22	7.17 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···Cg1i	0.95	2.72	3.5461 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯Cg1i	0.95	2.72	3.5461 (15)	146

Symmetry code: (i) .