catena-Poly[[[bis­(thio­urea-κS)cadmium]-di-μ-thio­cyanato-κ2N:S;κ2S:N] dihydrate]

Mietlarek-Kropidłowska, A.; Chojnacki, J.

doi:10.1107/S1600536812030267

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1051-m1052

https://doi.org/10.1107/S1600536812030267

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catena-Poly[[[bis(thiourea-κS)cadmium]-di-μ-thiocyanato-κ²N:S;κ²S:N] dihydrate]

Anna Mietlarek-Kropidłowska ^a ^* and Jaroslaw Chojnacki ^a

^aDepartment of Inorganic Chemistry, Chemical Faculty, Gdansk University of Technology, 11/12 G. Narutowicza Str., 80-233 Gdańsk, Poland
^*Correspondence e-mail: anna.mietlarek-kropidlowska@pg.gda.pl

(Received 18 June 2012; accepted 3 July 2012; online 10 July 2012)

The title compound, {[Cd(NCS)₂(CH₄N₂S)₂]·2H₂O}_n, forms a one-dimensional chain parallel to the a axis, caused by the presence of the bridging thiocyanate groups. Two solvent molecules per complex are present in the lattice. The Cd^II ion is situated on an inversion centre and is coordinated in a distorted octahedral fashion by two N and two S atoms from four thiocyanate ligands and by two S atoms from two thiourea molecules. Weak O—H⋯S, N—H⋯O and N—H⋯N interactions reinforce the structure.

Related literature

For a general introduction to thiocyanato complexes, see: Nardelli et al. (1957 ). For the syntheses and structures of a series of cadmium complexes with thiourea derivatives and thiocyanato ligands, see: Wang et al. (2002 ); Cavalca et al. (1960 ); Zhu et al. (2000 ); Yang et al. (2001 ); Ahmad et al. (2008 ); Williams et al. (1992 ). For information on the properties of complexes incorporating these ligands, see: Yuan et al. (1997 ); Krunks et al. (1997 ); Amutha et al. (2011 ); Machura et al. (2011 ). For the use of Cd^II complexes with mixed S-donor ligands as precursors to CdS, see: Kropidłowska et al. (2008 ).

Experimental

Crystal data

[Cd(NCS)₂(CH₄N₂S)₂]·2H₂O
M_r = 416.84
Triclinic, $[P \overline 1]$
a = 5.8533 (3) Å
b = 7.3527 (3) Å
c = 8.8630 (4) Å
α = 73.413 (4)°
β = 76.926 (4)°
γ = 88.856 (4)°
V = 355.69 (3) Å³
Z = 1
Mo Kα radiation
μ = 2.12 mm⁻¹
T = 293 K
0.53 × 0.42 × 0.23 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.558, T_max = 0.725
7642 measured reflections
2268 independent reflections
1985 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.062
S = 1.05
2268 reflections
85 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.26	3.049 (3)	153
N1—H1B⋯N3ⁱⁱ	0.86	2.3	3.147 (3)	167
N2—H2A⋯O1ⁱ	0.86	2.4	3.159 (3)	147
N2—H2B⋯O1ⁱⁱⁱ	0.86	2.19	3.050 (3)	175
O1—H1C⋯S2	0.80 (2)	2.54 (2)	3.340 (2)	177 (4)
O1—H1D⋯S1^iv	0.81 (2)	2.59 (2)	3.377 (2)	165 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x, -y+1, -z+1; (iv) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812030267/fj2575sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030267/fj2575Isup2.hkl

checkCIF report

Comment top

The interest in the coordination compounds possessing simultaneously thiourea and thiocyanato ligands dates back to the 1950s (e.g. Nardelli et al., 1957) when the nature of coordination compounds formed by divalent cations (M = Mn, Co, Ni, Cd, Pb) and organic molecules containing sulfur was extensively studied. Besides the polymeric catena-poly[bis(thiocyanato-κN)bis(µ-thiourea-κ²S:S)cadmium(II)] (Wang et al., 2002), also structures of four other complexes with thiourea derivatives of [Cd(SCN)₂(TU)₂]_n type, where TU = ethylenethiourea (Cavalca et al., 1960), N,N'-diphenylthiourea (Zhu et al., 2000), N-phenylthiourea (Yang et al., 2001; Ahmad et al., 2008) or 1,3-dimethyl-2(3H)-imidazolethione (Williams et al., 1992), can be found. The interest in these compounds is related either with their non-linear optical properties (Yuan et al., 1997) or with the possibility to use them as single-source precursors of semiconducting materials based on CdS (Krunks et al., 1997; Amutha et al., 2011). Moreover, the use of SCN ligands, with bridging abilities, may lead to intriguing architectures and topologies, often generating one-dimensional chains (Machura et al., 2011). It was the reason why, during our studies on the new molecular precursors (Kropidłowska et al., 2008), we have turned our attention to systems of this type now and we have obtained a new complex containing thiourea and thiocyanato ligands connected to cadmium center.

The cadmium atom in catena-Poly[[[bis(thiourea-κS)cadmium]-di-µ-thiocyanato-κ²N:S;κ²S:N] dihydrate] is located at the inversion center and is octahedrically coordinated by two S atoms and two N atoms from four thiocyanate groups as well as by two S atoms from thiourea molecules. The neighbouring Cd^II ions are bridged by two µ-SCN-κ²N:S ligands, thus forming eight-membered ring of [Cd-SCN]₂ type with the Cd···Cd distance of 5.853 Å, which is close to the values observed in other bridged systems (Machura et al., 2011). These units form one-dimensional chains of slightly distorted edge-shared Cd-centered octahedra along the [100] crystallographic direction. The Cd—S i Cd—N distances are typical for cadmium(II) thiocyanate complexes. The IR spectra clearly show the presence of the thiocyanato groups (with the maxima of ν_CN absorption at 2078 cm^-1).

In the structure of [[Cd{SC(NH₂)₂}₂(SCN)₂]^.2H₂O]_n, several weak interactions may be assumed, leading to the alternating arrangement of water and complex molecules. Each water molecule interacts with S or N atoms from the three neighboring polymeric chains. Thus, it can serve as a donor of a weak hydrogen bond to the sulfur atom from one of the thiourea moieties (O1(H1D)—S1^viii) in one chain, as well as to sulfur from one thiocyanato ligand (O1(H1C) —S2) in the other. The oxygen lone pairs act as acceptors towards NH₂ groups from thiourea moieties located within the third chain (N2(H2B) —O1^vii, N1(H1A) —O1^v, N2(H2A)—O1^v). Finally, one "interchain" interaction, N1—H1B···N3ⁱ, operates between NH₂ and SCN groups.

Related literature top

For a general introduction to thiocyanato complexes, see: Nardelli et al. (1957). For the syntheses and structures of a series of cadmium complexes with thiourea derivatives and thiocyanato ligands, see: Wang et al. (2002); Cavalca et al. (1960); Zhu et al. (2000); Yang et al. (2001); Ahmad et al. (2008); Williams et al. (1992). For information on the properties of complexes incorporating these ligands, see: Yuan et al. (1997); Krunks et al. (1997); Amutha et al. (2011); Machura et al. (2011). For the use of Cd^II complexes with mixed S-donor ligands as precursors to CdS, see: Kropidłowska et al. (2008).

Experimental top

The reaction was carried out between 0.50 g cadmium(II) thiocyanate, Cd(SCN)₂, and 1.34 g thiourea (molar ratio 1:8) which were dissolved in a small amount of water. The mixture was heated to 70°C and stirred using magnetic stirrer for 50 minutes and then left for crystallization at room temperature. After a few days two types of crystals appeared in the flask: needles (0.2 g) and blocks (0.1 g), which were mechanically separated under the microscope. The structure of needle-like crystals [Cd(SCN)₂{µ-SC(NH₂)₂}]_n (m.p. 189°C) has been already described (Wang et al., 2002), while the block-like crystals appeared to be a new compound, crystallizing as diaqua solvate [[Cd{SC(NH₂)₂}₂(SCN)₂].2H₂O]_n (m.p. 187°C). The product, when taken from the mother liquor and dried using the filter paper, changes - becomes opaque and finally takes the form of a powder (most probably because of the removal of the solvent molecules). IR spectra were recorded using Mattson Genesis II Gold spectrometer equipped with Momentum Microscope as detector.

Structure description top

For a general introduction to thiocyanato complexes, see: Nardelli et al. (1957). For the syntheses and structures of a series of cadmium complexes with thiourea derivatives and thiocyanato ligands, see: Wang et al. (2002); Cavalca et al. (1960); Zhu et al. (2000); Yang et al. (2001); Ahmad et al. (2008); Williams et al. (1992). For information on the properties of complexes incorporating these ligands, see: Yuan et al. (1997); Krunks et al. (1997); Amutha et al. (2011); Machura et al. (2011). For the use of Cd^II complexes with mixed S-donor ligands as precursors to CdS, see: Kropidłowska et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell refinement: CrysAlis PRO (Oxford Diffraction, 2008); data reduction: CrysAlis PRO (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure and atom-numbering scheme for [[Cd{SC(NH₂)₂}₂(SCN)₂]^.2H₂O]_n with displacement ellipsoids drawn at 50% probability level. H atoms are represented as arbitrary circles. Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z.
	Fig. 2. Weak interaction present in the crystal structure of [[Cd{SC(NH₂)₂}₂(SCN)₂].2H₂O]_n between the water and complex molecules (on the left). The arrangement of water and complex molecules in the crystal (on the right). Dashed lines denote the possible weak interactions.

catena-Poly[[[bis(thiourea-κS)cadmium]-di-µ-thiocyanato- κ²N:S;κ²S:N] dihydrate] top

Crystal data top

[Cd(NCS)₂(CH₄N₂S)₂]·2H₂O	Z = 1
M_r = 416.84	F(000) = 206
Triclinic, P1	D_x = 1.946 Mg m⁻³
Hall symbol: -P 1	Melting point: 460 K
a = 5.8533 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3527 (3) Å	Cell parameters from 4676 reflections
c = 8.8630 (4) Å	θ = 2.9–33.8°
α = 73.413 (4)°	µ = 2.12 mm⁻¹
β = 76.926 (4)°	T = 293 K
γ = 88.856 (4)°	Block, colourless
V = 355.69 (3) Å³	0.53 × 0.42 × 0.23 mm

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	1985 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω–scan	θ_max = 31°, θ_min = 2.9°
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2008), based on expressions derived by Clark & Reid (1995)]	h = −8→8
T_min = 0.558, T_max = 0.725	k = −10→10
7642 measured reflections	l = −12→12
2268 independent reflections

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0266P)²] where P = (F_o² + 2F_c²)/3
2268 reflections	(Δ/σ)_max < 0.001
85 parameters	Δρ_max = 0.47 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cd(NCS)₂(CH₄N₂S)₂]·2H₂O	γ = 88.856 (4)°
M_r = 416.84	V = 355.69 (3) Å³
Triclinic, P1	Z = 1
a = 5.8533 (3) Å	Mo Kα radiation
b = 7.3527 (3) Å	µ = 2.12 mm⁻¹
c = 8.8630 (4) Å	T = 293 K
α = 73.413 (4)°	0.53 × 0.42 × 0.23 mm
β = 76.926 (4)°

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	2268 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2008), based on expressions derived by Clark & Reid (1995)]	1985 reflections with I > 2σ(I)
T_min = 0.558, T_max = 0.725	R_int = 0.036
7642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	3 restraints
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.47 e Å⁻³
2268 reflections	Δρ_min = −0.51 e Å⁻³
85 parameters

Special details top

Experimental. CrysAlisPro, (Oxford Diffraction, 2008). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by (Clark & Reid, 1995).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cd1	0.5	0.5	0	0.03082 (8)
S1	0.24899 (10)	0.38566 (9)	0.30122 (7)	0.03890 (15)
S2	0.25651 (10)	0.82898 (8)	−0.03961 (7)	0.03377 (13)
N1	0.6502 (3)	0.3430 (3)	0.3988 (3)	0.0424 (5)
H1A	0.7326	0.2965	0.4686	0.051*
H1B	0.7155	0.4193	0.3061	0.051*
N2	0.3288 (4)	0.1803 (3)	0.5771 (3)	0.0481 (6)
H2A	0.4141	0.1352	0.6452	0.058*
H2B	0.1813	0.1488	0.6023	0.058*
N3	−0.1946 (3)	0.6528 (3)	0.0619 (3)	0.0391 (5)
C1	0.4240 (4)	0.2975 (3)	0.4340 (3)	0.0321 (5)
C2	−0.0091 (4)	0.7257 (3)	0.0194 (3)	0.0281 (4)
O1	0.1962 (4)	0.9249 (3)	0.3133 (2)	0.0524 (5)
H1C	0.216 (7)	0.902 (5)	0.229 (3)	0.079*
H1D	0.193 (7)	1.038 (3)	0.296 (4)	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02632 (12)	0.03241 (13)	0.03125 (13)	−0.00184 (9)	−0.00529 (9)	−0.00613 (10)
S1	0.0255 (3)	0.0545 (4)	0.0282 (3)	0.0010 (3)	−0.0048 (2)	0.0002 (3)
S2	0.0298 (3)	0.0265 (3)	0.0402 (3)	−0.0021 (2)	−0.0038 (2)	−0.0050 (2)
N1	0.0333 (10)	0.0557 (13)	0.0361 (11)	−0.0005 (10)	−0.0120 (9)	−0.0065 (10)
N2	0.0454 (12)	0.0560 (13)	0.0333 (11)	−0.0053 (11)	−0.0110 (10)	0.0044 (10)
N3	0.0330 (10)	0.0371 (11)	0.0500 (13)	−0.0009 (9)	−0.0106 (9)	−0.0158 (10)
C1	0.0357 (12)	0.0316 (11)	0.0295 (11)	0.0009 (9)	−0.0074 (9)	−0.0100 (9)
C2	0.0335 (11)	0.0264 (10)	0.0266 (10)	0.0050 (9)	−0.0101 (9)	−0.0088 (8)
O1	0.0662 (13)	0.0522 (11)	0.0412 (11)	−0.0028 (11)	−0.0197 (10)	−0.0113 (10)

Geometric parameters (Å, º) top

Cd1—N3ⁱ	2.3734 (19)	N1—H1A	0.86
Cd1—N3ⁱⁱ	2.3734 (19)	N1—H1B	0.86
Cd1—S1	2.6431 (6)	N2—C1	1.318 (3)
Cd1—S1ⁱⁱⁱ	2.6431 (6)	N2—H2A	0.86
Cd1—S2ⁱⁱⁱ	2.7585 (6)	N2—H2B	0.86
Cd1—S2	2.7585 (6)	N3—C2	1.154 (3)
S1—C1	1.714 (2)	N3—Cd1^iv	2.3734 (19)
S2—C2	1.649 (2)	O1—H1C	0.797 (17)
N1—C1	1.317 (3)	O1—H1D	0.805 (17)

N3ⁱ—Cd1—N3ⁱⁱ	180	C1—S1—Cd1	111.15 (8)
N3ⁱ—Cd1—S1	95.01 (6)	C2—S2—Cd1	96.75 (7)
N3ⁱⁱ—Cd1—S1	84.99 (6)	C1—N1—H1A	120
N3ⁱ—Cd1—S1ⁱⁱⁱ	84.99 (6)	C1—N1—H1B	120
N3ⁱⁱ—Cd1—S1ⁱⁱⁱ	95.01 (6)	H1A—N1—H1B	120
S1—Cd1—S1ⁱⁱⁱ	180	C1—N2—H2A	120
N3ⁱ—Cd1—S2ⁱⁱⁱ	89.81 (5)	C1—N2—H2B	120
N3ⁱⁱ—Cd1—S2ⁱⁱⁱ	90.19 (5)	H2A—N2—H2B	120
S1—Cd1—S2ⁱⁱⁱ	92.043 (19)	C2—N3—Cd1^iv	148.15 (19)
S1ⁱⁱⁱ—Cd1—S2ⁱⁱⁱ	87.957 (19)	N1—C1—N2	118.6 (2)
N3ⁱ—Cd1—S2	90.19 (5)	N1—C1—S1	122.51 (18)
N3ⁱⁱ—Cd1—S2	89.81 (5)	N2—C1—S1	118.87 (18)
S1—Cd1—S2	87.957 (19)	N3—C2—S2	179.5 (2)
S1ⁱⁱⁱ—Cd1—S2	92.043 (19)	H1C—O1—H1D	108 (3)
S2ⁱⁱⁱ—Cd1—S2	180.00 (3)

N3ⁱ—Cd1—S1—C1	−43.20 (10)	N3ⁱⁱ—Cd1—S2—C2	30.81 (10)
N3ⁱⁱ—Cd1—S1—C1	136.80 (10)	S1—Cd1—S2—C2	−54.18 (8)
S2ⁱⁱⁱ—Cd1—S1—C1	46.79 (9)	S1ⁱⁱⁱ—Cd1—S2—C2	125.82 (8)
S2—Cd1—S1—C1	−133.21 (9)	Cd1—S1—C1—N1	22.3 (2)
N3ⁱ—Cd1—S2—C2	−149.19 (10)	Cd1—S1—C1—N2	−157.98 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^v	0.86	2.26	3.049 (3)	153
N1—H1B···N3ⁱ	0.86	2.3	3.147 (3)	167
N2—H2A···O1^v	0.86	2.4	3.159 (3)	147
N2—H2B···O1^vi	0.86	2.19	3.050 (3)	175
O1—H1C···S2	0.80 (2)	2.54 (2)	3.340 (2)	177 (4)
O1—H1D···S1^vii	0.81 (2)	2.59 (2)	3.377 (2)	165 (3)

Symmetry codes: (i) x+1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Cd(NCS)₂(CH₄N₂S)₂]·2H₂O
M_r	416.84
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.8533 (3), 7.3527 (3), 8.8630 (4)
α, β, γ (°)	73.413 (4), 76.926 (4), 88.856 (4)
V (Å³)	355.69 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.12
Crystal size (mm)	0.53 × 0.42 × 0.23

Data collection
Diffractometer	Oxford Diffraction KM-4-CCD
Absorption correction	Analytical [CrysAlis PRO (Oxford Diffraction, 2008), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.558, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	7642, 2268, 1985
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.062, 1.05
No. of reflections	2268
No. of parameters	85
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.51

Computer programs: CrysAlis PRO (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.26	3.049 (3)	153
N1—H1B···N3ⁱⁱ	0.86	2.3	3.147 (3)	167
N2—H2A···O1ⁱ	0.86	2.4	3.159 (3)	147
N2—H2B···O1ⁱⁱⁱ	0.86	2.19	3.050 (3)	175
O1—H1C···S2	0.797 (17)	2.544 (18)	3.340 (2)	177 (4)
O1—H1D···S1^iv	0.805 (17)	2.593 (19)	3.377 (2)	165 (3)

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

Acknowledgements

The research was supported by grants from the Polish Ministry of Education and Science (grant Nos. N N204 543339 and N N204 150237).

References

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