Tris(O-cyclo-hexyl dithio-carbonato-κS)anti-mony(III).

In the mol-ecule of the title compound, [Sb(C(7)H(11)OS(2))(3)], the anti-mony(III) is coordinated by the S atoms of three O-alkyl xanthate groups acting as monodentate ligands, forming a distorted trigonal-pyramidal coordination.

Related literature

For the biological activity of anti­mony(III) complexes, see: Tiekink (2002 ▶); Wang et al. (2005 ▶). For a related structure, see: Baba et al. (2001 ▶).

Experimental

Crystal data

[Sb(C7H11OS2)3]

M = 646.58

Monoclinic,

a = 9.4187 (12) Å

b = 18.866 (2) Å

c = 15.8583 (18) Å

β = 93.944 (2)°

V = 2811.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.45 mm−1

T = 298 (2) K

0.30 × 0.25 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.664, T max = 0.773

14030 measured reflections

4946 independent reflections

3183 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.127

S = 1.00

4946 reflections

280 parameters

90 restraints

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.60 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040804/rz2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040804/rz2271Isup2.hkl

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

[Sb(C7H11OS2)3]	F(000) = 1316
Mr = 646.58	Dx = 1.528 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3706 reflections
a = 9.4187 (12) Å	θ = 2.5–25.0°
b = 18.866 (2) Å	µ = 1.45 mm−1
c = 15.8583 (18) Å	T = 298 K
β = 93.944 (2)°	Block, yellow
V = 2811.2 (6) Å3	0.30 × 0.25 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4946 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
graphite	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.664, Tmax = 0.773	k = −15→22
14030 measured reflections	l = −16→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
4946 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.86 e Å−3
90 restraints	Δρmin = −0.60 e Å−3

	x	y	z	Uiso*/Ueq
Sb1	0.23869 (4)	0.14457 (2)	0.75101 (2)	0.04805 (16)
O1	0.2841 (5)	−0.0631 (2)	0.6250 (2)	0.0678 (12)
O2	0.6257 (4)	0.2720 (2)	0.7766 (3)	0.0686 (11)
O3	−0.0197 (4)	0.1350 (3)	0.9707 (2)	0.0710 (13)
S1	0.25550 (19)	0.01168 (9)	0.75366 (9)	0.0625 (5)
S2	0.2947 (2)	0.07274 (9)	0.58338 (10)	0.0703 (5)
S3	0.50432 (16)	0.15233 (7)	0.77844 (10)	0.0522 (4)
S4	0.34846 (18)	0.28996 (8)	0.77444 (12)	0.0685 (5)
S5	0.21960 (15)	0.13712 (9)	0.90767 (9)	0.0551 (4)
S6	−0.05683 (19)	0.14457 (13)	0.80641 (10)	0.0940 (7)
C1	0.2778 (6)	0.0043 (3)	0.6466 (3)	0.0556 (15)
C2	0.2862 (7)	−0.0849 (3)	0.5356 (3)	0.0608 (17)
H2	0.3328	−0.0487	0.5028	0.073*
C3	0.3659 (7)	−0.1531 (4)	0.5347 (4)	0.0683 (19)
H3A	0.3241	−0.1869	0.5718	0.082*
H3B	0.4641	−0.1454	0.5552	0.082*
C4	0.3606 (7)	−0.1822 (4)	0.4458 (4)	0.075 (2)
H4A	0.4093	−0.1499	0.4099	0.090*
H4B	0.4096	−0.2274	0.4459	0.090*
C5	0.2105 (7)	−0.1918 (3)	0.4107 (4)	0.0684 (18)
H5A	0.2105	−0.2078	0.3526	0.082*
H5B	0.1653	−0.2281	0.4429	0.082*
C6	0.1273 (8)	−0.1250 (4)	0.4138 (4)	0.088 (2)
H6A	0.0287	−0.1343	0.3952	0.106*
H6B	0.1644	−0.0906	0.3755	0.106*
C7	0.1347 (8)	−0.0944 (4)	0.5030 (4)	0.079 (2)
H7A	0.0861	−0.0491	0.5025	0.095*
H7B	0.0870	−0.1261	0.5400	0.095*
C8	0.4972 (6)	0.2437 (3)	0.7757 (3)	0.0487 (14)
C9	0.6450 (7)	0.3490 (3)	0.7713 (4)	0.0678 (17)
H9	0.5588	0.3726	0.7884	0.081*
C10	0.7653 (11)	0.3685 (4)	0.8306 (6)	0.119 (3)
H10A	0.8486	0.3410	0.8187	0.143*
H10B	0.7422	0.3583	0.8881	0.143*
C11	0.7964 (12)	0.4479 (4)	0.8213 (6)	0.129 (3)
H11A	0.7172	0.4750	0.8404	0.155*
H11B	0.8805	0.4600	0.8571	0.155*
C12	0.8189 (10)	0.4673 (5)	0.7347 (7)	0.129 (4)
H12	0.9001	0.4896	0.7174	0.154*
C13	0.6975 (12)	0.4471 (4)	0.6787 (5)	0.123 (3)
H13A	0.7161	0.4591	0.6210	0.148*
H13B	0.6147	0.4737	0.6935	0.148*
C14	0.6660 (11)	0.3674 (4)	0.6843 (5)	0.102 (2)
H14A	0.5813	0.3559	0.6487	0.123*
H14B	0.7449	0.3404	0.6645	0.123*
C15	0.0345 (6)	0.1386 (3)	0.8972 (3)	0.0528 (15)
C16	−0.1749 (6)	0.1372 (4)	0.9774 (4)	0.0660 (19)
H16	−0.2231	0.1328	0.9209	0.079*
C17	−0.2112 (7)	0.2063 (4)	1.0141 (5)	0.081 (2)
H17A	−0.1850	0.2441	0.9767	0.097*
H17B	−0.1576	0.2125	1.0680	0.097*
C18	−0.3717 (7)	0.2105 (4)	1.0267 (5)	0.094 (2)
H18A	−0.3920	0.2539	1.0563	0.112*
H18B	−0.4248	0.2114	0.9721	0.112*
C19	−0.4176 (7)	0.1482 (5)	1.0765 (5)	0.088 (2)
H19A	−0.3746	0.1513	1.1338	0.106*
H19B	−0.5201	0.1496	1.0794	0.106*
C20	−0.3769 (8)	0.0802 (4)	1.0387 (5)	0.086 (2)
H20A	−0.4261	0.0752	0.9832	0.103*
H20B	−0.4062	0.0413	1.0737	0.103*
C21	−0.2153 (7)	0.0760 (4)	1.0305 (4)	0.080 (2)
H21A	−0.1651	0.0785	1.0859	0.096*
H21B	−0.1909	0.0317	1.0041	0.096*

	U11	U22	U33	U12	U13	U23
Sb1	0.0516 (3)	0.0496 (3)	0.0438 (2)	−0.00345 (19)	0.00902 (16)	−0.0031 (2)
O1	0.111 (4)	0.047 (3)	0.047 (2)	−0.013 (2)	0.014 (2)	−0.010 (2)
O2	0.061 (3)	0.042 (2)	0.103 (3)	−0.003 (2)	0.007 (2)	0.001 (2)
O3	0.050 (3)	0.125 (4)	0.040 (2)	0.001 (3)	0.0127 (18)	0.003 (2)
S1	0.0940 (13)	0.0493 (10)	0.0461 (8)	−0.0114 (9)	0.0185 (8)	−0.0035 (8)
S2	0.1089 (14)	0.0522 (11)	0.0518 (9)	−0.0140 (10)	0.0208 (9)	−0.0035 (8)
S3	0.0502 (9)	0.0390 (8)	0.0681 (9)	0.0022 (7)	0.0102 (7)	−0.0032 (7)
S4	0.0612 (10)	0.0473 (10)	0.0995 (13)	0.0073 (8)	0.0244 (9)	−0.0028 (9)
S5	0.0482 (9)	0.0748 (11)	0.0425 (7)	−0.0002 (8)	0.0054 (6)	−0.0058 (8)
S6	0.0518 (10)	0.185 (2)	0.0455 (9)	0.0012 (12)	0.0042 (7)	0.0083 (12)
C1	0.067 (4)	0.046 (4)	0.054 (4)	−0.013 (3)	0.010 (3)	−0.009 (3)
C2	0.095 (5)	0.051 (4)	0.036 (3)	−0.019 (4)	0.005 (3)	−0.008 (3)
C3	0.054 (4)	0.086 (5)	0.064 (4)	0.001 (4)	0.001 (3)	−0.012 (4)
C4	0.070 (5)	0.095 (6)	0.062 (4)	0.011 (4)	0.012 (3)	−0.019 (4)
C5	0.085 (5)	0.054 (4)	0.065 (4)	0.001 (4)	−0.001 (3)	−0.019 (3)
C6	0.097 (6)	0.092 (6)	0.072 (5)	0.019 (5)	−0.020 (4)	−0.021 (4)
C7	0.085 (5)	0.085 (6)	0.067 (4)	0.038 (4)	−0.005 (4)	−0.021 (4)
C8	0.054 (4)	0.047 (4)	0.046 (3)	0.000 (3)	0.013 (3)	−0.004 (3)
C9	0.072 (4)	0.041 (4)	0.091 (4)	−0.009 (3)	0.007 (3)	0.005 (3)
C10	0.163 (7)	0.068 (5)	0.118 (6)	−0.025 (5)	−0.045 (5)	0.002 (5)
C11	0.161 (7)	0.068 (5)	0.149 (6)	−0.031 (5)	−0.052 (6)	−0.014 (5)
C12	0.090 (7)	0.087 (7)	0.213 (11)	−0.048 (6)	0.039 (7)	0.014 (7)
C13	0.186 (7)	0.078 (5)	0.108 (5)	−0.025 (5)	0.020 (5)	0.021 (5)
C14	0.166 (7)	0.053 (4)	0.087 (5)	−0.024 (5)	0.003 (5)	0.002 (4)
C15	0.050 (3)	0.058 (4)	0.052 (3)	−0.002 (3)	0.015 (3)	−0.003 (3)
C16	0.045 (4)	0.112 (6)	0.042 (3)	0.000 (4)	0.010 (3)	0.003 (4)
C17	0.063 (5)	0.066 (5)	0.116 (6)	−0.002 (4)	0.024 (4)	0.023 (5)
C18	0.061 (5)	0.101 (7)	0.122 (6)	0.010 (4)	0.023 (4)	−0.001 (5)
C19	0.054 (4)	0.139 (8)	0.073 (5)	−0.015 (5)	0.018 (4)	−0.008 (5)
C20	0.072 (5)	0.106 (7)	0.079 (5)	−0.034 (5)	0.002 (4)	0.020 (5)
C21	0.071 (5)	0.075 (5)	0.096 (5)	−0.012 (4)	0.015 (4)	−0.005 (4)

Sb1—S5	2.5072 (14)	C9—C10	1.469 (10)
Sb1—S1	2.5123 (17)	C9—H9	0.9800
Sb1—S3	2.5140 (15)	C10—C11	1.535 (10)
O1—C1	1.320 (6)	C10—H10A	0.9700
O1—C2	1.477 (6)	C10—H10B	0.9700
O2—C8	1.322 (6)	C11—C12	1.451 (11)
O2—C9	1.468 (7)	C11—H11A	0.9700
O3—C15	1.306 (6)	C11—H11B	0.9700
O3—C16	1.474 (7)	C12—C13	1.449 (11)
S1—C1	1.731 (5)	C12—H12	0.9300
S2—C1	1.649 (6)	C13—C14	1.537 (10)
S3—C8	1.726 (6)	C13—H13A	0.9700
S4—C8	1.649 (6)	C13—H13B	0.9700
S5—C15	1.740 (6)	C14—H14A	0.9700
S6—C15	1.630 (6)	C14—H14B	0.9700
C2—C3	1.490 (8)	C16—C17	1.475 (9)
C2—C7	1.496 (9)	C16—C21	1.493 (9)
C2—H2	0.9800	C16—H16	0.9800
C3—C4	1.511 (8)	C17—C18	1.541 (9)
C3—H3A	0.9700	C17—H17A	0.9700
C3—H3B	0.9700	C17—H17B	0.9700
C4—C5	1.493 (8)	C18—C19	1.497 (10)
C4—H4A	0.9700	C18—H18A	0.9700
C4—H4B	0.9700	C18—H18B	0.9700
C5—C6	1.487 (9)	C19—C20	1.479 (10)
C5—H5A	0.9700	C19—H19A	0.9700
C5—H5B	0.9700	C19—H19B	0.9700
C6—C7	1.524 (8)	C20—C21	1.538 (9)
C6—H6A	0.9700	C20—H20A	0.9700
C6—H6B	0.9700	C20—H20B	0.9700
C7—H7A	0.9700	C21—H21A	0.9700
C7—H7B	0.9700	C21—H21B	0.9700
C9—C14	1.450 (10)
S5—Sb1—S1	86.34 (5)	H10A—C10—H10B	108.3
S5—Sb1—S3	88.29 (5)	C12—C11—C10	112.3 (8)
S1—Sb1—S3	89.68 (5)	C12—C11—H11A	109.1
C1—O1—C2	121.3 (5)	C10—C11—H11A	109.1
C8—O2—C9	121.0 (5)	C12—C11—H11B	109.1
C15—O3—C16	120.9 (4)	C10—C11—H11B	109.1
C1—S1—Sb1	94.3 (2)	H11A—C11—H11B	107.9
C8—S3—Sb1	91.0 (2)	C13—C12—C11	110.7 (7)
C15—S5—Sb1	92.54 (18)	C13—C12—H12	124.7
O1—C1—S2	126.1 (4)	C11—C12—H12	124.7
O1—C1—S1	110.0 (4)	C12—C13—C14	111.7 (8)
S2—C1—S1	123.8 (3)	C12—C13—H13A	109.3
O1—C2—C3	106.8 (5)	C14—C13—H13A	109.3
O1—C2—C7	106.9 (5)	C12—C13—H13B	109.3
C3—C2—C7	111.2 (5)	C14—C13—H13B	109.3
O1—C2—H2	110.6	H13A—C13—H13B	107.9
C3—C2—H2	110.6	C9—C14—C13	109.2 (6)
C7—C2—H2	110.6	C9—C14—H14A	109.8
C2—C3—C4	109.8 (5)	C13—C14—H14A	109.8
C2—C3—H3A	109.7	C9—C14—H14B	109.8
C4—C3—H3A	109.7	C13—C14—H14B	109.8
C2—C3—H3B	109.7	H14A—C14—H14B	108.3
C4—C3—H3B	109.7	O3—C15—S6	125.2 (4)
H3A—C3—H3B	108.2	O3—C15—S5	111.4 (4)
C5—C4—C3	111.2 (5)	S6—C15—S5	123.4 (3)
C5—C4—H4A	109.4	O3—C16—C17	108.1 (5)
C3—C4—H4A	109.4	O3—C16—C21	108.2 (5)
C5—C4—H4B	109.4	C17—C16—C21	112.7 (5)
C3—C4—H4B	109.4	O3—C16—H16	109.3
H4A—C4—H4B	108.0	C17—C16—H16	109.3
C6—C5—C4	111.8 (6)	C21—C16—H16	109.3
C6—C5—H5A	109.2	C16—C17—C18	110.7 (6)
C4—C5—H5A	109.2	C16—C17—H17A	109.5
C6—C5—H5B	109.2	C18—C17—H17A	109.5
C4—C5—H5B	109.2	C16—C17—H17B	109.5
H5A—C5—H5B	107.9	C18—C17—H17B	109.5
C5—C6—C7	111.1 (5)	H17A—C17—H17B	108.1
C5—C6—H6A	109.4	C19—C18—C17	110.5 (6)
C7—C6—H6A	109.4	C19—C18—H18A	109.6
C5—C6—H6B	109.4	C17—C18—H18A	109.6
C7—C6—H6B	109.4	C19—C18—H18B	109.6
H6A—C6—H6B	108.0	C17—C18—H18B	109.6
C2—C7—C6	110.4 (6)	H18A—C18—H18B	108.1
C2—C7—H7A	109.6	C20—C19—C18	112.0 (6)
C6—C7—H7A	109.6	C20—C19—H19A	109.2
C2—C7—H7B	109.6	C18—C19—H19A	109.2
C6—C7—H7B	109.6	C20—C19—H19B	109.2
H7A—C7—H7B	108.1	C18—C19—H19B	109.2
O2—C8—S4	124.3 (4)	H19A—C19—H19B	107.9
O2—C8—S3	111.6 (4)	C19—C20—C21	111.3 (6)
S4—C8—S3	124.1 (3)	C19—C20—H20A	109.4
C14—C9—O2	108.5 (6)	C21—C20—H20A	109.4
C14—C9—C10	113.6 (7)	C19—C20—H20B	109.4
O2—C9—C10	107.6 (6)	C21—C20—H20B	109.4
C14—C9—H9	109.0	H20A—C20—H20B	108.0
O2—C9—H9	109.0	C16—C21—C20	107.5 (6)
C10—C9—H9	109.0	C16—C21—H21A	110.2
C9—C10—C11	109.0 (7)	C20—C21—H21A	110.2
C9—C10—H10A	109.9	C16—C21—H21B	110.2
C11—C10—H10A	109.9	C20—C21—H21B	110.2
C9—C10—H10B	109.9	H21A—C21—H21B	108.5
C11—C10—H10B	109.9

Table 1

Selected bond lengths (Å)

Sb1—S5	2.5072 (14)
Sb1—S1	2.5123 (17)
Sb1—S3	2.5140 (15)