Abstract
The refinement of the crystal structure of the title compound, C20H34N6S2, was challenging, as a consequence of three issues: crystals are twinned, disordered, and include large empty voids corresponding to ca 8% of the unit-cell volume. A satisfactory model was obtained using data collected at 153 K. The diazecine ring is centrosymmetric, and displays the expected boat–chair–boat conformation. The 3-(methylsulfanyl)propyl chain is disordered over two sites with equal occupancies, and different conformations, i.e. trans–gauche–gauche for the first chain [Ndiaz—Cmeth—Cmeth—Cmeth torsion angles: 169.9 (4), 66.8 (5), 62.4 (5)°; diaz = diazecine and meth = methylene] and trans–trans–gauche for the second component [torsion angles: 169.9 (4), −177.6 (4), 64.4 (5)°]. In the crystal, N—H...N hydrogen bonds between imidazole rings are evident; weak intermolecular C—H...S contacts are also noted. The crystal studied was modelled as a two-component twin.
Highlights
The refinement of the crystal structure of the title compound, C20H34N6S2, was challenging, as a consequence of three issues: crystals are twinned, disordered, and include large empty voids corresponding to ca 8% of the unit-cell volume
The 3-(methylsulfanyl)propyl chain is disordered over two sites with equal occupancies, and different conformations, i.e. trans–gauche–gauche for the first chain [Ndiaz—Cmeth—Cmeth—Cmeth torsion angles: 169.9 (4), 66.8 (5), 62.4 (5); diaz = diazecine and meth = methylene] and trans–trans–gauche for the second component [torsion angles: 169.9 (4), À177.6 (4), 64.4 (5)]
The chemistry of [1,6]diazecine derivatives bearing imidazole rings started in the 19900s, through a collaboration between groups from Mexico and The Netherlands (MendozaDıaz et al, 1996), when a suitable methodology was established for their preparation, based on the Mannich reaction
Summary
The chemistry of [1,6]diazecine derivatives bearing imidazole rings started in the 19900s, through a collaboration between groups from Mexico and The Netherlands (MendozaDıaz et al, 1996), when a suitable methodology was established for their preparation, based on the Mannich reaction. The one-pot reaction between propylamine, formaldehyde and 2-methylimidazole resulted in the double addition of formaldehyde on the imidazole, followed by condensation with propylamine, to afford the ten-membered ring characterizing the diazecines. Some other related structures were characterized by X-ray diffraction, upon modification of the group substituting the N sites in positions 1 and 6 in the ring (Mendoza-Dıaz et al, 2002, 2010).
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