2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphthol

Dong, W.-K.; Wu, J.; Yao, J.; Li, L.; Gong, S.

doi:10.1107/S1600536809022508

Volume 65
Part 7
Page o1598
July 2009

Received 11 June 2009
Accepted 12 June 2009
Online 17 June 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.045
wR = 0.122
Data-to-parameter ratio = 13.1
Details

2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol

Wen-Kui Dong,^a ^* Jian-chao Wu,^a Jian Yao,^a Li Li ^a and Shang-sheng Gong ^a

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

The complete molecule of the title compound, C₂₆H₂₄N₂O₄, is generated by a crystallographic centre of inversion. There are two intramolecular O-HN hydrogen bonds. In the crystal structure, intermolecular C-HO hydrogen bonds result in zigzag chains.

Related literature

For the applications of Shiff base ligands, see: Calligaris & Randaccio (1987) For the applications bisoxime derivatives of salen-type compounds, see: Sun et al. (2004); Wang et al. (2007). For related structures, see: Dong et al. (2008a,b,c);

Experimental

Crystal data

C₂₆H₂₄N₂O₄
M_r = 428.47
Monoclinic, C 2/c
a = 12.6682 (18) Å
b = 9.3728 (15) Å
c = 18.335 (2) Å
= 97.478 (2)°
V = 2158.6 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.39 × 0.37 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.966, T_max = 0.989
5220 measured reflections
1894 independent reflections
1027 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.122
S = 1.06
1894 reflections
145 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N1	0.82	1.84	2.562 (3)	146
C10-H10O2ⁱ	0.93	2.63	3.446 (3)	146
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

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: HG2524 ).

Acknowledgements

The authors acknowledge finanical support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University.

References

Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715-738. London: Pergamon.
Dong, W.-K., He, X.-N., Guan, Y.-H., Xu, L. & Ren, Z.-L. (2008c). Acta Cryst. E64, o1600-o1601.
Dong, W.-K., He, X.-N., Li, L., Lv, Z.-W. & Tong, J.-F. (2008a). Acta Cryst. E64, o1405.
Dong, W.-K., Zhao, C.-Y., Zhong, J.-K., Tang, X.-L. & Yu, T.-Z. (2008b). Acta Cryst. E64, o1323.
Sheldrick, G. M. (1996). SADABS. University of Goöttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Sun, S. S., Stern, C. L., Nguyen, S. T. & Hupp, J. T. (2004). J. Am. Chem. Soc. 126, 6314-6326.
Wang, L., He, X., Sun, Y. & Xu, L. (2007). Acta Cryst. E63, o4517.

organic compounds