catena-Poly[[trimethyl­tin(IV)]-μ-[(E)-2-methyl-3-(3-methyl­phen­yl)acrylato-κ2 O:O′]]

Niaz Muhammad; M Nawaz Tahir; Saqib Ali; Zia-ur-Rehman

doi:10.1107/S1600536808019533

. 2008 Jul 5;64(Pt 8):m978. doi: 10.1107/S1600536808019533

catena-Poly[[trimethyltin(IV)]-μ-[(E)-2-methyl-3-(3-methylphenyl)acrylato-κ² O:O′]]

Niaz Muhammad ^a, M Nawaz Tahir ^b,^*, Saqib Ali ^a, Zia-ur-Rehman ^a

PMCID: PMC2961908 PMID: 21203077

Abstract

The title trimethyltin(IV) carboxylate, [Sn(CH₃)₃(C₁₁H₁₁O₂)]_n, is a carboxylate-bridged polymer in which the Sn atom exists in a trans-C₃SnO₂ trigonal bipyramidal coordination. One Sn—O bond is a covalent bond [2.114 (2) Å], whereas the other is a dative bond [2.607 (2) Å]. The polymeric chain propagates along the b axis of the monoclinic unit cell.

Related literature

For related crystal structures, see: Muhammad et al. (2008a ▶,b ▶); Niaz et al. (2008 ▶); Tahir et al. (1997a ▶,b ▶).

Experimental

Crystal data

[Sn(CH₃)₃(C₁₁H₁₁O₂)]
M _r = 339.01
Monoclinic,
a = 12.9530 (6) Å
b = 9.8756 (4) Å
c = 24.0728 (10) Å
β = 101.301 (2)°
V = 3019.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 296 (2) K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.705, T _max = 0.781
14486 measured reflections
3348 independent reflections
2874 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.068
S = 1.01
3348 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019533/ng2468sup1.cif

e-64-0m978-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019533/ng2468Isup2.hkl

e-64-0m978-Isup2.hkl^{(161KB, hkl)}

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

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

Sn1—O1	2.1144 (19)
Sn1—C12	2.1126 (17)
Sn1—C13	2.1072 (17)
Sn1—C14	2.1037 (18)
Sn1—O2ⁱ	2.607 (2)

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O1—Sn1—C12	90.17 (7)
O1—Sn1—C13	97.09 (7)
O1—Sn1—C14	98.56 (7)
O1—Sn1—O2ⁱ	175.64 (7)
C12—Sn1—C13	114.87 (7)
C12—Sn1—C14	116.04 (7)
C13—Sn1—C14	126.36 (7)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for financial support to NM for PhD studies under the Indigenous Scholarship Scheme.

supplementary crystallographic information

Comment

Organotin compounds have attracted much interest owing to their potential use in industry and agriculture. In the Pharmaceutical industry, a number of dialkyltin carboxylate derivatives are being used as efficient antitumor and anticancer agents. In continuation of synthesizing new ligands having carboxylate groups (Muhammad et al., 2008a, Niaz et al., 2008) and their complexation with organotin(IV) (Muhammad et al., 2008b), we report the crystal structure of title compound (I).

The title compound (I) (Fig 1.) is the trimethyltin(IV) complex of 3-(3-Methylphenyl)-2-methylacrylate (Muhammad et al., 2008a). The crystal structures of (II) {2-[(2,3-Dimethylphenyl)amino]benzoato-O:O'}trimethyltin(IV) (Tahir et al., 1997a) and (III) (Ketoprofenato)trimethyltin(IV) (Tahir et al., 1997b) have been reported. As the present complex have similar geometry around Sn-atom, so the bond lengths and bond angles are being compared with (II) and (III). The range of Sn—C [2.1037 (18)- 2.1126 (17) Å] bonds in (I) is reported as [2.106 (3)–2.113 (4) Å] in (II) and 2.106 (6)–2.116 (5) Å, in (III). The range of C—Sn—C [114.87 (7)- 126.36 (7)°] bond angles in (I) is reported as [113.9 (2)°-125.2 (1)°] in (II) and 117.0 (2)°-124.7 (3)°, in (III). Therefore, the C—Sn—C bond angles of trimethyltin moiety is mainly affected due to the change of coordinating ligand. The bond distances for Sn1—O1 [2.1144 (19) Å] and Sn1—O2ⁱ [2.607 (2) Å] (symmetry code i = -x + 1/2, y - 1/2, -z + 1/2) have different values compared to (II) and (III). These values in (II) and (III) are [2.153 (2) Å and 2.495 (2) Å] and [2.184 (3) Å and 2.433 (4) Å], respectively. The O1—Sn1—O2ⁱ bond angle is 175.64 (7)°, which is larger but not very different from (II) and (III). The dihedral angle between the plane of benzene ring A (C5—C10) and the plane formed by C11/C12/C13 is 76.16 (7)°, whereas it is 7.0 (7)° between O1/C1/O2 and C2/C3/C4. There is a single C—H···O interamolecular H-bond (Table 2, Fig 1.) forming a five-membered ring (O1/C1/C2/C4/H4···O1). There exist π-π-interactions between the centroids of benzene ring [CgA···CgAⁱⁱⁱ: symmetry code iii = 1 - x, -y, -z] and [CgA···CgA^iv: symmetry code iv = 1 - x, 1 - y, -z]. The perpendicular distance between the centroids for CgA···CgAⁱⁱⁱ and CgA···CgA^iv is 3.488 Å and 3.725 Å, respectively. The compound is polymeric in nature due to the bridging nature of carboxyl group.

Experimental

The title compound (I), was prepared by the reaction of stoichiometric amounts of the sodium 3-(3-methylphenyl)-2-methylacrylate (0.399 g, 2.02 mmol) and (0.402 g, 2.02 mmol)of trimethyltin(IV)chloride in dry toluene (100 ml). The reaction mixture was refluxed for 8 h and then allowed to stand overnight. The residual sodium salt was removed by filtration and the solvent was evaporated under reduced pressure leaving a solid residue. This was recrystallized from a mixture of chloroform/n-hexane (4:1). The yield was 80%.