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

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

doi:10.1107/S1600536807059740

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

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

The asymmetric unit of the title complex, [Bi(C₁₀H₉N₂O₄)₂Cl]·5H₂O, contains the Bi^III 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059740/sj2427sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059740/sj2427Isup2.hkl Contains datablock I

CCDC reference: 672695

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
Disorder in solvent or counterion
R factor = 0.041
wR factor = 0.106
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4A    ..  H10A    ..       1.89 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H12B   ..  H12B    ..       1.33 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O7
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      17.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT417_ALERT_2_C Short Inter D-H..H-D       H11B   ..  H12A    ..       2.14 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H12B   ..  H13G    ..       2.13 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.922
            Tmax scaled      0.507 Tmin scaled      0.100
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

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

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	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]·5H₂O	F(000) = 1520
M_r = 776.89	D_x = 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 = 2.3–28.1°
b = 29.432 (3) Å	µ = 6.79 mm⁻¹
c = 9.6869 (11) Å	T = 298 K
β = 114.331 (2)°	Block, orange
V = 2665.9 (5) Å³	0.59 × 0.18 × 0.10 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	4682 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→8
T_min = 0.108, T_max = 0.550	k = −35→32
12001 measured reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0583P)² + 4.9896P] where P = (F_o² + 2F_c²)/3
4682 reflections	(Δ/σ)_max = 0.001
358 parameters	Δρ_max = 2.01 e Å⁻³
7 restraints	Δρ_min = −2.68 e Å⁻³

Crystal data top

[Bi(C₁₀H₉N₂O₄)₂Cl]·5H₂O	V = 2665.9 (5) Å³
M_r = 776.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2622 (10) Å	µ = 6.79 mm⁻¹
b = 29.432 (3) Å	T = 298 K
c = 9.6869 (11) Å	0.59 × 0.18 × 0.10 mm
β = 114.331 (2)°

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)
T_min = 0.108, T_max = 0.550	R_int = 0.045
12001 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	7 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	Δρ_max = 2.01 e Å⁻³
4682 reflections	Δρ_min = −2.68 e Å⁻³
358 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.85	2.40	3.241 (9)	173
O11—H11A···O9	0.85	1.94	2.785 (12)	172
O10—H10B···Cl1^v	0.85	2.74	3.505 (6)	150
O10—H10A···O2^v	0.85	2.53	3.326 (8)	156
O10—H10A···O1^v	0.85	2.00	2.749 (7)	147
O9—H9B···O2^v	0.85	2.19	3.013 (9)	163
O9—H9A···O6	0.85	2.15	2.979 (10)	163
O8—H8···O12^vi	0.82	1.88	2.688 (14)	170
O4—H4A···O10^vii	0.82	1.84	2.651 (8)	172
N4—H4···O13′ⁱ	0.86	2.54	3.39 (2)	173
N2—H2···O5^viii	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.

Experimental details

Crystal data
Chemical formula	[Bi(C₁₀H₉N₂O₄)₂Cl]·5H₂O
M_r	776.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.2622 (10), 29.432 (3), 9.6869 (11)
β (°)	114.331 (2)
V (Å³)	2665.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.79
Crystal size (mm)	0.59 × 0.18 × 0.10

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.108, 0.550
No. of measured, independent and observed [I > 2σ(I)] reflections	12001, 4682, 3743
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.01
No. of reflections	4682
No. of parameters	358
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.01, −2.68

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13'—H13G···O12ⁱ	0.85	2.21	3.052 (18)	169.6
O13'—H13F···Cl1ⁱⁱ	0.85	2.15	2.991 (16)	172.1
O13—H13D···O7ⁱⁱ	0.85	2.40	3.24 (2)	169.1
O12—H12B···O12ⁱⁱⁱ	0.85	2.17	3.01 (3)	173.0
O12—H12A···O11	0.85	1.81	2.656 (15)	175.7
O11—H11B···Cl1^iv	0.85	2.40	3.241 (9)	172.6
O11—H11A···O9	0.85	1.94	2.785 (12)	172.0
O10—H10B···Cl1^v	0.85	2.74	3.505 (6)	150.1
O10—H10A···O2^v	0.85	2.53	3.326 (8)	155.6
O10—H10A···O1^v	0.85	2.00	2.749 (7)	147.3
O9—H9B···O2^v	0.85	2.19	3.013 (9)	163.1
O9—H9A···O6	0.85	2.15	2.979 (10)	163.4
O8—H8···O12^vi	0.82	1.88	2.688 (14)	169.9
O4—H4A···O10^vii	0.82	1.84	2.651 (8)	172.1
N4—H4···O13'ⁱ	0.86	2.54	3.39 (2)	173.0
N2—H2···O5^viii	0.86	2.29	3.029 (8)	144.6

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.

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