In the title compound, [Sn(C
6H
5)
3(C
5H
8NS
2)], the Sn
IV atom adopts a distorted SnC
3S tetrahedral coordination geometry [spread of bond angles = 94.43 (7)–120.74 (7)°]. A short intramolecular Sn

S contact [3.0270 (9) Å] occurs and two intramolecular C—H

S interactions help to establish the conformation. Three of the methylene groups of the pyrrolidine-1-carbodithioate ligand are disordered over two sets of sites of equal occupancy. In the crystal, very weak C—H

S interactions link the molecules into a three-dimensional network, with both S atoms acting as acceptors.
Supporting information
CCDC reference: 963423
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.022
- wR factor = 0.062
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B
Crystal system given = monoclinic
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Sn1 -- S2 .. 28.5 su
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. S2 .. 2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B .. S1 .. 2.98 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.725
Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do !
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Sn1 -- S1 .. 8.3 su
PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C4
PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 11 %
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Stoichiometric amount of sodium salt of pyrrolidine-1-carbodithioate was
suspended in dry toluene and to it calculated amount of triphenyltin(IV)
chloride, Ph3SnCl, (5 mmol of each, 1:1 ratio) was added. The mixture was
stirred and refluxed for 3–4 h, and then it was cooled and filtered to remove
NaCl. The filterate was rotary evaporated to get the product which was
recystallized from chloroform solution to yield colourless prisms.
The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as
riding with Uiso(H) = xUeq(C), where x = 1.5 for
methyl and x = 1.2 for other H-atoms.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Triphenyl(pyrrolidine-1-carbodithioato-
κS)tin(IV)
top
Crystal data top
[Sn(C6H5)3(C5H8NS2)] | Z = 4 |
Mr = 496.23 | F(000) = 1000 |
Monoclinic, P21/c | Dx = 1.516 Mg m−3 |
a = 12.3467 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3227 (3) Å | µ = 1.38 mm−1 |
c = 17.0611 (6) Å | T = 296 K |
β = 90.864 (2)° | Prism, colourless |
V = 2174.21 (12) Å3 | 0.32 × 0.26 × 0.24 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 3567 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −15→12 |
Tmin = 0.667, Tmax = 0.734 | k = −12→12 |
16466 measured reflections | l = −20→21 |
4265 independent reflections | |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0255P)2 + 1.8846P]
where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4265 reflections | Δρmax = 0.39 e Å−3 |
253 parameters | Δρmin = −0.47 e Å−3 |
Crystal data top
[Sn(C6H5)3(C5H8NS2)] | V = 2174.21 (12) Å3 |
Mr = 496.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.3467 (4) Å | µ = 1.38 mm−1 |
b = 10.3227 (3) Å | T = 296 K |
c = 17.0611 (6) Å | 0.32 × 0.26 × 0.24 mm |
β = 90.864 (2)° | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 4265 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3567 reflections with I > 2σ(I) |
Tmin = 0.667, Tmax = 0.734 | Rint = 0.020 |
16466 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.022 | 3 restraints |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.39 e Å−3 |
4265 reflections | Δρmin = −0.47 e Å−3 |
253 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.43914 (19) | 0.5449 (2) | 0.19935 (15) | 0.0395 (5) | |
C2 | 0.6278 (2) | 0.4746 (3) | 0.22777 (17) | 0.0523 (7) | |
H2A | 0.6637 | 0.5121 | 0.1830 | 0.063* | |
H2B | 0.6145 | 0.3835 | 0.2178 | 0.063* | |
C3 | 0.6941 (3) | 0.4935 (4) | 0.3019 (2) | 0.0806 (11) | 0.5 |
H3A | 0.6860 | 0.4194 | 0.3363 | 0.097* | 0.5 |
H3B | 0.7701 | 0.5026 | 0.2896 | 0.097* | 0.5 |
C4 | 0.6549 (5) | 0.6099 (7) | 0.3397 (4) | 0.0552 (17) | 0.5 |
H4A | 0.6913 | 0.6861 | 0.3198 | 0.066* | 0.5 |
H4B | 0.6665 | 0.6055 | 0.3960 | 0.066* | 0.5 |
C5 | 0.5338 (2) | 0.6133 (3) | 0.31911 (18) | 0.0670 (9) | 0.5 |
H5A | 0.4918 | 0.5703 | 0.3591 | 0.080* | 0.5 |
H5B | 0.5083 | 0.7017 | 0.3134 | 0.080* | 0.5 |
C3' | 0.6941 (3) | 0.4935 (4) | 0.3019 (2) | 0.0806 (11) | 0.5 |
H3'1 | 0.7241 | 0.4113 | 0.3192 | 0.097* | 0.5 |
H3'2 | 0.7536 | 0.5525 | 0.2923 | 0.097* | 0.5 |
C4' | 0.6248 (7) | 0.5461 (10) | 0.3617 (4) | 0.083 (3) | 0.5 |
H4'1 | 0.6646 | 0.6069 | 0.3945 | 0.100* | 0.5 |
H4'2 | 0.5970 | 0.4773 | 0.3945 | 0.100* | 0.5 |
C5' | 0.5338 (2) | 0.6133 (3) | 0.31911 (18) | 0.0670 (9) | 0.5 |
H5'1 | 0.4668 | 0.6064 | 0.3478 | 0.080* | 0.5 |
H5'2 | 0.5503 | 0.7041 | 0.3109 | 0.080* | 0.5 |
C6 | 0.2627 (2) | 0.3725 (2) | −0.03124 (14) | 0.0419 (5) | |
C7 | 0.3521 (2) | 0.2959 (3) | −0.04850 (16) | 0.0520 (6) | |
H7 | 0.4133 | 0.2995 | −0.0162 | 0.062* | |
C8 | 0.3512 (3) | 0.2147 (3) | −0.11275 (18) | 0.0650 (8) | |
H8 | 0.4119 | 0.1648 | −0.1234 | 0.078* | |
C9 | 0.2618 (3) | 0.2069 (3) | −0.16087 (18) | 0.0692 (9) | |
H9 | 0.2611 | 0.1504 | −0.2033 | 0.083* | |
C10 | 0.1735 (3) | 0.2826 (3) | −0.14625 (18) | 0.0677 (9) | |
H10 | 0.1131 | 0.2787 | −0.1794 | 0.081* | |
C11 | 0.1740 (2) | 0.3653 (3) | −0.08204 (16) | 0.0545 (7) | |
H11 | 0.1137 | 0.4169 | −0.0729 | 0.065* | |
C12 | 0.22278 (19) | 0.6899 (2) | 0.03333 (14) | 0.0402 (5) | |
C13 | 0.1372 (2) | 0.7587 (3) | 0.06383 (16) | 0.0508 (6) | |
H13 | 0.0922 | 0.7191 | 0.0999 | 0.061* | |
C14 | 0.1174 (2) | 0.8859 (3) | 0.04166 (17) | 0.0583 (7) | |
H14 | 0.0593 | 0.9305 | 0.0627 | 0.070* | |
C15 | 0.1829 (3) | 0.9458 (3) | −0.01099 (19) | 0.0636 (8) | |
H15 | 0.1707 | 1.0316 | −0.0250 | 0.076* | |
C16 | 0.2661 (3) | 0.8784 (3) | −0.0427 (2) | 0.0751 (10) | |
H16 | 0.3101 | 0.9182 | −0.0793 | 0.090* | |
C17 | 0.2860 (2) | 0.7515 (3) | −0.02123 (19) | 0.0641 (8) | |
H17 | 0.3430 | 0.7069 | −0.0439 | 0.077* | |
C18 | 0.12332 (19) | 0.4161 (2) | 0.13624 (14) | 0.0404 (5) | |
C19 | 0.0755 (2) | 0.3023 (3) | 0.11048 (17) | 0.0552 (7) | |
H19 | 0.1057 | 0.2566 | 0.0692 | 0.066* | |
C20 | −0.0173 (3) | 0.2559 (3) | 0.1459 (2) | 0.0666 (8) | |
H20 | −0.0485 | 0.1791 | 0.1282 | 0.080* | |
C21 | −0.0632 (2) | 0.3217 (3) | 0.20636 (18) | 0.0618 (8) | |
H21 | −0.1261 | 0.2908 | 0.2291 | 0.074* | |
C22 | −0.0157 (2) | 0.4337 (3) | 0.23320 (18) | 0.0579 (7) | |
H22 | −0.0459 | 0.4783 | 0.2749 | 0.069* | |
C23 | 0.0769 (2) | 0.4804 (3) | 0.19850 (17) | 0.0490 (6) | |
H23 | 0.1085 | 0.5562 | 0.2173 | 0.059* | |
N1 | 0.52626 (16) | 0.5437 (2) | 0.24462 (13) | 0.0433 (5) | |
S1 | 0.44472 (5) | 0.45725 (7) | 0.11166 (4) | 0.04934 (16) | |
S2 | 0.32513 (6) | 0.62405 (8) | 0.22271 (5) | 0.0592 (2) | |
Sn1 | 0.25469 (2) | 0.49609 (2) | 0.07066 (2) | 0.03669 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0373 (12) | 0.0355 (12) | 0.0456 (14) | −0.0018 (10) | −0.0042 (10) | 0.0014 (10) |
C2 | 0.0416 (14) | 0.0586 (16) | 0.0563 (17) | 0.0107 (12) | −0.0099 (12) | −0.0057 (13) |
C3 | 0.059 (2) | 0.105 (3) | 0.077 (2) | 0.0268 (19) | −0.0302 (18) | −0.022 (2) |
C4 | 0.045 (4) | 0.067 (4) | 0.053 (4) | 0.002 (3) | −0.018 (3) | −0.010 (3) |
C5 | 0.0516 (17) | 0.086 (2) | 0.0628 (19) | 0.0106 (16) | −0.0160 (14) | −0.0287 (17) |
C3' | 0.059 (2) | 0.105 (3) | 0.077 (2) | 0.0268 (19) | −0.0302 (18) | −0.022 (2) |
C4' | 0.065 (5) | 0.130 (8) | 0.053 (5) | 0.010 (5) | −0.023 (4) | −0.007 (5) |
C5' | 0.0516 (17) | 0.086 (2) | 0.0628 (19) | 0.0106 (16) | −0.0160 (14) | −0.0287 (17) |
C6 | 0.0453 (13) | 0.0420 (13) | 0.0383 (13) | −0.0054 (11) | −0.0002 (10) | 0.0002 (10) |
C7 | 0.0550 (16) | 0.0483 (15) | 0.0527 (16) | 0.0029 (13) | −0.0052 (13) | −0.0009 (13) |
C8 | 0.083 (2) | 0.0484 (16) | 0.0636 (19) | 0.0115 (15) | 0.0071 (17) | −0.0067 (14) |
C9 | 0.107 (3) | 0.0500 (17) | 0.0508 (17) | −0.0113 (18) | −0.0021 (18) | −0.0096 (14) |
C10 | 0.075 (2) | 0.074 (2) | 0.0537 (18) | −0.0202 (18) | −0.0182 (16) | −0.0070 (16) |
C11 | 0.0488 (15) | 0.0648 (18) | 0.0496 (16) | −0.0037 (13) | −0.0036 (12) | −0.0038 (13) |
C12 | 0.0369 (12) | 0.0403 (13) | 0.0433 (13) | 0.0008 (10) | −0.0051 (10) | 0.0001 (10) |
C13 | 0.0476 (14) | 0.0576 (16) | 0.0471 (15) | 0.0093 (12) | 0.0033 (12) | 0.0084 (12) |
C14 | 0.0624 (18) | 0.0587 (17) | 0.0534 (17) | 0.0233 (14) | −0.0073 (14) | −0.0023 (14) |
C15 | 0.077 (2) | 0.0455 (15) | 0.068 (2) | 0.0063 (15) | −0.0095 (17) | 0.0103 (15) |
C16 | 0.071 (2) | 0.061 (2) | 0.094 (3) | −0.0021 (17) | 0.0201 (19) | 0.0274 (18) |
C17 | 0.0563 (17) | 0.0556 (17) | 0.081 (2) | 0.0090 (14) | 0.0231 (16) | 0.0119 (15) |
C18 | 0.0362 (12) | 0.0435 (13) | 0.0413 (13) | −0.0033 (10) | −0.0030 (10) | 0.0049 (11) |
C19 | 0.0589 (17) | 0.0559 (16) | 0.0507 (16) | −0.0126 (14) | 0.0020 (13) | −0.0050 (13) |
C20 | 0.0636 (19) | 0.0608 (18) | 0.075 (2) | −0.0271 (16) | −0.0033 (16) | 0.0026 (16) |
C21 | 0.0462 (15) | 0.073 (2) | 0.0663 (19) | −0.0117 (15) | 0.0057 (14) | 0.0158 (16) |
C22 | 0.0481 (16) | 0.0658 (19) | 0.0601 (18) | 0.0026 (14) | 0.0113 (13) | 0.0057 (15) |
C23 | 0.0455 (14) | 0.0476 (15) | 0.0540 (16) | −0.0032 (11) | 0.0033 (12) | 0.0001 (12) |
N1 | 0.0353 (11) | 0.0441 (11) | 0.0502 (12) | 0.0024 (9) | −0.0086 (9) | −0.0053 (10) |
S1 | 0.0406 (3) | 0.0563 (4) | 0.0507 (4) | 0.0078 (3) | −0.0098 (3) | −0.0116 (3) |
S2 | 0.0398 (3) | 0.0698 (5) | 0.0678 (5) | 0.0120 (3) | −0.0098 (3) | −0.0196 (4) |
Sn1 | 0.03201 (10) | 0.03739 (10) | 0.04059 (10) | −0.00054 (6) | −0.00174 (7) | −0.00022 (7) |
Geometric parameters (Å, º) top
C1—N1 | 1.315 (3) | C11—H11 | 0.9300 |
C1—S2 | 1.681 (2) | C12—C17 | 1.379 (4) |
C1—S1 | 1.750 (3) | C12—C13 | 1.381 (3) |
C2—N1 | 1.474 (3) | C13—C14 | 1.387 (4) |
C2—C3 | 1.509 (4) | C13—H13 | 0.9300 |
C2—H2A | 0.9700 | C14—C15 | 1.365 (4) |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—C4 | 1.451 (7) | C15—C16 | 1.360 (5) |
C3—H3A | 0.9700 | C15—H15 | 0.9300 |
C3—H3B | 0.9700 | C16—C17 | 1.381 (4) |
C4—C5 | 1.532 (7) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C17—H17 | 0.9300 |
C4—H4B | 0.9700 | C18—C23 | 1.384 (4) |
C5—N1 | 1.462 (3) | C18—C19 | 1.384 (4) |
C5—H5A | 0.9700 | C19—C20 | 1.388 (4) |
C5—H5B | 0.9700 | C19—H19 | 0.9300 |
C4'—H4'1 | 0.9700 | C20—C21 | 1.366 (4) |
C4'—H4'2 | 0.9700 | C20—H20 | 0.9300 |
C6—C11 | 1.389 (4) | C21—C22 | 1.372 (4) |
C6—C7 | 1.393 (4) | C21—H21 | 0.9300 |
C7—C8 | 1.380 (4) | C22—C23 | 1.382 (4) |
C7—H7 | 0.9300 | C22—H22 | 0.9300 |
C8—C9 | 1.368 (5) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | Sn1—C6 | 2.160 (2) |
C9—C10 | 1.367 (5) | Sn1—C12 | 2.134 (2) |
C9—H9 | 0.9300 | Sn1—C18 | 2.149 (2) |
C10—C11 | 1.389 (4) | Sn1—S1 | 2.4710 (7) |
C10—H10 | 0.9300 | | |
| | | |
N1—C1—S2 | 123.1 (2) | C17—C12—C13 | 117.5 (2) |
N1—C1—S1 | 117.06 (18) | C17—C12—Sn1 | 121.97 (19) |
S2—C1—S1 | 119.85 (14) | C13—C12—Sn1 | 120.56 (19) |
N1—C2—C3 | 103.1 (2) | C12—C13—C14 | 121.1 (3) |
N1—C2—H2A | 111.1 | C12—C13—H13 | 119.4 |
C3—C2—H2A | 111.1 | C14—C13—H13 | 119.4 |
N1—C2—H2B | 111.1 | C15—C14—C13 | 120.3 (3) |
C3—C2—H2B | 111.1 | C15—C14—H14 | 119.9 |
H2A—C2—H2B | 109.1 | C13—C14—H14 | 119.9 |
C4—C3—C2 | 107.4 (4) | C16—C15—C14 | 119.3 (3) |
C4—C3—H3A | 110.2 | C16—C15—H15 | 120.4 |
C2—C3—H3A | 110.2 | C14—C15—H15 | 120.4 |
C4—C3—H3B | 110.2 | C15—C16—C17 | 120.8 (3) |
C2—C3—H3B | 110.2 | C15—C16—H16 | 119.6 |
H3A—C3—H3B | 108.5 | C17—C16—H16 | 119.6 |
C3—C4—C5 | 104.3 (4) | C12—C17—C16 | 121.0 (3) |
C3—C4—H4A | 110.9 | C12—C17—H17 | 119.5 |
C5—C4—H4A | 110.9 | C16—C17—H17 | 119.5 |
C3—C4—H4B | 110.9 | C23—C18—C19 | 118.1 (2) |
C5—C4—H4B | 110.9 | C23—C18—Sn1 | 122.71 (18) |
H4A—C4—H4B | 108.9 | C19—C18—Sn1 | 118.86 (19) |
N1—C5—C4 | 103.7 (3) | C18—C19—C20 | 120.4 (3) |
N1—C5—H5A | 111.0 | C18—C19—H19 | 119.8 |
C4—C5—H5A | 111.0 | C20—C19—H19 | 119.8 |
N1—C5—H5B | 111.0 | C21—C20—C19 | 120.8 (3) |
C4—C5—H5B | 111.0 | C21—C20—H20 | 119.6 |
H5A—C5—H5B | 109.0 | C19—C20—H20 | 119.6 |
H4'1—C4'—H4'2 | 108.7 | C20—C21—C22 | 119.4 (3) |
C11—C6—C7 | 117.2 (2) | C20—C21—H21 | 120.3 |
C11—C6—Sn1 | 119.27 (19) | C22—C21—H21 | 120.3 |
C7—C6—Sn1 | 123.48 (19) | C21—C22—C23 | 120.2 (3) |
C8—C7—C6 | 121.1 (3) | C21—C22—H22 | 119.9 |
C8—C7—H7 | 119.5 | C23—C22—H22 | 119.9 |
C6—C7—H7 | 119.5 | C18—C23—C22 | 121.1 (3) |
C9—C8—C7 | 120.6 (3) | C18—C23—H23 | 119.4 |
C9—C8—H8 | 119.7 | C22—C23—H23 | 119.4 |
C7—C8—H8 | 119.7 | C1—N1—C5 | 123.2 (2) |
C10—C9—C8 | 119.7 (3) | C1—N1—C2 | 125.5 (2) |
C10—C9—H9 | 120.2 | C5—N1—C2 | 111.4 (2) |
C8—C9—H9 | 120.2 | C1—S1—Sn1 | 96.24 (8) |
C9—C10—C11 | 120.1 (3) | C12—Sn1—C18 | 112.21 (9) |
C9—C10—H10 | 120.0 | C12—Sn1—C6 | 108.90 (9) |
C11—C10—H10 | 120.0 | C18—Sn1—C6 | 103.66 (9) |
C6—C11—C10 | 121.3 (3) | C12—Sn1—S1 | 114.00 (6) |
C6—C11—H11 | 119.4 | C18—Sn1—S1 | 120.74 (7) |
C10—C11—H11 | 119.4 | C6—Sn1—S1 | 94.43 (7) |
| | | |
N1—C2—C3—C4 | −24.6 (5) | C23—C18—C19—C20 | 0.9 (4) |
C2—C3—C4—C5 | 32.6 (6) | Sn1—C18—C19—C20 | −172.5 (2) |
C3—C4—C5—N1 | −27.4 (6) | C18—C19—C20—C21 | 0.2 (5) |
C11—C6—C7—C8 | −1.1 (4) | C19—C20—C21—C22 | −1.2 (5) |
Sn1—C6—C7—C8 | 177.4 (2) | C20—C21—C22—C23 | 1.0 (5) |
C6—C7—C8—C9 | −0.5 (5) | C19—C18—C23—C22 | −1.1 (4) |
C7—C8—C9—C10 | 1.6 (5) | Sn1—C18—C23—C22 | 172.0 (2) |
C8—C9—C10—C11 | −1.1 (5) | C21—C22—C23—C18 | 0.2 (4) |
C7—C6—C11—C10 | 1.6 (4) | S2—C1—N1—C5 | −1.3 (4) |
Sn1—C6—C11—C10 | −176.9 (2) | S1—C1—N1—C5 | 179.4 (2) |
C9—C10—C11—C6 | −0.5 (5) | S2—C1—N1—C2 | 179.1 (2) |
C17—C12—C13—C14 | −1.4 (4) | S1—C1—N1—C2 | −0.2 (4) |
Sn1—C12—C13—C14 | 178.2 (2) | C4—C5—N1—C1 | −167.1 (4) |
C12—C13—C14—C15 | −0.2 (4) | C4—C5—N1—C2 | 12.6 (4) |
C13—C14—C15—C16 | 1.5 (5) | C3—C2—N1—C1 | −173.9 (3) |
C14—C15—C16—C17 | −1.2 (6) | C3—C2—N1—C5 | 6.5 (3) |
C13—C12—C17—C16 | 1.8 (5) | N1—C1—S1—Sn1 | 176.18 (19) |
Sn1—C12—C17—C16 | −177.9 (3) | S2—C1—S1—Sn1 | −3.10 (16) |
C15—C16—C17—C12 | −0.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···S1 | 0.93 | 2.75 | 3.384 (3) | 127 |
C23—H23···S2 | 0.93 | 2.77 | 3.424 (3) | 129 |
C2—H2B···S2i | 0.97 | 2.96 | 3.759 (3) | 141 |
C5—H5B···S1ii | 0.97 | 2.98 | 3.750 (3) | 137 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
Selected bond lengths (Å) topSn1—C6 | 2.160 (2) | Sn1—C18 | 2.149 (2) |
Sn1—C12 | 2.134 (2) | Sn1—S1 | 2.4710 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···S1 | 0.93 | 2.75 | 3.384 (3) | 127 |
C23—H23···S2 | 0.93 | 2.77 | 3.424 (3) | 129 |
C2—H2B···S2i | 0.97 | 2.96 | 3.759 (3) | 141 |
C5—H5B···S1ii | 0.97 | 2.98 | 3.750 (3) | 137 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |