(N-sec-Butyl-N-n-propyl­dithio­carbamato-κ2S,S′)triphenyl­tin(IV)

Awang, N.; Baba, I.; Yamin, B.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810033039

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1144

https://doi.org/10.1107/S1600536810033039

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(N-sec-Butyl-N-n-propyldithiocarbamato-κ²S,S′)triphenyltin(IV)

Normah Awang,^a Ibrahim Baba,^a Bohari M. Yamin,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 16 August 2010; accepted 17 August 2010; online 21 August 2010)

The Sn atom in the title compound, [Sn(C₆H₅)₃(C₈H₁₆NS₂)], is pentacoordinated by two S atoms, derived from an asymmetrically coordinating dithiocarbamate ligand, and three ipso-C atoms. The coordination geometry is intermediate between square-pyramidal and trigonal-bipyramidal, with a leaning towards the latter. The presence of close intramolecular C—H⋯S contacts preclude the S atoms from forming significant intermolecular interactions. Rather, molecules are consolidated in the crystal structure by C—H⋯π interactions.

Related literature

For a review of the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008 ). For a related organotin structure having the same dithiocarbamate ligand, see: Abdul Muthalib et al. (2010 ). For additional structural analysis, see: Addison et al. (1984 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₈H₁₆NS₂)]
M_r = 540.33
Monoclinic, C 2/c
a = 14.7997 (5) Å
b = 12.1844 (5) Å
c = 28.8891 (11) Å
β = 97.348 (1)°
V = 5166.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.653, T_max = 0.801
17218 measured reflections
5923 independent reflections
5179 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.083
S = 1.02
5923 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯S2	0.93	2.75	3.433 (3)	131
C20—H20⋯S2	0.98	2.49	3.059 (3)	117
C24—H24a⋯S1	0.97	2.58	2.938 (3)	102
C25—H25b⋯S1	0.97	2.84	3.360 (4)	115
C16—H16⋯Cg1ⁱ	0.93	2.78	3.618 (3)	151
C23—H23a⋯Cg2ⁱⁱ	0.96	2.91	3.773 (4)	150
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ); 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: https://doi.org/10.1107/S1600536810033039/hg2701sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033039/hg2701Isup2.hkl

checkCIF report

Comment top

Organotin dithiocarbamates display properties that suggest their use as anti-cancer agents, anti-microbial agents and as insecticides (Tiekink, 2008). Such interest motivates on-going structural characterization of such compounds (Abdul Muthalib et al., 2010) and led to the investigation of the title compound, (I).

The Sn atom in (I) is penta-coordinated by two S atoms derived from an asymmetrically coordinating dithiocarbamate ligand and three ipso-C atoms from the phenyl substituents, Fig. 1. The resulting C₃S₂ coordination geometry is intermediate between square pyramidal and trigonal bi-pyramidal with a leaning towards the latter. Thus, compared to the ideal values for τ of 0.0 and 1.0 for ideal square pyramidal and trigonal bi-pyramidal geometries, respectively (Addison et al., 1984), the value for τ in (I) computes to 0.55. The asymmetric mode of coordination of the dithiocarbamate ligand is reflected in significant differences in the associated C–S bond distances with that formed by the S1 atom, involved in the shorter of the Sn–S bonds, being considerably longer [S1–C19 = 1.755 (3) Å] than that formed by the S2 atom [S2–C19 = 1.682 (3) Å]. The observed molecular structure is entirely consistent with literature precedents (Tiekink, 2008).

Each of the S atoms is involved in two intramolecular C–H···S contacts and these do not participate in intermolecular interactions, Table 2. The presence of C–H···π contacts are noted, Table 1, and occur between benzene- and methyl-H atoms with two of the Sn-bound benzene rings functioning as the acceptors. These serve to consolidate the molecules into the crystal structure, Fig. 2.

Related literature top

For a review of the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For a related organotin structure having the same dithiocarbamate ligand, see Abdul Muthalib et al., (2010). For additional structural analysis, see: Addison et al. (1984).

Experimental top

Carbon disulfide (30 mmol) was dropped into an ethanol solution (100 ml) of N-sec-butyl-N-n-propylamine (30 mmol). The solution was kept at 273 K for an hour. Triphenyltin chloride (30 mmol) dissolved in ethanol (100 ml) was added to give a white precipitate. This was collected and colourless crystals were obtained by recrystallization from its chloroform/ethanol (1/1) mixture.

Structure description top

For a review of the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For a related organotin structure having the same dithiocarbamate ligand, see Abdul Muthalib et al., (2010). For additional structural analysis, see: Addison et al. (1984).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009); 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 atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of (I) showing the unit-cell contents. The C–H···π contacts are shown as purple dashed lines.

(N-sec-Butyl-N-n-propyldithiocarbamato- κ²S,S')triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₈H₁₆NS₂)]	F(000) = 2208
M_r = 540.33	D_x = 1.389 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7436 reflections
a = 14.7997 (5) Å	θ = 2.1–27.2°
b = 12.1844 (5) Å	µ = 1.16 mm⁻¹
c = 28.8891 (11) Å	T = 293 K
β = 97.348 (1)°	Block, colourless
V = 5166.7 (3) Å³	0.40 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker SMART diffractometer	5923 independent reflections
Radiation source: fine-focus sealed tube	5179 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→17
T_min = 0.653, T_max = 0.801	k = −14→15
17218 measured reflections	l = −34→37

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0437P)² + 4.4496P] where P = (F_o² + 2F_c²)/3
5923 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₈H₁₆NS₂)]	V = 5166.7 (3) Å³
M_r = 540.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.7997 (5) Å	µ = 1.16 mm⁻¹
b = 12.1844 (5) Å	T = 293 K
c = 28.8891 (11) Å	0.40 × 0.30 × 0.20 mm
β = 97.348 (1)°

Data collection top

Bruker SMART diffractometer	5923 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5179 reflections with I > 2σ(I)
T_min = 0.653, T_max = 0.801	R_int = 0.020
17218 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.02	Δρ_max = 0.70 e Å⁻³
5923 reflections	Δρ_min = −0.30 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq
Sn	0.247917 (10)	0.577523 (13)	0.418770 (5)	0.04008 (7)
S1	0.22291 (6)	0.39926 (6)	0.37826 (2)	0.05486 (18)
S2	0.28766 (6)	0.56989 (6)	0.31823 (2)	0.0588 (2)
C1	0.21407 (15)	0.50813 (19)	0.48322 (8)	0.0397 (5)
C2	0.26523 (19)	0.4242 (2)	0.50565 (10)	0.0520 (6)
H2	0.3156	0.3979	0.4929	0.062*
C3	0.2432 (2)	0.3786 (3)	0.54658 (11)	0.0616 (7)
H3	0.2786	0.3222	0.5611	0.074*
C4	0.1697 (2)	0.4162 (3)	0.56561 (11)	0.0673 (9)
H4	0.1551	0.3861	0.5933	0.081*
C5	0.1171 (2)	0.4987 (3)	0.54404 (11)	0.0704 (9)
H5	0.0662	0.5235	0.5568	0.085*
C6	0.13936 (19)	0.5452 (2)	0.50331 (10)	0.0542 (6)
H6	0.1039	0.6019	0.4892	0.065*
C7	0.14476 (16)	0.6950 (2)	0.39602 (8)	0.0445 (5)
C8	0.06015 (19)	0.6649 (3)	0.37279 (11)	0.0649 (8)
H8	0.0484	0.5916	0.3654	0.078*
C9	−0.0062 (2)	0.7423 (4)	0.36066 (13)	0.0811 (11)
H9	−0.0623	0.7209	0.3450	0.097*
C10	0.0095 (2)	0.8508 (4)	0.37143 (12)	0.0774 (10)
H10	−0.0357	0.9028	0.3631	0.093*
C11	0.0915 (3)	0.8821 (3)	0.39429 (11)	0.0696 (9)
H11	0.1021	0.9556	0.4019	0.084*
C12	0.1597 (2)	0.8046 (2)	0.40645 (9)	0.0541 (6)
H12	0.2158	0.8270	0.4217	0.065*
C13	0.38064 (15)	0.6470 (2)	0.43524 (8)	0.0419 (5)
C14	0.42367 (19)	0.7084 (3)	0.40417 (10)	0.0585 (7)
H14	0.3981	0.7127	0.3731	0.070*
C15	0.5041 (2)	0.7634 (3)	0.41863 (11)	0.0650 (8)
H15	0.5320	0.8042	0.3973	0.078*
C16	0.54271 (18)	0.7581 (3)	0.46412 (11)	0.0593 (7)
H16	0.5967	0.7954	0.4737	0.071*
C17	0.50182 (19)	0.6978 (3)	0.49562 (11)	0.0599 (7)
H17	0.5279	0.6940	0.5266	0.072*
C18	0.42128 (18)	0.6423 (2)	0.48114 (9)	0.0523 (6)
H18	0.3940	0.6011	0.5027	0.063*
C19	0.24957 (19)	0.4410 (2)	0.32344 (9)	0.0473 (6)
C20	0.2709 (3)	0.3917 (3)	0.24303 (10)	0.0678 (9)
H20	0.2875	0.4696	0.2433	0.081*
C21	0.1982 (3)	0.3750 (4)	0.20404 (12)	0.0915 (12)
H21A	0.1746	0.3010	0.2054	0.110*
H21B	0.2233	0.3830	0.1748	0.110*
C22	0.1203 (3)	0.4571 (4)	0.20540 (17)	0.1028 (14)
H22A	0.0741	0.4437	0.1796	0.154*
H22B	0.1433	0.5304	0.2034	0.154*
H22C	0.0948	0.4487	0.2341	0.154*
C23	0.3572 (3)	0.3250 (3)	0.23634 (13)	0.0822 (11)
H23A	0.3761	0.3427	0.2067	0.123*
H23B	0.3440	0.2480	0.2374	0.123*
H23C	0.4052	0.3430	0.2608	0.123*
C24	0.2103 (2)	0.2516 (2)	0.29729 (10)	0.0591 (7)
H24A	0.2382	0.2270	0.3277	0.071*
H24B	0.2312	0.2036	0.2741	0.071*
C25	0.1091 (2)	0.2416 (3)	0.29490 (12)	0.0711 (8)
H25A	0.0810	0.2550	0.2632	0.085*
H25B	0.0865	0.2962	0.3150	0.085*
C27	0.0838 (3)	0.1271 (3)	0.31025 (17)	0.0987 (13)
H27A	0.0188	0.1211	0.3082	0.148*
H27B	0.1105	0.1148	0.3419	0.148*
H27C	0.1063	0.0733	0.2903	0.148*
N1	0.24161 (17)	0.36613 (19)	0.28932 (7)	0.0540 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.04146 (10)	0.04203 (11)	0.03675 (10)	−0.00450 (7)	0.00505 (7)	0.00138 (6)
S1	0.0814 (5)	0.0478 (4)	0.0381 (3)	−0.0154 (3)	0.0179 (3)	−0.0017 (3)
S2	0.0903 (5)	0.0459 (4)	0.0421 (4)	−0.0182 (3)	0.0164 (3)	−0.0020 (3)
C1	0.0419 (11)	0.0412 (12)	0.0364 (11)	−0.0039 (10)	0.0066 (9)	−0.0017 (9)
C2	0.0474 (14)	0.0594 (17)	0.0509 (15)	0.0071 (12)	0.0129 (12)	0.0080 (12)
C3	0.0612 (17)	0.0668 (19)	0.0568 (17)	0.0063 (15)	0.0070 (13)	0.0203 (14)
C4	0.080 (2)	0.080 (2)	0.0455 (16)	−0.0051 (17)	0.0205 (15)	0.0131 (14)
C5	0.0710 (19)	0.083 (2)	0.0644 (19)	0.0102 (17)	0.0366 (15)	0.0018 (17)
C6	0.0553 (15)	0.0532 (15)	0.0566 (16)	0.0098 (12)	0.0164 (12)	0.0027 (12)
C7	0.0437 (12)	0.0550 (15)	0.0355 (12)	−0.0011 (11)	0.0074 (9)	0.0085 (10)
C8	0.0526 (15)	0.069 (2)	0.0700 (19)	−0.0120 (14)	−0.0053 (14)	0.0156 (15)
C9	0.0464 (16)	0.109 (3)	0.084 (2)	−0.0040 (18)	−0.0042 (15)	0.035 (2)
C10	0.070 (2)	0.097 (3)	0.068 (2)	0.031 (2)	0.0197 (17)	0.0336 (19)
C11	0.096 (2)	0.0607 (19)	0.0541 (17)	0.0186 (18)	0.0150 (17)	0.0078 (14)
C12	0.0634 (16)	0.0553 (16)	0.0427 (14)	0.0011 (13)	0.0036 (12)	0.0021 (11)
C13	0.0386 (11)	0.0462 (13)	0.0415 (12)	−0.0025 (10)	0.0073 (9)	−0.0015 (10)
C14	0.0583 (16)	0.072 (2)	0.0449 (14)	−0.0156 (14)	0.0058 (12)	0.0049 (13)
C15	0.0580 (17)	0.076 (2)	0.0632 (18)	−0.0208 (15)	0.0179 (14)	0.0008 (15)
C16	0.0394 (13)	0.0664 (19)	0.0721 (19)	−0.0072 (12)	0.0073 (12)	−0.0128 (15)
C17	0.0488 (14)	0.075 (2)	0.0538 (16)	−0.0035 (14)	−0.0026 (12)	−0.0035 (14)
C18	0.0491 (14)	0.0628 (17)	0.0451 (14)	−0.0060 (12)	0.0059 (11)	0.0030 (12)
C19	0.0597 (15)	0.0479 (14)	0.0350 (12)	−0.0078 (11)	0.0089 (11)	−0.0007 (10)
C20	0.095 (2)	0.0675 (19)	0.0435 (15)	−0.0198 (18)	0.0200 (15)	−0.0022 (13)
C21	0.140 (4)	0.084 (3)	0.0484 (18)	−0.018 (3)	0.005 (2)	0.0025 (17)
C22	0.107 (3)	0.090 (3)	0.104 (3)	0.009 (3)	−0.015 (3)	0.023 (3)
C23	0.095 (3)	0.090 (3)	0.070 (2)	0.003 (2)	0.041 (2)	−0.0058 (18)
C24	0.0743 (19)	0.0518 (16)	0.0531 (16)	0.0002 (14)	0.0152 (13)	−0.0078 (13)
C25	0.075 (2)	0.070 (2)	0.069 (2)	−0.0063 (17)	0.0095 (16)	−0.0089 (16)
C27	0.111 (3)	0.066 (2)	0.127 (4)	−0.029 (2)	0.049 (3)	−0.005 (2)
N1	0.0759 (15)	0.0499 (13)	0.0382 (11)	−0.0122 (11)	0.0150 (10)	−0.0048 (9)

Geometric parameters (Å, º) top

Sn—C1	2.161 (2)	C14—H14	0.9300
Sn—C7	2.134 (3)	C15—C16	1.366 (4)
Sn—C1	2.161 (2)	C15—H15	0.9300
Sn—C13	2.136 (2)	C16—C17	1.370 (4)
Sn—C1	2.161 (2)	C16—H16	0.9300
Sn—S1	2.4725 (7)	C17—C18	1.388 (4)
S1—C19	1.755 (3)	C17—H17	0.9300
S2—C19	1.682 (3)	C18—H18	0.9300
C1—C6	1.388 (3)	C19—N1	1.337 (3)
C1—C2	1.383 (3)	C20—C21	1.468 (5)
C2—C3	1.383 (4)	C20—N1	1.491 (4)
C2—H2	0.9300	C20—C23	1.548 (5)
C3—C4	1.360 (4)	C20—H20	0.9800
C3—H3	0.9300	C21—C22	1.530 (6)
C4—C5	1.371 (5)	C21—H21A	0.9700
C4—H4	0.9300	C21—H21B	0.9700
C5—C6	1.383 (4)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C12	1.381 (4)	C23—H23A	0.9600
C7—C8	1.392 (4)	C23—H23B	0.9600
C8—C9	1.374 (5)	C23—H23C	0.9600
C8—H8	0.9300	C24—N1	1.497 (4)
C9—C10	1.371 (6)	C24—C25	1.496 (4)
C9—H9	0.9300	C24—H24A	0.9700
C10—C11	1.360 (5)	C24—H24B	0.9700
C10—H10	0.9300	C25—C27	1.526 (5)
C11—C12	1.394 (4)	C25—H25A	0.9700
C11—H11	0.9300	C25—H25B	0.9700
C12—H12	0.9300	C27—H27A	0.9600
C13—C18	1.385 (3)	C27—H27B	0.9600
C13—C14	1.385 (4)	C27—H27C	0.9600
C14—C15	1.383 (4)

C7—Sn—C13	113.84 (10)	C16—C17—C18	119.8 (3)
C7—Sn—C1	106.99 (9)	C16—C17—H17	120.1
C13—Sn—C1	105.72 (9)	C18—C17—H17	120.1
C7—Sn—S1	112.67 (7)	C13—C18—C17	121.3 (3)
C13—Sn—S1	122.09 (7)	C13—C18—H18	119.4
C1—Sn—S1	91.54 (6)	C17—C18—H18	119.4
C19—S1—Sn	97.79 (9)	N1—C19—S2	124.7 (2)
C6—C1—C2	117.5 (2)	N1—C19—S1	117.3 (2)
C6—C1—Sn	121.17 (19)	S2—C19—S1	117.87 (15)
C2—C1—Sn	121.29 (18)	C21—C20—N1	113.0 (3)
C3—C2—C1	121.5 (3)	C21—C20—C23	111.5 (3)
C3—C2—H2	119.2	N1—C20—C23	110.0 (3)
C1—C2—H2	119.2	C21—C20—H20	107.4
C4—C3—C2	119.9 (3)	N1—C20—H20	107.4
C4—C3—H3	120.1	C23—C20—H20	107.4
C2—C3—H3	120.1	C20—C21—C22	111.7 (3)
C3—C4—C5	120.1 (3)	C20—C21—H21A	109.3
C3—C4—H4	120.0	C22—C21—H21A	109.3
C5—C4—H4	120.0	C20—C21—H21B	109.3
C6—C5—C4	120.2 (3)	C22—C21—H21B	109.3
C6—C5—H5	119.9	H21A—C21—H21B	107.9
C4—C5—H5	119.9	C21—C22—H22A	109.5
C5—C6—C1	120.8 (3)	C21—C22—H22B	109.5
C5—C6—H6	119.6	H22A—C22—H22B	109.5
C1—C6—H6	119.6	C21—C22—H22C	109.5
C12—C7—C8	118.0 (3)	H22A—C22—H22C	109.5
C12—C7—Sn	119.54 (19)	H22B—C22—H22C	109.5
C8—C7—Sn	122.4 (2)	C20—C23—H23A	109.5
C9—C8—C7	120.8 (3)	C20—C23—H23B	109.5
C9—C8—H8	119.6	H23A—C23—H23B	109.5
C7—C8—H8	119.6	C20—C23—H23C	109.5
C8—C9—C10	120.6 (3)	H23A—C23—H23C	109.5
C8—C9—H9	119.7	H23B—C23—H23C	109.5
C10—C9—H9	119.7	N1—C24—C25	113.3 (3)
C11—C10—C9	119.7 (3)	N1—C24—H24A	108.9
C11—C10—H10	120.1	C25—C24—H24A	108.9
C9—C10—H10	120.1	N1—C24—H24B	108.9
C10—C11—C12	120.3 (3)	C25—C24—H24B	108.9
C10—C11—H11	119.8	H24A—C24—H24B	107.7
C12—C11—H11	119.8	C24—C25—C27	110.0 (3)
C7—C12—C11	120.6 (3)	C24—C25—H25A	109.7
C7—C12—H12	119.7	C27—C25—H25A	109.7
C11—C12—H12	119.7	C24—C25—H25B	109.7
C18—C13—C14	117.6 (2)	C27—C25—H25B	109.7
C18—C13—Sn	118.10 (18)	H25A—C25—H25B	108.2
C14—C13—Sn	123.77 (18)	C25—C27—H27A	109.5
C15—C14—C13	121.0 (3)	C25—C27—H27B	109.5
C15—C14—H14	119.5	H27A—C27—H27B	109.5
C13—C14—H14	119.5	C25—C27—H27C	109.5
C16—C15—C14	120.4 (3)	H27A—C27—H27C	109.5
C16—C15—H15	119.8	H27B—C27—H27C	109.5
C14—C15—H15	119.8	C19—N1—C20	120.7 (2)
C15—C16—C17	119.9 (3)	C19—N1—C24	121.5 (2)
C15—C16—H16	120.0	C20—N1—C24	117.7 (2)
C17—C16—H16	120.0

C7—Sn—S1—C19	71.53 (12)	C10—C11—C12—C7	−0.8 (5)
C13—Sn—S1—C19	−69.63 (13)	C7—Sn—C13—C18	114.8 (2)
C1—Sn—S1—C19	−179.32 (11)	C1—Sn—C13—C18	−2.4 (2)
C7—Sn—C1—C6	−2.9 (2)	S1—Sn—C13—C18	−104.5 (2)
C13—Sn—C1—C6	118.8 (2)	C7—Sn—C13—C14	−56.8 (3)
S1—Sn—C1—C6	−117.2 (2)	C1—Sn—C13—C14	−173.9 (2)
C7—Sn—C1—C2	176.2 (2)	S1—Sn—C13—C14	84.0 (2)
C13—Sn—C1—C2	−62.1 (2)	C18—C13—C14—C15	−0.3 (4)
S1—Sn—C1—C2	62.0 (2)	Sn—C13—C14—C15	171.3 (2)
C6—C1—C2—C3	0.0 (4)	C13—C14—C15—C16	0.0 (5)
Sn—C1—C2—C3	−179.2 (2)	C14—C15—C16—C17	0.2 (5)
C1—C2—C3—C4	0.0 (5)	C15—C16—C17—C18	0.0 (5)
C2—C3—C4—C5	0.6 (5)	C14—C13—C18—C17	0.5 (4)
C3—C4—C5—C6	−1.1 (5)	Sn—C13—C18—C17	−171.6 (2)
C4—C5—C6—C1	1.1 (5)	C16—C17—C18—C13	−0.4 (5)
C2—C1—C6—C5	−0.5 (4)	Sn—S1—C19—N1	−178.0 (2)
Sn—C1—C6—C5	178.6 (2)	Sn—S1—C19—S2	4.69 (18)
C13—Sn—C7—C12	−19.9 (2)	N1—C20—C21—C22	66.8 (4)
C1—Sn—C7—C12	96.5 (2)	C23—C20—C21—C22	−168.7 (3)
S1—Sn—C7—C12	−164.36 (18)	N1—C24—C25—C27	−171.8 (3)
C13—Sn—C7—C8	163.4 (2)	S2—C19—N1—C20	2.7 (4)
C1—Sn—C7—C8	−80.2 (2)	S1—C19—N1—C20	−174.4 (2)
S1—Sn—C7—C8	18.9 (2)	S2—C19—N1—C24	177.7 (2)
C12—C7—C8—C9	0.0 (4)	S1—C19—N1—C24	0.6 (4)
Sn—C7—C8—C9	176.8 (3)	C21—C20—N1—C19	−124.4 (3)
C7—C8—C9—C10	−0.3 (5)	C23—C20—N1—C19	110.2 (3)
C8—C9—C10—C11	0.0 (5)	C21—C20—N1—C24	60.4 (4)
C9—C10—C11—C12	0.5 (5)	C23—C20—N1—C24	−65.0 (4)
C8—C7—C12—C11	0.5 (4)	C25—C24—N1—C19	80.9 (3)
Sn—C7—C12—C11	−176.3 (2)	C25—C24—N1—C20	−103.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···S2	0.93	2.75	3.433 (3)	131
C20—H20···S2	0.98	2.49	3.059 (3)	117
C24—H24a···S1	0.97	2.58	2.938 (3)	102
C25—H25b···S1	0.97	2.84	3.360 (4)	115
C16—H16···Cg1ⁱ	0.93	2.78	3.618 (3)	151
C23—H23a···Cg2ⁱⁱ	0.96	2.91	3.773 (4)	150

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₈H₁₆NS₂)]
M_r	540.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	14.7997 (5), 12.1844 (5), 28.8891 (11)
β (°)	97.348 (1)
V (Å³)	5166.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.653, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	17218, 5923, 5179
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.02
No. of reflections	5923
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.30

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···S2	0.93	2.75	3.433 (3)	131
C20—H20···S2	0.98	2.49	3.059 (3)	117
C24—H24a···S1	0.97	2.58	2.938 (3)	102
C25—H25b···S1	0.97	2.84	3.360 (4)	115
C16—H16···Cg1ⁱ	0.93	2.78	3.618 (3)	151
C23—H23a···Cg2ⁱⁱ	0.96	2.91	3.773 (4)	150

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

Acknowledgements

We thank UKM (UKM-GUP-NBT-08–27-111 and UKM-ST-06-FRGS0092–2010) and the University of Malaya for supporting this study.

References

Abdul Muthalib, A. F., Baba, I., Mohamed Tahir, M. I., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1087. Web of Science CSD CrossRef IUCr Journals Google Scholar
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533–550. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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