Ethyl 2-(4-chloro-phenyl)-3-(2,4-di-fluoro-phenoxy)acrylate.

In the mol-ecule of the title compound, C(17)H(13)ClF(2)O(3), the dihedral angles formed by the aromatic rings of the chloro-benzene and difluoro-benzene groups with the plane of the acrylate unit are 48.85 (12) and 9.07 (14)°, respectively. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen-bond inter-actions, forming chains along the c axis.

Related literature

For the synthesis and crystal structures of related compounds, see: Li, Xue et al. (2008 ▶); Li, Wang & Jian (2008 ▶); Lin & Jian (2008 ▶); Liu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13ClF2O3

M = 338.72

Monoclinic,

a = 16.275 (3) Å

b = 7.503 (2) Å

c = 13.812 (3) Å

β = 111.11 (3)°

V = 1573.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.922, T max = 0.973

2956 measured reflections

2823 independent reflections

1566 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.189

S = 1.02

2823 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 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/S1600536808037318/rz2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037318/rz2266Isup2.hkl

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

C17H13ClF2O3	F000 = 696
Mr = 338.72	Dx = 1.430 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1002 reflections
a = 16.275 (3) Å	θ = 2.4–24.5º
b = 7.503 (2) Å	µ = 0.28 mm−1
c = 13.812 (3) Å	T = 298 (2) K
β = 111.11 (3)º	Block, colorless
V = 1573.4 (7) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2823 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 298(2) K	θmax = 25.2º
ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −19→18
Tmin = 0.922, Tmax = 0.973	k = −9→10
2956 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065	w = 1/[σ2(Fo2) + (0.0904P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.38 e Å−3
2823 reflections	Δρmin = −0.34 e Å−3
210 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: 0.018 (3)
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
C1	1.0187 (2)	0.7796 (5)	0.9699 (3)	0.0450 (9)
C2	1.1022 (2)	0.7724 (5)	1.0453 (3)	0.0473 (9)
C3	1.1764 (2)	0.8337 (6)	1.0319 (3)	0.0581 (11)
H3	1.2315	0.8266	1.0844	0.070*
C4	1.1654 (3)	0.9066 (6)	0.9368 (3)	0.0597 (11)
C5	1.0851 (3)	0.9178 (6)	0.8598 (3)	0.0621 (12)
H5	1.0797	0.9691	0.7964	0.074*
C6	1.0121 (3)	0.8535 (6)	0.8755 (3)	0.0561 (11)
H6	0.9574	0.8596	0.8222	0.067*
C7	0.7054 (2)	0.6469 (5)	0.8670 (3)	0.0423 (9)
C8	0.6325 (2)	0.7234 (5)	0.8808 (3)	0.0540 (10)
H8	0.6376	0.7663	0.9459	0.065*
C9	0.5527 (2)	0.7366 (6)	0.7996 (3)	0.0571 (11)
H9	0.5045	0.7876	0.8100	0.069*
C10	0.5451 (2)	0.6742 (5)	0.7036 (3)	0.0543 (11)
C11	0.6147 (3)	0.5952 (6)	0.6881 (3)	0.0572 (11)
H11	0.6086	0.5513	0.6229	0.069*
C12	0.6947 (2)	0.5804 (5)	0.7696 (3)	0.0482 (10)
H12	0.7418	0.5252	0.7588	0.058*
C13	0.8635 (2)	0.7022 (5)	0.9293 (3)	0.0465 (9)
H13	0.8526	0.7373	0.8612	0.056*
C14	0.7936 (2)	0.6482 (5)	0.9511 (3)	0.0426 (9)
C15	0.8065 (2)	0.5946 (5)	1.0579 (3)	0.0483 (10)
C16	0.7414 (3)	0.4744 (6)	1.1715 (3)	0.0627 (12)
H16A	0.7580	0.5754	1.2185	0.075*
H16B	0.7858	0.3824	1.1975	0.075*
C17	0.6537 (3)	0.4055 (7)	1.1643 (3)	0.0716 (13)
H17A	0.6093	0.4922	1.1303	0.107*
H17B	0.6538	0.3831	1.2327	0.107*
H17C	0.6415	0.2968	1.1250	0.107*
Cl1	0.44478 (7)	0.69754 (19)	0.60039 (9)	0.0891 (5)
F1	1.10978 (13)	0.7012 (3)	1.13855 (15)	0.0663 (7)
F2	1.23761 (16)	0.9699 (4)	0.9209 (2)	0.0858 (9)
O3	0.94846 (18)	0.7113 (4)	0.9954 (2)	0.0723 (9)
O1	0.87704 (17)	0.6033 (4)	1.13049 (18)	0.0666 (9)
O2	0.73412 (16)	0.5282 (4)	1.06775 (17)	0.0525 (7)

	U11	U22	U33	U12	U13	U23
C1	0.043 (2)	0.048 (2)	0.043 (2)	−0.0032 (18)	0.0138 (16)	−0.0068 (18)
C2	0.047 (2)	0.057 (2)	0.0348 (19)	0.0045 (19)	0.0106 (16)	−0.0028 (18)
C3	0.042 (2)	0.078 (3)	0.049 (2)	−0.007 (2)	0.0090 (17)	−0.010 (2)
C4	0.053 (2)	0.070 (3)	0.062 (3)	−0.008 (2)	0.028 (2)	−0.011 (2)
C5	0.071 (3)	0.074 (3)	0.044 (2)	−0.001 (2)	0.024 (2)	0.001 (2)
C6	0.049 (2)	0.073 (3)	0.040 (2)	−0.005 (2)	0.0084 (17)	−0.002 (2)
C7	0.042 (2)	0.043 (2)	0.039 (2)	−0.0041 (17)	0.0112 (15)	0.0051 (16)
C8	0.048 (2)	0.062 (3)	0.046 (2)	0.002 (2)	0.0106 (17)	−0.004 (2)
C9	0.044 (2)	0.063 (3)	0.060 (3)	0.007 (2)	0.0137 (19)	0.004 (2)
C10	0.044 (2)	0.056 (3)	0.048 (2)	−0.003 (2)	−0.0007 (17)	0.0099 (19)
C11	0.059 (2)	0.067 (3)	0.038 (2)	−0.006 (2)	0.0081 (18)	−0.001 (2)
C12	0.048 (2)	0.054 (2)	0.041 (2)	−0.0005 (19)	0.0140 (16)	−0.0013 (18)
C13	0.045 (2)	0.055 (2)	0.0329 (18)	0.0044 (19)	0.0056 (16)	0.0002 (17)
C14	0.042 (2)	0.047 (2)	0.0327 (18)	0.0010 (17)	0.0072 (15)	−0.0008 (16)
C15	0.049 (2)	0.052 (2)	0.039 (2)	−0.0023 (19)	0.0113 (18)	−0.0016 (18)
C16	0.069 (3)	0.076 (3)	0.038 (2)	−0.006 (2)	0.0140 (19)	0.002 (2)
C17	0.075 (3)	0.084 (3)	0.057 (3)	−0.013 (3)	0.025 (2)	−0.001 (2)
Cl1	0.0572 (7)	0.1132 (11)	0.0671 (8)	0.0017 (7)	−0.0137 (5)	0.0169 (7)
F1	0.0541 (13)	0.0976 (19)	0.0380 (12)	−0.0022 (13)	0.0054 (10)	0.0107 (12)
F2	0.0689 (16)	0.119 (2)	0.0845 (18)	−0.0260 (16)	0.0462 (14)	−0.0119 (17)
O3	0.0592 (18)	0.086 (2)	0.0644 (19)	−0.0014 (17)	0.0134 (15)	−0.0021 (17)
O1	0.0509 (16)	0.099 (2)	0.0377 (15)	−0.0153 (16)	0.0018 (12)	0.0063 (15)
O2	0.0487 (15)	0.0678 (18)	0.0382 (13)	−0.0050 (14)	0.0123 (11)	0.0020 (13)

C1—C6	1.384 (5)	C10—C11	1.363 (5)
C1—C2	1.385 (5)	C10—Cl1	1.747 (4)
C1—O3	1.409 (4)	C11—C12	1.385 (5)
C2—F1	1.358 (4)	C11—H11	0.9300
C2—C3	1.365 (5)	C12—H12	0.9300
C3—C4	1.373 (6)	C13—C14	1.340 (5)
C3—H3	0.9300	C13—O3	1.356 (4)
C4—F2	1.357 (4)	C13—H13	0.9300
C4—C5	1.359 (5)	C14—C15	1.469 (5)
C5—C6	1.370 (5)	C15—O1	1.224 (4)
C5—H5	0.9300	C15—O2	1.331 (4)
C6—H6	0.9300	C16—O2	1.452 (4)
C7—C12	1.386 (5)	C16—C17	1.486 (5)
C7—C8	1.392 (5)	C16—H16A	0.9700
C7—C14	1.486 (4)	C16—H16B	0.9700
C8—C9	1.380 (5)	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C9—C10	1.368 (5)	C17—H17C	0.9600
C9—H9	0.9300
C6—C1—C2	116.5 (3)	C10—C11—C12	119.9 (4)
C6—C1—O3	125.9 (3)	C10—C11—H11	120.1
C2—C1—O3	117.6 (3)	C12—C11—H11	120.1
F1—C2—C3	118.6 (3)	C11—C12—C7	120.8 (4)
F1—C2—C1	117.2 (3)	C11—C12—H12	119.6
C3—C2—C1	124.1 (4)	C7—C12—H12	119.6
C2—C3—C4	116.6 (4)	C14—C13—O3	127.3 (3)
C2—C3—H3	121.7	C14—C13—H13	116.3
C4—C3—H3	121.7	O3—C13—H13	116.3
F2—C4—C5	119.7 (4)	C13—C14—C15	118.8 (3)
F2—C4—C3	118.2 (4)	C13—C14—C7	119.1 (3)
C5—C4—C3	122.1 (4)	C15—C14—C7	122.1 (3)
C4—C5—C6	119.8 (4)	O1—C15—O2	122.7 (3)
C4—C5—H5	120.1	O1—C15—C14	124.1 (4)
C6—C5—H5	120.1	O2—C15—C14	113.2 (3)
C5—C6—C1	120.9 (4)	O2—C16—C17	107.1 (3)
C5—C6—H6	119.6	O2—C16—H16A	110.3
C1—C6—H6	119.6	C17—C16—H16A	110.3
C12—C7—C8	117.8 (3)	O2—C16—H16B	110.3
C12—C7—C14	120.6 (3)	C17—C16—H16B	110.3
C8—C7—C14	121.4 (3)	H16A—C16—H16B	108.5
C9—C8—C7	121.1 (4)	C16—C17—H17A	109.5
C9—C8—H8	119.4	C16—C17—H17B	109.5
C7—C8—H8	119.4	H17A—C17—H17B	109.5
C10—C9—C8	119.6 (4)	C16—C17—H17C	109.5
C10—C9—H9	120.2	H17A—C17—H17C	109.5
C8—C9—H9	120.2	H17B—C17—H17C	109.5
C11—C10—C9	120.7 (3)	C13—O3—C1	124.9 (3)
C11—C10—Cl1	120.0 (3)	C15—O2—C16	116.4 (3)
C9—C10—Cl1	119.2 (3)
C6—C1—C2—F1	179.6 (3)	C10—C11—C12—C7	−0.7 (6)
O3—C1—C2—F1	−0.6 (5)	C8—C7—C12—C11	2.1 (6)
C6—C1—C2—C3	0.4 (6)	C14—C7—C12—C11	−173.4 (4)
O3—C1—C2—C3	−179.8 (4)	O3—C13—C14—C15	1.2 (6)
F1—C2—C3—C4	−179.2 (3)	O3—C13—C14—C7	−179.6 (3)
C1—C2—C3—C4	0.0 (6)	C12—C7—C14—C13	44.5 (5)
C2—C3—C4—F2	179.6 (4)	C8—C7—C14—C13	−130.9 (4)
C2—C3—C4—C5	0.1 (7)	C12—C7—C14—C15	−136.4 (4)
F2—C4—C5—C6	179.8 (4)	C8—C7—C14—C15	48.3 (5)
C3—C4—C5—C6	−0.7 (7)	C13—C14—C15—O1	3.5 (6)
C4—C5—C6—C1	1.1 (7)	C7—C14—C15—O1	−175.7 (4)
C2—C1—C6—C5	−1.0 (6)	C13—C14—C15—O2	−174.1 (3)
O3—C1—C6—C5	179.3 (4)	C7—C14—C15—O2	6.8 (5)
C12—C7—C8—C9	−1.6 (6)	C14—C13—O3—C1	−175.8 (4)
C14—C7—C8—C9	173.9 (4)	C6—C1—O3—C13	2.4 (6)
C7—C8—C9—C10	−0.2 (6)	C2—C1—O3—C13	−177.4 (4)
C8—C9—C10—C11	1.6 (6)	O1—C15—O2—C16	3.3 (6)
C8—C9—C10—Cl1	−178.1 (3)	C14—C15—O2—C16	−179.1 (3)
C9—C10—C11—C12	−1.2 (6)	C17—C16—O2—C15	179.9 (3)
Cl1—C10—C11—C12	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.51	3.321 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.51	3.321 (4)	146

Symmetry code: (i) .