catena-Poly[[triphenyl­tin(IV)]-μ-5-amino-2-nitro­benzoato-κ2 O 1:O 1′]

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

doi:10.1107/S1600536811033332

. 2011 Aug 27;67(Pt 9):m1276–m1277. doi: 10.1107/S1600536811033332

catena-Poly[[triphenyltin(IV)]-μ-5-amino-2-nitrobenzoato-κ² O ¹:O ^1′]

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

PMCID: PMC3200871 PMID: 22064934

Abstract

The title compound, [Sn(C₆H₅)₃(C₇H₅N₂O₄)]_n, forms polymeric chains along [010]. The Sn^IV ion is five-coordinated in a distorted trigonal–bipyramidal geometry by two monodentate carboxylate groups and three phenyl rings. The axial sites are occupied by the O atoms of two symmetry-related carboxylate groups [O—Sn—O = 170.88 (3)°]. The benzene ring of the 5-amino-2-nitrobenzoate ligand forms dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings. In the crystal, the chains are linked by intermolecular N—H⋯O and weak C—H⋯O interactions into a three-dimensional network. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and the coordination environment of triphenyltin(IV) carboxylate complexes, see: Yeap & Teoh (2003 ▶); Win et al. (2006 ▶, 2008 ▶, 2011a ▶,b ▶,c ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₇H₅N₂O₄)]
M _r = 531.12
Monoclinic,
a = 10.9752 (1) Å
b = 11.8342 (1) Å
c = 17.4160 (2) Å
β = 102.164 (1)°
V = 2211.25 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 100 K
0.37 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.671, T _max = 0.783
27219 measured reflections
7981 independent reflections
7370 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.018
wR(F ²) = 0.046
S = 1.07
7981 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 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/S1600536811033332/lh5316sup1.cif

e-67-m1276-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033332/lh5316Isup2.hkl

e-67-m1276-Isup2.hkl^{(390.5KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯O1ⁱ	0.85 (2)	2.498 (19)	3.0619 (14)	124.3 (15)
C5—H5A⋯O4ⁱⁱ	0.95	2.40	3.3288 (16)	167
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.58	3.4430 (14)	152
C21—H21A⋯Cg1^iv	0.95	2.70	3.4669 (12)	138

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

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

Generally, the tin(IV) atom moiety of triphenyltin(IV) carboxylate complexes could existed as four- or five-coordinated depending on the coordination manner of the carboxylate anions and the coordinating solvent (Yeap and Teoh, 2003; Win et al., 2006; 2008; 2011a,b,c). In this study, the title complex is found to be similar to the reported structure of (2-amino-5-nitrobenzoato)triphenyltin(IV) (Win et al., 2006) except that the amino group is substituted at meta-position and the nitro group is substituted at ortho-position to the benzoate group.

The asymmetric unit of the title compound is shown in Fig. 1. The overall structure consists of polymeric one-dimensional chains along [010] (Fig. 2). The Sn1 atom is five-coordinate, with a distorted trigonal-bipyramidal coordination geometry, formed by two monodentate symmetry related carboxylate groups and three phenyl rings. The axial sites are occupied by the O atoms of the two carboxylate groups [O1-Sn1-O2ⁱ = 170.88 (3)°, symmetry code: (i) 2-x,-1/2+y,1/2-z], 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 the 5-amino-2-nitrobenzoato ligand makes dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings (C1-C6, C7-C12 and C13-C18).

In the crystal (Fig. 3), the polymeric one-dimensional chains are linked by intermolecular N1–H2N1···O1ⁱⁱⁱ and weak C5–H5A···O4^iv interactions into a three-dimensional network. The crystal structure is further consolidated by C21–H21A···Cg1ⁱⁱ and C3–H3A···Cg2^v (Table 1) interactions, where Cg1 and Cg2 are the centroids of C1-C6 and C7-C12 phenyl rings, repectively.

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 5-amino-2-nitrobenzoic acid (0.36 g, 2 mmol) in methanol (50 ml) for 3 h. A clear yellow transparent solution was separated by filtration and kept in a bottle. After a few days, yellow crystals (0.48 g, 89.0 % yield) were collected. Melting point: 442-443 K. Analysis for C₂₅H₂₀N₂O₄Sn: C, 55.89; H, 3.84; N, 5.14 %. Calculated for C₂₅H₂₀N₂O₄Sn: C, 56.53; H, 3.80; N, 5.27 %.