(μ-Piperazine-1,4-dicarbodithioato-κ4S,S′:S′′,S′′′)bis­[triphenyl­tin(IV)] dichloro­methane solvate

Poplaukhin, P.; Tiekink, E.R.T.

doi:10.1107/S1600536808025890

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1177

doi:10.1107/S1600536808025890

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(μ-Piperazine-1,4-dicarbodithioato-κ⁴S,S′:S′′,S′′′)bis[triphenyltin(IV)] dichloromethane solvate

Pavel Poplaukhin ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698, USA
^*Correspondence e-mail: edward.tiekink@utsa.edu

(Received 1 August 2008; accepted 11 August 2008; online 16 August 2008)

The dinuclear centrosymmetric title compound, [Sn₂(C₆H₅)₆(C₆H₈N₂S₄)]·CH₂Cl₂, features a distorted cis-trigonal–bipyramidal coordination geometry for Sn based on a C₃S₂ donor set. The dinuclear molecule lies across a centre of inversion. The solvent dichloromethane molecule is disordered about a centre of inversion.

Related literature

For a review of tin dithiocarbamates, see: Tiekink (2008 ). For a related structure, see: Yin et al. (2002 ). For analysis of trigonal–bipyramidal geometries, see: Addison et al. (1984 ).

Experimental

Crystal data

[Sn₂(C₆H₅)₆(C₆H₈N₂S₄)]·CH₂Cl₂
M_r = 1021.37
Monoclinic, P 2₁ /c
a = 14.681 (5) Å
b = 10.758 (3) Å
c = 13.470 (4) Å
β = 90.379 (6)°
V = 2127.3 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 98 (2) K
0.35 × 0.15 × 0.01 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.354, T_max = 1 (expected range = 0.346–0.977)
14400 measured reflections
4389 independent reflections
4021 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.113
S = 1.10
4389 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −1.12 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025890/ng2481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025890/ng2481Isup2.hkl

checkCIF report

Comment top

Tin dithiocarbamates continue to attract interest owing to their variety of applications (Tiekink, 2008). The title compound, Ph₃SnS₂CN(CH₂CH₂)₂NCS₂SnPh₃, has been reported previously as a methanol solvate (Yin et al., 2002). The present structure (I) has been isolated as a dichloromethane solvate, Fig. 1. The molecule is centrosymmetric so that the Ph₃Sn entities lie to either side of the pyrrolidine ring which adopts a chair conformation. The dithiocarbamate ligand coordinates in an asymmetric mode, forming Sn—S1 and Sn—S2 distances of 2.4699 (13) and 3.0715 (13) Å, respectively. The coordination geometry is based on a distorted trigonal bipyramid as indicated by the value of τ = 0.64 (Addison et al., 1984).

Related literature top

For a review of tin dithiocarbamates, see: Tiekink (2008). For a related structure, see: Yin et al. (2002). For analysis of trigonal–bipyramidal geometries, see: Addison et al. (1984).

Experimental top

The title compound was prepared by following a literature procedure (Yin et al., 2002). Colourless crystals were isolated by the slow evaporation of a dichloromethane solution of (I); m.p. 487–489 K (crystal turned opaque at 363–368 K). TGA: two steps, First mass loss 7.2% (onset 388.3 K, midpoint 392.6 K, endset 396.9 K) corresponds to loss CH₂Cl₂ (8.2% theoretical). Second mass loss 69.3% (onset 558.5 K, midpoint 620 K, endset 680 K), corresponds to decomposition to SnS (total experimental mass loss 76.5% cf. theoretical value 70.5%). IR (cm^-1): 1427, 1416 (strong, C═N), 1214 (strong, C—S).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008.

Figures top

Fig. 1. Molecular structure of (I) showing the crystallographic numbering scheme. Displacement ellipsoids are shown at the 70% probability level. Unlabelled atoms are related by the symmetry operation i: -x, 1-y, 1-z. The disordered dichloromethane molecule is omitted.

(µ-Piperazine-1,4-dicarbodithioto- κ⁴S,S':S'',S''')bis[triphenyltin(IV)] dichloromethane solvate top

Crystal data top

[Sn₂(C₆H₅)₆(C₆H₈N₂S₄)]·CH₂Cl₂	F(000) = 1020
M_r = 1021.37	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 13756 reflections
a = 14.681 (5) Å	θ = 2.4–40.7°
b = 10.758 (3) Å	µ = 1.53 mm⁻¹
c = 13.470 (4) Å	T = 98 K
β = 90.379 (6)°	Plate, colourless
V = 2127.3 (11) Å³	0.35 × 0.15 × 0.02 mm
Z = 2

Data collection top

Rigaku AFC12κ/SATURN724 diffractometer	4389 independent reflections
Radiation source: fine-focus sealed tube	4021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 26.5°, θ_min = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→18
T_min = 0.354, T_max = 1	k = −13→13
14400 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.04P)² + 8.4194P] where P = (F_o² + 2F_c²)/3
4389 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

[Sn₂(C₆H₅)₆(C₆H₈N₂S₄)]·CH₂Cl₂	V = 2127.3 (11) Å³
M_r = 1021.37	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.681 (5) Å	µ = 1.53 mm⁻¹
b = 10.758 (3) Å	T = 98 K
c = 13.470 (4) Å	0.35 × 0.15 × 0.02 mm
β = 90.379 (6)°

Data collection top

Rigaku AFC12κ/SATURN724 diffractometer	4389 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4021 reflections with I > 2σ(I)
T_min = 0.354, T_max = 1	R_int = 0.048
14400 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.10	Δρ_max = 0.77 e Å⁻³
4389 reflections	Δρ_min = −1.12 e Å⁻³
244 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn	0.23132 (2)	0.37950 (3)	0.17164 (2)	0.02056 (11)
S1	0.10733 (8)	0.32408 (10)	0.28651 (9)	0.0237 (3)
S2	0.12861 (8)	0.59723 (11)	0.26696 (9)	0.0244 (3)
N1	0.0190 (3)	0.4872 (4)	0.3970 (3)	0.0250 (9)
C1	0.0795 (3)	0.4757 (4)	0.3239 (3)	0.0228 (9)
C2	−0.0077 (3)	0.6087 (4)	0.4381 (4)	0.0264 (11)
H2A	−0.0745	0.6193	0.4320	0.032*
H2B	0.0220	0.6761	0.4002	0.032*
C3	0.0208 (3)	0.6161 (4)	0.5471 (4)	0.0260 (10)
H3A	0.0880	0.6128	0.5525	0.031*
H3B	0.0001	0.6961	0.5756	0.031*
C4	0.2559 (3)	0.1881 (4)	0.1326 (3)	0.0212 (9)
C5	0.2678 (3)	0.1546 (5)	0.0335 (4)	0.0238 (10)
H5	0.2690	0.2174	−0.0160	0.029*
C6	0.2780 (3)	0.0316 (5)	0.0060 (4)	0.0284 (11)
H6	0.2846	0.0103	−0.0620	0.034*
C7	0.2785 (3)	−0.0610 (4)	0.0782 (4)	0.0284 (11)
H7	0.2869	−0.1453	0.0596	0.034*
C8	0.2666 (4)	−0.0303 (5)	0.1768 (4)	0.0320 (12)
H8	0.2664	−0.0936	0.2259	0.038*
C9	0.2549 (3)	0.0934 (4)	0.2042 (4)	0.0270 (10)
H9	0.2462	0.1139	0.2721	0.032*
C10	0.1869 (3)	0.4710 (4)	0.0402 (3)	0.0231 (10)
C11	0.2262 (4)	0.5821 (5)	0.0088 (4)	0.0413 (14)
H11	0.2767	0.6157	0.0442	0.050*
C12	0.1920 (4)	0.6440 (5)	−0.0742 (5)	0.0424 (15)
H12	0.2184	0.7205	−0.0944	0.051*
C13	0.1199 (4)	0.5948 (4)	−0.1273 (4)	0.0272 (10)
H13	0.0966	0.6377	−0.1836	0.033*
C14	0.0818 (4)	0.4841 (5)	−0.0989 (4)	0.0344 (12)
H14	0.0324	0.4497	−0.1356	0.041*
C15	0.1166 (4)	0.4223 (5)	−0.0151 (4)	0.0307 (11)
H15	0.0908	0.3449	0.0038	0.037*
C16	0.3474 (3)	0.4550 (4)	0.2475 (4)	0.0238 (10)
C17	0.4094 (3)	0.3737 (5)	0.2921 (4)	0.0297 (11)
H17	0.4011	0.2865	0.2860	0.036*
C18	0.4830 (4)	0.4199 (5)	0.3453 (4)	0.0369 (12)
H18	0.5247	0.3640	0.3759	0.044*
C19	0.4966 (4)	0.5477 (5)	0.3543 (4)	0.0378 (13)
H19	0.5475	0.5791	0.3904	0.045*
C20	0.4352 (3)	0.6280 (5)	0.3103 (4)	0.0308 (11)
H20	0.4439	0.7151	0.3165	0.037*
C21	0.3608 (3)	0.5833 (4)	0.2570 (4)	0.0247 (10)
H21	0.3191	0.6397	0.2270	0.030*
C22	0.5409 (12)	0.0134 (14)	0.5721 (11)	0.066 (4)	0.50
H22A	0.6046	0.0434	0.5764	0.080*	0.50
H22B	0.5172	0.0006	0.6400	0.080*	0.50
Cl1	0.4667 (2)	0.1259 (2)	0.4994 (2)	0.0958 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02652 (19)	0.01628 (17)	0.01887 (18)	−0.00089 (12)	−0.00114 (13)	0.00000 (11)
S1	0.0281 (6)	0.0167 (5)	0.0263 (6)	−0.0002 (4)	0.0029 (5)	−0.0026 (4)
S2	0.0294 (6)	0.0191 (5)	0.0247 (6)	0.0000 (5)	0.0020 (5)	−0.0025 (4)
N1	0.027 (2)	0.0180 (19)	0.030 (2)	0.0038 (16)	0.0035 (17)	0.0006 (16)
C1	0.024 (2)	0.023 (2)	0.021 (2)	0.0046 (18)	−0.0024 (18)	−0.0055 (18)
C2	0.025 (2)	0.019 (2)	0.035 (3)	0.0045 (18)	0.010 (2)	−0.0009 (19)
C3	0.024 (2)	0.018 (2)	0.036 (3)	0.0017 (18)	0.007 (2)	−0.001 (2)
C4	0.026 (2)	0.015 (2)	0.023 (2)	0.0014 (17)	0.0030 (18)	−0.0032 (17)
C5	0.024 (2)	0.027 (2)	0.021 (2)	0.0037 (19)	0.0010 (18)	−0.0005 (19)
C6	0.032 (3)	0.030 (3)	0.023 (3)	0.001 (2)	−0.001 (2)	−0.008 (2)
C7	0.029 (3)	0.018 (2)	0.038 (3)	−0.0012 (19)	−0.002 (2)	−0.007 (2)
C8	0.043 (3)	0.021 (2)	0.032 (3)	0.001 (2)	0.007 (2)	0.006 (2)
C9	0.035 (3)	0.024 (2)	0.022 (2)	0.001 (2)	0.003 (2)	0.0007 (19)
C10	0.032 (2)	0.018 (2)	0.019 (2)	0.0025 (18)	0.0003 (19)	−0.0009 (17)
C11	0.057 (4)	0.033 (3)	0.034 (3)	−0.019 (3)	−0.024 (3)	0.012 (2)
C12	0.060 (4)	0.029 (3)	0.039 (3)	−0.014 (3)	−0.013 (3)	0.013 (2)
C13	0.041 (3)	0.022 (2)	0.019 (2)	0.006 (2)	−0.001 (2)	−0.0006 (19)
C14	0.039 (3)	0.029 (3)	0.035 (3)	−0.004 (2)	−0.016 (2)	0.002 (2)
C15	0.038 (3)	0.024 (2)	0.030 (3)	−0.007 (2)	−0.009 (2)	0.003 (2)
C16	0.018 (2)	0.027 (2)	0.026 (3)	−0.0031 (18)	−0.0007 (18)	−0.0023 (19)
C17	0.028 (3)	0.031 (3)	0.030 (3)	0.001 (2)	−0.004 (2)	0.001 (2)
C18	0.029 (3)	0.036 (3)	0.045 (3)	0.002 (2)	−0.006 (2)	0.004 (3)
C19	0.032 (3)	0.040 (3)	0.041 (3)	−0.011 (2)	−0.005 (2)	−0.005 (3)
C20	0.026 (3)	0.032 (3)	0.034 (3)	−0.009 (2)	−0.002 (2)	−0.003 (2)
C21	0.023 (2)	0.023 (2)	0.027 (3)	−0.0027 (19)	0.0017 (19)	0.0021 (19)
C22	0.102 (12)	0.050 (8)	0.048 (9)	0.001 (8)	0.023 (8)	0.001 (7)
Cl1	0.155 (3)	0.0477 (11)	0.0854 (17)	0.0173 (13)	0.0274 (17)	0.0024 (11)

Geometric parameters (Å, º) top

Sn—C10	2.125 (5)	C10—C15	1.373 (7)
Sn—C16	2.141 (5)	C10—C11	1.394 (7)
Sn—C4	2.157 (4)	C11—C12	1.392 (8)
Sn—S1	2.4699 (13)	C11—H11	0.9500
Sn—S2	3.0715 (13)	C12—C13	1.378 (8)
S1—C1	1.756 (5)	C12—H12	0.9500
S2—C1	1.680 (5)	C13—C14	1.370 (7)
N1—C1	1.337 (6)	C13—H13	0.9500
N1—C3ⁱ	1.466 (6)	C14—C15	1.403 (7)
N1—C2	1.473 (6)	C14—H14	0.9500
C2—C3	1.527 (7)	C15—H15	0.9500
C2—H2A	0.9900	C16—C17	1.396 (7)
C2—H2B	0.9900	C16—C21	1.400 (7)
C3—N1ⁱ	1.466 (6)	C17—C18	1.385 (7)
C3—H3A	0.9900	C17—H17	0.9500
C3—H3B	0.9900	C18—C19	1.395 (8)
C4—C5	1.394 (6)	C18—H18	0.9500
C4—C9	1.403 (7)	C19—C20	1.380 (8)
C5—C6	1.382 (7)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.389 (7)
C6—C7	1.392 (7)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.380 (7)	C22—Cl1ⁱⁱ	1.784 (15)
C7—H7	0.9500	C22—Cl1	1.896 (16)
C8—C9	1.392 (7)	C22—H22A	0.9900
C8—H8	0.9500	C22—H22B	0.9900
C9—H9	0.9500	Cl1—C22ⁱⁱ	1.784 (15)

C10—Sn—C16	117.43 (18)	C8—C9—H9	119.7
C10—Sn—C4	106.86 (18)	C4—C9—H9	119.7
C16—Sn—C4	110.16 (18)	C15—C10—C11	118.3 (5)
C10—Sn—S1	114.23 (13)	C15—C10—Sn	120.1 (4)
C16—Sn—S1	112.36 (13)	C11—C10—Sn	121.7 (4)
C4—Sn—S1	92.74 (12)	C12—C11—C10	120.4 (5)
C10—Sn—S2	81.15 (12)	C12—C11—H11	119.8
C16—Sn—S2	84.41 (13)	C10—C11—H11	119.8
C4—Sn—S2	156.03 (12)	C13—C12—C11	120.3 (5)
S1—Sn—S2	63.66 (4)	C13—C12—H12	119.9
C1—S1—Sn	97.41 (16)	C11—C12—H12	119.9
C1—S2—Sn	79.09 (16)	C14—C13—C12	120.2 (5)
C1—N1—C3ⁱ	125.3 (4)	C14—C13—H13	119.9
C1—N1—C2	122.6 (4)	C12—C13—H13	119.9
C3ⁱ—N1—C2	111.8 (4)	C13—C14—C15	119.3 (5)
N1—C1—S2	123.6 (4)	C13—C14—H14	120.4
N1—C1—S1	117.0 (4)	C15—C14—H14	120.4
S2—C1—S1	119.4 (3)	C10—C15—C14	121.6 (5)
N1—C2—C3	109.6 (4)	C10—C15—H15	119.2
N1—C2—H2A	109.7	C14—C15—H15	119.2
C3—C2—H2A	109.7	C17—C16—C21	119.2 (5)
N1—C2—H2B	109.7	C17—C16—Sn	118.9 (4)
C3—C2—H2B	109.7	C21—C16—Sn	121.9 (4)
H2A—C2—H2B	108.2	C18—C17—C16	120.2 (5)
N1ⁱ—C3—C2	110.3 (4)	C18—C17—H17	119.9
N1ⁱ—C3—H3A	109.6	C16—C17—H17	119.9
C2—C3—H3A	109.6	C17—C18—C19	120.6 (5)
N1ⁱ—C3—H3B	109.6	C17—C18—H18	119.7
C2—C3—H3B	109.6	C19—C18—H18	119.7
H3A—C3—H3B	108.1	C20—C19—C18	119.1 (5)
C5—C4—C9	118.2 (4)	C20—C19—H19	120.4
C5—C4—Sn	120.2 (3)	C18—C19—H19	120.4
C9—C4—Sn	121.5 (3)	C19—C20—C21	121.0 (5)
C6—C5—C4	121.2 (5)	C19—C20—H20	119.5
C6—C5—H5	119.4	C21—C20—H20	119.5
C4—C5—H5	119.4	C20—C21—C16	119.8 (5)
C5—C6—C7	119.8 (5)	C20—C21—H21	120.1
C5—C6—H6	120.1	C16—C21—H21	120.1
C7—C6—H6	120.1	Cl1ⁱⁱ—C22—Cl1	102.9 (8)
C8—C7—C6	120.1 (5)	Cl1ⁱⁱ—C22—H22A	111.2
C8—C7—H7	120.0	Cl1—C22—H22A	111.2
C6—C7—H7	120.0	Cl1ⁱⁱ—C22—H22B	111.2
C7—C8—C9	120.0 (5)	Cl1—C22—H22B	111.2
C7—C8—H8	120.0	H22A—C22—H22B	109.1
C9—C8—H8	120.0	C22ⁱⁱ—Cl1—C22	77.1 (8)
C8—C9—C4	120.6 (5)

C10—Sn—S1—C1	−69.6 (2)	Sn—C4—C9—C8	176.9 (4)
C16—Sn—S1—C1	67.4 (2)	C16—Sn—C10—C15	175.8 (4)
C4—Sn—S1—C1	−179.5 (2)	C4—Sn—C10—C15	51.5 (4)
S2—Sn—S1—C1	−3.88 (16)	S1—Sn—C10—C15	−49.5 (4)
C10—Sn—S2—C1	126.8 (2)	S2—Sn—C10—C15	−105.3 (4)
C16—Sn—S2—C1	−114.3 (2)	C16—Sn—C10—C11	−5.6 (5)
C4—Sn—S2—C1	15.0 (4)	C4—Sn—C10—C11	−129.8 (5)
S1—Sn—S2—C1	4.10 (17)	S1—Sn—C10—C11	129.2 (4)
C3ⁱ—N1—C1—S2	−175.8 (4)	S2—Sn—C10—C11	73.4 (4)
C2—N1—C1—S2	−2.8 (7)	C15—C10—C11—C12	2.7 (9)
C3ⁱ—N1—C1—S1	4.6 (7)	Sn—C10—C11—C12	−176.0 (5)
C2—N1—C1—S1	177.6 (4)	C10—C11—C12—C13	−1.2 (10)
Sn—S2—C1—N1	174.5 (4)	C11—C12—C13—C14	−0.4 (9)
Sn—S2—C1—S1	−5.9 (2)	C12—C13—C14—C15	0.5 (8)
Sn—S1—C1—N1	−173.0 (3)	C11—C10—C15—C14	−2.6 (8)
Sn—S1—C1—S2	7.3 (3)	Sn—C10—C15—C14	176.1 (4)
C1—N1—C2—C3	−116.5 (5)	C13—C14—C15—C10	1.1 (8)
C3ⁱ—N1—C2—C3	57.4 (5)	C10—Sn—C16—C17	−143.2 (4)
N1—C2—C3—N1ⁱ	−56.4 (5)	C4—Sn—C16—C17	−20.6 (4)
C10—Sn—C4—C5	18.7 (4)	S1—Sn—C16—C17	81.2 (4)
C16—Sn—C4—C5	−110.0 (4)	S2—Sn—C16—C17	139.8 (4)
S1—Sn—C4—C5	135.0 (4)	C10—Sn—C16—C21	39.4 (5)
S2—Sn—C4—C5	125.3 (3)	C4—Sn—C16—C21	162.0 (4)
C10—Sn—C4—C9	−157.4 (4)	S1—Sn—C16—C21	−96.1 (4)
C16—Sn—C4—C9	74.0 (4)	S2—Sn—C16—C21	−37.6 (4)
S1—Sn—C4—C9	−41.1 (4)	C21—C16—C17—C18	0.2 (8)
S2—Sn—C4—C9	−50.8 (6)	Sn—C16—C17—C18	−177.2 (4)
C9—C4—C5—C6	0.3 (7)	C16—C17—C18—C19	−0.5 (9)
Sn—C4—C5—C6	−175.9 (4)	C17—C18—C19—C20	0.6 (9)
C4—C5—C6—C7	−1.4 (7)	C18—C19—C20—C21	−0.4 (9)
C5—C6—C7—C8	1.6 (8)	C19—C20—C21—C16	0.0 (8)
C6—C7—C8—C9	−0.5 (8)	C17—C16—C21—C20	0.0 (7)
C7—C8—C9—C4	−0.6 (8)	Sn—C16—C21—C20	177.4 (4)
C5—C4—C9—C8	0.7 (7)	Cl1ⁱⁱ—C22—Cl1—C22ⁱⁱ	0.000 (2)

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

Experimental details

Crystal data
Chemical formula	[Sn₂(C₆H₅)₆(C₆H₈N₂S₄)]·CH₂Cl₂
M_r	1021.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	98
a, b, c (Å)	14.681 (5), 10.758 (3), 13.470 (4)
β (°)	90.379 (6)
V (Å³)	2127.3 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.35 × 0.15 × 0.02

Data collection
Diffractometer	Rigaku AFC12κ/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.354, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	14400, 4389, 4021
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.113, 1.10
No. of reflections	4389
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −1.12

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008.

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
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 553–550. Web of Science CrossRef Google Scholar
Yin, H.-D., Ma, C.-L., Wang, Y., Fang, H.-X. & Shao, J.-X. (2002). Chin. J. Chem. 60, 897–903. CAS Google Scholar

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