metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Teo, Y. Y., Lo, K. M. & Ng, S. W. (2004). Acta Cryst. E60, m1478-m1480.]). For other oxygen-donor adducts of triorganotin carboxyl­ates, see: Ng & Kumar Das (1997[Ng, S. W. & Kumar Das, V. G. (1997). Trends Organomet. Chem. 2, 107-115.]). For a review of the structural chemistry of organotin carboxyl­ates, see: Tiekink (1991[Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.], 1994[Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn2(C5H9)2(C6H5)4(C2F3O2)2(C28H28O2P2)]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.794, Tmax = 0.868

  • 31739 measured reflections

  • 7363 independent reflections

  • 6394 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.088

  • S = 1.06

  • 7363 reflections

  • 370 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


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.

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 1.2Ueq(C).

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. 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
Mr = 1368.51Dx = 1.535 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9914 reflections
a = 17.3833 (3) Åθ = 2.3–28.3°
b = 12.9181 (2) ŵ = 0.97 mm1
c = 28.2447 (4) ÅT = 100 K
β = 110.990 (1)°Block, colorless
V = 5921.7 (2) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
7363 independent reflections
Radiation source: fine-focus sealed tube6394 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2318
Tmin = 0.794, Tmax = 0.868k = 1717
31739 measured reflectionsl = 3737
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0451P)2 + 12.9939P]
where P = (Fo2 + 2Fc2)/3
7363 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.76 e Å3
Crystal data top
[Sn2(C5H9)2(C6H5)4(C2F3O2)2(C28H28O2P2)]V = 5921.7 (2) Å3
Mr = 1368.51Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.3833 (3) ŵ = 0.97 mm1
b = 12.9181 (2) ÅT = 100 K
c = 28.2447 (4) Å0.25 × 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)
Tmin = 0.794, Tmax = 0.868Rint = 0.033
31739 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0451P)2 + 12.9939P]
where P = (Fo2 + 2Fc2)/3
7363 reflectionsΔρmax = 0.82 e Å3
370 parametersΔρmin = 0.76 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.407012 (10)0.526354 (11)0.127309 (6)0.01344 (6)
P10.42844 (4)0.77398 (4)0.07214 (2)0.01343 (12)
F10.4117 (2)0.2664 (2)0.25350 (8)0.0863 (11)
F20.29101 (16)0.25091 (18)0.20104 (13)0.0759 (9)
F30.38056 (15)0.14285 (14)0.19985 (9)0.0524 (6)
O10.37049 (12)0.40659 (13)0.17112 (7)0.0196 (4)
O20.42139 (13)0.27301 (15)0.14034 (7)0.0259 (4)
O30.44361 (11)0.66128 (13)0.08677 (7)0.0177 (4)
C10.53511 (16)0.49164 (19)0.16173 (10)0.0189 (5)
H10.53960.42170.17770.023*
C20.58724 (17)0.4890 (2)0.12735 (10)0.0266 (6)
H2A0.59450.41680.11790.032*
H2B0.55990.52920.09600.032*
C30.67078 (19)0.5373 (2)0.15837 (11)0.0270 (6)
H3A0.67680.60600.14460.032*
H3B0.71650.49220.15780.032*
C40.67096 (18)0.5474 (2)0.21267 (11)0.0265 (6)
H4A0.69040.48280.23220.032*
H4B0.70620.60570.23090.032*
C50.58063 (17)0.5679 (2)0.20397 (10)0.0258 (6)
H5A0.56540.64030.19310.031*
H5B0.56850.55400.23510.031*
C60.32668 (16)0.46764 (18)0.05610 (10)0.0177 (5)
C70.25672 (17)0.4121 (2)0.05365 (11)0.0252 (6)
H70.24540.40120.08380.030*
C80.2032 (2)0.3724 (2)0.00810 (13)0.0361 (8)
H80.15560.33510.00720.043*
C90.2192 (2)0.3870 (2)0.03592 (12)0.0386 (8)
H90.18280.35980.06720.046*
C100.2891 (2)0.4418 (2)0.03419 (11)0.0341 (7)
H100.30080.45120.06430.041*
C110.34163 (18)0.4828 (2)0.01122 (10)0.0233 (6)
H110.38840.52170.01180.028*
C120.35061 (16)0.63869 (18)0.15955 (9)0.0157 (5)
C130.26575 (17)0.6385 (2)0.14839 (10)0.0217 (5)
H130.23310.58570.12720.026*
C140.22813 (19)0.7136 (2)0.16749 (11)0.0282 (6)
H140.17010.71270.15900.034*
C150.2752 (2)0.7901 (2)0.19905 (11)0.0301 (6)
H150.24950.84100.21260.036*
C160.3596 (2)0.7924 (2)0.21080 (11)0.0281 (6)
H160.39170.84500.23240.034*
C170.39753 (17)0.71774 (19)0.19097 (9)0.0199 (5)
H170.45540.72030.19870.024*
C180.38999 (16)0.31217 (18)0.16788 (10)0.0182 (5)
C190.36869 (19)0.2422 (2)0.20599 (12)0.0284 (6)
C200.45092 (15)0.79534 (18)0.01553 (9)0.0147 (5)
C210.49076 (16)0.71801 (18)0.00151 (10)0.0177 (5)
H210.50540.65470.01670.021*
C220.50906 (16)0.73336 (19)0.04496 (10)0.0196 (5)
H220.53640.68080.05640.023*
C230.48729 (16)0.8256 (2)0.07160 (9)0.0192 (5)
H230.49910.83560.10160.023*
C240.44851 (16)0.90303 (19)0.05467 (10)0.0190 (5)
H240.43410.96620.07300.023*
C250.43071 (16)0.88863 (18)0.01101 (10)0.0175 (5)
H250.40480.94220.00080.021*
C260.49735 (15)0.85895 (18)0.11890 (9)0.0155 (5)
C270.47046 (17)0.94103 (19)0.14122 (10)0.0196 (5)
H270.41310.95290.13260.024*
C280.52691 (18)1.0053 (2)0.17594 (10)0.0224 (5)
H280.50821.06070.19120.027*
C290.61071 (18)0.9889 (2)0.18842 (10)0.0228 (5)
H290.64921.03330.21200.027*
C300.63854 (17)0.9076 (2)0.16660 (10)0.0230 (5)
H300.69600.89640.17520.028*
C310.58197 (16)0.84317 (19)0.13223 (10)0.0192 (5)
H310.60100.78730.11750.023*
C320.32534 (15)0.81759 (18)0.06190 (9)0.0159 (5)
H32A0.31930.82420.09530.019*
H32B0.31850.88760.04670.019*
C330.25520 (15)0.74897 (19)0.02804 (9)0.0168 (5)
H33A0.26560.67670.04040.020*
H33B0.20300.77170.03140.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01497 (9)0.01195 (8)0.01275 (9)0.00079 (6)0.00417 (6)0.00029 (5)
P10.0143 (3)0.0118 (3)0.0149 (3)0.0004 (2)0.0061 (2)0.0006 (2)
F10.149 (3)0.0775 (18)0.0259 (11)0.0438 (19)0.0234 (15)0.0105 (11)
F20.0637 (16)0.0447 (12)0.156 (3)0.0222 (11)0.0836 (19)0.0462 (15)
F30.0724 (16)0.0185 (8)0.0899 (17)0.0124 (9)0.0578 (14)0.0185 (9)
O10.0267 (10)0.0141 (8)0.0214 (9)0.0011 (7)0.0125 (8)0.0015 (7)
O20.0327 (11)0.0236 (9)0.0254 (10)0.0019 (8)0.0153 (9)0.0021 (8)
O30.0208 (9)0.0128 (8)0.0224 (9)0.0001 (7)0.0111 (7)0.0025 (6)
C10.0170 (12)0.0187 (11)0.0188 (12)0.0009 (9)0.0036 (10)0.0009 (9)
C20.0212 (14)0.0369 (15)0.0197 (13)0.0039 (12)0.0048 (11)0.0061 (11)
C30.0235 (14)0.0299 (14)0.0277 (15)0.0019 (11)0.0093 (12)0.0043 (11)
C40.0207 (14)0.0297 (13)0.0235 (14)0.0006 (11)0.0010 (11)0.0058 (11)
C50.0211 (14)0.0346 (14)0.0177 (13)0.0027 (11)0.0020 (11)0.0072 (11)
C60.0173 (12)0.0146 (10)0.0175 (12)0.0027 (9)0.0016 (10)0.0005 (9)
C70.0218 (14)0.0181 (12)0.0291 (14)0.0029 (10)0.0009 (11)0.0001 (10)
C80.0259 (16)0.0207 (13)0.0439 (19)0.0029 (11)0.0093 (14)0.0035 (12)
C90.043 (2)0.0209 (13)0.0313 (16)0.0073 (13)0.0116 (14)0.0109 (12)
C100.045 (2)0.0332 (15)0.0172 (13)0.0154 (14)0.0030 (13)0.0053 (11)
C110.0262 (15)0.0225 (12)0.0184 (13)0.0062 (10)0.0045 (11)0.0014 (10)
C120.0222 (13)0.0156 (10)0.0101 (10)0.0022 (9)0.0066 (9)0.0021 (8)
C130.0225 (13)0.0208 (12)0.0220 (13)0.0006 (10)0.0080 (11)0.0018 (10)
C140.0271 (15)0.0296 (14)0.0325 (15)0.0073 (12)0.0162 (13)0.0042 (12)
C150.0444 (18)0.0237 (13)0.0299 (15)0.0120 (12)0.0227 (14)0.0038 (11)
C160.0421 (18)0.0210 (12)0.0238 (14)0.0002 (12)0.0147 (13)0.0052 (10)
C170.0251 (14)0.0188 (11)0.0146 (11)0.0002 (10)0.0055 (10)0.0010 (9)
C180.0166 (12)0.0169 (11)0.0209 (12)0.0002 (9)0.0064 (10)0.0003 (9)
C190.0332 (16)0.0185 (12)0.0400 (17)0.0037 (11)0.0210 (14)0.0064 (11)
C200.0135 (11)0.0144 (10)0.0159 (11)0.0025 (8)0.0049 (9)0.0006 (8)
C210.0191 (12)0.0139 (10)0.0214 (12)0.0003 (9)0.0087 (10)0.0013 (9)
C220.0189 (13)0.0179 (11)0.0232 (13)0.0007 (9)0.0091 (10)0.0031 (9)
C230.0193 (13)0.0247 (12)0.0137 (11)0.0033 (10)0.0060 (10)0.0005 (9)
C240.0199 (13)0.0168 (11)0.0190 (12)0.0001 (9)0.0054 (10)0.0044 (9)
C250.0174 (12)0.0143 (10)0.0214 (12)0.0008 (9)0.0077 (10)0.0008 (9)
C260.0157 (12)0.0138 (10)0.0160 (11)0.0013 (9)0.0045 (9)0.0035 (8)
C270.0179 (13)0.0189 (11)0.0218 (13)0.0012 (9)0.0068 (10)0.0009 (9)
C280.0252 (14)0.0203 (11)0.0218 (13)0.0021 (10)0.0084 (11)0.0037 (10)
C290.0235 (14)0.0206 (12)0.0199 (13)0.0063 (10)0.0025 (11)0.0013 (10)
C300.0162 (13)0.0250 (13)0.0230 (13)0.0003 (10)0.0013 (11)0.0046 (10)
C310.0171 (12)0.0175 (11)0.0215 (12)0.0036 (9)0.0052 (10)0.0036 (9)
C320.0147 (12)0.0179 (11)0.0170 (11)0.0003 (9)0.0080 (9)0.0005 (9)
C330.0149 (12)0.0183 (11)0.0174 (12)0.0015 (9)0.0059 (10)0.0011 (9)
Geometric parameters (Å, º) top
Sn1—C12.134 (3)C12—C171.406 (3)
Sn1—C122.130 (2)C13—C141.382 (4)
Sn1—C62.135 (2)C13—H130.9500
Sn1—O12.212 (2)C14—C151.385 (4)
Sn1—O32.297 (2)C14—H140.9500
P1—O31.5105 (17)C15—C161.383 (5)
P1—C201.798 (2)C15—H150.9500
P1—C321.801 (3)C16—C171.394 (4)
P1—C261.803 (2)C16—H160.9500
F1—C191.318 (4)C17—H170.9500
F2—C191.312 (4)C18—C191.549 (4)
F3—C191.321 (3)C20—C211.396 (3)
O1—C181.278 (3)C20—C251.396 (3)
O2—C181.210 (3)C21—C221.388 (4)
C1—C51.531 (4)C21—H210.9500
C1—C21.548 (4)C22—C231.387 (4)
C1—H11.0000C22—H220.9500
C2—C31.534 (4)C23—C241.384 (4)
C2—H2A0.9900C23—H230.9500
C2—H2B0.9900C24—C251.387 (4)
C3—C41.538 (4)C24—H240.9500
C3—H3A0.9900C25—H250.9500
C3—H3B0.9900C26—C311.397 (3)
C4—C51.523 (4)C26—C271.397 (3)
C4—H4A0.9900C27—C281.388 (4)
C4—H4B0.9900C27—H270.9500
C5—H5A0.9900C28—C291.387 (4)
C5—H5B0.9900C28—H280.9500
C6—C71.392 (4)C29—C301.389 (4)
C6—C111.396 (4)C29—H290.9500
C7—C81.388 (4)C30—C311.385 (4)
C7—H70.9500C30—H300.9500
C8—C91.381 (5)C31—H310.9500
C8—H80.9500C32—C331.534 (3)
C9—C101.392 (5)C32—H32A0.9900
C9—H90.9500C32—H32B0.9900
C10—C111.386 (4)C33—C33i1.529 (5)
C10—H100.9500C33—H33A0.9900
C11—H110.9500C33—H33B0.9900
C12—C131.394 (4)
C1—Sn1—C6125.3 (1)C12—C13—H13119.3
C1—Sn1—C12120.9 (1)C13—C14—C15119.9 (3)
C1—Sn1—O193.4 (1)C13—C14—H14120.0
C1—Sn1—O387.5 (1)C15—C14—H14120.0
C6—Sn1—C12113.5 (1)C14—C15—C16120.0 (3)
C6—Sn1—O193.2 (1)C14—C15—H15120.0
C6—Sn1—O390.3 (1)C16—C15—H15120.0
C12—Sn1—O188.2 (1)C15—C16—C17120.2 (3)
C12—Sn1—O387.0 (1)C15—C16—H16119.9
O1—Sn1—O3174.9 (1)C17—C16—H16119.9
O3—P1—C20108.59 (11)C16—C17—C12120.3 (3)
O3—P1—C32114.31 (11)C16—C17—H17119.8
C20—P1—C32109.27 (11)C12—C17—H17119.8
O3—P1—C26112.42 (11)O2—C18—O1129.6 (2)
C20—P1—C26105.01 (11)O2—C18—C19118.6 (2)
C32—P1—C26106.80 (11)O1—C18—C19111.8 (2)
C18—O1—Sn1119.40 (16)F2—C19—F3105.8 (3)
P1—O3—Sn1144.62 (11)F2—C19—F1105.9 (3)
C5—C1—C2104.4 (2)F3—C19—F1107.8 (3)
C5—C1—Sn1112.55 (17)F2—C19—C18111.7 (2)
C2—C1—Sn1117.95 (18)F3—C19—C18112.8 (2)
C5—C1—H1107.1F1—C19—C18112.3 (2)
C2—C1—H1107.1C21—C20—C25119.6 (2)
Sn1—C1—H1107.1C21—C20—P1119.31 (18)
C3—C2—C1106.2 (2)C25—C20—P1121.12 (19)
C3—C2—H2A110.5C22—C21—C20120.1 (2)
C1—C2—H2A110.5C22—C21—H21119.9
C3—C2—H2B110.5C20—C21—H21119.9
C1—C2—H2B110.5C21—C22—C23119.9 (2)
H2A—C2—H2B108.7C21—C22—H22120.1
C2—C3—C4105.5 (2)C23—C22—H22120.1
C2—C3—H3A110.6C24—C23—C22120.3 (2)
C4—C3—H3A110.6C24—C23—H23119.8
C2—C3—H3B110.6C22—C23—H23119.8
C4—C3—H3B110.6C23—C24—C25120.1 (2)
H3A—C3—H3B108.8C23—C24—H24119.9
C5—C4—C3102.7 (2)C25—C24—H24119.9
C5—C4—H4A111.2C24—C25—C20120.0 (2)
C3—C4—H4A111.2C24—C25—H25120.0
C5—C4—H4B111.2C20—C25—H25120.0
C3—C4—H4B111.2C31—C26—C27118.7 (2)
H4A—C4—H4B109.1C31—C26—P1117.90 (19)
C4—C5—C1103.3 (2)C27—C26—P1123.42 (19)
C4—C5—H5A111.1C28—C27—C26120.5 (2)
C1—C5—H5A111.1C28—C27—H27119.8
C4—C5—H5B111.1C26—C27—H27119.8
C1—C5—H5B111.1C27—C28—C29120.0 (3)
H5A—C5—H5B109.1C27—C28—H28120.0
C7—C6—C11118.1 (2)C29—C28—H28120.0
C7—C6—Sn1119.7 (2)C28—C29—C30120.3 (2)
C11—C6—Sn1122.3 (2)C28—C29—H29119.9
C8—C7—C6121.3 (3)C30—C29—H29119.9
C8—C7—H7119.3C31—C30—C29119.5 (3)
C6—C7—H7119.3C31—C30—H30120.3
C9—C8—C7120.0 (3)C29—C30—H30120.3
C9—C8—H8120.0C30—C31—C26121.1 (2)
C7—C8—H8120.0C30—C31—H31119.5
C8—C9—C10119.5 (3)C26—C31—H31119.5
C8—C9—H9120.2C33—C32—P1116.27 (17)
C10—C9—H9120.2C33—C32—H32A108.2
C11—C10—C9120.3 (3)P1—C32—H32A108.2
C11—C10—H10119.8C33—C32—H32B108.2
C9—C10—H10119.8P1—C32—H32B108.2
C10—C11—C6120.7 (3)H32A—C32—H32B107.4
C10—C11—H11119.6C33i—C33—C32114.1 (3)
C6—C11—H11119.6C33i—C33—H33A108.7
C13—C12—C17118.1 (2)C32—C33—H33A108.7
C13—C12—Sn1120.94 (18)C33i—C33—H33B108.7
C17—C12—Sn1120.86 (19)C32—C33—H33B108.7
C14—C13—C12121.4 (3)H33A—C33—H33B107.6
C14—C13—H13119.3
C12—Sn1—O1—C18179.10 (19)C17—C12—C13—C140.0 (4)
C1—Sn1—O1—C1858.3 (2)Sn1—C12—C13—C14177.4 (2)
C6—Sn1—O1—C1867.4 (2)C12—C13—C14—C151.0 (4)
C20—P1—O3—Sn1152.55 (17)C13—C14—C15—C161.0 (4)
C32—P1—O3—Sn130.3 (2)C14—C15—C16—C170.1 (4)
C26—P1—O3—Sn191.7 (2)C15—C16—C17—C121.0 (4)
C12—Sn1—O3—P114.6 (2)C13—C12—C17—C161.0 (4)
C1—Sn1—O3—P1135.7 (2)Sn1—C12—C17—C16178.35 (19)
C6—Sn1—O3—P198.9 (2)Sn1—O1—C18—O26.8 (4)
C12—Sn1—C1—C510.2 (2)Sn1—O1—C18—C19173.03 (17)
C6—Sn1—C1—C5163.39 (18)O2—C18—C19—F2125.6 (3)
O1—Sn1—C1—C5100.18 (19)O1—C18—C19—F254.5 (3)
O3—Sn1—C1—C574.84 (19)O2—C18—C19—F36.6 (4)
C12—Sn1—C1—C2131.82 (19)O1—C18—C19—F3173.6 (3)
C6—Sn1—C1—C241.8 (2)O2—C18—C19—F1115.5 (3)
O1—Sn1—C1—C2138.19 (19)O1—C18—C19—F164.3 (3)
O3—Sn1—C1—C246.78 (19)O3—P1—C20—C2111.0 (2)
C5—C1—C2—C315.7 (3)C32—P1—C20—C21136.3 (2)
Sn1—C1—C2—C3141.46 (19)C26—P1—C20—C21109.4 (2)
C1—C2—C3—C410.5 (3)O3—P1—C20—C25170.3 (2)
C2—C3—C4—C532.7 (3)C32—P1—C20—C2545.0 (2)
C3—C4—C5—C142.7 (3)C26—P1—C20—C2569.3 (2)
C2—C1—C5—C436.2 (3)C25—C20—C21—C220.9 (4)
Sn1—C1—C5—C4165.27 (18)P1—C20—C21—C22179.61 (19)
C12—Sn1—C6—C763.7 (2)C20—C21—C22—C230.3 (4)
C1—Sn1—C6—C7122.3 (2)C21—C22—C23—C241.0 (4)
O1—Sn1—C6—C725.7 (2)C22—C23—C24—C250.4 (4)
O3—Sn1—C6—C7150.6 (2)C23—C24—C25—C200.9 (4)
C12—Sn1—C6—C11116.3 (2)C21—C20—C25—C241.5 (4)
C1—Sn1—C6—C1157.7 (2)P1—C20—C25—C24179.82 (19)
O1—Sn1—C6—C11154.2 (2)O3—P1—C26—C3156.0 (2)
O3—Sn1—C6—C1129.4 (2)C20—P1—C26—C3161.9 (2)
C11—C6—C7—C80.2 (4)C32—P1—C26—C31177.84 (19)
Sn1—C6—C7—C8179.7 (2)O3—P1—C26—C27125.9 (2)
C6—C7—C8—C90.4 (4)C20—P1—C26—C27116.2 (2)
C7—C8—C9—C100.1 (4)C32—P1—C26—C270.3 (2)
C8—C9—C10—C111.0 (4)C31—C26—C27—C280.1 (4)
C9—C10—C11—C61.7 (4)P1—C26—C27—C28178.2 (2)
C7—C6—C11—C101.3 (4)C26—C27—C28—C290.5 (4)
Sn1—C6—C11—C10178.7 (2)C27—C28—C29—C300.5 (4)
C1—Sn1—C12—C13158.74 (19)C28—C29—C30—C310.0 (4)
C6—Sn1—C12—C1327.0 (2)C29—C30—C31—C260.4 (4)
O1—Sn1—C12—C1365.8 (2)C27—C26—C31—C300.4 (4)
O3—Sn1—C12—C13116.0 (2)P1—C26—C31—C30177.8 (2)
C1—Sn1—C12—C1724.0 (2)O3—P1—C32—C3348.0 (2)
C6—Sn1—C12—C17150.30 (18)C20—P1—C32—C3373.9 (2)
O1—Sn1—C12—C17116.93 (19)C26—P1—C32—C33173.00 (17)
O3—Sn1—C12—C1761.31 (19)P1—C32—C33—C33i70.9 (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)]
Mr1368.51
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)17.3833 (3), 12.9181 (2), 28.2447 (4)
β (°) 110.990 (1)
V3)5921.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.97
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.794, 0.868
No. of measured, independent and
observed [I > 2σ(I)] reflections
31739, 7363, 6394
Rint0.033
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.088, 1.06
No. of reflections7363
No. of parameters370
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0451P)2 + 12.9939P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)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—C6125.3 (1)C6—Sn1—O193.2 (1)
C1—Sn1—C12120.9 (1)C6—Sn1—O390.3 (1)
C1—Sn1—O193.4 (1)C12—Sn1—O188.2 (1)
C1—Sn1—O387.5 (1)C12—Sn1—O387.0 (1)
C6—Sn1—C12113.5 (1)O1—Sn1—O3174.9 (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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNg, S. W. & Kumar Das, V. G. (1997). Trends Organomet. Chem. 2, 107–115.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTeo, Y. Y., Lo, K. M. & Ng, S. W. (2004). Acta Cryst. E60, m1478–m1480.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23.  CrossRef CAS Web of Science Google Scholar
First citationTiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116.  Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds