{[(N-Butyl-N-methylcarbamothioyl)sulfanyl]acetato-κO}tris(2-chloro­benz­yl)tin(IV)

Keng, T.C.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810005830

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m307

doi:10.1107/S1600536810005830

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{[(N-Butyl-N-methylcarbamothioyl)sulfanyl]acetato-κO}tris(2-chlorobenzyl)tin(IV)

Thy Chun Keng,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 February 2010; accepted 12 February 2010; online 17 February 2010)

The Sn atom in the title compound, [Sn(C₇H₆Cl)₃(C₈H₁₄NO₂S₂)], is coordinated by three chlorobenzyl ligands and one carboxylate O atom of the substituted acetate ligand in a distorted tetrahedral environment. Three of the C atoms of the n-butyl group are disordered over two sites with equal occupancies.

Related literature

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng et al. (1988 ). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961 ). For the synthesis of dithiocarbamoylacetic acids, see: Nachmias (1952 ). For background to the triorganotin derivatives of dithiocarbamylacetic acids, see: Ng & Kumar Das (1991 ).

Experimental

Crystal data

[Sn(C₇H₆Cl)₃(C₈H₁₄NO₂S₂)]
M_r = 715.72
Triclinic, $[P \overline 1]$
a = 10.2485 (2) Å
b = 11.7943 (2) Å
c = 13.1704 (3) Å
α = 84.417 (1)°
β = 84.113 (1)°
γ = 86.387 (1)°
V = 1573.79 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.710, T_max = 0.887
11006 measured reflections
6949 independent reflections
5708 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.078
S = 1.03
6949 reflections
353 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005830/lh2995sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005830/lh2995Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1.

Related literature top

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng et al. (1988). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961). For the synthesis of dithiocarbamoylacetic acids, see: Nachmias (1952). For background to the triorganotin derivatives of dithiocarbamylacetic acids, see: Ng & Kumar Das (1991).

Experimental top

n-Butylmethyldithiocarbomylacetic acid was synthesized from n-butylmethylamine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tri(o-chlorobenzyl)tin chloride was prepared by direct synthesis from o-chlorobenzyl chloride and tin powder in a mixture of toluene and water (Sisido et al., 1961). The triorganotin chloride was hydrolyzed with dilute sodium hydroxide solution to give tri(o-chlorobenzyl)tin hydroxide. The carboxylic acid (0.1 g, 0.45 mmol) and the organotin hydroxide (0.23 g, 0.45 mmol) were heated in ethanol (100 ml) for 1 hour. After filtering the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Sn(C₇H₆Cl)₃(C₈H₁₄N₂O₂S₂) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the butyl chain is not shown.

{[(N-Butyl-N-methylcarbamothioyl)sulfanyl]acetato- κO}tris(2-chlorobenzyl)tin(IV) top

Crystal data top

[Sn(C₇H₆Cl)₃(C₈H₁₄NO₂S₂)]	Z = 2
M_r = 715.72	F(000) = 724
Triclinic, P1	D_x = 1.510 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2485 (2) Å	Cell parameters from 3482 reflections
b = 11.7943 (2) Å	θ = 2.4–24.9°
c = 13.1704 (3) Å	µ = 1.23 mm⁻¹
α = 84.417 (1)°	T = 293 K
β = 84.113 (1)°	Block, colorless
γ = 86.387 (1)°	0.30 × 0.20 × 0.10 mm
V = 1573.79 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	6949 independent reflections
Radiation source: fine-focus sealed tube	5708 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.710, T_max = 0.887	k = −15→15
11006 measured reflections	l = −15→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.032P)² + 0.1764P] where P = (F_o² + 2F_c²)/3
6949 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.49 e Å⁻³
10 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Sn(C₇H₆Cl)₃(C₈H₁₄NO₂S₂)]	γ = 86.387 (1)°
M_r = 715.72	V = 1573.79 (5) Å³
Triclinic, P1	Z = 2
a = 10.2485 (2) Å	Mo Kα radiation
b = 11.7943 (2) Å	µ = 1.23 mm⁻¹
c = 13.1704 (3) Å	T = 293 K
α = 84.417 (1)°	0.30 × 0.20 × 0.10 mm
β = 84.113 (1)°

Data collection top

Bruker SMART APEX diffractometer	6949 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5708 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.887	R_int = 0.023
11006 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	10 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
6949 reflections	Δρ_min = −0.69 e Å⁻³
353 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.204624 (18)	0.556101 (16)	0.639187 (15)	0.03536 (7)
Cl1	0.34853 (10)	0.32147 (9)	0.86752 (8)	0.0813 (3)
Cl2	0.14093 (9)	0.31598 (8)	0.51718 (7)	0.0639 (2)
Cl3	0.14793 (11)	0.58144 (9)	0.91177 (8)	0.0797 (3)
S1	0.40006 (8)	0.83118 (6)	0.30222 (6)	0.0476 (2)
S2	0.22340 (9)	0.95231 (8)	0.45925 (7)	0.0589 (2)
O1	0.18941 (19)	0.61434 (17)	0.48768 (15)	0.0440 (5)
O2	0.38538 (19)	0.67862 (17)	0.50007 (15)	0.0447 (5)
N1	0.4466 (3)	1.0273 (2)	0.3635 (2)	0.0517 (7)
C1	0.3727 (3)	0.4388 (3)	0.6482 (2)	0.0460 (7)
H1A	0.3428	0.3630	0.6699	0.055*
H1B	0.4190	0.4366	0.5803	0.055*
C2	0.4663 (3)	0.4680 (2)	0.7200 (2)	0.0418 (7)
C3	0.5614 (3)	0.5462 (3)	0.6885 (3)	0.0490 (8)
H3	0.5636	0.5823	0.6224	0.059*
C4	0.6529 (4)	0.5726 (3)	0.7516 (3)	0.0645 (10)
H4	0.7152	0.6254	0.7279	0.077*
C5	0.6513 (4)	0.5205 (4)	0.8489 (3)	0.0723 (11)
H5	0.7129	0.5374	0.8916	0.087*
C6	0.5586 (4)	0.4433 (3)	0.8837 (3)	0.0673 (11)
H6	0.5577	0.4074	0.9498	0.081*
C7	0.4664 (3)	0.4186 (3)	0.8204 (2)	0.0498 (8)
C8	0.0185 (3)	0.4777 (2)	0.6709 (2)	0.0393 (6)
H8A	−0.0351	0.5175	0.7228	0.047*
H8B	−0.0266	0.4866	0.6092	0.047*
C9	0.0306 (3)	0.3539 (2)	0.7071 (2)	0.0393 (6)
C10	−0.0111 (3)	0.3140 (3)	0.8071 (2)	0.0543 (8)
H10	−0.0457	0.3660	0.8528	0.065*
C11	−0.0028 (4)	0.1998 (4)	0.8405 (3)	0.0763 (12)
H11	−0.0320	0.1752	0.9078	0.092*
C12	0.0493 (5)	0.1219 (3)	0.7732 (4)	0.0847 (14)
H12	0.0544	0.0445	0.7954	0.102*
C13	0.0931 (4)	0.1575 (3)	0.6746 (3)	0.0668 (10)
H13	0.1287	0.1051	0.6295	0.080*
C14	0.0838 (3)	0.2722 (3)	0.6428 (2)	0.0464 (7)
C15	0.2045 (3)	0.7154 (3)	0.7065 (2)	0.0503 (8)
H15A	0.2742	0.7113	0.7515	0.060*
H15B	0.2226	0.7761	0.6526	0.060*
C16	0.0771 (3)	0.7435 (2)	0.7657 (2)	0.0402 (7)
C17	−0.0152 (3)	0.8235 (3)	0.7272 (3)	0.0549 (8)
H17	0.0037	0.8617	0.6627	0.066*
C18	−0.1340 (4)	0.8476 (3)	0.7821 (3)	0.0659 (10)
H18	−0.1932	0.9021	0.7545	0.079*
C19	−0.1655 (4)	0.7923 (3)	0.8764 (3)	0.0666 (10)
H19	−0.2455	0.8094	0.9132	0.080*
C20	−0.0780 (3)	0.7112 (3)	0.9169 (3)	0.0571 (9)
H20	−0.0985	0.6728	0.9810	0.068*
C21	0.0404 (3)	0.6876 (2)	0.8614 (2)	0.0431 (7)
C22	0.2903 (3)	0.6740 (2)	0.4527 (2)	0.0369 (6)
C23	0.2751 (3)	0.7353 (2)	0.3481 (2)	0.0416 (7)
H23A	0.1908	0.7777	0.3505	0.050*
H23B	0.2739	0.6789	0.2994	0.050*
C24	0.3591 (3)	0.9463 (2)	0.3791 (2)	0.0427 (7)
C25	0.4238 (4)	1.1315 (3)	0.4164 (3)	0.0721 (11)
H25A	0.4044	1.1116	0.4886	0.108*
H25B	0.3511	1.1764	0.3903	0.108*
H25C	0.5011	1.1748	0.4051	0.108*
C26	0.5641 (3)	1.0227 (3)	0.2910 (3)	0.0594 (9)
H26A	0.5949	0.9436	0.2868	0.071*	0.50
H26B	0.6326	1.0619	0.3166	0.071*	0.50
H26C	0.5873	0.9438	0.2787	0.071*	0.50
H26D	0.6365	1.0517	0.3209	0.071*	0.50
C27	0.541 (3)	1.076 (3)	0.1840 (11)	0.070 (3)	0.50
H27A	0.5063	1.1541	0.1878	0.083*	0.50
H27B	0.4774	1.0340	0.1558	0.083*	0.50
C28	0.670 (3)	1.075 (3)	0.1132 (11)	0.097 (3)	0.50
H28A	0.7269	1.1307	0.1323	0.116*	0.50
H28B	0.7153	1.0004	0.1214	0.116*	0.50
C29	0.644 (5)	1.103 (3)	0.0016 (9)	0.140 (8)	0.50
H29A	0.7228	1.0885	−0.0420	0.210*	0.50
H29B	0.6150	1.1818	−0.0094	0.210*	0.50
H29C	0.5766	1.0560	−0.0141	0.210*	0.50
C27'	0.545 (3)	1.091 (3)	0.1895 (11)	0.070 (3)	0.50
H27C	0.5421	1.1721	0.1988	0.083*	0.50
H27D	0.4623	1.0743	0.1665	0.083*	0.50
C28'	0.658 (3)	1.064 (3)	0.1076 (11)	0.097 (3)	0.50
H28C	0.7411	1.0656	0.1358	0.116*	0.50
H28D	0.6498	0.9875	0.0880	0.116*	0.50
C29'	0.654 (5)	1.149 (3)	0.0135 (10)	0.140 (8)	0.50
H29D	0.7279	1.1336	−0.0348	0.210*	0.50
H29E	0.6571	1.2251	0.0335	0.210*	0.50
H29F	0.5741	1.1431	−0.0175	0.210*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03237 (11)	0.03689 (11)	0.03697 (11)	−0.00267 (7)	−0.00229 (8)	−0.00472 (8)
Cl1	0.0721 (6)	0.0797 (7)	0.0813 (7)	−0.0031 (5)	0.0255 (5)	0.0124 (5)
Cl2	0.0628 (5)	0.0761 (6)	0.0531 (5)	0.0057 (4)	0.0016 (4)	−0.0211 (4)
Cl3	0.0783 (7)	0.0837 (7)	0.0698 (6)	0.0212 (6)	−0.0118 (5)	0.0175 (5)
S1	0.0548 (5)	0.0414 (4)	0.0446 (4)	−0.0085 (4)	0.0098 (4)	−0.0048 (3)
S2	0.0646 (6)	0.0545 (5)	0.0544 (5)	0.0056 (4)	0.0069 (4)	−0.0086 (4)
O1	0.0434 (11)	0.0509 (12)	0.0382 (11)	−0.0141 (10)	−0.0055 (9)	0.0025 (9)
O2	0.0377 (11)	0.0518 (13)	0.0451 (12)	−0.0035 (9)	−0.0086 (10)	−0.0018 (10)
N1	0.0565 (17)	0.0378 (14)	0.0614 (18)	−0.0043 (12)	−0.0096 (14)	−0.0032 (12)
C1	0.0373 (16)	0.0455 (17)	0.0560 (19)	0.0023 (13)	−0.0082 (14)	−0.0074 (14)
C2	0.0348 (15)	0.0441 (17)	0.0462 (18)	0.0068 (13)	−0.0048 (13)	−0.0078 (14)
C3	0.0468 (18)	0.0492 (18)	0.0508 (19)	−0.0010 (15)	−0.0080 (15)	−0.0016 (15)
C4	0.055 (2)	0.060 (2)	0.082 (3)	−0.0074 (17)	−0.022 (2)	−0.006 (2)
C5	0.073 (3)	0.078 (3)	0.074 (3)	0.004 (2)	−0.039 (2)	−0.015 (2)
C6	0.082 (3)	0.074 (3)	0.045 (2)	0.018 (2)	−0.016 (2)	−0.0052 (18)
C7	0.0459 (18)	0.053 (2)	0.0474 (19)	0.0085 (15)	0.0000 (15)	−0.0025 (15)
C8	0.0331 (14)	0.0414 (16)	0.0442 (17)	−0.0026 (12)	−0.0032 (13)	−0.0086 (13)
C9	0.0338 (15)	0.0433 (16)	0.0426 (17)	−0.0076 (12)	−0.0079 (13)	−0.0057 (13)
C10	0.059 (2)	0.061 (2)	0.0442 (18)	−0.0208 (17)	−0.0066 (16)	0.0004 (16)
C11	0.088 (3)	0.081 (3)	0.061 (2)	−0.037 (2)	−0.019 (2)	0.021 (2)
C12	0.101 (3)	0.048 (2)	0.109 (4)	−0.019 (2)	−0.039 (3)	0.012 (2)
C13	0.070 (2)	0.046 (2)	0.088 (3)	−0.0021 (18)	−0.023 (2)	−0.012 (2)
C14	0.0458 (17)	0.0434 (17)	0.0521 (19)	−0.0043 (14)	−0.0121 (15)	−0.0063 (14)
C15	0.0547 (19)	0.0476 (18)	0.0502 (19)	−0.0136 (15)	0.0046 (15)	−0.0148 (15)
C16	0.0487 (17)	0.0340 (15)	0.0398 (16)	−0.0109 (13)	−0.0014 (13)	−0.0098 (12)
C17	0.070 (2)	0.0461 (19)	0.0468 (19)	−0.0034 (17)	−0.0067 (17)	0.0046 (15)
C18	0.064 (2)	0.057 (2)	0.075 (3)	0.0117 (18)	−0.014 (2)	0.0041 (19)
C19	0.048 (2)	0.072 (3)	0.077 (3)	0.0065 (18)	0.0035 (19)	−0.012 (2)
C20	0.061 (2)	0.068 (2)	0.0411 (18)	−0.0057 (18)	0.0018 (16)	−0.0061 (16)
C21	0.0488 (18)	0.0421 (17)	0.0386 (16)	0.0002 (13)	−0.0068 (14)	−0.0038 (13)
C22	0.0368 (15)	0.0360 (15)	0.0382 (16)	−0.0021 (12)	−0.0009 (13)	−0.0075 (12)
C23	0.0445 (17)	0.0417 (16)	0.0391 (16)	−0.0054 (13)	−0.0062 (13)	−0.0020 (13)
C24	0.0523 (18)	0.0371 (16)	0.0387 (16)	0.0017 (13)	−0.0095 (14)	−0.0006 (13)
C25	0.095 (3)	0.044 (2)	0.083 (3)	−0.0074 (19)	−0.023 (2)	−0.0156 (19)
C26	0.049 (2)	0.053 (2)	0.076 (3)	−0.0141 (16)	−0.0088 (18)	0.0018 (18)
C27	0.064 (3)	0.069 (6)	0.074 (3)	−0.014 (3)	−0.007 (2)	0.007 (3)
C28	0.072 (6)	0.125 (7)	0.090 (4)	−0.025 (4)	−0.003 (4)	0.014 (3)
C29	0.153 (10)	0.17 (3)	0.094 (5)	−0.051 (17)	0.005 (7)	0.016 (8)
C27'	0.064 (3)	0.069 (6)	0.074 (3)	−0.014 (3)	−0.007 (2)	0.007 (3)
C28'	0.072 (6)	0.125 (7)	0.090 (4)	−0.025 (4)	−0.003 (4)	0.014 (3)
C29'	0.153 (10)	0.17 (3)	0.094 (5)	−0.051 (17)	0.005 (7)	0.016 (8)

Geometric parameters (Å, º) top

Sn1—O1	2.0643 (19)	C15—H15A	0.9700
Sn1—C1	2.146 (3)	C15—H15B	0.9700
Sn1—C15	2.154 (3)	C16—C21	1.391 (4)
Sn1—C8	2.157 (3)	C16—C17	1.392 (4)
Cl1—C7	1.743 (4)	C17—C18	1.379 (5)
Cl2—C14	1.738 (3)	C17—H17	0.9300
Cl3—C21	1.743 (3)	C18—C19	1.363 (5)
S1—C24	1.775 (3)	C18—H18	0.9300
S1—C23	1.782 (3)	C19—C20	1.376 (5)
S2—C24	1.659 (3)	C19—H19	0.9300
O1—C22	1.307 (3)	C20—C21	1.378 (4)
O2—C22	1.217 (3)	C20—H20	0.9300
N1—C24	1.339 (4)	C22—C23	1.510 (4)
N1—C26	1.460 (4)	C23—H23A	0.9700
N1—C25	1.466 (4)	C23—H23B	0.9700
C1—C2	1.491 (4)	C25—H25A	0.9600
C1—H1A	0.9700	C25—H25B	0.9600
C1—H1B	0.9700	C25—H25C	0.9600
C2—C3	1.389 (4)	C26—C27'	1.518 (8)
C2—C7	1.392 (4)	C26—C27	1.521 (8)
C3—C4	1.383 (4)	C26—H26A	0.9700
C3—H3	0.9300	C26—H26B	0.9700
C4—C5	1.365 (5)	C26—H26C	0.9700
C4—H4	0.9300	C26—H26D	0.9700
C5—C6	1.371 (5)	C27—C28	1.537 (9)
C5—H5	0.9300	C27—H27A	0.9700
C6—C7	1.384 (5)	C27—H27B	0.9700
C6—H6	0.9300	C28—C29	1.522 (10)
C8—C9	1.492 (4)	C28—H28A	0.9700
C8—H8A	0.9700	C28—H28B	0.9700
C8—H8B	0.9700	C29—H29A	0.9600
C9—C10	1.389 (4)	C29—H29B	0.9600
C9—C14	1.393 (4)	C29—H29C	0.9600
C10—C11	1.376 (5)	C27'—C28'	1.536 (9)
C10—H10	0.9300	C27'—H27C	0.9700
C11—C12	1.384 (6)	C27'—H27D	0.9700
C11—H11	0.9300	C28'—C29'	1.522 (10)
C12—C13	1.366 (6)	C28'—H28C	0.9700
C12—H12	0.9300	C28'—H28D	0.9700
C13—C14	1.377 (5)	C29'—H29D	0.9600
C13—H13	0.9300	C29'—H29E	0.9600
C15—C16	1.487 (4)	C29'—H29F	0.9600

O1—Sn1—C1	109.03 (10)	C19—C20—C21	119.3 (3)
O1—Sn1—C15	100.56 (11)	C19—C20—H20	120.3
C1—Sn1—C15	118.90 (12)	C21—C20—H20	120.3
O1—Sn1—C8	98.45 (10)	C20—C21—C16	122.8 (3)
C1—Sn1—C8	114.34 (11)	C20—C21—Cl3	118.8 (2)
C15—Sn1—C8	112.37 (11)	C16—C21—Cl3	118.3 (2)
C24—S1—C23	101.94 (14)	O2—C22—O1	123.0 (3)
C22—O1—Sn1	109.69 (17)	O2—C22—C23	124.4 (3)
C24—N1—C26	124.0 (3)	O1—C22—C23	112.6 (2)
C24—N1—C25	120.2 (3)	C22—C23—S1	114.9 (2)
C26—N1—C25	115.7 (3)	C22—C23—H23A	108.5
C2—C1—Sn1	113.91 (19)	S1—C23—H23A	108.5
C2—C1—H1A	108.8	C22—C23—H23B	108.5
Sn1—C1—H1A	108.8	S1—C23—H23B	108.5
C2—C1—H1B	108.8	H23A—C23—H23B	107.5
Sn1—C1—H1B	108.8	N1—C24—S2	124.3 (2)
H1A—C1—H1B	107.7	N1—C24—S1	113.1 (2)
C3—C2—C7	116.0 (3)	S2—C24—S1	122.57 (18)
C3—C2—C1	120.8 (3)	N1—C25—H25A	109.5
C7—C2—C1	123.2 (3)	N1—C25—H25B	109.5
C4—C3—C2	122.6 (3)	H25A—C25—H25B	109.5
C4—C3—H3	118.7	N1—C25—H25C	109.5
C2—C3—H3	118.7	H25A—C25—H25C	109.5
C5—C4—C3	119.6 (4)	H25B—C25—H25C	109.5
C5—C4—H4	120.2	N1—C26—C27'	112.5 (10)
C3—C4—H4	120.2	N1—C26—C27	113.3 (10)
C4—C5—C6	119.9 (4)	N1—C26—H26A	108.9
C4—C5—H5	120.0	C27'—C26—H26A	115.9
C6—C5—H5	120.0	C27—C26—H26A	108.9
C5—C6—C7	120.1 (4)	N1—C26—H26B	108.9
C5—C6—H6	120.0	C27'—C26—H26B	102.5
C7—C6—H6	120.0	C27—C26—H26B	108.9
C6—C7—C2	121.8 (3)	H26A—C26—H26B	107.7
C6—C7—Cl1	118.9 (3)	N1—C26—H26C	109.1
C2—C7—Cl1	119.2 (3)	C27'—C26—H26C	109.1
C9—C8—Sn1	113.64 (18)	C27—C26—H26C	101.9
C9—C8—H8A	108.8	N1—C26—H26D	109.1
Sn1—C8—H8A	108.8	C27'—C26—H26D	109.1
C9—C8—H8B	108.8	C27—C26—H26D	115.2
Sn1—C8—H8B	108.8	H26C—C26—H26D	107.8
H8A—C8—H8B	107.7	C26—C27—C28	110.7 (8)
C10—C9—C14	116.3 (3)	C26—C27—H27A	109.5
C10—C9—C8	121.5 (3)	C28—C27—H27A	109.5
C14—C9—C8	122.1 (3)	C26—C27—H27B	109.5
C11—C10—C9	121.9 (3)	C28—C27—H27B	109.5
C11—C10—H10	119.0	H27A—C27—H27B	108.1
C9—C10—H10	119.0	C29—C28—C27	110.9 (10)
C10—C11—C12	119.5 (4)	C29—C28—H28A	109.5
C10—C11—H11	120.3	C27—C28—H28A	109.5
C12—C11—H11	120.3	C29—C28—H28B	109.5
C13—C12—C11	120.6 (4)	C27—C28—H28B	109.5
C13—C12—H12	119.7	H28A—C28—H28B	108.1
C11—C12—H12	119.7	C28—C29—H29A	109.5
C12—C13—C14	118.9 (4)	C28—C29—H29B	109.5
C12—C13—H13	120.5	H29A—C29—H29B	109.5
C14—C13—H13	120.5	C28—C29—H29C	109.5
C13—C14—C9	122.8 (3)	H29A—C29—H29C	109.5
C13—C14—Cl2	118.3 (3)	H29B—C29—H29C	109.5
C9—C14—Cl2	119.0 (2)	C26—C27'—C28'	111.1 (8)
C16—C15—Sn1	112.23 (19)	C26—C27'—H27C	109.4
C16—C15—H15A	109.2	C28'—C27'—H27C	109.4
Sn1—C15—H15A	109.2	C26—C27'—H27D	109.4
C16—C15—H15B	109.2	C28'—C27'—H27D	109.4
Sn1—C15—H15B	109.2	H27C—C27'—H27D	108.0
H15A—C15—H15B	107.9	C29'—C28'—C27'	110.8 (9)
C21—C16—C17	115.8 (3)	C29'—C28'—H28C	109.5
C21—C16—C15	122.0 (3)	C27'—C28'—H28C	109.5
C17—C16—C15	122.2 (3)	C29'—C28'—H28D	109.5
C18—C17—C16	121.7 (3)	C27'—C28'—H28D	109.5
C18—C17—H17	119.1	H28C—C28'—H28D	108.1
C16—C17—H17	119.1	C28'—C29'—H29D	109.5
C19—C18—C17	120.7 (3)	C28'—C29'—H29E	109.5
C19—C18—H18	119.7	H29D—C29'—H29E	109.5
C17—C18—H18	119.7	C28'—C29'—H29F	109.5
C18—C19—C20	119.6 (3)	H29D—C29'—H29F	109.5
C18—C19—H19	120.2	H29E—C29'—H29F	109.5
C20—C19—H19	120.2

C1—Sn1—O1—C22	−65.14 (19)	C1—Sn1—C15—C16	−136.0 (2)
C15—Sn1—O1—C22	60.61 (19)	C8—Sn1—C15—C16	1.4 (3)
C8—Sn1—O1—C22	175.38 (18)	Sn1—C15—C16—C21	74.5 (3)
O1—Sn1—C1—C2	126.2 (2)	Sn1—C15—C16—C17	−102.6 (3)
C15—Sn1—C1—C2	11.9 (3)	C21—C16—C17—C18	1.7 (5)
C8—Sn1—C1—C2	−124.7 (2)	C15—C16—C17—C18	179.0 (3)
Sn1—C1—C2—C3	−84.0 (3)	C16—C17—C18—C19	−0.7 (6)
Sn1—C1—C2—C7	97.2 (3)	C17—C18—C19—C20	−0.4 (6)
C7—C2—C3—C4	1.3 (4)	C18—C19—C20—C21	0.3 (6)
C1—C2—C3—C4	−177.6 (3)	C19—C20—C21—C16	0.9 (5)
C2—C3—C4—C5	0.0 (5)	C19—C20—C21—Cl3	−178.0 (3)
C3—C4—C5—C6	−0.5 (6)	C17—C16—C21—C20	−1.8 (4)
C4—C5—C6—C7	−0.4 (6)	C15—C16—C21—C20	−179.1 (3)
C5—C6—C7—C2	1.7 (5)	C17—C16—C21—Cl3	177.0 (2)
C5—C6—C7—Cl1	−179.1 (3)	C15—C16—C21—Cl3	−0.2 (4)
C3—C2—C7—C6	−2.1 (4)	Sn1—O1—C22—O2	9.4 (3)
C1—C2—C7—C6	176.8 (3)	Sn1—O1—C22—C23	−170.59 (17)
C3—C2—C7—Cl1	178.7 (2)	O2—C22—C23—S1	−7.0 (4)
C1—C2—C7—Cl1	−2.3 (4)	O1—C22—C23—S1	173.06 (19)
O1—Sn1—C8—C9	122.2 (2)	C24—S1—C23—C22	−73.4 (2)
C1—Sn1—C8—C9	6.8 (2)	C26—N1—C24—S2	−178.4 (2)
C15—Sn1—C8—C9	−132.6 (2)	C25—N1—C24—S2	−2.0 (4)
Sn1—C8—C9—C10	111.1 (3)	C26—N1—C24—S1	0.0 (4)
Sn1—C8—C9—C14	−69.0 (3)	C25—N1—C24—S1	176.5 (2)
C14—C9—C10—C11	−1.2 (5)	C23—S1—C24—N1	175.4 (2)
C8—C9—C10—C11	178.7 (3)	C23—S1—C24—S2	−6.2 (2)
C9—C10—C11—C12	0.4 (6)	C24—N1—C26—C27'	98.0 (16)
C10—C11—C12—C13	0.5 (6)	C25—N1—C26—C27'	−78.6 (16)
C11—C12—C13—C14	−0.5 (6)	C24—N1—C26—C27	89.5 (16)
C12—C13—C14—C9	−0.4 (5)	C25—N1—C26—C27	−87.1 (16)
C12—C13—C14—Cl2	179.7 (3)	N1—C26—C27—C28	176.6 (17)
C10—C9—C14—C13	1.2 (5)	C27'—C26—C27—C28	91 (14)
C8—C9—C14—C13	−178.6 (3)	C26—C27—C28—C29	167 (2)
C10—C9—C14—Cl2	−178.9 (2)	N1—C26—C27'—C28'	−167.3 (17)
C8—C9—C14—Cl2	1.3 (4)	C27—C26—C27'—C28'	−70 (13)
O1—Sn1—C15—C16	105.2 (2)	C26—C27'—C28'—C29'	−168 (2)

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆Cl)₃(C₈H₁₄NO₂S₂)]
M_r	715.72
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.2485 (2), 11.7943 (2), 13.1704 (3)
α, β, γ (°)	84.417 (1), 84.113 (1), 86.387 (1)
V (Å³)	1573.79 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.710, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	11006, 6949, 5708
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.078, 1.03
No. of reflections	6949
No. of parameters	353
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.69

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya (RG020/09AFR and PS338/2009C) for supporting this study.

References

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