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A triclinic polymorph of tri ­ cyclo ­ hexyl ­ phosphane sulfide: crystal structure and Hirshfeld surface analysis

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ABSTRACT

55211: The title compound, (C6H11)3PS (systematic name: tri­cyclo­hexyl-λ5-phosphane­thione), is a triclinic (P-1, Z′ = 1) polymorph of the previously reported ortho­rhom­bic form (Pnma, Z′ = 1/2) [Kerr et al. (1977 ▸). Can. J. Chem. , 3081–3085; Reibenspies et al. (1996 ▸). Z. Kristallogr. , 400]. While conformational differences exist between the non-symmetric mol­ecule in the triclinic polymorph, cf. the mirror-symmetric mol­ecule in the ortho­rhom­bic form, these differences are not chemically significant. The major feature of the mol­ecular packing in the triclinic polymorph is the formation of linear chains along the a axis sustained by methine-C—H⋯S(thione) inter­actions. The chains pack with no directional inter­actions between them. The analysis of the Hirshfeld surface for both polymorphs indicates a high degree of similarity, being dominated by H⋯H (ca 90%) and S⋯H/H⋯S contacts.

No MeSH data available.


Views of the Hirshfeld surface for polymorph (I) mapped over dnorm over the range −0.160 to 1.823 au.
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fig6: Views of the Hirshfeld surface for polymorph (I) mapped over dnorm over the range −0.160 to 1.823 au.

Mentions: The different shapes of Hirshfeld surfaces mapped over electrostatic potential in Fig. 5 ▸ are indicative of the different mol­ecular conformations adopted by the cyclo­hexane rings in (I) and (II). A pair of bright-red spots appearing on the Hirshfeld surface mapped over dnorm near methine-H7 and thione-S1 for (I), Fig. 6 ▸, on the extremities of the mol­ecule represent the donor and acceptor of the C—H⋯S inter­action, Table 2 ▸. They are viewed as the respective blue (positive) and red (negative) regions on the Hirshfeld surface mapped over electrostatic potential, Fig. 5 ▸. The absence of characteristic spots on the dnorm-mapped Hirshfeld surfaces in the ortho­rhom­bic polymorph (II) (not shown) indicates no similar inter­actions within the sum of the van der Waals radii; see below. The immediate environments about reference mol­ecules of (I) and (II) within the dnorm-mapped Hirshfeld surfaces showing inter­molecular C—H⋯S inter­actions are displayed in Fig. 7 ▸a and b, respectively. In the crystal of (II), the zigzag chain of weak inter­molecular methyl­ene-C—H⋯S(thione) contacts on either side of the crystallographic mirror plane is viewed as the pair of red dashed lines in Fig. 7 ▸b (see above).


A triclinic polymorph of tri ­ cyclo ­ hexyl ­ phosphane sulfide: crystal structure and Hirshfeld surface analysis
Views of the Hirshfeld surface for polymorph (I) mapped over dnorm over the range −0.160 to 1.823 au.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382606&req=5

fig6: Views of the Hirshfeld surface for polymorph (I) mapped over dnorm over the range −0.160 to 1.823 au.
Mentions: The different shapes of Hirshfeld surfaces mapped over electrostatic potential in Fig. 5 ▸ are indicative of the different mol­ecular conformations adopted by the cyclo­hexane rings in (I) and (II). A pair of bright-red spots appearing on the Hirshfeld surface mapped over dnorm near methine-H7 and thione-S1 for (I), Fig. 6 ▸, on the extremities of the mol­ecule represent the donor and acceptor of the C—H⋯S inter­action, Table 2 ▸. They are viewed as the respective blue (positive) and red (negative) regions on the Hirshfeld surface mapped over electrostatic potential, Fig. 5 ▸. The absence of characteristic spots on the dnorm-mapped Hirshfeld surfaces in the ortho­rhom­bic polymorph (II) (not shown) indicates no similar inter­actions within the sum of the van der Waals radii; see below. The immediate environments about reference mol­ecules of (I) and (II) within the dnorm-mapped Hirshfeld surfaces showing inter­molecular C—H⋯S inter­actions are displayed in Fig. 7 ▸a and b, respectively. In the crystal of (II), the zigzag chain of weak inter­molecular methyl­ene-C—H⋯S(thione) contacts on either side of the crystallographic mirror plane is viewed as the pair of red dashed lines in Fig. 7 ▸b (see above).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

55211: The title compound, (C6H11)3PS (systematic name: tri­cyclo­hexyl-λ5-phosphane­thione), is a triclinic (P-1, Z′ = 1) polymorph of the previously reported ortho­rhom­bic form (Pnma, Z′ = 1/2) [Kerr et al. (1977 ▸). Can. J. Chem. , 3081–3085; Reibenspies et al. (1996 ▸). Z. Kristallogr. , 400]. While conformational differences exist between the non-symmetric mol­ecule in the triclinic polymorph, cf. the mirror-symmetric mol­ecule in the ortho­rhom­bic form, these differences are not chemically significant. The major feature of the mol­ecular packing in the triclinic polymorph is the formation of linear chains along the a axis sustained by methine-C—H⋯S(thione) inter­actions. The chains pack with no directional inter­actions between them. The analysis of the Hirshfeld surface for both polymorphs indicates a high degree of similarity, being dominated by H⋯H (ca 90%) and S⋯H/H⋯S contacts.

No MeSH data available.