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lh2611 scheme

Acta Cryst. (2008). E64, m700    [ doi:10.1107/S1600536808010775 ]

Dicyclohexylammonium bis(chlorodifluoroacetato-[kappa]O)cyclopentyldiphenylstannate(IV)

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

Abstract top

The five-coordinate Sn atom in the title mixed organyl stannate compound, (C12H24N)[Sn(C5H9)(C6H5)2(C2ClF2O2)], is in a trans-C3SnO2 trigonal-bipyramidal coordination environment. The NH2 groups of the cations act as hydrogen-bond donors to two symmetry-related anions, resulting in the formation of linear chains. One of the phenyl rings is disordered over two sites with equal occupancies.

Comment top

The preceding study reports the crystal structure of dicyclohexylammonium bis(chlorodifluroacetato)cyclohexyldiphenylstannate (Teo et al., 2008).

Replacing the cyclohexyl ligand on tin by the cyclopentyl ligand furnishes a similar stannate compound(I), (Fig. 1). The cation engages in hydrogen bonding to the anion to give rise to a chain structure.

Related literature top

For details of the crystal structure of dicyclohexylammonium bis(chlorodifluoroacetato)cyclohexyldiphenylstannate, see Teo et al. (2008). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Cyclopentyldiphenyltin hydroxide (0.36 g, 1 mmol) was added to an ethanol solution (50 ml) of dicyclohexylamine (0.20 ml, 2 mmol) and chlorodifluoroacetic acid (0.1 ml, 2 mmol). The solution was heated to dissolve the reactants completely; the filtered solution yielded the salt in 70% yield.

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). The ammonium H atoms (N–H 0.88 Å) were similarly treated.

For the cyclopentyl ligand, the 1,2-relatd C–C distances were restrained to 1.54±0.01 Å and the 1,3-related one to 2.51 + 0.01 Å. One of the aromatic rings is disordered over two sites; the occupancies could not be refined, and was assumed to be 1:1. For this ring, the 1,2-related distances were restrained to 1.39±0.01 Å and the 1,4-related ones to 2.78±0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones; the six atoms of each ring were restrained to be approximately flat.

There is minor disorder in the chlorodifluoromethyl groups; the C–Cl distance was restrained to 1.75±0.01 Å and the C–F distances to 1.35±0.01 Å. The final difference Fourier map had a large peak in the vicinity of Sn1.

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. 50% Probability thermal ellipsoid plot of the two independent formula units of [(C6H11)2NH2)] [Sn(C5H9)(C6H5)2(O2CClF2)2]. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclopentylhexyldiphenylstannate(IV)] top
Crystal data top
(C12H24N)[Sn(C5H9)(C6H5)2(C2ClF2O2)]F000 = 800
Mr = 783.27Dx = 1.508 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4999 reflections
a = 8.8610 (2) Åθ = 2.3–24.4º
b = 19.3132 (3) ŵ = 0.95 mm−1
c = 10.6823 (2) ÅT = 100 (2) K
β = 109.385 (1)ºIrregular block, colorless
V = 1724.47 (6) Å30.30 × 0.20 × 0.15 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		7831 independent reflections
Radiation source: fine-focus sealed tube6637 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 100(2) Kθmax = 27.5º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→10
Tmin = 0.679, Tmax = 0.870k = −25→25
18017 measured reflectionsl = −13→13
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050  w = 1/[σ2(Fo2) + (0.0717P)2 + 1.4264P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132(Δ/σ)max = 0.001
S = 1.04Δρmax = 1.11 e Å−3
7831 reflectionsΔρmin = −0.71 e Å−3
421 parametersExtinction correction: none
41 restraintsAbsolute structure: Flack (1983), 3766 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (3)
Secondary atom site location: difference Fourier map
Crystal data top
(C12H24N)[Sn(C5H9)(C6H5)2(C2ClF2O2)]V = 1724.47 (6) Å3
Mr = 783.27Z = 2
Monoclinic, P21Mo Kα
a = 8.8610 (2) ŵ = 0.95 mm−1
b = 19.3132 (3) ÅT = 100 (2) K
c = 10.6823 (2) Å0.30 × 0.20 × 0.15 mm
β = 109.385 (1)º
Data collection top
Bruker SMART APEX
diffractometer		7831 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6637 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.870Rint = 0.038
18017 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.132Δρmax = 1.11 e Å−3
S = 1.04Δρmin = −0.71 e Å−3
7831 reflectionsAbsolute structure: Flack (1983), 3766 Friedel pairs
421 parametersFlack parameter: −0.03 (3)
41 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.41483 (4)0.50001 (7)0.27785 (3)0.03273 (11)
Cl10.5652 (5)0.7213 (2)0.0894 (3)0.1213 (13)
Cl20.1779 (5)0.25792 (18)0.2051 (3)0.1310 (16)
F10.7544 (5)0.7106 (2)0.3078 (5)0.0684 (13)
F20.5523 (5)0.7777 (2)0.2839 (5)0.0622 (12)
F30.3331 (6)0.2399 (2)0.4277 (5)0.0721 (14)
F40.1352 (6)0.3071 (3)0.4035 (6)0.0776 (15)
O10.5515 (5)0.5970 (2)0.2551 (5)0.0389 (10)
O20.4078 (5)0.6683 (2)0.3391 (5)0.0372 (10)
O30.2746 (5)0.4049 (2)0.2913 (4)0.0366 (9)
O40.4990 (6)0.3475 (2)0.4043 (5)0.0419 (10)
N10.2491 (6)0.7638 (2)0.4417 (4)0.0264 (9)
H1N10.29760.73560.40260.032*
H1N20.31960.79470.48610.032*
C10.5036 (5)0.5092 (2)0.4901 (5)0.0335 (12)
C20.445 (4)0.4703 (16)0.574 (4)0.034 (3)0.50
H20.36040.43890.53360.040*0.50
C30.502 (6)0.474 (2)0.711 (4)0.040 (5)0.50
H30.45810.44620.76450.047*0.50
C40.625 (6)0.520 (3)0.7657 (10)0.0475 (18)0.50
H40.66660.52370.85970.057*0.50
C50.693 (5)0.561 (2)0.692 (4)0.037 (4)0.50
H50.77790.59260.73320.045*0.50
C60.6282 (18)0.5547 (12)0.555 (4)0.033 (3)0.50
H60.67140.58260.50180.039*0.50
C2'0.420 (4)0.4798 (14)0.567 (4)0.034 (3)0.50
H2'0.32120.45650.52610.040*0.50
C3'0.484 (6)0.486 (2)0.703 (4)0.040 (5)0.50
H3'0.42790.46570.75640.047*0.50
C4'0.627 (6)0.519 (3)0.7660 (10)0.0475 (18)0.50
H4'0.66970.52240.85990.057*0.50
C5'0.707 (5)0.548 (2)0.686 (4)0.037 (4)0.50
H5'0.80610.57060.72780.045*0.50
C6'0.6483 (16)0.5438 (12)0.549 (4)0.033 (3)0.50
H6'0.70460.56400.49590.039*0.50
C70.1931 (7)0.5482 (3)0.1691 (6)0.0315 (12)
C80.1848 (8)0.5921 (3)0.0642 (6)0.0373 (13)
H80.27460.59770.03550.045*
C90.0415 (8)0.6283 (4)0.0009 (7)0.0447 (15)
H90.03480.6580−0.07180.054*
C10−0.0874 (8)0.6213 (3)0.0426 (6)0.0409 (14)
H10−0.18230.64690.00000.049*
C11−0.0815 (7)0.5781 (3)0.1447 (7)0.0373 (13)
H11−0.17200.57310.17280.045*
C120.0584 (7)0.5410 (3)0.2081 (6)0.0340 (12)
H120.06190.51050.27880.041*
C130.5521 (7)0.4533 (4)0.1721 (7)0.056 (2)
H130.56770.49120.11390.068*
C140.4920 (7)0.3925 (4)0.0773 (8)0.062 (2)
H14A0.41100.4081−0.00640.075*
H14B0.44370.35650.11820.075*
C150.6441 (9)0.3636 (4)0.0507 (7)0.074 (3)
H15A0.64320.31230.05010.089*
H15B0.64800.3802−0.03580.089*
C160.7884 (7)0.3909 (4)0.1650 (7)0.0494 (17)
H16A0.85640.42040.12970.059*
H16B0.85390.35190.21420.059*
C170.7225 (7)0.4334 (4)0.2575 (6)0.0433 (15)
H17A0.72150.40540.33480.052*
H17B0.78830.47530.28980.052*
C180.5096 (7)0.6545 (3)0.2852 (6)0.0358 (13)
C190.5981 (7)0.7165 (3)0.2514 (6)0.0458 (16)
C200.3529 (8)0.3533 (3)0.3501 (7)0.0358 (14)
C210.2525 (7)0.2913 (3)0.3561 (5)0.0415 (14)
C220.1928 (7)0.7229 (3)0.5380 (6)0.0306 (12)
H220.11090.75090.56110.037*
C230.3314 (9)0.7076 (3)0.6660 (6)0.0437 (15)
H23A0.41270.67860.64580.052*
H23B0.38300.75140.70630.052*
C240.2667 (10)0.6697 (4)0.7623 (7)0.0514 (18)
H24A0.19150.70030.78700.062*
H24B0.35630.65850.84410.062*
C250.1806 (9)0.6031 (3)0.7024 (7)0.0423 (15)
H25A0.25900.56980.68930.051*
H25B0.13250.58200.76480.051*
C260.0522 (8)0.6162 (3)0.5720 (7)0.0433 (15)
H26A−0.03490.64330.58740.052*
H26B0.00690.57140.53180.052*
C270.1156 (8)0.6560 (3)0.4746 (6)0.0361 (13)
H27A0.19500.62720.45140.043*
H27B0.02630.66620.39200.043*
C290.1158 (7)0.8005 (3)0.3367 (6)0.0317 (12)
H290.01770.77110.31600.038*
C300.1550 (8)0.8094 (4)0.2104 (7)0.0463 (16)
H30A0.17320.76350.17660.056*
H30B0.25410.83700.22860.056*
C310.0151 (9)0.8464 (5)0.1056 (8)0.061 (2)
H31A0.04410.85450.02490.074*
H31B−0.08020.81600.08090.074*
C32−0.0264 (9)0.9144 (4)0.1539 (8)0.057 (2)
H32A−0.12220.93400.08620.069*
H32B0.06320.94730.16670.069*
C33−0.0591 (9)0.9056 (4)0.2842 (8)0.057 (2)
H33A−0.15790.87800.26860.069*
H33B−0.07650.95170.31780.069*
C340.0797 (9)0.8696 (4)0.3879 (7)0.0471 (16)
H34A0.17580.89940.41060.057*
H34B0.05250.86220.46960.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01949 (15)0.02969 (16)0.0492 (2)0.0012 (2)0.01167 (12)−0.0076 (2)
Cl10.153 (4)0.124 (3)0.103 (2)−0.027 (2)0.065 (2)−0.0111 (19)
Cl20.164 (3)0.085 (2)0.0910 (19)−0.061 (2)−0.029 (2)0.0079 (15)
F10.031 (2)0.050 (2)0.128 (4)−0.0105 (18)0.031 (2)0.006 (2)
F20.045 (3)0.035 (2)0.115 (4)−0.0008 (18)0.037 (3)0.002 (2)
F30.062 (3)0.057 (3)0.110 (4)0.019 (2)0.045 (3)0.048 (3)
F40.049 (3)0.063 (3)0.134 (5)0.010 (2)0.049 (3)0.024 (3)
O10.021 (2)0.045 (2)0.058 (3)−0.0021 (18)0.022 (2)−0.004 (2)
O20.027 (2)0.040 (2)0.050 (3)−0.0052 (19)0.020 (2)−0.010 (2)
O30.024 (2)0.0246 (19)0.053 (3)0.0051 (16)0.0032 (18)−0.0040 (17)
O40.031 (2)0.039 (2)0.054 (3)0.0095 (19)0.013 (2)−0.0006 (19)
N10.021 (2)0.029 (2)0.031 (2)−0.0031 (18)0.0116 (19)−0.0055 (17)
C10.020 (2)0.027 (3)0.052 (3)0.006 (2)0.011 (2)0.001 (2)
C20.011 (8)0.037 (7)0.049 (5)0.011 (5)0.007 (6)−0.012 (4)
C30.029 (9)0.038 (14)0.054 (5)0.010 (8)0.016 (5)−0.005 (5)
C40.043 (4)0.053 (5)0.046 (3)0.007 (3)0.013 (3)−0.012 (3)
C50.029 (6)0.023 (13)0.053 (5)0.008 (8)0.003 (5)−0.018 (7)
C60.024 (4)0.019 (6)0.054 (5)0.008 (5)0.012 (5)−0.009 (6)
C2'0.011 (8)0.037 (7)0.049 (5)0.011 (5)0.007 (6)−0.012 (4)
C3'0.029 (9)0.038 (14)0.054 (5)0.010 (8)0.016 (5)−0.005 (5)
C4'0.043 (4)0.053 (5)0.046 (3)0.007 (3)0.013 (3)−0.012 (3)
C5'0.029 (6)0.023 (13)0.053 (5)0.008 (8)0.003 (5)−0.018 (7)
C6'0.024 (4)0.019 (6)0.054 (5)0.008 (5)0.012 (5)−0.009 (6)
C70.028 (3)0.022 (2)0.042 (3)0.005 (2)0.009 (2)−0.007 (2)
C80.032 (3)0.047 (3)0.036 (3)−0.006 (3)0.016 (3)−0.001 (2)
C90.038 (4)0.053 (4)0.040 (4)0.002 (3)0.010 (3)0.004 (3)
C100.030 (3)0.039 (3)0.046 (4)0.006 (3)0.003 (3)−0.004 (3)
C110.023 (3)0.038 (3)0.053 (4)−0.001 (2)0.014 (3)−0.004 (3)
C120.024 (3)0.033 (3)0.043 (3)−0.006 (2)0.010 (2)−0.006 (2)
C130.028 (3)0.084 (6)0.050 (4)0.015 (4)0.004 (3)−0.030 (4)
C140.061 (5)0.066 (5)0.059 (5)−0.006 (4)0.019 (4)0.005 (4)
C150.098 (8)0.067 (5)0.070 (6)0.022 (5)0.045 (5)−0.003 (4)
C160.039 (4)0.049 (4)0.068 (5)0.013 (3)0.027 (3)−0.008 (3)
C170.026 (3)0.059 (4)0.047 (4)0.014 (3)0.015 (3)−0.004 (3)
C180.022 (3)0.037 (3)0.046 (3)−0.005 (2)0.009 (2)−0.008 (3)
C190.031 (3)0.049 (4)0.066 (5)−0.001 (3)0.027 (3)0.005 (3)
C200.032 (4)0.026 (3)0.050 (4)0.008 (2)0.014 (3)−0.003 (2)
C210.035 (3)0.037 (3)0.054 (4)0.005 (3)0.016 (3)0.010 (3)
C220.032 (3)0.021 (2)0.045 (3)0.001 (2)0.022 (3)−0.001 (2)
C230.052 (4)0.042 (3)0.034 (3)−0.021 (3)0.011 (3)0.000 (3)
C240.065 (5)0.047 (4)0.047 (4)−0.019 (3)0.026 (4)−0.004 (3)
C250.058 (4)0.025 (3)0.055 (4)−0.007 (3)0.033 (3)0.002 (3)
C260.040 (4)0.032 (3)0.064 (4)−0.009 (3)0.025 (3)−0.003 (3)
C270.031 (3)0.030 (3)0.047 (3)−0.009 (2)0.013 (3)−0.005 (3)
C290.023 (3)0.031 (3)0.039 (3)−0.006 (2)0.008 (2)0.001 (2)
C300.031 (3)0.066 (5)0.043 (4)−0.005 (3)0.012 (3)0.008 (3)
C310.034 (4)0.093 (6)0.050 (4)−0.012 (4)0.004 (3)0.025 (4)
C320.034 (4)0.050 (4)0.073 (5)−0.010 (3)−0.003 (3)0.030 (4)
C330.046 (5)0.043 (4)0.075 (5)0.011 (3)0.009 (4)0.011 (3)
C340.041 (4)0.043 (4)0.055 (4)0.008 (3)0.014 (3)0.003 (3)
Geometric parameters (Å, °) top
Sn1—C12.147 (5)C12—H120.9500
Sn1—C72.136 (6)C13—C141.527 (7)
Sn1—C132.117 (6)C13—C171.530 (7)
Sn1—O12.287 (4)C13—H131.0000
Sn1—O32.249 (4)C14—C151.569 (7)
Cl1—C191.660 (6)C14—H14A0.9900
Cl2—C211.657 (6)C14—H14B0.9900
F1—C191.319 (6)C15—C161.539 (7)
F2—C191.331 (6)C15—H15A0.9900
F3—C211.311 (6)C15—H15B0.9900
F4—C211.334 (6)C16—C171.541 (6)
O1—C181.246 (7)C16—H16A0.9900
O2—C181.249 (7)C16—H16B0.9900
O3—C201.257 (7)C17—H17A0.9900
O4—C201.235 (8)C17—H17B0.9900
N1—C291.508 (7)C18—C191.540 (9)
N1—C221.508 (7)C20—C211.506 (9)
N1—H1N10.8800C22—C271.512 (8)
N1—H1N20.8800C22—C231.534 (9)
C1—C21.391 (9)C22—H221.0000
C1—C2'1.394 (9)C23—C241.522 (9)
C1—C6'1.396 (9)C23—H23A0.9900
C1—C61.401 (9)C23—H23B0.9900
C2—C31.387 (9)C24—C251.524 (9)
C2—H20.9500C24—H24A0.9900
C3—C41.383 (9)C24—H24B0.9900
C3—H30.9500C25—C261.499 (10)
C4—C51.388 (9)C25—H25A0.9900
C4—H40.9500C25—H25B0.9900
C5—C61.393 (9)C26—C271.542 (9)
C5—H50.9500C26—H26A0.9900
C6—H60.9500C26—H26B0.9900
C2'—C3'1.386 (9)C27—H27A0.9900
C2'—H2'0.9500C27—H27B0.9900
C3'—C4'1.382 (9)C29—C301.510 (8)
C3'—H3'0.9500C29—C341.516 (9)
C4'—C5'1.387 (9)C29—H291.0000
C4'—H4'0.9500C30—C311.543 (10)
C5'—C6'1.393 (9)C30—H30A0.9900
C5'—H5'0.9500C30—H30B0.9900
C6'—H6'0.9500C31—C321.499 (12)
C7—C81.388 (9)C31—H31A0.9900
C7—C121.396 (8)C31—H31B0.9900
C8—C91.410 (9)C32—C331.523 (11)
C8—H80.9500C32—H32A0.9900
C9—C101.365 (10)C32—H32B0.9900
C9—H90.9500C33—C341.523 (10)
C10—C111.361 (9)C33—H33A0.9900
C10—H100.9500C33—H33B0.9900
C11—C121.396 (9)C34—H34A0.9900
C11—H110.9500C34—H34B0.9900
C1—Sn1—C7119.2 (2)C13—C17—C16105.1 (4)
C1—Sn1—C13121.7 (2)C13—C17—H17A110.7
C1—Sn1—O191.3 (2)C16—C17—H17A110.7
C1—Sn1—O390.9 (2)C13—C17—H17B110.7
C7—Sn1—C13118.9 (2)C16—C17—H17B110.7
C7—Sn1—O190.6 (2)H17A—C17—H17B108.8
C7—Sn1—O387.8 (2)O1—C18—O2129.2 (6)
C13—Sn1—O182.8 (3)O1—C18—C19114.5 (5)
C13—Sn1—O396.5 (3)O2—C18—C19116.3 (5)
O1—Sn1—O3177.7 (2)F1—C19—F2108.8 (5)
C18—O1—Sn1119.3 (4)F1—C19—C18111.3 (5)
C20—O3—Sn1117.0 (4)F2—C19—C18114.0 (5)
C29—N1—C22113.5 (4)F1—C19—Cl1106.0 (4)
C29—N1—H1N1108.9F2—C19—Cl1105.0 (5)
C29—N1—H1N1108.9C18—C19—Cl1111.2 (5)
C22—N1—H1N2108.9O4—C20—O3128.7 (6)
C22—N1—H1N2108.9O4—C20—C21116.7 (5)
H1N1—N1—H1N2107.7O3—C20—C21114.6 (6)
C2'—C1—C6'121 (3)F3—C21—F4107.1 (5)
C2—C1—C6115 (3)F3—C21—C20114.3 (5)
C2—C1—Sn1123.3 (19)F4—C21—C20112.3 (5)
C2'—C1—Sn1120.4 (18)F3—C21—Cl2103.7 (5)
C6'—C1—Sn1118 (2)F4—C21—Cl2110.4 (5)
C6—C1—Sn1122 (2)C20—C21—Cl2108.6 (4)
C3—C2—C1125 (3)N1—C22—C27110.2 (5)
C3—C2—H2117.5N1—C22—C23111.1 (5)
C1—C2—H2117.5C27—C22—C23110.1 (5)
C4—C3—C2116 (3)N1—C22—H22108.4
C4—C3—H3122.1C27—C22—H22108.4
C2—C3—H3122.1C23—C22—H22108.4
C3—C4—C5124 (3)C24—C23—C22109.0 (6)
C3—C4—H4117.8C24—C23—H23A109.9
C5—C4—H4117.8C22—C23—H23A109.9
C4—C5—C6116 (3)C24—C23—H23B109.9
C4—C5—H5122.0C22—C23—H23B109.9
C6—C5—H5122.0H23A—C23—H23B108.3
C5—C6—C1124 (3)C23—C24—C25111.7 (5)
C5—C6—H6118.0C23—C24—H24A109.3
C1—C6—H6118.0C25—C24—H24A109.3
C3'—C2'—C1118 (3)C23—C24—H24B109.3
C3'—C2'—H2'120.9C25—C24—H24B109.3
C1—C2'—H2'120.9H24A—C24—H24B107.9
C4'—C3'—C2'122 (3)C26—C25—C24111.5 (5)
C4'—C3'—H3'118.8C26—C25—H25A109.3
C2'—C3'—H3'118.8C24—C25—H25A109.3
C3'—C4'—C5'118 (3)C26—C25—H25B109.3
C3'—C4'—H4'121.2C24—C25—H25B109.3
C5'—C4'—H4'121.2H25A—C25—H25B108.0
C4'—C5'—C6'123 (3)C25—C26—C27112.1 (5)
C4'—C5'—H5'118.7C25—C26—H26A109.2
C6'—C5'—H5'118.7C27—C26—H26A109.2
C5'—C6'—C1118 (3)C25—C26—H26B109.2
C5'—C6'—H6'121.2C27—C26—H26B109.2
C1—C6'—H6'121.2H26A—C26—H26B107.9
C8—C7—C12118.7 (5)C22—C27—C26109.6 (5)
C8—C7—Sn1119.9 (4)C22—C27—H27A109.8
C12—C7—Sn1121.2 (4)C26—C27—H27A109.8
C7—C8—C9119.3 (6)C22—C27—H27B109.8
C7—C8—H8120.4C26—C27—H27B109.8
C9—C8—H8120.4H27A—C27—H27B108.2
C10—C9—C8120.8 (6)N1—C29—C30111.2 (5)
C10—C9—H9119.6N1—C29—C34110.6 (5)
C8—C9—H9119.6C30—C29—C34111.2 (5)
C11—C10—C9120.6 (6)N1—C29—H29107.9
C11—C10—H10119.7C30—C29—H29107.9
C9—C10—H10119.7C34—C29—H29107.9
C10—C11—C12119.7 (6)C29—C30—C31109.5 (6)
C10—C11—H11120.1C29—C30—H30A109.8
C12—C11—H11120.1C31—C30—H30A109.8
C7—C12—C11120.9 (6)C29—C30—H30B109.8
C7—C12—H12119.5C31—C30—H30B109.8
C11—C12—H12119.5H30A—C30—H30B108.2
C14—C13—C17105.1 (5)C32—C31—C30112.7 (7)
C14—C13—Sn1123.1 (5)C32—C31—H31A109.1
C17—C13—Sn1114.6 (4)C30—C31—H31A109.1
C14—C13—H13104.0C32—C31—H31B109.1
C17—C13—H13104.0C30—C31—H31B109.1
Sn1—C13—H13104.0H31A—C31—H31B107.8
C13—C14—C15105.2 (5)C31—C32—C33111.1 (6)
C13—C14—H14A110.7C31—C32—H32A109.4
C15—C14—H14A110.7C33—C32—H32A109.4
C13—C14—H14B110.7C31—C32—H32B109.4
C15—C14—H14B110.7C33—C32—H32B109.4
H14A—C14—H14B108.8H32A—C32—H32B108.0
C16—C15—C14105.8 (4)C32—C33—C34111.3 (6)
C16—C15—H15A110.6C32—C33—H33A109.4
C14—C15—H15A110.6C34—C33—H33A109.4
C16—C15—H15B110.6C32—C33—H33B109.4
C14—C15—H15B110.6C34—C33—H33B109.4
H15A—C15—H15B108.7H33A—C33—H33B108.0
C15—C16—C17107.4 (4)C29—C34—C33110.9 (6)
C15—C16—H16A110.2C29—C34—H34A109.5
C17—C16—H16A110.2C33—C34—H34A109.5
C15—C16—H16B110.2C29—C34—H34B109.5
C17—C16—H16B110.2C33—C34—H34B109.5
H16A—C16—H16B108.5H34A—C34—H34B108.1
C13—Sn1—O1—C18169.9 (5)C8—C9—C10—C11−1.3 (10)
C7—Sn1—O1—C1850.8 (5)C9—C10—C11—C120.6 (10)
C1—Sn1—O1—C18−68.4 (5)C8—C7—C12—C11−1.0 (9)
C13—Sn1—O3—C2060.0 (5)Sn1—C7—C12—C11173.6 (4)
C7—Sn1—O3—C20178.9 (5)C10—C11—C12—C70.6 (9)
C1—Sn1—O3—C20−62.0 (5)C7—Sn1—C13—C14−61.9 (8)
C13—Sn1—C1—C2−108.5 (13)C1—Sn1—C13—C14124.4 (6)
C7—Sn1—C1—C277.8 (13)O3—Sn1—C13—C1429.2 (7)
O3—Sn1—C1—C2−10.2 (13)O1—Sn1—C13—C14−148.5 (7)
O1—Sn1—C1—C2169.2 (13)C7—Sn1—C13—C17168.2 (5)
C13—Sn1—C1—C2'−121.7 (13)C1—Sn1—C13—C17−5.5 (7)
C7—Sn1—C1—C2'64.6 (13)O3—Sn1—C13—C17−100.6 (6)
O3—Sn1—C1—C2'−23.5 (13)O1—Sn1—C13—C1781.6 (6)
O1—Sn1—C1—C2'155.9 (13)C17—C13—C14—C15−32.5 (8)
C13—Sn1—C1—C6'56.8 (11)Sn1—C13—C14—C15−166.2 (6)
C7—Sn1—C1—C6'−116.9 (11)C13—C14—C15—C1619.2 (9)
O3—Sn1—C1—C6'155.1 (11)C14—C15—C16—C171.1 (9)
O1—Sn1—C1—C6'−25.5 (11)C14—C13—C17—C1633.2 (8)
C13—Sn1—C1—C670.4 (11)Sn1—C13—C17—C16171.5 (5)
C7—Sn1—C1—C6−103.4 (11)C15—C16—C17—C13−21.0 (8)
O3—Sn1—C1—C6168.6 (11)Sn1—O1—C18—O26.9 (9)
O1—Sn1—C1—C6−12.0 (11)Sn1—O1—C18—C19−173.6 (4)
C2'—C1—C2—C3−102 (18)O1—C18—C19—F1−56.4 (7)
C6'—C1—C2—C313.2 (19)O2—C18—C19—F1123.1 (6)
C6—C1—C2—C3−0.2 (3)O1—C18—C19—F2180.0 (5)
Sn1—C1—C2—C3178.7 (11)O2—C18—C19—F2−0.5 (8)
C1—C2—C3—C40.0 (3)O1—C18—C19—Cl161.5 (6)
C2—C3—C4—C50.0 (7)O2—C18—C19—Cl1−118.9 (5)
C3—C4—C5—C60.2 (9)Sn1—O3—C20—O41.0 (9)
C4—C5—C6—C1−0.5 (9)Sn1—O3—C20—C21179.9 (4)
C2—C1—C6—C50.5 (7)O4—C20—C21—F34.9 (8)
C2'—C1—C6—C513 (2)O3—C20—C21—F3−174.1 (6)
C6'—C1—C6—C5−102 (19)O4—C20—C21—F4127.2 (6)
Sn1—C1—C6—C5−178.4 (12)O3—C20—C21—F4−51.8 (7)
C2—C1—C2'—C3'70 (18)O4—C20—C21—Cl2−110.4 (6)
C6'—C1—C2'—C3'−0.2 (3)O3—C20—C21—Cl270.6 (6)
C6—C1—C2'—C3'−13 (2)C29—N1—C22—C2776.9 (6)
Sn1—C1—C2'—C3'178.3 (11)C29—N1—C22—C23−160.8 (5)
C1—C2'—C3'—C4'0.0 (3)N1—C22—C23—C24177.0 (5)
C2'—C3'—C4'—C5'0.0 (6)C27—C22—C23—C24−60.6 (7)
C3'—C4'—C5'—C6'0.2 (8)C22—C23—C24—C2557.4 (8)
C4'—C5'—C6'—C1−0.5 (8)C23—C24—C25—C26−54.2 (9)
C2—C1—C6'—C5'−12 (3)C24—C25—C26—C2753.0 (7)
C2'—C1—C6'—C5'0.5 (6)N1—C22—C27—C26−177.6 (5)
C6—C1—C6'—C5'72 (18)C23—C22—C27—C2659.5 (7)
Sn1—C1—C6'—C5'−178.1 (11)C25—C26—C27—C22−56.0 (7)
C13—Sn1—C7—C8−46.3 (6)C22—N1—C29—C30−151.5 (5)
C1—Sn1—C7—C8127.6 (4)C22—N1—C29—C3484.5 (6)
O3—Sn1—C7—C8−142.5 (5)N1—C29—C30—C31179.5 (6)
O1—Sn1—C7—C835.8 (5)C34—C29—C30—C31−56.8 (7)
C13—Sn1—C7—C12139.2 (5)C29—C30—C31—C3255.6 (8)
C1—Sn1—C7—C12−46.9 (5)C30—C31—C32—C33−54.3 (8)
O3—Sn1—C7—C1242.9 (4)C31—C32—C33—C3454.0 (9)
O1—Sn1—C7—C12−138.8 (4)N1—C29—C34—C33−177.8 (5)
C12—C7—C8—C90.3 (9)C30—C29—C34—C3358.1 (8)
Sn1—C7—C8—C9−174.4 (5)C32—C33—C34—C29−55.9 (8)
C7—C8—C9—C100.9 (10)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O20.881.882.758 (6)173
N1—H1N2···O4i0.881.932.804 (6)169
Symmetry codes: (i) −x+1, y+1/2, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Sn1—C12.147 (5)Sn1—O12.287 (4)
Sn1—C72.136 (6)Sn1—O32.249 (4)
Sn1—C132.117 (6)
C1—Sn1—C7119.2 (2)C7—Sn1—O190.6 (2)
C1—Sn1—C13121.7 (2)C7—Sn1—O387.8 (2)
C1—Sn1—O191.3 (2)C13—Sn1—O182.8 (3)
C1—Sn1—O390.9 (2)C13—Sn1—O396.5 (3)
C7—Sn1—C13118.9 (2)O1—Sn1—O3177.7 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O20.881.882.758 (6)173
N1—H1N2···O4i0.881.932.804 (6)169
Symmetry codes: (i) −x+1, y+1/2, −z+1.
Acknowledgements top

The authors thank the University of Malaya for funding this study (grant No. SF022155/2007 A) and also for the purchase of the diffractometer.

references
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