Cyclo­pentyl­diphen­yl(4-thio­semi­carbazonopenta­noato-κO)tin(IV)

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808011112

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m722-m723

doi:10.1107/S1600536808011112

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Cyclopentyldiphenyl(4-thiosemicarbazonopentanoato-κO)tin(IV)

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 March 2008; accepted 20 April 2008; online 26 April 2008)

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.

Related literature

For the antibacterial and antifungal 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

Crystal data

[Sn(C₅H₉)(C₆H₅)₂(C₆H₁₀N₃O₂S)]
M_r = 530.24
Triclinic, $[P \overline 1]$
a = 9.5780 (1) Å
b = 10.2375 (1) Å
c = 13.4205 (1) Å
α = 86.901 (1)°
β = 83.370 (1)°
γ = 63.667 (1)°
V = 1171.50 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 100 (2) K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.779, T_max = 0.889
15020 measured reflections
5350 independent reflections
5186 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.078
S = 1.03
5350 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 1.99 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.063 (2)
Sn1—C1	2.131 (3)
Sn1—C6	2.125 (2)
Sn1—C12	2.134 (2)

O1—Sn1—C1	112.7 (1)
O1—Sn1—C6	108.6 (1)
O1—Sn1—C12	95.9 (1)
C1—Sn1—C6	116.5 (1)
C1—Sn1—C12	112.1 (1)
C6—Sn1—C12	109.2 (1)
Sn1—O1—C18	109.3 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O2ⁱ	0.88	2.12	2.975 (3)	163
N3—H3n1⋯O1ⁱⁱ	0.88	2.43	3.121 (3)	136
N3—H3n2⋯S1ⁱⁱⁱ	0.88	2.54	3.389 (2)	161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011112/tk2255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011112/tk2255Isup2.hkl

checkCIF report

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%).

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

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
M_r = 530.24	F(000) = 540
Triclinic, P1	D_x = 1.503 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5780 (1) Å	Cell parameters from 9905 reflections
b = 10.2375 (1) Å	θ = 2.4–28.3°
c = 13.4205 (1) Å	µ = 1.20 mm⁻¹
α = 86.901 (1)°	T = 100 K
β = 83.370 (1)°	Irregular block, colorless
γ = 63.667 (1)°	0.30 × 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 tube	5186 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.779, T_max = 0.889	k = −13→13
15020 measured reflections	l = −17→17

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0431P)² + 2.3757P] where P = (F_o² + 2F_c²)/3
5350 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 1.99 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Sn(C₅H₉)(C₆H₅)₂(C₆H₁₀N₃O₂S)]	γ = 63.667 (1)°
M_r = 530.24	V = 1171.50 (2) Å³
Triclinic, P1	Z = 2
a = 9.5780 (1) Å	Mo Kα radiation
b = 10.2375 (1) Å	µ = 1.20 mm⁻¹
c = 13.4205 (1) Å	T = 100 K
α = 86.901 (1)°	0.30 × 0.15 × 0.10 mm
β = 83.370 (1)°

Data collection top

Bruker SMART APEXII diffractometer	5350 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5186 reflections with I > 2σ(I)
T_min = 0.779, T_max = 0.889	R_int = 0.014
15020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	Δρ_max = 1.99 e Å⁻³
5350 reflections	Δρ_min = −0.91 e Å⁻³
272 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.400900 (17)	0.628156 (16)	0.232609 (11)	0.01648 (6)
S1	0.24404 (7)	0.05406 (6)	0.56139 (5)	0.02291 (13)
O1	0.4075 (2)	0.63541 (19)	0.38521 (13)	0.0191 (3)
O2	0.1648 (2)	0.66366 (19)	0.38475 (13)	0.0188 (3)
N1	0.1747 (2)	0.4584 (2)	0.57946 (15)	0.0161 (4)
N2	0.1483 (2)	0.3354 (2)	0.58783 (15)	0.0160 (4)
H2N	0.0552	0.3410	0.6087	0.019*
N3	0.4100 (2)	0.2066 (2)	0.54086 (17)	0.0215 (4)
H3N1	0.4187	0.2883	0.5433	0.026*
H3N2	0.4933	0.1248	0.5240	0.026*
C1	0.2123 (3)	0.8151 (3)	0.1783 (2)	0.0269 (5)
H1	0.1189	0.7944	0.1863	0.032*
C2	0.2415 (5)	0.8439 (5)	0.0673 (3)	0.0712 (16)
H2A	0.1932	0.8001	0.0267	0.085*
H2B	0.3553	0.8010	0.0460	0.085*
C3	0.1675 (4)	1.0097 (4)	0.0531 (2)	0.0359 (7)
H3A	0.2491	1.0442	0.0376	0.043*
H3B	0.0987	1.0397	−0.0019	0.043*
C4	0.0732 (5)	1.0696 (4)	0.1530 (3)	0.0495 (9)
H4A	−0.0343	1.0788	0.1542	0.059*
H4B	0.0672	1.1663	0.1663	0.059*
C5	0.1651 (4)	0.9556 (3)	0.2307 (3)	0.0398 (7)
H5A	0.2577	0.9674	0.2456	0.048*
H5B	0.0978	0.9625	0.2940	0.048*
C6	0.4168 (3)	0.4221 (3)	0.19650 (18)	0.0199 (5)
C7	0.4926 (3)	0.2975 (3)	0.2541 (2)	0.0245 (5)
H7	0.5361	0.3044	0.3126	0.029*
C8	0.5049 (3)	0.1635 (3)	0.2263 (2)	0.0285 (6)
H8	0.5560	0.0794	0.2661	0.034*
C9	0.4429 (3)	0.1523 (3)	0.1411 (2)	0.0271 (5)
H9	0.4516	0.0607	0.1223	0.032*
C10	0.3684 (3)	0.2743 (3)	0.08321 (19)	0.0238 (5)
H10	0.3244	0.2668	0.0251	0.029*
C11	0.3575 (3)	0.4079 (3)	0.10956 (19)	0.0225 (5)
H11	0.3093	0.4906	0.0680	0.027*
C12	0.6217 (3)	0.6303 (3)	0.19063 (17)	0.0176 (4)
C13	0.7494 (3)	0.5069 (3)	0.14887 (18)	0.0201 (5)
H13	0.7382	0.4206	0.1403	0.024*
C14	0.8925 (3)	0.5089 (3)	0.11974 (19)	0.0236 (5)
H14	0.9784	0.4245	0.0913	0.028*
C15	0.9095 (3)	0.6343 (3)	0.13229 (19)	0.0243 (5)
H15	1.0070	0.6359	0.1118	0.029*
C16	0.7847 (3)	0.7577 (3)	0.17470 (19)	0.0231 (5)
H16	0.7970	0.8432	0.1841	0.028*
C17	0.6419 (3)	0.7553 (3)	0.20323 (18)	0.0198 (5)
H17	0.5565	0.8400	0.2318	0.024*
C18	0.2692 (3)	0.6595 (2)	0.43182 (18)	0.0163 (4)
C19	0.2537 (3)	0.6844 (3)	0.54288 (18)	0.0184 (4)
H19A	0.2739	0.7692	0.5536	0.022*
H19B	0.3354	0.5982	0.5733	0.022*
C20	0.0950 (3)	0.7117 (3)	0.59732 (18)	0.0194 (5)
H20A	0.0866	0.7515	0.6645	0.023*
H20B	0.0126	0.7872	0.5600	0.023*
C21	0.0628 (3)	0.5805 (2)	0.61014 (17)	0.0162 (4)
C22	−0.0961 (3)	0.6051 (3)	0.65817 (19)	0.0211 (5)
H22A	−0.1493	0.7023	0.6884	0.032*
H22B	−0.0851	0.5313	0.7103	0.032*
H22C	−0.1579	0.5979	0.6073	0.032*
C23	0.2715 (3)	0.2065 (2)	0.56254 (17)	0.0170 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01453 (9)	0.01349 (9)	0.02213 (10)	−0.00650 (6)	−0.00357 (6)	0.00085 (6)
S1	0.0168 (3)	0.0119 (3)	0.0404 (4)	−0.0064 (2)	−0.0043 (2)	0.0007 (2)
O1	0.0150 (8)	0.0209 (8)	0.0235 (8)	−0.0098 (7)	−0.0020 (6)	−0.0008 (6)
O2	0.0167 (8)	0.0197 (8)	0.0223 (8)	−0.0099 (7)	−0.0036 (6)	0.0004 (6)
N1	0.0180 (9)	0.0135 (9)	0.0185 (9)	−0.0081 (8)	−0.0033 (7)	−0.0001 (7)
N2	0.0139 (9)	0.0128 (9)	0.0219 (9)	−0.0065 (7)	−0.0021 (7)	0.0007 (7)
N3	0.0148 (9)	0.0140 (9)	0.0349 (11)	−0.0058 (8)	0.0000 (8)	−0.0047 (8)
C1	0.0213 (12)	0.0260 (13)	0.0251 (12)	−0.0028 (10)	−0.0042 (10)	0.0019 (10)
C2	0.046 (2)	0.068 (3)	0.040 (2)	0.023 (2)	0.0084 (16)	0.0231 (19)
C3	0.0378 (16)	0.0442 (18)	0.0334 (15)	−0.0241 (14)	−0.0144 (12)	0.0166 (13)
C4	0.049 (2)	0.0292 (16)	0.064 (2)	−0.0123 (15)	−0.0080 (18)	0.0046 (15)
C5	0.0435 (18)	0.0289 (15)	0.0423 (17)	−0.0111 (14)	−0.0067 (14)	0.0004 (13)
C6	0.0214 (11)	0.0190 (11)	0.0228 (11)	−0.0120 (10)	−0.0032 (9)	0.0000 (9)
C7	0.0274 (13)	0.0209 (12)	0.0287 (13)	−0.0120 (10)	−0.0120 (10)	0.0026 (10)
C8	0.0327 (14)	0.0183 (12)	0.0366 (14)	−0.0120 (11)	−0.0105 (11)	0.0048 (10)
C9	0.0285 (14)	0.0221 (12)	0.0323 (14)	−0.0124 (11)	−0.0035 (11)	−0.0021 (10)
C10	0.0257 (13)	0.0257 (13)	0.0224 (12)	−0.0133 (11)	−0.0020 (10)	−0.0032 (9)
C11	0.0236 (12)	0.0205 (12)	0.0230 (12)	−0.0091 (10)	−0.0052 (9)	0.0021 (9)
C12	0.0163 (11)	0.0177 (11)	0.0186 (10)	−0.0072 (9)	−0.0035 (8)	0.0027 (8)
C13	0.0215 (12)	0.0169 (11)	0.0209 (11)	−0.0075 (9)	−0.0030 (9)	0.0021 (9)
C14	0.0188 (12)	0.0238 (12)	0.0227 (12)	−0.0050 (10)	−0.0008 (9)	0.0009 (9)
C15	0.0200 (12)	0.0322 (14)	0.0232 (12)	−0.0144 (11)	−0.0020 (9)	0.0040 (10)
C16	0.0265 (13)	0.0260 (12)	0.0233 (12)	−0.0171 (11)	−0.0041 (10)	0.0015 (9)
C17	0.0194 (11)	0.0185 (11)	0.0211 (11)	−0.0079 (9)	−0.0026 (9)	−0.0003 (9)
C18	0.0165 (11)	0.0098 (9)	0.0234 (11)	−0.0063 (8)	−0.0023 (8)	−0.0002 (8)
C19	0.0206 (11)	0.0142 (10)	0.0228 (11)	−0.0095 (9)	−0.0038 (9)	−0.0014 (8)
C20	0.0202 (11)	0.0143 (10)	0.0226 (11)	−0.0064 (9)	−0.0013 (9)	−0.0029 (8)
C21	0.0163 (11)	0.0157 (10)	0.0162 (10)	−0.0063 (9)	−0.0033 (8)	−0.0009 (8)
C22	0.0172 (11)	0.0209 (11)	0.0234 (11)	−0.0070 (9)	−0.0006 (9)	−0.0032 (9)
C23	0.0173 (11)	0.0139 (10)	0.0203 (11)	−0.0068 (9)	−0.0050 (8)	0.0006 (8)

Geometric parameters (Å, º) top

Sn1—O1	2.063 (2)	C7—H7	0.9500
Sn1—C1	2.131 (3)	C8—C9	1.379 (4)
Sn1—C6	2.125 (2)	C8—H8	0.9500
Sn1—C12	2.134 (2)	C9—C10	1.380 (4)
S1—C23	1.695 (2)	C9—H9	0.9500
O1—C18	1.320 (3)	C10—C11	1.387 (4)
O2—C18	1.227 (3)	C10—H10	0.9500
N1—C21	1.283 (3)	C11—H11	0.9500
N1—N2	1.387 (3)	C12—C13	1.398 (3)
N2—C23	1.350 (3)	C12—C17	1.399 (3)
N2—H2N	0.8800	C13—C14	1.391 (4)
N3—C23	1.325 (3)	C13—H13	0.9500
N3—H3N1	0.8800	C14—C15	1.384 (4)
N3—H3N2	0.8800	C14—H14	0.9500
C1—C5	1.492 (4)	C15—C16	1.389 (4)
C1—C2	1.522 (4)	C15—H15	0.9500
C1—H1	1.0000	C16—C17	1.388 (4)
C2—C3	1.532 (5)	C16—H16	0.9500
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—C19	1.505 (3)
C3—C4	1.519 (5)	C19—C20	1.520 (3)
C3—H3A	0.9900	C19—H19A	0.9900
C3—H3B	0.9900	C19—H19B	0.9900
C4—C5	1.547 (5)	C20—C21	1.503 (3)
C4—H4A	0.9900	C20—H20A	0.9900
C4—H4B	0.9900	C20—H20B	0.9900
C5—H5A	0.9900	C21—C22	1.499 (3)
C5—H5B	0.9900	C22—H22A	0.9800
C6—C11	1.396 (3)	C22—H22B	0.9800
C6—C7	1.398 (3)	C22—H22C	0.9800
C7—C8	1.393 (4)

O1—Sn1—C1	112.7 (1)	C8—C9—H9	120.0
O1—Sn1—C6	108.6 (1)	C10—C9—H9	120.0
O1—Sn1—C12	95.9 (1)	C9—C10—C11	120.2 (2)
C1—Sn1—C6	116.5 (1)	C9—C10—H10	119.9
C1—Sn1—C12	112.1 (1)	C11—C10—H10	119.9
C6—Sn1—C12	109.2 (1)	C10—C11—C6	120.7 (2)
Sn1—O1—C18	109.3 (1)	C10—C11—H11	119.7
C21—N1—N2	118.3 (2)	C6—C11—H11	119.7
C23—N2—N1	117.11 (19)	C13—C12—C17	118.4 (2)
C23—N2—H2N	121.4	C13—C12—Sn1	120.71 (18)
N1—N2—H2N	121.4	C17—C12—Sn1	120.94 (18)
C23—N3—H3N1	120.0	C14—C13—C12	120.8 (2)
C23—N3—H3N2	120.0	C14—C13—H13	119.6
H3N1—N3—H3N2	120.0	C12—C13—H13	119.6
C5—C1—C2	106.2 (3)	C15—C14—C13	119.9 (2)
C5—C1—Sn1	116.7 (2)	C15—C14—H14	120.1
C2—C1—Sn1	113.0 (2)	C13—C14—H14	120.1
C5—C1—H1	106.8	C14—C15—C16	120.4 (2)
C2—C1—H1	106.8	C14—C15—H15	119.8
Sn1—C1—H1	106.8	C16—C15—H15	119.8
C1—C2—C3	106.9 (3)	C17—C16—C15	119.5 (2)
C1—C2—H2A	110.3	C17—C16—H16	120.2
C3—C2—H2A	110.3	C15—C16—H16	120.2
C1—C2—H2B	110.3	C16—C17—C12	121.1 (2)
C3—C2—H2B	110.3	C16—C17—H17	119.5
H2A—C2—H2B	108.6	C12—C17—H17	119.5
C4—C3—C2	104.5 (3)	O2—C18—O1	120.5 (2)
C4—C3—H3A	110.9	O2—C18—C19	125.2 (2)
C2—C3—H3A	110.9	O1—C18—C19	114.2 (2)
C4—C3—H3B	110.9	C18—C19—C20	114.6 (2)
C2—C3—H3B	110.9	C18—C19—H19A	108.6
H3A—C3—H3B	108.9	C20—C19—H19A	108.6
C3—C4—C5	104.1 (3)	C18—C19—H19B	108.6
C3—C4—H4A	110.9	C20—C19—H19B	108.6
C5—C4—H4A	110.9	H19A—C19—H19B	107.6
C3—C4—H4B	110.9	C21—C20—C19	115.40 (19)
C5—C4—H4B	110.9	C21—C20—H20A	108.4
H4A—C4—H4B	109.0	C19—C20—H20A	108.4
C1—C5—C4	102.4 (3)	C21—C20—H20B	108.4
C1—C5—H5A	111.3	C19—C20—H20B	108.4
C4—C5—H5A	111.3	H20A—C20—H20B	107.5
C1—C5—H5B	111.3	N1—C21—C22	126.5 (2)
C4—C5—H5B	111.3	N1—C21—C20	116.6 (2)
H5A—C5—H5B	109.2	C22—C21—C20	116.8 (2)
C11—C6—C7	118.4 (2)	C21—C22—H22A	109.5
C11—C6—Sn1	119.38 (18)	C21—C22—H22B	109.5
C7—C6—Sn1	122.09 (18)	H22A—C22—H22B	109.5
C8—C7—C6	120.4 (2)	C21—C22—H22C	109.5
C8—C7—H7	119.8	H22A—C22—H22C	109.5
C6—C7—H7	119.8	H22B—C22—H22C	109.5
C9—C8—C7	120.2 (3)	N3—C23—N2	117.2 (2)
C9—C8—H8	119.9	N3—C23—S1	123.29 (18)
C7—C8—H8	119.9	N2—C23—S1	119.54 (18)
C8—C9—C10	120.0 (2)

C6—Sn1—O1—C18	−77.70 (16)	C9—C10—C11—C6	−2.2 (4)
C1—Sn1—O1—C18	52.80 (17)	C7—C6—C11—C10	2.5 (4)
C12—Sn1—O1—C18	169.72 (15)	Sn1—C6—C11—C10	179.0 (2)
C21—N1—N2—C23	−174.8 (2)	O1—Sn1—C12—C13	110.54 (19)
O1—Sn1—C1—C5	32.7 (3)	C6—Sn1—C12—C13	−1.5 (2)
C6—Sn1—C1—C5	159.1 (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—C2	156.3 (3)	C6—Sn1—C12—C17	177.87 (18)
C6—Sn1—C1—C2	−77.3 (3)	C1—Sn1—C12—C17	47.3 (2)
C12—Sn1—C1—C2	49.4 (3)	C17—C12—C13—C14	−0.6 (4)
C5—C1—C2—C3	−15.5 (4)	Sn1—C12—C13—C14	178.79 (18)
Sn1—C1—C2—C3	−144.7 (3)	C12—C13—C14—C15	0.2 (4)
C1—C2—C3—C4	−9.9 (5)	C13—C14—C15—C16	0.6 (4)
C2—C3—C4—C5	30.7 (4)	C14—C15—C16—C17	−0.9 (4)
C2—C1—C5—C4	34.0 (4)	C15—C16—C17—C12	0.4 (4)
Sn1—C1—C5—C4	161.0 (2)	C13—C12—C17—C16	0.3 (4)
C3—C4—C5—C1	−40.3 (4)	Sn1—C12—C17—C16	−179.07 (18)
O1—Sn1—C6—C11	155.98 (19)	Sn1—O1—C18—O2	5.1 (3)
C1—Sn1—C6—C11	27.6 (2)	Sn1—O1—C18—C19	−173.25 (14)
C12—Sn1—C6—C11	−100.6 (2)	O2—C18—C19—C20	2.0 (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—C21	72.7 (3)
C12—Sn1—C6—C7	75.7 (2)	N2—N1—C21—C22	2.0 (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—N1	3.9 (3)
C6—C7—C8—C9	0.4 (4)	C19—C20—C21—C22	−176.6 (2)
C7—C8—C9—C10	−0.1 (4)	N1—N2—C23—N3	6.1 (3)
C8—C9—C10—C11	1.0 (4)	N1—N2—C23—S1	−174.76 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O2ⁱ	0.88	2.12	2.975 (3)	163
N3—H3n1···O1ⁱⁱ	0.88	2.43	3.121 (3)	136
N3—H3n2···S1ⁱⁱⁱ	0.88	2.54	3.389 (2)	161

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₅H₉)(C₆H₅)₂(C₆H₁₀N₃O₂S)]
M_r	530.24
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5780 (1), 10.2375 (1), 13.4205 (1)
α, β, γ (°)	86.901 (1), 83.370 (1), 63.667 (1)
V (Å³)	1171.50 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.779, 0.889
No. of measured, independent and observed [I > 2σ(I)] reflections	15020, 5350, 5186
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.078, 1.03
No. of reflections	5350
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.99, −0.91

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Sn1—O1	2.063 (2)	Sn1—C6	2.125 (2)
Sn1—C1	2.131 (3)	Sn1—C12	2.134 (2)

O1—Sn1—C1	112.7 (1)	C1—Sn1—C12	112.1 (1)
O1—Sn1—C6	108.6 (1)	C6—Sn1—C12	109.2 (1)
O1—Sn1—C12	95.9 (1)	Sn1—O1—C18	109.3 (1)
C1—Sn1—C6	116.5 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O2ⁱ	0.88	2.12	2.975 (3)	163
N3—H3n1···O1ⁱⁱ	0.88	2.43	3.121 (3)	136
N3—H3n2···S1ⁱⁱⁱ	0.88	2.54	3.389 (2)	161

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Acknowledgements

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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