metal-organic compounds
Chloridobis(2-chlorobenzyl)(quinolin-8-olato-κ2N,O)tin(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The SnIV atom in the three independent molecules of the title compound, [Sn(C7H6Cl)2(C9H6NO)Cl], is N,O-chelated by the quinolin-8-olate anion and exists in a cis-C2SnNOCl trigonal–bipyramidal geometry; the O atom of the anion and the two benzyl C atoms lie in the equatorial plane.
Related literature
For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961). For related structures, see: Shi & Hu (1987); Vafaee et al. (2010).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT; data reduction: SAINT (Bruker, 2009); 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, 2010).
Supporting information
10.1107/S160053681101573X/bt5528sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681101573X/bt5528Isup2.hkl
The diorganotin dichloride was synthesized by the direct reaction of 2-chlorobenzyl chloride and metallic tin according to a literature procedure (Sisido et al., 1961). The diorganotin dichloride (0.44 g, 1 mmol) and 8-hydroxyquinoline (0.15 g, 1 mmol) were dissolved in chloroform (50 ml) to give a yellow solution. The solution was filtered and the solvent allowed to evaporate to yield yellow crystals.
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 1.2 times Ueq(C).The final difference Fourier map had a peak in the vicinity of Sn1 as well as a hole in the vicinity of the same atom.
The second parameter of the weighting scheme is rather large; however, as lowering this number to less than 10 had only a minor effect on the
with regard to the peak/hole. This high value was retained.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).[Sn(C7H6Cl)2(C9H6NO)Cl] | F(000) = 3264 |
Mr = 549.42 | Dx = 1.710 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9252 reflections |
a = 10.2504 (1) Å | θ = 2.4–28.3° |
b = 41.2573 (6) Å | µ = 1.59 mm−1 |
c = 15.3882 (2) Å | T = 100 K |
β = 100.3433 (6)° | Block, colorless |
V = 6401.98 (14) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 12 |
Bruker SMART APEX diffractometer | 14589 independent reflections |
Radiation source: fine-focus sealed tube | 13128 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.692, Tmax = 0.797 | k = −53→40 |
41105 measured reflections | l = −19→19 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0318P)2 + 14.3485P] where P = (Fo2 + 2Fc2)/3 |
14589 reflections | (Δ/σ)max = 0.001 |
784 parameters | Δρmax = 1.27 e Å−3 |
0 restraints | Δρmin = −1.42 e Å−3 |
[Sn(C7H6Cl)2(C9H6NO)Cl] | V = 6401.98 (14) Å3 |
Mr = 549.42 | Z = 12 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.2504 (1) Å | µ = 1.59 mm−1 |
b = 41.2573 (6) Å | T = 100 K |
c = 15.3882 (2) Å | 0.25 × 0.20 × 0.15 mm |
β = 100.3433 (6)° |
Bruker SMART APEX diffractometer | 14589 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 13128 reflections with I > 2σ(I) |
Tmin = 0.692, Tmax = 0.797 | Rint = 0.024 |
41105 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0318P)2 + 14.3485P] where P = (Fo2 + 2Fc2)/3 |
14589 reflections | Δρmax = 1.27 e Å−3 |
784 parameters | Δρmin = −1.42 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.51891 (2) | 0.342454 (5) | 0.664659 (14) | 0.01383 (5) | |
Sn2 | 0.51124 (2) | 0.325014 (5) | 0.306586 (14) | 0.01375 (5) | |
Sn3 | 0.49861 (2) | 0.005273 (5) | 0.701013 (14) | 0.01335 (5) | |
Cl1 | 0.35889 (8) | 0.30078 (2) | 0.60004 (6) | 0.02297 (17) | |
Cl2 | 0.28721 (9) | 0.35808 (3) | 0.86345 (6) | 0.0307 (2) | |
Cl3 | 0.37714 (9) | 0.41474 (2) | 0.73481 (6) | 0.02583 (18) | |
Cl4 | 0.66348 (8) | 0.36906 (2) | 0.36650 (6) | 0.02405 (18) | |
Cl5 | 0.65041 (10) | 0.24788 (2) | 0.24180 (6) | 0.0301 (2) | |
Cl6 | 0.76770 (9) | 0.31831 (2) | 0.15379 (6) | 0.02775 (19) | |
Cl7 | 0.33400 (8) | −0.036560 (19) | 0.64966 (6) | 0.02048 (16) | |
Cl8 | 0.38458 (10) | 0.09956 (2) | 0.74145 (6) | 0.0296 (2) | |
Cl9 | 0.26222 (8) | 0.02390 (2) | 0.83358 (5) | 0.02545 (18) | |
O1 | 0.6547 (2) | 0.31709 (5) | 0.60960 (14) | 0.0158 (4) | |
O2 | 0.3754 (2) | 0.34906 (5) | 0.36442 (14) | 0.0160 (4) | |
O3 | 0.6230 (2) | −0.01859 (5) | 0.63342 (15) | 0.0172 (5) | |
N1 | 0.7171 (3) | 0.37103 (6) | 0.70561 (17) | 0.0152 (5) | |
N2 | 0.3191 (3) | 0.29384 (6) | 0.27310 (17) | 0.0149 (5) | |
N3 | 0.6961 (3) | 0.03576 (6) | 0.72578 (17) | 0.0155 (5) | |
C1 | 0.5196 (4) | 0.32487 (8) | 0.7971 (2) | 0.0228 (7) | |
H1A | 0.4312 | 0.3154 | 0.7984 | 0.027* | |
H1B | 0.5847 | 0.3070 | 0.8083 | 0.027* | |
C2 | 0.5502 (3) | 0.34804 (8) | 0.8716 (2) | 0.0181 (7) | |
C3 | 0.6818 (4) | 0.35385 (10) | 0.9111 (3) | 0.0296 (8) | |
H3 | 0.7503 | 0.3422 | 0.8907 | 0.036* | |
C4 | 0.7155 (4) | 0.37575 (11) | 0.9782 (3) | 0.0390 (11) | |
H4 | 0.8062 | 0.3792 | 1.0030 | 0.047* | |
C5 | 0.6192 (5) | 0.39269 (10) | 1.0095 (2) | 0.0403 (12) | |
H5 | 0.6430 | 0.4080 | 1.0557 | 0.048* | |
C6 | 0.4858 (5) | 0.38745 (9) | 0.9736 (2) | 0.0321 (9) | |
H6 | 0.4180 | 0.3989 | 0.9955 | 0.039* | |
C7 | 0.4539 (3) | 0.36523 (8) | 0.9056 (2) | 0.0197 (7) | |
C8 | 0.4283 (3) | 0.37879 (8) | 0.5727 (2) | 0.0195 (7) | |
H8A | 0.4374 | 0.3717 | 0.5126 | 0.023* | |
H8B | 0.3323 | 0.3792 | 0.5747 | 0.023* | |
C9 | 0.4790 (3) | 0.41255 (8) | 0.5851 (2) | 0.0165 (6) | |
C10 | 0.5479 (4) | 0.42694 (9) | 0.5246 (2) | 0.0227 (7) | |
H10 | 0.5657 | 0.4146 | 0.4759 | 0.027* | |
C11 | 0.5910 (4) | 0.45888 (10) | 0.5344 (3) | 0.0302 (8) | |
H11 | 0.6367 | 0.4682 | 0.4921 | 0.036* | |
C12 | 0.5676 (4) | 0.47723 (9) | 0.6057 (2) | 0.0265 (8) | |
H12 | 0.5977 | 0.4990 | 0.6123 | 0.032* | |
C13 | 0.5003 (3) | 0.46368 (8) | 0.6667 (2) | 0.0210 (7) | |
H13 | 0.4830 | 0.4760 | 0.7155 | 0.025* | |
C14 | 0.4584 (3) | 0.43187 (8) | 0.6559 (2) | 0.0161 (6) | |
C15 | 0.7455 (3) | 0.39726 (8) | 0.7550 (2) | 0.0178 (6) | |
H15 | 0.6763 | 0.4076 | 0.7781 | 0.021* | |
C16 | 0.8738 (3) | 0.41027 (8) | 0.7745 (2) | 0.0221 (7) | |
H16 | 0.8910 | 0.4289 | 0.8109 | 0.027* | |
C17 | 0.9739 (3) | 0.39583 (8) | 0.7406 (2) | 0.0214 (7) | |
H17 | 1.0609 | 0.4046 | 0.7530 | 0.026* | |
C18 | 0.9483 (3) | 0.36779 (8) | 0.6871 (2) | 0.0162 (6) | |
C19 | 1.0442 (3) | 0.35066 (8) | 0.6496 (2) | 0.0193 (7) | |
H19 | 1.1330 | 0.3583 | 0.6577 | 0.023* | |
C20 | 1.0088 (3) | 0.32306 (9) | 0.6017 (2) | 0.0211 (7) | |
H20 | 1.0742 | 0.3117 | 0.5772 | 0.025* | |
C21 | 0.8782 (3) | 0.31108 (8) | 0.5878 (2) | 0.0171 (6) | |
H21 | 0.8569 | 0.2917 | 0.5549 | 0.020* | |
C22 | 0.7806 (3) | 0.32750 (8) | 0.62184 (19) | 0.0144 (6) | |
C23 | 0.8163 (3) | 0.35615 (8) | 0.67214 (19) | 0.0144 (6) | |
C24 | 0.4908 (4) | 0.34026 (8) | 0.1706 (2) | 0.0223 (7) | |
H24A | 0.4032 | 0.3508 | 0.1536 | 0.027* | |
H24B | 0.5592 | 0.3569 | 0.1670 | 0.027* | |
C25 | 0.5024 (3) | 0.31453 (8) | 0.1037 (2) | 0.0165 (6) | |
C26 | 0.3891 (4) | 0.30107 (9) | 0.0511 (2) | 0.0248 (8) | |
H26 | 0.3037 | 0.3085 | 0.0575 | 0.030* | |
C27 | 0.4002 (4) | 0.27714 (10) | −0.0099 (2) | 0.0302 (9) | |
H27 | 0.3223 | 0.2685 | −0.0451 | 0.036* | |
C28 | 0.5223 (4) | 0.26566 (9) | −0.0205 (2) | 0.0300 (9) | |
H28 | 0.5287 | 0.2490 | −0.0621 | 0.036* | |
C29 | 0.6358 (4) | 0.27858 (9) | 0.0299 (2) | 0.0250 (8) | |
H29 | 0.7207 | 0.2709 | 0.0232 | 0.030* | |
C30 | 0.6244 (3) | 0.30281 (8) | 0.0901 (2) | 0.0179 (6) | |
C31 | 0.6184 (3) | 0.29074 (8) | 0.3978 (2) | 0.0211 (7) | |
H31A | 0.7108 | 0.2902 | 0.3871 | 0.025* | |
H31B | 0.6217 | 0.2995 | 0.4580 | 0.025* | |
C32 | 0.5725 (3) | 0.25673 (8) | 0.3986 (2) | 0.0165 (6) | |
C33 | 0.5197 (4) | 0.24448 (10) | 0.4697 (2) | 0.0270 (8) | |
H33 | 0.5067 | 0.2588 | 0.5158 | 0.032* | |
C34 | 0.4858 (4) | 0.21223 (11) | 0.4750 (3) | 0.0345 (9) | |
H34 | 0.4518 | 0.2046 | 0.5247 | 0.041* | |
C35 | 0.5013 (4) | 0.19110 (10) | 0.4077 (3) | 0.0313 (9) | |
H35 | 0.4785 | 0.1689 | 0.4115 | 0.038* | |
C36 | 0.5498 (4) | 0.20224 (9) | 0.3353 (2) | 0.0244 (7) | |
H36 | 0.5591 | 0.1880 | 0.2883 | 0.029* | |
C37 | 0.5848 (3) | 0.23456 (8) | 0.3323 (2) | 0.0174 (6) | |
C38 | 0.2936 (3) | 0.26708 (8) | 0.2257 (2) | 0.0183 (6) | |
H38 | 0.3630 | 0.2573 | 0.2014 | 0.022* | |
C39 | 0.1678 (4) | 0.25257 (8) | 0.2101 (2) | 0.0227 (7) | |
H39 | 0.1524 | 0.2334 | 0.1754 | 0.027* | |
C40 | 0.0673 (3) | 0.26633 (8) | 0.2456 (2) | 0.0217 (7) | |
H40 | −0.0182 | 0.2566 | 0.2355 | 0.026* | |
C41 | 0.0902 (3) | 0.29479 (8) | 0.2971 (2) | 0.0185 (7) | |
C42 | −0.0053 (3) | 0.31081 (9) | 0.3369 (2) | 0.0218 (7) | |
H42 | −0.0920 | 0.3020 | 0.3322 | 0.026* | |
C43 | 0.0271 (3) | 0.33903 (9) | 0.3824 (2) | 0.0218 (7) | |
H43 | −0.0385 | 0.3498 | 0.4081 | 0.026* | |
C44 | 0.1552 (3) | 0.35252 (9) | 0.3923 (2) | 0.0193 (7) | |
H44 | 0.1746 | 0.3722 | 0.4240 | 0.023* | |
C45 | 0.2524 (3) | 0.33724 (8) | 0.35614 (19) | 0.0144 (6) | |
C46 | 0.2201 (3) | 0.30805 (8) | 0.3085 (2) | 0.0151 (6) | |
C47 | 0.3890 (3) | 0.04155 (8) | 0.6179 (2) | 0.0177 (6) | |
H47A | 0.3528 | 0.0315 | 0.5602 | 0.021* | |
H47B | 0.3127 | 0.0483 | 0.6450 | 0.021* | |
C48 | 0.4642 (3) | 0.07106 (8) | 0.6015 (2) | 0.0158 (6) | |
C49 | 0.5337 (3) | 0.07149 (9) | 0.5316 (2) | 0.0232 (7) | |
H49 | 0.5317 | 0.0530 | 0.4947 | 0.028* | |
C50 | 0.6058 (4) | 0.09847 (11) | 0.5153 (3) | 0.0334 (9) | |
H50 | 0.6516 | 0.0985 | 0.4668 | 0.040* | |
C51 | 0.6113 (4) | 0.12534 (10) | 0.5691 (3) | 0.0311 (9) | |
H51 | 0.6623 | 0.1436 | 0.5582 | 0.037* | |
C52 | 0.5433 (4) | 0.12588 (9) | 0.6389 (2) | 0.0244 (7) | |
H52 | 0.5463 | 0.1444 | 0.6757 | 0.029* | |
C53 | 0.4706 (3) | 0.09875 (8) | 0.6540 (2) | 0.0175 (6) | |
C54 | 0.5296 (4) | −0.00778 (8) | 0.8390 (2) | 0.0211 (7) | |
H54A | 0.4609 | −0.0237 | 0.8482 | 0.025* | |
H54B | 0.6170 | −0.0185 | 0.8551 | 0.025* | |
C55 | 0.5246 (3) | 0.02044 (8) | 0.8991 (2) | 0.0182 (7) | |
C56 | 0.6380 (4) | 0.03202 (9) | 0.9556 (2) | 0.0238 (7) | |
H56 | 0.7202 | 0.0212 | 0.9572 | 0.029* | |
C57 | 0.6332 (4) | 0.05867 (10) | 1.0089 (2) | 0.0292 (9) | |
H57 | 0.7115 | 0.0658 | 1.0467 | 0.035* | |
C58 | 0.5157 (4) | 0.07504 (9) | 1.0076 (2) | 0.0280 (8) | |
H58 | 0.5136 | 0.0936 | 1.0437 | 0.034* | |
C59 | 0.3999 (4) | 0.06433 (9) | 0.9535 (2) | 0.0234 (7) | |
H59 | 0.3181 | 0.0753 | 0.9524 | 0.028* | |
C60 | 0.4070 (3) | 0.03732 (8) | 0.9013 (2) | 0.0178 (7) | |
C61 | 0.7283 (3) | 0.06276 (8) | 0.7710 (2) | 0.0194 (7) | |
H61 | 0.6642 | 0.0728 | 0.7996 | 0.023* | |
C62 | 0.8548 (4) | 0.07705 (8) | 0.7782 (2) | 0.0243 (7) | |
H62 | 0.8755 | 0.0964 | 0.8115 | 0.029* | |
C63 | 0.9477 (3) | 0.06275 (9) | 0.7366 (2) | 0.0236 (7) | |
H63 | 1.0329 | 0.0723 | 0.7408 | 0.028* | |
C64 | 0.9170 (3) | 0.03384 (8) | 0.6874 (2) | 0.0193 (7) | |
C65 | 1.0060 (3) | 0.01673 (9) | 0.6442 (2) | 0.0234 (7) | |
H65 | 1.0927 | 0.0250 | 0.6447 | 0.028* | |
C66 | 0.9673 (3) | −0.01177 (9) | 0.6017 (2) | 0.0217 (7) | |
H66 | 1.0287 | −0.0234 | 0.5741 | 0.026* | |
C67 | 0.8383 (3) | −0.02427 (9) | 0.5979 (2) | 0.0191 (7) | |
H67 | 0.8140 | −0.0441 | 0.5680 | 0.023* | |
C68 | 0.7474 (3) | −0.00779 (8) | 0.6374 (2) | 0.0161 (6) | |
C69 | 0.7877 (3) | 0.02121 (8) | 0.6840 (2) | 0.0153 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01268 (10) | 0.01196 (11) | 0.01760 (10) | 0.00043 (8) | 0.00474 (8) | −0.00269 (8) |
Sn2 | 0.01284 (10) | 0.01225 (11) | 0.01672 (10) | −0.00010 (8) | 0.00417 (8) | −0.00330 (8) |
Sn3 | 0.01349 (10) | 0.01096 (11) | 0.01619 (10) | −0.00032 (8) | 0.00426 (8) | 0.00004 (8) |
Cl1 | 0.0155 (4) | 0.0190 (4) | 0.0347 (4) | −0.0035 (3) | 0.0052 (3) | −0.0078 (3) |
Cl2 | 0.0187 (4) | 0.0405 (6) | 0.0346 (5) | −0.0005 (4) | 0.0093 (4) | 0.0044 (4) |
Cl3 | 0.0314 (5) | 0.0270 (5) | 0.0231 (4) | 0.0010 (4) | 0.0154 (3) | 0.0016 (3) |
Cl4 | 0.0185 (4) | 0.0203 (4) | 0.0347 (4) | −0.0064 (3) | 0.0084 (3) | −0.0108 (3) |
Cl5 | 0.0408 (5) | 0.0321 (5) | 0.0213 (4) | 0.0002 (4) | 0.0160 (4) | 0.0001 (3) |
Cl6 | 0.0199 (4) | 0.0336 (5) | 0.0279 (4) | −0.0079 (4) | −0.0007 (3) | 0.0006 (4) |
Cl7 | 0.0163 (4) | 0.0156 (4) | 0.0305 (4) | −0.0040 (3) | 0.0067 (3) | −0.0021 (3) |
Cl8 | 0.0376 (5) | 0.0311 (5) | 0.0222 (4) | 0.0009 (4) | 0.0114 (4) | −0.0044 (3) |
Cl9 | 0.0158 (4) | 0.0385 (5) | 0.0219 (4) | −0.0020 (3) | 0.0028 (3) | −0.0009 (3) |
O1 | 0.0125 (11) | 0.0147 (11) | 0.0211 (11) | 0.0009 (8) | 0.0054 (9) | −0.0039 (9) |
O2 | 0.0141 (11) | 0.0158 (12) | 0.0186 (11) | 0.0012 (9) | 0.0039 (9) | −0.0045 (9) |
O3 | 0.0140 (11) | 0.0151 (12) | 0.0232 (11) | −0.0024 (9) | 0.0057 (9) | −0.0038 (9) |
N1 | 0.0151 (13) | 0.0127 (13) | 0.0172 (12) | 0.0038 (10) | 0.0013 (10) | 0.0017 (10) |
N2 | 0.0160 (13) | 0.0134 (13) | 0.0150 (12) | 0.0012 (10) | 0.0021 (10) | −0.0002 (10) |
N3 | 0.0173 (13) | 0.0112 (13) | 0.0174 (12) | 0.0001 (10) | 0.0014 (10) | 0.0016 (10) |
C1 | 0.0310 (19) | 0.0171 (17) | 0.0235 (17) | 0.0012 (14) | 0.0134 (15) | 0.0009 (13) |
C2 | 0.0188 (16) | 0.0215 (17) | 0.0148 (14) | −0.0005 (13) | 0.0052 (12) | 0.0041 (12) |
C3 | 0.0224 (18) | 0.036 (2) | 0.0301 (19) | −0.0018 (16) | 0.0036 (15) | 0.0105 (16) |
C4 | 0.037 (2) | 0.045 (3) | 0.029 (2) | −0.021 (2) | −0.0089 (18) | 0.0123 (18) |
C5 | 0.075 (3) | 0.030 (2) | 0.0127 (16) | −0.031 (2) | −0.0031 (19) | −0.0002 (15) |
C6 | 0.055 (3) | 0.023 (2) | 0.0227 (17) | −0.0014 (18) | 0.0174 (18) | −0.0007 (15) |
C7 | 0.0234 (17) | 0.0186 (17) | 0.0173 (15) | −0.0042 (13) | 0.0039 (13) | −0.0003 (12) |
C8 | 0.0173 (16) | 0.0193 (17) | 0.0212 (16) | 0.0018 (13) | 0.0015 (13) | −0.0023 (13) |
C9 | 0.0167 (15) | 0.0180 (17) | 0.0141 (14) | 0.0066 (13) | 0.0009 (12) | 0.0005 (12) |
C10 | 0.0277 (19) | 0.0236 (19) | 0.0184 (16) | 0.0060 (14) | 0.0089 (14) | 0.0005 (13) |
C11 | 0.038 (2) | 0.028 (2) | 0.0294 (19) | 0.0008 (17) | 0.0174 (17) | 0.0054 (15) |
C12 | 0.034 (2) | 0.0150 (17) | 0.0311 (19) | −0.0002 (15) | 0.0071 (16) | 0.0019 (14) |
C13 | 0.0235 (17) | 0.0202 (17) | 0.0191 (15) | 0.0059 (14) | 0.0035 (13) | −0.0035 (13) |
C14 | 0.0160 (15) | 0.0187 (17) | 0.0140 (14) | 0.0032 (12) | 0.0039 (12) | 0.0017 (12) |
C15 | 0.0205 (16) | 0.0126 (15) | 0.0192 (15) | 0.0025 (12) | 0.0003 (13) | 0.0010 (12) |
C16 | 0.0259 (18) | 0.0138 (16) | 0.0255 (17) | −0.0007 (14) | 0.0013 (14) | −0.0003 (13) |
C17 | 0.0204 (17) | 0.0194 (17) | 0.0228 (16) | −0.0057 (13) | −0.0005 (13) | 0.0039 (13) |
C18 | 0.0151 (15) | 0.0166 (16) | 0.0165 (14) | 0.0001 (12) | 0.0016 (12) | 0.0059 (12) |
C19 | 0.0124 (15) | 0.0230 (18) | 0.0227 (16) | 0.0018 (13) | 0.0039 (13) | 0.0078 (13) |
C20 | 0.0161 (16) | 0.031 (2) | 0.0170 (15) | 0.0067 (14) | 0.0052 (13) | 0.0051 (13) |
C21 | 0.0169 (15) | 0.0199 (17) | 0.0146 (14) | 0.0022 (13) | 0.0034 (12) | 0.0002 (12) |
C22 | 0.0129 (14) | 0.0176 (16) | 0.0127 (13) | 0.0021 (12) | 0.0027 (11) | 0.0040 (11) |
C23 | 0.0153 (15) | 0.0148 (16) | 0.0134 (14) | −0.0008 (12) | 0.0034 (12) | 0.0029 (11) |
C24 | 0.0309 (19) | 0.0156 (17) | 0.0223 (16) | 0.0018 (14) | 0.0100 (14) | 0.0020 (13) |
C25 | 0.0247 (17) | 0.0093 (15) | 0.0159 (14) | 0.0019 (12) | 0.0048 (13) | 0.0068 (11) |
C26 | 0.0214 (17) | 0.026 (2) | 0.0249 (17) | −0.0017 (14) | −0.0011 (14) | 0.0080 (14) |
C27 | 0.038 (2) | 0.028 (2) | 0.0204 (17) | −0.0175 (17) | −0.0062 (15) | 0.0017 (15) |
C28 | 0.053 (3) | 0.0219 (19) | 0.0163 (16) | −0.0087 (17) | 0.0086 (16) | −0.0043 (14) |
C29 | 0.033 (2) | 0.0232 (19) | 0.0227 (17) | −0.0016 (15) | 0.0143 (15) | −0.0028 (14) |
C30 | 0.0211 (16) | 0.0187 (17) | 0.0133 (14) | −0.0068 (13) | 0.0014 (12) | 0.0012 (12) |
C31 | 0.0188 (16) | 0.0184 (17) | 0.0235 (17) | 0.0036 (13) | −0.0028 (13) | −0.0024 (13) |
C32 | 0.0153 (15) | 0.0184 (17) | 0.0149 (14) | 0.0057 (12) | 0.0000 (12) | −0.0010 (12) |
C33 | 0.030 (2) | 0.035 (2) | 0.0174 (16) | 0.0131 (16) | 0.0094 (14) | 0.0024 (14) |
C34 | 0.028 (2) | 0.042 (3) | 0.038 (2) | 0.0057 (17) | 0.0169 (17) | 0.0187 (18) |
C35 | 0.027 (2) | 0.021 (2) | 0.046 (2) | 0.0004 (15) | 0.0058 (17) | 0.0113 (17) |
C36 | 0.0228 (18) | 0.0191 (18) | 0.0293 (18) | 0.0019 (14) | −0.0004 (15) | −0.0026 (14) |
C37 | 0.0175 (16) | 0.0223 (17) | 0.0130 (14) | 0.0018 (13) | 0.0046 (12) | 0.0014 (12) |
C38 | 0.0210 (16) | 0.0137 (16) | 0.0196 (15) | 0.0014 (13) | 0.0019 (13) | −0.0010 (12) |
C39 | 0.0283 (19) | 0.0137 (17) | 0.0240 (17) | −0.0061 (14) | −0.0007 (14) | 0.0015 (13) |
C40 | 0.0217 (17) | 0.0200 (18) | 0.0219 (16) | −0.0050 (14) | −0.0003 (13) | 0.0060 (13) |
C41 | 0.0168 (16) | 0.0214 (17) | 0.0163 (15) | −0.0025 (13) | 0.0004 (12) | 0.0054 (12) |
C42 | 0.0135 (16) | 0.030 (2) | 0.0224 (16) | −0.0001 (14) | 0.0041 (13) | 0.0094 (14) |
C43 | 0.0182 (16) | 0.031 (2) | 0.0169 (15) | 0.0054 (14) | 0.0066 (13) | 0.0055 (13) |
C44 | 0.0198 (16) | 0.0226 (18) | 0.0152 (15) | 0.0046 (13) | 0.0024 (12) | −0.0004 (12) |
C45 | 0.0142 (15) | 0.0171 (16) | 0.0116 (13) | 0.0017 (12) | 0.0016 (11) | 0.0027 (11) |
C46 | 0.0168 (15) | 0.0141 (16) | 0.0141 (14) | 0.0022 (12) | 0.0015 (12) | 0.0026 (11) |
C47 | 0.0178 (16) | 0.0124 (16) | 0.0221 (16) | −0.0021 (12) | 0.0011 (13) | 0.0005 (12) |
C48 | 0.0144 (15) | 0.0137 (16) | 0.0178 (15) | 0.0013 (12) | −0.0009 (12) | 0.0026 (12) |
C49 | 0.0221 (17) | 0.0271 (19) | 0.0210 (16) | 0.0019 (14) | 0.0061 (14) | 0.0008 (14) |
C50 | 0.031 (2) | 0.043 (3) | 0.0288 (19) | −0.0078 (18) | 0.0110 (16) | 0.0082 (17) |
C51 | 0.027 (2) | 0.029 (2) | 0.035 (2) | −0.0109 (16) | 0.0002 (16) | 0.0112 (16) |
C52 | 0.0253 (18) | 0.0165 (17) | 0.0271 (17) | −0.0022 (14) | −0.0066 (14) | 0.0016 (14) |
C53 | 0.0169 (16) | 0.0192 (17) | 0.0150 (14) | 0.0027 (12) | −0.0006 (12) | 0.0018 (12) |
C54 | 0.0230 (17) | 0.0200 (18) | 0.0213 (16) | 0.0026 (13) | 0.0071 (14) | 0.0026 (13) |
C55 | 0.0197 (16) | 0.0187 (17) | 0.0165 (15) | −0.0010 (13) | 0.0040 (12) | 0.0092 (12) |
C56 | 0.0206 (17) | 0.031 (2) | 0.0202 (16) | 0.0000 (14) | 0.0048 (13) | 0.0065 (14) |
C57 | 0.029 (2) | 0.041 (2) | 0.0172 (16) | −0.0162 (17) | 0.0018 (14) | 0.0013 (15) |
C58 | 0.044 (2) | 0.0230 (19) | 0.0194 (16) | −0.0084 (16) | 0.0115 (16) | −0.0030 (14) |
C59 | 0.0303 (19) | 0.0229 (19) | 0.0186 (16) | 0.0043 (15) | 0.0089 (14) | 0.0000 (13) |
C60 | 0.0174 (16) | 0.0238 (18) | 0.0125 (14) | −0.0018 (13) | 0.0036 (12) | 0.0027 (12) |
C61 | 0.0209 (17) | 0.0146 (16) | 0.0202 (15) | 0.0007 (13) | −0.0033 (13) | 0.0010 (12) |
C62 | 0.0263 (18) | 0.0126 (17) | 0.0299 (18) | −0.0026 (14) | −0.0062 (15) | 0.0027 (13) |
C63 | 0.0194 (17) | 0.0198 (18) | 0.0283 (18) | −0.0068 (14) | −0.0042 (14) | 0.0072 (14) |
C64 | 0.0165 (16) | 0.0204 (17) | 0.0191 (15) | −0.0039 (13) | −0.0022 (12) | 0.0066 (13) |
C65 | 0.0160 (16) | 0.034 (2) | 0.0205 (16) | −0.0020 (14) | 0.0039 (13) | 0.0086 (14) |
C66 | 0.0166 (16) | 0.034 (2) | 0.0164 (15) | 0.0036 (14) | 0.0069 (13) | 0.0043 (13) |
C67 | 0.0197 (16) | 0.0229 (18) | 0.0143 (14) | 0.0017 (13) | 0.0020 (12) | −0.0001 (12) |
C68 | 0.0146 (15) | 0.0171 (16) | 0.0159 (14) | −0.0008 (12) | 0.0014 (12) | 0.0032 (12) |
C69 | 0.0173 (15) | 0.0127 (15) | 0.0154 (14) | −0.0005 (12) | 0.0014 (12) | 0.0035 (11) |
Sn1—O1 | 2.043 (2) | C26—H26 | 0.9500 |
Sn1—C8 | 2.154 (3) | C27—C28 | 1.375 (6) |
Sn1—C1 | 2.162 (3) | C27—H27 | 0.9500 |
Sn1—N1 | 2.335 (3) | C28—C29 | 1.384 (5) |
Sn1—Cl1 | 2.4596 (8) | C28—H28 | 0.9500 |
Sn2—O2 | 2.039 (2) | C29—C30 | 1.382 (5) |
Sn2—C31 | 2.150 (3) | C29—H29 | 0.9500 |
Sn2—C24 | 2.159 (3) | C31—C32 | 1.481 (5) |
Sn2—N2 | 2.331 (3) | C31—H31A | 0.9900 |
Sn2—Cl4 | 2.4638 (8) | C31—H31B | 0.9900 |
Sn3—O3 | 2.038 (2) | C32—C37 | 1.393 (4) |
Sn3—C47 | 2.150 (3) | C32—C33 | 1.399 (5) |
Sn3—C54 | 2.159 (3) | C33—C34 | 1.381 (6) |
Sn3—N3 | 2.355 (3) | C33—H33 | 0.9500 |
Sn3—Cl7 | 2.4437 (8) | C34—C35 | 1.384 (6) |
Cl2—C7 | 1.740 (4) | C34—H34 | 0.9500 |
Cl3—C14 | 1.741 (3) | C35—C36 | 1.378 (5) |
Cl5—C37 | 1.741 (3) | C35—H35 | 0.9500 |
Cl6—C30 | 1.735 (3) | C36—C37 | 1.384 (5) |
Cl8—C53 | 1.736 (3) | C36—H36 | 0.9500 |
Cl9—C60 | 1.743 (3) | C38—C39 | 1.403 (5) |
O1—C22 | 1.341 (4) | C38—H38 | 0.9500 |
O2—C45 | 1.337 (4) | C39—C40 | 1.373 (5) |
O3—C68 | 1.342 (4) | C39—H39 | 0.9500 |
N1—C15 | 1.325 (4) | C40—C41 | 1.412 (5) |
N1—C23 | 1.365 (4) | C40—H40 | 0.9500 |
N2—C38 | 1.323 (4) | C41—C42 | 1.410 (5) |
N2—C46 | 1.367 (4) | C41—C46 | 1.421 (4) |
N3—C61 | 1.324 (4) | C42—C43 | 1.368 (5) |
N3—C69 | 1.368 (4) | C42—H42 | 0.9500 |
C1—C2 | 1.483 (5) | C43—C44 | 1.408 (5) |
C1—H1A | 0.9900 | C43—H43 | 0.9500 |
C1—H1B | 0.9900 | C44—C45 | 1.378 (4) |
C2—C7 | 1.391 (5) | C44—H44 | 0.9500 |
C2—C3 | 1.397 (5) | C45—C46 | 1.418 (4) |
C3—C4 | 1.368 (6) | C47—C48 | 1.486 (4) |
C3—H3 | 0.9500 | C47—H47A | 0.9900 |
C4—C5 | 1.366 (7) | C47—H47B | 0.9900 |
C4—H4 | 0.9500 | C48—C49 | 1.393 (5) |
C5—C6 | 1.397 (6) | C48—C53 | 1.394 (5) |
C5—H5 | 0.9500 | C49—C50 | 1.384 (5) |
C6—C7 | 1.386 (5) | C49—H49 | 0.9500 |
C6—H6 | 0.9500 | C50—C51 | 1.379 (6) |
C8—C9 | 1.487 (5) | C50—H50 | 0.9500 |
C8—H8A | 0.9900 | C51—C52 | 1.381 (5) |
C8—H8B | 0.9900 | C51—H51 | 0.9500 |
C9—C14 | 1.396 (4) | C52—C53 | 1.388 (5) |
C9—C10 | 1.397 (5) | C52—H52 | 0.9500 |
C10—C11 | 1.389 (5) | C54—C55 | 1.493 (5) |
C10—H10 | 0.9500 | C54—H54A | 0.9900 |
C11—C12 | 1.388 (5) | C54—H54B | 0.9900 |
C11—H11 | 0.9500 | C55—C60 | 1.398 (5) |
C12—C13 | 1.379 (5) | C55—C56 | 1.405 (5) |
C12—H12 | 0.9500 | C56—C57 | 1.377 (5) |
C13—C14 | 1.382 (5) | C56—H56 | 0.9500 |
C13—H13 | 0.9500 | C57—C58 | 1.379 (6) |
C15—C16 | 1.402 (5) | C57—H57 | 0.9500 |
C15—H15 | 0.9500 | C58—C59 | 1.394 (5) |
C16—C17 | 1.369 (5) | C58—H58 | 0.9500 |
C16—H16 | 0.9500 | C59—C60 | 1.383 (5) |
C17—C18 | 1.416 (5) | C59—H59 | 0.9500 |
C17—H17 | 0.9500 | C61—C62 | 1.411 (5) |
C18—C19 | 1.415 (5) | C61—H61 | 0.9500 |
C18—C23 | 1.415 (4) | C62—C63 | 1.372 (5) |
C19—C20 | 1.370 (5) | C62—H62 | 0.9500 |
C19—H19 | 0.9500 | C63—C64 | 1.417 (5) |
C20—C21 | 1.407 (5) | C63—H63 | 0.9500 |
C20—H20 | 0.9500 | C64—C65 | 1.411 (5) |
C21—C22 | 1.387 (4) | C64—C69 | 1.417 (4) |
C21—H21 | 0.9500 | C65—C66 | 1.369 (5) |
C22—C23 | 1.424 (4) | C65—H65 | 0.9500 |
C24—C25 | 1.498 (5) | C66—C67 | 1.410 (5) |
C24—H24A | 0.9900 | C66—H66 | 0.9500 |
C24—H24B | 0.9900 | C67—C68 | 1.380 (4) |
C25—C30 | 1.392 (5) | C67—H67 | 0.9500 |
C25—C26 | 1.405 (5) | C68—C69 | 1.418 (4) |
C26—C27 | 1.381 (5) | ||
O1—Sn1—C8 | 109.26 (11) | C29—C28—H28 | 120.2 |
O1—Sn1—C1 | 109.37 (11) | C30—C29—C28 | 119.4 (3) |
C8—Sn1—C1 | 141.32 (13) | C30—C29—H29 | 120.3 |
O1—Sn1—N1 | 75.30 (9) | C28—C29—H29 | 120.3 |
C8—Sn1—N1 | 94.45 (11) | C29—C30—C25 | 122.6 (3) |
C1—Sn1—N1 | 93.41 (12) | C29—C30—Cl6 | 118.7 (3) |
O1—Sn1—Cl1 | 85.92 (7) | C25—C30—Cl6 | 118.7 (3) |
C8—Sn1—Cl1 | 92.48 (9) | C32—C31—Sn2 | 120.2 (2) |
C1—Sn1—Cl1 | 92.04 (10) | C32—C31—H31A | 107.3 |
N1—Sn1—Cl1 | 161.20 (7) | Sn2—C31—H31A | 107.3 |
O2—Sn2—C31 | 110.12 (11) | C32—C31—H31B | 107.3 |
O2—Sn2—C24 | 109.04 (11) | Sn2—C31—H31B | 107.3 |
C31—Sn2—C24 | 140.67 (13) | H31A—C31—H31B | 106.9 |
O2—Sn2—N2 | 75.47 (9) | C37—C32—C33 | 115.7 (3) |
C31—Sn2—N2 | 95.38 (11) | C37—C32—C31 | 123.0 (3) |
C24—Sn2—N2 | 90.89 (12) | C33—C32—C31 | 121.2 (3) |
O2—Sn2—Cl4 | 85.07 (7) | C34—C33—C32 | 122.1 (3) |
C31—Sn2—Cl4 | 91.48 (9) | C34—C33—H33 | 119.0 |
C24—Sn2—Cl4 | 95.31 (10) | C32—C33—H33 | 119.0 |
N2—Sn2—Cl4 | 160.53 (7) | C33—C34—C35 | 119.9 (3) |
O3—Sn3—C47 | 109.91 (11) | C33—C34—H34 | 120.0 |
O3—Sn3—C54 | 112.76 (11) | C35—C34—H34 | 120.0 |
C47—Sn3—C54 | 136.71 (13) | C36—C35—C34 | 120.1 (4) |
O3—Sn3—N3 | 75.07 (9) | C36—C35—H35 | 120.0 |
C47—Sn3—N3 | 93.83 (11) | C34—C35—H35 | 120.0 |
C54—Sn3—N3 | 90.22 (11) | C35—C36—C37 | 118.8 (3) |
O3—Sn3—Cl7 | 87.28 (6) | C35—C36—H36 | 120.6 |
C47—Sn3—Cl7 | 92.43 (9) | C37—C36—H36 | 120.6 |
C54—Sn3—Cl7 | 96.48 (10) | C36—C37—C32 | 123.4 (3) |
N3—Sn3—Cl7 | 162.35 (7) | C36—C37—Cl5 | 118.1 (3) |
C22—O1—Sn1 | 119.21 (19) | C32—C37—Cl5 | 118.5 (3) |
C45—O2—Sn2 | 119.16 (19) | N2—C38—C39 | 122.3 (3) |
C68—O3—Sn3 | 119.50 (19) | N2—C38—H38 | 118.8 |
C15—N1—C23 | 118.8 (3) | C39—C38—H38 | 118.8 |
C15—N1—Sn1 | 131.2 (2) | C40—C39—C38 | 119.2 (3) |
C23—N1—Sn1 | 110.0 (2) | C40—C39—H39 | 120.4 |
C38—N2—C46 | 119.4 (3) | C38—C39—H39 | 120.4 |
C38—N2—Sn2 | 131.1 (2) | C39—C40—C41 | 120.4 (3) |
C46—N2—Sn2 | 109.5 (2) | C39—C40—H40 | 119.8 |
C61—N3—C69 | 119.3 (3) | C41—C40—H40 | 119.8 |
C61—N3—Sn3 | 131.3 (2) | C42—C41—C40 | 125.1 (3) |
C69—N3—Sn3 | 109.4 (2) | C42—C41—C46 | 118.3 (3) |
C2—C1—Sn1 | 118.5 (2) | C40—C41—C46 | 116.5 (3) |
C2—C1—H1A | 107.7 | C43—C42—C41 | 119.8 (3) |
Sn1—C1—H1A | 107.7 | C43—C42—H42 | 120.1 |
C2—C1—H1B | 107.7 | C41—C42—H42 | 120.1 |
Sn1—C1—H1B | 107.7 | C42—C43—C44 | 121.9 (3) |
H1A—C1—H1B | 107.1 | C42—C43—H43 | 119.1 |
C7—C2—C3 | 116.3 (3) | C44—C43—H43 | 119.1 |
C7—C2—C1 | 123.6 (3) | C45—C44—C43 | 120.2 (3) |
C3—C2—C1 | 120.0 (3) | C45—C44—H44 | 119.9 |
C4—C3—C2 | 122.3 (4) | C43—C44—H44 | 119.9 |
C4—C3—H3 | 118.8 | O2—C45—C44 | 122.2 (3) |
C2—C3—H3 | 118.8 | O2—C45—C46 | 119.2 (3) |
C5—C4—C3 | 120.2 (4) | C44—C45—C46 | 118.6 (3) |
C5—C4—H4 | 119.9 | N2—C46—C45 | 116.7 (3) |
C3—C4—H4 | 119.9 | N2—C46—C41 | 122.1 (3) |
C4—C5—C6 | 120.0 (4) | C45—C46—C41 | 121.2 (3) |
C4—C5—H5 | 120.0 | C48—C47—Sn3 | 116.1 (2) |
C6—C5—H5 | 120.0 | C48—C47—H47A | 108.3 |
C7—C6—C5 | 118.8 (4) | Sn3—C47—H47A | 108.3 |
C7—C6—H6 | 120.6 | C48—C47—H47B | 108.3 |
C5—C6—H6 | 120.6 | Sn3—C47—H47B | 108.3 |
C6—C7—C2 | 122.3 (3) | H47A—C47—H47B | 107.4 |
C6—C7—Cl2 | 118.4 (3) | C49—C48—C53 | 117.4 (3) |
C2—C7—Cl2 | 119.3 (3) | C49—C48—C47 | 119.6 (3) |
C9—C8—Sn1 | 117.9 (2) | C53—C48—C47 | 123.0 (3) |
C9—C8—H8A | 107.8 | C50—C49—C48 | 121.0 (3) |
Sn1—C8—H8A | 107.8 | C50—C49—H49 | 119.5 |
C9—C8—H8B | 107.8 | C48—C49—H49 | 119.5 |
Sn1—C8—H8B | 107.8 | C51—C50—C49 | 120.2 (4) |
H8A—C8—H8B | 107.2 | C51—C50—H50 | 119.9 |
C14—C9—C10 | 116.2 (3) | C49—C50—H50 | 119.9 |
C14—C9—C8 | 122.4 (3) | C50—C51—C52 | 120.5 (3) |
C10—C9—C8 | 121.3 (3) | C50—C51—H51 | 119.7 |
C11—C10—C9 | 121.3 (3) | C52—C51—H51 | 119.7 |
C11—C10—H10 | 119.3 | C51—C52—C53 | 118.6 (3) |
C9—C10—H10 | 119.3 | C51—C52—H52 | 120.7 |
C12—C11—C10 | 120.4 (3) | C53—C52—H52 | 120.7 |
C12—C11—H11 | 119.8 | C52—C53—C48 | 122.3 (3) |
C10—C11—H11 | 119.8 | C52—C53—Cl8 | 118.5 (3) |
C13—C12—C11 | 119.7 (3) | C48—C53—Cl8 | 119.2 (3) |
C13—C12—H12 | 120.2 | C55—C54—Sn3 | 113.5 (2) |
C11—C12—H12 | 120.2 | C55—C54—H54A | 108.9 |
C12—C13—C14 | 119.0 (3) | Sn3—C54—H54A | 108.9 |
C12—C13—H13 | 120.5 | C55—C54—H54B | 108.9 |
C14—C13—H13 | 120.5 | Sn3—C54—H54B | 108.9 |
C13—C14—C9 | 123.3 (3) | H54A—C54—H54B | 107.7 |
C13—C14—Cl3 | 118.6 (2) | C60—C55—C56 | 115.9 (3) |
C9—C14—Cl3 | 118.1 (3) | C60—C55—C54 | 121.9 (3) |
N1—C15—C16 | 122.4 (3) | C56—C55—C54 | 122.1 (3) |
N1—C15—H15 | 118.8 | C57—C56—C55 | 121.7 (3) |
C16—C15—H15 | 118.8 | C57—C56—H56 | 119.1 |
C17—C16—C15 | 119.4 (3) | C55—C56—H56 | 119.1 |
C17—C16—H16 | 120.3 | C56—C57—C58 | 120.5 (3) |
C15—C16—H16 | 120.3 | C56—C57—H57 | 119.8 |
C16—C17—C18 | 120.2 (3) | C58—C57—H57 | 119.8 |
C16—C17—H17 | 119.9 | C57—C58—C59 | 120.1 (3) |
C18—C17—H17 | 119.9 | C57—C58—H58 | 119.9 |
C19—C18—C23 | 118.6 (3) | C59—C58—H58 | 119.9 |
C19—C18—C17 | 125.1 (3) | C60—C59—C58 | 118.3 (3) |
C23—C18—C17 | 116.4 (3) | C60—C59—H59 | 120.8 |
C20—C19—C18 | 119.9 (3) | C58—C59—H59 | 120.8 |
C20—C19—H19 | 120.1 | C59—C60—C55 | 123.4 (3) |
C18—C19—H19 | 120.1 | C59—C60—Cl9 | 118.3 (3) |
C19—C20—C21 | 121.8 (3) | C55—C60—Cl9 | 118.2 (3) |
C19—C20—H20 | 119.1 | N3—C61—C62 | 122.1 (3) |
C21—C20—H20 | 119.1 | N3—C61—H61 | 118.9 |
C22—C21—C20 | 120.1 (3) | C62—C61—H61 | 118.9 |
C22—C21—H21 | 120.0 | C63—C62—C61 | 119.2 (3) |
C20—C21—H21 | 120.0 | C63—C62—H62 | 120.4 |
O1—C22—C21 | 122.1 (3) | C61—C62—H62 | 120.4 |
O1—C22—C23 | 119.2 (3) | C62—C63—C64 | 120.4 (3) |
C21—C22—C23 | 118.6 (3) | C62—C63—H63 | 119.8 |
N1—C23—C18 | 122.8 (3) | C64—C63—H63 | 119.8 |
N1—C23—C22 | 116.3 (3) | C65—C64—C69 | 118.6 (3) |
C18—C23—C22 | 121.0 (3) | C65—C64—C63 | 125.0 (3) |
C25—C24—Sn2 | 117.0 (2) | C69—C64—C63 | 116.5 (3) |
C25—C24—H24A | 108.1 | C66—C65—C64 | 119.9 (3) |
Sn2—C24—H24A | 108.1 | C66—C65—H65 | 120.0 |
C25—C24—H24B | 108.1 | C64—C65—H65 | 120.0 |
Sn2—C24—H24B | 108.1 | C65—C66—C67 | 121.5 (3) |
H24A—C24—H24B | 107.3 | C65—C66—H66 | 119.2 |
C30—C25—C26 | 116.6 (3) | C67—C66—H66 | 119.2 |
C30—C25—C24 | 122.2 (3) | C68—C67—C66 | 120.3 (3) |
C26—C25—C24 | 121.1 (3) | C68—C67—H67 | 119.9 |
C27—C26—C25 | 120.9 (3) | C66—C67—H67 | 119.9 |
C27—C26—H26 | 119.5 | O3—C68—C67 | 121.9 (3) |
C25—C26—H26 | 119.5 | O3—C68—C69 | 119.5 (3) |
C28—C27—C26 | 121.0 (3) | C67—C68—C69 | 118.7 (3) |
C28—C27—H27 | 119.5 | N3—C69—C64 | 122.5 (3) |
C26—C27—H27 | 119.5 | N3—C69—C68 | 116.5 (3) |
C27—C28—C29 | 119.5 (3) | C64—C69—C68 | 121.0 (3) |
C27—C28—H28 | 120.2 | ||
C8—Sn1—O1—C22 | 89.9 (2) | C28—C29—C30—Cl6 | 179.1 (3) |
C1—Sn1—O1—C22 | −88.1 (2) | C26—C25—C30—C29 | −1.7 (5) |
N1—Sn1—O1—C22 | 0.3 (2) | C24—C25—C30—C29 | 178.5 (3) |
Cl1—Sn1—O1—C22 | −178.8 (2) | C26—C25—C30—Cl6 | −179.5 (2) |
C31—Sn2—O2—C45 | −91.2 (2) | C24—C25—C30—Cl6 | 0.7 (4) |
C24—Sn2—O2—C45 | 85.1 (2) | O2—Sn2—C31—C32 | 92.9 (3) |
N2—Sn2—O2—C45 | −0.7 (2) | C24—Sn2—C31—C32 | −81.6 (3) |
Cl4—Sn2—O2—C45 | 179.0 (2) | N2—Sn2—C31—C32 | 16.4 (3) |
C47—Sn3—O3—C68 | 91.4 (2) | Cl4—Sn2—C31—C32 | 178.2 (3) |
C54—Sn3—O3—C68 | −81.2 (2) | Sn2—C31—C32—C37 | 72.5 (4) |
N3—Sn3—O3—C68 | 2.7 (2) | Sn2—C31—C32—C33 | −110.9 (3) |
Cl7—Sn3—O3—C68 | −177.0 (2) | C37—C32—C33—C34 | 1.9 (5) |
O1—Sn1—N1—C15 | −178.2 (3) | C31—C32—C33—C34 | −174.9 (3) |
C8—Sn1—N1—C15 | 73.1 (3) | C32—C33—C34—C35 | −1.3 (6) |
C1—Sn1—N1—C15 | −69.0 (3) | C33—C34—C35—C36 | −0.4 (6) |
Cl1—Sn1—N1—C15 | −175.6 (2) | C34—C35—C36—C37 | 1.3 (6) |
O1—Sn1—N1—C23 | −0.01 (19) | C35—C36—C37—C32 | −0.6 (5) |
C8—Sn1—N1—C23 | −108.8 (2) | C35—C36—C37—Cl5 | 178.2 (3) |
C1—Sn1—N1—C23 | 109.1 (2) | C33—C32—C37—C36 | −1.0 (5) |
Cl1—Sn1—N1—C23 | 2.5 (4) | C31—C32—C37—C36 | 175.8 (3) |
O2—Sn2—N2—C38 | 177.9 (3) | C33—C32—C37—Cl5 | −179.7 (3) |
C31—Sn2—N2—C38 | −72.6 (3) | C31—C32—C37—Cl5 | −2.9 (4) |
C24—Sn2—N2—C38 | 68.5 (3) | C46—N2—C38—C39 | 0.1 (5) |
Cl4—Sn2—N2—C38 | 177.2 (2) | Sn2—N2—C38—C39 | −177.2 (2) |
O2—Sn2—N2—C46 | 0.46 (19) | N2—C38—C39—C40 | −0.6 (5) |
C31—Sn2—N2—C46 | 109.9 (2) | C38—C39—C40—C41 | 0.1 (5) |
C24—Sn2—N2—C46 | −109.0 (2) | C39—C40—C41—C42 | −179.6 (3) |
Cl4—Sn2—N2—C46 | −0.2 (4) | C39—C40—C41—C46 | 0.6 (5) |
O3—Sn3—N3—C61 | 179.1 (3) | C40—C41—C42—C43 | −177.3 (3) |
C47—Sn3—N3—C61 | 69.5 (3) | C46—C41—C42—C43 | 2.4 (5) |
C54—Sn3—N3—C61 | −67.4 (3) | C41—C42—C43—C44 | −1.2 (5) |
Cl7—Sn3—N3—C61 | −180.0 (2) | C42—C43—C44—C45 | −0.3 (5) |
O3—Sn3—N3—C69 | −1.12 (19) | Sn2—O2—C45—C44 | −179.0 (2) |
C47—Sn3—N3—C69 | −110.7 (2) | Sn2—O2—C45—C46 | 0.9 (4) |
C54—Sn3—N3—C69 | 112.4 (2) | C43—C44—C45—O2 | −179.5 (3) |
Cl7—Sn3—N3—C69 | −0.2 (4) | C43—C44—C45—C46 | 0.5 (5) |
O1—Sn1—C1—C2 | 121.1 (3) | C38—N2—C46—C45 | −178.0 (3) |
C8—Sn1—C1—C2 | −56.0 (4) | Sn2—N2—C46—C45 | −0.2 (3) |
N1—Sn1—C1—C2 | 45.5 (3) | C38—N2—C46—C41 | 0.8 (5) |
Cl1—Sn1—C1—C2 | −152.5 (3) | Sn2—N2—C46—C41 | 178.6 (2) |
Sn1—C1—C2—C7 | 92.8 (4) | O2—C45—C46—N2 | −0.5 (4) |
Sn1—C1—C2—C3 | −86.5 (4) | C44—C45—C46—N2 | 179.5 (3) |
C7—C2—C3—C4 | −1.5 (5) | O2—C45—C46—C41 | −179.2 (3) |
C1—C2—C3—C4 | 177.9 (3) | C44—C45—C46—C41 | 0.7 (5) |
C2—C3—C4—C5 | 0.6 (6) | C42—C41—C46—N2 | 179.2 (3) |
C3—C4—C5—C6 | 0.6 (6) | C40—C41—C46—N2 | −1.1 (5) |
C4—C5—C6—C7 | −0.8 (6) | C42—C41—C46—C45 | −2.2 (5) |
C5—C6—C7—C2 | −0.2 (5) | C40—C41—C46—C45 | 177.6 (3) |
C5—C6—C7—Cl2 | 178.2 (3) | O3—Sn3—C47—C48 | −74.1 (2) |
C3—C2—C7—C6 | 1.3 (5) | C54—Sn3—C47—C48 | 95.8 (3) |
C1—C2—C7—C6 | −178.1 (3) | N3—Sn3—C47—C48 | 1.4 (2) |
C3—C2—C7—Cl2 | −177.1 (3) | Cl7—Sn3—C47—C48 | −162.1 (2) |
C1—C2—C7—Cl2 | 3.5 (5) | Sn3—C47—C48—C49 | 87.5 (3) |
O1—Sn1—C8—C9 | −98.9 (2) | Sn3—C47—C48—C53 | −91.6 (3) |
C1—Sn1—C8—C9 | 78.1 (3) | C53—C48—C49—C50 | −0.2 (5) |
N1—Sn1—C8—C9 | −23.0 (3) | C47—C48—C49—C50 | −179.3 (3) |
Cl1—Sn1—C8—C9 | 174.5 (2) | C48—C49—C50—C51 | 0.9 (6) |
Sn1—C8—C9—C14 | −69.7 (4) | C49—C50—C51—C52 | −1.2 (6) |
Sn1—C8—C9—C10 | 111.7 (3) | C50—C51—C52—C53 | 0.6 (6) |
C14—C9—C10—C11 | −1.1 (5) | C51—C52—C53—C48 | 0.2 (5) |
C8—C9—C10—C11 | 177.6 (3) | C51—C52—C53—Cl8 | −179.7 (3) |
C9—C10—C11—C12 | 0.7 (6) | C49—C48—C53—C52 | −0.4 (5) |
C10—C11—C12—C13 | −0.4 (6) | C47—C48—C53—C52 | 178.7 (3) |
C11—C12—C13—C14 | 0.5 (5) | C49—C48—C53—Cl8 | 179.5 (2) |
C12—C13—C14—C9 | −0.9 (5) | C47—C48—C53—Cl8 | −1.4 (4) |
C12—C13—C14—Cl3 | 178.5 (3) | O3—Sn3—C54—C55 | 138.4 (2) |
C10—C9—C14—C13 | 1.2 (5) | C47—Sn3—C54—C55 | −31.3 (3) |
C8—C9—C14—C13 | −177.4 (3) | N3—Sn3—C54—C55 | 64.5 (2) |
C10—C9—C14—Cl3 | −178.2 (2) | Cl7—Sn3—C54—C55 | −131.8 (2) |
C8—C9—C14—Cl3 | 3.2 (4) | Sn3—C54—C55—C60 | 68.4 (4) |
C23—N1—C15—C16 | −0.2 (5) | Sn3—C54—C55—C56 | −110.4 (3) |
Sn1—N1—C15—C16 | 177.8 (2) | C60—C55—C56—C57 | −0.8 (5) |
N1—C15—C16—C17 | 0.9 (5) | C54—C55—C56—C57 | 178.0 (3) |
C15—C16—C17—C18 | −0.7 (5) | C55—C56—C57—C58 | −0.5 (5) |
C16—C17—C18—C19 | −179.1 (3) | C56—C57—C58—C59 | 1.2 (5) |
C16—C17—C18—C23 | −0.3 (5) | C57—C58—C59—C60 | −0.5 (5) |
C23—C18—C19—C20 | −1.4 (5) | C58—C59—C60—C55 | −0.9 (5) |
C17—C18—C19—C20 | 177.5 (3) | C58—C59—C60—Cl9 | 180.0 (3) |
C18—C19—C20—C21 | 0.4 (5) | C56—C55—C60—C59 | 1.5 (5) |
C19—C20—C21—C22 | 0.9 (5) | C54—C55—C60—C59 | −177.3 (3) |
Sn1—O1—C22—C21 | 178.7 (2) | C56—C55—C60—Cl9 | −179.3 (2) |
Sn1—O1—C22—C23 | −0.6 (4) | C54—C55—C60—Cl9 | 1.8 (4) |
C20—C21—C22—O1 | 179.5 (3) | C69—N3—C61—C62 | −0.4 (5) |
C20—C21—C22—C23 | −1.1 (5) | Sn3—N3—C61—C62 | 179.3 (2) |
C15—N1—C23—C18 | −0.8 (5) | N3—C61—C62—C63 | 0.5 (5) |
Sn1—N1—C23—C18 | −179.2 (2) | C61—C62—C63—C64 | −0.4 (5) |
C15—N1—C23—C22 | 178.1 (3) | C62—C63—C64—C65 | −178.2 (3) |
Sn1—N1—C23—C22 | −0.3 (3) | C62—C63—C64—C69 | 0.3 (5) |
C19—C18—C23—N1 | 179.9 (3) | C69—C64—C65—C66 | −1.2 (5) |
C17—C18—C23—N1 | 1.0 (5) | C63—C64—C65—C66 | 177.2 (3) |
C19—C18—C23—C22 | 1.1 (5) | C64—C65—C66—C67 | 1.6 (5) |
C17—C18—C23—C22 | −177.8 (3) | C65—C66—C67—C68 | 0.1 (5) |
O1—C22—C23—N1 | 0.6 (4) | Sn3—O3—C68—C67 | 175.5 (2) |
C21—C22—C23—N1 | −178.8 (3) | Sn3—O3—C68—C69 | −4.0 (4) |
O1—C22—C23—C18 | 179.5 (3) | C66—C67—C68—O3 | 178.4 (3) |
C21—C22—C23—C18 | 0.2 (4) | C66—C67—C68—C69 | −2.0 (5) |
O2—Sn2—C24—C25 | −139.5 (2) | C61—N3—C69—C64 | 0.3 (5) |
C31—Sn2—C24—C25 | 35.0 (4) | Sn3—N3—C69—C64 | −179.5 (2) |
N2—Sn2—C24—C25 | −64.6 (3) | C61—N3—C69—C68 | 179.4 (3) |
Cl4—Sn2—C24—C25 | 133.9 (3) | Sn3—N3—C69—C68 | −0.4 (3) |
Sn2—C24—C25—C30 | −80.0 (4) | C65—C64—C69—N3 | 178.4 (3) |
Sn2—C24—C25—C26 | 100.2 (3) | C63—C64—C69—N3 | −0.2 (5) |
C30—C25—C26—C27 | 0.8 (5) | C65—C64—C69—C68 | −0.7 (5) |
C24—C25—C26—C27 | −179.4 (3) | C63—C64—C69—C68 | −179.3 (3) |
C25—C26—C27—C28 | 0.4 (5) | O3—C68—C69—N3 | 2.8 (4) |
C26—C27—C28—C29 | −0.9 (6) | C67—C68—C69—N3 | −176.8 (3) |
C27—C28—C29—C30 | 0.1 (5) | O3—C68—C69—C64 | −178.1 (3) |
C28—C29—C30—C25 | 1.2 (5) | C67—C68—C69—C64 | 2.3 (5) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C7H6Cl)2(C9H6NO)Cl] |
Mr | 549.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 10.2504 (1), 41.2573 (6), 15.3882 (2) |
β (°) | 100.3433 (6) |
V (Å3) | 6401.98 (14) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.25 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.692, 0.797 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41105, 14589, 13128 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.086, 1.11 |
No. of reflections | 14589 |
No. of parameters | 784 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0318P)2 + 14.3485P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.27, −1.42 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Shi, D.-S. & Hu, S.-Z. (1987). Chin. J. Struct. Chem. 6, 193–197. CAS Google Scholar
Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541. CrossRef Web of Science Google Scholar
Vafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m964. Web of Science CSD CrossRef IUCr Journals Google Scholar
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8-Hydroxyquinoline forms a large number of derivatives with organotin systems; when the reaction is carried out with diorganotin dichlorides, in some cases only one chloride is displaced whereas in other cases both are displaced. No base is added to abstract the acid hydroxy proton. In the present study, the reaction of 8-hydroxyquinoline with bis(2-chlorobenzyl)tin dichloride affords SnCl(C7H6Cl)2(C9H6NO) (Scheme I). The SnIV atom in the three independent molecules N,O-chelated by the quinolinato group and it exists in a cis-C2SnNOCl trigonal bipyramidal geometry; the O atom lies in the equatorial plane and the Cl and N atoms comprise the axial sites (Figs. 1, 2, 3). The molecules are positioned such that two are disposed about a false-center of inversion (Fig. 2). There are no Sn···Cl contacts and the distortion of geometry from the idealized trigonal bipyramid is minimal (14.7% in the first molecule, 13.7% in the second and only 9.9% in the third).
In the diethytin derivative, an intermolecule Sn···Cl interaction raises the coordination number of Sn to six in the chain structure (Shi & Hu, 1987). On the other hand, the methylphenyltin derivative also has Sn in a six-coordinate environment, but the higher coordination number arises from bridging by the quinolinate ion that results in a dinuclear molecule (Vafaee et al., 2010).