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

In the title compound, C(18)H(18)FNO(3), the dihedral angles between the two benzene rings and the plane through the acrylate group and the fluoro-phenyl ring are 61.58 (8) and 13.33 (9)°, respectively. Mol-ecules are linked into ribbons through C-H⋯O and N-H⋯O hydrogen bonds, and further linked by C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For related literature regarding the anti­microbial activity of 3-aryl­amino-2-aryl acrylates, see: Shi et al. (2007 ▶); Xiao et al. (2007 ▶, 2008 ▶); Xue et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H18FNO3

M = 315.33

Monoclinic,

a = 19.000 (4) Å

b = 6.0400 (12) Å

c = 15.081 (3) Å

β = 109.64 (3)°

V = 1630.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.972, T max = 0.981

3073 measured reflections

2943 independent reflections

1807 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.162

S = 1.02

2943 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039184/ez2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039184/ez2149Isup2.hkl

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

C18H18FNO3	F000 = 664
Mr = 315.33	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 19.000 (4) Å	Cell parameters from 1632 reflections
b = 6.0400 (12) Å	θ = 1.4–24.7º
c = 15.081 (3) Å	µ = 0.10 mm−1
β = 109.64 (3)º	T = 293 (2) K
V = 1630.0 (6) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2943 independent reflections
Radiation source: fine-focus sealed tube	1807 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 293(2) K	θmax = 25.3º
ω/2θ scans	θmin = 1.1º
Absorption correction: ψ scan(North et al., 1968)	h = −22→21
Tmin = 0.972, Tmax = 0.981	k = −7→0
3073 measured reflections	l = 0→18

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)] = 0.050	w = 1/[σ2(Fo2) + (0.0863P)2 + 0.0162P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.15 e Å−3
2943 reflections	Δρmin = −0.16 e Å−3
215 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: 0.044 (4)
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	0.78366 (12)	0.7249 (4)	0.02705 (17)	0.0468 (6)
C2	0.86057 (14)	0.7171 (5)	0.0575 (2)	0.0637 (8)
H2	0.8858	0.6095	0.1005	0.076*
C3	0.90034 (15)	0.8673 (6)	0.0246 (2)	0.0733 (9)
H3	0.9523	0.8617	0.0451	0.088*
C4	0.86292 (16)	1.0237 (5)	−0.0380 (2)	0.0682 (9)
C5	0.78687 (17)	1.0339 (5)	−0.0708 (2)	0.0721 (9)
H5	0.7620	1.1403	−0.1148	0.086*
C6	0.74779 (15)	0.8829 (5)	−0.0373 (2)	0.0640 (8)
H6	0.6958	0.8882	−0.0588	0.077*
C7	0.64691 (12)	0.3267 (4)	0.14607 (16)	0.0431 (6)
C8	0.59236 (13)	0.1688 (4)	0.10497 (18)	0.0494 (7)
H8	0.6063	0.0338	0.0862	0.059*
C9	0.51803 (13)	0.2090 (5)	0.09161 (18)	0.0513 (7)
H9	0.4825	0.1013	0.0639	0.062*
C10	0.49607 (13)	0.4075 (4)	0.11902 (17)	0.0470 (6)
C11	0.54911 (13)	0.5661 (4)	0.16114 (19)	0.0523 (7)
H11	0.5350	0.7002	0.1804	0.063*
C12	0.62356 (13)	0.5233 (4)	0.17434 (19)	0.0510 (7)
H12	0.6591	0.6302	0.2032	0.061*
C13	0.76733 (13)	0.4059 (4)	0.12087 (17)	0.0465 (6)
H13	0.8176	0.3699	0.1356	0.056*
C14	0.72695 (12)	0.2824 (4)	0.16064 (16)	0.0433 (6)
C15	0.76226 (13)	0.0959 (4)	0.22121 (18)	0.0458 (6)
C16	0.87264 (15)	−0.1081 (5)	0.2948 (2)	0.0669 (8)
H16A	0.8550	−0.2514	0.2671	0.080*
H16B	0.8630	−0.0960	0.3538	0.080*
C17	0.95460 (15)	−0.0844 (6)	0.3113 (3)	0.0887 (11)
H17A	0.9637	−0.1045	0.2530	0.133*
H17B	0.9817	−0.1941	0.3558	0.133*
H17C	0.9709	0.0606	0.3358	0.133*
C18	0.39590 (15)	0.6241 (5)	0.1368 (2)	0.0751 (9)
H18A	0.4220	0.6374	0.2032	0.113*
H18B	0.3432	0.6130	0.1255	0.113*
H18C	0.4057	0.7521	0.1051	0.113*
F1	0.90279 (11)	1.1721 (4)	−0.07006 (17)	0.1125 (8)
H1	0.6954 (14)	0.606 (4)	0.0454 (19)	0.059 (8)*
N1	0.74101 (12)	0.5785 (4)	0.06106 (16)	0.0567 (6)
O1	0.73060 (10)	−0.0227 (3)	0.26022 (14)	0.0667 (6)
O2	0.83483 (9)	0.0669 (3)	0.23152 (13)	0.0584 (5)
O3	0.42082 (9)	0.4306 (3)	0.10206 (13)	0.0618 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0401 (13)	0.0536 (15)	0.0482 (14)	−0.0053 (12)	0.0170 (11)	0.0019 (13)
C2	0.0465 (15)	0.076 (2)	0.0642 (17)	−0.0017 (15)	0.0135 (13)	0.0221 (16)
C3	0.0434 (15)	0.093 (2)	0.082 (2)	−0.0056 (16)	0.0193 (15)	0.026 (2)
C4	0.0596 (18)	0.073 (2)	0.082 (2)	−0.0085 (16)	0.0371 (16)	0.0172 (18)
C5	0.074 (2)	0.065 (2)	0.085 (2)	0.0109 (16)	0.0370 (17)	0.0304 (18)
C6	0.0450 (15)	0.0681 (19)	0.078 (2)	0.0063 (14)	0.0193 (14)	0.0157 (17)
C7	0.0403 (13)	0.0433 (14)	0.0443 (14)	−0.0067 (11)	0.0125 (10)	0.0005 (12)
C8	0.0456 (14)	0.0464 (15)	0.0548 (15)	−0.0018 (12)	0.0150 (12)	−0.0075 (13)
C9	0.0412 (13)	0.0540 (17)	0.0528 (15)	−0.0131 (12)	0.0081 (11)	−0.0127 (13)
C10	0.0361 (12)	0.0550 (16)	0.0482 (14)	−0.0008 (12)	0.0118 (11)	0.0038 (13)
C11	0.0490 (15)	0.0417 (14)	0.0668 (17)	−0.0045 (12)	0.0202 (13)	−0.0085 (13)
C12	0.0449 (14)	0.0364 (14)	0.0694 (18)	−0.0074 (11)	0.0164 (13)	−0.0033 (13)
C13	0.0364 (12)	0.0493 (15)	0.0502 (15)	−0.0021 (12)	0.0097 (11)	0.0004 (13)
C14	0.0410 (13)	0.0406 (14)	0.0471 (14)	−0.0060 (11)	0.0133 (11)	−0.0046 (12)
C15	0.0441 (13)	0.0422 (14)	0.0521 (15)	−0.0065 (12)	0.0174 (12)	−0.0088 (13)
C16	0.0616 (17)	0.0523 (17)	0.076 (2)	0.0087 (15)	0.0087 (15)	0.0069 (16)
C17	0.0565 (18)	0.093 (3)	0.104 (3)	0.0198 (18)	0.0101 (18)	0.004 (2)
C18	0.0521 (16)	0.091 (2)	0.085 (2)	0.0079 (16)	0.0267 (16)	−0.0201 (19)
F1	0.0896 (13)	0.1078 (17)	0.154 (2)	−0.0112 (12)	0.0592 (14)	0.0556 (15)
N1	0.0359 (12)	0.0658 (15)	0.0665 (15)	0.0010 (12)	0.0146 (11)	0.0177 (13)
O1	0.0589 (11)	0.0540 (12)	0.0889 (15)	−0.0014 (10)	0.0272 (11)	0.0181 (11)
O2	0.0439 (10)	0.0583 (12)	0.0718 (13)	0.0047 (9)	0.0177 (9)	0.0084 (10)
O3	0.0399 (10)	0.0733 (13)	0.0714 (13)	0.0012 (9)	0.0177 (9)	−0.0061 (11)

C1—C6	1.368 (4)	C11—C12	1.385 (3)
C1—C2	1.377 (3)	C11—H11	0.9300
C1—N1	1.408 (3)	C12—H12	0.9300
C2—C3	1.375 (4)	C13—C14	1.347 (3)
C2—H2	0.9300	C13—N1	1.359 (3)
C3—C4	1.355 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.463 (3)
C4—C5	1.362 (4)	C15—O1	1.208 (3)
C4—F1	1.363 (3)	C15—O2	1.346 (3)
C5—C6	1.375 (4)	C16—O2	1.444 (3)
C5—H5	0.9300	C16—C17	1.499 (4)
C6—H6	0.9300	C16—H16A	0.9700
C7—C12	1.384 (3)	C16—H16B	0.9700
C7—C8	1.392 (3)	C17—H17A	0.9600
C7—C14	1.486 (3)	C17—H17B	0.9600
C8—C9	1.379 (3)	C17—H17C	0.9600
C8—H8	0.9300	C18—O3	1.425 (3)
C9—C10	1.378 (4)	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—O3	1.372 (3)	C18—H18C	0.9600
C10—C11	1.381 (3)	N1—H1	0.83 (2)
C6—C1—C2	118.7 (2)	C7—C12—H12	118.9
C6—C1—N1	119.1 (2)	C11—C12—H12	118.9
C2—C1—N1	122.2 (2)	C14—C13—N1	125.6 (2)
C3—C2—C1	120.5 (3)	C14—C13—H13	117.2
C3—C2—H2	119.8	N1—C13—H13	117.2
C1—C2—H2	119.8	C13—C14—C15	119.6 (2)
C4—C3—C2	119.2 (2)	C13—C14—C7	122.8 (2)
C4—C3—H3	120.4	C15—C14—C7	117.6 (2)
C2—C3—H3	120.4	O1—C15—O2	121.7 (2)
C3—C4—C5	121.9 (3)	O1—C15—C14	124.2 (2)
C3—C4—F1	118.8 (3)	O2—C15—C14	114.2 (2)
C5—C4—F1	119.3 (3)	O2—C16—C17	107.4 (2)
C4—C5—C6	118.3 (3)	O2—C16—H16A	110.2
C4—C5—H5	120.8	C17—C16—H16A	110.2
C6—C5—H5	120.8	O2—C16—H16B	110.2
C1—C6—C5	121.4 (2)	C17—C16—H16B	110.2
C1—C6—H6	119.3	H16A—C16—H16B	108.5
C5—C6—H6	119.3	C16—C17—H17A	109.5
C12—C7—C8	117.2 (2)	C16—C17—H17B	109.5
C12—C7—C14	121.8 (2)	H17A—C17—H17B	109.5
C8—C7—C14	120.9 (2)	C16—C17—H17C	109.5
C9—C8—C7	121.1 (2)	H17A—C17—H17C	109.5
C9—C8—H8	119.4	H17B—C17—H17C	109.5
C7—C8—H8	119.4	O3—C18—H18A	109.5
C10—C9—C8	120.5 (2)	O3—C18—H18B	109.5
C10—C9—H9	119.7	H18A—C18—H18B	109.5
C8—C9—H9	119.7	O3—C18—H18C	109.5
O3—C10—C9	115.8 (2)	H18A—C18—H18C	109.5
O3—C10—C11	124.6 (2)	H18B—C18—H18C	109.5
C9—C10—C11	119.6 (2)	C13—N1—C1	126.5 (2)
C10—C11—C12	119.2 (2)	C13—N1—H1	117.1 (19)
C10—C11—H11	120.4	C1—N1—H1	116.3 (19)
C12—C11—H11	120.4	C15—O2—C16	115.8 (2)
C7—C12—C11	122.3 (2)	C10—O3—C18	118.0 (2)
C6—C1—C2—C3	0.9 (4)	C10—C11—C12—C7	0.5 (4)
N1—C1—C2—C3	−178.1 (3)	N1—C13—C14—C15	177.8 (2)
C1—C2—C3—C4	0.1 (5)	N1—C13—C14—C7	−2.3 (4)
C2—C3—C4—C5	−1.3 (5)	C12—C7—C14—C13	−62.1 (3)
C2—C3—C4—F1	179.9 (3)	C8—C7—C14—C13	119.3 (3)
C3—C4—C5—C6	1.4 (5)	C12—C7—C14—C15	117.8 (3)
F1—C4—C5—C6	−179.8 (3)	C8—C7—C14—C15	−60.8 (3)
C2—C1—C6—C5	−0.8 (4)	C13—C14—C15—O1	179.5 (2)
N1—C1—C6—C5	178.2 (3)	C7—C14—C15—O1	−0.4 (4)
C4—C5—C6—C1	−0.3 (5)	C13—C14—C15—O2	0.3 (3)
C12—C7—C8—C9	1.2 (4)	C7—C14—C15—O2	−179.6 (2)
C14—C7—C8—C9	179.8 (2)	C14—C13—N1—C1	172.4 (2)
C7—C8—C9—C10	−0.1 (4)	C6—C1—N1—C13	176.2 (3)
C8—C9—C10—O3	179.7 (2)	C2—C1—N1—C13	−4.8 (4)
C8—C9—C10—C11	−0.7 (4)	O1—C15—O2—C16	−2.4 (3)
O3—C10—C11—C12	−179.9 (2)	C14—C15—O2—C16	176.8 (2)
C9—C10—C11—C12	0.5 (4)	C17—C16—O2—C15	−169.0 (2)
C8—C7—C12—C11	−1.3 (4)	C9—C10—O3—C18	174.3 (2)
C14—C7—C12—C11	−180.0 (2)	C11—C10—O3—C18	−5.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.49	3.401 (3)	167
N1—H1···O3ii	0.83 (2)	2.56 (3)	3.229 (3)	138 (2)
C16—H16B···Cg1iii	0.97	2.99	3.788 (3)	141
C18—H18A···Cg2iv	0.96	2.80	3.626 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.49	3.401 (3)	167
N1—H1⋯O3ii	0.83 (2)	2.56 (3)	3.229 (3)	138 (2)
C16—H16B⋯Cg1iii	0.97	2.99	3.788 (3)	141
C18—H18A⋯Cg2iv	0.96	2.80	3.626 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.