(N-Ethyl-N-phenyl­dithio­carbamato-κS)triphenyl­tin(IV)

Kamaludin, N.F.; Baba, I.; Awang, N.; Mohamed Tahir, M.I.; Tiekink, E.R.T.

doi:10.1107/S1600536811053591

(N-Ethyl-N-phenyldithiocarbamato-κS)triphenyltin(IV)

N. F. Kamaludin, I. Baba, N. Awang, M. I. Mohamed Tahir and E. R. T. Tiekink

The title compound, [Sn(C₆H₅)₃(C₉H₁₀NS₂)], has two independent molecules in the asymmetric unit and each features a tetrahedrally coordinated Sn^IV atom as the dithiocarbamate ligand coordinates in a monodentate fashion. As the non-coordinating thione S atom is proximate to the Sn atom [Sn

S(thione) = 3.1477 (6) and 2.9970 (5) Å for the independent molecules], distortions from the ideal geometry are evident [the widest angle being 120.48 (5)°]. The most notable feature of the crystal packing is the formation of C—H

π interactions that lead to the formation of supramolecular layers parallel to ( $\overline{3}$ 2 $\overline{1}$ ).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811053591/qm2044sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811053591/qm2044Isup2.hkl Contains datablock I

CCDC reference: 861704

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.022
wR factor = 0.055
Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn2    --  S4      ..       14.3 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        3.2 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     --  C7      ..        5.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C51    --  C52     ..        5.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C52    --  C53     ..        5.5 su
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         43 A   3 
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Potential applications as anti-cancer agents, anti-microbials and insecticides, and as convenient synthetic precursors for tin sulfide nanoparticles, characterize organotin dithiocarbamates (Tiekink, 2008). This background motivates our interest in this class of compound and led to the investigation of the title compound, (I). Recently, the structure of the n-butyl derivative was described (Kamaludin et al., 2011) and herein, we describe the analysis of (I).

There are two independent molecules in the asymmetric unit of (I): the molecular structures are shown in Fig. 1. Each molecule features Sn coordinated by the dithiocarbamate ligand and three ipso-C atoms of three benzene rings. The dithiocarbamate ligand coordinates essentially in a monodentate fashion, an assignment supported by the large disparity in the C—S bond distances, Table 1. The coordination geometry is based on a tetrahedron with the range of tetrahedral angles being 94.46 (5) to 120.48 (5)° for the Sn1-containing molecule and 95.28 (5) to 118.66 (5)° for the other. The wider angles are ascribed to the influence of the proximate thione-S atom [Sn1···S2 = 3.1477 (6) Å and Sn2···S4 = 2.9970 (5) Å]. The major differences between the independent molecules is highlighted in the overlay diagram, Fig. 2, showing that the chemically equivalent phenyl rings do not overlap significantly.

The crystal packing of (I) features C—H···π interactions involving the Sn- and N-phenyl rings as donors, and Sn-bound phenyl rings as acceptors, Table 2. The result is the formation of supramolecular layers parallel to (3 2 1), Fig. 3.

Related literature top

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For the recently reported n-butyl derivative, see: Kamaludin et al. (2011).

Experimental top

The title compound was prepared using an in situ method. A mixture of ethanol (50 ml) and N-ethylaniline (30 mM) was added to an ammonia solution (0.25%). The solution was stirred for half an hour at approximately 277 K. Carbon disulfide (30 mM) was added drop-wise and stirring was continued for another 6–8 h at 277 K. Triphenytin(IV) chloride (30 mM), dissolved in ethanol (20 ml), was added and stirring continued for a further 3 h. The white precipitate formed was filtered, washed with cold ethanol and dried in a vacuum desiccator. Recrystallization was from its ethanol:ethyl acetate (1:1) solution. Yield: 32%. M.pt. 381–382 K. Elemental analysis. Found (calculated) for C₂₇H₂₅NS₂Sn: C, 59.19 (59.36); H 4.33 (4.61); N 2.52 (2.56); S 11.30 (11.74) %. IR (KBr): ν(C—H) 2986 m; ν(C≐N) 1478 m; ν(N—C) 1125 s; ν(C≐S) 997 s; ν(Sn—S) 357 s cm^{-1. 13}C NMR (CDCl₃): δ (CS₂) 198.63 p.p.m..

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the two independent molecules comprising (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. An overlay diagram of the two independent molecules comprising (I) aligned so that the Sn—S—C planes are superimposed. The red image illustrates the molecule containing the Sn1 atom.
	Fig. 3. A view of the supramolecular layer parallel to [3 2 1] in (I) mediated by C—H···π interactions (purple dashed lines).

(N-Ethyl-N-phenyldithiocarbamato-κS)triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₉H₁₀NS₂)]	Z = 4
M_r = 546.29	F(000) = 1104
Triclinic, P1	D_x = 1.461 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6973 (2) Å	Cell parameters from 39367 reflections
b = 12.2804 (2) Å	θ = 2–29°
c = 22.8523 (4) Å	µ = 1.21 mm⁻¹
α = 90.588 (2)°	T = 150 K
β = 101.573 (2)°	Block, colourless
γ = 110.687 (2)°	0.30 × 0.24 × 0.19 mm
V = 2484.39 (8) Å³

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	10558 independent reflections
Radiation source: fine-focus sealed tube	9633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 16.1952 pixels mm^-1	θ_max = 26.8°, θ_min = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −15→15
T_min = 0.748, T_max = 0.795	l = −28→28
62467 measured reflections

Refinement top

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.055	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0259P)² + 1.489P] where P = (F_o² + 2F_c²)/3
10558 reflections	(Δ/σ)_max = 0.004
561 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₉H₁₀NS₂)]	γ = 110.687 (2)°
M_r = 546.29	V = 2484.39 (8) Å³
Triclinic, P1	Z = 4
a = 9.6973 (2) Å	Mo Kα radiation
b = 12.2804 (2) Å	µ = 1.21 mm⁻¹
c = 22.8523 (4) Å	T = 150 K
α = 90.588 (2)°	0.30 × 0.24 × 0.19 mm
β = 101.573 (2)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	10558 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	9633 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.795	R_int = 0.038
62467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.055	H-atom parameters constrained
S = 1.00	Δρ_max = 0.55 e Å⁻³
10558 reflections	Δρ_min = −0.44 e Å⁻³
561 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Sn1	0.425600 (14)	0.868539 (11)	0.613068 (5)	0.02407 (4)
S1	0.25460 (6)	0.77901 (4)	0.51651 (2)	0.02845 (10)
S2	0.39527 (6)	0.61380 (5)	0.57263 (2)	0.03395 (11)
N1	0.2447 (2)	0.58873 (15)	0.45887 (7)	0.0337 (4)
C1	0.2955 (2)	0.65087 (17)	0.51249 (8)	0.0284 (4)
C2	0.2836 (3)	0.4851 (2)	0.44586 (11)	0.0478 (6)
H2A	0.3831	0.4944	0.4715	0.057*
H2B	0.2923	0.4815	0.4035	0.057*
C3	0.1682 (3)	0.3731 (2)	0.45672 (13)	0.0614 (8)
H3A	0.1678	0.3723	0.4996	0.092*
H3B	0.1931	0.3071	0.4439	0.092*
H3C	0.0682	0.3663	0.4338	0.092*
C4	0.1517 (2)	0.62092 (17)	0.40950 (8)	0.0314 (4)
C5	−0.0031 (3)	0.5806 (2)	0.40371 (10)	0.0386 (5)
H5	−0.0482	0.5333	0.4324	0.046*
C6	−0.0915 (3)	0.6096 (2)	0.35598 (11)	0.0510 (6)
H6	−0.1980	0.5823	0.3517	0.061*
C7	−0.0259 (4)	0.6780 (3)	0.31455 (11)	0.0610 (8)
H7	−0.0871	0.6985	0.2819	0.073*
C8	0.1281 (4)	0.7169 (2)	0.32016 (11)	0.0602 (8)
H8	0.1725	0.7636	0.2911	0.072*
C9	0.2197 (3)	0.6885 (2)	0.36788 (10)	0.0440 (5)
H9	0.3260	0.7149	0.3717	0.053*
C10	0.6605 (2)	0.89709 (18)	0.62716 (8)	0.0293 (4)
C11	0.7603 (2)	0.9959 (2)	0.60893 (10)	0.0408 (5)
H11	0.7239	1.0507	0.5885	0.049*
C12	0.9148 (3)	1.0149 (3)	0.62057 (13)	0.0574 (7)
H12	0.9828	1.0815	0.6072	0.069*
C13	0.9681 (3)	0.9371 (3)	0.65134 (14)	0.0624 (8)
H13	1.0730	0.9503	0.6591	0.075*
C14	0.8709 (3)	0.8402 (2)	0.67092 (12)	0.0517 (7)
H14	0.9086	0.7877	0.6929	0.062*
C15	0.7171 (2)	0.8197 (2)	0.65846 (9)	0.0359 (5)
H15	0.6499	0.7521	0.6714	0.043*
C16	0.4002 (2)	1.03524 (16)	0.60391 (8)	0.0271 (4)
C17	0.3810 (2)	1.09529 (17)	0.65201 (9)	0.0332 (4)
H17	0.3829	1.0632	0.6897	0.040*
C18	0.3592 (3)	1.20067 (19)	0.64607 (10)	0.0408 (5)
H18	0.3465	1.2399	0.6795	0.049*
C19	0.3559 (3)	1.24854 (19)	0.59177 (11)	0.0421 (5)
H19	0.3412	1.3208	0.5877	0.051*
C20	0.3740 (3)	1.1909 (2)	0.54327 (10)	0.0415 (5)
H20	0.3716	1.2235	0.5057	0.050*
C21	0.3956 (2)	1.08579 (19)	0.54950 (9)	0.0350 (5)
H21	0.4077	1.0469	0.5158	0.042*
C22	0.3337 (2)	0.80327 (17)	0.68794 (8)	0.0268 (4)
C23	0.1960 (2)	0.7136 (2)	0.68340 (10)	0.0386 (5)
H23	0.1416	0.6716	0.6457	0.046*
C24	0.1371 (3)	0.6849 (2)	0.73484 (14)	0.0581 (7)
H24	0.0423	0.6237	0.7321	0.070*
C25	0.2182 (4)	0.7465 (3)	0.78978 (12)	0.0635 (8)
H25	0.1774	0.7282	0.8245	0.076*
C26	0.3555 (4)	0.8328 (2)	0.79434 (11)	0.0593 (8)
H26	0.4117	0.8730	0.8322	0.071*
C27	0.4122 (3)	0.8612 (2)	0.74395 (9)	0.0410 (5)
H27	0.5076	0.9221	0.7474	0.049*
Sn2	0.849644 (14)	0.767651 (10)	0.914470 (5)	0.02217 (4)
S3	0.73045 (6)	0.77465 (4)	0.99945 (2)	0.02867 (10)
S4	0.82367 (6)	0.56918 (4)	0.99206 (2)	0.03252 (11)
N2	0.71753 (19)	0.62538 (13)	1.08192 (7)	0.0289 (3)
C28	0.7555 (2)	0.65068 (16)	1.02941 (8)	0.0257 (4)
C29	0.7378 (3)	0.52486 (19)	1.11280 (11)	0.0483 (6)
H29A	0.7194	0.4601	1.0826	0.058*
H29B	0.6630	0.4970	1.1382	0.058*
C30	0.8959 (4)	0.5582 (3)	1.15146 (13)	0.0726 (9)
H30A	0.9696	0.5783	1.1258	0.109*
H30B	0.9035	0.4921	1.1738	0.109*
H30C	0.9168	0.6256	1.1797	0.109*
C31	0.6641 (2)	0.69863 (16)	1.11445 (8)	0.0273 (4)
C32	0.7662 (2)	0.79839 (17)	1.14875 (9)	0.0335 (4)
H32	0.8711	0.8217	1.1497	0.040*
C33	0.7126 (3)	0.86425 (19)	1.18188 (10)	0.0409 (5)
H33	0.7811	0.9330	1.2059	0.049*
C34	0.5593 (3)	0.8294 (2)	1.17981 (10)	0.0420 (5)
H34	0.5227	0.8747	1.2022	0.050*
C35	0.4607 (3)	0.7303 (2)	1.14582 (11)	0.0440 (5)
H35	0.3557	0.7072	1.1447	0.053*
C36	0.5116 (2)	0.66293 (19)	1.11289 (10)	0.0360 (5)
H36	0.4427	0.5934	1.0897	0.043*
C37	1.0884 (2)	0.80657 (15)	0.93488 (8)	0.0225 (4)
C38	1.1777 (2)	0.91710 (16)	0.92315 (8)	0.0251 (4)
H38	1.1314	0.9708	0.9084	0.030*
C39	1.3336 (2)	0.95029 (17)	0.93266 (8)	0.0297 (4)
H39	1.3931	1.0261	0.9244	0.036*
C40	1.4021 (2)	0.87260 (18)	0.95422 (9)	0.0313 (4)
H40	1.5086	0.8947	0.9605	0.038*
C41	1.3150 (2)	0.76280 (18)	0.96660 (9)	0.0320 (4)
H41	1.3621	0.7099	0.9818	0.038*
C42	1.1587 (2)	0.72925 (17)	0.95689 (8)	0.0284 (4)
H42	1.0997	0.6534	0.9653	0.034*
C43	0.8300 (2)	0.92594 (16)	0.88000 (8)	0.0249 (4)
C44	0.8243 (2)	1.01716 (18)	0.91533 (9)	0.0329 (4)
H44	0.8266	1.0101	0.9568	0.040*
C45	0.8153 (3)	1.1176 (2)	0.89075 (10)	0.0413 (5)
H45	0.8109	1.1786	0.9154	0.050*
C46	0.8125 (2)	1.12962 (18)	0.83056 (9)	0.0350 (5)
H46	0.8052	1.1983	0.8137	0.042*
C47	0.8206 (2)	1.04148 (18)	0.79481 (9)	0.0330 (4)
H47	0.8205	1.0499	0.7535	0.040*
C48	0.8287 (2)	0.94077 (17)	0.81961 (8)	0.0300 (4)
H48	0.8335	0.8803	0.7947	0.036*
C49	0.7240 (2)	0.64207 (16)	0.83962 (8)	0.0285 (4)
C50	0.5873 (3)	0.6435 (2)	0.80722 (10)	0.0440 (5)
H50	0.5436	0.6937	0.8215	0.053*
C51	0.5138 (3)	0.5727 (2)	0.75430 (12)	0.0630 (8)
H51	0.4197	0.5741	0.7329	0.076*
C52	0.5760 (4)	0.5013 (2)	0.73294 (12)	0.0695 (10)
H52	0.5261	0.4539	0.6963	0.083*
C53	0.7108 (4)	0.4976 (2)	0.76434 (13)	0.0670 (9)
H53	0.7537	0.4474	0.7494	0.080*
C54	0.7849 (3)	0.5676 (2)	0.81818 (11)	0.0456 (6)
H54	0.8772	0.5639	0.8401	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02483 (7)	0.02598 (7)	0.01999 (7)	0.00680 (5)	0.00633 (5)	0.00045 (5)
S1	0.0337 (3)	0.0290 (2)	0.0217 (2)	0.0118 (2)	0.00338 (19)	−0.00109 (18)
S2	0.0372 (3)	0.0334 (3)	0.0284 (2)	0.0131 (2)	0.0004 (2)	0.0015 (2)
N1	0.0406 (10)	0.0317 (9)	0.0273 (8)	0.0143 (8)	0.0021 (7)	−0.0043 (7)
C1	0.0275 (10)	0.0282 (10)	0.0256 (9)	0.0054 (8)	0.0061 (8)	0.0005 (7)
C2	0.0574 (15)	0.0529 (15)	0.0401 (13)	0.0336 (13)	0.0016 (11)	−0.0077 (11)
C3	0.0743 (19)	0.0410 (14)	0.0637 (18)	0.0265 (14)	−0.0058 (15)	−0.0103 (12)
C4	0.0423 (12)	0.0292 (10)	0.0209 (9)	0.0136 (9)	0.0017 (8)	−0.0057 (7)
C5	0.0437 (13)	0.0378 (12)	0.0331 (11)	0.0155 (10)	0.0043 (9)	−0.0046 (9)
C6	0.0518 (15)	0.0561 (15)	0.0439 (14)	0.0285 (13)	−0.0079 (11)	−0.0133 (12)
C7	0.094 (2)	0.0664 (18)	0.0312 (13)	0.0537 (18)	−0.0121 (14)	−0.0081 (12)
C8	0.105 (3)	0.0555 (16)	0.0303 (12)	0.0382 (17)	0.0208 (14)	0.0141 (11)
C9	0.0528 (14)	0.0423 (13)	0.0371 (12)	0.0143 (11)	0.0156 (11)	0.0035 (10)
C10	0.0262 (10)	0.0353 (11)	0.0235 (9)	0.0072 (8)	0.0067 (7)	−0.0044 (8)
C11	0.0342 (11)	0.0423 (12)	0.0364 (12)	0.0015 (10)	0.0102 (9)	−0.0028 (9)
C12	0.0339 (13)	0.0641 (17)	0.0583 (16)	−0.0058 (12)	0.0190 (12)	−0.0106 (13)
C13	0.0251 (12)	0.085 (2)	0.0691 (18)	0.0136 (13)	0.0054 (12)	−0.0264 (16)
C14	0.0388 (13)	0.0656 (17)	0.0501 (14)	0.0266 (13)	−0.0048 (11)	−0.0192 (12)
C15	0.0327 (11)	0.0408 (12)	0.0313 (11)	0.0131 (9)	0.0017 (8)	−0.0062 (9)
C16	0.0255 (9)	0.0253 (9)	0.0284 (10)	0.0057 (8)	0.0077 (8)	0.0004 (7)
C17	0.0392 (11)	0.0293 (10)	0.0294 (10)	0.0074 (9)	0.0133 (9)	0.0011 (8)
C18	0.0484 (13)	0.0341 (11)	0.0426 (12)	0.0136 (10)	0.0187 (10)	−0.0035 (9)
C19	0.0488 (13)	0.0317 (11)	0.0518 (14)	0.0192 (10)	0.0158 (11)	0.0055 (10)
C20	0.0521 (14)	0.0416 (12)	0.0377 (12)	0.0227 (11)	0.0139 (10)	0.0119 (10)
C21	0.0427 (12)	0.0358 (11)	0.0295 (10)	0.0157 (10)	0.0119 (9)	0.0030 (8)
C22	0.0322 (10)	0.0313 (10)	0.0222 (9)	0.0163 (8)	0.0085 (8)	0.0059 (7)
C23	0.0366 (12)	0.0419 (12)	0.0376 (12)	0.0122 (10)	0.0116 (9)	0.0128 (9)
C24	0.0554 (16)	0.0576 (16)	0.075 (2)	0.0238 (14)	0.0380 (15)	0.0376 (15)
C25	0.106 (3)	0.0722 (19)	0.0443 (15)	0.0525 (19)	0.0494 (17)	0.0245 (14)
C26	0.105 (2)	0.0549 (16)	0.0273 (12)	0.0363 (17)	0.0212 (14)	0.0058 (11)
C27	0.0556 (14)	0.0401 (12)	0.0254 (10)	0.0173 (11)	0.0050 (10)	0.0002 (9)
Sn2	0.02496 (7)	0.02192 (7)	0.01935 (6)	0.00797 (5)	0.00520 (5)	0.00102 (5)
S3	0.0357 (3)	0.0334 (3)	0.0260 (2)	0.0199 (2)	0.0129 (2)	0.00964 (19)
S4	0.0459 (3)	0.0260 (2)	0.0315 (3)	0.0154 (2)	0.0169 (2)	0.00464 (19)
N2	0.0399 (9)	0.0213 (8)	0.0287 (8)	0.0100 (7)	0.0164 (7)	0.0061 (6)
C28	0.0257 (9)	0.0238 (9)	0.0252 (9)	0.0054 (8)	0.0066 (7)	0.0018 (7)
C29	0.0849 (19)	0.0261 (11)	0.0492 (14)	0.0252 (12)	0.0386 (14)	0.0172 (10)
C30	0.122 (3)	0.0634 (19)	0.0487 (16)	0.059 (2)	0.0063 (17)	0.0182 (14)
C31	0.0375 (11)	0.0254 (9)	0.0216 (9)	0.0116 (8)	0.0119 (8)	0.0063 (7)
C32	0.0340 (11)	0.0281 (10)	0.0365 (11)	0.0086 (9)	0.0081 (9)	0.0031 (8)
C33	0.0569 (15)	0.0311 (11)	0.0318 (11)	0.0141 (10)	0.0072 (10)	−0.0033 (9)
C34	0.0608 (15)	0.0445 (13)	0.0341 (11)	0.0281 (12)	0.0233 (11)	0.0073 (10)
C35	0.0404 (13)	0.0488 (14)	0.0498 (14)	0.0173 (11)	0.0231 (11)	0.0099 (11)
C36	0.0363 (11)	0.0335 (11)	0.0346 (11)	0.0063 (9)	0.0113 (9)	0.0027 (9)
C37	0.0259 (9)	0.0247 (9)	0.0173 (8)	0.0100 (7)	0.0042 (7)	−0.0011 (7)
C38	0.0295 (10)	0.0253 (9)	0.0210 (9)	0.0117 (8)	0.0031 (7)	0.0005 (7)
C39	0.0287 (10)	0.0296 (10)	0.0259 (9)	0.0052 (8)	0.0050 (8)	0.0004 (8)
C40	0.0258 (10)	0.0387 (11)	0.0267 (10)	0.0117 (9)	0.0002 (8)	−0.0069 (8)
C41	0.0349 (11)	0.0341 (11)	0.0290 (10)	0.0190 (9)	−0.0002 (8)	−0.0031 (8)
C42	0.0346 (10)	0.0243 (9)	0.0272 (9)	0.0123 (8)	0.0054 (8)	0.0007 (7)
C43	0.0243 (9)	0.0270 (9)	0.0234 (9)	0.0101 (8)	0.0038 (7)	0.0019 (7)
C44	0.0471 (12)	0.0356 (11)	0.0222 (9)	0.0210 (10)	0.0098 (9)	0.0026 (8)
C45	0.0644 (15)	0.0368 (12)	0.0362 (12)	0.0303 (11)	0.0188 (11)	0.0054 (9)
C46	0.0422 (12)	0.0311 (11)	0.0366 (11)	0.0179 (9)	0.0105 (9)	0.0110 (9)
C47	0.0391 (11)	0.0333 (11)	0.0224 (9)	0.0100 (9)	0.0034 (8)	0.0052 (8)
C48	0.0391 (11)	0.0259 (10)	0.0228 (9)	0.0090 (8)	0.0071 (8)	−0.0003 (7)
C49	0.0334 (10)	0.0222 (9)	0.0230 (9)	0.0011 (8)	0.0072 (8)	0.0007 (7)
C50	0.0428 (13)	0.0346 (12)	0.0420 (13)	0.0060 (10)	−0.0040 (10)	0.0021 (10)
C51	0.0662 (18)	0.0442 (15)	0.0438 (14)	−0.0060 (13)	−0.0172 (13)	0.0028 (12)
C52	0.092 (2)	0.0412 (15)	0.0336 (13)	−0.0187 (15)	0.0006 (14)	−0.0061 (11)
C53	0.095 (2)	0.0418 (15)	0.0559 (17)	0.0058 (15)	0.0331 (17)	−0.0173 (13)
C54	0.0497 (14)	0.0393 (13)	0.0450 (13)	0.0111 (11)	0.0139 (11)	−0.0103 (10)

Geometric parameters (Å, º) top

Sn1—C10	2.1339 (19)	Sn2—C37	2.1413 (18)
Sn1—C16	2.1541 (19)	Sn2—C43	2.1605 (19)
Sn1—C22	2.1210 (18)	Sn2—C49	2.1379 (19)
Sn1—S1	2.4539 (5)	Sn2—S3	2.4662 (5)
S1—C1	1.759 (2)	S3—C28	1.7496 (19)
S2—C1	1.680 (2)	S4—C28	1.6862 (19)
N1—C1	1.342 (2)	N2—C28	1.333 (2)
N1—C4	1.448 (3)	N2—C31	1.449 (2)
N1—C2	1.492 (3)	N2—C29	1.481 (3)
C2—C3	1.496 (4)	C29—C30	1.518 (4)
C2—H2A	0.9900	C29—H29A	0.9900
C2—H2B	0.9900	C29—H29B	0.9900
C3—H3A	0.9800	C30—H30A	0.9800
C3—H3B	0.9800	C30—H30B	0.9800
C3—H3C	0.9800	C30—H30C	0.9800
C4—C9	1.382 (3)	C31—C32	1.381 (3)
C4—C5	1.382 (3)	C31—C36	1.379 (3)
C5—C6	1.379 (3)	C32—C33	1.393 (3)
C5—H5	0.9500	C32—H32	0.9500
C6—C7	1.374 (4)	C33—C34	1.384 (3)
C6—H6	0.9500	C33—H33	0.9500
C7—C8	1.376 (4)	C34—C35	1.363 (3)
C7—H7	0.9500	C34—H34	0.9500
C8—C9	1.391 (4)	C35—C36	1.386 (3)
C8—H8	0.9500	C35—H35	0.9500
C9—H9	0.9500	C36—H36	0.9500
C10—C15	1.393 (3)	C37—C38	1.391 (3)
C10—C11	1.388 (3)	C37—C42	1.396 (3)
C11—C12	1.400 (3)	C38—C39	1.389 (3)
C11—H11	0.9500	C38—H38	0.9500
C12—C13	1.375 (4)	C39—C40	1.386 (3)
C12—H12	0.9500	C39—H39	0.9500
C13—C14	1.375 (4)	C40—C41	1.382 (3)
C13—H13	0.9500	C40—H40	0.9500
C14—C15	1.389 (3)	C41—C42	1.392 (3)
C14—H14	0.9500	C41—H41	0.9500
C15—H15	0.9500	C42—H42	0.9500
C16—C17	1.396 (3)	C43—C48	1.392 (3)
C16—C21	1.395 (3)	C43—C44	1.398 (3)
C17—C18	1.387 (3)	C44—C45	1.384 (3)
C17—H17	0.9500	C44—H44	0.9500
C18—C19	1.378 (3)	C45—C46	1.381 (3)
C18—H18	0.9500	C45—H45	0.9500
C19—C20	1.382 (3)	C46—C47	1.383 (3)
C19—H19	0.9500	C46—H46	0.9500
C20—C21	1.384 (3)	C47—C48	1.386 (3)
C20—H20	0.9500	C47—H47	0.9500
C21—H21	0.9500	C48—H48	0.9500
C22—C27	1.390 (3)	C49—C50	1.389 (3)
C22—C23	1.382 (3)	C49—C54	1.384 (3)
C23—C24	1.403 (3)	C50—C51	1.386 (3)
C23—H23	0.9500	C50—H50	0.9500
C24—C25	1.390 (4)	C51—C52	1.362 (5)
C24—H24	0.9500	C51—H51	0.9500
C25—C26	1.361 (4)	C52—C53	1.376 (5)
C25—H25	0.9500	C52—H52	0.9500
C26—C27	1.370 (3)	C53—C54	1.398 (4)
C26—H26	0.9500	C53—H53	0.9500
C27—H27	0.9500	C54—H54	0.9500

C22—Sn1—C10	112.49 (7)	C49—Sn2—C37	115.41 (7)
C22—Sn1—C16	105.17 (7)	C49—Sn2—C43	101.51 (7)
C10—Sn1—C16	108.02 (8)	C37—Sn2—C43	103.22 (7)
C22—Sn1—S1	113.28 (6)	C49—Sn2—S3	118.66 (5)
C10—Sn1—S1	120.48 (5)	C37—Sn2—S3	117.12 (5)
C16—Sn1—S1	94.46 (5)	C43—Sn2—S3	95.28 (5)
C1—S1—Sn1	98.20 (7)	C28—S3—Sn2	95.09 (6)
C1—N1—C4	121.45 (17)	C28—N2—C31	122.39 (15)
C1—N1—C2	122.48 (18)	C28—N2—C29	121.82 (16)
C4—N1—C2	116.05 (16)	C31—N2—C29	115.65 (15)
N1—C1—S2	123.77 (16)	N2—C28—S4	123.09 (14)
N1—C1—S1	115.59 (15)	N2—C28—S3	116.67 (14)
S2—C1—S1	120.63 (11)	S4—C28—S3	120.24 (11)
N1—C2—C3	112.3 (2)	N2—C29—C30	111.3 (2)
N1—C2—H2A	109.1	N2—C29—H29A	109.4
C3—C2—H2A	109.1	C30—C29—H29A	109.4
N1—C2—H2B	109.1	N2—C29—H29B	109.4
C3—C2—H2B	109.1	C30—C29—H29B	109.4
H2A—C2—H2B	107.9	H29A—C29—H29B	108.0
C2—C3—H3A	109.5	C29—C30—H30A	109.5
C2—C3—H3B	109.5	C29—C30—H30B	109.5
H3A—C3—H3B	109.5	H30A—C30—H30B	109.5
C2—C3—H3C	109.5	C29—C30—H30C	109.5
H3A—C3—H3C	109.5	H30A—C30—H30C	109.5
H3B—C3—H3C	109.5	H30B—C30—H30C	109.5
C9—C4—C5	121.3 (2)	C32—C31—C36	121.41 (19)
C9—C4—N1	119.0 (2)	C32—C31—N2	119.92 (18)
C5—C4—N1	119.70 (19)	C36—C31—N2	118.56 (18)
C6—C5—C4	119.5 (2)	C31—C32—C33	118.8 (2)
C6—C5—H5	120.2	C31—C32—H32	120.6
C4—C5—H5	120.2	C33—C32—H32	120.6
C7—C6—C5	120.1 (3)	C34—C33—C32	119.9 (2)
C7—C6—H6	120.0	C34—C33—H33	120.0
C5—C6—H6	120.0	C32—C33—H33	120.0
C8—C7—C6	120.2 (2)	C35—C34—C33	120.3 (2)
C8—C7—H7	119.9	C35—C34—H34	119.9
C6—C7—H7	119.9	C33—C34—H34	119.9
C7—C8—C9	120.8 (3)	C34—C35—C36	120.8 (2)
C7—C8—H8	119.6	C34—C35—H35	119.6
C9—C8—H8	119.6	C36—C35—H35	119.6
C4—C9—C8	118.2 (2)	C31—C36—C35	118.8 (2)
C4—C9—H9	120.9	C31—C36—H36	120.6
C8—C9—H9	120.9	C35—C36—H36	120.6
C15—C10—C11	118.9 (2)	C38—C37—C42	118.60 (17)
C15—C10—Sn1	119.93 (15)	C38—C37—Sn2	116.12 (13)
C11—C10—Sn1	121.02 (16)	C42—C37—Sn2	125.26 (14)
C10—C11—C12	120.0 (2)	C39—C38—C37	121.05 (17)
C10—C11—H11	120.0	C39—C38—H38	119.5
C12—C11—H11	120.0	C37—C38—H38	119.5
C13—C12—C11	120.0 (3)	C38—C39—C40	119.83 (19)
C13—C12—H12	120.0	C38—C39—H39	120.1
C11—C12—H12	120.0	C40—C39—H39	120.1
C12—C13—C14	120.6 (2)	C41—C40—C39	119.82 (19)
C12—C13—H13	119.7	C41—C40—H40	120.1
C14—C13—H13	119.7	C39—C40—H40	120.1
C13—C14—C15	119.7 (3)	C40—C41—C42	120.42 (18)
C13—C14—H14	120.2	C40—C41—H41	119.8
C15—C14—H14	120.2	C42—C41—H41	119.8
C10—C15—C14	120.8 (2)	C41—C42—C37	120.28 (18)
C10—C15—H15	119.6	C41—C42—H42	119.9
C14—C15—H15	119.6	C37—C42—H42	119.9
C17—C16—C21	116.95 (18)	C48—C43—C44	117.55 (17)
C17—C16—Sn1	121.01 (14)	C48—C43—Sn2	118.58 (13)
C21—C16—Sn1	121.99 (14)	C44—C43—Sn2	123.82 (14)
C18—C17—C16	121.53 (19)	C45—C44—C43	121.00 (18)
C18—C17—H17	119.2	C45—C44—H44	119.5
C16—C17—H17	119.2	C43—C44—H44	119.5
C19—C18—C17	120.1 (2)	C44—C45—C46	120.29 (19)
C19—C18—H18	120.0	C44—C45—H45	119.9
C17—C18—H18	120.0	C46—C45—H45	119.9
C20—C19—C18	119.7 (2)	C47—C46—C45	119.88 (19)
C20—C19—H19	120.1	C47—C46—H46	120.1
C18—C19—H19	120.1	C45—C46—H46	120.1
C19—C20—C21	119.9 (2)	C46—C47—C48	119.56 (18)
C19—C20—H20	120.1	C46—C47—H47	120.2
C21—C20—H20	120.1	C48—C47—H47	120.2
C20—C21—C16	121.82 (19)	C43—C48—C47	121.71 (18)
C20—C21—H21	119.1	C43—C48—H48	119.1
C16—C21—H21	119.1	C47—C48—H48	119.1
C27—C22—C23	118.84 (19)	C50—C49—C54	118.5 (2)
C27—C22—Sn1	117.20 (16)	C50—C49—Sn2	120.19 (16)
C23—C22—Sn1	123.75 (15)	C54—C49—Sn2	120.84 (16)
C22—C23—C24	119.6 (2)	C51—C50—C49	120.9 (3)
C22—C23—H23	120.2	C51—C50—H50	119.5
C24—C23—H23	120.2	C49—C50—H50	119.5
C25—C24—C23	119.7 (3)	C52—C51—C50	120.1 (3)
C25—C24—H24	120.2	C52—C51—H51	119.9
C23—C24—H24	120.2	C50—C51—H51	119.9
C26—C25—C24	120.6 (2)	C51—C52—C53	120.1 (2)
C26—C25—H25	119.7	C51—C52—H52	119.9
C24—C25—H25	119.7	C53—C52—H52	119.9
C25—C26—C27	119.6 (3)	C52—C53—C54	120.2 (3)
C25—C26—H26	120.2	C52—C53—H53	119.9
C27—C26—H26	120.2	C54—C53—H53	119.9
C26—C27—C22	121.7 (2)	C53—C54—C49	120.1 (3)
C26—C27—H27	119.1	C53—C54—H54	120.0
C22—C27—H27	119.1	C49—C54—H54	120.0

C22—Sn1—S1—C1	−82.34 (8)	C49—Sn2—S3—C28	76.70 (9)
C10—Sn1—S1—C1	55.09 (9)	C37—Sn2—S3—C28	−69.32 (8)
C16—Sn1—S1—C1	169.04 (8)	C43—Sn2—S3—C28	−177.10 (8)
C4—N1—C1—S2	176.31 (16)	C31—N2—C28—S4	177.77 (15)
C2—N1—C1—S2	−5.4 (3)	C29—N2—C28—S4	2.3 (3)
C4—N1—C1—S1	−5.0 (3)	C31—N2—C28—S3	−2.6 (3)
C2—N1—C1—S1	173.26 (17)	C29—N2—C28—S3	−178.10 (17)
Sn1—S1—C1—N1	−166.86 (14)	Sn2—S3—C28—N2	174.02 (14)
Sn1—S1—C1—S2	11.88 (12)	Sn2—S3—C28—S4	−6.32 (12)
C1—N1—C2—C3	92.9 (3)	C28—N2—C29—C30	86.3 (3)
C4—N1—C2—C3	−88.7 (2)	C31—N2—C29—C30	−89.5 (2)
C1—N1—C4—C9	95.5 (2)	C28—N2—C31—C32	−80.5 (2)
C2—N1—C4—C9	−82.9 (3)	C29—N2—C31—C32	95.2 (2)
C1—N1—C4—C5	−86.6 (2)	C28—N2—C31—C36	103.0 (2)
C2—N1—C4—C5	95.0 (2)	C29—N2—C31—C36	−81.2 (2)
C9—C4—C5—C6	−0.9 (3)	C36—C31—C32—C33	−0.6 (3)
N1—C4—C5—C6	−178.75 (19)	N2—C31—C32—C33	−176.94 (18)
C4—C5—C6—C7	0.0 (3)	C31—C32—C33—C34	−0.2 (3)
C5—C6—C7—C8	0.7 (4)	C32—C33—C34—C35	0.5 (3)
C6—C7—C8—C9	−0.5 (4)	C33—C34—C35—C36	0.0 (4)
C5—C4—C9—C8	1.0 (3)	C32—C31—C36—C35	1.1 (3)
N1—C4—C9—C8	178.9 (2)	N2—C31—C36—C35	177.50 (19)
C7—C8—C9—C4	−0.3 (4)	C34—C35—C36—C31	−0.8 (3)
C22—Sn1—C10—C15	37.46 (17)	C49—Sn2—C37—C38	109.91 (13)
C16—Sn1—C10—C15	153.09 (15)	C43—Sn2—C37—C38	0.12 (14)
S1—Sn1—C10—C15	−100.26 (15)	S3—Sn2—C37—C38	−102.97 (13)
C22—Sn1—C10—C11	−138.42 (16)	C49—Sn2—C37—C42	−68.03 (17)
C16—Sn1—C10—C11	−22.79 (18)	C43—Sn2—C37—C42	−177.83 (15)
S1—Sn1—C10—C11	83.85 (16)	S3—Sn2—C37—C42	79.09 (15)
C15—C10—C11—C12	1.8 (3)	C42—C37—C38—C39	0.4 (3)
Sn1—C10—C11—C12	177.71 (17)	Sn2—C37—C38—C39	−177.68 (14)
C10—C11—C12—C13	−1.6 (4)	C37—C38—C39—C40	−0.1 (3)
C11—C12—C13—C14	0.0 (4)	C38—C39—C40—C41	−0.5 (3)
C12—C13—C14—C15	1.3 (4)	C39—C40—C41—C42	0.7 (3)
C11—C10—C15—C14	−0.5 (3)	C40—C41—C42—C37	−0.4 (3)
Sn1—C10—C15—C14	−176.47 (16)	C38—C37—C42—C41	−0.2 (3)
C13—C14—C15—C10	−1.0 (3)	Sn2—C37—C42—C41	177.73 (14)
C22—Sn1—C16—C17	20.76 (18)	C49—Sn2—C43—C48	−35.27 (16)
C10—Sn1—C16—C17	−99.57 (17)	C37—Sn2—C43—C48	84.57 (16)
S1—Sn1—C16—C17	136.35 (16)	S3—Sn2—C43—C48	−155.95 (15)
C22—Sn1—C16—C21	−156.46 (16)	C49—Sn2—C43—C44	147.26 (17)
C10—Sn1—C16—C21	83.20 (17)	C37—Sn2—C43—C44	−92.89 (17)
S1—Sn1—C16—C21	−40.88 (17)	S3—Sn2—C43—C44	26.58 (17)
C21—C16—C17—C18	−0.3 (3)	C48—C43—C44—C45	1.0 (3)
Sn1—C16—C17—C18	−177.70 (17)	Sn2—C43—C44—C45	178.45 (17)
C16—C17—C18—C19	0.1 (3)	C43—C44—C45—C46	−0.3 (4)
C17—C18—C19—C20	0.2 (4)	C44—C45—C46—C47	−0.7 (4)
C18—C19—C20—C21	−0.1 (4)	C45—C46—C47—C48	1.1 (3)
C19—C20—C21—C16	−0.1 (4)	C44—C43—C48—C47	−0.6 (3)
C17—C16—C21—C20	0.4 (3)	Sn2—C43—C48—C47	−178.21 (16)
Sn1—C16—C21—C20	177.70 (17)	C46—C47—C48—C43	−0.4 (3)
C10—Sn1—C22—C27	48.80 (17)	C37—Sn2—C49—C50	−153.78 (16)
C16—Sn1—C22—C27	−68.54 (17)	C43—Sn2—C49—C50	−42.98 (18)
S1—Sn1—C22—C27	−170.33 (14)	S3—Sn2—C49—C50	59.63 (18)
C10—Sn1—C22—C23	−136.57 (17)	C37—Sn2—C49—C54	18.37 (19)
C16—Sn1—C22—C23	106.10 (17)	C43—Sn2—C49—C54	129.18 (17)
S1—Sn1—C22—C23	4.30 (18)	S3—Sn2—C49—C54	−128.22 (16)
C27—C22—C23—C24	1.5 (3)	C54—C49—C50—C51	−0.5 (3)
Sn1—C22—C23—C24	−173.10 (17)	Sn2—C49—C50—C51	171.82 (19)
C22—C23—C24—C25	−0.3 (4)	C49—C50—C51—C52	−0.7 (4)
C23—C24—C25—C26	−1.3 (4)	C50—C51—C52—C53	1.1 (4)
C24—C25—C26—C27	1.8 (4)	C51—C52—C53—C54	−0.3 (4)
C25—C26—C27—C22	−0.7 (4)	C52—C53—C54—C49	−1.0 (4)
C23—C22—C27—C26	−1.0 (3)	C50—C49—C54—C53	1.3 (3)
Sn1—C22—C27—C26	173.95 (19)	Sn2—C49—C54—C53	−170.94 (19)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, and Cg3 are the centroids of the C16–C21, C37–C42 and C43–C48 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1ⁱ	0.95	2.72	3.630 (3)	160
C25—H25···Cg2ⁱⁱ	0.95	2.90	3.639 (3)	135
C32—H32···Cg3ⁱⁱⁱ	0.95	2.92	3.824 (2)	160

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₉H₁₀NS₂)]
M_r	546.29
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.6973 (2), 12.2804 (2), 22.8523 (4)
α, β, γ (°)	90.588 (2), 101.573 (2), 110.687 (2)
V (Å³)	2484.39 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.30 × 0.24 × 0.19

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.748, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	62467, 10558, 9633
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.055, 1.00
No. of reflections	10558
No. of parameters	561
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.44

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—C10	2.1339 (19)	Sn2—C37	2.1413 (18)
Sn1—C16	2.1541 (19)	Sn2—C43	2.1605 (19)
Sn1—C22	2.1210 (18)	Sn2—C49	2.1379 (19)
Sn1—S1	2.4539 (5)	Sn2—S3	2.4662 (5)
S1—C1	1.759 (2)	S3—C28	1.7496 (19)
S2—C1	1.680 (2)	S4—C28	1.6862 (19)