supplementary materials


sj2427 scheme

Acta Cryst. (2007). E63, m3066    [ doi:10.1107/S1600536807059740 ]

Chloridobis((E)-2-{(Z)-[(4-hydroxyphenyl)(oxido)methylene]hydrazono}propanoato)bismuth(III) pentahydrate

J. Zhai, H. Yin, F. Li and D. Wang

Abstract top

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.

Comment top

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.

Related literature top

For a related structure, see: Hong et al. (2005)

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Crystal packing of (I),showing a two-dimensional supramolecular network, linked by O—H···O hydrogen bonds (dashed lines). H atoms have been omitted for clarity.
Chloridobis((E)-2-{(Z)-[(4- hydroxyphenyl)(oxido)methylene]hydrazono}propanoato)bismuth(III) pentahydrate top
Crystal data top
[Bi(C10H9N2O4)2Cl]·5H2OF000 = 1520
Mr = 776.89Dx = 1.936 Mg m3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5343 reflections
a = 10.2622 (10) Åθ = 2.3–28.1º
b = 29.432 (3) ŵ = 6.79 mm1
c = 9.6869 (11) ÅT = 298 (2) K
β = 114.331 (2)ºBlock, orange
V = 2665.9 (5) Å30.59 × 0.18 × 0.10 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
4682 independent reflections
Radiation source: fine-focus sealed tube3743 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 12→8
Tmin = 0.108, Tmax = 0.550k = 35→32
12001 measured reflectionsl = 11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 2.01 e Å3
358 parametersΔρmin = 2.67 e Å3
7 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Bi(C10H9N2O4)2Cl]·5H2OV = 2665.9 (5) Å3
Mr = 776.89Z = 4
Monoclinic, P21/cMo Kα
a = 10.2622 (10) ŵ = 6.79 mm1
b = 29.432 (3) ÅT = 298 (2) K
c = 9.6869 (11) Å0.59 × 0.18 × 0.10 mm
β = 114.331 (2)º
Data collection top
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 = 0.550Rint = 0.045
12001 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0417 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.01Δρmax = 2.01 e Å3
4682 reflectionsΔρmin = 2.67 e Å3
358 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Bi10.04673 (3)0.168890 (9)0.47561 (3)0.02567 (12)
Cl10.1881 (2)0.11864 (8)0.2294 (3)0.0477 (6)
N10.0589 (6)0.2481 (2)0.5622 (6)0.0223 (13)
N20.1561 (6)0.25210 (19)0.7095 (6)0.0243 (14)
H20.18030.27800.75390.029*
N30.1003 (7)0.0968 (2)0.5409 (7)0.0272 (14)
N40.0703 (7)0.0622 (2)0.6195 (8)0.0343 (16)
H40.12330.03840.64810.041*
O10.1202 (5)0.22702 (16)0.2883 (6)0.0286 (12)
O20.1310 (6)0.29888 (17)0.2168 (6)0.0358 (13)
O30.1708 (6)0.17552 (16)0.7129 (6)0.0356 (14)
O40.6275 (6)0.20384 (18)1.3799 (6)0.0372 (13)
H4A0.65930.22901.41370.056*
O50.1261 (6)0.16861 (17)0.3936 (6)0.0315 (12)
O60.3224 (6)0.1396 (2)0.3877 (7)0.0466 (16)
O70.1204 (7)0.10203 (19)0.6070 (8)0.0528 (18)
O80.2118 (8)0.0677 (2)0.9533 (8)0.065 (2)
H80.27860.05870.97170.098*
O90.6106 (8)0.1415 (2)0.6445 (10)0.078 (2)
H9A0.53490.14560.56450.093*
H9B0.67250.16110.64730.093*
O100.7055 (6)0.2870 (2)0.4876 (6)0.0465 (15)
H10A0.75510.27190.56680.056*
H10B0.71080.31480.51280.056*
O110.5671 (10)0.1060 (3)0.8888 (10)0.111 (3)
H11A0.58830.11760.82030.133*
H11B0.63600.11070.97430.133*
O120.4145 (15)0.0433 (5)0.9531 (14)0.177 (6)
H12A0.46490.06380.93720.212*
H12B0.46650.01990.98720.212*
O130.569 (2)0.0642 (7)0.378 (2)0.118 (5)0.486 (11)
H13D0.64570.07470.44680.141*0.486 (11)
H13E0.58540.03810.35060.141*0.486 (11)
O13'0.7088 (18)0.0292 (6)0.2920 (19)0.118 (5)0.514 (11)
H13F0.73680.05360.26570.141*0.514 (11)
H13G0.67910.01110.21720.141*0.514 (11)
C10.0913 (8)0.2690 (2)0.3151 (8)0.0265 (17)
C20.0044 (8)0.2826 (3)0.4759 (8)0.0238 (16)
C30.0291 (9)0.3312 (2)0.5176 (9)0.037 (2)
H3A0.03450.34080.56210.056*
H3B0.01140.34900.42850.056*
H3C0.12630.33550.58910.056*
C40.2126 (8)0.2119 (2)0.7816 (8)0.0252 (16)
C50.3226 (8)0.2133 (2)0.9364 (8)0.0255 (16)
C60.3894 (8)0.2529 (3)1.0144 (9)0.0294 (18)
H60.36590.28100.96700.035*
C70.4894 (8)0.2496 (3)1.1610 (9)0.0352 (19)
H70.53270.27601.21260.042*
C80.5277 (8)0.2082 (3)1.2344 (8)0.0289 (17)
C90.4633 (9)0.1687 (2)1.1568 (9)0.0337 (19)
H90.48860.14061.20470.040*
C100.3635 (8)0.1710 (2)1.0110 (9)0.0331 (19)
H100.32180.14450.96000.040*
C110.2214 (8)0.1369 (3)0.4249 (8)0.0314 (18)
C120.2063 (8)0.0953 (3)0.5075 (9)0.0295 (17)
C130.3157 (10)0.0584 (3)0.5435 (12)0.049 (2)
H13A0.40530.06900.61890.074*
H13B0.32750.05020.45340.074*
H13C0.28460.03240.58140.074*
C140.0469 (9)0.0674 (3)0.6499 (9)0.0328 (19)
C150.0870 (9)0.0308 (2)0.7282 (9)0.0331 (19)
C160.2006 (10)0.0389 (3)0.7675 (11)0.044 (2)
H160.24870.06650.74240.053*
C170.2436 (10)0.0065 (3)0.8435 (11)0.048 (2)
H170.31860.01240.87100.057*
C180.1741 (10)0.0347 (3)0.8779 (10)0.042 (2)
C190.0620 (10)0.0439 (3)0.8380 (11)0.046 (2)
H190.01640.07200.86010.055*
C200.0187 (9)0.0110 (3)0.7651 (11)0.044 (2)
H200.05790.01680.74000.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.02656 (17)0.02425 (17)0.02060 (17)0.00148 (13)0.00408 (12)0.00184 (12)
Cl10.0423 (12)0.0460 (13)0.0384 (13)0.0040 (10)0.0002 (10)0.0123 (10)
N10.021 (3)0.022 (3)0.015 (3)0.003 (3)0.001 (2)0.002 (2)
N20.028 (3)0.016 (3)0.018 (3)0.004 (3)0.002 (3)0.003 (2)
N30.033 (3)0.022 (3)0.019 (3)0.002 (3)0.003 (3)0.002 (3)
N40.041 (4)0.022 (3)0.041 (4)0.003 (3)0.018 (3)0.009 (3)
O10.035 (3)0.015 (3)0.024 (3)0.001 (2)0.000 (2)0.005 (2)
O20.043 (3)0.029 (3)0.024 (3)0.000 (3)0.002 (3)0.007 (2)
O30.034 (3)0.023 (3)0.030 (3)0.004 (2)0.007 (2)0.002 (2)
O40.040 (3)0.038 (3)0.018 (3)0.002 (3)0.003 (2)0.001 (2)
O50.031 (3)0.039 (3)0.020 (3)0.004 (3)0.006 (2)0.004 (2)
O60.037 (3)0.052 (4)0.058 (4)0.000 (3)0.027 (3)0.005 (3)
O70.059 (4)0.035 (4)0.083 (5)0.008 (3)0.048 (4)0.020 (3)
O80.088 (5)0.039 (4)0.082 (6)0.003 (4)0.050 (5)0.022 (4)
O90.054 (4)0.058 (5)0.112 (7)0.004 (4)0.025 (5)0.029 (5)
O100.048 (4)0.047 (4)0.029 (3)0.007 (3)0.000 (3)0.003 (3)
O110.107 (7)0.160 (10)0.070 (6)0.027 (7)0.041 (6)0.032 (6)
O120.219 (10)0.168 (9)0.208 (10)0.014 (7)0.153 (8)0.041 (7)
O130.104 (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)
C10.022 (4)0.029 (4)0.024 (4)0.007 (3)0.004 (3)0.008 (3)
C20.022 (3)0.029 (4)0.019 (4)0.004 (3)0.007 (3)0.001 (3)
C30.040 (5)0.029 (4)0.035 (5)0.002 (4)0.008 (4)0.000 (4)
C40.029 (4)0.015 (4)0.028 (4)0.001 (3)0.007 (3)0.002 (3)
C50.024 (4)0.029 (4)0.017 (4)0.002 (3)0.003 (3)0.000 (3)
C60.025 (4)0.027 (4)0.028 (4)0.001 (3)0.003 (3)0.000 (3)
C70.034 (4)0.034 (5)0.029 (5)0.006 (4)0.004 (4)0.003 (4)
C80.029 (4)0.036 (4)0.020 (4)0.004 (4)0.008 (3)0.002 (3)
C90.036 (4)0.024 (4)0.028 (4)0.006 (4)0.000 (4)0.009 (3)
C100.028 (4)0.025 (4)0.034 (5)0.001 (3)0.001 (4)0.002 (3)
C110.029 (4)0.040 (5)0.017 (4)0.004 (4)0.001 (3)0.007 (3)
C120.027 (4)0.026 (4)0.032 (5)0.004 (3)0.009 (3)0.001 (3)
C130.053 (6)0.033 (5)0.064 (7)0.011 (4)0.026 (5)0.007 (4)
C140.038 (5)0.022 (4)0.033 (5)0.004 (4)0.010 (4)0.003 (3)
C150.043 (5)0.016 (4)0.039 (5)0.002 (4)0.015 (4)0.002 (3)
C160.055 (6)0.026 (4)0.053 (6)0.007 (4)0.025 (5)0.010 (4)
C170.057 (5)0.034 (5)0.068 (7)0.003 (5)0.042 (5)0.010 (5)
C180.054 (5)0.035 (5)0.036 (5)0.003 (4)0.018 (4)0.007 (4)
C190.061 (6)0.023 (4)0.054 (6)0.005 (4)0.024 (5)0.008 (4)
C200.046 (5)0.025 (4)0.062 (6)0.004 (4)0.023 (5)0.011 (4)
Geometric parameters (Å, °) top
Bi1—O52.222 (5)O13'—H13F0.8501
Bi1—O12.379 (5)O13'—H13G0.8499
Bi1—O32.465 (5)C1—C21.514 (10)
Bi1—N32.529 (6)C2—C31.481 (10)
Bi1—N12.562 (6)C3—H3A0.9600
Bi1—O72.619 (5)C3—H3B0.9600
Bi1—Cl12.670 (2)C3—H3C0.9600
N1—C21.287 (9)C4—C51.460 (10)
N1—N21.368 (8)C5—C61.404 (10)
N2—C41.376 (8)C5—C101.411 (10)
N2—H20.8600C6—C71.370 (11)
N3—C121.257 (9)C6—H60.9300
N3—N41.380 (9)C7—C81.384 (11)
N4—C141.358 (10)C7—H70.9300
N4—H40.8600C8—C91.395 (10)
O1—C11.272 (9)C9—C101.362 (11)
O2—C11.236 (8)C9—H90.9300
O3—C41.239 (8)C10—H100.9300
O4—C81.365 (9)C11—C121.505 (11)
O4—H4A0.8200C12—C131.497 (11)
O5—C111.294 (9)C13—H13A0.9600
O6—C111.232 (9)C13—H13B0.9600
O7—C141.234 (9)C13—H13C0.9600
O8—C181.364 (10)C14—C151.470 (11)
O8—H80.8200C15—C201.388 (11)
O9—H9A0.8500C15—C161.389 (12)
O9—H9B0.8501C16—C171.383 (12)
O10—H10A0.8500C16—H160.9300
O10—H10B0.8502C17—C181.376 (12)
O11—H11A0.8501C17—H170.9300
O11—H11B0.8500C18—C191.383 (13)
O12—H12A0.8500C19—C201.377 (12)
O12—H12B0.8498C19—H190.9300
O13—H13D0.8501C20—H200.9300
O13—H13E0.8501
O5—Bi1—O177.22 (18)H3B—C3—H3C109.5
O5—Bi1—O377.6 (2)O3—C4—N2119.3 (7)
O1—Bi1—O3122.34 (17)O3—C4—C5121.7 (6)
O5—Bi1—N366.70 (19)N2—C4—C5118.9 (6)
O1—Bi1—N3139.76 (19)C6—C5—C10118.6 (7)
O3—Bi1—N367.38 (17)C6—C5—C4125.1 (7)
O5—Bi1—N180.10 (19)C10—C5—C4116.3 (6)
O1—Bi1—N163.50 (17)C7—C6—C5119.4 (7)
O3—Bi1—N161.59 (16)C7—C6—H6120.3
N3—Bi1—N1123.59 (19)C5—C6—H6120.3
O5—Bi1—O7127.15 (18)C6—C7—C8121.7 (7)
O1—Bi1—O7147.87 (19)C6—C7—H7119.1
O3—Bi1—O786.4 (2)C8—C7—H7119.1
N3—Bi1—O760.64 (19)O4—C8—C7123.2 (7)
N1—Bi1—O7133.8 (2)O4—C8—C9117.7 (7)
O5—Bi1—Cl184.18 (14)C7—C8—C9119.1 (7)
O1—Bi1—Cl180.34 (13)C10—C9—C8120.2 (7)
O3—Bi1—Cl1145.78 (13)C10—C9—H9119.9
N3—Bi1—Cl178.89 (14)C8—C9—H9119.9
N1—Bi1—Cl1142.88 (14)C9—C10—C5120.9 (7)
O7—Bi1—Cl181.87 (17)C9—C10—H10119.5
C2—N1—N2123.0 (6)C5—C10—H10119.5
C2—N1—Bi1119.5 (5)O6—C11—O5122.1 (8)
N2—N1—Bi1116.6 (4)O6—C11—C12119.4 (7)
N1—N2—C4115.4 (6)O5—C11—C12118.5 (7)
N1—N2—H2122.3N3—C12—C13127.6 (7)
C4—N2—H2122.3N3—C12—C11113.5 (7)
C12—N3—N4122.1 (7)C13—C12—C11118.9 (7)
C12—N3—Bi1117.0 (5)C12—C13—H13A109.5
N4—N3—Bi1120.8 (5)C12—C13—H13B109.5
C14—N4—N3117.0 (6)H13A—C13—H13B109.5
C14—N4—H4121.5C12—C13—H13C109.5
N3—N4—H4121.5H13A—C13—H13C109.5
C1—O1—Bi1124.7 (5)H13B—C13—H13C109.5
C4—O3—Bi1123.3 (4)O7—C14—N4119.6 (7)
C8—O4—H4A109.5O7—C14—C15121.0 (7)
C11—O5—Bi1123.8 (5)N4—C14—C15119.3 (7)
C14—O7—Bi1121.7 (5)C20—C15—C16118.2 (7)
C18—O8—H8109.5C20—C15—C14124.3 (7)
H9A—O9—H9B108.8C16—C15—C14117.6 (7)
H10A—O10—H10B107.6C17—C16—C15121.1 (8)
H11A—O11—H11B108.6C17—C16—H16119.5
H12A—O12—H12B108.3C15—C16—H16119.5
H13D—O13—H13E110.0C18—C17—C16119.3 (8)
H13F—O13'—H13G108.7C18—C17—H17120.3
O2—C1—O1124.0 (7)C16—C17—H17120.3
O2—C1—C2118.2 (7)O8—C18—C17121.6 (8)
O1—C1—C2117.7 (6)O8—C18—C19117.5 (8)
N1—C2—C3127.3 (7)C17—C18—C19120.8 (8)
N1—C2—C1112.6 (6)C20—C19—C18119.1 (8)
C3—C2—C1120.1 (6)C20—C19—H19120.5
C2—C3—H3A109.5C18—C19—H19120.5
C2—C3—H3B109.5C19—C20—C15121.5 (8)
H3A—C3—H3B109.5C19—C20—H20119.3
C2—C3—H3C109.5C15—C20—H20119.3
H3A—C3—H3C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O13'—H13G···O12i0.852.213.052 (18)170
O13'—H13F···Cl1ii0.852.152.991 (16)172
O13—H13D···O7ii0.852.403.24 (2)169
O12—H12B···O12iii0.852.173.01 (3)173
O12—H12A···O110.851.812.656 (15)176
O11—H11B···Cl1iv0.852.403.241 (9)173
O11—H11A···O90.851.942.785 (12)172
O10—H10B···Cl1v0.852.743.505 (6)150
O10—H10A···O2v0.852.533.326 (8)156
O10—H10A···O1v0.852.002.749 (7)147
O9—H9B···O2v0.852.193.013 (9)163
O9—H9A···O60.852.152.979 (10)163
O8—H8···O12vi0.821.882.688 (14)170
O4—H4A···O10vii0.821.842.651 (8)172
N4—H4···O13'i0.862.543.39 (2)173
N2—H2···O5viii0.862.293.029 (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.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O13'—H13G···O12i0.852.213.052 (18)170
O13'—H13F···Cl1ii0.852.152.991 (16)172
O13—H13D···O7ii0.852.403.24 (2)169
O12—H12B···O12iii0.852.173.01 (3)173
O12—H12A···O110.851.812.656 (15)176
O11—H11B···Cl1iv0.852.403.241 (9)173
O11—H11A···O90.851.942.785 (12)172
O10—H10B···Cl1v0.852.743.505 (6)150
O10—H10A···O2v0.852.533.326 (8)156
O10—H10A···O1v0.852.002.749 (7)147
O9—H9B···O2v0.852.193.013 (9)163
O9—H9A···O60.852.152.979 (10)163
O8—H8···O12vi0.821.882.688 (14)170
O4—H4A···O10vii0.821.842.651 (8)172
N4—H4···O13'i0.862.543.39 (2)173
N2—H2···O5viii0.862.293.029 (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.
Acknowledgements top

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.

references
References top

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.