Bis(5-amino-4-amino-carbonyl-1H-imid-azol-3-ium) (5-amino-4-amino-carbonyl-1H-imidazol-3-ium-κO)-di-μ-chlorido-hepta-chlorido-dibismuth(III) mono-hydrate.

The title compound, (C(4)H(7)N(4)O)(2)[Bi(2)Cl(9)(C(4)H(7)N(4)O)]·H(2)O, was prepared by the reaction of bis-muth trichloride and 5-amino-1H-imidazole-4-carboxamide in a dilute HCl medium. The asymmetric unit contains two 5-amino-4-amino-carbonyl-1H-imidazol-3-ium cations, one edge-shared non-centrosymmetric biocta-hedral [Bi(2)C1(9)(C(4)H(7)N(4)O)](2-) dianion and a water mol-ecule. In the dianion, the planar 5-amino-4-amino-carbonyl-1H-imidazol-3-ium ligand occupies an equatorial site and is inclined at an angle of 75.7 (2)° to the Bi(2)(μ-C1)(2) plane. The salt forms a three-dimensional network arising from hydrogen bonds between cations, anions and water mol-ecules.

Related literature

For general background, see: Turel et al. (1998 ▶); Goforth et al. (2004 ▶). For related structures, see: Fu et al. (2005 ▶); Wu et al. (2005 ▶); Kyriakidis et al., (1990 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

(C4H7N4O)2[Bi2Cl9(C4H7N4O)]·H2O

M = 1136.43

Triclinic,

a = 11.3365 (5) Å

b = 12.2486 (6) Å

c = 12.7919 (6) Å

α = 74.433 (3)°

β = 65.939 (3)°

γ = 75.397 (3)°

V = 1541.71 (12) Å3

Z = 2

Mo Kα radiation

μ = 12.22 mm−1

T = 123 (2) K

0.25 × 0.22 × 0.20 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.150, T max = 0.194 (expected range = 0.067–0.087)

18217 measured reflections

5695 independent reflections

4988 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.223

S = 1.10

5695 reflections

359 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 5.85 e Å−3

Δρmin = −4.41 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009367/ci2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009367/ci2573Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C4H7N4O)2[Bi2Cl9(C4H7N4O)]·H2O	Z = 2
Mr = 1136.43	F000 = 1060
Triclinic, P1	Dx = 2.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.3365 (5) Å	Cell parameters from 5695 reflections
b = 12.2486 (6) Å	θ = 1.8–25.5º
c = 12.7919 (6) Å	µ = 12.22 mm−1
α = 74.433 (3)º	T = 123 (2) K
β = 65.939 (3)º	Block, yellow
γ = 75.397 (3)º	0.25 × 0.22 × 0.20 mm
V = 1541.71 (12) Å3

Rigaku Mercury diffractometer	5695 independent reflections
Radiation source: fine-focus sealed tube	4988 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.063
Detector resolution: 7.31 pixels mm-1	θmax = 25.5º
T = 123(2) K	θmin = 1.8º
ω scans	h = −13→13
Absorption correction: multi-scan(Jacobson, 1998)	k = −14→12
Tmin = 0.150, Tmax = 0.194	l = −15→15
18217 measured reflections

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)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.223	w = 1/[σ2(Fo2) + (0.1568P)2 + 11.6845P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
5695 reflections	Δρmax = 5.85 e Å−3
359 parameters	Δρmin = −4.41 e Å−3
2 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: 0.0044 (6)

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
Bi1	0.88808 (4)	0.20130 (4)	0.77380 (4)	0.0190 (2)
Bi2	1.29373 (4)	0.22332 (4)	0.68713 (4)	0.0197 (2)
Cl1	0.7650 (4)	0.0403 (3)	0.9119 (3)	0.0322 (8)
Cl2	0.6905 (4)	0.3183 (3)	0.7184 (3)	0.0327 (8)
Cl3	0.9668 (4)	0.0975 (3)	0.5986 (3)	0.0260 (8)
Cl4	1.1107 (4)	0.0608 (3)	0.8230 (3)	0.0279 (8)
Cl5	1.0678 (4)	0.3675 (3)	0.6497 (3)	0.0351 (9)
Cl6	1.3711 (4)	0.1462 (3)	0.4887 (3)	0.0303 (8)
Cl7	1.4310 (4)	0.3802 (3)	0.5692 (3)	0.0310 (8)
Cl8	1.4877 (4)	0.0783 (3)	0.7303 (3)	0.0297 (8)
Cl9	1.2315 (4)	0.3140 (3)	0.8792 (3)	0.0332 (9)
O1	0.8130 (11)	0.2826 (10)	0.9511 (9)	0.032 (2)
O2	0.6215 (10)	0.5277 (8)	0.8614 (8)	0.028 (2)
O3	0.9864 (12)	0.3596 (10)	0.1801 (10)	0.037 (3)
O4	0.4595 (11)	0.1325 (10)	0.9725 (9)	0.036 (2)
H4C	0.448 (17)	0.134 (15)	0.913 (9)	0.043*
H4D	0.535 (6)	0.100 (14)	0.965 (16)	0.043*
N1	0.5550 (11)	0.3189 (10)	1.2864 (10)	0.023 (2)
H1	0.5002	0.2801	1.3472	0.027*
N2	0.6655 (10)	0.4515 (9)	1.1772 (9)	0.021 (2)
H2	0.6968	0.5165	1.1522	0.025*
N3	0.6306 (14)	0.1787 (11)	1.1651 (12)	0.030 (3)
H3A	0.6824	0.1572	1.0986	0.036*
H3B	0.5778	0.1332	1.2196	0.036*
N4	0.8721 (12)	0.4479 (11)	0.9441 (11)	0.032 (3)
H4A	0.9323	0.4469	0.8739	0.038*
H4B	0.8592	0.5043	0.9799	0.038*
N5	0.7091 (11)	0.8051 (10)	0.8213 (10)	0.026 (3)
H5	0.6647	0.8364	0.8836	0.031*
N6	0.8406 (12)	0.7822 (10)	0.6487 (10)	0.026 (3)
H6	0.8993	0.7956	0.5778	0.032*
N7	0.8068 (18)	0.5992 (14)	0.6422 (13)	0.049 (4)
H7A	0.8624	0.6028	0.5697	0.059*
H7B	0.7669	0.5390	0.6781	0.059*
N8	0.5411 (11)	0.6387 (11)	1.0021 (10)	0.029 (3)
H8A	0.4925	0.5889	1.0546	0.035*
H8B	0.5414	0.7033	1.0198	0.035*
N9	0.7241 (11)	0.2073 (10)	0.4935 (10)	0.024 (2)
H9	0.6776	0.2215	0.5642	0.029*
N10	0.8048 (11)	0.1235 (10)	0.3465 (10)	0.023 (2)
H10	0.8222	0.0725	0.3029	0.028*
N11	0.8338 (14)	0.3714 (11)	0.4186 (12)	0.036 (3)
H11A	0.8904	0.4112	0.3607	0.043*
H11B	0.7929	0.3944	0.4859	0.043*
N12	0.9985 (13)	0.2033 (12)	0.1141 (11)	0.030 (3)
H12A	1.0563	0.2282	0.0459	0.037*
H12B	0.9727	0.1373	0.1270	0.037*
C1	0.7034 (12)	0.3655 (11)	1.1141 (11)	0.020 (3)
C2	0.6319 (12)	0.2801 (11)	1.1833 (11)	0.019 (3)
C3	0.5752 (16)	0.4227 (14)	1.2810 (13)	0.030 (3)
H3	0.5331	0.4677	1.3402	0.036*
C4	0.7999 (13)	0.3635 (13)	0.9963 (11)	0.025 (3)
C5	0.7001 (12)	0.7001 (11)	0.8102 (12)	0.021 (3)
C6	0.7828 (13)	0.6855 (13)	0.6981 (12)	0.023 (3)
C7	0.7944 (16)	0.8524 (17)	0.7245 (16)	0.036 (4)
H7	0.8190	0.9250	0.7110	0.043*
C8	0.6157 (13)	0.6159 (12)	0.8940 (11)	0.022 (3)
C9	0.8589 (13)	0.2245 (12)	0.3115 (12)	0.022 (3)
C10	0.8098 (13)	0.2759 (12)	0.4041 (12)	0.023 (3)
C11	0.7240 (12)	0.1182 (10)	0.4551 (11)	0.020 (3)
H11	0.6732	0.0589	0.4993	0.024*
C12	0.9513 (13)	0.2642 (12)	0.1958 (12)	0.022 (3)

	U11	U22	U33	U12	U13	U23
Bi1	0.0240 (3)	0.0227 (4)	0.0089 (3)	−0.0076 (2)	−0.0030 (2)	−0.0021 (2)
Bi2	0.0241 (3)	0.0198 (4)	0.0132 (3)	−0.0090 (2)	−0.0041 (2)	0.0009 (2)
Cl1	0.0335 (17)	0.0309 (19)	0.0273 (19)	−0.0177 (15)	−0.0048 (15)	0.0037 (15)
Cl2	0.0371 (18)	0.039 (2)	0.0231 (18)	0.0031 (16)	−0.0130 (15)	−0.0127 (15)
Cl3	0.0366 (17)	0.0275 (18)	0.0119 (16)	−0.0086 (14)	−0.0055 (13)	−0.0029 (13)
Cl4	0.0378 (19)	0.0293 (19)	0.0177 (17)	−0.0132 (15)	−0.0102 (14)	0.0013 (14)
Cl5	0.041 (2)	0.031 (2)	0.0256 (19)	−0.0096 (16)	−0.0075 (16)	0.0039 (16)
Cl6	0.047 (2)	0.0273 (19)	0.0214 (18)	−0.0161 (16)	−0.0126 (16)	−0.0019 (15)
Cl7	0.0423 (19)	0.0284 (19)	0.0200 (18)	−0.0222 (15)	−0.0033 (15)	0.0016 (14)
Cl8	0.0342 (17)	0.0319 (19)	0.0198 (17)	−0.0073 (15)	−0.0083 (14)	−0.0003 (14)
Cl9	0.043 (2)	0.035 (2)	0.0185 (18)	−0.0209 (16)	−0.0029 (15)	−0.0004 (15)
O1	0.050 (6)	0.035 (6)	0.012 (5)	−0.008 (5)	−0.008 (5)	−0.012 (4)
O2	0.042 (5)	0.032 (6)	0.013 (5)	−0.018 (4)	−0.008 (4)	−0.003 (4)
O3	0.049 (6)	0.032 (6)	0.022 (6)	−0.011 (5)	−0.004 (5)	−0.002 (5)
O4	0.039 (6)	0.052 (7)	0.018 (5)	−0.015 (5)	−0.004 (5)	−0.014 (5)
N1	0.035 (6)	0.015 (6)	0.014 (6)	−0.007 (5)	−0.004 (5)	0.001 (5)
N2	0.030 (5)	0.017 (6)	0.018 (6)	−0.010 (5)	−0.011 (5)	0.005 (4)
N3	0.048 (8)	0.020 (7)	0.019 (7)	−0.016 (6)	−0.006 (6)	0.003 (5)
N4	0.042 (7)	0.030 (7)	0.019 (6)	−0.020 (6)	−0.001 (5)	0.000 (5)
N5	0.034 (6)	0.025 (6)	0.021 (6)	−0.011 (5)	−0.008 (5)	−0.003 (5)
N6	0.032 (6)	0.024 (7)	0.015 (6)	−0.008 (5)	−0.004 (5)	0.002 (5)
N7	0.074 (11)	0.032 (8)	0.021 (8)	−0.008 (8)	0.003 (7)	−0.007 (6)
N8	0.034 (6)	0.041 (7)	0.016 (6)	−0.024 (6)	−0.007 (5)	0.003 (5)
N9	0.030 (6)	0.024 (6)	0.014 (6)	−0.004 (5)	−0.006 (5)	0.001 (5)
N10	0.031 (6)	0.026 (6)	0.013 (6)	−0.011 (5)	−0.002 (5)	−0.007 (5)
N11	0.053 (8)	0.024 (7)	0.028 (7)	−0.014 (6)	−0.008 (6)	−0.005 (6)
N12	0.033 (6)	0.029 (7)	0.017 (7)	−0.008 (5)	0.001 (5)	0.001 (5)
C1	0.024 (6)	0.017 (6)	0.012 (6)	0.001 (5)	−0.003 (5)	−0.002 (5)
C2	0.024 (6)	0.021 (7)	0.012 (6)	−0.002 (5)	−0.009 (5)	−0.001 (5)
C3	0.047 (9)	0.027 (8)	0.014 (7)	−0.006 (7)	−0.008 (6)	−0.006 (6)
C4	0.031 (7)	0.037 (8)	0.008 (6)	−0.013 (6)	−0.007 (5)	0.001 (6)
C5	0.023 (6)	0.018 (7)	0.017 (7)	−0.002 (5)	−0.009 (5)	0.003 (5)
C6	0.024 (6)	0.023 (7)	0.013 (7)	0.001 (5)	−0.004 (5)	0.003 (5)
C7	0.029 (8)	0.040 (10)	0.034 (10)	−0.013 (7)	−0.013 (7)	0.009 (8)
C8	0.023 (6)	0.025 (8)	0.011 (6)	0.001 (6)	−0.006 (5)	0.003 (6)
C9	0.027 (6)	0.021 (7)	0.016 (7)	−0.003 (5)	−0.009 (6)	0.001 (6)
C10	0.027 (6)	0.027 (7)	0.016 (7)	−0.010 (6)	−0.010 (6)	0.001 (6)
C11	0.031 (6)	0.007 (6)	0.013 (6)	0.000 (5)	0.000 (5)	−0.001 (5)
C12	0.024 (6)	0.024 (7)	0.015 (7)	−0.009 (5)	−0.007 (5)	0.003 (6)

Bi1—O1	2.464 (10)	N5—H5	0.88
Bi1—Cl1	2.543 (3)	N6—C7	1.33 (2)
Bi1—Cl2	2.589 (4)	N6—C6	1.372 (19)
Bi1—Cl3	2.601 (4)	N6—H6	0.88
Bi1—Cl4	2.872 (4)	N7—C6	1.34 (2)
Bi1—Cl5	2.921 (4)	N7—H7A	0.88
Bi2—Cl7	2.535 (3)	N7—H7B	0.88
Bi2—Cl8	2.606 (4)	N8—C8	1.356 (18)
Bi2—Cl6	2.676 (4)	N8—H8A	0.88
Bi2—Cl9	2.725 (4)	N8—H8B	0.88
Bi2—Cl5	2.859 (4)	N9—C11	1.312 (17)
Bi2—Cl4	2.928 (4)	N9—C10	1.395 (17)
O1—C4	1.226 (18)	N9—H9	0.88
O2—C8	1.237 (17)	N10—C11	1.311 (16)
O3—C12	1.267 (18)	N10—C9	1.403 (18)
O4—H4C	0.82 (12)	N10—H10	0.88
O4—H4D	0.83 (12)	N11—C10	1.340 (19)
N1—C3	1.33 (2)	N11—H11A	0.88
N1—C2	1.383 (18)	N11—H11B	0.88
N1—H1	0.88	N12—C12	1.30 (2)
N2—C3	1.326 (19)	N12—H12A	0.88
N2—C1	1.375 (17)	N12—H12B	0.88
N2—H2	0.88	C1—C2	1.371 (18)
N3—C2	1.328 (19)	C1—C4	1.459 (18)
N3—H3A	0.88	C3—H3	0.95
N3—H3B	0.88	C5—C6	1.39 (2)
N4—C4	1.340 (18)	C5—C8	1.482 (19)
N4—H4A	0.88	C7—H7	0.95
N4—H4B	0.88	C9—C10	1.34 (2)
N5—C7	1.31 (2)	C9—C12	1.459 (19)
N5—C5	1.364 (18)	C11—H11	0.95
O1—Bi1—Cl1	83.9 (3)	C6—N7—H7B	120.0
O1—Bi1—Cl2	92.6 (3)	H7A—N7—H7B	120.0
Cl1—Bi1—Cl2	94.34 (13)	C8—N8—H8A	120.0
O1—Bi1—Cl3	174.9 (3)	C8—N8—H8B	120.0
Cl1—Bi1—Cl3	91.66 (12)	H8A—N8—H8B	120.0
Cl2—Bi1—Cl3	90.18 (12)	C11—N9—C10	108.9 (11)
O1—Bi1—Cl4	91.6 (3)	C11—N9—H9	125.5
Cl1—Bi1—Cl4	84.94 (12)	C10—N9—H9	125.5
Cl2—Bi1—Cl4	175.67 (11)	C11—N10—C9	108.3 (11)
Cl3—Bi1—Cl4	85.58 (11)	C11—N10—H10	125.9
O1—Bi1—Cl5	89.9 (3)	C9—N10—H10	125.9
Cl1—Bi1—Cl5	166.27 (13)	C10—N11—H11A	120.0
Cl2—Bi1—Cl5	98.13 (12)	C10—N11—H11B	120.0
Cl3—Bi1—Cl5	94.01 (12)	H11A—N11—H11B	120.0
Cl4—Bi1—Cl5	83.05 (11)	C12—N12—H12A	120.0
Cl7—Bi2—Cl8	93.94 (13)	C12—N12—H12B	120.0
Cl7—Bi2—Cl6	86.98 (12)	H12A—N12—H12B	120.0
Cl8—Bi2—Cl6	87.69 (12)	C2—C1—N2	106.6 (11)
Cl7—Bi2—Cl9	88.05 (12)	C2—C1—C4	125.7 (12)
Cl8—Bi2—Cl9	91.62 (12)	N2—C1—C4	127.6 (12)
Cl6—Bi2—Cl9	174.93 (11)	N3—C2—C1	131.4 (13)
Cl7—Bi2—Cl5	90.85 (13)	N3—C2—N1	123.2 (12)
Cl8—Bi2—Cl5	175.20 (11)	C1—C2—N1	105.4 (12)
Cl6—Bi2—Cl5	92.26 (12)	N2—C3—N1	106.9 (13)
Cl9—Bi2—Cl5	88.84 (13)	N2—C3—H3	126.6
Cl7—Bi2—Cl4	173.86 (12)	N1—C3—H3	126.6
Cl8—Bi2—Cl4	92.07 (11)	O1—C4—N4	123.2 (13)
Cl6—Bi2—Cl4	94.49 (11)	O1—C4—C1	118.0 (12)
Cl9—Bi2—Cl4	90.55 (11)	N4—C4—C1	118.8 (13)
Cl5—Bi2—Cl4	83.14 (11)	N5—C5—C6	106.7 (12)
Bi1—Cl4—Bi2	96.60 (11)	N5—C5—C8	129.6 (13)
Bi2—Cl5—Bi1	97.04 (12)	C6—C5—C8	123.6 (13)
C4—O1—Bi1	149.3 (9)	N7—C6—N6	123.7 (13)
H4C—O4—H4D	108 (19)	N7—C6—C5	130.7 (14)
C3—N1—C2	110.8 (12)	N6—C6—C5	105.5 (13)
C3—N1—H1	124.6	N5—C7—N6	109.0 (16)
C2—N1—H1	124.6	N5—C7—H7	125.5
C3—N2—C1	110.4 (12)	N6—C7—H7	125.5
C3—N2—H2	124.8	O2—C8—N8	124.5 (13)
C1—N2—H2	124.8	O2—C8—C5	117.4 (12)
C2—N3—H3A	120.0	N8—C8—C5	118.0 (13)
C2—N3—H3B	120.0	C10—C9—N10	106.9 (12)
H3A—N3—H3B	120.0	C10—C9—C12	127.4 (13)
C4—N4—H4A	120.0	N10—C9—C12	125.8 (13)
C4—N4—H4B	120.0	N11—C10—C9	130.9 (13)
H4A—N4—H4B	120.0	N11—C10—N9	122.7 (13)
C7—N5—C5	109.4 (14)	C9—C10—N9	106.4 (12)
C7—N5—H5	125.3	N10—C11—N9	109.5 (12)
C5—N5—H5	125.3	N10—C11—H11	125.3
C7—N6—C6	109.3 (13)	N9—C11—H11	125.3
C7—N6—H6	125.3	O3—C12—N12	121.6 (13)
C6—N6—H6	125.3	O3—C12—C9	116.4 (13)
C6—N7—H7A	120.0	N12—C12—C9	121.9 (13)
O1—Bi1—Cl4—Bi2	−92.7 (3)	C2—C1—C4—O1	5(2)
Cl1—Bi1—Cl4—Bi2	−176.40 (12)	N2—C1—C4—O1	−174.4 (13)
Cl3—Bi1—Cl4—Bi2	91.54 (12)	C2—C1—C4—N4	−173.0 (13)
Cl5—Bi1—Cl4—Bi2	−3.06 (9)	N2—C1—C4—N4	7(2)
Cl8—Bi2—Cl4—Bi1	−176.47 (11)	C7—N5—C5—C6	−1.8 (16)
Cl6—Bi2—Cl4—Bi1	−88.62 (12)	C7—N5—C5—C8	−178.5 (13)
Cl9—Bi2—Cl4—Bi1	91.89 (12)	C7—N6—C6—N7	178.3 (15)
Cl5—Bi2—Cl4—Bi1	3.12 (10)	C7—N6—C6—C5	−1.2 (15)
Cl7—Bi2—Cl5—Bi1	178.20 (12)	N5—C5—C6—N7	−177.7 (16)
Cl6—Bi2—Cl5—Bi1	91.18 (12)	C8—C5—C6—N7	−1(2)
Cl9—Bi2—Cl5—Bi1	−93.77 (12)	N5—C5—C6—N6	1.8 (14)
Cl4—Bi2—Cl5—Bi1	−3.07 (10)	C8—C5—C6—N6	178.7 (11)
O1—Bi1—Cl5—Bi2	94.8 (3)	C5—N5—C7—N6	1.0 (17)
Cl1—Bi1—Cl5—Bi2	32.2 (6)	C6—N6—C7—N5	0.2 (17)
Cl2—Bi1—Cl5—Bi2	−172.67 (11)	N5—C5—C8—O2	177.0 (13)
Cl3—Bi1—Cl5—Bi2	−81.91 (13)	C6—C5—C8—O2	0.9 (19)
Cl4—Bi1—Cl5—Bi2	3.13 (10)	N5—C5—C8—N8	−5(2)
Cl1—Bi1—O1—C4	−170 (2)	C6—C5—C8—N8	178.5 (12)
Cl2—Bi1—O1—C4	−75.7 (19)	C11—N10—C9—C10	1.7 (15)
Cl4—Bi1—O1—C4	105.4 (19)	C11—N10—C9—C12	−178.5 (12)
Cl5—Bi1—O1—C4	22.4 (19)	N10—C9—C10—N11	176.9 (15)
C3—N2—C1—C2	0.2 (15)	C12—C9—C10—N11	−3(2)
C3—N2—C1—C4	179.9 (13)	N10—C9—C10—N9	−1.4 (14)
N2—C1—C2—N3	−179.8 (14)	C12—C9—C10—N9	178.8 (12)
C4—C1—C2—N3	1(2)	C11—N9—C10—N11	−177.8 (13)
N2—C1—C2—N1	−0.8 (13)	C11—N9—C10—C9	0.7 (14)
C4—C1—C2—N1	179.5 (12)	C9—N10—C11—N9	−1.3 (15)
C3—N1—C2—N3	−179.8 (13)	C10—N9—C11—N10	0.4 (15)
C3—N1—C2—C1	1.2 (15)	C10—C9—C12—O3	−2(2)
C1—N2—C3—N1	0.5 (16)	N10—C9—C12—O3	178.1 (13)
C2—N1—C3—N2	−1.0 (17)	C10—C9—C12—N12	175.8 (14)
Bi1—O1—C4—N4	−22 (3)	N10—C9—C12—N12	−4(2)
Bi1—O1—C4—C1	160.0 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4C···Cl8i	0.82 (12)	2.44 (14)	3.215 (11)	158 (16)
O4—H4D···Cl1	0.83 (12)	2.38 (13)	3.190 (12)	168 (17)
N1—H1···Cl6ii	0.88	2.36	3.226 (12)	169
N2—H2···Cl9iii	0.88	2.30	3.166 (11)	170
N3—H3A···O1	0.88	2.33	2.869 (17)	120
N3—H3A···Cl1	0.88	2.82	3.649 (15)	157
N3—H3B···Cl8iv	0.88	2.71	3.451 (14)	142
N5—H5···O4v	0.88	1.87	2.725 (16)	163
N6—H6···Cl3vi	0.88	2.40	3.230 (12)	158
N7—H7A···Cl5vi	0.88	2.53	3.358 (16)	156
N7—H7B···O2	0.88	2.24	2.802 (18)	121
N8—H8A···O2v	0.88	1.96	2.821 (15)	166
N8—H8B···O4v	0.88	2.04	2.905 (18)	168
N9—H9···Cl2	0.88	2.63	3.348 (13)	140
N10—H10···Cl4vii	0.88	2.37	3.249 (12)	175
N11—H11A···O3	0.88	2.30	2.850 (18)	120
N11—H11A···Cl5vi	0.88	2.83	3.426 (14)	127
N11—H11B···Cl2	0.88	2.70	3.447 (15)	143
N12—H12A···Cl9viii	0.88	2.45	3.315 (13)	168
N12—H12B···Cl4vii	0.88	2.65	3.529 (15)	177

Table 1

Selected bond lengths (Å)

Bi1—O1	2.464 (10)
Bi1—Cl1	2.543 (3)
Bi1—Cl2	2.589 (4)
Bi1—Cl3	2.601 (4)
Bi1—Cl4	2.872 (4)
Bi1—Cl5	2.921 (4)
Bi2—Cl7	2.535 (3)
Bi2—Cl8	2.606 (4)
Bi2—Cl6	2.676 (4)
Bi2—Cl9	2.725 (4)
Bi2—Cl5	2.859 (4)
Bi2—Cl4	2.928 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4C⋯Cl8i	0.82 (12)	2.44 (14)	3.215 (11)	158 (16)
O4—H4D⋯Cl1	0.83 (12)	2.38 (13)	3.190 (12)	168 (17)
N1—H1⋯Cl6ii	0.88	2.36	3.226 (12)	169
N2—H2⋯Cl9iii	0.88	2.30	3.166 (11)	170
N3—H3A⋯O1	0.88	2.33	2.869 (17)	120
N3—H3A⋯Cl1	0.88	2.82	3.649 (15)	157
N3—H3B⋯Cl8iv	0.88	2.71	3.451 (14)	142
N5—H5⋯O4v	0.88	1.87	2.725 (16)	163
N6—H6⋯Cl3vi	0.88	2.40	3.230 (12)	158
N7—H7A⋯Cl5vi	0.88	2.53	3.358 (16)	156
N7—H7B⋯O2	0.88	2.24	2.802 (18)	121
N8—H8A⋯O2v	0.88	1.96	2.821 (15)	166
N8—H8B⋯O4v	0.88	2.04	2.905 (18)	168
N9—H9⋯Cl2	0.88	2.63	3.348 (13)	140
N10—H10⋯Cl4vii	0.88	2.37	3.249 (12)	175
N11—H11A⋯O3	0.88	2.30	2.850 (18)	120
N11—H11A⋯Cl5vi	0.88	2.83	3.426 (14)	127
N11—H11B⋯Cl2	0.88	2.70	3.447 (15)	143
N12—H12A⋯Cl9viii	0.88	2.45	3.315 (13)	168
N12—H12B⋯Cl4vii	0.88	2.65	3.529 (15)	177

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .