Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053962/lx2025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053962/lx2025Isup2.hkl |
CCDC reference: 625167
The title compound were prepared by reaction of antimony trichloride (22.8 mg, 0.1 mmol) with the corresponding sodium dithiocarbamate (33.8 mg, 0.2 mmol), in absolute acetone. After stirring for 5 h at room temperature, the yellow paste was obtained and then filtered. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol/dichloromethane (1:2 v/v) solution over a period of two weeks (yield 85%. m.p. 421k).
All methylene H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: Please supply; 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.
[Sb(C5H8NS2)2Cl] | Z = 2 |
Mr = 449.69 | F(000) = 444 |
Triclinic, P1 | Dx = 1.869 Mg m−3 |
Hall symbol: -p_1 | Melting point: 421 K |
a = 6.367 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.368 (3) Å | Cell parameters from 2270 reflections |
c = 13.414 (4) Å | θ = 2.2–27.2° |
α = 111.451 (3)° | µ = 2.40 mm−1 |
β = 91.950 (3)° | T = 298 K |
γ = 102.334 (3)° | Block, yellow |
V = 799.0 (4) Å3 | 0.43 × 0.22 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 2764 independent reflections |
Radiation source: fine-focus sealed tube | 2300 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 1.6° |
ϕ and ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.540, Tmax = 0.748 | l = −15→14 |
4147 measured reflections |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0198P)2 + 0.5878P] where P = (Fo2 + 2Fc2)/3 |
2764 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Sb(C5H8NS2)2Cl] | γ = 102.334 (3)° |
Mr = 449.69 | V = 799.0 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.367 (2) Å | Mo Kα radiation |
b = 10.368 (3) Å | µ = 2.40 mm−1 |
c = 13.414 (4) Å | T = 298 K |
α = 111.451 (3)° | 0.43 × 0.22 × 0.12 mm |
β = 91.950 (3)° |
Bruker SMART CCD area-detector diffractometer | 2764 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2300 reflections with I > 2σ(I) |
Tmin = 0.540, Tmax = 0.748 | Rint = 0.016 |
4147 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.50 e Å−3 |
2764 reflections | Δρmin = −0.39 e Å−3 |
163 parameters |
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. |
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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
Sb | 0.47864 (4) | 0.69539 (3) | 0.67024 (2) | 0.04236 (10) | |
Cl | 0.55811 (19) | 0.51311 (11) | 0.75268 (10) | 0.0617 (3) | |
N1 | 0.8661 (5) | 0.7553 (3) | 0.4252 (2) | 0.0407 (7) | |
N2 | 0.6570 (5) | 1.1281 (3) | 0.9245 (2) | 0.0422 (8) | |
S1 | 0.79220 (18) | 0.62807 (11) | 0.56520 (8) | 0.0470 (3) | |
S2 | 0.57692 (18) | 0.84792 (11) | 0.55290 (9) | 0.0494 (3) | |
S3 | 0.73312 (16) | 0.87619 (11) | 0.82510 (8) | 0.0461 (3) | |
S4 | 0.32233 (16) | 0.95228 (11) | 0.78277 (9) | 0.0492 (3) | |
C1 | 0.7584 (6) | 0.7455 (4) | 0.5043 (3) | 0.0409 (9) | |
C2 | 1.0227 (7) | 0.6709 (4) | 0.3792 (3) | 0.0491 (10) | |
H2A | 0.9501 | 0.5719 | 0.3370 | 0.059* | |
H2B | 1.1267 | 0.6746 | 0.4354 | 0.059* | |
C3 | 1.1315 (8) | 0.7439 (5) | 0.3083 (4) | 0.0653 (13) | |
H3A | 1.2543 | 0.8217 | 0.3491 | 0.078* | |
H3B | 1.1805 | 0.6766 | 0.2476 | 0.078* | |
C4 | 0.9570 (7) | 0.7985 (5) | 0.2707 (4) | 0.0607 (12) | |
H4A | 0.8640 | 0.7239 | 0.2087 | 0.073* | |
H4B | 1.0193 | 0.8785 | 0.2511 | 0.073* | |
C5 | 0.8312 (7) | 0.8447 (4) | 0.3655 (3) | 0.0493 (10) | |
H5A | 0.8865 | 0.9454 | 0.4097 | 0.059* | |
H5B | 0.6785 | 0.8272 | 0.3416 | 0.059* | |
C6 | 0.5738 (6) | 1.0000 (4) | 0.8510 (3) | 0.0373 (9) | |
C7 | 0.5537 (7) | 1.2488 (4) | 0.9503 (4) | 0.0542 (11) | |
H7A | 0.4385 | 1.2397 | 0.9946 | 0.065* | |
H7B | 0.4950 | 1.2553 | 0.8851 | 0.065* | |
C8 | 0.7370 (8) | 1.3764 (5) | 1.0113 (4) | 0.0682 (13) | |
H8A | 0.6835 | 1.4527 | 1.0620 | 0.082* | |
H8B | 0.8160 | 1.4119 | 0.9623 | 0.082* | |
C9 | 0.8783 (8) | 1.3204 (5) | 1.0696 (4) | 0.0726 (14) | |
H9A | 0.8228 | 1.3188 | 1.1357 | 0.087* | |
H9B | 1.0257 | 1.3790 | 1.0872 | 0.087* | |
C10 | 0.8697 (6) | 1.1707 (4) | 0.9909 (3) | 0.0513 (11) | |
H10A | 0.9873 | 1.1702 | 0.9468 | 0.062* | |
H10B | 0.8773 | 1.1074 | 1.0285 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sb | 0.04020 (17) | 0.03755 (16) | 0.04356 (17) | 0.00320 (11) | −0.00365 (11) | 0.01315 (12) |
Cl | 0.0679 (8) | 0.0477 (6) | 0.0738 (8) | 0.0122 (5) | 0.0030 (6) | 0.0298 (6) |
N1 | 0.0409 (19) | 0.0416 (18) | 0.0417 (19) | 0.0116 (15) | −0.0013 (15) | 0.0180 (15) |
N2 | 0.0419 (19) | 0.0383 (18) | 0.0404 (19) | 0.0063 (15) | 0.0001 (15) | 0.0105 (15) |
S1 | 0.0551 (7) | 0.0439 (6) | 0.0477 (6) | 0.0167 (5) | 0.0046 (5) | 0.0214 (5) |
S2 | 0.0574 (7) | 0.0480 (6) | 0.0487 (6) | 0.0223 (5) | 0.0068 (5) | 0.0201 (5) |
S3 | 0.0399 (6) | 0.0441 (6) | 0.0479 (6) | 0.0109 (5) | −0.0091 (5) | 0.0112 (5) |
S4 | 0.0333 (5) | 0.0490 (6) | 0.0586 (7) | 0.0080 (5) | −0.0051 (5) | 0.0149 (5) |
C1 | 0.041 (2) | 0.034 (2) | 0.040 (2) | 0.0037 (17) | −0.0081 (18) | 0.0107 (17) |
C2 | 0.046 (2) | 0.048 (2) | 0.059 (3) | 0.014 (2) | 0.007 (2) | 0.025 (2) |
C3 | 0.064 (3) | 0.074 (3) | 0.077 (3) | 0.030 (3) | 0.026 (3) | 0.041 (3) |
C4 | 0.063 (3) | 0.071 (3) | 0.061 (3) | 0.021 (2) | 0.014 (2) | 0.036 (3) |
C5 | 0.053 (3) | 0.052 (2) | 0.050 (3) | 0.013 (2) | 0.001 (2) | 0.027 (2) |
C6 | 0.033 (2) | 0.041 (2) | 0.037 (2) | 0.0022 (17) | 0.0027 (16) | 0.0185 (18) |
C7 | 0.057 (3) | 0.043 (2) | 0.056 (3) | 0.016 (2) | 0.007 (2) | 0.010 (2) |
C8 | 0.084 (4) | 0.046 (3) | 0.063 (3) | 0.006 (3) | 0.006 (3) | 0.012 (2) |
C9 | 0.079 (4) | 0.056 (3) | 0.060 (3) | −0.006 (3) | −0.010 (3) | 0.009 (2) |
C10 | 0.044 (2) | 0.056 (3) | 0.041 (2) | 0.000 (2) | −0.0083 (19) | 0.012 (2) |
Sb—S1 | 2.555 (1) | C3—C4 | 1.499 (6) |
Sb—S2 | 2.614 (1) | C3—H3A | 0.9700 |
Sb—S3 | 2.466 (1) | C3—H3B | 0.9700 |
Sb—S4 | 2.942 (1) | C4—C5 | 1.509 (6) |
Sb—S1i | 3.689 (2) | C4—H4A | 0.9700 |
Sb—Cl | 2.636 (1) | C4—H4B | 0.9700 |
N1—C1 | 1.306 (5) | C5—H5A | 0.9700 |
N1—C2 | 1.469 (5) | C5—H5B | 0.9700 |
N1—C5 | 1.473 (4) | C7—C8 | 1.505 (6) |
N2—C6 | 1.312 (5) | C7—H7A | 0.9700 |
N2—C7 | 1.473 (5) | C7—H7B | 0.9700 |
N2—C10 | 1.482 (5) | C8—C9 | 1.505 (6) |
S1—C1 | 1.739 (4) | C8—H8A | 0.9700 |
S2—C1 | 1.719 (4) | C8—H8B | 0.9700 |
S3—C6 | 1.747 (4) | C9—C10 | 1.513 (6) |
S4—C6 | 1.696 (4) | C9—H9A | 0.9700 |
C2—C3 | 1.519 (5) | C9—H9B | 0.9700 |
C2—H2A | 0.9700 | C10—H10A | 0.9700 |
C2—H2B | 0.9700 | C10—H10B | 0.9700 |
S3—Sb—S1 | 91.14 (4) | C3—C4—C5 | 105.1 (3) |
S3—Sb—S2 | 91.50 (4) | C3—C4—H4A | 110.7 |
S1—Sb—S2 | 69.56 (3) | C5—C4—H4A | 110.7 |
S3—Sb—Cl | 84.64 (4) | C3—C4—H4B | 110.7 |
S1—Sb—Cl | 82.23 (4) | C5—C4—H4B | 110.7 |
S2—Sb—Cl | 151.46 (4) | H4A—C4—H4B | 108.8 |
S3—Sb—S4 | 66.25 (4) | N1—C5—C4 | 103.4 (3) |
S1—Sb—S4 | 138.73 (3) | N1—C5—H5A | 111.1 |
S2—Sb—S4 | 76.71 (4) | C4—C5—H5A | 111.1 |
Cl—Sb—S4 | 126.19 (4) | N1—C5—H5B | 111.1 |
S3—Sb—S1i | 164.90 (3) | C4—C5—H5B | 111.1 |
S1—Sb—S1i | 77.01 (4) | H5A—C5—H5B | 109.0 |
S2—Sb—S1i | 93.03 (4) | N2—C6—S4 | 122.8 (3) |
Cl—Sb—S1i | 84.50 (4) | N2—C6—S3 | 117.2 (3) |
S4—Sb—S1i | 128.84 (3) | S4—C6—S3 | 120.0 (2) |
C1—N1—C2 | 124.6 (3) | N2—C7—C8 | 103.3 (3) |
C1—N1—C5 | 123.4 (3) | N2—C7—H7A | 111.1 |
C2—N1—C5 | 111.8 (3) | C8—C7—H7A | 111.1 |
C6—N2—C7 | 124.5 (3) | N2—C7—H7B | 111.1 |
C6—N2—C10 | 124.3 (3) | C8—C7—H7B | 111.1 |
C7—N2—C10 | 111.2 (3) | H7A—C7—H7B | 109.1 |
C1—S1—Sb | 87.21 (14) | C7—C8—C9 | 104.1 (4) |
C1—S2—Sb | 85.70 (13) | C7—C8—H8A | 110.9 |
C6—S3—Sb | 93.81 (13) | C9—C8—H8A | 110.9 |
C6—S4—Sb | 79.43 (13) | C7—C8—H8B | 110.9 |
N1—C1—S2 | 121.6 (3) | C9—C8—H8B | 110.9 |
N1—C1—S1 | 121.4 (3) | H8A—C8—H8B | 109.0 |
S2—C1—S1 | 117.0 (2) | C8—C9—C10 | 104.5 (4) |
N1—C2—C3 | 102.8 (3) | C8—C9—H9A | 110.8 |
N1—C2—H2A | 111.2 | C10—C9—H9A | 110.8 |
C3—C2—H2A | 111.2 | C8—C9—H9B | 110.8 |
N1—C2—H2B | 111.2 | C10—C9—H9B | 110.8 |
C3—C2—H2B | 111.2 | H9A—C9—H9B | 108.9 |
H2A—C2—H2B | 109.1 | N2—C10—C9 | 103.4 (3) |
C4—C3—C2 | 103.9 (3) | N2—C10—H10A | 111.1 |
C4—C3—H3A | 111.0 | C9—C10—H10A | 111.1 |
C2—C3—H3A | 111.0 | N2—C10—H10B | 111.1 |
C4—C3—H3B | 111.0 | C9—C10—H10B | 111.1 |
C2—C3—H3B | 111.0 | H10A—C10—H10B | 109.0 |
H3A—C3—H3B | 109.0 | ||
S3—Sb—S1—C1 | −95.47 (13) | Sb—S2—C1—S1 | −6.72 (19) |
S2—Sb—S1—C1 | −4.29 (12) | Sb—S1—C1—N1 | −173.1 (3) |
Cl—Sb—S1—C1 | −179.90 (13) | Sb—S1—C1—S2 | 6.9 (2) |
S4—Sb—S1—C1 | −41.48 (14) | C1—N1—C2—C3 | −168.9 (4) |
S1i—Sb—S1—C1 | 93.98 (13) | C5—N1—C2—C3 | 15.7 (5) |
S3—Sb—S2—C1 | 95.01 (13) | N1—C2—C3—C4 | −31.5 (5) |
S1—Sb—S2—C1 | 4.35 (13) | C2—C3—C4—C5 | 36.4 (5) |
Cl—Sb—S2—C1 | 13.47 (16) | C1—N1—C5—C4 | −169.2 (4) |
S4—Sb—S2—C1 | 160.16 (13) | C2—N1—C5—C4 | 6.3 (4) |
S1i—Sb—S2—C1 | −70.58 (13) | C3—C4—C5—N1 | −26.3 (5) |
S1—Sb—S3—C6 | 140.29 (12) | C7—N2—C6—S4 | −5.7 (5) |
S2—Sb—S3—C6 | 70.71 (12) | C10—N2—C6—S4 | 175.7 (3) |
Cl—Sb—S3—C6 | −137.62 (12) | C7—N2—C6—S3 | 174.7 (3) |
S4—Sb—S3—C6 | −4.06 (12) | C10—N2—C6—S3 | −3.9 (5) |
S1i—Sb—S3—C6 | 178.18 (14) | Sb—S4—C6—N2 | 174.1 (3) |
S3—Sb—S4—C6 | 4.24 (12) | Sb—S4—C6—S3 | −6.34 (18) |
S1—Sb—S4—C6 | −57.83 (13) | Sb—S3—C6—N2 | −172.9 (3) |
S2—Sb—S4—C6 | −93.42 (12) | Sb—S3—C6—S4 | 7.5 (2) |
Cl—Sb—S4—C6 | 67.61 (13) | C6—N2—C7—C8 | −163.2 (4) |
S1i—Sb—S4—C6 | −176.51 (12) | C10—N2—C7—C8 | 15.6 (4) |
C2—N1—C1—S2 | −179.7 (3) | N2—C7—C8—C9 | −32.2 (5) |
C5—N1—C1—S2 | −4.8 (5) | C7—C8—C9—C10 | 37.3 (5) |
C2—N1—C1—S1 | 0.3 (5) | C6—N2—C10—C9 | −174.1 (4) |
C5—N1—C1—S1 | 175.2 (3) | C7—N2—C10—C9 | 7.1 (4) |
Sb—S2—C1—N1 | 173.3 (3) | C8—C9—C10—N2 | −27.1 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sb(C5H8NS2)2Cl] |
Mr | 449.69 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 6.367 (2), 10.368 (3), 13.414 (4) |
α, β, γ (°) | 111.451 (3), 91.950 (3), 102.334 (3) |
V (Å3) | 799.0 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.40 |
Crystal size (mm) | 0.43 × 0.22 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.540, 0.748 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4147, 2764, 2300 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.060, 1.06 |
No. of reflections | 2764 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.39 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), Please supply, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Dithiocarbamates have been known as effective ligands for transition metal ions, which can form chelates (Xu et al., 2001) or act as bridging ligands (Bardaji et al., 1994). We have reported a similar compound, C10H16N2S4SbBr (Zhai et al., 2007). As part of our continuing studies on the chemistry of main-group metal complexes with dithiocarbamates, we have recently described the crystal structure of a similar compound, [SbBr(C5H8NS2]2, (Zhai et al., 2007). Herein we report the crystal structure of the title compound, bis(pyrrolidine-1-dithiocarboxylato-κ2S,S') chloridoantimony(III) (Fig. 1).
In the title compound (Fig. 1), the SbIII ion is coordinated by the four S atoms [Sb—S; 2.466 (1)–2.942 (1) Å] from two pyrrolidine-1-dithiocarboxylate ligands and a chloride atom in a distorted trigonal-bipyramid geometry, with S2, Cl in the axial sites and S1, S3, S4, Sb occupying the equatorial plane. The angles at Sb confirm that the complex has a distorted trigonal-bipyramid configuration. The short intermolecular distance Sb···S1i of 3.689 (1) Å suggests a presence of Sb···S interactions (Symmetry code as in Fig. 2).