metal-organic compounds
3-(Piperidin-1-yl)propionic acid, C8H15NO2, forms a 1:2 adduct, bis-chlorotriphenyl[3-(piperidinium-1-yl)propionato]tin(IV (C8H15NO2)[Sn(C6H5)3Cl]2, with triphenyltin chloride, [Sn(C6H5)3Cl]. The acidic H atom is transferred to the imine N atom and an N—HO intramolecular hydrogen bond is formed. The carboxylate group bridges the two Sn atoms.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010792/hb6170sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010792/hb6170Isup2.hkl |
CCDC reference: 139427
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1997) and KRYSTAL (Hazell, 1995); program(s) used to refine structure: modified ORFLS (Busing et al., 1962) and KRYSTAL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL; software used to prepare material for publication: KRYSTAL.
3-(Piperidin-1-yl)propionic acid–triphenyltin chloride (1/2) top
Crystal data top
(C8H15NO2)[Sn(C6H5)3Cl]2 | F(000) = 1864 |
Mr = 928.13 | Dx = 1.538 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6353 reflections |
a = 13.223 (3) Å | θ = 2.0–29.8° |
b = 15.779 (3) Å | µ = 1.42 mm−1 |
c = 19.574 (4) Å | T = 120 K |
β = 101.065 (4)° | Block, colourless |
V = 4008 (1) Å3 | 0.36 × 0.22 × 0.17 mm |
Z = 4 |
Data collection top
Siemens SMART CCD area-detector diffractometer | 10724 independent reflections |
Radiation source: x-ray tube | 7497 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 29.5°, θmin = 2.0° |
Absorption correction: integration (XPREP; Siemens, 1995) | h = −18→17 |
Tmin = 0.683, Tmax = 0.802 | k = −18→22 |
27396 measured reflections | l = −27→23 |
Refinement top
Refinement on F | 0 constraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.022 | w = 1/{[σcs(F2) + 1.03F2]1/2-|F|}2 |
wR(F2) = 0.025 | (Δ/σ)max = 0.003 |
S = 0.81 | Δρmax = 0.81 (7) e Å−3 |
7497 reflections | Δρmin = −0.65 (7) e Å−3 |
465 parameters | Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction coefficient: 24 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.36449 (1) | 0.03856 (1) | 0.66912 (1) | 0.0182 (1) | |
Sn2 | 0.04048 (1) | 0.07856 (1) | 0.81628 (1) | 0.0174 (1) | |
Cl1 | 0.50796 (5) | −0.06834 (4) | 0.67486 (3) | 0.0302 (3) | |
Cl2 | −0.04250 (5) | 0.08458 (4) | 0.92033 (3) | 0.0292 (3) | |
O1 | 0.2367 (1) | 0.1461 (1) | 0.6630 (1) | 0.020 (1) | |
O2 | 0.1352 (1) | 0.0769 (1) | 0.7229 (1) | 0.020 (1) | |
N | 0.1996 (1) | 0.3224 (1) | 0.6449 (1) | 0.022 (1) | |
C1 | 0.1542 (2) | 0.1381 (1) | 0.6870 (1) | 0.019 (1) | |
C2 | 0.0748 (2) | 0.2083 (1) | 0.6670 (1) | 0.024 (1) | |
C3 | 0.1159 (2) | 0.2970 (2) | 0.6835 (1) | 0.027 (1) | |
C4 | 0.2568 (2) | 0.3982 (1) | 0.6803 (1) | 0.029 (1) | |
C5 | 0.3405 (2) | 0.4278 (2) | 0.6435 (1) | 0.031 (1) | |
C6 | 0.2994 (2) | 0.4447 (2) | 0.5672 (1) | 0.036 (2) | |
C7 | 0.2447 (2) | 0.3664 (2) | 0.5328 (1) | 0.039 (2) | |
C8 | 0.1584 (2) | 0.3400 (2) | 0.5691 (1) | 0.033 (1) | |
C11 | 0.4307 (2) | 0.1252 (1) | 0.6067 (1) | 0.022 (1) | |
C12 | 0.4495 (2) | 0.1000 (2) | 0.5419 (1) | 0.031 (1) | |
C13 | 0.5044 (2) | 0.1521 (2) | 0.5045 (1) | 0.040 (2) | |
C14 | 0.5428 (2) | 0.2286 (2) | 0.5318 (2) | 0.040 (2) | |
C15 | 0.5228 (2) | 0.2557 (2) | 0.5944 (1) | 0.034 (2) | |
C16 | 0.4664 (2) | 0.2051 (1) | 0.6311 (1) | 0.026 (1) | |
C21 | 0.4049 (2) | 0.0549 (1) | 0.7788 (1) | 0.019 (1) | |
C22 | 0.3712 (2) | −0.0018 (1) | 0.8243 (1) | 0.023 (1) | |
C23 | 0.4000 (2) | 0.0082 (2) | 0.8960 (1) | 0.026 (1) | |
C24 | 0.4642 (2) | 0.0744 (2) | 0.9233 (1) | 0.028 (1) | |
C25 | 0.5000 (2) | 0.1301 (2) | 0.8788 (1) | 0.027 (1) | |
C26 | 0.4703 (2) | 0.1209 (1) | 0.8072 (1) | 0.023 (1) | |
C31 | 0.2521 (2) | −0.0495 (1) | 0.6176 (1) | 0.023 (1) | |
C32 | 0.2657 (2) | −0.1361 (2) | 0.6297 (1) | 0.031 (1) | |
C33 | 0.1967 (2) | −0.1948 (2) | 0.5932 (2) | 0.038 (2) | |
C34 | 0.1145 (2) | −0.1681 (2) | 0.5442 (1) | 0.039 (2) | |
C35 | 0.0996 (2) | −0.0824 (2) | 0.5314 (2) | 0.041 (2) | |
C36 | 0.1678 (2) | −0.0232 (2) | 0.5684 (1) | 0.032 (1) | |
C41 | 0.1053 (2) | −0.0444 (1) | 0.8384 (1) | 0.021 (1) | |
C42 | 0.1213 (2) | −0.0981 (1) | 0.7847 (1) | 0.026 (1) | |
C43 | 0.1618 (2) | −0.1786 (2) | 0.7996 (2) | 0.033 (2) | |
C44 | 0.1873 (2) | −0.2066 (2) | 0.8672 (2) | 0.039 (2) | |
C45 | 0.1712 (2) | −0.1544 (2) | 0.9209 (2) | 0.038 (2) | |
C46 | 0.1295 (2) | −0.0734 (1) | 0.9067 (1) | 0.028 (1) | |
C51 | −0.1013 (2) | 0.0813 (1) | 0.7421 (1) | 0.021 (1) | |
C52 | −0.1934 (2) | 0.1033 (2) | 0.7629 (1) | 0.029 (1) | |
C53 | −0.2869 (2) | 0.1006 (2) | 0.7158 (2) | 0.036 (2) | |
C54 | −0.2908 (2) | 0.0763 (2) | 0.6479 (2) | 0.035 (2) | |
C55 | −0.2003 (2) | 0.0554 (2) | 0.6264 (1) | 0.031 (1) | |
C56 | −0.1062 (2) | 0.0570 (1) | 0.6734 (1) | 0.025 (1) | |
C61 | 0.1256 (2) | 0.1919 (1) | 0.8457 (1) | 0.020 (1) | |
C62 | 0.0755 (2) | 0.2631 (2) | 0.8652 (1) | 0.029 (1) | |
C63 | 0.1307 (2) | 0.3374 (2) | 0.8853 (2) | 0.038 (2) | |
C64 | 0.2351 (2) | 0.3415 (2) | 0.8857 (2) | 0.038 (2) | |
C65 | 0.2863 (2) | 0.2711 (2) | 0.8667 (1) | 0.032 (1) | |
C66 | 0.2314 (2) | 0.1967 (1) | 0.8468 (1) | 0.025 (1) | |
H1N | 0.244 (2) | 0.274 (2) | 0.647 (1) | 0.041 (8)* | |
H2A | 0.0201 | 0.1990 | 0.6913 | 0.029* | |
H2B | 0.0491 | 0.2048 | 0.6183 | 0.029* | |
H3A | 0.0604 | 0.3358 | 0.6717 | 0.033* | |
H3B | 0.1430 | 0.3003 | 0.7320 | 0.033* | |
H4A | 0.2870 | 0.3832 | 0.7267 | 0.035* | |
H4B | 0.2092 | 0.4432 | 0.6809 | 0.035* | |
H5A | 0.3923 | 0.3854 | 0.6476 | 0.038* | |
H5B | 0.3697 | 0.4786 | 0.6648 | 0.038* | |
H6A | 0.3550 | 0.4587 | 0.5450 | 0.043* | |
H6B | 0.2521 | 0.4906 | 0.5628 | 0.043* | |
H7A | 0.2928 | 0.3213 | 0.5352 | 0.047* | |
H7B | 0.2168 | 0.3787 | 0.4854 | 0.047* | |
H8A | 0.1089 | 0.3842 | 0.5652 | 0.040* | |
H8B | 0.1266 | 0.2902 | 0.5477 | 0.040* | |
H12 | 0.4246 | 0.0468 | 0.5231 | 0.038* | |
H13 | 0.5154 | 0.1347 | 0.4600 | 0.048* | |
H14 | 0.5831 | 0.2627 | 0.5072 | 0.048* | |
H15 | 0.5476 | 0.3092 | 0.6126 | 0.041* | |
H16 | 0.4516 | 0.2252 | 0.6739 | 0.032* | |
H22 | 0.3281 | −0.0479 | 0.8060 | 0.027* | |
H23 | 0.3757 | −0.0305 | 0.9264 | 0.031* | |
H24 | 0.4834 | 0.0815 | 0.9722 | 0.033* | |
H25 | 0.5452 | 0.1748 | 0.8973 | 0.033* | |
H26 | 0.4947 | 0.1600 | 0.7772 | 0.028* | |
H32 | 0.3227 | −0.1555 | 0.6633 | 0.037* | |
H33 | 0.2067 | −0.2536 | 0.6024 | 0.045* | |
H34 | 0.0681 | −0.2082 | 0.5192 | 0.047* | |
H35 | 0.0429 | −0.0636 | 0.4974 | 0.049* | |
H36 | 0.1562 | 0.0356 | 0.5598 | 0.038* | |
H42 | 0.1043 | −0.0794 | 0.7377 | 0.031* | |
H43 | 0.1721 | −0.2147 | 0.7627 | 0.040* | |
H44 | 0.2158 | −0.2615 | 0.8770 | 0.047* | |
H45 | 0.1885 | −0.1737 | 0.9676 | 0.045* | |
H46 | 0.1177 | −0.0382 | 0.9437 | 0.034* | |
H52 | −0.1922 | 0.1202 | 0.8096 | 0.034* | |
H53 | −0.3487 | 0.1157 | 0.7308 | 0.043* | |
H54 | −0.3549 | 0.0740 | 0.6162 | 0.042* | |
H55 | −0.2020 | 0.0398 | 0.5793 | 0.037* | |
H56 | −0.0449 | 0.0412 | 0.6581 | 0.030* | |
H62 | 0.0036 | 0.2611 | 0.8648 | 0.034* | |
H63 | 0.0961 | 0.3856 | 0.8988 | 0.045* | |
H64 | 0.2719 | 0.3924 | 0.8990 | 0.046* | |
H65 | 0.3582 | 0.2735 | 0.8673 | 0.038* | |
H66 | 0.2665 | 0.1485 | 0.8339 | 0.030* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01610 (8) | 0.01943 (8) | 0.01838 (8) | −0.00024 (6) | 0.00178 (6) | −0.00330 (6) |
Sn2 | 0.01639 (8) | 0.01617 (8) | 0.01955 (9) | −0.00007 (6) | 0.00360 (6) | 0.00101 (6) |
Cl1 | 0.0252 (3) | 0.0302 (3) | 0.0340 (4) | 0.0077 (2) | 0.0023 (3) | −0.0067 (3) |
Cl2 | 0.0332 (3) | 0.0320 (3) | 0.0254 (3) | 0.0021 (3) | 0.0131 (3) | 0.0028 (2) |
O1 | 0.016 (1) | 0.021 (1) | 0.024 (1) | 0.001 (1) | 0.006 (1) | 0.001 (1) |
O2 | 0.021 (1) | 0.018 (1) | 0.023 (1) | 0.000 (1) | 0.005 (1) | 0.000 (1) |
N | 0.020 (1) | 0.021 (1) | 0.026 (1) | 0.001 (1) | 0.006 (1) | 0.004 (1) |
C1 | 0.016 (1) | 0.020 (1) | 0.020 (1) | −0.001 (1) | 0.001 (1) | −0.004 (1) |
C2 | 0.016 (1) | 0.024 (1) | 0.033 (1) | 0.000 (1) | 0.006 (1) | 0.007 (1) |
C3 | 0.024 (1) | 0.027 (1) | 0.033 (1) | 0.005 (1) | 0.010 (1) | 0.008 (1) |
C4 | 0.037 (1) | 0.025 (1) | 0.026 (1) | −0.003 (1) | 0.008 (1) | −0.002 (1) |
C5 | 0.030 (1) | 0.030 (1) | 0.033 (2) | −0.010 (1) | 0.005 (1) | −0.004 (1) |
C6 | 0.032 (1) | 0.044 (2) | 0.034 (2) | −0.007 (1) | 0.011 (1) | 0.011 (1) |
C7 | 0.038 (2) | 0.058 (2) | 0.021 (1) | −0.007 (1) | 0.005 (1) | 0.004 (1) |
C8 | 0.028 (1) | 0.043 (2) | 0.026 (1) | −0.006 (1) | −0.003 (1) | 0.003 (1) |
C11 | 0.014 (1) | 0.030 (1) | 0.021 (1) | 0.005 (1) | 0.001 (1) | 0.002 (1) |
C12 | 0.025 (1) | 0.043 (2) | 0.024 (1) | 0.007 (1) | −0.002 (1) | 0.001 (1) |
C13 | 0.039 (2) | 0.064 (2) | 0.019 (1) | 0.014 (1) | 0.009 (1) | 0.013 (1) |
C14 | 0.032 (2) | 0.051 (2) | 0.037 (2) | 0.008 (1) | 0.010 (1) | 0.024 (1) |
C15 | 0.029 (1) | 0.033 (1) | 0.040 (2) | 0.002 (1) | 0.004 (1) | 0.015 (1) |
C16 | 0.024 (1) | 0.028 (1) | 0.028 (1) | 0.004 (1) | 0.007 (1) | 0.005 (1) |
C21 | 0.016 (1) | 0.020 (1) | 0.022 (1) | 0.004 (1) | 0.003 (1) | −0.002 (1) |
C22 | 0.020 (1) | 0.021 (1) | 0.027 (1) | 0.003 (1) | 0.003 (1) | −0.002 (1) |
C23 | 0.026 (1) | 0.027 (1) | 0.025 (1) | 0.005 (1) | 0.006 (1) | 0.004 (1) |
C24 | 0.027 (1) | 0.034 (1) | 0.020 (1) | 0.006 (1) | 0.000 (1) | −0.003 (1) |
C25 | 0.027 (1) | 0.028 (1) | 0.026 (1) | −0.003 (1) | 0.002 (1) | −0.008 (1) |
C26 | 0.023 (1) | 0.024 (1) | 0.024 (1) | −0.001 (1) | 0.004 (1) | −0.002 (1) |
C31 | 0.024 (1) | 0.026 (1) | 0.020 (1) | −0.004 (1) | 0.006 (1) | −0.007 (1) |
C32 | 0.033 (1) | 0.028 (1) | 0.030 (1) | −0.006 (1) | 0.003 (1) | −0.002 (1) |
C33 | 0.049 (2) | 0.029 (1) | 0.038 (2) | −0.013 (1) | 0.013 (1) | −0.005 (1) |
C34 | 0.036 (2) | 0.046 (2) | 0.036 (2) | −0.019 (1) | 0.010 (1) | −0.018 (1) |
C35 | 0.032 (1) | 0.047 (2) | 0.040 (2) | −0.006 (1) | −0.005 (1) | −0.014 (1) |
C36 | 0.029 (1) | 0.032 (1) | 0.033 (2) | −0.001 (1) | −0.001 (1) | −0.009 (1) |
C41 | 0.016 (1) | 0.018 (1) | 0.028 (1) | −0.002 (1) | 0.004 (1) | 0.004 (1) |
C42 | 0.024 (1) | 0.023 (1) | 0.032 (1) | −0.004 (1) | 0.009 (1) | 0.000 (1) |
C43 | 0.030 (1) | 0.020 (1) | 0.053 (2) | −0.003 (1) | 0.016 (1) | −0.004 (1) |
C44 | 0.030 (1) | 0.019 (1) | 0.066 (2) | 0.003 (1) | 0.008 (1) | 0.009 (1) |
C45 | 0.036 (2) | 0.032 (1) | 0.043 (2) | 0.002 (1) | 0.000 (1) | 0.017 (1) |
C46 | 0.027 (1) | 0.025 (1) | 0.031 (1) | −0.001 (1) | 0.003 (1) | 0.003 (1) |
C51 | 0.016 (1) | 0.017 (1) | 0.029 (1) | −0.001 (1) | 0.004 (1) | 0.004 (1) |
C52 | 0.027 (1) | 0.026 (1) | 0.035 (2) | 0.003 (1) | 0.011 (1) | 0.010 (1) |
C53 | 0.020 (1) | 0.039 (2) | 0.049 (2) | 0.007 (1) | 0.007 (1) | 0.018 (1) |
C54 | 0.020 (1) | 0.031 (1) | 0.049 (2) | −0.006 (1) | −0.006 (1) | 0.017 (1) |
C55 | 0.031 (1) | 0.026 (1) | 0.032 (1) | −0.005 (1) | −0.003 (1) | 0.001 (1) |
C56 | 0.020 (1) | 0.023 (1) | 0.032 (1) | −0.003 (1) | 0.002 (1) | −0.001 (1) |
C61 | 0.022 (1) | 0.018 (1) | 0.019 (1) | 0.002 (1) | 0.001 (1) | 0.002 (1) |
C62 | 0.023 (1) | 0.025 (1) | 0.038 (2) | 0.003 (1) | 0.007 (1) | −0.002 (1) |
C63 | 0.033 (1) | 0.019 (1) | 0.061 (2) | 0.004 (1) | 0.008 (1) | −0.009 (1) |
C64 | 0.032 (1) | 0.022 (1) | 0.056 (2) | −0.003 (1) | −0.003 (1) | −0.009 (1) |
C65 | 0.021 (1) | 0.026 (1) | 0.045 (2) | −0.001 (1) | −0.002 (1) | −0.003 (1) |
C66 | 0.022 (1) | 0.019 (1) | 0.032 (1) | 0.002 (1) | 0.000 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
Sn1—Cl1 | 2.525 (1) | C61—C62 | 1.392 (3) |
Sn1—O1 | 2.382 (2) | C61—C66 | 1.397 (3) |
Sn1—C11 | 2.131 (2) | C62—C63 | 1.398 (3) |
Sn1—C21 | 2.126 (2) | C63—C64 | 1.380 (4) |
Sn1—C31 | 2.140 (2) | C64—C65 | 1.388 (4) |
Sn2—Cl2 | 2.494 (1) | C65—C66 | 1.396 (3) |
Sn2—O2 | 2.406 (2) | N—H1N | 0.96 (3) |
Sn2—C41 | 2.131 (2) | C2—H2A | 0.950 |
Sn2—C51 | 2.140 (2) | C2—H2B | 0.950 |
Sn2—C61 | 2.133 (2) | C3—H3A | 0.950 |
C1—O1 | 1.274 (3) | C3—H3B | 0.950 |
C1—O2 | 1.249 (3) | C4—H4A | 0.950 |
N—C8 | 1.504 (3) | C4—H4B | 0.950 |
N—C3 | 1.509 (3) | C5—H5A | 0.950 |
N—C4 | 1.511 (3) | C5—H5B | 0.950 |
C1—C2 | 1.524 (3) | C6—H6A | 0.950 |
C2—C3 | 1.515 (3) | C6—H6B | 0.950 |
C4—C5 | 1.507 (4) | C7—H7A | 0.950 |
C5—C6 | 1.511 (4) | C7—H7B | 0.950 |
C6—C7 | 1.523 (4) | C8—H8A | 0.950 |
C7—C8 | 1.514 (4) | C8—H8B | 0.950 |
C11—C12 | 1.395 (3) | C12—H12 | 0.950 |
C11—C16 | 1.399 (3) | C13—H13 | 0.950 |
C12—C13 | 1.394 (4) | C14—H14 | 0.950 |
C13—C14 | 1.378 (4) | C15—H15 | 0.950 |
C14—C15 | 1.371 (4) | C16—H16 | 0.950 |
C15—C16 | 1.383 (3) | C22—H22 | 0.950 |
C21—C22 | 1.394 (3) | C23—H23 | 0.950 |
C21—C26 | 1.400 (3) | C24—H24 | 0.950 |
C22—C23 | 1.391 (3) | C25—H25 | 0.950 |
C23—C24 | 1.387 (4) | C26—H26 | 0.950 |
C24—C25 | 1.383 (3) | C32—H32 | 0.950 |
C25—C26 | 1.388 (3) | C33—H33 | 0.950 |
C31—C36 | 1.389 (3) | C34—H34 | 0.950 |
C31—C32 | 1.393 (3) | C35—H35 | 0.950 |
C32—C33 | 1.397 (4) | C36—H36 | 0.950 |
C33—C34 | 1.370 (4) | C42—H42 | 0.950 |
C34—C35 | 1.382 (4) | C43—H43 | 0.950 |
C35—C36 | 1.399 (4) | C44—H44 | 0.950 |
C41—C46 | 1.392 (3) | C45—H45 | 0.950 |
C41—C42 | 1.397 (3) | C46—H46 | 0.950 |
C42—C43 | 1.388 (3) | C52—H52 | 0.950 |
C43—C44 | 1.374 (4) | C53—H53 | 0.950 |
C44—C45 | 1.383 (4) | C54—H54 | 0.950 |
C45—C46 | 1.399 (3) | C55—H55 | 0.950 |
C51—C56 | 1.388 (3) | C56—H56 | 0.950 |
C51—C52 | 1.400 (3) | C62—H62 | 0.950 |
C52—C53 | 1.393 (4) | C63—H63 | 0.950 |
C53—C54 | 1.375 (4) | C64—H64 | 0.950 |
C54—C55 | 1.383 (4) | C65—H65 | 0.950 |
C55—C56 | 1.398 (3) | C66—H66 | 0.950 |
Cl1—Sn1—O1 | 176.43 (6) | C1—C2—H2B | 108.2 |
Cl1—Sn1—C11 | 93.79 (6) | H3A—C3—H3B | 109.5 |
Cl1—Sn1—C21 | 89.72 (6) | N—C3—H3A | 108.3 |
Cl1—Sn1—C31 | 92.03 (7) | C2—C3—H3A | 108.3 |
O1—Sn1—C11 | 83.10 (7) | N—C3—H3B | 108.3 |
O1—Sn1—C21 | 90.14 (7) | C2—C3—H3B | 108.3 |
O1—Sn1—C31 | 90.98 (7) | H4A—C4—H4B | 109.5 |
C11—Sn1—C21 | 116.76 (9) | C5—C4—H4A | 108.8 |
C11—Sn1—C31 | 118.06 (9) | N—C4—H4A | 108.8 |
C21—Sn1—C31 | 124.89 (9) | C5—C4—H4B | 108.8 |
Cl2—Sn2—O2 | 174.63 (5) | N—C4—H4B | 108.8 |
Cl2—Sn2—C41 | 95.28 (6) | H5A—C5—H5B | 109.5 |
Cl2—Sn2—C51 | 95.05 (6) | C4—C5—H5A | 108.9 |
Cl2—Sn2—C61 | 92.24 (6) | C6—C5—H5A | 108.9 |
O2—Sn2—C41 | 84.03 (7) | C4—C5—H5B | 108.9 |
O2—Sn2—C51 | 90.06 (7) | C6—C5—H5B | 108.9 |
O2—Sn2—C61 | 83.68 (7) | H6A—C6—H6B | 109.5 |
C41—Sn2—C51 | 114.97 (8) | C5—C6—H6A | 109.3 |
C41—Sn2—C61 | 122.53 (9) | C7—C6—H6A | 109.3 |
C51—Sn2—C61 | 120.95 (8) | C5—C6—H6B | 109.3 |
Sn1—O1—C1 | 124.1 (1) | C7—C6—H6B | 109.3 |
Sn2—O2—C1 | 127.5 (1) | H7A—C7—H7B | 109.5 |
Sn1—C11—C12 | 120.2 (2) | C8—C7—H7A | 109.2 |
Sn1—C11—C16 | 122.1 (2) | C6—C7—H7A | 109.2 |
Sn1—C21—C22 | 121.2 (2) | C8—C7—H7B | 109.2 |
Sn1—C21—C26 | 120.5 (2) | C6—C7—H7B | 109.2 |
Sn1—C31—C32 | 120.0 (2) | H8A—C8—H8B | 109.5 |
Sn1—C31—C36 | 121.7 (2) | N—C8—H8A | 109.2 |
Sn2—C41—C42 | 120.8 (2) | C7—C8—H8A | 109.2 |
Sn2—C41—C46 | 120.3 (2) | N—C8—H8B | 109.2 |
Sn2—C51—C52 | 120.4 (2) | C7—C8—H8B | 109.2 |
Sn2—C51—C56 | 121.6 (2) | C13—C12—H12 | 119.6 |
Sn2—C61—C62 | 119.8 (2) | C11—C12—H12 | 119.6 |
Sn2—C61—C66 | 121.6 (2) | C14—C13—H13 | 119.9 |
C3—N—C8 | 112.4 (2) | C12—C13—H13 | 119.9 |
C4—N—C8 | 111.2 (2) | C15—C14—H14 | 120.0 |
C3—N—C4 | 109.3 (2) | C13—C14—H14 | 120.0 |
O1—C1—O2 | 124.2 (2) | C14—C15—H15 | 120.0 |
O1—C1—C2 | 115.4 (2) | C16—C15—H15 | 120.0 |
O2—C1—C2 | 120.3 (2) | C15—C16—H16 | 119.3 |
O2—C1—C2 | 120.3 (2) | C11—C16—H16 | 119.3 |
C1—C2—C3 | 114.5 (2) | C23—C22—H22 | 119.6 |
N—C3—C2 | 114.0 (2) | C21—C22—H22 | 119.6 |
N—C4—C5 | 112.0 (2) | C24—C23—H23 | 119.9 |
C4—C5—C6 | 111.6 (2) | C22—C23—H23 | 119.9 |
C5—C6—C7 | 110.2 (2) | C25—C24—H24 | 120.2 |
C6—C7—C8 | 110.6 (2) | C23—C24—H24 | 120.2 |
N—C8—C7 | 110.5 (2) | C24—C25—H25 | 119.8 |
C12—C11—C16 | 117.4 (2) | C26—C25—H25 | 119.8 |
C11—C12—C13 | 120.7 (3) | C25—C26—H26 | 119.6 |
C12—C13—C14 | 120.2 (3) | C21—C26—H26 | 119.6 |
C13—C14—C15 | 120.0 (3) | C31—C32—H32 | 119.6 |
C14—C15—C16 | 120.0 (3) | C33—C32—H32 | 119.6 |
C11—C16—C15 | 121.5 (2) | C34—C33—H33 | 119.8 |
C22—C21—C26 | 118.2 (2) | C32—C33—H33 | 119.8 |
C21—C22—C23 | 120.8 (2) | C33—C34—H34 | 120.2 |
C22—C23—C24 | 120.2 (2) | C35—C34—H34 | 120.2 |
C23—C24—C25 | 119.6 (2) | C34—C35—H35 | 119.9 |
C24—C25—C26 | 120.3 (2) | C36—C35—H35 | 119.9 |
C21—C26—C25 | 120.8 (2) | C31—C36—H36 | 119.6 |
C32—C31—C36 | 118.1 (2) | C35—C36—H36 | 119.6 |
C31—C32—C33 | 120.8 (3) | C43—C42—H42 | 119.9 |
C32—C33—C34 | 120.4 (3) | C41—C42—H42 | 119.9 |
C33—C34—C35 | 119.6 (2) | C44—C43—H43 | 119.6 |
C34—C35—C36 | 120.2 (3) | C42—C43—H43 | 119.6 |
C31—C36—C35 | 120.8 (2) | C43—C44—H44 | 120.2 |
C42—C41—C46 | 118.9 (2) | C45—C44—H44 | 120.2 |
C41—C42—C43 | 120.3 (2) | C44—C45—H45 | 119.8 |
C42—C43—C44 | 120.7 (2) | C46—C45—H45 | 119.8 |
C43—C44—C45 | 119.6 (2) | C41—C46—H46 | 120.0 |
C44—C45—C46 | 120.4 (3) | C45—C46—H46 | 120.0 |
C41—C46—C45 | 120.0 (2) | C53—C52—H52 | 119.6 |
C52—C51—C56 | 117.9 (2) | C51—C52—H52 | 119.6 |
C51—C52—C53 | 120.8 (2) | C54—C53—H53 | 119.6 |
C52—C53—C54 | 120.8 (2) | C52—C53—H53 | 119.6 |
C53—C54—C55 | 119.1 (2) | C53—C54—H54 | 120.4 |
C54—C55—C56 | 120.5 (2) | C55—C54—H54 | 120.4 |
C51—C56—C55 | 120.9 (2) | C54—C55—H55 | 119.7 |
C62—C61—C66 | 118.7 (2) | C56—C55—H55 | 119.7 |
C61—C62—C63 | 120.3 (2) | C51—C56—H56 | 119.6 |
C62—C63—C64 | 120.5 (2) | C55—C56—H56 | 119.6 |
C63—C64—C65 | 120.0 (2) | C61—C62—H62 | 119.9 |
C64—C65—C66 | 119.6 (2) | C63—C62—H62 | 119.9 |
C61—C66—C65 | 121.0 (2) | C64—C63—H63 | 119.8 |
C3—N—H1N | 106 (2) | C62—C63—H63 | 119.8 |
C4—N—H1N | 111 (2) | C63—C64—H64 | 120.0 |
C8—N—H1N | 107 (2) | C65—C64—H64 | 120.0 |
H2A—C2—H2B | 109.5 | C64—C65—H65 | 120.2 |
C3—C2—H2A | 108.2 | C66—C65—H65 | 120.2 |
C1—C2—H2A | 108.2 | C65—C66—H66 | 119.5 |
C3—C2—H2B | 108.2 | C61—C66—H66 | 119.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···O1 | 0.96 (3) | 2.05 (3) | 2.835 (3) | 138 (2) |