(E)-Methyl 2-benzyl-3-o-tolyl-acrylate.

In the title compound, C(18)H(18)O(2), the methyl acrylate substituent adopts an extended E conformation with all torsion angles close to 180°. The mean plane of the acrylate unit and the phenyl ring are approximately orthogonal to each other, making a dihedral angle of 81.40 (6)°. The position of the carbonyl group with respect to the olefinic double bond is typically S-trans. The crystal packing is stabilized by inter-molecular C-H⋯π inter-actions.

Related literature

For applications of acrylate derivatives, see: Xiao et al. (2008 ▶); De Fraine & Martin, (1991 ▶). For a related structure, see: Madhanraj et al. (2011 ▶). For E-conformation aspects, see: Dunitz & Schweizer (1982 ▶). For resonance effects in acrylate, see: Merlino (1971 ▶); Varghese et al. (1986 ▶).

Experimental

Crystal data

C18H18O2

M = 266.32

Monoclinic,

a = 7.6277 (3) Å

b = 16.2167 (7) Å

c = 11.7990 (5) Å

β = 92.419 (2)°

V = 1458.19 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

16396 measured reflections

3397 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.03

3397 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013438/rk2348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013438/rk2348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013438/rk2348Isup3.cml

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

C18H18O2	F(000) = 568
Mr = 266.32	Dx = 1.213 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3397 reflections
a = 7.6277 (3) Å	θ = 2.1–27.7°
b = 16.2167 (7) Å	µ = 0.08 mm−1
c = 11.7990 (5) Å	T = 295 K
β = 92.419 (2)°	Block, colourless
V = 1458.19 (11) Å3	0.28 × 0.25 × 0.23 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.7°, θmin = 2.1°
ω and φ scans	h = −6→9
16396 measured reflections	k = −21→20
3397 independent reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1449P] where P = (Fo2 + 2Fc2)/3
3397 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.7834 (3)	0.43187 (11)	0.45429 (16)	0.0774 (6)
H1A	0.6742	0.4614	0.4486	0.116*
H1B	0.8577	0.4500	0.3956	0.116*
H1C	0.8402	0.4422	0.5270	0.116*
C2	0.74883 (18)	0.34125 (10)	0.44130 (12)	0.0506 (4)
C3	0.8329 (2)	0.29632 (11)	0.35940 (14)	0.0621 (4)
H3	0.9075	0.3235	0.3115	0.075*
C4	0.8091 (2)	0.21326 (12)	0.34737 (15)	0.0675 (5)
H4	0.8673	0.1846	0.2919	0.081*
C5	0.6995 (2)	0.17216 (11)	0.41701 (15)	0.0682 (5)
H5	0.6844	0.1155	0.4098	0.082*
C6	0.6119 (2)	0.21510 (10)	0.49768 (14)	0.0578 (4)
H6	0.5372	0.1869	0.5445	0.069*
C7	0.63261 (17)	0.29962 (9)	0.51076 (11)	0.0456 (3)
C8	0.54009 (18)	0.34614 (9)	0.59692 (12)	0.0473 (3)
H8	0.6046	0.3874	0.6342	0.057*
C9	0.37474 (18)	0.33670 (9)	0.62856 (12)	0.0467 (3)
C10	0.3070 (2)	0.39142 (9)	0.71775 (14)	0.0547 (4)
C11	0.3689 (3)	0.49930 (12)	0.84739 (16)	0.0810 (6)
H11A	0.2801	0.5356	0.8158	0.122*
H11B	0.4670	0.5312	0.8762	0.122*
H11C	0.3217	0.4679	0.9080	0.122*
C12	0.24399 (19)	0.27684 (9)	0.57786 (13)	0.0533 (4)
H12A	0.2757	0.2653	0.5007	0.064*
H12B	0.1300	0.3034	0.5738	0.064*
C13	0.22600 (17)	0.19546 (9)	0.63919 (12)	0.0441 (3)
C14	0.1264 (2)	0.13340 (10)	0.58785 (13)	0.0585 (4)
H14	0.0726	0.1426	0.5168	0.070*
C15	0.1058 (2)	0.05841 (10)	0.64005 (15)	0.0628 (4)
H15	0.0390	0.0175	0.6038	0.075*
C16	0.1829 (2)	0.04364 (10)	0.74494 (14)	0.0578 (4)
H16	0.1678	−0.0068	0.7806	0.069*
C17	0.2824 (2)	0.10417 (10)	0.79654 (13)	0.0573 (4)
H17	0.3355	0.0946	0.8677	0.069*
C18	0.30491 (19)	0.17931 (9)	0.74421 (12)	0.0512 (4)
H18	0.3741	0.2195	0.7802	0.061*
O1	0.42556 (14)	0.44424 (7)	0.76084 (9)	0.0645 (3)
O2	0.15923 (17)	0.38981 (8)	0.74826 (13)	0.0893 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0861 (13)	0.0688 (12)	0.0800 (12)	−0.0192 (10)	0.0347 (10)	0.0019 (9)
C2	0.0454 (8)	0.0596 (9)	0.0473 (8)	−0.0022 (7)	0.0069 (6)	0.0007 (7)
C3	0.0513 (9)	0.0832 (13)	0.0529 (9)	−0.0022 (8)	0.0148 (7)	−0.0043 (8)
C4	0.0553 (10)	0.0832 (13)	0.0644 (10)	0.0093 (9)	0.0075 (8)	−0.0217 (9)
C5	0.0640 (10)	0.0587 (10)	0.0824 (12)	0.0037 (8)	0.0077 (9)	−0.0152 (9)
C6	0.0576 (9)	0.0523 (9)	0.0644 (10)	−0.0009 (7)	0.0137 (8)	−0.0010 (7)
C7	0.0424 (7)	0.0508 (8)	0.0437 (8)	0.0006 (6)	0.0050 (6)	0.0005 (6)
C8	0.0509 (8)	0.0461 (8)	0.0455 (8)	−0.0028 (6)	0.0093 (6)	0.0035 (6)
C9	0.0485 (8)	0.0449 (8)	0.0475 (8)	0.0012 (6)	0.0099 (6)	0.0085 (6)
C10	0.0562 (9)	0.0488 (9)	0.0607 (9)	0.0010 (7)	0.0203 (8)	0.0087 (7)
C11	0.0874 (13)	0.0835 (14)	0.0743 (12)	0.0042 (10)	0.0280 (10)	−0.0253 (10)
C12	0.0499 (9)	0.0599 (9)	0.0502 (8)	−0.0003 (7)	0.0028 (7)	0.0097 (7)
C13	0.0374 (7)	0.0516 (8)	0.0438 (7)	−0.0019 (6)	0.0083 (6)	0.0011 (6)
C14	0.0546 (9)	0.0716 (11)	0.0489 (8)	−0.0106 (8)	−0.0030 (7)	0.0000 (8)
C15	0.0607 (10)	0.0588 (10)	0.0692 (11)	−0.0163 (8)	0.0066 (8)	−0.0077 (8)
C16	0.0636 (10)	0.0472 (9)	0.0637 (10)	−0.0007 (7)	0.0172 (8)	0.0039 (8)
C17	0.0668 (10)	0.0565 (10)	0.0488 (9)	0.0022 (8)	0.0035 (7)	0.0073 (7)
C18	0.0555 (9)	0.0517 (9)	0.0461 (8)	−0.0068 (7)	−0.0011 (7)	−0.0004 (7)
O1	0.0613 (7)	0.0686 (7)	0.0651 (7)	0.0003 (6)	0.0204 (5)	−0.0162 (6)
O2	0.0663 (8)	0.0823 (9)	0.1234 (11)	−0.0109 (6)	0.0506 (8)	−0.0197 (8)

C1—C2	1.500 (2)	C10—O1	1.3307 (19)
C1—H1A	0.9600	C11—O1	1.4368 (18)
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C3	1.389 (2)	C11—H11C	0.9600
C2—C7	1.4051 (19)	C12—C13	1.514 (2)
C3—C4	1.366 (2)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.370 (2)	C13—C18	1.380 (2)
C4—H4	0.9300	C13—C14	1.385 (2)
C5—C6	1.375 (2)	C14—C15	1.375 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.388 (2)	C15—C16	1.369 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.4701 (19)	C16—C17	1.368 (2)
C8—C9	1.3390 (18)	C16—H16	0.9300
C8—H8	0.9300	C17—C18	1.380 (2)
C9—C10	1.486 (2)	C17—H17	0.9300
C9—C12	1.498 (2)	C18—H18	0.9300
C10—O2	1.1981 (17)
C2—C1—H1A	109.5	O1—C10—C9	113.84 (12)
C2—C1—H1B	109.5	O1—C11—H11A	109.5
H1A—C1—H1B	109.5	O1—C11—H11B	109.5
C2—C1—H1C	109.5	H11A—C11—H11B	109.5
H1A—C1—H1C	109.5	O1—C11—H11C	109.5
H1B—C1—H1C	109.5	H11A—C11—H11C	109.5
C3—C2—C7	118.37 (14)	H11B—C11—H11C	109.5
C3—C2—C1	120.06 (14)	C9—C12—C13	116.50 (12)
C7—C2—C1	121.57 (13)	C9—C12—H12A	108.2
C4—C3—C2	121.76 (15)	C13—C12—H12A	108.2
C4—C3—H3	119.1	C9—C12—H12B	108.2
C2—C3—H3	119.1	C13—C12—H12B	108.2
C3—C4—C5	119.96 (15)	H12A—C12—H12B	107.3
C3—C4—H4	120.0	C18—C13—C14	117.74 (13)
C5—C4—H4	120.0	C18—C13—C12	123.35 (13)
C4—C5—C6	119.70 (16)	C14—C13—C12	118.91 (13)
C4—C5—H5	120.1	C15—C14—C13	121.19 (15)
C6—C5—H5	120.1	C15—C14—H14	119.4
C5—C6—C7	121.39 (15)	C13—C14—H14	119.4
C5—C6—H6	119.3	C16—C15—C14	120.44 (15)
C7—C6—H6	119.3	C16—C15—H15	119.8
C6—C7—C2	118.77 (13)	C14—C15—H15	119.8
C6—C7—C8	121.87 (13)	C17—C16—C15	119.08 (15)
C2—C7—C8	119.34 (13)	C17—C16—H16	120.5
C9—C8—C7	128.28 (14)	C15—C16—H16	120.5
C9—C8—H8	115.9	C16—C17—C18	120.78 (14)
C7—C8—H8	115.9	C16—C17—H17	119.6
C8—C9—C10	119.27 (14)	C18—C17—H17	119.6
C8—C9—C12	125.57 (13)	C13—C18—C17	120.77 (14)
C10—C9—C12	115.11 (12)	C13—C18—H18	119.6
O2—C10—O1	122.14 (15)	C17—C18—H18	119.6
O2—C10—C9	124.02 (16)	C10—O1—C11	116.85 (12)
C7—C2—C3—C4	−1.9 (2)	C8—C9—C10—O1	−2.2 (2)
C1—C2—C3—C4	177.90 (16)	C12—C9—C10—O1	−179.66 (12)
C2—C3—C4—C5	0.2 (3)	C8—C9—C12—C13	96.20 (17)
C3—C4—C5—C6	1.0 (3)	C10—C9—C12—C13	−86.57 (16)
C4—C5—C6—C7	−0.3 (3)	C9—C12—C13—C18	8.8 (2)
C5—C6—C7—C2	−1.4 (2)	C9—C12—C13—C14	−170.83 (13)
C5—C6—C7—C8	−179.81 (15)	C18—C13—C14—C15	0.5 (2)
C3—C2—C7—C6	2.5 (2)	C12—C13—C14—C15	−179.90 (14)
C1—C2—C7—C6	−177.32 (16)	C13—C14—C15—C16	0.4 (2)
C3—C2—C7—C8	−179.11 (14)	C14—C15—C16—C17	−0.7 (2)
C1—C2—C7—C8	1.1 (2)	C15—C16—C17—C18	0.2 (2)
C6—C7—C8—C9	−39.7 (2)	C14—C13—C18—C17	−1.0 (2)
C2—C7—C8—C9	141.93 (15)	C12—C13—C18—C17	179.36 (13)
C7—C8—C9—C10	−179.57 (13)	C16—C17—C18—C13	0.7 (2)
C7—C8—C9—C12	−2.4 (2)	O2—C10—O1—C11	0.7 (2)
C8—C9—C10—O2	176.88 (16)	C9—C10—O1—C11	179.81 (14)
C12—C9—C10—O2	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.87	3.7809 (17)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.87	3.7809 (17)	165

Symmetry code: (i) .