Bis{3-amino-1-carbamo­thioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)meth­yl]sulfan­yl}eth­yl)amino]-1H-1,2,4-triazol-4-ium} hexa­chloridobismuthate(III) nitrate dihydrate

Hossain, G.M.G.

doi:10.1107/S1600536813016449

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m402-m403

https://doi.org/10.1107/S1600536813016449

Open

access

Bis{3-amino-1-carbamothioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)methyl]sulfanyl}ethyl)amino]-1H-1,2,4-triazol-4-ium} hexachloridobismuthate(III) nitrate dihydrate

G. M. Golzar Hossain ^a ^*

^aDepartment of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh
^*Correspondence e-mail: acsbd@yahoo.com

(Received 8 May 2013; accepted 13 June 2013; online 19 June 2013)

The asymmetric unit of the title hydrated salt, (C₁₀H₁₈N₈S₂)₂[BiCl₆]NO₃·2H₂O, contains two independent 3-amino-1-carbamothioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)methyl]sulfanyl}ethyl)amino]-1H-1,2,4-triazol-4-ium cations, one hexachloridobismuthate anion, one nitrate anion and two solvent water molecules. The dihedral angles between the imidazole and triazole rings in the cations are 44.7 (3) and 89.4 (3)°. The Bi^III ion is coordinated by six chloride ligands in a slightly distorted octahedral geometry. In each cation, an intramolecular N—H⋯S hydrogen bond is observed. In the crystal, N—H⋯Cl, N—H⋯S, N—H⋯O, O—H⋯Cl, O—H⋯S and O—H⋯O hydrogen bonds connect the components into a three-dimensional network. In addtion, π–π stacking interactions between inversion-related triazole rings are observed, with a centroid–centroid distance of 3.322 (3) Å

Related literature

For background to hexachloridobismuthate(III) complexes with organic cations, see: Lazarini (1987 ); Jarraya et al. (1993 ); Battaglia & Corradi (1986 ); Bednarska-Bolek et al. (2000 ).

Experimental

Crystal data

(C₁₀H₁₈N₈S₂)₂[BiCl₆]NO₃·2H₂O
M_r = 1148.61
Triclinic, $[P \overline 1]$
a = 8.8750 (1) Å
b = 14.2860 (2) Å
c = 16.6500 (2) Å
α = 94.376 (1)°
β = 100.717 (1)°
γ = 92.167 (1)°
V = 2065.24 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.91 mm⁻¹
T = 150 K
0.20 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.440, T_max = 0.440
34173 measured reflections
9432 independent reflections
8522 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.05
9432 reflections
541 parameters
24 restraints
Δρ_max = 2.72 e Å⁻³
Δρ_min = −2.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl6ⁱ	0.89 (4)	2.54 (3)	3.379 (6)	158 (7)
N2—H2N⋯Cl6ⁱⁱ	0.88 (5)	2.58 (5)	3.406 (5)	156 (6)
N3—H3N⋯S2	0.89 (5)	2.23 (6)	3.019 (6)	148 (7)
N4—H4N⋯O2	0.91 (7)	1.74 (7)	2.608 (7)	160 (7)
N7—H7A⋯S2ⁱⁱⁱ	0.91 (6)	2.46 (7)	3.296 (6)	155 (6)
N7—H7B⋯O1^iv	0.90 (4)	1.97 (5)	2.842 (8)	162 (6)
N8—H8A⋯Cl5^iv	0.89 (5)	2.83 (6)	3.550 (5)	140 (5)
O1—H11⋯Cl5	0.84 (6)	2.39 (6)	3.138 (5)	149 (6)
N11—H11N⋯O1^v	0.89 (2)	1.83 (3)	2.703 (6)	170 (9)
O1—H12⋯Cl4^vi	0.85 (6)	2.27 (5)	3.116 (5)	172 (7)
N12—H12N⋯O3ⁱⁱ	0.88 (6)	1.99 (7)	2.835 (6)	162 (6)
N12—H12N⋯O4ⁱⁱ	0.88 (6)	2.58 (6)	3.307 (8)	142 (5)
N13—H13N⋯S4	0.88 (3)	2.27 (6)	3.025 (4)	144 (7)
N14—H14N⋯O3^vii	0.87 (6)	1.91 (6)	2.772 (5)	175 (5)
N14—H14N⋯O5^vii	0.87 (6)	2.43 (8)	2.960 (7)	120 (7)
N17—H17A⋯S4ⁱⁱⁱ	0.87 (6)	2.60 (6)	3.423 (5)	159 (6)
N17—H17B⋯Cl3ⁱⁱⁱ	0.87 (3)	2.52 (5)	3.337 (5)	158 (6)
N18—H18A⋯Cl2	0.87 (5)	2.56 (7)	3.304 (5)	144 (5)
N18—H18B⋯Cl3	0.88 (4)	2.59 (7)	3.332 (5)	143 (7)
O2—H21⋯Cl4	0.86 (4)	2.62 (6)	3.326 (5)	139 (6)
O2—H21⋯S2ⁱⁱⁱ	0.86 (4)	2.59 (8)	3.168 (5)	126 (7)
O2—H22⋯O4	0.86 (3)	2.52 (5)	3.227 (7)	139 (7)
O2—H22⋯O5	0.86 (3)	1.88 (5)	2.717 (6)	162 (9)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) -x+1, -y+1, -z; (v) -x+1, -y, -z+1; (vi) x+1, y, z; (vii) -x, -y+1, -z+1.

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813016449/lh5614sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016449/lh5614Isup2.hkl

checkCIF report

Comment top

The hexachlorobismuthate(III) anion, [BiCl₆]^3–, forms complexes with organic cations in the presence of excess chloride ions (Lazarini, 1987; Jarraya et al., 1993; Battaglia & Corradi, 1986). Cimetidine, N-cyano-N'-methyl-N"-{2-[5-methy-1H-imidazole-4-yl]methylthio-ethyl}-guanidine, consists of three main functional units: a 4,5-disubstituted imidazolic ring, a cysteine and an N-cyanoazamethine or guanidine derivative. The N-cyanoazamethine part of cimetidine reacts with thiosemicarbazide when the reaction is carried out with Bi(NO₃)₃ in presence of hydrochloric acid. The crystal structure of the title compound is presented herein.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit compound, contains of two dicationic ligands, one [BiCl₆]^3– anion, one NO₃^- anion and two solvent water molecules. The Bi^III ion is coordinated by six chloride ions forming a slightly distorted octahedral configuration with Bi—Cl bond lengths ranging from 2.6312 (13) to 2.7984 (12)Å. The Bi–Cl bond lengths are comparable with the reported values in a related halogenobismuthate (Bednarska-Bolek et al., 2000). The bond angles within the [BiCl₆]^3– anion of the compound do not suggest any steric interactions are present (Bednarska-Bolek et al., 2000; Jarraya et al., 1993). The dihedral angles between the imidazole and triazole rings in the cations are 44.7 (3) [C1-C3/N1/N2 and N4-N6/C7/C8] and 89.4 (3)° [C11-C13/N11/N12 and C17/C18/N14-N16]. In each cation, an intramolecular N—H···S hydrogen bond is observed. In the crystal, N—H···Cl, N—H···S, N—H···O, O—H···Cl, O—H···S and O—H···O hydrogen bonds connect the components of the structure into a three-dimensional network (Fig. 2). In addtion, π–π stacking interactions with Cg···Cg(1-x, 1-y, -z) = 3.322 (3)Å are observed [Cg is the centroid of the N4/C7/N6/N5/C8 ring].

Related literature top

For background to hexachloridobismuthate(III) complexes with organic cations, see: Lazarini (1987); Jarraya et al. (1993); Battaglia & Corradi (1986); Bednarska-Bolek et al. (2000).

Experimental top

Bismuth nitrate (0.4851 g, 1.0 mmol) was dissolved in 4M hydrochloric acid (30 ml). An ethanolic solution of cimetidine (0.5047 g, 2.0 mmol) and thiosemicarbazide (0.1823 g, 2.0 mmol) were added slowly to the solution with constant stirring. The solution was stirred further for 3 h and then it was filtered and left with slow evaporation of the solvent. Colorless crystals suitable for X-ray analysis separated out from the solution after a week.

Structure description top

For background to hexachloridobismuthate(III) complexes with organic cations, see: Lazarini (1987); Jarraya et al. (1993); Battaglia & Corradi (1986); Bednarska-Bolek et al. (2000).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% dispalcement ellipsoids (arbitrary spheres for the H atoms). Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. Packing diagram of the complex. Hydrogen bonds are shown by dashed lines.

Bis{3-amino-1-carbamothioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)methyl]sulfanyl}ethyl)amino]-1H-1,2,4-triazol-4-ium} hexachloridobismuthate(III) nitrate dihydrate top

Crystal data top

(C₁₀H₁₈N₈S₂)₂[BiCl₆]NO₃·2H₂O	Z = 2
M_r = 1148.61	F(000) = 1136
Triclinic, P1	D_x = 1.850 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8750 (1) Å	Cell parameters from 9432 reflections
b = 14.2860 (2) Å	θ = 2.7–27.5°
c = 16.6500 (2) Å	µ = 4.91 mm⁻¹
α = 94.376 (1)°	T = 150 K
β = 100.717 (1)°	Block, colorless
γ = 92.167 (1)°	0.20 × 0.20 × 0.20 mm
V = 2065.24 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	9432 independent reflections
Radiation source: fine-focus sealed tube	8522 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −11→11
T_min = 0.440, T_max = 0.440	k = −18→18
34173 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0527P)² + 5.0184P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
9432 reflections	Δρ_max = 2.72 e Å⁻³
541 parameters	Δρ_min = −2.16 e Å⁻³
24 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Crystal data top

(C₁₀H₁₈N₈S₂)₂[BiCl₆]NO₃·2H₂O	γ = 92.167 (1)°
M_r = 1148.61	V = 2065.24 (4) Å³
Triclinic, P1	Z = 2
a = 8.8750 (1) Å	Mo Kα radiation
b = 14.2860 (2) Å	µ = 4.91 mm⁻¹
c = 16.6500 (2) Å	T = 150 K
α = 94.376 (1)°	0.20 × 0.20 × 0.20 mm
β = 100.717 (1)°

Data collection top

Nonius KappaCCD diffractometer	9432 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	8522 reflections with I > 2σ(I)
T_min = 0.440, T_max = 0.440	R_int = 0.061
34173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	24 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 2.72 e Å⁻³
9432 reflections	Δρ_min = −2.16 e Å⁻³
541 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.94732 (15)	0.67239 (9)	0.34141 (8)	0.0342 (3)
S2	0.98090 (19)	0.58775 (13)	0.08391 (10)	0.0496 (4)
N1	1.3722 (6)	0.6664 (4)	0.5461 (3)	0.0407 (11)
N2	1.1338 (5)	0.6703 (3)	0.5467 (3)	0.0362 (10)
N3	0.7375 (6)	0.5559 (4)	0.1852 (3)	0.0397 (11)
N4	0.4915 (6)	0.5895 (4)	0.1124 (3)	0.0395 (11)
N5	0.5433 (6)	0.6162 (4)	−0.0108 (3)	0.0416 (11)
N6	0.6766 (5)	0.5934 (3)	0.0442 (3)	0.0381 (10)
N7	0.2906 (7)	0.6302 (5)	0.0070 (4)	0.0582 (15)
N8	0.8045 (6)	0.6170 (4)	−0.0581 (3)	0.0488 (13)
C1	1.2997 (6)	0.6179 (4)	0.4738 (3)	0.0327 (11)
C2	1.2710 (8)	0.6972 (5)	0.5884 (4)	0.0447 (14)
H2	1.2929	0.7327	0.6402	0.054*
C3	1.1469 (6)	0.6205 (4)	0.4735 (3)	0.0307 (10)
C4	1.0117 (6)	0.5830 (4)	0.4118 (3)	0.0321 (11)
H4A	0.9275	0.5644	0.4398	0.038*
H4B	1.0389	0.5265	0.3804	0.038*
C5	0.7434 (6)	0.6431 (4)	0.3189 (4)	0.0369 (12)
H5A	0.7072	0.6377	0.3712	0.044*
H5B	0.6905	0.6953	0.2917	0.044*
C6	0.6977 (6)	0.5536 (4)	0.2652 (3)	0.0397 (13)
H6A	0.7485	0.5010	0.2927	0.048*
H6B	0.5853	0.5412	0.2585	0.048*
C7	0.6429 (6)	0.5785 (4)	0.1187 (3)	0.0354 (12)
C8	0.4379 (7)	0.6133 (4)	0.0328 (4)	0.0430 (13)
C9	1.3858 (7)	0.5787 (5)	0.4114 (4)	0.0427 (13)
H9A	1.4099	0.6285	0.3777	0.064*
H9B	1.3230	0.5280	0.3764	0.064*
H9C	1.4814	0.5539	0.4391	0.064*
C10	0.8161 (7)	0.6009 (4)	0.0190 (4)	0.0424 (13)
S3	0.24517 (18)	0.19615 (10)	0.86591 (9)	0.0416 (3)
S4	0.32138 (14)	0.09271 (11)	0.62576 (8)	0.0352 (3)
N11	0.3547 (5)	−0.1218 (3)	0.8769 (3)	0.0345 (10)
N12	0.4499 (5)	0.0078 (4)	0.8468 (3)	0.0376 (10)
N13	0.0633 (4)	0.0708 (3)	0.7198 (2)	0.0281 (9)
N14	−0.1794 (5)	0.0852 (3)	0.6379 (2)	0.0270 (9)
N15	−0.1160 (4)	0.1080 (3)	0.5168 (2)	0.0277 (9)
N16	0.0146 (4)	0.0950 (3)	0.5773 (2)	0.0239 (8)
N17	−0.3771 (5)	0.1081 (5)	0.5248 (3)	0.0467 (13)
N18	0.1552 (5)	0.1189 (3)	0.4797 (3)	0.0315 (9)
C11	0.3124 (6)	−0.0522 (4)	0.9296 (3)	0.0297 (10)
C12	0.4370 (6)	−0.0842 (4)	0.8284 (3)	0.0383 (12)
H12A	0.4798	−0.1175	0.7871	0.046*
C13	0.3730 (6)	0.0303 (4)	0.9106 (3)	0.0313 (11)
C14	0.3565 (7)	0.1286 (4)	0.9417 (3)	0.0368 (12)
H14A	0.4600	0.1600	0.9599	0.044*
H14B	0.3064	0.1282	0.9900	0.044*
C15	0.0509 (6)	0.1450 (5)	0.8563 (4)	0.0421 (13)
H15A	0.0348	0.1296	0.9112	0.051*
H15B	−0.0230	0.1925	0.8373	0.051*
C16	0.0160 (6)	0.0566 (4)	0.7974 (3)	0.0314 (11)
H16A	0.0706	0.0038	0.8226	0.038*
H16B	−0.0956	0.0398	0.7872	0.038*
C17	−0.0274 (5)	0.0827 (3)	0.6512 (3)	0.0222 (9)
C18	−0.2286 (6)	0.1011 (4)	0.5559 (3)	0.0304 (11)
C19	0.2162 (6)	−0.0740 (5)	0.9913 (3)	0.0402 (13)
H19A	0.2623	−0.1235	1.0239	0.060*
H19B	0.1125	−0.0955	0.9628	0.060*
H19C	0.2108	−0.0173	1.0274	0.060*
C20	0.1598 (5)	0.1032 (3)	0.5573 (3)	0.0253 (9)
Bi1	0.200467 (18)	0.255209 (11)	0.278175 (10)	0.02225 (8)
Cl1	0.16339 (17)	0.16319 (11)	0.13224 (8)	0.0416 (3)
Cl2	−0.05587 (14)	0.17031 (9)	0.30498 (8)	0.0328 (3)
Cl3	0.38963 (14)	0.12542 (9)	0.34520 (7)	0.0301 (3)
Cl4	0.03748 (16)	0.40620 (10)	0.23050 (9)	0.0392 (3)
Cl5	0.44926 (16)	0.35260 (11)	0.24484 (9)	0.0454 (3)
Cl6	0.24345 (15)	0.34255 (9)	0.43761 (8)	0.0341 (3)
O3	0.3595 (4)	0.8967 (3)	0.2430 (2)	0.0373 (9)
O4	0.4022 (7)	0.7788 (4)	0.1648 (4)	0.0764 (17)
O5	0.2846 (7)	0.7574 (3)	0.2640 (4)	0.0723 (16)
N19	0.3509 (5)	0.8126 (3)	0.2230 (3)	0.0330 (9)
O1	0.7188 (6)	0.3082 (3)	0.1521 (3)	0.0549 (12)
O2	0.2936 (6)	0.5740 (3)	0.2091 (3)	0.0565 (12)
H1N	1.473 (3)	0.679 (5)	0.560 (5)	0.068*
H2N	1.049 (5)	0.673 (5)	0.567 (4)	0.068*
H3N	0.831 (4)	0.569 (6)	0.176 (5)	0.068*
H4N	0.436 (8)	0.573 (6)	0.150 (4)	0.068*
H7A	0.226 (7)	0.627 (6)	0.043 (4)	0.068*
H7B	0.270 (9)	0.641 (6)	−0.0466 (18)	0.068*
H8A	0.711 (4)	0.629 (6)	−0.084 (4)	0.068*
H8B	0.898 (4)	0.623 (6)	−0.070 (5)	0.068*
H11N	0.341 (9)	−0.1839 (15)	0.871 (5)	0.068*
H12N	0.498 (8)	0.048 (4)	0.822 (4)	0.068*
H13N	0.160 (3)	0.073 (6)	0.715 (5)	0.068*
H14N	−0.232 (7)	0.089 (6)	0.677 (3)	0.068*
H17A	−0.446 (7)	0.088 (5)	0.551 (4)	0.068*
H17B	−0.414 (8)	0.110 (6)	0.4731 (16)	0.068*
H18A	0.068 (5)	0.122 (6)	0.446 (4)	0.068*
H18B	0.246 (4)	0.127 (6)	0.467 (5)	0.068*
H11	0.646 (5)	0.338 (5)	0.165 (5)	0.085*
H12	0.803 (4)	0.334 (5)	0.179 (5)	0.085*
H21	0.199 (4)	0.554 (5)	0.203 (6)	0.085*
H22	0.292 (8)	0.6343 (15)	0.216 (6)	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0337 (7)	0.0303 (7)	0.0368 (7)	−0.0021 (5)	0.0027 (5)	0.0041 (5)
S2	0.0429 (8)	0.0642 (11)	0.0432 (8)	0.0111 (7)	0.0087 (7)	0.0089 (8)
N1	0.034 (2)	0.047 (3)	0.038 (3)	0.005 (2)	0.001 (2)	0.002 (2)
N2	0.039 (3)	0.039 (3)	0.033 (2)	0.014 (2)	0.012 (2)	0.000 (2)
N3	0.038 (3)	0.039 (3)	0.039 (3)	0.000 (2)	−0.001 (2)	0.004 (2)
N4	0.039 (3)	0.039 (3)	0.039 (3)	0.004 (2)	0.006 (2)	0.002 (2)
N5	0.037 (3)	0.042 (3)	0.044 (3)	0.006 (2)	0.002 (2)	0.003 (2)
N6	0.036 (2)	0.044 (3)	0.033 (2)	0.002 (2)	0.0037 (19)	0.003 (2)
N7	0.041 (3)	0.082 (4)	0.051 (3)	0.014 (3)	0.003 (3)	0.013 (3)
N8	0.044 (3)	0.061 (4)	0.044 (3)	0.009 (3)	0.009 (2)	0.016 (3)
C1	0.032 (3)	0.034 (3)	0.032 (3)	0.005 (2)	0.005 (2)	0.005 (2)
C2	0.055 (4)	0.050 (4)	0.027 (3)	0.014 (3)	0.003 (3)	−0.004 (2)
C3	0.034 (3)	0.028 (3)	0.031 (3)	0.007 (2)	0.007 (2)	0.004 (2)
C4	0.031 (3)	0.026 (3)	0.039 (3)	0.002 (2)	0.006 (2)	0.001 (2)
C5	0.030 (3)	0.041 (3)	0.042 (3)	0.007 (2)	0.009 (2)	0.004 (2)
C6	0.033 (3)	0.047 (3)	0.037 (3)	−0.006 (2)	0.000 (2)	0.011 (3)
C7	0.039 (3)	0.026 (3)	0.040 (3)	0.001 (2)	0.004 (2)	0.001 (2)
C8	0.043 (3)	0.046 (3)	0.039 (3)	0.004 (3)	0.004 (3)	0.003 (3)
C9	0.043 (3)	0.052 (4)	0.038 (3)	0.009 (3)	0.017 (3)	0.004 (3)
C10	0.053 (4)	0.035 (3)	0.039 (3)	0.004 (3)	0.008 (3)	0.003 (2)
S3	0.0484 (8)	0.0323 (7)	0.0426 (8)	0.0018 (6)	0.0043 (6)	0.0042 (6)
S4	0.0211 (6)	0.0537 (8)	0.0322 (6)	0.0046 (5)	0.0071 (5)	0.0069 (6)
N11	0.036 (2)	0.035 (2)	0.034 (2)	0.0098 (19)	0.0080 (19)	0.002 (2)
N12	0.034 (2)	0.047 (3)	0.035 (2)	0.001 (2)	0.0139 (19)	0.008 (2)
N13	0.0219 (19)	0.038 (2)	0.025 (2)	0.0053 (17)	0.0041 (16)	0.0081 (18)
N14	0.022 (2)	0.036 (2)	0.024 (2)	0.0007 (16)	0.0057 (16)	0.0053 (17)
N15	0.0228 (19)	0.038 (2)	0.025 (2)	0.0043 (17)	0.0064 (16)	0.0087 (18)
N16	0.0197 (18)	0.028 (2)	0.0250 (19)	−0.0008 (15)	0.0055 (15)	0.0045 (16)
N17	0.025 (2)	0.084 (4)	0.035 (3)	0.009 (2)	0.009 (2)	0.017 (3)
N18	0.027 (2)	0.039 (3)	0.032 (2)	0.0053 (19)	0.0112 (18)	0.0116 (19)
C11	0.025 (2)	0.040 (3)	0.023 (2)	0.001 (2)	0.0019 (19)	0.005 (2)
C12	0.039 (3)	0.048 (3)	0.029 (3)	0.011 (2)	0.009 (2)	−0.003 (2)
C13	0.028 (2)	0.039 (3)	0.027 (2)	0.004 (2)	0.006 (2)	0.004 (2)
C14	0.044 (3)	0.037 (3)	0.028 (3)	0.000 (2)	0.004 (2)	−0.001 (2)
C15	0.034 (3)	0.052 (4)	0.042 (3)	0.009 (3)	0.011 (2)	0.002 (3)
C16	0.028 (2)	0.043 (3)	0.024 (2)	0.003 (2)	0.0054 (19)	0.010 (2)
C17	0.025 (2)	0.020 (2)	0.024 (2)	0.0003 (17)	0.0088 (18)	0.0030 (17)
C18	0.025 (2)	0.042 (3)	0.026 (2)	0.002 (2)	0.0066 (19)	0.006 (2)
C19	0.036 (3)	0.054 (4)	0.035 (3)	0.006 (3)	0.014 (2)	0.009 (3)
C20	0.025 (2)	0.024 (2)	0.030 (2)	−0.0001 (18)	0.0120 (19)	0.0038 (19)
Bi1	0.02270 (10)	0.02247 (11)	0.02244 (11)	0.00348 (6)	0.00593 (6)	0.00206 (6)
Cl1	0.0499 (8)	0.0454 (8)	0.0284 (6)	−0.0034 (6)	0.0096 (6)	−0.0064 (6)
Cl2	0.0273 (6)	0.0376 (7)	0.0335 (6)	−0.0020 (5)	0.0070 (5)	0.0013 (5)
Cl3	0.0298 (6)	0.0349 (6)	0.0288 (6)	0.0121 (5)	0.0096 (5)	0.0087 (5)
Cl4	0.0394 (7)	0.0322 (7)	0.0489 (8)	0.0130 (5)	0.0111 (6)	0.0099 (6)
Cl5	0.0355 (7)	0.0524 (9)	0.0486 (8)	−0.0115 (6)	0.0085 (6)	0.0105 (7)
Cl6	0.0362 (6)	0.0353 (7)	0.0301 (6)	−0.0006 (5)	0.0084 (5)	−0.0050 (5)
O3	0.034 (2)	0.036 (2)	0.045 (2)	0.0017 (16)	0.0146 (17)	0.0069 (17)
O4	0.104 (4)	0.052 (3)	0.089 (4)	−0.002 (3)	0.065 (4)	−0.011 (3)
O5	0.109 (4)	0.037 (3)	0.084 (4)	−0.009 (3)	0.056 (3)	0.005 (3)
N19	0.032 (2)	0.037 (3)	0.033 (2)	0.0059 (18)	0.0158 (18)	−0.0033 (19)
O1	0.049 (3)	0.048 (3)	0.063 (3)	0.009 (2)	−0.003 (2)	0.002 (2)
O2	0.065 (3)	0.048 (3)	0.060 (3)	−0.003 (2)	0.022 (3)	0.004 (2)

Geometric parameters (Å, º) top

S1—C5	1.805 (5)	N12—C13	1.388 (7)
S1—C4	1.834 (5)	N12—H12N	0.88 (2)
S2—C10	1.676 (6)	N13—C17	1.296 (6)
N1—C2	1.310 (8)	N13—C16	1.456 (6)
N1—C1	1.376 (7)	N13—H13N	0.87 (2)
N1—H1N	0.88 (2)	N14—C17	1.328 (6)
N2—C2	1.312 (8)	N14—C18	1.391 (6)
N2—C3	1.389 (7)	N14—H14N	0.87 (2)
N2—H2N	0.88 (2)	N15—C18	1.296 (6)
N3—C7	1.327 (7)	N15—N16	1.415 (5)
N3—C6	1.443 (7)	N16—C17	1.372 (6)
N3—H3N	0.89 (2)	N16—C20	1.393 (6)
N4—C7	1.345 (7)	N17—C18	1.333 (7)
N4—C8	1.393 (8)	N17—H17A	0.87 (2)
N4—H4N	0.90 (2)	N17—H17B	0.86 (2)
N5—C8	1.288 (8)	N18—C20	1.320 (6)
N5—N6	1.421 (7)	N18—H18A	0.87 (2)
N6—C7	1.359 (7)	N18—H18B	0.88 (2)
N6—C10	1.382 (8)	C11—C13	1.360 (7)
N7—C8	1.336 (8)	C11—C19	1.494 (7)
N7—H7A	0.90 (2)	C12—H12A	0.9500
N7—H7B	0.90 (2)	C13—C14	1.482 (8)
N8—C10	1.308 (8)	C14—H14A	0.9900
N8—H8A	0.89 (2)	C14—H14B	0.9900
N8—H8B	0.89 (2)	C15—C16	1.523 (8)
C1—C3	1.356 (7)	C15—H15A	0.9900
C1—C9	1.488 (8)	C15—H15B	0.9900
C2—H2	0.9500	C16—H16A	0.9900
C3—C4	1.480 (7)	C16—H16B	0.9900
C4—H4A	0.9900	C19—H19A	0.9800
C4—H4B	0.9900	C19—H19B	0.9800
C5—C6	1.499 (8)	C19—H19C	0.9800
C5—H5A	0.9900	Bi1—Cl1	2.6312 (13)
C5—H5B	0.9900	Bi1—Cl2	2.6641 (12)
C6—H6A	0.9900	Bi1—Cl3	2.7122 (11)
C6—H6B	0.9900	Bi1—Cl4	2.7286 (13)
C9—H9A	0.9800	Bi1—Cl5	2.7314 (13)
C9—H9B	0.9800	Bi1—Cl6	2.7984 (12)
C9—H9C	0.9800	O3—N19	1.218 (6)
S3—C14	1.815 (6)	O4—N19	1.220 (6)
S3—C15	1.822 (6)	O5—N19	1.276 (6)
S4—C20	1.677 (5)	O1—H11	0.85 (2)
N11—C12	1.315 (7)	O1—H12	0.85 (2)
N11—C11	1.385 (7)	O2—H21	0.86 (2)
N11—H11N	0.89 (2)	O2—H22	0.86 (2)
N12—C12	1.323 (8)

C5—S1—C4	100.1 (3)	C17—N14—C18	107.7 (4)
C2—N1—C1	110.3 (5)	C17—N14—H14N	123 (5)
C2—N1—H1N	125 (5)	C18—N14—H14N	128 (5)
C1—N1—H1N	125 (5)	C18—N15—N16	103.3 (4)
C2—N2—C3	109.7 (5)	C17—N16—C20	130.2 (4)
C2—N2—H2N	124 (5)	C17—N16—N15	110.6 (4)
C3—N2—H2N	125 (5)	C20—N16—N15	119.0 (4)
C7—N3—C6	124.6 (5)	C18—N17—H17A	120 (5)
C7—N3—H3N	105 (5)	C18—N17—H17B	124 (5)
C6—N3—H3N	125 (5)	H17A—N17—H17B	111 (7)
C7—N4—C8	106.4 (5)	C20—N18—H18A	122 (5)
C7—N4—H4N	124 (5)	C20—N18—H18B	114 (5)
C8—N4—H4N	128 (5)	H18A—N18—H18B	124 (7)
C8—N5—N6	103.1 (5)	C13—C11—N11	106.1 (4)
C7—N6—C10	130.8 (5)	C13—C11—C19	132.0 (5)
C7—N6—N5	110.7 (5)	N11—C11—C19	121.9 (5)
C10—N6—N5	117.9 (5)	N11—C12—N12	108.3 (5)
C8—N7—H7A	118 (5)	N11—C12—H12A	125.8
C8—N7—H7B	112 (5)	N12—C12—H12A	125.8
H7A—N7—H7B	130 (7)	C11—C13—N12	106.5 (5)
C10—N8—H8A	116 (5)	C11—C13—C14	130.8 (5)
C10—N8—H8B	110 (5)	N12—C13—C14	122.5 (5)
H8A—N8—H8B	134 (7)	C13—C14—S3	113.3 (4)
C3—C1—N1	106.1 (5)	C13—C14—H14A	108.9
C3—C1—C9	131.6 (5)	S3—C14—H14A	108.9
N1—C1—C9	122.2 (5)	C13—C14—H14B	108.9
N1—C2—N2	107.9 (5)	S3—C14—H14B	108.9
N1—C2—H2	126.0	H14A—C14—H14B	107.7
N2—C2—H2	126.0	C16—C15—S3	114.0 (4)
C1—C3—N2	106.0 (5)	C16—C15—H15A	108.8
C1—C3—C4	131.4 (5)	S3—C15—H15A	108.8
N2—C3—C4	122.6 (5)	C16—C15—H15B	108.8
C3—C4—S1	110.1 (4)	S3—C15—H15B	108.8
C3—C4—H4A	109.6	H15A—C15—H15B	107.6
S1—C4—H4A	109.6	N13—C16—C15	111.0 (4)
C3—C4—H4B	109.6	N13—C16—H16A	109.4
S1—C4—H4B	109.6	C15—C16—H16A	109.4
H4A—C4—H4B	108.1	N13—C16—H16B	109.4
C6—C5—S1	114.4 (4)	C15—C16—H16B	109.4
C6—C5—H5A	108.7	H16A—C16—H16B	108.0
S1—C5—H5A	108.7	N13—C17—N14	127.2 (4)
C6—C5—H5B	108.7	N13—C17—N16	126.8 (4)
S1—C5—H5B	108.7	N14—C17—N16	106.0 (4)
H5A—C5—H5B	107.6	N15—C18—N17	126.3 (5)
N3—C6—C5	113.2 (5)	N15—C18—N14	112.5 (4)
N3—C6—H6A	108.9	N17—C18—N14	121.2 (4)
C5—C6—H6A	108.9	C11—C19—H19A	109.5
N3—C6—H6B	108.9	C11—C19—H19B	109.5
C5—C6—H6B	108.9	H19A—C19—H19B	109.5
H6A—C6—H6B	107.8	C11—C19—H19C	109.5
N3—C7—N4	125.6 (5)	H19A—C19—H19C	109.5
N3—C7—N6	128.0 (5)	H19B—C19—H19C	109.5
N4—C7—N6	106.4 (5)	N18—C20—N16	113.0 (4)
N5—C8—N7	125.2 (6)	N18—C20—S4	124.6 (4)
N5—C8—N4	113.3 (5)	N16—C20—S4	122.4 (4)
N7—C8—N4	121.4 (6)	Cl1—Bi1—Cl2	90.41 (4)
C1—C9—H9A	109.5	Cl1—Bi1—Cl3	91.37 (4)
C1—C9—H9B	109.5	Cl2—Bi1—Cl3	95.21 (4)
H9A—C9—H9B	109.5	Cl1—Bi1—Cl4	96.86 (5)
C1—C9—H9C	109.5	Cl2—Bi1—Cl4	89.39 (4)
H9A—C9—H9C	109.5	Cl3—Bi1—Cl4	170.54 (4)
H9B—C9—H9C	109.5	Cl1—Bi1—Cl5	89.31 (5)
N8—C10—N6	113.9 (6)	Cl2—Bi1—Cl5	175.50 (4)
N8—C10—S2	125.2 (5)	Cl3—Bi1—Cl5	89.29 (4)
N6—C10—S2	120.9 (4)	Cl4—Bi1—Cl5	86.18 (5)
C14—S3—C15	103.0 (3)	Cl1—Bi1—Cl6	176.47 (4)
C12—N11—C11	109.9 (5)	Cl2—Bi1—Cl6	88.29 (4)
C12—N11—H11N	116 (5)	Cl3—Bi1—Cl6	85.48 (4)
C11—N11—H11N	134 (5)	Cl4—Bi1—Cl6	86.40 (4)
C12—N12—C13	109.2 (5)	Cl5—Bi1—Cl6	92.24 (4)
C12—N12—H12N	125 (5)	O3—N19—O4	122.6 (5)
C13—N12—H12N	126 (5)	O3—N19—O5	119.0 (4)
C17—N13—C16	125.9 (4)	O4—N19—O5	118.5 (5)
C17—N13—H13N	112 (5)	H11—O1—H12	109 (3)
C16—N13—H13N	122 (5)	H21—O2—H22	105 (3)

C8—N5—N6—C7	−0.3 (6)	C18—N15—N16—C17	−1.2 (5)
C8—N5—N6—C10	−172.7 (5)	C18—N15—N16—C20	−176.5 (4)
C2—N1—C1—C3	0.1 (7)	C12—N11—C11—C13	0.2 (6)
C2—N1—C1—C9	177.0 (5)	C12—N11—C11—C19	179.2 (5)
C1—N1—C2—N2	0.3 (7)	C11—N11—C12—N12	−0.3 (6)
C3—N2—C2—N1	−0.5 (7)	C13—N12—C12—N11	0.3 (6)
N1—C1—C3—N2	−0.4 (6)	N11—C11—C13—N12	0.1 (5)
C9—C1—C3—N2	−176.9 (6)	C19—C11—C13—N12	−178.9 (5)
N1—C1—C3—C4	178.3 (5)	N11—C11—C13—C14	174.8 (5)
C9—C1—C3—C4	1.8 (10)	C19—C11—C13—C14	−4.1 (10)
C2—N2—C3—C1	0.6 (6)	C12—N12—C13—C11	−0.2 (6)
C2—N2—C3—C4	−178.2 (5)	C12—N12—C13—C14	−175.6 (5)
C1—C3—C4—S1	−91.1 (6)	C11—C13—C14—S3	−110.4 (6)
N2—C3—C4—S1	87.4 (5)	N12—C13—C14—S3	63.7 (6)
C5—S1—C4—C3	−147.7 (4)	C15—S3—C14—C13	70.6 (5)
C4—S1—C5—C6	−71.8 (5)	C14—S3—C15—C16	−83.8 (5)
C7—N3—C6—C5	−94.9 (6)	C17—N13—C16—C15	−105.3 (6)
S1—C5—C6—N3	−61.7 (6)	S3—C15—C16—N13	−48.5 (6)
C6—N3—C7—N4	−9.9 (9)	C16—N13—C17—N14	0.8 (8)
C6—N3—C7—N6	171.2 (5)	C16—N13—C17—N16	−179.1 (5)
C8—N4—C7—N3	179.7 (6)	C18—N14—C17—N13	178.9 (5)
C8—N4—C7—N6	−1.2 (6)	C18—N14—C17—N16	−1.2 (5)
C10—N6—C7—N3	−8.8 (10)	C20—N16—C17—N13	−4.0 (8)
N5—N6—C7—N3	−180.0 (5)	N15—N16—C17—N13	−178.6 (5)
C10—N6—C7—N4	172.1 (6)	C20—N16—C17—N14	176.1 (5)
N5—N6—C7—N4	0.9 (6)	N15—N16—C17—N14	1.5 (5)
N6—N5—C8—N7	179.9 (6)	N16—N15—C18—N17	−179.7 (6)
N6—N5—C8—N4	−0.5 (7)	N16—N15—C18—N14	0.4 (6)
C7—N4—C8—N5	1.1 (7)	C17—N14—C18—N15	0.5 (6)
C7—N4—C8—N7	−179.3 (6)	C17—N14—C18—N17	−179.3 (5)
C7—N6—C10—N8	−179.0 (6)	C17—N16—C20—N18	−177.0 (5)
N5—N6—C10—N8	−8.3 (8)	N15—N16—C20—N18	−2.8 (6)
C7—N6—C10—S2	2.1 (9)	C17—N16—C20—S4	3.7 (7)
N5—N6—C10—S2	172.8 (4)	N15—N16—C20—S4	177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl6ⁱ	0.89 (4)	2.54 (3)	3.379 (6)	158 (7)
N2—H2N···Cl6ⁱⁱ	0.88 (5)	2.58 (5)	3.406 (5)	156 (6)
N3—H3N···S2	0.89 (5)	2.23 (6)	3.019 (6)	148 (7)
N4—H4N···O2	0.91 (7)	1.74 (7)	2.608 (7)	160 (7)
N7—H7A···S2ⁱⁱⁱ	0.91 (6)	2.46 (7)	3.296 (6)	155 (6)
N7—H7B···O1^iv	0.90 (4)	1.97 (5)	2.842 (8)	162 (6)
N8—H8A···Cl5^iv	0.89 (5)	2.83 (6)	3.550 (5)	140 (5)
O1—H11···Cl5	0.84 (6)	2.39 (6)	3.138 (5)	149 (6)
N11—H11N···O1^v	0.89 (2)	1.83 (3)	2.703 (6)	170 (9)
O1—H12···Cl4^vi	0.85 (6)	2.27 (5)	3.116 (5)	172 (7)
N12—H12N···O3ⁱⁱ	0.88 (6)	1.99 (7)	2.835 (6)	162 (6)
N12—H12N···O4ⁱⁱ	0.88 (6)	2.58 (6)	3.307 (8)	142 (5)
N13—H13N···S4	0.88 (3)	2.27 (6)	3.025 (4)	144 (7)
N14—H14N···O3^vii	0.87 (6)	1.91 (6)	2.772 (5)	175 (5)
N14—H14N···O5^vii	0.87 (6)	2.43 (8)	2.960 (7)	120 (7)
N17—H17A···S4ⁱⁱⁱ	0.87 (6)	2.60 (6)	3.423 (5)	159 (6)
N17—H17B···Cl3ⁱⁱⁱ	0.87 (3)	2.52 (5)	3.337 (5)	158 (6)
N18—H18A···Cl2	0.87 (5)	2.56 (7)	3.304 (5)	144 (5)
N18—H18B···Cl3	0.88 (4)	2.59 (7)	3.332 (5)	143 (7)
O2—H21···Cl4	0.86 (4)	2.62 (6)	3.326 (5)	139 (6)
O2—H21···S2ⁱⁱⁱ	0.86 (4)	2.59 (8)	3.168 (5)	126 (7)
O2—H22···O4	0.86 (3)	2.52 (5)	3.227 (7)	139 (7)
O2—H22···O5	0.86 (3)	1.88 (5)	2.717 (6)	162 (9)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₈N₈S₂)₂[BiCl₆]NO₃·2H₂O
M_r	1148.61
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.8750 (1), 14.2860 (2), 16.6500 (2)
α, β, γ (°)	94.376 (1), 100.717 (1), 92.167 (1)
V (Å³)	2065.24 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.91
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.440, 0.440
No. of measured, independent and observed [I > 2σ(I)] reflections	34173, 9432, 8522
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.05
No. of reflections	9432
No. of parameters	541
No. of restraints	24
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.72, −2.16

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl6ⁱ	0.89 (4)	2.54 (3)	3.379 (6)	158 (7)
N2—H2N···Cl6ⁱⁱ	0.88 (5)	2.58 (5)	3.406 (5)	156 (6)
N3—H3N···S2	0.89 (5)	2.23 (6)	3.019 (6)	148 (7)
N4—H4N···O2	0.91 (7)	1.74 (7)	2.608 (7)	160 (7)
N7—H7A···S2ⁱⁱⁱ	0.91 (6)	2.46 (7)	3.296 (6)	155 (6)
N7—H7B···O1^iv	0.90 (4)	1.97 (5)	2.842 (8)	162 (6)
N8—H8A···Cl5^iv	0.89 (5)	2.83 (6)	3.550 (5)	140 (5)
O1—H11···Cl5	0.84 (6)	2.39 (6)	3.138 (5)	149 (6)
N11—H11N···O1^v	0.89 (2)	1.83 (3)	2.703 (6)	170 (9)
O1—H12···Cl4^vi	0.85 (6)	2.27 (5)	3.116 (5)	172 (7)
N12—H12N···O3ⁱⁱ	0.88 (6)	1.99 (7)	2.835 (6)	162 (6)
N12—H12N···O4ⁱⁱ	0.88 (6)	2.58 (6)	3.307 (8)	142 (5)
N13—H13N···S4	0.88 (3)	2.27 (6)	3.025 (4)	144 (7)
N14—H14N···O3^vii	0.87 (6)	1.91 (6)	2.772 (5)	175 (5)
N14—H14N···O5^vii	0.87 (6)	2.43 (8)	2.960 (7)	120 (7)
N17—H17A···S4ⁱⁱⁱ	0.87 (6)	2.60 (6)	3.423 (5)	159 (6)
N17—H17B···Cl3ⁱⁱⁱ	0.87 (3)	2.52 (5)	3.337 (5)	158 (6)
N18—H18A···Cl2	0.87 (5)	2.56 (7)	3.304 (5)	144 (5)
N18—H18B···Cl3	0.88 (4)	2.59 (7)	3.332 (5)	143 (7)
O2—H21···Cl4	0.86 (4)	2.62 (6)	3.326 (5)	139 (6)
O2—H21···S2ⁱⁱⁱ	0.86 (4)	2.59 (8)	3.168 (5)	126 (7)
O2—H22···O4	0.86 (3)	2.52 (5)	3.227 (7)	139 (7)
O2—H22···O5	0.86 (3)	1.88 (5)	2.717 (6)	162 (9)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) −x, −y+1, −z+1.

Acknowledgements

The author acknowledges the School of Chemistry, Cardiff University, Wales.

References

Battaglia, L. P. & Corradi, A. B. (1986). Inorg. Chim. Acta, 121, 131–136. CSD CrossRef CAS Web of Science Google Scholar
Bednarska-Bolek, B., Zaleski, J., Bator, G. & Jakubas, R. (2000). J. Phys. Chem. Solids, 61, 1249–1261. CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hooft, R. W. W. (1998). COLLECT. Bruker AXS Inc., Delft, The Netherlands. Google Scholar
Jarraya, S., Salah, A. B., Daoud, A., Rothammel, W. & Burzlaff, H. (1993). Acta Cryst. C49, 1594–1596. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Lazarini, F. (1987). Acta Cryst. C43, 637–638. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m402-m403

https://doi.org/10.1107/S1600536813016449

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{3-amino-1-carbamo­thioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)meth­yl]sulfan­yl}eth­yl)amino]-1H-1,2,4-triazol-4-ium} hexa­chloridobismuthate(III) nitrate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{3-amino-1-carbamothioyl-5-[(2-{[(5-methyl-1H-imidazol-3-ium-4-yl)methyl]sulfanyl}ethyl)amino]-1H-1,2,4-triazol-4-ium} hexachloridobismuthate(III) nitrate dihydrate