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In the title compound, [Sn(C6H5)3(C5H8NS2)], the SnIV atom adopts a distorted SnC3S 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813022472/hb7122sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536813022472/hb7122Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813022472/hb7122Isup3.cml
Supplementary material

CCDC reference: 963423

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Related literature top

For background to the structures and applications of organotin compounds, see: Abbas et al. (2013); Pellerito & Nagy (2002); Ronconi et al. (2005); Shahzadi et al. (2006, 2008); Sirajuddin et al. (2012).

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The partial packing, which shows that molecules form dimers due to C—H···S bonds.
Triphenyl(pyrrolidine-1-carbodithioato-κS)tin(IV) top
Crystal data top
[Sn(C6H5)3(C5H8NS2)]Z = 4
Mr = 496.23F(000) = 1000
Monoclinic, P21/cDx = 1.516 Mg m3
a = 12.3467 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3227 (3) ŵ = 1.38 mm1
c = 17.0611 (6) ÅT = 296 K
β = 90.864 (2)°Prism, colourless
V = 2174.21 (12) Å30.32 × 0.26 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1512
Tmin = 0.667, Tmax = 0.734k = 1212
16466 measured reflectionsl = 2021
4265 independent reflections
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-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 reflectionsΔρmax = 0.39 e Å3
253 parametersΔρmin = 0.47 e Å3
Crystal data top
[Sn(C6H5)3(C5H8NS2)]V = 2174.21 (12) Å3
Mr = 496.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.3467 (4) ŵ = 1.38 mm1
b = 10.3227 (3) ÅT = 296 K
c = 17.0611 (6) Å0.32 × 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 = 0.734Rint = 0.020
16466 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0223 restraints
wR(F2) = 0.062H-atom parameters constrained
S = 1.01Δρmax = 0.39 e Å3
4265 reflectionsΔρmin = 0.47 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.43914 (19)0.5449 (2)0.19935 (15)0.0395 (5)
C20.6278 (2)0.4746 (3)0.22777 (17)0.0523 (7)
H2A0.66370.51210.18300.063*
H2B0.61450.38350.21780.063*
C30.6941 (3)0.4935 (4)0.3019 (2)0.0806 (11)0.5
H3A0.68600.41940.33630.097*0.5
H3B0.77010.50260.28960.097*0.5
C40.6549 (5)0.6099 (7)0.3397 (4)0.0552 (17)0.5
H4A0.69130.68610.31980.066*0.5
H4B0.66650.60550.39600.066*0.5
C50.5338 (2)0.6133 (3)0.31911 (18)0.0670 (9)0.5
H5A0.49180.57030.35910.080*0.5
H5B0.50830.70170.31340.080*0.5
C3'0.6941 (3)0.4935 (4)0.3019 (2)0.0806 (11)0.5
H3'10.72410.41130.31920.097*0.5
H3'20.75360.55250.29230.097*0.5
C4'0.6248 (7)0.5461 (10)0.3617 (4)0.083 (3)0.5
H4'10.66460.60690.39450.100*0.5
H4'20.59700.47730.39450.100*0.5
C5'0.5338 (2)0.6133 (3)0.31911 (18)0.0670 (9)0.5
H5'10.46680.60640.34780.080*0.5
H5'20.55030.70410.31090.080*0.5
C60.2627 (2)0.3725 (2)0.03124 (14)0.0419 (5)
C70.3521 (2)0.2959 (3)0.04850 (16)0.0520 (6)
H70.41330.29950.01620.062*
C80.3512 (3)0.2147 (3)0.11275 (18)0.0650 (8)
H80.41190.16480.12340.078*
C90.2618 (3)0.2069 (3)0.16087 (18)0.0692 (9)
H90.26110.15040.20330.083*
C100.1735 (3)0.2826 (3)0.14625 (18)0.0677 (9)
H100.11310.27870.17940.081*
C110.1740 (2)0.3653 (3)0.08204 (16)0.0545 (7)
H110.11370.41690.07290.065*
C120.22278 (19)0.6899 (2)0.03333 (14)0.0402 (5)
C130.1372 (2)0.7587 (3)0.06383 (16)0.0508 (6)
H130.09220.71910.09990.061*
C140.1174 (2)0.8859 (3)0.04166 (17)0.0583 (7)
H140.05930.93050.06270.070*
C150.1829 (3)0.9458 (3)0.01099 (19)0.0636 (8)
H150.17071.03160.02500.076*
C160.2661 (3)0.8784 (3)0.0427 (2)0.0751 (10)
H160.31010.91820.07930.090*
C170.2860 (2)0.7515 (3)0.02123 (19)0.0641 (8)
H170.34300.70690.04390.077*
C180.12332 (19)0.4161 (2)0.13624 (14)0.0404 (5)
C190.0755 (2)0.3023 (3)0.11048 (17)0.0552 (7)
H190.10570.25660.06920.066*
C200.0173 (3)0.2559 (3)0.1459 (2)0.0666 (8)
H200.04850.17910.12820.080*
C210.0632 (2)0.3217 (3)0.20636 (18)0.0618 (8)
H210.12610.29080.22910.074*
C220.0157 (2)0.4337 (3)0.23320 (18)0.0579 (7)
H220.04590.47830.27490.069*
C230.0769 (2)0.4804 (3)0.19850 (17)0.0490 (6)
H230.10850.55620.21730.059*
N10.52626 (16)0.5437 (2)0.24462 (13)0.0433 (5)
S10.44472 (5)0.45725 (7)0.11166 (4)0.04934 (16)
S20.32513 (6)0.62405 (8)0.22271 (5)0.0592 (2)
Sn10.25469 (2)0.49609 (2)0.07066 (2)0.03669 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0373 (12)0.0355 (12)0.0456 (14)0.0018 (10)0.0042 (10)0.0014 (10)
C20.0416 (14)0.0586 (16)0.0563 (17)0.0107 (12)0.0099 (12)0.0057 (13)
C30.059 (2)0.105 (3)0.077 (2)0.0268 (19)0.0302 (18)0.022 (2)
C40.045 (4)0.067 (4)0.053 (4)0.002 (3)0.018 (3)0.010 (3)
C50.0516 (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)
C60.0453 (13)0.0420 (13)0.0383 (13)0.0054 (11)0.0002 (10)0.0002 (10)
C70.0550 (16)0.0483 (15)0.0527 (16)0.0029 (13)0.0052 (13)0.0009 (13)
C80.083 (2)0.0484 (16)0.0636 (19)0.0115 (15)0.0071 (17)0.0067 (14)
C90.107 (3)0.0500 (17)0.0508 (17)0.0113 (18)0.0021 (18)0.0096 (14)
C100.075 (2)0.074 (2)0.0537 (18)0.0202 (18)0.0182 (16)0.0070 (16)
C110.0488 (15)0.0648 (18)0.0496 (16)0.0037 (13)0.0036 (12)0.0038 (13)
C120.0369 (12)0.0403 (13)0.0433 (13)0.0008 (10)0.0051 (10)0.0001 (10)
C130.0476 (14)0.0576 (16)0.0471 (15)0.0093 (12)0.0033 (12)0.0084 (12)
C140.0624 (18)0.0587 (17)0.0534 (17)0.0233 (14)0.0073 (14)0.0023 (14)
C150.077 (2)0.0455 (15)0.068 (2)0.0063 (15)0.0095 (17)0.0103 (15)
C160.071 (2)0.061 (2)0.094 (3)0.0021 (17)0.0201 (19)0.0274 (18)
C170.0563 (17)0.0556 (17)0.081 (2)0.0090 (14)0.0231 (16)0.0119 (15)
C180.0362 (12)0.0435 (13)0.0413 (13)0.0033 (10)0.0030 (10)0.0049 (11)
C190.0589 (17)0.0559 (16)0.0507 (16)0.0126 (14)0.0020 (13)0.0050 (13)
C200.0636 (19)0.0608 (18)0.075 (2)0.0271 (16)0.0033 (16)0.0026 (16)
C210.0462 (15)0.073 (2)0.0663 (19)0.0117 (15)0.0057 (14)0.0158 (16)
C220.0481 (16)0.0658 (19)0.0601 (18)0.0026 (14)0.0113 (13)0.0057 (15)
C230.0455 (14)0.0476 (15)0.0540 (16)0.0032 (11)0.0033 (12)0.0001 (12)
N10.0353 (11)0.0441 (11)0.0502 (12)0.0024 (9)0.0086 (9)0.0053 (10)
S10.0406 (3)0.0563 (4)0.0507 (4)0.0078 (3)0.0098 (3)0.0116 (3)
S20.0398 (3)0.0698 (5)0.0678 (5)0.0120 (3)0.0098 (3)0.0196 (4)
Sn10.03201 (10)0.03739 (10)0.04059 (10)0.00054 (6)0.00174 (7)0.00022 (7)
Geometric parameters (Å, º) top
C1—N11.315 (3)C11—H110.9300
C1—S21.681 (2)C12—C171.379 (4)
C1—S11.750 (3)C12—C131.381 (3)
C2—N11.474 (3)C13—C141.387 (4)
C2—C31.509 (4)C13—H130.9300
C2—H2A0.9700C14—C151.365 (4)
C2—H2B0.9700C14—H140.9300
C3—C41.451 (7)C15—C161.360 (5)
C3—H3A0.9700C15—H150.9300
C3—H3B0.9700C16—C171.381 (4)
C4—C51.532 (7)C16—H160.9300
C4—H4A0.9700C17—H170.9300
C4—H4B0.9700C18—C231.384 (4)
C5—N11.462 (3)C18—C191.384 (4)
C5—H5A0.9700C19—C201.388 (4)
C5—H5B0.9700C19—H190.9300
C4'—H4'10.9700C20—C211.366 (4)
C4'—H4'20.9700C20—H200.9300
C6—C111.389 (4)C21—C221.372 (4)
C6—C71.393 (4)C21—H210.9300
C7—C81.380 (4)C22—C231.382 (4)
C7—H70.9300C22—H220.9300
C8—C91.368 (5)C23—H230.9300
C8—H80.9300Sn1—C62.160 (2)
C9—C101.367 (5)Sn1—C122.134 (2)
C9—H90.9300Sn1—C182.149 (2)
C10—C111.389 (4)Sn1—S12.4710 (7)
C10—H100.9300
N1—C1—S2123.1 (2)C17—C12—C13117.5 (2)
N1—C1—S1117.06 (18)C17—C12—Sn1121.97 (19)
S2—C1—S1119.85 (14)C13—C12—Sn1120.56 (19)
N1—C2—C3103.1 (2)C12—C13—C14121.1 (3)
N1—C2—H2A111.1C12—C13—H13119.4
C3—C2—H2A111.1C14—C13—H13119.4
N1—C2—H2B111.1C15—C14—C13120.3 (3)
C3—C2—H2B111.1C15—C14—H14119.9
H2A—C2—H2B109.1C13—C14—H14119.9
C4—C3—C2107.4 (4)C16—C15—C14119.3 (3)
C4—C3—H3A110.2C16—C15—H15120.4
C2—C3—H3A110.2C14—C15—H15120.4
C4—C3—H3B110.2C15—C16—C17120.8 (3)
C2—C3—H3B110.2C15—C16—H16119.6
H3A—C3—H3B108.5C17—C16—H16119.6
C3—C4—C5104.3 (4)C12—C17—C16121.0 (3)
C3—C4—H4A110.9C12—C17—H17119.5
C5—C4—H4A110.9C16—C17—H17119.5
C3—C4—H4B110.9C23—C18—C19118.1 (2)
C5—C4—H4B110.9C23—C18—Sn1122.71 (18)
H4A—C4—H4B108.9C19—C18—Sn1118.86 (19)
N1—C5—C4103.7 (3)C18—C19—C20120.4 (3)
N1—C5—H5A111.0C18—C19—H19119.8
C4—C5—H5A111.0C20—C19—H19119.8
N1—C5—H5B111.0C21—C20—C19120.8 (3)
C4—C5—H5B111.0C21—C20—H20119.6
H5A—C5—H5B109.0C19—C20—H20119.6
H4'1—C4'—H4'2108.7C20—C21—C22119.4 (3)
C11—C6—C7117.2 (2)C20—C21—H21120.3
C11—C6—Sn1119.27 (19)C22—C21—H21120.3
C7—C6—Sn1123.48 (19)C21—C22—C23120.2 (3)
C8—C7—C6121.1 (3)C21—C22—H22119.9
C8—C7—H7119.5C23—C22—H22119.9
C6—C7—H7119.5C18—C23—C22121.1 (3)
C9—C8—C7120.6 (3)C18—C23—H23119.4
C9—C8—H8119.7C22—C23—H23119.4
C7—C8—H8119.7C1—N1—C5123.2 (2)
C10—C9—C8119.7 (3)C1—N1—C2125.5 (2)
C10—C9—H9120.2C5—N1—C2111.4 (2)
C8—C9—H9120.2C1—S1—Sn196.24 (8)
C9—C10—C11120.1 (3)C12—Sn1—C18112.21 (9)
C9—C10—H10120.0C12—Sn1—C6108.90 (9)
C11—C10—H10120.0C18—Sn1—C6103.66 (9)
C6—C11—C10121.3 (3)C12—Sn1—S1114.00 (6)
C6—C11—H11119.4C18—Sn1—S1120.74 (7)
C10—C11—H11119.4C6—Sn1—S194.43 (7)
N1—C2—C3—C424.6 (5)C23—C18—C19—C200.9 (4)
C2—C3—C4—C532.6 (6)Sn1—C18—C19—C20172.5 (2)
C3—C4—C5—N127.4 (6)C18—C19—C20—C210.2 (5)
C11—C6—C7—C81.1 (4)C19—C20—C21—C221.2 (5)
Sn1—C6—C7—C8177.4 (2)C20—C21—C22—C231.0 (5)
C6—C7—C8—C90.5 (5)C19—C18—C23—C221.1 (4)
C7—C8—C9—C101.6 (5)Sn1—C18—C23—C22172.0 (2)
C8—C9—C10—C111.1 (5)C21—C22—C23—C180.2 (4)
C7—C6—C11—C101.6 (4)S2—C1—N1—C51.3 (4)
Sn1—C6—C11—C10176.9 (2)S1—C1—N1—C5179.4 (2)
C9—C10—C11—C60.5 (5)S2—C1—N1—C2179.1 (2)
C17—C12—C13—C141.4 (4)S1—C1—N1—C20.2 (4)
Sn1—C12—C13—C14178.2 (2)C4—C5—N1—C1167.1 (4)
C12—C13—C14—C150.2 (4)C4—C5—N1—C212.6 (4)
C13—C14—C15—C161.5 (5)C3—C2—N1—C1173.9 (3)
C14—C15—C16—C171.2 (6)C3—C2—N1—C56.5 (3)
C13—C12—C17—C161.8 (5)N1—C1—S1—Sn1176.18 (19)
Sn1—C12—C17—C16177.9 (3)S2—C1—S1—Sn13.10 (16)
C15—C16—C17—C120.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···S10.932.753.384 (3)127
C23—H23···S20.932.773.424 (3)129
C2—H2B···S2i0.972.963.759 (3)141
C5—H5B···S1ii0.972.983.750 (3)137
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2.
Selected bond lengths (Å) top
Sn1—C62.160 (2)Sn1—C182.149 (2)
Sn1—C122.134 (2)Sn1—S12.4710 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···S10.932.753.384 (3)127
C23—H23···S20.932.773.424 (3)129
C2—H2B···S2i0.972.963.759 (3)141
C5—H5B···S1ii0.972.983.750 (3)137
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2.
 

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