(2-Chloro-4-nitro­benzoato)(methanol)triphenyl­tin(IV)

Yip-Foo Win; Chen-Shang Choong; Sie-Tiong Ha; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536811011962

. 2011 Apr 7;67(Pt 5):m535. doi: 10.1107/S1600536811011962

(2-Chloro-4-nitrobenzoato)(methanol)triphenyltin(IV)

Yip-Foo Win ^a, Chen-Shang Choong ^a, Sie-Tiong Ha ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3089065 PMID: 21754275

Abstract

In the title complex, [Sn(C₆H₅)₃(C₇H₃ClNO₄)(CH₄O)], the five-coordinate Sn^IV atom exists in a trigonal–bipyramidal environment, formed by a monodentate carboxylate group, three phenyl rings and a methanol molecule. The axial sites are occupied by the O atoms of the methanol molecule and the carboxylate group, while the equatorial plane is formed by the C atoms of three phenyl rings. The benzene ring of the 2-chloro-4-nitrobenzoate ligand makes dihedral angles of 66.18 (7), 74.71 (7) and 77.39 (7)° with respect to the three phenyl rings. In the crystal, the molecules are linked via intermolecular O—H⋯O and C—H⋯O hydrogen bonds into a column along the b axis.

Related literature

For general background to and the coordination environment of the title complex, see: Yeap & Teoh (2003 ▶); Szorcsik et al. (2006 ▶); Álvarez-Boo et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₇H₃ClNO₄)(CH₄O)]
M _r = 582.59
Monoclinic,
a = 9.0287 (3) Å
b = 13.5239 (4) Å
c = 20.7505 (6) Å
β = 108.894 (1)°
V = 2397.19 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 100 K
0.27 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.739, T _max = 0.835
42634 measured reflections
10460 independent reflections
9263 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.060
S = 1.04
10460 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.82 e Å⁻³
Δρ_min = −1.27 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011962/is2695sup1.cif

e-67-0m535-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011962/is2695Isup2.hkl

e-67-0m535-Isup2.hkl^{(511.5KB, 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
O3—H1O3⋯O2ⁱ	0.79 (3)	1.83 (3)	2.6082 (14)	170 (3)
C16—H16A⋯O4ⁱⁱ	0.93	2.58	3.312 (2)	136

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors would like to thank Universiti Tunku Abdul Rahman (UTAR) and Universiti Sains Malaysia (USM) for financial support as well as technical assistance and facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

There are a number of well documented literature indicating triphenyltin(IV) carboxylate complexes existing in monomeric five-coordinated structures, e.g. in structures in which the carboxylate anion is bonded to the tin(IV) atom in a monodentate mode and extra coordination being contributed from the coordinating ligands (Yeap & Teoh, 2003; Szorcsik et al., 2006; Álvarez-Boo et al., 2006). The coordinating ligands may be derivatives of coordinating solvents or from pyridine derivatives or amine. Complex (2,6-difluorobenzoato)triphenyltin(IV) showed that the two fluorine atoms at the ortho positions of the benzene fragment while the ethanol molecule was attached to the tin(IV) atom resulting the tin(IV) atom being five-coordinated (Yeap & Teoh, 2003).

The structure of the titled complex (Fig. 1) is similar to (2,6-difluorobenzoato)triphenyltin(IV). The only difference is that the methanol molecule participated in the crystal structure. In the title complex, the five-coordinate tin(IV) (Sn1) atom exists in a trigonal-bipyramidal environment, formed by a monodentate carboxylate group, three phenyl rings and a coordinated methanol molecule. The axial sites are occupied by the O atoms of the methanol and carboxylate [O1—Sn1—O3 = 169.05 (3)°], with the three phenyl rings occupying the equatorial plane. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzene ring (C20–C25) of 2-chloro-4-nitrobenzoate ligand makes dihedral angles of 66.18 (7), 74.71 (7) and 77.39 (7)° with respect to the three phenyl rings (C1–C6, C7–C12 and C13–C18). In the crystal structure, the molecules are linked via intermolecular O3–H1O3···O2 and C16–H16A···O4 hydrogen bonds (Table 1) into a column along the b axis (Fig. 2).

Experimental

The title complex was obtained by heating under reflux a 1:1 molar mixture of triphenyltin(IV) hydroxide (1.10 g, 3 mmol) and 2-chloro-4-nitrobenzoic acid (0.60 g, 3 mmol) in methanol (50 mL) for 2 h. A clear transparent solution was isolated by filtration and kept in a bottle. After a few days, crystals (1.36 g, 78.2 % yield) were collected (m.p.: 119.0-120.0 °C). Analysis for C₂₆H₂₂NO₅ClSn: C 53.45, H 3.74, N 2.34%. Calculated for C₂₆H₂₂NO₅ClSn: C 53.60, H 3.81, N 2.40%.