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

Guo, Y.-N.; Ge, C.-H.; Zhang, X.-D.; Zhang, X.-Y.; Liu, Q.-T.

doi:10.1107/S1600536807061740

Volume 64
Part 2
Page o505
February 2008

Received 12 November 2007
Accepted 21 November 2007
Online 23 January 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.095
Data-to-parameter ratio = 14.1
Details

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

Ya-Nan Guo,^a Chun-Hua Ge,^a ^* Xiang-Dong Zhang,^a Xiao-Yan Zhang ^a and Qi-Tao Liu ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
Correspondence e-mail: chhge@lnu.edu.cn

The title compound, C₂₆H₂₄N₂O₃, was synthesized by reduction of the corresponding Schiff base. The molecule does not possess crystallographic or non-crystallographic symmetry. The dihedral angle between the oxygen-bridged benzene rings is 67.98 (8)°. Both hydroxyl groups are involved in O-HO intramolecular hydrogen bonding. The molecules are linked into a two-dimensional network parallel to the (010) plane by N-HO hydrogen bonds.

Related literature

For related literature, see: Ge, Zhang, Zhang, Guan et al. (2003); Ge, Zhang, Zhang, Guo et al. (2003).

Experimental

Crystal data

C₂₆H₂₄N₂O₃
M_r = 412.47
Monoclinic, P 2₁ /n
a = 5.8241 (5) Å
b = 43.960 (4) Å
c = 8.2874 (7) Å
= 92.287 (1)°
V = 2120.1 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 295 (2) K
0.30 × 0.26 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.971, T_max = 0.982
11851 measured reflections
4170 independent reflections
2737 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.095
S = 0.93
4170 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.90 (2)	1.80 (2)	2.628 (2)	152 (2)
O3-H3N2	0.94 (3)	1.82 (3)	2.670 (2)	150 (2)
N1-H1BO3ⁱ	0.88 (2)	2.00 (2)	2.876 (2)	179 (2)
N2-H2BO1ⁱⁱ	0.88 (2)	2.03 (2)	2.914 (2)	176 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2520 ).

Acknowledgements

This work was supported by the Natural Science Foundation of the Education Bureau of Liaoning Province (grant No. 05 L159).

References

Bruker (2001). SMART (Version 5.624), SAINT (Version 6.04) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
Ge, C. H., Zhang, X. D., Zhang, P., Guan, W., Guo, F. & Liu, Q. T. (2003). Polyhedron, 22, 3493-3497.
Ge, C. H., Zhang, X. D., Zhang, P., Guo, F. & Liu, Q. T. (2003). Inorg. Chem. Commun. 6, 1061-1064.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

organic compounds