Bis[4-(2-hydr-oxy-3-methoxy-benzyl-ideneamino)phen-yl] ether.

The title compound, C(28)H(24)N(2)O(5), a flexible Schiff base ligand, was prepared in high yield by a Schiff base condensation of 3-methoxy-salicylaldehyde and bis-(4-amino-phen-yl) ether in methanol. The mol-ecule lies on a twofold rotation axis, and each half exhibits an imine E configuration and an O-H⋯N hydrogen bond. The dihedral angle between the two benzene rings attached to the central O atom is 69.22 (6)°, and that between each of these rings and the other benzene ring in the same half of the mol-ecule is 24.29 (11)°, illustrating the degree of twisting of the flexible mol-ecule.

Related literature

For related literature, see: Chu et al. (2007 ▶); Guo et al. (2002 ▶); He et al. (2000 ▶); Tesouro Vallina et al. (2001 ▶); Yoshida et al. (1999 ▶).

Experimental

Crystal data

C28H24N2O5

M = 468.49

Monoclinic,

a = 15.585 (7) Å

b = 7.578 (4) Å

c = 19.859 (9) Å

β = 92.760 (8)°

V = 2342.7 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8736 measured reflections

2689 independent reflections

2016 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.166

S = 1.11

2689 reflections

165 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014980/cf2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014980/cf2200Isup2.hkl

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

C28H24N2O5	F000 = 984
Mr = 468.49	Dx = 1.328 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
a = 15.585 (7) Å	Cell parameters from 2635 reflections
b = 7.578 (4) Å	θ = 1.7–25.1º
c = 19.859 (9) Å	µ = 0.09 mm−1
β = 92.760 (8)º	T = 173 (2) K
V = 2342.7 (19) Å3	Prism, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Monochromator: graphite	θmax = 27.5º
T = 173(2) K	θmin = 2.6º
ω scans	h = −20→19
Absorption correction: none	k = −9→9
8736 measured reflections	l = −22→25
2689 independent reflections

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.5764P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2689 reflections	Δρmax = 0.15 e Å−3
165 parameters	Δρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.88064 (10)	0.0091 (2)	0.52377 (7)	0.0561 (4)
O1	1.0000	−0.3717 (3)	0.7500	0.0694 (6)
O2	0.78593 (9)	0.02484 (16)	0.41186 (7)	0.0660 (4)
H3	0.8101	−0.0219	0.4461	0.079*
C4	0.91503 (11)	−0.0853 (3)	0.58068 (8)	0.0527 (5)
C13	0.80476 (12)	0.1980 (2)	0.41092 (9)	0.0521 (4)
O3	0.71769 (10)	0.21180 (19)	0.31172 (8)	0.0739 (5)
C12	0.77074 (13)	0.3000 (2)	0.35765 (10)	0.0572 (5)
C3	0.98968 (12)	−0.0344 (3)	0.61733 (9)	0.0574 (5)
H8	1.0210	0.0659	0.6036	0.069*
C6	0.90099 (13)	−0.3309 (3)	0.65622 (10)	0.0610 (5)
H9	0.8709	−0.4333	0.6694	0.073*
C5	0.87355 (12)	−0.2368 (3)	0.59967 (10)	0.0591 (5)
H10	0.8250	−0.2772	0.5733	0.071*
C8	0.85726 (12)	0.2774 (2)	0.46152 (10)	0.0564 (5)
C2	1.01805 (12)	−0.1291 (3)	0.67334 (9)	0.0581 (5)
H12	1.0689	−0.0941	0.6981	0.070*
C7	0.89139 (13)	0.1765 (3)	0.51873 (10)	0.0602 (5)
C1	0.97295 (13)	−0.2738 (3)	0.69341 (9)	0.0562 (5)
C11	0.79102 (15)	0.4744 (3)	0.35347 (12)	0.0718 (6)
H15	0.7685	0.5426	0.3165	0.086*
C14	0.66750 (17)	0.3156 (3)	0.26521 (12)	0.0825 (7)
H16A	0.6388	0.4096	0.2895	0.124*
H16B	0.6243	0.2408	0.2418	0.124*
H16C	0.7048	0.3679	0.2322	0.124*
C9	0.87598 (16)	0.4578 (3)	0.45639 (12)	0.0744 (6)
H17	0.9110	0.5138	0.4905	0.089*
C10	0.84410 (17)	0.5530 (3)	0.40260 (14)	0.0825 (7)
H18	0.8584	0.6743	0.3988	0.099*
H4	0.9250 (14)	0.249 (3)	0.5555 (12)	0.082 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0574 (9)	0.0669 (10)	0.0438 (8)	−0.0043 (8)	0.0010 (7)	−0.0009 (7)
O1	0.0892 (14)	0.0622 (12)	0.0554 (11)	0.000	−0.0097 (10)	0.000
O2	0.0793 (10)	0.0517 (7)	0.0653 (9)	−0.0103 (7)	−0.0143 (7)	0.0074 (6)
C4	0.0519 (10)	0.0664 (11)	0.0400 (9)	−0.0021 (8)	0.0041 (7)	−0.0068 (8)
C13	0.0562 (10)	0.0481 (10)	0.0528 (10)	−0.0019 (8)	0.0097 (8)	0.0000 (8)
O3	0.0880 (11)	0.0637 (9)	0.0679 (9)	0.0048 (7)	−0.0170 (8)	0.0087 (7)
C12	0.0614 (11)	0.0546 (11)	0.0561 (11)	0.0051 (9)	0.0081 (9)	0.0020 (9)
C3	0.0554 (10)	0.0723 (12)	0.0448 (10)	−0.0124 (9)	0.0057 (8)	−0.0027 (9)
C6	0.0654 (12)	0.0565 (11)	0.0610 (12)	−0.0098 (9)	0.0007 (10)	−0.0014 (9)
C5	0.0557 (11)	0.0639 (11)	0.0566 (11)	−0.0071 (9)	−0.0074 (9)	−0.0077 (9)
C8	0.0591 (11)	0.0536 (10)	0.0571 (11)	0.0004 (8)	0.0091 (9)	−0.0054 (8)
C2	0.0528 (10)	0.0767 (13)	0.0446 (10)	−0.0101 (9)	−0.0009 (8)	−0.0068 (9)
C7	0.0628 (12)	0.0658 (12)	0.0521 (11)	−0.0022 (10)	0.0030 (9)	−0.0116 (9)
C1	0.0614 (11)	0.0625 (11)	0.0443 (10)	0.0019 (9)	−0.0013 (8)	−0.0048 (8)
C11	0.0819 (15)	0.0571 (12)	0.0768 (14)	0.0050 (11)	0.0087 (12)	0.0074 (11)
C14	0.1016 (18)	0.0836 (15)	0.0610 (13)	0.0289 (13)	−0.0081 (12)	0.0036 (11)
C9	0.0833 (15)	0.0583 (12)	0.0814 (15)	−0.0083 (11)	0.0010 (12)	−0.0145 (11)
C10	0.1018 (18)	0.0466 (11)	0.0993 (19)	−0.0044 (12)	0.0076 (15)	0.0029 (12)

N1—C7	1.284 (3)	C6—C1	1.382 (3)
N1—C4	1.421 (2)	C6—H9	0.950
O1—C1i	1.394 (2)	C5—H10	0.950
O1—C1	1.394 (2)	C8—C9	1.402 (3)
O2—C13	1.345 (2)	C8—C7	1.449 (3)
O2—H3	0.840	C2—C1	1.372 (3)
C4—C5	1.379 (3)	C2—H12	0.950
C4—C3	1.397 (3)	C7—H4	1.04 (2)
C13—C12	1.394 (3)	C11—C10	1.383 (3)
C13—C8	1.401 (3)	C11—H15	0.950
O3—C12	1.375 (2)	C14—H16A	0.980
O3—C14	1.419 (2)	C14—H16B	0.980
C12—C11	1.363 (3)	C14—H16C	0.980
C3—C2	1.379 (3)	C9—C10	1.363 (3)
C3—H8	0.950	C9—H17	0.950
C6—C5	1.381 (3)	C10—H18	0.950
C7—N1—C4	120.94 (16)	C1—C2—C3	120.11 (17)
C1i—O1—C1	115.8 (2)	C1—C2—H12	119.9
C13—O2—H3	109.5	C3—C2—H12	119.9
C5—C4—C3	118.51 (17)	N1—C7—C8	122.55 (17)
C5—C4—N1	118.23 (16)	N1—C7—H4	122.3 (12)
C3—C4—N1	123.24 (18)	C8—C7—H4	115.2 (12)
O2—C13—C12	118.43 (17)	C2—C1—C6	120.57 (17)
O2—C13—C8	121.98 (16)	C2—C1—O1	121.33 (16)
C12—C13—C8	119.59 (17)	C6—C1—O1	118.06 (18)
C12—O3—C14	117.23 (17)	C12—C11—C10	120.5 (2)
C11—C12—O3	124.41 (18)	C12—C11—H15	119.8
C11—C12—C13	120.21 (19)	C10—C11—H15	119.8
O3—C12—C13	115.39 (17)	O3—C14—H16A	109.5
C2—C3—C4	120.22 (18)	O3—C14—H16B	109.5
C2—C3—H8	119.9	H16A—C14—H16B	109.5
C4—C3—H8	119.9	O3—C14—H16C	109.5
C5—C6—C1	118.99 (19)	H16A—C14—H16C	109.5
C5—C6—H9	120.5	H16B—C14—H16C	109.5
C1—C6—H9	120.5	C10—C9—C8	120.2 (2)
C4—C5—C6	121.44 (17)	C10—C9—H17	119.9
C4—C5—H10	119.3	C8—C9—H17	119.9
C6—C5—H10	119.3	C9—C10—C11	120.5 (2)
C13—C8—C9	118.89 (19)	C9—C10—H18	119.7
C13—C8—C7	121.02 (17)	C11—C10—H18	119.7
C9—C8—C7	120.09 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···N1	0.84	1.87	2.611 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H3⋯N1	0.84	1.87	2.611 (2)	147