metal-organic compounds
Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclopentyldiphenylstannate(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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.
Related literature
For details of the et al. (2008). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).
of dicyclohexylammonium bis(chlorodifluoroacetato)cyclohexyldiphenylstannate(IV), see TeoExperimental
Crystal data
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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/S1600536808010775/lh2611sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010775/lh2611Isup2.hkl
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.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 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 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.
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(C5H9)(C6H5)2(C2ClF2O2)] | F(000) = 800 |
Mr = 783.27 | Dx = 1.508 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4999 reflections |
a = 8.8610 (2) Å | θ = 2.3–24.4° |
b = 19.3132 (3) Å | µ = 0.95 mm−1 |
c = 10.6823 (2) Å | T = 100 K |
β = 109.385 (1)° | Irregular block, colorless |
V = 1724.47 (6) Å3 | 0.30 × 0.20 × 0.15 mm |
Z = 2 |
Bruker SMART APEX diffractometer | 7831 independent reflections |
Radiation source: fine-focus sealed tube | 6637 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.679, Tmax = 0.870 | k = −25→25 |
18017 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0717P)2 + 1.4264P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
7831 reflections | Δρmax = 1.11 e Å−3 |
421 parameters | Δρmin = −0.71 e Å−3 |
41 restraints | Absolute structure: Flack (1983), 3766 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (3) |
(C12H24N)[Sn(C5H9)(C6H5)2(C2ClF2O2)] | V = 1724.47 (6) Å3 |
Mr = 783.27 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.8610 (2) Å | µ = 0.95 mm−1 |
b = 19.3132 (3) Å | T = 100 K |
c = 10.6823 (2) Å | 0.30 × 0.20 × 0.15 mm |
β = 109.385 (1)° |
Bruker SMART APEX diffractometer | 7831 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6637 reflections with I > 2σ(I) |
Tmin = 0.679, Tmax = 0.870 | Rint = 0.038 |
18017 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.132 | Δρmax = 1.11 e Å−3 |
S = 1.04 | Δρmin = −0.71 e Å−3 |
7831 reflections | Absolute structure: Flack (1983), 3766 Friedel pairs |
421 parameters | Absolute structure parameter: −0.03 (3) |
41 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.41483 (4) | 0.50001 (7) | 0.27785 (3) | 0.03273 (11) | |
Cl1 | 0.5652 (5) | 0.7213 (2) | 0.0894 (3) | 0.1213 (13) | |
Cl2 | 0.1779 (5) | 0.25792 (18) | 0.2051 (3) | 0.1310 (16) | |
F1 | 0.7544 (5) | 0.7106 (2) | 0.3078 (5) | 0.0684 (13) | |
F2 | 0.5523 (5) | 0.7777 (2) | 0.2839 (5) | 0.0622 (12) | |
F3 | 0.3331 (6) | 0.2399 (2) | 0.4277 (5) | 0.0721 (14) | |
F4 | 0.1352 (6) | 0.3071 (3) | 0.4035 (6) | 0.0776 (15) | |
O1 | 0.5515 (5) | 0.5970 (2) | 0.2551 (5) | 0.0389 (10) | |
O2 | 0.4078 (5) | 0.6683 (2) | 0.3391 (5) | 0.0372 (10) | |
O3 | 0.2746 (5) | 0.4049 (2) | 0.2913 (4) | 0.0366 (9) | |
O4 | 0.4990 (6) | 0.3475 (2) | 0.4043 (5) | 0.0419 (10) | |
N1 | 0.2491 (6) | 0.7638 (2) | 0.4417 (4) | 0.0264 (9) | |
H1N1 | 0.2976 | 0.7356 | 0.4026 | 0.032* | |
H1N2 | 0.3196 | 0.7947 | 0.4861 | 0.032* | |
C1 | 0.5036 (5) | 0.5092 (2) | 0.4901 (5) | 0.0335 (12) | |
C2 | 0.445 (4) | 0.4703 (16) | 0.574 (4) | 0.034 (3) | 0.50 |
H2 | 0.3604 | 0.4389 | 0.5336 | 0.040* | 0.50 |
C3 | 0.502 (6) | 0.474 (2) | 0.711 (4) | 0.040 (5) | 0.50 |
H3 | 0.4581 | 0.4462 | 0.7645 | 0.047* | 0.50 |
C4 | 0.625 (6) | 0.520 (3) | 0.7657 (10) | 0.0475 (18) | 0.50 |
H4 | 0.6666 | 0.5237 | 0.8597 | 0.057* | 0.50 |
C5 | 0.693 (5) | 0.561 (2) | 0.692 (4) | 0.037 (4) | 0.50 |
H5 | 0.7779 | 0.5926 | 0.7332 | 0.045* | 0.50 |
C6 | 0.6282 (18) | 0.5547 (12) | 0.555 (4) | 0.033 (3) | 0.50 |
H6 | 0.6714 | 0.5826 | 0.5018 | 0.039* | 0.50 |
C2' | 0.420 (4) | 0.4798 (14) | 0.567 (4) | 0.034 (3) | 0.50 |
H2' | 0.3212 | 0.4565 | 0.5261 | 0.040* | 0.50 |
C3' | 0.484 (6) | 0.486 (2) | 0.703 (4) | 0.040 (5) | 0.50 |
H3' | 0.4279 | 0.4657 | 0.7564 | 0.047* | 0.50 |
C4' | 0.627 (6) | 0.519 (3) | 0.7660 (10) | 0.0475 (18) | 0.50 |
H4' | 0.6697 | 0.5224 | 0.8599 | 0.057* | 0.50 |
C5' | 0.707 (5) | 0.548 (2) | 0.686 (4) | 0.037 (4) | 0.50 |
H5' | 0.8061 | 0.5706 | 0.7278 | 0.045* | 0.50 |
C6' | 0.6483 (16) | 0.5438 (12) | 0.549 (4) | 0.033 (3) | 0.50 |
H6' | 0.7046 | 0.5640 | 0.4959 | 0.039* | 0.50 |
C7 | 0.1931 (7) | 0.5482 (3) | 0.1691 (6) | 0.0315 (12) | |
C8 | 0.1848 (8) | 0.5921 (3) | 0.0642 (6) | 0.0373 (13) | |
H8 | 0.2746 | 0.5977 | 0.0355 | 0.045* | |
C9 | 0.0415 (8) | 0.6283 (4) | 0.0009 (7) | 0.0447 (15) | |
H9 | 0.0348 | 0.6580 | −0.0718 | 0.054* | |
C10 | −0.0874 (8) | 0.6213 (3) | 0.0426 (6) | 0.0409 (14) | |
H10 | −0.1823 | 0.6469 | 0.0000 | 0.049* | |
C11 | −0.0815 (7) | 0.5781 (3) | 0.1447 (7) | 0.0373 (13) | |
H11 | −0.1720 | 0.5731 | 0.1728 | 0.045* | |
C12 | 0.0584 (7) | 0.5410 (3) | 0.2081 (6) | 0.0340 (12) | |
H12 | 0.0619 | 0.5105 | 0.2788 | 0.041* | |
C13 | 0.5521 (7) | 0.4533 (4) | 0.1721 (7) | 0.056 (2) | |
H13 | 0.5677 | 0.4912 | 0.1139 | 0.068* | |
C14 | 0.4920 (7) | 0.3925 (4) | 0.0773 (8) | 0.062 (2) | |
H14A | 0.4110 | 0.4081 | −0.0064 | 0.075* | |
H14B | 0.4437 | 0.3565 | 0.1182 | 0.075* | |
C15 | 0.6441 (9) | 0.3636 (4) | 0.0507 (7) | 0.074 (3) | |
H15A | 0.6432 | 0.3123 | 0.0501 | 0.089* | |
H15B | 0.6480 | 0.3802 | −0.0358 | 0.089* | |
C16 | 0.7884 (7) | 0.3909 (4) | 0.1650 (7) | 0.0494 (17) | |
H16A | 0.8564 | 0.4204 | 0.1297 | 0.059* | |
H16B | 0.8539 | 0.3519 | 0.2142 | 0.059* | |
C17 | 0.7225 (7) | 0.4334 (4) | 0.2575 (6) | 0.0433 (15) | |
H17A | 0.7215 | 0.4054 | 0.3348 | 0.052* | |
H17B | 0.7883 | 0.4753 | 0.2898 | 0.052* | |
C18 | 0.5096 (7) | 0.6545 (3) | 0.2852 (6) | 0.0358 (13) | |
C19 | 0.5981 (7) | 0.7165 (3) | 0.2514 (6) | 0.0458 (16) | |
C20 | 0.3529 (8) | 0.3533 (3) | 0.3501 (7) | 0.0358 (14) | |
C21 | 0.2525 (7) | 0.2913 (3) | 0.3561 (5) | 0.0415 (14) | |
C22 | 0.1928 (7) | 0.7229 (3) | 0.5380 (6) | 0.0306 (12) | |
H22 | 0.1109 | 0.7509 | 0.5611 | 0.037* | |
C23 | 0.3314 (9) | 0.7076 (3) | 0.6660 (6) | 0.0437 (15) | |
H23A | 0.4127 | 0.6786 | 0.6458 | 0.052* | |
H23B | 0.3830 | 0.7514 | 0.7063 | 0.052* | |
C24 | 0.2667 (10) | 0.6697 (4) | 0.7623 (7) | 0.0514 (18) | |
H24A | 0.1915 | 0.7003 | 0.7870 | 0.062* | |
H24B | 0.3563 | 0.6585 | 0.8441 | 0.062* | |
C25 | 0.1806 (9) | 0.6031 (3) | 0.7024 (7) | 0.0423 (15) | |
H25A | 0.2590 | 0.5698 | 0.6893 | 0.051* | |
H25B | 0.1325 | 0.5820 | 0.7648 | 0.051* | |
C26 | 0.0522 (8) | 0.6162 (3) | 0.5720 (7) | 0.0433 (15) | |
H26A | −0.0349 | 0.6433 | 0.5874 | 0.052* | |
H26B | 0.0069 | 0.5714 | 0.5318 | 0.052* | |
C27 | 0.1156 (8) | 0.6560 (3) | 0.4746 (6) | 0.0361 (13) | |
H27A | 0.1950 | 0.6272 | 0.4514 | 0.043* | |
H27B | 0.0263 | 0.6662 | 0.3920 | 0.043* | |
C29 | 0.1158 (7) | 0.8005 (3) | 0.3367 (6) | 0.0317 (12) | |
H29 | 0.0177 | 0.7711 | 0.3160 | 0.038* | |
C30 | 0.1550 (8) | 0.8094 (4) | 0.2104 (7) | 0.0463 (16) | |
H30A | 0.1732 | 0.7635 | 0.1766 | 0.056* | |
H30B | 0.2541 | 0.8370 | 0.2286 | 0.056* | |
C31 | 0.0151 (9) | 0.8464 (5) | 0.1056 (8) | 0.061 (2) | |
H31A | 0.0441 | 0.8545 | 0.0249 | 0.074* | |
H31B | −0.0802 | 0.8160 | 0.0809 | 0.074* | |
C32 | −0.0264 (9) | 0.9144 (4) | 0.1539 (8) | 0.057 (2) | |
H32A | −0.1222 | 0.9340 | 0.0862 | 0.069* | |
H32B | 0.0632 | 0.9473 | 0.1667 | 0.069* | |
C33 | −0.0591 (9) | 0.9056 (4) | 0.2842 (8) | 0.057 (2) | |
H33A | −0.1579 | 0.8780 | 0.2686 | 0.069* | |
H33B | −0.0765 | 0.9517 | 0.3178 | 0.069* | |
C34 | 0.0797 (9) | 0.8696 (4) | 0.3879 (7) | 0.0471 (16) | |
H34A | 0.1758 | 0.8994 | 0.4106 | 0.057* | |
H34B | 0.0525 | 0.8622 | 0.4696 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01949 (15) | 0.02969 (16) | 0.0492 (2) | 0.0012 (2) | 0.01167 (12) | −0.0076 (2) |
Cl1 | 0.153 (4) | 0.124 (3) | 0.103 (2) | −0.027 (2) | 0.065 (2) | −0.0111 (19) |
Cl2 | 0.164 (3) | 0.085 (2) | 0.0910 (19) | −0.061 (2) | −0.029 (2) | 0.0079 (15) |
F1 | 0.031 (2) | 0.050 (2) | 0.128 (4) | −0.0105 (18) | 0.031 (2) | 0.006 (2) |
F2 | 0.045 (3) | 0.035 (2) | 0.115 (4) | −0.0008 (18) | 0.037 (3) | 0.002 (2) |
F3 | 0.062 (3) | 0.057 (3) | 0.110 (4) | 0.019 (2) | 0.045 (3) | 0.048 (3) |
F4 | 0.049 (3) | 0.063 (3) | 0.134 (5) | 0.010 (2) | 0.049 (3) | 0.024 (3) |
O1 | 0.021 (2) | 0.045 (2) | 0.058 (3) | −0.0021 (18) | 0.022 (2) | −0.004 (2) |
O2 | 0.027 (2) | 0.040 (2) | 0.050 (3) | −0.0052 (19) | 0.020 (2) | −0.010 (2) |
O3 | 0.024 (2) | 0.0246 (19) | 0.053 (3) | 0.0051 (16) | 0.0032 (18) | −0.0040 (17) |
O4 | 0.031 (2) | 0.039 (2) | 0.054 (3) | 0.0095 (19) | 0.013 (2) | −0.0006 (19) |
N1 | 0.021 (2) | 0.029 (2) | 0.031 (2) | −0.0031 (18) | 0.0116 (19) | −0.0055 (17) |
C1 | 0.020 (2) | 0.027 (3) | 0.052 (3) | 0.006 (2) | 0.011 (2) | 0.001 (2) |
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) |
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) |
C7 | 0.028 (3) | 0.022 (2) | 0.042 (3) | 0.005 (2) | 0.009 (2) | −0.007 (2) |
C8 | 0.032 (3) | 0.047 (3) | 0.036 (3) | −0.006 (3) | 0.016 (3) | −0.001 (2) |
C9 | 0.038 (4) | 0.053 (4) | 0.040 (4) | 0.002 (3) | 0.010 (3) | 0.004 (3) |
C10 | 0.030 (3) | 0.039 (3) | 0.046 (4) | 0.006 (3) | 0.003 (3) | −0.004 (3) |
C11 | 0.023 (3) | 0.038 (3) | 0.053 (4) | −0.001 (2) | 0.014 (3) | −0.004 (3) |
C12 | 0.024 (3) | 0.033 (3) | 0.043 (3) | −0.006 (2) | 0.010 (2) | −0.006 (2) |
C13 | 0.028 (3) | 0.084 (6) | 0.050 (4) | 0.015 (4) | 0.004 (3) | −0.030 (4) |
C14 | 0.061 (5) | 0.066 (5) | 0.059 (5) | −0.006 (4) | 0.019 (4) | 0.005 (4) |
C15 | 0.098 (8) | 0.067 (5) | 0.070 (6) | 0.022 (5) | 0.045 (5) | −0.003 (4) |
C16 | 0.039 (4) | 0.049 (4) | 0.068 (5) | 0.013 (3) | 0.027 (3) | −0.008 (3) |
C17 | 0.026 (3) | 0.059 (4) | 0.047 (4) | 0.014 (3) | 0.015 (3) | −0.004 (3) |
C18 | 0.022 (3) | 0.037 (3) | 0.046 (3) | −0.005 (2) | 0.009 (2) | −0.008 (3) |
C19 | 0.031 (3) | 0.049 (4) | 0.066 (5) | −0.001 (3) | 0.027 (3) | 0.005 (3) |
C20 | 0.032 (4) | 0.026 (3) | 0.050 (4) | 0.008 (2) | 0.014 (3) | −0.003 (2) |
C21 | 0.035 (3) | 0.037 (3) | 0.054 (4) | 0.005 (3) | 0.016 (3) | 0.010 (3) |
C22 | 0.032 (3) | 0.021 (2) | 0.045 (3) | 0.001 (2) | 0.022 (3) | −0.001 (2) |
C23 | 0.052 (4) | 0.042 (3) | 0.034 (3) | −0.021 (3) | 0.011 (3) | 0.000 (3) |
C24 | 0.065 (5) | 0.047 (4) | 0.047 (4) | −0.019 (3) | 0.026 (4) | −0.004 (3) |
C25 | 0.058 (4) | 0.025 (3) | 0.055 (4) | −0.007 (3) | 0.033 (3) | 0.002 (3) |
C26 | 0.040 (4) | 0.032 (3) | 0.064 (4) | −0.009 (3) | 0.025 (3) | −0.003 (3) |
C27 | 0.031 (3) | 0.030 (3) | 0.047 (3) | −0.009 (2) | 0.013 (3) | −0.005 (3) |
C29 | 0.023 (3) | 0.031 (3) | 0.039 (3) | −0.006 (2) | 0.008 (2) | 0.001 (2) |
C30 | 0.031 (3) | 0.066 (5) | 0.043 (4) | −0.005 (3) | 0.012 (3) | 0.008 (3) |
C31 | 0.034 (4) | 0.093 (6) | 0.050 (4) | −0.012 (4) | 0.004 (3) | 0.025 (4) |
C32 | 0.034 (4) | 0.050 (4) | 0.073 (5) | −0.010 (3) | −0.003 (3) | 0.030 (4) |
C33 | 0.046 (5) | 0.043 (4) | 0.075 (5) | 0.011 (3) | 0.009 (4) | 0.011 (3) |
C34 | 0.041 (4) | 0.043 (4) | 0.055 (4) | 0.008 (3) | 0.014 (3) | 0.003 (3) |
Sn1—C1 | 2.147 (5) | C12—H12 | 0.9500 |
Sn1—C7 | 2.136 (6) | C13—C14 | 1.527 (7) |
Sn1—C13 | 2.117 (6) | C13—C17 | 1.530 (7) |
Sn1—O1 | 2.287 (4) | C13—H13 | 1.0000 |
Sn1—O3 | 2.249 (4) | C14—C15 | 1.569 (7) |
Cl1—C19 | 1.660 (6) | C14—H14A | 0.9900 |
Cl2—C21 | 1.657 (6) | C14—H14B | 0.9900 |
F1—C19 | 1.319 (6) | C15—C16 | 1.539 (7) |
F2—C19 | 1.331 (6) | C15—H15A | 0.9900 |
F3—C21 | 1.311 (6) | C15—H15B | 0.9900 |
F4—C21 | 1.334 (6) | C16—C17 | 1.541 (6) |
O1—C18 | 1.246 (7) | C16—H16A | 0.9900 |
O2—C18 | 1.249 (7) | C16—H16B | 0.9900 |
O3—C20 | 1.257 (7) | C17—H17A | 0.9900 |
O4—C20 | 1.235 (8) | C17—H17B | 0.9900 |
N1—C29 | 1.508 (7) | C18—C19 | 1.540 (9) |
N1—C22 | 1.508 (7) | C20—C21 | 1.506 (9) |
N1—H1N1 | 0.8800 | C22—C27 | 1.512 (8) |
N1—H1N2 | 0.8800 | C22—C23 | 1.534 (9) |
C1—C2 | 1.391 (9) | C22—H22 | 1.0000 |
C1—C2' | 1.394 (9) | C23—C24 | 1.522 (9) |
C1—C6' | 1.396 (9) | C23—H23A | 0.9900 |
C1—C6 | 1.401 (9) | C23—H23B | 0.9900 |
C2—C3 | 1.387 (9) | C24—C25 | 1.524 (9) |
C2—H2 | 0.9500 | C24—H24A | 0.9900 |
C3—C4 | 1.383 (9) | C24—H24B | 0.9900 |
C3—H3 | 0.9500 | C25—C26 | 1.499 (10) |
C4—C5 | 1.388 (9) | C25—H25A | 0.9900 |
C4—H4 | 0.9500 | C25—H25B | 0.9900 |
C5—C6 | 1.393 (9) | C26—C27 | 1.542 (9) |
C5—H5 | 0.9500 | C26—H26A | 0.9900 |
C6—H6 | 0.9500 | C26—H26B | 0.9900 |
C2'—C3' | 1.386 (9) | C27—H27A | 0.9900 |
C2'—H2' | 0.9500 | C27—H27B | 0.9900 |
C3'—C4' | 1.382 (9) | C29—C30 | 1.510 (8) |
C3'—H3' | 0.9500 | C29—C34 | 1.516 (9) |
C4'—C5' | 1.387 (9) | C29—H29 | 1.0000 |
C4'—H4' | 0.9500 | C30—C31 | 1.543 (10) |
C5'—C6' | 1.393 (9) | C30—H30A | 0.9900 |
C5'—H5' | 0.9500 | C30—H30B | 0.9900 |
C6'—H6' | 0.9500 | C31—C32 | 1.499 (12) |
C7—C8 | 1.388 (9) | C31—H31A | 0.9900 |
C7—C12 | 1.396 (8) | C31—H31B | 0.9900 |
C8—C9 | 1.410 (9) | C32—C33 | 1.523 (11) |
C8—H8 | 0.9500 | C32—H32A | 0.9900 |
C9—C10 | 1.365 (10) | C32—H32B | 0.9900 |
C9—H9 | 0.9500 | C33—C34 | 1.523 (10) |
C10—C11 | 1.361 (9) | C33—H33A | 0.9900 |
C10—H10 | 0.9500 | C33—H33B | 0.9900 |
C11—C12 | 1.396 (9) | C34—H34A | 0.9900 |
C11—H11 | 0.9500 | C34—H34B | 0.9900 |
C1—Sn1—C7 | 119.2 (2) | C13—C17—C16 | 105.1 (4) |
C1—Sn1—C13 | 121.7 (2) | C13—C17—H17A | 110.7 |
C1—Sn1—O1 | 91.3 (2) | C16—C17—H17A | 110.7 |
C1—Sn1—O3 | 90.9 (2) | C13—C17—H17B | 110.7 |
C7—Sn1—C13 | 118.9 (2) | C16—C17—H17B | 110.7 |
C7—Sn1—O1 | 90.6 (2) | H17A—C17—H17B | 108.8 |
C7—Sn1—O3 | 87.8 (2) | O1—C18—O2 | 129.2 (6) |
C13—Sn1—O1 | 82.8 (3) | O1—C18—C19 | 114.5 (5) |
C13—Sn1—O3 | 96.5 (3) | O2—C18—C19 | 116.3 (5) |
O1—Sn1—O3 | 177.7 (2) | F1—C19—F2 | 108.8 (5) |
C18—O1—Sn1 | 119.3 (4) | F1—C19—C18 | 111.3 (5) |
C20—O3—Sn1 | 117.0 (4) | F2—C19—C18 | 114.0 (5) |
C29—N1—C22 | 113.5 (4) | F1—C19—Cl1 | 106.0 (4) |
C29—N1—H1N1 | 108.9 | F2—C19—Cl1 | 105.0 (5) |
C29—N1—H1N1 | 108.9 | C18—C19—Cl1 | 111.2 (5) |
C22—N1—H1N2 | 108.9 | O4—C20—O3 | 128.7 (6) |
C22—N1—H1N2 | 108.9 | O4—C20—C21 | 116.7 (5) |
H1N1—N1—H1N2 | 107.7 | O3—C20—C21 | 114.6 (6) |
C2'—C1—C6' | 121 (3) | F3—C21—F4 | 107.1 (5) |
C2—C1—C6 | 115 (3) | F3—C21—C20 | 114.3 (5) |
C2—C1—Sn1 | 123.3 (19) | F4—C21—C20 | 112.3 (5) |
C2'—C1—Sn1 | 120.4 (18) | F3—C21—Cl2 | 103.7 (5) |
C6'—C1—Sn1 | 118 (2) | F4—C21—Cl2 | 110.4 (5) |
C6—C1—Sn1 | 122 (2) | C20—C21—Cl2 | 108.6 (4) |
C3—C2—C1 | 125 (3) | N1—C22—C27 | 110.2 (5) |
C3—C2—H2 | 117.5 | N1—C22—C23 | 111.1 (5) |
C1—C2—H2 | 117.5 | C27—C22—C23 | 110.1 (5) |
C4—C3—C2 | 116 (3) | N1—C22—H22 | 108.4 |
C4—C3—H3 | 122.1 | C27—C22—H22 | 108.4 |
C2—C3—H3 | 122.1 | C23—C22—H22 | 108.4 |
C3—C4—C5 | 124 (3) | C24—C23—C22 | 109.0 (6) |
C3—C4—H4 | 117.8 | C24—C23—H23A | 109.9 |
C5—C4—H4 | 117.8 | C22—C23—H23A | 109.9 |
C4—C5—C6 | 116 (3) | C24—C23—H23B | 109.9 |
C4—C5—H5 | 122.0 | C22—C23—H23B | 109.9 |
C6—C5—H5 | 122.0 | H23A—C23—H23B | 108.3 |
C5—C6—C1 | 124 (3) | C23—C24—C25 | 111.7 (5) |
C5—C6—H6 | 118.0 | C23—C24—H24A | 109.3 |
C1—C6—H6 | 118.0 | C25—C24—H24A | 109.3 |
C3'—C2'—C1 | 118 (3) | C23—C24—H24B | 109.3 |
C3'—C2'—H2' | 120.9 | C25—C24—H24B | 109.3 |
C1—C2'—H2' | 120.9 | H24A—C24—H24B | 107.9 |
C4'—C3'—C2' | 122 (3) | C26—C25—C24 | 111.5 (5) |
C4'—C3'—H3' | 118.8 | C26—C25—H25A | 109.3 |
C2'—C3'—H3' | 118.8 | C24—C25—H25A | 109.3 |
C3'—C4'—C5' | 118 (3) | C26—C25—H25B | 109.3 |
C3'—C4'—H4' | 121.2 | C24—C25—H25B | 109.3 |
C5'—C4'—H4' | 121.2 | H25A—C25—H25B | 108.0 |
C4'—C5'—C6' | 123 (3) | C25—C26—C27 | 112.1 (5) |
C4'—C5'—H5' | 118.7 | C25—C26—H26A | 109.2 |
C6'—C5'—H5' | 118.7 | C27—C26—H26A | 109.2 |
C5'—C6'—C1 | 118 (3) | C25—C26—H26B | 109.2 |
C5'—C6'—H6' | 121.2 | C27—C26—H26B | 109.2 |
C1—C6'—H6' | 121.2 | H26A—C26—H26B | 107.9 |
C8—C7—C12 | 118.7 (5) | C22—C27—C26 | 109.6 (5) |
C8—C7—Sn1 | 119.9 (4) | C22—C27—H27A | 109.8 |
C12—C7—Sn1 | 121.2 (4) | C26—C27—H27A | 109.8 |
C7—C8—C9 | 119.3 (6) | C22—C27—H27B | 109.8 |
C7—C8—H8 | 120.4 | C26—C27—H27B | 109.8 |
C9—C8—H8 | 120.4 | H27A—C27—H27B | 108.2 |
C10—C9—C8 | 120.8 (6) | N1—C29—C30 | 111.2 (5) |
C10—C9—H9 | 119.6 | N1—C29—C34 | 110.6 (5) |
C8—C9—H9 | 119.6 | C30—C29—C34 | 111.2 (5) |
C11—C10—C9 | 120.6 (6) | N1—C29—H29 | 107.9 |
C11—C10—H10 | 119.7 | C30—C29—H29 | 107.9 |
C9—C10—H10 | 119.7 | C34—C29—H29 | 107.9 |
C10—C11—C12 | 119.7 (6) | C29—C30—C31 | 109.5 (6) |
C10—C11—H11 | 120.1 | C29—C30—H30A | 109.8 |
C12—C11—H11 | 120.1 | C31—C30—H30A | 109.8 |
C7—C12—C11 | 120.9 (6) | C29—C30—H30B | 109.8 |
C7—C12—H12 | 119.5 | C31—C30—H30B | 109.8 |
C11—C12—H12 | 119.5 | H30A—C30—H30B | 108.2 |
C14—C13—C17 | 105.1 (5) | C32—C31—C30 | 112.7 (7) |
C14—C13—Sn1 | 123.1 (5) | C32—C31—H31A | 109.1 |
C17—C13—Sn1 | 114.6 (4) | C30—C31—H31A | 109.1 |
C14—C13—H13 | 104.0 | C32—C31—H31B | 109.1 |
C17—C13—H13 | 104.0 | C30—C31—H31B | 109.1 |
Sn1—C13—H13 | 104.0 | H31A—C31—H31B | 107.8 |
C13—C14—C15 | 105.2 (5) | C31—C32—C33 | 111.1 (6) |
C13—C14—H14A | 110.7 | C31—C32—H32A | 109.4 |
C15—C14—H14A | 110.7 | C33—C32—H32A | 109.4 |
C13—C14—H14B | 110.7 | C31—C32—H32B | 109.4 |
C15—C14—H14B | 110.7 | C33—C32—H32B | 109.4 |
H14A—C14—H14B | 108.8 | H32A—C32—H32B | 108.0 |
C16—C15—C14 | 105.8 (4) | C32—C33—C34 | 111.3 (6) |
C16—C15—H15A | 110.6 | C32—C33—H33A | 109.4 |
C14—C15—H15A | 110.6 | C34—C33—H33A | 109.4 |
C16—C15—H15B | 110.6 | C32—C33—H33B | 109.4 |
C14—C15—H15B | 110.6 | C34—C33—H33B | 109.4 |
H15A—C15—H15B | 108.7 | H33A—C33—H33B | 108.0 |
C15—C16—C17 | 107.4 (4) | C29—C34—C33 | 110.9 (6) |
C15—C16—H16A | 110.2 | C29—C34—H34A | 109.5 |
C17—C16—H16A | 110.2 | C33—C34—H34A | 109.5 |
C15—C16—H16B | 110.2 | C29—C34—H34B | 109.5 |
C17—C16—H16B | 110.2 | C33—C34—H34B | 109.5 |
H16A—C16—H16B | 108.5 | H34A—C34—H34B | 108.1 |
C13—Sn1—O1—C18 | 169.9 (5) | C8—C9—C10—C11 | −1.3 (10) |
C7—Sn1—O1—C18 | 50.8 (5) | C9—C10—C11—C12 | 0.6 (10) |
C1—Sn1—O1—C18 | −68.4 (5) | C8—C7—C12—C11 | −1.0 (9) |
C13—Sn1—O3—C20 | 60.0 (5) | Sn1—C7—C12—C11 | 173.6 (4) |
C7—Sn1—O3—C20 | 178.9 (5) | C10—C11—C12—C7 | 0.6 (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—C14 | 124.4 (6) |
C7—Sn1—C1—C2 | 77.8 (13) | O3—Sn1—C13—C14 | 29.2 (7) |
O3—Sn1—C1—C2 | −10.2 (13) | O1—Sn1—C13—C14 | −148.5 (7) |
O1—Sn1—C1—C2 | 169.2 (13) | C7—Sn1—C13—C17 | 168.2 (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—C17 | 81.6 (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—C16 | 19.2 (9) |
O3—Sn1—C1—C6' | 155.1 (11) | C14—C15—C16—C17 | 1.1 (9) |
O1—Sn1—C1—C6' | −25.5 (11) | C14—C13—C17—C16 | 33.2 (8) |
C13—Sn1—C1—C6 | 70.4 (11) | Sn1—C13—C17—C16 | 171.5 (5) |
C7—Sn1—C1—C6 | −103.4 (11) | C15—C16—C17—C13 | −21.0 (8) |
O3—Sn1—C1—C6 | 168.6 (11) | Sn1—O1—C18—O2 | 6.9 (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—C3 | 13.2 (19) | O2—C18—C19—F1 | 123.1 (6) |
C6—C1—C2—C3 | −0.2 (3) | O1—C18—C19—F2 | 180.0 (5) |
Sn1—C1—C2—C3 | 178.7 (11) | O2—C18—C19—F2 | −0.5 (8) |
C1—C2—C3—C4 | 0.0 (3) | O1—C18—C19—Cl1 | 61.5 (6) |
C2—C3—C4—C5 | 0.0 (7) | O2—C18—C19—Cl1 | −118.9 (5) |
C3—C4—C5—C6 | 0.2 (9) | Sn1—O3—C20—O4 | 1.0 (9) |
C4—C5—C6—C1 | −0.5 (9) | Sn1—O3—C20—C21 | 179.9 (4) |
C2—C1—C6—C5 | 0.5 (7) | O4—C20—C21—F3 | 4.9 (8) |
C2'—C1—C6—C5 | 13 (2) | O3—C20—C21—F3 | −174.1 (6) |
C6'—C1—C6—C5 | −102 (19) | O4—C20—C21—F4 | 127.2 (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—Cl2 | 70.6 (6) |
C6—C1—C2'—C3' | −13 (2) | C29—N1—C22—C27 | 76.9 (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—C24 | 177.0 (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—C25 | 57.4 (8) |
C4'—C5'—C6'—C1 | −0.5 (8) | C23—C24—C25—C26 | −54.2 (9) |
C2—C1—C6'—C5' | −12 (3) | C24—C25—C26—C27 | 53.0 (7) |
C2'—C1—C6'—C5' | 0.5 (6) | N1—C22—C27—C26 | −177.6 (5) |
C6—C1—C6'—C5' | 72 (18) | C23—C22—C27—C26 | 59.5 (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—C8 | 127.6 (4) | C22—N1—C29—C34 | 84.5 (6) |
O3—Sn1—C7—C8 | −142.5 (5) | N1—C29—C30—C31 | 179.5 (6) |
O1—Sn1—C7—C8 | 35.8 (5) | C34—C29—C30—C31 | −56.8 (7) |
C13—Sn1—C7—C12 | 139.2 (5) | C29—C30—C31—C32 | 55.6 (8) |
C1—Sn1—C7—C12 | −46.9 (5) | C30—C31—C32—C33 | −54.3 (8) |
O3—Sn1—C7—C12 | 42.9 (4) | C31—C32—C33—C34 | 54.0 (9) |
O1—Sn1—C7—C12 | −138.8 (4) | N1—C29—C34—C33 | −177.8 (5) |
C12—C7—C8—C9 | 0.3 (9) | C30—C29—C34—C33 | 58.1 (8) |
Sn1—C7—C8—C9 | −174.4 (5) | C32—C33—C34—C29 | −55.9 (8) |
C7—C8—C9—C10 | 0.9 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O2 | 0.88 | 1.88 | 2.758 (6) | 173 |
N1—H1N2···O4i | 0.88 | 1.93 | 2.804 (6) | 169 |
Symmetry code: (i) −x+1, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | (C12H24N)[Sn(C5H9)(C6H5)2(C2ClF2O2)] |
Mr | 783.27 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 8.8610 (2), 19.3132 (3), 10.6823 (2) |
β (°) | 109.385 (1) |
V (Å3) | 1724.47 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.95 |
Crystal size (mm) | 0.30 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.679, 0.870 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18017, 7831, 6637 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.132, 1.04 |
No. of reflections | 7831 |
No. of parameters | 421 |
No. of restraints | 41 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.11, −0.71 |
Absolute structure | Flack (1983), 3766 Friedel pairs |
Absolute structure parameter | −0.03 (3) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Sn1—C1 | 2.147 (5) | Sn1—O1 | 2.287 (4) |
Sn1—C7 | 2.136 (6) | Sn1—O3 | 2.249 (4) |
Sn1—C13 | 2.117 (6) | ||
C1—Sn1—C7 | 119.2 (2) | C7—Sn1—O1 | 90.6 (2) |
C1—Sn1—C13 | 121.7 (2) | C7—Sn1—O3 | 87.8 (2) |
C1—Sn1—O1 | 91.3 (2) | C13—Sn1—O1 | 82.8 (3) |
C1—Sn1—O3 | 90.9 (2) | C13—Sn1—O3 | 96.5 (3) |
C7—Sn1—C13 | 118.9 (2) | O1—Sn1—O3 | 177.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O2 | 0.88 | 1.88 | 2.758 (6) | 173 |
N1—H1N2···O4i | 0.88 | 1.93 | 2.804 (6) | 169 |
Symmetry code: (i) −x+1, y+1/2, −z+1. |
Acknowledgements
The authors thank the University of Malaya for funding this study (grant No. SF022155/2007A) and also for the purchase of the diffractometer.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Teo, Y. Y., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m726–m727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23. CrossRef CAS Web of Science Google Scholar
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116. Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.