metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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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

(Received 20 April 2011; accepted 26 April 2011; online 7 May 2011)

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[Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.]). For related structures, see: Shi & Hu (1987[Shi, D.-S. & Hu, S.-Z. (1987). Chin. J. Struct. Chem. 6, 193-197.]); Vafaee et al. (2010[Vafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m964.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C7H6Cl)2(C9H6NO)Cl]

  • Mr = 549.42

  • Monoclinic, P 21 /n

  • a = 10.2504 (1) Å

  • b = 41.2573 (6) Å

  • c = 15.3882 (2) Å

  • β = 100.3433 (6)°

  • V = 6401.98 (14) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 1.59 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.692, Tmax = 0.797

  • 41105 measured reflections

  • 14589 independent reflections

  • 13128 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.086

  • S = 1.11

  • 14589 reflections

  • 784 parameters

  • H-atom parameters constrained

  • Δρmax = 1.27 e Å−3

  • Δρmin = −1.42 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT; data reduction: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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).

Related literature top

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 top

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.

Refinement top

H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement 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 refinement with regard to the peak/hole. This high value was retained.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of molecule 1 of SnCl(C7H6Cl)2(C9H6NO) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Anisotropic displacement ellipsoid plot (Barbour, 2001) of molecule 2 of SnCl(C7H6Cl)2(C9H6NO) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 3] Fig. 3. Anisotropic displacement ellipsoid plot (Barbour, 2001) of molecule 3 of SnCl(C7H6Cl)2(C9H6NO) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 4] Fig. 4. Positions of molecules 1 and 2, and the inversion-related pair of molecule 3.
Chloridobis(2-chlorobenzyl)(quinolin-8-olato-κ2N,O)tin(IV) top
Crystal data top
[Sn(C7H6Cl)2(C9H6NO)Cl]F(000) = 3264
Mr = 549.42Dx = 1.710 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9252 reflections
a = 10.2504 (1) Åθ = 2.4–28.3°
b = 41.2573 (6) ŵ = 1.59 mm1
c = 15.3882 (2) ÅT = 100 K
β = 100.3433 (6)°Block, colorless
V = 6401.98 (14) Å30.25 × 0.20 × 0.15 mm
Z = 12
Data collection top
Bruker SMART APEX
diffractometer
14589 independent reflections
Radiation source: fine-focus sealed tube13128 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.692, Tmax = 0.797k = 5340
41105 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-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 parametersΔρmax = 1.27 e Å3
0 restraintsΔρmin = 1.42 e Å3
Crystal data top
[Sn(C7H6Cl)2(C9H6NO)Cl]V = 6401.98 (14) Å3
Mr = 549.42Z = 12
Monoclinic, P21/nMo Kα radiation
a = 10.2504 (1) ŵ = 1.59 mm1
b = 41.2573 (6) ÅT = 100 K
c = 15.3882 (2) Å0.25 × 0.20 × 0.15 mm
β = 100.3433 (6)°
Data collection top
Bruker SMART APEX
diffractometer
14589 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
13128 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.797Rint = 0.024
41105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0318P)2 + 14.3485P]
where P = (Fo2 + 2Fc2)/3
14589 reflectionsΔρmax = 1.27 e Å3
784 parametersΔρmin = 1.42 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.51891 (2)0.342454 (5)0.664659 (14)0.01383 (5)
Sn20.51124 (2)0.325014 (5)0.306586 (14)0.01375 (5)
Sn30.49861 (2)0.005273 (5)0.701013 (14)0.01335 (5)
Cl10.35889 (8)0.30078 (2)0.60004 (6)0.02297 (17)
Cl20.28721 (9)0.35808 (3)0.86345 (6)0.0307 (2)
Cl30.37714 (9)0.41474 (2)0.73481 (6)0.02583 (18)
Cl40.66348 (8)0.36906 (2)0.36650 (6)0.02405 (18)
Cl50.65041 (10)0.24788 (2)0.24180 (6)0.0301 (2)
Cl60.76770 (9)0.31831 (2)0.15379 (6)0.02775 (19)
Cl70.33400 (8)0.036560 (19)0.64966 (6)0.02048 (16)
Cl80.38458 (10)0.09956 (2)0.74145 (6)0.0296 (2)
Cl90.26222 (8)0.02390 (2)0.83358 (5)0.02545 (18)
O10.6547 (2)0.31709 (5)0.60960 (14)0.0158 (4)
O20.3754 (2)0.34906 (5)0.36442 (14)0.0160 (4)
O30.6230 (2)0.01859 (5)0.63342 (15)0.0172 (5)
N10.7171 (3)0.37103 (6)0.70561 (17)0.0152 (5)
N20.3191 (3)0.29384 (6)0.27310 (17)0.0149 (5)
N30.6961 (3)0.03576 (6)0.72578 (17)0.0155 (5)
C10.5196 (4)0.32487 (8)0.7971 (2)0.0228 (7)
H1A0.43120.31540.79840.027*
H1B0.58470.30700.80830.027*
C20.5502 (3)0.34804 (8)0.8716 (2)0.0181 (7)
C30.6818 (4)0.35385 (10)0.9111 (3)0.0296 (8)
H30.75030.34220.89070.036*
C40.7155 (4)0.37575 (11)0.9782 (3)0.0390 (11)
H40.80620.37921.00300.047*
C50.6192 (5)0.39269 (10)1.0095 (2)0.0403 (12)
H50.64300.40801.05570.048*
C60.4858 (5)0.38745 (9)0.9736 (2)0.0321 (9)
H60.41800.39890.99550.039*
C70.4539 (3)0.36523 (8)0.9056 (2)0.0197 (7)
C80.4283 (3)0.37879 (8)0.5727 (2)0.0195 (7)
H8A0.43740.37170.51260.023*
H8B0.33230.37920.57470.023*
C90.4790 (3)0.41255 (8)0.5851 (2)0.0165 (6)
C100.5479 (4)0.42694 (9)0.5246 (2)0.0227 (7)
H100.56570.41460.47590.027*
C110.5910 (4)0.45888 (10)0.5344 (3)0.0302 (8)
H110.63670.46820.49210.036*
C120.5676 (4)0.47723 (9)0.6057 (2)0.0265 (8)
H120.59770.49900.61230.032*
C130.5003 (3)0.46368 (8)0.6667 (2)0.0210 (7)
H130.48300.47600.71550.025*
C140.4584 (3)0.43187 (8)0.6559 (2)0.0161 (6)
C150.7455 (3)0.39726 (8)0.7550 (2)0.0178 (6)
H150.67630.40760.77810.021*
C160.8738 (3)0.41027 (8)0.7745 (2)0.0221 (7)
H160.89100.42890.81090.027*
C170.9739 (3)0.39583 (8)0.7406 (2)0.0214 (7)
H171.06090.40460.75300.026*
C180.9483 (3)0.36779 (8)0.6871 (2)0.0162 (6)
C191.0442 (3)0.35066 (8)0.6496 (2)0.0193 (7)
H191.13300.35830.65770.023*
C201.0088 (3)0.32306 (9)0.6017 (2)0.0211 (7)
H201.07420.31170.57720.025*
C210.8782 (3)0.31108 (8)0.5878 (2)0.0171 (6)
H210.85690.29170.55490.020*
C220.7806 (3)0.32750 (8)0.62184 (19)0.0144 (6)
C230.8163 (3)0.35615 (8)0.67214 (19)0.0144 (6)
C240.4908 (4)0.34026 (8)0.1706 (2)0.0223 (7)
H24A0.40320.35080.15360.027*
H24B0.55920.35690.16700.027*
C250.5024 (3)0.31453 (8)0.1037 (2)0.0165 (6)
C260.3891 (4)0.30107 (9)0.0511 (2)0.0248 (8)
H260.30370.30850.05750.030*
C270.4002 (4)0.27714 (10)0.0099 (2)0.0302 (9)
H270.32230.26850.04510.036*
C280.5223 (4)0.26566 (9)0.0205 (2)0.0300 (9)
H280.52870.24900.06210.036*
C290.6358 (4)0.27858 (9)0.0299 (2)0.0250 (8)
H290.72070.27090.02320.030*
C300.6244 (3)0.30281 (8)0.0901 (2)0.0179 (6)
C310.6184 (3)0.29074 (8)0.3978 (2)0.0211 (7)
H31A0.71080.29020.38710.025*
H31B0.62170.29950.45800.025*
C320.5725 (3)0.25673 (8)0.3986 (2)0.0165 (6)
C330.5197 (4)0.24448 (10)0.4697 (2)0.0270 (8)
H330.50670.25880.51580.032*
C340.4858 (4)0.21223 (11)0.4750 (3)0.0345 (9)
H340.45180.20460.52470.041*
C350.5013 (4)0.19110 (10)0.4077 (3)0.0313 (9)
H350.47850.16890.41150.038*
C360.5498 (4)0.20224 (9)0.3353 (2)0.0244 (7)
H360.55910.18800.28830.029*
C370.5848 (3)0.23456 (8)0.3323 (2)0.0174 (6)
C380.2936 (3)0.26708 (8)0.2257 (2)0.0183 (6)
H380.36300.25730.20140.022*
C390.1678 (4)0.25257 (8)0.2101 (2)0.0227 (7)
H390.15240.23340.17540.027*
C400.0673 (3)0.26633 (8)0.2456 (2)0.0217 (7)
H400.01820.25660.23550.026*
C410.0902 (3)0.29479 (8)0.2971 (2)0.0185 (7)
C420.0053 (3)0.31081 (9)0.3369 (2)0.0218 (7)
H420.09200.30200.33220.026*
C430.0271 (3)0.33903 (9)0.3824 (2)0.0218 (7)
H430.03850.34980.40810.026*
C440.1552 (3)0.35252 (9)0.3923 (2)0.0193 (7)
H440.17460.37220.42400.023*
C450.2524 (3)0.33724 (8)0.35614 (19)0.0144 (6)
C460.2201 (3)0.30805 (8)0.3085 (2)0.0151 (6)
C470.3890 (3)0.04155 (8)0.6179 (2)0.0177 (6)
H47A0.35280.03150.56020.021*
H47B0.31270.04830.64500.021*
C480.4642 (3)0.07106 (8)0.6015 (2)0.0158 (6)
C490.5337 (3)0.07149 (9)0.5316 (2)0.0232 (7)
H490.53170.05300.49470.028*
C500.6058 (4)0.09847 (11)0.5153 (3)0.0334 (9)
H500.65160.09850.46680.040*
C510.6113 (4)0.12534 (10)0.5691 (3)0.0311 (9)
H510.66230.14360.55820.037*
C520.5433 (4)0.12588 (9)0.6389 (2)0.0244 (7)
H520.54630.14440.67570.029*
C530.4706 (3)0.09875 (8)0.6540 (2)0.0175 (6)
C540.5296 (4)0.00778 (8)0.8390 (2)0.0211 (7)
H54A0.46090.02370.84820.025*
H54B0.61700.01850.85510.025*
C550.5246 (3)0.02044 (8)0.8991 (2)0.0182 (7)
C560.6380 (4)0.03202 (9)0.9556 (2)0.0238 (7)
H560.72020.02120.95720.029*
C570.6332 (4)0.05867 (10)1.0089 (2)0.0292 (9)
H570.71150.06581.04670.035*
C580.5157 (4)0.07504 (9)1.0076 (2)0.0280 (8)
H580.51360.09361.04370.034*
C590.3999 (4)0.06433 (9)0.9535 (2)0.0234 (7)
H590.31810.07530.95240.028*
C600.4070 (3)0.03732 (8)0.9013 (2)0.0178 (7)
C610.7283 (3)0.06276 (8)0.7710 (2)0.0194 (7)
H610.66420.07280.79960.023*
C620.8548 (4)0.07705 (8)0.7782 (2)0.0243 (7)
H620.87550.09640.81150.029*
C630.9477 (3)0.06275 (9)0.7366 (2)0.0236 (7)
H631.03290.07230.74080.028*
C640.9170 (3)0.03384 (8)0.6874 (2)0.0193 (7)
C651.0060 (3)0.01673 (9)0.6442 (2)0.0234 (7)
H651.09270.02500.64470.028*
C660.9673 (3)0.01177 (9)0.6017 (2)0.0217 (7)
H661.02870.02340.57410.026*
C670.8383 (3)0.02427 (9)0.5979 (2)0.0191 (7)
H670.81400.04410.56800.023*
C680.7474 (3)0.00779 (8)0.6374 (2)0.0161 (6)
C690.7877 (3)0.02121 (8)0.6840 (2)0.0153 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01268 (10)0.01196 (11)0.01760 (10)0.00043 (8)0.00474 (8)0.00269 (8)
Sn20.01284 (10)0.01225 (11)0.01672 (10)0.00010 (8)0.00417 (8)0.00330 (8)
Sn30.01349 (10)0.01096 (11)0.01619 (10)0.00032 (8)0.00426 (8)0.00004 (8)
Cl10.0155 (4)0.0190 (4)0.0347 (4)0.0035 (3)0.0052 (3)0.0078 (3)
Cl20.0187 (4)0.0405 (6)0.0346 (5)0.0005 (4)0.0093 (4)0.0044 (4)
Cl30.0314 (5)0.0270 (5)0.0231 (4)0.0010 (4)0.0154 (3)0.0016 (3)
Cl40.0185 (4)0.0203 (4)0.0347 (4)0.0064 (3)0.0084 (3)0.0108 (3)
Cl50.0408 (5)0.0321 (5)0.0213 (4)0.0002 (4)0.0160 (4)0.0001 (3)
Cl60.0199 (4)0.0336 (5)0.0279 (4)0.0079 (4)0.0007 (3)0.0006 (4)
Cl70.0163 (4)0.0156 (4)0.0305 (4)0.0040 (3)0.0067 (3)0.0021 (3)
Cl80.0376 (5)0.0311 (5)0.0222 (4)0.0009 (4)0.0114 (4)0.0044 (3)
Cl90.0158 (4)0.0385 (5)0.0219 (4)0.0020 (3)0.0028 (3)0.0009 (3)
O10.0125 (11)0.0147 (11)0.0211 (11)0.0009 (8)0.0054 (9)0.0039 (9)
O20.0141 (11)0.0158 (12)0.0186 (11)0.0012 (9)0.0039 (9)0.0045 (9)
O30.0140 (11)0.0151 (12)0.0232 (11)0.0024 (9)0.0057 (9)0.0038 (9)
N10.0151 (13)0.0127 (13)0.0172 (12)0.0038 (10)0.0013 (10)0.0017 (10)
N20.0160 (13)0.0134 (13)0.0150 (12)0.0012 (10)0.0021 (10)0.0002 (10)
N30.0173 (13)0.0112 (13)0.0174 (12)0.0001 (10)0.0014 (10)0.0016 (10)
C10.0310 (19)0.0171 (17)0.0235 (17)0.0012 (14)0.0134 (15)0.0009 (13)
C20.0188 (16)0.0215 (17)0.0148 (14)0.0005 (13)0.0052 (12)0.0041 (12)
C30.0224 (18)0.036 (2)0.0301 (19)0.0018 (16)0.0036 (15)0.0105 (16)
C40.037 (2)0.045 (3)0.029 (2)0.021 (2)0.0089 (18)0.0123 (18)
C50.075 (3)0.030 (2)0.0127 (16)0.031 (2)0.0031 (19)0.0002 (15)
C60.055 (3)0.023 (2)0.0227 (17)0.0014 (18)0.0174 (18)0.0007 (15)
C70.0234 (17)0.0186 (17)0.0173 (15)0.0042 (13)0.0039 (13)0.0003 (12)
C80.0173 (16)0.0193 (17)0.0212 (16)0.0018 (13)0.0015 (13)0.0023 (13)
C90.0167 (15)0.0180 (17)0.0141 (14)0.0066 (13)0.0009 (12)0.0005 (12)
C100.0277 (19)0.0236 (19)0.0184 (16)0.0060 (14)0.0089 (14)0.0005 (13)
C110.038 (2)0.028 (2)0.0294 (19)0.0008 (17)0.0174 (17)0.0054 (15)
C120.034 (2)0.0150 (17)0.0311 (19)0.0002 (15)0.0071 (16)0.0019 (14)
C130.0235 (17)0.0202 (17)0.0191 (15)0.0059 (14)0.0035 (13)0.0035 (13)
C140.0160 (15)0.0187 (17)0.0140 (14)0.0032 (12)0.0039 (12)0.0017 (12)
C150.0205 (16)0.0126 (15)0.0192 (15)0.0025 (12)0.0003 (13)0.0010 (12)
C160.0259 (18)0.0138 (16)0.0255 (17)0.0007 (14)0.0013 (14)0.0003 (13)
C170.0204 (17)0.0194 (17)0.0228 (16)0.0057 (13)0.0005 (13)0.0039 (13)
C180.0151 (15)0.0166 (16)0.0165 (14)0.0001 (12)0.0016 (12)0.0059 (12)
C190.0124 (15)0.0230 (18)0.0227 (16)0.0018 (13)0.0039 (13)0.0078 (13)
C200.0161 (16)0.031 (2)0.0170 (15)0.0067 (14)0.0052 (13)0.0051 (13)
C210.0169 (15)0.0199 (17)0.0146 (14)0.0022 (13)0.0034 (12)0.0002 (12)
C220.0129 (14)0.0176 (16)0.0127 (13)0.0021 (12)0.0027 (11)0.0040 (11)
C230.0153 (15)0.0148 (16)0.0134 (14)0.0008 (12)0.0034 (12)0.0029 (11)
C240.0309 (19)0.0156 (17)0.0223 (16)0.0018 (14)0.0100 (14)0.0020 (13)
C250.0247 (17)0.0093 (15)0.0159 (14)0.0019 (12)0.0048 (13)0.0068 (11)
C260.0214 (17)0.026 (2)0.0249 (17)0.0017 (14)0.0011 (14)0.0080 (14)
C270.038 (2)0.028 (2)0.0204 (17)0.0175 (17)0.0062 (15)0.0017 (15)
C280.053 (3)0.0219 (19)0.0163 (16)0.0087 (17)0.0086 (16)0.0043 (14)
C290.033 (2)0.0232 (19)0.0227 (17)0.0016 (15)0.0143 (15)0.0028 (14)
C300.0211 (16)0.0187 (17)0.0133 (14)0.0068 (13)0.0014 (12)0.0012 (12)
C310.0188 (16)0.0184 (17)0.0235 (17)0.0036 (13)0.0028 (13)0.0024 (13)
C320.0153 (15)0.0184 (17)0.0149 (14)0.0057 (12)0.0000 (12)0.0010 (12)
C330.030 (2)0.035 (2)0.0174 (16)0.0131 (16)0.0094 (14)0.0024 (14)
C340.028 (2)0.042 (3)0.038 (2)0.0057 (17)0.0169 (17)0.0187 (18)
C350.027 (2)0.021 (2)0.046 (2)0.0004 (15)0.0058 (17)0.0113 (17)
C360.0228 (18)0.0191 (18)0.0293 (18)0.0019 (14)0.0004 (15)0.0026 (14)
C370.0175 (16)0.0223 (17)0.0130 (14)0.0018 (13)0.0046 (12)0.0014 (12)
C380.0210 (16)0.0137 (16)0.0196 (15)0.0014 (13)0.0019 (13)0.0010 (12)
C390.0283 (19)0.0137 (17)0.0240 (17)0.0061 (14)0.0007 (14)0.0015 (13)
C400.0217 (17)0.0200 (18)0.0219 (16)0.0050 (14)0.0003 (13)0.0060 (13)
C410.0168 (16)0.0214 (17)0.0163 (15)0.0025 (13)0.0004 (12)0.0054 (12)
C420.0135 (16)0.030 (2)0.0224 (16)0.0001 (14)0.0041 (13)0.0094 (14)
C430.0182 (16)0.031 (2)0.0169 (15)0.0054 (14)0.0066 (13)0.0055 (13)
C440.0198 (16)0.0226 (18)0.0152 (15)0.0046 (13)0.0024 (12)0.0004 (12)
C450.0142 (15)0.0171 (16)0.0116 (13)0.0017 (12)0.0016 (11)0.0027 (11)
C460.0168 (15)0.0141 (16)0.0141 (14)0.0022 (12)0.0015 (12)0.0026 (11)
C470.0178 (16)0.0124 (16)0.0221 (16)0.0021 (12)0.0011 (13)0.0005 (12)
C480.0144 (15)0.0137 (16)0.0178 (15)0.0013 (12)0.0009 (12)0.0026 (12)
C490.0221 (17)0.0271 (19)0.0210 (16)0.0019 (14)0.0061 (14)0.0008 (14)
C500.031 (2)0.043 (3)0.0288 (19)0.0078 (18)0.0110 (16)0.0082 (17)
C510.027 (2)0.029 (2)0.035 (2)0.0109 (16)0.0002 (16)0.0112 (16)
C520.0253 (18)0.0165 (17)0.0271 (17)0.0022 (14)0.0066 (14)0.0016 (14)
C530.0169 (16)0.0192 (17)0.0150 (14)0.0027 (12)0.0006 (12)0.0018 (12)
C540.0230 (17)0.0200 (18)0.0213 (16)0.0026 (13)0.0071 (14)0.0026 (13)
C550.0197 (16)0.0187 (17)0.0165 (15)0.0010 (13)0.0040 (12)0.0092 (12)
C560.0206 (17)0.031 (2)0.0202 (16)0.0000 (14)0.0048 (13)0.0065 (14)
C570.029 (2)0.041 (2)0.0172 (16)0.0162 (17)0.0018 (14)0.0013 (15)
C580.044 (2)0.0230 (19)0.0194 (16)0.0084 (16)0.0115 (16)0.0030 (14)
C590.0303 (19)0.0229 (19)0.0186 (16)0.0043 (15)0.0089 (14)0.0000 (13)
C600.0174 (16)0.0238 (18)0.0125 (14)0.0018 (13)0.0036 (12)0.0027 (12)
C610.0209 (17)0.0146 (16)0.0202 (15)0.0007 (13)0.0033 (13)0.0010 (12)
C620.0263 (18)0.0126 (17)0.0299 (18)0.0026 (14)0.0062 (15)0.0027 (13)
C630.0194 (17)0.0198 (18)0.0283 (18)0.0068 (14)0.0042 (14)0.0072 (14)
C640.0165 (16)0.0204 (17)0.0191 (15)0.0039 (13)0.0022 (12)0.0066 (13)
C650.0160 (16)0.034 (2)0.0205 (16)0.0020 (14)0.0039 (13)0.0086 (14)
C660.0166 (16)0.034 (2)0.0164 (15)0.0036 (14)0.0069 (13)0.0043 (13)
C670.0197 (16)0.0229 (18)0.0143 (14)0.0017 (13)0.0020 (12)0.0001 (12)
C680.0146 (15)0.0171 (16)0.0159 (14)0.0008 (12)0.0014 (12)0.0032 (12)
C690.0173 (15)0.0127 (15)0.0154 (14)0.0005 (12)0.0014 (12)0.0035 (11)
Geometric parameters (Å, º) top
Sn1—O12.043 (2)C26—H260.9500
Sn1—C82.154 (3)C27—C281.375 (6)
Sn1—C12.162 (3)C27—H270.9500
Sn1—N12.335 (3)C28—C291.384 (5)
Sn1—Cl12.4596 (8)C28—H280.9500
Sn2—O22.039 (2)C29—C301.382 (5)
Sn2—C312.150 (3)C29—H290.9500
Sn2—C242.159 (3)C31—C321.481 (5)
Sn2—N22.331 (3)C31—H31A0.9900
Sn2—Cl42.4638 (8)C31—H31B0.9900
Sn3—O32.038 (2)C32—C371.393 (4)
Sn3—C472.150 (3)C32—C331.399 (5)
Sn3—C542.159 (3)C33—C341.381 (6)
Sn3—N32.355 (3)C33—H330.9500
Sn3—Cl72.4437 (8)C34—C351.384 (6)
Cl2—C71.740 (4)C34—H340.9500
Cl3—C141.741 (3)C35—C361.378 (5)
Cl5—C371.741 (3)C35—H350.9500
Cl6—C301.735 (3)C36—C371.384 (5)
Cl8—C531.736 (3)C36—H360.9500
Cl9—C601.743 (3)C38—C391.403 (5)
O1—C221.341 (4)C38—H380.9500
O2—C451.337 (4)C39—C401.373 (5)
O3—C681.342 (4)C39—H390.9500
N1—C151.325 (4)C40—C411.412 (5)
N1—C231.365 (4)C40—H400.9500
N2—C381.323 (4)C41—C421.410 (5)
N2—C461.367 (4)C41—C461.421 (4)
N3—C611.324 (4)C42—C431.368 (5)
N3—C691.368 (4)C42—H420.9500
C1—C21.483 (5)C43—C441.408 (5)
C1—H1A0.9900C43—H430.9500
C1—H1B0.9900C44—C451.378 (4)
C2—C71.391 (5)C44—H440.9500
C2—C31.397 (5)C45—C461.418 (4)
C3—C41.368 (6)C47—C481.486 (4)
C3—H30.9500C47—H47A0.9900
C4—C51.366 (7)C47—H47B0.9900
C4—H40.9500C48—C491.393 (5)
C5—C61.397 (6)C48—C531.394 (5)
C5—H50.9500C49—C501.384 (5)
C6—C71.386 (5)C49—H490.9500
C6—H60.9500C50—C511.379 (6)
C8—C91.487 (5)C50—H500.9500
C8—H8A0.9900C51—C521.381 (5)
C8—H8B0.9900C51—H510.9500
C9—C141.396 (4)C52—C531.388 (5)
C9—C101.397 (5)C52—H520.9500
C10—C111.389 (5)C54—C551.493 (5)
C10—H100.9500C54—H54A0.9900
C11—C121.388 (5)C54—H54B0.9900
C11—H110.9500C55—C601.398 (5)
C12—C131.379 (5)C55—C561.405 (5)
C12—H120.9500C56—C571.377 (5)
C13—C141.382 (5)C56—H560.9500
C13—H130.9500C57—C581.379 (6)
C15—C161.402 (5)C57—H570.9500
C15—H150.9500C58—C591.394 (5)
C16—C171.369 (5)C58—H580.9500
C16—H160.9500C59—C601.383 (5)
C17—C181.416 (5)C59—H590.9500
C17—H170.9500C61—C621.411 (5)
C18—C191.415 (5)C61—H610.9500
C18—C231.415 (4)C62—C631.372 (5)
C19—C201.370 (5)C62—H620.9500
C19—H190.9500C63—C641.417 (5)
C20—C211.407 (5)C63—H630.9500
C20—H200.9500C64—C651.411 (5)
C21—C221.387 (4)C64—C691.417 (4)
C21—H210.9500C65—C661.369 (5)
C22—C231.424 (4)C65—H650.9500
C24—C251.498 (5)C66—C671.410 (5)
C24—H24A0.9900C66—H660.9500
C24—H24B0.9900C67—C681.380 (4)
C25—C301.392 (5)C67—H670.9500
C25—C261.405 (5)C68—C691.418 (4)
C26—C271.381 (5)
O1—Sn1—C8109.26 (11)C29—C28—H28120.2
O1—Sn1—C1109.37 (11)C30—C29—C28119.4 (3)
C8—Sn1—C1141.32 (13)C30—C29—H29120.3
O1—Sn1—N175.30 (9)C28—C29—H29120.3
C8—Sn1—N194.45 (11)C29—C30—C25122.6 (3)
C1—Sn1—N193.41 (12)C29—C30—Cl6118.7 (3)
O1—Sn1—Cl185.92 (7)C25—C30—Cl6118.7 (3)
C8—Sn1—Cl192.48 (9)C32—C31—Sn2120.2 (2)
C1—Sn1—Cl192.04 (10)C32—C31—H31A107.3
N1—Sn1—Cl1161.20 (7)Sn2—C31—H31A107.3
O2—Sn2—C31110.12 (11)C32—C31—H31B107.3
O2—Sn2—C24109.04 (11)Sn2—C31—H31B107.3
C31—Sn2—C24140.67 (13)H31A—C31—H31B106.9
O2—Sn2—N275.47 (9)C37—C32—C33115.7 (3)
C31—Sn2—N295.38 (11)C37—C32—C31123.0 (3)
C24—Sn2—N290.89 (12)C33—C32—C31121.2 (3)
O2—Sn2—Cl485.07 (7)C34—C33—C32122.1 (3)
C31—Sn2—Cl491.48 (9)C34—C33—H33119.0
C24—Sn2—Cl495.31 (10)C32—C33—H33119.0
N2—Sn2—Cl4160.53 (7)C33—C34—C35119.9 (3)
O3—Sn3—C47109.91 (11)C33—C34—H34120.0
O3—Sn3—C54112.76 (11)C35—C34—H34120.0
C47—Sn3—C54136.71 (13)C36—C35—C34120.1 (4)
O3—Sn3—N375.07 (9)C36—C35—H35120.0
C47—Sn3—N393.83 (11)C34—C35—H35120.0
C54—Sn3—N390.22 (11)C35—C36—C37118.8 (3)
O3—Sn3—Cl787.28 (6)C35—C36—H36120.6
C47—Sn3—Cl792.43 (9)C37—C36—H36120.6
C54—Sn3—Cl796.48 (10)C36—C37—C32123.4 (3)
N3—Sn3—Cl7162.35 (7)C36—C37—Cl5118.1 (3)
C22—O1—Sn1119.21 (19)C32—C37—Cl5118.5 (3)
C45—O2—Sn2119.16 (19)N2—C38—C39122.3 (3)
C68—O3—Sn3119.50 (19)N2—C38—H38118.8
C15—N1—C23118.8 (3)C39—C38—H38118.8
C15—N1—Sn1131.2 (2)C40—C39—C38119.2 (3)
C23—N1—Sn1110.0 (2)C40—C39—H39120.4
C38—N2—C46119.4 (3)C38—C39—H39120.4
C38—N2—Sn2131.1 (2)C39—C40—C41120.4 (3)
C46—N2—Sn2109.5 (2)C39—C40—H40119.8
C61—N3—C69119.3 (3)C41—C40—H40119.8
C61—N3—Sn3131.3 (2)C42—C41—C40125.1 (3)
C69—N3—Sn3109.4 (2)C42—C41—C46118.3 (3)
C2—C1—Sn1118.5 (2)C40—C41—C46116.5 (3)
C2—C1—H1A107.7C43—C42—C41119.8 (3)
Sn1—C1—H1A107.7C43—C42—H42120.1
C2—C1—H1B107.7C41—C42—H42120.1
Sn1—C1—H1B107.7C42—C43—C44121.9 (3)
H1A—C1—H1B107.1C42—C43—H43119.1
C7—C2—C3116.3 (3)C44—C43—H43119.1
C7—C2—C1123.6 (3)C45—C44—C43120.2 (3)
C3—C2—C1120.0 (3)C45—C44—H44119.9
C4—C3—C2122.3 (4)C43—C44—H44119.9
C4—C3—H3118.8O2—C45—C44122.2 (3)
C2—C3—H3118.8O2—C45—C46119.2 (3)
C5—C4—C3120.2 (4)C44—C45—C46118.6 (3)
C5—C4—H4119.9N2—C46—C45116.7 (3)
C3—C4—H4119.9N2—C46—C41122.1 (3)
C4—C5—C6120.0 (4)C45—C46—C41121.2 (3)
C4—C5—H5120.0C48—C47—Sn3116.1 (2)
C6—C5—H5120.0C48—C47—H47A108.3
C7—C6—C5118.8 (4)Sn3—C47—H47A108.3
C7—C6—H6120.6C48—C47—H47B108.3
C5—C6—H6120.6Sn3—C47—H47B108.3
C6—C7—C2122.3 (3)H47A—C47—H47B107.4
C6—C7—Cl2118.4 (3)C49—C48—C53117.4 (3)
C2—C7—Cl2119.3 (3)C49—C48—C47119.6 (3)
C9—C8—Sn1117.9 (2)C53—C48—C47123.0 (3)
C9—C8—H8A107.8C50—C49—C48121.0 (3)
Sn1—C8—H8A107.8C50—C49—H49119.5
C9—C8—H8B107.8C48—C49—H49119.5
Sn1—C8—H8B107.8C51—C50—C49120.2 (4)
H8A—C8—H8B107.2C51—C50—H50119.9
C14—C9—C10116.2 (3)C49—C50—H50119.9
C14—C9—C8122.4 (3)C50—C51—C52120.5 (3)
C10—C9—C8121.3 (3)C50—C51—H51119.7
C11—C10—C9121.3 (3)C52—C51—H51119.7
C11—C10—H10119.3C51—C52—C53118.6 (3)
C9—C10—H10119.3C51—C52—H52120.7
C12—C11—C10120.4 (3)C53—C52—H52120.7
C12—C11—H11119.8C52—C53—C48122.3 (3)
C10—C11—H11119.8C52—C53—Cl8118.5 (3)
C13—C12—C11119.7 (3)C48—C53—Cl8119.2 (3)
C13—C12—H12120.2C55—C54—Sn3113.5 (2)
C11—C12—H12120.2C55—C54—H54A108.9
C12—C13—C14119.0 (3)Sn3—C54—H54A108.9
C12—C13—H13120.5C55—C54—H54B108.9
C14—C13—H13120.5Sn3—C54—H54B108.9
C13—C14—C9123.3 (3)H54A—C54—H54B107.7
C13—C14—Cl3118.6 (2)C60—C55—C56115.9 (3)
C9—C14—Cl3118.1 (3)C60—C55—C54121.9 (3)
N1—C15—C16122.4 (3)C56—C55—C54122.1 (3)
N1—C15—H15118.8C57—C56—C55121.7 (3)
C16—C15—H15118.8C57—C56—H56119.1
C17—C16—C15119.4 (3)C55—C56—H56119.1
C17—C16—H16120.3C56—C57—C58120.5 (3)
C15—C16—H16120.3C56—C57—H57119.8
C16—C17—C18120.2 (3)C58—C57—H57119.8
C16—C17—H17119.9C57—C58—C59120.1 (3)
C18—C17—H17119.9C57—C58—H58119.9
C19—C18—C23118.6 (3)C59—C58—H58119.9
C19—C18—C17125.1 (3)C60—C59—C58118.3 (3)
C23—C18—C17116.4 (3)C60—C59—H59120.8
C20—C19—C18119.9 (3)C58—C59—H59120.8
C20—C19—H19120.1C59—C60—C55123.4 (3)
C18—C19—H19120.1C59—C60—Cl9118.3 (3)
C19—C20—C21121.8 (3)C55—C60—Cl9118.2 (3)
C19—C20—H20119.1N3—C61—C62122.1 (3)
C21—C20—H20119.1N3—C61—H61118.9
C22—C21—C20120.1 (3)C62—C61—H61118.9
C22—C21—H21120.0C63—C62—C61119.2 (3)
C20—C21—H21120.0C63—C62—H62120.4
O1—C22—C21122.1 (3)C61—C62—H62120.4
O1—C22—C23119.2 (3)C62—C63—C64120.4 (3)
C21—C22—C23118.6 (3)C62—C63—H63119.8
N1—C23—C18122.8 (3)C64—C63—H63119.8
N1—C23—C22116.3 (3)C65—C64—C69118.6 (3)
C18—C23—C22121.0 (3)C65—C64—C63125.0 (3)
C25—C24—Sn2117.0 (2)C69—C64—C63116.5 (3)
C25—C24—H24A108.1C66—C65—C64119.9 (3)
Sn2—C24—H24A108.1C66—C65—H65120.0
C25—C24—H24B108.1C64—C65—H65120.0
Sn2—C24—H24B108.1C65—C66—C67121.5 (3)
H24A—C24—H24B107.3C65—C66—H66119.2
C30—C25—C26116.6 (3)C67—C66—H66119.2
C30—C25—C24122.2 (3)C68—C67—C66120.3 (3)
C26—C25—C24121.1 (3)C68—C67—H67119.9
C27—C26—C25120.9 (3)C66—C67—H67119.9
C27—C26—H26119.5O3—C68—C67121.9 (3)
C25—C26—H26119.5O3—C68—C69119.5 (3)
C28—C27—C26121.0 (3)C67—C68—C69118.7 (3)
C28—C27—H27119.5N3—C69—C64122.5 (3)
C26—C27—H27119.5N3—C69—C68116.5 (3)
C27—C28—C29119.5 (3)C64—C69—C68121.0 (3)
C27—C28—H28120.2
C8—Sn1—O1—C2289.9 (2)C28—C29—C30—Cl6179.1 (3)
C1—Sn1—O1—C2288.1 (2)C26—C25—C30—C291.7 (5)
N1—Sn1—O1—C220.3 (2)C24—C25—C30—C29178.5 (3)
Cl1—Sn1—O1—C22178.8 (2)C26—C25—C30—Cl6179.5 (2)
C31—Sn2—O2—C4591.2 (2)C24—C25—C30—Cl60.7 (4)
C24—Sn2—O2—C4585.1 (2)O2—Sn2—C31—C3292.9 (3)
N2—Sn2—O2—C450.7 (2)C24—Sn2—C31—C3281.6 (3)
Cl4—Sn2—O2—C45179.0 (2)N2—Sn2—C31—C3216.4 (3)
C47—Sn3—O3—C6891.4 (2)Cl4—Sn2—C31—C32178.2 (3)
C54—Sn3—O3—C6881.2 (2)Sn2—C31—C32—C3772.5 (4)
N3—Sn3—O3—C682.7 (2)Sn2—C31—C32—C33110.9 (3)
Cl7—Sn3—O3—C68177.0 (2)C37—C32—C33—C341.9 (5)
O1—Sn1—N1—C15178.2 (3)C31—C32—C33—C34174.9 (3)
C8—Sn1—N1—C1573.1 (3)C32—C33—C34—C351.3 (6)
C1—Sn1—N1—C1569.0 (3)C33—C34—C35—C360.4 (6)
Cl1—Sn1—N1—C15175.6 (2)C34—C35—C36—C371.3 (6)
O1—Sn1—N1—C230.01 (19)C35—C36—C37—C320.6 (5)
C8—Sn1—N1—C23108.8 (2)C35—C36—C37—Cl5178.2 (3)
C1—Sn1—N1—C23109.1 (2)C33—C32—C37—C361.0 (5)
Cl1—Sn1—N1—C232.5 (4)C31—C32—C37—C36175.8 (3)
O2—Sn2—N2—C38177.9 (3)C33—C32—C37—Cl5179.7 (3)
C31—Sn2—N2—C3872.6 (3)C31—C32—C37—Cl52.9 (4)
C24—Sn2—N2—C3868.5 (3)C46—N2—C38—C390.1 (5)
Cl4—Sn2—N2—C38177.2 (2)Sn2—N2—C38—C39177.2 (2)
O2—Sn2—N2—C460.46 (19)N2—C38—C39—C400.6 (5)
C31—Sn2—N2—C46109.9 (2)C38—C39—C40—C410.1 (5)
C24—Sn2—N2—C46109.0 (2)C39—C40—C41—C42179.6 (3)
Cl4—Sn2—N2—C460.2 (4)C39—C40—C41—C460.6 (5)
O3—Sn3—N3—C61179.1 (3)C40—C41—C42—C43177.3 (3)
C47—Sn3—N3—C6169.5 (3)C46—C41—C42—C432.4 (5)
C54—Sn3—N3—C6167.4 (3)C41—C42—C43—C441.2 (5)
Cl7—Sn3—N3—C61180.0 (2)C42—C43—C44—C450.3 (5)
O3—Sn3—N3—C691.12 (19)Sn2—O2—C45—C44179.0 (2)
C47—Sn3—N3—C69110.7 (2)Sn2—O2—C45—C460.9 (4)
C54—Sn3—N3—C69112.4 (2)C43—C44—C45—O2179.5 (3)
Cl7—Sn3—N3—C690.2 (4)C43—C44—C45—C460.5 (5)
O1—Sn1—C1—C2121.1 (3)C38—N2—C46—C45178.0 (3)
C8—Sn1—C1—C256.0 (4)Sn2—N2—C46—C450.2 (3)
N1—Sn1—C1—C245.5 (3)C38—N2—C46—C410.8 (5)
Cl1—Sn1—C1—C2152.5 (3)Sn2—N2—C46—C41178.6 (2)
Sn1—C1—C2—C792.8 (4)O2—C45—C46—N20.5 (4)
Sn1—C1—C2—C386.5 (4)C44—C45—C46—N2179.5 (3)
C7—C2—C3—C41.5 (5)O2—C45—C46—C41179.2 (3)
C1—C2—C3—C4177.9 (3)C44—C45—C46—C410.7 (5)
C2—C3—C4—C50.6 (6)C42—C41—C46—N2179.2 (3)
C3—C4—C5—C60.6 (6)C40—C41—C46—N21.1 (5)
C4—C5—C6—C70.8 (6)C42—C41—C46—C452.2 (5)
C5—C6—C7—C20.2 (5)C40—C41—C46—C45177.6 (3)
C5—C6—C7—Cl2178.2 (3)O3—Sn3—C47—C4874.1 (2)
C3—C2—C7—C61.3 (5)C54—Sn3—C47—C4895.8 (3)
C1—C2—C7—C6178.1 (3)N3—Sn3—C47—C481.4 (2)
C3—C2—C7—Cl2177.1 (3)Cl7—Sn3—C47—C48162.1 (2)
C1—C2—C7—Cl23.5 (5)Sn3—C47—C48—C4987.5 (3)
O1—Sn1—C8—C998.9 (2)Sn3—C47—C48—C5391.6 (3)
C1—Sn1—C8—C978.1 (3)C53—C48—C49—C500.2 (5)
N1—Sn1—C8—C923.0 (3)C47—C48—C49—C50179.3 (3)
Cl1—Sn1—C8—C9174.5 (2)C48—C49—C50—C510.9 (6)
Sn1—C8—C9—C1469.7 (4)C49—C50—C51—C521.2 (6)
Sn1—C8—C9—C10111.7 (3)C50—C51—C52—C530.6 (6)
C14—C9—C10—C111.1 (5)C51—C52—C53—C480.2 (5)
C8—C9—C10—C11177.6 (3)C51—C52—C53—Cl8179.7 (3)
C9—C10—C11—C120.7 (6)C49—C48—C53—C520.4 (5)
C10—C11—C12—C130.4 (6)C47—C48—C53—C52178.7 (3)
C11—C12—C13—C140.5 (5)C49—C48—C53—Cl8179.5 (2)
C12—C13—C14—C90.9 (5)C47—C48—C53—Cl81.4 (4)
C12—C13—C14—Cl3178.5 (3)O3—Sn3—C54—C55138.4 (2)
C10—C9—C14—C131.2 (5)C47—Sn3—C54—C5531.3 (3)
C8—C9—C14—C13177.4 (3)N3—Sn3—C54—C5564.5 (2)
C10—C9—C14—Cl3178.2 (2)Cl7—Sn3—C54—C55131.8 (2)
C8—C9—C14—Cl33.2 (4)Sn3—C54—C55—C6068.4 (4)
C23—N1—C15—C160.2 (5)Sn3—C54—C55—C56110.4 (3)
Sn1—N1—C15—C16177.8 (2)C60—C55—C56—C570.8 (5)
N1—C15—C16—C170.9 (5)C54—C55—C56—C57178.0 (3)
C15—C16—C17—C180.7 (5)C55—C56—C57—C580.5 (5)
C16—C17—C18—C19179.1 (3)C56—C57—C58—C591.2 (5)
C16—C17—C18—C230.3 (5)C57—C58—C59—C600.5 (5)
C23—C18—C19—C201.4 (5)C58—C59—C60—C550.9 (5)
C17—C18—C19—C20177.5 (3)C58—C59—C60—Cl9180.0 (3)
C18—C19—C20—C210.4 (5)C56—C55—C60—C591.5 (5)
C19—C20—C21—C220.9 (5)C54—C55—C60—C59177.3 (3)
Sn1—O1—C22—C21178.7 (2)C56—C55—C60—Cl9179.3 (2)
Sn1—O1—C22—C230.6 (4)C54—C55—C60—Cl91.8 (4)
C20—C21—C22—O1179.5 (3)C69—N3—C61—C620.4 (5)
C20—C21—C22—C231.1 (5)Sn3—N3—C61—C62179.3 (2)
C15—N1—C23—C180.8 (5)N3—C61—C62—C630.5 (5)
Sn1—N1—C23—C18179.2 (2)C61—C62—C63—C640.4 (5)
C15—N1—C23—C22178.1 (3)C62—C63—C64—C65178.2 (3)
Sn1—N1—C23—C220.3 (3)C62—C63—C64—C690.3 (5)
C19—C18—C23—N1179.9 (3)C69—C64—C65—C661.2 (5)
C17—C18—C23—N11.0 (5)C63—C64—C65—C66177.2 (3)
C19—C18—C23—C221.1 (5)C64—C65—C66—C671.6 (5)
C17—C18—C23—C22177.8 (3)C65—C66—C67—C680.1 (5)
O1—C22—C23—N10.6 (4)Sn3—O3—C68—C67175.5 (2)
C21—C22—C23—N1178.8 (3)Sn3—O3—C68—C694.0 (4)
O1—C22—C23—C18179.5 (3)C66—C67—C68—O3178.4 (3)
C21—C22—C23—C180.2 (4)C66—C67—C68—C692.0 (5)
O2—Sn2—C24—C25139.5 (2)C61—N3—C69—C640.3 (5)
C31—Sn2—C24—C2535.0 (4)Sn3—N3—C69—C64179.5 (2)
N2—Sn2—C24—C2564.6 (3)C61—N3—C69—C68179.4 (3)
Cl4—Sn2—C24—C25133.9 (3)Sn3—N3—C69—C680.4 (3)
Sn2—C24—C25—C3080.0 (4)C65—C64—C69—N3178.4 (3)
Sn2—C24—C25—C26100.2 (3)C63—C64—C69—N30.2 (5)
C30—C25—C26—C270.8 (5)C65—C64—C69—C680.7 (5)
C24—C25—C26—C27179.4 (3)C63—C64—C69—C68179.3 (3)
C25—C26—C27—C280.4 (5)O3—C68—C69—N32.8 (4)
C26—C27—C28—C290.9 (6)C67—C68—C69—N3176.8 (3)
C27—C28—C29—C300.1 (5)O3—C68—C69—C64178.1 (3)
C28—C29—C30—C251.2 (5)C67—C68—C69—C642.3 (5)

Experimental details

Crystal data
Chemical formula[Sn(C7H6Cl)2(C9H6NO)Cl]
Mr549.42
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)10.2504 (1), 41.2573 (6), 15.3882 (2)
β (°) 100.3433 (6)
V3)6401.98 (14)
Z12
Radiation typeMo Kα
µ (mm1)1.59
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.692, 0.797
No. of measured, independent and
observed [I > 2σ(I)] reflections
41105, 14589, 13128
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.086, 1.11
No. of reflections14589
No. of parameters784
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0318P)2 + 14.3485P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, D.-S. & Hu, S.-Z. (1987). Chin. J. Struct. Chem. 6, 193–197.  CAS Google Scholar
First citationSisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541.  CrossRef Web of Science Google Scholar
First citationVafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m964.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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