(Z)-Methyl 3-(2,4-dichloro-phen-yl)-2-[(2-formyl-phen-oxy)meth-yl]acrylate.

In the title compound, C(18)H(14)Cl(2)O(4), the mean planes of the methyl acrylate unit and the phenyl ring of the benzaldehyde are approximately orthogonal to each other, making a dihedral angle of 83.31 (6)°. The O atom of the aldehyde group is displaced significantly from the phenyl ring plane by 0.226 (2) Å. The methyl acrylate group adopts an E conformation. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(24) loops.

Related literature

For applications of acrylate derivatives, see: De Fraine & Martin (1991 ▶). For a related structure, see: Gong et al. (2008 ▶). For E-conformation aspects, see: Dunitz & Schweizer (1982 ▶). For resonance effects of acrylate, see: Merlino (1971 ▶); Varghese et al. (1986 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H14Cl2O4

M = 365.19

Monoclinic,

a = 17.8151 (7) Å

b = 4.9870 (2) Å

c = 18.8418 (8) Å

β = 97.834 (2)°

V = 1658.36 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 295 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

20245 measured reflections

5036 independent reflections

3310 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.149

S = 1.08

5036 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.31 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/S1600536811037925/rk2294sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037925/rk2294Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037925/rk2294Isup3.cml

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

C18H14Cl2O4	F(000) = 752
Mr = 365.19	Dx = 1.463 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5036 reflections
a = 17.8151 (7) Å	θ = 1.5–30.6°
b = 4.9870 (2) Å	µ = 0.41 mm−1
c = 18.8418 (8) Å	T = 295 K
β = 97.834 (2)°	Block, colourless
V = 1658.36 (12) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3310 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.032
graphite	θmax = 30.6°, θmin = 1.5°
ω and φ scans	h = −25→25
20245 measured reflections	k = −7→3
5036 independent reflections	l = −26→26

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0511P)2 + 1.2391P] where P = (Fo2 + 2Fc2)/3
5036 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.31 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	0.50976 (11)	0.5072 (5)	−0.12201 (11)	0.0361 (5)
C2	0.44223 (13)	0.4038 (6)	−0.15665 (13)	0.0485 (6)
H2	0.3966	0.4732	−0.1461	0.058*
C3	0.44138 (15)	0.2022 (6)	−0.20587 (15)	0.0570 (7)
H3	0.3957	0.1370	−0.2293	0.068*
C4	0.50939 (15)	0.0966 (6)	−0.22037 (13)	0.0535 (7)
H4	0.5091	−0.0430	−0.2532	0.064*
C5	0.57791 (13)	0.1942 (5)	−0.18709 (12)	0.0433 (5)
H5	0.6233	0.1199	−0.1968	0.052*
C6	0.57799 (11)	0.4045 (5)	−0.13900 (10)	0.0330 (4)
C7	0.50730 (12)	0.7188 (5)	−0.06754 (13)	0.0448 (5)
H7	0.5525	0.7996	−0.0480	0.054*
C8	0.71317 (11)	0.4083 (5)	−0.11953 (11)	0.0352 (5)
H8A	0.7138	0.3953	−0.1708	0.042*
H8B	0.7190	0.2295	−0.0993	0.042*
C9	0.77651 (11)	0.5838 (4)	−0.08667 (10)	0.0320 (4)
C10	0.80027 (12)	0.7915 (5)	−0.13589 (11)	0.0363 (5)
C11	0.89107 (15)	1.1174 (6)	−0.15499 (15)	0.0550 (7)
H11A	0.9213	1.0211	−0.1849	0.083*
H11B	0.9219	1.2478	−0.1272	0.083*
H11C	0.8503	1.2065	−0.1844	0.083*
C12	0.81596 (11)	0.5482 (5)	−0.02196 (10)	0.0341 (4)
H12	0.8557	0.6672	−0.0090	0.041*
C13	0.80390 (11)	0.3428 (5)	0.03113 (10)	0.0336 (4)
C14	0.86531 (11)	0.2247 (5)	0.07368 (11)	0.0385 (5)
C15	0.85715 (12)	0.0298 (5)	0.12376 (11)	0.0406 (5)
H15	0.8992	−0.0465	0.1510	0.049*
C16	0.78493 (12)	−0.0490 (5)	0.13245 (11)	0.0355 (4)
C17	0.72198 (12)	0.0627 (5)	0.09273 (12)	0.0396 (5)
H17	0.6736	0.0076	0.0994	0.048*
C18	0.73194 (11)	0.2575 (5)	0.04289 (11)	0.0379 (5)
H18	0.6895	0.3343	0.0163	0.046*
O1	0.44948 (10)	0.7910 (5)	−0.04748 (11)	0.0678 (6)
O2	0.64275 (7)	0.5222 (3)	−0.10540 (8)	0.0383 (4)
O3	0.76863 (12)	0.8266 (4)	−0.19514 (9)	0.0619 (5)
O4	0.86052 (9)	0.9328 (4)	−0.10778 (9)	0.0506 (4)
Cl1	0.77343 (4)	−0.29394 (13)	0.19535 (3)	0.04866 (17)
Cl2	0.95702 (3)	0.3180 (2)	0.06295 (4)	0.0730 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0322 (9)	0.0358 (12)	0.0396 (10)	0.0000 (9)	0.0021 (8)	0.0067 (9)
C2	0.0342 (11)	0.0538 (16)	0.0554 (14)	−0.0046 (11)	−0.0011 (9)	0.0064 (12)
C3	0.0452 (13)	0.0623 (19)	0.0596 (15)	−0.0194 (13)	−0.0069 (11)	−0.0025 (14)
C4	0.0615 (16)	0.0502 (17)	0.0471 (13)	−0.0177 (13)	0.0015 (11)	−0.0084 (12)
C5	0.0444 (12)	0.0437 (14)	0.0416 (11)	−0.0037 (10)	0.0055 (9)	−0.0036 (10)
C6	0.0311 (9)	0.0340 (12)	0.0329 (9)	−0.0020 (8)	0.0007 (7)	0.0038 (8)
C7	0.0311 (10)	0.0473 (15)	0.0557 (13)	0.0040 (10)	0.0045 (9)	−0.0018 (11)
C8	0.0306 (9)	0.0370 (12)	0.0381 (10)	0.0034 (8)	0.0058 (8)	−0.0056 (9)
C9	0.0297 (9)	0.0323 (11)	0.0355 (9)	0.0038 (8)	0.0095 (7)	−0.0019 (8)
C10	0.0395 (10)	0.0320 (12)	0.0390 (10)	0.0048 (9)	0.0113 (8)	−0.0029 (9)
C11	0.0554 (15)	0.0443 (16)	0.0707 (17)	−0.0052 (12)	0.0279 (13)	0.0070 (13)
C12	0.0302 (9)	0.0358 (12)	0.0370 (10)	−0.0040 (8)	0.0067 (7)	−0.0030 (9)
C13	0.0321 (9)	0.0367 (13)	0.0321 (9)	−0.0015 (8)	0.0052 (7)	−0.0017 (8)
C14	0.0274 (9)	0.0489 (14)	0.0390 (10)	−0.0018 (9)	0.0038 (8)	0.0005 (10)
C15	0.0346 (10)	0.0477 (15)	0.0382 (11)	0.0044 (10)	0.0008 (8)	0.0040 (10)
C16	0.0402 (10)	0.0320 (12)	0.0348 (9)	0.0008 (9)	0.0073 (8)	0.0011 (8)
C17	0.0306 (9)	0.0428 (14)	0.0466 (11)	−0.0009 (9)	0.0095 (8)	0.0032 (10)
C18	0.0288 (9)	0.0443 (14)	0.0410 (10)	0.0051 (9)	0.0058 (8)	0.0053 (9)
O1	0.0378 (9)	0.0831 (16)	0.0839 (14)	0.0108 (10)	0.0135 (9)	−0.0210 (12)
O2	0.0259 (6)	0.0416 (9)	0.0468 (8)	0.0029 (6)	0.0022 (6)	−0.0116 (7)
O3	0.0852 (14)	0.0552 (13)	0.0422 (9)	−0.0142 (10)	−0.0025 (9)	0.0084 (9)
O4	0.0436 (9)	0.0537 (12)	0.0549 (10)	−0.0114 (8)	0.0081 (7)	0.0109 (8)
Cl1	0.0563 (3)	0.0425 (4)	0.0483 (3)	0.0043 (3)	0.0113 (2)	0.0107 (3)
Cl2	0.0285 (3)	0.1081 (7)	0.0808 (5)	−0.0100 (3)	0.0017 (3)	0.0344 (5)

C1—C2	1.387 (3)	C10—O3	1.193 (3)
C1—C6	1.396 (3)	C10—O4	1.332 (3)
C1—C7	1.477 (3)	C11—O4	1.438 (3)
C2—C3	1.367 (4)	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.382 (4)	C11—H11C	0.9600
C3—H3	0.9300	C12—C13	1.468 (3)
C4—C5	1.383 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.396 (3)
C5—C6	1.386 (3)	C13—C18	1.397 (3)
C5—H5	0.9300	C14—C15	1.376 (3)
C6—O2	1.370 (2)	C14—Cl2	1.737 (2)
C7—O1	1.200 (3)	C15—C16	1.376 (3)
C7—H7	0.9300	C15—H15	0.9300
C8—O2	1.435 (2)	C16—C17	1.378 (3)
C8—C9	1.494 (3)	C16—Cl1	1.733 (2)
C8—H8A	0.9700	C17—C18	1.379 (3)
C8—H8B	0.9700	C17—H17	0.9300
C9—C12	1.334 (3)	C18—H18	0.9300
C9—C10	1.490 (3)
C2—C1—C6	118.8 (2)	O3—C10—C9	123.1 (2)
C2—C1—C7	119.1 (2)	O4—C10—C9	113.71 (18)
C6—C1—C7	122.06 (19)	O4—C11—H11A	109.5
C3—C2—C1	121.4 (2)	O4—C11—H11B	109.5
C3—C2—H2	119.3	H11A—C11—H11B	109.5
C1—C2—H2	119.3	O4—C11—H11C	109.5
C2—C3—C4	119.0 (2)	H11A—C11—H11C	109.5
C2—C3—H3	120.5	H11B—C11—H11C	109.5
C4—C3—H3	120.5	C9—C12—C13	127.44 (19)
C3—C4—C5	121.3 (3)	C9—C12—H12	116.3
C3—C4—H4	119.3	C13—C12—H12	116.3
C5—C4—H4	119.3	C14—C13—C18	116.4 (2)
C4—C5—C6	119.0 (2)	C14—C13—C12	120.66 (18)
C4—C5—H5	120.5	C18—C13—C12	122.91 (18)
C6—C5—H5	120.5	C15—C14—C13	122.98 (19)
O2—C6—C5	123.51 (19)	C15—C14—Cl2	117.26 (16)
O2—C6—C1	116.20 (19)	C13—C14—Cl2	119.75 (17)
C5—C6—C1	120.28 (19)	C14—C15—C16	118.11 (19)
O1—C7—C1	122.8 (2)	C14—C15—H15	120.9
O1—C7—H7	118.6	C16—C15—H15	120.9
C1—C7—H7	118.6	C15—C16—C17	121.6 (2)
O2—C8—C9	108.75 (17)	C15—C16—Cl1	118.83 (17)
O2—C8—H8A	109.9	C17—C16—Cl1	119.53 (17)
C9—C8—H8A	109.9	C16—C17—C18	118.94 (19)
O2—C8—H8B	109.9	C16—C17—H17	120.5
C9—C8—H8B	109.9	C18—C17—H17	120.5
H8A—C8—H8B	108.3	C17—C18—C13	121.90 (19)
C12—C9—C10	120.18 (19)	C17—C18—H18	119.0
C12—C9—C8	125.1 (2)	C13—C18—H18	119.0
C10—C9—C8	114.33 (17)	C6—O2—C8	116.56 (16)
O3—C10—O4	123.2 (2)	C10—O4—C11	116.43 (19)
C6—C1—C2—C3	1.0 (4)	C9—C12—C13—C14	143.0 (2)
C7—C1—C2—C3	−178.0 (2)	C9—C12—C13—C18	−38.0 (3)
C1—C2—C3—C4	1.1 (4)	C18—C13—C14—C15	1.5 (3)
C2—C3—C4—C5	−1.2 (4)	C12—C13—C14—C15	−179.4 (2)
C3—C4—C5—C6	−0.8 (4)	C18—C13—C14—Cl2	−179.99 (17)
C4—C5—C6—O2	−177.4 (2)	C12—C13—C14—Cl2	−0.9 (3)
C4—C5—C6—C1	3.0 (3)	C13—C14—C15—C16	−0.7 (4)
C2—C1—C6—O2	177.3 (2)	Cl2—C14—C15—C16	−179.27 (18)
C7—C1—C6—O2	−3.8 (3)	C14—C15—C16—C17	−0.2 (3)
C2—C1—C6—C5	−3.1 (3)	C14—C15—C16—Cl1	−179.91 (18)
C7—C1—C6—C5	175.9 (2)	C15—C16—C17—C18	0.3 (4)
C2—C1—C7—O1	6.2 (4)	Cl1—C16—C17—C18	179.96 (17)
C6—C1—C7—O1	−172.7 (2)	C16—C17—C18—C13	0.6 (3)
O2—C8—C9—C12	94.7 (2)	C14—C13—C18—C17	−1.4 (3)
O2—C8—C9—C10	−92.5 (2)	C12—C13—C18—C17	179.5 (2)
C12—C9—C10—O3	177.6 (2)	C5—C6—O2—C8	−3.0 (3)
C8—C9—C10—O3	4.4 (3)	C1—C6—O2—C8	176.68 (18)
C12—C9—C10—O4	−1.9 (3)	C9—C8—O2—C6	172.41 (17)
C8—C9—C10—O4	−175.07 (18)	O3—C10—O4—C11	−5.7 (3)
C10—C9—C12—C13	−175.53 (19)	C9—C10—O4—C11	173.79 (19)
C8—C9—C12—C13	−3.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.49	3.143 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.49	3.143 (3)	128

Symmetry code: (i) .