title: 4-Amino-N-isopropylbenzamidinium chloride ethanol solvate.
abstract: The title compound, C10H16N3+.Cl-.C2H6O, is an important intermediate in the convergent synthesis of amidine-substituted polycyclic heterocycles, a class of compounds that shows significant anticancer activity. The molecule of (I) is not planar, having a dihedral angle of 25.00 (7) degrees between the aniline and amidine (-C-NH=C=NH2) groups. The protonation of the amidine molecular fragment is accompanied by delocalized C-N bond distances of 1.320 (2) and 1.317 (2) A. The cations and chloride anions are involved in a network of hydrogen bonds, resulting in the formation of infinite chains propagating along the b direction. The chains are further grouped within the ab plane, in such a way that the structure is segregated into layers dominated by hydrophobic interactions involving N-isopropyl residues and layers dominated by N-H...Cl [N...Cl = 3.275 (2)-3.596 (2) A], O-H...Cl [O...Cl = 3.229 (3) A] and N-H...O [N...O = 2.965 (3) A] hydrogen bonds.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, PO Box 177, HR-10000 Zagreb, Croatia.
authors.forename: Ivana
authors.initials: I
authors.lastname: Jarak
authors.forename: Grace
authors.initials: G
authors.lastname: Karminski-Zamola
authors.forename: Gordana
authors.initials: G
authors.lastname: Pavlović
authors.forename: Zora
authors.initials: Z
authors.lastname: Popović
mesh_terms: D001550:Benzamidines / Q000138:chemical synthesis / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D000431:Ethanol / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012995:Solubility; D013055:Spectrophotometry, Infrared
chemical_list: D001550:Benzamidines; D002712:Chlorides; D000431:Ethanol