Bis(dimethyl­formamide-κO){4,4′,6,6′-tetra­chloro-2,2-[butane-1,4-di­yl(nitrilo­methanylyl­idene)]diphenolato-κ4 O,N,N′,O′}nickel(II)

Hadi Kargar; Reza Kia; Amir Adabi Ardakani; Muhammad Nawaz Tahir

doi:10.1107/S1600536812028681

. 2012 Jun 30;68(Pt 7):m997–m998. doi: 10.1107/S1600536812028681

Bis(dimethylformamide-κO){4,4′,6,6′-tetrachloro-2,2-[butane-1,4-diyl(nitrilomethanylylidene)]diphenolato-κ⁴ O,N,N′,O′}nickel(II)

Hadi Kargar ^a,^*, Reza Kia ^b,^‡, Amir Adabi Ardakani ^a, Muhammad Nawaz Tahir ^c,^*

PMCID: PMC3393240 PMID: 22807808

Abstract

In the title Schiff base complex, [Ni(C₁₈H₁₄Cl₄N₂O₂)(C₃H₇NO)₂], the geometry around the Ni^II atom is distorted octahedral. It is coordinated by the N₂O₂ donor atoms of the tetradentate Schiff base ligand and the O atoms of two dimethylformamide molecules, which are cis to one another. The benzene rings are almost normal to each other [dihedral angle = 88.60 (14)°]. The various intramolecular C—H⋯O hydrogen bonds make S(5) and S(6) ring motifs. In the crystal, molecules are linked by pairs of weak C—H⋯Cl interactions, forming inversion dimers.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff base ligands and their complexes, see: Kargar, Kia, Abbasian et al. (2012 ▶); Kargar et al. (2011 ▶); Kia et al. (2010 ▶). For the crystal structure of the ligand, see: Kargar, Kia, Ardakani et al. (2012 ▶).

Experimental

Crystal data

[Ni(C₁₈H₁₄Cl₄N₂O₂)(C₃H₇NO)₂]
M _r = 637.01
Monoclinic,
a = 9.7392 (11) Å
b = 19.165 (2) Å
c = 15.0197 (14) Å
β = 93.236 (3)°
V = 2799.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 291 K
0.36 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.690, T _max = 0.761
23789 measured reflections
6633 independent reflections
4349 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.123
S = 1.02
6633 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028681/su2463sup1.cif

e-68-0m997-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028681/su2463Isup2.hkl

e-68-0m997-Isup2.hkl^{(324.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O4	0.97	2.58	3.327 (4)	134
C11—H11B⋯O4	0.97	2.40	3.057 (4)	125
C19—H19⋯O1	0.93	2.25	2.865 (4)	123
C8—H8A⋯Cl3ⁱ	0.97	2.86	3.753 (3)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

HK and AAA thank PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

supplementary crystallographic information

Comment

In continuation of our work on the synthesis and crystal structure analysis of Schiff base ligands and their complexes (Kargar, Kia, Abbasian et al., 2012; Kargar, Kia, Ardakani et al., 2012; Kargar et al., 2011; Kia et al., 2010), we report herein on the synthesize and crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Ni^II Schiff base complex. The geometry around Ni^II is distorted octahedral being coordinated by N₂O₂ donor atoms of the tetradentate ligand, 6,6'-((butane-1,4-diylbis(azanylylidene))bis(methanylylidene)) bis(2,4-dichlorophenol) [Kargar, Kia, Ardakani et al., 2012] and by two oxygen atoms of dimethylformamide molecules that are cis to one another. The bond lengths (Allen et al., 1987) and angles are within the normal range. The intramolecular C—H···O hydrogen bonds makes S(5) and S(6) ring motif (Table 1; Bernstein et al., 1995). The substituted benzene rings [C1–C6 and C13–C18] are almost normal [88.60 (14)°] to each other.

In the crystal structure molecules are linked by pairs of weak C—H···Cl interactions into individual inversion dimers (Table 1 and Fig. 2).

Experimental

The title compound was synthesized by adding 3,5-dichlorosalicylaldehyde-1,4-butylenediimine (1 mmol) to a solution of NiCl₂ .6H₂O (1.1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Green prismatic single crystals of the title compound, suitable for X-ray structure determination, were obtained by recrystallization from ethanol on slow evaporation of the solvents at room temperature over several days.