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

Quan, L.; Yin, H.; Zhai, J.; Wang, D.

doi:10.1107/S1600536807063830

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m108

https://doi.org/10.1107/S1600536807063830

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

Li Quan,^a Handong Yin,^a ^* Jun Zhai ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 23 November 2007; accepted 27 November 2007; online 6 December 2007)

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 ); Feng Li et al. (2006 ). For discussion on C—H⋯S interactions, see: Srinivasan et al. (2007 ). For related literature, see: Kumar et al. (1990 ).

Experimental

Crystal data

[Sb(C₆H₅)₃Cl₂]·C₁₀H₁₆N₂S₄
M_r = 716.48
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.092
S = 1.00
5560 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯S4ⁱ	0.93	2.91	3.594 (5)	132
C13—H13⋯Cl2ⁱⁱ	0.93	2.83	3.509 (4)	131
C8—H8A⋯Cl1ⁱⁱⁱ	0.97	2.84	3.719 (6)	151
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z+1; (iii) -x, -y+2, -z.

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063830/si2063Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

Computing details top

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

Figures top

	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 by dashed lines. Symmetry codes are given in Table 1.

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

Crystal data top

[Sb(C₆H₅)₃Cl₂]·C₁₀H₁₆N₂S₄	F(000) = 1448
M_r = 716.48	D_x = 1.498 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7025 reflections
a = 14.8138 (18) Å	θ = 2.2–27.8°
b = 13.6440 (13) Å	µ = 1.32 mm⁻¹
c = 16.316 (3) Å	T = 298 K
β = 105.509 (2)°	Block, colorless
V = 3177.7 (8) Å³	0.50 × 0.42 × 0.39 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	5560 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→10
T_min = 0.558, T_max = 0.627	k = −16→16
14597 measured reflections	l = −19→19

Refinement top

Refinement on f²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.045P)² + 1.9404P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
5560 reflections	Δρ_max = 0.67 e Å⁻³
335 parameters	Δρ_min = −0.59 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (3)

Crystal data top

[Sb(C₆H₅)₃Cl₂]·C₁₀H₁₆N₂S₄	V = 3177.7 (8) Å³
M_r = 716.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.8138 (18) Å	µ = 1.32 mm⁻¹
b = 13.6440 (13) Å	T = 298 K
c = 16.316 (3) Å	0.50 × 0.42 × 0.39 mm
β = 105.509 (2)°

Data collection top

Siemens SMART CCD diffractometer	5560 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4333 reflections with I > 2σ(I)
T_min = 0.558, T_max = 0.627	R_int = 0.041
14597 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.00	Δρ_max = 0.67 e Å⁻³
5560 reflections	Δρ_min = −0.59 e Å⁻³
335 parameters

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

	x	y	z	U_iso*/U_eq
Sb1	0.018116 (16)	0.991080 (17)	0.234502 (14)	0.03657 (11)
Cl1	−0.07709 (7)	1.08719 (7)	0.11362 (6)	0.0508 (3)
Cl2	0.11117 (8)	0.89132 (8)	0.35457 (6)	0.0569 (3)
N1	0.6750 (2)	0.8384 (2)	0.3780 (2)	0.0516 (8)
N2	0.4034 (2)	1.0375 (2)	0.0796 (2)	0.0534 (9)
S1	0.59570 (9)	0.82805 (9)	0.21567 (7)	0.0664 (3)
S2	0.50821 (9)	0.92203 (9)	0.34589 (8)	0.0665 (3)
S3	0.46930 (9)	0.86974 (9)	0.14467 (7)	0.0704 (4)
S4	0.58682 (9)	1.05180 (10)	0.13631 (8)	0.0742 (4)
C1	0.5950 (3)	0.8643 (3)	0.3226 (2)	0.0479 (10)
C2	0.7541 (3)	0.7877 (3)	0.3599 (3)	0.0660 (12)
H2A	0.7718	0.8181	0.3127	0.079*
H2B	0.7396	0.7192	0.3467	0.079*
C3	0.8311 (4)	0.7985 (4)	0.4418 (3)	0.0879 (17)
H3A	0.8735	0.7429	0.4505	0.106*
H3B	0.8667	0.8580	0.4415	0.106*
C4	0.7802 (4)	0.8025 (5)	0.5087 (3)	0.0972 (19)
H4A	0.8174	0.8356	0.5591	0.117*
H4B	0.7654	0.7371	0.5243	0.117*
C5	0.6926 (3)	0.8589 (4)	0.4697 (3)	0.0685 (13)
H5A	0.6410	0.8362	0.4910	0.082*
H5B	0.7017	0.9285	0.4812	0.082*
C6	0.4843 (3)	0.9968 (3)	0.1173 (2)	0.0531 (11)
C7	0.3104 (3)	0.9904 (3)	0.0625 (3)	0.0732 (14)
H7A	0.3029	0.9567	0.1126	0.088*
H7B	0.3015	0.9438	0.0161	0.088*
C8	0.2428 (4)	1.0747 (4)	0.0389 (4)	0.100 (2)
H8A	0.1850	1.0541	−0.0012	0.120*
H8B	0.2283	1.1018	0.0889	0.120*
C9	0.2927 (4)	1.1471 (5)	−0.0001 (4)	0.104 (2)
H9A	0.2703	1.2128	0.0061	0.124*
H9B	0.2828	1.1334	−0.0602	0.124*
C10	0.3956 (4)	1.1383 (3)	0.0462 (3)	0.0739 (14)
H10A	0.4345	1.1476	0.0076	0.089*
H10B	0.4133	1.1858	0.0920	0.089*
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)
H12	0.0328	1.0757	0.4095	0.059*
C13	−0.0893 (3)	1.1037 (3)	0.4366 (3)	0.0589 (11)
H13	−0.0632	1.1315	0.4897	0.071*
C14	−0.1851 (3)	1.0950 (3)	0.4067 (3)	0.0589 (11)
H14	−0.2235	1.1151	0.4403	0.071*
C15	−0.2239 (3)	1.0566 (3)	0.3274 (3)	0.0610 (11)
H15	−0.2886	1.0508	0.3075	0.073*
C16	−0.1680 (3)	1.0268 (3)	0.2772 (2)	0.0495 (10)
H16	−0.1950	1.0024	0.2230	0.059*
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	−0.0478	0.7808	0.2507	0.060*
C19	−0.0580 (3)	0.6933 (3)	0.1490 (3)	0.0607 (12)
H19	−0.0773	0.6374	0.1723	0.073*
C20	−0.0469 (3)	0.6908 (3)	0.0685 (3)	0.0650 (12)
H20	−0.0581	0.6329	0.0373	0.078*
C21	−0.0195 (3)	0.7731 (3)	0.0336 (3)	0.0611 (11)
H21	−0.0127	0.7709	−0.0214	0.073*
C22	−0.0018 (3)	0.8593 (3)	0.0794 (2)	0.0491 (10)
H22	0.0166	0.9152	0.0556	0.059*
C23	0.1365 (3)	1.0813 (3)	0.2432 (2)	0.0428 (9)
C24	0.2261 (3)	1.0430 (4)	0.2705 (3)	0.0642 (12)
H24	0.2351	0.9765	0.2825	0.077*
C25	0.3018 (3)	1.1049 (4)	0.2797 (4)	0.0844 (16)
H25	0.3622	1.0795	0.2967	0.101*
C26	0.2892 (4)	1.2026 (4)	0.2643 (4)	0.0859 (16)
H26	0.3408	1.2437	0.2714	0.103*
C27	0.2006 (4)	1.2404 (3)	0.2382 (3)	0.0757 (14)
H27	0.1923	1.3072	0.2278	0.091*
C28	0.1236 (3)	1.1801 (3)	0.2271 (2)	0.0505 (10)
H28	0.0635	1.2060	0.2089	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.03922 (16)	0.03827 (16)	0.03499 (15)	0.00222 (11)	0.01473 (11)	0.00279 (10)
Cl1	0.0587 (6)	0.0493 (6)	0.0422 (5)	0.0073 (5)	0.0095 (4)	0.0092 (4)
Cl2	0.0678 (7)	0.0605 (6)	0.0419 (5)	0.0145 (6)	0.0138 (5)	0.0138 (4)
N1	0.050 (2)	0.0453 (19)	0.0531 (19)	−0.0006 (17)	0.0033 (16)	0.0008 (15)
N2	0.059 (2)	0.0451 (19)	0.0507 (19)	−0.0064 (18)	0.0047 (17)	−0.0006 (15)
S1	0.0762 (8)	0.0609 (7)	0.0545 (6)	0.0119 (6)	0.0046 (6)	−0.0034 (5)
S2	0.0606 (7)	0.0570 (7)	0.0807 (8)	0.0096 (6)	0.0170 (6)	0.0004 (6)
S3	0.0749 (8)	0.0524 (7)	0.0655 (7)	−0.0139 (6)	−0.0136 (6)	0.0068 (5)
S4	0.0652 (8)	0.0727 (8)	0.0780 (8)	−0.0193 (7)	0.0074 (6)	0.0031 (6)
C1	0.053 (2)	0.034 (2)	0.054 (2)	−0.0035 (18)	0.0078 (19)	0.0020 (16)
C2	0.057 (3)	0.057 (3)	0.080 (3)	0.005 (2)	0.012 (2)	−0.004 (2)
C3	0.059 (3)	0.083 (4)	0.104 (4)	0.013 (3)	−0.010 (3)	−0.005 (3)
C4	0.085 (4)	0.111 (5)	0.076 (4)	0.005 (4)	−0.014 (3)	0.017 (3)
C5	0.072 (3)	0.072 (3)	0.055 (3)	−0.003 (3)	0.005 (2)	0.006 (2)
C6	0.066 (3)	0.048 (2)	0.040 (2)	−0.008 (2)	0.005 (2)	−0.0023 (17)
C7	0.059 (3)	0.066 (3)	0.085 (3)	−0.008 (3)	0.001 (3)	−0.005 (2)
C8	0.069 (4)	0.085 (4)	0.128 (5)	0.006 (3)	−0.001 (3)	−0.011 (4)
C9	0.095 (5)	0.091 (4)	0.116 (5)	0.031 (4)	0.014 (4)	0.029 (4)
C10	0.089 (4)	0.053 (3)	0.078 (3)	0.002 (3)	0.019 (3)	0.001 (2)
C11	0.039 (2)	0.047 (2)	0.0280 (17)	−0.0044 (18)	0.0112 (15)	0.0047 (15)
C12	0.047 (2)	0.059 (3)	0.045 (2)	0.001 (2)	0.0155 (18)	−0.0031 (18)
C13	0.066 (3)	0.068 (3)	0.046 (2)	−0.002 (2)	0.022 (2)	−0.011 (2)
C14	0.057 (3)	0.067 (3)	0.064 (3)	0.006 (2)	0.035 (2)	−0.008 (2)
C15	0.044 (2)	0.075 (3)	0.069 (3)	−0.001 (2)	0.025 (2)	−0.010 (2)
C16	0.047 (2)	0.060 (3)	0.041 (2)	−0.002 (2)	0.0133 (18)	−0.0061 (18)
C17	0.0344 (19)	0.038 (2)	0.0434 (19)	0.0001 (16)	0.0112 (16)	0.0024 (15)
C18	0.049 (2)	0.051 (2)	0.057 (2)	−0.001 (2)	0.0257 (19)	0.0049 (19)
C19	0.051 (3)	0.049 (3)	0.087 (3)	−0.011 (2)	0.026 (2)	0.004 (2)
C20	0.066 (3)	0.048 (3)	0.079 (3)	−0.002 (2)	0.017 (3)	−0.016 (2)
C21	0.078 (3)	0.059 (3)	0.050 (2)	0.003 (3)	0.024 (2)	−0.009 (2)
C22	0.065 (3)	0.045 (2)	0.043 (2)	0.003 (2)	0.0250 (19)	0.0023 (17)
C23	0.039 (2)	0.047 (2)	0.047 (2)	−0.0026 (18)	0.0181 (17)	−0.0019 (17)
C24	0.047 (3)	0.057 (3)	0.091 (3)	0.005 (2)	0.023 (2)	0.010 (2)
C25	0.038 (3)	0.081 (4)	0.131 (5)	0.000 (3)	0.017 (3)	0.013 (3)
C26	0.053 (3)	0.076 (4)	0.125 (5)	−0.022 (3)	0.018 (3)	0.004 (3)
C27	0.066 (3)	0.044 (3)	0.115 (4)	−0.010 (2)	0.021 (3)	0.004 (3)
C28	0.045 (2)	0.042 (2)	0.066 (3)	0.0014 (19)	0.017 (2)	0.0033 (19)

Geometric parameters (Å, º) top

Sb1—C11	2.079 (4)	C10—H10A	0.9700
Sb1—C23	2.116 (4)	C10—H10B	0.9700
Sb1—C17	2.120 (3)	C11—C12	1.392 (5)
Sb1—Cl1	2.4720 (9)	C11—C16	1.394 (5)
Sb1—Cl2	2.4792 (10)	C12—C13	1.377 (5)
N1—C1	1.332 (5)	C12—H12	0.9300
N1—C2	1.457 (5)	C13—C14	1.377 (6)
N1—C5	1.476 (5)	C13—H13	0.9300
N2—C6	1.315 (5)	C14—C15	1.371 (6)
N2—C10	1.473 (5)	C14—H14	0.9300
N2—C7	1.477 (6)	C15—C16	1.372 (5)
S1—C1	1.817 (4)	C15—H15	0.9300
S1—S3	2.0029 (17)	C16—H16	0.9300
S2—C1	1.636 (4)	C17—C18	1.375 (5)
S3—C6	1.818 (4)	C17—C22	1.379 (5)
S4—C6	1.648 (5)	C18—C19	1.382 (6)
C2—C3	1.515 (6)	C18—H18	0.9300
C2—H2A	0.9700	C19—C20	1.368 (6)
C2—H2B	0.9700	C19—H19	0.9300
C3—C4	1.484 (8)	C20—C21	1.369 (6)
C3—H3A	0.9700	C20—H20	0.9300
C3—H3B	0.9700	C21—C22	1.381 (6)
C4—C5	1.496 (7)	C21—H21	0.9300
C4—H4A	0.9700	C22—H22	0.9300
C4—H4B	0.9700	C23—C28	1.378 (5)
C5—H5A	0.9700	C23—C24	1.384 (6)
C5—H5B	0.9700	C24—C25	1.380 (6)
C7—C8	1.507 (7)	C24—H24	0.9300
C7—H7A	0.9700	C25—C26	1.360 (7)
C7—H7B	0.9700	C25—H25	0.9300
C8—C9	1.476 (8)	C26—C27	1.367 (7)
C8—H8A	0.9700	C26—H26	0.9300
C8—H8B	0.9700	C27—C28	1.378 (6)
C9—C10	1.514 (7)	C27—H27	0.9300
C9—H9A	0.9700	C28—H28	0.9300
C9—H9B	0.9700

C11—Sb1—C23	116.22 (14)	C8—C9—H9B	110.4
C11—Sb1—C17	119.09 (14)	C10—C9—H9B	110.4
C23—Sb1—C17	124.66 (14)	H9A—C9—H9B	108.6
C11—Sb1—Cl1	89.80 (10)	N2—C10—C9	103.2 (4)
C23—Sb1—Cl1	91.75 (10)	N2—C10—H10A	111.1
C17—Sb1—Cl1	90.23 (9)	C9—C10—H10A	111.1
C11—Sb1—Cl2	90.17 (10)	N2—C10—H10B	111.1
C23—Sb1—Cl2	89.47 (10)	C9—C10—H10B	111.1
C17—Sb1—Cl2	88.61 (9)	H10A—C10—H10B	109.1
Cl1—Sb1—Cl2	178.65 (4)	C12—C11—C16	119.1 (3)
C1—N1—C2	127.4 (3)	C12—C11—Sb1	118.7 (3)
C1—N1—C5	121.4 (4)	C16—C11—Sb1	122.2 (3)
C2—N1—C5	111.2 (3)	C13—C12—C11	119.9 (4)
C6—N2—C10	122.6 (4)	C13—C12—H12	120.0
C6—N2—C7	126.3 (4)	C11—C12—H12	120.0
C10—N2—C7	111.1 (4)	C12—C13—C14	120.4 (4)
C1—S1—S3	103.49 (15)	C12—C13—H13	119.8
C6—S3—S1	104.86 (16)	C14—C13—H13	119.8
N1—C1—S2	125.6 (3)	C15—C14—C13	119.9 (4)
N1—C1—S1	110.2 (3)	C15—C14—H14	120.1
S2—C1—S1	124.1 (2)	C13—C14—H14	120.1
N1—C2—C3	103.4 (4)	C14—C15—C16	120.6 (4)
N1—C2—H2A	111.1	C14—C15—H15	119.7
C3—C2—H2A	111.1	C16—C15—H15	119.7
N1—C2—H2B	111.1	C15—C16—C11	120.0 (4)
C3—C2—H2B	111.1	C15—C16—H16	120.0
H2A—C2—H2B	109.0	C11—C16—H16	120.0
C4—C3—C2	103.9 (4)	C18—C17—C22	120.6 (4)
C4—C3—H3A	111.0	C18—C17—Sb1	119.3 (3)
C2—C3—H3A	111.0	C22—C17—Sb1	120.1 (3)
C4—C3—H3B	111.0	C17—C18—C19	119.6 (4)
C2—C3—H3B	111.0	C17—C18—H18	120.2
H3A—C3—H3B	109.0	C19—C18—H18	120.2
C3—C4—C5	105.1 (4)	C20—C19—C18	120.0 (4)
C3—C4—H4A	110.7	C20—C19—H19	120.0
C5—C4—H4A	110.7	C18—C19—H19	120.0
C3—C4—H4B	110.7	C19—C20—C21	120.3 (4)
C5—C4—H4B	110.7	C19—C20—H20	119.9
H4A—C4—H4B	108.8	C21—C20—H20	119.9
N1—C5—C4	103.3 (4)	C20—C21—C22	120.5 (4)
N1—C5—H5A	111.1	C20—C21—H21	119.7
C4—C5—H5A	111.1	C22—C21—H21	119.7
N1—C5—H5B	111.1	C17—C22—C21	119.0 (4)
C4—C5—H5B	111.1	C17—C22—H22	120.5
H5A—C5—H5B	109.1	C21—C22—H22	120.5
N2—C6—S4	125.1 (3)	C28—C23—C24	120.2 (4)
N2—C6—S3	111.2 (3)	C28—C23—Sb1	119.1 (3)
S4—C6—S3	123.7 (3)	C24—C23—Sb1	120.5 (3)
N2—C7—C8	103.8 (4)	C25—C24—C23	119.0 (4)
N2—C7—H7A	111.0	C25—C24—H24	120.5
C8—C7—H7A	111.0	C23—C24—H24	120.5
N2—C7—H7B	111.0	C26—C25—C24	120.8 (5)
C8—C7—H7B	111.0	C26—C25—H25	119.6
H7A—C7—H7B	109.0	C24—C25—H25	119.6
C9—C8—C7	104.2 (5)	C25—C26—C27	120.0 (5)
C9—C8—H8A	110.9	C25—C26—H26	120.0
C7—C8—H8A	110.9	C27—C26—H26	120.0
C9—C8—H8B	110.9	C26—C27—C28	120.5 (4)
C7—C8—H8B	110.9	C26—C27—H27	119.7
H8A—C8—H8B	108.9	C28—C27—H27	119.7
C8—C9—C10	106.6 (4)	C27—C28—C23	119.5 (4)
C8—C9—H9A	110.4	C27—C28—H28	120.3
C10—C9—H9A	110.4	C23—C28—H28	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···S4ⁱ	0.93	2.91	3.594 (5)	132
C13—H13···Cl2ⁱⁱ	0.93	2.83	3.509 (4)	131
C8—H8A···Cl1ⁱⁱⁱ	0.97	2.84	3.719 (6)	151

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

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃Cl₂]·C₁₀H₁₆N₂S₄
M_r	716.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.8138 (18), 13.6440 (13), 16.316 (3)
β (°)	105.509 (2)
V (Å³)	3177.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.50 × 0.42 × 0.39

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.558, 0.627
No. of measured, independent and observed [I > 2σ(I)] reflections	14597, 5560, 4333
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.092, 1.00
No. of reflections	5560
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.59

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···S4ⁱ	0.93	2.91	3.594 (5)	131.8
C13—H13···Cl2ⁱⁱ	0.93	2.83	3.509 (4)	130.5
C8—H8A···Cl1ⁱⁱⁱ	0.97	2.84	3.719 (6)	151.1

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

Acknowledgements

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

References

Kumar, V., Aravamudan, G. & Seshasayee, M. (1990). Acta Cryst. C46, 674–676. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, F., Yin, H.-D., Hong, M., Zhai, J. & Wang, D.-Q. (2006). Acta Cryst. E62, m1417–m1418. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Srinivasan, B. R., Naik, A. R., Näther, C. & Bensch, W. (2007). Z. Anorg. Allg. Chem. 633, 582–588. Web of Science CSD CrossRef CAS Google Scholar
Williams, G. A., Statham, J. R. & White, A. H. (1983). Aust. J. Chem. 36, 1371–1377. CrossRef CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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