{4-Bromo-2-[(2-sulfido­phen­yl)imino­meth­yl]phenolato-κ3 S,N,O}(triphenyl­phosphane-κP)nickel(II)

M Muthu Tamizh; R Karvembu; B Varghese; Edward R T Tiekink

doi:10.1107/S1600536811008907

. 2011 Mar 12;67(Pt 4):m441. doi: 10.1107/S1600536811008907

{4-Bromo-2-[(2-sulfidophenyl)iminomethyl]phenolato-κ³ S,N,O}(triphenylphosphane-κP)nickel(II)

M Muthu Tamizh ^a, R Karvembu ^a,^‡, B Varghese ^b, Edward R T Tiekink ^c,^*

PMCID: PMC3099803 PMID: 21753963

Abstract

The Ni^II atom in the title complex, [Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)], is coordinated by the N, O and S atoms of the dianionic tridentate ligand, and its square-planar geometry is completed by a phosphane P atom. The dihedral angle between the aromatic rings in the 4-bromo-2-[(2-sulfidophenyl)iminomethyl]phenolate ligand is 2.01 (14)°. The most prominent feature of the packing is the presence of supramolecular chains aligned along the a axis, mediated by C—H⋯S interactions.

Related literature

For chemical background and related structures, see: Muthu Tamizh et al. (2009 ▶).

Experimental

Crystal data

[Ni(C₁₃H₈BrNOS)(C₁₈H₁₅P)]
M _r = 627.15
Orthorhombic,
a = 9.7197 (2) Å
b = 18.7729 (6) Å
c = 29.8372 (7) Å
V = 5444.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.592, T _max = 0.720
31370 measured reflections
6260 independent reflections
4184 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.092
S = 1.03
6260 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008907/hb5813sup1.cif

e-67-0m441-sup1.cif^{(25.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008907/hb5813Isup2.hkl

e-67-0m441-Isup2.hkl^{(300.3KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni—S1	2.1219 (7)
Ni—P1	2.1975 (7)
Ni—O1	1.8494 (18)
Ni—N1	1.900 (2)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯S1ⁱ	0.93	2.84	3.620 (3)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

RK and MMT gratefully acknowledge the CSIR [01 (2137)/07/EMR-II] for financial support. We also thank the SAIF, IIT-Madras, for the crystallographic data.

supplementary crystallographic information

Comment

The title complex, (I), was investigated as part of a wider investigation of complexes of interest owing to their relationship to Ni/Fe hydrogenases (Muthu Tamizh et al., 2009). The Ni^II atom exists within a square planar donor set defined by the N,O,S atoms of the dinegative tridentate ligand, and a P atom derived from the phosphane ligand. The S1, P1, O1 and N1 atoms deviate -0.0535 (7), 0.0556 (8), -0.0609 (8) and 0.0588 (8) Å, from their least-squares plane, respectively (r.m.s. deviation = 0.0573 Å), and the Ni atom lies 0.0548 (9) Å out of the plane. The geometric parameters about the Ni^II atom, Table 1, match closely those in the parent complex (Muthu Tamizh et al., 2009).

The most prominent interactions in the crystal structure are of the type C—H···S, Table 2. These connect molecules into linear supramolecular chains along the a axis, Fig. 2.

Experimental

Complex (I) was prepared from the reaction between [NiCl₂(PPh₃)₂] and N-(2-mercaptophenyl)-4-bromosalicylideneimine in ethanol solution following the literature procedure (Muthu Tamizh et al., 2009). Brown prisms of (I) were obtained by the diffusion of diethyl ether vapour into its dichloromethane solution. Characterization data are as given in Muthu Tamizh et al. (2009).