N,N'-Bis[(E)-4-nitro-benzyl-idene]-4,4'-oxydianiline.

The title compound, C(26)H(18)N(4)O(5), 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 inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions [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 = 466.44

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.02

3909 reflections

389 parameters

All H-atom parameters refined

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H18N4O5	Z = 2
Mr = 466.44	F(000) = 484
Triclinic, P1	Dx = 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

Siemens P4 diffractometer	Rint = 0.015
Radiation source: sealed tube	θmax = 25.0°, θmin = 2.5°
graphite	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 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(Fo2) + (0.0503P)2 + 0.1958P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3909 reflections	Δρmax = 0.14 e Å−3
389 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .