N,N′-Bis[(E)-4-nitro­benzyl­idene]-4,4′-oxydianiline

Lee, H.K.; Lee, S.W.

doi:10.1107/S1600536809033844

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2263

doi:10.1107/S1600536809033844

Open

access

N,N′-Bis[(E)-4-nitrobenzylidene]-4,4′-oxydianiline

Hee K. Lee ^a and Soon W. Lee ^a ^*

^aDepartment of Chemistry (BK21), Sungkyunkwan University, Natural Science Campus, Suwon 440-746, Republic of Korea
^*Correspondence e-mail: soonwlee@skku.edu

(Received 20 August 2009; accepted 24 August 2009; online 29 August 2009)

The title compound, C₂₆H₁₈N₄O₅, can be regarded as an extended ether with two terminal nitro groups. The two aryl rings bonded to the central O atom form a dihedral angle of 75.72 (6)°, and the terminal nitro groups are slightly twisted [by 6.4 (2) and 3.3 (3)°] from the benzene rings to which they are attached. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distances = 3.794 (3) Å].

Related literature

For applications of coordination polymers, see: Barnett & Champness (2003 ); Batten et al. (2009 ); Perry et al. (2009 ). For bis(pyridine)-, bis(furan)-, bis(thiophene)-, and (pyridine–amine)-type linking ligands as well as compounds that are structurally close to the title compound, see Yun et al. (2009 ) and references therein.

Experimental

Crystal data

C₂₆H₁₈N₄O₅
M_r = 466.44
Triclinic, $[P \overline 1]$
a = 8.3322 (11) Å
b = 9.0716 (16) Å
c = 17.107 (2) Å
α = 74.714 (9)°
β = 78.885 (10)°
γ = 64.643 (10)°
V = 1122.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.52 × 0.32 × 0.26 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
4200 measured reflections
3909 independent reflections
2972 reflections with I > 2σ(I)
R_int = 0.015
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.02
3909 reflections
389 parameters
All H-atom parameters refined
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O1ⁱ	0.956 (19)	2.57 (2)	3.375 (2)	142.4 (14)
C20—H20⋯O5ⁱⁱ	1.016 (19)	2.48 (2)	3.323 (2)	139.7 (14)
Symmetry codes: (i) -x+3, -y-2, -z+1; (ii) x, y-1, z.

Data collection: XSCANS (Siemens, 1995 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033844/cv2603sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033844/cv2603Isup2.hkl

checkCIF report

Comment top

Coordination polymers gain continuous attention due to their desirable zeolite-like properties applicable to catalysis, nonlinear optical activity, spin crossover, luminescence, long-range magnetism, adsorption-desorption, and gas storage (Barnett & Champness, 2003; Batten et al., 2009; Perry IV et al., 2009). Carefule choice of relevant linking ligands is one of the key factors for the successful preparation of such polymers. We have continually reported long bis(pyridine)-, bis(furan)-, bis(thiophene)-, and (pyridine–amine)-type linking ligands and their coordination polymers (Yun et al., 2009). To an extension of our ongoing study of novel linking ligands and their coordination polymers, we prepared a long, potential linking ligand containing two terminal nitro groups.

The molecular structure of the title compound with the atom-numbering scheme is shown in Fig. 1. The overall structure can be regarded as a long ether possessing two terminal nitro (NO₂) groups. Two bis(pyridine)-type linking ligands containing an intervening oxydianilne fragment, which are structurally close to the title compound, were recently reported by our research group: [(3-py)—CHN—C₆H₄—O—C₆H₄—NCH—(3-py)] and [(4-py)—CHN—C₆H₄—O—C₆H₄—NCH—(4-py)] (Yun et al., 2009), which, however, were not structurally characterized. In the title compound, the dihedral angle between two aryl rings (C8–13 and C14–C19) bonded to the central oxygen (O13) is 75.72 (6)°. Terminal nitro groups are not coplanar with the phenyl rings to which they are attached, with the dihedral angle 6.4 (2) (N1, O1, O2) or 3.3 (3)° (N2, O4, O5). These bonding parameters might indicate the flexibility of the title compound. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1) and π–π interactions proved by centroid-to-centroid distances of 3.794 (3) Å.

Related literature top

For applications of coordination polymers, see: Barnett & Champness (2003); Batten et al. (2009); Perry et al. (2009). For bis(pyridine)-, bis(furan)-, bis(thiophene)-, and (pyridine–amine)-type linking ligands as well as compounds that are structurally close to the title compound, see Yun et al. (2009).

Experimental top

4-Nitrobenzaldehyde (1.12 g, 7.41 mmol) and 4,4-oxydianiline (0.67 g, 3.31 mmol) were dissolved in methanol (80 ml), to which formic acid (0.15 ml) was added. The resulting mixture was stirred at room temperature for 1 h. Dichloromethane (50 ml) was then added to the mixture, which was further stirred for 24 h. The resulting solution was filtered to give a yellow solid, which was washed with hexane (20 ml × 2). X-ray quality crystals were obtained from dichloromethane/hexane. Yield: 92%. mp: 457–459 K. IR (KBr, cm^-1): 3427, 3099, 2846, 2441, 1595, 1517, 1490, 1340, 1240, 1104, 850.

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); data reduction: XSCANS (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing 50% probability displacement ellipsoids.

N,N'-Bis[(E)-4-nitrobenzylidene]-4,4'-oxydianiline top

Crystal data top

C₂₆H₁₈N₄O₅	Z = 2
M_r = 466.44	F(000) = 484
Triclinic, P1	D_x = 1.380 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3322 (11) Å	Cell parameters from 23 reflections
b = 9.0716 (16) Å	θ = 5.2–12.5°
c = 17.107 (2) Å	µ = 0.10 mm⁻¹
α = 74.714 (9)°	T = 293 K
β = 78.885 (10)°	Block, yellow
γ = 64.643 (10)°	0.52 × 0.32 × 0.26 mm
V = 1122.4 (3) Å³

Data collection top

Siemens P4 diffractometer	R_int = 0.015
Radiation source: sealed tube	θ_max = 25.0°, θ_min = 2.5°
Graphite monochromator	h = 0→9
ω scans	k = −9→10
4200 measured reflections	l = −19→20
3909 independent reflections	3 standard reflections every 97 reflections
2972 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	All H-atom parameters refined
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0503P)² + 0.1958P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3909 reflections	Δρ_max = 0.14 e Å⁻³
389 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0142 (18)

Crystal data top

C₂₆H₁₈N₄O₅	γ = 64.643 (10)°
M_r = 466.44	V = 1122.4 (3) Å³
Triclinic, P1	Z = 2
a = 8.3322 (11) Å	Mo Kα radiation
b = 9.0716 (16) Å	µ = 0.10 mm⁻¹
c = 17.107 (2) Å	T = 293 K
α = 74.714 (9)°	0.52 × 0.32 × 0.26 mm
β = 78.885 (10)°

Data collection top

Siemens P4 diffractometer	R_int = 0.015
4200 measured reflections	3 standard reflections every 97 reflections
3909 independent reflections	intensity decay: none
2972 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	All H-atom parameters refined
S = 1.02	Δρ_max = 0.14 e Å⁻³
3909 reflections	Δρ_min = −0.19 e Å⁻³
389 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	1.7461 (2)	−1.5786 (2)	0.74989 (10)	0.1006 (6)
O2	1.8293 (3)	−1.6837 (2)	0.64341 (12)	0.1072 (6)
O3	0.66294 (17)	−0.41925 (15)	0.27173 (8)	0.0675 (4)
O4	0.8910 (2)	0.87019 (18)	−0.12942 (11)	0.0838 (5)
O5	0.7292 (3)	0.9709 (2)	−0.02700 (11)	0.1184 (7)
N1	1.7396 (2)	−1.5702 (2)	0.67832 (12)	0.0737 (5)
N2	1.2107 (2)	−0.96099 (19)	0.43282 (10)	0.0631 (4)
N3	0.6330 (2)	0.22173 (17)	0.13724 (9)	0.0556 (4)
N4	0.7983 (2)	0.86027 (19)	−0.06546 (11)	0.0667 (4)
C1	1.6151 (2)	−1.4143 (2)	0.63208 (11)	0.0561 (4)
C2	1.5930 (3)	−1.4084 (3)	0.55334 (13)	0.0697 (5)
C3	1.4715 (3)	−1.2638 (3)	0.51122 (13)	0.0692 (5)
C4	1.3747 (2)	−1.1275 (2)	0.54727 (11)	0.0567 (4)
C5	1.4043 (3)	−1.1372 (3)	0.62583 (12)	0.0666 (5)
C6	1.5244 (3)	−1.2814 (3)	0.66859 (12)	0.0646 (5)
C7	1.2366 (3)	−0.9765 (3)	0.50481 (13)	0.0640 (5)
C8	1.0753 (2)	−0.8152 (2)	0.39338 (11)	0.0557 (4)
C9	1.0170 (3)	−0.8290 (2)	0.32617 (11)	0.0614 (5)
C10	0.8827 (3)	−0.6950 (2)	0.28467 (12)	0.0603 (5)
C11	0.8091 (2)	−0.5460 (2)	0.30985 (11)	0.0554 (4)
C12	0.8703 (3)	−0.5267 (2)	0.37428 (12)	0.0640 (5)
C13	1.0025 (3)	−0.6607 (2)	0.41617 (13)	0.0650 (5)
C14	0.6656 (2)	−0.2624 (2)	0.24132 (10)	0.0527 (4)
C15	0.5020 (2)	−0.1291 (2)	0.23764 (11)	0.0570 (4)
C16	0.4942 (2)	0.0295 (2)	0.20338 (11)	0.0560 (4)
C17	0.6481 (2)	0.0556 (2)	0.17089 (9)	0.0504 (4)
C18	0.8120 (2)	−0.0792 (2)	0.17666 (11)	0.0565 (4)
C19	0.8211 (2)	−0.2388 (2)	0.21218 (11)	0.0569 (4)
C20	0.7171 (2)	0.2500 (2)	0.06917 (11)	0.0534 (4)
C21	0.7241 (2)	0.4137 (2)	0.03302 (10)	0.0495 (4)
C22	0.8183 (3)	0.4350 (2)	−0.04281 (11)	0.0580 (5)
C23	0.8408 (3)	0.5821 (2)	−0.07591 (12)	0.0588 (5)
C24	0.7657 (2)	0.70731 (19)	−0.03286 (11)	0.0527 (4)
C25	0.6657 (3)	0.6929 (2)	0.04074 (11)	0.0606 (5)
C26	0.6447 (3)	0.5455 (2)	0.07374 (11)	0.0567 (4)
H2	1.657 (3)	−1.501 (3)	0.5313 (12)	0.079 (6)*
H3	1.454 (3)	−1.258 (3)	0.4561 (14)	0.089 (7)*
H5	1.332 (3)	−1.034 (3)	0.6515 (13)	0.089 (7)*
H6	1.542 (3)	−1.293 (2)	0.7242 (13)	0.077 (6)*
H7	1.167 (3)	−0.892 (3)	0.5362 (14)	0.099 (8)*
H9	1.073 (3)	−0.939 (2)	0.3098 (11)	0.072 (6)*
H10	0.839 (3)	−0.707 (2)	0.2398 (12)	0.077 (6)*
H12	0.822 (3)	−0.421 (3)	0.3907 (12)	0.075 (6)*
H13	1.044 (2)	−0.650 (2)	0.4595 (12)	0.063 (5)*
H15	0.397 (3)	−0.151 (2)	0.2596 (11)	0.071 (6)*
H16	0.381 (3)	0.125 (2)	0.2019 (11)	0.071 (6)*
H18	0.923 (3)	−0.061 (2)	0.1556 (11)	0.063 (5)*
H19	0.934 (3)	−0.331 (2)	0.2162 (11)	0.064 (5)*
H20	0.784 (3)	0.161 (2)	0.0355 (11)	0.066 (5)*
H22	0.876 (3)	0.342 (2)	−0.0724 (11)	0.071 (6)*
H23	0.904 (3)	0.597 (2)	−0.1244 (12)	0.075 (6)*
H25	0.616 (3)	0.777 (2)	0.0689 (12)	0.071 (6)*
H26	0.577 (3)	0.528 (2)	0.1242 (12)	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0832 (11)	0.1146 (13)	0.0768 (11)	−0.0193 (10)	−0.0332 (9)	0.0079 (9)
O2	0.1096 (14)	0.0678 (10)	0.1184 (14)	−0.0056 (10)	−0.0316 (11)	−0.0138 (10)
O3	0.0578 (8)	0.0524 (7)	0.0882 (9)	−0.0272 (6)	−0.0217 (7)	0.0123 (6)
O4	0.0881 (11)	0.0700 (9)	0.0968 (11)	−0.0467 (8)	−0.0059 (9)	0.0018 (8)
O5	0.200 (2)	0.0732 (10)	0.1070 (13)	−0.0782 (13)	0.0012 (13)	−0.0290 (10)
N1	0.0614 (11)	0.0742 (12)	0.0796 (13)	−0.0268 (9)	−0.0185 (9)	0.0020 (10)
N2	0.0586 (9)	0.0617 (9)	0.0639 (10)	−0.0236 (8)	−0.0106 (8)	−0.0018 (7)
N3	0.0617 (9)	0.0480 (8)	0.0558 (9)	−0.0231 (7)	−0.0096 (7)	−0.0031 (6)
N4	0.0812 (12)	0.0512 (9)	0.0746 (11)	−0.0319 (9)	−0.0258 (9)	−0.0009 (8)
C1	0.0512 (10)	0.0583 (10)	0.0584 (11)	−0.0253 (9)	−0.0112 (8)	−0.0007 (8)
C2	0.0724 (13)	0.0627 (12)	0.0707 (13)	−0.0205 (11)	−0.0128 (10)	−0.0147 (10)
C3	0.0763 (13)	0.0713 (13)	0.0579 (12)	−0.0268 (11)	−0.0163 (10)	−0.0073 (10)
C4	0.0542 (10)	0.0590 (10)	0.0568 (10)	−0.0278 (9)	−0.0060 (8)	−0.0018 (8)
C5	0.0674 (12)	0.0655 (12)	0.0615 (12)	−0.0217 (10)	−0.0082 (10)	−0.0108 (9)
C6	0.0667 (12)	0.0721 (13)	0.0549 (11)	−0.0286 (10)	−0.0128 (9)	−0.0061 (9)
C7	0.0611 (12)	0.0633 (12)	0.0619 (12)	−0.0249 (10)	−0.0042 (9)	−0.0045 (10)
C8	0.0493 (10)	0.0543 (10)	0.0570 (10)	−0.0224 (8)	−0.0051 (8)	0.0020 (8)
C9	0.0598 (11)	0.0569 (11)	0.0606 (11)	−0.0197 (9)	−0.0048 (9)	−0.0074 (9)
C10	0.0596 (11)	0.0620 (11)	0.0575 (11)	−0.0259 (9)	−0.0091 (9)	−0.0037 (9)
C11	0.0492 (10)	0.0511 (10)	0.0598 (10)	−0.0242 (8)	−0.0069 (8)	0.0071 (8)
C12	0.0705 (13)	0.0498 (10)	0.0674 (12)	−0.0228 (9)	−0.0100 (10)	−0.0047 (9)
C13	0.0733 (13)	0.0614 (12)	0.0618 (12)	−0.0294 (10)	−0.0179 (10)	−0.0022 (9)
C14	0.0561 (10)	0.0483 (9)	0.0528 (10)	−0.0247 (8)	−0.0109 (8)	0.0019 (7)
C15	0.0475 (10)	0.0582 (11)	0.0636 (11)	−0.0237 (9)	−0.0086 (8)	−0.0025 (8)
C16	0.0490 (10)	0.0518 (10)	0.0607 (11)	−0.0156 (8)	−0.0112 (8)	−0.0043 (8)
C17	0.0575 (10)	0.0481 (9)	0.0454 (9)	−0.0227 (8)	−0.0089 (8)	−0.0033 (7)
C18	0.0519 (10)	0.0543 (10)	0.0615 (11)	−0.0248 (9)	−0.0053 (8)	−0.0024 (8)
C19	0.0484 (10)	0.0509 (10)	0.0634 (11)	−0.0176 (8)	−0.0083 (8)	−0.0003 (8)
C20	0.0603 (11)	0.0473 (9)	0.0549 (10)	−0.0230 (8)	−0.0103 (8)	−0.0080 (8)
C21	0.0536 (10)	0.0456 (9)	0.0499 (9)	−0.0201 (8)	−0.0122 (7)	−0.0048 (7)
C22	0.0698 (12)	0.0462 (10)	0.0567 (11)	−0.0224 (9)	−0.0026 (9)	−0.0119 (8)
C23	0.0635 (11)	0.0524 (10)	0.0573 (11)	−0.0245 (9)	−0.0026 (9)	−0.0057 (8)
C24	0.0592 (10)	0.0431 (9)	0.0589 (10)	−0.0221 (8)	−0.0202 (8)	−0.0018 (7)
C25	0.0757 (13)	0.0463 (10)	0.0595 (11)	−0.0190 (9)	−0.0140 (10)	−0.0137 (8)
C26	0.0651 (11)	0.0524 (10)	0.0507 (10)	−0.0219 (9)	−0.0066 (9)	−0.0091 (8)

Geometric parameters (Å, º) top

O1—N1	1.217 (2)	C10—C11	1.373 (3)
O2—N1	1.211 (2)	C10—H10	0.96 (2)
O3—C14	1.388 (2)	C11—C12	1.379 (3)
O3—C11	1.394 (2)	C12—C13	1.379 (3)
O4—N4	1.218 (2)	C12—H12	0.97 (2)
O5—N4	1.216 (2)	C13—H13	0.920 (19)
N1—C1	1.474 (2)	C14—C19	1.380 (2)
N2—C7	1.252 (3)	C14—C15	1.381 (2)
N2—C8	1.422 (2)	C15—C16	1.381 (2)
N3—C20	1.262 (2)	C15—H15	0.97 (2)
N3—C17	1.424 (2)	C16—C17	1.387 (2)
N4—C24	1.472 (2)	C16—H16	0.97 (2)
C1—C6	1.360 (3)	C17—C18	1.389 (2)
C1—C2	1.378 (3)	C18—C19	1.389 (2)
C2—C3	1.382 (3)	C18—H18	0.990 (19)
C2—H2	0.92 (2)	C19—H19	0.956 (19)
C3—C4	1.384 (3)	C20—C21	1.472 (2)
C3—H3	0.97 (2)	C20—H20	1.016 (19)
C4—C5	1.386 (3)	C21—C26	1.392 (2)
C4—C7	1.475 (3)	C21—C22	1.393 (2)
C5—C6	1.380 (3)	C22—C23	1.383 (3)
C5—H5	1.03 (2)	C22—H22	0.99 (2)
C6—H6	0.96 (2)	C23—C24	1.371 (3)
C7—H7	0.96 (2)	C23—H23	0.90 (2)
C8—C9	1.385 (3)	C24—C25	1.378 (3)
C8—C13	1.397 (3)	C25—C26	1.378 (3)
C9—C10	1.386 (3)	C25—H25	0.92 (2)
C9—H9	0.99 (2)	C26—H26	0.953 (19)

C14—O3—C11	118.85 (13)	C13—C12—H12	119.3 (12)
O2—N1—O1	123.39 (19)	C12—C13—C8	120.5 (2)
O2—N1—C1	118.48 (19)	C12—C13—H13	120.5 (12)
O1—N1—C1	118.1 (2)	C8—C13—H13	119.0 (12)
C7—N2—C8	120.80 (18)	C19—C14—C15	120.83 (16)
C20—N3—C17	118.44 (15)	C19—C14—O3	122.74 (16)
O5—N4—O4	123.56 (17)	C15—C14—O3	116.35 (15)
O5—N4—C24	117.74 (18)	C14—C15—C16	119.40 (17)
O4—N4—C24	118.69 (16)	C14—C15—H15	118.0 (11)
C6—C1—C2	122.07 (18)	C16—C15—H15	122.6 (11)
C6—C1—N1	119.08 (18)	C15—C16—C17	120.79 (17)
C2—C1—N1	118.85 (19)	C15—C16—H16	120.6 (12)
C1—C2—C3	118.6 (2)	C17—C16—H16	118.6 (12)
C1—C2—H2	119.0 (13)	C16—C17—C18	119.11 (15)
C3—C2—H2	122.4 (13)	C16—C17—N3	118.57 (15)
C2—C3—C4	120.64 (19)	C18—C17—N3	122.20 (16)
C2—C3—H3	119.7 (13)	C17—C18—C19	120.35 (17)
C4—C3—H3	119.6 (13)	C17—C18—H18	119.4 (10)
C3—C4—C5	118.88 (18)	C19—C18—H18	120.2 (10)
C3—C4—C7	121.08 (18)	C14—C19—C18	119.44 (17)
C5—C4—C7	119.99 (19)	C14—C19—H19	120.4 (11)
C6—C5—C4	120.9 (2)	C18—C19—H19	120.2 (11)
C6—C5—H5	121.3 (12)	N3—C20—C21	122.54 (17)
C4—C5—H5	117.8 (12)	N3—C20—H20	122.0 (10)
C1—C6—C5	118.84 (19)	C21—C20—H20	115.4 (10)
C1—C6—H6	118.9 (12)	C26—C21—C22	119.25 (16)
C5—C6—H6	122.2 (12)	C26—C21—C20	121.80 (16)
N2—C7—C4	121.7 (2)	C22—C21—C20	118.91 (16)
N2—C7—H7	122.5 (14)	C23—C22—C21	120.78 (17)
C4—C7—H7	115.8 (14)	C23—C22—H22	119.2 (11)
C9—C8—C13	118.62 (17)	C21—C22—H22	120.0 (11)
C9—C8—N2	116.51 (17)	C24—C23—C22	118.32 (18)
C13—C8—N2	124.84 (17)	C24—C23—H23	119.8 (13)
C8—C9—C10	120.91 (19)	C22—C23—H23	121.9 (13)
C8—C9—H9	117.4 (11)	C23—C24—C25	122.38 (16)
C10—C9—H9	121.7 (11)	C23—C24—N4	118.52 (17)
C11—C10—C9	119.33 (19)	C25—C24—N4	119.07 (16)
C11—C10—H10	120.1 (12)	C24—C25—C26	119.05 (17)
C9—C10—H10	120.6 (12)	C24—C25—H25	121.6 (12)
C10—C11—C12	120.95 (17)	C26—C25—H25	119.3 (12)
C10—C11—O3	117.62 (17)	C25—C26—C21	120.13 (18)
C12—C11—O3	121.29 (17)	C25—C26—H26	123.1 (12)
C11—C12—C13	119.60 (19)	C21—C26—H26	116.8 (12)
C11—C12—H12	121.1 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱ	0.956 (19)	2.57 (2)	3.375 (2)	142.4 (14)
C20—H20···O5ⁱⁱ	1.016 (19)	2.48 (2)	3.323 (2)	139.7 (14)

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₄O₅
M_r	466.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3322 (11), 9.0716 (16), 17.107 (2)
α, β, γ (°)	74.714 (9), 78.885 (10), 64.643 (10)
V (Å³)	1122.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.52 × 0.32 × 0.26

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4200, 3909, 2972
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.02
No. of reflections	3909
No. of parameters	389
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: XSCANS (Siemens, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱ	0.956 (19)	2.57 (2)	3.375 (2)	142.4 (14)
C20—H20···O5ⁱⁱ	1.016 (19)	2.48 (2)	3.323 (2)	139.7 (14)

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

Acknowledgements

This work was supported by the Korean Science and Engineering Foundation (KOSEF) grant funded by the Korean government (MEST) (grant No. 2009–007996).

References

Barnett, S. A. & Champness, N. R. (2003). Coord. Chem. Rev. 246, 145–168. Web of Science CrossRef CAS Google Scholar
Batten, S. R., Neville, S. M. & Turner, D. R. (2009). Coordination Polymers: Design, Analysis and Application. Cambridge: The Royal Society of Chemistry. Google Scholar
Perry IV, J. J., Perman, J. A. & Zaworotko, M. J. (2009). Chem. Soc. Rev. 38, 1400–1417. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yun, H. J., Lim, S. H. & Lee, S. W. (2009). Polyhedron, 28, 614–620. Web of Science CSD CrossRef CAS Google Scholar