title: Two new thiophosphoramide structures: N,N',N''-tricyclohexylphosphorothioic triamide and O,O'-diethyl (2-phenylhydrazin-1-yl)thiophosphonate.
abstract: The compound N,N',N''-tricyclohexylphosphorothioic triamide, C18H36N3PS or P(S)[NHC6H11]3, (I), crystallizes in the space group Pnma with the molecule lying across a mirror plane; one N atom lies on the mirror plane, whereas the bond-angle sum at the other N atom has a deviation of some 8° from the ideal value of 360° for a planar configuration. The orientation of the atoms attached to this nonplanar N atom corresponds to an anti orientation of the corresponding lone electron pair (LEP) with respect to the P=S group. The P=S bond length of 1.9785 (6) Å is within the expected range for compounds with a P(S)[N]3 skeleton; however, it is in the region of the longest bond lengths found for analogous structures. This may be due to the involvement of the P=S group in N-H···S=P hydrogen bonds. In O,O'-diethyl (2-phenylhydrazin-1-yl)thiophosphonate, C10H17N2O2PS or P(S)[OC2H5]2[NHNHC6H5], (II), the bond-angle sum at the N atom attached to the phenyl ring is 345.1°, whereas, for the N atom bonded to the P atom, a practically planar environment is observed, with a bond-angle sum of 359.1°. A Cambridge Structural Database [CSD; Allen (2002). Acta Cryst. B58, 380-388] analysis shows a shift of the maximum population of P=S bond lengths in compounds with a P(S)[O]2[N] skeleton to the shorter bond lengths relative to compounds with a P(S)[N]3 skeleton. The influence of this difference on the collective tendencies of N···S distances in N-H···S hydrogen bonds for structures with P(S)[N]3 and P(S)[O]2[N] segments were studied through a CSD analysis.
authors.affiliation: Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran.
authors.forename: Mehrdad
authors.initials: M
authors.lastname: Pourayoubi
authors.affiliation: Department of Chemistry, Payame Noor University, 19395-4697 Tehran, Iran.
authors.forename: Mozhgan
authors.initials: M
authors.lastname: Abrishami
authors.affiliation: Department of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic.
authors.forename: Václav
authors.initials: V
authors.lastname: Eigner
authors.affiliation: CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic.
authors.forename: Marek
authors.initials: M
authors.lastname: Nečas
authors.affiliation: Institute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Dušek
authors.affiliation: Department of Chemistry, Payame Noor University, 19395-4697 Tehran, Iran.
authors.forename: Mahmoud
authors.initials: M
authors.lastname: Delavar
keywords: NMR experiment; N—H...S hydrogen bond; P(S)[N]3 skeleton; P(S)[O]2[N] skeleton; crystal structure; database analysis; phosphorothioic triamide; thiophosphoramide