Bis{μ-2-[(N,N-diisopropyl­carbamothio­yl)sulfan­yl]acetato-κ2O:O′}bis­(bis­(4-chloro­benz­yl){2-[(N,N-diisopropyl­carbamothio­yl)sulfan­yl]acetato-κ2O,O′}tin(IV))

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

doi:10.1107/S1600536811015716

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m661

doi:10.1107/S1600536811015716

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Bis{μ-2-[(N,N-diisopropylcarbamothioyl)sulfanyl]acetato-κ²O:O′}bis(bis(4-chlorobenzyl){2-[(N,N-diisopropylcarbamothioyl)sulfanyl]acetato-κ²O,O′}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 20 April 2011; accepted 26 April 2011; online 7 May 2011)

The dinuclear title complex, [Sn₂(C₇H₆Cl)₄(C₉H₁₆NO₂S₂)₄], lies on a center of inversion. The Sn^IV atoms are chelated by one of the two carboxylate ions; the other carboxylate ion bridges two metal atoms. The geometry of the six-coordinate Sn^IV atom is a distorted trans-C₂SnO₄ octahedron [C—Sn—C = 155.32 (8)°].

Related literature

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961 ). For the synthesis of the carboxylic acid, see: Nachmias (1952 ). For a review of the crystal structures of organotin carboxylates, see: Tiekink (1991 , 1994 ).

Experimental

Crystal data

[Sn₂(C₇H₆Cl)₄(C₉H₁₆NO₂S₂)₄]
M_r = 1677.04
Triclinic, $[P \overline 1]$
a = 11.0257 (1) Å
b = 13.1588 (2) Å
c = 14.5369 (2) Å
α = 96.4464 (5)°
β = 101.0660 (5)°
γ = 112.8168 (5)°
V = 1866.82 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.773, T_max = 0.854
17479 measured reflections
8479 independent reflections
7912 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.083
S = 0.93
8479 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.40 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/S1600536811015716/bt5526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015716/bt5526Isup2.hkl

checkCIF report

Comment top

Diorganotin dicarboxylates are generally six-coordinate compounds as the carboxyl –CO₂ portion of the anion functions either in a chelating or in a bridging mode (Tiekink, 1991, 1994). The title compound (Scheme I) exists as a centrosymmetric dinuclear molecule in which the anion of one formula unit functions in a chelating mode whereas the other anion functions in a chelating mode (Fig. 1). In dinuclear [Sn(C₇H₆Cl)₂(C₉H₁₆NO₂S₂)₂]₂, the Sn^IV atom is chelated by one of the two carboxylate ions; the other carboxylate ion bridges two metal atoms. The geometry of the six-coordinate Sn^IV atom is a trans-C₂SnO₄ octahedron [C–Sn–C 155.32 (8) °]. The chelation is not isobidentate.

Related literature top

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961). For the synthesis of the carboxylic acid, see: Nachmias (1952). For a review of the crystal structures of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Di(4-chlorobenzyl)tin oxide was prepared by the base hydrolysis of di(4-chlorobenzyl)tin dichloride with 10% sodium hydroxide. The diorganotin dichloride was synthesized by the direct reaction of 4-chlorobenzyl chloride and metallic tin according to a literature procedure (Sisido et al., 1961). The carboxylic acid was synthesized by using literature procedure (Nachmias, 1952). The diorganotin oxide (0.78 g, 2 mmol) and N,N-diisopropyldithiocarbamylacetic acid (0.94 g, 2 mmol) were heated in ethanol (100 ml) for an hour until the oxide dissolved. The solution was filtered; slow evaporation of the filtrate gave colorless crystals.

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Sn(C₇H₆Cl)₂(C₉H₁₆NO₂S₂)₂]₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis{µ-2-[(N,N-diisopropylcarbamothioyl)sulfanyl]acetato- κ²O:O'}bis(bis(4-chlorobenzyl){2-[(N,N- diisopropylcarbamothioyl)sulfanyl]acetato-κ²O,O'}tin(IV)) top

Crystal data top

[Sn₂(C₇H₆Cl)₄(C₉H₁₆NO₂S₄)₂]	Z = 1
M_r = 1677.04	F(000) = 860
Triclinic, P1	D_x = 1.492 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.0257 (1) Å	Cell parameters from 9894 reflections
b = 13.1588 (2) Å	θ = 2.5–28.4°
c = 14.5369 (2) Å	µ = 1.09 mm⁻¹
α = 96.4464 (5)°	T = 100 K
β = 101.0660 (5)°	Block, colorless
γ = 112.8168 (5)°	0.25 × 0.20 × 0.15 mm
V = 1866.82 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	8479 independent reflections
Radiation source: fine-focus sealed tube	7912 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.773, T_max = 0.854	k = −17→16
17479 measured reflections	l = −18→18

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0633P)² + 1.4914P] where P = (F_o² + 2F_c²)/3
8479 reflections	(Δ/σ)_max = 0.001
406 parameters	Δρ_max = 1.36 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Sn₂(C₇H₆Cl)₄(C₉H₁₆NO₂S₄)₂]	γ = 112.8168 (5)°
M_r = 1677.04	V = 1866.82 (4) Å³
Triclinic, P1	Z = 1
a = 11.0257 (1) Å	Mo Kα radiation
b = 13.1588 (2) Å	µ = 1.09 mm⁻¹
c = 14.5369 (2) Å	T = 100 K
α = 96.4464 (5)°	0.25 × 0.20 × 0.15 mm
β = 101.0660 (5)°

Data collection top

Bruker SMART APEX diffractometer	8479 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7912 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.854	R_int = 0.014
17479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 0.93	Δρ_max = 1.36 e Å⁻³
8479 reflections	Δρ_min = −0.40 e Å⁻³
406 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.406607 (11)	0.336032 (10)	0.363697 (8)	0.01541 (5)
Cl1	0.79909 (7)	0.41135 (6)	0.03727 (5)	0.04089 (15)
Cl2	0.49005 (7)	0.19243 (6)	0.83012 (4)	0.04131 (15)
S1	0.20626 (5)	−0.00123 (4)	0.06705 (3)	0.02075 (10)
S2	0.28467 (6)	−0.04328 (4)	0.26242 (4)	0.02568 (11)
S3	0.89452 (5)	0.59366 (4)	0.67643 (3)	0.01785 (10)
S4	0.96621 (5)	0.63196 (4)	0.49095 (3)	0.01809 (10)
O1	0.47770 (14)	0.23694 (12)	0.27828 (10)	0.0198 (3)
O2	0.27222 (14)	0.21691 (12)	0.20565 (10)	0.0199 (3)
O3	0.59477 (13)	0.37482 (11)	0.46061 (10)	0.0181 (3)
O4	0.64367 (13)	0.55367 (11)	0.52227 (10)	0.0169 (3)
N1	0.05428 (17)	−0.17675 (14)	0.12945 (12)	0.0187 (3)
N2	1.08837 (17)	0.78195 (14)	0.65749 (12)	0.0200 (3)
C1	0.4573 (2)	0.47745 (16)	0.29490 (14)	0.0191 (4)
H1A	0.3730	0.4786	0.2574	0.023*
H1B	0.5066	0.5483	0.3438	0.023*
C2	0.54474 (19)	0.46880 (16)	0.22990 (14)	0.0184 (4)
C3	0.4923 (2)	0.43674 (17)	0.13091 (15)	0.0215 (4)
H3	0.4018	0.4264	0.1037	0.026*
C4	0.5703 (2)	0.41951 (18)	0.07087 (15)	0.0255 (4)
H4	0.5337	0.3975	0.0034	0.031*
C5	0.7014 (2)	0.43497 (18)	0.11127 (17)	0.0264 (4)
C6	0.7578 (2)	0.46882 (18)	0.20934 (16)	0.0251 (4)
H6	0.8489	0.4800	0.2360	0.030*
C7	0.6792 (2)	0.48612 (17)	0.26803 (15)	0.0214 (4)
H7	0.7175	0.5101	0.3353	0.026*
C8	0.27651 (19)	0.20341 (16)	0.41890 (14)	0.0192 (4)
H8A	0.1884	0.2090	0.4126	0.023*
H8B	0.2584	0.1304	0.3791	0.023*
C9	0.33225 (19)	0.20376 (15)	0.52141 (14)	0.0177 (4)
C10	0.4326 (2)	0.16432 (18)	0.54665 (16)	0.0232 (4)
H10	0.4674	0.1392	0.4982	0.028*
C11	0.4821 (2)	0.16130 (19)	0.64091 (17)	0.0272 (4)
H11	0.5506	0.1348	0.6572	0.033*
C12	0.4302 (2)	0.19759 (18)	0.71133 (16)	0.0258 (4)
C13	0.3319 (2)	0.23779 (17)	0.68898 (15)	0.0232 (4)
H13	0.2976	0.2629	0.7377	0.028*
C14	0.2840 (2)	0.24098 (16)	0.59425 (15)	0.0207 (4)
H14	0.2169	0.2691	0.5787	0.025*
C15	0.37035 (19)	0.19069 (16)	0.20849 (14)	0.0185 (4)
C16	0.3714 (2)	0.10820 (17)	0.12758 (15)	0.0215 (4)
H16A	0.4317	0.0730	0.1536	0.026*
H16B	0.4107	0.1503	0.0803	0.026*
C17	0.1718 (2)	−0.08442 (16)	0.15656 (14)	0.0188 (4)
C18	0.0199 (2)	−0.26663 (17)	0.18707 (15)	0.0218 (4)
H18	−0.0696	−0.3276	0.1491	0.026*
C19	0.1204 (2)	−0.32062 (19)	0.19771 (17)	0.0281 (4)
H19A	0.1313	−0.3439	0.1345	0.042*
H19B	0.0858	−0.3866	0.2264	0.042*
H19C	0.2086	−0.2660	0.2390	0.042*
C20	−0.0031 (3)	−0.2275 (2)	0.28203 (17)	0.0324 (5)
H20A	−0.0682	−0.1936	0.2708	0.049*
H20B	0.0835	−0.1715	0.3244	0.049*
H20C	−0.0394	−0.2921	0.3121	0.049*
C21	−0.0494 (2)	−0.19933 (17)	0.03826 (14)	0.0213 (4)
H21	−0.0217	−0.1286	0.0126	0.026*
C22	−0.0516 (2)	−0.2910 (2)	−0.03654 (15)	0.0281 (4)
H22A	0.0401	−0.2707	−0.0456	0.042*
H22B	−0.1144	−0.2988	−0.0973	0.042*
H22C	−0.0820	−0.3626	−0.0149	0.042*
C23	−0.1897 (2)	−0.22522 (19)	0.05571 (16)	0.0263 (4)
H23A	−0.1834	−0.1640	0.1041	0.039*
H23B	−0.2219	−0.2960	0.0784	0.039*
H23C	−0.2537	−0.2323	−0.0042	0.039*
C24	0.66742 (17)	0.46904 (15)	0.52041 (12)	0.0144 (3)
C25	0.78688 (18)	0.46587 (15)	0.58999 (14)	0.0176 (3)
H25A	0.8435	0.4459	0.5526	0.021*
H25B	0.7510	0.4049	0.6249	0.021*
C26	0.99540 (18)	0.68054 (16)	0.60723 (14)	0.0167 (3)
C27	1.1767 (2)	0.87019 (16)	0.61264 (15)	0.0209 (4)
H27	1.2361	0.9355	0.6667	0.025*
C28	1.0951 (2)	0.91474 (17)	0.54522 (16)	0.0237 (4)
H28A	1.0353	0.9356	0.5775	0.036*
H28B	1.0400	0.8562	0.4876	0.036*
H28C	1.1575	0.9811	0.5271	0.036*
C29	1.2744 (2)	0.83578 (19)	0.56923 (18)	0.0282 (5)
H29A	1.3235	0.8079	0.6162	0.042*
H29B	1.3397	0.9012	0.5519	0.042*
H29C	1.2226	0.7762	0.5118	0.042*
C30	1.1115 (2)	0.81703 (18)	0.76301 (15)	0.0267 (4)
H30	1.0487	0.7518	0.7848	0.032*
C31	1.0746 (2)	0.9154 (2)	0.78689 (17)	0.0342 (5)
H31A	0.9812	0.8960	0.7509	0.051*
H31B	1.1373	0.9821	0.7694	0.051*
H31C	1.0818	0.9312	0.8557	0.051*
C32	1.2568 (3)	0.8413 (2)	0.81602 (17)	0.0349 (5)
H32A	1.2698	0.8646	0.8849	0.052*
H32B	1.3215	0.9018	0.7933	0.052*
H32C	1.2723	0.7732	0.8038	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01341 (8)	0.01605 (8)	0.01545 (8)	0.00530 (5)	0.00327 (5)	0.00229 (5)
Cl1	0.0447 (3)	0.0428 (3)	0.0452 (4)	0.0206 (3)	0.0307 (3)	0.0069 (3)
Cl2	0.0425 (3)	0.0562 (4)	0.0249 (3)	0.0218 (3)	0.0028 (2)	0.0132 (3)
S1	0.0221 (2)	0.0181 (2)	0.0158 (2)	0.00386 (18)	0.00156 (18)	0.00244 (17)
S2	0.0279 (3)	0.0224 (2)	0.0224 (2)	0.0108 (2)	−0.0030 (2)	0.00348 (19)
S3	0.0161 (2)	0.0179 (2)	0.0152 (2)	0.00339 (17)	0.00239 (16)	0.00325 (17)
S4	0.0186 (2)	0.0196 (2)	0.0171 (2)	0.00896 (18)	0.00526 (17)	0.00303 (17)
O1	0.0156 (6)	0.0191 (6)	0.0208 (7)	0.0053 (5)	0.0023 (5)	0.0001 (5)
O2	0.0169 (6)	0.0217 (7)	0.0207 (7)	0.0088 (5)	0.0036 (5)	0.0029 (5)
O3	0.0155 (6)	0.0164 (6)	0.0192 (6)	0.0057 (5)	0.0015 (5)	0.0002 (5)
O4	0.0149 (6)	0.0175 (6)	0.0202 (7)	0.0082 (5)	0.0055 (5)	0.0039 (5)
N1	0.0189 (8)	0.0218 (8)	0.0157 (8)	0.0091 (6)	0.0025 (6)	0.0056 (6)
N2	0.0182 (8)	0.0181 (8)	0.0202 (8)	0.0044 (6)	0.0048 (6)	0.0029 (6)
C1	0.0186 (9)	0.0193 (9)	0.0204 (9)	0.0079 (7)	0.0071 (7)	0.0046 (7)
C2	0.0183 (9)	0.0172 (8)	0.0191 (9)	0.0059 (7)	0.0064 (7)	0.0036 (7)
C3	0.0220 (9)	0.0228 (9)	0.0197 (9)	0.0091 (8)	0.0054 (8)	0.0049 (7)
C4	0.0332 (11)	0.0258 (10)	0.0185 (9)	0.0119 (9)	0.0103 (8)	0.0038 (8)
C5	0.0305 (11)	0.0235 (10)	0.0299 (11)	0.0108 (8)	0.0179 (9)	0.0071 (8)
C6	0.0194 (9)	0.0248 (10)	0.0319 (11)	0.0081 (8)	0.0098 (8)	0.0078 (8)
C7	0.0186 (9)	0.0222 (9)	0.0213 (9)	0.0058 (7)	0.0058 (7)	0.0055 (8)
C8	0.0152 (8)	0.0182 (9)	0.0219 (9)	0.0055 (7)	0.0039 (7)	0.0021 (7)
C9	0.0140 (8)	0.0150 (8)	0.0234 (9)	0.0048 (7)	0.0059 (7)	0.0045 (7)
C10	0.0207 (9)	0.0244 (10)	0.0278 (10)	0.0117 (8)	0.0086 (8)	0.0055 (8)
C11	0.0212 (10)	0.0318 (11)	0.0322 (11)	0.0145 (9)	0.0053 (8)	0.0105 (9)
C12	0.0236 (10)	0.0268 (10)	0.0234 (10)	0.0069 (8)	0.0034 (8)	0.0089 (8)
C13	0.0229 (9)	0.0225 (9)	0.0230 (10)	0.0073 (8)	0.0082 (8)	0.0043 (8)
C14	0.0196 (9)	0.0184 (9)	0.0258 (10)	0.0081 (7)	0.0086 (8)	0.0057 (8)
C15	0.0172 (8)	0.0184 (8)	0.0185 (9)	0.0061 (7)	0.0049 (7)	0.0032 (7)
C16	0.0183 (9)	0.0209 (9)	0.0205 (9)	0.0057 (7)	0.0033 (7)	−0.0014 (7)
C17	0.0204 (9)	0.0198 (9)	0.0180 (9)	0.0109 (7)	0.0037 (7)	0.0033 (7)
C18	0.0214 (9)	0.0240 (9)	0.0200 (9)	0.0078 (8)	0.0060 (7)	0.0098 (8)
C19	0.0294 (11)	0.0255 (10)	0.0333 (12)	0.0135 (9)	0.0086 (9)	0.0130 (9)
C20	0.0350 (12)	0.0403 (13)	0.0239 (11)	0.0147 (10)	0.0132 (9)	0.0086 (10)
C21	0.0197 (9)	0.0239 (9)	0.0165 (9)	0.0075 (8)	−0.0003 (7)	0.0049 (7)
C22	0.0313 (11)	0.0325 (11)	0.0186 (10)	0.0131 (9)	0.0043 (8)	0.0018 (8)
C23	0.0192 (9)	0.0289 (10)	0.0283 (11)	0.0096 (8)	0.0022 (8)	0.0048 (9)
C24	0.0112 (7)	0.0167 (8)	0.0145 (8)	0.0039 (6)	0.0052 (6)	0.0032 (7)
C25	0.0144 (8)	0.0145 (8)	0.0198 (9)	0.0037 (7)	0.0010 (7)	0.0021 (7)
C26	0.0141 (8)	0.0184 (8)	0.0194 (9)	0.0084 (7)	0.0044 (7)	0.0051 (7)
C27	0.0182 (9)	0.0179 (9)	0.0263 (10)	0.0056 (7)	0.0083 (8)	0.0059 (8)
C28	0.0235 (10)	0.0179 (9)	0.0310 (11)	0.0076 (8)	0.0101 (8)	0.0086 (8)
C29	0.0215 (10)	0.0270 (10)	0.0415 (13)	0.0123 (8)	0.0145 (9)	0.0093 (9)
C30	0.0259 (10)	0.0228 (10)	0.0185 (10)	−0.0003 (8)	0.0026 (8)	−0.0011 (8)
C31	0.0273 (11)	0.0430 (13)	0.0238 (11)	0.0110 (10)	0.0035 (9)	−0.0072 (10)
C32	0.0375 (13)	0.0333 (12)	0.0269 (11)	0.0144 (10)	−0.0040 (10)	0.0021 (9)

Geometric parameters (Å, º) top

Sn1—O3	2.1083 (13)	C12—C13	1.381 (3)
Sn1—C8	2.136 (2)	C13—C14	1.389 (3)
Sn1—C1	2.1451 (19)	C13—H13	0.9500
Sn1—O1	2.1585 (14)	C14—H14	0.9500
Sn1—O4ⁱ	2.3661 (13)	C15—C16	1.514 (3)
Sn1—O2	2.4524 (14)	C16—H16A	0.9900
Cl1—C5	1.744 (2)	C16—H16B	0.9900
Cl2—C12	1.745 (2)	C18—C20	1.520 (3)
S1—C17	1.795 (2)	C18—C19	1.525 (3)
S1—C16	1.798 (2)	C18—H18	1.0000
S2—C17	1.663 (2)	C19—H19A	0.9800
S3—C25	1.7945 (19)	C19—H19B	0.9800
S3—C26	1.805 (2)	C19—H19C	0.9800
S4—C26	1.6609 (19)	C20—H20A	0.9800
O1—C15	1.282 (2)	C20—H20B	0.9800
O2—C15	1.252 (2)	C20—H20C	0.9800
O3—C24	1.286 (2)	C21—C22	1.520 (3)
O4—C24	1.238 (2)	C21—C23	1.528 (3)
O4—Sn1ⁱ	2.3661 (13)	C21—H21	1.0000
N1—C17	1.336 (3)	C22—H22A	0.9800
N1—C21	1.489 (2)	C22—H22B	0.9800
N1—C18	1.497 (2)	C22—H22C	0.9800
N2—C26	1.341 (2)	C23—H23A	0.9800
N2—C30	1.494 (3)	C23—H23B	0.9800
N2—C27	1.503 (2)	C23—H23C	0.9800
C1—C2	1.499 (3)	C24—C25	1.517 (2)
C1—H1A	0.9900	C25—H25A	0.9900
C1—H1B	0.9900	C25—H25B	0.9900
C2—C3	1.392 (3)	C27—C28	1.521 (3)
C2—C7	1.397 (3)	C27—C29	1.529 (3)
C3—C4	1.396 (3)	C27—H27	1.0000
C3—H3	0.9500	C28—H28A	0.9800
C4—C5	1.377 (3)	C28—H28B	0.9800
C4—H4	0.9500	C28—H28C	0.9800
C5—C6	1.386 (3)	C29—H29A	0.9800
C6—C7	1.387 (3)	C29—H29B	0.9800
C6—H6	0.9500	C29—H29C	0.9800
C7—H7	0.9500	C30—C31	1.523 (3)
C8—C9	1.498 (3)	C30—C32	1.529 (3)
C8—H8A	0.9900	C30—H30	1.0000
C8—H8B	0.9900	C31—H31A	0.9800
C9—C14	1.395 (3)	C31—H31B	0.9800
C9—C10	1.400 (3)	C31—H31C	0.9800
C10—C11	1.385 (3)	C32—H32A	0.9800
C10—H10	0.9500	C32—H32B	0.9800
C11—C12	1.389 (3)	C32—H32C	0.9800
C11—H11	0.9500

O3—Sn1—C8	99.59 (6)	S2—C17—S1	119.19 (12)
O3—Sn1—C1	101.45 (6)	N1—C18—C20	112.71 (18)
C8—Sn1—C1	155.32 (8)	N1—C18—C19	112.50 (16)
O3—Sn1—O1	81.59 (5)	C20—C18—C19	113.09 (18)
C8—Sn1—O1	97.84 (7)	N1—C18—H18	105.9
C1—Sn1—O1	97.86 (6)	C20—C18—H18	105.9
O3—Sn1—O4ⁱ	89.62 (5)	C19—C18—H18	105.9
C8—Sn1—O4ⁱ	81.34 (6)	C18—C19—H19A	109.5
C1—Sn1—O4ⁱ	86.03 (6)	C18—C19—H19B	109.5
O1—Sn1—O4ⁱ	170.93 (5)	H19A—C19—H19B	109.5
O3—Sn1—O2	138.32 (5)	C18—C19—H19C	109.5
C8—Sn1—O2	85.30 (6)	H19A—C19—H19C	109.5
C1—Sn1—O2	87.52 (6)	H19B—C19—H19C	109.5
O1—Sn1—O2	56.78 (5)	C18—C20—H20A	109.5
O4ⁱ—Sn1—O2	131.86 (5)	C18—C20—H20B	109.5
C17—S1—C16	101.28 (10)	H20A—C20—H20B	109.5
C25—S3—C26	102.78 (9)	C18—C20—H20C	109.5
C15—O1—Sn1	97.25 (12)	H20A—C20—H20C	109.5
C15—O2—Sn1	84.57 (11)	H20B—C20—H20C	109.5
C24—O3—Sn1	124.97 (12)	N1—C21—C22	111.51 (17)
C24—O4—Sn1ⁱ	134.92 (12)	N1—C21—C23	111.22 (17)
C17—N1—C21	122.40 (16)	C22—C21—C23	112.33 (18)
C17—N1—C18	122.23 (16)	N1—C21—H21	107.2
C21—N1—C18	115.34 (16)	C22—C21—H21	107.2
C26—N2—C30	122.54 (17)	C23—C21—H21	107.2
C26—N2—C27	123.08 (17)	C21—C22—H22A	109.5
C30—N2—C27	114.38 (16)	C21—C22—H22B	109.5
C2—C1—Sn1	109.47 (13)	H22A—C22—H22B	109.5
C2—C1—H1A	109.8	C21—C22—H22C	109.5
Sn1—C1—H1A	109.8	H22A—C22—H22C	109.5
C2—C1—H1B	109.8	H22B—C22—H22C	109.5
Sn1—C1—H1B	109.8	C21—C23—H23A	109.5
H1A—C1—H1B	108.2	C21—C23—H23B	109.5
C3—C2—C7	118.34 (18)	H23A—C23—H23B	109.5
C3—C2—C1	121.19 (18)	C21—C23—H23C	109.5
C7—C2—C1	120.35 (18)	H23A—C23—H23C	109.5
C2—C3—C4	121.21 (19)	H23B—C23—H23C	109.5
C2—C3—H3	119.4	O4—C24—O3	124.49 (17)
C4—C3—H3	119.4	O4—C24—C25	122.89 (16)
C5—C4—C3	118.7 (2)	O3—C24—C25	112.62 (15)
C5—C4—H4	120.6	C24—C25—S3	115.96 (13)
C3—C4—H4	120.6	C24—C25—H25A	108.3
C4—C5—C6	121.64 (19)	S3—C25—H25A	108.3
C4—C5—Cl1	119.24 (18)	C24—C25—H25B	108.3
C6—C5—Cl1	119.12 (17)	S3—C25—H25B	108.3
C5—C6—C7	118.9 (2)	H25A—C25—H25B	107.4
C5—C6—H6	120.5	N2—C26—S4	126.15 (15)
C7—C6—H6	120.5	N2—C26—S3	114.39 (14)
C6—C7—C2	121.11 (19)	S4—C26—S3	119.44 (11)
C6—C7—H7	119.4	N2—C27—C28	112.35 (16)
C2—C7—H7	119.4	N2—C27—C29	113.67 (16)
C9—C8—Sn1	114.60 (13)	C28—C27—C29	113.65 (18)
C9—C8—H8A	108.6	N2—C27—H27	105.4
Sn1—C8—H8A	108.6	C28—C27—H27	105.4
C9—C8—H8B	108.6	C29—C27—H27	105.4
Sn1—C8—H8B	108.6	C27—C28—H28A	109.5
H8A—C8—H8B	107.6	C27—C28—H28B	109.5
C14—C9—C10	118.02 (19)	H28A—C28—H28B	109.5
C14—C9—C8	121.19 (17)	C27—C28—H28C	109.5
C10—C9—C8	120.77 (18)	H28A—C28—H28C	109.5
C11—C10—C9	121.24 (19)	H28B—C28—H28C	109.5
C11—C10—H10	119.4	C27—C29—H29A	109.5
C9—C10—H10	119.4	C27—C29—H29B	109.5
C10—C11—C12	119.10 (19)	H29A—C29—H29B	109.5
C10—C11—H11	120.5	C27—C29—H29C	109.5
C12—C11—H11	120.5	H29A—C29—H29C	109.5
C13—C12—C11	121.1 (2)	H29B—C29—H29C	109.5
C13—C12—Cl2	119.33 (17)	N2—C30—C31	111.48 (18)
C11—C12—Cl2	119.54 (17)	N2—C30—C32	110.90 (19)
C12—C13—C14	119.1 (2)	C31—C30—C32	112.58 (19)
C12—C13—H13	120.5	N2—C30—H30	107.2
C14—C13—H13	120.5	C31—C30—H30	107.2
C13—C14—C9	121.42 (19)	C32—C30—H30	107.2
C13—C14—H14	119.3	C30—C31—H31A	109.5
C9—C14—H14	119.3	C30—C31—H31B	109.5
O2—C15—O1	121.24 (18)	H31A—C31—H31B	109.5
O2—C15—C16	121.85 (17)	C30—C31—H31C	109.5
O1—C15—C16	116.83 (17)	H31A—C31—H31C	109.5
C15—C16—S1	114.07 (14)	H31B—C31—H31C	109.5
C15—C16—H16A	108.7	C30—C32—H32A	109.5
S1—C16—H16A	108.7	C30—C32—H32B	109.5
C15—C16—H16B	108.7	H32A—C32—H32B	109.5
S1—C16—H16B	108.7	C30—C32—H32C	109.5
H16A—C16—H16B	107.6	H32A—C32—H32C	109.5
N1—C17—S2	126.05 (15)	H32B—C32—H32C	109.5
N1—C17—S1	114.75 (14)

O3—Sn1—O1—C15	175.44 (12)	C12—C13—C14—C9	0.5 (3)
C8—Sn1—O1—C15	76.84 (12)	C10—C9—C14—C13	−0.9 (3)
C1—Sn1—O1—C15	−84.06 (12)	C8—C9—C14—C13	177.72 (18)
O2—Sn1—O1—C15	−2.27 (11)	Sn1—O2—C15—O1	−3.81 (18)
O3—Sn1—O2—C15	−1.10 (14)	Sn1—O2—C15—C16	179.68 (18)
C8—Sn1—O2—C15	−100.24 (12)	Sn1—O1—C15—O2	4.3 (2)
C1—Sn1—O2—C15	103.39 (12)	Sn1—O1—C15—C16	−178.97 (14)
O1—Sn1—O2—C15	2.31 (11)	O2—C15—C16—S1	−33.0 (2)
O4ⁱ—Sn1—O2—C15	−174.20 (10)	O1—C15—C16—S1	150.36 (15)
C8—Sn1—O3—C24	−115.23 (15)	C17—S1—C16—C15	−70.97 (16)
C1—Sn1—O3—C24	51.79 (15)	C21—N1—C17—S2	171.63 (15)
O1—Sn1—O3—C24	148.18 (15)	C18—N1—C17—S2	−10.5 (3)
O4ⁱ—Sn1—O3—C24	−34.08 (14)	C21—N1—C17—S1	−9.1 (2)
O2—Sn1—O3—C24	151.06 (13)	C18—N1—C17—S1	168.77 (14)
O3—Sn1—C1—C2	71.86 (14)	C16—S1—C17—N1	−177.62 (15)
C8—Sn1—C1—C2	−140.16 (17)	C16—S1—C17—S2	1.75 (14)
O1—Sn1—C1—C2	−11.10 (14)	C17—N1—C18—C20	68.3 (2)
O4ⁱ—Sn1—C1—C2	160.66 (13)	C21—N1—C18—C20	−113.7 (2)
O2—Sn1—C1—C2	−67.08 (13)	C17—N1—C18—C19	−61.0 (2)
Sn1—C1—C2—C3	104.94 (18)	C21—N1—C18—C19	116.98 (19)
Sn1—C1—C2—C7	−71.1 (2)	C17—N1—C21—C22	105.8 (2)
C7—C2—C3—C4	1.5 (3)	C18—N1—C21—C22	−72.1 (2)
C1—C2—C3—C4	−174.57 (19)	C17—N1—C21—C23	−127.9 (2)
C2—C3—C4—C5	−0.1 (3)	C18—N1—C21—C23	54.1 (2)
C3—C4—C5—C6	−1.1 (3)	Sn1ⁱ—O4—C24—O3	118.97 (18)
C3—C4—C5—Cl1	178.89 (16)	Sn1ⁱ—O4—C24—C25	−60.7 (2)
C4—C5—C6—C7	0.8 (3)	Sn1—O3—C24—O4	−7.9 (3)
Cl1—C5—C6—C7	−179.18 (16)	Sn1—O3—C24—C25	171.81 (11)
C5—C6—C7—C2	0.7 (3)	O4—C24—C25—S3	−0.3 (2)
C3—C2—C7—C6	−1.8 (3)	O3—C24—C25—S3	179.99 (13)
C1—C2—C7—C6	174.30 (18)	C26—S3—C25—C24	−77.30 (15)
O3—Sn1—C8—C9	22.00 (14)	C30—N2—C26—S4	−177.53 (15)
C1—Sn1—C8—C9	−126.20 (18)	C27—N2—C26—S4	3.2 (3)
O1—Sn1—C8—C9	104.73 (14)	C30—N2—C26—S3	3.3 (2)
O4ⁱ—Sn1—C8—C9	−66.14 (13)	C27—N2—C26—S3	−175.90 (14)
O2—Sn1—C8—C9	160.25 (14)	C25—S3—C26—N2	−178.38 (14)
Sn1—C8—C9—C14	104.11 (18)	C25—S3—C26—S4	2.42 (13)
Sn1—C8—C9—C10	−77.3 (2)	C26—N2—C27—C28	66.6 (2)
C14—C9—C10—C11	0.5 (3)	C30—N2—C27—C28	−112.7 (2)
C8—C9—C10—C11	−178.15 (19)	C26—N2—C27—C29	−64.3 (2)
C9—C10—C11—C12	0.4 (3)	C30—N2—C27—C29	116.4 (2)
C10—C11—C12—C13	−0.9 (3)	C26—N2—C30—C31	−115.4 (2)
C10—C11—C12—Cl2	179.14 (17)	C27—N2—C30—C31	63.9 (2)
C11—C12—C13—C14	0.5 (3)	C26—N2—C30—C32	118.3 (2)
Cl2—C12—C13—C14	−179.55 (16)	C27—N2—C30—C32	−62.4 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn₂(C₇H₆Cl)₄(C₉H₁₆NO₂S₄)₂]
M_r	1677.04
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	11.0257 (1), 13.1588 (2), 14.5369 (2)
α, β, γ (°)	96.4464 (5), 101.0660 (5), 112.8168 (5)
V (Å³)	1866.82 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.773, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	17479, 8479, 7912
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.083, 0.93
No. of reflections	8479
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −0.40

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 (grant No. RG020/09AFR) for supporting this study.

References

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