(E)-Ethyl 3-(2-fluoro-anilino)-2-(4-methoxy-phen-yl)acrylate.

The title compound, C(18)H(18)FNO(3), consists of three individually planar subunits, namely two substituted benzene rings and one amino-acrylate group. The dihedral angle between the two benzene rings is 47.48 (8)°. The amino-acrylate group forms dihedral angles of 57.95 (7) and 11.27 (6)° with the methoxy-phenyl and fluorophenyl rings, respectively.

Related literature

For related literature, see: Xiao et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C18H18FNO3

M = 315.33

Triclinic,

a = 6.3630 (13) Å

b = 9.4700 (19) Å

c = 13.981 (3) Å

α = 97.68 (3)°

β = 97.38 (3)°

γ = 95.40 (3)°

V = 822.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.963, T max = 0.981

3273 measured reflections

2980 independent reflections

1922 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.175

S = 1.09

2980 reflections

209 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.21 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800175X/pv2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800175X/pv2066Isup2.hkl

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

C18H18FNO3	Z = 2
Mr = 315.33	F000 = 332
Triclinic, P1	Dx = 1.273 Mg m−3
a = 6.3630 (13) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.4700 (19) Å	Cell parameters from 1625 reflections
c = 13.981 (3) Å	θ = 1.5–25.0º
α = 97.68 (3)º	µ = 0.09 mm−1
β = 97.38 (3)º	T = 298 (2) K
γ = 95.40 (3)º	Block, colorless
V = 822.7 (3) Å3	0.40 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2980 independent reflections
Radiation source: fine-focus sealed tube	1922 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
T = 298(2) K	θmax = 25.3º
ω/2θ scans	θmin = 1.5º
Absorption correction: ψ scan(North et al., 1968)	h = 0→7
Tmin = 0.963, Tmax = 0.981	k = −11→11
3273 measured reflections	l = −16→16

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)] = 0.058	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.314P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.175	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.26 e Å−3
2980 reflections	Δρmin = −0.21 e Å−3
209 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: 0.107 (9)
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
O3	0.4465 (3)	0.2358 (2)	0.49646 (15)	0.0698 (6)
O2	−0.0514 (3)	0.6582 (2)	0.10142 (15)	0.0714 (6)
O1	−0.1278 (3)	0.4580 (2)	0.16366 (17)	0.0771 (7)
F1	0.9092 (3)	0.8076 (2)	0.36459 (16)	0.090
C14	0.2001 (4)	0.6001 (3)	0.2237 (2)	0.0519 (7)
C7	0.2661 (4)	0.5043 (3)	0.29442 (19)	0.0490 (6)
C12	0.4551 (4)	0.4418 (3)	0.2923 (2)	0.0555 (7)
H12	0.5395	0.4604	0.2448	0.067*
N1	0.5153 (4)	0.7686 (3)	0.26886 (18)	0.0571 (6)
C9	0.2078 (4)	0.3844 (3)	0.4321 (2)	0.0566 (7)
H9	0.1244	0.3656	0.4799	0.068*
C15	−0.0076 (4)	0.5629 (3)	0.1627 (2)	0.0557 (7)
C1	0.6532 (4)	0.8864 (3)	0.25557 (19)	0.0508 (7)
C10	0.3977 (4)	0.3237 (3)	0.4281 (2)	0.0507 (7)
C8	0.1423 (4)	0.4720 (3)	0.3660 (2)	0.0533 (7)
H8	0.0137	0.5105	0.3689	0.064*
C13	0.3239 (4)	0.7195 (3)	0.2132 (2)	0.0543 (7)
H13	0.2752	0.7717	0.1646	0.065*
C5	1.0048 (5)	1.0171 (3)	0.2990 (3)	0.0709 (9)
H5	1.1400	1.0267	0.3351	0.085*
C11	0.5217 (4)	0.3533 (3)	0.3579 (2)	0.0589 (8)
H11	0.6496	0.3139	0.3549	0.071*
C6	0.8571 (4)	0.9063 (3)	0.3057 (2)	0.0580 (7)
C2	0.6015 (5)	0.9858 (3)	0.1961 (2)	0.0691 (9)
H2	0.4652	0.9776	0.1612	0.083*
C4	0.9513 (5)	1.1144 (3)	0.2383 (2)	0.0738 (9)
H4	1.0502	1.1902	0.2319	0.089*
C3	0.7505 (6)	1.0982 (3)	0.1874 (3)	0.0780 (10)
H3	0.7130	1.1638	0.1461	0.094*
C18	0.6409 (5)	0.1735 (4)	0.4950 (3)	0.0800 (10)
H18A	0.6384	0.1153	0.4330	0.120*
H18B	0.6575	0.1151	0.5459	0.120*
H18C	0.7581	0.2480	0.5050	0.120*
C16	−0.2489 (5)	0.6276 (4)	0.0363 (3)	0.0823 (10)
H16A	−0.3683	0.6266	0.0731	0.099*
H16B	−0.2552	0.5344	−0.0031	0.099*
C17	−0.2589 (7)	0.7410 (5)	−0.0268 (3)	0.1111 (15)
H17A	−0.2568	0.8323	0.0128	0.167*
H17B	−0.3881	0.7218	−0.0724	0.167*
H17C	−0.1384	0.7425	−0.0616	0.167*
H1	0.567 (5)	0.714 (4)	0.313 (3)	0.089 (11)*

	U11	U22	U33	U12	U13	U23
O3	0.0550 (12)	0.0796 (14)	0.0784 (14)	0.0045 (10)	0.0128 (10)	0.0239 (12)
O2	0.0526 (12)	0.0798 (15)	0.0765 (14)	−0.0031 (10)	−0.0079 (10)	0.0156 (12)
O1	0.0451 (12)	0.0827 (15)	0.0974 (17)	−0.0184 (11)	0.0068 (11)	0.0121 (12)
F1	0.054	0.096	0.121	−0.007	−0.008	0.048
C14	0.0367 (14)	0.0573 (16)	0.0594 (17)	−0.0039 (12)	0.0121 (12)	0.0024 (13)
C7	0.0382 (14)	0.0497 (15)	0.0562 (16)	−0.0067 (11)	0.0083 (12)	0.0041 (12)
C12	0.0409 (15)	0.0671 (18)	0.0596 (17)	−0.0034 (13)	0.0197 (13)	0.0080 (15)
N1	0.0470 (13)	0.0586 (15)	0.0633 (15)	−0.0110 (11)	−0.0012 (11)	0.0207 (12)
C9	0.0448 (16)	0.0693 (18)	0.0545 (17)	−0.0053 (13)	0.0166 (13)	0.0043 (14)
C15	0.0419 (15)	0.0633 (18)	0.0626 (18)	0.0018 (14)	0.0141 (13)	0.0089 (15)
C1	0.0462 (15)	0.0485 (15)	0.0563 (16)	−0.0034 (12)	0.0086 (12)	0.0084 (13)
C10	0.0418 (15)	0.0516 (15)	0.0560 (16)	−0.0051 (12)	0.0060 (12)	0.0072 (13)
C8	0.0366 (14)	0.0622 (17)	0.0602 (17)	−0.0019 (12)	0.0151 (12)	0.0037 (14)
C13	0.0442 (15)	0.0602 (17)	0.0574 (17)	−0.0025 (13)	0.0080 (13)	0.0098 (13)
C5	0.0482 (17)	0.0658 (19)	0.093 (2)	−0.0126 (15)	0.0047 (16)	0.0110 (18)
C11	0.0365 (14)	0.0654 (18)	0.074 (2)	0.0014 (13)	0.0133 (14)	0.0038 (15)
C6	0.0461 (16)	0.0542 (16)	0.075 (2)	0.0027 (13)	0.0055 (14)	0.0190 (15)
C2	0.0575 (19)	0.068 (2)	0.078 (2)	−0.0089 (15)	−0.0015 (16)	0.0184 (17)
C4	0.070 (2)	0.0584 (19)	0.088 (2)	−0.0192 (16)	0.0142 (18)	0.0082 (17)
C3	0.087 (3)	0.058 (2)	0.088 (2)	−0.0072 (17)	0.004 (2)	0.0278 (18)
C18	0.063 (2)	0.081 (2)	0.097 (3)	0.0125 (17)	0.0042 (18)	0.020 (2)
C16	0.0512 (19)	0.113 (3)	0.074 (2)	0.0140 (18)	−0.0053 (16)	−0.005 (2)
C17	0.112 (3)	0.133 (4)	0.085 (3)	0.041 (3)	−0.017 (2)	0.018 (3)

O3—C10	1.374 (3)	C10—C11	1.376 (4)
O3—C18	1.421 (4)	C8—H8	0.9300
O2—C15	1.349 (3)	C13—H13	0.9300
O2—C16	1.435 (4)	C5—C6	1.363 (4)
O1—C15	1.198 (3)	C5—C4	1.370 (4)
F1—C6	1.362 (3)	C5—H5	0.9300
C14—C13	1.351 (4)	C11—H11	0.9300
C14—C15	1.463 (4)	C2—C3	1.386 (4)
C14—C7	1.478 (4)	C2—H2	0.9300
C7—C12	1.392 (4)	C4—C3	1.365 (5)
C7—C8	1.397 (4)	C4—H4	0.9300
C12—C11	1.377 (4)	C3—H3	0.9300
C12—H12	0.9300	C18—H18A	0.9600
N1—C13	1.364 (3)	C18—H18B	0.9600
N1—C1	1.400 (3)	C18—H18C	0.9600
N1—H1	0.91 (3)	C16—C17	1.479 (5)
C9—C8	1.374 (4)	C16—H16A	0.9700
C9—C10	1.391 (4)	C16—H16B	0.9700
C9—H9	0.9300	C17—H17A	0.9600
C1—C2	1.373 (4)	C17—H17B	0.9600
C1—C6	1.377 (4)	C17—H17C	0.9600
C10—O3—C18	117.1 (2)	C4—C5—H5	120.5
C15—O2—C16	116.8 (3)	C10—C11—C12	119.5 (3)
C13—C14—C15	119.2 (3)	C10—C11—H11	120.2
C13—C14—C7	122.7 (2)	C12—C11—H11	120.2
C15—C14—C7	118.2 (2)	F1—C6—C5	119.7 (3)
C12—C7—C8	117.1 (3)	F1—C6—C1	116.6 (2)
C12—C7—C14	121.1 (2)	C5—C6—C1	123.7 (3)
C8—C7—C14	121.8 (2)	C1—C2—C3	120.7 (3)
C11—C12—C7	122.4 (2)	C1—C2—H2	119.7
C11—C12—H12	118.8	C3—C2—H2	119.7
C7—C12—H12	118.8	C3—C4—C5	118.9 (3)
C13—N1—C1	125.7 (2)	C3—C4—H4	120.6
C13—N1—H1	117 (2)	C5—C4—H4	120.6
C1—N1—H1	116 (2)	C4—C3—C2	121.2 (3)
C8—C9—C10	120.5 (3)	C4—C3—H3	119.4
C8—C9—H9	119.8	C2—C3—H3	119.4
C10—C9—H9	119.8	O3—C18—H18A	109.5
O1—C15—O2	122.0 (3)	O3—C18—H18B	109.5
O1—C15—C14	125.0 (3)	H18A—C18—H18B	109.5
O2—C15—C14	113.0 (2)	O3—C18—H18C	109.5
C2—C1—C6	116.4 (2)	H18A—C18—H18C	109.5
C2—C1—N1	125.1 (3)	H18B—C18—H18C	109.5
C6—C1—N1	118.5 (2)	O2—C16—C17	107.6 (3)
O3—C10—C11	124.7 (3)	O2—C16—H16A	110.2
O3—C10—C9	115.8 (2)	C17—C16—H16A	110.2
C11—C10—C9	119.5 (3)	O2—C16—H16B	110.2
C9—C8—C7	121.0 (3)	C17—C16—H16B	110.2
C9—C8—H8	119.5	H16A—C16—H16B	108.5
C7—C8—H8	119.5	C16—C17—H17A	109.5
C14—C13—N1	124.4 (3)	C16—C17—H17B	109.5
C14—C13—H13	117.8	H17A—C17—H17B	109.5
N1—C13—H13	117.8	C16—C17—H17C	109.5
C6—C5—C4	119.1 (3)	H17A—C17—H17C	109.5
C6—C5—H5	120.5	H17B—C17—H17C	109.5
C13—C14—C7—C12	−56.8 (4)	C14—C7—C8—C9	−179.0 (2)
C15—C14—C7—C12	122.9 (3)	C15—C14—C13—N1	176.7 (3)
C13—C14—C7—C8	123.3 (3)	C7—C14—C13—N1	−3.5 (4)
C15—C14—C7—C8	−57.0 (3)	C1—N1—C13—C14	175.6 (3)
C8—C7—C12—C11	−0.8 (4)	O3—C10—C11—C12	179.2 (2)
C14—C7—C12—C11	179.3 (2)	C9—C10—C11—C12	−0.5 (4)
C16—O2—C15—O1	−0.6 (4)	C7—C12—C11—C10	0.5 (4)
C16—O2—C15—C14	177.9 (2)	C4—C5—C6—F1	179.0 (3)
C13—C14—C15—O1	177.8 (3)	C4—C5—C6—C1	−0.9 (5)
C7—C14—C15—O1	−2.0 (4)	C2—C1—C6—F1	−179.8 (3)
C13—C14—C15—O2	−0.6 (4)	N1—C1—C6—F1	0.4 (4)
C7—C14—C15—O2	179.7 (2)	C2—C1—C6—C5	0.1 (5)
C13—N1—C1—C2	12.3 (5)	N1—C1—C6—C5	−179.7 (3)
C13—N1—C1—C6	−168.0 (3)	C6—C1—C2—C3	0.7 (5)
C18—O3—C10—C11	1.1 (4)	N1—C1—C2—C3	−179.5 (3)
C18—O3—C10—C9	−179.3 (3)	C6—C5—C4—C3	0.9 (5)
C8—C9—C10—O3	−178.9 (2)	C5—C4—C3—C2	−0.1 (5)
C8—C9—C10—C11	0.8 (4)	C1—C2—C3—C4	−0.8 (5)
C10—C9—C8—C7	−1.1 (4)	C15—O2—C16—C17	−177.3 (3)
C12—C7—C8—C9	1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.91 (3)	2.65 (3)	3.256 (3)	125 (3)
C12—H12···O1ii	0.93	2.53	3.394 (3)	155
N1—H1···F1	0.91 (3)	2.26 (3)	2.654 (3)	102 (2)
C13—H13···O2	93.0	2.26	2.649 (3)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.91 (3)	2.65 (3)	3.256 (3)	125 (3)
C12—H12⋯O1ii	0.93	2.53	3.394 (3)	155
N1—H1⋯F1	0.91 (3)	2.26 (3)	2.654 (3)	102 (2)
C13—H13⋯O2	93.0	2.26	2.649 (3)	104

Symmetry codes: (i) ; (ii) .