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
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
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 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
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Refinement
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Data collection: CrystalClear (Rigaku, 2001); cell 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
10.1107/S1600536808009367/ci2573sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009367/ci2573Isup2.hkl
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.
Water H atoms were located in a difference map and their positional parameters were refined with a O-H distance restraint of 0.85 (3) Å. All other H atoms were placed at calculated positions (N-H = 0.88 Å and C-H = 0.95 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N,O). The highest residual density peak is located 0.89 Å from atom Bi1 and the deepest hole is located 0.77 Å from atom Bi2.
Data collection: CrystalClear (Rigaku, 2001); cell
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).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. |
(C4H7N4O)2[Bi2Cl9(C4H7N4O)]·H2O | Z = 2 |
Mr = 1136.43 | F(000) = 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 = 1.8–25.5° |
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 |
Rigaku Mercury diffractometer | 5695 independent reflections |
Radiation source: fine-focus sealed tube | 4988 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.5°, θmin = 1.8° |
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) |
(C4H7N4O)2[Bi2Cl9(C4H7N4O)]·H2O | γ = 75.397 (3)° |
Mr = 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)° |
Rigaku Mercury diffractometer | 5695 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 4988 reflections with I > 2σ(I) |
Tmin = 0.150, Tmax = 0.194 | Rint = 0.063 |
18217 measured reflections |
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(Fo2) + (0.1568P)2 + 11.6845P] where P = (Fo2 + 2Fc2)/3 |
5695 reflections | Δρmax = 5.85 e Å−3 |
359 parameters | Δρmin = −4.41 e Å−3 |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.150, 0.194 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18217, 5695, 4988 |
Rint | 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(Fo2) + (0.1568P)2 + 11.6845P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (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).
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) |
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) 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. |
Acknowledgements
The authors acknowledge financial support from Hangzhou Vocational and Technical College, China.
References
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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.
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).