Home Physical Sciences The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
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The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 5

Abstract

[SbCl3(C9H11N3S2)2], monoclinic, P21/n (no. 14), a = 13.8069(4) Å, b = 13.5739(6) Å, c = 14.0182(5) Å, β = 94.231(3)°, V = 2,620.04(17) Å3, Z = 4, R gt (F) = 0.0329, wRref(F2) = 0.0726, T = 153 K.

CCDC no.: 2374488

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow prism
Size: 0.32 × 0.28 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.70 mm−1
Diffractometer, scan mode: STOE IPDS 2, rotation method
θmax, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 34,269, 5,965, 0.039
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 5,231
N(param)refined: 309
Programs: X-RED, 1 X-AREA, 1 SHELX, 2 , 3 ORTEP-3 4
Table 2:

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

Atom x y z Uiso*/Ueq
Sb1 0.64366 (2) 0.24601 (2) 0.53951 (2) 0.01768 (6)
Cl1 0.78386 (6) 0.14400 (6) 0.57836 (6) 0.02799 (17)
Cl2 0.67120 (6) 0.33885 (6) 0.68384 (5) 0.02716 (16)
Cl3 0.53975 (6) 0.13044 (6) 0.61169 (6) 0.03006 (18)
S1A 0.08071 (5) 0.39812 (6) 0.86473 (5) 0.02098 (15)
S2A 0.45442 (6) 0.36408 (9) 0.47917 (7) 0.0397 (2)
N1A 0.23472 (17) 0.34382 (17) 0.64476 (17) 0.0166 (5)
N2A 0.05054 (18) 0.3262 (2) 0.69011 (19) 0.0208 (5)
H1N 0.069 (3) 0.310 (3) 0.638 (3) 0.024 (10)*
N3A 0.2649 (2) 0.3541 (2) 0.46135 (19) 0.0243 (6)
H2N 0.211 (3) 0.348 (3) 0.488 (3) 0.051 (13)*
C1A 0.2180 (2) 0.34679 (19) 0.7378 (2) 0.0148 (5)
C2A 0.2914 (2) 0.3423 (2) 0.8109 (2) 0.0197 (6)
H2A 0.276750 0.345868 0.875933 0.024*
C3A 0.3865 (2) 0.3326 (2) 0.7867 (2) 0.0240 (6)
H3A 0.438097 0.326279 0.834938 0.029*
C4A 0.4047 (2) 0.3324 (2) 0.6912 (2) 0.0235 (6)
H4A 0.469456 0.327467 0.672841 0.028*
C5A 0.3277 (2) 0.3395 (2) 0.6223 (2) 0.0186 (6)
C6A 0.1134 (2) 0.3545 (2) 0.7597 (2) 0.0158 (5)
C7A −0.0541 (2) 0.3225 (3) 0.6984 (3) 0.0315 (8)
H7A −0.068097 0.279183 0.751592 0.047*
H7B −0.086215 0.296775 0.638804 0.047*
H7C −0.078327 0.388874 0.710227 0.047*
C8A 0.3439 (2) 0.3505 (2) 0.5183 (2) 0.0204 (6)
C9A 0.2612 (3) 0.3709 (3) 0.3583 (2) 0.0327 (8)
H9A 0.273164 0.440766 0.345879 0.049*
H9B 0.197014 0.352417 0.329416 0.049*
H9C 0.311049 0.330898 0.330463 0.049*
S1B 0.59722 (6) 0.32279 (8) −0.03756 (7) 0.0350 (2)
S2B 0.80156 (6) 0.40692 (6) 0.48082 (5) 0.02731 (17)
N1B 0.73429 (17) 0.40148 (17) 0.20157 (17) 0.0166 (5)
N2B 0.76630 (19) 0.4087 (2) 0.01454 (18) 0.0218 (5)
H3N 0.800 (3) 0.440 (3) 0.059 (3) 0.023 (9)*
N3B 0.88898 (19) 0.4177 (2) 0.31998 (19) 0.0219 (5)
H4N 0.888 (3) 0.421 (3) 0.262 (3) 0.035 (11)*
C1B 0.6576 (2) 0.4000 (2) 0.1375 (2) 0.0180 (6)
C2B 0.5622 (2) 0.4135 (2) 0.1621 (2) 0.0245 (6)
H2B 0.509376 0.413291 0.114652 0.029*
C3B 0.5472 (2) 0.4273 (3) 0.2575 (2) 0.0272 (7)
H3B 0.483334 0.437372 0.276534 0.033*
C4B 0.6256 (2) 0.4264 (2) 0.3255 (2) 0.0222 (6)
H4B 0.616374 0.434493 0.391498 0.027*
C5B 0.7176 (2) 0.4134 (2) 0.2941 (2) 0.0175 (5)
C6B 0.6791 (2) 0.3809 (2) 0.0363 (2) 0.0196 (6)
C7B 0.8055 (3) 0.3971 (3) −0.0785 (2) 0.0284 (7)
H7D 0.856477 0.346790 −0.074292 0.043*
H7E 0.832859 0.459950 −0.098104 0.043*
H7F 0.753427 0.376911 −0.125787 0.043*
C8B 0.8070 (2) 0.4124 (2) 0.3621 (2) 0.0184 (6)
C9B 0.9852 (2) 0.4178 (3) 0.3698 (3) 0.0340 (8)
H9D 0.994569 0.478947 0.406517 0.051*
H9E 1.034461 0.413155 0.323167 0.051*
H9F 0.991378 0.361325 0.413434 0.051*

1 Source of materials

The synthesis of the title compound was performed using standard Schlenk technique 5 with Argon (5.9 Nippon gases) as inert gas. Pyridine-2,6-dithiocarbomethylamide was prepared according to a literature procedure. 6

In a representative experiment 495 mg (2.2 mmol) of pyridine-2,6-dithiocarbomethylamide was dissolved in 10 mL THF (purified in Mbraun SPS 800, VWR AnalaR). The solution was cooled in an ice-ethanol bath to −10 °C. 2 mL of n-butyllithium (2.5 M in hexanes, Merck) were added slowly. The solution turns red and was allowed to reach room temperature over 20 min. Afterward the solution was cooled down to −10 °C again and 0.5 g of SbCl3 (Merck, distilled before use, 2.2 mmol) dissolved in THF (40 mass%) and 10 mL of pure THF were added. The solution turned yellowish-green immediately. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and was replaced with 10 mL of chloroform (Fisher scientific, stabilized with amylene, dried over molecular sieves 3 Å and activated alumina). The suspension was filtrated, the residue was washed with additional 5 mL of CHCl3. The solvent was removed under reduced pressure from the filtrate. 1 mL of CDCl3 was added for NMR. NMR analysis of the bulk product showed the formation of a product mixture. From the residue suspension orange crystals of the title compound suitable for X-ray diffraction were obtained after 6 weeks standing at room temperature. Large yellow prisms, decomposition point: 157 °C.

2 Experimental details

The carbon-bound H atoms were geometrically placed (C–H = 0.95–0.98 Å) and refined as riding atoms with Uiso(H) = 1.2–1.5 Ueq(C). The N-bound H-atoms were located in a difference Fourier map and their positions and isotropic displacement parameters were refined using isotropic approximation.

3 Comment

Pyridine-2,6-dithiocarbomethylamide has been used as chelate ligand to prepare several nickel, iron, and copper complexes. 6 , 7 , 8 , 9 Herein we describe the crystal structure of an adduct formed out of pyridine-2,6-dithiocarbomethylamide and antimony trichloride. The crystal structure was obtained as a side product during our work about chelate complexes of antimony. 10 , 11

The asymmetric unit of the crystal structure contains one molecule antimony trichloride, SbCl3, and two molecules of pyridine-2,6-dithiocarbomethylamide. The formation of a chelate complex, as initially intended, was not observed. Instead an adduct or simple coordination compound was formed, wherein three pyridine-2,6-dithiocarbomethylamide molecules coordinate via one sulfur atom each at the antimony atom. The bond lengths Sb1–Cl1 [2.4095(8) Å], Sb1–Cl2 [2.3901(8) Å], and Sb1–Cl3 [2.3995(8) Å] correspond well with the sum of covalent radii of 2.40 Å [r(Sb) = 1.41 Å, r(Cl) = 0.99 Å]. 12 The atomic distances Sb1⋯S2A [3.128(1) Å], Sb1⋯S2B [3.2349(8) Å] and Sb1⋯S1A [3.2050(8) Å] are substantial longer than the sum of covalent radii of 2.45 Å [r(S) = 1.04 Å], but shorter than the sum of van der Waals radii of 3.86 Å [r(Sb) = 2.06 Å, r(S) = 1.80 Å]. 13 The last interaction between Sb1 and S1A is not shown in the figure, since the sulfur atom belongs to a symmetry equivalent molecule of pyridine-2,6-dithiocarbomethylamide on the position x + 1/2, −y + 1/2, z − 1/2. The interactions with three chlorine and three sulfur atoms making the antimony atom hexacoordinated. The coordination geometry at the antimony atom can be classified as distorted octahedral. The trans bond angles vary between 169.68(3)° for Cl3–Sb1–S2B and 175.32(3)° for Cl1–Sb1–S2A. The cis bond angles in the distorted octahedron vary from 77.67(2)° for Cl3–Sb1–S1A to 111.57(2)° for S2B–Sb1–S1A.

The thiocarbomethylamide units of the ligand molecules have conformational flexibility to rotate around the bonds C1–C6 and C5–C8 (in both molecules A and B). Both groups adopt a conformation in the solid state where the sulfur atoms are oriented away from the pyridine nitrogen atom. The same conformation of thiocarbomethylamide units was observed in the crystal structure of pyridine-2,6-dithiocarbomethylamide. 14 This conformation allows the formation of hydrogen bonds between the N–H groups at N2 and N3 with the pyridine nitrogen atom N1 (in molecules A and B). On the other side, the sulfur atoms are oriented in lateral positions at the pyridine-2,6-dithiocarbomethylamide and allow coordination with the antimony atom in the present structure. Further hydrogen bonds are formed between N–H respectively C–H groups and sulfur atoms, forming a complicated threedimensional network in the solid state.

There are a few related crystal structures containing pyridine-2,6-dithiocarbomethylamide as ligand in nickel and copper complexes. 7 , 8 , 9 However, a comparison of these structures with the title compound is not fruitful, since the ligand molecule acts in these complexes as chelate ligand.

Corresponding author: Uwe Böhme, Institut für Anorganische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, 09599 Freiberg, Germany, E-mail:

Acknowledgments

The authors thank TU Bergakademie Freiberg (Freiberg, Germany) for financial support. Open Access Funding by the Publication Fund of the TU Bergakademie Freiberg.

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  3. Research funding: TU Bergakademie Freiberg (Freiberg, Germany).

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Received: 2024-06-24
Accepted: 2024-07-30
Published Online: 2024-08-09
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/ncrs-2024-0258
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Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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