(2-Amino-3-nitro­benzoato-κO)triphenyl­tin(IV)

Yip-Foo Win; Chen-Shang Choong; Mei-Hsuan Heng; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S160053681101244X

. 2011 Apr 13;67(Pt 5):m561–m562. doi: 10.1107/S160053681101244X

(2-Amino-3-nitrobenzoato-κO)triphenyltin(IV)

Yip-Foo Win ^a, Chen-Shang Choong ^a, Mei-Hsuan Heng ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3089114 PMID: 21754293

Abstract

The asymmetric unit of the title compound, [Sn(C₆H₅)₃(C₇H₅N₂O₄)], consists of two independent molecules. In each molecule, the four-coordinated Sn^IV atom exists in a distorted tetrahedral geometry and two intramolecular N—H⋯O hydrogen bonds with S(6) ring motifs are present. In one molecule, the benzene ring of the 2-amino-3-nitrobenzoate ligand makes dihedral angles of 42.74 (11), 89.66 (13) and 53.04 (10)° with the three phenyl rings. The corresponding dihedral angles for the other molecule are 6.29 (11), 66.55 (11) and 62.33 (10)°. In the crystal, a weak intermolecular C—H⋯π interaction and a π–π stacking interaction with a centroid–centroid distance of 3.5877 (12) Å are observed.

Related literature

For general background to and the coordination environment of the title complex, see: Yeap & Teoh (2003 ▶); Win et al. (2007 ▶, 2008 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₇H₅N₂O₄)]
M _r = 531.12
Triclinic,
a = 11.2836 (1) Å
b = 14.9600 (2) Å
c = 15.1828 (3) Å
α = 109.257 (1)°
β = 98.503 (1)°
γ = 105.743 (1)°
V = 2247.89 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 296 K
0.44 × 0.32 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.628, T _max = 0.810
69259 measured reflections
18711 independent reflections
12707 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.080
S = 1.01
18711 reflections
593 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.42 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/S160053681101244X/is2696sup1.cif

e-67-0m561-sup1.cif^{(36.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101244X/is2696Isup2.hkl

e-67-0m561-Isup2.hkl^{(914.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1A–C6A phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O3A	0.84 (3)	2.02 (3)	2.632 (3)	129 (2)
N1A—H2NA⋯O2A	0.84 (3)	1.99 (3)	2.671 (3)	138 (2)
N1B—H1NB⋯O2B	0.84 (2)	1.98 (3)	2.643 (3)	135 (2)
N1B—H2NB⋯O3B	0.83 (2)	1.96 (2)	2.607 (3)	135.3 (19)
C15B—H15B⋯Cg1ⁱ	0.93	2.84	3.596 (3)	139

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Symmetry code: (i) Inline graphic .

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

Commonly, triphenyltin(IV) carboxylate complexes exist as a monomeric and polymeric structures (Yeap &Teoh, 2003; Win et al., 2007, 2008, 2010). For monomeric structures, the tin(IV) moiety could be either four- or five-coordinated. However, for polymeric structures, the tin(IV) moiety normally exist in five-coordinated (Win et al., 2010). The title complex is found to be similar to the reported structure of (2-amino-5-nitrobenzoato)triphenyltin(IV) (Win et al., 2007) with the exception that the nitro group is in a different position at the benzoate moiety in this study.

The asymmetric unit contains two independent molecules (Fig. 1), A and B. In each molecule, the four-coordinate tin atom (Sn1A/Sn1B) exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The molecular structure is stabilized by intramolecular N1A—H1NA···O3A, N1A—H2NA···O2A, N1B—H1NB···O2B and N1B—H2NB···O3B hydrogen bonds (Table 1) which generate S(6) ring motifs (Fig. 1; Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal ranges. In molecule A, the phenyl ring (C20A–C25A) of 2-amino-3-nitrobenzoate moiety makes dihedral angles of 42.74 (11), 89.66 (13) and 53.04 (10)° with respect to the three phenyl rings (C1A–C6A, C7A–C12A and C13A–C18A). The corresponding dihedral angles for molecule B are 6.29 (11), 66.55 (11) and 62.33 (10)°.

In the crystal (Fig. 2), a weak intermolecular C—H···π interaction (Table 1) and a π–π stacking interaction between two phenyl rings (C20B–C25B, centroid Cg2), with a Cg2···Cg2 distance of 3.5877 (12) Å are observed. No significant intermolecular hydrogen bond is observed.

Experimental

The title complex was obtained by heating under reflux a 1:1 molar mixture of triphenyltin(IV) hydroxide (0.73 g, 2 mmol) and 2-amino-3-nitrobenzoic acid (0.36 g, 2 mmol) in methanol (60 mL) for 2 h. A clear yellow transparent solution was separated by filtration and kept in a bottle. After a few days, yellow crystals (0.46 g, 86.0 % yield) were collected (m.p. 155.0–156.0 °C). Analysis for C₂₅H₂₀N₂O₄Sn: C 56.72, H 3.73, N 5.24%. Calculated for C₂₅H₂₀N₂O₄Sn: C 56.53, H 3.80, N, 5.27%.