(E)-2-{N-Ethyl-4-[(4-nitro­phen­yl)diazen­yl]anilino}ethyl acrylate

Yousefi, M.; Hosseini, H.; Amani, V.; Arab Chamjangali, M.; Khavasi, H.R.

doi:10.1107/S1600536808003085

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o789

doi:10.1107/S1600536808003085

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(E)-2-{N-Ethyl-4-[(4-nitrophenyl)diazenyl]anilino}ethyl acrylate

Mohammad Yousefi,^a ^* Hossein Hosseini,^b Vahid Amani,^a Mansour Arab Chamjangali ^c and Hamid Reza Khavasi ^d

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, ^bDepartment of Chemistry, Faculty of Science and Engineering, Imam Hossein University, Tehran, Iran, ^cDepartment of Chemistry, Shahrood University of Technology, Shahrood, Iran, and ^dDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: myousefi50@yahoo.com

(Received 24 January 2008; accepted 31 March 2008; online 2 April 2008)

In the molecule of the title compound, C₁₉H₂₀N₄O₄, the rings are almost coplanar, forming a dihedral angle of 0.76 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Peters & Freeman (1991 ); Gregory (1991 ); Gur et al. (2007 ); Venkataraman (1970 ); Srinivasa et al. (2003 ). For bond-length data, see: Lacroix et al. (2000 ); Gunnlaugsson et al. (2001 ).

Experimental

Crystal data

C₁₉H₂₀N₄O₄
M_r = 368.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.1518 (9) Å
b = 10.6651 (11) Å
c = 20.6782 (19) Å
V = 1797.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
0.5 × 0.2 × 0.06 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005 )] T_min = 0.980, T_max = 0.990
15596 measured reflections
2456 independent reflections
2346 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.079
S = 1.12
2456 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O4ⁱ	0.97	2.40	3.189 (2)	138
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-STEP32 (Stoe & Cie, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003085/hk2424sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003085/hk2424Isup2.hkl

checkCIF report

Comment top

It is well known for many years that dyes have been most widely used in fields such as dyeing textile fibers, biomedical studies, advanced applications in organic synthesis and high technology areas like lasers, liquid crystalline displays, electrooptical devices and ink-jet printers (Peters & Freeman, 1991; Gregory 1991; Gur et al., 2007). Azo colorants are the most versatile class of dyes (Venkataraman 1970). They can also be used as indicators in chemical laboratories and as stains in the biological field (Srinivasa et al., 2003). We report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges (Lacroix et al., 2000; Gunnlaugsson et al., 2001). Rings A (C1—C6) and B (C7—C12) are, of course, planar and the dihedral angle between them is 0.76 (3)°, so they are also almost coplanar. The atoms N1, N2, N3, N4, O1 and O2 are at the distances of -0.124 (2) Å, 0.070 (3) Å, -0.016 (2) Å, 0.162 (3) Å, -0.066 (3) Å and -0.255 (2) Å, respectively, to the best plane of the coplanar rings.

In the crystal structure, intermolecular C—H···O hydrogen bonds link the molecules, in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Peters & Freeman (1991); Gregory (1991); Gur et al. (2007); Venkataraman (1970); Srinivasa et al. (2003); For bond-length data, see: Lacroix et al. (2000); Gunnlaugsson et al. (2001).

Experimental top

For the preparation of the title compound, (I), to a magnetically stirred solution of 4-nitro-4'-[N-ethyl-N-(2-hydroxyethyl)-amino]azobenzene (2.48 mmol) in THF (20 ml), was added dropwise acryloyl chloride (2.48 mmol) in dry nitrogen atmosphere. After 2 h, the mixture was filtered and the desired product was precipitated out by adding water. The solid filtered and washed several times with water, and then dried. The orange precipitated product was recrystallized from ethyl alcohol. After 72 h, orange plate crystals of (I) were isolated (yield; 52.0%, m.p. 397–398 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-STEP32 (Stoe & Cie, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(E)-2-{N-Ethyl-4-[(4-nitrophenyl)diazenyl]anilino}ethyl acrylate top

Crystal data top

C₁₉H₂₀N₄O₄	F(000) = 776
M_r = 368.39	D_x = 1.361 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5000 reflections
a = 8.1518 (9) Å	θ = 2.0–27.9°
b = 10.6651 (11) Å	µ = 0.10 mm⁻¹
c = 20.6782 (19) Å	T = 120 K
V = 1797.8 (3) Å³	Plate, orange
Z = 4	0.5 × 0.2 × 0.06 mm

Data collection top

Stoe IPDSII diffractometer	2456 independent reflections
Radiation source: fine-focus sealed tube	2346 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
rotation method scans	h = −10→10
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)]	k = −14→14
T_min = 0.980, T_max = 0.990	l = −27→26
15596 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.041P)² + 0.3046P] where P = (F_o² + 2F_c²)/3
2456 reflections	(Δ/σ)_max = 0.005
244 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₂₀N₄O₄	V = 1797.8 (3) Å³
M_r = 368.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.1518 (9) Å	µ = 0.10 mm⁻¹
b = 10.6651 (11) Å	T = 120 K
c = 20.6782 (19) Å	0.5 × 0.2 × 0.06 mm

Data collection top

Stoe IPDSII diffractometer	2456 independent reflections
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)]	2346 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.047
15596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.12	Δρ_max = 0.21 e Å⁻³
2456 reflections	Δρ_min = −0.22 e Å⁻³
244 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	1.10305 (16)	0.14200 (13)	0.09457 (7)	0.0364 (3)
O2	1.03152 (16)	−0.04894 (11)	0.07258 (7)	0.0313 (3)
O3	−0.36429 (14)	0.34551 (10)	0.47252 (5)	0.0216 (2)
O4	−0.21122 (16)	0.32212 (12)	0.56227 (6)	0.0294 (3)
N1	1.00462 (17)	0.05502 (13)	0.09634 (7)	0.0222 (3)
N2	0.40683 (16)	0.13800 (12)	0.22729 (6)	0.0205 (3)
N3	0.30983 (16)	0.04473 (12)	0.22891 (6)	0.0192 (3)
N4	−0.29651 (17)	0.09198 (12)	0.35372 (6)	0.0190 (3)
C1	0.84626 (18)	0.07543 (14)	0.12848 (7)	0.0189 (3)
C2	0.8210 (2)	0.18816 (14)	0.16069 (8)	0.0207 (3)
H2	0.9010	0.2503	0.1607	0.025*
C3	0.6730 (2)	0.20566 (14)	0.19291 (8)	0.0207 (3)
H3	0.6533	0.2803	0.2148	0.025*
C4	0.55405 (18)	0.11203 (14)	0.19253 (7)	0.0188 (3)
C5	0.5827 (2)	−0.00013 (15)	0.15898 (8)	0.0236 (3)
H5	0.5026	−0.0622	0.1585	0.028*
C6	0.7296 (2)	−0.01923 (14)	0.12656 (8)	0.0224 (3)
H6	0.7493	−0.0934	0.1042	0.027*
C7	0.16339 (18)	0.06323 (14)	0.26308 (7)	0.0182 (3)
C8	0.12233 (19)	0.17040 (14)	0.29917 (7)	0.0184 (3)
H8	0.1962	0.2367	0.3020	0.022*
C9	−0.02636 (19)	0.17795 (13)	0.33038 (7)	0.0185 (3)
H9	−0.0505	0.2492	0.3545	0.022*
C10	−0.14435 (18)	0.07970 (14)	0.32673 (7)	0.0170 (3)
C11	−0.0979 (2)	−0.03058 (13)	0.29288 (7)	0.0190 (3)
H11	−0.1685	−0.0990	0.2917	0.023*
C12	0.05171 (19)	−0.03651 (14)	0.26169 (7)	0.0190 (3)
H12	0.0791	−0.1089	0.2391	0.023*
C13	−0.4126 (2)	−0.01280 (14)	0.35654 (8)	0.0218 (3)
H13A	−0.4112	−0.0565	0.3154	0.026*
H13B	−0.5223	0.0202	0.3629	0.026*
C14	−0.3749 (2)	−0.10628 (16)	0.41043 (9)	0.0302 (4)
H14A	−0.3785	−0.0642	0.4514	0.036*
H14B	−0.2676	−0.1411	0.4039	0.036*
H14C	−0.4549	−0.1723	0.4098	0.036*
C15	−0.35038 (19)	0.21176 (14)	0.38075 (8)	0.0197 (3)
H15A	−0.4682	0.2195	0.3756	0.024*
H15B	−0.2990	0.2797	0.3571	0.024*
C16	−0.3070 (2)	0.22308 (14)	0.45203 (7)	0.0212 (3)
H16A	−0.3605	0.1575	0.4768	0.025*
H16B	−0.1894	0.2161	0.4581	0.025*
C17	−0.3027 (2)	0.38472 (15)	0.52915 (8)	0.0218 (3)
C18	−0.3577 (2)	0.51211 (16)	0.54784 (8)	0.0263 (3)
H18	−0.3365	0.5385	0.5899	0.032*
C19	−0.4339 (3)	0.58999 (18)	0.50938 (10)	0.0398 (5)
H19A	−0.4570	0.5667	0.4670	0.048*
H19B	−0.4649	0.6687	0.5244	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0293 (6)	0.0269 (6)	0.0529 (8)	−0.0081 (5)	0.0145 (6)	−0.0026 (6)
O2	0.0316 (6)	0.0222 (5)	0.0401 (7)	0.0030 (5)	0.0113 (6)	−0.0058 (5)
O3	0.0232 (5)	0.0183 (5)	0.0235 (5)	0.0039 (4)	−0.0010 (4)	−0.0038 (4)
O4	0.0289 (6)	0.0331 (6)	0.0261 (6)	0.0055 (6)	−0.0039 (5)	−0.0022 (5)
N1	0.0223 (6)	0.0194 (6)	0.0250 (7)	0.0007 (5)	0.0034 (5)	0.0016 (5)
N2	0.0205 (6)	0.0176 (6)	0.0233 (6)	−0.0009 (5)	0.0001 (5)	−0.0010 (5)
N3	0.0196 (6)	0.0169 (6)	0.0211 (6)	−0.0001 (5)	0.0006 (5)	0.0007 (5)
N4	0.0204 (6)	0.0143 (5)	0.0224 (6)	0.0011 (5)	0.0014 (5)	−0.0009 (5)
C1	0.0198 (7)	0.0177 (7)	0.0193 (7)	0.0007 (6)	0.0014 (6)	0.0012 (6)
C2	0.0211 (7)	0.0161 (6)	0.0248 (7)	−0.0023 (6)	−0.0005 (6)	0.0008 (6)
C3	0.0235 (8)	0.0145 (6)	0.0240 (7)	−0.0001 (6)	−0.0003 (6)	−0.0021 (6)
C4	0.0187 (7)	0.0179 (7)	0.0198 (6)	0.0003 (6)	−0.0006 (6)	0.0005 (6)
C5	0.0242 (7)	0.0185 (7)	0.0281 (8)	−0.0051 (6)	0.0029 (6)	−0.0048 (6)
C6	0.0256 (8)	0.0165 (7)	0.0252 (7)	−0.0015 (6)	0.0029 (6)	−0.0038 (6)
C7	0.0189 (7)	0.0161 (7)	0.0195 (7)	0.0015 (6)	−0.0007 (6)	0.0008 (5)
C8	0.0208 (7)	0.0138 (6)	0.0206 (6)	−0.0004 (6)	−0.0007 (6)	0.0005 (6)
C9	0.0233 (7)	0.0124 (6)	0.0196 (6)	0.0010 (6)	−0.0005 (6)	−0.0006 (5)
C10	0.0199 (7)	0.0146 (6)	0.0166 (6)	0.0018 (5)	−0.0014 (5)	0.0018 (5)
C11	0.0217 (7)	0.0144 (6)	0.0208 (7)	−0.0014 (6)	−0.0008 (6)	−0.0008 (6)
C12	0.0232 (7)	0.0129 (6)	0.0210 (7)	0.0025 (6)	−0.0001 (6)	−0.0019 (6)
C13	0.0197 (7)	0.0199 (7)	0.0258 (7)	−0.0021 (6)	0.0009 (6)	−0.0009 (6)
C14	0.0395 (9)	0.0207 (7)	0.0303 (8)	−0.0048 (7)	0.0005 (8)	0.0047 (7)
C15	0.0205 (7)	0.0154 (6)	0.0233 (7)	0.0049 (6)	0.0012 (6)	0.0009 (6)
C16	0.0247 (7)	0.0167 (6)	0.0221 (7)	0.0042 (6)	0.0005 (6)	−0.0005 (6)
C17	0.0208 (7)	0.0231 (7)	0.0214 (7)	−0.0010 (6)	0.0037 (6)	−0.0002 (6)
C18	0.0306 (8)	0.0232 (7)	0.0251 (7)	−0.0011 (7)	0.0025 (7)	−0.0063 (6)
C19	0.0603 (13)	0.0257 (8)	0.0333 (9)	0.0090 (9)	−0.0009 (9)	−0.0063 (8)

Geometric parameters (Å, º) top

C1—C6	1.388 (2)	C13—N4	1.466 (2)
C1—C2	1.390 (2)	C13—C14	1.527 (2)
C1—N1	1.4681 (19)	C13—H13A	0.9700
C2—C3	1.391 (2)	C13—H13B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.392 (2)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.402 (2)	C15—N4	1.4618 (18)
C4—N2	1.4261 (19)	C15—C16	1.520 (2)
C5—C6	1.387 (2)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—H6	0.9300	C16—O3	1.4500 (17)
C7—C12	1.400 (2)	C16—H16A	0.9700
C7—N3	1.4012 (19)	C16—H16B	0.9700
C7—C8	1.406 (2)	C17—O4	1.213 (2)
C8—C9	1.376 (2)	C17—O3	1.3412 (19)
C8—H8	0.9300	C17—C18	1.482 (2)
C9—C10	1.424 (2)	C18—C19	1.307 (3)
C9—H9	0.9300	C18—H18	0.9300
C10—N4	1.367 (2)	C19—H19A	0.9300
C10—C11	1.420 (2)	C19—H19B	0.9300
C11—C12	1.381 (2)	N1—O1	1.2271 (18)
C11—H11	0.9300	N1—O2	1.2323 (18)
C12—H12	0.9300	N2—N3	1.2712 (18)

C6—C1—C2	122.79 (14)	N4—C13—H13B	108.9
C6—C1—N1	118.80 (13)	C14—C13—H13B	108.9
C2—C1—N1	118.39 (13)	H13A—C13—H13B	107.7
C1—C2—C3	118.30 (14)	C13—C14—H14A	109.5
C1—C2—H2	120.8	C13—C14—H14B	109.5
C3—C2—H2	120.8	H14A—C14—H14B	109.5
C2—C3—C4	120.35 (14)	C13—C14—H14C	109.5
C2—C3—H3	119.8	H14A—C14—H14C	109.5
C4—C3—H3	119.8	H14B—C14—H14C	109.5
C3—C4—C5	119.92 (14)	N4—C15—C16	111.73 (13)
C3—C4—N2	116.35 (13)	N4—C15—H15A	109.3
C5—C4—N2	123.73 (14)	C16—C15—H15A	109.3
C6—C5—C4	120.54 (15)	N4—C15—H15B	109.3
C6—C5—H5	119.7	C16—C15—H15B	109.3
C4—C5—H5	119.7	H15A—C15—H15B	107.9
C5—C6—C1	118.09 (14)	O3—C16—C15	106.25 (12)
C5—C6—H6	121.0	O3—C16—H16A	110.5
C1—C6—H6	121.0	C15—C16—H16A	110.5
C12—C7—N3	115.89 (13)	O3—C16—H16B	110.5
C12—C7—C8	118.28 (13)	C15—C16—H16B	110.5
N3—C7—C8	125.81 (14)	H16A—C16—H16B	108.7
C9—C8—C7	120.43 (14)	O4—C17—O3	123.49 (15)
C9—C8—H8	119.8	O4—C17—C18	122.93 (15)
C7—C8—H8	119.8	O3—C17—C18	113.59 (14)
C8—C9—C10	121.81 (13)	C19—C18—C17	124.60 (16)
C8—C9—H9	119.1	C19—C18—H18	117.7
C10—C9—H9	119.1	C17—C18—H18	117.7
N4—C10—C11	121.51 (13)	C18—C19—H19A	120.0
N4—C10—C9	121.39 (13)	C18—C19—H19B	120.0
C11—C10—C9	117.09 (13)	H19A—C19—H19B	120.0
C12—C11—C10	120.23 (14)	O1—N1—O2	123.50 (13)
C12—C11—H11	119.9	O1—N1—C1	118.44 (13)
C10—C11—H11	119.9	O2—N1—C1	118.05 (13)
C11—C12—C7	121.99 (14)	N3—N2—C4	112.63 (12)
C11—C12—H12	119.0	N2—N3—C7	115.66 (12)
C7—C12—H12	119.0	C10—N4—C15	120.84 (13)
N4—C13—C14	113.39 (14)	C10—N4—C13	121.96 (12)
N4—C13—H13A	108.9	C15—N4—C13	117.20 (13)
C14—C13—H13A	108.9	C17—O3—C16	114.54 (12)

C6—C1—C2—C3	0.8 (2)	O3—C17—C18—C19	−11.8 (3)
N1—C1—C2—C3	−177.92 (13)	C6—C1—N1—O1	175.31 (15)
C1—C2—C3—C4	0.0 (2)	C2—C1—N1—O1	−6.0 (2)
C2—C3—C4—C5	−0.6 (2)	C6—C1—N1—O2	−4.8 (2)
C2—C3—C4—N2	179.52 (14)	C2—C1—N1—O2	173.98 (15)
C3—C4—C5—C6	0.6 (2)	C3—C4—N2—N3	−174.90 (13)
N2—C4—C5—C6	−179.55 (15)	C5—C4—N2—N3	5.3 (2)
C4—C5—C6—C1	0.1 (2)	C4—N2—N3—C7	179.20 (12)
C2—C1—C6—C5	−0.8 (2)	C12—C7—N3—N2	176.24 (13)
N1—C1—C6—C5	177.89 (14)	C8—C7—N3—N2	−5.4 (2)
C12—C7—C8—C9	−2.1 (2)	C11—C10—N4—C15	−171.70 (14)
N3—C7—C8—C9	179.54 (14)	C9—C10—N4—C15	7.2 (2)
C7—C8—C9—C10	−0.9 (2)	C11—C10—N4—C13	7.9 (2)
C8—C9—C10—N4	−174.91 (14)	C9—C10—N4—C13	−173.24 (14)
C8—C9—C10—C11	4.0 (2)	C16—C15—N4—C10	−90.19 (16)
N4—C10—C11—C12	174.82 (13)	C16—C15—N4—C13	90.21 (17)
C9—C10—C11—C12	−4.1 (2)	C14—C13—N4—C10	78.35 (18)
C10—C11—C12—C7	1.2 (2)	C14—C13—N4—C15	−102.06 (16)
N3—C7—C12—C11	−179.50 (14)	O4—C17—O3—C16	−2.6 (2)
C8—C7—C12—C11	2.0 (2)	C18—C17—O3—C16	177.69 (13)
N4—C15—C16—O3	179.17 (12)	C15—C16—O3—C17	−164.62 (13)
O4—C17—C18—C19	168.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O4ⁱ	0.97	2.40	3.189 (2)	138

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₄O₄
M_r	368.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	8.1518 (9), 10.6651 (11), 20.6782 (19)
V (Å³)	1797.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.5 × 0.2 × 0.06

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical [shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)]
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	15596, 2456, 2346
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 1.12
No. of reflections	2456
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-STEP32 (Stoe & Cie, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O4ⁱ	0.97	2.40	3.189 (2)	138.00

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, and Imam Hossein University for financial support.

References

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