Octa-n-butyl-1κ2C,2κ2C,3κ2C,4κ2C-tetra­kis(μ-2-hydroxy­benzoato)-1:2κ2O:O;2:3κ2O:O′;3:4κ2O:O;1:4κ2O:O′-di-μ3-oxido-1:2:3κ3O:O:O;1:3:4κ3O:O:O-tetra­tin(IV)

Reisi, R.; Siti Munirah, S.; Misran, M.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808023787

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1103

doi:10.1107/S1600536808023787

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Octa-n-butyl-1κ²C,2κ²C,3κ²C,4κ²C-tetrakis(μ-2-hydroxybenzoato)-1:2κ²O:O;2:3κ²O:O′;3:4κ²O:O;1:4κ²O:O′-di-μ₃-oxido-1:2:3κ³O:O:O;1:3:4κ³O:O:O-tetratin(IV)

Reza Reisi,^a Shahirin Siti Munirah,^a Misni Misran,^a 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 22 July 2008; accepted 28 July 2008; online 31 July 2008)

In the centrosymmetric tetranuclear title compound, [Sn₄(C₄H₉)₈(C₇H₅O₃)₄O₂], one of the two independent Sn atoms is five-coordinate in a cis-C₂SnO₃ trigonal-bipyramidal geometry [C—Sn—C = 142.7 (1)°]; the geometry is distorted owing to a long Sn⋯O(double bond) interaction [Sn⋯O = 2.862 (1) Å]. The other Sn atom has a bent R₂Sn skeleton [C—Sn—C = 144.0 (1)°], but the geometry is best regarded as being a trans-C₂SnO₄ octahedron as the Sn–O(single bond) interaction is shorter [Sn—O = 2.674 (1) Å].

Related literature

For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991 , 1994 ). For a description of carboxylato-distannoxanes, see: Ng et al. (1991 ).

Experimental

Crystal data

[Sn₄(C₄H₉)₈(C₇H₅O₃)₄O₂]
M_r = 1512.10
Triclinic, $[P \overline 1]$
a = 11.4549 (2) Å
b = 12.1610 (2) Å
c = 13.4436 (2) Å
α = 106.300 (1)°
β = 92.532 (1)°
γ = 115.204 (1)°
V = 1597.18 (5) Å³
Z = 1
Mo Kα radiation
μ = 1.60 mm⁻¹
T = 100 (2) K
0.38 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.581, T_max = 0.761
9253 measured reflections
7210 independent reflections
6583 reflections with I > 2σ(I)
R_int = 0.008

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.067
S = 1.17
7210 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84	2.02	2.638 (2)	130
O6—H6⋯O5	0.84	1.91	2.548 (2)	132

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/S1600536808023787/tk2287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023787/tk2287Isup2.hkl

checkCIF report

Comment top

Diorganotin dicarboxylates are conveniently synthesized by condensing a diorganotin oxide with a carboxylic acid; occasionally, only one molar portion of the acid is used up to afford a tetranuclear distannoxane. The strucutural chemistry of distannoxanes has been reviewed (Ng et al., 1991; Tiekink, 1991; 1994). The title compound (Scheme I, Fig. 1) is formed in a 1:2 condensation between di-n-butyltin oxide and 2-hydroxybenzoic acid. The hydroxyl-H atoms form intramolecular hydrogen bonds to the more weakly bound O atoms (Table 1).

Related literature top

For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994). For a description of carboxylato-distannoxanes, see: Ng et al. (1991).

Experimental top

Dibutyltin oxide (2 g, 8 mmol) and salicylic acid (2.2 g, 16 mmol) were acid heated in ethanol (100 ml) until the reactants dissolved completely. Slow evaporation of the filtered solution yielded colorless crystals.

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. Thermal ellipsoid plot (Barbour, 2001) plot of [Sn₂(C₄H₉)₄(C₇H₅O₃)₂O]₂ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabelled atoms are related by a center of inversion.

Octa-n-butyl-1κ²C,2κ²C,3κ²C,4κ²C- tetrakis(-µ-2-hydroxybenzoato)-1:2κ²O:O;2:3κ²O: O';3:4κ²O:O;1:4κ²O:O'-di- µ₃-oxido-1:2:3κ³O:O:O; 1:3:4k³O:O:O-tetratin(IV) top

Crystal data top

[Sn₄(C₄H₉)₈(C₇H₅O₃)₄O₂]	Z = 1
M_r = 1512.10	F(000) = 764
Triclinic, P1	D_x = 1.572 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4549 (2) Å	Cell parameters from 8563 reflections
b = 12.1610 (2) Å	θ = 2.1–30.4°
c = 13.4436 (2) Å	µ = 1.61 mm⁻¹
α = 106.300 (1)°	T = 100 K
β = 92.532 (1)°	Block, colorless
γ = 115.204 (1)°	0.38 × 0.30 × 0.18 mm
V = 1597.18 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	7210 independent reflections
Radiation source: fine-focus sealed tube	6583 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.008
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→14
T_min = 0.581, T_max = 0.761	k = −15→15
9253 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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0396P)² + 0.6175P] where P = (F_o² + 2F_c²)/3
7210 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

[Sn₄(C₄H₉)₈(C₇H₅O₃)₄O₂]	γ = 115.204 (1)°
M_r = 1512.10	V = 1597.18 (5) Å³
Triclinic, P1	Z = 1
a = 11.4549 (2) Å	Mo Kα radiation
b = 12.1610 (2) Å	µ = 1.61 mm⁻¹
c = 13.4436 (2) Å	T = 100 K
α = 106.300 (1)°	0.38 × 0.30 × 0.18 mm
β = 92.532 (1)°

Data collection top

Bruker SMART APEX diffractometer	7210 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6583 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.761	R_int = 0.008
9253 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.17	Δρ_max = 0.91 e Å⁻³
7210 reflections	Δρ_min = −0.86 e Å⁻³
352 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.474718 (13)	0.580180 (13)	0.753402 (10)	0.01404 (5)
Sn2	0.456706 (13)	0.604166 (12)	0.476911 (10)	0.01191 (5)
O1	0.41023 (18)	0.72441 (17)	0.74041 (13)	0.0253 (4)
O2	0.40862 (16)	0.75903 (15)	0.58632 (12)	0.0191 (3)
O3	0.37161 (16)	0.95576 (15)	0.57647 (12)	0.0214 (3)
H3	0.3993	0.9035	0.5466	0.032*
O4	0.54344 (15)	0.43088 (14)	0.72857 (11)	0.0163 (3)
O5	0.51748 (16)	0.45675 (15)	0.89385 (12)	0.0201 (3)
O6	0.55126 (18)	0.31818 (17)	0.99204 (13)	0.0265 (4)
H6	0.5272	0.3749	0.9937	0.040*
O7	0.48810 (14)	0.54280 (13)	0.59784 (11)	0.0140 (3)
C1	0.2821 (2)	0.4578 (2)	0.76932 (18)	0.0209 (4)
H1A	0.2382	0.3872	0.7011	0.025*
H1B	0.2912	0.4181	0.8223	0.025*
C2	0.1914 (2)	0.5184 (2)	0.80106 (18)	0.0214 (4)
H2A	0.1675	0.5439	0.7426	0.026*
H2B	0.2387	0.5972	0.8633	0.026*
C3	0.0665 (2)	0.4265 (2)	0.8274 (2)	0.0274 (5)
H3A	0.0195	0.3475	0.7652	0.033*
H3B	0.0905	0.4013	0.8860	0.033*
C4	−0.0249 (3)	0.4862 (3)	0.8588 (2)	0.0366 (6)
H4A	−0.1034	0.4240	0.8752	0.055*
H4B	−0.0508	0.5094	0.8003	0.055*
H4C	0.0206	0.5637	0.9210	0.055*
C5	0.6564 (2)	0.7396 (2)	0.84066 (17)	0.0197 (4)
H5A	0.7011	0.7831	0.7912	0.024*
H5B	0.6361	0.8013	0.8931	0.024*
C6	0.7543 (2)	0.7138 (2)	0.89931 (18)	0.0228 (4)
H6A	0.7175	0.6846	0.9577	0.027*
H6B	0.7669	0.6437	0.8504	0.027*
C7	0.8873 (2)	0.8329 (2)	0.94411 (18)	0.0239 (5)
H7A	0.9283	0.8563	0.8850	0.029*
H7B	0.8734	0.9057	0.9865	0.029*
C8	0.9803 (3)	0.8134 (3)	1.0124 (2)	0.0369 (6)
H8A	1.0637	0.8925	1.0386	0.055*
H8B	0.9960	0.7425	0.9706	0.055*
H8C	0.9414	0.7925	1.0722	0.055*
C9	0.2521 (2)	0.4950 (2)	0.41335 (16)	0.0172 (4)
H9A	0.2197	0.5510	0.3934	0.021*
H9B	0.2380	0.4239	0.3485	0.021*
C10	0.1726 (2)	0.4388 (2)	0.49052 (17)	0.0183 (4)
H10A	0.1809	0.5104	0.5527	0.022*
H10B	0.2104	0.3894	0.5152	0.022*
C11	0.0273 (2)	0.3510 (2)	0.44359 (19)	0.0252 (5)
H11A	0.0181	0.2778	0.3824	0.030*
H11B	−0.0110	0.3995	0.4180	0.030*
C12	−0.0483 (2)	0.2992 (3)	0.5246 (2)	0.0330 (6)
H12A	−0.1410	0.2432	0.4920	0.050*
H12B	−0.0406	0.3714	0.5847	0.050*
H12C	−0.0115	0.2498	0.5492	0.050*
C13	0.6307 (2)	0.76707 (19)	0.47831 (16)	0.0160 (4)
H13A	0.6772	0.7380	0.4247	0.019*
H13B	0.6055	0.8266	0.4568	0.019*
C14	0.7264 (2)	0.8419 (2)	0.58388 (16)	0.0171 (4)
H14A	0.6834	0.8776	0.6370	0.021*
H14B	0.7488	0.7824	0.6082	0.021*
C15	0.8518 (2)	0.9512 (2)	0.57547 (18)	0.0231 (5)
H15A	0.8287	1.0088	0.5488	0.028*
H15B	0.8956	0.9149	0.5237	0.028*
C16	0.9473 (2)	1.0299 (2)	0.6806 (2)	0.0314 (5)
H16A	1.0258	1.0991	0.6709	0.047*
H16B	0.9725	0.9740	0.7065	0.047*
H16C	0.9050	1.0674	0.7319	0.047*
C17	0.5490 (2)	0.4027 (2)	0.81372 (16)	0.0154 (4)
C18	0.5934 (2)	0.30563 (19)	0.81605 (16)	0.0155 (4)
C19	0.5912 (2)	0.2678 (2)	0.90565 (17)	0.0210 (4)
C20	0.6303 (3)	0.1737 (2)	0.9064 (2)	0.0295 (5)
H20	0.6281	0.1472	0.9666	0.035*
C21	0.6721 (3)	0.1191 (2)	0.8199 (2)	0.0313 (6)
H21	0.6990	0.0556	0.8215	0.038*
C22	0.6754 (2)	0.1561 (2)	0.73042 (19)	0.0250 (5)
H22	0.7044	0.1183	0.6712	0.030*
C23	0.6359 (2)	0.2481 (2)	0.72919 (17)	0.0186 (4)
H23	0.6375	0.2732	0.6682	0.022*
C24	0.39034 (19)	0.78038 (19)	0.68108 (17)	0.0148 (4)
C25	0.3413 (2)	0.8755 (2)	0.72378 (16)	0.0167 (4)
C26	0.3334 (2)	0.9564 (2)	0.67047 (17)	0.0179 (4)
C27	0.2884 (2)	1.0455 (2)	0.71614 (18)	0.0224 (4)
H27	0.2829	1.1005	0.6801	0.027*
C28	0.2519 (2)	1.0542 (2)	0.81310 (19)	0.0266 (5)
H28	0.2229	1.1162	0.8442	0.032*
C29	0.2572 (3)	0.9720 (2)	0.86622 (19)	0.0286 (5)
H29	0.2307	0.9772	0.9326	0.034*
C30	0.3010 (2)	0.8841 (2)	0.82159 (19)	0.0251 (5)
H30	0.3042	0.8280	0.8574	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01990 (8)	0.01605 (8)	0.01136 (8)	0.01119 (6)	0.00618 (5)	0.00671 (6)
Sn2	0.01459 (8)	0.01233 (8)	0.01148 (8)	0.00713 (6)	0.00409 (5)	0.00591 (5)
O1	0.0400 (10)	0.0301 (9)	0.0223 (8)	0.0263 (8)	0.0132 (7)	0.0147 (7)
O2	0.0282 (8)	0.0202 (7)	0.0158 (7)	0.0162 (7)	0.0086 (6)	0.0070 (6)
O3	0.0302 (8)	0.0235 (8)	0.0191 (7)	0.0171 (7)	0.0104 (6)	0.0109 (6)
O4	0.0236 (7)	0.0180 (7)	0.0122 (7)	0.0122 (6)	0.0061 (6)	0.0073 (6)
O5	0.0297 (8)	0.0245 (8)	0.0150 (7)	0.0177 (7)	0.0091 (6)	0.0098 (6)
O6	0.0423 (10)	0.0318 (9)	0.0164 (8)	0.0234 (8)	0.0087 (7)	0.0128 (7)
O7	0.0192 (7)	0.0157 (7)	0.0119 (6)	0.0104 (6)	0.0053 (5)	0.0072 (5)
C1	0.0233 (11)	0.0226 (11)	0.0223 (11)	0.0123 (9)	0.0092 (9)	0.0114 (9)
C2	0.0211 (11)	0.0251 (11)	0.0205 (10)	0.0128 (9)	0.0073 (8)	0.0071 (9)
C3	0.0250 (12)	0.0308 (12)	0.0275 (12)	0.0129 (10)	0.0109 (9)	0.0101 (10)
C4	0.0250 (13)	0.0423 (15)	0.0392 (16)	0.0164 (12)	0.0111 (11)	0.0062 (12)
C5	0.0256 (11)	0.0177 (10)	0.0160 (10)	0.0100 (9)	0.0049 (8)	0.0056 (8)
C6	0.0273 (12)	0.0204 (11)	0.0196 (10)	0.0108 (9)	0.0010 (9)	0.0057 (9)
C7	0.0256 (11)	0.0223 (11)	0.0219 (11)	0.0095 (9)	0.0047 (9)	0.0068 (9)
C8	0.0357 (14)	0.0285 (13)	0.0418 (15)	0.0128 (12)	−0.0047 (12)	0.0097 (12)
C9	0.0166 (10)	0.0213 (10)	0.0147 (9)	0.0089 (8)	0.0035 (8)	0.0071 (8)
C10	0.0170 (10)	0.0202 (10)	0.0182 (10)	0.0078 (8)	0.0049 (8)	0.0079 (8)
C11	0.0197 (11)	0.0267 (12)	0.0240 (11)	0.0065 (9)	0.0041 (9)	0.0078 (9)
C12	0.0210 (12)	0.0326 (13)	0.0364 (14)	0.0031 (10)	0.0091 (10)	0.0125 (11)
C13	0.0202 (10)	0.0154 (9)	0.0148 (9)	0.0084 (8)	0.0065 (8)	0.0075 (8)
C14	0.0198 (10)	0.0152 (9)	0.0161 (10)	0.0074 (8)	0.0043 (8)	0.0057 (8)
C15	0.0206 (11)	0.0201 (11)	0.0245 (11)	0.0056 (9)	0.0064 (9)	0.0075 (9)
C16	0.0219 (12)	0.0273 (12)	0.0337 (13)	0.0053 (10)	−0.0005 (10)	0.0046 (10)
C17	0.0143 (9)	0.0159 (9)	0.0153 (10)	0.0051 (8)	0.0029 (7)	0.0071 (8)
C18	0.0157 (9)	0.0149 (9)	0.0171 (10)	0.0075 (8)	0.0019 (7)	0.0063 (8)
C19	0.0266 (11)	0.0201 (10)	0.0180 (10)	0.0114 (9)	0.0025 (8)	0.0080 (9)
C20	0.0454 (15)	0.0299 (13)	0.0231 (12)	0.0236 (12)	0.0022 (10)	0.0134 (10)
C21	0.0398 (14)	0.0286 (13)	0.0336 (13)	0.0237 (12)	−0.0009 (11)	0.0101 (11)
C22	0.0294 (12)	0.0228 (11)	0.0260 (12)	0.0168 (10)	0.0041 (9)	0.0051 (9)
C23	0.0200 (10)	0.0180 (10)	0.0193 (10)	0.0096 (9)	0.0036 (8)	0.0070 (8)
C24	0.0125 (9)	0.0123 (9)	0.0200 (10)	0.0049 (8)	0.0049 (7)	0.0067 (8)
C25	0.0185 (10)	0.0172 (10)	0.0159 (10)	0.0096 (8)	0.0044 (8)	0.0050 (8)
C26	0.0194 (10)	0.0195 (10)	0.0172 (10)	0.0099 (8)	0.0057 (8)	0.0078 (8)
C27	0.0273 (12)	0.0220 (11)	0.0261 (11)	0.0154 (10)	0.0093 (9)	0.0125 (9)
C28	0.0326 (13)	0.0279 (12)	0.0274 (12)	0.0219 (11)	0.0098 (10)	0.0071 (10)
C29	0.0425 (14)	0.0348 (13)	0.0210 (11)	0.0258 (12)	0.0156 (10)	0.0124 (10)
C30	0.0350 (13)	0.0290 (12)	0.0224 (11)	0.0210 (11)	0.0109 (10)	0.0132 (10)

Geometric parameters (Å, º) top

Sn1—C1	2.134 (2)	C9—H9A	0.9900
Sn1—C5	2.130 (2)	C9—H9B	0.9900
Sn1—O1	2.217 (2)	C10—C11	1.525 (3)
Sn1—O4	2.220 (1)	C10—H10A	0.9900
Sn1—O7	2.039 (1)	C10—H10B	0.9900
Sn2—C9	2.127 (2)	C11—C12	1.528 (3)
Sn2—C13	2.124 (2)	C11—H11A	0.9900
Sn2—O2	2.327 (2)	C11—H11B	0.9900
Sn2—O4ⁱ	2.674 (1)	C12—H12A	0.9800
Sn2—O7	2.046 (1)	C12—H12B	0.9800
Sn2—O7ⁱ	2.148 (1)	C12—H12C	0.9800
Sn2—Sn2ⁱ	3.2797 (3)	C13—C14	1.527 (3)
O1—C24	1.254 (3)	C13—H13A	0.9900
O2—C24	1.272 (3)	C13—H13B	0.9900
O3—C26	1.355 (3)	C14—C15	1.522 (3)
O3—H3	0.8400	C14—H14A	0.9900
O4—C17	1.290 (2)	C14—H14B	0.9900
O5—C17	1.249 (3)	C15—C16	1.524 (3)
O6—C19	1.349 (3)	C15—H15A	0.9900
O6—H6	0.8400	C15—H15B	0.9900
O7—Sn2ⁱ	2.1481 (14)	C16—H16A	0.9800
C1—C2	1.523 (3)	C16—H16B	0.9800
C1—H1A	0.9900	C16—H16C	0.9800
C1—H1B	0.9900	C17—C18	1.478 (3)
C2—C3	1.526 (3)	C18—C19	1.403 (3)
C2—H2A	0.9900	C18—C23	1.404 (3)
C2—H2B	0.9900	C19—C20	1.396 (3)
C3—C4	1.522 (3)	C20—C21	1.381 (4)
C3—H3A	0.9900	C20—H20	0.9500
C3—H3B	0.9900	C21—C22	1.395 (4)
C4—H4A	0.9800	C21—H21	0.9500
C4—H4B	0.9800	C22—C23	1.378 (3)
C4—H4C	0.9800	C22—H22	0.9500
C5—C6	1.529 (3)	C23—H23	0.9500
C5—H5A	0.9900	C24—C25	1.481 (3)
C5—H5B	0.9900	C25—C26	1.398 (3)
C6—C7	1.526 (3)	C25—C30	1.403 (3)
C6—H6A	0.9900	C26—C27	1.396 (3)
C6—H6B	0.9900	C27—C28	1.376 (3)
C7—C8	1.511 (3)	C27—H27	0.9500
C7—H7A	0.9900	C28—C29	1.400 (3)
C7—H7B	0.9900	C28—H28	0.9500
C8—H8A	0.9800	C29—C30	1.371 (3)
C8—H8B	0.9800	C29—H29	0.9500
C8—H8C	0.9800	C30—H30	0.9500
C9—C10	1.524 (3)

O7—Sn1—C5	106.97 (7)	Sn2—C9—H9A	109.0
O7—Sn1—C1	110.04 (7)	C10—C9—H9B	109.0
C1—Sn1—C5	142.7 (1)	Sn2—C9—H9B	109.0
O7—Sn1—O1	88.26 (6)	H9A—C9—H9B	107.8
C5—Sn1—O1	86.54 (8)	C9—C10—C11	113.68 (18)
C1—Sn1—O1	90.33 (8)	C9—C10—H10A	108.8
O7—Sn1—O4	78.77 (5)	C11—C10—H10A	108.8
C5—Sn1—O4	96.61 (7)	C9—C10—H10B	108.8
C1—Sn1—O4	94.63 (7)	C11—C10—H10B	108.8
O1—Sn1—O4	167.02 (6)	H10A—C10—H10B	107.7
O7—Sn2—C13	109.41 (7)	C10—C11—C12	111.6 (2)
O7—Sn2—C9	105.66 (7)	C10—C11—H11A	109.3
C9—Sn2—C13	144.0 (1)	C12—C11—H11A	109.3
O7—Sn2—O7ⁱ	77.15 (6)	C10—C11—H11B	109.3
C13—Sn2—O7ⁱ	98.31 (7)	C12—C11—H11B	109.3
C9—Sn2—O7ⁱ	97.06 (7)	H11A—C11—H11B	108.0
O7—Sn2—O2	92.54 (5)	C11—C12—H12A	109.5
C13—Sn2—O2	83.38 (7)	C11—C12—H12B	109.5
C9—Sn2—O2	87.28 (7)	H12A—C12—H12B	109.5
O7ⁱ—Sn2—O2	169.55 (5)	C11—C12—H12C	109.5
O7—Sn2—O4ⁱ	144.40 (5)	H12A—C12—H12C	109.5
C13—Sn2—O4ⁱ	77.34 (6)	H12B—C12—H12C	109.5
C9—Sn2—O4ⁱ	78.99 (6)	C14—C13—Sn2	115.51 (13)
O7ⁱ—Sn2—O4ⁱ	67.25 (5)	C14—C13—H13A	108.4
O2—Sn2—O4ⁱ	123.06 (5)	Sn2—C13—H13A	108.4
O7—Sn2—Sn2ⁱ	39.68 (4)	C14—C13—H13B	108.4
C13—Sn2—Sn2ⁱ	107.57 (6)	Sn2—C13—H13B	108.4
C9—Sn2—Sn2ⁱ	104.41 (6)	H13A—C13—H13B	107.5
O7ⁱ—Sn2—Sn2ⁱ	37.46 (4)	C15—C14—C13	111.74 (17)
O2—Sn2—Sn2ⁱ	132.20 (4)	C15—C14—H14A	109.3
O4ⁱ—Sn2—Sn2ⁱ	104.71 (3)	C13—C14—H14A	109.3
C24—O1—Sn1	145.23 (14)	C15—C14—H14B	109.3
C24—O2—Sn2	131.75 (13)	C13—C14—H14B	109.3
C26—O3—H3	120.0	H14A—C14—H14B	107.9
C17—O4—Sn1	109.71 (13)	C14—C15—C16	112.79 (19)
C19—O6—H6	120.0	C14—C15—H15A	109.0
Sn1—O7—Sn2	137.90 (7)	C16—C15—H15A	109.0
Sn1—O7—Sn2ⁱ	119.21 (6)	C14—C15—H15B	109.0
Sn2—O7—Sn2ⁱ	102.85 (6)	C16—C15—H15B	109.0
C2—C1—Sn1	117.60 (15)	H15A—C15—H15B	107.8
C2—C1—H1A	107.9	C15—C16—H16A	109.5
Sn1—C1—H1A	107.9	C15—C16—H16B	109.5
C2—C1—H1B	107.9	H16A—C16—H16B	109.5
Sn1—C1—H1B	107.9	C15—C16—H16C	109.5
H1A—C1—H1B	107.2	H16A—C16—H16C	109.5
C1—C2—C3	112.06 (19)	H16B—C16—H16C	109.5
C1—C2—H2A	109.2	O5—C17—O4	120.69 (19)
C3—C2—H2A	109.2	O5—C17—C18	119.94 (18)
C1—C2—H2B	109.2	O4—C17—C18	119.37 (18)
C3—C2—H2B	109.2	C19—C18—C23	118.82 (19)
H2A—C2—H2B	107.9	C19—C18—C17	119.86 (19)
C4—C3—C2	112.4 (2)	C23—C18—C17	121.30 (19)
C4—C3—H3A	109.1	O6—C19—C20	118.1 (2)
C2—C3—H3A	109.1	O6—C19—C18	122.4 (2)
C4—C3—H3B	109.1	C20—C19—C18	119.6 (2)
C2—C3—H3B	109.1	C21—C20—C19	120.3 (2)
H3A—C3—H3B	107.9	C21—C20—H20	119.8
C3—C4—H4A	109.5	C19—C20—H20	119.8
C3—C4—H4B	109.5	C20—C21—C22	120.8 (2)
H4A—C4—H4B	109.5	C20—C21—H21	119.6
C3—C4—H4C	109.5	C22—C21—H21	119.6
H4A—C4—H4C	109.5	C23—C22—C21	119.0 (2)
H4B—C4—H4C	109.5	C23—C22—H22	120.5
C6—C5—Sn1	118.38 (15)	C21—C22—H22	120.5
C6—C5—H5A	107.7	C22—C23—C18	121.5 (2)
Sn1—C5—H5A	107.7	C22—C23—H23	119.3
C6—C5—H5B	107.7	C18—C23—H23	119.3
Sn1—C5—H5B	107.7	O1—C24—O2	123.73 (19)
H5A—C5—H5B	107.1	O1—C24—C25	117.86 (18)
C7—C6—C5	112.48 (19)	O2—C24—C25	118.40 (18)
C7—C6—H6A	109.1	C26—C25—C30	119.1 (2)
C5—C6—H6A	109.1	C26—C25—C24	122.59 (19)
C7—C6—H6B	109.1	C30—C25—C24	118.34 (19)
C5—C6—H6B	109.1	O3—C26—C27	117.32 (19)
H6A—C6—H6B	107.8	O3—C26—C25	123.03 (19)
C8—C7—C6	113.1 (2)	C27—C26—C25	119.6 (2)
C8—C7—H7A	108.9	C28—C27—C26	120.4 (2)
C6—C7—H7A	108.9	C28—C27—H27	119.8
C8—C7—H7B	108.9	C26—C27—H27	119.8
C6—C7—H7B	108.9	C27—C28—C29	120.4 (2)
H7A—C7—H7B	107.8	C27—C28—H28	119.8
C7—C8—H8A	109.5	C29—C28—H28	119.8
C7—C8—H8B	109.5	C30—C29—C28	119.4 (2)
H8A—C8—H8B	109.5	C30—C29—H29	120.3
C7—C8—H8C	109.5	C28—C29—H29	120.3
H8A—C8—H8C	109.5	C29—C30—C25	121.1 (2)
H8B—C8—H8C	109.5	C29—C30—H30	119.5
C10—C9—Sn2	112.74 (13)	C25—C30—H30	119.5
C10—C9—H9A	109.0

O7—Sn1—O1—C24	−4.1 (3)	O4ⁱ—Sn2—C9—C10	164.52 (16)
C5—Sn1—O1—C24	103.0 (3)	Sn2ⁱ—Sn2—C9—C10	61.98 (15)
C1—Sn1—O1—C24	−114.1 (3)	Sn2—C9—C10—C11	−175.14 (15)
O4—Sn1—O1—C24	−1.5 (5)	C9—C10—C11—C12	−179.0 (2)
O7—Sn2—O2—C24	−9.13 (19)	O7—Sn2—C13—C14	−22.38 (17)
C13—Sn2—O2—C24	−118.38 (19)	C9—Sn2—C13—C14	144.04 (15)
C9—Sn2—O2—C24	96.44 (19)	O7ⁱ—Sn2—C13—C14	−101.60 (15)
O7ⁱ—Sn2—O2—C24	−18.4 (4)	O2—Sn2—C13—C14	67.99 (15)
O4ⁱ—Sn2—O2—C24	171.42 (17)	O4ⁱ—Sn2—C13—C14	−165.93 (16)
Sn2ⁱ—Sn2—O2—C24	−10.6 (2)	Sn2ⁱ—Sn2—C13—C14	−64.28 (15)
O7—Sn1—O4—C17	−176.32 (14)	Sn2—C13—C14—C15	176.22 (14)
C5—Sn1—O4—C17	77.63 (14)	C13—C14—C15—C16	178.31 (19)
C1—Sn1—O4—C17	−66.79 (14)	Sn1—O4—C17—O5	0.3 (2)
O1—Sn1—O4—C17	−178.9 (2)	Sn1—O4—C17—C18	−179.56 (14)
C5—Sn1—O7—Sn2	−86.37 (12)	O5—C17—C18—C19	4.5 (3)
C1—Sn1—O7—Sn2	89.20 (12)	O4—C17—C18—C19	−175.62 (19)
O1—Sn1—O7—Sn2	−0.52 (11)	O5—C17—C18—C23	−176.68 (19)
O4—Sn1—O7—Sn2	−179.93 (12)	O4—C17—C18—C23	3.2 (3)
C5—Sn1—O7—Sn2ⁱ	96.30 (9)	C23—C18—C19—O6	−179.8 (2)
C1—Sn1—O7—Sn2ⁱ	−88.14 (9)	C17—C18—C19—O6	−0.9 (3)
O1—Sn1—O7—Sn2ⁱ	−177.85 (8)	C23—C18—C19—C20	−0.4 (3)
O4—Sn1—O7—Sn2ⁱ	2.74 (7)	C17—C18—C19—C20	178.5 (2)
C13—Sn2—O7—Sn1	87.99 (12)	O6—C19—C20—C21	−180.0 (2)
C9—Sn2—O7—Sn1	−83.77 (12)	C18—C19—C20—C21	0.6 (4)
O7ⁱ—Sn2—O7—Sn1	−177.61 (15)	C19—C20—C21—C22	−0.4 (4)
O2—Sn2—O7—Sn1	4.11 (11)	C20—C21—C22—C23	−0.1 (4)
O4ⁱ—Sn2—O7—Sn1	−176.69 (7)	C21—C22—C23—C18	0.4 (4)
Sn2ⁱ—Sn2—O7—Sn1	−177.61 (15)	C19—C18—C23—C22	−0.1 (3)
C13—Sn2—O7—Sn2ⁱ	−94.40 (8)	C17—C18—C23—C22	−178.9 (2)
C9—Sn2—O7—Sn2ⁱ	93.84 (8)	Sn1—O1—C24—O2	0.2 (4)
O7ⁱ—Sn2—O7—Sn2ⁱ	0.0	Sn1—O1—C24—C25	179.42 (19)
O2—Sn2—O7—Sn2ⁱ	−178.28 (6)	Sn2—O2—C24—O1	8.3 (3)
O4ⁱ—Sn2—O7—Sn2ⁱ	0.93 (12)	Sn2—O2—C24—C25	−170.89 (14)
O7—Sn1—C1—C2	−106.97 (16)	O1—C24—C25—C26	170.7 (2)
C5—Sn1—C1—C2	66.0 (2)	O2—C24—C25—C26	−10.0 (3)
O1—Sn1—C1—C2	−18.70 (17)	O1—C24—C25—C30	−9.4 (3)
O4—Sn1—C1—C2	173.31 (16)	O2—C24—C25—C30	169.9 (2)
Sn1—C1—C2—C3	−170.46 (16)	C30—C25—C26—O3	179.1 (2)
C1—C2—C3—C4	−179.8 (2)	C24—C25—C26—O3	−1.0 (3)
O7—Sn1—C5—C6	−104.35 (16)	C30—C25—C26—C27	1.3 (3)
C1—Sn1—C5—C6	82.5 (2)	C24—C25—C26—C27	−178.9 (2)
O1—Sn1—C5—C6	168.54 (17)	O3—C26—C27—C28	−178.0 (2)
O4—Sn1—C5—C6	−24.11 (17)	C25—C26—C27—C28	0.0 (3)
Sn1—C5—C6—C7	171.31 (15)	C26—C27—C28—C29	−1.2 (4)
C5—C6—C7—C8	173.7 (2)	C27—C28—C29—C30	1.0 (4)
O7—Sn2—C9—C10	20.85 (16)	C28—C29—C30—C25	0.3 (4)
C13—Sn2—C9—C10	−145.86 (15)	C26—C25—C30—C29	−1.4 (4)
O7ⁱ—Sn2—C9—C10	99.42 (15)	C24—C25—C30—C29	178.7 (2)
O2—Sn2—C9—C10	−71.03 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	2.02	2.638 (2)	130
O6—H6···O5	0.84	1.91	2.548 (2)	132

Experimental details

Crystal data
Chemical formula	[Sn₄(C₄H₉)₈(C₇H₅O₃)₄O₂]
M_r	1512.10
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	11.4549 (2), 12.1610 (2), 13.4436 (2)
α, β, γ (°)	106.300 (1), 92.532 (1), 115.204 (1)
V (Å³)	1597.18 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.38 × 0.30 × 0.18

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.581, 0.761
No. of measured, independent and observed [I > 2σ(I)] reflections	9253, 7210, 6583
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.067, 1.17
No. of reflections	7210
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.86

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	2.02	2.638 (2)	130.3
O6—H6···O5	0.84	1.91	2.548 (2)	132.1

Acknowledgements

We thank the University of Malaya for funding this study (SF022/2007 A, FS339/2008 A) and also for the purchase of the diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, S. W., Chen, W. & Kumar Das, V. G. (1991). J. Organomet. Chem. 412, 39–45. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23. CrossRef CAS Web of Science Google Scholar
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116. Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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