4-(4-Chlorophenyl)-5-[1-(4-chlorophenyl)-2-methyl-2-nitropropyl]-1,2,3-selenadiazole

Abstract

In the title compound, C18H15Cl2N3O2Se, the selenadiazole ring makes dihedral angles of 49.87 (3) and 55.70 (3)° with the two benzene rings. The dihedral angle between the two benzene rings is 11.90 (5)°. In the crystal structure, intra­molecular C—H⋯O and C—H⋯Se inter­actions and inter­molecular C—H⋯O, C—H⋯Cl and C—H⋯N inter­actions are observed.

Ethyl 3-(4-chlorophenyl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propanoate

“…The attached phenyl ring is twisted away at an angle of 50.6 (1)° with respect to selenadiazol ring. The bond lengths [Se1-N2] 1.874 (2) Å, [Se1-C8] 1.838 (2) Å & [Cl1-C13] 1.736 (2)° are comparable with the values reported in the literature (Marx et al 2008;Muthukumaran et al 2011). The bond C9-C16 is slightly lengthened due to streic interaction between the phenyl and chlorophenyl rings.…”

3-(4-Methylphenyl)-1-phenyl-3-(4,5,6,7-tetrahydro-1,2,3-benzoselenadiazol-4-yl)propan-1-one

“…The five-membered 1,2,3-selenadiazole moiety (C1/N1/N2/Se1/C2) of the title compound adopts a planar conformation as observed in the selenadiazole moieties of several crystal structures (Arsenyan et al, 2007;Saravanan et al, 2006a;Saravanan et al, 2006b;Saravanan et al, 2007;Saravanan et al, 2008;Marx et al, 2007;Marx et al, 2008a;Marx et al, 2008b;Gunasekaran et al, 2007a;Gunasekaran et al, 2007b). Cremer & Pople puckering analysis (Cremer & Pople, 1975) cannot be performed, for its weighted average absolute torsion angle is 0.89°, which is less than 5.0°.…”

“…For bond lengths in compounds containing a 1,2,3-selenadiazole group, see: Arsenyan et al (2007); Saravanan et al (2006aSaravanan et al ( ,b, 2007Saravanan et al ( , 2008; Marx et al (2007Marx et al ( , 2008a; Gunasekaran et al (2007a,b). For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al (2001); El-Bahaie et al (1990); El-Kashef et al (1986); Plano et al (2010); Padmavathi et al (2002).…”

“…Considering the importances of the 1,2,3-selenadiazole derivatives, we present herein the single-crystal structure analysis of the title compound. The bond lengths of the 1,2,3-selenadiazole moiety in the title compound are comparable to those observed for selenadiazole moieties in several crystal structures such as 4-methyl-5-ethoxycarbonyl-1,2,3-selenadiazole phenylboronic acid (Arsenyan et al, 2007), diethyl 2-((4-methylphenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl)malonate (Saravanan et al, 2006a), 4-(4-chlorophenyl)-5-(1-(4-methoxyphenyl)-2-methyl-2-nitropropyl)-1,2,3-selenadiazole (Saravanan et al, 2006b), 3-(4-methylphenyl)-3-(4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl)-2-phenylpropanenitrile , ethyl (Z)-3-(4-chlorophenyl)-2-cyano-3-(4-phenyl-1,2,3-selenadiazol-5-yl)prop-2-enoate (Saravanan et al, 2008), 5-(2-methyl-2-nitro-1-phenylpropyl)-4-phenyl-1,2,3-selenadiazole (Marx et al, 2007), 4-(4-Chlorophenyl)-5-(1-(4-chlorophenyl)-2-methyl-2-nitropropyl)-1,2,3-selenadiazole (Marx et al, 2008a), diethyl 2-((4-nitrophenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl)malonate (Marx et al, 2008b), 5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-4-phenyl-1,2,3-selenadiazole (Gunasekaran et al, 2007a) and 4-(4-chlorophenyl)-5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-1,2,3-selenadiazole (Gunasekaran et al, 2007b). The molecular structure of the title compound is shown in Fig.…”

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

“…It is notable that in 41 an appended pyridyl substituent is also available for interaction but it does not do so. The next five crystals, that is, 42 [86], 43 [87], 44 [88], Fig. 7c, 45 [68] and 46 [89] feature 1,2,3selenadiazole rings and form centrosymmetric dimers via {SeN … }2 synthons.…”