Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses

Abstract

A hydrogen sulfate salt, C15H18NSe+·HSO4 −·H2O or [BnSeCH2CH(Ph)NH3 +](HSO4 −), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (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 nitrogen 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 molecules form an R 4 4(12) tetrameric type of assembly comprised of alternating HSO4 − anions and water molecules via discrete D(2) O—H...O hydrogen bonds. This tetrameric assembly aggregates along the b-axis direction as an infinite one-dimensional tape. Adjacent tapes are interconnected 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 interactions between adjacent cations running as chains down the [010] axis. Secondary Se...O [3.1474 (4) Å] interactions 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 molecule, was carried out to confirm the presence of various interactions in the crystal structure.

Foreword to the special virtual issue in tribute to Jerry P. Jasinski

“…We were especially pleased to see that four of the articles had direct contributions from Jerry himself, as well as some of his former students and postdocs from Keene State College. The topical coverage of the articles spans the full spectrum of non-biological crystallography, including organic and main-group compounds (Thiruvalluvar et al, 2021;Mahesha et al, 2021;Allah et al, 2021;Malla et al, 2022;Rajegowda et al, 2021;Purdy et al, 2021), complexes of transition metals and lanthanides (Addison et al, 2022;Frey et al, 2021;Ullery et al, 2021;Sghyar et al, 2021;Tinapple et al, 2021;Mikhalyova et al, 2022;Pavlischuk et al, 2021), transition metal and actinide clusters (Park et al, 2022;Patel et al, 2022;Kelley et al, 2021), and coordination polymers (Lobana et al, 2022). It also includes two articles (Foxman, 2021;Zheng & Campbell, 2021) first published as part of the 'Modern approaches and tools for teaching crystallography' special issue in Acta E that describe the tutorial for teaching space groups and crystallographic symmetry that Jerry developed with Bruce Foxman.…”