
Acta Cryst. (2007). E63, m3066 [ doi:10.1107/S1600536807059740 ]
The asymmetric unit of the title complex, [Bi(C10H9N2O4)2Cl]·5H2O, contains the BiIII complex and five solvent water molecules. The Bi atom is chelated by four O atoms and two N atoms of two (E)-2-{(Z)-[(4-hydroxyphenyl)oxidomethylene]hydrazono}propanoate ligands. A chloride anion completes the coordination environment, with the seven-coordinate Bi atom adopting a distorted capped octahedral geometry. The molecules are connected by extensive O-H
O hydrogen-bonding interactions involving the solvent water molecules into a two-dimensional supramolecular network. One water molecule is disordered over two sites with almost equal occupancy factors.
Pyruvic acid 4-hydroxybenzoylhydrazone (1 mmol) were added to acetone(20 ml) and then bismuth trichloride (0.5 mmol) was added. The reaction mixture was stirred for 6 h at room temperature and then filtered. Orange crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol/dichloromethane (1:1 v/v) solution over a period of two weeks (yield 90%. m.p. 450k). Anal. Calcd (%) for C20H28N4O13ClBi (Mr = 776.89): C, 30.92; H, 3.63; N, 7.21. Found (%): C, 31.06; H, 3.52; N, 7.34.
One of the water molecules is disordered over two positions with occupancies that refined to 0.486 (11) for O13, H13D and H13E, and 0.514 (11) for O13', H13F and H13G. All H atoms were placed in calculated positions, with C—H = 0.93–0.96 Å, O—H = 0.82–0.85 Å, and treated as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, O) or 1.5 Ueq(C) for the methyl group.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
| [Bi(C10H9N2O4)2Cl]·5H2O | F000 = 1520 |
| Mr = 776.89 | Dx = 1.936 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 5343 reflections |
| a = 10.2622 (10) Å | θ = 2.3–28.1º |
| b = 29.432 (3) Å | µ = 6.79 mm−1 |
| c = 9.6869 (11) Å | T = 298 (2) K |
| β = 114.331 (2)º | Block, orange |
| V = 2665.9 (5) Å3 | 0.59 × 0.18 × 0.10 mm |
| Z = 4 |
| Siemens SMART CCD area-detector diffractometer | 4682 independent reflections |
| Radiation source: fine-focus sealed tube | 3743 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.045 |
| T = 298(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→8 |
| Tmin = 0.108, Tmax = 0.550 | k = −35→32 |
| 12001 measured reflections | l = −11→11 |
| 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)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0583P)2 + 4.9896P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 4682 reflections | Δρmax = 2.01 e Å−3 |
| 358 parameters | Δρmin = −2.67 e Å−3 |
| 7 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Bi(C10H9N2O4)2Cl]·5H2O | V = 2665.9 (5) Å3 |
| Mr = 776.89 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 10.2622 (10) Å | µ = 6.79 mm−1 |
| b = 29.432 (3) Å | T = 298 (2) K |
| c = 9.6869 (11) Å | 0.59 × 0.18 × 0.10 mm |
| β = 114.331 (2)º |
| Siemens SMART CCD area-detector diffractometer | 4682 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3743 reflections with I > 2σ(I) |
| Tmin = 0.108, Tmax = 0.550 | Rint = 0.045 |
| 12001 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 7 restraints |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 2.01 e Å−3 |
| 4682 reflections | Δρmin = −2.67 e Å−3 |
| 358 parameters |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Bi1 | −0.04673 (3) | 0.168890 (9) | 0.47561 (3) | 0.02567 (12) | |
| Cl1 | −0.1881 (2) | 0.11864 (8) | 0.2294 (3) | 0.0477 (6) | |
| N1 | 0.0589 (6) | 0.2481 (2) | 0.5622 (6) | 0.0223 (13) | |
| N2 | 0.1561 (6) | 0.25210 (19) | 0.7095 (6) | 0.0243 (14) | |
| H2 | 0.1803 | 0.2780 | 0.7539 | 0.029* | |
| N3 | 0.1003 (7) | 0.0968 (2) | 0.5409 (7) | 0.0272 (14) | |
| N4 | 0.0703 (7) | 0.0622 (2) | 0.6195 (8) | 0.0343 (16) | |
| H4 | 0.1233 | 0.0384 | 0.6481 | 0.041* | |
| O1 | −0.1202 (5) | 0.22702 (16) | 0.2883 (6) | 0.0286 (12) | |
| O2 | −0.1310 (6) | 0.29888 (17) | 0.2168 (6) | 0.0358 (13) | |
| O3 | 0.1708 (6) | 0.17552 (16) | 0.7129 (6) | 0.0356 (14) | |
| O4 | 0.6275 (6) | 0.20384 (18) | 1.3799 (6) | 0.0372 (13) | |
| H4A | 0.6593 | 0.2290 | 1.4137 | 0.056* | |
| O5 | 0.1261 (6) | 0.16861 (17) | 0.3936 (6) | 0.0315 (12) | |
| O6 | 0.3224 (6) | 0.1396 (2) | 0.3877 (7) | 0.0466 (16) | |
| O7 | −0.1204 (7) | 0.10203 (19) | 0.6070 (8) | 0.0528 (18) | |
| O8 | −0.2118 (8) | −0.0677 (2) | 0.9533 (8) | 0.065 (2) | |
| H8 | −0.2786 | −0.0587 | 0.9717 | 0.098* | |
| O9 | 0.6106 (8) | 0.1415 (2) | 0.6445 (10) | 0.078 (2) | |
| H9A | 0.5349 | 0.1456 | 0.5645 | 0.093* | |
| H9B | 0.6725 | 0.1611 | 0.6473 | 0.093* | |
| O10 | 0.7055 (6) | 0.2870 (2) | 0.4876 (6) | 0.0465 (15) | |
| H10A | 0.7551 | 0.2719 | 0.5668 | 0.056* | |
| H10B | 0.7108 | 0.3148 | 0.5128 | 0.056* | |
| O11 | 0.5671 (10) | 0.1060 (3) | 0.8888 (10) | 0.111 (3) | |
| H11A | 0.5883 | 0.1176 | 0.8203 | 0.133* | |
| H11B | 0.6360 | 0.1107 | 0.9743 | 0.133* | |
| O12 | 0.4145 (15) | 0.0433 (5) | 0.9531 (14) | 0.177 (6) | |
| H12A | 0.4649 | 0.0638 | 0.9372 | 0.212* | |
| H12B | 0.4665 | 0.0199 | 0.9872 | 0.212* | |
| O13 | 0.569 (2) | 0.0642 (7) | 0.378 (2) | 0.118 (5) | 0.486 (11) |
| H13D | 0.6457 | 0.0747 | 0.4468 | 0.141* | 0.486 (11) |
| H13E | 0.5854 | 0.0381 | 0.3506 | 0.141* | 0.486 (11) |
| O13' | 0.7088 (18) | 0.0292 (6) | 0.2920 (19) | 0.118 (5) | 0.514 (11) |
| H13F | 0.7368 | 0.0536 | 0.2657 | 0.141* | 0.514 (11) |
| H13G | 0.6791 | 0.0111 | 0.2172 | 0.141* | 0.514 (11) |
| C1 | −0.0913 (8) | 0.2690 (2) | 0.3151 (8) | 0.0265 (17) | |
| C2 | 0.0044 (8) | 0.2826 (3) | 0.4759 (8) | 0.0238 (16) | |
| C3 | 0.0291 (9) | 0.3312 (2) | 0.5176 (9) | 0.037 (2) | |
| H3A | −0.0345 | 0.3408 | 0.5621 | 0.056* | |
| H3B | 0.0114 | 0.3490 | 0.4285 | 0.056* | |
| H3C | 0.1263 | 0.3355 | 0.5891 | 0.056* | |
| C4 | 0.2126 (8) | 0.2119 (2) | 0.7816 (8) | 0.0252 (16) | |
| C5 | 0.3226 (8) | 0.2133 (2) | 0.9364 (8) | 0.0255 (16) | |
| C6 | 0.3894 (8) | 0.2529 (3) | 1.0144 (9) | 0.0294 (18) | |
| H6 | 0.3659 | 0.2810 | 0.9670 | 0.035* | |
| C7 | 0.4894 (8) | 0.2496 (3) | 1.1610 (9) | 0.0352 (19) | |
| H7 | 0.5327 | 0.2760 | 1.2126 | 0.042* | |
| C8 | 0.5277 (8) | 0.2082 (3) | 1.2344 (8) | 0.0289 (17) | |
| C9 | 0.4633 (9) | 0.1687 (2) | 1.1568 (9) | 0.0337 (19) | |
| H9 | 0.4886 | 0.1406 | 1.2047 | 0.040* | |
| C10 | 0.3635 (8) | 0.1710 (2) | 1.0110 (9) | 0.0331 (19) | |
| H10 | 0.3218 | 0.1445 | 0.9600 | 0.040* | |
| C11 | 0.2214 (8) | 0.1369 (3) | 0.4249 (8) | 0.0314 (18) | |
| C12 | 0.2063 (8) | 0.0953 (3) | 0.5075 (9) | 0.0295 (17) | |
| C13 | 0.3157 (10) | 0.0584 (3) | 0.5435 (12) | 0.049 (2) | |
| H13A | 0.4053 | 0.0690 | 0.6189 | 0.074* | |
| H13B | 0.3275 | 0.0502 | 0.4534 | 0.074* | |
| H13C | 0.2846 | 0.0324 | 0.5814 | 0.074* | |
| C14 | −0.0469 (9) | 0.0674 (3) | 0.6499 (9) | 0.0328 (19) | |
| C15 | −0.0870 (9) | 0.0308 (2) | 0.7282 (9) | 0.0331 (19) | |
| C16 | −0.2006 (10) | 0.0389 (3) | 0.7675 (11) | 0.044 (2) | |
| H16 | −0.2487 | 0.0665 | 0.7424 | 0.053* | |
| C17 | −0.2436 (10) | 0.0065 (3) | 0.8435 (11) | 0.048 (2) | |
| H17 | −0.3186 | 0.0124 | 0.8710 | 0.057* | |
| C18 | −0.1741 (10) | −0.0347 (3) | 0.8779 (10) | 0.042 (2) | |
| C19 | −0.0620 (10) | −0.0439 (3) | 0.8380 (11) | 0.046 (2) | |
| H19 | −0.0164 | −0.0720 | 0.8601 | 0.055* | |
| C20 | −0.0187 (9) | −0.0110 (3) | 0.7651 (11) | 0.044 (2) | |
| H20 | 0.0579 | −0.0168 | 0.7400 | 0.053* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Bi1 | 0.02656 (17) | 0.02425 (17) | 0.02060 (17) | −0.00148 (13) | 0.00408 (12) | 0.00184 (12) |
| Cl1 | 0.0423 (12) | 0.0460 (13) | 0.0384 (13) | −0.0040 (10) | 0.0002 (10) | −0.0123 (10) |
| N1 | 0.021 (3) | 0.022 (3) | 0.015 (3) | −0.003 (3) | −0.001 (2) | 0.002 (2) |
| N2 | 0.028 (3) | 0.016 (3) | 0.018 (3) | −0.004 (3) | −0.002 (3) | −0.003 (2) |
| N3 | 0.033 (3) | 0.022 (3) | 0.019 (3) | −0.002 (3) | 0.003 (3) | 0.002 (3) |
| N4 | 0.041 (4) | 0.022 (3) | 0.041 (4) | 0.003 (3) | 0.018 (3) | 0.009 (3) |
| O1 | 0.035 (3) | 0.015 (3) | 0.024 (3) | 0.001 (2) | 0.000 (2) | 0.005 (2) |
| O2 | 0.043 (3) | 0.029 (3) | 0.024 (3) | 0.000 (3) | 0.002 (3) | 0.007 (2) |
| O3 | 0.034 (3) | 0.023 (3) | 0.030 (3) | 0.004 (2) | −0.007 (2) | −0.002 (2) |
| O4 | 0.040 (3) | 0.038 (3) | 0.018 (3) | −0.002 (3) | −0.003 (2) | −0.001 (2) |
| O5 | 0.031 (3) | 0.039 (3) | 0.020 (3) | −0.004 (3) | 0.006 (2) | 0.004 (2) |
| O6 | 0.037 (3) | 0.052 (4) | 0.058 (4) | 0.000 (3) | 0.027 (3) | 0.005 (3) |
| O7 | 0.059 (4) | 0.035 (4) | 0.083 (5) | 0.008 (3) | 0.048 (4) | 0.020 (3) |
| O8 | 0.088 (5) | 0.039 (4) | 0.082 (6) | −0.003 (4) | 0.050 (5) | 0.022 (4) |
| O9 | 0.054 (4) | 0.058 (5) | 0.112 (7) | 0.004 (4) | 0.025 (5) | 0.029 (5) |
| O10 | 0.048 (4) | 0.047 (4) | 0.029 (3) | −0.007 (3) | 0.000 (3) | −0.003 (3) |
| O11 | 0.107 (7) | 0.160 (10) | 0.070 (6) | −0.027 (7) | 0.041 (6) | −0.032 (6) |
| O12 | 0.219 (10) | 0.168 (9) | 0.208 (10) | 0.014 (7) | 0.153 (8) | 0.041 (7) |
| O13 | 0.104 (10) | 0.105 (10) | 0.127 (13) | −0.032 (9) | 0.031 (9) | 0.044 (9) |
| O13' | 0.104 (10) | 0.105 (10) | 0.127 (13) | −0.032 (9) | 0.031 (9) | 0.044 (9) |
| C1 | 0.022 (4) | 0.029 (4) | 0.024 (4) | 0.007 (3) | 0.004 (3) | 0.008 (3) |
| C2 | 0.022 (3) | 0.029 (4) | 0.019 (4) | −0.004 (3) | 0.007 (3) | −0.001 (3) |
| C3 | 0.040 (5) | 0.029 (4) | 0.035 (5) | 0.002 (4) | 0.008 (4) | 0.000 (4) |
| C4 | 0.029 (4) | 0.015 (4) | 0.028 (4) | 0.001 (3) | 0.007 (3) | 0.002 (3) |
| C5 | 0.024 (4) | 0.029 (4) | 0.017 (4) | 0.002 (3) | 0.003 (3) | 0.000 (3) |
| C6 | 0.025 (4) | 0.027 (4) | 0.028 (4) | 0.001 (3) | 0.003 (3) | 0.000 (3) |
| C7 | 0.034 (4) | 0.034 (5) | 0.029 (5) | −0.006 (4) | 0.004 (4) | −0.003 (4) |
| C8 | 0.029 (4) | 0.036 (4) | 0.020 (4) | 0.004 (4) | 0.008 (3) | 0.002 (3) |
| C9 | 0.036 (4) | 0.024 (4) | 0.028 (4) | 0.006 (4) | 0.000 (4) | 0.009 (3) |
| C10 | 0.028 (4) | 0.025 (4) | 0.034 (5) | −0.001 (3) | 0.001 (4) | −0.002 (3) |
| C11 | 0.029 (4) | 0.040 (5) | 0.017 (4) | −0.004 (4) | 0.001 (3) | −0.007 (3) |
| C12 | 0.027 (4) | 0.026 (4) | 0.032 (5) | −0.004 (3) | 0.009 (3) | −0.001 (3) |
| C13 | 0.053 (6) | 0.033 (5) | 0.064 (7) | 0.011 (4) | 0.026 (5) | 0.007 (4) |
| C14 | 0.038 (5) | 0.022 (4) | 0.033 (5) | 0.004 (4) | 0.010 (4) | 0.003 (3) |
| C15 | 0.043 (5) | 0.016 (4) | 0.039 (5) | −0.002 (4) | 0.015 (4) | 0.002 (3) |
| C16 | 0.055 (6) | 0.026 (4) | 0.053 (6) | 0.007 (4) | 0.025 (5) | 0.010 (4) |
| C17 | 0.057 (5) | 0.034 (5) | 0.068 (7) | 0.003 (5) | 0.042 (5) | 0.010 (5) |
| C18 | 0.054 (5) | 0.035 (5) | 0.036 (5) | −0.003 (4) | 0.018 (4) | 0.007 (4) |
| C19 | 0.061 (6) | 0.023 (4) | 0.054 (6) | 0.005 (4) | 0.024 (5) | 0.008 (4) |
| C20 | 0.046 (5) | 0.025 (4) | 0.062 (6) | 0.004 (4) | 0.023 (5) | 0.011 (4) |
| Bi1—O5 | 2.222 (5) | O13'—H13F | 0.8501 |
| Bi1—O1 | 2.379 (5) | O13'—H13G | 0.8499 |
| Bi1—O3 | 2.465 (5) | C1—C2 | 1.514 (10) |
| Bi1—N3 | 2.529 (6) | C2—C3 | 1.481 (10) |
| Bi1—N1 | 2.562 (6) | C3—H3A | 0.9600 |
| Bi1—O7 | 2.619 (5) | C3—H3B | 0.9600 |
| Bi1—Cl1 | 2.670 (2) | C3—H3C | 0.9600 |
| N1—C2 | 1.287 (9) | C4—C5 | 1.460 (10) |
| N1—N2 | 1.368 (8) | C5—C6 | 1.404 (10) |
| N2—C4 | 1.376 (8) | C5—C10 | 1.411 (10) |
| N2—H2 | 0.8600 | C6—C7 | 1.370 (11) |
| N3—C12 | 1.257 (9) | C6—H6 | 0.9300 |
| N3—N4 | 1.380 (9) | C7—C8 | 1.384 (11) |
| N4—C14 | 1.358 (10) | C7—H7 | 0.9300 |
| N4—H4 | 0.8600 | C8—C9 | 1.395 (10) |
| O1—C1 | 1.272 (9) | C9—C10 | 1.362 (11) |
| O2—C1 | 1.236 (8) | C9—H9 | 0.9300 |
| O3—C4 | 1.239 (8) | C10—H10 | 0.9300 |
| O4—C8 | 1.365 (9) | C11—C12 | 1.505 (11) |
| O4—H4A | 0.8200 | C12—C13 | 1.497 (11) |
| O5—C11 | 1.294 (9) | C13—H13A | 0.9600 |
| O6—C11 | 1.232 (9) | C13—H13B | 0.9600 |
| O7—C14 | 1.234 (9) | C13—H13C | 0.9600 |
| O8—C18 | 1.364 (10) | C14—C15 | 1.470 (11) |
| O8—H8 | 0.8200 | C15—C20 | 1.388 (11) |
| O9—H9A | 0.8500 | C15—C16 | 1.389 (12) |
| O9—H9B | 0.8501 | C16—C17 | 1.383 (12) |
| O10—H10A | 0.8500 | C16—H16 | 0.9300 |
| O10—H10B | 0.8502 | C17—C18 | 1.376 (12) |
| O11—H11A | 0.8501 | C17—H17 | 0.9300 |
| O11—H11B | 0.8500 | C18—C19 | 1.383 (13) |
| O12—H12A | 0.8500 | C19—C20 | 1.377 (12) |
| O12—H12B | 0.8498 | C19—H19 | 0.9300 |
| O13—H13D | 0.8501 | C20—H20 | 0.9300 |
| O13—H13E | 0.8501 | ||
| O5—Bi1—O1 | 77.22 (18) | H3B—C3—H3C | 109.5 |
| O5—Bi1—O3 | 77.6 (2) | O3—C4—N2 | 119.3 (7) |
| O1—Bi1—O3 | 122.34 (17) | O3—C4—C5 | 121.7 (6) |
| O5—Bi1—N3 | 66.70 (19) | N2—C4—C5 | 118.9 (6) |
| O1—Bi1—N3 | 139.76 (19) | C6—C5—C10 | 118.6 (7) |
| O3—Bi1—N3 | 67.38 (17) | C6—C5—C4 | 125.1 (7) |
| O5—Bi1—N1 | 80.10 (19) | C10—C5—C4 | 116.3 (6) |
| O1—Bi1—N1 | 63.50 (17) | C7—C6—C5 | 119.4 (7) |
| O3—Bi1—N1 | 61.59 (16) | C7—C6—H6 | 120.3 |
| N3—Bi1—N1 | 123.59 (19) | C5—C6—H6 | 120.3 |
| O5—Bi1—O7 | 127.15 (18) | C6—C7—C8 | 121.7 (7) |
| O1—Bi1—O7 | 147.87 (19) | C6—C7—H7 | 119.1 |
| O3—Bi1—O7 | 86.4 (2) | C8—C7—H7 | 119.1 |
| N3—Bi1—O7 | 60.64 (19) | O4—C8—C7 | 123.2 (7) |
| N1—Bi1—O7 | 133.8 (2) | O4—C8—C9 | 117.7 (7) |
| O5—Bi1—Cl1 | 84.18 (14) | C7—C8—C9 | 119.1 (7) |
| O1—Bi1—Cl1 | 80.34 (13) | C10—C9—C8 | 120.2 (7) |
| O3—Bi1—Cl1 | 145.78 (13) | C10—C9—H9 | 119.9 |
| N3—Bi1—Cl1 | 78.89 (14) | C8—C9—H9 | 119.9 |
| N1—Bi1—Cl1 | 142.88 (14) | C9—C10—C5 | 120.9 (7) |
| O7—Bi1—Cl1 | 81.87 (17) | C9—C10—H10 | 119.5 |
| C2—N1—N2 | 123.0 (6) | C5—C10—H10 | 119.5 |
| C2—N1—Bi1 | 119.5 (5) | O6—C11—O5 | 122.1 (8) |
| N2—N1—Bi1 | 116.6 (4) | O6—C11—C12 | 119.4 (7) |
| N1—N2—C4 | 115.4 (6) | O5—C11—C12 | 118.5 (7) |
| N1—N2—H2 | 122.3 | N3—C12—C13 | 127.6 (7) |
| C4—N2—H2 | 122.3 | N3—C12—C11 | 113.5 (7) |
| C12—N3—N4 | 122.1 (7) | C13—C12—C11 | 118.9 (7) |
| C12—N3—Bi1 | 117.0 (5) | C12—C13—H13A | 109.5 |
| N4—N3—Bi1 | 120.8 (5) | C12—C13—H13B | 109.5 |
| C14—N4—N3 | 117.0 (6) | H13A—C13—H13B | 109.5 |
| C14—N4—H4 | 121.5 | C12—C13—H13C | 109.5 |
| N3—N4—H4 | 121.5 | H13A—C13—H13C | 109.5 |
| C1—O1—Bi1 | 124.7 (5) | H13B—C13—H13C | 109.5 |
| C4—O3—Bi1 | 123.3 (4) | O7—C14—N4 | 119.6 (7) |
| C8—O4—H4A | 109.5 | O7—C14—C15 | 121.0 (7) |
| C11—O5—Bi1 | 123.8 (5) | N4—C14—C15 | 119.3 (7) |
| C14—O7—Bi1 | 121.7 (5) | C20—C15—C16 | 118.2 (7) |
| C18—O8—H8 | 109.5 | C20—C15—C14 | 124.3 (7) |
| H9A—O9—H9B | 108.8 | C16—C15—C14 | 117.6 (7) |
| H10A—O10—H10B | 107.6 | C17—C16—C15 | 121.1 (8) |
| H11A—O11—H11B | 108.6 | C17—C16—H16 | 119.5 |
| H12A—O12—H12B | 108.3 | C15—C16—H16 | 119.5 |
| H13D—O13—H13E | 110.0 | C18—C17—C16 | 119.3 (8) |
| H13F—O13'—H13G | 108.7 | C18—C17—H17 | 120.3 |
| O2—C1—O1 | 124.0 (7) | C16—C17—H17 | 120.3 |
| O2—C1—C2 | 118.2 (7) | O8—C18—C17 | 121.6 (8) |
| O1—C1—C2 | 117.7 (6) | O8—C18—C19 | 117.5 (8) |
| N1—C2—C3 | 127.3 (7) | C17—C18—C19 | 120.8 (8) |
| N1—C2—C1 | 112.6 (6) | C20—C19—C18 | 119.1 (8) |
| C3—C2—C1 | 120.1 (6) | C20—C19—H19 | 120.5 |
| C2—C3—H3A | 109.5 | C18—C19—H19 | 120.5 |
| C2—C3—H3B | 109.5 | C19—C20—C15 | 121.5 (8) |
| H3A—C3—H3B | 109.5 | C19—C20—H20 | 119.3 |
| C2—C3—H3C | 109.5 | C15—C20—H20 | 119.3 |
| H3A—C3—H3C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O13'—H13G···O12i | 0.85 | 2.21 | 3.052 (18) | 170 |
| O13'—H13F···Cl1ii | 0.85 | 2.15 | 2.991 (16) | 172 |
| O13—H13D···O7ii | 0.85 | 2.40 | 3.24 (2) | 169 |
| O12—H12B···O12iii | 0.85 | 2.17 | 3.01 (3) | 173 |
| O12—H12A···O11 | 0.85 | 1.81 | 2.656 (15) | 176 |
| O11—H11B···Cl1iv | 0.85 | 2.40 | 3.241 (9) | 173 |
| O11—H11A···O9 | 0.85 | 1.94 | 2.785 (12) | 172 |
| O10—H10B···Cl1v | 0.85 | 2.74 | 3.505 (6) | 150 |
| O10—H10A···O2v | 0.85 | 2.53 | 3.326 (8) | 156 |
| O10—H10A···O1v | 0.85 | 2.00 | 2.749 (7) | 147 |
| O9—H9B···O2v | 0.85 | 2.19 | 3.013 (9) | 163 |
| O9—H9A···O6 | 0.85 | 2.15 | 2.979 (10) | 163 |
| O8—H8···O12vi | 0.82 | 1.88 | 2.688 (14) | 170 |
| O4—H4A···O10vii | 0.82 | 1.84 | 2.651 (8) | 172 |
| N4—H4···O13'i | 0.86 | 2.54 | 3.39 (2) | 173 |
| N2—H2···O5viii | 0.86 | 2.29 | 3.029 (8) | 145 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+2; (iv) x+1, y, z+1; (v) x+1, −y+1/2, z+1/2; (vi) −x, −y, −z+2; (vii) x, y, z+1; (viii) x, −y+1/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O13'—H13G···O12i | 0.85 | 2.21 | 3.052 (18) | 170 |
| O13'—H13F···Cl1ii | 0.85 | 2.15 | 2.991 (16) | 172 |
| O13—H13D···O7ii | 0.85 | 2.40 | 3.24 (2) | 169 |
| O12—H12B···O12iii | 0.85 | 2.17 | 3.01 (3) | 173 |
| O12—H12A···O11 | 0.85 | 1.81 | 2.656 (15) | 176 |
| O11—H11B···Cl1iv | 0.85 | 2.40 | 3.241 (9) | 173 |
| O11—H11A···O9 | 0.85 | 1.94 | 2.785 (12) | 172 |
| O10—H10B···Cl1v | 0.85 | 2.74 | 3.505 (6) | 150 |
| O10—H10A···O2v | 0.85 | 2.53 | 3.326 (8) | 156 |
| O10—H10A···O1v | 0.85 | 2.00 | 2.749 (7) | 147 |
| O9—H9B···O2v | 0.85 | 2.19 | 3.013 (9) | 163 |
| O9—H9A···O6 | 0.85 | 2.15 | 2.979 (10) | 163 |
| O8—H8···O12vi | 0.82 | 1.88 | 2.688 (14) | 170 |
| O4—H4A···O10vii | 0.82 | 1.84 | 2.651 (8) | 172 |
| N4—H4···O13'i | 0.86 | 2.54 | 3.39 (2) | 173 |
| N2—H2···O5viii | 0.86 | 2.29 | 3.029 (8) | 145 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+2; (iv) x+1, y, z+1; (v) x+1, −y+1/2, z+1/2; (vi) −x, −y, −z+2; (vii) x, y, z+1; (viii) x, −y+1/2, z+1/2. |
We acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystal Materials, Shandong University, People's Republic of China.
Hong, M., Yin, H., Wang, D. & Li, G. (2005). Acta Cryst. E61, m1006–m1008.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
In the title complex, (I), the Bi(III) atom exists in a distorted capped octahedral coordination environment in which two tridentate pyruvic acid 4-hydroxybenzoylhydrazone ligands and a chloride anion coordinate to each Bi(III) center. Atoms O1, O7 lie in axial positions, with the axial angleO1—Bi1—O7 147.87 (19)°, deviating substantially from the linear value of 180° and atoms N1, N3, O3, Cl1 in the equatorial plane. The remaining O5 atom caps the N1/N3/O3 face of this octahedron, giving a highly distorted capped octahedral coordination geometry.
The water molecules play a significant role in the crystal packing linking the complex molecules by O—H···O hydrogen bonds to form a two-dimensional supramolecular network.