(E)-N′-(4-Nitro­benzyl­idene)-4-(8-quinol­yloxy)butano­hydrazide

XiaHou, G.-L.; Ding, Y.-C.; Fan, X.-N.

doi:10.1107/S1600536810020039

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1522

doi:10.1107/S1600536810020039

Open

access

(E)-N′-(4-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide

Guo-Lun XiaHou,^a Ye-Chun Ding ^a and Xiao-Na Fan ^a ^*

^aKey Lab of Natural Medicine Research and Development in Jiangxi, Gannan Medical University, Ganzhou, Jiangxi 341000, People's Republic of China
^*Correspondence e-mail: xiaonafanll@yahoo.cn

(Received 20 May 2010; accepted 27 May 2010; online 5 June 2010)

In the title compound, C₂₀H₁₈N₄O₄, conformation along the bond sequence linking the benzene and quinoline rings, which have a mean interplanar dihedral angle of 2.7 (5)°, is trans–(+)gauche–trans–trans–(−)gauche–trans–trans. In the crystal structure, a pair of intermolecular N—H⋯O hydrogen bonds links the molecules into centrosymmetric cyclic R₂²(8) dimers, which are aggregated via π–π interactions into parallel sheets [quinoline–benzene ring centroid separation = 3.6173 (16)–3.6511 (16) Å]. The sheets are further connected through weak C—H⋯O interactions, giving a supramolecular two-dimensional network.

Related literature

For general background to Schiff bases in coordination chemistry, see: Calligaris & Randaccio (1987 ). For related structures, see: Zheng, Li et al. (2008 ); Zheng, Qiu et al. (2006 ); Zheng, Wu, Lu et al. (2006 ); Zheng (2006 ); Zheng, Wu, Li et al. (2006 , 2007 ); Xie et al. (2008 ); Chen & Li (2009 ); Zhang et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₈N₄O₄
M_r = 378.38
Monoclinic, P 2₁ /c
a = 9.836 (3) Å
b = 10.633 (3) Å
c = 17.566 (5) Å
β = 92.365 (7)°
V = 1835.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.22 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.986
9957 measured reflections
3256 independent reflections
2345 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.146
S = 1.07
3256 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.03	2.876 (3)	170
C10—H10B⋯O3ⁱⁱ	0.97	2.45	3.311 (3)	148
C2—H2⋯O4ⁱⁱⁱ	0.93	2.58	3.496 (3)	167
Symmetry codes: (i) -x+2, -y+2, -z; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020039/zs2040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020039/zs2040Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry, playing an important role in the development of the chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Calligaris & Randaccio, 1987). Structures of Schiff bases derived from substituted 4-(quinolin-8-yloxy)butanehydrazide and closely related to the title compound have been reported earlier (Zheng, Li et al., 2008; Zheng, Wu, Lu et al., 2006; Zheng, 2006; Zheng, Wu, Li et al., 2006, 2007; Xie et al., 2008; Chen & Li, 2009; Zhang et al., 2009). In this contribution, we present the synthesis and crystal structure of a new ligand C₂₀H₁₈N₄O₄ (I), which contains oxygen and nitrogen donors and a flexible aliphatic spacer.

In (I) (Fig.1) the asymmetric unit contains a crystallographically independent molecule with a trans-(+)gauche-trans-trans-(-)gauche-trans-trans conformation along the quinoline ring–benzene ring bond sequence [torsion angles (°): C8–O1–C10–C11, 179.83 (18); O1–C10–C11–C12, 65.1 (3); C10–C11–C12–C13, -178.24; C11–C12–C13–N2, 114.1 (2); C12–C13–N2–N3, -0.1 (3); C13–N2–N3–C14, -178.96 (7); N2–N3–C14–C15, -179.17 (16)]. The bond lengths and angles in (I) are in good agreement with the expected values (Allen et al., 1987) and are comparable to those in the related compounds (Zheng, Wu, Lu et al., 2006; Zheng, 2006; Zheng, Wu, Li et al., 2006, 2007; Xie et al., 2008; Chen et al., 2009; Zhang, XiaHou et al., 2009). The C14—N3 and C13—O2 bond lengths [1.269 (3) and 1.235 (2) Å, respectively] indicate the presence of a typical C═N and C═O. The C═N—N angle of 115.79 (18)° is significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms, probably due to repulsion between the nitrogen lone pairs and the adjacent N atom (Zheng, Qiu et al., 2006). The benzene and quinoline ring systems are close to coplanar [dihedral angle, 2.7 (5)°]. In the crystal structure, intramolecular C—H···N and C—H···O interactions (Table 1, Fig. 1) produce two edge-sharing S(5) ring motifs (Bernstein et al., 1995) and a pair of intermolecular N—H···O hydrogen bonds link the molecules into centrosymmetric cyclic R²₂(8) dimers (Fig. 2), which are aggregated via π–π interactions into parallel sheets [quinoline–benzene ring centroid separation: 3.6173 (16)–3.6511 (16) Å], which are further connected through weak C—H···O interactions, giving a supramolecular two-dimensional network (Fig. 3).

Related literature top

For general background to Schiff bases in coordination chemistry, see: Calligaris & Randaccio (1987). For related structures, see: Zheng, Li et al. (2008); Zheng, Qiu et al. (2006); Zheng, Wu, Lu et al. (2006); Zheng (2006); Zheng, Wu, Li et al. (2006, 2007); Xie et al. (2008); Chen & Li (2009); Zhang et al. (2009). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Reagents and solvents used were of commercially available quality. The title compound (I) was synthesized according to the method of Zheng, Li et al., 2008. 4-(Quinolin-8-yloxy)butanehydrazide (0.01 mol), p-formylnitrobenzene (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Yellow single crystals of (I) suitable for the X-ray diffraction study were obtained by slow evaporation of a tetrahydrofuran solution over a period of four days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 30% probability level. Intramolecular C–H···N and C–H···O interactions are shown as dashed lines.
	Fig. 2. The cyclic hydrogen-bonded dimer with hydrogen bonds shown as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.
	Fig. 3. Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

(E)-N'-(4-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide top

Crystal data top

C₂₀H₁₈N₄O₄	F(000) = 792
M_r = 378.38	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3279 reflections
a = 9.836 (3) Å	θ = 2.2–27.9°
b = 10.633 (3) Å	µ = 0.10 mm⁻¹
c = 17.566 (5) Å	T = 296 K
β = 92.365 (7)°	Prism, yellow
V = 1835.6 (9) Å³	0.22 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3256 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→11
T_min = 0.979, T_max = 0.986	k = −12→12
9957 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0719P)² + 0.3873P] where P = (F_o² + 2F_c²)/3
3256 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈N₄O₄	V = 1835.6 (9) Å³
M_r = 378.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.836 (3) Å	µ = 0.10 mm⁻¹
b = 10.633 (3) Å	T = 296 K
c = 17.566 (5) Å	0.22 × 0.17 × 0.15 mm
β = 92.365 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3256 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2345 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.036
9957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
3256 reflections	Δρ_min = −0.23 e Å⁻³
253 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.75513 (15)	0.53054 (15)	0.16112 (8)	0.0599 (4)
O2	1.05475 (15)	0.89991 (18)	0.07985 (10)	0.0749 (5)
O3	0.0388 (2)	0.8161 (3)	−0.16156 (15)	0.1302 (10)
O4	0.04918 (18)	0.6940 (2)	−0.06516 (13)	0.0903 (6)
N1	0.50202 (18)	0.48897 (16)	0.10959 (10)	0.0542 (5)
N2	0.85327 (17)	0.90258 (17)	0.01739 (10)	0.0499 (4)
H2A	0.8844	0.9544	−0.0152	0.060*
N3	0.71999 (16)	0.86354 (16)	0.00912 (10)	0.0466 (4)
N4	0.0993 (2)	0.7717 (2)	−0.10668 (13)	0.0710 (6)
C1	0.3767 (2)	0.4663 (2)	0.08357 (15)	0.0651 (7)
H1	0.3479	0.5042	0.0380	0.078*
C2	0.2845 (2)	0.3894 (2)	0.11982 (17)	0.0685 (7)
H2	0.1962	0.3793	0.0998	0.082*
C3	0.3263 (2)	0.3297 (2)	0.18475 (15)	0.0642 (7)
H3	0.2665	0.2777	0.2097	0.077*
C4	0.4606 (2)	0.34635 (18)	0.21447 (11)	0.0472 (5)
C5	0.5148 (3)	0.2828 (2)	0.28008 (12)	0.0601 (6)
H5	0.4608	0.2271	0.3063	0.072*
C6	0.6447 (3)	0.3036 (2)	0.30424 (12)	0.0605 (6)
H6	0.6793	0.2610	0.3471	0.073*
C7	0.7296 (2)	0.3877 (2)	0.26657 (11)	0.0521 (5)
H7	0.8184	0.4012	0.2851	0.063*
C8	0.6817 (2)	0.44914 (18)	0.20301 (11)	0.0444 (5)
C9	0.5446 (2)	0.42934 (17)	0.17467 (10)	0.0410 (5)
C10	0.8940 (2)	0.5533 (2)	0.18444 (13)	0.0587 (6)
H10A	0.9454	0.4755	0.1842	0.070*
H10B	0.8996	0.5879	0.2356	0.070*
C11	0.9503 (2)	0.6450 (2)	0.12900 (15)	0.0663 (7)
H11A	0.9384	0.6113	0.0779	0.080*
H11B	1.0472	0.6550	0.1401	0.080*
C12	0.8825 (2)	0.7721 (2)	0.13204 (13)	0.0615 (6)
H12A	0.7853	0.7618	0.1225	0.074*
H12B	0.8969	0.8070	0.1827	0.074*
C13	0.9360 (2)	0.8621 (2)	0.07498 (13)	0.0561 (6)
C14	0.6530 (2)	0.90707 (19)	−0.04826 (11)	0.0451 (5)
H14	0.6949	0.9608	−0.0818	0.054*
C15	0.5098 (2)	0.87299 (17)	−0.06186 (10)	0.0422 (5)
C16	0.4388 (2)	0.9199 (2)	−0.12587 (12)	0.0528 (5)
H16	0.4825	0.9730	−0.1591	0.063*
C17	0.3046 (2)	0.8885 (2)	−0.14041 (13)	0.0581 (6)
H17	0.2572	0.9203	−0.1831	0.070*
C18	0.2416 (2)	0.8095 (2)	−0.09103 (12)	0.0503 (5)
C19	0.3084 (2)	0.7626 (2)	−0.02718 (12)	0.0518 (5)
H19	0.2635	0.7104	0.0060	0.062*
C20	0.4429 (2)	0.79389 (19)	−0.01275 (11)	0.0475 (5)
H20	0.4892	0.7618	0.0302	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0511 (9)	0.0703 (10)	0.0573 (9)	−0.0236 (8)	−0.0086 (7)	0.0125 (8)
O2	0.0459 (9)	0.1000 (13)	0.0779 (11)	−0.0223 (9)	−0.0080 (8)	0.0215 (10)
O3	0.0686 (13)	0.181 (2)	0.1362 (19)	0.0046 (16)	−0.0528 (14)	0.0321 (19)
O4	0.0516 (10)	0.1168 (17)	0.1021 (15)	−0.0198 (11)	−0.0025 (10)	−0.0187 (13)
N1	0.0546 (11)	0.0479 (10)	0.0592 (11)	−0.0031 (9)	−0.0103 (9)	0.0030 (8)
N2	0.0389 (9)	0.0549 (10)	0.0559 (10)	−0.0102 (8)	0.0021 (8)	0.0007 (8)
N3	0.0387 (9)	0.0472 (10)	0.0541 (10)	−0.0061 (8)	0.0047 (8)	−0.0070 (8)
N4	0.0460 (11)	0.0887 (16)	0.0770 (14)	0.0091 (12)	−0.0111 (11)	−0.0183 (13)
C1	0.0564 (14)	0.0588 (14)	0.0781 (16)	0.0060 (12)	−0.0205 (12)	−0.0039 (12)
C2	0.0432 (12)	0.0687 (16)	0.0928 (19)	0.0000 (12)	−0.0065 (13)	−0.0211 (14)
C3	0.0516 (13)	0.0623 (14)	0.0801 (17)	−0.0155 (12)	0.0208 (12)	−0.0221 (13)
C4	0.0523 (12)	0.0399 (11)	0.0505 (11)	−0.0051 (10)	0.0143 (9)	−0.0121 (9)
C5	0.0829 (17)	0.0493 (13)	0.0499 (12)	−0.0090 (12)	0.0230 (12)	−0.0003 (10)
C6	0.0850 (18)	0.0582 (13)	0.0385 (11)	0.0083 (13)	0.0041 (11)	0.0062 (10)
C7	0.0559 (12)	0.0575 (13)	0.0425 (11)	0.0029 (11)	−0.0035 (9)	−0.0026 (10)
C8	0.0461 (11)	0.0435 (10)	0.0435 (11)	−0.0048 (9)	0.0020 (9)	−0.0023 (9)
C9	0.0455 (11)	0.0357 (10)	0.0416 (10)	−0.0021 (9)	0.0014 (8)	−0.0041 (8)
C10	0.0422 (12)	0.0608 (13)	0.0725 (15)	−0.0079 (11)	−0.0037 (11)	−0.0013 (11)
C11	0.0520 (13)	0.0645 (15)	0.0831 (16)	−0.0131 (12)	0.0126 (12)	−0.0032 (13)
C12	0.0461 (12)	0.0765 (16)	0.0622 (14)	−0.0066 (12)	0.0054 (10)	0.0092 (12)
C13	0.0434 (12)	0.0658 (14)	0.0590 (13)	−0.0086 (11)	0.0026 (10)	0.0016 (11)
C14	0.0462 (11)	0.0437 (11)	0.0458 (11)	−0.0065 (9)	0.0059 (9)	−0.0052 (9)
C15	0.0454 (11)	0.0391 (10)	0.0422 (10)	0.0025 (9)	0.0026 (9)	−0.0075 (8)
C16	0.0618 (13)	0.0492 (12)	0.0473 (11)	0.0026 (11)	0.0006 (10)	0.0035 (9)
C17	0.0603 (14)	0.0613 (14)	0.0514 (12)	0.0178 (12)	−0.0125 (11)	−0.0031 (11)
C18	0.0391 (10)	0.0548 (12)	0.0563 (12)	0.0081 (10)	−0.0063 (9)	−0.0134 (10)
C19	0.0436 (11)	0.0564 (13)	0.0555 (12)	−0.0039 (10)	0.0018 (9)	−0.0008 (10)
C20	0.0430 (11)	0.0543 (12)	0.0448 (11)	−0.0013 (10)	−0.0047 (9)	0.0012 (9)

Geometric parameters (Å, º) top

O1—C8	1.363 (2)	C7—C8	1.361 (3)
O1—C10	1.430 (2)	C7—H7	0.9300
O2—C13	1.235 (2)	C8—C9	1.433 (3)
O3—N4	1.208 (3)	C10—C11	1.500 (3)
O4—N4	1.220 (3)	C10—H10A	0.9700
N1—C1	1.319 (3)	C10—H10B	0.9700
N1—C9	1.358 (2)	C11—C12	1.508 (3)
N2—C13	1.343 (3)	C11—H11A	0.9700
N2—N3	1.377 (2)	C11—H11B	0.9700
N2—H2A	0.8600	C12—C13	1.497 (3)
N3—C14	1.269 (3)	C12—H12A	0.9700
N4—C18	1.471 (3)	C12—H12B	0.9700
C1—C2	1.394 (4)	C14—C15	1.464 (3)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.354 (4)	C15—C20	1.390 (3)
C2—H2	0.9300	C15—C16	1.392 (3)
C3—C4	1.412 (3)	C16—C17	1.375 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C9	1.413 (3)	C17—C18	1.374 (3)
C4—C5	1.421 (3)	C17—H17	0.9300
C5—C6	1.348 (3)	C18—C19	1.370 (3)
C5—H5	0.9300	C19—C20	1.377 (3)
C6—C7	1.407 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300

C8—O1—C10	118.32 (16)	O1—C10—H10B	110.2
C1—N1—C9	117.24 (19)	C11—C10—H10B	110.2
C13—N2—N3	121.83 (18)	H10A—C10—H10B	108.5
C13—N2—H2A	119.1	C10—C11—C12	112.5 (2)
N3—N2—H2A	119.1	C10—C11—H11A	109.1
C14—N3—N2	115.79 (18)	C12—C11—H11A	109.1
O3—N4—O4	123.0 (2)	C10—C11—H11B	109.1
O3—N4—C18	118.4 (3)	C12—C11—H11B	109.1
O4—N4—C18	118.6 (2)	H11A—C11—H11B	107.8
N1—C1—C2	124.4 (2)	C13—C12—C11	112.35 (19)
N1—C1—H1	117.8	C13—C12—H12A	109.1
C2—C1—H1	117.8	C11—C12—H12A	109.1
C3—C2—C1	118.6 (2)	C13—C12—H12B	109.1
C3—C2—H2	120.7	C11—C12—H12B	109.1
C1—C2—H2	120.7	H12A—C12—H12B	107.9
C2—C3—C4	120.0 (2)	O2—C13—N2	119.3 (2)
C2—C3—H3	120.0	O2—C13—C12	121.3 (2)
C4—C3—H3	120.0	N2—C13—C12	119.38 (19)
C3—C4—C9	116.9 (2)	N3—C14—C15	120.28 (19)
C3—C4—C5	123.6 (2)	N3—C14—H14	119.9
C9—C4—C5	119.41 (19)	C15—C14—H14	119.9
C6—C5—C4	119.8 (2)	C20—C15—C16	118.90 (19)
C6—C5—H5	120.1	C20—C15—C14	121.72 (18)
C4—C5—H5	120.1	C16—C15—C14	119.38 (19)
C5—C6—C7	121.9 (2)	C17—C16—C15	120.6 (2)
C5—C6—H6	119.0	C17—C16—H16	119.7
C7—C6—H6	119.0	C15—C16—H16	119.7
C8—C7—C6	119.9 (2)	C18—C17—C16	119.1 (2)
C8—C7—H7	120.0	C18—C17—H17	120.5
C6—C7—H7	120.0	C16—C17—H17	120.5
C7—C8—O1	125.06 (19)	C19—C18—C17	121.7 (2)
C7—C8—C9	120.23 (19)	C19—C18—N4	118.3 (2)
O1—C8—C9	114.71 (16)	C17—C18—N4	120.0 (2)
N1—C9—C4	122.77 (18)	C18—C19—C20	119.2 (2)
N1—C9—C8	118.49 (17)	C18—C19—H19	120.4
C4—C9—C8	118.73 (17)	C20—C19—H19	120.4
O1—C10—C11	107.34 (19)	C19—C20—C15	120.53 (19)
O1—C10—H10A	110.2	C19—C20—H20	119.7
C11—C10—H10A	110.2	C15—C20—H20	119.7

C13—N2—N3—C14	−178.96 (19)	C8—O1—C10—C11	179.83 (18)
C9—N1—C1—C2	2.4 (3)	O1—C10—C11—C12	65.1 (3)
N1—C1—C2—C3	−2.5 (4)	C10—C11—C12—C13	−178.24 (19)
C1—C2—C3—C4	0.2 (3)	N3—N2—C13—O2	180.00 (19)
C2—C3—C4—C9	1.7 (3)	N3—N2—C13—C12	−0.1 (3)
C2—C3—C4—C5	−176.9 (2)	C11—C12—C13—O2	−66.0 (3)
C3—C4—C5—C6	179.5 (2)	C11—C12—C13—N2	114.1 (2)
C9—C4—C5—C6	0.9 (3)	N2—N3—C14—C15	−179.17 (16)
C4—C5—C6—C7	0.4 (3)	N3—C14—C15—C20	0.6 (3)
C5—C6—C7—C8	−1.1 (3)	N3—C14—C15—C16	−178.84 (18)
C6—C7—C8—O1	−178.65 (19)	C20—C15—C16—C17	−0.1 (3)
C6—C7—C8—C9	0.5 (3)	C14—C15—C16—C17	179.41 (18)
C10—O1—C8—C7	0.7 (3)	C15—C16—C17—C18	−0.3 (3)
C10—O1—C8—C9	−178.53 (17)	C16—C17—C18—C19	0.9 (3)
C1—N1—C9—C4	−0.3 (3)	C16—C17—C18—N4	−178.20 (19)
C1—N1—C9—C8	178.11 (19)	O3—N4—C18—C19	177.6 (2)
C3—C4—C9—N1	−1.7 (3)	O4—N4—C18—C19	−4.7 (3)
C5—C4—C9—N1	176.92 (18)	O3—N4—C18—C17	−3.2 (3)
C3—C4—C9—C8	179.88 (18)	O4—N4—C18—C17	174.4 (2)
C5—C4—C9—C8	−1.5 (3)	C17—C18—C19—C20	−1.1 (3)
C7—C8—C9—N1	−177.70 (18)	N4—C18—C19—C20	178.07 (18)
O1—C8—C9—N1	1.6 (3)	C18—C19—C20—C15	0.6 (3)
C7—C8—C9—C4	0.8 (3)	C16—C15—C20—C19	−0.1 (3)
O1—C8—C9—C4	−179.99 (16)	C14—C15—C20—C19	−179.55 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.03	2.876 (3)	170
C12—H12A···O1	0.97	2.57	2.912 (3)	101
C12—H12A···N3	0.97	2.33	2.807 (3)	109
C10—H10B···O3ⁱⁱ	0.97	2.45	3.311 (3)	148
C2—H2···O4ⁱⁱⁱ	0.93	2.58	3.496 (3)	167

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x+1, −y+3/2, z+1/2; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄O₄
M_r	378.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.836 (3), 10.633 (3), 17.566 (5)
β (°)	92.365 (7)
V (Å³)	1835.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	9957, 3256, 2345
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.146, 1.07
No. of reflections	3256
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.03	2.876 (3)	169.9
C12—H12A···O1	0.97	2.57	2.912 (3)	101
C12—H12A···N3	0.97	2.33	2.807 (3)	109.3
C10—H10B···O3ⁱⁱ	0.97	2.45	3.311 (3)	148.4
C2—H2···O4ⁱⁱⁱ	0.93	2.58	3.496 (3)	166.6

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x+1, −y+3/2, z+1/2; (iii) −x, −y+1, −z.

Acknowledgements

The authors thank the Key Lab of Natural Medicine Research and Development in Jiangxi for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. J. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715–738. London: Pergamon. Google Scholar
Chen, M.-E. & Li, J.-M. (2009). Acta Cryst. E65, o295. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, H., Meng, S.-M., Fan, Y.-Q. & Yang, G.-C. (2008). Acta Cryst. E64, o2114. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, J., XiaHou, G.-L., Zhang, S.-S. & Zeng, J. (2009). Acta Cryst. E65, o1695–o1696. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B. (2006). Acta Cryst. E62, o5146–o5147. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Li, J.-K., Sun, Y.-F. & Wu, R.-T. (2008). Acta Cryst. E64, o297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, P.-W., Qiu, Q.-M., Lin, Y.-Y. & Liu, K.-F. (2006). Acta Cryst. E62, o1913–o1914. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Li, J.-K. & Lu, J.-R. (2007). Acta Cryst. E63, o3284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Li, J.-K. & Sun, Y.-F. (2006). Acta Cryst. E62, o4882–o4883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Lu, J.-R. & Sun, Y.-F. (2006). Acta Cryst. E62, o4293–o4295. Web of Science CSD CrossRef IUCr Journals Google Scholar