Di-tert-butyl­chlorido(N,N-dibenzyl­dithio­carbamato)tin(IV)

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

doi:10.1107/S1600536811006866

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m386

doi:10.1107/S1600536811006866

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Di-tert-butylchlorido(N,N-dibenzyldithiocarbamato)tin(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 Kebangsaan 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 17 February 2011; accepted 22 February 2011; online 26 February 2011)

The Sn^IV atom in the title diorganotin dithiocarbamate, [Sn(C₄H₉)₂(C₁₅H₁₄NS₂)Cl], is pentacoordinated by an asymmetrically coordinating dithiocarbamate ligand, a Cl atom 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.

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)₂(C₁₅H₁₄NS₂)Cl]
M_r = 540.76
Monoclinic, P 2₁
a = 9.0600 (2) Å
b = 10.9238 (2) Å
c = 12.7845 (3) Å
β = 102.759 (2)°
V = 1234.03 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 150 K
0.26 × 0.15 × 0.06 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 = 0.820, T_max = 0.924
15537 measured reflections
5443 independent reflections
5087 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.072
S = 1.05
5443 reflections
259 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.66 e Å⁻³
Absolute structure: Flack (1983 ), 2497 Friedel pairs
Flack parameter: −0.035 (18)

Table 1
Selected bond lengths (Å)

Sn—Cl1	2.4942 (9)
Sn—S1	2.4857 (10)
Sn—S2	2.7366 (10)
Sn—C16	2.191 (4)
Sn—C20	2.188 (3)

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006866/pk2305sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006866/pk2305Isup2.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). 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 disparity in the C1–S1,2 bond distances reflects the asymmetric mode of coordination observed for the dithiocarbamate ligand, Table 1.

The coordination geometry is intermediate between square pyramidal and trigonal bi-pyramidal with a very slight leaning towards the former description. This assignment is based on the value calculated for τ of 0.49 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).

No specific intermolecular interactions are noted in the crystal packing.

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 title compound was prepared using an in situ method by addition of carbon disulfide (0.01 mol) to an ethanolic solution (20 ml) of dibenzylamine (0.01 mol). The mixture was stirred for 1 h at 277 K. The resulting solution was then added drop wise to a solution of di-tert-butyltin(IV) dichloride (0.005 mol) in ethanol (20 ml) and stirred again for 1 h. The white precipitate was filtered, washed with cold ethanol and dried in a desiccator. Crystallization was from its ethanol:chloroform (1:2) solution. Yield 71%; M.pt. 475–477 K. Elemental analysis. Found (calculated) for C₂₃H₃₂ClNS₂Sn: C, 50.94 (51.50); H 5.89 (5.92); N 2.59 (2.93); S 11.59 (11.86); Sn 21.25 (21.90) %. UV (CHCl₃) λ_max 228 (L(π) → L(π*)). IR(KBr): ν(C—H) 2939m, 2849m; ν(C≐N) 1487m; ν(N—C) 1154 s; ν(C≐S) 988 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); 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.

Di-tert-butylchlorido(N,N-dibenzyldithiocarbamato)tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₁₅H₁₄NS₂)Cl]	F(000) = 552
M_r = 540.76	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 10382 reflections
a = 9.0600 (2) Å	θ = 2.0–29.0°
b = 10.9238 (2) Å	µ = 1.32 mm⁻¹
c = 12.7845 (3) Å	T = 150 K
β = 102.759 (2)°	Prism, colourless
V = 1234.03 (5) Å³	0.26 × 0.15 × 0.06 mm
Z = 2

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5443 independent reflections
Radiation source: fine-focus sealed tube	5087 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 16.1952 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→13
T_min = 0.820, T_max = 0.924	l = −16→16
15537 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0329P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5443 reflections	Δρ_max = 0.78 e Å⁻³
259 parameters	Δρ_min = −0.66 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.035 (18)

Crystal data top

[Sn(C₄H₉)₂(C₁₅H₁₄NS₂)Cl]	V = 1234.03 (5) Å³
M_r = 540.76	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.0600 (2) Å	µ = 1.32 mm⁻¹
b = 10.9238 (2) Å	T = 150 K
c = 12.7845 (3) Å	0.26 × 0.15 × 0.06 mm
β = 102.759 (2)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5443 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	5087 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.924	R_int = 0.046
15537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.072	Δρ_max = 0.78 e Å⁻³
S = 1.05	Δρ_min = −0.66 e Å⁻³
5443 reflections	Absolute structure: Flack (1983), 2497 Friedel pairs
259 parameters	Absolute structure parameter: −0.035 (18)
1 restraint

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	0.25541 (2)	0.701510 (17)	0.187046 (15)	0.02052 (7)
Cl1	0.25531 (12)	0.53028 (10)	0.31609 (8)	0.0317 (2)
S1	0.30831 (12)	0.83033 (9)	0.35137 (8)	0.0254 (2)
S2	0.30370 (12)	0.94068 (9)	0.14035 (8)	0.0306 (2)
N1	0.3893 (3)	1.0614 (3)	0.3258 (2)	0.0234 (6)
C1	0.3381 (4)	0.9583 (3)	0.2768 (3)	0.0238 (8)
C2	0.4241 (4)	1.0768 (3)	0.4447 (3)	0.0238 (8)
H2A	0.5187	1.1245	0.4670	0.029*
H2B	0.4411	0.9952	0.4791	0.029*
C3	0.2986 (5)	1.1410 (4)	0.4836 (4)	0.0242 (10)
C4	0.2986 (6)	1.2679 (4)	0.4919 (4)	0.0280 (11)
H4	0.3768	1.3142	0.4720	0.034*
C5	0.1848 (6)	1.3273 (5)	0.5292 (4)	0.0354 (12)
H5	0.1847	1.4141	0.5342	0.043*
C6	0.0719 (7)	1.2598 (5)	0.5588 (4)	0.0389 (13)
H6	−0.0061	1.3007	0.5841	0.047*
C7	0.0709 (6)	1.1341 (6)	0.5523 (4)	0.0409 (13)
H7	−0.0061	1.0881	0.5740	0.049*
C8	0.1841 (6)	1.0751 (5)	0.5135 (4)	0.0325 (11)
H8	0.1827	0.9884	0.5074	0.039*
C9	0.4247 (4)	1.1692 (3)	0.2665 (3)	0.0295 (9)
H9A	0.3846	1.2436	0.2948	0.035*
H9B	0.3737	1.1610	0.1899	0.035*
C10	0.5930 (4)	1.1841 (4)	0.2756 (3)	0.0268 (9)
C11	0.6844 (5)	1.0857 (4)	0.2644 (4)	0.0343 (11)
H11	0.6415	1.0061	0.2527	0.041*
C12	0.8369 (6)	1.1017 (5)	0.2698 (4)	0.0401 (12)
H12	0.8984	1.0328	0.2634	0.048*
C13	0.9007 (5)	1.2160 (6)	0.2844 (3)	0.0426 (12)
H13	1.0054	1.2268	0.2864	0.051*
C14	0.8115 (6)	1.3152 (5)	0.2963 (4)	0.0426 (13)
H14	0.8549	1.3947	0.3062	0.051*
C15	0.6585 (6)	1.2997 (4)	0.2939 (4)	0.0347 (11)
H15	0.5986	1.3680	0.3047	0.042*
C16	0.4451 (4)	0.6314 (3)	0.1240 (3)	0.0264 (8)
C17	0.4057 (5)	0.5006 (4)	0.0873 (4)	0.0399 (11)
H17A	0.3221	0.5014	0.0239	0.060*
H17B	0.3754	0.4548	0.1451	0.060*
H17C	0.4943	0.4615	0.0694	0.060*
C18	0.4710 (4)	0.7083 (6)	0.0303 (3)	0.0384 (9)
H18A	0.5510	0.6709	0.0003	0.058*
H18B	0.5016	0.7912	0.0553	0.058*
H18C	0.3772	0.7122	−0.0252	0.058*
C19	0.5852 (4)	0.6347 (4)	0.2167 (3)	0.0345 (10)
H19A	0.6711	0.5977	0.1934	0.052*
H19B	0.5646	0.5887	0.2778	0.052*
H19C	0.6092	0.7198	0.2381	0.052*
C20	0.0212 (3)	0.6974 (5)	0.0950 (2)	0.0256 (6)
C21	−0.0476 (5)	0.5706 (4)	0.1105 (4)	0.0349 (11)
H21A	−0.0504	0.5597	0.1861	0.052*
H21B	0.0147	0.5061	0.0889	0.052*
H21C	−0.1506	0.5657	0.0663	0.052*
C22	0.0276 (4)	0.7156 (5)	−0.0218 (3)	0.0379 (10)
H22A	−0.0755	0.7231	−0.0655	0.057*
H22B	0.0776	0.6451	−0.0464	0.057*
H22C	0.0846	0.7902	−0.0288	0.057*
C23	−0.0699 (5)	0.7973 (4)	0.1328 (4)	0.0368 (11)
H23A	−0.0221	0.8767	0.1269	0.055*
H23B	−0.0737	0.7824	0.2078	0.055*
H23C	−0.1729	0.7975	0.0883	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02131 (11)	0.01858 (11)	0.02188 (12)	−0.00037 (13)	0.00521 (8)	−0.00032 (13)
Cl1	0.0404 (6)	0.0249 (5)	0.0314 (6)	0.0007 (4)	0.0112 (5)	0.0098 (4)
S1	0.0309 (5)	0.0229 (5)	0.0229 (5)	−0.0029 (4)	0.0071 (4)	−0.0003 (4)
S2	0.0448 (6)	0.0238 (5)	0.0221 (5)	−0.0044 (4)	0.0052 (4)	0.0002 (4)
N1	0.0296 (16)	0.0181 (14)	0.0230 (16)	−0.0007 (13)	0.0071 (13)	−0.0008 (12)
C1	0.0210 (17)	0.0223 (19)	0.027 (2)	0.0001 (15)	0.0031 (15)	0.0009 (15)
C2	0.0272 (19)	0.0202 (18)	0.0226 (19)	0.0006 (15)	0.0026 (16)	−0.0022 (15)
C3	0.029 (2)	0.020 (2)	0.022 (2)	−0.0015 (19)	0.0013 (19)	−0.0019 (18)
C4	0.031 (3)	0.027 (2)	0.025 (2)	−0.004 (2)	0.004 (2)	0.000 (2)
C5	0.047 (3)	0.027 (2)	0.031 (3)	0.018 (2)	0.005 (2)	−0.0026 (19)
C6	0.042 (3)	0.051 (3)	0.026 (3)	0.015 (3)	0.011 (2)	−0.004 (2)
C7	0.032 (3)	0.059 (4)	0.033 (3)	−0.005 (3)	0.010 (2)	−0.005 (3)
C8	0.039 (3)	0.032 (2)	0.026 (2)	0.000 (2)	0.007 (2)	−0.003 (2)
C9	0.040 (2)	0.020 (2)	0.027 (2)	0.0029 (14)	0.0044 (17)	0.0019 (13)
C10	0.0390 (19)	0.021 (2)	0.0202 (17)	−0.0046 (18)	0.0064 (14)	0.0024 (16)
C11	0.041 (3)	0.023 (2)	0.040 (3)	−0.0027 (19)	0.013 (2)	−0.005 (2)
C12	0.043 (3)	0.041 (3)	0.038 (3)	0.001 (2)	0.014 (2)	−0.008 (2)
C13	0.042 (2)	0.059 (3)	0.028 (2)	−0.018 (3)	0.0092 (17)	−0.001 (3)
C14	0.052 (3)	0.031 (2)	0.044 (3)	−0.020 (2)	0.010 (2)	−0.002 (2)
C15	0.046 (3)	0.023 (2)	0.033 (3)	−0.005 (2)	0.005 (2)	0.0005 (18)
C16	0.0282 (19)	0.0257 (19)	0.028 (2)	0.0031 (16)	0.0110 (17)	−0.0038 (16)
C17	0.044 (3)	0.028 (2)	0.049 (3)	0.0033 (19)	0.015 (2)	−0.0148 (19)
C18	0.0387 (19)	0.049 (2)	0.032 (2)	0.008 (3)	0.0173 (16)	−0.001 (3)
C19	0.025 (2)	0.038 (2)	0.042 (3)	0.0033 (18)	0.0096 (18)	0.000 (2)
C20	0.0210 (14)	0.0275 (16)	0.0262 (16)	0.000 (2)	0.0010 (12)	−0.001 (2)
C21	0.029 (2)	0.030 (2)	0.043 (3)	−0.0082 (19)	0.0025 (19)	−0.004 (2)
C22	0.0338 (19)	0.048 (3)	0.031 (2)	−0.001 (2)	0.0042 (15)	−0.004 (2)
C23	0.028 (2)	0.034 (3)	0.045 (3)	0.0035 (19)	0.000 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Sn—Cl1	2.4942 (9)	C12—C13	1.372 (7)
Sn—S1	2.4857 (10)	C12—H12	0.9500
Sn—S2	2.7366 (10)	C13—C14	1.380 (8)
Sn—C16	2.191 (4)	C13—H13	0.9500
Sn—C20	2.188 (3)	C14—C15	1.389 (8)
S1—C1	1.746 (4)	C14—H14	0.9500
S2—C1	1.714 (4)	C15—H15	0.9500
N1—C1	1.321 (5)	C16—C17	1.521 (5)
N1—C9	1.474 (5)	C16—C18	1.524 (6)
N1—C2	1.493 (4)	C16—C19	1.533 (6)
C2—C3	1.510 (6)	C17—H17A	0.9800
C2—H2A	0.9900	C17—H17B	0.9800
C2—H2B	0.9900	C17—H17C	0.9800
C3—C8	1.384 (6)	C18—H18A	0.9800
C3—C4	1.390 (4)	C18—H18B	0.9800
C4—C5	1.389 (6)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.381 (8)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.376 (5)	C20—C23	1.510 (6)
C6—H6	0.9500	C20—C22	1.519 (5)
C7—C8	1.392 (7)	C20—C21	1.550 (6)
C7—H7	0.9500	C21—H21A	0.9800
C8—H8	0.9500	C21—H21B	0.9800
C9—C10	1.512 (5)	C21—H21C	0.9800
C9—H9A	0.9900	C22—H22A	0.9800
C9—H9B	0.9900	C22—H22B	0.9800
C10—C11	1.383 (6)	C22—H22C	0.9800
C10—C15	1.394 (6)	C23—H23A	0.9800
C11—C12	1.380 (7)	C23—H23B	0.9800
C11—H11	0.9500	C23—H23C	0.9800

C20—Sn—C16	122.78 (14)	C12—C13—C14	119.3 (4)
C20—Sn—S1	116.70 (11)	C12—C13—H13	120.3
C16—Sn—S1	119.21 (10)	C14—C13—H13	120.3
C20—Sn—Cl1	101.46 (13)	C13—C14—C15	120.5 (4)
C16—Sn—Cl1	95.51 (10)	C13—C14—H14	119.7
S1—Sn—Cl1	83.90 (4)	C15—C14—H14	119.7
C20—Sn—S2	94.87 (14)	C14—C15—C10	120.0 (4)
C16—Sn—S2	94.43 (10)	C14—C15—H15	120.0
S1—Sn—S2	68.51 (3)	C10—C15—H15	120.0
Cl1—Sn—S2	152.09 (3)	C17—C16—C18	110.0 (4)
C1—S1—Sn	90.91 (13)	C17—C16—C19	111.0 (3)
C1—S2—Sn	83.51 (12)	C18—C16—C19	110.5 (3)
C1—N1—C9	122.1 (3)	C17—C16—Sn	107.0 (3)
C1—N1—C2	123.5 (3)	C18—C16—Sn	111.5 (3)
C9—N1—C2	114.4 (3)	C19—C16—Sn	106.9 (2)
N1—C1—S2	122.9 (3)	C16—C17—H17A	109.5
N1—C1—S1	120.3 (3)	C16—C17—H17B	109.5
S2—C1—S1	116.8 (2)	H17A—C17—H17B	109.5
N1—C2—C3	112.5 (3)	C16—C17—H17C	109.5
N1—C2—H2A	109.1	H17A—C17—H17C	109.5
C3—C2—H2A	109.1	H17B—C17—H17C	109.5
N1—C2—H2B	109.1	C16—C18—H18A	109.5
C3—C2—H2B	109.1	C16—C18—H18B	109.5
H2A—C2—H2B	107.8	H18A—C18—H18B	109.5
C8—C3—C4	119.0 (5)	C16—C18—H18C	109.5
C8—C3—C2	120.9 (4)	H18A—C18—H18C	109.5
C4—C3—C2	120.1 (5)	H18B—C18—H18C	109.5
C5—C4—C3	120.3 (5)	C16—C19—H19A	109.5
C5—C4—H4	119.8	C16—C19—H19B	109.5
C3—C4—H4	119.8	H19A—C19—H19B	109.5
C6—C5—C4	119.7 (5)	C16—C19—H19C	109.5
C6—C5—H5	120.1	H19A—C19—H19C	109.5
C4—C5—H5	120.1	H19B—C19—H19C	109.5
C7—C6—C5	120.7 (6)	C23—C20—C22	111.2 (4)
C7—C6—H6	119.6	C23—C20—C21	109.9 (3)
C5—C6—H6	119.6	C22—C20—C21	110.3 (4)
C6—C7—C8	119.3 (6)	C23—C20—Sn	110.3 (3)
C6—C7—H7	120.4	C22—C20—Sn	106.5 (2)
C8—C7—H7	120.4	C21—C20—Sn	108.6 (3)
C3—C8—C7	120.9 (5)	C20—C21—H21A	109.5
C3—C8—H8	119.6	C20—C21—H21B	109.5
C7—C8—H8	119.6	H21A—C21—H21B	109.5
N1—C9—C10	112.1 (3)	C20—C21—H21C	109.5
N1—C9—H9A	109.2	H21A—C21—H21C	109.5
C10—C9—H9A	109.2	H21B—C21—H21C	109.5
N1—C9—H9B	109.2	C20—C22—H22A	109.5
C10—C9—H9B	109.2	C20—C22—H22B	109.5
H9A—C9—H9B	107.9	H22A—C22—H22B	109.5
C11—C10—C15	118.6 (4)	C20—C22—H22C	109.5
C11—C10—C9	121.7 (4)	H22A—C22—H22C	109.5
C15—C10—C9	119.7 (4)	H22B—C22—H22C	109.5
C12—C11—C10	120.8 (4)	C20—C23—H23A	109.5
C12—C11—H11	119.6	C20—C23—H23B	109.5
C10—C11—H11	119.6	H23A—C23—H23B	109.5
C13—C12—C11	120.6 (5)	C20—C23—H23C	109.5
C13—C12—H12	119.7	H23A—C23—H23C	109.5
C11—C12—H12	119.7	H23B—C23—H23C	109.5

C20—Sn—S1—C1	−87.69 (18)	C15—C10—C11—C12	−0.7 (6)
C16—Sn—S1—C1	79.62 (17)	C9—C10—C11—C12	178.1 (4)
Cl1—Sn—S1—C1	172.53 (12)	C10—C11—C12—C13	−1.3 (7)
S2—Sn—S1—C1	−3.20 (12)	C11—C12—C13—C14	1.5 (7)
C20—Sn—S2—C1	120.10 (15)	C12—C13—C14—C15	0.2 (7)
C16—Sn—S2—C1	−116.43 (16)	C13—C14—C15—C10	−2.3 (7)
S1—Sn—S2—C1	3.28 (12)	C11—C10—C15—C14	2.5 (6)
Cl1—Sn—S2—C1	−5.82 (15)	C9—C10—C15—C14	−176.3 (4)
C9—N1—C1—S2	−1.6 (5)	C20—Sn—C16—C17	−53.6 (3)
C2—N1—C1—S2	−178.1 (3)	S1—Sn—C16—C17	139.9 (2)
C9—N1—C1—S1	176.3 (3)	Cl1—Sn—C16—C17	53.8 (3)
C2—N1—C1—S1	−0.2 (5)	S2—Sn—C16—C17	−152.3 (3)
Sn—S2—C1—N1	173.1 (3)	C20—Sn—C16—C18	66.6 (3)
Sn—S2—C1—S1	−4.87 (18)	S1—Sn—C16—C18	−99.9 (3)
Sn—S1—C1—N1	−172.7 (3)	Cl1—Sn—C16—C18	174.0 (3)
Sn—S1—C1—S2	5.3 (2)	S2—Sn—C16—C18	−32.1 (3)
C1—N1—C2—C3	−99.7 (4)	C20—Sn—C16—C19	−172.6 (3)
C9—N1—C2—C3	83.5 (4)	S1—Sn—C16—C19	20.9 (3)
N1—C2—C3—C8	91.7 (5)	Cl1—Sn—C16—C19	−65.1 (3)
N1—C2—C3—C4	−89.6 (5)	S2—Sn—C16—C19	88.7 (3)
C8—C3—C4—C5	−0.3 (9)	C16—Sn—C20—C23	−154.4 (3)
C2—C3—C4—C5	−179.0 (3)	S1—Sn—C20—C23	12.4 (3)
C3—C4—C5—C6	0.5 (8)	Cl1—Sn—C20—C23	101.3 (3)
C4—C5—C6—C7	0.2 (9)	S2—Sn—C20—C23	−55.9 (3)
C5—C6—C7—C8	−1.1 (10)	C16—Sn—C20—C22	−33.6 (5)
C4—C3—C8—C7	−0.6 (8)	S1—Sn—C20—C22	133.2 (3)
C2—C3—C8—C7	178.1 (4)	Cl1—Sn—C20—C22	−137.9 (4)
C6—C7—C8—C3	1.3 (9)	S2—Sn—C20—C22	64.9 (4)
C1—N1—C9—C10	−102.5 (4)	C16—Sn—C20—C21	85.1 (3)
C2—N1—C9—C10	74.3 (4)	S1—Sn—C20—C21	−108.0 (3)
N1—C9—C10—C11	44.6 (5)	Cl1—Sn—C20—C21	−19.2 (3)
N1—C9—C10—C15	−136.6 (4)	S2—Sn—C20—C21	−176.4 (2)

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₁₅H₁₄NS₂)Cl]
M_r	540.76
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	9.0600 (2), 10.9238 (2), 12.7845 (3)
β (°)	102.759 (2)
V (Å³)	1234.03 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.26 × 0.15 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.820, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	15537, 5443, 5087
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.072, 1.05
No. of reflections	5443
No. of parameters	259
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.66
Absolute structure	Flack (1983), 2497 Friedel pairs
Absolute structure parameter	−0.035 (18)

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

Selected bond lengths (Å) top

Sn—Cl1	2.4942 (9)	Sn—C20	2.188 (3)
Sn—S1	2.4857 (10)	S1—C1	1.746 (4)
Sn—S2	2.7366 (10)	S2—C1	1.714 (4)
Sn—C16	2.191 (4)

Footnotes

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

Acknowledgements

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

References

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