Synthesis, crystal structure, computational analysis and biological properties of 1-(4-chlorobenzoyl)-3-[2-(2-{2-[3-(4-chlorobenzoyl)-thioureido]-ethoxy}ethoxy)ethyl]-thiourea and its Ni(II) and Cu(II) complexes

Abstract

, crystal structure, computational analysis and biological properties of 1-(4-chlorobenzoyl)-3-[2-(2-{2-[3-(4-chlorobenzoyl)-thioureido]-ethoxy}ethoxy)ethyl]thiourea and its Ni(II) and Cu(II) complexes

Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione

“…The C-C bond lengths of the aromatic rings are typical of sp 2 -hybridized carbons while the C2-C3 bond of the thioglycoluril moiety [1.542 (3) Å ] shows sp 3 hybridization. These bond lengths are consistent with previous reports for thioglycourils and acylthioureas (Binzet et al, 2009;Oyeka et al, 2018;Wang & Xi, 2009;Yang, 2010). The imidazole carbon atoms, C2 and C3, each have a distorted tetrahedral geometry with the N1-C3-N4 and N2-C2-N3 bond angles being 112.0 (4) and 112.9 (2) , respectively.…”

“…While several glycoluril analogues have been synthesized and characterized, reports on dithioglycolurils are quite rare. In the course of our search for thioureas with bioactivity, we had intended to isolate (2E)-N-[(4-methoxyphenyl)carbamothioyl]-3-phenylprop-2-enamide using well-documented methods (Asegbeloyin et al, 2018; Douglass & Dains, 1934;Oyeka et al, 2018); however, we obtained crystals of 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione, a new dithioglycoluril. As a result of the importance of glucolurils and their analogues and our current interest in the construction of novel heterocycles with good bioactivity (Asegbeloyin et al, 2019), we decided to investigate the title compound, and we report herein on its synthesis, crystal structure and Hirshfeld surface analysis.…”

“…The thione C S bond lengths of 1.674 (2) Å are longer than those in previous reports where all N atoms were substituted (Deng et al, 2010;Wang et al, 2011;Wu & Sun, 2009;Zhang et al, 2011). The C-N bonds around the thione moiety [C1-N1, C1-N2, C5-N3 and C5-N4 = 1.350 (3), 1.357 (3), 1.355 (3) and 1.353 (3) Å , respectively] are significantly shorter than the average C-N single bond length of 1.48 Å (Oyeka et al, 2018), as has also been observed in other thioglycoluril systems (Wu & Sun, 2009;Zhang et al, 2011) and acyl thiourea derivatives (Asegbeloyin et al, 2018;Oyeka et al, 2018). This is probably due to the conjugation between the -electrons on C S and the lone pairs of electrons on the nitrogen atoms.…”

“…The title compound was synthesized according to the reported method (Asegbeloyin et al, 2018;Douglass & Dains, 1934;Oyeka et al, 2018). A solution of cinnamoyl chloride (0.02 mol) dissolved in 40 ml acetone was mixed with a 30 ml acetone solution of potassium thiocyanate (0.02 mol).…”

Crystal structure ofN,N′-[(ethane-1,2-diyl)bis(azanediylcarbonothioyl)]bis(benzamide)

“…Six structures in which the spacer is different from the spacer in the symmetrical bis(thioureido) molecule studied here appear in the literature. The angles between the phenyl rings are: 63.1 for DAVHOZ (Aydın et al, 2012), 10.2 for EGUYAH (Sow et al, 2009), 35.4 for NEWJIL (Light, 2018), 0.0 for QIXQUK (Ding et al, 2008), 3.2 for TIFQAD (Oyeka et al, 2018) and 0.0 for XIQPAP (Dong et al, 2007). In addition, 23 structures which contain only one arm with a thioureido moiety similar to the studied molecules are reported, while the other arm consists of diverse moieties: CIGDAZ (Karipcin et al, 2013), DELMUD (Ngah et al, 2006), EYACIQ (Shutalev et al, 2004), GIHMIV (Haynes et al, 2014), GIHMOB (Haynes et al, 2014), IFUZOZ (Hassan et al, 2008a,b), NIQROV (Yamin & Malik, 2007), NIQROV01 (Nguyen & Abram, 2008), POFKIG (Ngah et al, 2014), QEWHUY (Rakhshani et al, 2018), RUGKOU (Hassan et al, 2009), SAFPAT (Wei, 2016) (16) 150Symmetry codes: (i) x; Ày þ 3 2 ; z À 1 2 ; (ii) Àx þ 1; Ày þ 1; Àz þ 1; (iii) x; Ày þ 3 2 ; z þ 1 2 .…”