organic compounds
Ethyl (Z)-3-(4-methylanilino)-2-[(4-methylphenyl)carbamoyl]prop-2-enoate
aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
The title compound, C20H22N2O3, 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. Intramolecular N—H⋯O hydrogen bonds occur. In the crystal, C—H⋯O contacts connect the molecules 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
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Refinement
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Data collection: APEX2 (Bruker, 2010); cell 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).
Supporting information
10.1107/S1600536812043723/zq2185sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812043723/zq2185Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812043723/zq2185Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812043723/zq2185Isup4.cml
A mixture of diethyl-{[(4-methylphenyl)amino]methylidene}propanedioate (1.0 g, 0.0036 mol) and 4-methylaniline (0.19 g, 0.0018 mol) in dowtherm (10 ml) was stirred at 150 °C for 2 h. The reaction mixture was then cooled to 25 °C and stirred in n-hexane (20 ml) for 10 min. The solid product obtained was filtered, dried and further purified by
using petrol ether and ethyl acetate (v:v = 5:5) as the to get a white solid. Crystals were grown by slow evaporation of a dilute ethanol solution at room temperature, yield: 0.52 g (42.6%).Carbon-bound H atoms were placed in calculated positions (C—H = 0.95 Å for aromatic and vinylic carbon atoms, C—H = 0.99 Å for the methylene group, and C—H = 0.98 Å for the methyl groups) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2 or 1.5Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density [HFIX 137 in the SHELX program suite (Sheldrick, 2008), with Uiso(H) set to 1.5Ueq(C)]. Both nitrogen-bound H atoms were located on a difference Fourier map and refined freely.Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).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 |
C20H22N2O3 | V = 3515.07 (15) Å3 |
Mr = 338.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.8170 (4) Å | µ = 0.09 mm−1 |
b = 11.9752 (3) Å | T = 200 K |
c = 15.6043 (4) Å | 0.42 × 0.26 × 0.19 mm |
β = 91.470 (1)° |
Bruker APEXII CCD diffractometer | 4353 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3411 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.984 | Rint = 0.022 |
16569 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.56 e Å−3 |
4353 reflections | Δρmin = −0.22 e Å−3 |
237 parameters |
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) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1/2, −y+3/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H22N2O3 |
Mr | 338.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 200 |
a, b, c (Å) | 18.8170 (4), 11.9752 (3), 15.6043 (4) |
β (°) | 91.470 (1) |
V (Å3) | 3515.07 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.26 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.965, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16569, 4353, 3411 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.147, 1.05 |
No. of reflections | 4353 |
No. of parameters | 237 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.56, −0.22 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O1i | 0.95 | 2.68 | 3.620 (2) | 170.3 |
C25—H25···O2ii | 0.95 | 2.70 | 3.4685 (19) | 138.8 |
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) −x+1/2, −y+1/2, −z; (ii) −x+1/2, −y+3/2, −z. |
Acknowledgements
AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear sciences, Government of India, for the Young Scientist award.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The study of aniline derivatives is important due to the presence of amines in natural products and nucleic acids (Berry & Royd, 1984). Aniline compounds find widespread applications in the field of synthetic chemistry such as the synthesis of quinolines and indoles (Garudachari et al., 2012; Sridharan et al., 2006). Aniline derivatives are also widely used in many industries such as in the production of dyes and agrochemicals (Kasthuri et al., 2008). Keeping in mind the importance of aniline derivatives, the title compound was synthesized to study its crystal structure.
The molecule can – simultaneously – be regarded as a secondary amide, an enamine, an ester as well as featuring a Michael system. The C=C bond is (E) configured. The least-squares planes defined by the respective carbon atoms of the phenyl rings intersect at an angle of 49.57 (8) °. The central part of the molecule, including the ethyl group, is essentially planar (r.m.s. of the least-squares plane defined by all the non-hydrogen atoms of the respective part of this molecule = 0.0569 Å) with the oxygen atom of the ethoxy group deviating most from this plane (0.095 (1) Å) (Fig. 1).
In the crystal, intramolecular N–H···O bonds involving all secondary amine groups and double bonded oxygen atoms are observed. In addition, intermolecular C–H···O contacts whose range falls slightly below the sum of van-der-Waals radii of the atoms participating are present. The latter contacts are supported by hydrogen atoms on the phenyl group that is bonded to the amide-type nitrogen atom and exclusively have ketonic oxygen atoms as acceptors. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is S(6)S(6)R22(14)R22(18) on the unary level. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In total, the molecules are connected to chains along the crystallographic b axis. The shortest intercentroid distance between two aromatic systems was measured at 4.5754 (9) Å and is observed between the two different aromatic moieties in neighbouring molecules (Fig 2).
The packing of the title compound in the crystal structure is shown in Figure 3.