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. 2025 Aug 27;81(Pt 9):874-878.
doi: 10.1107/S2056989025007303. eCollection 2025 Sep 1.

Bis[1,2-bis-(4-fluoro-phen-yl)ethyl-ene-1,2-di-thiol-ato(1-)]nickel(II)

Joseph B Donahue  1 , Titir Das Gupta  2 , Laura Fiabane  2 , Xiaodong Zhang  2 , James P Donahue  2
Affiliations

Bis[1,2-bis-(4-fluoro-phen-yl)ethyl-ene-1,2-di-thiol-ato(1-)]nickel(II)

Joseph B Donahue et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The crystal structure of the title compound, [Ni(C14H8F2S2)2] (I), reveals averaged S-C [1.708 (2) Å] and C-Cchelate [1.395 (4) Å] bond lengths that are consistent with radical monoanionic ligands paired with a divalent Ni2+ ion. Mol-ecules of I associate as dyads via inter-molecular Ni⋯S close contacts of 3.396 (2) Å. This close association is enabled by a bending of both di-thiol-ene ligands to the same side and away from the NiS4 planar inter-ior such that the angle between the seven atom mean planes defined by each NiS2C2 ring and the first C atom of each aryl substituent is 22.91 (8)°. These dyads form sheets in the bc plane that are held together in part by inter-molecular C-H⋯F hydrogen bonds of 2.47 (4) Å.

Keywords: C—H→F hydrogen bonds; crystal structure; di­thiol­ene; electron-withdrawing; nickel; radical monoanion.

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Figures

Figure 1
Figure 1
Displacement ellipsoid plot (50% probability) of [Ni(S2C2(C6H4-4-F)2)2] with complete atom labeling.
Figure 2
Figure 2
Redox levels of the di­thiol­ene ligand with experimentally determined intra­ligand S—C and C—C bond lengths that are diagnostic of each redox state.
Figure 3
Figure 3
Displacement ellipsoid plot (50% probability) of [Ni(S2C2(C6H4-4-F)2)2] showing its close inter­action with a neighboring mol­ecule across an inversion center.
Figure 4
Figure 4
View down the a axis of the cell illustrating how the dyads shown in Fig. 2 ▸ are related by translation along the b axis. Displacement ellipsoids are shown at 50% probability, and all H atoms are omitted for clarity.
Figure 5
Figure 5
View down the b axis of the cell illustrating how the dyads shown in Fig. 2 ▸ form stacks in this axis direction. Displacement ellipsoids are shown at 50% probability, and all H atoms are omitted for clarity.
Figure 6
Figure 6
View down the a axis of the cell illustrating how the dyads of I inter­act in the bc plane via F⋯C—H hydrogen bonds. All H atoms are omitted except those involved in the F⋯C—H hydrogen bonding. The symmetry operation relating mol­ecules that are participants in a F⋯C—H hydrogen bond is x, y + 1, z + 1. Displacement ellipsoids are presented at the 50% probability level.
Figure 7
Figure 7
View along the bc plane of the packing for I, emphasizing the sheet-like arrangement of mol­ecules in this direction. Displacement ellipsoids are shown at the 50% level, and all H atoms are omitted for clarity.
Figure 8
Figure 8
Contrast between the dyadic pairs of [Ni(S2C2(C6H4-4-F)2)2] (a) vs. [Ni(S2C2(C6H4-4-Cl)2)2] (b). Closer association of mol­ecules in (a) than (b) is enabled by greater bending of the di­thiol­ene ligands away from one another. Displacement ellipsoids are shown at 50% probability, and all H atoms are omitted for clarity.
Figure 9
Figure 9
Known dimeric Ni bis­(di­thiol­ene) complexes shown with inter­molecular Ni⋯S and Ni⋯Ni distances.
See this image and copyright information in PMC

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