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Acta Cryst. (2008). E64, m726-m727    [ doi:10.1107/S1600536808011057 ]

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

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

Abstract top

In the title mixed-organyl stannate, (C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2], there are two cations and two anions in the asymmetric unit. Each five-coordinate Sn atom shows trans-C3SnO2 trigonal bipyramidal coordination. The four Sn-O distances are approximately equal in the two independent anions. Each ammonium cation serves as a hydrogen-bond donor to two stannates, the hydrogen-bonding interactions giving rise to linear hydrogen-bonded chains.

Comment top

Mixed alkyl/diaryltin compounds possess much more useful activity against plant pathogens than the symmetrical triorganotin homologs, particularly if one of the alkyl substituent is a cyclic unit. An earlier study reported the bis(chlorodifluroacetato)cyclohexyldiphenylstannate ion as its bis(1,2-diphenylphosphino)ethane-chelated silver salt (Teo et al., 2007).

Replacing the cation by the dicyclohexylammonium cation furnishes a similar stannate (I, Fig. 1 & Table 1). However, the cation engages in hydrogen bonding to give rise to a chain structure (Fig. 2 & Table 2). The dicyclohexylammonium counterion is particularly effective in stabilizing di(carboxylato)triorganostannates, as shown by previous studies (Ng & Hook, 1999; Ng & Kumar Das, 1992; 1993; Ng & Rae, 2000; Ng et al., 1990; 1991a, b,c; 1992; 2000).

Related literature top

For the structure of the bis(chlorodifluoroacetato)cyclohexyldiphenylstannate ion, see: Teo et al. (2007). For other dicyclohexylammonium di(carboxylato)triorganostannates, see: Ng & Hook (1999); Ng & Kumar Das (1992; 1993); Ng & Rae (2000); Ng et al. (1990; 1991a,b,c; 1992; 2000). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Cyclohexyldiphenyltin hydroxide (Teo et al., 2007) (0.38 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 1.00 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 cyclohexylammonium cation, C–C distances were restrained to 1.50±0.01 Å; the anisotropic displacement factors of the C atoms were restrained to be nearly isotropic. Those of the Cl and F atoms were similarly restrained.

There is minor disorder in the chlorodifluoromethyl groups; attempts to treat the group as two overlapping groups required numerous restraints but they did not lead to more meaningful outcome. The final difference Fourier map had a large peak at 1 Å from Sn1. The deepest hole is 1 Å from Cl4.

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 displacement plot of the two independent formula units of [(C6H11)2NH2)][Sn(C6H11)(C6H5)2(O2CClF2)2] (I). Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Supramolecular chain formation in (I) with hydrogen bonding interactions shown as dotted lines.
Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclohexyldiphenylstannate(IV) top
Crystal data top
(C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2]F000 = 3256
Mr = 796.29Dx = 1.452 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9887 reflections
a = 22.5469 (3) Åθ = 2.4–26.7º
b = 17.2799 (2) ŵ = 0.91 mm−1
c = 18.6963 (2) ÅT = 100 (2) K
β = 90.324 (1)ºBlock, colorless
V = 7284 (2) Å30.15 × 0.15 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEXII
diffractometer		16710 independent reflections
Radiation source: fine-focus sealed tube12483 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→29
Tmin = 0.788, Tmax = 0.915k = −22→22
93218 measured reflectionsl = −24→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.216  w = 1/[σ2(Fo2) + (0.1P)2 + 10.P]
where P = (Fo2 + 2Fc2)/3
S = 1.33(Δ/σ)max = 0.001
16710 reflectionsΔρmax = 2.24 e Å−3
829 parametersΔρmin = −2.03 e Å−3
240 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
(C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2]V = 7284 (2) Å3
Mr = 796.29Z = 8
Monoclinic, P21/cMo Kα
a = 22.5469 (3) ŵ = 0.91 mm−1
b = 17.2799 (2) ÅT = 100 (2) K
c = 18.6963 (2) Å0.15 × 0.15 × 0.10 mm
β = 90.324 (1)º
Data collection top
Bruker SMART APEXII
diffractometer		16710 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		12483 reflections with I > 2σ(I)
Tmin = 0.788, Tmax = 0.915Rint = 0.033
93218 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066240 restraints
wR(F2) = 0.216H-atom parameters constrained
S = 1.33Δρmax = 2.24 e Å−3
16710 reflectionsΔρmin = −2.03 e Å−3
829 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.284701 (16)0.222219 (19)0.298255 (19)0.03342 (12)
Sn20.775686 (16)0.22690 (2)0.496405 (19)0.03377 (12)
Cl10.13872 (17)0.4284 (2)0.4183 (2)0.1571 (17)
Cl20.44626 (10)0.03716 (11)0.19078 (10)0.0721 (5)
Cl30.9786 (2)0.3980 (2)0.49323 (19)0.1445 (15)
Cl40.5730 (3)0.0456 (3)0.4528 (2)0.214 (3)
F10.0785 (2)0.3704 (3)0.3231 (4)0.1029 (18)
F20.1537 (3)0.4350 (4)0.2914 (4)0.132 (3)
F30.4614 (3)0.0058 (3)0.3216 (3)0.0965 (17)
F40.3759 (2)−0.0238 (2)0.2785 (3)0.0901 (16)
F50.8999 (4)0.4183 (4)0.3985 (5)0.165 (3)
F60.9681 (3)0.3555 (5)0.3664 (3)0.127 (2)
F70.6311 (2)0.0371 (3)0.5612 (3)0.0911 (16)
F80.5625 (2)0.1215 (3)0.5607 (3)0.110 (2)
O10.22169 (17)0.3198 (2)0.3140 (2)0.0401 (9)
O20.14688 (19)0.2487 (3)0.3569 (2)0.0493 (10)
O30.3450 (2)0.1222 (2)0.2786 (2)0.0497 (10)
O40.4272 (2)0.1529 (3)0.3378 (3)0.0597 (12)
O50.85359 (17)0.3027 (2)0.4714 (2)0.0467 (10)
O60.9297 (2)0.2306 (3)0.4326 (3)0.0521 (11)
O70.69738 (17)0.1509 (2)0.5241 (2)0.0414 (9)
O80.6311 (2)0.2002 (3)0.4491 (3)0.0582 (12)
N10.0384 (2)0.1755 (3)0.3823 (3)0.0535 (14)
H1N10.06930.20560.37550.064*
H1N20.00800.20560.39210.064*
N20.5314 (2)0.2345 (3)0.3689 (3)0.0471 (12)
H2N10.55810.20980.39480.056*
H2N20.49980.20460.36660.056*
C10.2933 (4)0.2025 (4)0.4110 (3)0.0546 (17)
H10.33740.19930.41530.066*
C20.2818 (4)0.2676 (4)0.4589 (4)0.0542 (16)
H2A0.23950.28220.45450.065*
H2B0.30570.31240.44280.065*
C30.2955 (4)0.2525 (5)0.5361 (4)0.072 (2)
H3A0.33890.25700.54360.086*
H3B0.27630.29300.56540.086*
C40.2763 (4)0.1775 (5)0.5611 (4)0.075 (2)
H4A0.23300.17960.56910.091*
H4B0.29550.16730.60790.091*
C50.2888 (4)0.1125 (4)0.5141 (4)0.0620 (18)
H50.30320.06450.53170.074*
C60.2774 (3)0.1261 (4)0.4361 (4)0.0527 (15)
H6A0.30000.08730.40830.063*
H6B0.23470.11740.42620.063*
C70.2255 (3)0.1671 (3)0.2256 (3)0.0472 (14)
C80.1881 (3)0.2108 (4)0.1814 (3)0.0529 (16)
H80.18710.26550.18620.063*
C90.1523 (4)0.1746 (5)0.1306 (4)0.067 (2)
H90.12880.20510.09910.081*
C100.1504 (4)0.0959 (6)0.1256 (4)0.076 (2)
H100.12380.07180.09290.091*
C110.1864 (4)0.0523 (5)0.1670 (5)0.084 (3)
H110.1874−0.00220.16050.100*
C120.2225 (4)0.0868 (4)0.2198 (5)0.074 (2)
H120.24490.05520.25150.089*
C130.3433 (2)0.3020 (3)0.2476 (3)0.0400 (12)
C140.3381 (3)0.3809 (4)0.2582 (4)0.0538 (16)
H140.30860.40070.28930.065*
C150.3768 (4)0.4319 (4)0.2224 (5)0.075 (2)
H150.37380.48620.22930.090*
C160.4199 (4)0.4013 (6)0.1767 (5)0.082 (3)
H160.44630.43520.15270.098*
C170.4244 (3)0.3234 (5)0.1660 (4)0.066 (2)
H170.45360.30320.13470.079*
C180.3867 (3)0.2750 (4)0.2007 (3)0.0505 (15)
H180.39000.22090.19280.061*
C190.1706 (3)0.3086 (3)0.3373 (3)0.0381 (12)
C200.1339 (3)0.3826 (4)0.3392 (5)0.063 (2)
C210.3960 (3)0.1105 (3)0.3025 (3)0.0440 (13)
C220.4191 (3)0.0316 (4)0.2792 (4)0.0586 (17)
C230.7271 (2)0.3332 (3)0.5050 (3)0.0410 (13)
H230.68540.31960.51810.049*
C240.7247 (3)0.3753 (3)0.4336 (4)0.0488 (15)
H24A0.70640.34130.39710.059*
H24B0.76550.38760.41800.059*
C250.6888 (3)0.4500 (4)0.4394 (5)0.069 (2)
H25A0.68990.47810.39330.083*
H25B0.64700.43750.45020.083*
C260.7143 (3)0.5010 (4)0.4983 (6)0.078 (3)
H26A0.75480.51720.48500.093*
H26B0.68960.54810.50270.093*
C270.7164 (3)0.4598 (5)0.5694 (5)0.074 (2)
H27A0.73500.49390.60570.089*
H27B0.67550.44800.58520.089*
C280.7514 (3)0.3856 (4)0.5634 (4)0.0529 (16)
H28A0.75030.35790.60970.063*
H28B0.79330.39810.55300.063*
C290.7813 (2)0.1707 (3)0.3953 (3)0.0345 (11)
C300.7970 (3)0.2110 (3)0.3339 (3)0.0407 (12)
H300.80620.26450.33710.049*
C310.7994 (3)0.1744 (4)0.2682 (3)0.0517 (15)
H310.81030.20270.22680.062*
C320.7860 (3)0.0963 (4)0.2628 (4)0.0595 (19)
H320.78700.07130.21750.071*
C330.7714 (3)0.0555 (4)0.3226 (4)0.0556 (17)
H330.76350.00160.31920.067*
C340.7681 (3)0.0926 (3)0.3886 (3)0.0449 (13)
H340.75660.06400.42970.054*
C350.8191 (3)0.1774 (4)0.5875 (3)0.0477 (14)
C360.8771 (4)0.1882 (8)0.6018 (4)0.100 (4)
H360.89970.21850.56960.120*
C370.9055 (5)0.1574 (10)0.6611 (5)0.122 (5)
H370.94650.16680.66900.147*
C380.8746 (5)0.1139 (6)0.7075 (5)0.099 (4)
H380.89470.08630.74440.119*
C390.8136 (6)0.1093 (7)0.7016 (6)0.127 (5)
H390.79030.08740.73870.152*
C400.7869 (5)0.1383 (7)0.6382 (6)0.121 (5)
H400.74560.13060.63050.145*
C410.9035 (2)0.2914 (4)0.4443 (3)0.0406 (12)
C420.9356 (3)0.3665 (5)0.4250 (4)0.066 (2)
C430.6485 (3)0.1538 (3)0.4938 (3)0.0415 (13)
C440.6046 (3)0.0908 (4)0.5189 (4)0.0644 (19)
C450.0254 (3)0.1347 (5)0.3142 (5)0.078 (3)
H450.06090.10370.30000.093*
C46−0.0273 (5)0.0812 (7)0.3223 (6)0.123 (4)
H46A−0.06330.11230.33230.148*
H46B−0.02050.04620.36340.148*
C47−0.0372 (8)0.0343 (8)0.2561 (7)0.176 (6)
H47A−0.00110.00490.24350.211*
H47B−0.0704−0.00240.26250.211*
C48−0.0515 (5)0.0922 (7)0.2003 (6)0.107 (4)
H48−0.08790.09220.17440.128*
C49−0.0025 (5)0.1524 (7)0.1877 (5)0.117 (4)
H49A−0.01600.19080.15190.140*
H49B0.03340.12650.16900.140*
C500.0124 (4)0.1931 (6)0.2575 (4)0.095 (3)
H50A0.04730.22700.25080.114*
H50B−0.02150.22580.27230.114*
C510.0505 (3)0.1262 (3)0.4461 (4)0.0616 (19)
H510.01380.09600.45650.074*
C520.1002 (5)0.0695 (6)0.4357 (6)0.114 (4)
H52A0.09000.03360.39620.136*
H52B0.13680.09760.42260.136*
C530.1106 (6)0.0242 (7)0.5036 (7)0.132 (4)
H53A0.1447−0.01080.49610.158*
H53B0.0753−0.00840.51250.158*
C540.1224 (5)0.0714 (7)0.5684 (7)0.131 (5)
H54A0.16060.09910.56350.157*
H54B0.12480.03750.61100.157*
C550.0729 (4)0.1283 (5)0.5769 (5)0.090 (3)
H55A0.08200.16330.61740.108*
H55B0.03590.10020.58820.108*
C560.0636 (3)0.1759 (4)0.5097 (4)0.0640 (19)
H56A0.03020.21220.51710.077*
H56B0.09960.20690.50040.077*
C570.5143 (3)0.3081 (4)0.4094 (3)0.0517 (15)
H570.55020.34170.41330.062*
C580.4662 (3)0.3537 (4)0.3721 (3)0.0557 (16)
H58A0.43090.32040.36440.067*
H58B0.48040.37140.32490.067*
C590.4495 (3)0.4228 (4)0.4175 (3)0.0589 (17)
H59A0.48360.45890.41980.071*
H59B0.41600.45030.39440.071*
C600.4321 (3)0.4006 (4)0.4925 (3)0.0566 (17)
H60A0.42400.44800.52060.068*
H60B0.39530.36940.49090.068*
C610.4800 (4)0.3552 (5)0.5284 (4)0.082 (3)
H61A0.46660.33860.57630.098*
H61B0.51550.38820.53470.098*
C620.4961 (5)0.2842 (5)0.4841 (4)0.083 (3)
H62A0.52920.25610.50760.100*
H62B0.46160.24890.48130.100*
C630.5551 (3)0.2424 (4)0.2958 (4)0.0548 (16)
H630.52290.26380.26460.066*
C640.5719 (4)0.1637 (4)0.2675 (4)0.075 (2)
H64A0.53760.12830.27120.090*
H64B0.60470.14210.29690.090*
C650.5914 (4)0.1684 (6)0.1899 (4)0.088 (3)
H65A0.60190.11630.17220.105*
H65B0.55860.18880.15990.105*
C660.6437 (4)0.2207 (4)0.1852 (5)0.082 (3)
H66A0.65490.22680.13440.099*
H66B0.67760.19660.21060.099*
C670.6317 (6)0.2998 (5)0.2171 (5)0.106 (3)
H67A0.66910.32990.21800.128*
H67B0.60310.32770.18610.128*
C680.6073 (4)0.2957 (5)0.2917 (4)0.078 (2)
H68A0.63870.27730.32480.093*
H68B0.59520.34810.30710.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0336 (2)0.02637 (19)0.0404 (2)−0.00191 (13)0.00458 (15)−0.00010 (13)
Sn20.0254 (2)0.0388 (2)0.0371 (2)0.00561 (13)0.00435 (14)0.00539 (14)
Cl10.120 (3)0.137 (3)0.214 (4)0.010 (2)0.019 (2)−0.125 (3)
Cl20.0926 (15)0.0621 (10)0.0618 (10)0.0017 (10)0.0293 (10)−0.0192 (8)
Cl30.196 (4)0.114 (2)0.124 (2)−0.087 (2)−0.012 (2)−0.0278 (19)
Cl40.353 (6)0.173 (3)0.114 (2)−0.182 (4)−0.079 (3)0.026 (2)
F10.037 (2)0.085 (3)0.187 (5)0.011 (2)−0.017 (3)−0.013 (3)
F20.098 (4)0.092 (4)0.206 (6)0.040 (3)0.046 (4)0.073 (4)
F30.094 (4)0.103 (4)0.093 (3)0.061 (3)0.010 (3)0.027 (3)
F40.093 (4)0.041 (2)0.137 (4)−0.001 (2)0.036 (3)0.014 (2)
F50.165 (6)0.114 (5)0.214 (7)0.028 (4)−0.001 (5)0.105 (5)
F60.128 (5)0.169 (5)0.087 (3)−0.056 (4)0.055 (3)0.013 (4)
F70.077 (3)0.059 (3)0.137 (4)0.008 (2)0.021 (3)0.050 (3)
F80.087 (3)0.099 (4)0.146 (4)0.038 (3)0.083 (3)0.060 (3)
O10.035 (2)0.0314 (18)0.054 (2)0.0011 (15)0.0059 (17)0.0039 (16)
O20.040 (2)0.046 (2)0.062 (3)−0.0093 (19)0.007 (2)−0.004 (2)
O30.051 (3)0.038 (2)0.060 (3)0.0083 (19)−0.004 (2)−0.0127 (18)
O40.046 (3)0.080 (3)0.054 (3)0.004 (2)0.000 (2)−0.014 (2)
O50.028 (2)0.047 (2)0.066 (3)0.0013 (17)0.0140 (18)−0.003 (2)
O60.036 (2)0.060 (3)0.061 (3)0.0089 (19)0.009 (2)−0.005 (2)
O70.033 (2)0.045 (2)0.046 (2)0.0036 (17)0.0068 (17)0.0152 (17)
O80.038 (2)0.043 (2)0.094 (4)−0.0035 (19)−0.018 (2)0.022 (2)
N10.029 (3)0.045 (3)0.086 (4)−0.008 (2)0.011 (3)−0.025 (3)
N20.030 (3)0.057 (3)0.054 (3)0.017 (2)−0.006 (2)−0.014 (2)
C10.080 (5)0.039 (3)0.044 (3)0.003 (3)0.010 (3)0.006 (3)
C20.061 (4)0.051 (4)0.050 (4)−0.005 (3)−0.002 (3)−0.001 (3)
C30.088 (6)0.075 (5)0.053 (4)−0.017 (5)0.004 (4)0.003 (4)
C40.092 (6)0.083 (6)0.051 (4)−0.017 (5)−0.014 (4)0.012 (4)
C50.071 (5)0.056 (4)0.059 (4)0.001 (4)0.004 (4)0.022 (3)
C60.061 (4)0.040 (3)0.057 (4)−0.004 (3)−0.001 (3)0.010 (3)
C70.047 (4)0.038 (3)0.056 (3)−0.010 (3)−0.002 (3)0.003 (3)
C80.061 (4)0.055 (4)0.043 (3)−0.001 (3)0.004 (3)−0.003 (3)
C90.057 (4)0.084 (6)0.062 (4)−0.013 (4)−0.004 (3)0.014 (4)
C100.076 (6)0.091 (6)0.060 (4)−0.016 (5)−0.010 (4)−0.019 (4)
C110.093 (7)0.062 (5)0.096 (6)−0.031 (5)−0.013 (5)−0.016 (4)
C120.095 (6)0.040 (4)0.086 (5)−0.009 (4)−0.036 (5)−0.006 (3)
C130.030 (3)0.047 (3)0.042 (3)−0.010 (2)−0.005 (2)0.006 (2)
C140.046 (4)0.045 (3)0.071 (4)−0.018 (3)−0.007 (3)0.010 (3)
C150.063 (5)0.046 (4)0.114 (7)−0.025 (4)−0.020 (5)0.024 (4)
C160.040 (4)0.114 (8)0.091 (6)−0.025 (5)0.005 (4)0.035 (5)
C170.046 (4)0.091 (6)0.061 (4)−0.007 (4)0.006 (3)0.017 (4)
C180.036 (3)0.071 (4)0.044 (3)−0.006 (3)0.002 (3)0.004 (3)
C190.035 (3)0.037 (3)0.043 (3)−0.004 (2)−0.004 (2)−0.002 (2)
C200.031 (3)0.048 (4)0.110 (6)0.004 (3)0.015 (4)0.004 (4)
C210.051 (4)0.043 (3)0.038 (3)0.009 (3)0.009 (3)−0.002 (2)
C220.061 (4)0.049 (4)0.066 (4)0.016 (3)0.011 (3)0.005 (3)
C230.024 (3)0.038 (3)0.061 (4)0.001 (2)0.010 (2)−0.006 (2)
C240.038 (3)0.036 (3)0.072 (4)0.008 (2)−0.006 (3)−0.002 (3)
C250.046 (4)0.033 (3)0.128 (7)0.012 (3)−0.017 (4)−0.002 (4)
C260.041 (4)0.038 (3)0.154 (9)0.009 (3)−0.001 (5)−0.023 (4)
C270.049 (4)0.066 (5)0.107 (7)−0.001 (4)0.019 (4)−0.038 (5)
C280.039 (3)0.057 (4)0.063 (4)−0.002 (3)0.011 (3)−0.016 (3)
C290.029 (3)0.034 (2)0.041 (3)0.010 (2)0.005 (2)0.007 (2)
C300.037 (3)0.045 (3)0.040 (3)0.007 (2)0.005 (2)0.010 (2)
C310.051 (4)0.064 (4)0.040 (3)0.013 (3)0.000 (3)0.006 (3)
C320.062 (4)0.072 (5)0.045 (3)0.031 (4)−0.013 (3)−0.009 (3)
C330.057 (4)0.040 (3)0.070 (4)0.012 (3)−0.011 (3)−0.007 (3)
C340.046 (3)0.036 (3)0.052 (3)0.010 (2)0.000 (3)0.006 (2)
C350.044 (3)0.061 (4)0.038 (3)0.016 (3)−0.003 (2)0.000 (3)
C360.049 (5)0.212 (12)0.039 (4)−0.003 (6)−0.009 (3)0.029 (6)
C370.057 (6)0.260 (17)0.050 (5)0.027 (8)−0.013 (4)0.008 (7)
C380.109 (8)0.114 (8)0.075 (6)0.036 (7)−0.051 (6)0.002 (5)
C390.122 (10)0.144 (10)0.114 (9)−0.011 (8)−0.047 (7)0.084 (8)
C400.094 (8)0.143 (10)0.125 (9)−0.033 (7)−0.054 (7)0.093 (8)
C410.027 (3)0.051 (3)0.044 (3)0.002 (2)0.003 (2)0.008 (2)
C420.043 (4)0.068 (5)0.086 (5)0.007 (3)0.020 (4)0.032 (4)
C430.031 (3)0.033 (3)0.060 (3)0.000 (2)0.011 (3)0.004 (2)
C440.056 (4)0.051 (4)0.086 (5)−0.013 (3)0.004 (4)0.009 (4)
C450.043 (4)0.084 (5)0.106 (6)−0.011 (4)0.012 (4)−0.057 (5)
C460.105 (7)0.127 (7)0.137 (7)−0.061 (6)0.009 (6)−0.066 (6)
C470.172 (10)0.166 (9)0.189 (10)−0.078 (8)−0.017 (8)−0.065 (8)
C480.073 (5)0.140 (7)0.108 (6)−0.040 (5)−0.016 (5)−0.056 (6)
C490.089 (6)0.176 (8)0.086 (6)−0.026 (6)0.010 (5)−0.069 (6)
C500.064 (5)0.148 (7)0.073 (5)−0.018 (5)0.005 (4)−0.058 (5)
C510.039 (3)0.036 (3)0.110 (5)0.002 (3)0.009 (3)0.007 (3)
C520.096 (7)0.084 (6)0.161 (8)0.044 (5)0.010 (6)−0.007 (6)
C530.108 (7)0.100 (7)0.187 (9)0.051 (6)0.015 (7)0.054 (7)
C540.107 (7)0.124 (8)0.162 (9)0.035 (6)−0.008 (7)0.060 (7)
C550.061 (5)0.093 (6)0.116 (6)−0.001 (4)−0.007 (4)0.057 (5)
C560.053 (4)0.051 (4)0.089 (5)−0.003 (3)−0.007 (4)0.021 (3)
C570.045 (3)0.053 (3)0.057 (3)0.017 (3)0.001 (3)−0.014 (3)
C580.057 (4)0.057 (4)0.053 (3)0.018 (3)−0.002 (3)−0.005 (3)
C590.062 (4)0.052 (4)0.064 (4)0.017 (3)0.008 (3)−0.001 (3)
C600.063 (4)0.045 (3)0.061 (4)0.012 (3)0.013 (3)−0.013 (3)
C610.102 (6)0.081 (5)0.062 (4)0.036 (5)0.002 (4)−0.017 (4)
C620.108 (6)0.080 (5)0.062 (4)0.056 (5)−0.005 (4)−0.014 (4)
C630.048 (4)0.059 (4)0.057 (4)0.019 (3)−0.001 (3)−0.010 (3)
C640.069 (5)0.069 (4)0.087 (5)−0.004 (4)0.025 (4)−0.031 (4)
C650.076 (5)0.100 (6)0.088 (5)0.018 (5)0.005 (4)−0.040 (5)
C660.097 (6)0.075 (5)0.076 (5)0.022 (4)0.033 (5)−0.003 (4)
C670.137 (8)0.078 (5)0.106 (6)0.011 (6)0.043 (6)0.002 (5)
C680.104 (6)0.054 (4)0.076 (5)0.010 (4)0.025 (4)−0.009 (4)
Geometric parameters (Å, °) top
Sn1—C12.144 (6)C28—H28A0.9900
Sn1—C72.125 (6)C28—H28B0.9900
Sn1—C132.134 (6)C29—C341.388 (8)
Sn1—O12.226 (4)C29—C301.389 (7)
Sn1—O32.231 (4)C30—C311.382 (9)
Sn2—C232.145 (5)C30—H300.9500
Sn2—C292.130 (5)C31—C321.386 (10)
Sn2—C352.138 (6)C31—H310.9500
Sn2—O52.243 (4)C32—C331.363 (10)
Sn2—O72.263 (4)C32—H320.9500
Cl1—C201.682 (9)C33—C341.394 (9)
Cl2—C221.769 (7)C33—H330.9500
Cl3—C421.689 (10)C34—H340.9500
Cl4—C441.623 (9)C35—C361.347 (10)
F1—C201.299 (8)C35—C401.374 (12)
F2—C201.350 (9)C36—C371.383 (12)
F3—C221.315 (9)C36—H360.9500
F4—C221.365 (9)C37—C381.345 (16)
F5—C421.298 (9)C37—H370.9500
F6—C421.336 (9)C38—C391.382 (16)
F7—C441.355 (9)C38—H380.9500
F8—C441.341 (9)C39—C401.420 (12)
O1—C191.248 (7)C39—H390.9500
O2—C191.223 (7)C40—H400.9500
O3—C211.247 (8)C41—C421.531 (9)
O4—C211.209 (8)C43—C441.546 (9)
O5—C411.251 (7)C45—C501.491 (9)
O6—C411.224 (7)C45—C461.514 (8)
O7—C431.236 (7)C45—H451.0000
O8—C431.222 (7)C46—C471.495 (9)
N1—C511.490 (9)C46—H46A0.9900
N1—C451.482 (9)C46—H46B0.9900
N1—H1N10.8800C47—C481.479 (10)
N1—H1N20.8800C47—H47A0.9900
N2—C631.476 (9)C47—H47B0.9900
N2—C571.531 (8)C48—C491.538 (9)
N2—H2N10.8800C48—H480.9500
N2—H2N20.8800C49—C501.517 (8)
C1—C61.447 (8)C49—H49A0.9900
C1—C21.461 (9)C49—H49B0.9900
C1—H11.0000C50—H50A0.9900
C2—C31.499 (10)C50—H50B0.9900
C2—H2A0.9900C51—C561.494 (8)
C2—H2B0.9900C51—C521.501 (8)
C3—C41.446 (11)C51—H511.0000
C3—H3A0.9900C52—C531.508 (9)
C3—H3B0.9900C52—H52A0.9900
C4—C51.454 (11)C52—H52B0.9900
C4—H4A0.9900C53—C541.483 (9)
C4—H4B0.9900C53—H53A0.9900
C5—C61.497 (9)C53—H53B0.9900
C5—H50.9500C54—C551.496 (9)
C6—H6A0.9900C54—H54A0.9900
C6—H6B0.9900C54—H54B0.9900
C7—C121.394 (9)C55—C561.515 (8)
C7—C81.398 (9)C55—H55A0.9900
C8—C91.392 (10)C55—H55B0.9900
C8—H80.9500C56—H56A0.9900
C9—C101.364 (12)C56—H56B0.9900
C9—H90.9500C57—C581.507 (7)
C10—C111.348 (13)C57—C621.516 (8)
C10—H100.9500C57—H571.0000
C11—C121.407 (11)C58—C591.513 (7)
C11—H110.9500C58—H58A0.9900
C12—H120.9500C58—H58B0.9900
C13—C141.382 (9)C59—C601.509 (7)
C13—C181.398 (9)C59—H59A0.9900
C14—C151.411 (9)C59—H59B0.9900
C14—H140.9500C60—C611.492 (8)
C15—C161.401 (13)C60—H60A0.9900
C15—H150.9500C60—H60B0.9900
C16—C171.364 (13)C61—C621.524 (7)
C16—H160.9500C61—H61A0.9900
C17—C181.360 (10)C61—H61B0.9900
C17—H170.9500C62—H62A0.9900
C18—H180.9500C62—H62B0.9900
C19—C201.524 (9)C63—C681.497 (8)
C21—C221.524 (9)C63—C641.510 (7)
C23—C281.520 (8)C63—H631.0000
C23—C241.521 (9)C64—C651.520 (8)
C23—H231.0000C64—H64A0.9900
C24—C251.527 (8)C64—H64B0.9900
C24—H24A0.9900C65—C661.488 (9)
C24—H24B0.9900C65—H65A0.9900
C25—C261.518 (11)C65—H65B0.9900
C25—H25A0.9900C66—C671.517 (8)
C25—H25B0.9900C66—H66A0.9900
C26—C271.508 (13)C66—H66B0.9900
C26—H26A0.9900C67—C681.503 (8)
C26—H26B0.9900C67—H67A0.9900
C27—C281.511 (10)C67—H67B0.9900
C27—H27A0.9900C68—H68A0.9900
C27—H27B0.9900C68—H68B0.9900
C7—Sn1—C13113.2 (2)C36—C35—C40116.6 (7)
C7—Sn1—C1127.6 (3)C36—C35—Sn2122.9 (6)
C13—Sn1—C1119.1 (3)C40—C35—Sn2120.3 (5)
C7—Sn1—O191.4 (2)C35—C36—C37123.4 (10)
C13—Sn1—O188.04 (19)C35—C36—H36118.3
C1—Sn1—O192.6 (2)C37—C36—H36118.3
C7—Sn1—O385.9 (2)C38—C37—C36119.6 (10)
C13—Sn1—O392.7 (2)C38—C37—H37120.2
C1—Sn1—O389.3 (2)C36—C37—H37120.2
O1—Sn1—O3177.3 (2)C37—C38—C39119.9 (8)
C29—Sn2—C35119.7 (2)C37—C38—H38120.0
C29—Sn2—C23119.3 (2)C39—C38—H38120.0
C35—Sn2—C23121.0 (2)C38—C39—C40117.7 (11)
C29—Sn2—O591.75 (18)C38—C39—H39121.2
C35—Sn2—O592.6 (2)C40—C39—H39121.2
C23—Sn2—O585.22 (18)C35—C40—C39121.7 (10)
C29—Sn2—O789.36 (18)C35—C40—H40119.1
C35—Sn2—O786.5 (2)C39—C40—H40119.1
C23—Sn2—O794.60 (17)O6—C41—O5129.9 (6)
O5—Sn2—O7178.8 (2)O6—C41—C42117.2 (5)
C19—O1—Sn1121.2 (3)O5—C41—C42112.9 (5)
C21—O3—Sn1128.9 (4)F5—C42—F697.3 (7)
C41—O5—Sn2134.4 (4)F5—C42—C41112.4 (7)
C43—O7—Sn2124.4 (3)F6—C42—C41109.6 (7)
C51—N1—H1N1108.1F5—C42—Cl3114.7 (8)
C45—N1—H1N1108.1F6—C42—Cl3110.5 (6)
C51—N1—H1N2108.1C41—C42—Cl3111.4 (5)
C45—N1—H1N2108.1O8—C43—O7128.4 (5)
H1N1—N1—H1N2107.3O8—C43—C44117.8 (6)
C45—N1—C51116.8 (6)O7—C43—C44113.7 (5)
C57—N2—C63118.3 (5)F8—C44—F7104.0 (6)
C63—N2—H2N1107.7F8—C44—C43110.8 (6)
C57—N2—H2N1107.7F7—C44—C43112.2 (6)
C63—N2—H2N2107.7F8—C44—Cl4108.9 (7)
C57—N2—H2N2107.7F7—C44—Cl4107.7 (6)
H2N1—N2—H2N2107.1C43—C44—Cl4112.7 (6)
C6—C1—C2117.4 (6)N1—C45—C50109.0 (6)
C6—C1—Sn1116.3 (5)N1—C45—C46110.8 (7)
C2—C1—Sn1117.7 (4)C50—C45—C46109.4 (9)
C6—C1—H199.9N1—C45—H45109.2
C2—C1—H199.9C50—C45—H45109.2
Sn1—C1—H199.9C46—C45—H45109.2
C1—C2—C3114.8 (6)C45—C46—C47111.2 (9)
C1—C2—H2A108.6C45—C46—H46A109.4
C3—C2—H2A108.6C47—C46—H46A109.4
C1—C2—H2B108.6C45—C46—H46B109.4
C3—C2—H2B108.6C47—C46—H46B109.4
H2A—C2—H2B107.5H46A—C46—H46B108.0
C4—C3—C2114.0 (7)C48—C47—C46104.4 (11)
C4—C3—H3A108.8C48—C47—H47A110.9
C2—C3—H3A108.8C46—C47—H47A110.9
C4—C3—H3B108.8C48—C47—H47B110.9
C2—C3—H3B108.8C46—C47—H47B110.9
H3A—C3—H3B107.6H47A—C47—H47B108.9
C3—C4—C5115.9 (7)C49—C48—C47114.3 (10)
C3—C4—H4A108.3C49—C48—H48122.9
C5—C4—H4A108.3C47—C48—H48122.9
C3—C4—H4B108.3C48—C49—C50109.7 (8)
C5—C4—H4B108.3C48—C49—H49A109.7
H4A—C4—H4B107.4C50—C49—H49A109.7
C4—C5—C6115.8 (6)C48—C49—H49B109.7
C4—C5—H5122.1C50—C49—H49B109.7
C6—C5—H5122.1H49A—C49—H49B108.2
C1—C6—C5114.6 (6)C45—C50—C49109.8 (9)
C1—C6—H6A108.6C45—C50—H50A109.7
C5—C6—H6A108.6C49—C50—H50A109.7
C1—C6—H6B108.6C45—C50—H50B109.7
C5—C6—H6B108.6C49—C50—H50B109.7
H6A—C6—H6B107.6H50A—C50—H50B108.2
C12—C7—C8117.6 (6)N1—C51—C56110.1 (5)
C12—C7—Sn1121.8 (5)N1—C51—C52113.7 (7)
C8—C7—Sn1120.7 (5)C56—C51—C52109.6 (7)
C9—C8—C7120.4 (7)N1—C51—H51107.7
C9—C8—H8119.8C56—C51—H51107.7
C7—C8—H8119.8C52—C51—H51107.7
C10—C9—C8120.8 (8)C53—C52—C51110.0 (8)
C10—C9—H9119.6C53—C52—H52A109.7
C8—C9—H9119.6C51—C52—H52A109.7
C11—C10—C9120.0 (8)C53—C52—H52B109.7
C11—C10—H10120.0C51—C52—H52B109.7
C9—C10—H10120.0H52A—C52—H52B108.2
C10—C11—C12120.6 (8)C52—C53—C54115.4 (10)
C10—C11—H11119.7C52—C53—H53A108.4
C12—C11—H11119.7C54—C53—H53A108.4
C7—C12—C11120.3 (8)C52—C53—H53B108.4
C7—C12—H12119.9C54—C53—H53B108.4
C11—C12—H12119.9H53A—C53—H53B107.5
C14—C13—C18118.6 (6)C53—C54—C55108.5 (10)
C14—C13—Sn1121.4 (5)C53—C54—H54A110.0
C18—C13—Sn1120.0 (5)C55—C54—H54A110.0
C13—C14—C15119.7 (7)C53—C54—H54B110.0
C13—C14—H14120.2C55—C54—H54B110.0
C15—C14—H14120.2H54A—C54—H54B108.4
C16—C15—C14119.1 (8)C54—C55—C56111.7 (8)
C16—C15—H15120.4C54—C55—H55A109.3
C14—C15—H15120.4C56—C55—H55A109.3
C17—C16—C15120.9 (7)C54—C55—H55B109.3
C17—C16—H16119.5C56—C55—H55B109.3
C15—C16—H16119.5H55A—C55—H55B107.9
C18—C17—C16119.3 (8)C51—C56—C55111.9 (7)
C18—C17—H17120.4C51—C56—H56A109.2
C16—C17—H17120.4C55—C56—H56A109.2
C17—C18—C13122.4 (7)C51—C56—H56B109.2
C17—C18—H18118.8C55—C56—H56B109.2
C13—C18—H18118.8H56A—C56—H56B107.9
O2—C19—O1130.0 (6)C58—C57—C62111.8 (6)
O2—C19—C20117.7 (5)C58—C57—N2112.9 (5)
O1—C19—C20112.3 (5)C62—C57—N2107.4 (5)
F1—C20—F2106.1 (7)C58—C57—H57108.2
F1—C20—C19112.3 (6)C62—C57—H57108.2
F2—C20—C19111.4 (6)N2—C57—H57108.2
F1—C20—Cl1109.7 (6)C57—C58—C59109.5 (5)
F2—C20—Cl1104.3 (6)C57—C58—H58A109.8
C19—C20—Cl1112.5 (6)C59—C58—H58A109.8
O4—C21—O3129.0 (6)C57—C58—H58B109.8
O4—C21—C22119.9 (6)C59—C58—H58B109.8
O3—C21—C22111.0 (6)H58A—C58—H58B108.2
F3—C22—F4106.4 (6)C60—C59—C58112.8 (5)
F3—C22—C21112.3 (6)C60—C59—H59A109.0
F4—C22—C21112.7 (6)C58—C59—H59A109.0
F3—C22—Cl2109.1 (5)C60—C59—H59B109.0
F4—C22—Cl2106.3 (5)C58—C59—H59B109.0
C21—C22—Cl2109.8 (5)H59A—C59—H59B107.8
C28—C23—C24110.9 (5)C61—C60—C59111.1 (6)
C28—C23—Sn2112.4 (4)C61—C60—H60A109.4
C24—C23—Sn2111.1 (4)C59—C60—H60A109.4
C28—C23—H23107.4C61—C60—H60B109.4
C24—C23—H23107.4C59—C60—H60B109.4
Sn2—C23—H23107.4H60A—C60—H60B108.0
C23—C24—C25111.0 (6)C60—C61—C62110.7 (6)
C23—C24—H24A109.4C60—C61—H61A109.5
C25—C24—H24A109.4C62—C61—H61A109.5
C23—C24—H24B109.4C60—C61—H61B109.5
C25—C24—H24B109.4C62—C61—H61B109.5
H24A—C24—H24B108.0H61A—C61—H61B108.1
C26—C25—C24110.1 (6)C57—C62—C61110.3 (6)
C26—C25—H25A109.6C57—C62—H62A109.6
C24—C25—H25A109.6C61—C62—H62A109.6
C26—C25—H25B109.6C57—C62—H62B109.6
C24—C25—H25B109.6C61—C62—H62B109.6
H25A—C25—H25B108.1H62A—C62—H62B108.1
C27—C26—C25112.0 (7)N2—C63—C68113.2 (6)
C27—C26—H26A109.2N2—C63—C64109.6 (6)
C25—C26—H26A109.2C68—C63—C64109.6 (6)
C27—C26—H26B109.2N2—C63—H63108.1
C25—C26—H26B109.2C68—C63—H63108.1
H26A—C26—H26B107.9C64—C63—H63108.1
C28—C27—C26110.4 (6)C63—C64—C65111.2 (7)
C28—C27—H27A109.6C63—C64—H64A109.4
C26—C27—H27A109.6C65—C64—H64A109.4
C28—C27—H27B109.6C63—C64—H64B109.4
C26—C27—H27B109.6C65—C64—H64B109.4
H27A—C27—H27B108.1H64A—C64—H64B108.0
C27—C28—C23111.8 (6)C66—C65—C64108.8 (7)
C27—C28—H28A109.2C66—C65—H65A109.9
C23—C28—H28A109.2C64—C65—H65A109.9
C27—C28—H28B109.2C66—C65—H65B109.9
C23—C28—H28B109.2C64—C65—H65B109.9
H28A—C28—H28B107.9H65A—C65—H65B108.3
C34—C29—C30117.9 (5)C65—C66—C67112.3 (8)
C34—C29—Sn2120.6 (4)C65—C66—H66A109.1
C30—C29—Sn2121.5 (4)C67—C66—H66A109.1
C31—C30—C29121.1 (6)C65—C66—H66B109.1
C31—C30—H30119.5C67—C66—H66B109.1
C29—C30—H30119.5H66A—C66—H66B107.9
C32—C31—C30120.1 (6)C68—C67—C66112.9 (8)
C32—C31—H31120.0C68—C67—H67A109.0
C30—C31—H31120.0C66—C67—H67A109.0
C33—C32—C31119.8 (6)C68—C67—H67B109.0
C33—C32—H32120.1C66—C67—H67B109.0
C31—C32—H32120.1H67A—C67—H67B107.8
C32—C33—C34120.2 (6)C63—C68—C67111.7 (8)
C32—C33—H33119.9C63—C68—H68A109.3
C34—C33—H33119.9C67—C68—H68A109.3
C33—C34—C29121.0 (6)C63—C68—H68B109.3
C33—C34—H34119.5C67—C68—H68B109.3
C29—C34—H34119.5H68A—C68—H68B107.9
C7—Sn1—O1—C1959.3 (4)C24—C23—C28—C2755.6 (7)
C13—Sn1—O1—C19172.4 (4)Sn2—C23—C28—C27−179.4 (5)
C1—Sn1—O1—C19−68.5 (5)C35—Sn2—C29—C3450.7 (5)
C7—Sn1—O3—C21177.4 (6)C23—Sn2—C29—C34−129.8 (4)
C13—Sn1—O3—C2164.3 (5)O5—Sn2—C29—C34144.7 (5)
C1—Sn1—O3—C21−54.8 (6)O7—Sn2—C29—C34−34.9 (4)
C29—Sn2—O5—C41−44.5 (6)C35—Sn2—C29—C30−130.6 (5)
C35—Sn2—O5—C4175.4 (6)C23—Sn2—C29—C3048.9 (5)
C23—Sn2—O5—C41−163.7 (6)O5—Sn2—C29—C30−36.6 (5)
C29—Sn2—O7—C43−66.8 (5)O7—Sn2—C29—C30143.8 (4)
C35—Sn2—O7—C43173.4 (5)C34—C29—C30—C31−0.1 (8)
C23—Sn2—O7—C4352.5 (5)Sn2—C29—C30—C31−178.8 (5)
C7—Sn1—C1—C627.9 (7)C29—C30—C31—C320.1 (10)
C13—Sn1—C1—C6−149.2 (5)C30—C31—C32—C33−1.1 (10)
O1—Sn1—C1—C6121.7 (6)C31—C32—C33—C342.1 (10)
O3—Sn1—C1—C6−56.4 (6)C32—C33—C34—C29−2.1 (10)
C7—Sn1—C1—C2−119.0 (6)C30—C29—C34—C331.0 (9)
C13—Sn1—C1—C263.9 (7)Sn2—C29—C34—C33179.8 (5)
O1—Sn1—C1—C2−25.3 (6)C29—Sn2—C35—C3682.8 (8)
O3—Sn1—C1—C2156.7 (6)C23—Sn2—C35—C36−96.7 (8)
C6—C1—C2—C340.4 (10)O5—Sn2—C35—C36−10.7 (8)
Sn1—C1—C2—C3−173.1 (6)O7—Sn2—C35—C36170.1 (8)
C1—C2—C3—C4−42.7 (11)C29—Sn2—C35—C40−103.3 (8)
C2—C3—C4—C544.4 (12)C23—Sn2—C35—C4077.3 (9)
C3—C4—C5—C6−42.6 (11)O5—Sn2—C35—C40163.3 (8)
C2—C1—C6—C5−37.9 (10)O7—Sn2—C35—C40−16.0 (8)
Sn1—C1—C6—C5175.1 (5)C40—C35—C36—C374.9 (18)
C4—C5—C6—C138.4 (10)Sn2—C35—C36—C37179.1 (10)
C13—Sn1—C7—C12123.5 (7)C35—C36—C37—C380(2)
C1—Sn1—C7—C12−53.6 (8)C36—C37—C38—C39−9(2)
O1—Sn1—C7—C12−148.0 (7)C37—C38—C39—C4012 (2)
O3—Sn1—C7—C1232.3 (7)C36—C35—C40—C39−1.4 (18)
C13—Sn1—C7—C8−56.3 (6)Sn2—C35—C40—C39−175.7 (11)
C1—Sn1—C7—C8126.5 (5)C38—C39—C40—C35−7(2)
O1—Sn1—C7—C832.2 (6)Sn2—O5—C41—O6−13.2 (11)
O3—Sn1—C7—C8−147.5 (6)Sn2—O5—C41—C42168.1 (5)
C12—C7—C8—C9−4.1 (11)O6—C41—C42—F5141.8 (8)
Sn1—C7—C8—C9175.8 (5)O5—C41—C42—F5−39.4 (10)
C7—C8—C9—C103.7 (12)O6—C41—C42—F634.8 (9)
C8—C9—C10—C11−4.2 (14)O5—C41—C42—F6−146.4 (6)
C9—C10—C11—C125.2 (15)O6—C41—C42—Cl3−87.8 (7)
C8—C7—C12—C115.1 (13)O5—C41—C42—Cl391.0 (6)
Sn1—C7—C12—C11−174.8 (7)Sn2—O7—C43—O8−6.7 (9)
C10—C11—C12—C7−5.8 (15)Sn2—O7—C43—C44175.1 (4)
C7—Sn1—C13—C14110.5 (5)O8—C43—C44—F8−72.2 (9)
C1—Sn1—C13—C14−72.0 (6)O7—C43—C44—F8106.1 (7)
O1—Sn1—C13—C1419.8 (5)O8—C43—C44—F7172.0 (6)
O3—Sn1—C13—C14−162.7 (5)O7—C43—C44—F7−9.7 (9)
C7—Sn1—C13—C18−67.3 (5)O8—C43—C44—Cl450.2 (8)
C1—Sn1—C13—C18110.2 (5)O7—C43—C44—Cl4−131.5 (6)
O1—Sn1—C13—C18−158.0 (5)C51—N1—C45—C50178.0 (6)
O3—Sn1—C13—C1819.5 (5)C51—N1—C45—C4657.6 (10)
C18—C13—C14—C15−0.7 (10)N1—C45—C46—C47−174.6 (11)
Sn1—C13—C14—C15−178.6 (5)C50—C45—C46—C4765.2 (13)
C13—C14—C15—C160.1 (11)C45—C46—C47—C48−63.4 (16)
C14—C15—C16—C170.5 (13)C46—C47—C48—C4959.7 (15)
C15—C16—C17—C18−0.3 (13)C47—C48—C49—C50−56.2 (14)
C16—C17—C18—C13−0.4 (11)N1—C45—C50—C49−178.7 (7)
C14—C13—C18—C170.9 (10)C46—C45—C50—C49−57.3 (10)
Sn1—C13—C18—C17178.8 (5)C48—C49—C50—C4552.3 (12)
Sn1—O1—C19—O22.6 (8)C45—N1—C51—C56179.2 (6)
Sn1—O1—C19—C20−176.3 (4)C45—N1—C51—C5255.8 (9)
O2—C19—C20—F1−35.6 (10)N1—C51—C52—C53178.2 (9)
O1—C19—C20—F1143.4 (7)C56—C51—C52—C5354.5 (12)
O2—C19—C20—F2−154.5 (7)C51—C52—C53—C54−55.5 (15)
O1—C19—C20—F224.5 (9)C52—C53—C54—C5554.2 (15)
O2—C19—C20—Cl188.8 (6)C53—C54—C55—C56−53.9 (13)
O1—C19—C20—Cl1−92.2 (6)N1—C51—C56—C55176.8 (6)
Sn1—O3—C21—O4−6.3 (10)C52—C51—C56—C55−57.4 (9)
Sn1—O3—C21—C22175.9 (4)C54—C55—C56—C5158.0 (11)
O4—C21—C22—F324.2 (9)C63—N2—C57—C5860.7 (8)
O3—C21—C22—F3−157.7 (6)C63—N2—C57—C62−175.7 (6)
O4—C21—C22—F4144.4 (7)C62—C57—C58—C5955.6 (8)
O3—C21—C22—F4−37.6 (8)N2—C57—C58—C59176.8 (6)
O4—C21—C22—Cl2−97.4 (7)C57—C58—C59—C60−54.8 (9)
O3—C21—C22—Cl280.7 (6)C58—C59—C60—C6155.7 (9)
C29—Sn2—C23—C28−150.3 (4)C59—C60—C61—C62−55.7 (10)
C35—Sn2—C23—C2829.1 (5)C58—C57—C62—C61−57.2 (10)
O5—Sn2—C23—C28−61.0 (4)N2—C57—C62—C61178.4 (7)
O7—Sn2—C23—C28117.8 (4)C60—C61—C62—C5756.7 (11)
C29—Sn2—C23—C24−25.4 (5)C57—N2—C63—C6854.4 (8)
C35—Sn2—C23—C24154.0 (4)C57—N2—C63—C64177.1 (6)
O5—Sn2—C23—C2463.9 (4)N2—C63—C64—C65175.0 (6)
O7—Sn2—C23—C24−117.3 (4)C68—C63—C64—C65−60.3 (9)
C28—C23—C24—C25−55.6 (7)C63—C64—C65—C6660.1 (10)
Sn2—C23—C24—C25178.7 (4)C64—C65—C66—C67−55.0 (11)
C23—C24—C25—C2655.9 (8)C65—C66—C67—C6851.9 (13)
C24—C25—C26—C27−56.7 (9)N2—C63—C68—C67177.7 (7)
C25—C26—C27—C2856.4 (8)C64—C63—C68—C6755.0 (10)
C26—C27—C28—C23−55.5 (8)C66—C67—C68—C63−51.3 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1n1···O20.881.932.797 (7)166
N1—H1n2···O6i0.881.972.798 (7)155
N2—H2n2···O40.881.942.798 (7)165
N2—H2n1···O80.881.942.759 (6)155
Symmetry codes: (i) x−1, y, z.
Table 1
Selected geometric parameters (Å, °) top
Sn1—C12.144 (6)Sn2—C232.145 (5)
Sn1—C72.125 (6)Sn2—C292.130 (5)
Sn1—C132.134 (6)Sn2—C352.138 (6)
Sn1—O12.226 (4)Sn2—O52.243 (4)
Sn1—O32.231 (4)Sn2—O72.263 (4)
O1—Sn1—O3177.3 (2)C41—O5—Sn2134.4 (4)
O5—Sn2—O7178.8 (2)C43—O7—Sn2124.4 (3)
C19—O1—Sn1121.2 (3)C45—N1—C51116.8 (6)
C21—O3—Sn1128.9 (4)C57—N2—C63118.3 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1n1···O20.881.932.797 (7)166
N1—H1n2···O6i0.881.972.798 (7)155
N2—H2n2···O40.881.942.798 (7)165
N2—H2n1···O80.881.942.759 (6)155
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Ng, S. W. & Hook, J. M. (1999). Main Group Met. Chem. 22, 163–174.

Ng, S. W. & Kumar Das, V. G. (1992). J. Crystallogr. Spectrosc. Res. 22, 507–509.

Ng, S. W. & Kumar Das, V. G. (1993). J. Crystallogr. Spectrosc. Res. 23, 925–928.

Ng, S. W., Kumar Das, V. G., Hossain, M. B., Goerlitz, F. & van der Helm, D. (1990). J. Organomet. Chem. 390, 19–28.

Ng, S. W., Kumar Das, V. G., Skelton, B. W. & White, A. H. (1992). J. Organomet. Chem. 430, 139–148.

Ng, S. W., Kumar Das, V. G. & Tiekink, E. R. T. (1991a). J. Organomet. Chem. 403, 111–117.

Ng, S. W., Kumar Das, V. G. & Tiekink, E. R. T. (1991b). J. Organomet. Chem. 411, 121–129.

Ng, S. W., Kumar Das, V. G., Xiao, G., van der Helm, D., Holecek, J. & Lycka, A. (1991c). Heteroat. Chem. 2, 495–498.

Ng, S. W. & Rae, A. D. (2000). Z. Kristallogr. 215, 100–204.

Ng, S. W., Shanmuga Sundara Raj, S., Fun, H.-K., Razak, I. A. & Hook, J. M. (2000). Acta Cryst. C56, 966–968.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Teo, Y. Y., Lo, K. M. & Ng, S. W. (2007). Acta Cryst. E63, m1365–m1367.

Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23.

Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116.

Westrip, S. P. (2008). publCIF. In preparation.