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

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

doi:10.1107/S1600536811012426

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m555-m556

doi:10.1107/S1600536811012426

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

Nurul Farahana Kamaludin,^a Ibrahim Baba,^b ‡ Normah Awang,^a Mohamed Ibrahim Mohamed Tahir ^c and Edward R. T. Tiekink ^d ^*

^aEnvironmental Health Programme, Faculty of Allied Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Aziz, 50300 Kuala Lumpur, Malaysia, ^bSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Malaysia, ^cDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 3 April 2011; accepted 4 April 2011; online 7 April 2011)

The title compound, [Sn(C₆H₅)₃(C₁₁H₁₄NS₂)], features a tetrahedrally coordinated Sn atom, as the dithiocarbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetrahedral geometry about the metal atom are evident with the widest C—Sn—S angle being 117.26 (5)°. In the crystal, molecules are linked by C—H⋯S interactions, which generate helical supramolecular chains along the b axis.

Related literature

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008 ). For a recently reported related structure, see: Awang et al. (2010 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]
M_r = 574.34
Monoclinic, P 2₁ /n
a = 10.0488 (1) Å
b = 18.0008 (2) Å
c = 15.2054 (2) Å
β = 102.442 (1)°
V = 2685.85 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 150 K
0.24 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.781, T_max = 0.894
34109 measured reflections
6099 independent reflections
5277 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.060
S = 1.02
6099 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn—S1	2.4772 (5)
Sn—S2	3.1048 (5)
Sn—C12	2.1286 (18)
Sn—C18	2.1380 (19)
Sn—C24	2.1521 (18)
S1—C1	1.758 (2)
S2—C1	1.675 (2)

C12—Sn—C18	113.76 (7)
C12—Sn—C24	107.51 (7)
C18—Sn—C24	107.45 (7)
C12—Sn—S1	117.26 (5)
C18—Sn—S1	115.54 (5)
C24—Sn—S1	92.18 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯S2ⁱ	0.95	2.83	3.612 (2)	140
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012426/hb5836sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012426/hb5836Isup2.hkl

checkCIF report

Comment top

Their potential as anti-cancer agents, anti-microbials and insecticides, and as convenient synthetic precursors for tin sulfide nanoparticles, attract continued attention to organotin dithiocarbamates (Tiekink, 2008). As part of on-going of structural studies of triphenyltin(IV) dithiocarbamates (Awang et al., 2010), the analysis of the title compound, (I), was undertaken.

The molecular structure, Fig. 1, features Sn coordinated by the dithiocarbamate ligand and three ipso-C atoms of three benzene rings. The dithiocarbamte 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 92.18 (5) to 117.26 (5) °. The wider angles are ascribed to the influence of the proximate S2 atom. The crystal packing of (I) features helical supramolecular chains along the b axis that is sustained by C—H···S interactions, Fig. 2 and Table 2.

Related literature top

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For a recently reported related structure, see: Awang et al. (2010).

Experimental top

The title compound was prepared using an in situ method by the addition of carbon disulfide (0.01 mol) to an ethanolic solution of N-butylphenylamine (0.01 mol). The mixture was stirred for 1 h at 277 K. The solution was then added drop-wise to a solution of triphenyltin(IV) chloride (0.01 mol) in ethanol (20 ml). The mixture was stirred for 1 h. The white precipitate that formed was filtered, washed with cold ethanol and dried in a desiccator. Crystallization was carried out by using an ethanol:chloroform (1:1 v/v) mixture to yield colourless prisms of (I). Yield: 34%. M.pt. 374–375 K. Elemental analysis. Found (calculated) for C₂₉H₂₉NS₂Sn: C, 60.54 (60.64); H 5.08 (5.09); N 2.34 (2.44); S 11.31 (11.17); Sn 20.19 (20.66) %. UV (CHCl₃) λ_max 252 nm (L(π) → L(π*)). IR (KBr): ν(C—H) 2960 m; ν(C≐N) 1477 m; ν(N—C) 1139 s; ν(C≐S) 997 s; ν(Cd—S) 356 s cm^-1.

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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the helical supramolecular chain in (I) mediated by C—H···S interactions (orange dashed lines) along the b axis in (I).

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

Crystal data top

[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]	F(000) = 1168
M_r = 574.34	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18395 reflections
a = 10.0488 (1) Å	θ = 2–29°
b = 18.0008 (2) Å	µ = 1.12 mm⁻¹
c = 15.2054 (2) Å	T = 150 K
β = 102.442 (1)°	Prism, colourless
V = 2685.85 (5) Å³	0.24 × 0.22 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	6099 independent reflections
Radiation source: fine-focus sealed tube	5277 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 16.1952 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −23→23
T_min = 0.781, T_max = 0.894	l = −19→19
34109 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0284P)² + 0.6995P] where P = (F_o² + 2F_c²)/3
6099 reflections	(Δ/σ)_max = 0.003
299 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]	V = 2685.85 (5) Å³
M_r = 574.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0488 (1) Å	µ = 1.12 mm⁻¹
b = 18.0008 (2) Å	T = 150 K
c = 15.2054 (2) Å	0.24 × 0.22 × 0.10 mm
β = 102.442 (1)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	6099 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	5277 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.894	R_int = 0.044
34109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
6099 reflections	Δρ_min = −0.27 e Å⁻³
299 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
Sn	0.636843 (12)	0.514323 (7)	0.706567 (8)	0.02366 (5)
S1	0.74819 (5)	0.56428 (3)	0.85614 (3)	0.03110 (11)
S2	0.60687 (5)	0.42144 (3)	0.87326 (3)	0.03087 (11)
N1	0.72072 (18)	0.50776 (9)	1.01112 (11)	0.0316 (4)
C1	0.6917 (2)	0.49591 (10)	0.92221 (13)	0.0280 (4)
C2	0.6806 (2)	0.45399 (12)	1.07424 (13)	0.0366 (5)
H2A	0.5941	0.4299	1.0445	0.044*
H2B	0.6642	0.4811	1.1276	0.044*
C3	0.7875 (2)	0.39454 (12)	1.10512 (14)	0.0392 (5)
H3A	0.8713	0.4180	1.1404	0.047*
H3B	0.8106	0.3705	1.0518	0.047*
C4	0.7378 (3)	0.33576 (13)	1.16269 (15)	0.0471 (6)
H4A	0.6524	0.3135	1.1280	0.057*
H4B	0.7172	0.3597	1.2168	0.057*
C5	0.8423 (3)	0.27455 (16)	1.19190 (19)	0.0671 (8)
H5A	0.8668	0.2525	1.1386	0.101*
H5B	0.8035	0.2362	1.2247	0.101*
H5C	0.9239	0.2955	1.2312	0.101*
C6	0.7940 (2)	0.57343 (12)	1.05062 (13)	0.0338 (5)
C7	0.7210 (2)	0.63472 (12)	1.06800 (14)	0.0365 (5)
H7	0.6242	0.6337	1.0544	0.044*
C8	0.7902 (3)	0.69796 (13)	1.10562 (15)	0.0442 (5)
H8	0.7407	0.7403	1.1178	0.053*
C9	0.9303 (3)	0.69916 (15)	1.12510 (15)	0.0518 (6)
H9	0.9775	0.7427	1.1498	0.062*
C10	1.0025 (3)	0.63747 (16)	1.10886 (17)	0.0578 (7)
H10	1.0993	0.6384	1.1228	0.069*
C11	0.9344 (2)	0.57402 (15)	1.07221 (15)	0.0485 (6)
H11	0.9842	0.5312	1.0620	0.058*
C12	0.71232 (19)	0.41209 (10)	0.66655 (12)	0.0258 (4)
C13	0.8499 (2)	0.40110 (12)	0.67362 (15)	0.0377 (5)
H13	0.9118	0.4400	0.6962	0.045*
C14	0.8999 (2)	0.33402 (12)	0.64823 (16)	0.0442 (5)
H14	0.9952	0.3274	0.6540	0.053*
C15	0.8124 (3)	0.27783 (12)	0.61507 (15)	0.0421 (5)
H15	0.8465	0.2319	0.5986	0.050*
C16	0.6745 (3)	0.28803 (12)	0.60564 (17)	0.0498 (6)
H16	0.6132	0.2494	0.5811	0.060*
C17	0.6240 (2)	0.35448 (12)	0.63171 (15)	0.0404 (5)
H17	0.5285	0.3607	0.6257	0.048*
C18	0.41962 (19)	0.52313 (10)	0.67250 (13)	0.0263 (4)
C19	0.3332 (2)	0.47347 (11)	0.70304 (14)	0.0329 (4)
H19	0.3709	0.4336	0.7413	0.039*
C20	0.1932 (2)	0.48155 (13)	0.67828 (17)	0.0439 (6)
H20	0.1357	0.4477	0.7004	0.053*
C21	0.1365 (2)	0.53874 (15)	0.62151 (17)	0.0489 (6)
H21	0.0403	0.5446	0.6052	0.059*
C22	0.2205 (2)	0.58712 (13)	0.58878 (15)	0.0426 (5)
H22	0.1819	0.6256	0.5485	0.051*
C23	0.3614 (2)	0.57999 (11)	0.61427 (13)	0.0328 (4)
H23	0.4184	0.6140	0.5919	0.039*
C24	0.71761 (18)	0.60219 (10)	0.63749 (12)	0.0260 (4)
C25	0.7478 (2)	0.59142 (12)	0.55345 (14)	0.0388 (5)
H25	0.7282	0.5450	0.5238	0.047*
C26	0.8063 (3)	0.64789 (14)	0.51222 (16)	0.0510 (6)
H26	0.8271	0.6395	0.4550	0.061*
C27	0.8344 (2)	0.71606 (13)	0.55379 (16)	0.0472 (6)
H27	0.8737	0.7546	0.5252	0.057*
C28	0.8049 (3)	0.72759 (12)	0.63682 (16)	0.0455 (6)
H28	0.8242	0.7743	0.6659	0.055*
C29	0.7472 (2)	0.67142 (11)	0.67806 (14)	0.0383 (5)
H29	0.7272	0.6802	0.7355	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02646 (8)	0.02098 (8)	0.02380 (8)	−0.00103 (5)	0.00594 (5)	−0.00096 (5)
S1	0.0410 (3)	0.0271 (2)	0.0234 (2)	−0.0021 (2)	0.0029 (2)	0.00049 (19)
S2	0.0389 (3)	0.0250 (2)	0.0299 (2)	0.0037 (2)	0.0100 (2)	0.00173 (19)
N1	0.0396 (10)	0.0330 (9)	0.0223 (8)	0.0080 (7)	0.0072 (7)	0.0010 (7)
C1	0.0301 (10)	0.0281 (10)	0.0259 (10)	0.0106 (8)	0.0061 (8)	0.0028 (8)
C2	0.0456 (12)	0.0418 (12)	0.0253 (10)	0.0110 (10)	0.0138 (9)	0.0053 (9)
C3	0.0446 (13)	0.0421 (12)	0.0316 (11)	0.0116 (10)	0.0101 (10)	0.0074 (9)
C4	0.0654 (16)	0.0486 (14)	0.0314 (11)	0.0150 (12)	0.0196 (11)	0.0083 (10)
C5	0.087 (2)	0.0596 (17)	0.0554 (17)	0.0233 (16)	0.0181 (15)	0.0239 (14)
C6	0.0410 (12)	0.0404 (12)	0.0194 (9)	0.0069 (9)	0.0051 (8)	0.0001 (8)
C7	0.0408 (12)	0.0376 (12)	0.0317 (11)	0.0069 (9)	0.0091 (9)	0.0032 (9)
C8	0.0604 (15)	0.0376 (12)	0.0352 (12)	0.0068 (11)	0.0111 (11)	−0.0012 (10)
C9	0.0596 (16)	0.0566 (15)	0.0342 (12)	−0.0082 (13)	−0.0009 (11)	−0.0076 (11)
C10	0.0419 (14)	0.078 (2)	0.0483 (15)	0.0000 (13)	−0.0023 (12)	−0.0180 (14)
C11	0.0415 (13)	0.0615 (16)	0.0389 (13)	0.0146 (11)	0.0005 (10)	−0.0115 (11)
C12	0.0340 (10)	0.0218 (9)	0.0230 (9)	−0.0014 (8)	0.0090 (8)	0.0004 (7)
C13	0.0342 (11)	0.0316 (11)	0.0468 (13)	−0.0021 (9)	0.0076 (10)	−0.0081 (9)
C14	0.0435 (13)	0.0396 (12)	0.0501 (14)	0.0115 (10)	0.0111 (11)	−0.0039 (11)
C15	0.0688 (16)	0.0272 (11)	0.0359 (12)	0.0091 (11)	0.0238 (11)	0.0014 (9)
C16	0.0684 (17)	0.0299 (12)	0.0554 (15)	−0.0169 (11)	0.0226 (13)	−0.0156 (11)
C17	0.0415 (12)	0.0348 (12)	0.0482 (13)	−0.0096 (9)	0.0171 (10)	−0.0120 (10)
C18	0.0270 (9)	0.0280 (10)	0.0234 (9)	0.0008 (7)	0.0046 (8)	−0.0057 (7)
C19	0.0310 (10)	0.0334 (11)	0.0344 (11)	−0.0019 (8)	0.0073 (9)	0.0015 (9)
C20	0.0322 (11)	0.0515 (14)	0.0491 (14)	−0.0063 (10)	0.0111 (10)	−0.0004 (11)
C21	0.0295 (11)	0.0597 (15)	0.0526 (15)	0.0049 (11)	−0.0017 (11)	−0.0041 (12)
C22	0.0413 (12)	0.0402 (12)	0.0402 (12)	0.0093 (10)	−0.0045 (10)	−0.0001 (10)
C23	0.0393 (11)	0.0291 (10)	0.0276 (10)	−0.0006 (9)	0.0023 (9)	−0.0013 (8)
C24	0.0265 (9)	0.0249 (9)	0.0253 (9)	−0.0006 (7)	0.0025 (8)	0.0026 (7)
C25	0.0540 (14)	0.0325 (11)	0.0312 (11)	−0.0070 (10)	0.0122 (10)	−0.0023 (9)
C26	0.0723 (17)	0.0504 (15)	0.0358 (12)	−0.0063 (13)	0.0237 (12)	0.0062 (11)
C27	0.0547 (14)	0.0398 (13)	0.0481 (14)	−0.0105 (11)	0.0131 (12)	0.0156 (11)
C28	0.0639 (15)	0.0261 (11)	0.0432 (13)	−0.0108 (10)	0.0046 (12)	0.0037 (9)
C29	0.0588 (14)	0.0265 (10)	0.0308 (11)	−0.0036 (10)	0.0122 (10)	−0.0013 (8)

Geometric parameters (Å, º) top

Sn—S1	2.4772 (5)	C12—C13	1.377 (3)
Sn—S2	3.1048 (5)	C12—C17	1.393 (3)
Sn—C12	2.1286 (18)	C13—C14	1.394 (3)
Sn—C18	2.1380 (19)	C13—H13	0.9500
Sn—C24	2.1521 (18)	C14—C15	1.364 (3)
S1—C1	1.758 (2)	C14—H14	0.9500
S2—C1	1.675 (2)	C15—C16	1.374 (3)
N1—C1	1.337 (2)	C15—H15	0.9500
N1—C6	1.453 (3)	C16—C17	1.390 (3)
N1—C2	1.479 (3)	C16—H16	0.9500
C2—C3	1.517 (3)	C17—H17	0.9500
C2—H2A	0.9900	C18—C19	1.394 (3)
C2—H2B	0.9900	C18—C23	1.396 (3)
C3—C4	1.524 (3)	C19—C20	1.384 (3)
C3—H3A	0.9900	C19—H19	0.9500
C3—H3B	0.9900	C20—C21	1.385 (3)
C4—C5	1.521 (3)	C20—H20	0.9500
C4—H4A	0.9900	C21—C22	1.378 (3)
C4—H4B	0.9900	C21—H21	0.9500
C5—H5A	0.9800	C22—C23	1.391 (3)
C5—H5B	0.9800	C22—H22	0.9500
C5—H5C	0.9800	C23—H23	0.9500
C6—C11	1.378 (3)	C24—C25	1.389 (3)
C6—C7	1.382 (3)	C24—C29	1.394 (3)
C7—C8	1.391 (3)	C25—C26	1.390 (3)
C7—H7	0.9500	C25—H25	0.9500
C8—C9	1.375 (3)	C26—C27	1.381 (3)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.377 (4)	C27—C28	1.373 (3)
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.385 (4)	C28—C29	1.382 (3)
C10—H10	0.9500	C28—H28	0.9500
C11—H11	0.9500	C29—H29	0.9500

C12—Sn—C18	113.76 (7)	C13—C12—C17	118.00 (18)
C12—Sn—C24	107.51 (7)	C13—C12—Sn	121.01 (14)
C18—Sn—C24	107.45 (7)	C17—C12—Sn	120.99 (15)
C12—Sn—S1	117.26 (5)	C12—C13—C14	121.2 (2)
C18—Sn—S1	115.54 (5)	C12—C13—H13	119.4
C24—Sn—S1	92.18 (5)	C14—C13—H13	119.4
C1—S1—Sn	97.64 (7)	C15—C14—C13	120.1 (2)
C1—N1—C6	121.91 (17)	C15—C14—H14	119.9
C1—N1—C2	121.41 (18)	C13—C14—H14	119.9
C6—N1—C2	116.68 (16)	C16—C15—C14	119.7 (2)
N1—C1—S2	123.79 (16)	C16—C15—H15	120.2
N1—C1—S1	116.04 (15)	C14—C15—H15	120.2
S2—C1—S1	120.16 (12)	C15—C16—C17	120.5 (2)
N1—C2—C3	112.88 (17)	C15—C16—H16	119.8
N1—C2—H2A	109.0	C17—C16—H16	119.8
C3—C2—H2A	109.0	C16—C17—C12	120.5 (2)
N1—C2—H2B	109.0	C16—C17—H17	119.8
C3—C2—H2B	109.0	C12—C17—H17	119.8
H2A—C2—H2B	107.8	C19—C18—C23	118.40 (18)
C2—C3—C4	111.70 (18)	C19—C18—Sn	123.25 (14)
C2—C3—H3A	109.3	C23—C18—Sn	118.31 (14)
C4—C3—H3A	109.3	C20—C19—C18	120.8 (2)
C2—C3—H3B	109.3	C20—C19—H19	119.6
C4—C3—H3B	109.3	C18—C19—H19	119.6
H3A—C3—H3B	107.9	C19—C20—C21	120.4 (2)
C3—C4—C5	112.3 (2)	C19—C20—H20	119.8
C3—C4—H4A	109.1	C21—C20—H20	119.8
C5—C4—H4A	109.1	C22—C21—C20	119.5 (2)
C3—C4—H4B	109.1	C22—C21—H21	120.2
C5—C4—H4B	109.1	C20—C21—H21	120.2
H4A—C4—H4B	107.9	C21—C22—C23	120.5 (2)
C4—C5—H5A	109.5	C21—C22—H22	119.8
C4—C5—H5B	109.5	C23—C22—H22	119.8
H5A—C5—H5B	109.5	C22—C23—C18	120.4 (2)
C4—C5—H5C	109.5	C22—C23—H23	119.8
H5A—C5—H5C	109.5	C18—C23—H23	119.8
H5B—C5—H5C	109.5	C25—C24—C29	117.65 (18)
C11—C6—C7	120.5 (2)	C25—C24—Sn	121.76 (14)
C11—C6—N1	120.44 (19)	C29—C24—Sn	120.53 (14)
C7—C6—N1	119.07 (19)	C24—C25—C26	120.7 (2)
C6—C7—C8	119.5 (2)	C24—C25—H25	119.7
C6—C7—H7	120.2	C26—C25—H25	119.7
C8—C7—H7	120.2	C27—C26—C25	120.5 (2)
C9—C8—C7	120.0 (2)	C27—C26—H26	119.7
C9—C8—H8	120.0	C25—C26—H26	119.7
C7—C8—H8	120.0	C28—C27—C26	119.5 (2)
C8—C9—C10	120.2 (2)	C28—C27—H27	120.3
C8—C9—H9	119.9	C26—C27—H27	120.3
C10—C9—H9	119.9	C29—C28—C27	120.1 (2)
C9—C10—C11	120.2 (2)	C29—C28—H28	120.0
C9—C10—H10	119.9	C27—C28—H28	120.0
C11—C10—H10	119.9	C28—C29—C24	121.6 (2)
C6—C11—C10	119.6 (2)	C28—C29—H29	119.2
C6—C11—H11	120.2	C24—C29—H29	119.2
C10—C11—H11	120.2

C12—Sn—S1—C1	−68.43 (8)	C13—C14—C15—C16	0.9 (4)
C18—Sn—S1—C1	70.03 (8)	C14—C15—C16—C17	−1.6 (4)
C24—Sn—S1—C1	−179.43 (8)	C15—C16—C17—C12	1.0 (4)
C6—N1—C1—S2	−179.67 (14)	C13—C12—C17—C16	0.4 (3)
C2—N1—C1—S2	0.9 (3)	Sn—C12—C17—C16	179.86 (17)
C6—N1—C1—S1	0.3 (2)	C12—Sn—C18—C19	58.98 (18)
C2—N1—C1—S1	−179.14 (14)	C24—Sn—C18—C19	177.86 (16)
Sn—S1—C1—N1	−173.43 (14)	S1—Sn—C18—C19	−80.93 (16)
Sn—S1—C1—S2	6.51 (12)	C12—Sn—C18—C23	−118.75 (14)
C1—N1—C2—C3	88.8 (2)	C24—Sn—C18—C23	0.13 (16)
C6—N1—C2—C3	−90.7 (2)	S1—Sn—C18—C23	101.34 (14)
N1—C2—C3—C4	−174.46 (18)	C23—C18—C19—C20	−1.8 (3)
C2—C3—C4—C5	178.3 (2)	Sn—C18—C19—C20	−179.52 (16)
C1—N1—C6—C11	−87.1 (2)	C18—C19—C20—C21	0.9 (4)
C2—N1—C6—C11	92.3 (2)	C19—C20—C21—C22	0.8 (4)
C1—N1—C6—C7	94.2 (2)	C20—C21—C22—C23	−1.7 (4)
C2—N1—C6—C7	−86.3 (2)	C21—C22—C23—C18	0.8 (3)
C11—C6—C7—C8	1.5 (3)	C19—C18—C23—C22	0.9 (3)
N1—C6—C7—C8	−179.84 (18)	Sn—C18—C23—C22	178.78 (15)
C6—C7—C8—C9	0.1 (3)	C12—Sn—C24—C25	29.77 (18)
C7—C8—C9—C10	−1.1 (4)	C18—Sn—C24—C25	−93.05 (17)
C8—C9—C10—C11	0.5 (4)	S1—Sn—C24—C25	149.29 (16)
C7—C6—C11—C10	−2.1 (3)	C12—Sn—C24—C29	−147.32 (16)
N1—C6—C11—C10	179.2 (2)	C18—Sn—C24—C29	89.86 (17)
C9—C10—C11—C6	1.1 (4)	S1—Sn—C24—C29	−27.81 (16)
C18—Sn—C12—C13	172.10 (15)	C29—C24—C25—C26	0.5 (3)
C24—Sn—C12—C13	53.25 (18)	Sn—C24—C25—C26	−176.71 (18)
S1—Sn—C12—C13	−48.72 (17)	C24—C25—C26—C27	−0.6 (4)
C18—Sn—C12—C17	−7.36 (19)	C25—C26—C27—C28	0.5 (4)
C24—Sn—C12—C17	−126.21 (16)	C26—C27—C28—C29	−0.2 (4)
S1—Sn—C12—C17	131.82 (15)	C27—C28—C29—C24	0.1 (4)
C17—C12—C13—C14	−1.1 (3)	C25—C24—C29—C28	−0.2 (3)
Sn—C12—C13—C14	179.44 (17)	Sn—C24—C29—C28	177.00 (17)
C12—C13—C14—C15	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···S2ⁱ	0.95	2.83	3.612 (2)	140

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]
M_r	574.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.0488 (1), 18.0008 (2), 15.2054 (2)
β (°)	102.442 (1)
V (Å³)	2685.85 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.24 × 0.22 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.781, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	34109, 6099, 5277
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.060, 1.02
No. of reflections	6099
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.27

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

Selected geometric parameters (Å, º) top

Sn—S1	2.4772 (5)	Sn—C24	2.1521 (18)
Sn—S2	3.1048 (5)	S1—C1	1.758 (2)
Sn—C12	2.1286 (18)	S2—C1	1.675 (2)
Sn—C18	2.1380 (19)

C12—Sn—C18	113.76 (7)	C12—Sn—S1	117.26 (5)
C12—Sn—C24	107.51 (7)	C18—Sn—S1	115.54 (5)
C18—Sn—C24	107.45 (7)	C24—Sn—S1	92.18 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···S2ⁱ	0.95	2.83	3.612 (2)	140

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Footnotes

‡Additional correspondence author, e-mail: aibi@ukm.my.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08–27-111), the Ministry of Higher Education (UKM-ST-06-FRGS0092–2010), Universiti Putra Malaysia and the University of Malaya for supporting this study.

References

Awang, N., Baba, I., Yamin, B. M., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1144. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
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