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Acta Cryst. (2008). E64, m978    [ doi:10.1107/S1600536808019533 ]

catena-Poly[[trimethyltin(IV)]-[mu]-[(E)-2-methyl-3-(3-methylphenyl)acrylato-[kappa]2O:O']]

N. Muhammad, M. N. Tahir, S. Ali and Zia-ur-Rehman

Abstract top

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.

Comment top

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···CgAiv: symmetry code iv = 1 - x, 1 - y, -z]. The perpendicular distance between the centroids for CgA···CgAiii and CgA···CgAiv is 3.488 Å and 3.725 Å, respectively. The compound is polymeric in nature due to the bridging nature of carboxyl group.

Related literature top

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

Experimental top

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%.

Refinement top

H atoms were positioned geometrically, with C-H= 0.93, and 0.96 Å for aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the title compound, (C11H11O2)Sn(CH3)3 with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The interamolecular H-bond is shown by dotted lines.
[Figure 2] Fig. 2. The figure showing the polymeric compound.
catena-Poly[[trimethyltin(IV)]-µ-[(E)-2-methyl-3-\ (3-methylphenyl)acrylato-κ2O:O']] top
Crystal data top
[Sn(CH3)3(C11H11O2)]F000 = 1360
Mr = 339.01Dx = 1.491 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3348 reflections
a = 12.9530 (6) Åθ = 2.6–27.1º
b = 9.8756 (4) ŵ = 1.68 mm−1
c = 24.0728 (10) ÅT = 296 (2) K
β = 101.301 (2)ºPrismatic, colourless
V = 3019.7 (2) Å30.25 × 0.18 × 0.15 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3348 independent reflections
Radiation source: fine-focus sealed tube2874 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
Detector resolution: 7.5 pixels mm-1θmax = 27.2º
T = 296(2) Kθmin = 2.6º
ω sans scansh = −16→15
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −7→12
Tmin = 0.705, Tmax = 0.781l = −30→30
14486 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.068  w = 1/[σ2(Fo2) + (0.0374P)2 + 3.5913P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3348 reflectionsΔρmax = 0.63 e Å−3
145 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Sn(CH3)3(C11H11O2)]V = 3019.7 (2) Å3
Mr = 339.01Z = 8
Monoclinic, C2/cMo Kα
a = 12.9530 (6) ŵ = 1.68 mm−1
b = 9.8756 (4) ÅT = 296 (2) K
c = 24.0728 (10) Å0.25 × 0.18 × 0.15 mm
β = 101.301 (2)º
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3348 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2874 reflections with I > 2σ(I)
Tmin = 0.705, Tmax = 0.781Rint = 0.023
14486 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024145 parameters
wR(F2) = 0.068H-atom parameters constrained
S = 1.01Δρmax = 0.63 e Å−3
3348 reflectionsΔρmin = −0.41 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.28429 (1)−0.16993 (2)0.22816 (1)0.0380 (1)
O10.32929 (16)−0.03474 (18)0.16907 (8)0.0498 (6)
O20.26730 (17)0.1483 (2)0.20361 (9)0.0529 (7)
C10.3143 (2)0.0940 (3)0.17022 (10)0.0389 (7)
C20.3576 (2)0.1747 (2)0.12708 (11)0.0401 (8)
C30.3324 (3)0.3224 (3)0.12430 (15)0.0591 (10)
C40.4185 (2)0.1119 (3)0.09665 (11)0.0426 (8)
C50.4713 (2)0.1667 (3)0.05244 (12)0.0482 (9)
C60.5691 (3)0.1139 (4)0.04886 (14)0.0663 (11)
C70.6223 (3)0.1596 (5)0.00784 (19)0.0870 (18)
C80.5750 (3)0.2546 (5)−0.03080 (15)0.0809 (15)
C90.4775 (3)0.3064 (4)−0.02935 (13)0.0663 (11)
C100.4254 (3)0.2612 (3)0.01229 (12)0.0534 (10)
C110.42742 (14)0.40923 (17)−0.07152 (7)0.0932 (18)
C120.35163 (14)−0.33276 (17)0.19080 (7)0.0624 (11)
C130.38060 (14)−0.08820 (17)0.30121 (7)0.0547 (10)
C140.12000 (14)−0.14855 (17)0.20410 (7)0.0586 (10)
H3A0.334960.356440.161900.0885*
H3B0.263050.335840.102070.0885*
H3C0.382770.369740.107160.0885*
H40.429330.020180.104340.0511*
H60.599150.047280.074220.0792*
H70.689000.126600.006420.1042*
H80.610250.28430−0.058660.0972*
H100.358720.294540.013360.0640*
H11A0.370700.45259−0.058050.1396*
H11B0.400550.36550−0.107020.1396*
H11C0.478780.47577−0.076620.1396*
H12A0.30201−0.405920.183500.0935*
H12B0.41411−0.362950.216100.0935*
H12C0.36936−0.303410.155820.0935*
H13A0.34336−0.017170.316120.0820*
H13B0.44368−0.052210.291600.0820*
H13C0.39864−0.158000.329190.0820*
H14A0.09961−0.060490.214970.0879*
H14B0.08599−0.216720.222560.0879*
H14C0.09943−0.158690.163780.0879*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0438 (1)0.0315 (1)0.0422 (1)−0.0025 (1)0.0169 (1)−0.0026 (1)
O10.0662 (12)0.0339 (9)0.0574 (11)−0.0025 (9)0.0322 (10)0.0049 (8)
O20.0681 (13)0.0464 (11)0.0518 (11)0.0016 (9)0.0307 (10)−0.0030 (9)
C10.0445 (14)0.0348 (12)0.0393 (12)−0.0037 (11)0.0131 (11)−0.0012 (10)
C20.0499 (15)0.0326 (12)0.0405 (13)−0.0067 (11)0.0152 (11)0.0005 (10)
C30.086 (2)0.0339 (14)0.0670 (19)−0.0010 (14)0.0383 (18)0.0022 (13)
C40.0512 (15)0.0386 (13)0.0409 (13)−0.0029 (12)0.0162 (11)0.0015 (11)
C50.0548 (16)0.0507 (16)0.0432 (14)−0.0101 (13)0.0196 (12)−0.0023 (12)
C60.063 (2)0.082 (2)0.0602 (19)0.0021 (18)0.0278 (16)0.0043 (18)
C70.068 (2)0.126 (4)0.078 (3)−0.014 (2)0.041 (2)−0.008 (3)
C80.083 (3)0.115 (3)0.0525 (19)−0.036 (2)0.0324 (19)0.002 (2)
C90.081 (2)0.075 (2)0.0420 (16)−0.0339 (19)0.0099 (15)0.0009 (15)
C100.0604 (18)0.0567 (18)0.0434 (14)−0.0169 (14)0.0111 (13)0.0004 (13)
C110.121 (4)0.100 (3)0.053 (2)−0.040 (3)0.003 (2)0.023 (2)
C120.085 (2)0.0397 (15)0.075 (2)0.0003 (15)0.0463 (19)−0.0039 (14)
C130.0519 (16)0.0603 (18)0.0517 (16)−0.0072 (14)0.0099 (13)−0.0042 (14)
C140.0489 (16)0.0635 (19)0.0629 (18)−0.0053 (14)0.0095 (14)0.0069 (15)
Geometric parameters (Å, °) top
Sn1—O12.1144 (19)C3—H3B0.9600
Sn1—C122.1126 (17)C3—H3C0.9600
Sn1—C132.1072 (17)C4—H40.9300
Sn1—C142.1037 (18)C6—H60.9300
Sn1—O2i2.607 (2)C7—H70.9300
O1—C11.287 (3)C8—H80.9300
O2—C11.223 (3)C10—H100.9300
C1—C21.502 (4)C11—H11A0.9600
C2—C31.493 (4)C11—H11B0.9600
C2—C41.330 (4)C11—H11C0.9600
C4—C51.476 (4)C12—H12A0.9600
C5—C61.388 (5)C12—H12B0.9600
C5—C101.391 (4)C12—H12C0.9600
C6—C71.386 (6)C13—H13A0.9600
C7—C81.378 (6)C13—H13B0.9600
C8—C91.369 (6)C13—H13C0.9600
C9—C101.387 (5)C14—H14A0.9600
C9—C111.492 (4)C14—H14B0.9600
C3—H3A0.9600C14—H14C0.9600
O1—Sn1—C1290.17 (7)C5—C4—H4115.00
O1—Sn1—C1397.09 (7)C5—C6—H6120.00
O1—Sn1—C1498.56 (7)C7—C6—H6120.00
O1—Sn1—O2i175.64 (7)C6—C7—H7120.00
C12—Sn1—C13114.87 (7)C8—C7—H7120.00
C12—Sn1—C14116.04 (7)C7—C8—H8119.00
C13—Sn1—C14126.36 (7)C9—C8—H8119.00
Sn1—O1—C1123.13 (17)C5—C10—H10119.00
Sn1ii—O2—C1159.7 (2)C9—C10—H10119.00
O1—C1—O2122.9 (2)C9—C11—H11A109.00
O1—C1—C2115.5 (2)C9—C11—H11B109.00
O2—C1—C2121.5 (3)C9—C11—H11C109.00
C1—C2—C3116.2 (2)H11A—C11—H11B109.00
C1—C2—C4118.4 (2)H11A—C11—H11C109.00
C3—C2—C4125.4 (3)H11B—C11—H11C109.00
C2—C4—C5129.4 (3)Sn1—C12—H12A109.00
C4—C5—C6117.7 (3)Sn1—C12—H12B109.00
C4—C5—C10123.5 (3)Sn1—C12—H12C109.00
C6—C5—C10118.7 (3)H12A—C12—H12B109.00
C5—C6—C7120.6 (3)H12A—C12—H12C109.00
C6—C7—C8119.1 (4)H12B—C12—H12C109.00
C7—C8—C9121.8 (4)Sn1—C13—H13A109.00
C8—C9—C10118.7 (3)Sn1—C13—H13B109.00
C8—C9—C11121.2 (3)Sn1—C13—H13C109.00
C10—C9—C11120.2 (3)H13A—C13—H13B109.00
C5—C10—C9121.1 (3)H13A—C13—H13C109.00
C2—C3—H3A109.00H13B—C13—H13C109.00
C2—C3—H3B109.00Sn1—C14—H14A109.00
C2—C3—H3C110.00Sn1—C14—H14B109.00
H3A—C3—H3B109.00Sn1—C14—H14C109.00
H3A—C3—H3C110.00H14A—C14—H14B109.00
H3B—C3—H3C109.00H14A—C14—H14C109.00
C2—C4—H4115.00H14B—C14—H14C109.00
C12—Sn1—O1—C1−176.6 (2)C1—C2—C4—C5−179.4 (3)
C13—Sn1—O1—C1−61.5 (2)C3—C2—C4—C5−2.8 (5)
C14—Sn1—O1—C167.0 (2)C2—C4—C5—C6145.1 (3)
C12—Sn1—O2i—C1i−157.4 (5)C2—C4—C5—C10−39.2 (5)
C13—Sn1—O2i—C1i87.2 (5)C4—C5—C6—C7179.2 (3)
C14—Sn1—O2i—C1i−40.4 (5)C10—C5—C6—C73.3 (5)
Sn1—O1—C1—O2−4.3 (4)C4—C5—C10—C9−178.1 (3)
Sn1—O1—C1—C2176.30 (16)C6—C5—C10—C9−2.5 (5)
Sn1ii—O2—C1—O1146.2 (4)C5—C6—C7—C8−2.5 (6)
Sn1ii—O2—C1—C2−34.4 (7)C6—C7—C8—C90.9 (7)
O1—C1—C2—C3174.6 (3)C7—C8—C9—C10−0.1 (6)
O1—C1—C2—C4−8.5 (4)C7—C8—C9—C11180.0 (4)
O2—C1—C2—C3−4.8 (4)C8—C9—C10—C50.9 (5)
O2—C1—C2—C4172.1 (3)C11—C9—C10—C5−179.2 (3)
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O10.93002.28002.695 (3)107.00
Table 1
Selected geometric parameters (Å, °) top
Sn1—O12.1144 (19)Sn1—C142.1037 (18)
Sn1—C122.1126 (17)Sn1—O2i2.607 (2)
Sn1—C132.1072 (17)
O1—Sn1—C1290.17 (7)C12—Sn1—C13114.87 (7)
O1—Sn1—C1397.09 (7)C12—Sn1—C14116.04 (7)
O1—Sn1—C1498.56 (7)C13—Sn1—C14126.36 (7)
O1—Sn1—O2i175.64 (7)
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2.
Acknowledgements top

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.

references
References top

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