Download citation
Download citation
link to html
The title compound, [Sn(C6H5)3{S2CN(Et)C6H11}], has a similar geometry to its methyl analogue, between tetrahedral and distorted trigonal bipyramidal but closer to the latter. The long intramolecular Sn...S interaction of 2.9426 (10) Å is slightly shorter than in its methyl analogue, 3.0134 (8) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015277/ww6099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015277/ww6099Isup2.hkl
Contains datablock I

CCDC reference: 221627

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.025
  • wR factor = 0.071
  • Data-to-parameter ratio = 20.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(N-cyclohexyl-N-ethyldithiocarbamato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C9H16NS2)]Z = 2
Mr = 552.34F(000) = 564
Triclinic, P1Dx = 1.442 Mg m3
a = 10.036 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.435 (3) ÅCell parameters from 6453 reflections
c = 11.989 (3) Åθ = 1.8–27.5°
α = 105.586 (4)°µ = 1.18 mm1
β = 105.443 (4)°T = 293 K
γ = 90.646 (4)°Block, colourless
V = 1272.4 (5) Å30.55 × 0.35 × 0.26 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5793 independent reflections
Radiation source: fine-focus sealed tube5492 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 83.66 pixels mm-1θmax = 27.5°, θmin = 1.8°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.562, Tmax = 0.748l = 1515
16186 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0385P)2 + 0.5044P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5793 reflectionsΔρmax = 0.73 e Å3
282 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (7)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.378286 (13)0.195479 (11)0.183589 (11)0.04154 (6)
S10.20887 (6)0.05736 (5)0.00579 (5)0.04883 (12)
S20.18159 (7)0.31887 (5)0.03356 (6)0.05788 (15)
N10.0302 (2)0.14166 (16)0.15371 (17)0.0502 (4)
C10.0446 (5)0.2319 (5)0.3249 (4)0.1248 (19)
H1A0.09340.15640.38120.150*
H1B0.05060.23490.32890.150*
C20.1143 (5)0.3406 (6)0.3586 (6)0.151 (3)
H2A0.05910.41530.30720.181*
H2B0.11730.33550.44130.181*
C30.2558 (4)0.3455 (3)0.3461 (3)0.0929 (12)
H3A0.31440.27620.40510.111*
H3B0.29300.41910.36230.111*
C40.2589 (4)0.3442 (4)0.2217 (5)0.1049 (13)
H4A0.35450.33900.21910.126*
H4B0.21250.41970.16400.126*
C50.1879 (4)0.2366 (3)0.1866 (4)0.0938 (11)
H5A0.18400.24230.10360.113*
H5B0.24140.16100.23750.113*
C60.0475 (3)0.2362 (2)0.2000 (2)0.0571 (6)
H60.00110.31480.14800.068*
C70.0111 (3)0.0128 (2)0.2233 (2)0.0557 (5)
H7A0.10760.00510.27000.067*
H7B0.00380.03610.16760.067*
C80.0762 (4)0.0370 (3)0.3080 (3)0.0757 (8)
H8A0.06230.00560.36860.113*
H8B0.04920.12230.34600.113*
H8C0.17240.02590.26320.113*
C90.1284 (2)0.17330 (19)0.04969 (19)0.0443 (4)
C100.1634 (3)0.3007 (2)0.3225 (2)0.0579 (6)
H100.09760.26570.24920.069*
C110.1201 (3)0.3622 (3)0.4221 (3)0.0717 (7)
H110.02600.36780.41490.086*
C120.2157 (4)0.4144 (3)0.5303 (3)0.0714 (7)
H120.18690.45510.59690.086*
C130.3539 (3)0.4064 (3)0.5400 (2)0.0678 (7)
H130.41920.44210.61340.081*
C140.3970 (3)0.3453 (2)0.4411 (2)0.0548 (5)
H140.49130.34080.44890.066*
C150.3022 (2)0.29093 (18)0.33098 (18)0.0429 (4)
C160.5343 (3)0.0466 (2)0.3554 (2)0.0629 (6)
H160.52630.11470.41570.075*
C170.6013 (3)0.0499 (3)0.3869 (3)0.0745 (8)
H170.63810.04600.46780.089*
C180.6133 (3)0.1506 (3)0.2994 (3)0.0699 (7)
H180.65800.21540.32080.084*
C190.5594 (3)0.1563 (2)0.1798 (3)0.0667 (7)
H190.56730.22500.12010.080*
C200.4937 (3)0.0596 (2)0.1488 (2)0.0555 (5)
H200.45840.06380.06770.067*
C210.4788 (2)0.04363 (19)0.23554 (19)0.0449 (4)
C220.5429 (2)0.29629 (18)0.15622 (17)0.0426 (4)
C230.6672 (2)0.2448 (2)0.1581 (2)0.0569 (5)
H230.67750.16870.17190.068*
C240.7766 (3)0.3048 (3)0.1396 (3)0.0706 (7)
H240.85870.26790.13940.085*
C250.7647 (3)0.4181 (3)0.1217 (3)0.0685 (7)
H250.83820.45820.10920.082*
C260.6433 (3)0.4719 (2)0.1222 (2)0.0630 (6)
H260.63520.54950.11190.076*
C270.5326 (3)0.4110 (2)0.1381 (2)0.0514 (5)
H270.45020.44770.13660.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04504 (9)0.04078 (9)0.03771 (9)0.00792 (6)0.01037 (6)0.01032 (6)
S10.0528 (3)0.0438 (3)0.0466 (3)0.0080 (2)0.0051 (2)0.0159 (2)
S20.0622 (3)0.0434 (3)0.0512 (3)0.0046 (2)0.0080 (3)0.0092 (2)
N10.0519 (10)0.0426 (9)0.0469 (9)0.0005 (7)0.0028 (8)0.0141 (7)
C10.117 (3)0.189 (5)0.153 (4)0.094 (3)0.086 (3)0.137 (4)
C20.137 (4)0.216 (6)0.205 (6)0.107 (4)0.097 (4)0.178 (5)
C30.081 (2)0.080 (2)0.089 (2)0.0238 (16)0.0232 (18)0.0221 (17)
C40.098 (3)0.089 (2)0.155 (4)0.048 (2)0.056 (3)0.057 (3)
C50.099 (2)0.094 (2)0.127 (3)0.051 (2)0.065 (2)0.061 (2)
C60.0569 (13)0.0452 (11)0.0547 (13)0.0005 (9)0.0111 (10)0.0169 (10)
C70.0599 (13)0.0444 (11)0.0534 (12)0.0018 (9)0.0016 (10)0.0122 (9)
C80.094 (2)0.0644 (16)0.0659 (17)0.0072 (15)0.0245 (15)0.0119 (13)
C90.0441 (10)0.0458 (10)0.0414 (10)0.0049 (8)0.0068 (8)0.0146 (8)
C100.0477 (11)0.0579 (13)0.0602 (14)0.0042 (10)0.0135 (10)0.0053 (11)
C110.0661 (16)0.0731 (17)0.085 (2)0.0172 (13)0.0395 (15)0.0181 (15)
C120.101 (2)0.0612 (15)0.0605 (15)0.0218 (15)0.0411 (16)0.0115 (12)
C130.0891 (19)0.0654 (15)0.0394 (11)0.0138 (14)0.0113 (12)0.0056 (10)
C140.0542 (12)0.0599 (13)0.0435 (11)0.0109 (10)0.0067 (9)0.0101 (10)
C150.0470 (10)0.0406 (9)0.0397 (9)0.0073 (8)0.0117 (8)0.0089 (8)
C160.0806 (17)0.0610 (14)0.0456 (12)0.0197 (12)0.0128 (11)0.0169 (11)
C170.089 (2)0.088 (2)0.0572 (15)0.0261 (16)0.0167 (14)0.0414 (15)
C180.0773 (18)0.0653 (15)0.087 (2)0.0283 (13)0.0311 (15)0.0455 (15)
C190.0830 (18)0.0523 (13)0.0732 (17)0.0243 (12)0.0304 (14)0.0223 (12)
C200.0680 (14)0.0526 (12)0.0490 (12)0.0172 (11)0.0183 (10)0.0171 (10)
C210.0482 (11)0.0458 (10)0.0444 (10)0.0085 (8)0.0139 (8)0.0176 (8)
C220.0451 (10)0.0439 (10)0.0353 (9)0.0048 (8)0.0067 (7)0.0099 (7)
C230.0487 (12)0.0548 (13)0.0668 (14)0.0096 (10)0.0092 (10)0.0229 (11)
C240.0461 (13)0.0823 (19)0.0852 (19)0.0081 (12)0.0174 (12)0.0274 (16)
C250.0611 (15)0.0755 (17)0.0661 (16)0.0134 (13)0.0138 (12)0.0202 (13)
C260.0735 (16)0.0523 (13)0.0608 (14)0.0053 (11)0.0097 (12)0.0215 (11)
C270.0581 (12)0.0439 (11)0.0499 (12)0.0076 (9)0.0112 (10)0.0129 (9)
Geometric parameters (Å, º) top
Sn1—S12.4758 (7)C10—C151.378 (3)
Sn1—S22.9426 (10)C10—C111.393 (4)
Sn1—C152.144 (2)C10—H100.9300
Sn1—C222.148 (2)C11—C121.367 (5)
Sn1—C212.170 (2)C11—H110.9300
S1—C91.750 (2)C12—C131.366 (4)
S2—C91.690 (2)C12—H120.9300
N1—C91.324 (3)C13—C141.384 (3)
N1—C71.477 (3)C13—H130.9300
N1—C61.482 (3)C14—C151.382 (3)
C1—C61.493 (5)C14—H140.9300
C1—C21.529 (5)C16—C171.385 (4)
C1—H1A0.9700C16—C211.386 (3)
C1—H1B0.9700C16—H160.9300
C2—C31.468 (6)C17—C181.364 (4)
C2—H2A0.9700C17—H170.9300
C2—H2B0.9700C18—C191.374 (4)
C3—C41.503 (6)C18—H180.9300
C3—H3A0.9700C19—C201.379 (3)
C3—H3B0.9700C19—H190.9300
C4—C51.529 (4)C20—C211.387 (3)
C4—H4A0.9700C20—H200.9300
C4—H4B0.9700C22—C231.383 (3)
C5—C61.460 (4)C22—C271.387 (3)
C5—H5A0.9700C23—C241.385 (4)
C5—H5B0.9700C23—H230.9300
C6—H60.9800C24—C251.371 (4)
C7—C81.516 (4)C24—H240.9300
C7—H7A0.9700C25—C261.372 (4)
C7—H7B0.9700C25—H250.9300
C8—H8A0.9600C26—C271.386 (4)
C8—H8B0.9600C26—H260.9300
C8—H8C0.9600C27—H270.9300
C15—Sn1—C22114.20 (8)H8B—C8—H8C109.5
C15—Sn1—S1117.41 (6)N1—C9—S2124.22 (16)
C22—Sn1—S1118.88 (5)N1—C9—S1118.17 (16)
C21—Sn1—S2157.11 (6)S2—C9—S1117.61 (12)
C15—Sn1—C21106.21 (8)C15—C10—C11121.0 (2)
C22—Sn1—C21103.04 (8)C15—C10—H10119.5
C21—Sn1—S192.04 (6)C11—C10—H10119.5
C9—S1—Sn195.63 (7)C12—C11—C10120.1 (3)
C9—N1—C7121.90 (18)C12—C11—H11119.9
C9—N1—C6120.04 (18)C10—C11—H11119.9
C7—N1—C6117.97 (17)C13—C12—C11119.6 (2)
C6—C1—C2108.9 (4)C13—C12—H12120.2
C6—C1—H1A109.9C11—C12—H12120.2
C2—C1—H1A109.9C12—C13—C14120.3 (3)
C6—C1—H1B109.9C12—C13—H13119.9
C2—C1—H1B109.9C14—C13—H13119.9
H1A—C1—H1B108.3C15—C14—C13121.2 (2)
C3—C2—C1112.4 (4)C15—C14—H14119.4
C3—C2—H2A109.1C13—C14—H14119.4
C1—C2—H2A109.1C10—C15—C14117.8 (2)
C3—C2—H2B109.1C10—C15—Sn1123.62 (16)
C1—C2—H2B109.1C14—C15—Sn1118.60 (16)
H2A—C2—H2B107.9C17—C16—C21121.2 (2)
C2—C3—C4111.5 (3)C17—C16—H16119.4
C2—C3—H3A109.3C21—C16—H16119.4
C4—C3—H3A109.3C18—C17—C16120.1 (3)
C2—C3—H3B109.3C18—C17—H17119.9
C4—C3—H3B109.3C16—C17—H17119.9
H3A—C3—H3B108.0C17—C18—C19120.1 (2)
C3—C4—C5111.4 (3)C17—C18—H18120.0
C3—C4—H4A109.3C19—C18—H18120.0
C5—C4—H4A109.3C18—C19—C20119.7 (2)
C3—C4—H4B109.3C18—C19—H19120.2
C5—C4—H4B109.3C20—C19—H19120.2
H4A—C4—H4B108.0C19—C20—C21121.7 (2)
C6—C5—C4110.5 (3)C19—C20—H20119.2
C6—C5—H5A109.5C21—C20—H20119.2
C4—C5—H5A109.5C16—C21—C20117.3 (2)
C6—C5—H5B109.5C16—C21—Sn1121.99 (17)
C4—C5—H5B109.5C20—C21—Sn1120.71 (16)
H5A—C5—H5B108.1C23—C22—C27117.8 (2)
C5—C6—N1112.0 (2)C23—C22—Sn1118.33 (16)
C5—C6—C1112.7 (3)C27—C22—Sn1123.84 (16)
N1—C6—C1113.3 (2)C22—C23—C24121.0 (2)
C5—C6—H6106.0C22—C23—H23119.5
N1—C6—H6106.0C24—C23—H23119.5
C1—C6—H6106.0C25—C24—C23120.5 (3)
N1—C7—C8113.4 (2)C25—C24—H24119.8
N1—C7—H7A108.9C23—C24—H24119.8
C8—C7—H7A108.9C24—C25—C26119.4 (3)
N1—C7—H7B108.9C24—C25—H25120.3
C8—C7—H7B108.9C26—C25—H25120.3
H7A—C7—H7B107.7C25—C26—C27120.3 (2)
C7—C8—H8A109.5C25—C26—H26119.9
C7—C8—H8B109.5C27—C26—H26119.9
H8A—C8—H8B109.5C26—C27—C22121.0 (2)
C7—C8—H8C109.5C26—C27—H27119.5
H8A—C8—H8C109.5C22—C27—H27119.5
C15—Sn1—S1—C974.45 (10)S1—Sn1—C15—C1014.6 (2)
C22—Sn1—S1—C969.98 (10)C22—Sn1—C15—C1448.96 (19)
C21—Sn1—S1—C9176.10 (9)C21—Sn1—C15—C1463.89 (19)
C6—C1—C2—C355.6 (6)S1—Sn1—C15—C14164.99 (16)
C1—C2—C3—C454.6 (6)C21—C16—C17—C180.3 (5)
C2—C3—C4—C553.2 (5)C16—C17—C18—C190.3 (5)
C3—C4—C5—C654.1 (5)C17—C18—C19—C200.2 (5)
C4—C5—C6—N1173.5 (3)C18—C19—C20—C210.7 (4)
C4—C5—C6—C157.3 (5)C17—C16—C21—C200.2 (4)
C9—N1—C6—C5105.3 (3)C17—C16—C21—Sn1178.3 (2)
C7—N1—C6—C571.2 (3)C19—C20—C21—C160.7 (4)
C9—N1—C6—C1125.8 (3)C19—C20—C21—Sn1178.8 (2)
C7—N1—C6—C157.6 (4)C15—Sn1—C21—C1626.0 (2)
C2—C1—C6—C557.3 (5)C22—Sn1—C21—C1694.4 (2)
C2—C1—C6—N1174.2 (3)S1—Sn1—C21—C16145.3 (2)
C9—N1—C7—C887.1 (3)C15—Sn1—C21—C20156.05 (19)
C6—N1—C7—C896.5 (3)C22—Sn1—C21—C2083.6 (2)
C7—N1—C9—S2179.36 (18)S1—Sn1—C21—C2036.70 (19)
C6—N1—C9—S24.2 (3)C15—Sn1—C22—C23123.35 (18)
C7—N1—C9—S10.7 (3)C21—Sn1—C22—C238.62 (19)
C6—N1—C9—S1175.74 (18)S1—Sn1—C22—C2391.14 (17)
Sn1—S1—C9—N1176.15 (17)C15—Sn1—C22—C2755.87 (19)
Sn1—S1—C9—S23.88 (13)C21—Sn1—C22—C27170.59 (17)
C15—C10—C11—C120.2 (4)S1—Sn1—C22—C2789.65 (18)
C10—C11—C12—C130.4 (5)C27—C22—C23—C241.5 (4)
C11—C12—C13—C140.3 (5)Sn1—C22—C23—C24179.3 (2)
C12—C13—C14—C150.2 (4)C22—C23—C24—C251.4 (4)
C11—C10—C15—C140.7 (4)C23—C24—C25—C260.0 (5)
C11—C10—C15—Sn1178.9 (2)C24—C25—C26—C271.4 (4)
C13—C14—C15—C100.7 (4)C25—C26—C27—C221.3 (4)
C13—C14—C15—Sn1178.9 (2)C23—C22—C27—C260.1 (3)
C22—Sn1—C15—C10131.44 (19)Sn1—C22—C27—C26179.32 (18)
C21—Sn1—C15—C10115.7 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds