(Z)-Ethyl 2-(4-chloro-phen-yl)-3-[(2,4-difluoro-phen-yl)amino]-prop-2-enoate.

In the title compound, C(17)H(14)ClF(2)NO(2), the amino-acrylo-yloxy group makes dihedral angles of 47.55 (11)° with the 4-chloro-phenyl group and 8.74 (12)° with the difluoro-phenyl group; the dihedral angle between the rings is 52.32 (11)°. The structure of the title compound reveals a Z configuration with respect to the C=C double bond in the amino-acrylate fragment. A bifurcated intramolecular N-H⋯(O,F) hydrogen bond occurs. In the crystal, molecules are linked into chains by C-H⋯O hydrogen bonds.

Related literature

For background to Schiff bases, see: You & Zhu, 2006 ▶. For applications of enamines, see: Xiao et al. (2007 ▶, 2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C17H14ClF2NO2

M = 337.74

Monoclinic,

a = 16.276 (3) Å

b = 7.5030 (15) Å

c = 13.812 (3) Å

β = 111.11 (3)°

V = 1573.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.923, T max = 0.973

2957 measured reflections

2824 independent reflections

1566 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.170

S = 0.99

2824 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043801/bq2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043801/bq2244Isup2.hkl

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

C17H14ClF2NO2	F(000) = 696
Mr = 337.74	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1318 reflections
a = 16.276 (3) Å	θ = 1.8–24.7°
b = 7.5030 (15) Å	µ = 0.27 mm−1
c = 13.812 (3) Å	T = 298 K
β = 111.11 (3)°	Block, colourless
V = 1573.5 (5) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2824 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.3°, θmin = 1.3°
Absorption correction: ψ scan (North et al., 1968)	h = −19→18
Tmin = 0.923, Tmax = 0.973	k = −9→0
2957 measured reflections	l = 0→16

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) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0804P)2] where P = (Fo2 + 2Fc2)/3
2824 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 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	1.0185 (2)	0.7793 (5)	0.9700 (2)	0.0447 (9)
C2	1.1023 (2)	0.7723 (5)	1.0451 (2)	0.0473 (9)
C3	1.1764 (2)	0.8338 (5)	1.0316 (3)	0.0575 (10)
H3	1.2316	0.8267	1.0841	0.069*
C4	1.1653 (2)	0.9062 (6)	0.9370 (3)	0.0591 (10)
C5	1.0852 (3)	0.9180 (5)	0.8598 (3)	0.0614 (11)
H5	1.0799	0.9696	0.7966	0.074*
C6	1.0122 (2)	0.8536 (5)	0.8756 (3)	0.0561 (10)
H6	0.9575	0.8598	0.8222	0.067*
C7	0.7054 (2)	0.6470 (5)	0.8669 (2)	0.0418 (8)
C8	0.6325 (2)	0.7235 (5)	0.8805 (3)	0.0534 (10)
H8	0.6377	0.7669	0.9456	0.064*
C9	0.5528 (2)	0.7365 (5)	0.7997 (3)	0.0568 (10)
H9	0.5046	0.7872	0.8103	0.068*
C10	0.5451 (2)	0.6741 (5)	0.7036 (3)	0.0538 (10)
C11	0.6148 (2)	0.5949 (5)	0.6881 (3)	0.0567 (10)
H11	0.6087	0.5507	0.6229	0.068*
C12	0.6946 (2)	0.5807 (5)	0.7697 (2)	0.0474 (9)
H12	0.7418	0.5255	0.7590	0.057*
C13	0.8638 (2)	0.7024 (5)	0.9292 (2)	0.0463 (9)
H13	0.8524	0.7370	0.8610	0.056*
C14	0.7936 (2)	0.6482 (5)	0.9515 (2)	0.0423 (8)
C15	0.8066 (2)	0.5946 (5)	1.0578 (2)	0.0480 (9)
C16	0.7412 (2)	0.4743 (6)	1.1713 (2)	0.0622 (11)
H16A	0.7579	0.5751	1.2184	0.075*
H16B	0.7856	0.3821	1.1972	0.075*
C17	0.6536 (2)	0.4057 (6)	1.1638 (3)	0.0708 (12)
H17A	0.6094	0.4936	1.1312	0.106*
H17B	0.6540	0.3807	1.2321	0.106*
H17C	0.6408	0.2985	1.1231	0.106*
Cl1	0.44479 (7)	0.69755 (18)	0.60035 (8)	0.0887 (5)
F1	1.10991 (12)	0.7013 (3)	1.13887 (14)	0.0654 (7)
F2	1.23767 (15)	0.9700 (4)	0.92091 (18)	0.0856 (8)
N1	0.94818 (18)	0.7123 (4)	0.9939 (2)	0.0483 (8)
O1	0.87698 (16)	0.6036 (4)	1.13063 (17)	0.0660 (8)
O2	0.73408 (15)	0.5283 (3)	1.06790 (16)	0.0521 (7)
H18	0.961 (2)	0.673 (4)	1.054 (3)	0.050 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0458 (19)	0.047 (2)	0.0377 (18)	0.0000 (17)	0.0109 (15)	−0.0070 (17)
C2	0.047 (2)	0.056 (2)	0.0355 (18)	0.0045 (18)	0.0104 (15)	−0.0033 (17)
C3	0.041 (2)	0.077 (3)	0.049 (2)	−0.006 (2)	0.0093 (16)	−0.010 (2)
C4	0.052 (2)	0.070 (3)	0.062 (2)	−0.007 (2)	0.028 (2)	−0.011 (2)
C5	0.070 (3)	0.073 (3)	0.044 (2)	−0.002 (2)	0.024 (2)	0.001 (2)
C6	0.049 (2)	0.073 (3)	0.0389 (19)	−0.004 (2)	0.0072 (16)	−0.0010 (19)
C7	0.0405 (18)	0.043 (2)	0.0397 (18)	−0.0037 (16)	0.0115 (14)	0.0044 (16)
C8	0.047 (2)	0.063 (2)	0.045 (2)	0.0019 (19)	0.0100 (16)	−0.0049 (19)
C9	0.043 (2)	0.062 (3)	0.061 (2)	0.0066 (19)	0.0144 (18)	0.005 (2)
C10	0.045 (2)	0.055 (2)	0.046 (2)	−0.0034 (19)	−0.0015 (16)	0.0091 (18)
C11	0.058 (2)	0.065 (3)	0.0392 (19)	−0.005 (2)	0.0082 (17)	−0.0021 (19)
C12	0.0463 (19)	0.054 (2)	0.0399 (18)	0.0003 (18)	0.0130 (15)	−0.0008 (17)
C13	0.047 (2)	0.053 (2)	0.0334 (17)	0.0049 (18)	0.0082 (15)	0.0008 (16)
C14	0.0426 (19)	0.048 (2)	0.0317 (17)	0.0011 (17)	0.0079 (14)	−0.0009 (15)
C15	0.047 (2)	0.052 (2)	0.0404 (19)	−0.0026 (18)	0.0103 (16)	−0.0019 (17)
C16	0.069 (3)	0.077 (3)	0.0365 (19)	−0.007 (2)	0.0138 (18)	0.001 (2)
C17	0.075 (3)	0.081 (3)	0.058 (2)	−0.013 (3)	0.026 (2)	0.000 (2)
Cl1	0.0566 (7)	0.1127 (10)	0.0672 (7)	0.0014 (7)	−0.0135 (5)	0.0174 (7)
F1	0.0531 (12)	0.0978 (18)	0.0363 (11)	−0.0016 (12)	0.0051 (9)	0.0110 (12)
F2	0.0689 (15)	0.119 (2)	0.0838 (17)	−0.0253 (15)	0.0458 (13)	−0.0121 (16)
N1	0.0402 (17)	0.063 (2)	0.0353 (16)	−0.0006 (15)	0.0063 (13)	0.0050 (16)
O1	0.0500 (15)	0.099 (2)	0.0373 (14)	−0.0152 (15)	0.0018 (12)	0.0058 (14)
O2	0.0481 (14)	0.0676 (17)	0.0374 (12)	−0.0045 (13)	0.0116 (10)	0.0026 (12)

C1—C2	1.385 (4)	C10—C11	1.364 (5)
C1—C6	1.387 (5)	C10—Cl1	1.747 (3)
C1—N1	1.394 (4)	C11—C12	1.384 (5)
C2—F1	1.365 (4)	C11—H11	0.9300
C2—C3	1.365 (5)	C12—H12	0.9300
C3—C4	1.366 (5)	C13—N1	1.344 (4)
C3—H3	0.9300	C13—C14	1.348 (5)
C4—C5	1.357 (5)	C13—H13	0.9300
C4—F2	1.362 (4)	C14—C15	1.463 (4)
C5—C6	1.371 (5)	C15—O1	1.225 (4)
C5—H5	0.9300	C15—O2	1.333 (4)
C6—H6	0.9300	C16—O2	1.449 (4)
C7—C12	1.383 (4)	C16—C17	1.484 (5)
C7—C8	1.390 (5)	C16—H16A	0.9700
C7—C14	1.489 (4)	C16—H16B	0.9700
C8—C9	1.377 (4)	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C9—C10	1.370 (5)	C17—H17C	0.9600
C9—H9	0.9300	N1—H18	0.83 (3)
C2—C1—C6	116.0 (3)	C10—C11—H11	120.2
C2—C1—N1	118.7 (3)	C12—C11—H11	120.2
C6—C1—N1	125.3 (3)	C7—C12—C11	121.1 (3)
F1—C2—C3	118.6 (3)	C7—C12—H12	119.4
F1—C2—C1	117.0 (3)	C11—C12—H12	119.4
C3—C2—C1	124.4 (3)	N1—C13—C14	127.8 (3)
C2—C3—C4	116.4 (3)	N1—C13—H13	116.1
C2—C3—H3	121.8	C14—C13—H13	116.1
C4—C3—H3	121.8	C13—C14—C15	119.0 (3)
C5—C4—F2	119.4 (4)	C13—C14—C7	118.7 (3)
C5—C4—C3	122.5 (4)	C15—C14—C7	122.4 (3)
F2—C4—C3	118.1 (4)	O1—C15—O2	122.4 (3)
C4—C5—C6	119.6 (4)	O1—C15—C14	124.3 (3)
C4—C5—H5	120.2	O2—C15—C14	113.2 (3)
C6—C5—H5	120.2	O2—C16—C17	107.1 (3)
C5—C6—C1	121.1 (3)	O2—C16—H16A	110.3
C5—C6—H6	119.5	C17—C16—H16A	110.3
C1—C6—H6	119.5	O2—C16—H16B	110.3
C12—C7—C8	117.7 (3)	C17—C16—H16B	110.3
C12—C7—C14	120.8 (3)	H16A—C16—H16B	108.6
C8—C7—C14	121.3 (3)	C16—C17—H17A	109.5
C9—C8—C7	121.3 (3)	C16—C17—H17B	109.5
C9—C8—H8	119.3	H17A—C17—H17B	109.5
C7—C8—H8	119.3	C16—C17—H17C	109.5
C10—C9—C8	119.5 (4)	H17A—C17—H17C	109.5
C10—C9—H9	120.3	H17B—C17—H17C	109.5
C8—C9—H9	120.3	C13—N1—C1	126.4 (3)
C11—C10—C9	120.7 (3)	C13—N1—H18	118 (2)
C11—C10—Cl1	120.1 (3)	C1—N1—H18	116 (2)
C9—C10—Cl1	119.3 (3)	C15—O2—C16	116.6 (3)
C10—C11—C12	119.7 (3)
C6—C1—C2—F1	179.4 (3)	C8—C7—C12—C11	1.9 (5)
N1—C1—C2—F1	−0.8 (5)	C14—C7—C12—C11	−173.6 (3)
C6—C1—C2—C3	0.4 (6)	C10—C11—C12—C7	−0.6 (6)
N1—C1—C2—C3	−179.8 (4)	N1—C13—C14—C15	1.0 (6)
F1—C2—C3—C4	−179.0 (3)	N1—C13—C14—C7	−179.7 (3)
C1—C2—C3—C4	−0.1 (6)	C12—C7—C14—C13	44.5 (5)
C2—C3—C4—C5	0.3 (6)	C8—C7—C14—C13	−130.9 (4)
C2—C3—C4—F2	179.6 (3)	C12—C7—C14—C15	−136.2 (3)
F2—C4—C5—C6	179.8 (4)	C8—C7—C14—C15	48.4 (5)
C3—C4—C5—C6	−0.9 (6)	C13—C14—C15—O1	3.8 (6)
C4—C5—C6—C1	1.2 (6)	C7—C14—C15—O1	−175.5 (4)
C2—C1—C6—C5	−1.0 (5)	C13—C14—C15—O2	−174.1 (3)
N1—C1—C6—C5	179.2 (4)	C7—C14—C15—O2	6.5 (5)
C12—C7—C8—C9	−1.3 (6)	C14—C13—N1—C1	−175.8 (4)
C14—C7—C8—C9	174.2 (3)	C2—C1—N1—C13	−177.2 (3)
C7—C8—C9—C10	−0.5 (6)	C6—C1—N1—C13	2.6 (6)
C8—C9—C10—C11	1.9 (6)	O1—C15—O2—C16	2.9 (5)
C8—C9—C10—Cl1	−177.9 (3)	C14—C15—O2—C16	−179.2 (3)
C9—C10—C11—C12	−1.3 (6)	C17—C16—O2—C15	180.0 (3)
Cl1—C10—C11—C12	178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H18···F1	0.83 (3)	2.29 (3)	2.674 (3)	108 (3)
N1—H18···O1	0.83 (3)	2.07 (3)	2.675 (4)	129 (3)
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
N1—H18⋯F1	0.83 (3)	2.29 (3)	2.674 (3)	108 (3)
N1—H18⋯O1	0.83 (3)	2.07 (3)	2.675 (4)	129 (3)
C6—H6⋯O1i	0.93	2.51	3.321 (4)	146

Symmetry code: (i) .