Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis­(triphenyl­phosphane-κP)copper(I) methanol monosolvate

Yu-Han Jiang; Qi-Ming Qiu; Rui-Xia Jiang; Xu Huang; Qiong-Hua Jin

doi:10.1107/S1600536812039165

. 2012 Sep 26;68(Pt 10):m1295. doi: 10.1107/S1600536812039165

Iodido[5-methyl-1H-benzimidazole-2(3H)-thione-κS]bis(triphenylphosphane-κP)copper(I) methanol monosolvate

Yu-Han Jiang ^a, Qi-Ming Qiu ^a, Rui-Xia Jiang ^b, Xu Huang ^a, Qiong-Hua Jin ^a,^*

PMCID: PMC3470167 PMID: 23125611

Abstract

In the title compound, [CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₃OH, the coordination environment around the Cu^I atom is distorted tetrahedral, defined by two P atoms of two triphenylphosphane ligands, one S atom of a 5-methyl-1H-benzimidazole-2(3H)-thione ligand and one I atom. The complex molecules and the methanol solvent molecules are connected via N—H⋯O and O—H⋯I hydrogen bonds, forming a chain along [010]. An intramolecular N—H⋯I hydrogen bond is also observed.

Related literature

For the structures and properties of transition metal complexes with phosphanes, see: Baxter et al. (1994 ▶); Kitagawa et al. (1995 ▶); Lewis et al. (1996 ▶). For complexes with a 2-mercapto-5-methylbenzimidazole ligand, see: Ozturk et al. (2009 ▶); Schneider et al. (2008 ▶). For related structures, see: Aslanidis et al. (1993 ▶); Li et al. (2004 ▶); Lobana et al. (2005 ▶).

Experimental

Crystal data

[CuI(C₈H₈N₂S)(C₁₈H₁₅P)₂]·CH₄O
M _r = 911.27
Monoclinic,
a = 15.6081 (11) Å
b = 10.5938 (8) Å
c = 25.976 (2) Å
β = 96.919 (1)°
V = 4263.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 298 K
0.43 × 0.38 × 0.35 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.585, T _max = 0.641
20808 measured reflections
7504 independent reflections
5465 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.088
S = 1.09
7504 reflections
478 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039165/hy2586sup1.cif

e-68-m1295-sup1.cif^{(32KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039165/hy2586Isup2.hkl

e-68-m1295-Isup2.hkl^{(367.2KB, 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
N1—H1⋯O1ⁱ	0.86	1.97	2.755 (7)	152
N2—H2⋯I1	0.86	2.80	3.539 (3)	145
O1—H1A⋯I1	0.82	2.67	3.469 (5)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 21171119), the National High Technology Research and Development Program of China (863 Program) (2012 A A063201), Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) (grant Nos. 2007CB310408 and 2006CB302901) and and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).

supplementary crystallographic information

Comment

Various transition metal complexes with bridging phosphanes or functionalized phosphanes have drawn much attention in recent years for their special structures, novel reactivity performances, catalytic properties and luminescence (Baxter et al., 1994; Kitagawa et al., 1995; Lewis et al., 1996). The 2-mercapto-5-methylbenzimidazole (MMBI) ligand, with an -SH group and two potential coordination N atoms, is excellent in building supramolecular structures (Ozturk et al., 2009; Schneider et al., 2008). However, to our best knowledge, Cu(I) complexes with the MMBI ligand have not been reported. In this paper, one Cu(I) complex with PPh₃ and MMBI is reported.

In the title compound, MMBI acts as a neutral, monodentate ligand with the S atom as a coordination atom. Other sites of the coordination tetrahedron are occupied by two P atoms from two PPh₃ ligands and an iodide anion (Fig. 1). The Cu—S, Cu—P and Cu—I bond lengths agree with those in [CuI(H₂itsc)(Ph₃P)₂] (H₂itsc = isatin-3-thiosemicarbazones) (Lobana et al., 2005) and [CuI(C₄H₆N₂S)(C₁₈H₁₅P)₂] (Li et al., 2004). Similarly, in the title complex, angles around the Cu atom ranging from 102.31 (4) to 122.72 (4)° are close to those in [CuI(PPh₃)₂(pymtH)] (pymtH = pyrimidine-2-thione) (Aslanidis et al., 1993). The complex molecules and the solvent methanol molecules are connected via N—H···O and O—H···I hydrogen bonds (Table 1), forming a chain along [0 1 0]. An intramolecular N—H···I hydrogen bond is also observed.

Experimental

A mixture of CuI (0.2 mmol) and 2-mercapto-5-methylbenzimidazole (0.2 mmol) in MeOH and CH₂Cl₂ (10 ml, v/v = 1:1) was stirred for 2 h. PPh₃ (0.2 mmol) was added to the mixture, which was stirred for another 4 h. The insoluble residues were removed by filtration, and filtrate was evaporated slowly at room temperature for a week to yield colorless crystalline products.