Bis(5-amino-4-amino­carbonyl-1H-imid­azol-3-ium) (5-amino-4-amino­carbonyl-1H-imidazol-3-ium-κO)-di-μ-chlorido-hepta­chlorido-dibismuth(III) mono­hydrate

Lv, L.-P.; He, L.-J.; Li, W.-W.; Yu, W.-B.; Hu, X.-C.

doi:10.1107/S1600536808009367

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m643-m644

doi:10.1107/S1600536808009367

Open

access

Bis(5-amino-4-aminocarbonyl-1H-imidazol-3-ium) (5-amino-4-aminocarbonyl-1H-imidazol-3-ium-κO)-di-μ-chlorido-heptachlorido-dibismuth(III) monohydrate

Lu-Ping Lv,^a Lian-Jun He,^a Wei-Wei Li,^a Wen-Bo Yu ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center for Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 26 March 2008; accepted 6 April 2008; online 10 April 2008)

The title compound, (C₄H₇N₄O)₂[Bi₂Cl₉(C₄H₇N₄O)]·H₂O, was prepared by the reaction of bismuth trichloride and 5-amino-1H-imidazole-4-carboxamide in a dilute HCl medium. The asymmetric unit contains two 5-amino-4-aminocarbonyl-1H-imidazol-3-ium cations, one edge-shared non-centrosymmetric bioctahedral [Bi₂C1₉(C₄H₇N₄O)]²⁻ dianion and a water molecule. In the dianion, the planar 5-amino-4-aminocarbonyl-1H-imidazol-3-ium ligand occupies an equatorial site and is inclined at an angle of 75.7 (2)° to the Bi₂(μ-C1)₂ plane. The salt forms a three-dimensional network arising from hydrogen bonds between cations, anions and water molecules.

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_r = 1136.43
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.223
S = 1.10
5695 reflections
359 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 5.85 e Å⁻³
Δρ_min = −4.41 e Å⁻³

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⋯Cl8^iv	0.88	2.71	3.451 (14)	142
N5—H5⋯O4^v	0.88	1.87	2.725 (16)	163
N6—H6⋯Cl3^vi	0.88	2.40	3.230 (12)	158
N7—H7A⋯Cl5^vi	0.88	2.53	3.358 (16)	156
N7—H7B⋯O2	0.88	2.24	2.802 (18)	121
N8—H8A⋯O2^v	0.88	1.96	2.821 (15)	166
N8—H8B⋯O4^v	0.88	2.04	2.905 (18)	168
N9—H9⋯Cl2	0.88	2.63	3.348 (13)	140
N10—H10⋯Cl4^vii	0.88	2.37	3.249 (12)	175
N11—H11A⋯O3	0.88	2.30	2.850 (18)	120
N11—H11A⋯Cl5^vi	0.88	2.83	3.426 (14)	127
N11—H11B⋯Cl2	0.88	2.70	3.447 (15)	143
N12—H12A⋯Cl9^viii	0.88	2.45	3.315 (13)	168
N12—H12B⋯Cl4^vii	0.88	2.65	3.529 (15)	177
Symmetry codes: (i) x-1, y, z; (ii) x-1, y, z+1; (iii) -x+2, -y+1, -z+2; (iv) -x+2, -y, -z+2; (v) -x+1, -y+1, -z+2; (vi) -x+2, -y+1, -z+1; (vii) -x+2, -y, -z+1; (viii) x, y, z-1.

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.

Supporting information

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

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

checkCIF report

Comment top

Bismuth trihalides have an extensive coordination chemistry as a result of the Lewis acidity of the group 15 element centre. Recently, there is increasing interest in halobismuthate(III) compounds, due to their anti-ulcer activity (Turel et al., 1998) and their unique optical and electronic properties, including nonlinear optical activity, luminescence and semiconductivity (Goforth et al., 2004). We report here the crystal structure of the title organic–inorganic hybrid complex.

The asymmetric unit of the title compound contains two 5-amino-4-aminocarbonyl-1H-imidazol-3-ium (C₄H₇N₄O⁺) cations, an edge-shared bi-octahedral dianion {[Bi₂C1₉(C₄H₇N₄O)]^2-} and a water molecule. The dianion of the title compound is non-centrosymmetric compared to large number of centrosymmetric decanchlorobismuthates that have been crystallographically verified, as exemplified by (C₅H₁₄N₂)₂[Bi₂Cl₁₀].2H₂O (Fu et al., 2005) and (C₄H₁₂N₂)₂[Bi₂Cl₁₀].3H₂O (Wu et al., 2005). A search of the Cambridge Structural Database (Version 5.29, January 2008; Allen, 2002) yielded no hits for noncentrosymmetric octanchlorobismuthates.

In the noncentrosymmetric edge-shared bi-octahedral dianion, the planar 5-amino-4-aminocarbonyl-1H-imidazol-3-ium ligand occupied a octahedral terminal site, inclined at angle of 75.7 (2)° to the Bi₂(µ-C1)₂ plane. Atoms Cl1, Cl2, Cl4, Cl5, Cl7, Cl8, Bi1 and Bi2 are coplaner, with an r.m.s. deviation of 0.120 Å. The Bi—O distance of 2.464 (10) Å is slightly longer compared to the reported value of of 2.424 (10) Å (Kyriakidis et al., 1990). The Bi—Cl distances (Table 1) lie in the range 2.535 (3) Å-2.928 (4) Å, with the Bi—C1 distances involving the bridging C1 atoms being longer (2.859 (4) Å-2.928 (4) Å). None of the interbond angles deviate significantly (>10°) from idealized octahedral angles.

The N—H···O, N—H···Cl and O—H···Cl hydrogen bonds (Table 2) link the constituent ions and water molecules into a three-dimensional network (Fig.2).

Related literature top

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 top

The title compound was prepared by the reaction of bismuth trichloride (0.500 g, 1.59 mmol) and 5-amino-4-carboxamide-1H-imidazole (0.601,4.9 mmol) in a hydrochloric acid medium. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution of the title compound at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. The crystal packing of the title compound, viewed approximately down the c axis. Dashed lines indicate intermolecular hydrogen bonds.

Bis(5-amino-4-aminocarbonyl-1H-imidazol-3-ium)(5-amino-4-aminocarbonyl- 1H-imidazol-3-ium-κO)-di-µ-chlorido-heptachlorido-dibismuth(III) monohydrate top

Crystal data top

(C₄H₇N₄O)₂[Bi₂Cl₉(C₄H₇N₄O)]·H₂O	Z = 2
M_r = 1136.43	F(000) = 1060
Triclinic, P1	D_x = 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 = 1.8–25.5°
c = 12.7919 (6) Å	µ = 12.22 mm⁻¹
α = 74.433 (3)°	T = 123 K
β = 65.939 (3)°	Block, yellow
γ = 75.397 (3)°	0.25 × 0.22 × 0.20 mm
V = 1541.71 (12) Å³

Data collection top

Rigaku Mercury diffractometer	5695 independent reflections
Radiation source: fine-focus sealed tube	4988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.5°, θ_min = 1.8°
ω scans	h = −13→13
Absorption correction: multi-scan (Jacobson, 1998)	k = −14→12
T_min = 0.150, T_max = 0.194	l = −15→15
18217 measured reflections

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)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.223	w = 1/[σ²(F_o²) + (0.1568P)² + 11.6845P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
5695 reflections	Δρ_max = 5.85 e Å⁻³
359 parameters	Δρ_min = −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)

Crystal data top

(C₄H₇N₄O)₂[Bi₂Cl₉(C₄H₇N₄O)]·H₂O	γ = 75.397 (3)°
M_r = 1136.43	V = 1541.71 (12) Å³
Triclinic, P1	Z = 2
a = 11.3365 (5) Å	Mo Kα radiation
b = 12.2486 (6) Å	µ = 12.22 mm⁻¹
c = 12.7919 (6) Å	T = 123 K
α = 74.433 (3)°	0.25 × 0.22 × 0.20 mm
β = 65.939 (3)°

Data collection top

Rigaku Mercury diffractometer	5695 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	4988 reflections with I > 2σ(I)
T_min = 0.150, T_max = 0.194	R_int = 0.063
18217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	2 restraints
wR(F²) = 0.223	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.1568P)² + 11.6845P] where P = (F_o² + 2F_c²)/3
5695 reflections	Δρ_max = 5.85 e Å⁻³
359 parameters	Δρ_min = −4.41 e Å⁻³

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cl8^iv	0.88	2.71	3.451 (14)	142
N5—H5···O4^v	0.88	1.87	2.725 (16)	163
N6—H6···Cl3^vi	0.88	2.40	3.230 (12)	158
N7—H7A···Cl5^vi	0.88	2.53	3.358 (16)	156
N7—H7B···O2	0.88	2.24	2.802 (18)	121
N8—H8A···O2^v	0.88	1.96	2.821 (15)	166
N8—H8B···O4^v	0.88	2.04	2.905 (18)	168
N9—H9···Cl2	0.88	2.63	3.348 (13)	140
N10—H10···Cl4^vii	0.88	2.37	3.249 (12)	175
N11—H11A···O3	0.88	2.30	2.850 (18)	120
N11—H11A···Cl5^vi	0.88	2.83	3.426 (14)	127
N11—H11B···Cl2	0.88	2.70	3.447 (15)	143
N12—H12A···Cl9^viii	0.88	2.45	3.315 (13)	168
N12—H12B···Cl4^vii	0.88	2.65	3.529 (15)	177

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

Experimental details

Crystal data
Chemical formula	(C₄H₇N₄O)₂[Bi₂Cl₉(C₄H₇N₄O)]·H₂O
M_r	1136.43
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	11.3365 (5), 12.2486 (6), 12.7919 (6)
α, β, γ (°)	74.433 (3), 65.939 (3), 75.397 (3)
V (Å³)	1541.71 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	12.22
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.150, 0.194
No. of measured, independent and observed [I > 2σ(I)] reflections	18217, 5695, 4988
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.223, 1.10
No. of reflections	5695
No. of parameters	359
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.1568P)² + 11.6845P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	5.85, −4.41

Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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···Cl8^iv	0.88	2.71	3.451 (14)	142
N5—H5···O4^v	0.88	1.87	2.725 (16)	163
N6—H6···Cl3^vi	0.88	2.40	3.230 (12)	158
N7—H7A···Cl5^vi	0.88	2.53	3.358 (16)	156
N7—H7B···O2	0.88	2.24	2.802 (18)	121
N8—H8A···O2^v	0.88	1.96	2.821 (15)	166
N8—H8B···O4^v	0.88	2.04	2.905 (18)	168
N9—H9···Cl2	0.88	2.63	3.348 (13)	140
N10—H10···Cl4^vii	0.88	2.37	3.249 (12)	175
N11—H11A···O3	0.88	2.30	2.850 (18)	120
N11—H11A···Cl5^vi	0.88	2.83	3.426 (14)	127
N11—H11B···Cl2	0.88	2.70	3.447 (15)	143
N12—H12A···Cl9^viii	0.88	2.45	3.315 (13)	168
N12—H12B···Cl4^vii	0.88	2.65	3.529 (15)	177

Acknowledgements

The authors acknowledge financial support from Hangzhou Vocational and Technical College, China.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fu, Y.-L., Xu, Z.-W., Ren, J.-L. & Ng, S. W. (2005). Acta Cryst. E61, m1719–m1720. Web of Science CSD CrossRef IUCr Journals Google Scholar
Goforth, A. M., Smith, M. D., Peterson, L. Jr & Zur Loye, H.-C. (2004). Inorg. Chem. 43, 7042–7049. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jacobson, R. (1998). Private communication to Rigaku Corporation, Tokyo, Japan. Google Scholar
Kyriakidis, C. E., Christidis, P. C., Rentzeperis, P. J., Tossidis, I. A. & Bolos, C. A. (1990). Z. Kristallogr. 193, 101–110. CrossRef CAS Google Scholar
Rigaku (2001). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turel, I., Golic, L., Bukovec, P. & Gubina, M. (1998). Inorg. Biochem. 71, 53–60. Web of Science CrossRef CAS Google Scholar
Wu, P.-F., Tan, X.-F., Meng, X.-G., Li, D.-S., Zhu, Y.-L. & Wei, Y.-G. (2005). Acta Cryst. E61, m1506–m1508. Web of Science CSD CrossRef 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 64| Part 5| May 2008| Pages m643-m644

doi:10.1107/S1600536808009367

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(5-amino-4-amino­carbonyl-1H-imid­azol-3-ium) (5-amino-4-amino­carbonyl-1H-imidazol-3-ium-κO)-di-μ-chlorido-hepta­chlorido-dibismuth(III) mono­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(5-amino-4-aminocarbonyl-1H-imidazol-3-ium) (5-amino-4-aminocarbonyl-1H-imidazol-3-ium-κO)-di-μ-chlorido-heptachlorido-dibismuth(III) monohydrate