metal-organic compounds
catena-Poly[[trimethyltin(IV)]-μ-[(E)-2-methyl-3-(3-methylphenyl)acrylato-κ2O:O′]]
aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bUniversity of Sargodha, Department of Physics, Sagrodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
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 [2.114 (2) Å], whereas the other is a [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
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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).
Supporting information
10.1107/S1600536808019533/ng2468sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808019533/ng2468Isup2.hkl
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%.
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.
Data collection: APEX2 (Bruker, 2007); cell
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).[Sn(CH3)3(C11H11O2)] | F(000) = 1360 |
Mr = 339.01 | Dx = 1.491 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3348 reflections |
a = 12.9530 (6) Å | θ = 2.6–27.1° |
b = 9.8756 (4) Å | µ = 1.68 mm−1 |
c = 24.0728 (10) Å | T = 296 K |
β = 101.301 (2)° | Prismatic, colourless |
V = 3019.7 (2) Å3 | 0.25 × 0.18 × 0.15 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 3348 independent reflections |
Radiation source: fine-focus sealed tube | 2874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 7.5 pixels mm-1 | θmax = 27.2°, θmin = 2.6° |
ω sans scans | h = −16→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −7→12 |
Tmin = 0.705, Tmax = 0.781 | l = −30→30 |
14486 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0374P)2 + 3.5913P] where P = (Fo2 + 2Fc2)/3 |
3348 reflections | (Δ/σ)max = 0.001 |
145 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
[Sn(CH3)3(C11H11O2)] | V = 3019.7 (2) Å3 |
Mr = 339.01 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.9530 (6) Å | µ = 1.68 mm−1 |
b = 9.8756 (4) Å | T = 296 K |
c = 24.0728 (10) Å | 0.25 × 0.18 × 0.15 mm |
β = 101.301 (2)° |
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 = 0.781 | Rint = 0.023 |
14486 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.63 e Å−3 |
3348 reflections | Δρmin = −0.41 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.28429 (1) | −0.16993 (2) | 0.22816 (1) | 0.0380 (1) | |
O1 | 0.32929 (16) | −0.03474 (18) | 0.16907 (8) | 0.0498 (6) | |
O2 | 0.26730 (17) | 0.1483 (2) | 0.20361 (9) | 0.0529 (7) | |
C1 | 0.3143 (2) | 0.0940 (3) | 0.17022 (10) | 0.0389 (7) | |
C2 | 0.3576 (2) | 0.1747 (2) | 0.12708 (11) | 0.0401 (8) | |
C3 | 0.3324 (3) | 0.3224 (3) | 0.12430 (15) | 0.0591 (10) | |
C4 | 0.4185 (2) | 0.1119 (3) | 0.09665 (11) | 0.0426 (8) | |
C5 | 0.4713 (2) | 0.1667 (3) | 0.05244 (12) | 0.0482 (9) | |
C6 | 0.5691 (3) | 0.1139 (4) | 0.04886 (14) | 0.0663 (11) | |
C7 | 0.6223 (3) | 0.1596 (5) | 0.00784 (19) | 0.0870 (18) | |
C8 | 0.5750 (3) | 0.2546 (5) | −0.03080 (15) | 0.0809 (15) | |
C9 | 0.4775 (3) | 0.3064 (4) | −0.02935 (13) | 0.0663 (11) | |
C10 | 0.4254 (3) | 0.2612 (3) | 0.01229 (12) | 0.0534 (10) | |
C11 | 0.42742 (14) | 0.40923 (17) | −0.07152 (7) | 0.0932 (18) | |
C12 | 0.35163 (14) | −0.33276 (17) | 0.19080 (7) | 0.0624 (11) | |
C13 | 0.38060 (14) | −0.08820 (17) | 0.30121 (7) | 0.0547 (10) | |
C14 | 0.12000 (14) | −0.14855 (17) | 0.20410 (7) | 0.0586 (10) | |
H3A | 0.33496 | 0.35644 | 0.16190 | 0.0885* | |
H3B | 0.26305 | 0.33584 | 0.10207 | 0.0885* | |
H3C | 0.38277 | 0.36974 | 0.10716 | 0.0885* | |
H4 | 0.42933 | 0.02018 | 0.10434 | 0.0511* | |
H6 | 0.59915 | 0.04728 | 0.07422 | 0.0792* | |
H7 | 0.68900 | 0.12660 | 0.00642 | 0.1042* | |
H8 | 0.61025 | 0.28430 | −0.05866 | 0.0972* | |
H10 | 0.35872 | 0.29454 | 0.01336 | 0.0640* | |
H11A | 0.37070 | 0.45259 | −0.05805 | 0.1396* | |
H11B | 0.40055 | 0.36550 | −0.10702 | 0.1396* | |
H11C | 0.47878 | 0.47577 | −0.07662 | 0.1396* | |
H12A | 0.30201 | −0.40592 | 0.18350 | 0.0935* | |
H12B | 0.41411 | −0.36295 | 0.21610 | 0.0935* | |
H12C | 0.36936 | −0.30341 | 0.15582 | 0.0935* | |
H13A | 0.34336 | −0.01717 | 0.31612 | 0.0820* | |
H13B | 0.44368 | −0.05221 | 0.29160 | 0.0820* | |
H13C | 0.39864 | −0.15800 | 0.32919 | 0.0820* | |
H14A | 0.09961 | −0.06049 | 0.21497 | 0.0879* | |
H14B | 0.08599 | −0.21672 | 0.22256 | 0.0879* | |
H14C | 0.09943 | −0.15869 | 0.16378 | 0.0879* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0438 (1) | 0.0315 (1) | 0.0422 (1) | −0.0025 (1) | 0.0169 (1) | −0.0026 (1) |
O1 | 0.0662 (12) | 0.0339 (9) | 0.0574 (11) | −0.0025 (9) | 0.0322 (10) | 0.0049 (8) |
O2 | 0.0681 (13) | 0.0464 (11) | 0.0518 (11) | 0.0016 (9) | 0.0307 (10) | −0.0030 (9) |
C1 | 0.0445 (14) | 0.0348 (12) | 0.0393 (12) | −0.0037 (11) | 0.0131 (11) | −0.0012 (10) |
C2 | 0.0499 (15) | 0.0326 (12) | 0.0405 (13) | −0.0067 (11) | 0.0152 (11) | 0.0005 (10) |
C3 | 0.086 (2) | 0.0339 (14) | 0.0670 (19) | −0.0010 (14) | 0.0383 (18) | 0.0022 (13) |
C4 | 0.0512 (15) | 0.0386 (13) | 0.0409 (13) | −0.0029 (12) | 0.0162 (11) | 0.0015 (11) |
C5 | 0.0548 (16) | 0.0507 (16) | 0.0432 (14) | −0.0101 (13) | 0.0196 (12) | −0.0023 (12) |
C6 | 0.063 (2) | 0.082 (2) | 0.0602 (19) | 0.0021 (18) | 0.0278 (16) | 0.0043 (18) |
C7 | 0.068 (2) | 0.126 (4) | 0.078 (3) | −0.014 (2) | 0.041 (2) | −0.008 (3) |
C8 | 0.083 (3) | 0.115 (3) | 0.0525 (19) | −0.036 (2) | 0.0324 (19) | 0.002 (2) |
C9 | 0.081 (2) | 0.075 (2) | 0.0420 (16) | −0.0339 (19) | 0.0099 (15) | 0.0009 (15) |
C10 | 0.0604 (18) | 0.0567 (18) | 0.0434 (14) | −0.0169 (14) | 0.0111 (13) | 0.0004 (13) |
C11 | 0.121 (4) | 0.100 (3) | 0.053 (2) | −0.040 (3) | 0.003 (2) | 0.023 (2) |
C12 | 0.085 (2) | 0.0397 (15) | 0.075 (2) | 0.0003 (15) | 0.0463 (19) | −0.0039 (14) |
C13 | 0.0519 (16) | 0.0603 (18) | 0.0517 (16) | −0.0072 (14) | 0.0099 (13) | −0.0042 (14) |
C14 | 0.0489 (16) | 0.0635 (19) | 0.0629 (18) | −0.0053 (14) | 0.0095 (14) | 0.0069 (15) |
Sn1—O1 | 2.1144 (19) | C3—H3B | 0.9600 |
Sn1—C12 | 2.1126 (17) | C3—H3C | 0.9600 |
Sn1—C13 | 2.1072 (17) | C4—H4 | 0.9300 |
Sn1—C14 | 2.1037 (18) | C6—H6 | 0.9300 |
Sn1—O2i | 2.607 (2) | C7—H7 | 0.9300 |
O1—C1 | 1.287 (3) | C8—H8 | 0.9300 |
O2—C1 | 1.223 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.502 (4) | C11—H11A | 0.9600 |
C2—C3 | 1.493 (4) | C11—H11B | 0.9600 |
C2—C4 | 1.330 (4) | C11—H11C | 0.9600 |
C4—C5 | 1.476 (4) | C12—H12A | 0.9600 |
C5—C6 | 1.388 (5) | C12—H12B | 0.9600 |
C5—C10 | 1.391 (4) | C12—H12C | 0.9600 |
C6—C7 | 1.386 (6) | C13—H13A | 0.9600 |
C7—C8 | 1.378 (6) | C13—H13B | 0.9600 |
C8—C9 | 1.369 (6) | C13—H13C | 0.9600 |
C9—C10 | 1.387 (5) | C14—H14A | 0.9600 |
C9—C11 | 1.492 (4) | C14—H14B | 0.9600 |
C3—H3A | 0.9600 | C14—H14C | 0.9600 |
O1—Sn1—C12 | 90.17 (7) | C5—C4—H4 | 115.00 |
O1—Sn1—C13 | 97.09 (7) | C5—C6—H6 | 120.00 |
O1—Sn1—C14 | 98.56 (7) | C7—C6—H6 | 120.00 |
O1—Sn1—O2i | 175.64 (7) | C6—C7—H7 | 120.00 |
C12—Sn1—C13 | 114.87 (7) | C8—C7—H7 | 120.00 |
C12—Sn1—C14 | 116.04 (7) | C7—C8—H8 | 119.00 |
C13—Sn1—C14 | 126.36 (7) | C9—C8—H8 | 119.00 |
Sn1—O1—C1 | 123.13 (17) | C5—C10—H10 | 119.00 |
Sn1ii—O2—C1 | 159.7 (2) | C9—C10—H10 | 119.00 |
O1—C1—O2 | 122.9 (2) | C9—C11—H11A | 109.00 |
O1—C1—C2 | 115.5 (2) | C9—C11—H11B | 109.00 |
O2—C1—C2 | 121.5 (3) | C9—C11—H11C | 109.00 |
C1—C2—C3 | 116.2 (2) | H11A—C11—H11B | 109.00 |
C1—C2—C4 | 118.4 (2) | H11A—C11—H11C | 109.00 |
C3—C2—C4 | 125.4 (3) | H11B—C11—H11C | 109.00 |
C2—C4—C5 | 129.4 (3) | Sn1—C12—H12A | 109.00 |
C4—C5—C6 | 117.7 (3) | Sn1—C12—H12B | 109.00 |
C4—C5—C10 | 123.5 (3) | Sn1—C12—H12C | 109.00 |
C6—C5—C10 | 118.7 (3) | H12A—C12—H12B | 109.00 |
C5—C6—C7 | 120.6 (3) | H12A—C12—H12C | 109.00 |
C6—C7—C8 | 119.1 (4) | H12B—C12—H12C | 109.00 |
C7—C8—C9 | 121.8 (4) | Sn1—C13—H13A | 109.00 |
C8—C9—C10 | 118.7 (3) | Sn1—C13—H13B | 109.00 |
C8—C9—C11 | 121.2 (3) | Sn1—C13—H13C | 109.00 |
C10—C9—C11 | 120.2 (3) | H13A—C13—H13B | 109.00 |
C5—C10—C9 | 121.1 (3) | H13A—C13—H13C | 109.00 |
C2—C3—H3A | 109.00 | H13B—C13—H13C | 109.00 |
C2—C3—H3B | 109.00 | Sn1—C14—H14A | 109.00 |
C2—C3—H3C | 110.00 | Sn1—C14—H14B | 109.00 |
H3A—C3—H3B | 109.00 | Sn1—C14—H14C | 109.00 |
H3A—C3—H3C | 110.00 | H14A—C14—H14B | 109.00 |
H3B—C3—H3C | 109.00 | H14A—C14—H14C | 109.00 |
C2—C4—H4 | 115.00 | H14B—C14—H14C | 109.00 |
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—C1 | 67.0 (2) | C2—C4—C5—C6 | 145.1 (3) |
C12—Sn1—O2i—C1i | −157.4 (5) | C2—C4—C5—C10 | −39.2 (5) |
C13—Sn1—O2i—C1i | 87.2 (5) | C4—C5—C6—C7 | 179.2 (3) |
C14—Sn1—O2i—C1i | −40.4 (5) | C10—C5—C6—C7 | 3.3 (5) |
Sn1—O1—C1—O2 | −4.3 (4) | C4—C5—C10—C9 | −178.1 (3) |
Sn1—O1—C1—C2 | 176.30 (16) | C6—C5—C10—C9 | −2.5 (5) |
Sn1ii—O2—C1—O1 | 146.2 (4) | C5—C6—C7—C8 | −2.5 (6) |
Sn1ii—O2—C1—C2 | −34.4 (7) | C6—C7—C8—C9 | 0.9 (7) |
O1—C1—C2—C3 | 174.6 (3) | C7—C8—C9—C10 | −0.1 (6) |
O1—C1—C2—C4 | −8.5 (4) | C7—C8—C9—C11 | 180.0 (4) |
O2—C1—C2—C3 | −4.8 (4) | C8—C9—C10—C5 | 0.9 (5) |
O2—C1—C2—C4 | 172.1 (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. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)3(C11H11O2)] |
Mr | 339.01 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.9530 (6), 9.8756 (4), 24.0728 (10) |
β (°) | 101.301 (2) |
V (Å3) | 3019.7 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.68 |
Crystal size (mm) | 0.25 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.705, 0.781 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14486, 3348, 2874 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.642 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.068, 1.01 |
No. of reflections | 3348 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.41 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
Sn1—O1 | 2.1144 (19) | Sn1—C14 | 2.1037 (18) |
Sn1—C12 | 2.1126 (17) | Sn1—O2i | 2.607 (2) |
Sn1—C13 | 2.1072 (17) | ||
O1—Sn1—C12 | 90.17 (7) | C12—Sn1—C13 | 114.87 (7) |
O1—Sn1—C13 | 97.09 (7) | C12—Sn1—C14 | 116.04 (7) |
O1—Sn1—C14 | 98.56 (7) | C13—Sn1—C14 | 126.36 (7) |
O1—Sn1—O2i | 175.64 (7) |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
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
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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.