(N-Benzyl-N-isopropyl­dithio­carbamato)chloridodiphenyl­tin(IV)

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

doi:10.1107/S1600536810031636

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1087

https://doi.org/10.1107/S1600536810031636

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(N-Benzyl-N-isopropyldithiocarbamato)chloridodiphenyltin(IV)

Amirah Faizah Abdul Muthalib,^a Ibrahim Baba,^a Mohamed Ibrahim Mohamed Tahir,^b Seik Weng Ng ^c 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 6 August 2010; accepted 6 August 2010; online 11 August 2010)

The Sn^IV atom in the title organotin dithiocarbamate, [Sn(C₆H₅)₂(C₁₁H₁₄NS₂)Cl], is penta-coordinated by an asymmetrically coordinating dithiocarbamate ligand, a Cl and two ispo-C atoms of the Sn-bound phenyl groups. The resulting C₂ClS₂ donor set defines a coordination geometry intermediate between square-pyramidal and trigonal-bipyramidal with a slight tendency towards the latter. The formation of close intramolecular C–H⋯Cl and C–H⋯S contacts precludes the Cl and S atoms from forming significant intermolecular contacts. The presence of C–H⋯π contacts leads to the formation of supramolecular arrays that stack along the b axis.

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 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₁₁H₁₄NS₂Cl]
M_r = 532.69
Monoclinic, P 2₁ /n
a = 9.1934 (1) Å
b = 15.1720 (2) Å
c = 16.8740 (2) Å
β = 96.497 (1)°
V = 2338.51 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, UK.]$ ) T_min = 0.887, T_max = 1.000
54748 measured reflections
5345 independent reflections
4746 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.045
S = 1.04
5345 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1	0.95	2.80	3.4477 (17)	126
C6—H6⋯S2	0.95	2.80	3.4996 (16)	131
C14—H14⋯S2	1.00	2.51	3.0291 (15)	112
C3—H3⋯Cg1ⁱ	0.95	2.92	3.8002 (18)	154
C16—H16c⋯Cg1ⁱⁱ	0.98	2.81	3.4512 (18)	124
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, UK.]$ ); 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: https://doi.org/10.1107/S1600536810031636/su2203sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031636/su2203Isup2.hkl

checkCIF report

Comment top

Tin, including organotin, dithiocarbamates continue to attract attention as they are known to exhibit properties suggesting their potential as anti-cancer agents, anti-microbial agents and insecticides (Tiekink, 2008).

The Sn^IV atom in the structure of the title compound is five-coordinated, being chelated by an asymmetrically coordinating dithiocarbamate ligand, a chloride and two ispo-C atoms of the Sn-bound phenyl groups, Fig. 1. The coordination geometry is intermediate between square pyramidal and trigonal bi-pyramidal with a leaning towards the latter. This assignment is based on the value calculated for τ of 0.54 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 (Addison et al., 1984; Spek, 2009). The mode of coordination of the dithiocarbamate ligand, the disposition of the ligand donor set, and the intermediate coordination geometry matches with the literature precedents (Tiekink, 2008).

The formation of close intramolecular C–H···Cl and C–H···S contacts, Table 1, preclude the Cl and S atoms from forming significant intermolecular contacts. The most prominent intermolecular interactions are of the type C–H···π, involving the Sn-bound C7–C12 ring interacting with a methyl-H on one side and a phenyl-H on the other, Fig. 2 and Table 1. This results in the formation of supramolecular arrays in the ac plane which stack along the b 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).

Experimental top

Carbon disulfide (10 mmol) was added dropwise to an ethanol solution (100 ml) of N-benzyl-N-isopropyl (10 mmol). The solution was kept at 273 K for 1 h. Diphenyltin dichloride (5 mmol) dissolved in ethanol (20 ml) was added to give a white precipitate. This was collected and recrystallized from a chloroform/ethanol (1/2) mixture.

Structure description 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).

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 the title complex showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the 2-D supramolecular array in the ac plane of the crystal structure of the title complex, with the C–H···π contacts shown as purple dashed lines.
	Fig. 3. A view in projection down the a axis of the crystal structure of the title complex, showing the stacking of the 2-D arrays along the b axis. The C–H···π contacts are shown as purple dashed lines.

(N-Benzyl-N-isopropyldithiocarbamato)chloridodiphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₁₁H₁₄NS₂)Cl]	F(000) = 1072
M_r = 532.69	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 34829 reflections
a = 9.1934 (1) Å	θ = 2.2–29.2°
b = 15.1720 (2) Å	µ = 1.39 mm⁻¹
c = 16.8740 (2) Å	T = 100 K
β = 96.497 (1)°	Block, colourless
V = 2338.51 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5345 independent reflections
Radiation source: fine-focus sealed tube	4746 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
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 = −19→19
T_min = 0.887, T_max = 1.000	l = −21→21
54748 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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.045	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0285P)²] where P = (F_o² + 2F_c²)/3
5345 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₁₁H₁₄NS₂)Cl]	V = 2338.51 (5) Å³
M_r = 532.69	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1934 (1) Å	µ = 1.39 mm⁻¹
b = 15.1720 (2) Å	T = 100 K
c = 16.8740 (2) Å	0.30 × 0.25 × 0.20 mm
β = 96.497 (1)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5345 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4746 reflections with I > 2σ(I)
T_min = 0.887, T_max = 1.000	R_int = 0.042
54748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.045	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
5345 reflections	Δρ_min = −0.33 e Å⁻³
253 parameters

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

	x	y	z	U_iso*/U_eq
Sn	0.677004 (10)	0.690203 (6)	0.688075 (5)	0.01845 (4)
Cl1	0.76007 (4)	0.53663 (2)	0.68888 (2)	0.03259 (9)
S1	0.58215 (4)	0.65598 (2)	0.81529 (2)	0.02475 (8)
S2	0.54077 (4)	0.83082 (2)	0.73935 (2)	0.02118 (8)
N1	0.41603 (13)	0.78207 (8)	0.86783 (7)	0.0232 (3)
C1	0.88272 (15)	0.75295 (10)	0.67971 (8)	0.0240 (3)
C2	0.99547 (18)	0.70469 (11)	0.65168 (10)	0.0325 (4)
H2	0.9832	0.6434	0.6416	0.039*
C3	1.12574 (18)	0.74585 (15)	0.63840 (10)	0.0439 (5)
H3	1.2024	0.7127	0.6195	0.053*
C4	1.14323 (19)	0.83449 (15)	0.65269 (12)	0.0482 (5)
H4	1.2318	0.8627	0.6429	0.058*
C5	1.03361 (19)	0.88287 (13)	0.68104 (11)	0.0438 (5)
H5	1.0469	0.9441	0.6910	0.053*
C6	0.90314 (17)	0.84220 (11)	0.69513 (10)	0.0318 (4)
H6	0.8281	0.8756	0.7153	0.038*
C7	0.52428 (15)	0.68234 (8)	0.58354 (8)	0.0185 (3)
C8	0.49266 (16)	0.75798 (10)	0.53744 (9)	0.0242 (3)
H8	0.5373	0.8125	0.5539	0.029*
C9	0.39670 (17)	0.75412 (11)	0.46787 (9)	0.0292 (3)
H9	0.3767	0.8057	0.4366	0.035*
C10	0.33020 (17)	0.67518 (11)	0.44404 (10)	0.0297 (4)
H10	0.2646	0.6725	0.3964	0.036*
C11	0.35952 (16)	0.59975 (10)	0.48987 (9)	0.0274 (3)
H11	0.3130	0.5457	0.4739	0.033*
C12	0.45682 (15)	0.60357 (9)	0.55895 (9)	0.0227 (3)
H12	0.4775	0.5517	0.5897	0.027*
C13	0.50196 (15)	0.76049 (9)	0.81307 (8)	0.0199 (3)
C14	0.34197 (16)	0.86968 (10)	0.86646 (9)	0.0289 (3)
H14	0.3399	0.8938	0.8112	0.035*
C15	0.4319 (2)	0.93275 (12)	0.92244 (12)	0.0431 (4)
H15A	0.5321	0.9355	0.9081	0.065*
H15B	0.4335	0.9118	0.9775	0.065*
H15C	0.3879	0.9916	0.9178	0.065*
C16	0.18495 (18)	0.86220 (12)	0.88488 (11)	0.0400 (4)
H16A	0.1320	0.8206	0.8477	0.060*
H16B	0.1379	0.9202	0.8792	0.060*
H16C	0.1835	0.8410	0.9397	0.060*
C17	0.40459 (18)	0.72348 (11)	0.93638 (9)	0.0294 (3)
H17A	0.3741	0.7592	0.9808	0.035*
H17B	0.5030	0.6994	0.9541	0.035*
C18	0.29886 (16)	0.64710 (10)	0.92112 (9)	0.0249 (3)
C19	0.20502 (18)	0.63709 (11)	0.85206 (9)	0.0316 (3)
H19A	0.2080	0.6781	0.8097	0.038*
C20	0.1059 (2)	0.56752 (11)	0.84380 (12)	0.0411 (4)
H20	0.0412	0.5614	0.7961	0.049*
C21	0.1015 (2)	0.50811 (12)	0.90402 (13)	0.0519 (5)
H21	0.0325	0.4612	0.8988	0.062*
C22	0.1979 (3)	0.51627 (13)	0.97299 (13)	0.0581 (6)
H22	0.1962	0.4743	1.0146	0.070*
C23	0.2960 (2)	0.58509 (11)	0.98129 (10)	0.0406 (4)
H23	0.3622	0.5901	1.0286	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01680 (6)	0.01905 (6)	0.01915 (6)	0.00046 (4)	0.00050 (4)	−0.00322 (3)
Cl1	0.0362 (2)	0.02243 (19)	0.0372 (2)	0.00957 (16)	−0.00441 (17)	−0.00494 (15)
S1	0.0298 (2)	0.02159 (18)	0.02287 (18)	−0.00067 (15)	0.00296 (15)	0.00143 (14)
S2	0.02277 (18)	0.01888 (17)	0.02314 (18)	−0.00102 (13)	0.00801 (14)	−0.00170 (13)
N1	0.0239 (6)	0.0260 (6)	0.0202 (6)	−0.0069 (5)	0.0053 (5)	−0.0045 (5)
C1	0.0161 (7)	0.0360 (9)	0.0193 (7)	−0.0015 (6)	−0.0004 (5)	0.0015 (6)
C2	0.0256 (8)	0.0448 (10)	0.0275 (8)	0.0053 (7)	0.0045 (7)	0.0010 (7)
C3	0.0212 (8)	0.0748 (14)	0.0370 (10)	0.0076 (9)	0.0090 (7)	0.0106 (9)
C4	0.0207 (9)	0.0789 (15)	0.0442 (11)	−0.0136 (9)	0.0004 (8)	0.0186 (10)
C5	0.0319 (9)	0.0488 (11)	0.0491 (11)	−0.0161 (8)	−0.0028 (8)	0.0075 (9)
C6	0.0242 (8)	0.0358 (9)	0.0348 (9)	−0.0062 (7)	0.0010 (7)	−0.0008 (7)
C7	0.0158 (6)	0.0212 (7)	0.0186 (7)	0.0015 (5)	0.0014 (5)	−0.0037 (5)
C8	0.0244 (8)	0.0208 (8)	0.0274 (8)	0.0002 (6)	0.0037 (6)	−0.0017 (6)
C9	0.0291 (8)	0.0311 (9)	0.0267 (8)	0.0091 (7)	0.0007 (6)	0.0044 (6)
C10	0.0219 (8)	0.0421 (10)	0.0236 (8)	0.0054 (7)	−0.0042 (6)	−0.0049 (7)
C11	0.0212 (7)	0.0296 (8)	0.0309 (8)	−0.0034 (6)	0.0011 (6)	−0.0092 (6)
C12	0.0219 (7)	0.0206 (7)	0.0256 (7)	0.0004 (6)	0.0031 (6)	−0.0017 (6)
C13	0.0183 (7)	0.0222 (7)	0.0188 (7)	−0.0066 (6)	0.0003 (5)	−0.0053 (5)
C14	0.0297 (8)	0.0274 (8)	0.0317 (8)	−0.0026 (7)	0.0132 (7)	−0.0076 (6)
C15	0.0418 (10)	0.0331 (10)	0.0560 (12)	−0.0112 (8)	0.0128 (9)	−0.0188 (8)
C16	0.0332 (9)	0.0421 (10)	0.0477 (11)	−0.0030 (8)	0.0179 (8)	−0.0098 (8)
C17	0.0318 (8)	0.0393 (9)	0.0177 (7)	−0.0093 (7)	0.0046 (6)	−0.0023 (6)
C18	0.0271 (8)	0.0251 (8)	0.0241 (7)	−0.0007 (6)	0.0095 (6)	−0.0019 (6)
C19	0.0343 (9)	0.0287 (9)	0.0316 (8)	−0.0063 (7)	0.0026 (7)	−0.0001 (7)
C20	0.0382 (10)	0.0344 (10)	0.0516 (11)	−0.0104 (8)	0.0083 (8)	−0.0124 (8)
C21	0.0649 (13)	0.0325 (10)	0.0636 (13)	−0.0202 (9)	0.0301 (11)	−0.0113 (9)
C22	0.0979 (18)	0.0314 (10)	0.0502 (12)	−0.0109 (11)	0.0309 (12)	0.0071 (9)
C23	0.0587 (12)	0.0353 (10)	0.0288 (9)	0.0018 (9)	0.0100 (8)	0.0027 (7)

Geometric parameters (Å, º) top

Sn—S1	2.4621 (4)	C10—H10	0.9500
Sn—S2	2.6672 (4)	C11—C12	1.388 (2)
Sn—C1	2.1362 (14)	C11—H11	0.9500
Sn—C7	2.1300 (14)	C12—H12	0.9500
Sn—Cl1	2.4515 (4)	C14—C16	1.515 (2)
S1—C13	1.7472 (15)	C14—C15	1.521 (2)
S2—C13	1.7070 (14)	C14—H14	1.0000
N1—C13	1.3230 (18)	C15—H15A	0.9800
N1—C17	1.4721 (19)	C15—H15B	0.9800
N1—C14	1.492 (2)	C15—H15C	0.9800
C1—C6	1.388 (2)	C16—H16A	0.9800
C1—C2	1.395 (2)	C16—H16B	0.9800
C2—C3	1.391 (2)	C16—H16C	0.9800
C2—H2	0.9500	C17—C18	1.516 (2)
C3—C4	1.373 (3)	C17—H17A	0.9900
C3—H3	0.9500	C17—H17B	0.9900
C4—C5	1.376 (3)	C18—C19	1.378 (2)
C4—H4	0.9500	C18—C23	1.387 (2)
C5—C6	1.393 (2)	C19—C20	1.391 (2)
C5—H5	0.9500	C19—H19A	0.9500
C6—H6	0.9500	C20—C21	1.363 (3)
C7—C12	1.3881 (19)	C20—H20	0.9500
C7—C8	1.3984 (19)	C21—C22	1.386 (3)
C8—C9	1.388 (2)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.377 (3)
C9—C10	1.384 (2)	C22—H22	0.9500
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.390 (2)

C7—Sn—C1	118.41 (5)	C11—C12—C7	120.71 (13)
C7—Sn—Cl1	97.30 (4)	C11—C12—H12	119.6
C1—Sn—Cl1	98.42 (4)	C7—C12—H12	119.6
C7—Sn—S1	116.42 (4)	N1—C13—S2	123.01 (11)
C1—Sn—S1	123.72 (4)	N1—C13—S1	119.57 (11)
Cl1—Sn—S1	86.307 (14)	S2—C13—S1	117.42 (8)
C7—Sn—S2	91.36 (4)	N1—C14—C16	111.95 (13)
C1—Sn—S2	96.70 (4)	N1—C14—C15	109.62 (13)
Cl1—Sn—S2	156.326 (13)	C16—C14—C15	112.52 (13)
S1—Sn—S2	70.135 (12)	N1—C14—H14	107.5
C13—S1—Sn	88.86 (5)	C16—C14—H14	107.5
C13—S2—Sn	83.16 (5)	C15—C14—H14	107.5
C13—N1—C17	120.05 (13)	C14—C15—H15A	109.5
C13—N1—C14	121.13 (12)	C14—C15—H15B	109.5
C17—N1—C14	118.49 (12)	H15A—C15—H15B	109.5
C6—C1—C2	119.07 (14)	C14—C15—H15C	109.5
C6—C1—Sn	121.63 (11)	H15A—C15—H15C	109.5
C2—C1—Sn	119.07 (12)	H15B—C15—H15C	109.5
C1—C2—C3	120.35 (17)	C14—C16—H16A	109.5
C1—C2—H2	119.8	C14—C16—H16B	109.5
C3—C2—H2	119.8	H16A—C16—H16B	109.5
C4—C3—C2	119.83 (17)	C14—C16—H16C	109.5
C4—C3—H3	120.1	H16A—C16—H16C	109.5
C2—C3—H3	120.1	H16B—C16—H16C	109.5
C3—C4—C5	120.53 (17)	N1—C17—C18	115.44 (12)
C3—C4—H4	119.7	N1—C17—H17A	108.4
C5—C4—H4	119.7	C18—C17—H17A	108.4
C4—C5—C6	120.12 (18)	N1—C17—H17B	108.4
C4—C5—H5	119.9	C18—C17—H17B	108.4
C6—C5—H5	119.9	H17A—C17—H17B	107.5
C1—C6—C5	120.07 (16)	C19—C18—C23	118.87 (15)
C1—C6—H6	120.0	C19—C18—C17	123.79 (14)
C5—C6—H6	120.0	C23—C18—C17	117.33 (14)
C12—C7—C8	118.86 (13)	C18—C19—C20	120.58 (16)
C12—C7—Sn	121.74 (10)	C18—C19—H19A	119.7
C8—C7—Sn	119.39 (10)	C20—C19—H19A	119.7
C9—C8—C7	120.54 (14)	C21—C20—C19	120.13 (18)
C9—C8—H8	119.7	C21—C20—H20	119.9
C7—C8—H8	119.7	C19—C20—H20	119.9
C8—C9—C10	120.02 (15)	C20—C21—C22	119.78 (18)
C8—C9—H9	120.0	C20—C21—H21	120.1
C10—C9—H9	120.0	C22—C21—H21	120.1
C9—C10—C11	119.95 (14)	C23—C22—C21	120.17 (18)
C9—C10—H10	120.0	C23—C22—H22	119.9
C11—C10—H10	120.0	C21—C22—H22	119.9
C12—C11—C10	119.92 (14)	C22—C23—C18	120.43 (18)
C12—C11—H11	120.0	C22—C23—H23	119.8
C10—C11—H11	120.0	C18—C23—H23	119.8

C7—Sn—S1—C13	−77.41 (6)	C12—C7—C8—C9	−0.7 (2)
C1—Sn—S1—C13	88.60 (7)	Sn—C7—C8—C9	178.20 (11)
Cl1—Sn—S1—C13	−173.74 (5)	C7—C8—C9—C10	0.7 (2)
S2—Sn—S1—C13	3.88 (4)	C8—C9—C10—C11	0.0 (2)
C7—Sn—S2—C13	113.69 (6)	C9—C10—C11—C12	−0.8 (2)
C1—Sn—S2—C13	−127.49 (6)	C10—C11—C12—C7	0.8 (2)
Cl1—Sn—S2—C13	1.93 (6)	C8—C7—C12—C11	−0.1 (2)
S1—Sn—S2—C13	−4.00 (5)	Sn—C7—C12—C11	−178.90 (11)
C7—Sn—C1—C6	91.75 (12)	C17—N1—C13—S2	−170.93 (10)
Cl1—Sn—C1—C6	−165.18 (11)	C14—N1—C13—S2	2.41 (18)
S1—Sn—C1—C6	−74.01 (12)	C17—N1—C13—S1	8.53 (17)
S2—Sn—C1—C6	−3.45 (12)	C14—N1—C13—S1	−178.13 (10)
C7—Sn—C1—C2	−82.83 (13)	Sn—S2—C13—N1	−174.56 (12)
Cl1—Sn—C1—C2	20.24 (12)	Sn—S2—C13—S1	5.98 (7)
S1—Sn—C1—C2	111.41 (11)	Sn—S1—C13—N1	174.08 (11)
S2—Sn—C1—C2	−178.04 (11)	Sn—S1—C13—S2	−6.43 (7)
C6—C1—C2—C3	−0.8 (2)	C13—N1—C14—C16	137.97 (14)
Sn—C1—C2—C3	173.88 (12)	C17—N1—C14—C16	−48.59 (18)
C1—C2—C3—C4	−0.2 (3)	C13—N1—C14—C15	−96.44 (16)
C2—C3—C4—C5	0.8 (3)	C17—N1—C14—C15	77.01 (16)
C3—C4—C5—C6	−0.3 (3)	C13—N1—C17—C18	−82.58 (17)
C2—C1—C6—C5	1.3 (2)	C14—N1—C17—C18	103.90 (16)
Sn—C1—C6—C5	−173.25 (12)	N1—C17—C18—C19	−7.8 (2)
C4—C5—C6—C1	−0.8 (3)	N1—C17—C18—C23	173.37 (14)
C1—Sn—C7—C12	130.17 (12)	C23—C18—C19—C20	2.0 (2)
Cl1—Sn—C7—C12	26.46 (12)	C17—C18—C19—C20	−176.85 (15)
S1—Sn—C7—C12	−63.03 (12)	C18—C19—C20—C21	−0.4 (3)
S2—Sn—C7—C12	−131.46 (11)	C19—C20—C21—C22	−1.2 (3)
C1—Sn—C7—C8	−48.66 (13)	C20—C21—C22—C23	1.2 (3)
Cl1—Sn—C7—C8	−152.38 (11)	C21—C22—C23—C18	0.4 (3)
S1—Sn—C7—C8	118.13 (11)	C19—C18—C23—C22	−2.0 (3)
S2—Sn—C7—C8	49.71 (11)	C17—C18—C23—C22	176.94 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	0.95	2.80	3.4477 (17)	126
C6—H6···S2	0.95	2.80	3.4996 (16)	131
C14—H14···S2	1.00	2.51	3.0291 (15)	112
C3—H3···Cg1ⁱ	0.95	2.92	3.8002 (18)	154
C16—H16c···Cg1ⁱⁱ	0.98	2.81	3.4512 (18)	124

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₁₁H₁₄NS₂)Cl]
M_r	532.69
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.1934 (1), 15.1720 (2), 16.8740 (2)
β (°)	96.497 (1)
V (Å³)	2338.51 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.887, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	54748, 5345, 4746
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.045, 1.04
No. of reflections	5345
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	0.95	2.80	3.4477 (17)	126
C6—H6···S2	0.95	2.80	3.4996 (16)	131
C14—H14···S2	1.00	2.51	3.0291 (15)	112
C3—H3···Cg1ⁱ	0.95	2.92	3.8002 (18)	154
C16—H16c···Cg1ⁱⁱ	0.98	2.81	3.4512 (18)	124

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

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

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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, UK. 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 66| Part 9| September 2010| Page m1087

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