Bis­[4-(2-pyridyl­methyl­ene­amino)­phenyl] ether

The title compound, C₂₄H₁₈N₄O, is a bis-bidentate Schiff base ligand exhibiting pseudo-C₂ symmetry. The mol­ecule is twisted about the central ether linkage and exhibits an imine E configuration. In the crystal, the mol­ecules are linked by weak intermolecular C—H...N hydrogen bonds.

Computing details

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97).

(I)

Crystal data

C24H18N4O	F(000) = 792
Mr = 378.42	Dx = 1.291 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.3403 (8) Å	Cell parameters from 5000 reflections
b = 18.3849 (17) Å	θ = 2.0–25.9°
c = 8.5868 (6) Å	µ = 0.08 mm^−1
β = 91.958 (8)°	T = 153 K
V = 1947.0 (3) Å^3	Block, yellow
Z = 4	0.55 × 0.50 × 0.35 mm

Data collection

STOE IPDS diffractometer	2904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.9°, θmin = 2.0°
Detector resolution: 0.81Å pixels mm^-1	h = −14→15
φ oscillation scans	k = −22→22
14238 measured reflections	l = −10→10
3716 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: difference Fourier map
wR(F^2) = 0.094	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.1419P] where P = (Fo^2 + 2Fc^2)/3
3716 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.19492 (9)	0.18318 (8)	−0.25245 (15)	0.0586 (3)
N2	0.42393 (7)	0.11855 (5)	−0.03145 (11)	0.0353 (2)
N3	0.89625 (8)	−0.04533 (6)	0.85138 (13)	0.0444 (3)
N4	1.15560 (9)	−0.12726 (7)	0.83900 (13)	0.0531 (3)
O1	0.62405 (7)	0.15817 (4)	0.55555 (10)	0.0415 (2)
C1	0.15263 (14)	0.18432 (10)	−0.3984 (2)	0.0676 (5)
H1	0.0842 (16)	0.2090 (11)	−0.410 (2)	0.094 (6)*
C2	0.20045 (13)	0.15302 (9)	−0.52382 (18)	0.0585 (4)
H2	0.1649 (13)	0.1581 (9)	−0.625 (2)	0.070 (5)*
C3	0.29796 (12)	0.11791 (8)	−0.49962 (17)	0.0509 (3)
H3	0.3340 (14)	0.0957 (9)	−0.590 (2)	0.072 (5)*
C4	0.34383 (10)	0.11572 (7)	−0.35085 (15)	0.0416 (3)
H4	0.4160 (13)	0.0922 (8)	−0.3283 (18)	0.060 (4)*
C5	0.28982 (9)	0.14844 (6)	−0.23027 (14)	0.0383 (3)
C6	0.33588 (10)	0.15064 (7)	−0.06976 (15)	0.0388 (3)
H6	0.2944 (11)	0.1796 (8)	0.0061 (18)	0.052 (4)*
C7	0.47095 (8)	0.12860 (6)	0.11985 (13)	0.0326 (2)
C8	0.47424 (9)	0.19635 (6)	0.19436 (14)	0.0347 (3)
H8	0.4408 (10)	0.2389 (8)	0.1432 (16)	0.047 (4)*
C9	0.52812 (9)	0.20472 (6)	0.33687 (14)	0.0348 (3)
H9	0.5329 (10)	0.2512 (7)	0.3860 (15)	0.040 (3)*
C10	0.57698 (9)	0.14531 (6)	0.40985 (13)	0.0334 (3)
C11	0.57441 (10)	0.07771 (6)	0.33773 (15)	0.0385 (3)
H11	0.6093 (10)	0.0376 (7)	0.3857 (16)	0.042 (3)*
C12	0.52391 (9)	0.07033 (6)	0.19232 (15)	0.0370 (3)
H12	0.5232 (10)	0.0246 (8)	0.1399 (16)	0.045 (4)*
C13	0.69384 (9)	0.10627 (6)	0.62260 (14)	0.0360 (3)
C14	0.66890 (10)	0.07921 (7)	0.76643 (15)	0.0387 (3)
H14	0.6027 (12)	0.0929 (7)	0.8145 (17)	0.048 (4)*
C15	0.73845 (9)	0.02957 (7)	0.83957 (15)	0.0387 (3)
H15	0.7213 (10)	0.0097 (7)	0.9386 (17)	0.045 (4)*
C16	0.83293 (9)	0.00778 (7)	0.77040 (14)	0.0389 (3)
C17	0.85625 (11)	0.03622 (8)	0.62480 (16)	0.0476 (3)
H17	0.9225 (12)	0.0224 (8)	0.5713 (19)	0.060 (4)*
C18	0.78724 (11)	0.08536 (8)	0.55046 (16)	0.0456 (3)
H18	0.8029 (12)	0.1044 (8)	0.449 (2)	0.061 (4)*
C19	0.99335 (11)	−0.05683 (8)	0.81938 (16)	0.0475 (3)
H19	1.0315 (14)	−0.0257 (10)	0.740 (2)	0.081 (5)*
C20	1.05838 (9)	−0.11380 (7)	0.89892 (15)	0.0414 (3)
C21	1.02147 (11)	−0.15013 (8)	1.02727 (18)	0.0514 (3)
H21	0.9473 (13)	−0.1382 (9)	1.0666 (19)	0.067 (5)*
C22	1.08610 (12)	−0.20248 (8)	1.0971 (2)	0.0576 (4)
H22	1.0636 (14)	−0.2306 (10)	1.180 (2)	0.076 (5)*
C23	1.18595 (11)	−0.21664 (8)	1.03724 (18)	0.0515 (3)
H23	1.2346 (12)	−0.2519 (9)	1.0876 (19)	0.061 (4)*
C24	1.21686 (11)	−0.17804 (8)	0.90864 (17)	0.0519 (4)
H24	1.2860 (13)	−0.1873 (8)	0.8612 (18)	0.062 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0478 (6)	0.0782 (9)	0.0491 (8)	0.0168 (6)	−0.0072 (5)	−0.0018 (6)
N2	0.0390 (5)	0.0333 (5)	0.0335 (6)	−0.0007 (4)	−0.0015 (4)	0.0010 (4)
N3	0.0428 (6)	0.0512 (6)	0.0390 (6)	0.0065 (5)	−0.0031 (4)	0.0056 (5)
N4	0.0460 (6)	0.0752 (8)	0.0381 (7)	0.0124 (6)	0.0015 (5)	0.0025 (6)
O1	0.0518 (5)	0.0380 (4)	0.0339 (5)	0.0091 (4)	−0.0092 (4)	−0.0047 (3)
C1	0.0585 (9)	0.0865 (12)	0.0565 (11)	0.0204 (8)	−0.0176 (8)	0.0026 (8)
C2	0.0673 (9)	0.0655 (9)	0.0414 (9)	−0.0043 (7)	−0.0161 (7)	0.0052 (7)
C3	0.0579 (8)	0.0541 (8)	0.0403 (8)	−0.0079 (6)	−0.0028 (6)	−0.0046 (6)
C4	0.0437 (7)	0.0401 (6)	0.0406 (8)	−0.0033 (5)	−0.0029 (5)	−0.0025 (5)
C5	0.0376 (6)	0.0380 (6)	0.0391 (7)	−0.0020 (5)	−0.0022 (5)	0.0041 (5)
C6	0.0387 (6)	0.0423 (6)	0.0355 (7)	0.0015 (5)	0.0024 (5)	0.0006 (5)
C7	0.0332 (5)	0.0347 (6)	0.0300 (6)	−0.0003 (4)	0.0019 (4)	0.0008 (5)
C8	0.0389 (6)	0.0328 (6)	0.0326 (7)	0.0055 (5)	0.0029 (5)	0.0027 (5)
C9	0.0421 (6)	0.0295 (6)	0.0330 (7)	0.0035 (4)	0.0033 (5)	−0.0033 (5)
C10	0.0350 (6)	0.0358 (6)	0.0293 (6)	0.0011 (4)	−0.0005 (4)	−0.0008 (4)
C11	0.0451 (6)	0.0293 (6)	0.0405 (7)	0.0045 (5)	−0.0071 (5)	0.0017 (5)
C12	0.0438 (6)	0.0291 (6)	0.0379 (7)	0.0018 (5)	−0.0033 (5)	−0.0037 (5)
C13	0.0403 (6)	0.0347 (6)	0.0325 (7)	0.0009 (5)	−0.0072 (5)	−0.0027 (5)
C14	0.0366 (6)	0.0422 (6)	0.0371 (7)	−0.0004 (5)	0.0003 (5)	−0.0021 (5)
C15	0.0405 (6)	0.0435 (6)	0.0319 (7)	−0.0029 (5)	−0.0006 (5)	0.0033 (5)
C16	0.0396 (6)	0.0422 (6)	0.0345 (7)	0.0011 (5)	−0.0056 (5)	0.0012 (5)
C17	0.0436 (7)	0.0613 (8)	0.0382 (8)	0.0110 (6)	0.0046 (5)	0.0051 (6)
C18	0.0501 (7)	0.0542 (8)	0.0325 (7)	0.0072 (6)	0.0028 (5)	0.0065 (6)
C19	0.0449 (7)	0.0593 (8)	0.0381 (8)	0.0040 (6)	−0.0030 (5)	0.0064 (6)
C20	0.0390 (6)	0.0496 (7)	0.0350 (7)	0.0025 (5)	−0.0057 (5)	−0.0018 (5)
C21	0.0406 (7)	0.0599 (8)	0.0537 (9)	0.0028 (6)	0.0018 (6)	0.0090 (7)
C22	0.0547 (8)	0.0578 (9)	0.0602 (10)	0.0007 (7)	0.0004 (7)	0.0192 (7)
C23	0.0512 (8)	0.0462 (7)	0.0562 (9)	0.0082 (6)	−0.0107 (6)	−0.0022 (6)
C24	0.0446 (7)	0.0685 (9)	0.0422 (8)	0.0148 (6)	−0.0033 (6)	−0.0093 (7)

Geometric parameters (Å, º)

N1—C1	1.341 (2)	C9—H9	0.954 (13)
N1—C5	1.3418 (16)	C10—C11	1.3885 (16)
N2—C6	1.2698 (15)	C11—C12	1.3830 (17)
N2—C7	1.4167 (15)	C11—H11	0.941 (14)
N3—C19	1.2564 (17)	C12—H12	0.953 (14)
N3—C16	1.4179 (15)	C13—C14	1.3760 (18)
N4—C24	1.3302 (18)	C13—C18	1.3816 (18)
N4—C20	1.3445 (16)	C14—C15	1.3882 (17)
O1—C10	1.3817 (14)	C14—H14	0.961 (15)
O1—C13	1.3963 (13)	C15—C16	1.3857 (17)
C1—C2	1.372 (2)	C15—H15	0.955 (15)
C1—H1	0.96 (2)	C16—C17	1.3943 (19)
C2—C3	1.375 (2)	C17—C18	1.3827 (18)
C2—H2	0.965 (17)	C17—H17	0.984 (16)
C3—C4	1.3800 (19)	C18—H18	0.966 (17)
C3—H3	0.995 (18)	C19—C20	1.4731 (18)
C4—C5	1.3874 (18)	C19—H19	1.02 (2)
C4—H4	1.003 (16)	C20—C21	1.3793 (19)
C5—C6	1.4734 (17)	C21—C22	1.375 (2)
C6—H6	0.996 (15)	C21—H21	1.010 (16)
C7—C12	1.3908 (16)	C22—C23	1.376 (2)
C7—C8	1.4002 (16)	C22—H22	0.932 (19)
C8—C9	1.3811 (17)	C23—C24	1.377 (2)
C8—H8	0.981 (14)	C23—H23	0.974 (16)
C9—C10	1.3869 (16)	C24—H24	0.973 (16)
C1—N1—C5	116.74 (13)	C11—C12—H12	120.7 (8)
C6—N2—C7	119.80 (10)	C7—C12—H12	118.1 (8)
C19—N3—C16	121.48 (12)	C14—C13—C18	121.16 (11)
C24—N4—C20	117.26 (12)	C14—C13—O1	117.61 (11)
C10—O1—C13	119.39 (9)	C18—C13—O1	121.17 (11)
N1—C1—C2	124.25 (15)	C13—C14—C15	119.34 (12)
N1—C1—H1	114.6 (12)	C13—C14—H14	120.7 (9)
C2—C1—H1	121.2 (12)	C15—C14—H14	120.0 (9)
C1—C2—C3	118.42 (14)	C16—C15—C14	120.82 (12)
C1—C2—H2	118.2 (10)	C16—C15—H15	119.1 (8)
C3—C2—H2	123.4 (10)	C14—C15—H15	120.1 (8)
C2—C3—C4	118.86 (14)	C15—C16—C17	118.58 (11)
C2—C3—H3	119.1 (10)	C15—C16—N3	116.52 (11)
C4—C3—H3	122.1 (10)	C17—C16—N3	124.81 (11)
C3—C4—C5	119.07 (12)	C18—C17—C16	121.09 (12)
C3—C4—H4	121.6 (9)	C18—C17—H17	117.5 (9)
C5—C4—H4	119.3 (9)	C16—C17—H17	121.4 (9)
N1—C5—C4	122.66 (12)	C13—C18—C17	119.01 (12)
N1—C5—C6	115.25 (11)	C13—C18—H18	120.0 (9)
C4—C5—C6	122.02 (11)	C17—C18—H18	121.0 (9)
N2—C6—C5	121.93 (11)	N3—C19—C20	121.79 (13)
N2—C6—H6	122.2 (8)	N3—C19—H19	121.2 (10)
C5—C6—H6	115.9 (8)	C20—C19—H19	117.0 (10)
C12—C7—C8	118.35 (10)	N4—C20—C21	122.68 (12)
C12—C7—N2	118.77 (10)	N4—C20—C19	115.63 (12)
C8—C7—N2	122.66 (10)	C21—C20—C19	121.68 (12)
C9—C8—C7	120.63 (10)	C22—C21—C20	119.03 (13)
C9—C8—H8	119.3 (8)	C22—C21—H21	121.6 (9)
C7—C8—H8	120.0 (8)	C20—C21—H21	119.3 (9)
C8—C9—C10	120.09 (10)	C21—C22—C23	118.87 (15)
C8—C9—H9	120.8 (8)	C21—C22—H22	122.6 (11)
C10—C9—H9	119.1 (8)	C23—C22—H22	118.4 (11)
O1—C10—C9	115.93 (10)	C22—C23—C24	118.56 (13)
O1—C10—C11	124.02 (10)	C22—C23—H23	120.4 (9)
C9—C10—C11	120.03 (11)	C24—C23—H23	121.0 (9)
C12—C11—C10	119.55 (11)	N4—C24—C23	123.59 (13)
C12—C11—H11	120.2 (8)	N4—C24—H24	115.3 (9)
C10—C11—H11	120.2 (8)	C23—C24—H24	121.1 (9)
C11—C12—C7	121.25 (11)
C5—N1—C1—C2	−0.5 (3)	C10—O1—C13—C14	−123.27 (12)
N1—C1—C2—C3	0.2 (3)	C10—O1—C13—C18	59.70 (15)
C1—C2—C3—C4	−0.2 (2)	C18—C13—C14—C15	−0.55 (18)
C2—C3—C4—C5	0.5 (2)	O1—C13—C14—C15	−177.59 (10)
C1—N1—C5—C4	0.8 (2)	C13—C14—C15—C16	0.80 (18)
C1—N1—C5—C6	177.80 (14)	C14—C15—C16—C17	−0.64 (19)
C3—C4—C5—N1	−0.88 (19)	C14—C15—C16—N3	−177.49 (11)
C3—C4—C5—C6	−177.64 (12)	C19—N3—C16—C15	−163.59 (13)
C7—N2—C6—C5	173.27 (10)	C19—N3—C16—C17	19.8 (2)
N1—C5—C6—N2	178.26 (12)	C15—C16—C17—C18	0.2 (2)
C4—C5—C6—N2	−4.75 (18)	N3—C16—C17—C18	176.82 (12)
C6—N2—C7—C12	144.52 (11)	C14—C13—C18—C17	0.17 (19)
C6—N2—C7—C8	−40.95 (16)	O1—C13—C18—C17	177.09 (11)
C12—C7—C8—C9	−0.50 (17)	C16—C17—C18—C13	0.0 (2)
N2—C7—C8—C9	−175.05 (10)	C16—N3—C19—C20	−177.65 (12)
C7—C8—C9—C10	−1.88 (17)	C24—N4—C20—C21	0.1 (2)
C13—O1—C10—C9	−166.65 (10)	C24—N4—C20—C19	179.52 (12)
C13—O1—C10—C11	14.86 (17)	N3—C19—C20—N4	171.04 (13)
C8—C9—C10—O1	−176.76 (10)	N3—C19—C20—C21	−9.5 (2)
C8—C9—C10—C11	1.79 (17)	N4—C20—C21—C22	−0.2 (2)
O1—C10—C11—C12	179.13 (11)	C19—C20—C21—C22	−179.61 (14)
C9—C10—C11—C12	0.70 (18)	C20—C21—C22—C23	0.4 (2)
C10—C11—C12—C7	−3.15 (19)	C21—C22—C23—C24	−0.5 (2)
C8—C7—C12—C11	3.04 (17)	C20—N4—C24—C23	−0.2 (2)
N2—C7—C12—C11	177.80 (11)	C22—C23—C24—N4	0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N4^i	0.966 (17)	2.575 (17)	3.5265 (18)	168.1 (13)
C21—H21···N1^ii	1.010 (16)	2.550 (17)	3.4046 (19)	142.2 (12)

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