(N-Benzyl-N-ethyl­dithio­carbamato)di-tert-butyl­chloridotin(IV)

Abdul Muthalib, A.F.; Baba, I.; Mohamed Tahir, M.I.; Tiekink, E.R.T.

doi:10.1107/S1600536811006398

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m372-m373

doi:10.1107/S1600536811006398

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(N-Benzyl-N-ethyldithiocarbamato)di-tert-butylchloridotin(IV)

Amirah Faizah Abdul Muthalib,^a Ibrahim Baba,^a ‡ Mohamed Ibrahim Mohamed Tahir ^b and Edward R. T. Tiekink ^c ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, ^bDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 16 February 2011; accepted 20 February 2011; online 26 February 2011)

The Sn^IV atom in the title diorganotin dithiocarbamate, [Sn(C₄H₉)₂Cl(C₁₀H₁₂NS₂)], is pentacoordinated by an asymmetrically coordinating dithiocarbamate ligand, a Cl and two C atoms of the Sn-bound tert-butyl groups. The resulting C₂ClS₂ donor set defines a coordination geometry intermediate between square pyramidal and trigonal bipyramidal with a slight tendency towards the former. In the crystal structure, C—H⋯π contacts link centrosymmetrically related molecules into dimeric aggregates.

Related literature

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008 ). For additional structural analysis, see: Addison et al. (1984 ); Spek (2009 ). For a recently reported related structure, see: Abdul Muthalib et al. (2010 ).

Experimental

Crystal data

[Sn(C₄H₉)₂Cl(C₁₀H₁₂NS₂)]
M_r = 478.69
Triclinic, $[P \overline 1]$
a = 8.6140 (2) Å
b = 10.9604 (3) Å
c = 11.4765 (3) Å
α = 91.858 (2)°
β = 96.193 (2)°
γ = 96.011 (2)°
V = 1070.24 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 150 K
0.30 × 0.23 × 0.16 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 = 0.935, T_max = 1.000
26998 measured reflections
4865 independent reflections
4707 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.046
S = 1.11
4865 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—Cl1	2.4847 (4)
Sn—S1	2.4760 (4)
Sn—S2	2.7409 (4)
Sn—C11	2.1884 (14)
Sn—C15	2.1879 (15)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3a⋯Cg1	0.98	2.78	3.6491 (18)	149
C13—H13b⋯Cg1ⁱ	0.98	2.96	3.5401 (18)	119
Symmetry code: (i) -x+1, -y, -z+1.

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/S1600536811006398/zs2099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006398/zs2099Isup2.hkl

checkCIF report

Comment top

Organotin dithiocarbamates attract attention as they exhibit properties suggesting their potential as anti-cancer agents, anti-microbials and insecticides (Tiekink, 2008). Motivated by these and in continuation of structural studies of these systems (Abdul Muthalib et al., 2010), the analysis of the title compound, (I), was undertaken.

The Sn^IV atom in (I) is five-coordinated, being chelated by an asymmetrically coordinating dithiocarbamate ligand, a Cl and two C atoms of the Sn-bound tert-butyl groups (Fig. 1 and Table 1). The asymmetric chelating mode of the non-symmetric dithiocarbamate ligand is reflected in the non-equivalence of the associated C≐S bond distances (Table 1). The coordination geometry is intermediate between square pyramidal and trigonal bi-pyramidal with a leaning towards the former. This assignment is based on the value calculated for τ of 0.45 for the Sn atom, which compares to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bi-pyramidal geometries, respectively (Spek, 2009; Addison et al., 1984). The mode of coordination of the dithiocarbamate ligand, the disposition of the ligand donor set, and the intermediate coordination geometry observed for (I) matches with the literature precedents (Tiekink, 2008).

The most prominent feature of the crystal packing is the presence of C–H···π interactions (Table 2). As shown in Fig. 2, these lead to dimeric aggregates. It is also noted that intramolecular C–H···π contacts are present so that the benzene ring participates in two such interactions (Table 2, Fig. 2). The dimeric aggregates stack into columns along the a axis (Fig. 3).

Related literature top

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For additional structural analysis, see: Addison et al. (1984); Spek (2009). For a recently reported related structure, see: Abdul Muthalib et al. (2010).

Experimental top

The dithiocarbamate ligand was prepared by the addition of carbon disulfide (0.01 mol) to an ethanolic solution (20 ml) of ethylbenzylamine (0.01 mol). The mixture was stirred for 1 h at 277 K, after which the solution was added drop wise to a solution of di-tert-butyltin(IV) dichloride (0.005 mol) in ethanol (20 ml). The resulting mixture was stirred for 1 h. The white precipitate was filtered, washed with cold ethanol and dried in a desiccator. Crystallization was carried out by using an ethanol:chloroform (1:2) mixture. Yield 76%; m.p. 451–453 K. Elemental analysis. Found (calculated) for C₁₈H₃₀ClNS₂Sn: C, 44.81 (45.16); H 6.27 (6.32), N 2.72 (2.93), S 13.23 (13.40); Sn 23.98 (24.80) %. UV (CHCl₃) λ_max 244 (L(π) → L(π*)). IR (KBr): ν(C—H) 2933m, 2958m; ν(C≐N) 1496m; ν(N—C) 1185 s; ν(C≐S) 950 s; ν(Sn—S) 351 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 of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the dimeric aggregate in (I) showing the intra- and intermolecular C–H···π contacts as purple dashed lines.
	Fig. 3. A view in projection down the a axis of (I) showing columns of dimeric aggregates along a. The intermolecular C–H···π contacts are shown as purple dashed lines.

(N-Benzyl-N-ethyldithiocarbamato)di-tert- butylchloridotin(IV) top

Crystal data top

[Sn(C₄H₉)₂Cl(C₁₀H₁₂NS₂)]	Z = 2
M_r = 478.69	F(000) = 488
Triclinic, P1	D_x = 1.485 Mg m⁻³
Hall symbol: -P 1	Melting point = 451–453 K
a = 8.6140 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9604 (3) Å	Cell parameters from 22888 reflections
c = 11.4765 (3) Å	θ = 2.4–28.8°
α = 91.858 (2)°	µ = 1.51 mm⁻¹
β = 96.193 (2)°	T = 150 K
γ = 96.011 (2)°	Block, colourless
V = 1070.24 (5) Å³	0.30 × 0.23 × 0.16 mm

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	4865 independent reflections
Radiation source: fine-focus sealed tube	4707 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1952 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.935, T_max = 1.000	l = −14→14
26998 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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.046	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0236P)² + 0.279P] where P = (F_o² + 2F_c²)/3
4865 reflections	(Δ/σ)_max = 0.003
215 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂Cl(C₁₀H₁₂NS₂)]	γ = 96.011 (2)°
M_r = 478.69	V = 1070.24 (5) Å³
Triclinic, P1	Z = 2
a = 8.6140 (2) Å	Mo Kα radiation
b = 10.9604 (3) Å	µ = 1.51 mm⁻¹
c = 11.4765 (3) Å	T = 150 K
α = 91.858 (2)°	0.30 × 0.23 × 0.16 mm
β = 96.193 (2)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	4865 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4707 reflections with I > 2σ(I)
T_min = 0.935, T_max = 1.000	R_int = 0.034
26998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.046	H-atom parameters constrained
S = 1.11	Δρ_max = 0.29 e Å⁻³
4865 reflections	Δρ_min = −0.50 e Å⁻³
215 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	0.908142 (10)	0.227855 (8)	0.757926 (8)	0.01355 (4)
Cl1	1.09329 (4)	0.40294 (3)	0.84821 (3)	0.02158 (8)
S1	0.88193 (4)	0.35904 (3)	0.58681 (3)	0.01801 (8)
S2	0.70139 (5)	0.11432 (3)	0.57914 (3)	0.02180 (8)
N1	0.69363 (14)	0.26534 (11)	0.39968 (10)	0.0152 (2)
C1	0.74996 (17)	0.24573 (13)	0.50861 (12)	0.0154 (3)
C2	0.73841 (18)	0.38150 (14)	0.34275 (13)	0.0192 (3)
H2A	0.7233	0.3660	0.2566	0.023*
H2B	0.8514	0.4073	0.3659	0.023*
C3	0.6448 (2)	0.48595 (15)	0.37411 (15)	0.0248 (3)
H3A	0.5338	0.4643	0.3450	0.037*
H3B	0.6849	0.5609	0.3380	0.037*
H3C	0.6555	0.4998	0.4595	0.037*
C4	0.58006 (18)	0.17438 (14)	0.32856 (13)	0.0185 (3)
H4A	0.5613	0.0996	0.3734	0.022*
H4B	0.6243	0.1508	0.2560	0.022*
C5	0.42662 (17)	0.22668 (13)	0.29687 (13)	0.0162 (3)
C6	0.38063 (18)	0.25643 (15)	0.18239 (13)	0.0206 (3)
H6	0.4422	0.2374	0.1217	0.025*
C7	0.24535 (19)	0.31377 (15)	0.15584 (14)	0.0248 (3)
H7	0.2146	0.3341	0.0775	0.030*
C8	0.15570 (19)	0.34106 (14)	0.24459 (15)	0.0244 (3)
H8	0.0644	0.3818	0.2273	0.029*
C9	0.19895 (18)	0.30901 (15)	0.35845 (15)	0.0230 (3)
H9	0.1362	0.3265	0.4188	0.028*
C10	0.33337 (17)	0.25166 (14)	0.38442 (13)	0.0185 (3)
H10	0.3621	0.2293	0.4624	0.022*
C11	1.08251 (17)	0.09669 (13)	0.75357 (13)	0.0182 (3)
C12	1.1743 (2)	0.09891 (18)	0.87481 (16)	0.0344 (4)
H12A	1.2538	0.0413	0.8745	0.052*
H12B	1.1022	0.0749	0.9326	0.052*
H12C	1.2258	0.1820	0.8954	0.052*
C13	1.0023 (2)	−0.03233 (15)	0.7207 (2)	0.0351 (4)
H13A	0.9457	−0.0337	0.6418	0.053*
H13B	0.9280	−0.0558	0.7771	0.053*
H13C	1.0816	−0.0903	0.7221	0.053*
C14	1.1918 (2)	0.13760 (17)	0.66298 (17)	0.0334 (4)
H14A	1.2413	0.2211	0.6843	0.050*
H14B	1.1312	0.1364	0.5855	0.050*
H14C	1.2731	0.0816	0.6609	0.050*
C15	0.72963 (18)	0.22899 (15)	0.87978 (13)	0.0210 (3)
C16	0.6414 (2)	0.10044 (16)	0.87739 (15)	0.0283 (4)
H16A	0.5648	0.0983	0.9347	0.042*
H16B	0.7162	0.0408	0.8971	0.042*
H16C	0.5866	0.0797	0.7988	0.042*
C17	0.8116 (2)	0.2629 (2)	1.00325 (15)	0.0356 (4)
H17A	0.8685	0.3453	1.0046	0.053*
H17B	0.8857	0.2034	1.0253	0.053*
H17C	0.7330	0.2618	1.0590	0.053*
C18	0.6177 (2)	0.32236 (19)	0.8403 (2)	0.0390 (5)
H18A	0.5717	0.3013	0.7594	0.059*
H18B	0.6756	0.4045	0.8444	0.059*
H18C	0.5339	0.3212	0.8918	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01353 (6)	0.01384 (6)	0.01283 (6)	0.00071 (4)	−0.00031 (4)	0.00204 (4)
Cl1	0.02389 (18)	0.01842 (18)	0.01980 (17)	−0.00371 (14)	−0.00377 (14)	0.00095 (13)
S1	0.02071 (18)	0.01593 (17)	0.01529 (16)	−0.00302 (13)	−0.00340 (13)	0.00330 (13)
S2	0.0271 (2)	0.01675 (18)	0.01827 (17)	−0.00533 (15)	−0.00567 (15)	0.00382 (14)
N1	0.0147 (6)	0.0160 (6)	0.0144 (6)	0.0026 (5)	−0.0006 (5)	0.0002 (5)
C1	0.0146 (6)	0.0164 (7)	0.0150 (6)	0.0026 (5)	0.0005 (5)	−0.0010 (5)
C2	0.0198 (7)	0.0232 (8)	0.0148 (7)	0.0010 (6)	0.0023 (6)	0.0058 (6)
C3	0.0268 (8)	0.0179 (8)	0.0292 (8)	0.0013 (6)	0.0012 (7)	0.0057 (6)
C4	0.0196 (7)	0.0188 (7)	0.0160 (7)	0.0042 (6)	−0.0031 (6)	−0.0051 (5)
C5	0.0170 (7)	0.0143 (7)	0.0160 (7)	−0.0001 (5)	−0.0019 (5)	−0.0014 (5)
C6	0.0218 (7)	0.0247 (8)	0.0152 (7)	0.0028 (6)	0.0007 (6)	−0.0009 (6)
C7	0.0262 (8)	0.0254 (8)	0.0210 (8)	0.0038 (6)	−0.0069 (6)	0.0033 (6)
C8	0.0190 (7)	0.0183 (8)	0.0351 (9)	0.0048 (6)	−0.0032 (7)	−0.0005 (7)
C9	0.0199 (7)	0.0220 (8)	0.0267 (8)	−0.0005 (6)	0.0054 (6)	−0.0057 (6)
C10	0.0198 (7)	0.0197 (7)	0.0151 (7)	−0.0009 (6)	0.0008 (6)	−0.0003 (5)
C11	0.0173 (7)	0.0152 (7)	0.0225 (7)	0.0034 (5)	0.0018 (6)	0.0023 (6)
C12	0.0352 (10)	0.0406 (11)	0.0287 (9)	0.0197 (8)	−0.0058 (8)	0.0024 (8)
C13	0.0275 (9)	0.0155 (8)	0.0613 (13)	0.0039 (7)	−0.0013 (9)	0.0013 (8)
C14	0.0362 (10)	0.0296 (10)	0.0402 (10)	0.0125 (8)	0.0202 (8)	0.0069 (8)
C15	0.0190 (7)	0.0236 (8)	0.0206 (7)	−0.0001 (6)	0.0057 (6)	0.0004 (6)
C16	0.0277 (9)	0.0297 (9)	0.0263 (8)	−0.0070 (7)	0.0070 (7)	0.0042 (7)
C17	0.0345 (10)	0.0516 (12)	0.0187 (8)	−0.0090 (8)	0.0097 (7)	−0.0082 (8)
C18	0.0289 (9)	0.0360 (11)	0.0577 (13)	0.0138 (8)	0.0180 (9)	0.0095 (9)

Geometric parameters (Å, º) top

Sn—Cl1	2.4847 (4)	C9—C10	1.384 (2)
Sn—S1	2.4760 (4)	C9—H9	0.9500
Sn—S2	2.7409 (4)	C10—H10	0.9500
Sn—C11	2.1884 (14)	C11—C12	1.522 (2)
Sn—C15	2.1879 (15)	C11—C14	1.523 (2)
S1—C1	1.7470 (15)	C11—C13	1.524 (2)
S2—C1	1.7109 (15)	C12—H12A	0.9800
N1—C1	1.3240 (18)	C12—H12B	0.9800
N1—C4	1.4791 (18)	C12—H12C	0.9800
N1—C2	1.4839 (19)	C13—H13A	0.9800
C2—C3	1.523 (2)	C13—H13B	0.9800
C2—H2A	0.9900	C13—H13C	0.9800
C2—H2B	0.9900	C14—H14A	0.9800
C3—H3A	0.9800	C14—H14B	0.9800
C3—H3B	0.9800	C14—H14C	0.9800
C3—H3C	0.9800	C15—C18	1.525 (2)
C4—C5	1.509 (2)	C15—C16	1.527 (2)
C4—H4A	0.9900	C15—C17	1.530 (2)
C4—H4B	0.9900	C16—H16A	0.9800
C5—C10	1.390 (2)	C16—H16B	0.9800
C5—C6	1.390 (2)	C16—H16C	0.9800
C6—C7	1.391 (2)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—C8	1.386 (2)	C17—H17C	0.9800
C7—H7	0.9500	C18—H18A	0.9800
C8—C9	1.386 (2)	C18—H18B	0.9800
C8—H8	0.9500	C18—H18C	0.9800

C15—Sn—C11	125.79 (6)	C9—C10—C5	120.31 (14)
C15—Sn—S1	117.55 (4)	C9—C10—H10	119.8
C11—Sn—S1	115.59 (4)	C5—C10—H10	119.8
C15—Sn—Cl1	98.77 (4)	C12—C11—C14	110.27 (15)
C11—Sn—Cl1	96.17 (4)	C12—C11—C13	109.80 (14)
S1—Sn—Cl1	84.342 (12)	C14—C11—C13	110.21 (14)
C15—Sn—S2	93.43 (4)	C12—C11—Sn	108.21 (10)
C11—Sn—S2	96.04 (4)	C14—C11—Sn	107.78 (10)
S1—Sn—S2	68.654 (12)	C13—C11—Sn	110.52 (10)
Cl1—Sn—S2	152.989 (12)	C11—C12—H12A	109.5
C1—S1—Sn	91.00 (5)	C11—C12—H12B	109.5
C1—S2—Sn	83.22 (5)	H12A—C12—H12B	109.5
C1—N1—C4	122.17 (12)	C11—C12—H12C	109.5
C1—N1—C2	121.73 (12)	H12A—C12—H12C	109.5
C4—N1—C2	116.09 (11)	H12B—C12—H12C	109.5
N1—C1—S2	123.80 (11)	C11—C13—H13A	109.5
N1—C1—S1	119.10 (11)	C11—C13—H13B	109.5
S2—C1—S1	117.10 (8)	H13A—C13—H13B	109.5
N1—C2—C3	113.75 (12)	C11—C13—H13C	109.5
N1—C2—H2A	108.8	H13A—C13—H13C	109.5
C3—C2—H2A	108.8	H13B—C13—H13C	109.5
N1—C2—H2B	108.8	C11—C14—H14A	109.5
C3—C2—H2B	108.8	C11—C14—H14B	109.5
H2A—C2—H2B	107.7	H14A—C14—H14B	109.5
C2—C3—H3A	109.5	C11—C14—H14C	109.5
C2—C3—H3B	109.5	H14A—C14—H14C	109.5
H3A—C3—H3B	109.5	H14B—C14—H14C	109.5
C2—C3—H3C	109.5	C18—C15—C16	110.55 (15)
H3A—C3—H3C	109.5	C18—C15—C17	111.09 (15)
H3B—C3—H3C	109.5	C16—C15—C17	109.57 (14)
N1—C4—C5	110.67 (12)	C18—C15—Sn	108.38 (11)
N1—C4—H4A	109.5	C16—C15—Sn	108.51 (10)
C5—C4—H4A	109.5	C17—C15—Sn	108.66 (10)
N1—C4—H4B	109.5	C15—C16—H16A	109.5
C5—C4—H4B	109.5	C15—C16—H16B	109.5
H4A—C4—H4B	108.1	H16A—C16—H16B	109.5
C10—C5—C6	119.24 (14)	C15—C16—H16C	109.5
C10—C5—C4	119.60 (13)	H16A—C16—H16C	109.5
C6—C5—C4	121.08 (14)	H16B—C16—H16C	109.5
C5—C6—C7	120.61 (15)	C15—C17—H17A	109.5
C5—C6—H6	119.7	C15—C17—H17B	109.5
C7—C6—H6	119.7	H17A—C17—H17B	109.5
C8—C7—C6	119.51 (15)	C15—C17—H17C	109.5
C8—C7—H7	120.2	H17A—C17—H17C	109.5
C6—C7—H7	120.2	H17B—C17—H17C	109.5
C9—C8—C7	120.14 (15)	C15—C18—H18A	109.5
C9—C8—H8	119.9	C15—C18—H18B	109.5
C7—C8—H8	119.9	H18A—C18—H18B	109.5
C10—C9—C8	120.15 (14)	C15—C18—H18C	109.5
C10—C9—H9	119.9	H18A—C18—H18C	109.5
C8—C9—H9	119.9	H18B—C18—H18C	109.5

C15—Sn—S1—C1	−83.40 (7)	C8—C9—C10—C5	0.5 (2)
C11—Sn—S1—C1	85.49 (6)	C6—C5—C10—C9	−2.0 (2)
Cl1—Sn—S1—C1	179.64 (5)	C4—C5—C10—C9	174.62 (14)
S2—Sn—S1—C1	−0.96 (5)	C15—Sn—C11—C12	−55.53 (13)
C15—Sn—S2—C1	119.28 (6)	S1—Sn—C11—C12	136.63 (11)
C11—Sn—S2—C1	−114.17 (6)	Cl1—Sn—C11—C12	49.96 (11)
S1—Sn—S2—C1	0.98 (5)	S2—Sn—C11—C12	−154.18 (11)
Cl1—Sn—S2—C1	2.29 (6)	C15—Sn—C11—C14	−174.77 (11)
C4—N1—C1—S2	0.84 (19)	S1—Sn—C11—C14	17.39 (12)
C2—N1—C1—S2	179.45 (10)	Cl1—Sn—C11—C14	−69.28 (11)
C4—N1—C1—S1	−179.25 (10)	S2—Sn—C11—C14	86.58 (11)
C2—N1—C1—S1	−0.64 (18)	C15—Sn—C11—C13	64.74 (14)
Sn—S2—C1—N1	178.46 (13)	S1—Sn—C11—C13	−103.11 (12)
Sn—S2—C1—S1	−1.46 (7)	Cl1—Sn—C11—C13	170.23 (12)
Sn—S1—C1—N1	−178.32 (11)	S2—Sn—C11—C13	−33.91 (12)
Sn—S1—C1—S2	1.60 (8)	C11—Sn—C15—C18	−171.31 (11)
C1—N1—C2—C3	−82.33 (17)	S1—Sn—C15—C18	−3.68 (13)
C4—N1—C2—C3	96.36 (15)	Cl1—Sn—C15—C18	84.49 (12)
C1—N1—C4—C5	117.52 (15)	S2—Sn—C15—C18	−71.34 (12)
C2—N1—C4—C5	−61.16 (16)	C11—Sn—C15—C16	−51.22 (13)
N1—C4—C5—C10	−67.27 (17)	S1—Sn—C15—C16	116.41 (10)
N1—C4—C5—C6	109.31 (16)	Cl1—Sn—C15—C16	−155.42 (10)
C10—C5—C6—C7	1.8 (2)	S2—Sn—C15—C16	48.75 (11)
C4—C5—C6—C7	−174.75 (14)	C11—Sn—C15—C17	67.86 (14)
C5—C6—C7—C8	−0.2 (2)	S1—Sn—C15—C17	−124.51 (11)
C6—C7—C8—C9	−1.4 (2)	Cl1—Sn—C15—C17	−36.34 (12)
C7—C8—C9—C10	1.2 (2)	S2—Sn—C15—C17	167.83 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3a···Cg1	0.98	2.78	3.6491 (18)	149
C13—H13b···Cg1ⁱ	0.98	2.96	3.5401 (18)	119

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂Cl(C₁₀H₁₂NS₂)]
M_r	478.69
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.6140 (2), 10.9604 (3), 11.4765 (3)
α, β, γ (°)	91.858 (2), 96.193 (2), 96.011 (2)
V (Å³)	1070.24 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.30 × 0.23 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.935, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	26998, 4865, 4707
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.046, 1.11
No. of reflections	4865
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.50

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 bond lengths (Å) top

Sn—Cl1	2.4847 (4)	Sn—C15	2.1879 (15)
Sn—S1	2.4760 (4)	S1—C1	1.7470 (15)
Sn—S2	2.7409 (4)	S2—C1	1.7109 (15)
Sn—C11	2.1884 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3a···Cg1	0.98	2.78	3.6491 (18)	149
C13—H13b···Cg1ⁱ	0.98	2.96	3.5401 (18)	119

Symmetry code: (i) −x+1, −y, −z+1.

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

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
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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
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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Volume 67| Part 3| March 2011| Pages m372-m373

doi:10.1107/S1600536811006398

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