Redetermination of tris­(N,N-diethyl­dithio­carbamato)anti­mony(III)

Que, M.; Zhang, Y.C.; Liu, Z.D.; Zhou, H.P.

doi:10.1107/S1600536809005303

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m311-m312

doi:10.1107/S1600536809005303

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Redetermination of tris(N,N-diethyldithiocarbamato)antimony(III)

Mei Que,^a Yu Chuan Zhang,^a ^* Zhao Di Liu ^a and Hong Ping Zhou ^a

^aDepartment of Chemistry Anhui University, Hefei 230039, People's Republic of China, and Key Laboratory of Enviromentally-Friendly Polymer Materials of Anhui Province, Hefei 230039, People's Republic of China
^*Correspondence e-mail: yuchuanzhang1946@yahoo.cn

(Received 11 November 2008; accepted 14 February 2009; online 21 February 2009)

The title compound, [Sb(C₅H₁₀NS₂)₃], was synthesized from Sb₂O₃, diethylamine, carbon disulfide, hydrochloric acid and sodium hydroxide. The structure has been published previously but H atoms were not included in the model [Raston & White (1976 ). Chem. Soc. Dalton Trans. p. 791]. The current determination has significantly higher precision than the original work. The complex has three ligands. The Sb atom is coordinated by three bidentate diethyldithiocarbamate groups, two in an almost planar fashion and the third perpendicular to that plane with a dihedral angle of 86.429 (13)°. One ethyl group is disordered over two positions of equal occupancy.

Related literature

For applications of dithiocarbamates, see: Fujii & Yoshimura (2000 ); Stary et al. (1992 ); Pazukhina et al. (1997 ). For the extraction efficiency of dithiocarbamate complexes in the presence of neutral N, S, O and P donor molecules, see: Ooi & Fernando (1967 ). For nitrogen donor adducts of dithiocarbamate complexes, see: O'Brien et al. (1992 , 1998 ); Chunggaze et al. (1997 ); Bessergenev et al. (1996 , 1997 ); Hovel (1975 ). For complexes with post-transition metals, see: Coucouvanis (1979 ) and for complexes involving Te(IV), Te(II) and Se(II) centres, see: Husebye & Svaeren (1973 ); Rout et al. (1983 ).

Experimental

Crystal data

[Sb(C₅H₁₀NS₂)₃]
M_r = 566.53
Monoclinic, P 2₁ /c
a = 12.6454 (2) Å
b = 13.6217 (2) Å
c = 14.6731 (2) Å
β = 99.858 (1)°
V = 2490.15 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 296 K
0.26 × 0.21 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.679, T_max = 0.817 (expected range = 0.591–0.712)
24761 measured reflections
5746 independent reflections
4947 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.059
S = 1.00
5746 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Sb1—S5	2.4842 (5)
Sb1—S3	2.6238 (5)
Sb1—S2	2.6328 (5)
Sb1—S1	2.8805 (6)
Sb1—S4	2.8938 (5)

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005303/fi2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005303/fi2068Isup2.hkl

checkCIF report

Comment top

Dithiocarbamates have found wide practical application as antioxidants and lubricants, as vulcanizing and NO-trapping agents (Fujii et al., 2000), as agents for the froth flotation process of sulfide minerals and for the liquid-liquid extraction of transition metals (Stary et al., 1992; Pazukhina et al., 1997). It has also been found that the extraction efficiency of dithiocarbamate complexes rises in the presence of neutral N, S, O, P-donor molecules, which could potentially imply formation of adducts (Ooi et al., 1967). Besides that, nitrogen donor adducts of dithiocarbamate complexes are also widely used in the preparation of thin semiconductor (O'Brien et al., 1992; Chunggaze et al., 1997; O'Brien et al., 1998) and electroluminescent (Bessergenev et al., 1996; Bessergenev et al., 1997) films of transition metal sulfides, the basis of electronics and solar cell technology (Hovel, 1975). The dithiocarbamate anion (R₁R₂NCS^2-=I^-) is known to be a strong nucleophile and to form stable complexs with many post-transition metals (Coucouvanis, 1979). Thus, complexes involving Te(IV), Te(II) and Se(II) centres have been reported, and structural studies on these have shown the presence of bidentate chelating ligands (Husebye et al., 1973; Rout et al., 1983). We have synthesized the title compound, C₁₅H₃₀N₃S₆Sb, and report here its crystal structure. The structure had been reported earlier (Raston & White, 1976), The syntheses and application of the crystal haven't been described in that paper. They mentioned simply that they examined samples of the antimony derivatives recrystallized from benzene solution. The crystal is monoclinic, Z=4, a=14.665 (5) Å, b=13.619 (5)Å, c=12.642 (4)Å, β=99.86 (4)°. These data of the crystal is similar to our crystal.but no hydrogen atoms were included in their structure model. The molecular structure and the atom-numbering scheme of the title compound are shown in Fig. 1. In the molecule, all bond lengths and angles agree well with values found in literature Table 1. The Sb atom is coordinated by three bidentate diethyldithiocarbamato groups, two groups in an almost planar fashion, the thirs group is perpendicular to that plane with a dihedral angle of 86.429 (13)°.

Related literature top

For applications of dithiocarbamates, see: Fujii & Yoshimura (2000); Stary et al. (1992); Pazukhina et al. (1997). For the extraction efficiency of dithiocarbamate complexes in the presence of neutral N, S,O, P-donor molecules, see: Ooi & Fernando (1967). For nitrogen donor adducts of dithiocarbamate complexes, see: O'Brien et al. (1992, 1998); Chunggaze et al. (1997); Bessergenev et al. (1996, 1997); Hovel (1975). For complexes with post-transition metals, see: Coucouvanis (1979) and for complexes involving Te(IV), Te(II) and Se(II) centres, see: Husebye & Svaeren (1973); Rout et al. (1983).

Experimental top

Water (200 ml), sodium hydroxide (4 g, 0.1 mol) and diethylamine (7.3 g, 0.1 mol) were added to a three-neck flask in an icewater bath under stirring. Carbon disulfide (7.8 g, 0.1 mol) was added dropwise into this solution during twenty minutes and the mixture was allowed to react for four hours yielding a light yellow liquid. Antimony trioxide (4.6 g, 0.016 mol) was dissolved in hydrochloric acid. The solution was added dropwise into the diethyl dithiocarbamate natrium under stirring and it was confirmed that the resulting solution was acidic. From this solution, a yellow deposit was obtained. It was collected by vacuum filtration, washed with a large amount of water and dried in air. Yellow single crystals were obtained after two weeks upon evaporation of a solution of the reaction product in a mixture of chloroform (5 ml) and methanol (30 ml).

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

tris(N,N-diethyldithiocarbamato)antimony(III) top

Crystal data top

[Sb(C₅H₁₀NS₂)₃]	F(000) = 1152
M_r = 566.53	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9907 reflections
a = 12.6454 (2) Å	θ = 2.2–27.5°
b = 13.6217 (2) Å	µ = 1.62 mm⁻¹
c = 14.6731 (2) Å	T = 296 K
β = 99.858 (1)°	Block, yellow
V = 2490.15 (6) Å³	0.26 × 0.21 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5746 independent reflections
Radiation source: fine-focus sealed tube	4947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
T_min = 0.679, T_max = 0.817	k = −17→17
24761 measured reflections	l = −18→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)] = 0.021	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0366P)² + 0.1807P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.003
5746 reflections	Δρ_max = 0.38 e Å⁻³
253 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (2)

Crystal data top

[Sb(C₅H₁₀NS₂)₃]	V = 2490.15 (6) Å³
M_r = 566.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6454 (2) Å	µ = 1.62 mm⁻¹
b = 13.6217 (2) Å	T = 296 K
c = 14.6731 (2) Å	0.26 × 0.21 × 0.21 mm
β = 99.858 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5746 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4947 reflections with I > 2σ(I)
T_min = 0.679, T_max = 0.817	R_int = 0.021
24761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.00	Δρ_max = 0.38 e Å⁻³
5746 reflections	Δρ_min = −0.29 e Å⁻³
253 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sb1	0.664203 (10)	0.489969 (8)	0.544433 (8)	0.03895 (6)
S5	0.82733 (4)	0.47481 (3)	0.47217 (3)	0.04547 (12)
S2	0.59116 (4)	0.32605 (3)	0.46160 (3)	0.04974 (12)
S1	0.55799 (5)	0.51072 (3)	0.35546 (4)	0.04951 (13)
S3	0.73733 (4)	0.34808 (3)	0.65900 (3)	0.04951 (12)
S6	0.75061 (4)	0.67918 (4)	0.48886 (4)	0.05794 (14)
S4	0.78957 (5)	0.55135 (4)	0.71886 (3)	0.05585 (13)
N1	0.88457 (11)	0.62440 (10)	0.37638 (9)	0.0413 (3)
N3	0.81757 (14)	0.39580 (12)	0.83190 (10)	0.0558 (4)
N2	0.50310 (13)	0.33416 (11)	0.28478 (10)	0.0495 (4)
C2	0.89233 (16)	0.72713 (14)	0.34826 (13)	0.0503 (4)
H2A	0.8274	0.7617	0.3560	0.060*
H2B	0.8984	0.7297	0.2833	0.060*
C5	0.82576 (13)	0.59892 (13)	0.43964 (11)	0.0397 (4)
C6	0.54573 (13)	0.38630 (13)	0.35802 (12)	0.0413 (4)
C7	0.78502 (15)	0.43078 (14)	0.74662 (12)	0.0457 (4)
C3	0.94447 (15)	0.55426 (14)	0.32952 (12)	0.0495 (4)
H3A	0.9652	0.4986	0.3699	0.059*
H3B	1.0094	0.5852	0.3168	0.059*
C10	0.82177 (18)	0.29025 (16)	0.85339 (14)	0.0616 (6)
H10A	0.7619	0.2575	0.8152	0.074*
H10B	0.8146	0.2810	0.9176	0.074*
C13	0.49020 (17)	0.22693 (15)	0.28767 (15)	0.0596 (5)
H13A	0.5502	0.1991	0.3298	0.071*
H13B	0.4913	0.2001	0.2266	0.071*
C12	0.38672 (19)	0.19757 (17)	0.31864 (19)	0.0797 (7)
H12A	0.3880	0.2189	0.3812	0.120*
H12B	0.3791	0.1275	0.3154	0.120*
H12C	0.3273	0.2277	0.2790	0.120*
C14	0.46194 (18)	0.38151 (18)	0.19505 (13)	0.0669 (6)
H14A	0.4376	0.4473	0.2060	0.080*
H14B	0.4008	0.3446	0.1635	0.080*
C1	0.98809 (18)	0.77734 (16)	0.40466 (15)	0.0672 (6)
H1A	0.9786	0.7809	0.4681	0.101*
H1B	0.9947	0.8425	0.3812	0.101*
H1C	1.0519	0.7406	0.4005	0.101*
C4	0.8789 (3)	0.51864 (19)	0.24026 (17)	0.0816 (8)
H4A	0.8182	0.4822	0.2533	0.122*
H4B	0.9223	0.4771	0.2088	0.122*
H4C	0.8544	0.5739	0.2018	0.122*
C11	0.9249 (2)	0.24437 (17)	0.83695 (16)	0.0733 (7)
H11A	0.9262	0.2427	0.7717	0.110*
H11B	0.9300	0.1787	0.8610	0.110*
H11C	0.9845	0.2824	0.8676	0.110*
C15	0.5461 (2)	0.3870 (2)	0.13415 (16)	0.0965 (9)
H15A	0.6062	0.4244	0.1647	0.145*
H15B	0.5165	0.4182	0.0768	0.145*
H15C	0.5693	0.3219	0.1221	0.145*
C9	0.8390 (10)	0.4544 (13)	0.9120 (12)	0.072 (3)	0.50
H9A	0.8534	0.5205	0.8927	0.087*	0.50
H9B	0.9048	0.4303	0.9492	0.087*	0.50
C8	0.7567 (14)	0.4614 (9)	0.9733 (10)	0.104 (4)	0.50
H8A	0.6917	0.4886	0.9391	0.156*	0.50
H8B	0.7828	0.5031	1.0250	0.156*	0.50
H8C	0.7425	0.3971	0.9952	0.156*	0.50
C9'	0.8734 (10)	0.4662 (11)	0.9077 (10)	0.060 (2)	0.50
H9'1	0.9315	0.4325	0.9473	0.072*	0.50
H9'2	0.9031	0.5220	0.8797	0.072*	0.50
C8'	0.7900 (13)	0.5005 (9)	0.9641 (9)	0.101 (4)	0.50
H8'1	0.7337	0.5349	0.9246	0.151*	0.50
H8'2	0.8232	0.5436	1.0124	0.151*	0.50
H8'3	0.7605	0.4447	0.9908	0.151*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.04014 (8)	0.03772 (8)	0.04160 (8)	−0.00181 (4)	0.01435 (6)	−0.00116 (4)
S5	0.0466 (3)	0.0374 (2)	0.0571 (3)	0.00373 (19)	0.0225 (2)	0.00350 (19)
S2	0.0617 (3)	0.0378 (2)	0.0487 (3)	−0.0062 (2)	0.0063 (2)	0.00249 (18)
S1	0.0591 (3)	0.0388 (2)	0.0515 (3)	0.0014 (2)	0.0121 (2)	0.00393 (18)
S3	0.0582 (3)	0.0423 (2)	0.0471 (3)	−0.0066 (2)	0.0065 (2)	0.00099 (19)
S6	0.0706 (3)	0.0388 (3)	0.0737 (3)	0.0029 (2)	0.0387 (3)	−0.0037 (2)
S4	0.0677 (3)	0.0433 (3)	0.0550 (3)	−0.0018 (2)	0.0059 (2)	−0.0053 (2)
N1	0.0389 (8)	0.0427 (8)	0.0442 (8)	−0.0013 (6)	0.0123 (6)	0.0028 (6)
N3	0.0663 (11)	0.0571 (10)	0.0432 (9)	−0.0020 (8)	0.0072 (8)	0.0013 (7)
N2	0.0515 (9)	0.0483 (9)	0.0484 (9)	0.0001 (7)	0.0078 (7)	−0.0079 (7)
C2	0.0534 (11)	0.0477 (10)	0.0521 (10)	−0.0010 (9)	0.0161 (9)	0.0103 (8)
C5	0.0378 (9)	0.0376 (9)	0.0450 (9)	−0.0025 (7)	0.0110 (7)	−0.0014 (7)
C6	0.0378 (9)	0.0430 (9)	0.0447 (9)	0.0016 (7)	0.0117 (8)	−0.0021 (7)
C7	0.0430 (10)	0.0503 (11)	0.0451 (10)	−0.0012 (8)	0.0116 (8)	−0.0015 (8)
C3	0.0456 (10)	0.0537 (11)	0.0538 (10)	0.0049 (9)	0.0219 (9)	0.0023 (9)
C10	0.0716 (14)	0.0657 (13)	0.0491 (11)	−0.0094 (11)	0.0145 (10)	0.0162 (10)
C13	0.0644 (14)	0.0482 (11)	0.0667 (12)	−0.0050 (10)	0.0128 (10)	−0.0186 (10)
C12	0.0692 (15)	0.0656 (15)	0.1058 (19)	−0.0162 (13)	0.0191 (14)	−0.0159 (14)
C14	0.0747 (15)	0.0742 (15)	0.0472 (11)	0.0074 (12)	−0.0027 (10)	−0.0055 (10)
C1	0.0729 (15)	0.0589 (13)	0.0704 (14)	−0.0189 (11)	0.0138 (12)	0.0004 (10)
C4	0.098 (2)	0.0876 (18)	0.0591 (15)	0.0177 (15)	0.0135 (14)	−0.0195 (12)
C11	0.0946 (19)	0.0606 (14)	0.0697 (14)	0.0029 (13)	0.0287 (13)	0.0149 (11)
C15	0.132 (2)	0.105 (2)	0.0598 (14)	0.0332 (19)	0.0349 (16)	0.0051 (13)
C9	0.073 (8)	0.074 (6)	0.062 (5)	−0.013 (5)	−0.010 (5)	0.003 (4)
C8	0.158 (11)	0.104 (8)	0.057 (4)	0.014 (7)	0.037 (5)	−0.013 (5)
C9'	0.072 (7)	0.060 (4)	0.042 (3)	−0.011 (4)	−0.005 (4)	−0.008 (3)
C8'	0.138 (11)	0.114 (10)	0.052 (4)	0.027 (7)	0.020 (5)	−0.007 (5)

Geometric parameters (Å, º) top

Sb1—S5	2.4842 (5)	C13—H13B	0.9700
Sb1—S3	2.6238 (5)	C12—H12A	0.9600
Sb1—S2	2.6328 (5)	C12—H12B	0.9600
Sb1—S1	2.8805 (6)	C12—H12C	0.9600
Sb1—S4	2.8938 (5)	C14—C15	1.504 (3)
S5—C5	1.7559 (17)	C14—H14A	0.9700
S2—C6	1.7362 (18)	C14—H14B	0.9700
S1—C6	1.7028 (18)	C1—H1A	0.9600
S3—C7	1.7378 (19)	C1—H1B	0.9600
S6—C5	1.6896 (17)	C1—H1C	0.9600
S4—C7	1.696 (2)	C4—H4A	0.9600
N1—C5	1.331 (2)	C4—H4B	0.9600
N1—C3	1.462 (2)	C4—H4C	0.9600
N1—C2	1.467 (2)	C11—H11A	0.9600
N3—C7	1.336 (2)	C11—H11B	0.9600
N3—C9	1.408 (17)	C11—H11C	0.9600
N3—C10	1.471 (3)	C15—H15A	0.9600
N3—C9'	1.545 (13)	C15—H15B	0.9600
N2—C6	1.324 (2)	C15—H15C	0.9600
N2—C13	1.471 (2)	C9—C8	1.49 (2)
N2—C14	1.478 (2)	C9—H9A	0.9700
C2—C1	1.509 (3)	C9—H9B	0.9700
C2—H2A	0.9700	C8—H8A	0.9600
C2—H2B	0.9700	C8—H8B	0.9600
C3—C4	1.505 (3)	C8—H8C	0.9600
C3—H3A	0.9700	C9'—C8'	1.52 (2)
C3—H3B	0.9700	C9'—H9'1	0.9700
C10—C11	1.503 (3)	C9'—H9'2	0.9700
C10—H10A	0.9700	C8'—H8'1	0.9600
C10—H10B	0.9700	C8'—H8'2	0.9600
C13—C12	1.511 (3)	C8'—H8'3	0.9600
C13—H13A	0.9700

S5—Sb1—S3	89.136 (16)	N2—C13—H13B	109.2
S5—Sb1—S2	89.071 (16)	C12—C13—H13B	109.2
S3—Sb1—S2	74.239 (14)	H13A—C13—H13B	107.9
S5—Sb1—S1	83.205 (17)	C13—C12—H12A	109.5
S3—Sb1—S1	138.085 (14)	C13—C12—H12B	109.5
S2—Sb1—S1	64.525 (14)	H12A—C12—H12B	109.5
S5—Sb1—S4	91.853 (17)	C13—C12—H12C	109.5
S3—Sb1—S4	64.313 (15)	H12A—C12—H12C	109.5
S2—Sb1—S4	138.518 (15)	H12B—C12—H12C	109.5
S1—Sb1—S4	156.580 (15)	N2—C14—C15	111.95 (18)
C5—S5—Sb1	93.69 (5)	N2—C14—H14A	109.2
C6—S2—Sb1	92.32 (6)	C15—C14—H14A	109.2
C6—S1—Sb1	84.85 (6)	N2—C14—H14B	109.2
C7—S3—Sb1	92.07 (7)	C15—C14—H14B	109.2
C7—S4—Sb1	84.06 (6)	H14A—C14—H14B	107.9
C5—N1—C3	123.63 (15)	C2—C1—H1A	109.5
C5—N1—C2	121.14 (15)	C2—C1—H1B	109.5
C3—N1—C2	115.22 (14)	H1A—C1—H1B	109.5
C7—N3—C9	124.3 (8)	C2—C1—H1C	109.5
C7—N3—C10	122.90 (16)	H1A—C1—H1C	109.5
C9—N3—C10	112.4 (7)	H1B—C1—H1C	109.5
C7—N3—C9'	118.9 (6)	C3—C4—H4A	109.5
C9—N3—C9'	17.9 (8)	C3—C4—H4B	109.5
C10—N3—C9'	117.2 (6)	H4A—C4—H4B	109.5
C6—N2—C13	122.77 (16)	C3—C4—H4C	109.5
C6—N2—C14	121.42 (16)	H4A—C4—H4C	109.5
C13—N2—C14	115.78 (15)	H4B—C4—H4C	109.5
N1—C2—C1	111.36 (16)	C10—C11—H11A	109.5
N1—C2—H2A	109.4	C10—C11—H11B	109.5
C1—C2—H2A	109.4	H11A—C11—H11B	109.5
N1—C2—H2B	109.4	C10—C11—H11C	109.5
C1—C2—H2B	109.4	H11A—C11—H11C	109.5
H2A—C2—H2B	108.0	H11B—C11—H11C	109.5
N1—C5—S6	123.48 (13)	C14—C15—H15A	109.5
N1—C5—S5	117.32 (12)	C14—C15—H15B	109.5
S6—C5—S5	119.20 (9)	H15A—C15—H15B	109.5
N2—C6—S1	122.83 (14)	C14—C15—H15C	109.5
N2—C6—S2	119.00 (14)	H15A—C15—H15C	109.5
S1—C6—S2	118.17 (10)	H15B—C15—H15C	109.5
N3—C7—S4	123.55 (14)	N3—C9—C8	119.0 (9)
N3—C7—S3	118.29 (15)	N3—C9—H9A	107.6
S4—C7—S3	118.16 (10)	C8—C9—H9A	107.6
N1—C3—C4	111.55 (17)	N3—C9—H9B	107.6
N1—C3—H3A	109.3	C8—C9—H9B	107.6
C4—C3—H3A	109.3	H9A—C9—H9B	107.0
N1—C3—H3B	109.3	C8'—C9'—N3	107.9 (9)
C4—C3—H3B	109.3	C8'—C9'—H9'1	110.1
H3A—C3—H3B	108.0	N3—C9'—H9'1	110.1
N3—C10—C11	111.87 (17)	C8'—C9'—H9'2	110.1
N3—C10—H10A	109.2	N3—C9'—H9'2	110.1
C11—C10—H10A	109.2	H9'1—C9'—H9'2	108.4
N3—C10—H10B	109.2	C9'—C8'—H8'1	109.5
C11—C10—H10B	109.2	C9'—C8'—H8'2	109.5
H10A—C10—H10B	107.9	H8'1—C8'—H8'2	109.5
N2—C13—C12	112.18 (17)	C9'—C8'—H8'3	109.5
N2—C13—H13A	109.2	H8'1—C8'—H8'3	109.5
C12—C13—H13A	109.2	H8'2—C8'—H8'3	109.5

S3—Sb1—S5—C5	−150.76 (6)	C14—N2—C6—S2	179.31 (14)
S2—Sb1—S5—C5	134.99 (6)	Sb1—S1—C6—N2	−176.81 (15)
S1—Sb1—S5—C5	70.53 (6)	Sb1—S1—C6—S2	3.31 (9)
S4—Sb1—S5—C5	−86.50 (6)	Sb1—S2—C6—N2	176.50 (13)
S5—Sb1—S2—C6	−80.83 (6)	Sb1—S2—C6—S1	−3.61 (10)
S3—Sb1—S2—C6	−170.20 (6)	C9—N3—C7—S4	13.3 (6)
S1—Sb1—S2—C6	2.08 (6)	C10—N3—C7—S4	−174.62 (15)
S4—Sb1—S2—C6	−172.58 (6)	C9'—N3—C7—S4	−6.7 (6)
S5—Sb1—S1—C6	90.09 (6)	C9—N3—C7—S3	−167.7 (6)
S3—Sb1—S1—C6	9.03 (7)	C10—N3—C7—S3	4.3 (3)
S2—Sb1—S1—C6	−2.13 (6)	C9'—N3—C7—S3	172.3 (6)
S4—Sb1—S1—C6	168.95 (6)	Sb1—S4—C7—N3	−170.09 (16)
S5—Sb1—S3—C7	99.33 (6)	Sb1—S4—C7—S3	10.93 (9)
S2—Sb1—S3—C7	−171.40 (6)	Sb1—S3—C7—N3	168.95 (14)
S1—Sb1—S3—C7	178.14 (6)	Sb1—S3—C7—S4	−12.02 (10)
S4—Sb1—S3—C7	6.85 (6)	C5—N1—C3—C4	92.1 (2)
S5—Sb1—S4—C7	−95.21 (6)	C2—N1—C3—C4	−87.3 (2)
S3—Sb1—S4—C7	−7.06 (6)	C7—N3—C10—C11	85.0 (2)
S2—Sb1—S4—C7	−4.51 (7)	C9—N3—C10—C11	−102.1 (6)
S1—Sb1—S4—C7	−172.31 (7)	C9'—N3—C10—C11	−83.1 (6)
C5—N1—C2—C1	92.8 (2)	C6—N2—C13—C12	86.1 (2)
C3—N1—C2—C1	−87.77 (19)	C14—N2—C13—C12	−91.9 (2)
C3—N1—C5—S6	−176.11 (13)	C6—N2—C14—C15	92.1 (2)
C2—N1—C5—S6	3.2 (2)	C13—N2—C14—C15	−89.8 (2)
C3—N1—C5—S5	3.6 (2)	C7—N3—C9—C8	100.7 (13)
C2—N1—C5—S5	−177.00 (13)	C10—N3—C9—C8	−72.1 (15)
Sb1—S5—C5—N1	−163.57 (12)	C9'—N3—C9—C8	178 (5)
Sb1—S5—C5—S6	16.20 (10)	C7—N3—C9'—C8'	98.3 (9)
C13—N2—C6—S1	−178.50 (14)	C9—N3—C9'—C8'	−15 (4)
C14—N2—C6—S1	−0.6 (3)	C10—N3—C9'—C8'	−93.1 (10)
C13—N2—C6—S2	1.4 (2)

Experimental details

Crystal data
Chemical formula	[Sb(C₅H₁₀NS₂)₃]
M_r	566.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.6454 (2), 13.6217 (2), 14.6731 (2)
β (°)	99.858 (1)
V (Å³)	2490.15 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.26 × 0.21 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.679, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	24761, 5746, 4947
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.059, 1.00
No. of reflections	5746
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sb1—S5	2.4842 (5)	Sb1—S1	2.8805 (6)
Sb1—S3	2.6238 (5)	Sb1—S4	2.8938 (5)
Sb1—S2	2.6328 (5)

Acknowledgements

This research was supported by the Chinese Ministry of Science and Technology (2005BA316C) and the Key Laboratory of Enviromentally-Friendly Polymer Materials of Anhui Province.

References

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