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Acta Cryst. (2008). E64, m722-m723    [ doi:10.1107/S1600536808011112 ]

Cyclopentyldiphenyl(4-thiosemicarbazonopentanoato-[kappa]O)tin(IV)

K. M. Lo and S. W. Ng

Abstract top

The Sn atom in the title compound, [Sn(C5H9)(C6H5)2(C6H10N3O2S)], exists within a tetrahedral geometry. The -NH2 group forms a weak hydrogen bond across a center of inversion to the S atom of an adjacent molecule, as well as another weaker hydrogen (across another center of inversion) to the Sn-bound O atom of another molecule. The hydrogen-bonded layer structure is consolidated by a strong hydrogen bond between the -NH- group and the uncoordinated O atom of a third molecule.

Comment top

Triorganotin carboxylates having two different organyl substituents possess ehanced anti-bacterial and anti-fungal properties compared with the symmetrical compounds (Koshy et al., 2001). The synthesis of cyclopentyldiphenyltin hydroxide, which is the principal reagent that condenses readily with carboxylic acids, is a multi-step synthesis. Previous studies have characterized a few cyclopentyldiphenyltin derivatives (Lo & Ng, 2004; Lo et al., 1999; Teo et al., 2004). In the reaction with levulinic acid thiosemicarbazone (Ng, 1992), the organotin hydroxide yields a four-coordinate compound (I) (Fig. 1 & Table 1). The tin atom exists in a tetrahedral geometry; adjacent molecules are linked by hydrogen bonds into a layer structure, Table 2.

Related literature top

For the anti-bacterial and anti-fungal applications of cyclopentyldiphenyltin carboxylates, see: Koshy et al. (2001). For the crystal structures of cyclopentyldiphenyltin derivatives, see: Lo & Ng (2004); Lo et al. (1999); Teo et al. (2004). For the synthesis of levulinic acid thiosemicarbazone, see: Ng (1992). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Levulinic acid thiosemicarbazone was synthesized from the reaction of levulinic acid and thiosemicarbazide (Ng, 1992). Cyclopentyldiphenyltin hydroxide was sythesized by using a multistep reaction, starting from the Grignard reaction of cyclopentylmagnesium bromide on triphenyltin chloride. One phenyl radical was then cleaved by iodine in DMF; the resulting iodide was then hydrolyzed with sodium hydroxide in acetone to give the mixed triorganotin hydroxide (Lo et al., 1999). The thiosemicarbazone (1.1 g, 5 mmol) and triorganotin hydroxide (2 g, 5 mmol) were dissolved in hot ethanol (50 ml). The clear solution was filtered and colorless crystals separated from the cool solution after a day (yield: 75%).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The nitrogen-bound H-atom were similarly generated (N–H 0.88±0.01 Å) and their temperature factors similarly tied.

The final difference Fourier map had a large peak at 1.4 Å from C1 but was otherwise diffuse.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. 70% Probability thermal ellipsoid plot of Sn(C5H9)(C6H5)2(C12H15N3O2S), (I), show atom-numbering scheme. Hydrogen atoms are drawn as spheres of arbitrary radius.
Cyclopentyldiphenyl(4-thiosemicarbazonopentanoato-κO)tin(IV) top
Crystal data top
[Sn(C5H9)(C6H5)2(C6H10N3O2S)]Z = 2
Mr = 530.24F000 = 540
Triclinic, P1Dx = 1.503 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.5780 (1) ÅCell parameters from 9905 reflections
b = 10.2375 (1) Åθ = 2.4–28.3º
c = 13.4205 (1) ŵ = 1.20 mm−1
α = 86.901 (1)ºT = 100 (2) K
β = 83.370 (1)ºIrregular block, colorless
γ = 63.667 (1)º0.30 × 0.15 × 0.10 mm
V = 1171.50 (2) Å3
Data collection top
Bruker SMART APEXII
diffractometer		5350 independent reflections
Radiation source: fine-focus sealed tube5186 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→12
Tmin = 0.779, Tmax = 0.889k = −13→13
15020 measured reflectionsl = −17→17
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)] = 0.028H-atom parameters constrained
wR(F2) = 0.078  w = 1/[σ2(Fo2) + (0.0431P)2 + 2.3757P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5350 reflectionsΔρmax = 1.99 e Å−3
272 parametersΔρmin = −0.91 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Sn(C5H9)(C6H5)2(C6H10N3O2S)]γ = 63.667 (1)º
Mr = 530.24V = 1171.50 (2) Å3
Triclinic, P1Z = 2
a = 9.5780 (1) ÅMo Kα
b = 10.2375 (1) ŵ = 1.20 mm−1
c = 13.4205 (1) ÅT = 100 (2) K
α = 86.901 (1)º0.30 × 0.15 × 0.10 mm
β = 83.370 (1)º
Data collection top
Bruker SMART APEXII
diffractometer		5350 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5186 reflections with I > 2σ(I)
Tmin = 0.779, Tmax = 0.889Rint = 0.014
15020 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028272 parameters
wR(F2) = 0.078H-atom parameters constrained
S = 1.03Δρmax = 1.99 e Å−3
5350 reflectionsΔρmin = −0.91 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.400900 (17)0.628156 (16)0.232609 (11)0.01648 (6)
S10.24404 (7)0.05406 (6)0.56139 (5)0.02291 (13)
O10.4075 (2)0.63541 (19)0.38521 (13)0.0191 (3)
O20.1648 (2)0.66366 (19)0.38475 (13)0.0188 (3)
N10.1747 (2)0.4584 (2)0.57946 (15)0.0161 (4)
N20.1483 (2)0.3354 (2)0.58783 (15)0.0160 (4)
H2N0.05520.34100.60870.019*
N30.4100 (2)0.2066 (2)0.54086 (17)0.0215 (4)
H3N10.41870.28830.54330.026*
H3N20.49330.12480.52400.026*
C10.2123 (3)0.8151 (3)0.1783 (2)0.0269 (5)
H10.11890.79440.18630.032*
C20.2415 (5)0.8439 (5)0.0673 (3)0.0712 (16)
H2A0.19320.80010.02670.085*
H2B0.35530.80100.04600.085*
C30.1675 (4)1.0097 (4)0.0531 (2)0.0359 (7)
H3A0.24911.04420.03760.043*
H3B0.09871.0397−0.00190.043*
C40.0732 (5)1.0696 (4)0.1530 (3)0.0495 (9)
H4A−0.03431.07880.15420.059*
H4B0.06721.16630.16630.059*
C50.1651 (4)0.9556 (3)0.2307 (3)0.0398 (7)
H5A0.25770.96740.24560.048*
H5B0.09780.96250.29400.048*
C60.4168 (3)0.4221 (3)0.19650 (18)0.0199 (5)
C70.4926 (3)0.2975 (3)0.2541 (2)0.0245 (5)
H70.53610.30440.31260.029*
C80.5049 (3)0.1635 (3)0.2263 (2)0.0285 (6)
H80.55600.07940.26610.034*
C90.4429 (3)0.1523 (3)0.1411 (2)0.0271 (5)
H90.45160.06070.12230.032*
C100.3684 (3)0.2743 (3)0.08321 (19)0.0238 (5)
H100.32440.26680.02510.029*
C110.3575 (3)0.4079 (3)0.10956 (19)0.0225 (5)
H110.30930.49060.06800.027*
C120.6217 (3)0.6303 (3)0.19063 (17)0.0176 (4)
C130.7494 (3)0.5069 (3)0.14887 (18)0.0201 (5)
H130.73820.42060.14030.024*
C140.8925 (3)0.5089 (3)0.11974 (19)0.0236 (5)
H140.97840.42450.09130.028*
C150.9095 (3)0.6343 (3)0.13229 (19)0.0243 (5)
H151.00700.63590.11180.029*
C160.7847 (3)0.7577 (3)0.17470 (19)0.0231 (5)
H160.79700.84320.18410.028*
C170.6419 (3)0.7553 (3)0.20323 (18)0.0198 (5)
H170.55650.84000.23180.024*
C180.2692 (3)0.6595 (2)0.43182 (18)0.0163 (4)
C190.2537 (3)0.6844 (3)0.54288 (18)0.0184 (4)
H19A0.27390.76920.55360.022*
H19B0.33540.59820.57330.022*
C200.0950 (3)0.7117 (3)0.59732 (18)0.0194 (5)
H20A0.08660.75150.66450.023*
H20B0.01260.78720.56000.023*
C210.0628 (3)0.5805 (2)0.61014 (17)0.0162 (4)
C22−0.0961 (3)0.6051 (3)0.65817 (19)0.0211 (5)
H22A−0.14930.70230.68840.032*
H22B−0.08510.53130.71030.032*
H22C−0.15790.59790.60730.032*
C230.2715 (3)0.2065 (2)0.56254 (17)0.0170 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01453 (9)0.01349 (9)0.02213 (10)−0.00650 (6)−0.00357 (6)0.00085 (6)
S10.0168 (3)0.0119 (3)0.0404 (4)−0.0064 (2)−0.0043 (2)0.0007 (2)
O10.0150 (8)0.0209 (8)0.0235 (8)−0.0098 (7)−0.0020 (6)−0.0008 (6)
O20.0167 (8)0.0197 (8)0.0223 (8)−0.0099 (7)−0.0036 (6)0.0004 (6)
N10.0180 (9)0.0135 (9)0.0185 (9)−0.0081 (8)−0.0033 (7)−0.0001 (7)
N20.0139 (9)0.0128 (9)0.0219 (9)−0.0065 (7)−0.0021 (7)0.0007 (7)
N30.0148 (9)0.0140 (9)0.0349 (11)−0.0058 (8)0.0000 (8)−0.0047 (8)
C10.0213 (12)0.0260 (13)0.0251 (12)−0.0028 (10)−0.0042 (10)0.0019 (10)
C20.046 (2)0.068 (3)0.040 (2)0.023 (2)0.0084 (16)0.0231 (19)
C30.0378 (16)0.0442 (18)0.0334 (15)−0.0241 (14)−0.0144 (12)0.0166 (13)
C40.049 (2)0.0292 (16)0.064 (2)−0.0123 (15)−0.0080 (18)0.0046 (15)
C50.0435 (18)0.0289 (15)0.0423 (17)−0.0111 (14)−0.0067 (14)0.0004 (13)
C60.0214 (11)0.0190 (11)0.0228 (11)−0.0120 (10)−0.0032 (9)0.0000 (9)
C70.0274 (13)0.0209 (12)0.0287 (13)−0.0120 (10)−0.0120 (10)0.0026 (10)
C80.0327 (14)0.0183 (12)0.0366 (14)−0.0120 (11)−0.0105 (11)0.0048 (10)
C90.0285 (14)0.0221 (12)0.0323 (14)−0.0124 (11)−0.0035 (11)−0.0021 (10)
C100.0257 (13)0.0257 (13)0.0224 (12)−0.0133 (11)−0.0020 (10)−0.0032 (9)
C110.0236 (12)0.0205 (12)0.0230 (12)−0.0091 (10)−0.0052 (9)0.0021 (9)
C120.0163 (11)0.0177 (11)0.0186 (10)−0.0072 (9)−0.0035 (8)0.0027 (8)
C130.0215 (12)0.0169 (11)0.0209 (11)−0.0075 (9)−0.0030 (9)0.0021 (9)
C140.0188 (12)0.0238 (12)0.0227 (12)−0.0050 (10)−0.0008 (9)0.0009 (9)
C150.0200 (12)0.0322 (14)0.0232 (12)−0.0144 (11)−0.0020 (9)0.0040 (10)
C160.0265 (13)0.0260 (12)0.0233 (12)−0.0171 (11)−0.0041 (10)0.0015 (9)
C170.0194 (11)0.0185 (11)0.0211 (11)−0.0079 (9)−0.0026 (9)−0.0003 (9)
C180.0165 (11)0.0098 (9)0.0234 (11)−0.0063 (8)−0.0023 (8)−0.0002 (8)
C190.0206 (11)0.0142 (10)0.0228 (11)−0.0095 (9)−0.0038 (9)−0.0014 (8)
C200.0202 (11)0.0143 (10)0.0226 (11)−0.0064 (9)−0.0013 (9)−0.0029 (8)
C210.0163 (11)0.0157 (10)0.0162 (10)−0.0063 (9)−0.0033 (8)−0.0009 (8)
C220.0172 (11)0.0209 (11)0.0234 (11)−0.0070 (9)−0.0006 (9)−0.0032 (9)
C230.0173 (11)0.0139 (10)0.0203 (11)−0.0068 (9)−0.0050 (8)0.0006 (8)
Geometric parameters (Å, °) top
Sn1—O12.063 (2)C7—H70.9500
Sn1—C12.131 (3)C8—C91.379 (4)
Sn1—C62.125 (2)C8—H80.9500
Sn1—C122.134 (2)C9—C101.380 (4)
S1—C231.695 (2)C9—H90.9500
O1—C181.320 (3)C10—C111.387 (4)
O2—C181.227 (3)C10—H100.9500
N1—C211.283 (3)C11—H110.9500
N1—N21.387 (3)C12—C131.398 (3)
N2—C231.350 (3)C12—C171.399 (3)
N2—H2N0.8800C13—C141.391 (4)
N3—C231.325 (3)C13—H130.9500
N3—H3N10.8800C14—C151.384 (4)
N3—H3N20.8800C14—H140.9500
C1—C51.492 (4)C15—C161.389 (4)
C1—C21.522 (4)C15—H150.9500
C1—H11.0000C16—C171.388 (4)
C2—C31.532 (5)C16—H160.9500
C2—H2A0.9900C17—H170.9500
C2—H2B0.9900C18—C191.505 (3)
C3—C41.519 (5)C19—C201.520 (3)
C3—H3A0.9900C19—H19A0.9900
C3—H3B0.9900C19—H19B0.9900
C4—C51.547 (5)C20—C211.503 (3)
C4—H4A0.9900C20—H20A0.9900
C4—H4B0.9900C20—H20B0.9900
C5—H5A0.9900C21—C221.499 (3)
C5—H5B0.9900C22—H22A0.9800
C6—C111.396 (3)C22—H22B0.9800
C6—C71.398 (3)C22—H22C0.9800
C7—C81.393 (4)
O1—Sn1—C1112.7 (1)C8—C9—H9120.0
O1—Sn1—C6108.6 (1)C10—C9—H9120.0
O1—Sn1—C1295.9 (1)C9—C10—C11120.2 (2)
C1—Sn1—C6116.5 (1)C9—C10—H10119.9
C1—Sn1—C12112.1 (1)C11—C10—H10119.9
C6—Sn1—C12109.2 (1)C10—C11—C6120.7 (2)
Sn1—O1—C18109.3 (1)C10—C11—H11119.7
C21—N1—N2118.3 (2)C6—C11—H11119.7
C23—N2—N1117.11 (19)C13—C12—C17118.4 (2)
C23—N2—H2N121.4C13—C12—Sn1120.71 (18)
N1—N2—H2N121.4C17—C12—Sn1120.94 (18)
C23—N3—H3N1120.0C14—C13—C12120.8 (2)
C23—N3—H3N2120.0C14—C13—H13119.6
H3N1—N3—H3N2120.0C12—C13—H13119.6
C5—C1—C2106.2 (3)C15—C14—C13119.9 (2)
C5—C1—Sn1116.7 (2)C15—C14—H14120.1
C2—C1—Sn1113.0 (2)C13—C14—H14120.1
C5—C1—H1106.8C14—C15—C16120.4 (2)
C2—C1—H1106.8C14—C15—H15119.8
Sn1—C1—H1106.8C16—C15—H15119.8
C1—C2—C3106.9 (3)C17—C16—C15119.5 (2)
C1—C2—H2A110.3C17—C16—H16120.2
C3—C2—H2A110.3C15—C16—H16120.2
C1—C2—H2B110.3C16—C17—C12121.1 (2)
C3—C2—H2B110.3C16—C17—H17119.5
H2A—C2—H2B108.6C12—C17—H17119.5
C4—C3—C2104.5 (3)O2—C18—O1120.5 (2)
C4—C3—H3A110.9O2—C18—C19125.2 (2)
C2—C3—H3A110.9O1—C18—C19114.2 (2)
C4—C3—H3B110.9C18—C19—C20114.6 (2)
C2—C3—H3B110.9C18—C19—H19A108.6
H3A—C3—H3B108.9C20—C19—H19A108.6
C3—C4—C5104.1 (3)C18—C19—H19B108.6
C3—C4—H4A110.9C20—C19—H19B108.6
C5—C4—H4A110.9H19A—C19—H19B107.6
C3—C4—H4B110.9C21—C20—C19115.40 (19)
C5—C4—H4B110.9C21—C20—H20A108.4
H4A—C4—H4B109.0C19—C20—H20A108.4
C1—C5—C4102.4 (3)C21—C20—H20B108.4
C1—C5—H5A111.3C19—C20—H20B108.4
C4—C5—H5A111.3H20A—C20—H20B107.5
C1—C5—H5B111.3N1—C21—C22126.5 (2)
C4—C5—H5B111.3N1—C21—C20116.6 (2)
H5A—C5—H5B109.2C22—C21—C20116.8 (2)
C11—C6—C7118.4 (2)C21—C22—H22A109.5
C11—C6—Sn1119.38 (18)C21—C22—H22B109.5
C7—C6—Sn1122.09 (18)H22A—C22—H22B109.5
C8—C7—C6120.4 (2)C21—C22—H22C109.5
C8—C7—H7119.8H22A—C22—H22C109.5
C6—C7—H7119.8H22B—C22—H22C109.5
C9—C8—C7120.2 (3)N3—C23—N2117.2 (2)
C9—C8—H8119.9N3—C23—S1123.29 (18)
C7—C8—H8119.9N2—C23—S1119.54 (18)
C8—C9—C10120.0 (2)
C6—Sn1—O1—C18−77.70 (16)C9—C10—C11—C6−2.2 (4)
C1—Sn1—O1—C1852.80 (17)C7—C6—C11—C102.5 (4)
C12—Sn1—O1—C18169.72 (15)Sn1—C6—C11—C10179.0 (2)
C21—N1—N2—C23−174.8 (2)O1—Sn1—C12—C13110.54 (19)
O1—Sn1—C1—C532.7 (3)C6—Sn1—C12—C13−1.5 (2)
C6—Sn1—C1—C5159.1 (2)C1—Sn1—C12—C13−132.09 (19)
C12—Sn1—C1—C5−74.2 (2)O1—Sn1—C12—C17−70.09 (19)
O1—Sn1—C1—C2156.3 (3)C6—Sn1—C12—C17177.87 (18)
C6—Sn1—C1—C2−77.3 (3)C1—Sn1—C12—C1747.3 (2)
C12—Sn1—C1—C249.4 (3)C17—C12—C13—C14−0.6 (4)
C5—C1—C2—C3−15.5 (4)Sn1—C12—C13—C14178.79 (18)
Sn1—C1—C2—C3−144.7 (3)C12—C13—C14—C150.2 (4)
C1—C2—C3—C4−9.9 (5)C13—C14—C15—C160.6 (4)
C2—C3—C4—C530.7 (4)C14—C15—C16—C17−0.9 (4)
C2—C1—C5—C434.0 (4)C15—C16—C17—C120.4 (4)
Sn1—C1—C5—C4161.0 (2)C13—C12—C17—C160.3 (4)
C3—C4—C5—C1−40.3 (4)Sn1—C12—C17—C16−179.07 (18)
O1—Sn1—C6—C11155.98 (19)Sn1—O1—C18—O25.1 (3)
C1—Sn1—C6—C1127.6 (2)Sn1—O1—C18—C19−173.25 (14)
C12—Sn1—C6—C11−100.6 (2)O2—C18—C19—C202.0 (3)
O1—Sn1—C6—C7−27.7 (2)O1—C18—C19—C20−179.78 (19)
C1—Sn1—C6—C7−156.1 (2)C18—C19—C20—C2172.7 (3)
C12—Sn1—C6—C775.7 (2)N2—N1—C21—C222.0 (3)
C11—C6—C7—C8−1.6 (4)N2—N1—C21—C20−178.51 (19)
Sn1—C6—C7—C8−178.0 (2)C19—C20—C21—N13.9 (3)
C6—C7—C8—C90.4 (4)C19—C20—C21—C22−176.6 (2)
C7—C8—C9—C10−0.1 (4)N1—N2—C23—N36.1 (3)
C8—C9—C10—C111.0 (4)N1—N2—C23—S1−174.76 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···O2i0.882.122.975 (3)163
N3—H3n1···O1ii0.882.433.121 (3)136
N3—H3n2···S1iii0.882.543.389 (2)161
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Sn1—O12.063 (2)Sn1—C62.125 (2)
Sn1—C12.131 (3)Sn1—C122.134 (2)
O1—Sn1—C1112.7 (1)C1—Sn1—C12112.1 (1)
O1—Sn1—C6108.6 (1)C6—Sn1—C12109.2 (1)
O1—Sn1—C1295.9 (1)Sn1—O1—C18109.3 (1)
C1—Sn1—C6116.5 (1)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···O2i0.882.122.975 (3)163
N3—H3n1···O1ii0.882.433.121 (3)136
N3—H3n2···S1iii0.882.543.389 (2)161
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.
Acknowledgements top

We thank the University of Malaya for funding this study (FR155/2007 A) and also for the purchase of the diffractometer.

references
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