2,2′-{1,1′-[Pentane-1,5-diyl­bis(oxy­nitrilo)]­diethyl­idyne}diphenol

Dong, W.-K.; Lv, Z.-W.; He, X.-N.; Guan, Y.-H.; Tong, J.-F.

doi:10.1107/S160053680803136X

Volume 64
Part 11
Page o2059
November 2008

Received 28 July 2008
Accepted 28 September 2008
Online 4 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.042
wR = 0.123
Data-to-parameter ratio = 7.9
Details

2,2'-{1,1'-[Pentane-1,5-diylbis(oxynitrilo)]diethylidyne}diphenol

Wen-Kui Dong,^a ^* Zhong-Wu Lv,^a Xue-Ni He,^a Yong-Hong Guan ^a and Jun-Feng Tong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: dongwk@mail.lzjtu.cn

In the title compound, C₂₁H₂₆N₂O₄, there is half a molecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the -CH=N-O-(CH₂)₅-O-N=CH- bridge. The dihedral angle formed by the two benzene rings is 80.85 (2)°. Strong intramolecular O-HN and C-HO hydrogen bonds help to establish the molecular conformation. There are also weak intermolecular [pi] - [pi] stacking interactions between neighbouring benzene rings [centroid-centroid separation = 3.502 (3) Å].

Related literature

For general background, see: Bhadbhade & Srinivas (1993). For related structures, see: Dong et al. (2007, 2008); Wang et al. (2007); Xu et al. (2007).

Experimental

Crystal data

C₂₁H₂₆N₂O₄
M_r = 370.44
Monoclinic, C 2
a = 12.9691 (13) Å
b = 4.601 (1) Å
c = 16.3639 (16) Å
= 91.621 (1)°
V = 976.1 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 298 (2) K
0.48 × 0.40 × 0.32 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.959, T_max = 0.973
2421 measured reflections
972 independent reflections
646 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.123
S = 1.04
972 reflections
123 parameters
2 restraints
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N1	0.82	1.84	2.553 (4)	144
C4-H4AO1	0.96	2.16	2.631 (5)	109

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2048 ).

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604-01) and the `Qing Lan' Talent Engineering Fund of Lanzhou Jiaotong University (No. QL-03-01A), which are gratefully acknowledged.

References

Bhadbhade, M. M. & Srinivas, D. (1993). Inorg. Chem. 32, 6122-6130.
Dong, W. K., He, X. N., Dong, C. M., Wang, L., Zhong, J. K., Chen, X. & Yu, T. Z. (2007). Z. Kristallogr. New Cryst. Struct. 222, 289-290.
Dong, W.-K., He, X.-N., Zhong, J.-K., Chen, X. & Yu, T.-Z. (2008). Acta Cryst. E64, o1098.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wang, L., He, X., Sun, Y. & Xu, L. (2007). Acta Cryst. E63, o4517.
Xu, L., Zhang, Y. P., Sun, Y. X., Shi, J. Y. & Dong, W. K. (2007). Chin. J. Struct. Chem. 23, 1999-2002.

organic compounds