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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m108.
Published online 2007 December 6. doi:  10.1107/S1600536807063830
PMCID: PMC2915061

Dichloridotriphenyl­anti­mony(V)–bis­(pyrrolidin-1-ylthio­carbon­yl) disulfide (1/1)

Abstract

The asymmetric unit of the title compound, [Sb(C6H5)3Cl2]·C10H16N2S4, comprises a bis­(pyrrolidinylthio­carbamo­yl) mol­ecule and a dichloro­triphenyl­anti­mony(V) complex. In the Sb complex, the central atom is coordinated by three C atoms of the three phenyl ligands and two Cl atoms in a slightly distorted trigonal-bipyramidal geometry. The thio­carbamoyl units, connected via the disulfide bond, are approximately perpendicular to each other. The mol­ecules are connected by weak C—H(...)S and C—H(...)Cl hydrogen-bonding inter­actions into two one-dimensional supra­molecular chains.

Related literature

For related structures, see: Williams et al. (1983 [triangle]); Feng Li et al. (2006 [triangle]). For discussion on C—H(...)S inter­actions, see: Srinivasan et al. (2007 [triangle]). For related literature, see: Kumar et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m108-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3Cl2]·C10H16N2S4
  • M r = 716.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m108-efi1.jpg
  • a = 14.8138 (18) Å
  • b = 13.6440 (13) Å
  • c = 16.316 (3) Å
  • β = 105.509 (2)°
  • V = 3177.7 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.32 mm−1
  • T = 298 (2) K
  • 0.50 × 0.42 × 0.39 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.558, T max = 0.627
  • 14597 measured reflections
  • 5560 independent reflections
  • 4333 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.092
  • S = 1.00
  • 5560 reflections
  • 335 parameters
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063830/si2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063830/si2063Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

supplementary crystallographic information

Comment

In the title complex, the antimony atom is coordinated by three C atoms of three phenyl ligands and two Cl atoms in a slightly distorted trigonal-bipyramidal geometry. Atoms Cl1, Cl2 of the complex lie in axial positions (Fig. 1), with the axial angle Cl1—Sb1—Cl2 178.65 (4)°, deviating substantially from the linear value of 180°. The distances Sb—Cl also vary merely with the role they play in the structure: Sb1—Cl1 = 2.4720 (9) Å and Sb1—Cl2 = 2.4792 (10) Å. In the bis(pyrrolidinylthiocarbamoyl) molecule of the title compound, the thiocarbamoyl moieties, connected via the disulfide bond (S1—S3 = 2.0029 (17) Å), are approximately perpendicular to each other. A Newman projection, calculated with PLATON, with a view along the disulfide bond results in a dihedral angle of 87 ° for C1—S1—S3—C6 (Spek, 2003).

The Dipyrrolidylthiuram disulfide molecule, (which is another name of the organic part in our structure) shows a planar model with crystallographic inversion symmetry in the midpoint of the S—S bond (Williams et al., 1983).

In the similar structure bis(N,N-dicyclohexylthiocarbamoyl) disulfide, a crystallographic twofold axis passes through the midpoint of the S—S bond (Li et al., 2006). The disulfide S—S distance is close to the distances observed in free (uncoordinated) disulfides (Kumar et al., 1990).

The S atoms of bis(pyrrolidinylthiocarbamoyl) and the Cl atoms of dichlorotriphenylantimony play a significant role in the crystal packing, linking the complex molecules by weak C—H···S and C—H···Cl (Table 1) hydrogen bonds to form two one-dimensional supramolecular chains (Fig. 2).

Experimental

Chlorotriphenylantimony (0.2 mmol) was dissolved in benzene (15 ml) and bis(pyrrolidinylthiocarbamoyl) (0.2 mmol) dissolved in methanol was added with stirring at room temperature for eight hours and then filtered. Orange crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum/dichloromethane (1:2 v/v) solution over a period of twenty days (yield 85%. m.p. 432k). Anal. Calcd (%) for C28H31N2S4Cl2Sb(Mr = 716.48): C, 46.94; H, 4.36; N, 3.91. Found (%): C, 46.89; H, 4.31; N, 3.87.

Refinement

The H atoms bound to C of pyrrolidine were located in a difference map and were refined as riding on their respective C atoms with distances C—H = 0.97 Å and with Uiso(H) = 1.2Ueq(C). The other H atoms were constraint at calculated positions (riding mode), with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Crystal packing of the title compound, showing catemer chains, linked by weak C15—H15···S4, C13—H13···Cl2, C8—H8A···Cl1 hydrogen bonding contacts, indicated ...

Crystal data

[Sb(C6H5)3Cl2]·C10H16N2S4F000 = 1448
Mr = 716.48Dx = 1.498 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7025 reflections
a = 14.8138 (18) Åθ = 2.2–27.8º
b = 13.6440 (13) ŵ = 1.32 mm1
c = 16.316 (3) ÅT = 298 (2) K
β = 105.509 (2)ºBlock, colorless
V = 3177.7 (8) Å30.50 × 0.42 × 0.39 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer5560 independent reflections
Radiation source: fine-focus sealed tube4333 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→10
Tmin = 0.558, Tmax = 0.627k = −16→16
14597 measured reflectionsl = −19→19

Refinement

Refinement on f2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031  w = 1/[σ2(Fo2) + (0.045P)2 + 1.9404P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.67 e Å3
5560 reflectionsΔρmin = −0.59 e Å3
335 parametersExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (3)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sb10.018116 (16)0.991080 (17)0.234502 (14)0.03657 (11)
Cl1−0.07709 (7)1.08719 (7)0.11362 (6)0.0508 (3)
Cl20.11117 (8)0.89132 (8)0.35457 (6)0.0569 (3)
N10.6750 (2)0.8384 (2)0.3780 (2)0.0516 (8)
N20.4034 (2)1.0375 (2)0.0796 (2)0.0534 (9)
S10.59570 (9)0.82805 (9)0.21567 (7)0.0664 (3)
S20.50821 (9)0.92203 (9)0.34589 (8)0.0665 (3)
S30.46930 (9)0.86974 (9)0.14467 (7)0.0704 (4)
S40.58682 (9)1.05180 (10)0.13631 (8)0.0742 (4)
C10.5950 (3)0.8643 (3)0.3226 (2)0.0479 (10)
C20.7541 (3)0.7877 (3)0.3599 (3)0.0660 (12)
H2A0.77180.81810.31270.079*
H2B0.73960.71920.34670.079*
C30.8311 (4)0.7985 (4)0.4418 (3)0.0879 (17)
H3A0.87350.74290.45050.106*
H3B0.86670.85800.44150.106*
C40.7802 (4)0.8025 (5)0.5087 (3)0.0972 (19)
H4A0.81740.83560.55910.117*
H4B0.76540.73710.52430.117*
C50.6926 (3)0.8589 (4)0.4697 (3)0.0685 (13)
H5A0.64100.83620.49100.082*
H5B0.70170.92850.48120.082*
C60.4843 (3)0.9968 (3)0.1173 (2)0.0531 (11)
C70.3104 (3)0.9904 (3)0.0625 (3)0.0732 (14)
H7A0.30290.95670.11260.088*
H7B0.30150.94380.01610.088*
C80.2428 (4)1.0747 (4)0.0389 (4)0.100 (2)
H8A0.18501.0541−0.00120.120*
H8B0.22831.10180.08890.120*
C90.2927 (4)1.1471 (5)−0.0001 (4)0.104 (2)
H9A0.27031.21280.00610.124*
H9B0.28281.1334−0.06020.124*
C100.3956 (4)1.1383 (3)0.0462 (3)0.0739 (14)
H10A0.43451.14760.00760.089*
H10B0.41331.18580.09200.089*
C11−0.0708 (2)1.0332 (3)0.3075 (2)0.0377 (8)
C12−0.0319 (3)1.0717 (3)0.3882 (2)0.0496 (10)
H120.03281.07570.40950.059*
C13−0.0893 (3)1.1037 (3)0.4366 (3)0.0589 (11)
H13−0.06321.13150.48970.071*
C14−0.1851 (3)1.0950 (3)0.4067 (3)0.0589 (11)
H14−0.22351.11510.44030.071*
C15−0.2239 (3)1.0566 (3)0.3274 (3)0.0610 (11)
H15−0.28861.05080.30750.073*
C16−0.1680 (3)1.0268 (3)0.2772 (2)0.0495 (10)
H16−0.19501.00240.22300.059*
C17−0.0118 (2)0.8611 (3)0.1610 (2)0.0384 (8)
C18−0.0404 (3)0.7789 (3)0.1959 (3)0.0503 (10)
H18−0.04780.78080.25070.060*
C19−0.0580 (3)0.6933 (3)0.1490 (3)0.0607 (12)
H19−0.07730.63740.17230.073*
C20−0.0469 (3)0.6908 (3)0.0685 (3)0.0650 (12)
H20−0.05810.63290.03730.078*
C21−0.0195 (3)0.7731 (3)0.0336 (3)0.0611 (11)
H21−0.01270.7709−0.02140.073*
C22−0.0018 (3)0.8593 (3)0.0794 (2)0.0491 (10)
H220.01660.91520.05560.059*
C230.1365 (3)1.0813 (3)0.2432 (2)0.0428 (9)
C240.2261 (3)1.0430 (4)0.2705 (3)0.0642 (12)
H240.23510.97650.28250.077*
C250.3018 (3)1.1049 (4)0.2797 (4)0.0844 (16)
H250.36221.07950.29670.101*
C260.2892 (4)1.2026 (4)0.2643 (4)0.0859 (16)
H260.34081.24370.27140.103*
C270.2006 (4)1.2404 (3)0.2382 (3)0.0757 (14)
H270.19231.30720.22780.091*
C280.1236 (3)1.1801 (3)0.2271 (2)0.0505 (10)
H280.06351.20600.20890.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.03922 (16)0.03827 (16)0.03499 (15)0.00222 (11)0.01473 (11)0.00279 (10)
Cl10.0587 (6)0.0493 (6)0.0422 (5)0.0073 (5)0.0095 (4)0.0092 (4)
Cl20.0678 (7)0.0605 (6)0.0419 (5)0.0145 (6)0.0138 (5)0.0138 (4)
N10.050 (2)0.0453 (19)0.0531 (19)−0.0006 (17)0.0033 (16)0.0008 (15)
N20.059 (2)0.0451 (19)0.0507 (19)−0.0064 (18)0.0047 (17)−0.0006 (15)
S10.0762 (8)0.0609 (7)0.0545 (6)0.0119 (6)0.0046 (6)−0.0034 (5)
S20.0606 (7)0.0570 (7)0.0807 (8)0.0096 (6)0.0170 (6)0.0004 (6)
S30.0749 (8)0.0524 (7)0.0655 (7)−0.0139 (6)−0.0136 (6)0.0068 (5)
S40.0652 (8)0.0727 (8)0.0780 (8)−0.0193 (7)0.0074 (6)0.0031 (6)
C10.053 (2)0.034 (2)0.054 (2)−0.0035 (18)0.0078 (19)0.0020 (16)
C20.057 (3)0.057 (3)0.080 (3)0.005 (2)0.012 (2)−0.004 (2)
C30.059 (3)0.083 (4)0.104 (4)0.013 (3)−0.010 (3)−0.005 (3)
C40.085 (4)0.111 (5)0.076 (4)0.005 (4)−0.014 (3)0.017 (3)
C50.072 (3)0.072 (3)0.055 (3)−0.003 (3)0.005 (2)0.006 (2)
C60.066 (3)0.048 (2)0.040 (2)−0.008 (2)0.005 (2)−0.0023 (17)
C70.059 (3)0.066 (3)0.085 (3)−0.008 (3)0.001 (3)−0.005 (2)
C80.069 (4)0.085 (4)0.128 (5)0.006 (3)−0.001 (3)−0.011 (4)
C90.095 (5)0.091 (4)0.116 (5)0.031 (4)0.014 (4)0.029 (4)
C100.089 (4)0.053 (3)0.078 (3)0.002 (3)0.019 (3)0.001 (2)
C110.039 (2)0.047 (2)0.0280 (17)−0.0044 (18)0.0112 (15)0.0047 (15)
C120.047 (2)0.059 (3)0.045 (2)0.001 (2)0.0155 (18)−0.0031 (18)
C130.066 (3)0.068 (3)0.046 (2)−0.002 (2)0.022 (2)−0.011 (2)
C140.057 (3)0.067 (3)0.064 (3)0.006 (2)0.035 (2)−0.008 (2)
C150.044 (2)0.075 (3)0.069 (3)−0.001 (2)0.025 (2)−0.010 (2)
C160.047 (2)0.060 (3)0.041 (2)−0.002 (2)0.0133 (18)−0.0061 (18)
C170.0344 (19)0.038 (2)0.0434 (19)0.0001 (16)0.0112 (16)0.0024 (15)
C180.049 (2)0.051 (2)0.057 (2)−0.001 (2)0.0257 (19)0.0049 (19)
C190.051 (3)0.049 (3)0.087 (3)−0.011 (2)0.026 (2)0.004 (2)
C200.066 (3)0.048 (3)0.079 (3)−0.002 (2)0.017 (3)−0.016 (2)
C210.078 (3)0.059 (3)0.050 (2)0.003 (3)0.024 (2)−0.009 (2)
C220.065 (3)0.045 (2)0.043 (2)0.003 (2)0.0250 (19)0.0023 (17)
C230.039 (2)0.047 (2)0.047 (2)−0.0026 (18)0.0181 (17)−0.0019 (17)
C240.047 (3)0.057 (3)0.091 (3)0.005 (2)0.023 (2)0.010 (2)
C250.038 (3)0.081 (4)0.131 (5)0.000 (3)0.017 (3)0.013 (3)
C260.053 (3)0.076 (4)0.125 (5)−0.022 (3)0.018 (3)0.004 (3)
C270.066 (3)0.044 (3)0.115 (4)−0.010 (2)0.021 (3)0.004 (3)
C280.045 (2)0.042 (2)0.066 (3)0.0014 (19)0.017 (2)0.0033 (19)

Geometric parameters (Å, °)

Sb1—C112.079 (4)C10—H10A0.9700
Sb1—C232.116 (4)C10—H10B0.9700
Sb1—C172.120 (3)C11—C121.392 (5)
Sb1—Cl12.4720 (9)C11—C161.394 (5)
Sb1—Cl22.4792 (10)C12—C131.377 (5)
N1—C11.332 (5)C12—H120.9300
N1—C21.457 (5)C13—C141.377 (6)
N1—C51.476 (5)C13—H130.9300
N2—C61.315 (5)C14—C151.371 (6)
N2—C101.473 (5)C14—H140.9300
N2—C71.477 (6)C15—C161.372 (5)
S1—C11.817 (4)C15—H150.9300
S1—S32.0029 (17)C16—H160.9300
S2—C11.636 (4)C17—C181.375 (5)
S3—C61.818 (4)C17—C221.379 (5)
S4—C61.648 (5)C18—C191.382 (6)
C2—C31.515 (6)C18—H180.9300
C2—H2A0.9700C19—C201.368 (6)
C2—H2B0.9700C19—H190.9300
C3—C41.484 (8)C20—C211.369 (6)
C3—H3A0.9700C20—H200.9300
C3—H3B0.9700C21—C221.381 (6)
C4—C51.496 (7)C21—H210.9300
C4—H4A0.9700C22—H220.9300
C4—H4B0.9700C23—C281.378 (5)
C5—H5A0.9700C23—C241.384 (6)
C5—H5B0.9700C24—C251.380 (6)
C7—C81.507 (7)C24—H240.9300
C7—H7A0.9700C25—C261.360 (7)
C7—H7B0.9700C25—H250.9300
C8—C91.476 (8)C26—C271.367 (7)
C8—H8A0.9700C26—H260.9300
C8—H8B0.9700C27—C281.378 (6)
C9—C101.514 (7)C27—H270.9300
C9—H9A0.9700C28—H280.9300
C9—H9B0.9700
C11—Sb1—C23116.22 (14)C8—C9—H9B110.4
C11—Sb1—C17119.09 (14)C10—C9—H9B110.4
C23—Sb1—C17124.66 (14)H9A—C9—H9B108.6
C11—Sb1—Cl189.80 (10)N2—C10—C9103.2 (4)
C23—Sb1—Cl191.75 (10)N2—C10—H10A111.1
C17—Sb1—Cl190.23 (9)C9—C10—H10A111.1
C11—Sb1—Cl290.17 (10)N2—C10—H10B111.1
C23—Sb1—Cl289.47 (10)C9—C10—H10B111.1
C17—Sb1—Cl288.61 (9)H10A—C10—H10B109.1
Cl1—Sb1—Cl2178.65 (4)C12—C11—C16119.1 (3)
C1—N1—C2127.4 (3)C12—C11—Sb1118.7 (3)
C1—N1—C5121.4 (4)C16—C11—Sb1122.2 (3)
C2—N1—C5111.2 (3)C13—C12—C11119.9 (4)
C6—N2—C10122.6 (4)C13—C12—H12120.0
C6—N2—C7126.3 (4)C11—C12—H12120.0
C10—N2—C7111.1 (4)C12—C13—C14120.4 (4)
C1—S1—S3103.49 (15)C12—C13—H13119.8
C6—S3—S1104.86 (16)C14—C13—H13119.8
N1—C1—S2125.6 (3)C15—C14—C13119.9 (4)
N1—C1—S1110.2 (3)C15—C14—H14120.1
S2—C1—S1124.1 (2)C13—C14—H14120.1
N1—C2—C3103.4 (4)C14—C15—C16120.6 (4)
N1—C2—H2A111.1C14—C15—H15119.7
C3—C2—H2A111.1C16—C15—H15119.7
N1—C2—H2B111.1C15—C16—C11120.0 (4)
C3—C2—H2B111.1C15—C16—H16120.0
H2A—C2—H2B109.0C11—C16—H16120.0
C4—C3—C2103.9 (4)C18—C17—C22120.6 (4)
C4—C3—H3A111.0C18—C17—Sb1119.3 (3)
C2—C3—H3A111.0C22—C17—Sb1120.1 (3)
C4—C3—H3B111.0C17—C18—C19119.6 (4)
C2—C3—H3B111.0C17—C18—H18120.2
H3A—C3—H3B109.0C19—C18—H18120.2
C3—C4—C5105.1 (4)C20—C19—C18120.0 (4)
C3—C4—H4A110.7C20—C19—H19120.0
C5—C4—H4A110.7C18—C19—H19120.0
C3—C4—H4B110.7C19—C20—C21120.3 (4)
C5—C4—H4B110.7C19—C20—H20119.9
H4A—C4—H4B108.8C21—C20—H20119.9
N1—C5—C4103.3 (4)C20—C21—C22120.5 (4)
N1—C5—H5A111.1C20—C21—H21119.7
C4—C5—H5A111.1C22—C21—H21119.7
N1—C5—H5B111.1C17—C22—C21119.0 (4)
C4—C5—H5B111.1C17—C22—H22120.5
H5A—C5—H5B109.1C21—C22—H22120.5
N2—C6—S4125.1 (3)C28—C23—C24120.2 (4)
N2—C6—S3111.2 (3)C28—C23—Sb1119.1 (3)
S4—C6—S3123.7 (3)C24—C23—Sb1120.5 (3)
N2—C7—C8103.8 (4)C25—C24—C23119.0 (4)
N2—C7—H7A111.0C25—C24—H24120.5
C8—C7—H7A111.0C23—C24—H24120.5
N2—C7—H7B111.0C26—C25—C24120.8 (5)
C8—C7—H7B111.0C26—C25—H25119.6
H7A—C7—H7B109.0C24—C25—H25119.6
C9—C8—C7104.2 (5)C25—C26—C27120.0 (5)
C9—C8—H8A110.9C25—C26—H26120.0
C7—C8—H8A110.9C27—C26—H26120.0
C9—C8—H8B110.9C26—C27—C28120.5 (4)
C7—C8—H8B110.9C26—C27—H27119.7
H8A—C8—H8B108.9C28—C27—H27119.7
C8—C9—C10106.6 (4)C27—C28—C23119.5 (4)
C8—C9—H9A110.4C27—C28—H28120.3
C10—C9—H9A110.4C23—C28—H28120.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15···S4i0.932.913.594 (5)132
C13—H13···Cl2ii0.932.833.509 (4)131
C8—H8A···Cl1iii0.972.843.719 (6)151

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z+1; (iii) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2063).

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