[1,2-Bis(diisopropylphosphanyl)ethane-κ2 P,P′](2-fluoro-N-{[(2-fluorophenyl)azanidyl]carbonyl}anilinido-κ2 N,N′)nickel(II)

The NiII atom in the title compound shows a distorted square-planar P2N2 coordination set provided by two bidentate ligands.

(12) motifs extending parallel to [100]. The title compound might be of interest with respect to the production of urea and carbamate derivatives of nickel(II).

Structure description
Isocyanates are compounds that contain the functional group -N C O and can be prepared in different ways, from rearrangements on a laboratory scale to the phosphogenation of primary amines (Saunders & Slocombe, 1948) used in industry. The importance of isocyanates is demonstrated by the multitude of reactions in which they can be either used directly or serve as reaction intermediates. For example, isocyanates are employed in the production of urea and carbamate derivatives, which find agrochemical and/or pharmaceutical applications (Braunstein & Nobel, 1989). In this context, studies regarding the reactivity of aromatic isocyanates with different substituents on the aromatic rings in the dimeric complex [Ni(dippe)] 2 (-H) 2 [dippe = 1,2-bis(diisopropylphosphino)ethane], which is an excellent precursor of nickel(II), were started.
The asymmetric unit of the title compound ( Fig. 1) consists of one [Ni(oFPU)(dippe)] molecule with oFPU = bis(2-fluorophenyl)urea. Both bidentate oFPU and dippe ligands data reports are coordinated to the Ni II ion, through the N and P atoms, respectively. The resulting coordination environment is distorted square-planar (Table 1), with the geometry index 4 = 0.195 ( 4 = 0 for an ideal square-planar arrangement; Yang et al., 2007). In the oFPU moiety, the fluorophenyl ring (F2, C22-C27) attached to N2 is disordered over two sets of sites. The aromatic rings are inclined to the NCON plane of urea by 62.90 (2) (C22-C27) and 70.58 (2) (C15-C2); the angle between the two aromatic rings is 57.47 (2) . Based on the relative orientation of the ortho substituents (considering only the major disorder component) with respect to the carbonyl group, the molecular conformation can be described as antianti, showing torsion angles (O) C21-N1-C15-C16 and (O) C21-N2-C22-C23 of 120.9 (6) and 117.0 (5) , respectively. These values are consistent with those reported in the literature (Solomos et al., 2017).

Synthesis and crystallization
A solution of 2-fluorophenylisocyanate (16 mg, 0.13 mmol) in THF (5 ml) was added dropwise to a stirring THF solution of [Ni(dippe)(-H)] 2 (35.9 mg, 0.058 mmol). A slight bubbling was observed, accompanied by colour changes from purple to green and then brown. The reaction mixture was subsequently heated at 353 K for 2 h. At the end of heating, the sample was placed in a vial, and left in an inert atmosphere for crystallization by evaporation of the solvent. After a few days, crystals formed, which were analyzed by single-crystal X-ray diffraction.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3. One of the fluorophenyl rings (F2/ C22-C27) was found to be disordered over two sets of sites in a refined 0.832 (7):0.168 (7) ratio. Restraints on bond lengths, angles and displacement ellipsoids were used to model the disorder.