Trichlorido(dimethyl sulfoxide-κO)(di-2-pyridyl­amine-κ2 N,N′)indium(III)

Sadif A Shirvan; Sara Haydari Dezfuli; Elyas Golabi

doi:10.1107/S1600536812038147

. 2012 Sep 12;68(Pt 10):m1256. doi: 10.1107/S1600536812038147

Trichlorido(dimethyl sulfoxide-κO)(di-2-pyridylamine-κ² N,N′)indium(III)

Sadif A Shirvan ^a,^*, Sara Haydari Dezfuli ^a, Elyas Golabi ^b

PMCID: PMC3470143 PMID: 23125587

Abstract

In the title compound, [InCl₃(C₁₀H₉N₃)(C₂H₆OS)], the In^III atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating di-2-pyridylamine ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. Intermolecular C—H⋯Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distance = 3.510 (3) Å] are present in the crystal.

Related literature

For related structures, see: Abedi et al. (2011 ▶, 2012a ▶,b ▶); Ahmadi et al. (2008 ▶); Clemente (2005 ▶); Dong et al. (1987 ▶); Ilyuhin & Malyarik (1994 ▶); Kalateh, Ahmadi et al. (2008 ▶); Kalateh, Norouzi et al. (2008 ▶); Malecki et al. (2011 ▶); Malyarick et al. (1992 ▶); Shi & Jiang (2006 ▶); Shirvan & Haydari Dezfuli (2012 ▶); Yoshikawa et al. (2004 ▶); Yousefi et al. (2009 ▶).

Experimental

Crystal data

[InCl₃(C₁₀H₉N₃)(C₂H₆OS)]
M _r = 470.51
Monoclinic,
a = 29.283 (2) Å
b = 7.7642 (7) Å
c = 15.9459 (12) Å
β = 104.891 (6)°
V = 3503.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.702, T _max = 0.796
14020 measured reflections
3448 independent reflections
2503 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.080
S = 0.99
3448 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) ▶.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038147/hy2584sup1.cif

e-68-m1256-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038147/hy2584Isup2.hkl

e-68-m1256-Isup2.hkl^{(169.2KB, 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
C11—H11C⋯Cl2ⁱ	0.96	2.74	3.499 (8)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

supplementary crystallographic information

Comment

Recently, we reported the synthesis and crystal structure of [In(4,4'-dmbipy)Cl₃(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine). Several In^III complexes with a formula [In(L₁)Cl₃(L₂)] (L₁ = an N,N'-chelating ligand, L₂ = DMSO, H₂O, MeOH or EtOH), such as [In(bipy)Cl₃(H₂O)], (III), [In(bipy)Cl₃(EtOH)], (IV), [In(bipy)Cl₃(H₂O)].H₂O, (V) (Malyarick et al., 1992), [In(phen)Cl₃(DMSO)], (VI) (Dong et al., 1987), [In(phen)Cl₃(H₂O)], (VII), [In(phen)Cl₃(EtOH)].EtOH, (VIII) (Ilyuhin & Malyarik, 1994), [In(4,4'-dmbipy)Cl₃(DMSO)], (IX) (Ahmadi et al., 2008), [In(5,5'-dmbipy)Cl₃(MeOH)], (X) (Kalateh, Ahmadi et al., 2008), [In(4,4'-dtbipy)Cl₃(MeOH)].0.5MeOH, (XI) (Abedi et al., 2012a), [In(4bt)Cl₃(MeOH)], (XII) and [In(4bt)Cl₃(DMSO)], (XIII) (Abedi et al., 2012b) (bipy = 2,2'-bipyridine, phen = 1,10-phenanthroline, DMSO = dimethyl sulfoxide, 4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbipy = 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine, 4bt = 4,4'-bithiazole), have been synthesized and characterized by single-crystal X-ray diffraction methods. Di-2-pyridylamine (DPA) is a good bidentate ligand, and numerous complexes with DPA have been prepared, such as that of [Hg(DPA)Br₂], (XIV) (Kalateh, Norouzi et al., 2008), [Hg(DPA)Cl₂], (XV) (Yousefi et al., 2009), [Pt(DPA)Cl₄].DMF, (XVI) (Abedi et al., 2011), [Ir(DPA)₂Cl₂](PF₆), (XVII) (Yoshikawa et al., 2004), [Cu(DPA)₂](BF₄)₂, (XVIII) (Clemente, 2005), [Mn(DPA)₂(NCS)₂].0.5H₂O, (XIX) (Malecki et al., 2011) and [Au(DPA)Cl₂]Cl, (XX) (Shi & Jiang, 2006). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the In^III atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating DPA ligand, one O atom from a dimethyl sulfoxide ligand and three Cl atoms. In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg3···Cg3ⁱ [symmetry code: (i) -x, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring], with a centroid–centroid distance of 3.510 (3) Å, stabilize the structure.

Experimental

For the preparation of the title compound, a solution of di-2-pyridylamine (0.29 g, 1.65 mmol) in methanol (10 ml) was added to a solution of InCl₃.4H₂O (0.48 g, 1.65 mmol) in methanol (10 ml) at room temperature. The suitable crystals for X-ray diffraction analysis were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.57 g, 73.4%).