Ethyl (Z)-3-(4-methyl-anilino)-2-[(4-methyl-phen-yl)carbamo-yl]prop-2-enoate.

The title compound, C(20)H(22)N(2)O(3), is a secondary amine featuring an amide and an ester functionality in connection with a Michael system. The conformation about the C=C bond is E. Intra-molecular N-H⋯O hydrogen bonds occur. In the crystal, C-H⋯O contacts connect the mol-ecules into chains along the b-axis direction.

Related literature

For general information about the synthetic and industrial importance of aniline and its derivatives, see: Berry & Royd (1984 ▶); Garudachari et al. (2012 ▶); Sridharan et al. (2006 ▶); Kasthuri et al. (2008 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H22N2O3

M = 338.40

Monoclinic,

a = 18.8170 (4) Å

b = 11.9752 (3) Å

c = 15.6043 (4) Å

β = 91.470 (1)°

V = 3515.07 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.42 × 0.26 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.965, T max = 0.984

16569 measured reflections

4353 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.147

S = 1.05

4353 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043723/zq2185sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043723/zq2185Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043723/zq2185Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043723/zq2185Isup4.cml

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

C20H22N2O3	F(000) = 1440
Mr = 338.40	Dx = 1.279 Mg m−3
Monoclinic, C2/c	Melting point = 438–440 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.8170 (4) Å	Cell parameters from 7492 reflections
b = 11.9752 (3) Å	θ = 2.4–28.3°
c = 15.6043 (4) Å	µ = 0.09 mm−1
β = 91.470 (1)°	T = 200 K
V = 3515.07 (15) Å3	Cubic, white
Z = 8	0.42 × 0.26 × 0.19 mm

Bruker APEXII CCD diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→25
Tmin = 0.965, Tmax = 0.984	k = −15→11
16569 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0721P)2 + 2.7716P] where P = (Fo2 + 2Fc2)/3
4353 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.10013 (6)	0.36356 (9)	0.05742 (8)	0.0390 (3)
O2	0.06034 (7)	0.70809 (10)	0.07895 (9)	0.0432 (3)
O3	−0.03953 (6)	0.66632 (10)	0.14650 (8)	0.0396 (3)
N1	−0.02327 (7)	0.33906 (11)	0.13174 (9)	0.0328 (3)
N2	0.14011 (7)	0.53822 (11)	0.02606 (9)	0.0311 (3)
C1	−0.25933 (9)	0.06696 (16)	0.22528 (12)	0.0427 (4)
H1A	−0.3026	0.0976	0.1980	0.064*
H1B	−0.2645	0.0658	0.2876	0.064*
H1C	−0.2516	−0.0092	0.2046	0.064*
C2	−0.02178 (8)	0.44917 (13)	0.13478 (10)	0.0312 (3)
H2A	−0.0606	0.4854	0.1608	0.037*
C3	0.03155 (8)	0.51666 (13)	0.10328 (9)	0.0297 (3)
C4	0.09288 (8)	0.46684 (13)	0.06104 (9)	0.0302 (3)
C5	0.02073 (8)	0.63730 (14)	0.10765 (10)	0.0326 (3)
C6	−0.05772 (10)	0.78362 (15)	0.14399 (13)	0.0469 (4)
H6A	−0.0622	0.8099	0.0839	0.056*
H6B	−0.0205	0.8283	0.1741	0.056*
C7	−0.12693 (12)	0.79542 (19)	0.18756 (17)	0.0635 (6)
H7A	−0.1402	0.8745	0.1898	0.095*
H7B	−0.1224	0.7658	0.2460	0.095*
H7C	−0.1637	0.7537	0.1556	0.095*
C8	0.41549 (10)	0.47429 (18)	−0.11452 (14)	0.0508 (5)
H8A	0.4139	0.4875	−0.1765	0.076*
H8B	0.4322	0.3981	−0.1029	0.076*
H8C	0.4481	0.5278	−0.0868	0.076*
C11	−0.08114 (8)	0.27242 (13)	0.15835 (10)	0.0309 (3)
C12	−0.09618 (8)	0.17563 (14)	0.11323 (10)	0.0341 (3)
H12	−0.0674	0.1541	0.0669	0.041*
C13	−0.15332 (9)	0.11012 (13)	0.13590 (10)	0.0334 (3)
H13	−0.1632	0.0436	0.1046	0.040*
C14	−0.19666 (8)	0.13884 (13)	0.20320 (10)	0.0318 (3)
C15	−0.18046 (9)	0.23622 (14)	0.24851 (10)	0.0345 (3)
H15	−0.2091	0.2575	0.2951	0.041*
C16	−0.12299 (9)	0.30289 (13)	0.22665 (10)	0.0339 (3)
H16	−0.1125	0.3689	0.2583	0.041*
C21	0.20602 (8)	0.51483 (13)	−0.01130 (10)	0.0291 (3)
C22	0.24017 (9)	0.41154 (13)	−0.00733 (11)	0.0348 (4)
H22	0.2177	0.3494	0.0184	0.042*
C23	0.30724 (9)	0.40025 (13)	−0.04125 (11)	0.0371 (4)
H23	0.3301	0.3296	−0.0382	0.044*
C24	0.34214 (8)	0.48883 (14)	−0.07960 (11)	0.0355 (4)
C25	0.30692 (9)	0.59088 (14)	−0.08402 (10)	0.0350 (4)
H25	0.3293	0.6528	−0.1102	0.042*
C26	0.23978 (8)	0.60390 (13)	−0.05100 (10)	0.0315 (3)
H26	0.2165	0.6741	−0.0554	0.038*
H1	0.0165 (11)	0.3084 (18)	0.1007 (13)	0.051 (6)*
H2	0.1286 (11)	0.6090 (19)	0.0307 (13)	0.046 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (6)	0.0282 (6)	0.0518 (7)	−0.0027 (5)	0.0111 (5)	0.0020 (5)
O2	0.0395 (6)	0.0313 (6)	0.0595 (8)	−0.0067 (5)	0.0168 (6)	0.0000 (5)
O3	0.0365 (6)	0.0332 (6)	0.0498 (7)	−0.0006 (5)	0.0139 (5)	0.0026 (5)
N1	0.0278 (6)	0.0320 (7)	0.0389 (7)	−0.0026 (5)	0.0048 (5)	0.0011 (5)
N2	0.0281 (6)	0.0269 (7)	0.0384 (7)	−0.0020 (5)	0.0039 (5)	0.0021 (5)
C1	0.0386 (9)	0.0414 (10)	0.0482 (10)	−0.0135 (7)	0.0049 (7)	0.0033 (8)
C2	0.0305 (7)	0.0325 (8)	0.0304 (7)	−0.0024 (6)	−0.0008 (6)	0.0011 (6)
C3	0.0286 (7)	0.0308 (8)	0.0297 (7)	−0.0047 (6)	−0.0001 (6)	0.0017 (6)
C4	0.0293 (7)	0.0311 (8)	0.0300 (7)	−0.0058 (6)	−0.0017 (6)	0.0026 (6)
C5	0.0309 (7)	0.0343 (8)	0.0329 (8)	−0.0039 (6)	0.0028 (6)	0.0001 (6)
C6	0.0472 (10)	0.0346 (9)	0.0599 (12)	0.0025 (8)	0.0159 (9)	0.0037 (8)
C7	0.0595 (13)	0.0477 (12)	0.0848 (16)	0.0138 (10)	0.0327 (12)	0.0098 (11)
C8	0.0335 (9)	0.0503 (11)	0.0694 (13)	−0.0037 (8)	0.0150 (9)	−0.0061 (9)
C11	0.0273 (7)	0.0308 (8)	0.0346 (8)	−0.0032 (6)	0.0000 (6)	0.0066 (6)
C12	0.0322 (8)	0.0349 (8)	0.0355 (8)	−0.0002 (6)	0.0042 (6)	0.0022 (6)
C13	0.0355 (8)	0.0277 (7)	0.0368 (8)	−0.0023 (6)	−0.0009 (6)	0.0017 (6)
C14	0.0285 (7)	0.0305 (8)	0.0365 (8)	−0.0034 (6)	−0.0004 (6)	0.0068 (6)
C15	0.0337 (8)	0.0346 (8)	0.0353 (8)	−0.0024 (6)	0.0034 (6)	0.0018 (6)
C16	0.0355 (8)	0.0311 (8)	0.0350 (8)	−0.0059 (6)	−0.0015 (6)	−0.0004 (6)
C21	0.0270 (7)	0.0288 (7)	0.0315 (7)	−0.0043 (6)	0.0003 (6)	0.0002 (6)
C22	0.0328 (8)	0.0256 (7)	0.0462 (9)	−0.0055 (6)	0.0041 (7)	0.0021 (6)
C23	0.0343 (8)	0.0261 (7)	0.0509 (10)	−0.0009 (6)	0.0024 (7)	−0.0028 (7)
C24	0.0291 (7)	0.0356 (8)	0.0419 (9)	−0.0043 (6)	0.0034 (6)	−0.0046 (7)
C25	0.0335 (8)	0.0325 (8)	0.0390 (8)	−0.0080 (6)	0.0043 (6)	0.0031 (6)
C26	0.0314 (8)	0.0274 (7)	0.0357 (8)	−0.0021 (6)	−0.0002 (6)	0.0037 (6)

O1—C4	1.2458 (19)	C8—C24	1.507 (2)
O2—C5	1.2214 (19)	C8—H8A	0.9800
O3—C5	1.3451 (19)	C8—H8B	0.9800
O3—C6	1.446 (2)	C8—H8C	0.9800
N1—C2	1.320 (2)	C11—C12	1.382 (2)
N1—C11	1.4207 (19)	C11—C16	1.390 (2)
N1—H1	0.97 (2)	C12—C13	1.384 (2)
N2—C4	1.3576 (19)	C12—H12	0.9500
N2—C21	1.412 (2)	C13—C14	1.389 (2)
N2—H2	0.88 (2)	C13—H13	0.9500
C1—C14	1.507 (2)	C14—C15	1.393 (2)
C1—H1A	0.9800	C15—C16	1.394 (2)
C1—H1B	0.9800	C15—H15	0.9500
C1—H1C	0.9800	C16—H16	0.9500
C2—C3	1.388 (2)	C21—C22	1.395 (2)
C2—H2A	0.9500	C21—C26	1.395 (2)
C3—C5	1.461 (2)	C22—C23	1.388 (2)
C3—C4	1.470 (2)	C22—H22	0.9500
C6—C7	1.491 (3)	C23—C24	1.391 (2)
C6—H6A	0.9900	C23—H23	0.9500
C6—H6B	0.9900	C24—C25	1.391 (2)
C7—H7A	0.9800	C25—C26	1.385 (2)
C7—H7B	0.9800	C25—H25	0.9500
C7—H7C	0.9800	C26—H26	0.9500
C5—O3—C6	116.13 (13)	C24—C8—H8C	109.5
C2—N1—C11	124.50 (14)	H8A—C8—H8C	109.5
C2—N1—H1	112.3 (13)	H8B—C8—H8C	109.5
C11—N1—H1	122.6 (13)	C12—C11—C16	119.89 (14)
C4—N2—C21	129.21 (14)	C12—C11—N1	118.09 (14)
C4—N2—H2	114.2 (14)	C16—C11—N1	122.02 (14)
C21—N2—H2	116.5 (13)	C11—C12—C13	119.70 (15)
C14—C1—H1A	109.5	C11—C12—H12	120.1
C14—C1—H1B	109.5	C13—C12—H12	120.1
H1A—C1—H1B	109.5	C12—C13—C14	121.85 (15)
C14—C1—H1C	109.5	C12—C13—H13	119.1
H1A—C1—H1C	109.5	C14—C13—H13	119.1
H1B—C1—H1C	109.5	C13—C14—C15	117.76 (14)
N1—C2—C3	125.72 (15)	C13—C14—C1	120.62 (15)
N1—C2—H2A	117.1	C15—C14—C1	121.62 (15)
C3—C2—H2A	117.1	C14—C15—C16	121.08 (15)
C2—C3—C5	117.15 (14)	C14—C15—H15	119.5
C2—C3—C4	120.36 (14)	C16—C15—H15	119.5
C5—C3—C4	122.29 (13)	C11—C16—C15	119.72 (15)
O1—C4—N2	122.23 (14)	C11—C16—H16	120.1
O1—C4—C3	120.75 (13)	C15—C16—H16	120.1
N2—C4—C3	117.02 (14)	C22—C21—C26	118.90 (14)
O2—C5—O3	121.02 (15)	C22—C21—N2	124.49 (14)
O2—C5—C3	125.61 (15)	C26—C21—N2	116.53 (14)
O3—C5—C3	113.37 (13)	C23—C22—C21	119.48 (14)
O3—C6—C7	106.77 (15)	C23—C22—H22	120.3
O3—C6—H6A	110.4	C21—C22—H22	120.3
C7—C6—H6A	110.4	C22—C23—C24	122.27 (15)
O3—C6—H6B	110.4	C22—C23—H23	118.9
C7—C6—H6B	110.4	C24—C23—H23	118.9
H6A—C6—H6B	108.6	C23—C24—C25	117.49 (15)
C6—C7—H7A	109.5	C23—C24—C8	120.95 (16)
C6—C7—H7B	109.5	C25—C24—C8	121.56 (16)
H7A—C7—H7B	109.5	C26—C25—C24	121.22 (15)
C6—C7—H7C	109.5	C26—C25—H25	119.4
H7A—C7—H7C	109.5	C24—C25—H25	119.4
H7B—C7—H7C	109.5	C25—C26—C21	120.62 (15)
C24—C8—H8A	109.5	C25—C26—H26	119.7
C24—C8—H8B	109.5	C21—C26—H26	119.7
H8A—C8—H8B	109.5
C11—N1—C2—C3	−174.78 (14)	C11—C12—C13—C14	0.1 (2)
N1—C2—C3—C5	175.86 (15)	C12—C13—C14—C15	−0.6 (2)
N1—C2—C3—C4	0.9 (2)	C12—C13—C14—C1	178.83 (15)
C21—N2—C4—O1	−6.6 (2)	C13—C14—C15—C16	0.4 (2)
C21—N2—C4—C3	173.92 (14)	C1—C14—C15—C16	−179.03 (15)
C2—C3—C4—O1	−4.3 (2)	C12—C11—C16—C15	−0.8 (2)
C5—C3—C4—O1	−179.08 (14)	N1—C11—C16—C15	178.07 (14)
C2—C3—C4—N2	175.10 (14)	C14—C15—C16—C11	0.3 (2)
C5—C3—C4—N2	0.4 (2)	C4—N2—C21—C22	−10.2 (3)
C6—O3—C5—O2	6.2 (2)	C4—N2—C21—C26	172.94 (15)
C6—O3—C5—C3	−172.92 (15)	C26—C21—C22—C23	1.3 (2)
C2—C3—C5—O2	−175.98 (15)	N2—C21—C22—C23	−175.49 (15)
C4—C3—C5—O2	−1.1 (3)	C21—C22—C23—C24	−0.1 (3)
C2—C3—C5—O3	3.1 (2)	C22—C23—C24—C25	−0.7 (3)
C4—C3—C5—O3	178.03 (13)	C22—C23—C24—C8	178.98 (17)
C5—O3—C6—C7	177.95 (16)	C23—C24—C25—C26	0.4 (2)
C2—N1—C11—C12	144.73 (16)	C8—C24—C25—C26	−179.34 (16)
C2—N1—C11—C16	−34.1 (2)	C24—C25—C26—C21	0.8 (2)
C16—C11—C12—C13	0.6 (2)	C22—C21—C26—C25	−1.7 (2)
N1—C11—C12—C13	−178.31 (14)	N2—C21—C26—C25	175.37 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1i	0.95	2.68	3.620 (2)	170
C25—H25···O2ii	0.95	2.70	3.4685 (19)	139
N1—H1···O1	0.97 (2)	1.85 (2)	2.6383 (17)	135.9 (18)
N2—H2···O2	0.88 (2)	1.92 (2)	2.6713 (18)	143.0 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O1i	0.95	2.68	3.620 (2)	170
C25—H25⋯O2ii	0.95	2.70	3.4685 (19)	139
N1—H1⋯O1	0.97 (2)	1.85 (2)	2.6383 (17)	135.9 (18)
N2—H2⋯O2	0.88 (2)	1.92 (2)	2.6713 (18)	143.0 (19)

Symmetry codes: (i) ; (ii) .