Ethyl (Z)-3-(4-methyl­anilino)-2-[(4-methyl­phen­yl)carbamo­yl]prop-2-enoate

Islor, A.M.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812043723

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3218

doi:10.1107/S1600536812043723

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Ethyl (Z)-3-(4-methylanilino)-2-[(4-methylphenyl)carbamoyl]prop-2-enoate

Arun M. Islor,^a B. Garudachari,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^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

(Received 18 October 2012; accepted 22 October 2012; online 27 October 2012)

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

C₂₀H₂₂N₂O₃
M_r = 338.40
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.147
S = 1.05
4353 reflections
237 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043723/zq2185sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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 column chromatography using petrol ether and ethyl acetate (v:v = 5:5) as the eluent 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%).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 0 - 1]. Intermolecular C–H···O contacts are depicted with green dashed lines, intramolecular N–H···O hydrogen bonds are depicted with blue dashed lines. Symmetry operators: (i) -x + 1/2, -y + 3/2, -z; (ii) -x + 1/2, -y + 1/2, -z.
	Fig. 3. Molecular packing of the title compound, viewed along [0 0 - 1] (anisotropic displacement ellipsoids drawn at 50% probability level).

Ethyl (Z)-3-(4-methylanilino)-2-[(4-methylphenyl)carbamoyl]prop-2-enoate top

Crystal data top

C₂₀H₂₂N₂O₃	F(000) = 1440
M_r = 338.40	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0721P)² + 2.7716P] where P = (F_o² + 2F_c²)/3
4353 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₃	V = 3515.07 (15) Å³
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	4353 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3411 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.984	R_int = 0.022
16569 measured reflections

Refinement top

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	Δρ_max = 0.56 e Å⁻³
4353 reflections	Δρ_min = −0.22 e Å⁻³
237 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.965, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	16569, 4353, 3411
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

References

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