catena-Poly[[tribenzyl­tin(IV)]-μ-2-(piperidin-1-ylcarbothio­ylsulfan­yl)acetato-κ2O:O′]

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

doi:10.1107/S1600536810035221

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1222

doi:10.1107/S1600536810035221

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catena-Poly[[tribenzyltin(IV)]-μ-2-(piperidin-1-ylcarbothioylsulfanyl)acetato-κ²O:O′]

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 24 August 2010; accepted 1 September 2010; online 8 September 2010)

The Sn atom in the title polymeric compound, [Sn(C₇H₇)₃(C₈H₁₂NO₂S₂)]_n, exists in a trans-C₃O₂ trigonal-bipyramidal coordination environment in the two independent formula units. The carboxylate moiety functions in a bridging mode, linking adjacent triorganotin cations into a linear chain running along the shortest axis of the triclinic unit cell; the repeat distance of the polymer is half the a-axial length. In one formula unit, the Sn atom is displaced out of the equatorial plane in the direction of the Sn—O_covalent bond by 0.093 (4) Å and in the second molecule, the Sn atom is displaced by 0.105 (4) Å in the same direction.

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(C₇H₇)₃(C₈H₁₂NO₂S₂)]
M_r = 610.37
Triclinic, P 1
a = 10.7500 (7) Å
b = 11.3594 (7) Å
c = 12.5494 (8) Å
α = 79.494 (1)°
β = 81.890 (1)°
γ = 75.294 (1)°
V = 1450.15 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.05 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 = 0.744, T_max = 0.902
13931 measured reflections
11121 independent reflections
9448 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.03
11121 reflections
559 parameters
89 restraints
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 4513 Friedel pairs
Flack parameter: −0.01 (2)

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.146 (5)
Sn1—C8	2.153 (5)
Sn1—C15	2.152 (5)
Sn1—O1	2.268 (3)
Sn1—O4ⁱ	2.276 (3)
Sn2—C22	2.144 (5)
Sn2—C29	2.146 (5)
Sn2—C36	2.143 (5)
Sn2—O2	2.272 (3)
Sn2—O3	2.277 (4)

O1—Sn1—O4ⁱ	174.2 (1)
O2—Sn2—O3	174.4 (1)
Symmetry code: (i) x+1, y, z.

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/S1600536810035221/bt5336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035221/bt5336Isup2.hkl

checkCIF report

Comment top

Trialkyltin carboxylates are generally exists as carboxylate-bridged polymers (Ng et al., 1988). We have reported the triorganotin derivatives of dithiocarbamylacetic acids, a class plant growth hormones (Ng & Kumar Das, 1991). The title tribenzyltin derivative crystallizes as two independent formula units; both have their tin atoms in a trans-C₃SnO₂ trigonal bipyramidal coordination environment (Figs. 1 and 2.) The carboxylate portion functions in a bridging mode to link adjacent triorganotin cations into a linear chain running along the shortest axis of the triclinic unit cell (Fig. 3).

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

Pentamethylenedithiocarbomylacetic acid was synthesized from piperidine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tribenzyltin chloride was prepared by direct synthesis from benzyl 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 tribenzyltin hydroxide. The carboxylic acid (0.14 g, 0.73 mmol) and the organotin hydroxide (0.30 g, 0.73 mmol) were heated in ethanol (100 ml) for 2 hours. 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: pubCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of one of the two independent formula of Sn(C₇H₇)₃(C₈H₁₂NO₂S₂) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the second formula unit of Sn(C₇H₇)₃(C₈H₁₂NO₂S₂) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The symmetry code is given in Table 1.
	Fig. 3. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the chain structure of polymeric Sn(C₇H₇)₃(C₈H₁₂NO₂S₂) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[tribenzyltin(IV)]-µ-2-(piperidin-1-ylcarbothioylsulfanyl)acetato-κ²O:O'] top

Crystal data top

[Sn(C₇H₇)₃(C₈H₁₂NO₂S₂)]	Z = 2
M_r = 610.37	F(000) = 624
Triclinic, P1	D_x = 1.398 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7500 (7) Å	Cell parameters from 6011 reflections
b = 11.3594 (7) Å	θ = 2.3–24.8°
c = 12.5494 (8) Å	µ = 1.05 mm⁻¹
α = 79.494 (1)°	T = 293 K
β = 81.890 (1)°	Wedge, yellow
γ = 75.294 (1)°	0.30 × 0.20 × 0.10 mm
V = 1450.15 (16) Å³

Data collection top

Bruker SMART APEX diffractometer	11121 independent reflections
Radiation source: fine-focus sealed tube	9448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.744, T_max = 0.902	k = −14→13
13931 measured reflections	l = −16→15

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0488P)² + ] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
11121 reflections	Δρ_max = 0.75 e Å⁻³
559 parameters	Δρ_min = −0.41 e Å⁻³
89 restraints	Absolute structure: Flack (1983), 4513 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

Crystal data top

[Sn(C₇H₇)₃(C₈H₁₂NO₂S₂)]	γ = 75.294 (1)°
M_r = 610.37	V = 1450.15 (16) Å³
Triclinic, P1	Z = 2
a = 10.7500 (7) Å	Mo Kα radiation
b = 11.3594 (7) Å	µ = 1.05 mm⁻¹
c = 12.5494 (8) Å	T = 293 K
α = 79.494 (1)°	0.30 × 0.20 × 0.10 mm
β = 81.890 (1)°

Data collection top

Bruker SMART APEX diffractometer	11121 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	9448 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.902	R_int = 0.020
13931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.75 e Å⁻³
S = 1.03	Δρ_min = −0.41 e Å⁻³
11121 reflections	Absolute structure: Flack (1983), 4513 Friedel pairs
559 parameters	Absolute structure parameter: −0.01 (2)
89 restraints

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

	x	y	z	U_iso*/U_eq
Sn1	0.49998 (2)	0.49997 (2)	1.00002 (2)	0.04882 (10)
Sn2	−0.01462 (2)	0.60583 (2)	0.92111 (2)	0.04867 (10)
S1	0.21418 (18)	0.20712 (15)	1.19010 (12)	0.0717 (4)
S2	0.1212 (3)	0.4148 (2)	1.31804 (19)	0.1085 (7)
S3	−0.39487 (16)	0.89805 (15)	0.73173 (13)	0.0716 (4)
S4	−0.3672 (4)	0.7164 (3)	0.5797 (3)	0.1691 (17)
O1	0.3468 (3)	0.3924 (4)	1.0643 (3)	0.0622 (9)
O2	0.1838 (3)	0.5164 (4)	0.9783 (3)	0.0584 (9)
O3	−0.2056 (3)	0.7115 (3)	0.8561 (3)	0.0627 (9)
O4	−0.3317 (3)	0.5915 (4)	0.9437 (3)	0.0560 (9)
N1	0.2493 (5)	0.1888 (5)	1.3937 (4)	0.0744 (13)
N2	−0.3464 (10)	0.9487 (7)	0.5250 (5)	0.134 (4)
C1	0.6270 (5)	0.3575 (5)	1.0974 (5)	0.0630 (14)
H1A	0.6022	0.2803	1.1012	0.076*
H1B	0.7144	0.3480	1.0619	0.076*
C2	0.6259 (4)	0.3822 (4)	1.2114 (3)	0.0600 (13)
C3	0.7312 (4)	0.4127 (5)	1.2428 (4)	0.089 (2)
H3	0.8039	0.4166	1.1936	0.106*
C4	0.7280 (6)	0.4374 (5)	1.3478 (5)	0.136 (4)
H4	0.7984	0.4578	1.3688	0.163*
C5	0.6194 (7)	0.4316 (5)	1.4213 (3)	0.123 (3)
H5	0.6172	0.4481	1.4916	0.147*
C6	0.5141 (5)	0.4011 (5)	1.3899 (3)	0.109 (3)
H6	0.4414	0.3972	1.4391	0.131*
C7	0.5173 (3)	0.3764 (5)	1.2850 (4)	0.0745 (17)
H7	0.4469	0.3560	1.2639	0.089*
C8	0.3774 (5)	0.6484 (5)	1.0777 (5)	0.0651 (14)
H8A	0.3061	0.6859	1.0338	0.078*
H8B	0.3411	0.6123	1.1474	0.078*
C9	0.4324 (4)	0.7496 (3)	1.0979 (4)	0.0598 (17)
C10	0.5249 (4)	0.7246 (3)	1.1711 (4)	0.0809 (18)
H10	0.5523	0.6450	1.2075	0.097*
C11	0.5763 (4)	0.8186 (5)	1.1901 (4)	0.107 (3)
H11	0.6381	0.8019	1.2391	0.129*
C12	0.5353 (5)	0.9376 (4)	1.1359 (5)	0.106 (3)
H12	0.5698	1.0005	1.1486	0.128*
C13	0.4429 (5)	0.9626 (3)	1.0626 (4)	0.093 (2)
H13	0.4155	1.0423	1.0263	0.112*
C14	0.3915 (4)	0.8687 (4)	1.0436 (3)	0.0708 (18)
H14	0.3296	0.8854	0.9946	0.085*
C15	0.4934 (5)	0.4621 (5)	0.8392 (5)	0.0613 (13)
H15A	0.4104	0.4456	0.8342	0.074*
H15B	0.5030	0.5335	0.7859	0.074*
C16	0.5989 (3)	0.3537 (4)	0.8154 (3)	0.0635 (15)
C17	0.5921 (5)	0.2361 (4)	0.8673 (4)	0.078 (2)
H17	0.5208	0.2248	0.9160	0.093*
C18	0.6917 (7)	0.1354 (3)	0.8465 (5)	0.118 (3)
H18	0.6872	0.0568	0.8813	0.142*
C19	0.7982 (5)	0.1523 (5)	0.7738 (5)	0.129 (4)
H19	0.8649	0.0849	0.7599	0.155*
C20	0.8050 (4)	0.2698 (7)	0.7219 (4)	0.128 (4)
H20	0.8762	0.2811	0.6732	0.153*
C21	0.7053 (4)	0.3705 (5)	0.7427 (3)	0.0796 (18)
H21	0.7099	0.4492	0.7079	0.096*
C22	0.0666 (6)	0.7431 (5)	0.8139 (5)	0.0632 (14)
H22A	0.0015	0.8201	0.8073	0.076*
H22B	0.1378	0.7559	0.8465	0.076*
C23	0.1147 (3)	0.7116 (4)	0.7022 (3)	0.0615 (13)
C24	0.2466 (3)	0.6838 (4)	0.6700 (4)	0.0773 (17)
H24	0.3047	0.6898	0.7160	0.093*
C25	0.2918 (4)	0.6470 (5)	0.5690 (4)	0.108 (3)
H25	0.3801	0.6284	0.5475	0.129*
C26	0.2050 (6)	0.6381 (5)	0.5003 (3)	0.120 (3)
H26	0.2353	0.6135	0.4327	0.144*
C27	0.0731 (6)	0.6659 (6)	0.5325 (4)	0.110 (3)
H27	0.0151	0.6599	0.4865	0.132*
C28	0.0279 (3)	0.7027 (5)	0.6335 (4)	0.087 (2)
H28	−0.0603	0.7213	0.6550	0.104*
C29	−0.0347 (5)	0.4565 (5)	0.8470 (5)	0.0593 (13)
H29A	−0.1040	0.4237	0.8901	0.071*
H29B	−0.0643	0.4919	0.7760	0.071*
C30	0.0768 (3)	0.3491 (3)	0.8305 (3)	0.0507 (14)
C31	0.0646 (4)	0.2318 (4)	0.8786 (3)	0.0695 (18)
H31	−0.0126	0.2207	0.9182	0.083*
C32	0.1677 (5)	0.1309 (3)	0.8674 (4)	0.089 (2)
H32	0.1596	0.0523	0.8996	0.107*
C33	0.2831 (4)	0.1474 (4)	0.8082 (4)	0.095 (2)
H33	0.3521	0.0799	0.8007	0.114*
C34	0.2952 (3)	0.2648 (4)	0.7601 (3)	0.0807 (19)
H34	0.3724	0.2758	0.7205	0.097*
C35	0.1921 (4)	0.3656 (3)	0.7713 (3)	0.0643 (14)
H35	0.2002	0.4442	0.7392	0.077*
C36	−0.0906 (6)	0.6499 (5)	1.0801 (5)	0.0614 (13)
H36A	−0.1839	0.6630	1.0875	0.074*
H36B	−0.0568	0.5812	1.1347	0.074*
C37	−0.0549 (4)	0.7638 (3)	1.0994 (3)	0.0590 (14)
C38	−0.1172 (4)	0.8787 (4)	1.0485 (3)	0.079 (2)
H38	−0.1827	0.8853	1.0052	0.095*
C39	−0.0815 (5)	0.9838 (3)	1.0626 (4)	0.092 (2)
H39	−0.1232	1.0607	1.0286	0.110*
C40	0.0164 (5)	0.9740 (4)	1.1274 (4)	0.100 (3)
H40	0.0403	1.0443	1.1368	0.120*
C41	0.0787 (4)	0.8591 (5)	1.1783 (4)	0.097 (3)
H41	0.1442	0.8525	1.2217	0.116*
C42	0.0430 (3)	0.7540 (4)	1.1642 (3)	0.0714 (16)
H42	0.0846	0.6771	1.1982	0.086*
C43	0.2326 (5)	0.4219 (5)	1.0437 (4)	0.0537 (12)
C44	0.1470 (6)	0.3360 (7)	1.0941 (5)	0.0790 (19)
H44A	0.1204	0.3053	1.0359	0.095*
H44B	0.0697	0.3836	1.1301	0.095*
C45	0.1957 (6)	0.2699 (5)	1.3110 (4)	0.0643 (14)
C46	0.3030 (8)	0.0580 (7)	1.3936 (6)	0.114 (3)
H46A	0.3822	0.0314	1.4291	0.136*
H46B	0.3222	0.0401	1.3196	0.136*
C47	0.2029 (11)	−0.0070 (9)	1.4547 (8)	0.159 (4)
H47A	0.1210	0.0250	1.4236	0.190*
H47B	0.2302	−0.0947	1.4522	0.190*
C48	0.1908 (11)	0.0177 (7)	1.5682 (6)	0.157 (5)
H48A	0.1386	−0.0326	1.6158	0.188*
H48B	0.2753	−0.0010	1.5945	0.188*
C49	0.1281 (6)	0.1499 (7)	1.5662 (6)	0.106 (3)
H49A	0.1060	0.1693	1.6397	0.128*
H49B	0.0499	0.1715	1.5296	0.128*
C50	0.2245 (7)	0.2179 (7)	1.5054 (5)	0.094 (2)
H50A	0.1911	0.3058	1.5043	0.113*
H50B	0.3040	0.1929	1.5404	0.113*
C51	−0.3112 (4)	0.6835 (5)	0.8757 (4)	0.0492 (11)
C52	−0.4235 (5)	0.7622 (6)	0.8183 (5)	0.0753 (17)
H52A	−0.4947	0.7864	0.8726	0.090*
H52B	−0.4506	0.7126	0.7747	0.090*
C53	−0.3661 (9)	0.8566 (8)	0.6014 (5)	0.104 (3)
C54	−0.3379 (7)	1.0693 (8)	0.5407 (7)	0.099 (3)
H54A	−0.3553	1.0779	0.6172	0.119*
H54B	−0.3995	1.1332	0.5002	0.119*
C55	−0.2030 (8)	1.0779 (11)	0.4995 (7)	0.138 (4)
H55A	−0.1412	1.0080	0.5332	0.166*
H55B	−0.1864	1.1530	0.5147	0.166*
C56	−0.1936 (11)	1.0785 (10)	0.3797 (7)	0.165 (5)
H56A	−0.1136	1.0983	0.3444	0.198*
H56B	−0.2656	1.1384	0.3480	0.198*
C57	−0.1970 (9)	0.9511 (10)	0.3672 (8)	0.154 (4)
H57A	−0.1784	0.9396	0.2913	0.185*
H57B	−0.1344	0.8903	0.4093	0.185*
C58	−0.3305 (10)	0.9407 (11)	0.4087 (7)	0.154 (4)
H58A	−0.3928	1.0068	0.3709	0.184*
H58B	−0.3438	0.8627	0.3975	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04022 (18)	0.0499 (2)	0.0563 (2)	−0.01081 (16)	−0.00841 (15)	−0.00493 (17)
Sn2	0.0437 (2)	0.0493 (2)	0.0570 (2)	−0.01849 (17)	−0.00312 (16)	−0.00898 (17)
S1	0.1022 (11)	0.0663 (9)	0.0563 (8)	−0.0390 (8)	−0.0048 (7)	−0.0097 (7)
S2	0.150 (2)	0.0718 (12)	0.1005 (15)	−0.0089 (12)	−0.0197 (13)	−0.0243 (10)
S3	0.0854 (10)	0.0612 (9)	0.0606 (9)	−0.0079 (7)	−0.0045 (7)	−0.0051 (7)
S4	0.245 (4)	0.163 (3)	0.154 (3)	−0.148 (3)	0.064 (3)	−0.089 (2)
O1	0.0495 (19)	0.067 (2)	0.071 (2)	−0.0237 (17)	−0.0126 (17)	0.0073 (18)
O2	0.0448 (17)	0.068 (2)	0.065 (2)	−0.0227 (16)	−0.0094 (15)	−0.0014 (19)
O3	0.0461 (19)	0.060 (2)	0.082 (3)	−0.0172 (17)	−0.0094 (17)	−0.0016 (18)
O4	0.0423 (17)	0.066 (2)	0.062 (2)	−0.0166 (15)	−0.0087 (15)	−0.0063 (18)
N1	0.080 (3)	0.083 (4)	0.057 (3)	−0.020 (3)	−0.007 (2)	−0.003 (3)
N2	0.227 (10)	0.157 (8)	0.060 (4)	−0.126 (8)	0.020 (5)	−0.032 (4)
C1	0.048 (3)	0.061 (3)	0.073 (4)	−0.006 (2)	−0.012 (2)	0.001 (3)
C2	0.054 (3)	0.053 (3)	0.073 (4)	−0.012 (2)	−0.017 (2)	−0.001 (2)
C3	0.088 (4)	0.080 (4)	0.107 (5)	−0.031 (4)	−0.047 (4)	0.009 (4)
C4	0.163 (10)	0.119 (8)	0.157 (10)	−0.075 (7)	−0.099 (8)	0.026 (7)
C5	0.183 (10)	0.089 (6)	0.105 (7)	−0.018 (6)	−0.073 (7)	−0.010 (5)
C6	0.113 (6)	0.115 (7)	0.080 (5)	−0.002 (5)	−0.009 (5)	0.001 (5)
C7	0.076 (4)	0.071 (4)	0.075 (4)	−0.018 (3)	−0.019 (3)	0.005 (3)
C8	0.043 (2)	0.067 (4)	0.083 (4)	−0.007 (2)	0.000 (2)	−0.019 (3)
C9	0.045 (3)	0.069 (4)	0.063 (4)	−0.007 (3)	0.005 (2)	−0.020 (3)
C10	0.090 (4)	0.065 (4)	0.086 (4)	0.002 (3)	−0.030 (4)	−0.021 (3)
C11	0.094 (5)	0.114 (6)	0.125 (7)	0.006 (5)	−0.039 (5)	−0.071 (6)
C12	0.107 (6)	0.082 (5)	0.145 (8)	−0.032 (5)	0.010 (5)	−0.060 (5)
C13	0.100 (5)	0.063 (4)	0.115 (6)	−0.015 (4)	−0.009 (4)	−0.017 (4)
C14	0.074 (4)	0.056 (4)	0.080 (5)	−0.003 (3)	−0.013 (3)	−0.019 (4)
C15	0.059 (3)	0.063 (3)	0.067 (3)	−0.019 (3)	−0.019 (3)	−0.008 (3)
C16	0.065 (3)	0.069 (4)	0.068 (4)	−0.019 (3)	−0.024 (3)	−0.020 (3)
C17	0.087 (5)	0.065 (5)	0.092 (6)	−0.028 (4)	−0.030 (4)	−0.010 (4)
C18	0.148 (8)	0.075 (5)	0.138 (8)	0.014 (5)	−0.072 (7)	−0.047 (5)
C19	0.129 (8)	0.115 (7)	0.149 (9)	0.037 (6)	−0.070 (7)	−0.084 (7)
C20	0.069 (4)	0.201 (12)	0.130 (7)	−0.010 (6)	−0.003 (4)	−0.105 (8)
C21	0.073 (4)	0.101 (5)	0.078 (4)	−0.025 (4)	−0.007 (3)	−0.040 (4)
C22	0.057 (3)	0.061 (3)	0.074 (4)	−0.023 (3)	−0.003 (3)	−0.005 (3)
C23	0.053 (3)	0.058 (3)	0.071 (4)	−0.018 (2)	−0.004 (2)	0.001 (3)
C24	0.058 (3)	0.073 (4)	0.092 (5)	−0.021 (3)	0.007 (3)	0.005 (3)
C25	0.089 (5)	0.095 (6)	0.117 (7)	−0.012 (4)	0.036 (5)	−0.009 (5)
C26	0.138 (8)	0.127 (7)	0.081 (6)	−0.025 (6)	0.028 (5)	−0.014 (5)
C27	0.143 (8)	0.133 (8)	0.062 (5)	−0.048 (6)	−0.016 (5)	−0.009 (5)
C28	0.071 (4)	0.103 (6)	0.080 (5)	−0.019 (4)	−0.013 (3)	0.006 (4)
C29	0.054 (3)	0.056 (3)	0.077 (4)	−0.018 (2)	−0.015 (2)	−0.019 (3)
C30	0.054 (3)	0.049 (3)	0.055 (3)	−0.014 (2)	−0.016 (2)	−0.012 (3)
C31	0.080 (4)	0.064 (5)	0.064 (4)	−0.017 (3)	−0.014 (3)	0.000 (3)
C32	0.114 (6)	0.068 (4)	0.081 (5)	−0.003 (4)	−0.030 (4)	−0.011 (3)
C33	0.091 (5)	0.087 (5)	0.095 (5)	0.028 (4)	−0.037 (4)	−0.033 (4)
C34	0.063 (4)	0.108 (6)	0.082 (4)	−0.021 (3)	−0.011 (3)	−0.042 (4)
C35	0.055 (3)	0.075 (4)	0.071 (4)	−0.021 (3)	−0.005 (2)	−0.027 (3)
C36	0.058 (3)	0.068 (4)	0.064 (3)	−0.026 (3)	0.001 (2)	−0.015 (3)
C37	0.061 (3)	0.066 (4)	0.055 (3)	−0.027 (3)	0.011 (3)	−0.018 (3)
C38	0.099 (6)	0.070 (5)	0.072 (5)	−0.023 (5)	−0.011 (4)	−0.015 (4)
C39	0.128 (6)	0.077 (5)	0.083 (5)	−0.053 (4)	−0.001 (4)	−0.012 (4)
C40	0.116 (6)	0.096 (6)	0.110 (6)	−0.066 (5)	0.030 (5)	−0.048 (5)
C41	0.065 (4)	0.143 (8)	0.106 (6)	−0.042 (4)	0.005 (4)	−0.066 (6)
C42	0.054 (3)	0.088 (4)	0.078 (4)	−0.015 (3)	−0.004 (3)	−0.031 (3)
C43	0.051 (2)	0.071 (3)	0.049 (3)	−0.029 (2)	−0.006 (2)	−0.012 (2)
C44	0.080 (4)	0.112 (5)	0.063 (4)	−0.060 (4)	−0.024 (3)	0.004 (3)
C45	0.077 (3)	0.069 (3)	0.054 (3)	−0.032 (3)	−0.006 (2)	−0.006 (3)
C46	0.111 (5)	0.111 (6)	0.102 (6)	0.011 (5)	−0.027 (4)	−0.012 (5)
C47	0.197 (9)	0.123 (7)	0.159 (8)	−0.056 (7)	−0.004 (7)	−0.014 (6)
C48	0.176 (8)	0.167 (9)	0.119 (7)	−0.054 (7)	−0.005 (6)	0.012 (6)
C49	0.085 (4)	0.153 (7)	0.079 (4)	−0.032 (5)	0.004 (4)	−0.016 (5)
C50	0.102 (5)	0.117 (5)	0.066 (4)	−0.031 (4)	−0.019 (3)	−0.009 (4)
C51	0.042 (2)	0.052 (3)	0.054 (3)	−0.007 (2)	−0.0028 (19)	−0.014 (2)
C52	0.052 (3)	0.087 (4)	0.075 (4)	−0.013 (3)	−0.005 (3)	0.014 (3)
C53	0.134 (6)	0.140 (7)	0.069 (4)	−0.093 (6)	0.023 (4)	−0.036 (5)
C54	0.102 (5)	0.098 (5)	0.083 (5)	−0.001 (4)	0.001 (4)	−0.013 (4)
C55	0.150 (7)	0.147 (7)	0.138 (7)	−0.061 (6)	0.006 (6)	−0.054 (6)
C56	0.180 (9)	0.156 (9)	0.144 (8)	−0.046 (7)	0.030 (7)	−0.009 (7)
C57	0.163 (8)	0.177 (8)	0.113 (6)	−0.029 (7)	0.034 (6)	−0.051 (6)
C58	0.169 (8)	0.196 (9)	0.121 (7)	−0.075 (7)	−0.009 (6)	−0.048 (6)

Geometric parameters (Å, º) top

Sn1—C1	2.146 (5)	C23—C28	1.3900
Sn1—C8	2.153 (5)	C24—C25	1.3900
Sn1—C15	2.152 (5)	C24—H24	0.9300
Sn1—O1	2.268 (3)	C25—C26	1.3900
Sn1—O4ⁱ	2.276 (3)	C25—H25	0.9300
Sn2—C22	2.144 (5)	C26—C27	1.3900
Sn2—C29	2.146 (5)	C26—H26	0.9300
Sn2—C36	2.143 (5)	C27—C28	1.3900
Sn2—O2	2.272 (3)	C27—H27	0.9300
Sn2—O3	2.277 (4)	C28—H28	0.9300
S1—C45	1.757 (6)	C29—C30	1.499 (6)
S1—C44	1.784 (7)	C29—H29A	0.9700
S2—C45	1.651 (6)	C29—H29B	0.9700
S3—C53	1.748 (7)	C30—C31	1.3900
S3—C52	1.787 (6)	C30—C35	1.3900
S4—C53	1.668 (8)	C31—C32	1.3900
O1—C43	1.239 (6)	C31—H31	0.9300
O2—C43	1.270 (6)	C32—C33	1.3900
O3—C51	1.236 (6)	C32—H32	0.9300
O4—C51	1.268 (6)	C33—C34	1.3900
O4—Sn1ⁱⁱ	2.276 (3)	C33—H33	0.9300
N1—C45	1.344 (6)	C34—C35	1.3900
N1—C46	1.451 (7)	C34—H34	0.9300
N1—C50	1.471 (7)	C35—H35	0.9300
N2—C53	1.322 (7)	C36—C37	1.507 (6)
N2—C54	1.445 (8)	C36—H36A	0.9700
N2—C58	1.462 (8)	C36—H36B	0.9700
C1—C2	1.505 (7)	C37—C38	1.3900
C1—H1A	0.9700	C37—C42	1.3900
C1—H1B	0.9700	C38—C39	1.3900
C2—C3	1.3900	C38—H38	0.9300
C2—C7	1.3900	C39—C40	1.3900
C3—C4	1.3900	C39—H39	0.9300
C3—H3	0.9300	C40—C41	1.3900
C4—C5	1.3900	C40—H40	0.9300
C4—H4	0.9300	C41—C42	1.3900
C5—C6	1.3900	C41—H41	0.9300
C5—H5	0.9300	C42—H42	0.9300
C6—C7	1.3900	C43—C44	1.505 (7)
C6—H6	0.9300	C44—H44A	0.9700
C7—H7	0.9300	C44—H44B	0.9700
C8—C9	1.493 (6)	C46—C47	1.501 (5)
C8—H8A	0.9700	C46—H46A	0.9700
C8—H8B	0.9700	C46—H46B	0.9700
C9—C10	1.3900	C47—C48	1.484 (5)
C9—C14	1.3900	C47—H47A	0.9700
C10—C11	1.3900	C47—H47B	0.9700
C10—H10	0.9300	C48—C49	1.479 (5)
C11—C12	1.3900	C48—H48A	0.9700
C11—H11	0.9300	C48—H48B	0.9700
C12—C13	1.3900	C49—C50	1.490 (5)
C12—H12	0.9300	C49—H49A	0.9700
C13—C14	1.3900	C49—H49B	0.9700
C13—H13	0.9300	C50—H50A	0.9700
C14—H14	0.9300	C50—H50B	0.9700
C15—C16	1.491 (6)	C51—C52	1.496 (7)
C15—H15A	0.9700	C52—H52A	0.9700
C15—H15B	0.9700	C52—H52B	0.9700
C16—C17	1.3900	C54—C55	1.491 (5)
C16—C21	1.3900	C54—H54A	0.9700
C17—C18	1.3900	C54—H54B	0.9700
C17—H17	0.9300	C55—C56	1.491 (5)
C18—C19	1.3900	C55—H55A	0.9700
C18—H18	0.9300	C55—H55B	0.9700
C19—C20	1.3900	C56—C57	1.493 (5)
C19—H19	0.9300	C56—H56A	0.9700
C20—C21	1.3900	C56—H56B	0.9700
C20—H20	0.9300	C57—C58	1.483 (5)
C21—H21	0.9300	C57—H57A	0.9700
C22—C23	1.498 (7)	C57—H57B	0.9700
C22—H22A	0.9700	C58—H58A	0.9700
C22—H22B	0.9700	C58—H58B	0.9700
C23—C24	1.3900

C1—Sn1—C15	114.1 (2)	Sn2—C29—H29A	107.0
C1—Sn1—C8	117.9 (2)	C30—C29—H29B	107.0
C15—Sn1—C8	127.4 (2)	Sn2—C29—H29B	107.0
C1—Sn1—O1	86.11 (19)	H29A—C29—H29B	106.7
C15—Sn1—O1	89.25 (19)	C31—C30—C35	120.0
C8—Sn1—O1	87.04 (18)	C31—C30—C29	118.8 (3)
C1—Sn1—O4ⁱ	88.16 (19)	C35—C30—C29	121.2 (3)
C15—Sn1—O4ⁱ	92.35 (18)	C30—C31—C32	120.0
C8—Sn1—O4ⁱ	96.38 (18)	C30—C31—H31	120.0
O1—Sn1—O4ⁱ	174.2 (1)	C32—C31—H31	120.0
C36—Sn2—C22	115.6 (2)	C31—C32—C33	120.0
C36—Sn2—C29	128.4 (2)	C31—C32—H32	120.0
C22—Sn2—C29	115.3 (2)	C33—C32—H32	120.0
C36—Sn2—O2	91.43 (19)	C34—C33—C32	120.0
C22—Sn2—O2	89.20 (19)	C34—C33—H33	120.0
C29—Sn2—O2	97.31 (17)	C32—C33—H33	120.0
C36—Sn2—O3	89.8 (2)	C33—C34—C35	120.0
C22—Sn2—O3	85.38 (19)	C33—C34—H34	120.0
C29—Sn2—O3	86.15 (17)	C35—C34—H34	120.0
O2—Sn2—O3	174.4 (1)	C34—C35—C30	120.0
C45—S1—C44	103.2 (3)	C34—C35—H35	120.0
C53—S3—C52	103.8 (4)	C30—C35—H35	120.0
C43—O1—Sn1	126.5 (3)	C37—C36—Sn2	111.3 (3)
C43—O2—Sn2	136.4 (3)	C37—C36—H36A	109.4
C51—O3—Sn2	127.9 (3)	Sn2—C36—H36A	109.4
C51—O4—Sn1ⁱⁱ	136.4 (3)	C37—C36—H36B	109.4
C45—N1—C46	126.1 (6)	Sn2—C36—H36B	109.4
C45—N1—C50	120.7 (6)	H36A—C36—H36B	108.0
C46—N1—C50	110.9 (5)	C38—C37—C42	120.0
C53—N2—C54	127.1 (6)	C38—C37—C36	119.6 (4)
C53—N2—C58	122.9 (7)	C42—C37—C36	120.3 (4)
C54—N2—C58	110.0 (7)	C37—C38—C39	120.0
C2—C1—Sn1	113.6 (3)	C37—C38—H38	120.0
C2—C1—H1A	108.8	C39—C38—H38	120.0
Sn1—C1—H1A	108.8	C38—C39—C40	120.0
C2—C1—H1B	108.8	C38—C39—H39	120.0
Sn1—C1—H1B	108.8	C40—C39—H39	120.0
H1A—C1—H1B	107.7	C39—C40—C41	120.0
C3—C2—C7	120.0	C39—C40—H40	120.0
C3—C2—C1	120.6 (4)	C41—C40—H40	120.0
C7—C2—C1	119.4 (4)	C42—C41—C40	120.0
C2—C3—C4	120.0	C42—C41—H41	120.0
C2—C3—H3	120.0	C40—C41—H41	120.0
C4—C3—H3	120.0	C41—C42—C37	120.0
C3—C4—C5	120.0	C41—C42—H42	120.0
C3—C4—H4	120.0	C37—C42—H42	120.0
C5—C4—H4	120.0	O1—C43—O2	124.8 (5)
C6—C5—C4	120.0	O1—C43—C44	117.9 (5)
C6—C5—H5	120.0	O2—C43—C44	117.2 (5)
C4—C5—H5	120.0	C43—C44—S1	116.9 (4)
C5—C6—C7	120.0	C43—C44—H44A	108.1
C5—C6—H6	120.0	S1—C44—H44A	108.1
C7—C6—H6	120.0	C43—C44—H44B	108.1
C6—C7—C2	120.0	S1—C44—H44B	108.1
C6—C7—H7	120.0	H44A—C44—H44B	107.3
C2—C7—H7	120.0	N1—C45—S2	125.0 (5)
C9—C8—Sn1	119.7 (3)	N1—C45—S1	113.2 (5)
C9—C8—H8A	107.4	S2—C45—S1	121.9 (3)
Sn1—C8—H8A	107.4	N1—C46—C47	106.8 (7)
C9—C8—H8B	107.4	N1—C46—H46A	110.4
Sn1—C8—H8B	107.4	C47—C46—H46A	110.4
H8A—C8—H8B	106.9	N1—C46—H46B	110.4
C10—C9—C14	120.0	C47—C46—H46B	110.4
C10—C9—C8	119.8 (4)	H46A—C46—H46B	108.6
C14—C9—C8	120.2 (4)	C48—C47—C46	105.3 (4)
C11—C10—C9	120.0	C48—C47—H47A	110.7
C11—C10—H10	120.0	C46—C47—H47A	110.7
C9—C10—H10	120.0	C48—C47—H47B	110.7
C10—C11—C12	120.0	C46—C47—H47B	110.7
C10—C11—H11	120.0	H47A—C47—H47B	108.8
C12—C11—H11	120.0	C49—C48—C47	106.6 (5)
C13—C12—C11	120.0	C49—C48—H48A	110.4
C13—C12—H12	120.0	C47—C48—H48A	110.4
C11—C12—H12	120.0	C49—C48—H48B	110.4
C14—C13—C12	120.0	C47—C48—H48B	110.4
C14—C13—H13	120.0	H48A—C48—H48B	108.6
C12—C13—H13	120.0	C48—C49—C50	105.8 (4)
C13—C14—C9	120.0	C48—C49—H49A	110.6
C13—C14—H14	120.0	C50—C49—H49A	110.6
C9—C14—H14	120.0	C48—C49—H49B	110.6
C16—C15—Sn1	110.2 (3)	C50—C49—H49B	110.6
C16—C15—H15A	109.6	H49A—C49—H49B	108.7
Sn1—C15—H15A	109.6	N1—C50—C49	107.8 (5)
C16—C15—H15B	109.6	N1—C50—H50A	110.1
Sn1—C15—H15B	109.6	C49—C50—H50A	110.1
H15A—C15—H15B	108.1	N1—C50—H50B	110.1
C17—C16—C21	120.0	C49—C50—H50B	110.1
C17—C16—C15	120.1 (4)	H50A—C50—H50B	108.5
C21—C16—C15	119.9 (4)	O3—C51—O4	123.8 (4)
C18—C17—C16	120.0	O3—C51—C52	119.3 (5)
C18—C17—H17	120.0	O4—C51—C52	117.0 (4)
C16—C17—H17	120.0	C51—C52—S3	115.8 (4)
C17—C18—C19	120.0	C51—C52—H52A	108.3
C17—C18—H18	120.0	S3—C52—H52A	108.3
C19—C18—H18	120.0	C51—C52—H52B	108.3
C20—C19—C18	120.0	S3—C52—H52B	108.3
C20—C19—H19	120.0	H52A—C52—H52B	107.4
C18—C19—H19	120.0	N2—C53—S4	125.4 (6)
C19—C20—C21	120.0	N2—C53—S3	112.3 (6)
C19—C20—H20	120.0	S4—C53—S3	122.3 (4)
C21—C20—H20	120.0	N2—C54—C55	105.6 (7)
C20—C21—C16	120.0	N2—C54—H54A	110.6
C20—C21—H21	120.0	C55—C54—H54A	110.6
C16—C21—H21	120.0	N2—C54—H54B	110.6
C23—C22—Sn2	114.3 (3)	C55—C54—H54B	110.6
C23—C22—H22A	108.7	H54A—C54—H54B	108.8
Sn2—C22—H22A	108.7	C54—C55—C56	105.3 (4)
C23—C22—H22B	108.7	C54—C55—H55A	110.7
Sn2—C22—H22B	108.7	C56—C55—H55A	110.7
H22A—C22—H22B	107.6	C54—C55—H55B	110.7
C24—C23—C28	120.0	C56—C55—H55B	110.7
C24—C23—C22	120.0 (3)	H55A—C55—H55B	108.8
C28—C23—C22	119.9 (3)	C55—C56—C57	105.3 (4)
C25—C24—C23	120.0	C55—C56—H56A	110.7
C25—C24—H24	120.0	C57—C56—H56A	110.7
C23—C24—H24	120.0	C55—C56—H56B	110.7
C24—C25—C26	120.0	C57—C56—H56B	110.7
C24—C25—H25	120.0	H56A—C56—H56B	108.8
C26—C25—H25	120.0	C58—C57—C56	104.8 (4)
C27—C26—C25	120.0	C58—C57—H57A	110.8
C27—C26—H26	120.0	C56—C57—H57A	110.8
C25—C26—H26	120.0	C58—C57—H57B	110.8
C26—C27—C28	120.0	C56—C57—H57B	110.8
C26—C27—H27	120.0	H57A—C57—H57B	108.9
C28—C27—H27	120.0	N2—C58—C57	107.0 (7)
C27—C28—C23	120.0	N2—C58—H58A	110.3
C27—C28—H28	120.0	C57—C58—H58A	110.3
C23—C28—H28	120.0	N2—C58—H58B	110.3
C30—C29—Sn2	121.3 (3)	C57—C58—H58B	110.3
C30—C29—H29A	107.0	H58A—C58—H58B	108.6

C1—Sn1—O1—C43	178.3 (5)	C29—Sn2—C36—C37	−179.3 (3)
C15—Sn1—O1—C43	−67.5 (5)	O2—Sn2—C36—C37	80.2 (4)
C8—Sn1—O1—C43	60.0 (5)	O3—Sn2—C36—C37	−94.4 (4)
C36—Sn2—O2—C43	66.6 (5)	Sn2—C36—C37—C38	74.1 (4)
C22—Sn2—O2—C43	−177.8 (5)	Sn2—C36—C37—C42	−103.4 (4)
C29—Sn2—O2—C43	−62.5 (5)	C36—C37—C38—C39	−177.6 (4)
C36—Sn2—O3—C51	−69.4 (5)	C36—C37—C42—C41	177.5 (4)
C22—Sn2—O3—C51	174.9 (5)	Sn1—O1—C43—O2	3.2 (8)
C29—Sn2—O3—C51	59.2 (5)	Sn1—O1—C43—C44	179.3 (4)
C15—Sn1—C1—C2	−177.2 (3)	Sn2—O2—C43—O1	−178.1 (4)
C8—Sn1—C1—C2	−5.2 (5)	Sn2—O2—C43—C44	5.8 (8)
O1—Sn1—C1—C2	−89.8 (4)	O1—C43—C44—S1	6.2 (8)
O4ⁱ—Sn1—C1—C2	91.0 (4)	O2—C43—C44—S1	−177.4 (4)
Sn1—C1—C2—C3	−108.5 (4)	C45—S1—C44—C43	81.4 (5)
Sn1—C1—C2—C7	70.4 (4)	C46—N1—C45—S2	172.9 (6)
C1—C2—C3—C4	178.9 (4)	C50—N1—C45—S2	11.4 (8)
C1—C2—C7—C6	−178.9 (4)	C46—N1—C45—S1	−8.0 (8)
C1—Sn1—C8—C9	78.6 (5)	C50—N1—C45—S1	−169.5 (4)
C15—Sn1—C8—C9	−110.6 (4)	C44—S1—C45—N1	−175.5 (4)
O1—Sn1—C8—C9	162.6 (4)	C44—S1—C45—S2	3.7 (5)
O4ⁱ—Sn1—C8—C9	−12.7 (4)	C45—N1—C46—C47	−100.7 (7)
Sn1—C8—C9—C10	−66.2 (5)	C50—N1—C46—C47	62.3 (8)
Sn1—C8—C9—C14	113.8 (4)	N1—C46—C47—C48	−65.1 (8)
C8—C9—C10—C11	180.0 (4)	C46—C47—C48—C49	69.7 (8)
C8—C9—C14—C13	−180.0 (4)	C47—C48—C49—C50	−68.5 (7)
C1—Sn1—C15—C16	−11.3 (4)	C45—N1—C50—C49	102.6 (7)
C8—Sn1—C15—C16	177.6 (3)	C46—N1—C50—C49	−61.5 (7)
O1—Sn1—C15—C16	−96.7 (4)	C48—C49—C50—N1	62.7 (7)
O4ⁱ—Sn1—C15—C16	77.7 (4)	Sn2—O3—C51—O4	4.9 (7)
Sn1—C15—C16—C17	71.6 (4)	Sn2—O3—C51—C52	−175.9 (4)
Sn1—C15—C16—C21	−107.2 (3)	Sn1ⁱⁱ—O4—C51—O3	−176.3 (4)
C15—C16—C17—C18	−178.7 (4)	Sn1ⁱⁱ—O4—C51—C52	4.5 (8)
C15—C16—C21—C20	178.7 (4)	O3—C51—C52—S3	−4.3 (8)
C36—Sn2—C22—C23	−178.0 (4)	O4—C51—C52—S3	175.0 (4)
C29—Sn2—C22—C23	−6.9 (5)	C53—S3—C52—C51	99.4 (6)
O2—Sn2—C22—C23	90.8 (4)	C54—N2—C53—S4	−176.5 (8)
O3—Sn2—C22—C23	−90.4 (4)	C58—N2—C53—S4	4.0 (16)
Sn2—C22—C23—C24	−110.2 (4)	C54—N2—C53—S3	4.6 (14)
Sn2—C22—C23—C28	65.8 (5)	C58—N2—C53—S3	−174.9 (8)
C22—C23—C24—C25	175.9 (4)	C52—S3—C53—N2	178.2 (7)
C36—Sn2—C29—C30	−107.8 (4)	C52—S3—C53—S4	−0.8 (7)
C22—Sn2—C29—C30	82.4 (5)	C53—N2—C54—C55	115.4 (11)
O2—Sn2—C29—C30	−10.1 (4)	C58—N2—C54—C55	−65.0 (10)
O3—Sn2—C29—C30	165.5 (4)	N2—C54—C55—C56	66.8 (8)
Sn2—C29—C30—C31	121.0 (3)	C54—C55—C56—C57	−70.3 (9)
Sn2—C29—C30—C35	−57.1 (5)	C55—C56—C57—C58	69.0 (8)
C29—C30—C31—C32	−178.1 (4)	C53—N2—C58—C57	−115.4 (10)
C29—C30—C35—C34	178.1 (4)	C54—N2—C58—C57	65.0 (11)
C22—Sn2—C36—C37	−9.6 (5)	C56—C57—C58—N2	−65.2 (10)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₇)₃(C₈H₁₂NO₂S₂)]
M_r	610.37
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.7500 (7), 11.3594 (7), 12.5494 (8)
α, β, γ (°)	79.494 (1), 81.890 (1), 75.294 (1)
V (Å³)	1450.15 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
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	0.744, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	13931, 11121, 9448
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.03
No. of reflections	11121
No. of parameters	559
No. of restraints	89
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.41
Absolute structure	Flack (1983), 4513 Friedel pairs
Absolute structure parameter	−0.01 (2)

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

Selected geometric parameters (Å, º) top

Sn1—C1	2.146 (5)	Sn2—C22	2.144 (5)
Sn1—C8	2.153 (5)	Sn2—C29	2.146 (5)
Sn1—C15	2.152 (5)	Sn2—C36	2.143 (5)
Sn1—O1	2.268 (3)	Sn2—O2	2.272 (3)
Sn1—O4ⁱ	2.276 (3)	Sn2—O3	2.277 (4)

O1—Sn1—O4ⁱ	174.2 (1)	O2—Sn2—O3	174.4 (1)

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

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