catena-Poly[[chlorido­tris­(1,3-thia­zolidine-2-thione-κS)cadmium(II)]-μ-chlorido]

Diop, A.; Diop, T.; Kama, A.B.; Diop, C.A.K.; Tumanov, N.

doi:10.1107/S2414314620014236

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 10| October 2020| x201423

https://doi.org/10.1107/S2414314620014236

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catena-Poly[[chloridotris(1,3-thiazolidine-2-thione-κS)cadmium(II)]-μ-chlorido]

Aboubacar Diop,^a ^* Tidiane Diop,^a Antoine Blaise Kama,^a Cheikh Abdou Khadre Diop ^a and Nikolay Tumanov ^b

^aLaboratoire de Chimie Minérale et Analytique (LA.CHI.MI.A), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDepartement de Chimie, Université de Namur, Rue de Bruxelles 61-5000, Namur, Belgium
^*Correspondence e-mail: aboubacar.diop@ucad.edu.sn

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 8 October 2020; accepted 26 October 2020; online 30 October 2020)

The synthesis and characterization of poly[dichloridotri(1,3-thiazolidine-2-thione)cadmium(II)], [CdCl₂(C₃H₅NS₂)₃]_n, prepared from CdCl₂·H₂O and C₃H₅NS₂ (tzdSH) in a 1:3 ratio, are described. The Cd^II cation is coordinated by three 1,3-thiazolidine-2-thione molecules and three Cl⁻ anions in a distorted octahedral environment. The Cd metal centres are connected via Cl⁻ ligands, creating polymeric chains running along the a-axis direction. The conformation of the chains is stabilized by N—H⋯Cl hydrogen bonds.

Keywords: crystal structure; 1,3-thiazolidine-2-thione; cadmium centre; hydrogen bonding.

CCDC reference: 2040604

Structure description

1,3-Thiazolidine-2-thione (tzdSH: C₃H₅NS₂), is a well-known heterocyclic thione/thiol ligand. Crystallographic studies and investigations of its modes of coordination have been reported (Saithong et al., 2007 ). We are interested in the coordination behaviour and structure of tzdSH complexes with Cd^II chloride. The synthesis is accompanied by a transformation of the tzdSH (tzdSH: C₃H₅NS₂, thiol form) into a tzdt ligand (tzdt: C₃H₅NS₂, thion form). A similar transformation was described previously by Saithong et al. (2014 ). Metal complexes of thiones and thionates were reviewed by Raper (1997 ).

Cadmium (II) is known to form a wide variety of 1:1 to 1:4 complexes with thiones, where the structural arrangements are generally tetrahedral and octahedral coordination environments (Mahmood et al., 2018 ). The 1:1 complexes, for example [Cd(Melmt)(S_eCN)] (Melmt = N-methylimidazolidine-2-thione; Fettouhi et al., 2008 ) usually exist in the polymeric form. The 1:2 complexes such as [Cd(Dmtu)₂X₂] (Dmtu = N,N′-dimethylthiourea-κS; X = Cl, Br, I; Ahmad et al., 2011 ) are the most common and often consist of discrete monomeric molecules with a terahedrally (Moloto et al., 2003 ) or octahedrally (Mahmood et al., 2012 ) coordinated Cd^II ion. The 1:3 compounds are rare: the structure of [Cd(Tu)₃(SO₄)] shows that the complex is a dimer, and the coordination around the metal atom is intermediate between square pyramidal and trigonal bipyramidal (Corao & Baggio, 1969 ). The 1:4 complexes may be ionic or non-ionic (Mahmood et al., 2018).

The above structural studies show that thiones coordinate to cadmium (II) via the sulfur atom. To further investigate the structural aspects of such complexes, we report in this work a complex with a Cd^II:thione ratio of 1:23. The asymmetric unit consists of a cadmium (II) ion bonded to three 1,3-thiazolidine-2-thione moieties via the exocyclic sulfur atom and two Cl atoms (Fig. 1). The Cd—S and Cd—Cl bond lengths are in the range 2.7004 (11)–2.7347 (13) and 2.5430 (12)–2.7258 (16) Å, respectively. The bond lengths are slightly different from those reported in the literature [Cd—S = 2.604 Å and Cd—Cl = 2.7105 Å; Bell et al., 2004 ]. This may be due to the intramolecular hydrogen bonds observed in the crystal structure.

Figure 1
The asymmetric unit of title compound with displacement ellipsoids drawn at the 50% probability level.

In the crystal, one of Cl⁻ anions connects two neighbouring Cd^II centers leading to polymeric chains. No hydrogen bonds are observed between the chains. The structure of the compound can be described as parallel chains running along the a-axis direction. The conformation of the chains is stabilized by N—H⋯Cl hydrogen bonds (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.86	2.43	3.260 (4)	163
N2—H2⋯Cl1ⁱ	0.86	2.47	3.314 (4)	168
N3—H3⋯Cl2	0.86	2.41	3.165 (4)	147
C8—H8B⋯Cl1ⁱⁱ	0.97	2.82	3.781 (6)	171
Symmetry codes: (i) $[-x-1, -y-1, z+{\script{1\over 2}}]$ ; (ii) .

Figure 2
Packing diagram of the title compound. N—H⋯Cl hydrogen bonds are show as light blue dashed lines.

Synthesis and crystallization

In a round-bottom flask, to the ligand (tzdSH: C₃H₅NS₂) (15 mmol, 1.79 g) in 5 mL of 1,4-dioxan, a solution of CdCl₂·H₂O (5 mmol, 1.01 g) in 5 mL of distilled water was added. The mixture was refluxed for 4 h. Light-yellow crystals appeared after the light yellow filtrate had been kept at room temperature for two days (yield 75%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[CdCl₂(C₃H₅NS₂)₃]
M_r	540.90
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	9.2014 (3), 19.3472 (6), 10.5827 (3)
V (Å³)	1883.94 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.10
Crystal size (mm)	0.76 × 0.50 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur, Ruby, Gemini Ultra
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.242, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12033, 5594, 4781
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.069, 1.01
No. of reflections	5594
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.79
Absolute structure	Flack x determined using 1872 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.010 (19)
Computer programs: CrysAlis PRO (Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ) and SHELXL2018/3 (Sheldrick, 2015b ).

Structural data

CCDC reference: 2040604

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620014236/bt4100sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620014236/bt4100Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b).

catena-Poly[[chloridotris(1,3-thiazolidine-2-thione-κS)cadmium(II)]-µ-chlorido] top

Crystal data top

[CdCl₂(C₃H₅NS₂)₃]	D_x = 1.907 Mg m⁻³
M_r = 540.90	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 4396 reflections
a = 9.2014 (3) Å	θ = 3.1–32.5°
b = 19.3472 (6) Å	µ = 2.10 mm⁻¹
c = 10.5827 (3) Å	T = 295 K
V = 1883.94 (9) Å³	Block, colourless
Z = 4	0.76 × 0.50 × 0.14 mm
F(000) = 1072

Data collection top

Oxford Diffraction Xcalibur, Ruby, Gemini Ultra diffractometer	5594 independent reflections
Graphite monochromator	4781 reflections with I > 2σ(I)
Detector resolution: 10.3712 pixels mm^-1	R_int = 0.026
ω scans	θ_max = 30.5°, θ_min = 2.1°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2018)	h = −12→13
T_min = 0.242, T_max = 1.000	k = −27→27
12033 measured reflections	l = −14→15

Refinement top

Refinement on F²	Secondary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0275P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
5594 reflections	Δρ_max = 0.40 e Å⁻³
190 parameters	Δρ_min = −0.78 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 1872 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: −0.010 (19)

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. H atoms were refined using a riding model with N—H = 0.86 Å or C—H = 0.97 Å and U(H)=1.2U_eq(C,N).

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

	x	y	z	U_iso*/U_eq
Cd1	−0.51629 (3)	−0.49641 (2)	−0.38259 (5)	0.03293 (9)
Cl1	−0.46306 (13)	−0.51075 (6)	−0.63461 (14)	0.0402 (3)
Cl2	−0.66097 (13)	−0.38657 (6)	−0.42258 (12)	0.0459 (3)
S4	−0.17107 (15)	−0.28169 (7)	−0.32587 (13)	0.0514 (3)
S5	−0.26212 (12)	−0.42407 (7)	−0.39534 (14)	0.0470 (3)
S6	−0.4464 (3)	−0.76006 (9)	−0.31381 (18)	0.0922 (7)
S7	−0.36450 (15)	−0.61793 (7)	−0.38167 (16)	0.0594 (4)
S8	−1.01474 (16)	−0.59987 (9)	−0.54807 (18)	0.0592 (4)
S9	−0.75414 (11)	−0.57811 (6)	−0.38890 (14)	0.0401 (2)
N1	−0.3576 (4)	−0.3483 (2)	−0.1994 (3)	0.0415 (9)
H1	−0.420149	−0.379411	−0.179291	0.050*
N2	−0.5236 (5)	−0.6583 (2)	−0.1835 (4)	0.0483 (11)
H2	−0.532251	−0.616145	−0.158878	0.058*
N3	−0.8589 (5)	−0.4936 (2)	−0.5693 (4)	0.0515 (12)
H3	−0.786934	−0.465732	−0.559655	0.062*
C1	−0.3397 (6)	−0.2853 (3)	−0.1234 (5)	0.0504 (13)
H1A	−0.282523	−0.295177	−0.048554	0.061*
H1B	−0.433815	−0.267960	−0.097001	0.061*
C2	−0.2647 (6)	−0.2334 (3)	−0.2030 (5)	0.0574 (14)
H2A	−0.195748	−0.207054	−0.153008	0.069*
H2B	−0.334355	−0.201629	−0.239964	0.069*
C3	−0.2750 (5)	−0.3550 (2)	−0.2982 (4)	0.0352 (10)
C4	−0.5903 (8)	−0.7138 (3)	−0.1123 (6)	0.0678 (18)
H4A	−0.695161	−0.708523	−0.112475	0.081*
H4B	−0.556857	−0.712710	−0.025382	0.081*
C5	−0.5487 (8)	−0.7815 (3)	−0.1731 (6)	0.075 (2)
H5A	−0.634932	−0.807737	−0.194980	0.090*
H5B	−0.489916	−0.808860	−0.115812	0.090*
C6	−0.4508 (5)	−0.6730 (3)	−0.2845 (4)	0.0403 (11)
C7	−0.9747 (5)	−0.4783 (3)	−0.6584 (6)	0.0509 (14)
H7A	−0.934127	−0.462911	−0.738207	0.061*
H7B	−1.036634	−0.441940	−0.625452	0.061*
C8	−1.0607 (6)	−0.5430 (3)	−0.6772 (6)	0.0596 (16)
H8A	−1.035978	−0.564345	−0.757395	0.072*
H8B	−1.163928	−0.532937	−0.676816	0.072*
C9	−0.8670 (5)	−0.5509 (3)	−0.5041 (4)	0.0356 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04166 (16)	0.03310 (15)	0.02402 (13)	−0.00411 (12)	0.0009 (2)	−0.00111 (16)
Cl1	0.0570 (9)	0.0418 (7)	0.0218 (4)	−0.0097 (5)	0.0013 (7)	−0.0008 (6)
Cl2	0.0537 (6)	0.0311 (6)	0.0529 (7)	0.0001 (5)	0.0046 (5)	−0.0039 (5)
S4	0.0563 (7)	0.0483 (8)	0.0496 (6)	−0.0205 (7)	0.0097 (6)	−0.0042 (7)
S5	0.0468 (6)	0.0463 (7)	0.0478 (7)	−0.0101 (5)	0.0080 (6)	−0.0116 (7)
S6	0.175 (2)	0.0366 (8)	0.0653 (9)	0.0215 (12)	0.0102 (13)	−0.0082 (8)
S7	0.0625 (7)	0.0549 (8)	0.0609 (8)	0.0190 (7)	0.0232 (9)	0.0123 (9)
S8	0.0489 (8)	0.0566 (10)	0.0720 (9)	−0.0200 (7)	−0.0169 (7)	0.0102 (8)
S9	0.0440 (5)	0.0367 (5)	0.0396 (5)	−0.0068 (4)	−0.0045 (6)	0.0030 (7)
N1	0.049 (2)	0.037 (2)	0.038 (2)	−0.012 (2)	0.0054 (18)	−0.0005 (18)
N2	0.070 (3)	0.034 (2)	0.041 (2)	−0.005 (2)	0.006 (2)	−0.0051 (19)
N3	0.048 (3)	0.045 (3)	0.062 (3)	−0.014 (2)	−0.018 (2)	0.011 (2)
C1	0.068 (3)	0.039 (3)	0.044 (3)	−0.002 (3)	0.003 (3)	−0.003 (3)
C2	0.075 (4)	0.042 (3)	0.056 (3)	−0.011 (3)	0.007 (3)	−0.010 (3)
C3	0.037 (2)	0.036 (2)	0.033 (2)	−0.005 (2)	−0.0081 (18)	0.0030 (19)
C4	0.085 (5)	0.058 (4)	0.060 (4)	−0.021 (4)	0.005 (3)	0.006 (3)
C5	0.092 (5)	0.047 (4)	0.087 (5)	−0.011 (4)	−0.014 (4)	0.010 (4)
C6	0.044 (2)	0.036 (3)	0.041 (3)	0.007 (2)	−0.008 (2)	−0.001 (2)
C7	0.047 (3)	0.049 (3)	0.057 (4)	0.009 (3)	−0.013 (3)	0.005 (3)
C8	0.044 (3)	0.064 (4)	0.071 (4)	−0.003 (3)	−0.021 (3)	0.002 (3)
C9	0.034 (2)	0.037 (3)	0.036 (2)	0.001 (2)	0.0045 (17)	−0.0071 (19)

Geometric parameters (Å, º) top

Cd1—Cl2	2.5430 (12)	N2—H2	0.8600
Cd1—Cl1ⁱ	2.6348 (16)	N3—C9	1.307 (6)
Cd1—S9	2.7004 (11)	N3—C7	1.454 (7)
Cd1—Cl1	2.7258 (16)	N3—H3	0.8600
Cd1—S5	2.7289 (12)	C1—C2	1.482 (7)
Cd1—S7	2.7347 (13)	C1—H1A	0.9700
S4—C3	1.736 (5)	C1—H1B	0.9700
S4—C2	1.818 (5)	C2—H2A	0.9700
S5—C3	1.690 (5)	C2—H2B	0.9700
S6—C6	1.714 (5)	C4—C5	1.509 (9)
S6—C5	1.810 (7)	C4—H4A	0.9700
S7—C6	1.679 (5)	C4—H4B	0.9700
S8—C9	1.721 (5)	C5—H5A	0.9700
S8—C8	1.804 (6)	C5—H5B	0.9700
S9—C9	1.686 (5)	C7—C8	1.495 (9)
N1—C3	1.299 (5)	C7—H7A	0.9700
N1—C1	1.469 (6)	C7—H7B	0.9700
N1—H1	0.8600	C8—H8A	0.9700
N2—C6	1.293 (6)	C8—H8B	0.9700
N2—C4	1.448 (7)

Cl2—Cd1—Cl1ⁱ	94.82 (4)	C1—C2—H2A	110.5
Cl2—Cd1—S9	93.48 (4)	S4—C2—H2A	110.5
Cl1ⁱ—Cd1—S9	89.83 (4)	C1—C2—H2B	110.5
Cl2—Cd1—Cl1	90.94 (4)	S4—C2—H2B	110.5
Cl1ⁱ—Cd1—Cl1	173.143 (17)	H2A—C2—H2B	108.7
S9—Cd1—Cl1	93.55 (4)	N1—C3—S5	127.6 (4)
Cl2—Cd1—S5	90.68 (4)	N1—C3—S4	112.1 (4)
Cl1ⁱ—Cd1—S5	94.82 (4)	S5—C3—S4	120.3 (3)
S9—Cd1—S5	173.48 (5)	N2—C4—C5	108.3 (5)
Cl1—Cd1—S5	81.36 (4)	N2—C4—H4A	110.0
Cl2—Cd1—S7	170.53 (6)	C5—C4—H4A	110.0
Cl1ⁱ—Cd1—S7	94.51 (5)	N2—C4—H4B	110.0
S9—Cd1—S7	84.88 (4)	C5—C4—H4B	110.0
Cl1—Cd1—S7	79.87 (5)	H4A—C4—H4B	108.4
S5—Cd1—S7	90.19 (4)	C4—C5—S6	106.5 (4)
Cd1ⁱⁱ—Cl1—Cd1	162.98 (5)	C4—C5—H5A	110.4
C3—S4—C2	92.2 (2)	S6—C5—H5A	110.4
C3—S5—Cd1	108.37 (16)	C4—C5—H5B	110.4
C6—S6—C5	93.7 (3)	S6—C5—H5B	110.4
C6—S7—Cd1	107.80 (17)	H5A—C5—H5B	108.6
C9—S8—C8	93.1 (3)	N2—C6—S7	127.7 (4)
C9—S9—Cd1	109.53 (18)	N2—C6—S6	112.2 (4)
C3—N1—C1	117.3 (4)	S7—C6—S6	120.1 (3)
C3—N1—H1	121.4	N3—C7—C8	107.7 (5)
C1—N1—H1	121.4	N3—C7—H7A	110.2
C6—N2—C4	119.2 (5)	C8—C7—H7A	110.2
C6—N2—H2	120.4	N3—C7—H7B	110.2
C4—N2—H2	120.4	C8—C7—H7B	110.2
C9—N3—C7	118.2 (5)	H7A—C7—H7B	108.5
C9—N3—H3	120.9	C7—C8—S8	106.6 (4)
C7—N3—H3	120.9	C7—C8—H8A	110.4
N1—C1—C2	107.7 (4)	S8—C8—H8A	110.4
N1—C1—H1A	110.2	C7—C8—H8B	110.4
C2—C1—H1A	110.2	S8—C8—H8B	110.4
N1—C1—H1B	110.2	H8A—C8—H8B	108.6
C2—C1—H1B	110.2	N3—C9—S9	127.7 (4)
H1A—C1—H1B	108.5	N3—C9—S8	111.7 (4)
C1—C2—S4	106.1 (4)	S9—C9—S8	120.7 (3)

C3—N1—C1—C2	18.9 (6)	Cd1—S7—C6—N2	−32.2 (5)
N1—C1—C2—S4	−21.9 (5)	Cd1—S7—C6—S6	148.6 (2)
C3—S4—C2—C1	17.1 (4)	C5—S6—C6—N2	−1.8 (4)
C1—N1—C3—S5	174.6 (4)	C5—S6—C6—S7	177.5 (3)
C1—N1—C3—S4	−5.7 (5)	C9—N3—C7—C8	−14.1 (7)
Cd1—S5—C3—N1	25.0 (4)	N3—C7—C8—S8	16.8 (6)
Cd1—S5—C3—S4	−154.7 (2)	C9—S8—C8—C7	−13.4 (4)
C2—S4—C3—N1	−7.2 (4)	C7—N3—C9—S9	−175.6 (4)
C2—S4—C3—S5	172.5 (3)	C7—N3—C9—S8	3.8 (6)
C6—N2—C4—C5	3.6 (7)	Cd1—S9—C9—N3	−10.5 (5)
N2—C4—C5—S6	−4.4 (7)	Cd1—S9—C9—S8	170.1 (2)
C6—S6—C5—C4	3.6 (5)	C8—S8—C9—N3	6.1 (4)
C4—N2—C6—S7	−180.0 (4)	C8—S8—C9—S9	−174.4 (3)
C4—N2—C6—S6	−0.8 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.86	2.43	3.260 (4)	163
N2—H2···Cl1ⁱ	0.86	2.47	3.314 (4)	168
N3—H3···Cl2	0.86	2.41	3.165 (4)	147
C8—H8B···Cl1ⁱⁱⁱ	0.97	2.82	3.781 (6)	171

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

Acknowledgements

The authors thank the crystallographic service of Chemistry Department of Namur University (Belgium) for the data collection.

Funding information

The authors acknowledge the Cheikh Anta Diop University of Dakar (Senegal) for financial support.

References

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