(Z)-Ethyl 3-(4-chloro-benzamido)-2-cyano-3-(4-fluoro-phen-yl)acrylate.

The title compound, C(19)H(14)ClFN(2)O(3), was prepared by the reaction of ethyl (Z)-3-amino-2-cyano-3-(4-fluoro-phen-yl)acrylate and 4-chloro-benzoyl chloride. The dihedral angle between the chloro-benzene and fluoro-benzene rings is 66.18 (19)°. In addition to an intra-molecular N-H⋯O hydrogen bond, there are inter-molecular C-H⋯O and C-H⋯N hydrogen bonding inter-actions, which stabilize the crystal structure.

Related literature

For the agrochemical activity of the title compound, see: Heller et al. (2004 ▶); Ibers & Hamilton (1964 ▶).

Experimental

Crystal data

C19H14ClFN2O3

M = 372.77

Monoclinic,

a = 6.1429 (5) Å

b = 13.1555 (6) Å

c = 22.9263 (10) Å

β = 92.280 (4)°

V = 1851.27 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 298 (2) K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: none

23332 measured reflections

3259 independent reflections

2138 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.140

S = 1.07

3259 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041469/rz2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041469/rz2277Isup2.hkl

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

C19H14ClFN2O3	F(000) = 768
Mr = 372.77	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1253 reflections
a = 6.1429 (5) Å	θ = 3.1–20.3°
b = 13.1555 (6) Å	µ = 0.24 mm−1
c = 22.9263 (10) Å	T = 298 K
β = 92.280 (4)°	Block, colourless
V = 1851.27 (19) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 25.0°, θmin = 1.8°
phi and ω scans	h = −7→7
23332 measured reflections	k = −15→15
3259 independent reflections	l = −24→27

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0335P)2 + 1.3651P] where P = (Fo2 + 2Fc2)/3
3259 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.4513 (5)	0.4421 (2)	0.11848 (12)	0.0510 (7)
C2	0.4752 (5)	0.3939 (2)	0.17187 (14)	0.0613 (9)
H2	0.3761	0.4064	0.2006	0.074*
C3	0.6452 (6)	0.3273 (3)	0.18272 (14)	0.0670 (9)
H3	0.6599	0.2942	0.2185	0.080*
C4	0.7924 (5)	0.3099 (2)	0.14056 (15)	0.0626 (9)
C5	0.7716 (6)	0.3559 (3)	0.08732 (15)	0.0696 (9)
H5	0.8718	0.3431	0.0589	0.084*
C6	0.6006 (6)	0.4213 (2)	0.07632 (14)	0.0673 (9)
H6	0.5848	0.4523	0.0399	0.081*
C7	0.2778 (5)	0.5173 (2)	0.10220 (14)	0.0582 (8)
C8	−0.0191 (5)	0.6171 (2)	0.14507 (13)	0.0531 (8)
C9	−0.0435 (5)	0.6899 (2)	0.09582 (13)	0.0557 (8)
C10	−0.2251 (6)	0.6897 (3)	0.05965 (16)	0.0790 (11)
H10	−0.3308	0.6400	0.0642	0.095*
C11	−0.2547 (7)	0.7618 (3)	0.01659 (16)	0.0873 (12)
H11	−0.3779	0.7598	−0.0083	0.105*
C12	−0.1070 (8)	0.8340 (3)	0.01079 (16)	0.0870 (13)
C13	0.0819 (9)	0.8367 (3)	0.04453 (19)	0.1072 (16)
H13	0.1867	0.8863	0.0388	0.129*
C14	0.1124 (7)	0.7635 (3)	0.08740 (17)	0.0879 (12)
H14	0.2395	0.7638	0.1108	0.106*
C15	−0.1571 (5)	0.6200 (2)	0.18996 (13)	0.0539 (8)
C16	−0.3251 (6)	0.6945 (3)	0.18956 (14)	0.0667 (9)
C17	−0.1424 (5)	0.5506 (2)	0.24042 (13)	0.0561 (8)
C18	−0.3118 (6)	0.4975 (3)	0.32660 (15)	0.0742 (10)
H18A	−0.1840	0.5102	0.3518	0.089*
H18B	−0.3126	0.4264	0.3155	0.089*
C19	−0.5130 (7)	0.5229 (4)	0.35748 (17)	0.1065 (15)
H19A	−0.5114	0.5937	0.3677	0.160*
H19B	−0.5193	0.4826	0.3923	0.160*
H19C	−0.6383	0.5088	0.3324	0.160*
Cl1	1.00991 (17)	0.22922 (8)	0.15591 (5)	0.0969 (4)
F1	−0.1365 (6)	0.90693 (18)	−0.03083 (11)	0.1356 (11)
N1	0.1499 (4)	0.54859 (19)	0.14698 (10)	0.0595 (7)
H1	0.1799	0.5216	0.1805	0.071*
N2	−0.4597 (6)	0.7536 (3)	0.19023 (14)	0.0981 (12)
O1	0.2500 (5)	0.5501 (2)	0.05344 (10)	0.0940 (9)
O2	0.0048 (4)	0.49015 (17)	0.24988 (10)	0.0701 (6)
O3	−0.3085 (4)	0.56200 (16)	0.27479 (9)	0.0628 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0583 (19)	0.0492 (16)	0.0460 (17)	−0.0001 (14)	0.0068 (15)	0.0007 (14)
C2	0.065 (2)	0.064 (2)	0.056 (2)	0.0058 (17)	0.0166 (17)	0.0054 (16)
C3	0.076 (2)	0.070 (2)	0.055 (2)	0.0070 (19)	0.0057 (18)	0.0142 (17)
C4	0.066 (2)	0.0532 (18)	0.069 (2)	0.0047 (16)	0.0076 (18)	0.0025 (16)
C5	0.077 (2)	0.073 (2)	0.061 (2)	0.0152 (19)	0.0198 (18)	0.0022 (18)
C6	0.085 (3)	0.066 (2)	0.0522 (19)	0.0133 (19)	0.0115 (18)	0.0070 (16)
C7	0.069 (2)	0.0603 (19)	0.0460 (19)	0.0017 (16)	0.0124 (16)	0.0019 (15)
C8	0.060 (2)	0.0509 (17)	0.0482 (18)	0.0018 (15)	−0.0006 (15)	−0.0051 (14)
C9	0.064 (2)	0.0523 (18)	0.0514 (18)	0.0036 (16)	0.0030 (16)	−0.0038 (15)
C10	0.083 (3)	0.086 (3)	0.067 (2)	−0.013 (2)	−0.011 (2)	0.013 (2)
C11	0.093 (3)	0.099 (3)	0.067 (2)	0.003 (3)	−0.025 (2)	0.008 (2)
C12	0.137 (4)	0.056 (2)	0.066 (2)	0.008 (2)	−0.021 (3)	0.0120 (19)
C13	0.150 (4)	0.066 (2)	0.102 (3)	−0.032 (3)	−0.038 (3)	0.026 (2)
C14	0.109 (3)	0.069 (2)	0.083 (3)	−0.014 (2)	−0.032 (2)	0.012 (2)
C15	0.060 (2)	0.0543 (17)	0.0471 (18)	0.0084 (15)	0.0011 (15)	−0.0003 (14)
C16	0.073 (2)	0.077 (2)	0.050 (2)	0.019 (2)	0.0033 (17)	0.0008 (17)
C17	0.057 (2)	0.0577 (19)	0.0537 (19)	0.0008 (16)	0.0027 (16)	−0.0077 (16)
C18	0.086 (3)	0.076 (2)	0.060 (2)	−0.013 (2)	0.0093 (19)	0.0138 (18)
C19	0.095 (3)	0.155 (4)	0.072 (3)	0.002 (3)	0.028 (2)	0.021 (3)
Cl1	0.0849 (7)	0.0965 (7)	0.1095 (8)	0.0329 (6)	0.0085 (6)	0.0214 (6)
F1	0.226 (3)	0.0791 (16)	0.0970 (18)	0.0063 (18)	−0.0458 (19)	0.0293 (14)
N1	0.0694 (18)	0.0653 (16)	0.0443 (14)	0.0139 (14)	0.0072 (13)	0.0055 (12)
N2	0.105 (3)	0.122 (3)	0.068 (2)	0.053 (2)	0.0133 (19)	0.0078 (19)
O1	0.110 (2)	0.119 (2)	0.0542 (15)	0.0513 (17)	0.0204 (14)	0.0236 (15)
O2	0.0746 (16)	0.0726 (14)	0.0636 (14)	0.0142 (13)	0.0100 (12)	0.0111 (12)
O3	0.0666 (14)	0.0682 (13)	0.0543 (13)	0.0006 (11)	0.0105 (11)	0.0010 (11)

C1—C2	1.381 (4)	C11—C12	1.324 (5)
C1—C6	1.386 (4)	C11—H11	0.9300
C1—C7	1.491 (4)	C12—F1	1.361 (4)
C2—C3	1.378 (4)	C12—C13	1.369 (6)
C2—H2	0.9300	C13—C14	1.383 (5)
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.364 (4)	C15—C16	1.423 (5)
C4—Cl1	1.732 (3)	C15—C17	1.473 (4)
C5—C6	1.374 (4)	C16—N2	1.135 (4)
C5—H5	0.9300	C17—O2	1.217 (4)
C6—H6	0.9300	C17—O3	1.322 (4)
C7—O1	1.204 (4)	C18—O3	1.461 (4)
C7—N1	1.380 (4)	C18—C19	1.487 (5)
C8—C15	1.360 (4)	C18—H18A	0.9700
C8—N1	1.374 (4)	C18—H18B	0.9700
C8—C9	1.484 (4)	C19—H19A	0.9600
C9—C10	1.363 (4)	C19—H19B	0.9600
C9—C14	1.381 (5)	C19—H19C	0.9600
C10—C11	1.376 (5)	N1—H1	0.8600
C10—H10	0.9300
C2—C1—C6	118.5 (3)	C11—C12—F1	120.2 (4)
C2—C1—C7	125.2 (3)	C11—C12—C13	122.1 (4)
C6—C1—C7	116.3 (3)	F1—C12—C13	117.7 (4)
C3—C2—C1	120.4 (3)	C12—C13—C14	118.1 (4)
C3—C2—H2	119.8	C12—C13—H13	121.0
C1—C2—H2	119.8	C14—C13—H13	121.0
C4—C3—C2	119.7 (3)	C9—C14—C13	120.8 (4)
C4—C3—H3	120.2	C9—C14—H14	119.6
C2—C3—H3	120.2	C13—C14—H14	119.6
C5—C4—C3	121.2 (3)	C8—C15—C16	119.2 (3)
C5—C4—Cl1	119.9 (3)	C8—C15—C17	123.8 (3)
C3—C4—Cl1	119.0 (3)	C16—C15—C17	117.0 (3)
C4—C5—C6	119.1 (3)	N2—C16—C15	178.8 (4)
C4—C5—H5	120.5	O2—C17—O3	123.6 (3)
C6—C5—H5	120.5	O2—C17—C15	124.5 (3)
C5—C6—C1	121.2 (3)	O3—C17—C15	111.9 (3)
C5—C6—H6	119.4	O3—C18—C19	107.2 (3)
C1—C6—H6	119.4	O3—C18—H18A	110.3
O1—C7—N1	121.3 (3)	C19—C18—H18A	110.3
O1—C7—C1	122.9 (3)	O3—C18—H18B	110.3
N1—C7—C1	115.7 (3)	C19—C18—H18B	110.3
C15—C8—N1	119.2 (3)	H18A—C18—H18B	108.5
C15—C8—C9	120.7 (3)	C18—C19—H19A	109.5
N1—C8—C9	120.1 (3)	C18—C19—H19B	109.5
C10—C9—C14	118.1 (3)	H19A—C19—H19B	109.5
C10—C9—C8	121.1 (3)	C18—C19—H19C	109.5
C14—C9—C8	120.6 (3)	H19A—C19—H19C	109.5
C9—C10—C11	121.1 (4)	H19B—C19—H19C	109.5
C9—C10—H10	119.4	C8—N1—C7	128.6 (3)
C11—C10—H10	119.4	C8—N1—H1	115.7
C12—C11—C10	119.7 (4)	C7—N1—H1	115.7
C12—C11—H11	120.2	C17—O3—C18	117.1 (3)
C10—C11—H11	120.2
C6—C1—C2—C3	0.5 (5)	C10—C11—C12—C13	3.4 (7)
C7—C1—C2—C3	−178.5 (3)	C11—C12—C13—C14	−2.7 (7)
C1—C2—C3—C4	0.8 (5)	F1—C12—C13—C14	179.3 (4)
C2—C3—C4—C5	−1.3 (5)	C10—C9—C14—C13	1.9 (6)
C2—C3—C4—Cl1	177.9 (3)	C8—C9—C14—C13	−174.7 (4)
C3—C4—C5—C6	0.6 (5)	C12—C13—C14—C9	0.0 (7)
Cl1—C4—C5—C6	−178.6 (3)	N1—C8—C15—C16	176.6 (3)
C4—C5—C6—C1	0.7 (5)	C9—C8—C15—C16	−0.5 (5)
C2—C1—C6—C5	−1.3 (5)	N1—C8—C15—C17	−2.5 (5)
C7—C1—C6—C5	177.8 (3)	C9—C8—C15—C17	−179.7 (3)
C2—C1—C7—O1	−172.5 (3)	C8—C15—C17—O2	7.0 (5)
C6—C1—C7—O1	8.5 (5)	C16—C15—C17—O2	−172.2 (3)
C2—C1—C7—N1	8.1 (5)	C8—C15—C17—O3	−173.4 (3)
C6—C1—C7—N1	−170.9 (3)	C16—C15—C17—O3	7.4 (4)
C15—C8—C9—C10	−64.0 (4)	C15—C8—N1—C7	164.6 (3)
N1—C8—C9—C10	118.9 (4)	C9—C8—N1—C7	−18.2 (5)
C15—C8—C9—C14	112.5 (4)	O1—C7—N1—C8	0.0 (5)
N1—C8—C9—C14	−64.7 (4)	C1—C7—N1—C8	179.4 (3)
C14—C9—C10—C11	−1.2 (6)	O2—C17—O3—C18	−0.1 (4)
C8—C9—C10—C11	175.4 (3)	C15—C17—O3—C18	−179.7 (3)
C9—C10—C11—C12	−1.4 (6)	C19—C18—O3—C17	−179.3 (3)
C10—C11—C12—F1	−178.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.00	2.668 (3)	134
C3—H3···N2i	0.93	2.53	3.314 (5)	143
C6—H6···O1ii	0.93	2.41	3.170 (4)	140
C14—H14···N2iii	0.93	2.55	3.463 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.00	2.668 (3)	134
C3—H3⋯N2i	0.93	2.53	3.314 (5)	143
C6—H6⋯O1ii	0.93	2.41	3.170 (4)	140
C14—H14⋯N2iii	0.93	2.55	3.463 (5)	169

Symmetry codes: (i) ; (ii) ; (iii) .