2-[N-(4-{4-[(2-Hy­droxy-5-meth­oxy­benzyl­idene)amino]­benz­yl}phen­yl)carboximido­yl]-4-meth­oxy­phenol

Ourari, A.; Baameur, L.; Bouet, G.; Allain, M.

doi:10.1107/S1600536812010550

Volume 68
Part 4
Page o1141
April 2012

Received 14 September 2011
Accepted 9 March 2012
Online 24 March 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.116
Data-to-parameter ratio = 14.0
Details

2-[N-(4-{4-[(2-Hydroxy-5-methoxybenzylidene)amino]benzyl}phenyl)carboximidoyl]-4-methoxyphenol

Ali Ourari,^a Lotfi Baameur,^a Gilles Bouet ^b and Magali Allain ^c ^*

^aLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria,^bLaboratoire SONAS, E.A. 921, Faculté de Pharmacie, 16 Boulevard Daviers, 49045 Angers Cedex 01, France, and ^cMOLTECH ANJOU UMR CNRS 6200, 2, bd Lavoisier, 49045 Angers Cedex, France
Correspondence e-mail: alourari@yahoo.fr

In the title Schiff base, C₂₉H₂₆N₂O₄, the complete molecule is generated by a crystallographic twofold axis and is V-shaped. The planes of the benzene rings of the central diphenylmethane unit make a dihedral angle of 78.11 (4)° while adjacent benzene and 5-methoxysalicylidene rings are twisted with respect to each other by a dihedral angle of 11.84 (8)°. The Schiff base is in the enol-imino form and an intramolecular O-HN hydrogen bond is observed.

Related literature

For related bis-bidentate Schiff base ligand structures, see: Birkedal & Pattison (2006); Shahverdizadeh & Tiekink (2011). For Schiff base ligands, see: Chu & Huang (2007); Yoshida & Ichikawa, (1997); Kruger et al. (2001); Moutet & Ourari (1997). For applications of bis-bidentate Schiff base ligands, see: Lin et al. (2008); Sadeghi et al. (2003).

Experimental

Crystal data

C₂₉H₂₆N₂O₄
M_r = 466.52
Monoclinic, C 2/c
a = 41.307 (4) Å
b = 4.5993 (3) Å
c = 12.2229 (13) Å
= 93.653 (12)°
V = 2317.4 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.69 × 0.38 × 0.06 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: gaussian (ABSGAUSS in PLATON; Spek, 2009) T_min = 0.953, T_max = 0.993
10694 measured reflections
2244 independent reflections
1662 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.116
S = 1.06
2244 reflections
160 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.89	1.81	2.6177 (15)	151

Data collection: EXPOSE (Stoe & Cie, 1995); cell refinement: X-RED (Stoe & Cie, 1995); data reduction: X-RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2024 ).

Acknowledgements

The authors are very grateful to Professor Jean-Claude Daran at the Laboratoire de Chimie de Coordination, UPR-CNRS 8241 (Toulouse) for his valuable contribution and insightful discussions.

References

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