Abstract
In 1-(2-iodo-benzo-yl)-4-(pyrimidin-2-yl)piperazine, C15H15IN4O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site. The planar amide unit makes a dihedral angle of 80.44 (7)° with the phenyl ring. A combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds links the mol-ecules into a complex three-dimensional network structure, augmented by a π-π stacking inter-action and an I⋯N halogen bond, all involving different pairs of inversion-related mol-ecules. Comparisons are made with the structures of a number of related compounds.
Highlights
In 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine, C15H15IN4O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site
A combination of C—HÁ Á ÁO and C— HÁ Á Á(arene) hydrogen bonds links the molecules into a complex threedimensional network structure, augmented by a – stacking interaction and an IÁ Á ÁN halogen bond, all involving different pairs of inversion-related molecules
Piperazine-based compounds exhibit anti-cancer properties (Abdel-Jalil et al, 2005), while the combination of pyrimidine and piperazine units is found in buspirone, 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione (Tollefson et al, 1991), which can be used in the treatment of anxiety
Summary
Pyrimidine derivatives are well represented amongst the range of heterocyclic compounds that exhibit a broad spectrum of biological activities such as analgesic and anti-inflammatory activity (Amin et al, 2009), antibacterial (Kuyper et al, 1996), antidepressant (Kim et al, 2010), antimicrobial and antioxidant (Padmaja et al, 2009) and antiviral activities (Ibrahim & El-Metwally, 2010). Piperazine-based compounds exhibit anti-cancer properties (Abdel-Jalil et al, 2005), while the combination of pyrimidine and piperazine units is found in buspirone, 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione (Tollefson et al, 1991), which can be used in the treatment of anxiety. With these considerations in mind, we have synthesized the title compound (I) (Fig. 1), and we report here its molecular and supramolecular structure. A second sub-structure can be identified in which the C— HÁ Á Á(arene) hydrogen bond links molecules related by a 21 screw axis to form a chain running parallel to the [010] direction (Fig. 3).
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