Ethyl 3-(2,4-difluoro-phen-oxy)-2-(4-methoxy-phen-yl)acrylate.

In the title mol-ecule, C(18)H(16)F(2)O(4), the two benzene rings form a dihedral angle of 55.2 (2)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating along the c axis.

Related literature

For a related crystal structure, see Fang et al. (2007 ▶). For the properties of phenyl­acetate and styrene derivatives, see: Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C18H16F2O4

M = 334.31

Monoclinic,

a = 17.295 (3) Å

b = 7.294 (2) Å

c = 14.233 (2) Å

β = 113.73 (3)°

V = 1643.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.31 × 0.30 × 0.28 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.967, T max = 0.970

3340 measured reflections

3198 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.173

S = 1.03

3198 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036945/cv2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036945/cv2469Isup2.hkl

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

C18H16F2O4	F000 = 696
Mr = 334.31	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1232 reflections
a = 17.295 (3) Å	θ = 2.3–24.5º
b = 7.294 (2) Å	µ = 0.11 mm−1
c = 14.233 (2) Å	T = 298 (2) K
β = 113.73 (3)º	Block, colorless
V = 1643.7 (7) Å3	0.31 × 0.30 × 0.28 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3198 independent reflections
Radiation source: fine-focus sealed tube	1959 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 298(2) K	θmax = 26.0º
ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −21→19
Tmin = 0.967, Tmax = 0.970	k = −8→0
3340 measured reflections	l = 0→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062	w = 1/[σ2(Fo2) + (0.0671P)2 + 1.0598P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.43 e Å−3
3198 reflections	Δρmin = −0.31 e Å−3
220 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)
Secondary atom site location: difference Fourier map

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
F1	−0.10160 (10)	0.2759 (3)	0.53359 (13)	0.0659 (6)
F2	−0.21582 (12)	0.0299 (3)	0.20055 (15)	0.0819 (7)
O1	0.11843 (13)	0.3874 (4)	0.73642 (16)	0.0643 (7)
O2	0.25578 (13)	0.4637 (3)	0.80903 (15)	0.0544 (6)
O3	0.52673 (12)	0.3660 (3)	0.63131 (16)	0.0587 (6)
O4	0.05420 (13)	0.2906 (4)	0.53932 (19)	0.0709 (7)
C1	−0.01146 (16)	0.2255 (4)	0.4503 (2)	0.0429 (7)
C2	−0.09183 (17)	0.2176 (4)	0.4484 (2)	0.0469 (7)
C3	−0.16113 (18)	0.1544 (5)	0.3667 (2)	0.0565 (9)
H3	−0.2144	0.1520	0.3682	0.068*
C4	−0.14818 (19)	0.0949 (5)	0.2827 (2)	0.0562 (8)
C5	−0.0706 (2)	0.0975 (5)	0.2794 (2)	0.0585 (9)
H5	−0.0637	0.0558	0.2215	0.070*
C6	−0.00211 (18)	0.1628 (5)	0.3632 (2)	0.0524 (8)
H6	0.0510	0.1649	0.3612	0.063*
C7	0.28913 (16)	0.3613 (4)	0.6413 (2)	0.0411 (7)
C8	0.35658 (17)	0.2736 (4)	0.7170 (2)	0.0457 (7)
H8	0.3479	0.2147	0.7699	0.055*
C9	0.43628 (17)	0.2708 (4)	0.7167 (2)	0.0485 (8)
H9	0.4803	0.2108	0.7686	0.058*
C10	0.45029 (17)	0.3582 (4)	0.6383 (2)	0.0440 (7)
C11	0.38402 (17)	0.4463 (4)	0.5619 (2)	0.0490 (8)
H11	0.3928	0.5041	0.5087	0.059*
C12	0.30513 (17)	0.4491 (4)	0.5639 (2)	0.0460 (7)
H12	0.2615	0.5109	0.5124	0.055*
C13	0.13631 (16)	0.3039 (4)	0.5529 (2)	0.0450 (7)
H13	0.1485	0.2747	0.4967	0.054*
C14	0.20244 (17)	0.3551 (4)	0.6398 (2)	0.0427 (7)
C15	0.18686 (18)	0.4008 (4)	0.7308 (2)	0.0476 (7)
C16	0.2474 (2)	0.5001 (6)	0.9039 (2)	0.0755 (11)
H16A	0.2254	0.3927	0.9251	0.091*
H16B	0.2085	0.6009	0.8950	0.091*
C17	0.3315 (3)	0.5472 (6)	0.9827 (3)	0.0840 (12)
H17A	0.3700	0.4482	0.9896	0.126*
H17B	0.3273	0.5675	1.0472	0.126*
H17C	0.3517	0.6565	0.9626	0.126*
C18	0.59573 (18)	0.2753 (5)	0.7078 (3)	0.0696 (10)
H18A	0.6035	0.3215	0.7741	0.104*
H18B	0.6460	0.2967	0.6962	0.104*
H18C	0.5846	0.1460	0.7049	0.104*

	U11	U22	U33	U12	U13	U23
F1	0.0494 (10)	0.1005 (16)	0.0561 (11)	0.0024 (10)	0.0299 (9)	−0.0084 (11)
F2	0.0591 (12)	0.1104 (18)	0.0587 (12)	−0.0114 (12)	0.0053 (10)	−0.0136 (12)
O1	0.0527 (13)	0.0918 (19)	0.0608 (14)	−0.0086 (12)	0.0358 (11)	−0.0089 (13)
O2	0.0562 (13)	0.0704 (16)	0.0429 (11)	−0.0079 (11)	0.0267 (10)	−0.0086 (11)
O3	0.0403 (11)	0.0748 (16)	0.0661 (14)	0.0039 (11)	0.0267 (10)	0.0059 (12)
O4	0.0547 (13)	0.0828 (18)	0.0761 (17)	−0.0016 (13)	0.0272 (12)	−0.0027 (14)
C1	0.0374 (14)	0.0455 (17)	0.0454 (16)	0.0002 (13)	0.0162 (13)	0.0024 (14)
C2	0.0463 (16)	0.0555 (19)	0.0440 (17)	0.0047 (14)	0.0235 (14)	0.0027 (15)
C3	0.0394 (16)	0.070 (2)	0.056 (2)	−0.0007 (16)	0.0150 (14)	0.0078 (18)
C4	0.0479 (18)	0.064 (2)	0.0462 (18)	−0.0024 (16)	0.0084 (15)	0.0012 (16)
C5	0.061 (2)	0.072 (2)	0.0460 (18)	0.0042 (18)	0.0242 (16)	−0.0044 (17)
C6	0.0447 (16)	0.067 (2)	0.0501 (18)	−0.0004 (15)	0.0239 (14)	−0.0033 (16)
C7	0.0401 (15)	0.0405 (17)	0.0440 (16)	−0.0023 (13)	0.0184 (13)	−0.0062 (13)
C8	0.0460 (16)	0.0496 (18)	0.0452 (16)	0.0030 (14)	0.0220 (13)	0.0043 (14)
C9	0.0431 (15)	0.053 (2)	0.0453 (17)	0.0089 (14)	0.0136 (13)	0.0044 (15)
C10	0.0392 (15)	0.0469 (18)	0.0484 (17)	0.0003 (13)	0.0201 (13)	−0.0052 (14)
C11	0.0462 (16)	0.058 (2)	0.0468 (17)	0.0006 (15)	0.0232 (14)	0.0080 (15)
C12	0.0409 (15)	0.0530 (19)	0.0424 (16)	0.0041 (14)	0.0151 (13)	0.0049 (15)
C13	0.0394 (15)	0.0490 (18)	0.0511 (17)	0.0018 (13)	0.0230 (13)	0.0003 (14)
C14	0.0417 (15)	0.0436 (17)	0.0470 (17)	−0.0008 (13)	0.0220 (13)	0.0003 (14)
C15	0.0500 (17)	0.0467 (18)	0.0510 (18)	−0.0026 (14)	0.0256 (15)	0.0012 (15)
C16	0.085 (3)	0.104 (3)	0.0470 (19)	−0.005 (2)	0.0371 (19)	−0.005 (2)
C17	0.109 (3)	0.090 (3)	0.047 (2)	−0.014 (3)	0.025 (2)	−0.006 (2)
C18	0.0424 (17)	0.086 (3)	0.077 (2)	0.0103 (18)	0.0202 (17)	0.003 (2)

F1—C2	1.358 (3)	C8—C9	1.380 (4)
F2—C4	1.364 (3)	C8—H8	0.9300
O1—C15	1.222 (3)	C9—C10	1.388 (4)
O2—C15	1.343 (3)	C9—H9	0.9300
O2—C16	1.440 (4)	C10—C11	1.381 (4)
O3—C10	1.366 (3)	C11—C12	1.376 (4)
O3—C18	1.415 (4)	C11—H11	0.9300
O4—C13	1.357 (3)	C12—H12	0.9300
O4—C1	1.401 (3)	C13—C14	1.356 (4)
C1—C2	1.380 (4)	C13—H13	0.9300
C1—C6	1.391 (4)	C14—C15	1.464 (4)
C2—C3	1.370 (4)	C16—C17	1.475 (5)
C3—C4	1.373 (4)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.362 (4)	C17—H17A	0.9600
C5—C6	1.384 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.385 (4)	C18—H18B	0.9600
C7—C12	1.395 (4)	C18—H18C	0.9600
C7—C14	1.491 (4)
C15—O2—C16	116.8 (2)	C12—C11—C10	120.4 (3)
C10—O3—C18	117.7 (2)	C12—C11—H11	119.8
C13—O4—C1	125.0 (2)	C10—C11—H11	119.8
C2—C1—C6	116.5 (3)	C11—C12—C7	121.5 (3)
C2—C1—O4	118.4 (3)	C11—C12—H12	119.2
C6—C1—O4	125.1 (2)	C7—C12—H12	119.2
F1—C2—C3	118.8 (3)	C14—C13—O4	126.9 (3)
F1—C2—C1	117.1 (3)	C14—C13—H13	116.6
C3—C2—C1	124.1 (3)	O4—C13—H13	116.6
C2—C3—C4	116.8 (3)	C13—C14—C15	118.8 (2)
C2—C3—H3	121.6	C13—C14—C7	119.7 (2)
C4—C3—H3	121.6	C15—C14—C7	121.5 (3)
C5—C4—F2	119.5 (3)	O1—C15—O2	122.2 (3)
C5—C4—C3	122.3 (3)	O1—C15—C14	124.6 (3)
F2—C4—C3	118.2 (3)	O2—C15—C14	113.2 (2)
C4—C5—C6	119.3 (3)	O2—C16—C17	108.4 (3)
C4—C5—H5	120.4	O2—C16—H16A	110.0
C6—C5—H5	120.4	C17—C16—H16A	110.0
C5—C6—C1	121.0 (3)	O2—C16—H16B	110.0
C5—C6—H6	119.5	C17—C16—H16B	110.0
C1—C6—H6	119.5	H16A—C16—H16B	108.4
C8—C7—C12	117.0 (2)	C16—C17—H17A	109.5
C8—C7—C14	121.6 (3)	C16—C17—H17B	109.5
C12—C7—C14	121.3 (3)	H17A—C17—H17B	109.5
C9—C8—C7	122.3 (3)	C16—C17—H17C	109.5
C9—C8—H8	118.9	H17A—C17—H17C	109.5
C7—C8—H8	118.9	H17B—C17—H17C	109.5
C8—C9—C10	119.6 (3)	O3—C18—H18A	109.5
C8—C9—H9	120.2	O3—C18—H18B	109.5
C10—C9—H9	120.2	H18A—C18—H18B	109.5
O3—C10—C11	116.3 (3)	O3—C18—H18C	109.5
O3—C10—C9	124.4 (3)	H18A—C18—H18C	109.5
C11—C10—C9	119.3 (3)	H18B—C18—H18C	109.5
C13—O4—C1—C2	179.1 (3)	C8—C9—C10—C11	−0.1 (5)
C13—O4—C1—C6	0.8 (5)	O3—C10—C11—C12	−178.6 (3)
C6—C1—C2—F1	179.1 (3)	C9—C10—C11—C12	0.6 (5)
O4—C1—C2—F1	0.6 (4)	C10—C11—C12—C7	−1.1 (5)
C6—C1—C2—C3	−0.6 (5)	C8—C7—C12—C11	1.0 (4)
O4—C1—C2—C3	−179.1 (3)	C14—C7—C12—C11	−176.3 (3)
F1—C2—C3—C4	−179.2 (3)	C1—O4—C13—C14	−175.5 (3)
C1—C2—C3—C4	0.4 (5)	O4—C13—C14—C15	0.6 (5)
C2—C3—C4—C5	0.0 (5)	O4—C13—C14—C7	179.7 (3)
C2—C3—C4—F2	179.5 (3)	C8—C7—C14—C13	−128.4 (3)
F2—C4—C5—C6	−179.7 (3)	C12—C7—C14—C13	48.7 (4)
C3—C4—C5—C6	−0.2 (6)	C8—C7—C14—C15	50.7 (4)
C4—C5—C6—C1	0.0 (5)	C12—C7—C14—C15	−132.1 (3)
C2—C1—C6—C5	0.4 (5)	C16—O2—C15—O1	5.3 (5)
O4—C1—C6—C5	178.7 (3)	C16—O2—C15—C14	−175.9 (3)
C12—C7—C8—C9	−0.4 (4)	C13—C14—C15—O1	3.9 (5)
C14—C7—C8—C9	176.8 (3)	C7—C14—C15—O1	−175.2 (3)
C7—C8—C9—C10	0.0 (5)	C13—C14—C15—O2	−174.9 (3)
C18—O3—C10—C11	−179.3 (3)	C7—C14—C15—O2	6.0 (4)
C18—O3—C10—C9	1.5 (4)	C15—O2—C16—C17	173.7 (3)
C8—C9—C10—O3	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.52	3.280 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.52	3.280 (2)	140

Symmetry code: (i) .