5,5′-Dimeth­oxy-2,2′-[(pentane-1,5-diyl­dioxy)bis­(nitrilo­methyl­idyne)]diphenol

Sun, Y.-X.; Li, L.; Dong, W.-K.; Wu, J.-C.; Tong, J.-F.

doi:10.1107/S1600536809014986

Volume 65
Part 5
Page o1160
May 2009

Received 17 April 2009
Accepted 22 April 2009
Online 30 April 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.052
wR = 0.124
Data-to-parameter ratio = 13.7
Details

5,5'-Dimethoxy-2,2'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol

Yin-Xia Sun,^a Li Li,^a Wen-Kui Dong,^a ^* Jian-Chao Wu ^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

The molecule of the title compound, C₂₁H₂₆N₂O₆, which lies across a crystallographic inversion centre, crystallizes with two unique half-molecules in the symmetric unit and adopts a linear configuration and the imino group is coplanar with the aromatic ring, making a dihedral angle of 3.26 (3)°. Strong intramolecular O-HN and weak intermolecular O-HO and C-HO hydrogen bonds and weak intermolecular [pi] - [pi] stacking interactions [centroid-centroid distance = 4.419 (2) Å]establish an infinite three-dimensional supramolecular structure.

Related literature

For the properties and uses of salen-type compounds, see: Lacroix (2001); Nishijo et al. (2006); Onda et al. (2007); Sun et al. (2004). For the structures of free salen-type compounds, see: Akine et al. (2005). For related structures, see: Dong et al. (2008a,b, 2009).

Experimental

Crystal data

C₂₁H₂₆N₂O₆
M_r = 402.44
Triclinic, $[P \overline 1]$
a = 7.3324 (15) Å
b = 7.6214 (17) Å
c = 20.372 (3) Å
= 81.525 (1)°
= 89.928 (2)°
= 67.870 (1)°
V = 1041.2 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.43 × 0.28 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.961, T_max = 0.987
5481 measured reflections
3618 independent reflections
1641 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.124
S = 1.01
3618 reflections
264 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3N1	0.82	1.90	2.610 (3)	144
O5-H5N2	0.82	1.90	2.628 (3)	147
O3-H3O3ⁱ	0.82	2.68	3.045 (3)	109
C2-H2AO3ⁱⁱ	0.97	2.58	3.533 (4)	168
C19-H19O5ⁱⁱ	0.93	2.44	3.300 (4)	154
Symmetry codes: (i) -x-1, -y+2, -z; (ii) x+1, y, z.

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: HG2502 ).

Acknowledgements

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

References

Akine, S., Taniguchi, T., Dong, W. K., Masubuchi, S. & Nabeshima, T. (2005). J. Org. Chem. 70, 1704-1711.
Dong, W.-K., He, X.-N., Guan, Y.-H., Xu, L. & Ren, Z.-L. (2008a). Acta Cryst. E64, o1600-o1601.
Dong, W.-K., Lv, Z.-W., He, X.-N., Guan, Y.-H. & Tong, J.-F. (2008b). Acta Cryst. E64, o2059.
Dong, W. K., Sun, Y. X., Zhang, Y. P., Li, L., He, X. N. & Tang, X. L. (2009). Inorg. Chim. Acta, 362, 117-124.
Lacroix, P. G. (2001). Eur. J. Inorg. Chem. pp. 339-348.
Nishijo, J., Okabe, C., Oishi, O. & Nishi, N. (2006). Carbon, 44, 2943-2949.
Onda, A., Hara, S., Kajiyoshi, K. & Yanagisawa, K. (2007). Appl. Catal. A Gen. 321, 71-78.
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.

organic compounds