[μ-1,4-Bis(diphenyl­phosphino­yl)butane-κ2O:O′]bis­[cyclo­pentyl­diphen­yl(trifluoro­acetato-κO)tin(IV)]

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

doi:10.1107/S1600536808013202

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m790

doi:10.1107/S1600536808013202

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[μ-1,4-Bis(diphenylphosphinoyl)butane-κ²O:O′]bis[cyclopentyldiphenyl(trifluoroacetato-κO)tin(IV)]

Yin Yin Teo,^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 9 April 2008; accepted 5 May 2008; online 10 May 2008)

The molecule of the dinuclear title compound, [Sn₂(C₅H₉)₂(C₆H₅)₄(C₂F₃O₂)₂(C₂₈H₂₈O₂P₂)], lies on a center of inversion at the mid-point of the central C—C bond of the bridging phosphine oxide ligand. The Sn atom is five-coordinate in a trans-C₃SnO₂ trigonal-bipyramidal geometry.

Related literature

For the 1/1 co-crystal of bis[1,3-bis(diphenylphosphino)propane]silver(I) cyclopentyldiphenylbis(trifluoroacetato)stannate(IV) with bis[1,3-bis(diphenylphosphino)propane]silver(I) triphenylbis(trifluoroacetato)stannate(IV), see: Teo et al. (2004 ). For other oxygen-donor adducts of triorganotin carboxylates, see: Ng & Kumar Das (1997 ). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991 , 1994 ).

Experimental

Crystal data

[Sn₂(C₅H₉)₂(C₆H₅)₄(C₂F₃O₂)₂(C₂₈H₂₈O₂P₂)]
M_r = 1368.51
Monoclinic, C 2/c
a = 17.3833 (3) Å
b = 12.9181 (2) Å
c = 28.2447 (4) Å
β = 110.990 (1)°
V = 5921.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 100 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.794, T_max = 0.868
31739 measured reflections
7363 independent reflections
6394 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.088
S = 1.06
7363 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Selected bond angles (°)

C1—Sn1—C6	125.3 (1)
C1—Sn1—C12	120.9 (1)
C1—Sn1—O1	93.4 (1)
C1—Sn1—O3	87.5 (1)
C6—Sn1—C12	113.5 (1)
C6—Sn1—O1	93.2 (1)
C6—Sn1—O3	90.3 (1)
C12—Sn1—O1	88.2 (1)
C12—Sn1—O3	87.0 (1)
O1—Sn1—O3	174.9 (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/S1600536808013202/bq2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013202/bq2075Isup2.hkl

checkCIF report

Related literature top

For the 1/1 co-crystal of bis[1,3-bis(diphenylphosphino)propane]silver cyclopentyldiphenylbis(trifluoroacetato)stannate with bis[1,3-bis(diphenylphosphino)propane]silver triphenylbis(trifluoroacetato)stannate, see: Teo et al. (2004). For other oxygen-donor adducts of triorganotin carboxylates, see: Ng & Kumar Das (1997). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Triphenyltin hydroxide (0.18 g, 0.5 mmol) and chorodifluoroacetic acid (0.05 ml, 0.5 mmol) were dissolved in dichloromethane/methanol (25 ml). The mixture was heated until the hydroxide dissolved completely. Another solution containing 1,4-bis(diphenylphosphino)butane (0.42 g, 1.0 mmol) and silver trifluoroacetate (0.11 g, 0.5 mmol) was prepared; this was also heated until the reagents dissolved completely. The two solutions were mixed; crystals were obtained by allowing the solvent to evaporate.

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. Molecular structure of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

[µ-1,4-Bis(diphenylphosphinoyl)butane- κ²O:O']bis[cyclopentyldiphenyl(trifluoroacetato- κO)tin(IV)] top

Crystal data top

[Sn₂(C₅H₉)₂(C₆H₅)₄(C₂F₃O₂)₂(C₂₈H₂₈O₂P₂)]	F(000) = 2776
M_r = 1368.51	D_x = 1.535 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9914 reflections
a = 17.3833 (3) Å	θ = 2.3–28.3°
b = 12.9181 (2) Å	µ = 0.97 mm⁻¹
c = 28.2447 (4) Å	T = 100 K
β = 110.990 (1)°	Block, colorless
V = 5921.7 (2) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	7363 independent reflections
Radiation source: fine-focus sealed tube	6394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 28.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→18
T_min = 0.794, T_max = 0.868	k = −17→17
31739 measured reflections	l = −37→37

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0451P)² + 12.9939P] where P = (F_o² + 2F_c²)/3
7363 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

[Sn₂(C₅H₉)₂(C₆H₅)₄(C₂F₃O₂)₂(C₂₈H₂₈O₂P₂)]	V = 5921.7 (2) Å³
M_r = 1368.51	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.3833 (3) Å	µ = 0.97 mm⁻¹
b = 12.9181 (2) Å	T = 100 K
c = 28.2447 (4) Å	0.25 × 0.20 × 0.15 mm
β = 110.990 (1)°

Data collection top

Bruker SMART APEX diffractometer	7363 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6394 reflections with I > 2σ(I)
T_min = 0.794, T_max = 0.868	R_int = 0.033
31739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0451P)² + 12.9939P] where P = (F_o² + 2F_c²)/3
7363 reflections	Δρ_max = 0.82 e Å⁻³
370 parameters	Δρ_min = −0.76 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Sn1	0.407012 (10)	0.526354 (11)	0.127309 (6)	0.01344 (6)
P1	0.42844 (4)	0.77398 (4)	0.07214 (2)	0.01343 (12)
F1	0.4117 (2)	0.2664 (2)	0.25350 (8)	0.0863 (11)
F2	0.29101 (16)	0.25091 (18)	0.20104 (13)	0.0759 (9)
F3	0.38056 (15)	0.14285 (14)	0.19985 (9)	0.0524 (6)
O1	0.37049 (12)	0.40659 (13)	0.17112 (7)	0.0196 (4)
O2	0.42139 (13)	0.27301 (15)	0.14034 (7)	0.0259 (4)
O3	0.44361 (11)	0.66128 (13)	0.08677 (7)	0.0177 (4)
C1	0.53511 (16)	0.49164 (19)	0.16173 (10)	0.0189 (5)
H1	0.5396	0.4217	0.1777	0.023*
C2	0.58724 (17)	0.4890 (2)	0.12735 (10)	0.0266 (6)
H2A	0.5945	0.4168	0.1179	0.032*
H2B	0.5599	0.5292	0.0960	0.032*
C3	0.67078 (19)	0.5373 (2)	0.15837 (11)	0.0270 (6)
H3A	0.6768	0.6060	0.1446	0.032*
H3B	0.7165	0.4922	0.1578	0.032*
C4	0.67096 (18)	0.5474 (2)	0.21267 (11)	0.0265 (6)
H4A	0.6904	0.4828	0.2322	0.032*
H4B	0.7062	0.6057	0.2309	0.032*
C5	0.58063 (17)	0.5679 (2)	0.20397 (10)	0.0258 (6)
H5A	0.5654	0.6403	0.1931	0.031*
H5B	0.5685	0.5540	0.2351	0.031*
C6	0.32668 (16)	0.46764 (18)	0.05610 (10)	0.0177 (5)
C7	0.25672 (17)	0.4121 (2)	0.05365 (11)	0.0252 (6)
H7	0.2454	0.4012	0.0838	0.030*
C8	0.2032 (2)	0.3724 (2)	0.00810 (13)	0.0361 (8)
H8	0.1556	0.3351	0.0072	0.043*
C9	0.2192 (2)	0.3870 (2)	−0.03592 (12)	0.0386 (8)
H9	0.1828	0.3598	−0.0672	0.046*
C10	0.2891 (2)	0.4418 (2)	−0.03419 (11)	0.0341 (7)
H10	0.3008	0.4512	−0.0643	0.041*
C11	0.34163 (18)	0.4828 (2)	0.01122 (10)	0.0233 (6)
H11	0.3884	0.5217	0.0118	0.028*
C12	0.35061 (16)	0.63869 (18)	0.15955 (9)	0.0157 (5)
C13	0.26575 (17)	0.6385 (2)	0.14839 (10)	0.0217 (5)
H13	0.2331	0.5857	0.1272	0.026*
C14	0.22813 (19)	0.7136 (2)	0.16749 (11)	0.0282 (6)
H14	0.1701	0.7127	0.1590	0.034*
C15	0.2752 (2)	0.7901 (2)	0.19905 (11)	0.0301 (6)
H15	0.2495	0.8410	0.2126	0.036*
C16	0.3596 (2)	0.7924 (2)	0.21080 (11)	0.0281 (6)
H16	0.3917	0.8450	0.2324	0.034*
C17	0.39753 (17)	0.71774 (19)	0.19097 (9)	0.0199 (5)
H17	0.4554	0.7203	0.1987	0.024*
C18	0.38999 (16)	0.31217 (18)	0.16788 (10)	0.0182 (5)
C19	0.36869 (19)	0.2422 (2)	0.20599 (12)	0.0284 (6)
C20	0.45092 (15)	0.79534 (18)	0.01553 (9)	0.0147 (5)
C21	0.49076 (16)	0.71801 (18)	−0.00151 (10)	0.0177 (5)
H21	0.5054	0.6547	0.0167	0.021*
C22	0.50906 (16)	0.73336 (19)	−0.04496 (10)	0.0196 (5)
H22	0.5364	0.6808	−0.0564	0.023*
C23	0.48729 (16)	0.8256 (2)	−0.07160 (9)	0.0192 (5)
H23	0.4991	0.8356	−0.1016	0.023*
C24	0.44851 (16)	0.90303 (19)	−0.05467 (10)	0.0190 (5)
H24	0.4341	0.9662	−0.0730	0.023*
C25	0.43071 (16)	0.88863 (18)	−0.01101 (10)	0.0175 (5)
H25	0.4048	0.9422	0.0008	0.021*
C26	0.49735 (15)	0.85895 (18)	0.11890 (9)	0.0155 (5)
C27	0.47046 (17)	0.94103 (19)	0.14122 (10)	0.0196 (5)
H27	0.4131	0.9529	0.1326	0.024*
C28	0.52691 (18)	1.0053 (2)	0.17594 (10)	0.0224 (5)
H28	0.5082	1.0607	0.1912	0.027*
C29	0.61071 (18)	0.9889 (2)	0.18842 (10)	0.0228 (5)
H29	0.6492	1.0333	0.2120	0.027*
C30	0.63854 (17)	0.9076 (2)	0.16660 (10)	0.0230 (5)
H30	0.6960	0.8964	0.1752	0.028*
C31	0.58197 (16)	0.84317 (19)	0.13223 (10)	0.0192 (5)
H31	0.6010	0.7873	0.1175	0.023*
C32	0.32534 (15)	0.81759 (18)	0.06190 (9)	0.0159 (5)
H32A	0.3193	0.8242	0.0953	0.019*
H32B	0.3185	0.8876	0.0467	0.019*
C33	0.25520 (15)	0.74897 (19)	0.02804 (9)	0.0168 (5)
H33A	0.2656	0.6767	0.0404	0.020*
H33B	0.2030	0.7717	0.0314	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01497 (9)	0.01195 (8)	0.01275 (9)	−0.00079 (6)	0.00417 (6)	−0.00029 (5)
P1	0.0143 (3)	0.0118 (3)	0.0149 (3)	−0.0004 (2)	0.0061 (2)	0.0006 (2)
F1	0.149 (3)	0.0775 (18)	0.0259 (11)	−0.0438 (19)	0.0234 (15)	0.0105 (11)
F2	0.0637 (16)	0.0447 (12)	0.156 (3)	0.0222 (11)	0.0836 (19)	0.0462 (15)
F3	0.0724 (16)	0.0185 (8)	0.0899 (17)	0.0124 (9)	0.0578 (14)	0.0185 (9)
O1	0.0267 (10)	0.0141 (8)	0.0214 (9)	0.0011 (7)	0.0125 (8)	0.0015 (7)
O2	0.0327 (11)	0.0236 (9)	0.0254 (10)	0.0019 (8)	0.0153 (9)	−0.0021 (8)
O3	0.0208 (9)	0.0128 (8)	0.0224 (9)	−0.0001 (7)	0.0111 (7)	0.0025 (6)
C1	0.0170 (12)	0.0187 (11)	0.0188 (12)	0.0009 (9)	0.0036 (10)	−0.0009 (9)
C2	0.0212 (14)	0.0369 (15)	0.0197 (13)	0.0039 (12)	0.0048 (11)	−0.0061 (11)
C3	0.0235 (14)	0.0299 (14)	0.0277 (15)	0.0019 (11)	0.0093 (12)	0.0043 (11)
C4	0.0207 (14)	0.0297 (13)	0.0235 (14)	0.0006 (11)	0.0010 (11)	−0.0058 (11)
C5	0.0211 (14)	0.0346 (14)	0.0177 (13)	0.0027 (11)	0.0020 (11)	−0.0072 (11)
C6	0.0173 (12)	0.0146 (10)	0.0175 (12)	0.0027 (9)	0.0016 (10)	−0.0005 (9)
C7	0.0218 (14)	0.0181 (12)	0.0291 (14)	−0.0029 (10)	0.0009 (11)	−0.0001 (10)
C8	0.0259 (16)	0.0207 (13)	0.0439 (19)	−0.0029 (11)	−0.0093 (14)	−0.0035 (12)
C9	0.043 (2)	0.0209 (13)	0.0313 (16)	0.0073 (13)	−0.0116 (14)	−0.0109 (12)
C10	0.045 (2)	0.0332 (15)	0.0172 (13)	0.0154 (14)	0.0030 (13)	−0.0053 (11)
C11	0.0262 (15)	0.0225 (12)	0.0184 (13)	0.0062 (10)	0.0045 (11)	−0.0014 (10)
C12	0.0222 (13)	0.0156 (10)	0.0101 (10)	0.0022 (9)	0.0066 (9)	0.0021 (8)
C13	0.0225 (13)	0.0208 (12)	0.0220 (13)	−0.0006 (10)	0.0080 (11)	0.0018 (10)
C14	0.0271 (15)	0.0296 (14)	0.0325 (15)	0.0073 (12)	0.0162 (13)	0.0042 (12)
C15	0.0444 (18)	0.0237 (13)	0.0299 (15)	0.0120 (12)	0.0227 (14)	0.0038 (11)
C16	0.0421 (18)	0.0210 (12)	0.0238 (14)	0.0002 (12)	0.0147 (13)	−0.0052 (10)
C17	0.0251 (14)	0.0188 (11)	0.0146 (11)	0.0002 (10)	0.0055 (10)	0.0010 (9)
C18	0.0166 (12)	0.0169 (11)	0.0209 (12)	−0.0002 (9)	0.0064 (10)	−0.0003 (9)
C19	0.0332 (16)	0.0185 (12)	0.0400 (17)	0.0037 (11)	0.0210 (14)	0.0064 (11)
C20	0.0135 (11)	0.0144 (10)	0.0159 (11)	−0.0025 (8)	0.0049 (9)	−0.0006 (8)
C21	0.0191 (12)	0.0139 (10)	0.0214 (12)	−0.0003 (9)	0.0087 (10)	0.0013 (9)
C22	0.0189 (13)	0.0179 (11)	0.0232 (13)	−0.0007 (9)	0.0091 (10)	−0.0031 (9)
C23	0.0193 (13)	0.0247 (12)	0.0137 (11)	−0.0033 (10)	0.0060 (10)	0.0005 (9)
C24	0.0199 (13)	0.0168 (11)	0.0190 (12)	−0.0001 (9)	0.0054 (10)	0.0044 (9)
C25	0.0174 (12)	0.0143 (10)	0.0214 (12)	0.0008 (9)	0.0077 (10)	0.0008 (9)
C26	0.0157 (12)	0.0138 (10)	0.0160 (11)	−0.0013 (9)	0.0045 (9)	0.0035 (8)
C27	0.0179 (13)	0.0189 (11)	0.0218 (13)	−0.0012 (9)	0.0068 (10)	−0.0009 (9)
C28	0.0252 (14)	0.0203 (11)	0.0218 (13)	−0.0021 (10)	0.0084 (11)	−0.0037 (10)
C29	0.0235 (14)	0.0206 (12)	0.0199 (13)	−0.0063 (10)	0.0025 (11)	0.0013 (10)
C30	0.0162 (13)	0.0250 (13)	0.0230 (13)	0.0003 (10)	0.0013 (11)	0.0046 (10)
C31	0.0171 (12)	0.0175 (11)	0.0215 (12)	0.0036 (9)	0.0052 (10)	0.0036 (9)
C32	0.0147 (12)	0.0179 (11)	0.0170 (11)	0.0003 (9)	0.0080 (9)	−0.0005 (9)
C33	0.0149 (12)	0.0183 (11)	0.0174 (12)	−0.0015 (9)	0.0059 (10)	0.0011 (9)

Geometric parameters (Å, º) top

Sn1—C1	2.134 (3)	C12—C17	1.406 (3)
Sn1—C12	2.130 (2)	C13—C14	1.382 (4)
Sn1—C6	2.135 (2)	C13—H13	0.9500
Sn1—O1	2.212 (2)	C14—C15	1.385 (4)
Sn1—O3	2.297 (2)	C14—H14	0.9500
P1—O3	1.5105 (17)	C15—C16	1.383 (5)
P1—C20	1.798 (2)	C15—H15	0.9500
P1—C32	1.801 (3)	C16—C17	1.394 (4)
P1—C26	1.803 (2)	C16—H16	0.9500
F1—C19	1.318 (4)	C17—H17	0.9500
F2—C19	1.312 (4)	C18—C19	1.549 (4)
F3—C19	1.321 (3)	C20—C21	1.396 (3)
O1—C18	1.278 (3)	C20—C25	1.396 (3)
O2—C18	1.210 (3)	C21—C22	1.388 (4)
C1—C5	1.531 (4)	C21—H21	0.9500
C1—C2	1.548 (4)	C22—C23	1.387 (4)
C1—H1	1.0000	C22—H22	0.9500
C2—C3	1.534 (4)	C23—C24	1.384 (4)
C2—H2A	0.9900	C23—H23	0.9500
C2—H2B	0.9900	C24—C25	1.387 (4)
C3—C4	1.538 (4)	C24—H24	0.9500
C3—H3A	0.9900	C25—H25	0.9500
C3—H3B	0.9900	C26—C31	1.397 (3)
C4—C5	1.523 (4)	C26—C27	1.397 (3)
C4—H4A	0.9900	C27—C28	1.388 (4)
C4—H4B	0.9900	C27—H27	0.9500
C5—H5A	0.9900	C28—C29	1.387 (4)
C5—H5B	0.9900	C28—H28	0.9500
C6—C7	1.392 (4)	C29—C30	1.389 (4)
C6—C11	1.396 (4)	C29—H29	0.9500
C7—C8	1.388 (4)	C30—C31	1.385 (4)
C7—H7	0.9500	C30—H30	0.9500
C8—C9	1.381 (5)	C31—H31	0.9500
C8—H8	0.9500	C32—C33	1.534 (3)
C9—C10	1.392 (5)	C32—H32A	0.9900
C9—H9	0.9500	C32—H32B	0.9900
C10—C11	1.386 (4)	C33—C33ⁱ	1.529 (5)
C10—H10	0.9500	C33—H33A	0.9900
C11—H11	0.9500	C33—H33B	0.9900
C12—C13	1.394 (4)

C1—Sn1—C6	125.3 (1)	C12—C13—H13	119.3
C1—Sn1—C12	120.9 (1)	C13—C14—C15	119.9 (3)
C1—Sn1—O1	93.4 (1)	C13—C14—H14	120.0
C1—Sn1—O3	87.5 (1)	C15—C14—H14	120.0
C6—Sn1—C12	113.5 (1)	C14—C15—C16	120.0 (3)
C6—Sn1—O1	93.2 (1)	C14—C15—H15	120.0
C6—Sn1—O3	90.3 (1)	C16—C15—H15	120.0
C12—Sn1—O1	88.2 (1)	C15—C16—C17	120.2 (3)
C12—Sn1—O3	87.0 (1)	C15—C16—H16	119.9
O1—Sn1—O3	174.9 (1)	C17—C16—H16	119.9
O3—P1—C20	108.59 (11)	C16—C17—C12	120.3 (3)
O3—P1—C32	114.31 (11)	C16—C17—H17	119.8
C20—P1—C32	109.27 (11)	C12—C17—H17	119.8
O3—P1—C26	112.42 (11)	O2—C18—O1	129.6 (2)
C20—P1—C26	105.01 (11)	O2—C18—C19	118.6 (2)
C32—P1—C26	106.80 (11)	O1—C18—C19	111.8 (2)
C18—O1—Sn1	119.40 (16)	F2—C19—F3	105.8 (3)
P1—O3—Sn1	144.62 (11)	F2—C19—F1	105.9 (3)
C5—C1—C2	104.4 (2)	F3—C19—F1	107.8 (3)
C5—C1—Sn1	112.55 (17)	F2—C19—C18	111.7 (2)
C2—C1—Sn1	117.95 (18)	F3—C19—C18	112.8 (2)
C5—C1—H1	107.1	F1—C19—C18	112.3 (2)
C2—C1—H1	107.1	C21—C20—C25	119.6 (2)
Sn1—C1—H1	107.1	C21—C20—P1	119.31 (18)
C3—C2—C1	106.2 (2)	C25—C20—P1	121.12 (19)
C3—C2—H2A	110.5	C22—C21—C20	120.1 (2)
C1—C2—H2A	110.5	C22—C21—H21	119.9
C3—C2—H2B	110.5	C20—C21—H21	119.9
C1—C2—H2B	110.5	C21—C22—C23	119.9 (2)
H2A—C2—H2B	108.7	C21—C22—H22	120.1
C2—C3—C4	105.5 (2)	C23—C22—H22	120.1
C2—C3—H3A	110.6	C24—C23—C22	120.3 (2)
C4—C3—H3A	110.6	C24—C23—H23	119.8
C2—C3—H3B	110.6	C22—C23—H23	119.8
C4—C3—H3B	110.6	C23—C24—C25	120.1 (2)
H3A—C3—H3B	108.8	C23—C24—H24	119.9
C5—C4—C3	102.7 (2)	C25—C24—H24	119.9
C5—C4—H4A	111.2	C24—C25—C20	120.0 (2)
C3—C4—H4A	111.2	C24—C25—H25	120.0
C5—C4—H4B	111.2	C20—C25—H25	120.0
C3—C4—H4B	111.2	C31—C26—C27	118.7 (2)
H4A—C4—H4B	109.1	C31—C26—P1	117.90 (19)
C4—C5—C1	103.3 (2)	C27—C26—P1	123.42 (19)
C4—C5—H5A	111.1	C28—C27—C26	120.5 (2)
C1—C5—H5A	111.1	C28—C27—H27	119.8
C4—C5—H5B	111.1	C26—C27—H27	119.8
C1—C5—H5B	111.1	C27—C28—C29	120.0 (3)
H5A—C5—H5B	109.1	C27—C28—H28	120.0
C7—C6—C11	118.1 (2)	C29—C28—H28	120.0
C7—C6—Sn1	119.7 (2)	C28—C29—C30	120.3 (2)
C11—C6—Sn1	122.3 (2)	C28—C29—H29	119.9
C8—C7—C6	121.3 (3)	C30—C29—H29	119.9
C8—C7—H7	119.3	C31—C30—C29	119.5 (3)
C6—C7—H7	119.3	C31—C30—H30	120.3
C9—C8—C7	120.0 (3)	C29—C30—H30	120.3
C9—C8—H8	120.0	C30—C31—C26	121.1 (2)
C7—C8—H8	120.0	C30—C31—H31	119.5
C8—C9—C10	119.5 (3)	C26—C31—H31	119.5
C8—C9—H9	120.2	C33—C32—P1	116.27 (17)
C10—C9—H9	120.2	C33—C32—H32A	108.2
C11—C10—C9	120.3 (3)	P1—C32—H32A	108.2
C11—C10—H10	119.8	C33—C32—H32B	108.2
C9—C10—H10	119.8	P1—C32—H32B	108.2
C10—C11—C6	120.7 (3)	H32A—C32—H32B	107.4
C10—C11—H11	119.6	C33ⁱ—C33—C32	114.1 (3)
C6—C11—H11	119.6	C33ⁱ—C33—H33A	108.7
C13—C12—C17	118.1 (2)	C32—C33—H33A	108.7
C13—C12—Sn1	120.94 (18)	C33ⁱ—C33—H33B	108.7
C17—C12—Sn1	120.86 (19)	C32—C33—H33B	108.7
C14—C13—C12	121.4 (3)	H33A—C33—H33B	107.6
C14—C13—H13	119.3

C12—Sn1—O1—C18	−179.10 (19)	C17—C12—C13—C14	0.0 (4)
C1—Sn1—O1—C18	−58.3 (2)	Sn1—C12—C13—C14	−177.4 (2)
C6—Sn1—O1—C18	67.4 (2)	C12—C13—C14—C15	−1.0 (4)
C20—P1—O3—Sn1	−152.55 (17)	C13—C14—C15—C16	1.0 (4)
C32—P1—O3—Sn1	−30.3 (2)	C14—C15—C16—C17	−0.1 (4)
C26—P1—O3—Sn1	91.7 (2)	C15—C16—C17—C12	−1.0 (4)
C12—Sn1—O3—P1	−14.6 (2)	C13—C12—C17—C16	1.0 (4)
C1—Sn1—O3—P1	−135.7 (2)	Sn1—C12—C17—C16	178.35 (19)
C6—Sn1—O3—P1	98.9 (2)	Sn1—O1—C18—O2	−6.8 (4)
C12—Sn1—C1—C5	−10.2 (2)	Sn1—O1—C18—C19	173.03 (17)
C6—Sn1—C1—C5	163.39 (18)	O2—C18—C19—F2	−125.6 (3)
O1—Sn1—C1—C5	−100.18 (19)	O1—C18—C19—F2	54.5 (3)
O3—Sn1—C1—C5	74.84 (19)	O2—C18—C19—F3	−6.6 (4)
C12—Sn1—C1—C2	−131.82 (19)	O1—C18—C19—F3	173.6 (3)
C6—Sn1—C1—C2	41.8 (2)	O2—C18—C19—F1	115.5 (3)
O1—Sn1—C1—C2	138.19 (19)	O1—C18—C19—F1	−64.3 (3)
O3—Sn1—C1—C2	−46.78 (19)	O3—P1—C20—C21	−11.0 (2)
C5—C1—C2—C3	15.7 (3)	C32—P1—C20—C21	−136.3 (2)
Sn1—C1—C2—C3	141.46 (19)	C26—P1—C20—C21	109.4 (2)
C1—C2—C3—C4	10.5 (3)	O3—P1—C20—C25	170.3 (2)
C2—C3—C4—C5	−32.7 (3)	C32—P1—C20—C25	45.0 (2)
C3—C4—C5—C1	42.7 (3)	C26—P1—C20—C25	−69.3 (2)
C2—C1—C5—C4	−36.2 (3)	C25—C20—C21—C22	−0.9 (4)
Sn1—C1—C5—C4	−165.27 (18)	P1—C20—C21—C22	−179.61 (19)
C12—Sn1—C6—C7	−63.7 (2)	C20—C21—C22—C23	−0.3 (4)
C1—Sn1—C6—C7	122.3 (2)	C21—C22—C23—C24	1.0 (4)
O1—Sn1—C6—C7	25.7 (2)	C22—C23—C24—C25	−0.4 (4)
O3—Sn1—C6—C7	−150.6 (2)	C23—C24—C25—C20	−0.9 (4)
C12—Sn1—C6—C11	116.3 (2)	C21—C20—C25—C24	1.5 (4)
C1—Sn1—C6—C11	−57.7 (2)	P1—C20—C25—C24	−179.82 (19)
O1—Sn1—C6—C11	−154.2 (2)	O3—P1—C26—C31	56.0 (2)
O3—Sn1—C6—C11	29.4 (2)	C20—P1—C26—C31	−61.9 (2)
C11—C6—C7—C8	0.2 (4)	C32—P1—C26—C31	−177.84 (19)
Sn1—C6—C7—C8	−179.7 (2)	O3—P1—C26—C27	−125.9 (2)
C6—C7—C8—C9	0.4 (4)	C20—P1—C26—C27	116.2 (2)
C7—C8—C9—C10	−0.1 (4)	C32—P1—C26—C27	0.3 (2)
C8—C9—C10—C11	−1.0 (4)	C31—C26—C27—C28	−0.1 (4)
C9—C10—C11—C6	1.7 (4)	P1—C26—C27—C28	−178.2 (2)
C7—C6—C11—C10	−1.3 (4)	C26—C27—C28—C29	0.5 (4)
Sn1—C6—C11—C10	178.7 (2)	C27—C28—C29—C30	−0.5 (4)
C1—Sn1—C12—C13	−158.74 (19)	C28—C29—C30—C31	0.0 (4)
C6—Sn1—C12—C13	27.0 (2)	C29—C30—C31—C26	0.4 (4)
O1—Sn1—C12—C13	−65.8 (2)	C27—C26—C31—C30	−0.4 (4)
O3—Sn1—C12—C13	116.0 (2)	P1—C26—C31—C30	177.8 (2)
C1—Sn1—C12—C17	24.0 (2)	O3—P1—C32—C33	−48.0 (2)
C6—Sn1—C12—C17	−150.30 (18)	C20—P1—C32—C33	73.9 (2)
O1—Sn1—C12—C17	116.93 (19)	C26—P1—C32—C33	−173.00 (17)
O3—Sn1—C12—C17	−61.31 (19)	P1—C32—C33—C33ⁱ	−70.9 (3)

Symmetry code: (i) −x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	[Sn₂(C₅H₉)₂(C₆H₅)₄(C₂F₃O₂)₂(C₂₈H₂₈O₂P₂)]
M_r	1368.51
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	17.3833 (3), 12.9181 (2), 28.2447 (4)
β (°)	110.990 (1)
V (Å³)	5921.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.794, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	31739, 7363, 6394
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.06
No. of reflections	7363
No. of parameters	370
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0451P)² + 12.9939P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.76

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

Selected bond angles (º) top

C1—Sn1—C6	125.3 (1)	C6—Sn1—O1	93.2 (1)
C1—Sn1—C12	120.9 (1)	C6—Sn1—O3	90.3 (1)
C1—Sn1—O1	93.4 (1)	C12—Sn1—O1	88.2 (1)
C1—Sn1—O3	87.5 (1)	C12—Sn1—O3	87.0 (1)
C6—Sn1—C12	113.5 (1)	O1—Sn1—O3	174.9 (1)

Acknowledgements

The authors thank the University of Malaya for funding this study (SF022155/2007 A) and also for the purchase of the diffractometer.

References

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