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

The title compound, C(18)H(17)F(2)NO(3), consists of three individually planar subunits, namely two benzene rings and one amino-acrylate group. The amino-acrylate group forms dihedral angles of 5.92 (7) and 50.21 (6)° with the difluoro and methoxy benzene rings, respectively. The dihedral angle between the two benzene rings is 55.25 (7)°. The mol-ecules exhibit intra-molecular N-H⋯O and N-H⋯F inter-actions and form a three-dimensional network via inter-molecular C-H⋯O and C-H⋯π hydrogen bonds.

Related literature

For general background, see: Xiao, Fang et al. (2008 ▶); Xiao, Li et al. (2008 ▶); Xiao, Xue et al. (2007 ▶). For related structures, see: Xiao, Li, Shi et al. (2008 ▶); Xiao, Lv et al. (2008 ▶); Xiao, Fang et al. (2007 ▶).

Experimental

Crystal data

C18H17F2NO3

M = 333.33

Monoclinic,

a = 17.295 (4) Å

b = 7.2940 (15) Å

c = 14.233 (3) Å

β = 113.73 (3)°

V = 1643.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.989

3108 measured reflections

2974 independent reflections

1889 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.156

S = 1.02

2974 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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/S1600536808036982/bq2102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036982/bq2102Isup2.hkl

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

C18H17F2NO3	F000 = 696
Mr = 333.33	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1729 reflections
a = 17.295 (4) Å	θ = 1.4–24.7º
b = 7.2940 (15) Å	µ = 0.11 mm−1
c = 14.233 (3) Å	T = 298 (2) K
β = 113.73 (3)º	Block, colorless
V = 1643.7 (7) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2974 independent reflections
Radiation source: fine-focus sealed tube	1889 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 298(2) K	θmax = 25.3º
ω/2θ scans	θmin = 1.3º
Absorption correction: ψ scan(North et al., 1968)	h = −20→19
Tmin = 0.969, Tmax = 0.989	k = −8→0
3108 measured reflections	l = 0→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.084P)2 + 0.0301P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156	(Δ/σ)max = 0.003
S = 1.02	Δρmax = 0.20 e Å−3
2974 reflections	Δρmin = −0.18 e Å−3
224 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (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	−0.01149 (13)	0.2255 (3)	0.45020 (18)	0.0442 (6)
C2	−0.09169 (14)	0.2175 (4)	0.44819 (18)	0.0482 (6)
C3	−0.16098 (15)	0.1544 (4)	0.3666 (2)	0.0577 (7)
H3	−0.2143	0.1519	0.3680	0.069*
C4	−0.14800 (15)	0.0951 (4)	0.28276 (19)	0.0569 (7)
C5	−0.07067 (16)	0.0977 (4)	0.27953 (19)	0.0601 (7)
H5	−0.0638	0.0562	0.2216	0.072*
C6	−0.00210 (15)	0.1628 (4)	0.36312 (18)	0.0536 (7)
H6	0.0510	0.1647	0.3611	0.064*
C7	0.28914 (13)	0.3614 (3)	0.64133 (17)	0.0420 (6)
C8	0.35651 (13)	0.2735 (3)	0.71676 (17)	0.0461 (6)
H8	0.3477	0.2142	0.7695	0.055*
C9	0.43614 (14)	0.2706 (4)	0.71668 (18)	0.0492 (6)
H9	0.4801	0.2104	0.7686	0.059*
C10	0.45026 (14)	0.3584 (3)	0.63826 (18)	0.0450 (6)
C11	0.38407 (14)	0.4464 (4)	0.56174 (19)	0.0501 (7)
H11	0.3928	0.5042	0.5086	0.060*
C12	0.30493 (14)	0.4487 (3)	0.56390 (17)	0.0472 (6)
H12	0.2612	0.5101	0.5124	0.057*
C13	0.13613 (13)	0.3038 (3)	0.55292 (18)	0.0454 (6)
H13	0.1487	0.2745	0.4970	0.055*
C14	0.20243 (14)	0.3552 (3)	0.64003 (17)	0.0438 (6)
C15	0.18698 (15)	0.4010 (3)	0.73038 (19)	0.0486 (6)
C16	0.24764 (19)	0.4999 (5)	0.9037 (2)	0.0767 (9)
H16A	0.2256	0.3925	0.9249	0.092*
H16B	0.2088	0.6007	0.8948	0.092*
C17	0.3318 (2)	0.5471 (5)	0.9828 (2)	0.0838 (10)
H17A	0.3708	0.4499	0.9881	0.126*
H17B	0.3280	0.5633	1.0477	0.126*
H17C	0.3513	0.6587	0.9639	0.126*
C18	0.59583 (14)	0.2750 (4)	0.7079 (2)	0.0709 (9)
H18A	0.6026	0.3184	0.7745	0.106*
H18B	0.6464	0.2995	0.6975	0.106*
H18C	0.5854	0.1453	0.7036	0.106*
F1	−0.10159 (8)	0.2760 (2)	0.53363 (11)	0.0670 (5)
F2	−0.21570 (10)	0.0299 (3)	0.20048 (12)	0.0843 (6)
H1	0.0432 (15)	0.311 (4)	0.5919 (19)	0.059 (8)*
N1	0.05458 (11)	0.2904 (3)	0.53817 (16)	0.0500 (6)
O1	0.11846 (11)	0.3870 (3)	0.73643 (13)	0.0660 (6)
O2	0.25571 (10)	0.4636 (3)	0.80903 (12)	0.0558 (5)
O3	0.52661 (9)	0.3660 (3)	0.63138 (13)	0.0598 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0416 (12)	0.0463 (15)	0.0459 (14)	0.0017 (11)	0.0188 (11)	0.0039 (12)
C2	0.0461 (14)	0.0581 (16)	0.0457 (14)	0.0045 (12)	0.0240 (12)	0.0035 (12)
C3	0.0407 (13)	0.0704 (19)	0.0578 (17)	−0.0009 (13)	0.0153 (12)	0.0069 (15)
C4	0.0483 (15)	0.0653 (18)	0.0465 (15)	−0.0029 (13)	0.0080 (12)	0.0009 (13)
C5	0.0618 (17)	0.0738 (19)	0.0476 (15)	0.0055 (15)	0.0249 (13)	−0.0054 (14)
C6	0.0467 (14)	0.0683 (18)	0.0505 (15)	−0.0002 (13)	0.0244 (12)	−0.0037 (14)
C7	0.0416 (13)	0.0416 (14)	0.0442 (13)	−0.0025 (11)	0.0185 (11)	−0.0061 (11)
C8	0.0469 (13)	0.0485 (15)	0.0463 (14)	0.0036 (12)	0.0223 (11)	0.0040 (12)
C9	0.0444 (13)	0.0539 (16)	0.0461 (14)	0.0096 (12)	0.0148 (11)	0.0048 (12)
C10	0.0402 (12)	0.0484 (15)	0.0486 (14)	0.0006 (11)	0.0203 (11)	−0.0049 (12)
C11	0.0473 (14)	0.0597 (17)	0.0478 (14)	0.0012 (12)	0.0236 (12)	0.0077 (13)
C12	0.0416 (13)	0.0531 (16)	0.0449 (14)	0.0037 (12)	0.0155 (11)	0.0054 (12)
C13	0.0429 (13)	0.0489 (15)	0.0497 (14)	0.0010 (11)	0.0240 (11)	−0.0006 (12)
C14	0.0438 (13)	0.0450 (15)	0.0469 (14)	−0.0007 (11)	0.0228 (11)	0.0010 (12)
C15	0.0491 (14)	0.0476 (15)	0.0536 (15)	−0.0027 (12)	0.0253 (13)	0.0020 (12)
C16	0.087 (2)	0.107 (3)	0.0471 (16)	−0.0039 (19)	0.0380 (16)	−0.0040 (17)
C17	0.107 (3)	0.089 (3)	0.0507 (17)	−0.012 (2)	0.0272 (18)	−0.0072 (17)
C18	0.0430 (14)	0.087 (2)	0.078 (2)	0.0110 (15)	0.0204 (14)	0.0032 (18)
F1	0.0506 (8)	0.1011 (13)	0.0573 (9)	0.0033 (8)	0.0300 (7)	−0.0085 (9)
F2	0.0611 (10)	0.1115 (15)	0.0617 (10)	−0.0110 (10)	0.0054 (8)	−0.0135 (10)
N1	0.0404 (11)	0.0651 (15)	0.0487 (13)	−0.0016 (10)	0.0222 (10)	−0.0053 (11)
O1	0.0548 (11)	0.0921 (15)	0.0633 (12)	−0.0091 (10)	0.0366 (9)	−0.0091 (11)
O2	0.0578 (11)	0.0708 (13)	0.0449 (10)	−0.0087 (9)	0.0271 (8)	−0.0088 (9)
O3	0.0412 (9)	0.0763 (13)	0.0671 (12)	0.0043 (9)	0.0274 (9)	0.0062 (10)

C1—C2	1.377 (3)	C11—C12	1.382 (3)
C1—C6	1.390 (3)	C11—H11	0.9300
C1—N1	1.395 (3)	C12—H12	0.9300
C2—F1	1.363 (3)	C13—N1	1.343 (3)
C2—C3	1.370 (3)	C13—C14	1.360 (3)
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.454 (3)
C4—C5	1.357 (3)	C15—O1	1.226 (3)
C4—F2	1.365 (3)	C15—O2	1.343 (3)
C5—C6	1.383 (3)	C16—O2	1.435 (3)
C5—H5	0.9300	C16—C17	1.479 (4)
C6—H6	0.9300	C16—H16A	0.9700
C7—C8	1.384 (3)	C16—H16B	0.9700
C7—C12	1.392 (3)	C17—H17A	0.9600
C7—C14	1.493 (3)	C17—H17B	0.9600
C8—C9	1.378 (3)	C17—H17C	0.9600
C8—H8	0.9300	C18—O3	1.418 (3)
C9—C10	1.391 (3)	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—O3	1.364 (3)	C18—H18C	0.9600
C10—C11	1.380 (3)	N1—H1	0.88 (2)
C2—C1—C6	116.5 (2)	C11—C12—H12	119.2
C2—C1—N1	119.2 (2)	C7—C12—H12	119.2
C6—C1—N1	124.4 (2)	N1—C13—C14	127.6 (2)
F1—C2—C3	118.7 (2)	N1—C13—H13	116.2
F1—C2—C1	117.1 (2)	C14—C13—H13	116.2
C3—C2—C1	124.2 (2)	C13—C14—C15	118.8 (2)
C4—C3—C2	116.8 (2)	C13—C14—C7	119.6 (2)
C4—C3—H3	121.6	C15—C14—C7	121.6 (2)
C2—C3—H3	121.6	O1—C15—O2	121.7 (2)
C5—C4—F2	119.5 (2)	O1—C15—C14	124.7 (2)
C5—C4—C3	122.3 (2)	O2—C15—C14	113.5 (2)
F2—C4—C3	118.2 (2)	O2—C16—C17	108.6 (2)
C4—C5—C6	119.4 (2)	O2—C16—H16A	110.0
C4—C5—H5	120.3	C17—C16—H16A	110.0
C6—C5—H5	120.3	O2—C16—H16B	110.0
C5—C6—C1	120.8 (2)	C17—C16—H16B	110.0
C5—C6—H6	119.6	H16A—C16—H16B	108.3
C1—C6—H6	119.6	C16—C17—H17A	109.5
C8—C7—C12	117.0 (2)	C16—C17—H17B	109.5
C8—C7—C14	121.6 (2)	H17A—C17—H17B	109.5
C12—C7—C14	121.3 (2)	C16—C17—H17C	109.5
C9—C8—C7	122.4 (2)	H17A—C17—H17C	109.5
C9—C8—H8	118.8	H17B—C17—H17C	109.5
C7—C8—H8	118.8	O3—C18—H18A	109.5
C8—C9—C10	119.5 (2)	O3—C18—H18B	109.5
C8—C9—H9	120.3	H18A—C18—H18B	109.5
C10—C9—H9	120.3	O3—C18—H18C	109.5
O3—C10—C11	116.4 (2)	H18A—C18—H18C	109.5
O3—C10—C9	124.3 (2)	H18B—C18—H18C	109.5
C11—C10—C9	119.3 (2)	C13—N1—C1	126.5 (2)
C10—C11—C12	120.2 (2)	C13—N1—H1	116.2 (16)
C10—C11—H11	119.9	C1—N1—H1	116.8 (16)
C12—C11—H11	119.9	C15—O2—C16	117.2 (2)
C11—C12—C7	121.6 (2)	C10—O3—C18	117.9 (2)
C6—C1—C2—F1	179.1 (2)	C8—C7—C12—C11	0.6 (3)
N1—C1—C2—F1	0.5 (4)	C14—C7—C12—C11	−176.4 (2)
C6—C1—C2—C3	−0.7 (4)	N1—C13—C14—C15	0.6 (4)
N1—C1—C2—C3	−179.2 (2)	N1—C13—C14—C7	179.9 (2)
F1—C2—C3—C4	−179.3 (2)	C8—C7—C14—C13	−128.3 (3)
C1—C2—C3—C4	0.4 (4)	C12—C7—C14—C13	48.6 (3)
C2—C3—C4—C5	0.0 (4)	C8—C7—C14—C15	51.0 (3)
C2—C3—C4—F2	179.5 (2)	C12—C7—C14—C15	−132.1 (2)
F2—C4—C5—C6	−179.7 (2)	C13—C14—C15—O1	4.3 (4)
C3—C4—C5—C6	−0.2 (5)	C7—C14—C15—O1	−174.9 (2)
C4—C5—C6—C1	0.0 (4)	C13—C14—C15—O2	−175.0 (2)
C2—C1—C6—C5	0.4 (4)	C7—C14—C15—O2	5.7 (3)
N1—C1—C6—C5	178.9 (2)	C14—C13—N1—C1	−175.4 (2)
C12—C7—C8—C9	−0.1 (4)	C2—C1—N1—C13	178.8 (2)
C14—C7—C8—C9	177.0 (2)	C6—C1—N1—C13	0.4 (4)
C7—C8—C9—C10	−0.1 (4)	O1—C15—O2—C16	4.9 (4)
C8—C9—C10—O3	179.2 (2)	C14—C15—O2—C16	−175.7 (2)
C8—C9—C10—C11	−0.2 (4)	C17—C16—O2—C15	173.7 (2)
O3—C10—C11—C12	−178.7 (2)	C11—C10—O3—C18	−179.2 (2)
C9—C10—C11—C12	0.7 (4)	C9—C10—O3—C18	1.5 (4)
C10—C11—C12—C7	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.51	3.280 (3)	140
C18—H18C···Cg1ii	0.96	2.92	3.631	132
N1—H1···F1	0.88 (2)	2.31 (2)	2.678 (2)	105.0 (18)
N1—H1···O1	0.88 (2)	2.02 (2)	2.678 (3)	131 (2)

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	3.280 (3)	140
C18—H18C⋯Cg1ii	0.96	2.92	3.631	132
N1—H1⋯F1	0.88 (2)	2.31 (2)	2.678 (2)	105.0 (18)
N1—H1⋯O1	0.88 (2)	2.02 (2)	2.678 (3)	131 (2)

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of C7–C12 ring.