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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1503–m1504.
Published online 2010 November 6. doi:  10.1107/S1600536810044247
PMCID: PMC3011751

Dichlorido{4-cyclo­hexyl-1-[1-(2-pyridyl-κN)ethyl­idene]thio­semicarbazidato-κ2 N 1,S}phenyl­tin(IV)

Abstract

The SnIV atom in the title compound, [Sn(C6H5)(C14H19N4S)Cl2], exists within a distorted octa­hedral geometry defined by the N,N′,S-tridentate monodeprotonated Schiff base ligand, two mutually trans Cl atoms, and the ipso-C atom of the Sn-bound phenyl group; the latter is trans to the azo-N atom. The greatest distortion from the ideal geometry is found in the nominally trans angle formed by the S and pyridyl-N atoms at Sn [151.03 (4)°]. With the exception of the cyclo­hexyl group (chair form), the Schiff base ligand is almost planar (r.m.s. deviation of non-H and Sn atoms = 0.053 Å). The nearly orthogonal orientation of the Sn-bound phenyl group [N—Sn—C—C torsion angle = 70.8 (5)°] to the planar portion of the Schiff base allows for the formation of significant intra­molecular C—H(...)Cl inter­actions which preclude the Cl atoms from participating in N—H(...)Cl hydrogen bonds. Instead, C—H(...)π contacts, involving methyl­ene H and the Sn-bound phenyl group, lead to the formation of supra­molecular chains that pack in the bc plane. Connections between these layers are of the type C—H(...)Cl.

Related literature

For the structure of the methyl­tin derivative, see: Salam et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1503-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H5)(C14H19N4S)Cl2]
  • M r = 542.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1503-efi1.jpg
  • a = 11.5213 (2) Å
  • b = 13.3795 (2) Å
  • c = 15.2648 (2) Å
  • β = 109.630 (2)°
  • V = 2216.30 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.50 mm−1
  • T = 150 K
  • 0.37 × 0.21 × 0.15 mm

Data collection

  • Area diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002 [triangle]) T min = 0.730, T max = 0.798
  • 23984 measured reflections
  • 3900 independent reflections
  • 3642 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.018
  • wR(F 2) = 0.047
  • S = 1.02
  • 3900 reflections
  • 257 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2002 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044247/hb5715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044247/hb5715Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank MOSTI (grant No. 06-01-09-SF0046) and the Universiti Malaysia Sarawak for supporting this study.

supplementary crystallographic information

Comment

The title compound, (I), is the phenyltin derivative of the recently described structure of dichlorido{4-cyclohexyl-1-[1-(2-pyridyl-κN)ethylidene]thiosemicarbazidato-κ2N1,S}methyltin(IV) (Salam et al., 2010).

The Sn atom in (I), Fig. 1, exists within a six atom CCl2N2S donor set defined by the tridentate monodeprotonated Schiff base ligand, two mutually trans chlorido atoms, and the ispo-C atom of the Sn-bound phenyl group which is trans to the azo-N atom, Table 1. Distortions from the ideal octahedral geometry are ascribed primarily to the restricted bite distances formed by the Schiff base which results in an angle of 151.03 (4) ° for the nominally trans S1—Sn—N1 angle. The disposition of donor atoms resembles that found in the structure of the methyltin derivative (Salam et al., 2010). With the exception of the cyclohexyl group, which adopts a chair conformation, the Schiff base ligand is planar. Thus, the r.m.s. deviation from the least-squares plane through the 15 non-H atoms in the conjugated part of the ligand including the Sn and methine-C15 atoms, i.e. Sn,S1,N1–N4,C1–C9, is 0.053 Å. The Sn-bound phenyl group occupies a position almost orthogonal to the chelate rings as seen in the N2—Sn—C15—C16 torsion angle of 70.8 (5) Å.

In the crystal, supramolecular chains along the b axis are mediated by C—H···π interactions involving a methylene-H interacting with the Sn-bound phenyl group, Table 1. The chains pack in the bc plane and connections between the layers stacked along the a axis are of the type C—H···Cl, Fig. 2 and Table 1. The non-participation of the N—H atom in forming a significant intermolecular interaction contrasts the formation of N—H···Cl interactions in the methyltin derivative (Salam et al., 2010). It is noted that the orthogonal orientation of the Sn-bound phenyl group allows for the formation of close intramolecular C—H···Cl contacts, Table 1, which probably deactivate the chlorido atoms from forming significant hydrogen bonds. Further, it is noted that the C—H···π interactions present in (I) involves the Sn-bound phenyl group as as the acceptor, and that these are not possible in the methyltin derivative. Together, these factors explain the absence of significant hydrogen bonding interactions involving the N—H atom.

Experimental

2-Acetylpyridine-N-cyclohexyl thiosemicarbazone (0.28 g, 1.0 mmol) was dissolved in absolute methanol (10 ml) in a Schlenk round bottom flask under a nitrogen atmosphere and stirred for 30 min. Then, a 10 ml me thanolic solution of phenyltin(IV) trichloride (0.302 g, 1.0 mmol) was added drop wise while stirring which resulted in the formation of a yellow solution. The reaction mixture was refluxed for 4 h. and then cooled to room temperature. Yellow micro crystals of (I) were obtained from the slow evaporation of the solution at room temperature. The micro crystals were filtered off, washed with a small amount of cool methanol and dried in vacuo over silica gel. Light-yellow crystals were obtained from the slow evaporation of a chloroform/methanol (1/1) solution of (I) held at room temperature. Yield: 0.45 g, 77%: M.pt.: 523–525 K. Anal. Calc. for C20H24Cl2N4SSn: C, 44.30; H, 4.46; N, 10.33%. Found: C, 44.12; H, 4.27; N, 10.18%.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H = 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C). The N-bound H atom was located from a difference map and refined with the distance restraint N–H = 0.88±0.01 Å, and with Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
Fig. 2.
Unit-cell contents shown in projection down the c axis in (I). The C–H···Cl and C–H···π contacts are shown as orange and purple dashed lines, respectively.

Crystal data

[Sn(C6H5)(C14H19N4S)Cl2]F(000) = 1088
Mr = 542.08Dx = 1.625 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 17836 reflections
a = 11.5213 (2) Åθ = 2.4–28.9°
b = 13.3795 (2) ŵ = 1.50 mm1
c = 15.2648 (2) ÅT = 150 K
β = 109.630 (2)°Prism, orange
V = 2216.30 (6) Å30.37 × 0.21 × 0.15 mm
Z = 4

Data collection

Area diffractometer3642 reflections with I > 2σ(I)
graphiteRint = 0.034
ω/2θ scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)h = −13→13
Tmin = 0.730, Tmax = 0.798k = −15→15
23984 measured reflectionsl = −18→18
3900 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.018Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0232P)2 + 1.3698P] where P = (Fo2 + 2Fc2)/3
3900 reflections(Δ/σ)max = 0.003
257 parametersΔρmax = 0.30 e Å3
1 restraintΔρmin = −0.45 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sn0.473542 (11)0.564452 (9)0.716818 (8)0.01429 (6)
Cl10.25305 (5)0.55811 (4)0.62427 (4)0.02697 (12)
Cl20.67571 (4)0.56343 (3)0.84773 (3)0.02149 (11)
S10.52690 (6)0.41751 (4)0.63924 (4)0.02665 (13)
N10.39962 (14)0.63184 (11)0.82288 (10)0.0162 (3)
N20.43068 (15)0.43990 (10)0.79821 (11)0.0163 (3)
N30.45002 (15)0.34299 (11)0.78079 (11)0.0186 (3)
N40.51413 (16)0.23328 (12)0.69436 (11)0.0214 (4)
H4N0.5435 (19)0.2243 (16)0.6499 (11)0.026*
C10.36701 (17)0.56662 (13)0.87825 (13)0.0160 (4)
C20.31498 (17)0.60120 (15)0.94234 (13)0.0198 (4)
H20.29450.55570.98270.024*
C30.29312 (18)0.70261 (15)0.94712 (13)0.0230 (4)
H30.25590.72690.98980.028*
C40.32570 (19)0.76806 (15)0.88952 (14)0.0242 (4)
H40.31100.83770.89160.029*
C50.38022 (18)0.72975 (14)0.82871 (13)0.0203 (4)
H50.40470.77440.78980.024*
C60.38569 (17)0.46014 (14)0.86329 (13)0.0166 (4)
C70.3507 (2)0.38016 (14)0.91856 (14)0.0240 (4)
H7A0.26080.37400.89780.036*
H7B0.38170.39780.98470.036*
H7C0.38670.31640.90930.036*
C80.49310 (18)0.32842 (14)0.71163 (12)0.0193 (4)
C90.49837 (18)0.14827 (13)0.75032 (13)0.0186 (4)
H90.41800.15600.76130.022*
C100.49480 (18)0.05184 (13)0.69666 (14)0.0179 (4)
H10A0.57310.04360.68410.022*
H10B0.42680.05480.63630.022*
C110.47560 (19)−0.03703 (14)0.75323 (14)0.0213 (4)
H11A0.3950−0.03040.76260.026*
H11B0.4745−0.09960.71840.026*
C120.5780 (2)−0.04246 (15)0.84755 (15)0.0301 (5)
H12A0.6577−0.05550.83830.036*
H12B0.5615−0.09850.88410.036*
C130.5861 (2)0.05525 (15)0.90122 (15)0.0305 (5)
H13A0.51030.06390.91730.037*
H13B0.65710.05220.95990.037*
C140.6013 (2)0.14412 (15)0.84392 (14)0.0272 (5)
H14A0.60110.20660.87860.033*
H14B0.68160.13920.83390.033*
C150.51354 (17)0.69707 (13)0.65203 (12)0.0151 (4)
C160.62574 (18)0.74626 (14)0.68942 (14)0.0204 (4)
H160.68490.72240.74530.024*
C170.65198 (19)0.83006 (14)0.64572 (15)0.0242 (4)
H170.72920.86280.67140.029*
C180.5663 (2)0.86581 (14)0.56524 (14)0.0245 (5)
H180.58450.92310.53550.029*
C190.45379 (19)0.81846 (15)0.52775 (13)0.0242 (4)
H190.39430.84390.47280.029*
C200.42738 (18)0.73337 (14)0.57055 (13)0.0199 (4)
H200.35060.70020.54410.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn0.01933 (9)0.01020 (8)0.01541 (8)−0.00154 (5)0.00855 (6)−0.00036 (4)
Cl10.0224 (3)0.0325 (3)0.0231 (3)−0.0101 (2)0.0038 (2)−0.0018 (2)
Cl20.0195 (2)0.0233 (3)0.0212 (2)0.00270 (18)0.00619 (19)0.00428 (18)
S10.0507 (4)0.0124 (2)0.0274 (3)−0.0002 (2)0.0270 (3)−0.0005 (2)
N10.0174 (8)0.0144 (8)0.0174 (8)−0.0014 (6)0.0068 (6)−0.0016 (6)
N20.0219 (9)0.0122 (8)0.0161 (8)−0.0020 (6)0.0081 (7)−0.0011 (6)
N30.0283 (9)0.0094 (7)0.0211 (8)−0.0005 (7)0.0122 (7)−0.0015 (6)
N40.0340 (10)0.0133 (8)0.0220 (9)0.0000 (7)0.0163 (8)−0.0012 (7)
C10.0135 (9)0.0182 (10)0.0153 (9)−0.0033 (7)0.0037 (7)−0.0016 (7)
C20.0200 (10)0.0242 (10)0.0162 (9)−0.0029 (8)0.0074 (8)−0.0020 (8)
C30.0213 (10)0.0274 (11)0.0226 (10)−0.0012 (9)0.0102 (8)−0.0098 (8)
C40.0271 (11)0.0163 (10)0.0290 (11)0.0008 (8)0.0094 (9)−0.0064 (8)
C50.0240 (10)0.0144 (9)0.0228 (10)−0.0025 (8)0.0081 (8)−0.0021 (8)
C60.0173 (9)0.0166 (9)0.0154 (9)−0.0020 (8)0.0048 (8)0.0004 (7)
C70.0318 (11)0.0207 (10)0.0248 (10)−0.0027 (9)0.0166 (9)0.0026 (8)
C80.0255 (10)0.0139 (9)0.0184 (9)0.0000 (8)0.0072 (8)−0.0010 (7)
C90.0241 (10)0.0132 (9)0.0199 (9)−0.0015 (8)0.0094 (8)0.0003 (8)
C100.0208 (10)0.0145 (9)0.0198 (10)0.0009 (8)0.0085 (8)−0.0012 (7)
C110.0271 (11)0.0128 (9)0.0270 (11)−0.0035 (8)0.0129 (9)−0.0024 (8)
C120.0369 (13)0.0184 (10)0.0322 (12)−0.0001 (9)0.0080 (10)0.0088 (9)
C130.0373 (13)0.0275 (12)0.0212 (11)−0.0025 (9)0.0024 (10)0.0039 (9)
C140.0309 (11)0.0200 (10)0.0261 (11)−0.0066 (9)0.0035 (9)−0.0006 (8)
C150.0206 (9)0.0108 (8)0.0183 (9)0.0021 (7)0.0121 (8)−0.0005 (7)
C160.0197 (10)0.0174 (9)0.0256 (10)0.0028 (8)0.0096 (8)0.0025 (8)
C170.0246 (10)0.0153 (9)0.0380 (12)−0.0016 (8)0.0173 (9)0.0002 (9)
C180.0379 (12)0.0142 (9)0.0322 (11)0.0037 (9)0.0261 (10)0.0057 (8)
C190.0347 (12)0.0226 (10)0.0197 (10)0.0100 (9)0.0150 (9)0.0064 (8)
C200.0227 (10)0.0194 (10)0.0196 (9)0.0017 (8)0.0096 (8)−0.0005 (8)

Geometric parameters (Å, °)

Sn—Cl12.4587 (5)C9—C101.521 (2)
Sn—Cl22.5083 (5)C9—C141.520 (3)
Sn—S12.4768 (5)C9—H91.0000
Sn—N12.2552 (15)C10—C111.529 (3)
Sn—N22.2309 (15)C10—H10A0.9900
Sn—C152.1552 (17)C10—H10B0.9900
S1—C81.7558 (19)C11—C121.526 (3)
N1—C51.337 (2)C11—H11A0.9900
N1—C11.353 (2)C11—H11B0.9900
N2—C61.294 (2)C12—C131.529 (3)
N2—N31.357 (2)C12—H12A0.9900
N3—C81.323 (2)C12—H12B0.9900
N4—C81.338 (2)C13—C141.520 (3)
N4—C91.470 (2)C13—H13A0.9900
N4—H4N0.863 (19)C13—H13B0.9900
C1—C21.387 (3)C14—H14A0.9900
C1—C61.470 (3)C14—H14B0.9900
C2—C31.386 (3)C15—C161.391 (3)
C2—H20.9500C15—C201.392 (3)
C3—C41.379 (3)C16—C171.389 (3)
C3—H30.9500C16—H160.9500
C4—C51.382 (3)C17—C181.378 (3)
C4—H40.9500C17—H170.9500
C5—H50.9500C18—C191.382 (3)
C6—C71.499 (3)C18—H180.9500
C7—H7A0.9800C19—C201.396 (3)
C7—H7B0.9800C19—H190.9500
C7—H7C0.9800C20—H200.9500
C15—Sn—N2172.75 (6)N4—C9—C14111.40 (16)
C15—Sn—N1101.00 (6)C10—C9—C14110.28 (16)
N2—Sn—N172.01 (5)N4—C9—H9108.6
C15—Sn—Cl195.95 (5)C10—C9—H9108.6
N2—Sn—Cl185.12 (4)C14—C9—H9108.6
N1—Sn—Cl181.94 (4)C9—C10—C11109.78 (16)
C15—Sn—S1107.97 (5)C9—C10—H10A109.7
N2—Sn—S179.07 (4)C11—C10—H10A109.7
N1—Sn—S1151.03 (4)C9—C10—H10B109.7
Cl1—Sn—S194.152 (19)C11—C10—H10B109.7
C15—Sn—Cl294.91 (5)H10A—C10—H10B108.2
N2—Sn—Cl282.66 (4)C12—C11—C10110.94 (16)
N1—Sn—Cl284.48 (4)C12—C11—H11A109.5
Cl1—Sn—Cl2164.001 (18)C10—C11—H11A109.5
S1—Sn—Cl293.632 (18)C12—C11—H11B109.5
C8—S1—Sn95.44 (6)C10—C11—H11B109.5
C5—N1—C1120.18 (16)H11A—C11—H11B108.0
C5—N1—Sn123.46 (13)C11—C12—C13110.71 (17)
C1—N1—Sn116.22 (11)C11—C12—H12A109.5
C6—N2—N3119.00 (15)C13—C12—H12A109.5
C6—N2—Sn119.47 (12)C11—C12—H12B109.5
N3—N2—Sn121.53 (11)C13—C12—H12B109.5
C8—N3—N2115.31 (15)H12A—C12—H12B108.1
C8—N4—C9123.75 (16)C14—C13—C12111.01 (18)
C8—N4—H4N115.6 (15)C14—C13—H13A109.4
C9—N4—H4N120.5 (14)C12—C13—H13A109.4
N1—C1—C2120.13 (16)C14—C13—H13B109.4
N1—C1—C6116.24 (16)C12—C13—H13B109.4
C2—C1—C6123.59 (17)H13A—C13—H13B108.0
C1—C2—C3119.52 (18)C9—C14—C13111.42 (16)
C1—C2—H2120.2C9—C14—H14A109.3
C3—C2—H2120.2C13—C14—H14A109.3
C4—C3—C2119.64 (18)C9—C14—H14B109.3
C4—C3—H3120.2C13—C14—H14B109.3
C2—C3—H3120.2H14A—C14—H14B108.0
C3—C4—C5118.37 (18)C16—C15—C20119.14 (17)
C3—C4—H4120.8C16—C15—Sn120.92 (13)
C5—C4—H4120.8C20—C15—Sn119.93 (13)
N1—C5—C4122.13 (18)C15—C16—C17120.47 (18)
N1—C5—H5118.9C15—C16—H16119.8
C4—C5—H5118.9C17—C16—H16119.8
N2—C6—C1116.06 (16)C18—C17—C16120.14 (19)
N2—C6—C7122.37 (17)C18—C17—H17119.9
C1—C6—C7121.55 (17)C16—C17—H17119.9
C6—C7—H7A109.5C17—C18—C19120.10 (18)
C6—C7—H7B109.5C17—C18—H18119.9
H7A—C7—H7B109.5C19—C18—H18119.9
C6—C7—H7C109.5C18—C19—C20120.10 (18)
H7A—C7—H7C109.5C18—C19—H19120.0
H7B—C7—H7C109.5C20—C19—H19120.0
N3—C8—N4116.01 (17)C15—C20—C19120.03 (18)
N3—C8—S1128.61 (14)C15—C20—H20120.0
N4—C8—S1115.38 (14)C19—C20—H20120.0
N4—C9—C10109.25 (15)
C15—Sn—S1—C8176.61 (8)N3—N2—C6—C7−1.8 (3)
N2—Sn—S1—C8−1.55 (8)Sn—N2—C6—C7177.87 (14)
N1—Sn—S1—C8−4.91 (11)N1—C1—C6—N2−0.4 (3)
Cl1—Sn—S1—C8−85.76 (7)C2—C1—C6—N2177.22 (17)
Cl2—Sn—S1—C880.26 (7)N1—C1—C6—C7−178.61 (17)
C15—Sn—N1—C55.52 (16)C2—C1—C6—C7−1.0 (3)
N2—Sn—N1—C5−176.48 (16)N2—N3—C8—N4179.18 (16)
Cl1—Sn—N1—C5−89.02 (15)N2—N3—C8—S1−0.7 (3)
S1—Sn—N1—C5−173.00 (11)C9—N4—C8—N3−3.4 (3)
Cl2—Sn—N1—C599.47 (15)C9—N4—C8—S1176.47 (14)
C15—Sn—N1—C1−178.78 (13)Sn—S1—C8—N31.86 (19)
N2—Sn—N1—C1−0.78 (12)Sn—S1—C8—N4−177.98 (14)
Cl1—Sn—N1—C186.68 (12)C8—N4—C9—C10164.24 (18)
S1—Sn—N1—C12.70 (18)C8—N4—C9—C14−73.7 (2)
Cl2—Sn—N1—C1−84.83 (12)N4—C9—C10—C11−178.77 (16)
C15—Sn—N2—C616.3 (6)C14—C9—C10—C1158.5 (2)
N1—Sn—N2—C60.57 (14)C9—C10—C11—C12−58.4 (2)
Cl1—Sn—N2—C6−82.53 (14)C10—C11—C12—C1356.4 (2)
S1—Sn—N2—C6−177.72 (15)C11—C12—C13—C14−54.7 (3)
Cl2—Sn—N2—C687.12 (14)N4—C9—C14—C13−179.10 (17)
C15—Sn—N2—N3−164.1 (4)C10—C9—C14—C13−57.6 (2)
N1—Sn—N2—N3−179.81 (15)C12—C13—C14—C955.6 (3)
Cl1—Sn—N2—N397.10 (13)N2—Sn—C15—C1670.8 (5)
S1—Sn—N2—N31.90 (13)N1—Sn—C15—C1686.01 (15)
Cl2—Sn—N2—N3−93.26 (13)Cl1—Sn—C15—C16168.92 (14)
C6—N2—N3—C8178.28 (17)S1—Sn—C15—C16−94.74 (14)
Sn—N2—N3—C8−1.3 (2)Cl2—Sn—C15—C160.69 (14)
C5—N1—C1—C2−1.0 (3)N2—Sn—C15—C20−110.5 (5)
Sn—N1—C1—C2−176.82 (14)N1—Sn—C15—C20−95.31 (14)
C5—N1—C1—C6176.77 (17)Cl1—Sn—C15—C20−12.40 (14)
Sn—N1—C1—C60.9 (2)S1—Sn—C15—C2083.93 (14)
N1—C1—C2—C32.0 (3)Cl2—Sn—C15—C20179.37 (13)
C6—C1—C2—C3−175.53 (18)C20—C15—C16—C17−0.5 (3)
C1—C2—C3—C4−1.4 (3)Sn—C15—C16—C17178.20 (14)
C2—C3—C4—C5−0.3 (3)C15—C16—C17—C180.6 (3)
C1—N1—C5—C4−0.8 (3)C16—C17—C18—C190.1 (3)
Sn—N1—C5—C4174.74 (14)C17—C18—C19—C20−1.0 (3)
C3—C4—C5—N11.4 (3)C16—C15—C20—C19−0.4 (3)
N3—N2—C6—C1−179.92 (15)Sn—C15—C20—C19−179.10 (13)
Sn—N2—C6—C1−0.3 (2)C18—C19—C20—C151.1 (3)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of benzene ring C15–C20.
D—H···AD—HH···AD···AD—H···A
C11—H11B···Cg1i0.992.603.522 (2)155
C13—H13B···Cl1ii0.992.803.632 (2)142
C16—H16···Cl20.952.663.350 (2)130
C20—H20···Cl10.952.703.363 (2)127

Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5715).

References

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