metal-organic compounds
Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclohexyldiphenylstannate(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title mixed-organyl stannate, (C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2], there are two cations and two anions in the 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.
Related literature
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
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536808011057/tk2258sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011057/tk2258Isup2.hkl
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.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the
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.
Data collection: APEX2 (Bruker, 2007); cell
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).(C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2] | F(000) = 3256 |
Mr = 796.29 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9887 reflections |
a = 22.5469 (3) Å | θ = 2.4–26.7° |
b = 17.2799 (2) Å | µ = 0.91 mm−1 |
c = 18.6963 (2) Å | T = 100 K |
β = 90.324 (1)° | Block, colorless |
V = 7284 (2) Å3 | 0.15 × 0.15 × 0.10 mm |
Z = 8 |
Bruker SMART APEXII diffractometer | 16710 independent reflections |
Radiation source: fine-focus sealed tube | 12483 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→29 |
Tmin = 0.788, Tmax = 0.915 | k = −22→22 |
93218 measured reflections | l = −24→24 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.33 | w = 1/[σ2(Fo2) + (0.1P)2 + 10.P] where P = (Fo2 + 2Fc2)/3 |
16710 reflections | (Δ/σ)max = 0.001 |
829 parameters | Δρmax = 2.24 e Å−3 |
240 restraints | Δρmin = −2.03 e Å−3 |
(C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2] | V = 7284 (2) Å3 |
Mr = 796.29 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.5469 (3) Å | µ = 0.91 mm−1 |
b = 17.2799 (2) Å | T = 100 K |
c = 18.6963 (2) Å | 0.15 × 0.15 × 0.10 mm |
β = 90.324 (1)° |
Bruker SMART APEXII diffractometer | 16710 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 12483 reflections with I > 2σ(I) |
Tmin = 0.788, Tmax = 0.915 | Rint = 0.033 |
93218 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 240 restraints |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.33 | Δρmax = 2.24 e Å−3 |
16710 reflections | Δρmin = −2.03 e Å−3 |
829 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.284701 (16) | 0.222219 (19) | 0.298255 (19) | 0.03342 (12) | |
Sn2 | 0.775686 (16) | 0.22690 (2) | 0.496405 (19) | 0.03377 (12) | |
Cl1 | 0.13872 (17) | 0.4284 (2) | 0.4183 (2) | 0.1571 (17) | |
Cl2 | 0.44626 (10) | 0.03716 (11) | 0.19078 (10) | 0.0721 (5) | |
Cl3 | 0.9786 (2) | 0.3980 (2) | 0.49323 (19) | 0.1445 (15) | |
Cl4 | 0.5730 (3) | 0.0456 (3) | 0.4528 (2) | 0.214 (3) | |
F1 | 0.0785 (2) | 0.3704 (3) | 0.3231 (4) | 0.1029 (18) | |
F2 | 0.1537 (3) | 0.4350 (4) | 0.2914 (4) | 0.132 (3) | |
F3 | 0.4614 (3) | 0.0058 (3) | 0.3216 (3) | 0.0965 (17) | |
F4 | 0.3759 (2) | −0.0238 (2) | 0.2785 (3) | 0.0901 (16) | |
F5 | 0.8999 (4) | 0.4183 (4) | 0.3985 (5) | 0.165 (3) | |
F6 | 0.9681 (3) | 0.3555 (5) | 0.3664 (3) | 0.127 (2) | |
F7 | 0.6311 (2) | 0.0371 (3) | 0.5612 (3) | 0.0911 (16) | |
F8 | 0.5625 (2) | 0.1215 (3) | 0.5607 (3) | 0.110 (2) | |
O1 | 0.22169 (17) | 0.3198 (2) | 0.3140 (2) | 0.0401 (9) | |
O2 | 0.14688 (19) | 0.2487 (3) | 0.3569 (2) | 0.0493 (10) | |
O3 | 0.3450 (2) | 0.1222 (2) | 0.2786 (2) | 0.0497 (10) | |
O4 | 0.4272 (2) | 0.1529 (3) | 0.3378 (3) | 0.0597 (12) | |
O5 | 0.85359 (17) | 0.3027 (2) | 0.4714 (2) | 0.0467 (10) | |
O6 | 0.9297 (2) | 0.2306 (3) | 0.4326 (3) | 0.0521 (11) | |
O7 | 0.69738 (17) | 0.1509 (2) | 0.5241 (2) | 0.0414 (9) | |
O8 | 0.6311 (2) | 0.2002 (3) | 0.4491 (3) | 0.0582 (12) | |
N1 | 0.0384 (2) | 0.1755 (3) | 0.3823 (3) | 0.0535 (14) | |
H1N1 | 0.0693 | 0.2056 | 0.3755 | 0.064* | |
H1N2 | 0.0080 | 0.2056 | 0.3921 | 0.064* | |
N2 | 0.5314 (2) | 0.2345 (3) | 0.3689 (3) | 0.0471 (12) | |
H2N1 | 0.5581 | 0.2098 | 0.3948 | 0.056* | |
H2N2 | 0.4998 | 0.2046 | 0.3666 | 0.056* | |
C1 | 0.2933 (4) | 0.2025 (4) | 0.4110 (3) | 0.0546 (17) | |
H1 | 0.3374 | 0.1993 | 0.4153 | 0.066* | |
C2 | 0.2818 (4) | 0.2676 (4) | 0.4589 (4) | 0.0542 (16) | |
H2A | 0.2395 | 0.2822 | 0.4545 | 0.065* | |
H2B | 0.3057 | 0.3124 | 0.4428 | 0.065* | |
C3 | 0.2955 (4) | 0.2525 (5) | 0.5361 (4) | 0.072 (2) | |
H3A | 0.3389 | 0.2570 | 0.5436 | 0.086* | |
H3B | 0.2763 | 0.2930 | 0.5654 | 0.086* | |
C4 | 0.2763 (4) | 0.1775 (5) | 0.5611 (4) | 0.075 (2) | |
H4A | 0.2330 | 0.1796 | 0.5691 | 0.091* | |
H4B | 0.2955 | 0.1673 | 0.6079 | 0.091* | |
C5 | 0.2888 (4) | 0.1125 (4) | 0.5141 (4) | 0.0620 (18) | |
H5 | 0.3032 | 0.0645 | 0.5317 | 0.074* | |
C6 | 0.2774 (3) | 0.1261 (4) | 0.4361 (4) | 0.0527 (15) | |
H6A | 0.3000 | 0.0873 | 0.4083 | 0.063* | |
H6B | 0.2347 | 0.1174 | 0.4262 | 0.063* | |
C7 | 0.2255 (3) | 0.1671 (3) | 0.2256 (3) | 0.0472 (14) | |
C8 | 0.1881 (3) | 0.2108 (4) | 0.1814 (3) | 0.0529 (16) | |
H8 | 0.1871 | 0.2655 | 0.1862 | 0.063* | |
C9 | 0.1523 (4) | 0.1746 (5) | 0.1306 (4) | 0.067 (2) | |
H9 | 0.1288 | 0.2051 | 0.0991 | 0.081* | |
C10 | 0.1504 (4) | 0.0959 (6) | 0.1256 (4) | 0.076 (2) | |
H10 | 0.1238 | 0.0718 | 0.0929 | 0.091* | |
C11 | 0.1864 (4) | 0.0523 (5) | 0.1670 (5) | 0.084 (3) | |
H11 | 0.1874 | −0.0022 | 0.1605 | 0.100* | |
C12 | 0.2225 (4) | 0.0868 (4) | 0.2198 (5) | 0.074 (2) | |
H12 | 0.2449 | 0.0552 | 0.2515 | 0.089* | |
C13 | 0.3433 (2) | 0.3020 (3) | 0.2476 (3) | 0.0400 (12) | |
C14 | 0.3381 (3) | 0.3809 (4) | 0.2582 (4) | 0.0538 (16) | |
H14 | 0.3086 | 0.4007 | 0.2893 | 0.065* | |
C15 | 0.3768 (4) | 0.4319 (4) | 0.2224 (5) | 0.075 (2) | |
H15 | 0.3738 | 0.4862 | 0.2293 | 0.090* | |
C16 | 0.4199 (4) | 0.4013 (6) | 0.1767 (5) | 0.082 (3) | |
H16 | 0.4463 | 0.4352 | 0.1527 | 0.098* | |
C17 | 0.4244 (3) | 0.3234 (5) | 0.1660 (4) | 0.066 (2) | |
H17 | 0.4536 | 0.3032 | 0.1347 | 0.079* | |
C18 | 0.3867 (3) | 0.2750 (4) | 0.2007 (3) | 0.0505 (15) | |
H18 | 0.3900 | 0.2209 | 0.1928 | 0.061* | |
C19 | 0.1706 (3) | 0.3086 (3) | 0.3373 (3) | 0.0381 (12) | |
C20 | 0.1339 (3) | 0.3826 (4) | 0.3392 (5) | 0.063 (2) | |
C21 | 0.3960 (3) | 0.1105 (3) | 0.3025 (3) | 0.0440 (13) | |
C22 | 0.4191 (3) | 0.0316 (4) | 0.2792 (4) | 0.0586 (17) | |
C23 | 0.7271 (2) | 0.3332 (3) | 0.5050 (3) | 0.0410 (13) | |
H23 | 0.6854 | 0.3196 | 0.5181 | 0.049* | |
C24 | 0.7247 (3) | 0.3753 (3) | 0.4336 (4) | 0.0488 (15) | |
H24A | 0.7064 | 0.3413 | 0.3971 | 0.059* | |
H24B | 0.7655 | 0.3876 | 0.4180 | 0.059* | |
C25 | 0.6888 (3) | 0.4500 (4) | 0.4394 (5) | 0.069 (2) | |
H25A | 0.6899 | 0.4781 | 0.3933 | 0.083* | |
H25B | 0.6470 | 0.4375 | 0.4502 | 0.083* | |
C26 | 0.7143 (3) | 0.5010 (4) | 0.4983 (6) | 0.078 (3) | |
H26A | 0.7548 | 0.5172 | 0.4850 | 0.093* | |
H26B | 0.6896 | 0.5481 | 0.5027 | 0.093* | |
C27 | 0.7164 (3) | 0.4598 (5) | 0.5694 (5) | 0.074 (2) | |
H27A | 0.7350 | 0.4939 | 0.6057 | 0.089* | |
H27B | 0.6755 | 0.4480 | 0.5852 | 0.089* | |
C28 | 0.7514 (3) | 0.3856 (4) | 0.5634 (4) | 0.0529 (16) | |
H28A | 0.7503 | 0.3579 | 0.6097 | 0.063* | |
H28B | 0.7933 | 0.3981 | 0.5530 | 0.063* | |
C29 | 0.7813 (2) | 0.1707 (3) | 0.3953 (3) | 0.0345 (11) | |
C30 | 0.7970 (3) | 0.2110 (3) | 0.3339 (3) | 0.0407 (12) | |
H30 | 0.8062 | 0.2645 | 0.3371 | 0.049* | |
C31 | 0.7994 (3) | 0.1744 (4) | 0.2682 (3) | 0.0517 (15) | |
H31 | 0.8103 | 0.2027 | 0.2268 | 0.062* | |
C32 | 0.7860 (3) | 0.0963 (4) | 0.2628 (4) | 0.0595 (19) | |
H32 | 0.7870 | 0.0713 | 0.2175 | 0.071* | |
C33 | 0.7714 (3) | 0.0555 (4) | 0.3226 (4) | 0.0556 (17) | |
H33 | 0.7635 | 0.0016 | 0.3192 | 0.067* | |
C34 | 0.7681 (3) | 0.0926 (3) | 0.3886 (3) | 0.0449 (13) | |
H34 | 0.7566 | 0.0640 | 0.4297 | 0.054* | |
C35 | 0.8191 (3) | 0.1774 (4) | 0.5875 (3) | 0.0477 (14) | |
C36 | 0.8771 (4) | 0.1882 (8) | 0.6018 (4) | 0.100 (4) | |
H36 | 0.8997 | 0.2185 | 0.5696 | 0.120* | |
C37 | 0.9055 (5) | 0.1574 (10) | 0.6611 (5) | 0.122 (5) | |
H37 | 0.9465 | 0.1668 | 0.6690 | 0.147* | |
C38 | 0.8746 (5) | 0.1139 (6) | 0.7075 (5) | 0.099 (4) | |
H38 | 0.8947 | 0.0863 | 0.7444 | 0.119* | |
C39 | 0.8136 (6) | 0.1093 (7) | 0.7016 (6) | 0.127 (5) | |
H39 | 0.7903 | 0.0874 | 0.7387 | 0.152* | |
C40 | 0.7869 (5) | 0.1383 (7) | 0.6382 (6) | 0.121 (5) | |
H40 | 0.7456 | 0.1306 | 0.6305 | 0.145* | |
C41 | 0.9035 (2) | 0.2914 (4) | 0.4443 (3) | 0.0406 (12) | |
C42 | 0.9356 (3) | 0.3665 (5) | 0.4250 (4) | 0.066 (2) | |
C43 | 0.6485 (3) | 0.1538 (3) | 0.4938 (3) | 0.0415 (13) | |
C44 | 0.6046 (3) | 0.0908 (4) | 0.5189 (4) | 0.0644 (19) | |
C45 | 0.0254 (3) | 0.1347 (5) | 0.3142 (5) | 0.078 (3) | |
H45 | 0.0609 | 0.1037 | 0.3000 | 0.093* | |
C46 | −0.0273 (5) | 0.0812 (7) | 0.3223 (6) | 0.123 (4) | |
H46A | −0.0633 | 0.1123 | 0.3323 | 0.148* | |
H46B | −0.0205 | 0.0462 | 0.3634 | 0.148* | |
C47 | −0.0372 (8) | 0.0343 (8) | 0.2561 (7) | 0.176 (6) | |
H47A | −0.0011 | 0.0049 | 0.2435 | 0.211* | |
H47B | −0.0704 | −0.0024 | 0.2625 | 0.211* | |
C48 | −0.0515 (5) | 0.0922 (7) | 0.2003 (6) | 0.107 (4) | |
H48 | −0.0879 | 0.0922 | 0.1744 | 0.128* | |
C49 | −0.0025 (5) | 0.1524 (7) | 0.1877 (5) | 0.117 (4) | |
H49A | −0.0160 | 0.1908 | 0.1519 | 0.140* | |
H49B | 0.0334 | 0.1265 | 0.1690 | 0.140* | |
C50 | 0.0124 (4) | 0.1931 (6) | 0.2575 (4) | 0.095 (3) | |
H50A | 0.0473 | 0.2270 | 0.2508 | 0.114* | |
H50B | −0.0215 | 0.2258 | 0.2723 | 0.114* | |
C51 | 0.0505 (3) | 0.1262 (3) | 0.4461 (4) | 0.0616 (19) | |
H51 | 0.0138 | 0.0960 | 0.4565 | 0.074* | |
C52 | 0.1002 (5) | 0.0695 (6) | 0.4357 (6) | 0.114 (4) | |
H52A | 0.0900 | 0.0336 | 0.3962 | 0.136* | |
H52B | 0.1368 | 0.0976 | 0.4226 | 0.136* | |
C53 | 0.1106 (6) | 0.0242 (7) | 0.5036 (7) | 0.132 (4) | |
H53A | 0.1447 | −0.0108 | 0.4961 | 0.158* | |
H53B | 0.0753 | −0.0084 | 0.5125 | 0.158* | |
C54 | 0.1224 (5) | 0.0714 (7) | 0.5684 (7) | 0.131 (5) | |
H54A | 0.1606 | 0.0991 | 0.5635 | 0.157* | |
H54B | 0.1248 | 0.0375 | 0.6110 | 0.157* | |
C55 | 0.0729 (4) | 0.1283 (5) | 0.5769 (5) | 0.090 (3) | |
H55A | 0.0820 | 0.1633 | 0.6174 | 0.108* | |
H55B | 0.0359 | 0.1002 | 0.5882 | 0.108* | |
C56 | 0.0636 (3) | 0.1759 (4) | 0.5097 (4) | 0.0640 (19) | |
H56A | 0.0302 | 0.2122 | 0.5171 | 0.077* | |
H56B | 0.0996 | 0.2069 | 0.5004 | 0.077* | |
C57 | 0.5143 (3) | 0.3081 (4) | 0.4094 (3) | 0.0517 (15) | |
H57 | 0.5502 | 0.3417 | 0.4133 | 0.062* | |
C58 | 0.4662 (3) | 0.3537 (4) | 0.3721 (3) | 0.0557 (16) | |
H58A | 0.4309 | 0.3204 | 0.3644 | 0.067* | |
H58B | 0.4804 | 0.3714 | 0.3249 | 0.067* | |
C59 | 0.4495 (3) | 0.4228 (4) | 0.4175 (3) | 0.0589 (17) | |
H59A | 0.4836 | 0.4589 | 0.4198 | 0.071* | |
H59B | 0.4160 | 0.4503 | 0.3944 | 0.071* | |
C60 | 0.4321 (3) | 0.4006 (4) | 0.4925 (3) | 0.0566 (17) | |
H60A | 0.4240 | 0.4480 | 0.5206 | 0.068* | |
H60B | 0.3953 | 0.3694 | 0.4909 | 0.068* | |
C61 | 0.4800 (4) | 0.3552 (5) | 0.5284 (4) | 0.082 (3) | |
H61A | 0.4666 | 0.3386 | 0.5763 | 0.098* | |
H61B | 0.5155 | 0.3882 | 0.5347 | 0.098* | |
C62 | 0.4961 (5) | 0.2842 (5) | 0.4841 (4) | 0.083 (3) | |
H62A | 0.5292 | 0.2561 | 0.5076 | 0.100* | |
H62B | 0.4616 | 0.2489 | 0.4813 | 0.100* | |
C63 | 0.5551 (3) | 0.2424 (4) | 0.2958 (4) | 0.0548 (16) | |
H63 | 0.5229 | 0.2638 | 0.2646 | 0.066* | |
C64 | 0.5719 (4) | 0.1637 (4) | 0.2675 (4) | 0.075 (2) | |
H64A | 0.5376 | 0.1283 | 0.2712 | 0.090* | |
H64B | 0.6047 | 0.1421 | 0.2969 | 0.090* | |
C65 | 0.5914 (4) | 0.1684 (6) | 0.1899 (4) | 0.088 (3) | |
H65A | 0.6019 | 0.1163 | 0.1722 | 0.105* | |
H65B | 0.5586 | 0.1888 | 0.1599 | 0.105* | |
C66 | 0.6437 (4) | 0.2207 (4) | 0.1852 (5) | 0.082 (3) | |
H66A | 0.6549 | 0.2268 | 0.1344 | 0.099* | |
H66B | 0.6776 | 0.1966 | 0.2106 | 0.099* | |
C67 | 0.6317 (6) | 0.2998 (5) | 0.2171 (5) | 0.106 (3) | |
H67A | 0.6691 | 0.3299 | 0.2180 | 0.128* | |
H67B | 0.6031 | 0.3277 | 0.1861 | 0.128* | |
C68 | 0.6073 (4) | 0.2957 (5) | 0.2917 (4) | 0.078 (2) | |
H68A | 0.6387 | 0.2773 | 0.3248 | 0.093* | |
H68B | 0.5952 | 0.3481 | 0.3071 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0336 (2) | 0.02637 (19) | 0.0404 (2) | −0.00191 (13) | 0.00458 (15) | −0.00010 (13) |
Sn2 | 0.0254 (2) | 0.0388 (2) | 0.0371 (2) | 0.00561 (13) | 0.00435 (14) | 0.00539 (14) |
Cl1 | 0.120 (3) | 0.137 (3) | 0.214 (4) | 0.010 (2) | 0.019 (2) | −0.125 (3) |
Cl2 | 0.0926 (15) | 0.0621 (10) | 0.0618 (10) | 0.0017 (10) | 0.0293 (10) | −0.0192 (8) |
Cl3 | 0.196 (4) | 0.114 (2) | 0.124 (2) | −0.087 (2) | −0.012 (2) | −0.0278 (19) |
Cl4 | 0.353 (6) | 0.173 (3) | 0.114 (2) | −0.182 (4) | −0.079 (3) | 0.026 (2) |
F1 | 0.037 (2) | 0.085 (3) | 0.187 (5) | 0.011 (2) | −0.017 (3) | −0.013 (3) |
F2 | 0.098 (4) | 0.092 (4) | 0.206 (6) | 0.040 (3) | 0.046 (4) | 0.073 (4) |
F3 | 0.094 (4) | 0.103 (4) | 0.093 (3) | 0.061 (3) | 0.010 (3) | 0.027 (3) |
F4 | 0.093 (4) | 0.041 (2) | 0.137 (4) | −0.001 (2) | 0.036 (3) | 0.014 (2) |
F5 | 0.165 (6) | 0.114 (5) | 0.214 (7) | 0.028 (4) | −0.001 (5) | 0.105 (5) |
F6 | 0.128 (5) | 0.169 (5) | 0.087 (3) | −0.056 (4) | 0.055 (3) | 0.013 (4) |
F7 | 0.077 (3) | 0.059 (3) | 0.137 (4) | 0.008 (2) | 0.021 (3) | 0.050 (3) |
F8 | 0.087 (3) | 0.099 (4) | 0.146 (4) | 0.038 (3) | 0.083 (3) | 0.060 (3) |
O1 | 0.035 (2) | 0.0314 (18) | 0.054 (2) | 0.0011 (15) | 0.0059 (17) | 0.0039 (16) |
O2 | 0.040 (2) | 0.046 (2) | 0.062 (3) | −0.0093 (19) | 0.007 (2) | −0.004 (2) |
O3 | 0.051 (3) | 0.038 (2) | 0.060 (3) | 0.0083 (19) | −0.004 (2) | −0.0127 (18) |
O4 | 0.046 (3) | 0.080 (3) | 0.054 (3) | 0.004 (2) | 0.000 (2) | −0.014 (2) |
O5 | 0.028 (2) | 0.047 (2) | 0.066 (3) | 0.0013 (17) | 0.0140 (18) | −0.003 (2) |
O6 | 0.036 (2) | 0.060 (3) | 0.061 (3) | 0.0089 (19) | 0.009 (2) | −0.005 (2) |
O7 | 0.033 (2) | 0.045 (2) | 0.046 (2) | 0.0036 (17) | 0.0068 (17) | 0.0152 (17) |
O8 | 0.038 (2) | 0.043 (2) | 0.094 (4) | −0.0035 (19) | −0.018 (2) | 0.022 (2) |
N1 | 0.029 (3) | 0.045 (3) | 0.086 (4) | −0.008 (2) | 0.011 (3) | −0.025 (3) |
N2 | 0.030 (3) | 0.057 (3) | 0.054 (3) | 0.017 (2) | −0.006 (2) | −0.014 (2) |
C1 | 0.080 (5) | 0.039 (3) | 0.044 (3) | 0.003 (3) | 0.010 (3) | 0.006 (3) |
C2 | 0.061 (4) | 0.051 (4) | 0.050 (4) | −0.005 (3) | −0.002 (3) | −0.001 (3) |
C3 | 0.088 (6) | 0.075 (5) | 0.053 (4) | −0.017 (5) | 0.004 (4) | 0.003 (4) |
C4 | 0.092 (6) | 0.083 (6) | 0.051 (4) | −0.017 (5) | −0.014 (4) | 0.012 (4) |
C5 | 0.071 (5) | 0.056 (4) | 0.059 (4) | 0.001 (4) | 0.004 (4) | 0.022 (3) |
C6 | 0.061 (4) | 0.040 (3) | 0.057 (4) | −0.004 (3) | −0.001 (3) | 0.010 (3) |
C7 | 0.047 (4) | 0.038 (3) | 0.056 (3) | −0.010 (3) | −0.002 (3) | 0.003 (3) |
C8 | 0.061 (4) | 0.055 (4) | 0.043 (3) | −0.001 (3) | 0.004 (3) | −0.003 (3) |
C9 | 0.057 (4) | 0.084 (6) | 0.062 (4) | −0.013 (4) | −0.004 (3) | 0.014 (4) |
C10 | 0.076 (6) | 0.091 (6) | 0.060 (4) | −0.016 (5) | −0.010 (4) | −0.019 (4) |
C11 | 0.093 (7) | 0.062 (5) | 0.096 (6) | −0.031 (5) | −0.013 (5) | −0.016 (4) |
C12 | 0.095 (6) | 0.040 (4) | 0.086 (5) | −0.009 (4) | −0.036 (5) | −0.006 (3) |
C13 | 0.030 (3) | 0.047 (3) | 0.042 (3) | −0.010 (2) | −0.005 (2) | 0.006 (2) |
C14 | 0.046 (4) | 0.045 (3) | 0.071 (4) | −0.018 (3) | −0.007 (3) | 0.010 (3) |
C15 | 0.063 (5) | 0.046 (4) | 0.114 (7) | −0.025 (4) | −0.020 (5) | 0.024 (4) |
C16 | 0.040 (4) | 0.114 (8) | 0.091 (6) | −0.025 (5) | 0.005 (4) | 0.035 (5) |
C17 | 0.046 (4) | 0.091 (6) | 0.061 (4) | −0.007 (4) | 0.006 (3) | 0.017 (4) |
C18 | 0.036 (3) | 0.071 (4) | 0.044 (3) | −0.006 (3) | 0.002 (3) | 0.004 (3) |
C19 | 0.035 (3) | 0.037 (3) | 0.043 (3) | −0.004 (2) | −0.004 (2) | −0.002 (2) |
C20 | 0.031 (3) | 0.048 (4) | 0.110 (6) | 0.004 (3) | 0.015 (4) | 0.004 (4) |
C21 | 0.051 (4) | 0.043 (3) | 0.038 (3) | 0.009 (3) | 0.009 (3) | −0.002 (2) |
C22 | 0.061 (4) | 0.049 (4) | 0.066 (4) | 0.016 (3) | 0.011 (3) | 0.005 (3) |
C23 | 0.024 (3) | 0.038 (3) | 0.061 (4) | 0.001 (2) | 0.010 (2) | −0.006 (2) |
C24 | 0.038 (3) | 0.036 (3) | 0.072 (4) | 0.008 (2) | −0.006 (3) | −0.002 (3) |
C25 | 0.046 (4) | 0.033 (3) | 0.128 (7) | 0.012 (3) | −0.017 (4) | −0.002 (4) |
C26 | 0.041 (4) | 0.038 (3) | 0.154 (9) | 0.009 (3) | −0.001 (5) | −0.023 (4) |
C27 | 0.049 (4) | 0.066 (5) | 0.107 (7) | −0.001 (4) | 0.019 (4) | −0.038 (5) |
C28 | 0.039 (3) | 0.057 (4) | 0.063 (4) | −0.002 (3) | 0.011 (3) | −0.016 (3) |
C29 | 0.029 (3) | 0.034 (2) | 0.041 (3) | 0.010 (2) | 0.005 (2) | 0.007 (2) |
C30 | 0.037 (3) | 0.045 (3) | 0.040 (3) | 0.007 (2) | 0.005 (2) | 0.010 (2) |
C31 | 0.051 (4) | 0.064 (4) | 0.040 (3) | 0.013 (3) | 0.000 (3) | 0.006 (3) |
C32 | 0.062 (4) | 0.072 (5) | 0.045 (3) | 0.031 (4) | −0.013 (3) | −0.009 (3) |
C33 | 0.057 (4) | 0.040 (3) | 0.070 (4) | 0.012 (3) | −0.011 (3) | −0.007 (3) |
C34 | 0.046 (3) | 0.036 (3) | 0.052 (3) | 0.010 (2) | 0.000 (3) | 0.006 (2) |
C35 | 0.044 (3) | 0.061 (4) | 0.038 (3) | 0.016 (3) | −0.003 (2) | 0.000 (3) |
C36 | 0.049 (5) | 0.212 (12) | 0.039 (4) | −0.003 (6) | −0.009 (3) | 0.029 (6) |
C37 | 0.057 (6) | 0.260 (17) | 0.050 (5) | 0.027 (8) | −0.013 (4) | 0.008 (7) |
C38 | 0.109 (8) | 0.114 (8) | 0.075 (6) | 0.036 (7) | −0.051 (6) | 0.002 (5) |
C39 | 0.122 (10) | 0.144 (10) | 0.114 (9) | −0.011 (8) | −0.047 (7) | 0.084 (8) |
C40 | 0.094 (8) | 0.143 (10) | 0.125 (9) | −0.033 (7) | −0.054 (7) | 0.093 (8) |
C41 | 0.027 (3) | 0.051 (3) | 0.044 (3) | 0.002 (2) | 0.003 (2) | 0.008 (2) |
C42 | 0.043 (4) | 0.068 (5) | 0.086 (5) | 0.007 (3) | 0.020 (4) | 0.032 (4) |
C43 | 0.031 (3) | 0.033 (3) | 0.060 (3) | 0.000 (2) | 0.011 (3) | 0.004 (2) |
C44 | 0.056 (4) | 0.051 (4) | 0.086 (5) | −0.013 (3) | 0.004 (4) | 0.009 (4) |
C45 | 0.043 (4) | 0.084 (5) | 0.106 (6) | −0.011 (4) | 0.012 (4) | −0.057 (5) |
C46 | 0.105 (7) | 0.127 (7) | 0.137 (7) | −0.061 (6) | 0.009 (6) | −0.066 (6) |
C47 | 0.172 (10) | 0.166 (9) | 0.189 (10) | −0.078 (8) | −0.017 (8) | −0.065 (8) |
C48 | 0.073 (5) | 0.140 (7) | 0.108 (6) | −0.040 (5) | −0.016 (5) | −0.056 (6) |
C49 | 0.089 (6) | 0.176 (8) | 0.086 (6) | −0.026 (6) | 0.010 (5) | −0.069 (6) |
C50 | 0.064 (5) | 0.148 (7) | 0.073 (5) | −0.018 (5) | 0.005 (4) | −0.058 (5) |
C51 | 0.039 (3) | 0.036 (3) | 0.110 (5) | 0.002 (3) | 0.009 (3) | 0.007 (3) |
C52 | 0.096 (7) | 0.084 (6) | 0.161 (8) | 0.044 (5) | 0.010 (6) | −0.007 (6) |
C53 | 0.108 (7) | 0.100 (7) | 0.187 (9) | 0.051 (6) | 0.015 (7) | 0.054 (7) |
C54 | 0.107 (7) | 0.124 (8) | 0.162 (9) | 0.035 (6) | −0.008 (7) | 0.060 (7) |
C55 | 0.061 (5) | 0.093 (6) | 0.116 (6) | −0.001 (4) | −0.007 (4) | 0.057 (5) |
C56 | 0.053 (4) | 0.051 (4) | 0.089 (5) | −0.003 (3) | −0.007 (4) | 0.021 (3) |
C57 | 0.045 (3) | 0.053 (3) | 0.057 (3) | 0.017 (3) | 0.001 (3) | −0.014 (3) |
C58 | 0.057 (4) | 0.057 (4) | 0.053 (3) | 0.018 (3) | −0.002 (3) | −0.005 (3) |
C59 | 0.062 (4) | 0.052 (4) | 0.064 (4) | 0.017 (3) | 0.008 (3) | −0.001 (3) |
C60 | 0.063 (4) | 0.045 (3) | 0.061 (4) | 0.012 (3) | 0.013 (3) | −0.013 (3) |
C61 | 0.102 (6) | 0.081 (5) | 0.062 (4) | 0.036 (5) | 0.002 (4) | −0.017 (4) |
C62 | 0.108 (6) | 0.080 (5) | 0.062 (4) | 0.056 (5) | −0.005 (4) | −0.014 (4) |
C63 | 0.048 (4) | 0.059 (4) | 0.057 (4) | 0.019 (3) | −0.001 (3) | −0.010 (3) |
C64 | 0.069 (5) | 0.069 (4) | 0.087 (5) | −0.004 (4) | 0.025 (4) | −0.031 (4) |
C65 | 0.076 (5) | 0.100 (6) | 0.088 (5) | 0.018 (5) | 0.005 (4) | −0.040 (5) |
C66 | 0.097 (6) | 0.075 (5) | 0.076 (5) | 0.022 (4) | 0.033 (5) | −0.003 (4) |
C67 | 0.137 (8) | 0.078 (5) | 0.106 (6) | 0.011 (6) | 0.043 (6) | 0.002 (5) |
C68 | 0.104 (6) | 0.054 (4) | 0.076 (5) | 0.010 (4) | 0.025 (4) | −0.009 (4) |
Sn1—C1 | 2.144 (6) | C28—H28A | 0.9900 |
Sn1—C7 | 2.125 (6) | C28—H28B | 0.9900 |
Sn1—C13 | 2.134 (6) | C29—C34 | 1.388 (8) |
Sn1—O1 | 2.226 (4) | C29—C30 | 1.389 (7) |
Sn1—O3 | 2.231 (4) | C30—C31 | 1.382 (9) |
Sn2—C23 | 2.145 (5) | C30—H30 | 0.9500 |
Sn2—C29 | 2.130 (5) | C31—C32 | 1.386 (10) |
Sn2—C35 | 2.138 (6) | C31—H31 | 0.9500 |
Sn2—O5 | 2.243 (4) | C32—C33 | 1.363 (10) |
Sn2—O7 | 2.263 (4) | C32—H32 | 0.9500 |
Cl1—C20 | 1.682 (9) | C33—C34 | 1.394 (9) |
Cl2—C22 | 1.769 (7) | C33—H33 | 0.9500 |
Cl3—C42 | 1.689 (10) | C34—H34 | 0.9500 |
Cl4—C44 | 1.623 (9) | C35—C36 | 1.347 (10) |
F1—C20 | 1.299 (8) | C35—C40 | 1.374 (12) |
F2—C20 | 1.350 (9) | C36—C37 | 1.383 (12) |
F3—C22 | 1.315 (9) | C36—H36 | 0.9500 |
F4—C22 | 1.365 (9) | C37—C38 | 1.345 (16) |
F5—C42 | 1.298 (9) | C37—H37 | 0.9500 |
F6—C42 | 1.336 (9) | C38—C39 | 1.382 (16) |
F7—C44 | 1.355 (9) | C38—H38 | 0.9500 |
F8—C44 | 1.341 (9) | C39—C40 | 1.420 (12) |
O1—C19 | 1.248 (7) | C39—H39 | 0.9500 |
O2—C19 | 1.223 (7) | C40—H40 | 0.9500 |
O3—C21 | 1.247 (8) | C41—C42 | 1.531 (9) |
O4—C21 | 1.209 (8) | C43—C44 | 1.546 (9) |
O5—C41 | 1.251 (7) | C45—C50 | 1.491 (9) |
O6—C41 | 1.224 (7) | C45—C46 | 1.514 (8) |
O7—C43 | 1.236 (7) | C45—H45 | 1.0000 |
O8—C43 | 1.222 (7) | C46—C47 | 1.495 (9) |
N1—C51 | 1.490 (9) | C46—H46A | 0.9900 |
N1—C45 | 1.482 (9) | C46—H46B | 0.9900 |
N1—H1N1 | 0.8800 | C47—C48 | 1.479 (10) |
N1—H1N2 | 0.8800 | C47—H47A | 0.9900 |
N2—C63 | 1.476 (9) | C47—H47B | 0.9900 |
N2—C57 | 1.531 (8) | C48—C49 | 1.538 (9) |
N2—H2N1 | 0.8800 | C48—H48 | 0.9500 |
N2—H2N2 | 0.8800 | C49—C50 | 1.517 (8) |
C1—C6 | 1.447 (8) | C49—H49A | 0.9900 |
C1—C2 | 1.461 (9) | C49—H49B | 0.9900 |
C1—H1 | 1.0000 | C50—H50A | 0.9900 |
C2—C3 | 1.499 (10) | C50—H50B | 0.9900 |
C2—H2A | 0.9900 | C51—C56 | 1.494 (8) |
C2—H2B | 0.9900 | C51—C52 | 1.501 (8) |
C3—C4 | 1.446 (11) | C51—H51 | 1.0000 |
C3—H3A | 0.9900 | C52—C53 | 1.508 (9) |
C3—H3B | 0.9900 | C52—H52A | 0.9900 |
C4—C5 | 1.454 (11) | C52—H52B | 0.9900 |
C4—H4A | 0.9900 | C53—C54 | 1.483 (9) |
C4—H4B | 0.9900 | C53—H53A | 0.9900 |
C5—C6 | 1.497 (9) | C53—H53B | 0.9900 |
C5—H5 | 0.9500 | C54—C55 | 1.496 (9) |
C6—H6A | 0.9900 | C54—H54A | 0.9900 |
C6—H6B | 0.9900 | C54—H54B | 0.9900 |
C7—C12 | 1.394 (9) | C55—C56 | 1.515 (8) |
C7—C8 | 1.398 (9) | C55—H55A | 0.9900 |
C8—C9 | 1.392 (10) | C55—H55B | 0.9900 |
C8—H8 | 0.9500 | C56—H56A | 0.9900 |
C9—C10 | 1.364 (12) | C56—H56B | 0.9900 |
C9—H9 | 0.9500 | C57—C58 | 1.507 (7) |
C10—C11 | 1.348 (13) | C57—C62 | 1.516 (8) |
C10—H10 | 0.9500 | C57—H57 | 1.0000 |
C11—C12 | 1.407 (11) | C58—C59 | 1.513 (7) |
C11—H11 | 0.9500 | C58—H58A | 0.9900 |
C12—H12 | 0.9500 | C58—H58B | 0.9900 |
C13—C14 | 1.382 (9) | C59—C60 | 1.509 (7) |
C13—C18 | 1.398 (9) | C59—H59A | 0.9900 |
C14—C15 | 1.411 (9) | C59—H59B | 0.9900 |
C14—H14 | 0.9500 | C60—C61 | 1.492 (8) |
C15—C16 | 1.401 (13) | C60—H60A | 0.9900 |
C15—H15 | 0.9500 | C60—H60B | 0.9900 |
C16—C17 | 1.364 (13) | C61—C62 | 1.524 (7) |
C16—H16 | 0.9500 | C61—H61A | 0.9900 |
C17—C18 | 1.360 (10) | C61—H61B | 0.9900 |
C17—H17 | 0.9500 | C62—H62A | 0.9900 |
C18—H18 | 0.9500 | C62—H62B | 0.9900 |
C19—C20 | 1.524 (9) | C63—C68 | 1.497 (8) |
C21—C22 | 1.524 (9) | C63—C64 | 1.510 (7) |
C23—C28 | 1.520 (8) | C63—H63 | 1.0000 |
C23—C24 | 1.521 (9) | C64—C65 | 1.520 (8) |
C23—H23 | 1.0000 | C64—H64A | 0.9900 |
C24—C25 | 1.527 (8) | C64—H64B | 0.9900 |
C24—H24A | 0.9900 | C65—C66 | 1.488 (9) |
C24—H24B | 0.9900 | C65—H65A | 0.9900 |
C25—C26 | 1.518 (11) | C65—H65B | 0.9900 |
C25—H25A | 0.9900 | C66—C67 | 1.517 (8) |
C25—H25B | 0.9900 | C66—H66A | 0.9900 |
C26—C27 | 1.508 (13) | C66—H66B | 0.9900 |
C26—H26A | 0.9900 | C67—C68 | 1.503 (8) |
C26—H26B | 0.9900 | C67—H67A | 0.9900 |
C27—C28 | 1.511 (10) | C67—H67B | 0.9900 |
C27—H27A | 0.9900 | C68—H68A | 0.9900 |
C27—H27B | 0.9900 | C68—H68B | 0.9900 |
C7—Sn1—C13 | 113.2 (2) | C36—C35—C40 | 116.6 (7) |
C7—Sn1—C1 | 127.6 (3) | C36—C35—Sn2 | 122.9 (6) |
C13—Sn1—C1 | 119.1 (3) | C40—C35—Sn2 | 120.3 (5) |
C7—Sn1—O1 | 91.4 (2) | C35—C36—C37 | 123.4 (10) |
C13—Sn1—O1 | 88.04 (19) | C35—C36—H36 | 118.3 |
C1—Sn1—O1 | 92.6 (2) | C37—C36—H36 | 118.3 |
C7—Sn1—O3 | 85.9 (2) | C38—C37—C36 | 119.6 (10) |
C13—Sn1—O3 | 92.7 (2) | C38—C37—H37 | 120.2 |
C1—Sn1—O3 | 89.3 (2) | C36—C37—H37 | 120.2 |
O1—Sn1—O3 | 177.3 (2) | C37—C38—C39 | 119.9 (8) |
C29—Sn2—C35 | 119.7 (2) | C37—C38—H38 | 120.0 |
C29—Sn2—C23 | 119.3 (2) | C39—C38—H38 | 120.0 |
C35—Sn2—C23 | 121.0 (2) | C38—C39—C40 | 117.7 (11) |
C29—Sn2—O5 | 91.75 (18) | C38—C39—H39 | 121.2 |
C35—Sn2—O5 | 92.6 (2) | C40—C39—H39 | 121.2 |
C23—Sn2—O5 | 85.22 (18) | C35—C40—C39 | 121.7 (10) |
C29—Sn2—O7 | 89.36 (18) | C35—C40—H40 | 119.1 |
C35—Sn2—O7 | 86.5 (2) | C39—C40—H40 | 119.1 |
C23—Sn2—O7 | 94.60 (17) | O6—C41—O5 | 129.9 (6) |
O5—Sn2—O7 | 178.8 (2) | O6—C41—C42 | 117.2 (5) |
C19—O1—Sn1 | 121.2 (3) | O5—C41—C42 | 112.9 (5) |
C21—O3—Sn1 | 128.9 (4) | F5—C42—F6 | 97.3 (7) |
C41—O5—Sn2 | 134.4 (4) | F5—C42—C41 | 112.4 (7) |
C43—O7—Sn2 | 124.4 (3) | F6—C42—C41 | 109.6 (7) |
C51—N1—H1N1 | 108.1 | F5—C42—Cl3 | 114.7 (8) |
C45—N1—H1N1 | 108.1 | F6—C42—Cl3 | 110.5 (6) |
C51—N1—H1N2 | 108.1 | C41—C42—Cl3 | 111.4 (5) |
C45—N1—H1N2 | 108.1 | O8—C43—O7 | 128.4 (5) |
H1N1—N1—H1N2 | 107.3 | O8—C43—C44 | 117.8 (6) |
C45—N1—C51 | 116.8 (6) | O7—C43—C44 | 113.7 (5) |
C57—N2—C63 | 118.3 (5) | F8—C44—F7 | 104.0 (6) |
C63—N2—H2N1 | 107.7 | F8—C44—C43 | 110.8 (6) |
C57—N2—H2N1 | 107.7 | F7—C44—C43 | 112.2 (6) |
C63—N2—H2N2 | 107.7 | F8—C44—Cl4 | 108.9 (7) |
C57—N2—H2N2 | 107.7 | F7—C44—Cl4 | 107.7 (6) |
H2N1—N2—H2N2 | 107.1 | C43—C44—Cl4 | 112.7 (6) |
C6—C1—C2 | 117.4 (6) | N1—C45—C50 | 109.0 (6) |
C6—C1—Sn1 | 116.3 (5) | N1—C45—C46 | 110.8 (7) |
C2—C1—Sn1 | 117.7 (4) | C50—C45—C46 | 109.4 (9) |
C6—C1—H1 | 99.9 | N1—C45—H45 | 109.2 |
C2—C1—H1 | 99.9 | C50—C45—H45 | 109.2 |
Sn1—C1—H1 | 99.9 | C46—C45—H45 | 109.2 |
C1—C2—C3 | 114.8 (6) | C45—C46—C47 | 111.2 (9) |
C1—C2—H2A | 108.6 | C45—C46—H46A | 109.4 |
C3—C2—H2A | 108.6 | C47—C46—H46A | 109.4 |
C1—C2—H2B | 108.6 | C45—C46—H46B | 109.4 |
C3—C2—H2B | 108.6 | C47—C46—H46B | 109.4 |
H2A—C2—H2B | 107.5 | H46A—C46—H46B | 108.0 |
C4—C3—C2 | 114.0 (7) | C48—C47—C46 | 104.4 (11) |
C4—C3—H3A | 108.8 | C48—C47—H47A | 110.9 |
C2—C3—H3A | 108.8 | C46—C47—H47A | 110.9 |
C4—C3—H3B | 108.8 | C48—C47—H47B | 110.9 |
C2—C3—H3B | 108.8 | C46—C47—H47B | 110.9 |
H3A—C3—H3B | 107.6 | H47A—C47—H47B | 108.9 |
C3—C4—C5 | 115.9 (7) | C49—C48—C47 | 114.3 (10) |
C3—C4—H4A | 108.3 | C49—C48—H48 | 122.9 |
C5—C4—H4A | 108.3 | C47—C48—H48 | 122.9 |
C3—C4—H4B | 108.3 | C48—C49—C50 | 109.7 (8) |
C5—C4—H4B | 108.3 | C48—C49—H49A | 109.7 |
H4A—C4—H4B | 107.4 | C50—C49—H49A | 109.7 |
C4—C5—C6 | 115.8 (6) | C48—C49—H49B | 109.7 |
C4—C5—H5 | 122.1 | C50—C49—H49B | 109.7 |
C6—C5—H5 | 122.1 | H49A—C49—H49B | 108.2 |
C1—C6—C5 | 114.6 (6) | C45—C50—C49 | 109.8 (9) |
C1—C6—H6A | 108.6 | C45—C50—H50A | 109.7 |
C5—C6—H6A | 108.6 | C49—C50—H50A | 109.7 |
C1—C6—H6B | 108.6 | C45—C50—H50B | 109.7 |
C5—C6—H6B | 108.6 | C49—C50—H50B | 109.7 |
H6A—C6—H6B | 107.6 | H50A—C50—H50B | 108.2 |
C12—C7—C8 | 117.6 (6) | N1—C51—C56 | 110.1 (5) |
C12—C7—Sn1 | 121.8 (5) | N1—C51—C52 | 113.7 (7) |
C8—C7—Sn1 | 120.7 (5) | C56—C51—C52 | 109.6 (7) |
C9—C8—C7 | 120.4 (7) | N1—C51—H51 | 107.7 |
C9—C8—H8 | 119.8 | C56—C51—H51 | 107.7 |
C7—C8—H8 | 119.8 | C52—C51—H51 | 107.7 |
C10—C9—C8 | 120.8 (8) | C53—C52—C51 | 110.0 (8) |
C10—C9—H9 | 119.6 | C53—C52—H52A | 109.7 |
C8—C9—H9 | 119.6 | C51—C52—H52A | 109.7 |
C11—C10—C9 | 120.0 (8) | C53—C52—H52B | 109.7 |
C11—C10—H10 | 120.0 | C51—C52—H52B | 109.7 |
C9—C10—H10 | 120.0 | H52A—C52—H52B | 108.2 |
C10—C11—C12 | 120.6 (8) | C52—C53—C54 | 115.4 (10) |
C10—C11—H11 | 119.7 | C52—C53—H53A | 108.4 |
C12—C11—H11 | 119.7 | C54—C53—H53A | 108.4 |
C7—C12—C11 | 120.3 (8) | C52—C53—H53B | 108.4 |
C7—C12—H12 | 119.9 | C54—C53—H53B | 108.4 |
C11—C12—H12 | 119.9 | H53A—C53—H53B | 107.5 |
C14—C13—C18 | 118.6 (6) | C53—C54—C55 | 108.5 (10) |
C14—C13—Sn1 | 121.4 (5) | C53—C54—H54A | 110.0 |
C18—C13—Sn1 | 120.0 (5) | C55—C54—H54A | 110.0 |
C13—C14—C15 | 119.7 (7) | C53—C54—H54B | 110.0 |
C13—C14—H14 | 120.2 | C55—C54—H54B | 110.0 |
C15—C14—H14 | 120.2 | H54A—C54—H54B | 108.4 |
C16—C15—C14 | 119.1 (8) | C54—C55—C56 | 111.7 (8) |
C16—C15—H15 | 120.4 | C54—C55—H55A | 109.3 |
C14—C15—H15 | 120.4 | C56—C55—H55A | 109.3 |
C17—C16—C15 | 120.9 (7) | C54—C55—H55B | 109.3 |
C17—C16—H16 | 119.5 | C56—C55—H55B | 109.3 |
C15—C16—H16 | 119.5 | H55A—C55—H55B | 107.9 |
C18—C17—C16 | 119.3 (8) | C51—C56—C55 | 111.9 (7) |
C18—C17—H17 | 120.4 | C51—C56—H56A | 109.2 |
C16—C17—H17 | 120.4 | C55—C56—H56A | 109.2 |
C17—C18—C13 | 122.4 (7) | C51—C56—H56B | 109.2 |
C17—C18—H18 | 118.8 | C55—C56—H56B | 109.2 |
C13—C18—H18 | 118.8 | H56A—C56—H56B | 107.9 |
O2—C19—O1 | 130.0 (6) | C58—C57—C62 | 111.8 (6) |
O2—C19—C20 | 117.7 (5) | C58—C57—N2 | 112.9 (5) |
O1—C19—C20 | 112.3 (5) | C62—C57—N2 | 107.4 (5) |
F1—C20—F2 | 106.1 (7) | C58—C57—H57 | 108.2 |
F1—C20—C19 | 112.3 (6) | C62—C57—H57 | 108.2 |
F2—C20—C19 | 111.4 (6) | N2—C57—H57 | 108.2 |
F1—C20—Cl1 | 109.7 (6) | C57—C58—C59 | 109.5 (5) |
F2—C20—Cl1 | 104.3 (6) | C57—C58—H58A | 109.8 |
C19—C20—Cl1 | 112.5 (6) | C59—C58—H58A | 109.8 |
O4—C21—O3 | 129.0 (6) | C57—C58—H58B | 109.8 |
O4—C21—C22 | 119.9 (6) | C59—C58—H58B | 109.8 |
O3—C21—C22 | 111.0 (6) | H58A—C58—H58B | 108.2 |
F3—C22—F4 | 106.4 (6) | C60—C59—C58 | 112.8 (5) |
F3—C22—C21 | 112.3 (6) | C60—C59—H59A | 109.0 |
F4—C22—C21 | 112.7 (6) | C58—C59—H59A | 109.0 |
F3—C22—Cl2 | 109.1 (5) | C60—C59—H59B | 109.0 |
F4—C22—Cl2 | 106.3 (5) | C58—C59—H59B | 109.0 |
C21—C22—Cl2 | 109.8 (5) | H59A—C59—H59B | 107.8 |
C28—C23—C24 | 110.9 (5) | C61—C60—C59 | 111.1 (6) |
C28—C23—Sn2 | 112.4 (4) | C61—C60—H60A | 109.4 |
C24—C23—Sn2 | 111.1 (4) | C59—C60—H60A | 109.4 |
C28—C23—H23 | 107.4 | C61—C60—H60B | 109.4 |
C24—C23—H23 | 107.4 | C59—C60—H60B | 109.4 |
Sn2—C23—H23 | 107.4 | H60A—C60—H60B | 108.0 |
C23—C24—C25 | 111.0 (6) | C60—C61—C62 | 110.7 (6) |
C23—C24—H24A | 109.4 | C60—C61—H61A | 109.5 |
C25—C24—H24A | 109.4 | C62—C61—H61A | 109.5 |
C23—C24—H24B | 109.4 | C60—C61—H61B | 109.5 |
C25—C24—H24B | 109.4 | C62—C61—H61B | 109.5 |
H24A—C24—H24B | 108.0 | H61A—C61—H61B | 108.1 |
C26—C25—C24 | 110.1 (6) | C57—C62—C61 | 110.3 (6) |
C26—C25—H25A | 109.6 | C57—C62—H62A | 109.6 |
C24—C25—H25A | 109.6 | C61—C62—H62A | 109.6 |
C26—C25—H25B | 109.6 | C57—C62—H62B | 109.6 |
C24—C25—H25B | 109.6 | C61—C62—H62B | 109.6 |
H25A—C25—H25B | 108.1 | H62A—C62—H62B | 108.1 |
C27—C26—C25 | 112.0 (7) | N2—C63—C68 | 113.2 (6) |
C27—C26—H26A | 109.2 | N2—C63—C64 | 109.6 (6) |
C25—C26—H26A | 109.2 | C68—C63—C64 | 109.6 (6) |
C27—C26—H26B | 109.2 | N2—C63—H63 | 108.1 |
C25—C26—H26B | 109.2 | C68—C63—H63 | 108.1 |
H26A—C26—H26B | 107.9 | C64—C63—H63 | 108.1 |
C28—C27—C26 | 110.4 (6) | C63—C64—C65 | 111.2 (7) |
C28—C27—H27A | 109.6 | C63—C64—H64A | 109.4 |
C26—C27—H27A | 109.6 | C65—C64—H64A | 109.4 |
C28—C27—H27B | 109.6 | C63—C64—H64B | 109.4 |
C26—C27—H27B | 109.6 | C65—C64—H64B | 109.4 |
H27A—C27—H27B | 108.1 | H64A—C64—H64B | 108.0 |
C27—C28—C23 | 111.8 (6) | C66—C65—C64 | 108.8 (7) |
C27—C28—H28A | 109.2 | C66—C65—H65A | 109.9 |
C23—C28—H28A | 109.2 | C64—C65—H65A | 109.9 |
C27—C28—H28B | 109.2 | C66—C65—H65B | 109.9 |
C23—C28—H28B | 109.2 | C64—C65—H65B | 109.9 |
H28A—C28—H28B | 107.9 | H65A—C65—H65B | 108.3 |
C34—C29—C30 | 117.9 (5) | C65—C66—C67 | 112.3 (8) |
C34—C29—Sn2 | 120.6 (4) | C65—C66—H66A | 109.1 |
C30—C29—Sn2 | 121.5 (4) | C67—C66—H66A | 109.1 |
C31—C30—C29 | 121.1 (6) | C65—C66—H66B | 109.1 |
C31—C30—H30 | 119.5 | C67—C66—H66B | 109.1 |
C29—C30—H30 | 119.5 | H66A—C66—H66B | 107.9 |
C32—C31—C30 | 120.1 (6) | C68—C67—C66 | 112.9 (8) |
C32—C31—H31 | 120.0 | C68—C67—H67A | 109.0 |
C30—C31—H31 | 120.0 | C66—C67—H67A | 109.0 |
C33—C32—C31 | 119.8 (6) | C68—C67—H67B | 109.0 |
C33—C32—H32 | 120.1 | C66—C67—H67B | 109.0 |
C31—C32—H32 | 120.1 | H67A—C67—H67B | 107.8 |
C32—C33—C34 | 120.2 (6) | C63—C68—C67 | 111.7 (8) |
C32—C33—H33 | 119.9 | C63—C68—H68A | 109.3 |
C34—C33—H33 | 119.9 | C67—C68—H68A | 109.3 |
C33—C34—C29 | 121.0 (6) | C63—C68—H68B | 109.3 |
C33—C34—H34 | 119.5 | C67—C68—H68B | 109.3 |
C29—C34—H34 | 119.5 | H68A—C68—H68B | 107.9 |
C7—Sn1—O1—C19 | 59.3 (4) | C24—C23—C28—C27 | 55.6 (7) |
C13—Sn1—O1—C19 | 172.4 (4) | Sn2—C23—C28—C27 | −179.4 (5) |
C1—Sn1—O1—C19 | −68.5 (5) | C35—Sn2—C29—C34 | 50.7 (5) |
C7—Sn1—O3—C21 | 177.4 (6) | C23—Sn2—C29—C34 | −129.8 (4) |
C13—Sn1—O3—C21 | 64.3 (5) | O5—Sn2—C29—C34 | 144.7 (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—C41 | 75.4 (6) | C23—Sn2—C29—C30 | 48.9 (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—C30 | 143.8 (4) |
C35—Sn2—O7—C43 | 173.4 (5) | C34—C29—C30—C31 | −0.1 (8) |
C23—Sn2—O7—C43 | 52.5 (5) | Sn2—C29—C30—C31 | −178.8 (5) |
C7—Sn1—C1—C6 | 27.9 (7) | C29—C30—C31—C32 | 0.1 (10) |
C13—Sn1—C1—C6 | −149.2 (5) | C30—C31—C32—C33 | −1.1 (10) |
O1—Sn1—C1—C6 | 121.7 (6) | C31—C32—C33—C34 | 2.1 (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—C33 | 1.0 (9) |
C13—Sn1—C1—C2 | 63.9 (7) | Sn2—C29—C34—C33 | 179.8 (5) |
O1—Sn1—C1—C2 | −25.3 (6) | C29—Sn2—C35—C36 | 82.8 (8) |
O3—Sn1—C1—C2 | 156.7 (6) | C23—Sn2—C35—C36 | −96.7 (8) |
C6—C1—C2—C3 | 40.4 (10) | O5—Sn2—C35—C36 | −10.7 (8) |
Sn1—C1—C2—C3 | −173.1 (6) | O7—Sn2—C35—C36 | 170.1 (8) |
C1—C2—C3—C4 | −42.7 (11) | C29—Sn2—C35—C40 | −103.3 (8) |
C2—C3—C4—C5 | 44.4 (12) | C23—Sn2—C35—C40 | 77.3 (9) |
C3—C4—C5—C6 | −42.6 (11) | O5—Sn2—C35—C40 | 163.3 (8) |
C2—C1—C6—C5 | −37.9 (10) | O7—Sn2—C35—C40 | −16.0 (8) |
Sn1—C1—C6—C5 | 175.1 (5) | C40—C35—C36—C37 | 4.9 (18) |
C4—C5—C6—C1 | 38.4 (10) | Sn2—C35—C36—C37 | 179.1 (10) |
C13—Sn1—C7—C12 | 123.5 (7) | C35—C36—C37—C38 | 0 (2) |
C1—Sn1—C7—C12 | −53.6 (8) | C36—C37—C38—C39 | −9 (2) |
O1—Sn1—C7—C12 | −148.0 (7) | C37—C38—C39—C40 | 12 (2) |
O3—Sn1—C7—C12 | 32.3 (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—C8 | 126.5 (5) | C38—C39—C40—C35 | −7 (2) |
O1—Sn1—C7—C8 | 32.2 (6) | Sn2—O5—C41—O6 | −13.2 (11) |
O3—Sn1—C7—C8 | −147.5 (6) | Sn2—O5—C41—C42 | 168.1 (5) |
C12—C7—C8—C9 | −4.1 (11) | O6—C41—C42—F5 | 141.8 (8) |
Sn1—C7—C8—C9 | 175.8 (5) | O5—C41—C42—F5 | −39.4 (10) |
C7—C8—C9—C10 | 3.7 (12) | O6—C41—C42—F6 | 34.8 (9) |
C8—C9—C10—C11 | −4.2 (14) | O5—C41—C42—F6 | −146.4 (6) |
C9—C10—C11—C12 | 5.2 (15) | O6—C41—C42—Cl3 | −87.8 (7) |
C8—C7—C12—C11 | 5.1 (13) | O5—C41—C42—Cl3 | 91.0 (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—C44 | 175.1 (4) |
C7—Sn1—C13—C14 | 110.5 (5) | O8—C43—C44—F8 | −72.2 (9) |
C1—Sn1—C13—C14 | −72.0 (6) | O7—C43—C44—F8 | 106.1 (7) |
O1—Sn1—C13—C14 | 19.8 (5) | O8—C43—C44—F7 | 172.0 (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—Cl4 | 50.2 (8) |
C1—Sn1—C13—C18 | 110.2 (5) | O7—C43—C44—Cl4 | −131.5 (6) |
O1—Sn1—C13—C18 | −158.0 (5) | C51—N1—C45—C50 | 178.0 (6) |
O3—Sn1—C13—C18 | 19.5 (5) | C51—N1—C45—C46 | 57.6 (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—C47 | 65.2 (13) |
C13—C14—C15—C16 | 0.1 (11) | C45—C46—C47—C48 | −63.4 (16) |
C14—C15—C16—C17 | 0.5 (13) | C46—C47—C48—C49 | 59.7 (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—C17 | 0.9 (10) | C46—C45—C50—C49 | −57.3 (10) |
Sn1—C13—C18—C17 | 178.8 (5) | C48—C49—C50—C45 | 52.3 (12) |
Sn1—O1—C19—O2 | 2.6 (8) | C45—N1—C51—C56 | 179.2 (6) |
Sn1—O1—C19—C20 | −176.3 (4) | C45—N1—C51—C52 | 55.8 (9) |
O2—C19—C20—F1 | −35.6 (10) | N1—C51—C52—C53 | 178.2 (9) |
O1—C19—C20—F1 | 143.4 (7) | C56—C51—C52—C53 | 54.5 (12) |
O2—C19—C20—F2 | −154.5 (7) | C51—C52—C53—C54 | −55.5 (15) |
O1—C19—C20—F2 | 24.5 (9) | C52—C53—C54—C55 | 54.2 (15) |
O2—C19—C20—Cl1 | 88.8 (6) | C53—C54—C55—C56 | −53.9 (13) |
O1—C19—C20—Cl1 | −92.2 (6) | N1—C51—C56—C55 | 176.8 (6) |
Sn1—O3—C21—O4 | −6.3 (10) | C52—C51—C56—C55 | −57.4 (9) |
Sn1—O3—C21—C22 | 175.9 (4) | C54—C55—C56—C51 | 58.0 (11) |
O4—C21—C22—F3 | 24.2 (9) | C63—N2—C57—C58 | 60.7 (8) |
O3—C21—C22—F3 | −157.7 (6) | C63—N2—C57—C62 | −175.7 (6) |
O4—C21—C22—F4 | 144.4 (7) | C62—C57—C58—C59 | 55.6 (8) |
O3—C21—C22—F4 | −37.6 (8) | N2—C57—C58—C59 | 176.8 (6) |
O4—C21—C22—Cl2 | −97.4 (7) | C57—C58—C59—C60 | −54.8 (9) |
O3—C21—C22—Cl2 | 80.7 (6) | C58—C59—C60—C61 | 55.7 (9) |
C29—Sn2—C23—C28 | −150.3 (4) | C59—C60—C61—C62 | −55.7 (10) |
C35—Sn2—C23—C28 | 29.1 (5) | C58—C57—C62—C61 | −57.2 (10) |
O5—Sn2—C23—C28 | −61.0 (4) | N2—C57—C62—C61 | 178.4 (7) |
O7—Sn2—C23—C28 | 117.8 (4) | C60—C61—C62—C57 | 56.7 (11) |
C29—Sn2—C23—C24 | −25.4 (5) | C57—N2—C63—C68 | 54.4 (8) |
C35—Sn2—C23—C24 | 154.0 (4) | C57—N2—C63—C64 | 177.1 (6) |
O5—Sn2—C23—C24 | 63.9 (4) | N2—C63—C64—C65 | 175.0 (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—C66 | 60.1 (10) |
Sn2—C23—C24—C25 | 178.7 (4) | C64—C65—C66—C67 | −55.0 (11) |
C23—C24—C25—C26 | 55.9 (8) | C65—C66—C67—C68 | 51.9 (13) |
C24—C25—C26—C27 | −56.7 (9) | N2—C63—C68—C67 | 177.7 (7) |
C25—C26—C27—C28 | 56.4 (8) | C64—C63—C68—C67 | 55.0 (10) |
C26—C27—C28—C23 | −55.5 (8) | C66—C67—C68—C63 | −51.3 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O2 | 0.88 | 1.93 | 2.797 (7) | 166 |
N1—H1n2···O6i | 0.88 | 1.97 | 2.798 (7) | 155 |
N2—H2n2···O4 | 0.88 | 1.94 | 2.798 (7) | 165 |
N2—H2n1···O8 | 0.88 | 1.94 | 2.759 (6) | 155 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | (C12H24N)[Sn(C6H5)2(C6H11)(CClF2O2)2] |
Mr | 796.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 22.5469 (3), 17.2799 (2), 18.6963 (2) |
β (°) | 90.324 (1) |
V (Å3) | 7284 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.15 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.788, 0.915 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 93218, 16710, 12483 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.216, 1.33 |
No. of reflections | 16710 |
No. of parameters | 829 |
No. of restraints | 240 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.24, −2.03 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Sn1—C1 | 2.144 (6) | Sn2—C23 | 2.145 (5) |
Sn1—C7 | 2.125 (6) | Sn2—C29 | 2.130 (5) |
Sn1—C13 | 2.134 (6) | Sn2—C35 | 2.138 (6) |
Sn1—O1 | 2.226 (4) | Sn2—O5 | 2.243 (4) |
Sn1—O3 | 2.231 (4) | Sn2—O7 | 2.263 (4) |
O1—Sn1—O3 | 177.3 (2) | C41—O5—Sn2 | 134.4 (4) |
O5—Sn2—O7 | 178.8 (2) | C43—O7—Sn2 | 124.4 (3) |
C19—O1—Sn1 | 121.2 (3) | C45—N1—C51 | 116.8 (6) |
C21—O3—Sn1 | 128.9 (4) | C57—N2—C63 | 118.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O2 | 0.88 | 1.93 | 2.797 (7) | 166 |
N1—H1n2···O6i | 0.88 | 1.97 | 2.798 (7) | 155 |
N2—H2n2···O4 | 0.88 | 1.94 | 2.798 (7) | 165 |
N2—H2n1···O8 | 0.88 | 1.94 | 2.759 (6) | 155 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
We thank the University of Malaya for funding this study (SF022155/2007 A) and also for the purchase of the diffractometer.
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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).