(4-Chloro-3-nitro­benzoato)triphenyl­tin(IV)

Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S160053681103282X

. 2011 Aug 27;67(Pt 9):m1270–m1271. doi: 10.1107/S160053681103282X

(4-Chloro-3-nitrobenzoato)triphenyltin(IV)

Yip-Foo Win ^a, Chen-Shang Choong ^a, Siang-Guan Teoh ^b, Ching Kheng Quah ^c,^‡, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3200665 PMID: 22065496

Abstract

In the title compound, [Sn(C₆H₅)₃(C₇H₃ClNO₄)], the four-coordinate Sn^IV atom exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitrobenzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds into chains running parallel to [010].

Related literature

For general background to and the metal coordination environment of the title complex, see: Win et al. (2008 ▶, 2010 ▶, 2011a ▶,b ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₇H₃ClNO₄)]
M _r = 550.54
Monoclinic,
a = 12.3926 (2) Å
b = 8.8033 (1) Å
c = 21.5592 (3) Å
β = 103.217 (1)°
V = 2289.72 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 100 K
0.35 × 0.31 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.668, T _max = 0.807
23882 measured reflections
5204 independent reflections
4817 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.056
S = 1.11
5204 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.68 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 datablock(s) global, I. DOI: 10.1107/S160053681103282X/hb6362sup1.cif

e-67-m1270-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103282X/hb6362Isup2.hkl

e-67-m1270-Isup2.hkl^{(254.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Sn1—O1	2.0558 (15)
Sn1—C6	2.121 (2)
Sn1—C18	2.124 (2)
Sn1—C12	2.127 (2)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.93	2.55	3.346 (3)	144
C17—H17A⋯O1	0.93	2.56	3.140 (3)	120

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank Universiti Tunku Abdul Rahman (UTAR) for the UTAR Research Fund (Project No. IPSR/RMC/UTARRF/C1-C11/C07) and Universiti Sains Malaysia (USM) for providing research facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

The study of triphenyltin(IV) carboxylate complexes have received tremendous attention due to their structural diversity for which their structure could be monomeric or polymeric although the reaction was carried out in 1:1 molar ratio between the triphenyltin(IV) hydroxide and the respective acid (Win et al., 2008; 2010; 2011a,b). In this study, the structure of the title complex is similar to (2-chloro-4-nitrobenzoato)(methanol) triphenyltin(IV) (Win et al., 2011a). The only exceptions are that the methanol is not part of the crystal structure and the 2-chloro-4-nitrobenzoic acid is substituted with 4-chloro-3-nitrobenzoic acid.

The molecular structure is shown in Fig. 1. The four-coordinate tin atom (Sn1) exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The molecular structure is stabilized by an intramolecular C17–H17A···O1 hydrogen bond (Table 1), which generates an S(5) ring motif (Fig. 1, Bernstein et al., 1995). The phenyl ring (C20-C25) of 4-chloro-3-nitrobenzoate moiety makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with respect to the other three phenyl rings (C1-C6, C7-C12 and C13-C18). Oxygen atoms (O3/O4) of the nitro group are disordered over two positions with refined site-occupancies of 0.817 (5) and 0.183 (5).

In the crystal (Fig. 2), molecules are linked via intermolecular C3–H3A···O2 hydrogen bonds (Table 1) into one-dimensional chains parallel to [010] direction.

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 4-chloro-3-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 few days, colourless blocks (1.43 g, 82.1% yield) were collected. Melting point: 408-410 K. Analysis for C₂₅H₁₈NO₄ClSn: C, 55.60; H, 3.30; N, 2.55 %. Calculated for C₂₅H₁₈NO₄ClSn: C, 54.54; H, 3.29; N, 2.54 %.