Redetermination of Crystal Structure of N,N'-bis (2-Hydroxybenzylidene)-2,2-Dimethyl-1,3-Propanediamine

Document Type: Research Note


1 Faculty of Chemistry, University of Tehran, P.O. Box 14155-6455 Tehran, I.R. IRAN

2 Department of Chemistry, Shahid Bahonar University, Kerman, I.R. IRAN


The structure of N,N'-bis(2-hydroxybenzylidene)-2,2-dimethyl-1,3-propanediamine, C19H22N2O2, has been studied at low temperature (120K) by means of single-crystal X-ray diffraction. Solving the structure shows an orthorhombic unit cell, with P212121 space group, Z = 4, a = 6.1046 (4) Å, b = 15.8349 (11)Å, c = 17.2898 (12) Å and V = 1671.3 (2) Å3. There are two relatively strong hydrogen bonds (average O—H···N, 2.59 Å), involving the hydroxyl group and the nearest N atom of the imine groups is an indicative of intra-molecular hydrogen bonding within each salicylideneimine moiety.  C-H…π interactions connect the neighboring molecules together, stabilizing the crystal network. No significant p-p interactions are present in the crystal structure.


Main Subjects

[1] Carey F.A., "Organic Chemistry", 5th ed.,New York, McGraw-Hill, (2003).
[2] Sonmez M., Levent A., Sekerci M., Oxidative Dehydrogenation of Cu(II) Complexes with N-Aryl-N-2- Hydroxybenzyl- and N-Aryl-N-2-Hydroxynaphthylmethyleneamine Derivatives, Russ. J. Coord. Chem., 30, p. 655 (2004).
[3] Tuncel M., Serin S., Synthesis and Characterization of Copper(II), Nickel(II) and Cobalt(II) Complexes with Azo-Linked Schiff Base Ligands, Synth. React. Inorg. Met.-Org. Chem., 35, p. 203 (2005).
[4]  Khandar A.A., Nejati K. , Rezvani Z., Synthesis, Characterization and Study of the Use of Cobalt (II) Schiff-Base Complexes as Catalysts for the Oxidation of Styrene by Molecular Oxygen, Molecules 10, p. 302 (2005).
[5] Refat M.S. El-Deen I.M., Ibrahim H.K., El-Ghool S., Synthesis and Characterization of Copper(II), Nickel(II) and Cobalt(II) Complexes with Azo-Linked Schiff Base Ligands, Spectrochim. Acta Part A, 65, p. 1208 (2006).
[6] Gusel'nikov L.E., AvakyanV.G., Guselnikov S.L., Effect of Geminal Substitution at Silicon on 1-Sila- and 1,3-Disilacyclobutanes' Strain Energies, Their 2+2 Cycloreversion Enthalpies, and Si=C π-Bond Energies in Silenes,  J. Am. Chem. Soc. 124,  p. 662 (2002).
[7] Aydogan F., Ocal N., Turgut Z., Yolacan C., Transformations of Aldimines Derived from Pyrrole- 2- Carbaldehyde. Synthesis of Thiazolidino-Fused Compounds, Bull. Korean Chem. Soc., 22, p. 476 (2001).
[8] Calligaris M., Randaccio, M., "Schiff Bases as Acyclic Polydentate Ligands, in Comprehensive Coordination Chemistry", 2, Wilkinson G., ed, Pregmon Press, (1987).
[9] Yamada S., Advancement in Stereochemical Aspects of Schiff Base Metal Complexes, Coord. Chem. Rev., 190, p. 537 (1999).
[10] Garnovskii A.D., Vasil Chenko I.S., Rational Design of Metal Coordination Compounds with Azomethine Ligands, Russ. Chem. Rev., 71, p.943 (2002).
[11] Garnovskii A.D., Nivorozhkin A.L., Minkin V.I., Ligand Environment and Structure of Schiff Base Adducts and Tetracoordinated Metal-Chelates, Coord. Chem. Rev., 126, p.1 (1993).
[12] Corden J.P., Errington W., Moore P., Wallbridge M.G.H., N,N'-Bis(2-Hydroxybenzylidene)-2,2-Dimethyl-1,3-Propanediamine, Acta Cryst., C52, p. 125 (1996). 
[13] Flack H.D., On Enantiomorph-Polarity Estimation, Acta Cryst.,A39, p. 876 (1983).
[14] a) "Bruker SAINTPlus Data Reduction and Correction Program", v. 6.01, Bruker AXS, Madison, Wisconsin, USA(1998).
        b) "Bruker SMART. Bruker Molecular Analysis Research Tool", v. 5.059. Bruker AXS, Madison, Wisconsin,USA(1998).
[15] Sheldrick G.M., SHELXS97and SHELXL97.University of Göttingen,Germany (1997).
[16] BrandenburgK., DIAMOND. "Crystal Impact GbR",Bonn,Germany (2001).
[17] Spek A.L., Single-Crystal Structure Validation with the Program PLATON, J. Appl. Cryst., 36 , p. 7 (2003).
[18] Abbasi A., Sheikhshoaei I., Saghaei A., Monadi N., {2,2'- [(2,2- Dimethylpropane -1,3- diyl) Bis(Nitrilomethylidyne)]Diphenolato}DioxidomolybDenum(VI),  Acta Cryst., E64, p. m1036 (2008).