Abstract
A hydrogen sulfate salt, C15H18NSe+·HSO4 -·H2O or [BnSeCH2CH(Ph)NH3 +](HSO4 -), of a chiral selenated amine (R)-2-(benzyl-selan-yl)-1-phenyl-ethan-amine (BnSeCH2CH(Ph)NH2) has been synthesized and characterized by elemental analysis,1H and 13C{1H} NMR, FT-IR analysis, and single-crystal X-ray diffraction studies. The title salt crystallizes in the monohydrate form in the non-centrosymmetric monoclinic P21 space group. The cation is somewhat W shaped with the dihedral angle between the two aromatic rings being 60.9 (4)°. The carbon atom attached to the amine nitro-gen atom is chiral and in the R configuration, and, the -C-C- bond of the -CH2-CH- fragment has a staggered conformation. In the crystal structure, two HSO4 - anions and two water mol-ecules form an R 4 4(12) tetra-meric type of assembly comprised of alternating HSO4 - anions and water mol-ecules via discrete D(2) O-H⋯O hydrogen bonds. This tetra-meric assembly aggregates along the b-axis direction as an infinite one-dimensional tape. Adjacent tapes are inter-connected via discrete D(2) N-H⋯O hydrogen bonds between the three amino hydrogen atoms of the cation sandwiched between the two tapes and the three HSO4 - anions of the nearest asymmetric units, resulting in a complex two-dimensional sheet along the ab plane. The pendant arrangement of the cations is stabilized by C-H⋯π inter-actions between adjacent cations running as chains down the [010] axis. Secondary Se⋯O [3.1474 (4) Å] inter-actions are also observed in the crystal structure. A Hirshfeld surface analysis, including d norm, shape-index and fingerprint plots of the cation, anion and solvent mol-ecule, was carried out to confirm the presence of various inter-actions in the crystal structure.
Highlights
Selenium is an important bio-element (Schwarz et al, 1957; Papp et al, 2007)
Two HSO4À anions and two water molecules are interconnected to form a tetrameric type of assembly comprising of alternating HSO4À anions and water molecules via discrete D(2) O1—H1DÁ Á ÁO2, O1—H1EÁ Á ÁO5 and O3—H3AÁ Á ÁO1 hydrogen bonds (Fig. 2, Table 1), with the O1—H1EÁ Á ÁO5 hydrogen bond appearing twice
Apart along the a axis, are interconnected via discrete D(2) N1—H1AÁ Á ÁO4, N1— H1BÁ Á ÁO4 and N1—H1CÁ Á ÁO2 hydrogen bonds (Fig. 3, Table 1) between the three amino hydrogen atoms of the cation sandwiched between the two tapes and the three HSO4À anions of the nearest asymmetric units, resulting in a complex two-dimensional sheet along the ab plane (Fig. 3)
Summary
The hypervalent nature of selenium results in interesting secondary bonding interactions (SBIs), known as non-bonded interactions, in organoselenium compounds (Musher et al, 1969; Raghavendra Kumar et al, 2006; Chivers & Laitinen, 2015; Bleiholder et al, 2006) These structural aspects are worth exploring as weak SBIs (Iwaoka et al, 2001, 2002a,b) in the compounds of heavy chalcogens (Se and Te) are ascribed important roles in structural chemistry, such as the stabilization of otherwise unstable organo-chalcogen compounds and supramolecular associations (Tiekink & Zukerman-Schpector, 2010; Werz et al, 2002) and possessing biological activities (Reich et al, 2016; Bartolini et al, 2017; Engman et al.,1992; Mukherjee et al, 2010). Symmetry codes: (i) x À 1; y þ 1; z; (ii) Àx; y þ 12; Àz; (iii) x À 1; y; z; (iv) x; y À 1; z; (v) Àx; y À 12; Àz; (vi) x; y þ 1; z
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