Bis[4-(2-hydr­oxy-3-methoxy­benzyl­ideneamino)phen­yl] ether

Xu, H.-W.; Li, J.-X.; Li, Y.-H.

doi:10.1107/S1600536808014980

organic compounds

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Volume 64| Part 6| June 2008| Page o1145

doi:10.1107/S1600536808014980

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Bis[4-(2-hydroxy-3-methoxybenzylideneamino)phenyl] ether

Hong-Wu Xu,^a ^* Jin-Xia Li ^a and Yin-Hua Li ^a

^aDepartment of Materials and Chemical Engineering, ZhongYuan University of Technology, Zhengzhou, Henan 450007, People's Republic of China
^*Correspondence e-mail: hongwuxu2006@126.com

(Received 7 May 2008; accepted 17 May 2008; online 24 May 2008)

The title compound, C₂₈H₂₄N₂O₅, a flexible Schiff base ligand, was prepared in high yield by a Schiff base condensation of 3-methoxysalicylaldehyde and bis(4-aminophenyl) ether in methanol. The molecule 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 molecule is 24.29 (11)°, illustrating the degree of twisting of the flexible molecule.

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_r = 468.49
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.166
S = 1.11
2689 reflections
165 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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

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.

Supporting information

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

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

checkCIF report

Comment top

Within the field of supramolecular inorganic chemistry, self-assembly is one of the most efficient methods for complex architectures comprising spatially and geometrically well defined arrays of metal ions. Because of easy syntheses by simple one-pot condensation reactions between aldehydes (or ketones) and amines and their coordinating ability with metal ions, multidentate Schiff base ligands such as pyridylimines (He et al., 2000; Guo et al., 2002; Tesouro Vallina et al., 2001) and salicyladimines (Yoshida et al., 1999; Chu et al., 2007) were designed and used to prepare complexes in recent years. Here we report the synthesis and structure of a new flexible Schiff base ligand, bis(N-(3-methoxysalicylidene)-4-aminophenyl) ether. The molecule 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 molecule is 24.29 (11)°, illustrating the degree of twisting of the flexible molecule. The bond lengths and angles are in agreement with those reported for other salicyladimines ligands (Chu et al., 2007).

Related literature top

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 top

The title compound was prepared by a Schiff-base condensation of 3-methoxysalicylaldehyde (3.04 g, 20 mmol) and bis(4-aminophenyl) ether (2.02 g, 10 mmol) in methanol (40 ml). The solution was stirred and refluxed for 1 day. The orange precipitate was filtered off, washed with a small amount of methanol and dried in vacuo. Yield: 91%. Well shaped orange crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a chloroform solution of the title compound at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code A: 2-x, y, 3/2-z.]

Bis[4-(2-hydroxy-3-methoxybenzylideneamino)phenyl] ether top

Crystal data top

C₂₈H₂₄N₂O₅	F(000) = 984
M_r = 468.49	D_x = 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 = 1.7–25.1°
c = 19.859 (9) Å	µ = 0.09 mm⁻¹
β = 92.760 (8)°	T = 173 K
V = 2342.7 (19) Å³	Prism, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −20→19
8736 measured reflections	k = −9→9
2689 independent reflections	l = −22→25

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0739P)² + 0.5764P] where P = (F_o² + 2F_c²)/3
2689 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₈H₂₄N₂O₅	V = 2342.7 (19) Å³
M_r = 468.49	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.585 (7) Å	µ = 0.09 mm⁻¹
b = 7.578 (4) Å	T = 173 K
c = 19.859 (9) Å	0.30 × 0.20 × 0.20 mm
β = 92.760 (8)°

Data collection top

Bruker SMART CCD diffractometer	2016 reflections with I > 2σ(I)
8736 measured reflections	R_int = 0.035
2689 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.15 e Å⁻³
2689 reflections	Δρ_min = −0.14 e Å⁻³
165 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄N₂O₅
M_r	468.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	15.585 (7), 7.578 (4), 19.859 (9)
β (°)	92.760 (8)
V (Å³)	2342.7 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8736, 2689, 2016
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.166, 1.11
No. of reflections	2689
No. of parameters	165
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O2—H3···N1	0.84	1.87	2.611 (2)	147

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chu, Z. L. & Huang, W. (2007). J. Mol. Struct. 837, 15–22. Web of Science CSD CrossRef CAS Google Scholar
Guo, D., Pang, K. L., Duan, C. Y., He, C. & Meng, Q. J. (2002). Inorg. Chem. 41, 5978–5985. PubMed Google Scholar
He, C., Duan, C. Y., Fang, C. J. & Meng, Q. J. (2000). J. Chem. Soc. Dalton Trans. pp. 2419–2424. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tesouro Vallina, A. & Stoeckli-Evans, H. (2001). Acta Cryst. E57, m59–m61. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yoshida, N., Oshio, H. & Ito, T. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 975–983. CrossRef Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1145

doi:10.1107/S1600536808014980

Open

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