Methyl­(phenyl)­bis­(quinoline-2-carbox­ylato-κ2 N,O)tin(IV) monohydrate

Marzieh Vafaee; Mostafa M Amini; Seik Weng Ng

doi:10.1107/S1600536810054437

. 2011 Jan 12;67(Pt 2):m156–m157. doi: 10.1107/S1600536810054437

Methyl(phenyl)bis(quinoline-2-carboxylato-κ² N,O)tin(IV) monohydrate

Marzieh Vafaee ^a, Mostafa M Amini ^a, Seik Weng Ng ^b,^*

PMCID: PMC3051546 PMID: 21522838

Abstract

The Sn^IV atom in each of the two independent molecules in the asymmetric unit of the title compound, [Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)₂]·H₂O, is N,O-chelated by two quinoline-2-carboxylate ions; the dative Sn—N bonds are significantly longer than the covalent Sn—O bonds. The two O and two N atoms comprise a trapezoid, and the diorganotin skeleton is bent over the longer N—N edge [C—Sn—C = 144.2 (1) and 144.5 (1)° in the two independent molecules]. The uncoordinated water molecules serve to connect the skew-trapezoidal bipyramidal tin-bearing molecules, generating a linear chain motif running along the ac diagonal. The crystal studied was a non-merohedral twin having a minor component of 33.2 (1)%.

Related literature

For other diorganotin bis(quinoline-2-carboxylates), see: Chen et al. (2006 ▶); Dakternieks et al. (2003a ▶,b ▶); Kuang et al. (2008a ▶,b ▶); Wang et al. (2004 ▶); Yin et al. (2005 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

[Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)₂]·H₂O
M _r = 573.16
Triclinic,
a = 10.1645 (5) Å
b = 13.9747 (6) Å
c = 17.0047 (8) Å
α = 103.8670 (6)°
β = 95.3560 (7)°
γ = 99.0625 (7)°
V = 2294.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2009 ▶) T _min = 0.846, T _max = 0.944
13450 measured reflections
11013 independent reflections
8760 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.101
S = 1.07
11013 reflections
634 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054437/hg2770sup1.cif

e-67-0m156-sup1.cif^{(38.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054437/hg2770Isup2.hkl

e-67-0m156-Isup2.hkl^{(538.4KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Sn1—O1	2.074 (2)
Sn1—C1	2.093 (3)
Sn1—O3	2.097 (2)
Sn1—C2	2.121 (3)
Sn1—N1	2.483 (3)
Sn1—N2	2.644 (3)
Sn2—O5	2.072 (2)
Sn2—O7	2.091 (2)
Sn2—C28	2.096 (3)
Sn2—C29	2.123 (3)
Sn2—N3	2.548 (3)
Sn2—N4	2.647 (3)

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C1—Sn1—C2	144.5 (1)
C28—Sn2—C29	144.2 (1)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O2	0.84	2.09	2.914 (4)	167
O1w—H1w2⋯O8	0.84	1.95	2.777 (4)	167
O2w—H2w1⋯O4	0.84	2.08	2.911 (4)	171
O2w—H2w2⋯O6ⁱ	0.84	2.07	2.898 (4)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The anion of quinoline-2-carboxylic acid N,O-chelates to diorganotin(IV) cations to confer a six-coordinate geometry to the tin atom. The geometry is better described as a skew-trapezoidal bipyramid. The reported compounds having two identical organic radicals bound to tin (see: Chen et al., 2006; Dakternieks et al., 2003a, 2003b; Kuang et al., 2008a, 2008b; Wang et al., 2004; Yin et al., 2005; Zhang et al., 2006). The mixed-organyl compound, Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)₂^.H₂O (Scheme I) is an example of a diorganotin quinoline-2-carboxylate having different organic groups; the synthesis of the parent diorganotin dichloride is a non-trivial synthesis. There are two independent molecules in the asymmetric unit. In both, the tin atom is N,O-chelated by two carboxylate ions; the dative Sn–N bond is significantly longer than the covalent Sn–O bond. The two O and two N atoms comprise a trapezoid, and the diorganotin skeleton is bent over the longer N–N edge (Table 1, (Fig. 1). The lattice water molecules serve to connect the skew-trapezoidal bipyramidal tin-bearing molecules to generate a linear chain motif (Fig. 2).

Experimental

Sodium quinoline-2-carboxylate was prepared by reacting sodium hydroxide and quinoline-2-carboxylic acid in toluene and removing of water in a Dean-Stark trap. The compound (0.20 g, 1 mmol) and methylphenyltin dichloride (0.35 g, 1 mmol) were stirred in a small volume of toluene at room temperature for an hour. The solid that formed was collected and recrystalized from methanol.