Crystal structure of trans-bis-[2-(1H-benzotriazol-1-yl)acetato-κO]bis-(ethano-lamine-κ2 N,O)copper(II).

Guloy K Alieva,Kasim A Zakhidov,Bakhtiyar T Ibragimov,Shahnoza A Kadirova,Jamshid M Ashurov

doi:10.1107/s2056989019000744

Abstract

The reaction of 2-(1H-benzotriazol-1-yl)acetic acid (HBTA; C8H7N3O2) and mono-ethano-lamine (MEA; C2H7NO) with CuCl2·2H2O resulted in the formation of the title complex, [Cu(C8H6N3O2)2(C2H7NO)2] or [Cu(BTA)2(MEA)2]. Its asymmetric unit comprises one BTA anion coordin-ating to the Cu2+ cation (site symmetry ) through the carboxyl O atom, and one MEA ligand chelating the metal cation by two heteroatoms (O and N). The equatorial Cu-O and Cu-N bond lengths are similar at 2.029 (1) and 1.980 (2) Å, respectively, while the length of the axial Cu-O bond is considerably greater [2.492 (2) Å], as is typical for Jahn-Teller-distorted systems. An intra-molecular hydrogen bond is present between the hy-droxy group of the MEA ligand and the non-coordinating O atom of the carboxyl-ate group. Inter-molecular hydrogen bonding involving the amino function of the MEA ligand and the carboxyl-ate group results in eight-membered rings with an R 2 2(8) graph-set motif. The mol-ecules are further linked by C-H⋯π inter-actions involving the triazole rings and methyl-ene groups of MEA, thus generating an overall three-dimensional supra-molecular framework.

Highlights

The reaction of 2-(1H-benzotriazol-1-yl)acetic acid (HBTA; C8H7N3O2) and monoethanolamine (MEA; C2H7NO) with CuCl2Á2H2O resulted in the formation of the title complex, [Cu(C8H6N3O2)2(C2H7NO)2] or [Cu(BTA)2(MEA)2]
Its asymmetric unit comprises one BTA anion coordinating to the Cu2+ cation through the carboxyl O atom, and one MEA ligand chelating the metal cation by two heteroatoms (O and N)
An intramolecular hydrogen bond is present between the hydroxy group of the MEA ligand and the non-coordinating O atom of the carboxylate group

Summary

Chemical context

Systematic studies of the structures and metal complex formation features of benzoic acid (Ibragimov et al, 2016a,b) and benzotriazole derivatives have been carried out by our group. Benzotriazoles consist of nitrogen-containing bicyclic ring systems and demonstrate many types of biological activities, such as antibacterial (Wan et al, 2010; Suma et al, 2012), antimicrobial (Nanjunda Swamy et al, 2006; Singh et al, 2009; Patel et al, 2012; Ramachandran et al, 2011), antifungal (Khabnadideh et al, 2012; Rezaei et al, 2009; Gaikwad et al, 2012; Rakesh et al, 2010), anticancer, anti-inflammatory, analgesic, antimalarial and antitubercular (Kopanska (nee Zastapiło) et al, 2004; Jamkhandi et al, 2015) Functional groups such as carboxylate, hydroxyl and pyridyl can be introduced to benzotriazole, increasing the coordination possibilities (Stoumpos et al, 2008; Wang et al, 2008a,b). The molecular structure is stabilized by an intramolecular O3—H3Á Á ÁO1 hydrogen bond between the OH group of the MEA ligand and the non-coordinating carboxylate O atom (Fig. 1, Table 1)

Supramolecular features

Database survey

Synthesis and crystallization

Refinement