Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024117/hb2416sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024117/hb2416Isup2.hkl |
CCDC reference: 651359
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.009 Å
- R factor = 0.043
- wR factor = 0.111
- Data-to-parameter ratio = 21.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.28 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized according to the literature method (Steliou & Mrani, 1982). The crystals of (I) were obtained from chloroform–methanol (1:1, v/v) by slow evaporation at 298 K (yield 85%, m.p. 405–406 K).
The C—C distances of the C13–C18 cyclohexyl ring were restrained to 1.53 (1) Å and 1,3-related distances to 2.50 (2) Å. The vibration of C14–C18 atoms were made approximately isotropic. The H atoms were placed at calculated positions (C—H = 0.97–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Bis(triorganotin) sulfides, (R3Sn)2S, show little tendency towards self-association. Bis(triphenyltin) sulfide, (Ph3Sn)2S (Glidewell & Liles, 1982), and bis(tri-tert-butyltin) sulfide, (tBu3Sn)2S (Batchelor et al., 1988), are both monomers with distorted tetrahedral tin atoms.
In the title compound, (I), which was synthesized by Steliou & Mrani in 1982, each Sn atom is also four-coordinate and possess a distorted SnSC3 tetrahedral geometry (Fig. 1 & Table 1). The mean Sn—S distance is 2.4089 (14) Å, which is very similar to that [2.411 (8) Å] found in (Ph3Sn)2S (Glidewell & Liles, 1982) and slightly shorter than that [2.427 (2) Å] of (tBu3Sn)2S (Batchelor et al., 1988). For steric reasons, the angle Sn—S—Sn [113.43 (5)°] and the seperation of Sn···Sn [4.027 (3) Å] in (I) are slightly larger than the corresponding values in (Ph3Sn)2S [107.3 (3)° and 3.883 (3) Å] and much smaller than in (tBu3Sn)2S [134.2 (2)° and 4.473 (1) Å].
For related structures, see Glidewell & Liles (1982) and Batchelor et al. (1988).
For related literature, see: Steliou & Mrani (1982).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
[Sn2(C6H11)6S] | F(000) = 1592 |
Mr = 768.33 | Dx = 1.381 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7158 reflections |
a = 10.3799 (15) Å | θ = 2.2–24.7° |
b = 14.418 (2) Å | µ = 1.43 mm−1 |
c = 24.862 (4) Å | T = 295 K |
β = 96.558 (2)° | Prism, colourless |
V = 3696.4 (9) Å3 | 0.44 × 0.11 × 0.11 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 7651 independent reflections |
Radiation source: fine-focus sealed tube | 6079 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 26.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→13 |
Tmin = 0.572, Tmax = 0.859 | k = −18→17 |
29484 measured reflections | l = −31→31 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.051P)2 + 3.1168P] where P = (Fo2 + 2Fc2)/3 |
7651 reflections | (Δ/σ)max = 0.001 |
352 parameters | Δρmax = 0.87 e Å−3 |
42 restraints | Δρmin = −0.38 e Å−3 |
[Sn2(C6H11)6S] | V = 3696.4 (9) Å3 |
Mr = 768.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.3799 (15) Å | µ = 1.43 mm−1 |
b = 14.418 (2) Å | T = 295 K |
c = 24.862 (4) Å | 0.44 × 0.11 × 0.11 mm |
β = 96.558 (2)° |
Bruker APEX CCD area-detector diffractometer | 7651 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 6079 reflections with I > 2σ(I) |
Tmin = 0.572, Tmax = 0.859 | Rint = 0.041 |
29484 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 42 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.87 e Å−3 |
7651 reflections | Δρmin = −0.38 e Å−3 |
352 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.51770 (3) | 0.27799 (2) | 0.103632 (12) | 0.04466 (11) | |
Sn2 | 0.61299 (3) | 0.45430 (2) | 0.227440 (12) | 0.04517 (11) | |
S1 | 0.52413 (15) | 0.30496 (10) | 0.19930 (5) | 0.0642 (4) | |
C1 | 0.4037 (4) | 0.3830 (3) | 0.05779 (17) | 0.0443 (10) | |
H1 | 0.4538 | 0.4407 | 0.0611 | 0.053* | |
C2 | 0.3788 (5) | 0.3599 (4) | −0.00249 (19) | 0.0611 (13) | |
H2A | 0.4614 | 0.3544 | −0.0170 | 0.073* | |
H2B | 0.3355 | 0.3003 | −0.0068 | 0.073* | |
C3 | 0.2973 (5) | 0.4317 (4) | −0.0349 (2) | 0.0682 (15) | |
H3A | 0.3462 | 0.4889 | −0.0356 | 0.082* | |
H3B | 0.2776 | 0.4101 | −0.0718 | 0.082* | |
C4 | 0.1734 (5) | 0.4503 (4) | −0.0114 (2) | 0.0693 (16) | |
H4A | 0.1185 | 0.3958 | −0.0158 | 0.083* | |
H4B | 0.1279 | 0.5010 | −0.0310 | 0.083* | |
C5 | 0.1975 (6) | 0.4749 (5) | 0.0477 (2) | 0.0749 (17) | |
H5A | 0.1149 | 0.4824 | 0.0620 | 0.090* | |
H5B | 0.2430 | 0.5337 | 0.0517 | 0.090* | |
C6 | 0.2769 (5) | 0.4013 (4) | 0.0805 (2) | 0.0634 (14) | |
H6A | 0.2946 | 0.4216 | 0.1178 | 0.076* | |
H6B | 0.2273 | 0.3442 | 0.0801 | 0.076* | |
C7 | 0.7155 (5) | 0.2691 (3) | 0.08308 (19) | 0.0510 (11) | |
H7 | 0.7607 | 0.3250 | 0.0974 | 0.061* | |
C8 | 0.7873 (5) | 0.1873 (4) | 0.1099 (2) | 0.0638 (14) | |
H8A | 0.7431 | 0.1305 | 0.0976 | 0.077* | |
H8B | 0.7862 | 0.1915 | 0.1487 | 0.077* | |
C9 | 0.9271 (6) | 0.1830 (5) | 0.0972 (2) | 0.0804 (18) | |
H9A | 0.9741 | 0.2360 | 0.1135 | 0.096* | |
H9B | 0.9677 | 0.1273 | 0.1131 | 0.096* | |
C10 | 0.9365 (6) | 0.1829 (5) | 0.0376 (3) | 0.0836 (19) | |
H10A | 0.9009 | 0.1253 | 0.0221 | 0.100* | |
H10B | 1.0270 | 0.1859 | 0.0314 | 0.100* | |
C11 | 0.8644 (6) | 0.2637 (5) | 0.0095 (2) | 0.0784 (17) | |
H11A | 0.8657 | 0.2580 | −0.0293 | 0.094* | |
H11B | 0.9079 | 0.3211 | 0.0211 | 0.094* | |
C12 | 0.7244 (5) | 0.2675 (4) | 0.0222 (2) | 0.0643 (14) | |
H12A | 0.6780 | 0.2139 | 0.0064 | 0.077* | |
H12B | 0.6830 | 0.3226 | 0.0059 | 0.077* | |
C13 | 0.4104 (8) | 0.1509 (4) | 0.0966 (2) | 0.096 (2) | |
H13 | 0.3213 | 0.1743 | 0.0938 | 0.115* | |
C14 | 0.4086 (8) | 0.1009 (5) | 0.0450 (2) | 0.105 (2) | |
H14A | 0.4964 | 0.0818 | 0.0407 | 0.125* | |
H14B | 0.3805 | 0.1434 | 0.0158 | 0.125* | |
C15 | 0.3211 (10) | 0.0156 (5) | 0.0396 (3) | 0.130 (3) | |
H15A | 0.2323 | 0.0360 | 0.0304 | 0.156* | |
H15B | 0.3444 | −0.0217 | 0.0097 | 0.156* | |
C16 | 0.3271 (11) | −0.0426 (5) | 0.0876 (3) | 0.136 (3) | |
H16A | 0.4076 | −0.0774 | 0.0910 | 0.164* | |
H16B | 0.2562 | −0.0868 | 0.0831 | 0.164* | |
C17 | 0.3193 (10) | 0.0111 (6) | 0.1379 (3) | 0.134 (3) | |
H17A | 0.3380 | −0.0298 | 0.1688 | 0.161* | |
H17B | 0.2315 | 0.0340 | 0.1382 | 0.161* | |
C18 | 0.4133 (10) | 0.0930 (5) | 0.1438 (3) | 0.137 (3) | |
H18A | 0.3935 | 0.1308 | 0.1740 | 0.164* | |
H18B | 0.5006 | 0.0692 | 0.1525 | 0.164* | |
C19 | 0.7906 (4) | 0.4806 (3) | 0.19223 (18) | 0.0473 (11) | |
H19 | 0.7673 | 0.4849 | 0.1530 | 0.057* | |
C20 | 0.8900 (5) | 0.4042 (4) | 0.2019 (2) | 0.0576 (12) | |
H20A | 0.8517 | 0.3460 | 0.1885 | 0.069* | |
H20B | 0.9152 | 0.3976 | 0.2404 | 0.069* | |
C21 | 1.0096 (5) | 0.4240 (4) | 0.1738 (2) | 0.0664 (15) | |
H21A | 1.0730 | 0.3750 | 0.1820 | 0.080* | |
H21B | 0.9861 | 0.4252 | 0.1349 | 0.080* | |
C22 | 1.0683 (5) | 0.5165 (4) | 0.1925 (3) | 0.0745 (17) | |
H22A | 1.0994 | 0.5128 | 0.2307 | 0.089* | |
H22B | 1.1420 | 0.5296 | 0.1730 | 0.089* | |
C23 | 0.9721 (6) | 0.5938 (4) | 0.1834 (3) | 0.0817 (18) | |
H23A | 0.9485 | 0.6023 | 0.1448 | 0.098* | |
H23B | 1.0113 | 0.6509 | 0.1979 | 0.098* | |
C24 | 0.8494 (6) | 0.5734 (4) | 0.2106 (3) | 0.0722 (16) | |
H24A | 0.8711 | 0.5727 | 0.2496 | 0.087* | |
H24B | 0.7863 | 0.6222 | 0.2017 | 0.087* | |
C25 | 0.4696 (5) | 0.5609 (4) | 0.2068 (2) | 0.0589 (13) | |
H25 | 0.3863 | 0.5285 | 0.2009 | 0.071* | |
C26 | 0.4829 (6) | 0.6117 (4) | 0.1544 (2) | 0.0660 (14) | |
H26A | 0.4797 | 0.5670 | 0.1251 | 0.079* | |
H26B | 0.5668 | 0.6420 | 0.1571 | 0.079* | |
C27 | 0.3775 (8) | 0.6836 (5) | 0.1409 (3) | 0.095 (2) | |
H27A | 0.3962 | 0.7187 | 0.1094 | 0.114* | |
H27B | 0.2951 | 0.6524 | 0.1319 | 0.114* | |
C28 | 0.3671 (8) | 0.7479 (5) | 0.1862 (3) | 0.105 (3) | |
H28A | 0.2934 | 0.7886 | 0.1770 | 0.126* | |
H28B | 0.4444 | 0.7861 | 0.1914 | 0.126* | |
C29 | 0.3510 (7) | 0.6991 (5) | 0.2379 (3) | 0.094 (2) | |
H29A | 0.2672 | 0.6687 | 0.2347 | 0.113* | |
H29B | 0.3533 | 0.7442 | 0.2669 | 0.113* | |
C30 | 0.4570 (7) | 0.6274 (5) | 0.2519 (3) | 0.090 (2) | |
H30A | 0.5391 | 0.6590 | 0.2609 | 0.108* | |
H30B | 0.4382 | 0.5930 | 0.2836 | 0.108* | |
C31 | 0.6426 (5) | 0.4330 (4) | 0.31450 (18) | 0.0532 (12) | |
H31 | 0.6595 | 0.4939 | 0.3314 | 0.064* | |
C32 | 0.7556 (6) | 0.3722 (5) | 0.3327 (2) | 0.0826 (19) | |
H32A | 0.8340 | 0.4006 | 0.3225 | 0.099* | |
H32B | 0.7444 | 0.3130 | 0.3143 | 0.099* | |
C33 | 0.7715 (7) | 0.3559 (6) | 0.3937 (2) | 0.104 (3) | |
H33A | 0.8413 | 0.3120 | 0.4030 | 0.124* | |
H33B | 0.7951 | 0.4138 | 0.4122 | 0.124* | |
C34 | 0.6512 (7) | 0.3198 (5) | 0.4124 (2) | 0.0847 (19) | |
H34A | 0.6341 | 0.2581 | 0.3978 | 0.102* | |
H34B | 0.6627 | 0.3150 | 0.4516 | 0.102* | |
C35 | 0.5390 (7) | 0.3800 (6) | 0.3956 (2) | 0.097 (2) | |
H35A | 0.5514 | 0.4395 | 0.4137 | 0.116* | |
H35B | 0.4612 | 0.3520 | 0.4067 | 0.116* | |
C36 | 0.5210 (6) | 0.3950 (5) | 0.3345 (2) | 0.0794 (18) | |
H36A | 0.4985 | 0.3365 | 0.3165 | 0.095* | |
H36B | 0.4500 | 0.4379 | 0.3252 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0527 (2) | 0.04650 (19) | 0.03447 (17) | −0.00494 (14) | 0.00339 (13) | 0.00176 (13) |
Sn2 | 0.0506 (2) | 0.0497 (2) | 0.03501 (17) | 0.00293 (14) | 0.00387 (13) | 0.00495 (13) |
S1 | 0.0901 (10) | 0.0663 (8) | 0.0361 (6) | −0.0237 (7) | 0.0074 (6) | 0.0007 (6) |
C1 | 0.042 (2) | 0.051 (3) | 0.040 (2) | −0.006 (2) | 0.0018 (19) | 0.003 (2) |
C2 | 0.065 (3) | 0.075 (4) | 0.043 (3) | 0.013 (3) | 0.007 (2) | 0.005 (2) |
C3 | 0.061 (3) | 0.097 (4) | 0.045 (3) | 0.002 (3) | −0.002 (2) | 0.012 (3) |
C4 | 0.052 (3) | 0.090 (4) | 0.063 (3) | 0.007 (3) | −0.006 (3) | 0.018 (3) |
C5 | 0.059 (3) | 0.101 (5) | 0.065 (4) | 0.023 (3) | 0.011 (3) | 0.006 (3) |
C6 | 0.053 (3) | 0.093 (4) | 0.045 (3) | 0.008 (3) | 0.009 (2) | 0.006 (3) |
C7 | 0.056 (3) | 0.051 (3) | 0.045 (3) | 0.007 (2) | 0.003 (2) | −0.003 (2) |
C8 | 0.069 (3) | 0.068 (3) | 0.055 (3) | 0.016 (3) | 0.007 (3) | 0.009 (3) |
C9 | 0.079 (4) | 0.086 (4) | 0.074 (4) | 0.028 (3) | 0.002 (3) | 0.004 (3) |
C10 | 0.079 (4) | 0.095 (5) | 0.080 (4) | 0.025 (4) | 0.022 (3) | −0.006 (4) |
C11 | 0.079 (4) | 0.096 (5) | 0.064 (4) | 0.011 (4) | 0.026 (3) | 0.011 (3) |
C12 | 0.063 (3) | 0.081 (4) | 0.050 (3) | 0.007 (3) | 0.009 (3) | 0.011 (3) |
C13 | 0.151 (7) | 0.065 (4) | 0.072 (4) | −0.043 (4) | 0.015 (4) | −0.005 (3) |
C14 | 0.148 (6) | 0.091 (5) | 0.073 (4) | −0.037 (4) | 0.009 (4) | −0.003 (4) |
C15 | 0.182 (7) | 0.090 (5) | 0.113 (6) | −0.051 (5) | −0.013 (5) | −0.016 (4) |
C16 | 0.195 (8) | 0.087 (5) | 0.124 (6) | −0.048 (5) | 0.004 (6) | −0.001 (5) |
C17 | 0.183 (7) | 0.103 (5) | 0.122 (6) | −0.062 (5) | 0.039 (6) | 0.008 (5) |
C18 | 0.211 (8) | 0.105 (5) | 0.091 (5) | −0.076 (5) | 0.001 (5) | 0.006 (4) |
C19 | 0.050 (3) | 0.052 (3) | 0.039 (2) | −0.005 (2) | 0.002 (2) | 0.003 (2) |
C20 | 0.058 (3) | 0.057 (3) | 0.059 (3) | 0.002 (2) | 0.012 (2) | 0.005 (2) |
C21 | 0.055 (3) | 0.076 (4) | 0.071 (4) | 0.008 (3) | 0.021 (3) | 0.001 (3) |
C22 | 0.054 (3) | 0.089 (4) | 0.081 (4) | −0.009 (3) | 0.010 (3) | −0.014 (3) |
C23 | 0.067 (4) | 0.062 (4) | 0.118 (5) | −0.021 (3) | 0.019 (4) | −0.003 (4) |
C24 | 0.067 (4) | 0.056 (3) | 0.092 (4) | −0.003 (3) | 0.004 (3) | −0.009 (3) |
C25 | 0.067 (3) | 0.054 (3) | 0.055 (3) | 0.014 (2) | 0.006 (3) | 0.001 (2) |
C26 | 0.076 (4) | 0.068 (3) | 0.053 (3) | 0.012 (3) | 0.002 (3) | 0.007 (3) |
C27 | 0.126 (6) | 0.076 (4) | 0.076 (4) | 0.029 (4) | −0.017 (4) | 0.019 (4) |
C28 | 0.124 (7) | 0.064 (4) | 0.120 (7) | 0.020 (4) | −0.011 (5) | 0.011 (4) |
C29 | 0.111 (6) | 0.072 (4) | 0.100 (5) | 0.022 (4) | 0.017 (4) | −0.020 (4) |
C30 | 0.121 (6) | 0.081 (4) | 0.065 (4) | 0.025 (4) | 0.003 (4) | −0.004 (3) |
C31 | 0.068 (3) | 0.057 (3) | 0.035 (2) | 0.001 (2) | 0.004 (2) | 0.002 (2) |
C32 | 0.072 (4) | 0.129 (6) | 0.046 (3) | 0.024 (4) | 0.006 (3) | 0.024 (3) |
C33 | 0.085 (5) | 0.176 (8) | 0.048 (3) | 0.020 (5) | 0.000 (3) | 0.037 (4) |
C34 | 0.116 (5) | 0.090 (5) | 0.048 (3) | 0.008 (4) | 0.009 (3) | 0.023 (3) |
C35 | 0.090 (5) | 0.139 (7) | 0.065 (4) | 0.014 (5) | 0.027 (3) | 0.034 (4) |
C36 | 0.067 (4) | 0.117 (5) | 0.056 (3) | 0.006 (4) | 0.015 (3) | 0.027 (3) |
Sn1—C13 | 2.141 (6) | C17—H17A | 0.9700 |
Sn1—C1 | 2.164 (4) | C17—H17B | 0.9700 |
Sn1—C7 | 2.176 (5) | C18—H18A | 0.9700 |
Sn1—S1 | 2.4034 (13) | C18—H18B | 0.9700 |
Sn2—C25 | 2.160 (5) | C19—C20 | 1.510 (7) |
Sn2—C19 | 2.163 (5) | C19—C24 | 1.519 (7) |
Sn2—C31 | 2.173 (4) | C19—H19 | 0.9800 |
Sn2—S1 | 2.4143 (14) | C20—C21 | 1.519 (7) |
C1—C6 | 1.513 (6) | C20—H20A | 0.9700 |
C1—C2 | 1.528 (6) | C20—H20B | 0.9700 |
C1—H1 | 0.9800 | C21—C22 | 1.517 (8) |
C2—C3 | 1.509 (7) | C21—H21A | 0.9700 |
C2—H2A | 0.9700 | C21—H21B | 0.9700 |
C2—H2B | 0.9700 | C22—C23 | 1.497 (8) |
C3—C4 | 1.496 (7) | C22—H22A | 0.9700 |
C3—H3A | 0.9700 | C22—H22B | 0.9700 |
C3—H3B | 0.9700 | C23—C24 | 1.538 (8) |
C4—C5 | 1.505 (8) | C23—H23A | 0.9700 |
C4—H4A | 0.9700 | C23—H23B | 0.9700 |
C4—H4B | 0.9700 | C24—H24A | 0.9700 |
C5—C6 | 1.522 (7) | C24—H24B | 0.9700 |
C5—H5A | 0.9700 | C25—C30 | 1.491 (7) |
C5—H5B | 0.9700 | C25—C26 | 1.516 (7) |
C6—H6A | 0.9700 | C25—H25 | 0.9800 |
C6—H6B | 0.9700 | C26—C27 | 1.517 (8) |
C7—C8 | 1.508 (7) | C26—H26A | 0.9700 |
C7—C12 | 1.527 (7) | C26—H26B | 0.9700 |
C7—H7 | 0.9800 | C27—C28 | 1.472 (10) |
C8—C9 | 1.521 (8) | C27—H27A | 0.9700 |
C8—H8A | 0.9700 | C27—H27B | 0.9700 |
C8—H8B | 0.9700 | C28—C29 | 1.491 (10) |
C9—C10 | 1.496 (8) | C28—H28A | 0.9700 |
C9—H9A | 0.9700 | C28—H28B | 0.9700 |
C9—H9B | 0.9700 | C29—C30 | 1.521 (9) |
C10—C11 | 1.512 (8) | C29—H29A | 0.9700 |
C10—H10A | 0.9700 | C29—H29B | 0.9700 |
C10—H10B | 0.9700 | C30—H30A | 0.9700 |
C11—C12 | 1.523 (8) | C30—H30B | 0.9700 |
C11—H11A | 0.9700 | C31—C32 | 1.493 (7) |
C11—H11B | 0.9700 | C31—C36 | 1.511 (7) |
C12—H12A | 0.9700 | C31—H31 | 0.9800 |
C12—H12B | 0.9700 | C32—C33 | 1.526 (7) |
C13—C18 | 1.437 (7) | C32—H32A | 0.9700 |
C13—C14 | 1.469 (7) | C32—H32B | 0.9700 |
C13—H13 | 0.9800 | C33—C34 | 1.476 (9) |
C14—C15 | 1.525 (7) | C33—H33A | 0.9700 |
C14—H14A | 0.9700 | C33—H33B | 0.9700 |
C14—H14B | 0.9700 | C34—C35 | 1.474 (9) |
C15—C16 | 1.454 (7) | C34—H34A | 0.9700 |
C15—H15A | 0.9700 | C34—H34B | 0.9700 |
C15—H15B | 0.9700 | C35—C36 | 1.526 (8) |
C16—C17 | 1.482 (7) | C35—H35A | 0.9700 |
C16—H16A | 0.9700 | C35—H35B | 0.9700 |
C16—H16B | 0.9700 | C36—H36A | 0.9700 |
C17—C18 | 1.528 (7) | C36—H36B | 0.9700 |
C13—Sn1—C1 | 107.9 (2) | C13—C18—C17 | 114.7 (6) |
C13—Sn1—C7 | 115.2 (3) | C13—C18—H18A | 108.6 |
C1—Sn1—C7 | 113.06 (17) | C17—C18—H18A | 108.6 |
C13—Sn1—S1 | 100.05 (16) | C13—C18—H18B | 108.6 |
C1—Sn1—S1 | 111.08 (12) | C17—C18—H18B | 108.6 |
C7—Sn1—S1 | 108.76 (13) | H18A—C18—H18B | 107.6 |
C25—Sn2—C19 | 112.03 (19) | C20—C19—C24 | 110.6 (4) |
C25—Sn2—C31 | 110.60 (19) | C20—C19—Sn2 | 114.0 (3) |
C19—Sn2—C31 | 113.45 (18) | C24—C19—Sn2 | 111.4 (3) |
C25—Sn2—S1 | 109.63 (16) | C20—C19—H19 | 106.8 |
C19—Sn2—S1 | 110.75 (13) | C24—C19—H19 | 106.8 |
C31—Sn2—S1 | 99.71 (14) | Sn2—C19—H19 | 106.8 |
Sn1—S1—Sn2 | 113.43 (5) | C19—C20—C21 | 111.7 (4) |
C6—C1—C2 | 110.3 (4) | C19—C20—H20A | 109.3 |
C6—C1—Sn1 | 111.8 (3) | C21—C20—H20A | 109.3 |
C2—C1—Sn1 | 112.7 (3) | C19—C20—H20B | 109.3 |
C6—C1—H1 | 107.2 | C21—C20—H20B | 109.3 |
C2—C1—H1 | 107.2 | H20A—C20—H20B | 107.9 |
Sn1—C1—H1 | 107.2 | C22—C21—C20 | 110.2 (5) |
C3—C2—C1 | 113.3 (4) | C22—C21—H21A | 109.6 |
C3—C2—H2A | 108.9 | C20—C21—H21A | 109.6 |
C1—C2—H2A | 108.9 | C22—C21—H21B | 109.6 |
C3—C2—H2B | 108.9 | C20—C21—H21B | 109.6 |
C1—C2—H2B | 108.9 | H21A—C21—H21B | 108.1 |
H2A—C2—H2B | 107.7 | C23—C22—C21 | 111.8 (5) |
C4—C3—C2 | 111.7 (4) | C23—C22—H22A | 109.3 |
C4—C3—H3A | 109.3 | C21—C22—H22A | 109.3 |
C2—C3—H3A | 109.3 | C23—C22—H22B | 109.3 |
C4—C3—H3B | 109.3 | C21—C22—H22B | 109.3 |
C2—C3—H3B | 109.3 | H22A—C22—H22B | 107.9 |
H3A—C3—H3B | 107.9 | C22—C23—C24 | 111.3 (5) |
C3—C4—C5 | 111.7 (4) | C22—C23—H23A | 109.4 |
C3—C4—H4A | 109.3 | C24—C23—H23A | 109.4 |
C5—C4—H4A | 109.3 | C22—C23—H23B | 109.4 |
C3—C4—H4B | 109.3 | C24—C23—H23B | 109.4 |
C5—C4—H4B | 109.3 | H23A—C23—H23B | 108.0 |
H4A—C4—H4B | 107.9 | C19—C24—C23 | 111.1 (5) |
C4—C5—C6 | 112.2 (5) | C19—C24—H24A | 109.4 |
C4—C5—H5A | 109.2 | C23—C24—H24A | 109.4 |
C6—C5—H5A | 109.2 | C19—C24—H24B | 109.4 |
C4—C5—H5B | 109.2 | C23—C24—H24B | 109.4 |
C6—C5—H5B | 109.2 | H24A—C24—H24B | 108.0 |
H5A—C5—H5B | 107.9 | C30—C25—C26 | 111.2 (5) |
C1—C6—C5 | 111.3 (4) | C30—C25—Sn2 | 113.3 (4) |
C1—C6—H6A | 109.4 | C26—C25—Sn2 | 114.8 (4) |
C5—C6—H6A | 109.4 | C30—C25—H25 | 105.5 |
C1—C6—H6B | 109.4 | C26—C25—H25 | 105.5 |
C5—C6—H6B | 109.4 | Sn2—C25—H25 | 105.5 |
H6A—C6—H6B | 108.0 | C25—C26—C27 | 112.7 (5) |
C8—C7—C12 | 110.1 (4) | C25—C26—H26A | 109.1 |
C8—C7—Sn1 | 112.0 (3) | C27—C26—H26A | 109.1 |
C12—C7—Sn1 | 113.5 (3) | C25—C26—H26B | 109.1 |
C8—C7—H7 | 107.0 | C27—C26—H26B | 109.1 |
C12—C7—H7 | 107.0 | H26A—C26—H26B | 107.8 |
Sn1—C7—H7 | 107.0 | C28—C27—C26 | 112.1 (5) |
C7—C8—C9 | 112.0 (5) | C28—C27—H27A | 109.2 |
C7—C8—H8A | 109.2 | C26—C27—H27A | 109.2 |
C9—C8—H8A | 109.2 | C28—C27—H27B | 109.2 |
C7—C8—H8B | 109.2 | C26—C27—H27B | 109.2 |
C9—C8—H8B | 109.2 | H27A—C27—H27B | 107.9 |
H8A—C8—H8B | 107.9 | C27—C28—C29 | 112.8 (6) |
C10—C9—C8 | 112.1 (5) | C27—C28—H28A | 109.0 |
C10—C9—H9A | 109.2 | C29—C28—H28A | 109.0 |
C8—C9—H9A | 109.2 | C27—C28—H28B | 109.0 |
C10—C9—H9B | 109.2 | C29—C28—H28B | 109.0 |
C8—C9—H9B | 109.2 | H28A—C28—H28B | 107.8 |
H9A—C9—H9B | 107.9 | C28—C29—C30 | 111.7 (6) |
C9—C10—C11 | 111.8 (5) | C28—C29—H29A | 109.3 |
C9—C10—H10A | 109.3 | C30—C29—H29A | 109.3 |
C11—C10—H10A | 109.3 | C28—C29—H29B | 109.3 |
C9—C10—H10B | 109.3 | C30—C29—H29B | 109.3 |
C11—C10—H10B | 109.3 | H29A—C29—H29B | 107.9 |
H10A—C10—H10B | 107.9 | C25—C30—C29 | 112.8 (5) |
C10—C11—C12 | 111.5 (5) | C25—C30—H30A | 109.0 |
C10—C11—H11A | 109.3 | C29—C30—H30A | 109.0 |
C12—C11—H11A | 109.3 | C25—C30—H30B | 109.0 |
C10—C11—H11B | 109.3 | C29—C30—H30B | 109.0 |
C12—C11—H11B | 109.3 | H30A—C30—H30B | 107.8 |
H11A—C11—H11B | 108.0 | C32—C31—C36 | 110.1 (5) |
C11—C12—C7 | 111.9 (5) | C32—C31—Sn2 | 113.7 (3) |
C11—C12—H12A | 109.2 | C36—C31—Sn2 | 110.5 (3) |
C7—C12—H12A | 109.2 | C32—C31—H31 | 107.4 |
C11—C12—H12B | 109.2 | C36—C31—H31 | 107.4 |
C7—C12—H12B | 109.2 | Sn2—C31—H31 | 107.4 |
H12A—C12—H12B | 107.9 | C31—C32—C33 | 112.6 (5) |
C18—C13—C14 | 115.1 (6) | C31—C32—H32A | 109.1 |
C18—C13—Sn1 | 118.0 (4) | C33—C32—H32A | 109.1 |
C14—C13—Sn1 | 116.5 (4) | C31—C32—H32B | 109.1 |
C18—C13—H13 | 100.9 | C33—C32—H32B | 109.1 |
C14—C13—H13 | 100.9 | H32A—C32—H32B | 107.8 |
Sn1—C13—H13 | 100.9 | C34—C33—C32 | 111.6 (6) |
C13—C14—C15 | 114.9 (6) | C34—C33—H33A | 109.3 |
C13—C14—H14A | 108.5 | C32—C33—H33A | 109.3 |
C15—C14—H14A | 108.5 | C34—C33—H33B | 109.3 |
C13—C14—H14B | 108.5 | C32—C33—H33B | 109.3 |
C15—C14—H14B | 108.5 | H33A—C33—H33B | 108.0 |
H14A—C14—H14B | 107.5 | C35—C34—C33 | 111.9 (6) |
C16—C15—C14 | 115.1 (6) | C35—C34—H34A | 109.2 |
C16—C15—H15A | 108.5 | C33—C34—H34A | 109.2 |
C14—C15—H15A | 108.5 | C35—C34—H34B | 109.2 |
C16—C15—H15B | 108.5 | C33—C34—H34B | 109.2 |
C14—C15—H15B | 108.5 | H34A—C34—H34B | 107.9 |
H15A—C15—H15B | 107.5 | C34—C35—C36 | 111.6 (6) |
C15—C16—C17 | 112.9 (7) | C34—C35—H35A | 109.3 |
C15—C16—H16A | 109.0 | C36—C35—H35A | 109.3 |
C17—C16—H16A | 109.0 | C34—C35—H35B | 109.3 |
C15—C16—H16B | 109.0 | C36—C35—H35B | 109.3 |
C17—C16—H16B | 109.0 | H35A—C35—H35B | 108.0 |
H16A—C16—H16B | 107.8 | C31—C36—C35 | 111.5 (5) |
C16—C17—C18 | 112.8 (6) | C31—C36—H36A | 109.3 |
C16—C17—H17A | 109.0 | C35—C36—H36A | 109.3 |
C18—C17—H17A | 109.0 | C31—C36—H36B | 109.3 |
C16—C17—H17B | 109.0 | C35—C36—H36B | 109.3 |
C18—C17—H17B | 109.0 | H36A—C36—H36B | 108.0 |
H17A—C17—H17B | 107.8 | ||
C13—Sn1—S1—Sn2 | −172.4 (2) | C14—C13—C18—C17 | −44.8 (12) |
C1—Sn1—S1—Sn2 | −58.56 (14) | Sn1—C13—C18—C17 | 171.5 (7) |
C7—Sn1—S1—Sn2 | 66.48 (15) | C16—C17—C18—C13 | 49.0 (13) |
C25—Sn2—S1—Sn1 | 77.05 (16) | C25—Sn2—C19—C20 | −175.5 (3) |
C19—Sn2—S1—Sn1 | −47.07 (15) | C31—Sn2—C19—C20 | 58.4 (4) |
C31—Sn2—S1—Sn1 | −166.84 (15) | S1—Sn2—C19—C20 | −52.7 (4) |
C13—Sn1—C1—C6 | 62.9 (4) | C25—Sn2—C19—C24 | 58.6 (4) |
C7—Sn1—C1—C6 | −168.4 (3) | C31—Sn2—C19—C24 | −67.5 (4) |
S1—Sn1—C1—C6 | −45.8 (4) | S1—Sn2—C19—C24 | −178.6 (3) |
C13—Sn1—C1—C2 | −62.0 (4) | C24—C19—C20—C21 | −56.7 (6) |
C7—Sn1—C1—C2 | 66.7 (4) | Sn2—C19—C20—C21 | 177.0 (4) |
S1—Sn1—C1—C2 | −170.7 (3) | C19—C20—C21—C22 | 56.8 (6) |
C6—C1—C2—C3 | 53.2 (6) | C20—C21—C22—C23 | −56.2 (7) |
Sn1—C1—C2—C3 | 178.9 (4) | C21—C22—C23—C24 | 55.4 (7) |
C1—C2—C3—C4 | −53.2 (7) | C20—C19—C24—C23 | 54.9 (6) |
C2—C3—C4—C5 | 53.3 (7) | Sn2—C19—C24—C23 | −177.3 (4) |
C3—C4—C5—C6 | −55.0 (7) | C22—C23—C24—C19 | −54.7 (7) |
C2—C1—C6—C5 | −53.6 (6) | C19—Sn2—C25—C30 | −103.2 (5) |
Sn1—C1—C6—C5 | −179.8 (4) | C31—Sn2—C25—C30 | 24.4 (5) |
C4—C5—C6—C1 | 55.6 (7) | S1—Sn2—C25—C30 | 133.4 (4) |
C13—Sn1—C7—C8 | −47.5 (4) | C19—Sn2—C25—C26 | 26.0 (5) |
C1—Sn1—C7—C8 | −172.3 (3) | C31—Sn2—C25—C26 | 153.7 (4) |
S1—Sn1—C7—C8 | 63.8 (4) | S1—Sn2—C25—C26 | −97.3 (4) |
C13—Sn1—C7—C12 | 77.9 (4) | C30—C25—C26—C27 | −51.5 (7) |
C1—Sn1—C7—C12 | −46.9 (4) | Sn2—C25—C26—C27 | 178.2 (4) |
S1—Sn1—C7—C12 | −170.8 (3) | C25—C26—C27—C28 | 52.4 (8) |
C12—C7—C8—C9 | 54.8 (6) | C26—C27—C28—C29 | −53.3 (10) |
Sn1—C7—C8—C9 | −177.9 (4) | C27—C28—C29—C30 | 53.4 (9) |
C7—C8—C9—C10 | −55.0 (7) | C26—C25—C30—C29 | 51.9 (8) |
C8—C9—C10—C11 | 53.7 (8) | Sn2—C25—C30—C29 | −177.0 (5) |
C9—C10—C11—C12 | −53.6 (8) | C28—C29—C30—C25 | −53.0 (9) |
C10—C11—C12—C7 | 54.7 (7) | C25—Sn2—C31—C32 | −170.2 (4) |
C8—C7—C12—C11 | −55.1 (6) | C19—Sn2—C31—C32 | −43.4 (5) |
Sn1—C7—C12—C11 | 178.5 (4) | S1—Sn2—C31—C32 | 74.4 (4) |
C1—Sn1—C13—C18 | −140.8 (7) | C25—Sn2—C31—C36 | 65.4 (4) |
C7—Sn1—C13—C18 | 91.8 (7) | C19—Sn2—C31—C36 | −167.8 (4) |
S1—Sn1—C13—C18 | −24.6 (8) | S1—Sn2—C31—C36 | −50.0 (4) |
C1—Sn1—C13—C14 | 76.0 (7) | C36—C31—C32—C33 | −53.5 (8) |
C7—Sn1—C13—C14 | −51.4 (7) | Sn2—C31—C32—C33 | −178.1 (5) |
S1—Sn1—C13—C14 | −167.8 (6) | C31—C32—C33—C34 | 54.1 (9) |
C18—C13—C14—C15 | 41.2 (11) | C32—C33—C34—C35 | −54.4 (9) |
Sn1—C13—C14—C15 | −174.6 (6) | C33—C34—C35—C36 | 55.4 (9) |
C13—C14—C15—C16 | −42.4 (12) | C32—C31—C36—C35 | 54.0 (7) |
C14—C15—C16—C17 | 46.7 (13) | Sn2—C31—C36—C35 | −179.6 (5) |
C15—C16—C17—C18 | −49.4 (13) | C34—C35—C36—C31 | −55.4 (8) |
Experimental details
Crystal data | |
Chemical formula | [Sn2(C6H11)6S] |
Mr | 768.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 10.3799 (15), 14.418 (2), 24.862 (4) |
β (°) | 96.558 (2) |
V (Å3) | 3696.4 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.43 |
Crystal size (mm) | 0.44 × 0.11 × 0.11 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.572, 0.859 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29484, 7651, 6079 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.111, 1.05 |
No. of reflections | 7651 |
No. of parameters | 352 |
No. of restraints | 42 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.87, −0.38 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Sn1—C13 | 2.141 (6) | Sn2—C25 | 2.160 (5) |
Sn1—C1 | 2.164 (4) | Sn2—C19 | 2.163 (5) |
Sn1—C7 | 2.176 (5) | Sn2—C31 | 2.173 (4) |
Sn1—S1 | 2.4034 (13) | Sn2—S1 | 2.4143 (14) |
Bis(triorganotin) sulfides, (R3Sn)2S, show little tendency towards self-association. Bis(triphenyltin) sulfide, (Ph3Sn)2S (Glidewell & Liles, 1982), and bis(tri-tert-butyltin) sulfide, (tBu3Sn)2S (Batchelor et al., 1988), are both monomers with distorted tetrahedral tin atoms.
In the title compound, (I), which was synthesized by Steliou & Mrani in 1982, each Sn atom is also four-coordinate and possess a distorted SnSC3 tetrahedral geometry (Fig. 1 & Table 1). The mean Sn—S distance is 2.4089 (14) Å, which is very similar to that [2.411 (8) Å] found in (Ph3Sn)2S (Glidewell & Liles, 1982) and slightly shorter than that [2.427 (2) Å] of (tBu3Sn)2S (Batchelor et al., 1988). For steric reasons, the angle Sn—S—Sn [113.43 (5)°] and the seperation of Sn···Sn [4.027 (3) Å] in (I) are slightly larger than the corresponding values in (Ph3Sn)2S [107.3 (3)° and 3.883 (3) Å] and much smaller than in (tBu3Sn)2S [134.2 (2)° and 4.473 (1) Å].