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The title compound, Ph3Sn[S2CN(Me)C6H11], has an iso­bidentate ligand, with the tin coordination geometry intermediate between tetrahedral and distorted trigonal bipyra­midal, owing to the presence of a long intramolecular Sn...S interaction of 3.0134 (8) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011991/cv6199sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011991/cv6199Isup2.hkl
Contains datablock I

CCDC reference: 217355

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.025
  • wR factor = 0.070
  • Data-to-parameter ratio = 20.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

(Dithiocarbamato)diorganotin complexes such as bis(dimethyldithiocarbamato) dimethyltin (Kimura, et al., 1972) and bis(diethyldithiocarbamato)diphenyltin (Lindley & Carr, 1974) are known to show an expansion and distortion in their geometries due to weak intramolecular Sn···S interaction. The nature of the ligands and the substituents at the tin atom also have an influence on the coordination environment of the complex. The title compound, (I), a triorganotin system with an unsymmetrical ligand is isostructural to (N-butyl-N-methyldithiocarbamato)triphenyltin(IV), Ph3Sn[S2CN(CH3C4 H9], (Kana et al., 2001) and (diethyldithiocarbamato)triphenyltin(IV) (Lindley & Carr, 1974). The isobidentate nature of the chelation, with Sn1—S1 = 2.4558 (6) Å and a weak intramolecular Sn1···S2 interaction of 3.0134 (8) Å [2.4631 (9) and 3.084 (1) Å respectively in Ph3Sn(S2CN(CH3)C4H9)] caused a coordination between tetrahedral and distorted trigonal bipyramidal. The angles C6—Sn1—S1, C6—Sn1—C18 and C18—Sn1—S1 [116.14 (5), 116.63 (8) and 116,28 (6) Å, respectively] are close to 120°, as expected at equatorial positions, and the Cl2—Sn1—S2 angle at the non-linear axial position is 158.43 (6)°. Other bond parameters of the ligand are normal and similar to those in bis(N-cyclohexyl-N-methyldithiocarbamato)dimethyltin(IV), which has a severely distorted octahedral geometry (Awang et al., 2003.)

Experimental top

The title compound was synthesized by the addition of carbon disulfide, CS2 (1.8 ml, 0.03 mol) to an ethanolic solution of N-methylcyclohaxylamine (4 ml, 0.03 mol) with stirring for one hour at 269 K. Triphenyltin(IV) chloride (11.6 g, 0.03 mol) solution was then added and the solution mixture was stirred for another hour. The resulting white precipitate was filtered, washed with cold ethanol and dried in vacuo. Some good quality crystals suitable for X-ray analysis were obained by recrystallization from a 1:1 mixture of ethanol and chloroform.

Refinement top

After their location in the difference Fourier map, all H-atoms were included in the refinement in geometrically calculated positions, and allowed to ride on the parent C atoms, with C—H = 0.93–0.98. respectively.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. : Molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
triphenyl(methylcyclohexyl)dithiocarbamato tin(IV) top
Crystal data top
[Sn(C8H14NS2)(C6H5)3]Z = 2
Mr = 538.31F(000) = 548
Triclinic, P1Dx = 1.438 Mg m3
a = 9.7951 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.342 (2) ÅCell parameters from 6115 reflections
c = 11.952 (2) Åθ = 1.8–27.6°
α = 75.037 (3)°µ = 1.21 mm1
β = 75.962 (3)°T = 273 K
γ = 89.058 (3)°Block, white
V = 1242.9 (4) Å30.53 × 0.42 × 0.26 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5658 independent reflections
Radiation source: fine-focus sealed tube5341 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 83.66 pixels mm-1θmax = 27.6°, θmin = 1.8°
ω scanh = 1212
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
k = 1414
Tmin = 0.566, Tmax = 0.744l = 1515
15537 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0401P)2 + 0.3014P]
where P = (Fo2 + 2Fc2)/3
5658 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Sn(C8H14NS2)(C6H5)3]γ = 89.058 (3)°
Mr = 538.31V = 1242.9 (4) Å3
Triclinic, P1Z = 2
a = 9.7951 (17) ÅMo Kα radiation
b = 11.342 (2) ŵ = 1.21 mm1
c = 11.952 (2) ÅT = 273 K
α = 75.037 (3)°0.53 × 0.42 × 0.26 mm
β = 75.962 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5658 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
5341 reflections with I > 2σ(I)
Tmin = 0.566, Tmax = 0.744Rint = 0.020
15537 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.06Δρmax = 0.53 e Å3
5658 reflectionsΔρmin = 0.41 e Å3
271 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.110896 (13)0.304553 (11)0.197516 (11)0.04381 (6)
S10.27879 (6)0.43476 (5)0.02397 (5)0.05226 (12)
S20.32599 (6)0.17194 (5)0.05500 (5)0.05533 (13)
N10.46193 (19)0.34731 (16)0.13134 (16)0.0518 (4)
C10.0336 (2)0.0920 (2)0.1389 (2)0.0546 (5)
H1A0.05100.05390.14050.066*
C20.1422 (3)0.0329 (2)0.1163 (2)0.0646 (6)
H2A0.13080.04480.10420.077*
C30.2672 (3)0.0889 (3)0.1115 (3)0.0697 (7)
H3A0.34010.04990.09520.084*
C40.2829 (3)0.2016 (3)0.1306 (3)0.0765 (8)
H4A0.36680.24010.12700.092*
C50.1760 (2)0.2597 (2)0.1554 (2)0.0627 (6)
H5A0.18950.33630.16990.075*
C60.0487 (2)0.20625 (18)0.15932 (17)0.0446 (4)
C70.0211 (3)0.5583 (2)0.1646 (2)0.0617 (6)
H7A0.01640.56370.08410.074*
C80.0971 (3)0.6525 (3)0.1965 (3)0.0786 (8)
H8A0.10960.72090.13790.094*
C90.1541 (3)0.6455 (3)0.3138 (4)0.0881 (10)
H9A0.20760.70830.33550.106*
C100.1329 (4)0.5472 (4)0.3990 (3)0.1023 (12)
H10A0.17050.54290.47940.123*
C110.0552 (4)0.4532 (3)0.3664 (3)0.0844 (9)
H11A0.04090.38620.42560.101*
C120.0012 (2)0.45617 (19)0.2486 (2)0.0501 (4)
C130.1034 (3)0.1495 (2)0.4481 (2)0.0579 (5)
H13A0.00710.14720.45350.069*
C140.1527 (3)0.0894 (3)0.5451 (2)0.0707 (7)
H14A0.08970.04680.61510.085*
C150.2923 (3)0.0918 (3)0.5393 (2)0.0720 (7)
H15A0.32520.05100.60500.086*
C160.3852 (3)0.1548 (3)0.4359 (3)0.0755 (7)
H16A0.48120.15700.43180.091*
C170.3369 (2)0.2146 (2)0.3385 (2)0.0603 (5)
H17A0.40060.25660.26860.072*
C180.1943 (2)0.21295 (18)0.34347 (17)0.0450 (4)
C190.3668 (2)0.31636 (18)0.02848 (18)0.0447 (4)
C200.4814 (3)0.4727 (2)0.2059 (2)0.0724 (7)
H20A0.41740.52330.16720.109*
H20B0.46320.47500.28180.109*
H20C0.57650.50220.21780.109*
C210.5516 (2)0.2543 (2)0.1756 (2)0.0507 (5)
H21A0.53650.18090.10850.061*
C220.5066 (3)0.2184 (3)0.2729 (3)0.0761 (8)
H22A0.51880.28820.34200.091*
H22B0.40760.19230.24640.091*
C230.5935 (3)0.1149 (3)0.3071 (3)0.0870 (9)
H23A0.57260.04230.24060.104*
H23B0.56780.09630.37440.104*
C240.7493 (3)0.1487 (3)0.3401 (3)0.0890 (10)
H24A0.80240.08000.35770.107*
H24B0.77200.21670.41120.107*
C250.7899 (3)0.1833 (4)0.2400 (4)0.1024 (13)
H25A0.88960.20660.26320.123*
H25C0.77340.11320.17080.123*
C260.7058 (3)0.2893 (3)0.2067 (4)0.0888 (10)
H26C0.73070.30740.13890.107*
H26A0.72760.36170.27330.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04635 (9)0.04229 (8)0.04407 (9)0.00936 (5)0.01259 (6)0.01267 (6)
S10.0553 (3)0.0446 (3)0.0552 (3)0.0075 (2)0.0056 (2)0.0180 (2)
S20.0554 (3)0.0465 (3)0.0541 (3)0.0077 (2)0.0016 (2)0.0101 (2)
N10.0519 (9)0.0471 (9)0.0499 (9)0.0021 (7)0.0000 (7)0.0132 (7)
C10.0553 (11)0.0490 (11)0.0583 (12)0.0068 (9)0.0107 (9)0.0153 (9)
C20.0720 (15)0.0549 (13)0.0659 (14)0.0072 (11)0.0068 (12)0.0232 (11)
C30.0576 (13)0.0791 (17)0.0716 (16)0.0144 (12)0.0108 (12)0.0225 (13)
C40.0470 (12)0.0844 (19)0.103 (2)0.0066 (12)0.0217 (13)0.0308 (16)
C50.0507 (11)0.0568 (13)0.0840 (17)0.0103 (10)0.0153 (11)0.0264 (12)
C60.0454 (9)0.0449 (10)0.0403 (9)0.0043 (7)0.0070 (7)0.0089 (8)
C70.0706 (14)0.0539 (12)0.0713 (15)0.0183 (11)0.0298 (12)0.0244 (11)
C80.0884 (19)0.0575 (14)0.114 (2)0.0301 (13)0.0532 (18)0.0403 (15)
C90.0798 (18)0.083 (2)0.133 (3)0.0376 (16)0.0431 (19)0.069 (2)
C100.116 (3)0.112 (3)0.086 (2)0.039 (2)0.007 (2)0.057 (2)
C110.109 (2)0.0761 (18)0.0599 (15)0.0291 (17)0.0041 (15)0.0215 (13)
C120.0508 (10)0.0487 (11)0.0554 (11)0.0097 (8)0.0147 (9)0.0206 (9)
C130.0542 (12)0.0675 (14)0.0487 (11)0.0061 (10)0.0092 (9)0.0130 (10)
C140.0920 (19)0.0711 (16)0.0444 (12)0.0066 (14)0.0149 (12)0.0089 (11)
C150.101 (2)0.0690 (16)0.0564 (14)0.0252 (14)0.0373 (14)0.0188 (12)
C160.0646 (15)0.0904 (19)0.0843 (19)0.0186 (14)0.0387 (14)0.0273 (16)
C170.0524 (12)0.0659 (14)0.0605 (13)0.0054 (10)0.0152 (10)0.0121 (11)
C180.0492 (10)0.0441 (9)0.0437 (9)0.0096 (8)0.0134 (8)0.0136 (8)
C190.0405 (9)0.0480 (10)0.0472 (10)0.0054 (7)0.0095 (7)0.0169 (8)
C200.0857 (18)0.0516 (13)0.0630 (15)0.0025 (12)0.0038 (13)0.0063 (11)
C210.0449 (10)0.0514 (11)0.0519 (11)0.0036 (8)0.0008 (8)0.0170 (9)
C220.0710 (16)0.0894 (19)0.0893 (19)0.0277 (14)0.0353 (14)0.0479 (16)
C230.0779 (18)0.104 (2)0.107 (2)0.0306 (17)0.0327 (17)0.069 (2)
C240.0739 (18)0.089 (2)0.088 (2)0.0141 (15)0.0211 (15)0.0327 (17)
C250.0450 (13)0.110 (3)0.171 (4)0.0178 (15)0.0224 (18)0.074 (3)
C260.0534 (14)0.093 (2)0.139 (3)0.0060 (13)0.0232 (16)0.063 (2)
Geometric parameters (Å, º) top
Sn1—S12.4558 (6)C13—C181.375 (3)
Sn1—S23.0134 (8)C13—C141.377 (4)
Sn1—C62.136 (2)C13—H13A0.9300
Sn1—C122.155 (2)C14—C151.352 (4)
Sn1—C182.125 (2)C14—H14A0.9300
S1—C191.753 (2)C15—C161.373 (4)
S2—C191.680 (2)C15—H15A0.9300
N1—C191.317 (3)C16—C171.375 (4)
N1—C201.457 (3)C16—H16A0.9300
N1—C211.482 (3)C17—C181.384 (3)
C1—C61.379 (3)C17—H17A0.9300
C1—C21.382 (3)C20—H20A0.9600
C1—H1A0.9300C20—H20B0.9600
C2—C31.377 (4)C20—H20C0.9600
C2—H2A0.9300C21—C221.486 (3)
C3—C41.355 (4)C21—C261.499 (3)
C3—H3A0.9300C21—H21A0.9800
C4—C51.376 (4)C22—C231.522 (4)
C4—H4A0.9300C22—H22A0.9700
C5—C61.383 (3)C22—H22B0.9700
C5—H5A0.9300C23—C241.511 (4)
C7—C81.373 (3)C23—H23A0.9700
C7—C121.376 (3)C23—H23B0.9700
C7—H7A0.9300C24—C251.490 (5)
C8—C91.360 (5)C24—H24A0.9700
C8—H8A0.9300C24—H24B0.9700
C9—C101.354 (5)C25—C261.529 (4)
C9—H9A0.9300C25—H25A0.9700
C10—C111.383 (4)C25—H25C0.9700
C10—H10A0.9300C26—H26C0.9700
C11—C121.374 (4)C26—H26A0.9700
C11—H11A0.9300
C6—Sn1—S1116.14 (5)C16—C15—H15A120.2
C18—Sn1—C6116.63 (8)C15—C16—C17120.3 (3)
C18—Sn1—S1116.28 (6)C15—C16—H16A119.9
C12—Sn1—S2158.43 (6)C17—C16—H16A119.9
C18—Sn1—C12106.24 (8)C16—C17—C18120.6 (2)
C6—Sn1—C12102.95 (8)C16—C17—H17A119.7
C12—Sn1—S194.08 (6)C18—C17—H17A119.7
C19—S1—Sn196.88 (7)C13—C18—C17118.0 (2)
C19—N1—C20121.57 (19)C13—C18—Sn1119.07 (16)
C19—N1—C21120.57 (17)C17—C18—Sn1122.89 (16)
C20—N1—C21117.85 (18)N1—C19—S2124.29 (15)
C6—C1—C2121.1 (2)N1—C19—S1117.26 (16)
C6—C1—H1A119.5S2—C19—S1118.46 (11)
C2—C1—H1A119.5N1—C20—H20A109.5
C3—C2—C1120.2 (2)N1—C20—H20B109.5
C3—C2—H2A119.9H20A—C20—H20B109.5
C1—C2—H2A119.9N1—C20—H20C109.5
C4—C3—C2119.2 (2)H20A—C20—H20C109.5
C4—C3—H3A120.4H20B—C20—H20C109.5
C2—C3—H3A120.4N1—C21—C22112.43 (19)
C3—C4—C5120.8 (3)N1—C21—C26112.7 (2)
C3—C4—H4A119.6C22—C21—C26113.1 (2)
C5—C4—H4A119.6N1—C21—H21A106.0
C4—C5—C6121.2 (2)C22—C21—H21A106.0
C4—C5—H5A119.4C26—C21—H21A106.0
C6—C5—H5A119.4C21—C22—C23110.2 (2)
C1—C6—C5117.5 (2)C21—C22—H22A109.6
C1—C6—Sn1124.21 (16)C23—C22—H22A109.6
C5—C6—Sn1118.26 (16)C21—C22—H22B109.6
C8—C7—C12121.9 (3)C23—C22—H22B109.6
C8—C7—H7A119.1H22A—C22—H22B108.1
C12—C7—H7A119.1C24—C23—C22111.2 (3)
C9—C8—C7119.9 (3)C24—C23—H23A109.4
C9—C8—H8A120.1C22—C23—H23A109.4
C7—C8—H8A120.1C24—C23—H23B109.4
C10—C9—C8119.9 (3)C22—C23—H23B109.4
C10—C9—H9A120.0H23A—C23—H23B108.0
C8—C9—H9A120.0C25—C24—C23110.3 (2)
C9—C10—C11119.9 (3)C25—C24—H24A109.6
C9—C10—H10A120.1C23—C24—H24A109.6
C11—C10—H10A120.1C25—C24—H24B109.6
C12—C11—C10121.7 (3)C23—C24—H24B109.6
C12—C11—H11A119.2H24A—C24—H24B108.1
C10—C11—H11A119.2C24—C25—C26111.5 (3)
C11—C12—C7116.8 (2)C24—C25—H25A109.3
C11—C12—Sn1121.58 (19)C26—C25—H25A109.3
C7—C12—Sn1121.61 (17)C24—C25—H25C109.3
C18—C13—C14121.0 (2)C26—C25—H25C109.3
C18—C13—H13A119.5H25A—C25—H25C108.0
C14—C13—H13A119.5C21—C26—C25109.0 (2)
C15—C14—C13120.4 (2)C21—C26—H26C109.9
C15—C14—H14A119.8C25—C26—H26C109.9
C13—C14—H14A119.8C21—C26—H26A109.9
C14—C15—C16119.7 (2)C25—C26—H26A109.9
C14—C15—H15A120.2H26C—C26—H26A108.3
C18—Sn1—S1—C1972.91 (9)C13—C14—C15—C160.0 (4)
C6—Sn1—S1—C1970.15 (9)C14—C15—C16—C170.3 (4)
C12—Sn1—S1—C19176.73 (9)C15—C16—C17—C180.4 (4)
C6—C1—C2—C31.2 (4)C14—C13—C18—C170.1 (4)
C1—C2—C3—C40.8 (4)C14—C13—C18—Sn1179.7 (2)
C2—C3—C4—C50.4 (5)C16—C17—C18—C130.2 (4)
C3—C4—C5—C61.3 (5)C16—C17—C18—Sn1179.4 (2)
C2—C1—C6—C50.4 (3)C6—Sn1—C18—C1344.2 (2)
C2—C1—C6—Sn1179.14 (17)C12—Sn1—C18—C1369.84 (19)
C4—C5—C6—C10.8 (4)S1—Sn1—C18—C13172.93 (16)
C4—C5—C6—Sn1179.6 (2)C6—Sn1—C18—C17136.21 (18)
C18—Sn1—C6—C154.5 (2)C12—Sn1—C18—C17109.76 (19)
C12—Sn1—C6—C1170.41 (18)S1—Sn1—C18—C176.7 (2)
S1—Sn1—C6—C188.39 (18)C20—N1—C19—S2173.0 (2)
C18—Sn1—C6—C5124.98 (18)C21—N1—C19—S26.1 (3)
C12—Sn1—C6—C59.11 (19)C20—N1—C19—S17.4 (3)
S1—Sn1—C6—C592.09 (18)C21—N1—C19—S1173.45 (15)
C12—C7—C8—C90.8 (4)Sn1—S1—C19—N1174.03 (16)
C7—C8—C9—C101.6 (5)Sn1—S1—C19—S26.39 (12)
C8—C9—C10—C111.1 (6)C19—N1—C21—C22104.1 (3)
C9—C10—C11—C120.3 (6)C20—N1—C21—C2275.0 (3)
C10—C11—C12—C71.1 (5)C19—N1—C21—C26126.6 (3)
C10—C11—C12—Sn1176.0 (3)C20—N1—C21—C2654.2 (3)
C8—C7—C12—C110.6 (4)N1—C21—C22—C23174.9 (2)
C8—C7—C12—Sn1176.6 (2)C26—C21—C22—C2356.0 (4)
C18—Sn1—C12—C1127.0 (3)C21—C22—C23—C2455.0 (4)
C6—Sn1—C12—C1196.1 (2)C22—C23—C24—C2556.5 (4)
S1—Sn1—C12—C11145.9 (2)C23—C24—C25—C2657.7 (4)
C18—Sn1—C12—C7155.96 (19)N1—C21—C26—C25174.7 (3)
C6—Sn1—C12—C780.9 (2)C22—C21—C26—C2556.4 (4)
S1—Sn1—C12—C737.07 (19)C24—C25—C26—C2156.8 (4)
C18—C13—C14—C150.2 (4)

Experimental details

Crystal data
Chemical formula[Sn(C8H14NS2)(C6H5)3]
Mr538.31
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)9.7951 (17), 11.342 (2), 11.952 (2)
α, β, γ (°)75.037 (3), 75.962 (3), 89.058 (3)
V3)1242.9 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.21
Crystal size (mm)0.53 × 0.42 × 0.26
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
SADABS (Sheldrick, 1996)
Tmin, Tmax0.566, 0.744
No. of measured, independent and
observed [I > 2σ(I)] reflections
15537, 5658, 5341
Rint0.020
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.070, 1.06
No. of reflections5658
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.41

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
Sn1—S12.4558 (6)S1—C191.753 (2)
Sn1—S23.0134 (8)S2—C191.680 (2)
Sn1—C62.136 (2)N1—C191.317 (3)
Sn1—C122.155 (2)N1—C201.457 (3)
Sn1—C182.125 (2)N1—C211.482 (3)
C6—Sn1—S1116.14 (5)C18—Sn1—C12106.24 (8)
C18—Sn1—C6116.63 (8)C6—Sn1—C12102.95 (8)
C18—Sn1—S1116.28 (6)C12—Sn1—S194.08 (6)
C12—Sn1—S2158.43 (6)C19—S1—Sn196.88 (7)
 

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