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The title compound, (C24H20P)2[Sn(C3S5)3], whose structure has been previously reported in the space group P\overline{1} at 120 K [de Assis, Chohan, Howie, Khan, Low, Spencer, Wardell & Wardell (1999), Polyhedron, 18, 3533–3544], has been crystallized in the space group C2/c and its structure has been determined at 293 K. The [Sn(C3S5)3]2− anion possesses C2 symmetry, with the SnIV atom and one C=S group lying on the twofold rotation axis. The crystal packing is stabilized by C—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012469/hy2045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012469/hy2045Isup2.hkl
Contains datablock I

CCDC reference: 643036

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.024
  • wR factor = 0.065
  • Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Sn1 - S4 .. 11.78 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - S5 .. 6.13 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - S6 .. 9.87 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(tetraphenylphosphonium) tris(2-thioxo-1,3-dithiole-4,5-dithiolato)stannate(IV) top
Crystal data top
(C24H20P)2[Sn(C3S5)3]F(000) = 2808
Mr = 1386.42Dx = 1.541 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8898 reflections
a = 24.7352 (6) Åθ = 2.5–27.6°
b = 14.7677 (4) ŵ = 1.04 mm1
c = 19.6210 (4) ÅT = 293 K
β = 123.532 (2)°Prism, purple–red
V = 5974.4 (3) Å30.36 × 0.12 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6936 independent reflections
Radiation source: fine-focus sealed tube6060 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 27.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 3230
Tmin = 0.706, Tmax = 0.895k = 1919
40822 measured reflectionsl = 2425
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0318P)2 + 4.1278P]
where P = (Fo2 + 2Fc2)/3
6936 reflections(Δ/σ)max = 0.001
340 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

Experimental. Along chemical bond of Sn1 and S4, the magnitude of the components of the anisotropic displacement parameters has larger difference. There was no significant improvement for this effect in the refinement using DELU etc instruction in the SHELXTL97 program as so as redo absorption correction for the original data.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.36637 (9)0.08672 (12)0.08963 (11)0.0428 (4)
C20.39171 (8)0.08716 (11)0.11338 (10)0.0361 (4)
C30.44805 (8)0.04790 (11)0.13238 (10)0.0366 (4)
C40.49057 (9)0.43890 (12)0.27602 (11)0.0411 (4)
C50.50000.61163 (19)0.25000.0594 (8)
S10.33102 (3)0.18687 (4)0.06668 (4)0.06359 (16)
S20.32684 (2)0.01314 (3)0.08100 (3)0.04214 (10)
S30.44663 (2)0.06984 (3)0.12443 (3)0.04594 (11)
S40.38207 (2)0.20063 (3)0.12721 (3)0.04336 (11)
S50.52109 (2)0.10405 (3)0.17151 (3)0.04444 (11)
S60.47533 (3)0.34592 (3)0.31770 (3)0.04668 (11)
S70.48042 (3)0.54604 (4)0.30613 (4)0.05676 (14)
S80.50000.72282 (6)0.25000.0977 (4)
Sn10.50000.221483 (10)0.25000.03296 (5)
C170.87001 (11)0.45376 (15)0.40971 (12)0.0556 (5)
H170.86790.47690.45230.067*
C180.72469 (9)0.61019 (13)0.20875 (11)0.0435 (4)
C190.66022 (10)0.58471 (16)0.16670 (13)0.0549 (5)
H190.64490.55080.19260.066*
C200.61854 (12)0.61020 (18)0.08539 (14)0.0655 (6)
H200.57510.59320.05680.079*
C210.64094 (13)0.66017 (17)0.04721 (13)0.0668 (7)
H210.61250.67790.00690.080*
C220.70506 (13)0.68421 (18)0.08817 (14)0.0682 (7)
H220.72010.71710.06140.082*
C230.74761 (12)0.65963 (16)0.16941 (13)0.0596 (6)
H230.79110.67610.19730.071*
C240.73080 (9)0.54458 (12)0.35312 (10)0.0386 (4)
C250.71628 (11)0.45288 (14)0.34807 (14)0.0560 (5)
H250.73230.41210.32730.067*
C260.67789 (12)0.42305 (16)0.37420 (16)0.0677 (7)
H260.66830.36170.37150.081*
C270.65391 (11)0.48258 (18)0.40383 (14)0.0634 (6)
H270.62810.46150.42140.076*
C280.66709 (11)0.57297 (17)0.40822 (14)0.0589 (5)
H280.65010.61320.42810.071*
C290.70608 (10)0.60430 (14)0.38275 (12)0.0471 (4)
H290.71540.66570.38580.057*
P10.77855 (2)0.58323 (3)0.31547 (3)0.03753 (10)
C60.82272 (9)0.68477 (12)0.36579 (11)0.0402 (4)
C70.78909 (11)0.76564 (14)0.34992 (15)0.0565 (5)
H70.74440.76720.31280.068*
C80.82229 (12)0.84360 (15)0.38947 (16)0.0694 (7)
H80.79970.89750.37990.083*
C90.88839 (13)0.84229 (17)0.44281 (16)0.0698 (7)
H90.91050.89520.46910.084*
C100.92177 (12)0.76317 (17)0.45740 (16)0.0687 (7)
H100.96670.76280.49330.082*
C110.88956 (10)0.68385 (15)0.41949 (13)0.0519 (5)
H110.91260.63020.42990.062*
C120.83270 (9)0.49259 (13)0.33190 (11)0.0412 (4)
C130.83656 (9)0.45780 (14)0.26932 (11)0.0459 (4)
H130.81230.48350.21740.055*
C140.87663 (11)0.38466 (15)0.28414 (13)0.0549 (5)
H140.87900.36100.24200.066*
C150.91276 (11)0.34696 (15)0.36048 (14)0.0564 (5)
H150.93950.29770.36980.068*
C160.90980 (12)0.38145 (16)0.42344 (14)0.0622 (6)
H160.93470.35590.47530.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0501 (10)0.0392 (9)0.0352 (8)0.0051 (8)0.0211 (8)0.0015 (7)
C20.0380 (9)0.0342 (8)0.0314 (8)0.0024 (7)0.0163 (7)0.0029 (6)
C30.0398 (9)0.0345 (8)0.0347 (8)0.0015 (7)0.0202 (7)0.0056 (6)
C40.0378 (9)0.0324 (8)0.0480 (10)0.0000 (7)0.0206 (8)0.0039 (7)
C50.0439 (15)0.0349 (14)0.080 (2)0.0000.0217 (15)0.000
S10.0754 (4)0.0430 (3)0.0646 (3)0.0193 (3)0.0338 (3)0.0051 (2)
S20.0382 (2)0.0443 (2)0.0400 (2)0.00440 (18)0.01906 (19)0.00298 (18)
S30.0485 (3)0.0339 (2)0.0522 (3)0.00102 (18)0.0259 (2)0.00564 (19)
S40.0385 (2)0.0349 (2)0.0426 (2)0.00669 (17)0.01353 (19)0.00002 (17)
S50.0403 (2)0.0438 (2)0.0542 (3)0.00455 (19)0.0292 (2)0.0126 (2)
S60.0627 (3)0.0394 (2)0.0488 (3)0.0008 (2)0.0376 (2)0.00240 (19)
S70.0522 (3)0.0389 (3)0.0748 (4)0.0024 (2)0.0323 (3)0.0114 (2)
S80.0973 (8)0.0327 (4)0.1423 (11)0.0000.0532 (8)0.000
Sn10.03601 (9)0.02899 (8)0.03119 (8)0.0000.01688 (7)0.000
C170.0664 (13)0.0606 (13)0.0395 (10)0.0182 (10)0.0291 (10)0.0057 (9)
C180.0460 (10)0.0472 (10)0.0362 (9)0.0069 (8)0.0220 (8)0.0050 (7)
C190.0491 (11)0.0633 (13)0.0457 (10)0.0038 (10)0.0219 (9)0.0036 (9)
C200.0521 (13)0.0772 (16)0.0479 (12)0.0100 (11)0.0154 (10)0.0013 (11)
C210.0825 (17)0.0660 (15)0.0382 (10)0.0238 (13)0.0246 (11)0.0072 (10)
C220.0857 (18)0.0760 (16)0.0477 (12)0.0129 (14)0.0399 (13)0.0185 (11)
C230.0614 (13)0.0703 (15)0.0463 (11)0.0028 (11)0.0293 (10)0.0135 (10)
C240.0404 (9)0.0380 (9)0.0372 (9)0.0031 (7)0.0213 (7)0.0030 (7)
C250.0638 (13)0.0409 (11)0.0653 (13)0.0076 (9)0.0369 (11)0.0023 (9)
C260.0588 (14)0.0516 (13)0.0786 (16)0.0168 (11)0.0291 (13)0.0124 (11)
C270.0431 (11)0.0836 (17)0.0606 (13)0.0054 (11)0.0267 (10)0.0248 (12)
C280.0540 (12)0.0725 (15)0.0631 (13)0.0035 (11)0.0405 (11)0.0087 (11)
C290.0521 (11)0.0437 (10)0.0523 (11)0.0017 (8)0.0332 (9)0.0024 (8)
P10.0409 (2)0.0387 (2)0.0346 (2)0.00180 (18)0.02182 (19)0.00393 (17)
C60.0432 (9)0.0417 (9)0.0410 (9)0.0012 (7)0.0266 (8)0.0056 (7)
C70.0468 (11)0.0424 (11)0.0710 (14)0.0014 (9)0.0268 (10)0.0093 (10)
C80.0705 (16)0.0384 (11)0.0890 (17)0.0013 (10)0.0376 (14)0.0063 (11)
C90.0711 (16)0.0503 (13)0.0780 (16)0.0168 (11)0.0350 (13)0.0066 (11)
C100.0477 (12)0.0659 (15)0.0735 (15)0.0098 (11)0.0214 (11)0.0042 (12)
C110.0452 (11)0.0517 (12)0.0565 (12)0.0029 (9)0.0266 (9)0.0019 (9)
C120.0439 (10)0.0413 (9)0.0382 (9)0.0038 (8)0.0226 (8)0.0018 (7)
C130.0477 (10)0.0524 (11)0.0382 (9)0.0003 (8)0.0242 (8)0.0001 (8)
C140.0604 (13)0.0576 (12)0.0555 (12)0.0017 (10)0.0375 (11)0.0080 (10)
C150.0542 (12)0.0497 (12)0.0657 (13)0.0107 (9)0.0334 (11)0.0022 (10)
C160.0668 (14)0.0623 (14)0.0490 (11)0.0201 (11)0.0266 (11)0.0131 (10)
Geometric parameters (Å, º) top
C1—S11.6491 (19)C23—H230.9300
C1—S31.724 (2)C24—C291.372 (3)
C1—S21.725 (2)C24—C251.391 (3)
C2—C31.358 (2)C24—P11.7975 (18)
C2—S41.7348 (17)C25—C261.377 (3)
C2—S21.7455 (17)C25—H250.9300
C3—S51.7346 (18)C26—C271.358 (4)
C3—S31.7443 (17)C26—H260.9300
C4—C4i1.337 (4)C27—C281.365 (3)
C4—S61.7427 (19)C27—H270.9300
C4—S71.7548 (18)C28—C291.388 (3)
C5—S81.642 (3)C28—H280.9300
C5—S7i1.7249 (17)C29—H290.9300
C5—S71.7249 (17)P1—C121.7924 (19)
S4—Sn12.5776 (4)P1—C61.7959 (19)
S5—Sn12.5572 (5)C6—C111.385 (3)
S6—Sn12.5318 (5)C6—C71.389 (3)
Sn1—S6i2.5318 (5)C7—C81.378 (3)
Sn1—S5i2.5572 (5)C7—H70.9300
Sn1—S4i2.5776 (4)C8—C91.371 (3)
C17—C161.374 (3)C8—H80.9300
C17—C121.398 (3)C9—C101.367 (4)
C17—H170.9300C9—H90.9300
C18—C191.383 (3)C10—C111.380 (3)
C18—C231.391 (3)C10—H100.9300
C18—P11.7989 (18)C11—H110.9300
C19—C201.390 (3)C12—C131.382 (3)
C19—H190.9300C13—C141.384 (3)
C20—C211.368 (4)C13—H130.9300
C20—H200.9300C14—C151.369 (3)
C21—C221.371 (4)C14—H140.9300
C21—H210.9300C15—C161.375 (3)
C22—C231.388 (3)C15—H150.9300
C22—H220.9300C16—H160.9300
S1—C1—S3123.97 (12)C29—C24—C25119.87 (18)
S1—C1—S2123.61 (12)C29—C24—P1121.20 (14)
S3—C1—S2112.42 (10)C25—C24—P1118.85 (16)
C3—C2—S4125.34 (13)C26—C25—C24119.3 (2)
C3—C2—S2115.48 (13)C26—C25—H25120.4
S4—C2—S2118.93 (10)C24—C25—H25120.4
C2—C3—S5125.28 (13)C27—C26—C25120.4 (2)
C2—C3—S3115.74 (13)C27—C26—H26119.8
S5—C3—S3118.73 (10)C25—C26—H26119.8
C4i—C4—S6128.01 (6)C26—C27—C28121.0 (2)
C4i—C4—S7115.62 (7)C26—C27—H27119.5
S6—C4—S7116.37 (11)C28—C27—H27119.5
S8—C5—S7i124.16 (8)C27—C28—C29119.5 (2)
S8—C5—S7124.16 (8)C27—C28—H28120.3
S7i—C5—S7111.67 (16)C29—C28—H28120.3
C1—S2—C298.19 (9)C24—C29—C28119.95 (19)
C1—S3—C398.13 (9)C24—C29—H29120.0
C2—S4—Sn194.54 (6)C28—C29—H29120.0
C3—S5—Sn194.68 (6)C12—P1—C6110.94 (9)
C4—S6—Sn198.53 (6)C12—P1—C24106.52 (9)
C5—S7—C498.54 (10)C6—P1—C24112.18 (8)
S6i—Sn1—S686.92 (2)C12—P1—C18111.97 (9)
S6i—Sn1—S589.297 (16)C6—P1—C18106.83 (9)
S6—Sn1—S5175.383 (16)C24—P1—C18108.45 (9)
S6i—Sn1—S5i175.383 (16)C11—C6—C7119.62 (19)
S6—Sn1—S5i89.297 (16)C11—C6—P1121.20 (15)
S5—Sn1—S5i94.60 (2)C7—C6—P1119.18 (15)
S6i—Sn1—S494.169 (17)C8—C7—C6119.7 (2)
S6—Sn1—S495.783 (16)C8—C7—H7120.2
S5—Sn1—S481.844 (15)C6—C7—H7120.2
S5i—Sn1—S488.843 (16)C9—C8—C7120.5 (2)
S6i—Sn1—S4i95.783 (16)C9—C8—H8119.8
S6—Sn1—S4i94.169 (17)C7—C8—H8119.8
S5—Sn1—S4i88.843 (16)C10—C9—C8120.0 (2)
S5i—Sn1—S4i81.844 (15)C10—C9—H9120.0
S4—Sn1—S4i166.27 (2)C8—C9—H9120.0
C16—C17—C12120.13 (19)C9—C10—C11120.7 (2)
C16—C17—H17119.9C9—C10—H10119.6
C12—C17—H17119.9C11—C10—H10119.6
C19—C18—C23120.07 (18)C10—C11—C6119.5 (2)
C19—C18—P1120.19 (15)C10—C11—H11120.2
C23—C18—P1119.70 (16)C6—C11—H11120.2
C18—C19—C20119.4 (2)C13—C12—C17119.33 (18)
C18—C19—H19120.3C13—C12—P1121.96 (14)
C20—C19—H19120.3C17—C12—P1118.66 (14)
C21—C20—C19120.4 (2)C12—C13—C14119.76 (18)
C21—C20—H20119.8C12—C13—H13120.1
C19—C20—H20119.8C14—C13—H13120.1
C20—C21—C22120.4 (2)C15—C14—C13120.42 (19)
C20—C21—H21119.8C15—C14—H14119.8
C22—C21—H21119.8C13—C14—H14119.8
C21—C22—C23120.2 (2)C14—C15—C16120.4 (2)
C21—C22—H22119.9C14—C15—H15119.8
C23—C22—H22119.9C16—C15—H15119.8
C22—C23—C18119.5 (2)C17—C16—C15120.0 (2)
C22—C23—H23120.3C17—C16—H16120.0
C18—C23—H23120.3C15—C16—H16120.0
S4—C2—C3—S52.0 (2)C25—C26—C27—C280.1 (4)
S2—C2—C3—S5176.16 (10)C26—C27—C28—C290.6 (4)
S4—C2—C3—S3172.12 (10)C25—C24—C29—C280.5 (3)
S2—C2—C3—S32.05 (18)P1—C24—C29—C28177.28 (16)
S1—C1—S2—C2179.44 (12)C27—C28—C29—C240.3 (3)
S3—C1—S2—C20.30 (11)C29—C24—P1—C12151.43 (15)
C3—C2—S2—C11.06 (15)C25—C24—P1—C1231.79 (18)
S4—C2—S2—C1173.51 (11)C29—C24—P1—C629.86 (18)
S1—C1—S3—C3178.55 (12)C25—C24—P1—C6153.36 (16)
S2—C1—S3—C31.19 (12)C29—C24—P1—C1887.89 (17)
C2—C3—S3—C11.98 (15)C25—C24—P1—C1888.89 (17)
S5—C3—S3—C1176.50 (11)C19—C18—P1—C12105.71 (18)
C3—C2—S4—Sn128.96 (16)C23—C18—P1—C1276.60 (19)
S2—C2—S4—Sn1145.02 (9)C19—C18—P1—C6132.64 (17)
C2—C3—S5—Sn131.82 (16)C23—C18—P1—C645.04 (19)
S3—C3—S5—Sn1142.13 (9)C19—C18—P1—C2411.5 (2)
C4i—C4—S6—Sn10.1 (2)C23—C18—P1—C24166.15 (17)
S7—C4—S6—Sn1179.54 (9)C12—P1—C6—C119.23 (19)
S8—C5—S7—C4179.81 (6)C24—P1—C6—C11109.77 (17)
S7i—C5—S7—C40.19 (6)C18—P1—C6—C11131.52 (16)
C4i—C4—S7—C50.7 (2)C12—P1—C6—C7170.28 (16)
S6—C4—S7—C5179.65 (9)C24—P1—C6—C770.72 (18)
C4—S6—Sn1—S6i0.03 (6)C18—P1—C6—C747.99 (18)
C4—S6—Sn1—S493.91 (6)C11—C6—C7—C81.9 (3)
C4—S6—Sn1—S4i95.55 (6)P1—C6—C7—C8178.63 (19)
C3—S5—Sn1—S6i127.73 (6)C6—C7—C8—C91.6 (4)
C3—S5—Sn1—S5i54.75 (6)C7—C8—C9—C100.4 (4)
C3—S5—Sn1—S433.42 (6)C8—C9—C10—C110.6 (4)
C3—S5—Sn1—S4i136.47 (6)C9—C10—C11—C60.3 (4)
C2—S4—Sn1—S6i121.50 (6)C7—C6—C11—C100.9 (3)
C2—S4—Sn1—S6151.18 (6)P1—C6—C11—C10179.58 (18)
C2—S4—Sn1—S532.81 (6)C16—C17—C12—C130.3 (3)
C2—S4—Sn1—S5i62.01 (6)C16—C17—C12—P1177.04 (19)
C2—S4—Sn1—S4i14.91 (6)C6—P1—C12—C13111.47 (17)
C23—C18—C19—C201.0 (3)C24—P1—C12—C13126.18 (17)
P1—C18—C19—C20176.67 (17)C18—P1—C12—C137.8 (2)
C18—C19—C20—C210.1 (4)C6—P1—C12—C1771.25 (19)
C19—C20—C21—C221.3 (4)C24—P1—C12—C1751.10 (19)
C20—C21—C22—C231.4 (4)C18—P1—C12—C17169.49 (17)
C21—C22—C23—C180.2 (4)C17—C12—C13—C140.7 (3)
C19—C18—C23—C220.9 (3)P1—C12—C13—C14176.60 (16)
P1—C18—C23—C22176.74 (19)C12—C13—C14—C150.4 (3)
C29—C24—C25—C261.0 (3)C13—C14—C15—C160.2 (4)
P1—C24—C25—C26177.82 (17)C12—C17—C16—C150.3 (4)
C24—C25—C26—C270.7 (4)C14—C15—C16—C170.5 (4)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···S4i0.932.693.598 (2)165
C29—H29···S1ii0.932.853.513 (2)129
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+1, z+1/2.
 

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