6,6′-Di-tert-butyl-4,4′-dimethyl-2,2′-[1,2-phenyl­enebis(nitrilo­methanylyl­idene)]diphenol

Ding, R.-F.; Wang, Q.-B.; Wen, X.-M.

doi:10.1107/S1600536811051257

Volume 68
Part 1
Page o40
January 2012

Received 2 November 2011
Accepted 29 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.075
wR = 0.271
Data-to-parameter ratio = 14.4
Details

6,6'-Di-tert-butyl-4,4'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethanylylidene)]diphenol

Rui-Fang Ding,^a Qi-Bao Wang ^a ^* and Xin-Min Wen ^a

^aDepartment of Pharmacy, Jining Medical College, Xueyuan Road 669, Rizhao, People's Republic of China
Correspondence e-mail: wqb_wangqibao@163.com

In the title molecule, C₃₀H₃₆N₂O₂, the dihedral angles between the central benzene ring and the two benzene rings of the butylsalicylaldimine groups are 14.3 (2) and 40.6 (2)°. There are two strong intramolecular O-HN hydrogen bonds which form S(6) rings. The crystal studied was a non-merohedral twin with refined components of 0.270 (4) and 0.730 (4).

Related literature

For applications of Schiff base ligands in pharmaceutical and catalytic research, see: Hashimoto & Maruoka (2007); Singh et al. (2009). For a related structure, see: You et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₃₀H₃₆N₂O₂
M_r = 456.61
Triclinic, $[P \overline 1]$
a = 10.578 (7) Å
b = 11.394 (7) Å
c = 12.217 (7) Å
= 72.195 (6)°
= 73.525 (6)°
= 72.975 (6)°
V = 1309.8 (14) Å³
Z = 2
Mo K radiation
= 0.07 mm^-1
T = 296 K
0.28 × 0.22 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.980, T_max = 0.989
4593 measured reflections
4593 independent reflections
2894 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.075
wR(F²) = 0.271
S = 1.13
4593 reflections
318 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.89	2.605 (4)	145
O2-H2N2	0.82	1.87	2.609 (4)	149

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5371 ).

Acknowledgements

This work was supported by the Foundation of Shandong Educational Committee (No. J10LB63) and the Key Project of Science and Technology of JNMC.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hashimoto, T. & Maruoka, K. (2007). Chem. Rev. 107, 5656-5682.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, S., Bharti, N. & Mohapatra, P. P. (2009). Chem. Rev. 109, 1900-1947.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
You, W., Yao, C. & Huang, W. (2010). Chin. J. Inorg. Chem. pp. 867-874.

organic compounds