Bis(2,3-diamino-pyridinium) bis-(μ-pyridine-2,6-dicarboxyl-ato)-κO,N,O:O;κO:O,N,O-bis-[aqua-(pyridine-2,6-dicarboxyl-ato-κO,N,O)bis-muthate(III)] tetra-hydrate.

In the centrosymmetric dinuclear complex anion of the title compound, (C(5)H(8)N(3))(2)[Bi(2)(C(7)H(3)NO(4))(4)(H(2)O)(2)]·4H(2)O, the Bi(III) atom is eight-coordinated in an N(2)O(6) environment and has a distorted bicapped trigonal-prismatic coordination environment. Extensive inter-molecular O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds lead to the stability of the crystal structure. Inter-actions between one C-H group of the 2,3-diamino-pyridinium [(2,3-dapyH)(+)] cation and the aromatic ring of the pyridine-2,6-dicarboxyl-ate (pydc) ligand (C-H⋯centroid distance = 2.78 Å) and π-π inter-actions between the (2,3-dapyH)(+) cations and between the (2,3-dapyH)(+) cation and the pydc ligand [centroid-centroid distances = 3.489 (5) and 3.694 (5) Å] are observed.

Related literature

For related structures, see: Aghabozorg et al. (2008 ▶, 2010 ▶); Sheshmani et al. (2005 ▶).

Experimental

Crystal data

(C5H8N3)2[Bi2(C7H3NO4)4(H2O)2]·4H2O

M = 1406.76

Triclinic,

a = 9.3462 (19) Å

b = 10.726 (2) Å

c = 11.098 (2) Å

α = 95.13 (3)°

β = 91.38 (3)°

γ = 90.47 (3)°

V = 1107.7 (4) Å3

Z = 1

Mo Kα radiation

μ = 8.03 mm−1

T = 298 K

0.33 × 0.27 × 0.23 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.083, T max = 0.156

12406 measured reflections

5940 independent reflections

5539 reflections with I > 2σ(I)

R int = 0.113

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.154

S = 1.05

5940 reflections

347 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.98 e Å−3

Δρmin = −2.93 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005629/hy2406sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005629/hy2406Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C5H8N3)2[Bi2(C7H3NO4)4(H2O)2]·4H2O	Z = 1
Mr = 1406.76	F(000) = 680
Triclinic, P1	Dx = 2.109 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3462 (19) Å	Cell parameters from 5940 reflections
b = 10.726 (2) Å	θ = 2.2–29.2°
c = 11.098 (2) Å	µ = 8.03 mm−1
α = 95.13 (3)°	T = 298 K
β = 91.38 (3)°	Prism, brown
γ = 90.47 (3)°	0.33 × 0.27 × 0.23 mm
V = 1107.7 (4) Å3

Stoe IPDS-2 diffractometer	5940 independent reflections
Radiation source: fine-focus sealed tube	5539 reflections with I > 2σ(I)
graphite	Rint = 0.113
ω scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −12→12
Tmin = 0.083, Tmax = 0.156	k = −14→14
12406 measured reflections	l = −15→15

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.1042P)2 + 3.0215P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5940 reflections	Δρmax = 2.98 e Å−3
347 parameters	Δρmin = −2.93 e Å−3
9 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: 0.0047 (13)

	x	y	z	Uiso*/Ueq
O10	0.8002 (8)	0.0220 (8)	0.8803 (9)	0.0534 (19)
O8	−0.0239 (8)	0.3014 (6)	1.0095 (8)	0.056 (2)
O11	0.9124 (8)	0.8479 (8)	0.7003 (7)	0.0502 (17)
O6	0.6729 (7)	0.3001 (6)	0.7953 (8)	0.0494 (17)
Bi1	0.32379 (2)	0.045644 (19)	0.88303 (2)	0.02387 (13)
N1	0.4091 (7)	−0.0927 (6)	0.7035 (5)	0.0265 (11)
C5	0.3481 (8)	−0.0744 (7)	0.5968 (7)	0.0297 (14)
C1	0.5057 (7)	−0.1819 (6)	0.7123 (6)	0.0247 (12)
C3	0.4867 (12)	−0.2374 (10)	0.4998 (8)	0.047 (2)
H3	0.5131	−0.2871	0.4312	0.056*
C7	0.2415 (9)	0.0299 (7)	0.5988 (8)	0.0359 (16)
C2	0.5469 (10)	−0.2566 (9)	0.6098 (8)	0.0426 (19)
H2	0.6147	−0.3188	0.6163	0.051*
C4	0.3855 (10)	−0.1434 (9)	0.4899 (8)	0.0388 (17)
H4	0.3450	−0.1277	0.4155	0.047*
N4	1.1655 (8)	0.4867 (7)	0.2534 (8)	0.0436 (18)
H4A	1.1986	0.4137	0.2319	0.052*
H4B	1.2133	0.5526	0.2398	0.052*
C15	1.0421 (8)	0.4974 (7)	0.3068 (7)	0.0300 (14)
C16	0.9763 (9)	0.6147 (8)	0.3425 (8)	0.0333 (15)
N3	0.9707 (9)	0.3919 (7)	0.3263 (7)	0.0383 (15)
N5	1.0463 (9)	0.7230 (6)	0.3244 (9)	0.0462 (19)
H5A	1.0086	0.7940	0.3469	0.055*
H5B	1.1281	0.7205	0.2904	0.055*
C17	0.8460 (10)	0.6133 (9)	0.3960 (10)	0.043 (2)
H17	0.8021	0.6885	0.4204	0.051*
C19	0.8402 (11)	0.3898 (9)	0.3806 (9)	0.046 (2)
H19	0.7959	0.3144	0.3938	0.055*
C18	0.7782 (10)	0.5004 (11)	0.4144 (10)	0.048 (2)
H18	0.6892	0.5012	0.4502	0.057*
O3	0.2133 (7)	0.0852 (6)	0.7009 (6)	0.0381 (13)
O7	0.0896 (6)	0.1326 (5)	0.9346 (6)	0.0340 (12)
O5	0.5370 (6)	0.1332 (5)	0.8106 (6)	0.0324 (11)
N2	0.3143 (7)	0.2700 (6)	0.8827 (6)	0.0262 (11)
C8	0.4311 (8)	0.3335 (7)	0.8530 (7)	0.0283 (13)
O4	0.1860 (11)	0.0529 (9)	0.5024 (7)	0.066 (2)
C14	0.0788 (9)	0.2486 (7)	0.9591 (8)	0.0331 (15)
C13	0.5562 (8)	0.2518 (7)	0.8158 (7)	0.0290 (14)
C12	0.1996 (8)	0.3318 (7)	0.9215 (7)	0.0294 (14)
C9	0.4360 (8)	0.4623 (7)	0.8582 (8)	0.0321 (15)
H9	0.5173	0.5045	0.8362	0.039*
C11	0.1952 (8)	0.4614 (7)	0.9293 (8)	0.0324 (15)
H11	0.1135	0.5036	0.9554	0.039*
C10	0.3145 (9)	0.5268 (7)	0.8975 (9)	0.0358 (17)
H10	0.3137	0.6138	0.9023	0.043*
O1	0.5240 (6)	−0.1236 (5)	0.9223 (5)	0.0290 (10)
O2	0.6605 (9)	−0.2791 (7)	0.8471 (6)	0.0489 (17)
C6	0.5695 (8)	−0.1989 (7)	0.8366 (7)	0.0276 (13)
O9	0.1606 (8)	−0.1496 (7)	0.8422 (7)	0.0455 (15)
H10B	0.867 (9)	0.064 (12)	0.906 (13)	0.055*
H11A	0.851 (13)	0.845 (14)	0.638 (9)	0.068*
H11B	0.860 (15)	0.908 (13)	0.742 (11)	0.068*
H9A	0.143 (14)	−0.171 (15)	0.909 (8)	0.068*
H9B	0.090 (13)	−0.126 (14)	0.802 (10)	0.068*
H10A	0.717 (9)	0.070 (11)	0.875 (12)	0.055*
H3A	1.007 (14)	0.325 (13)	0.289 (12)	0.055*

	U11	U22	U33	U12	U13	U23
O10	0.036 (3)	0.043 (3)	0.081 (6)	0.007 (3)	−0.001 (3)	0.005 (4)
O8	0.052 (4)	0.029 (3)	0.090 (6)	0.012 (3)	0.045 (4)	0.005 (3)
O11	0.049 (4)	0.054 (4)	0.049 (4)	0.022 (3)	−0.006 (3)	0.011 (3)
O6	0.034 (3)	0.034 (3)	0.080 (5)	−0.004 (2)	0.025 (3)	0.001 (3)
Bi1	0.02420 (17)	0.01863 (16)	0.02853 (18)	0.00371 (9)	0.00376 (9)	−0.00045 (9)
N1	0.030 (3)	0.026 (3)	0.024 (3)	0.004 (2)	0.004 (2)	0.000 (2)
C5	0.032 (3)	0.025 (3)	0.032 (4)	0.000 (3)	0.003 (3)	0.000 (3)
C1	0.025 (3)	0.022 (3)	0.026 (3)	0.002 (2)	0.003 (2)	−0.004 (2)
C3	0.060 (6)	0.049 (5)	0.030 (4)	0.014 (4)	0.012 (4)	−0.010 (4)
C7	0.039 (4)	0.028 (3)	0.042 (4)	0.006 (3)	0.004 (3)	0.006 (3)
C2	0.041 (4)	0.046 (5)	0.037 (4)	0.011 (4)	0.006 (3)	−0.015 (4)
C4	0.045 (4)	0.043 (4)	0.027 (4)	0.004 (3)	0.006 (3)	−0.003 (3)
N4	0.037 (4)	0.030 (3)	0.063 (5)	0.005 (3)	0.019 (3)	−0.004 (3)
C15	0.035 (4)	0.030 (3)	0.025 (3)	0.000 (3)	−0.001 (3)	0.002 (3)
C16	0.032 (4)	0.029 (3)	0.039 (4)	0.000 (3)	0.005 (3)	0.003 (3)
N3	0.045 (4)	0.027 (3)	0.043 (4)	−0.001 (3)	0.010 (3)	−0.002 (3)
N5	0.051 (4)	0.019 (3)	0.069 (5)	0.007 (3)	0.024 (4)	0.002 (3)
C17	0.037 (4)	0.036 (4)	0.055 (6)	0.012 (3)	0.013 (4)	0.002 (4)
C19	0.053 (5)	0.041 (4)	0.044 (5)	−0.009 (4)	0.013 (4)	0.003 (4)
C18	0.033 (4)	0.057 (6)	0.052 (5)	−0.011 (4)	0.015 (4)	−0.008 (4)
O3	0.044 (3)	0.034 (3)	0.036 (3)	0.018 (2)	−0.007 (2)	0.001 (2)
O7	0.029 (2)	0.024 (2)	0.048 (3)	−0.0006 (19)	0.007 (2)	0.004 (2)
O5	0.031 (3)	0.024 (2)	0.042 (3)	0.0096 (19)	0.014 (2)	0.002 (2)
N2	0.027 (3)	0.025 (3)	0.026 (3)	0.005 (2)	0.006 (2)	−0.002 (2)
C8	0.033 (3)	0.022 (3)	0.029 (3)	0.002 (2)	0.006 (3)	0.001 (2)
O4	0.082 (6)	0.073 (5)	0.042 (4)	0.035 (5)	−0.015 (4)	0.003 (4)
C14	0.033 (4)	0.024 (3)	0.043 (4)	0.005 (3)	0.008 (3)	0.008 (3)
C13	0.027 (3)	0.027 (3)	0.032 (3)	0.004 (2)	0.008 (3)	−0.001 (3)
C12	0.028 (3)	0.025 (3)	0.035 (4)	0.002 (2)	0.005 (3)	−0.003 (3)
C9	0.026 (3)	0.025 (3)	0.046 (4)	0.003 (2)	0.008 (3)	0.003 (3)
C11	0.028 (3)	0.026 (3)	0.043 (4)	0.006 (3)	0.007 (3)	−0.001 (3)
C10	0.036 (4)	0.023 (3)	0.048 (5)	0.007 (3)	0.006 (3)	0.000 (3)
O1	0.030 (2)	0.032 (2)	0.023 (2)	0.007 (2)	−0.0015 (19)	−0.0062 (19)
O2	0.067 (4)	0.040 (3)	0.039 (3)	0.029 (3)	−0.002 (3)	−0.002 (3)
C6	0.027 (3)	0.026 (3)	0.029 (3)	0.004 (2)	0.006 (3)	−0.002 (3)
O9	0.045 (3)	0.041 (3)	0.049 (4)	−0.012 (3)	0.010 (3)	−0.005 (3)

O10—H10B	0.80 (8)	C15—C16	1.433 (11)
O10—H10A	0.94 (8)	C16—N5	1.362 (11)
O8—C14	1.239 (10)	C16—C17	1.368 (12)
O11—H11A	0.89 (8)	N3—C19	1.374 (12)
O11—H11B	0.92 (9)	N3—H3A	0.87 (14)
O6—C13	1.238 (9)	N5—H5A	0.8600
Bi1—O3	2.323 (6)	N5—H5B	0.8600
Bi1—O5	2.384 (6)	C17—C18	1.396 (15)
Bi1—N2	2.409 (6)	C17—H17	0.9300
Bi1—O7	2.447 (6)	C19—C18	1.351 (15)
Bi1—N1	2.525 (6)	C19—H19	0.9300
Bi1—O9	2.581 (7)	C18—H18	0.9300
Bi1—O1i	2.627 (5)	O7—C14	1.255 (9)
Bi1—O1	2.673 (5)	O5—C13	1.279 (9)
N1—C1	1.329 (9)	N2—C12	1.325 (9)
N1—C5	1.333 (10)	N2—C8	1.346 (9)
C5—C4	1.394 (11)	C8—C9	1.377 (10)
C5—C7	1.504 (11)	C8—C13	1.510 (10)
C1—C2	1.395 (10)	C14—C12	1.522 (11)
C1—C6	1.516 (10)	C12—C11	1.386 (10)
C3—C2	1.364 (14)	C9—C10	1.394 (10)
C3—C4	1.398 (14)	C9—H9	0.9300
C3—H3	0.9300	C11—C10	1.381 (12)
C7—O4	1.224 (12)	C11—H11	0.9300
C7—O3	1.266 (11)	C10—H10	0.9300
C2—H2	0.9300	O1—C6	1.275 (9)
C4—H4	0.9300	O1—Bi1i	2.627 (5)
N4—C15	1.310 (11)	O2—C6	1.225 (10)
N4—H4A	0.8600	O9—H9A	0.81 (7)
N4—H4B	0.8600	O9—H9B	0.84 (8)
C15—N3	1.346 (10)
H10B—O10—H10A	112 (9)	N3—C15—C16	117.8 (7)
H11A—O11—H11B	91 (8)	N5—C16—C17	122.4 (8)
O3—Bi1—O5	87.5 (2)	N5—C16—C15	119.2 (7)
O3—Bi1—N2	73.7 (2)	C17—C16—C15	118.4 (8)
O5—Bi1—N2	67.26 (19)	C15—N3—C19	124.1 (8)
O3—Bi1—O7	74.0 (2)	C15—N3—H3A	113 (9)
O5—Bi1—O7	133.22 (18)	C19—N3—H3A	122 (9)
N2—Bi1—O7	66.40 (19)	C16—N5—H5A	120.0
O3—Bi1—N1	66.3 (2)	C16—N5—H5B	120.0
O5—Bi1—N1	70.7 (2)	H5A—N5—H5B	120.0
N2—Bi1—N1	122.1 (2)	C16—C17—C18	120.9 (8)
O7—Bi1—N1	132.5 (2)	C16—C17—H17	119.6
O3—Bi1—O9	79.0 (3)	C18—C17—H17	119.6
O5—Bi1—O9	140.1 (2)	C18—C19—N3	118.1 (9)
N2—Bi1—O9	140.2 (2)	C18—C19—H19	121.0
O7—Bi1—O9	78.7 (2)	N3—C19—H19	121.0
N1—Bi1—O9	69.4 (2)	C19—C18—C17	120.7 (8)
O3—Bi1—O1i	150.1 (2)	C19—C18—H18	119.6
O5—Bi1—O1i	74.6 (2)	C17—C18—H18	119.6
N2—Bi1—O1i	77.3 (2)	C7—O3—Bi1	124.9 (5)
O7—Bi1—O1i	100.97 (19)	C14—O7—Bi1	119.0 (5)
N1—Bi1—O1i	126.40 (18)	C13—O5—Bi1	121.0 (4)
O9—Bi1—O1i	129.7 (2)	C12—N2—C8	119.8 (6)
O3—Bi1—O1	128.33 (18)	C12—N2—Bi1	120.5 (5)
O5—Bi1—O1	76.04 (18)	C8—N2—Bi1	119.4 (5)
N2—Bi1—O1	136.45 (19)	N2—C8—C9	122.5 (7)
O7—Bi1—O1	147.79 (19)	N2—C8—C13	114.3 (6)
N1—Bi1—O1	61.99 (18)	C9—C8—C13	123.2 (7)
O9—Bi1—O1	83.3 (2)	O8—C14—O7	125.2 (8)
O1i—Bi1—O1	70.87 (18)	O8—C14—C12	117.1 (7)
C1—N1—C5	120.5 (6)	O7—C14—C12	117.7 (7)
C1—N1—Bi1	123.4 (5)	O6—C13—O5	122.5 (7)
C5—N1—Bi1	116.0 (5)	O6—C13—C8	120.1 (7)
N1—C5—C4	122.3 (7)	O5—C13—C8	117.4 (6)
N1—C5—C7	115.4 (7)	N2—C12—C11	121.4 (7)
C4—C5—C7	122.3 (8)	N2—C12—C14	114.3 (6)
N1—C1—C2	120.7 (7)	C11—C12—C14	124.3 (7)
N1—C1—C6	117.8 (6)	C8—C9—C10	117.5 (7)
C2—C1—C6	121.5 (7)	C8—C9—H9	121.3
C2—C3—C4	120.3 (8)	C10—C9—H9	121.3
C2—C3—H3	119.8	C10—C11—C12	118.8 (7)
C4—C3—H3	119.8	C10—C11—H11	120.6
O4—C7—O3	124.9 (8)	C12—C11—H11	120.6
O4—C7—C5	117.8 (8)	C11—C10—C9	119.9 (7)
O3—C7—C5	117.3 (7)	C11—C10—H10	120.0
C3—C2—C1	119.3 (8)	C9—C10—H10	120.0
C3—C2—H2	120.3	C6—O1—Bi1i	124.2 (5)
C1—C2—H2	120.3	C6—O1—Bi1	121.5 (5)
C5—C4—C3	116.9 (8)	Bi1i—O1—Bi1	109.13 (18)
C5—C4—H4	121.6	O2—C6—O1	125.5 (7)
C3—C4—H4	121.6	O2—C6—C1	119.2 (7)
C15—N4—H4A	120.0	O1—C6—C1	115.2 (6)
C15—N4—H4B	120.0	Bi1—O9—H9A	105 (10)
H4A—N4—H4B	120.0	Bi1—O9—H9B	106 (10)
N4—C15—N3	118.1 (8)	H9A—O9—H9B	116 (10)
N4—C15—C16	124.0 (7)
O3—Bi1—N1—C1	−178.5 (6)	O1i—Bi1—O5—C13	−75.3 (6)
O5—Bi1—N1—C1	85.6 (6)	O1—Bi1—O5—C13	−148.9 (6)
N2—Bi1—N1—C1	131.0 (5)	O3—Bi1—N2—C12	86.6 (6)
O7—Bi1—N1—C1	−142.8 (5)	O5—Bi1—N2—C12	−179.2 (6)
O9—Bi1—N1—C1	−91.8 (6)	O7—Bi1—N2—C12	7.3 (6)
O1i—Bi1—N1—C1	33.0 (6)	N1—Bi1—N2—C12	134.0 (6)
O1—Bi1—N1—C1	1.6 (5)	O9—Bi1—N2—C12	38.0 (7)
O3—Bi1—N1—C5	−0.5 (5)	O1i—Bi1—N2—C12	−100.8 (6)
O5—Bi1—N1—C5	−96.4 (5)	O1—Bi1—N2—C12	−144.4 (5)
N2—Bi1—N1—C5	−51.0 (6)	O3—Bi1—N2—C8	−99.3 (6)
O7—Bi1—N1—C5	35.2 (6)	O5—Bi1—N2—C8	−5.1 (5)
O9—Bi1—N1—C5	86.2 (5)	O7—Bi1—N2—C8	−178.5 (6)
O1i—Bi1—N1—C5	−149.0 (5)	N1—Bi1—N2—C8	−51.9 (6)
O1—Bi1—N1—C5	179.6 (6)	O9—Bi1—N2—C8	−147.8 (5)
C1—N1—C5—C4	−2.4 (11)	O1i—Bi1—N2—C8	73.3 (5)
Bi1—N1—C5—C4	179.5 (6)	O1—Bi1—N2—C8	29.8 (7)
C1—N1—C5—C7	−179.6 (7)	C12—N2—C8—C9	−1.7 (12)
Bi1—N1—C5—C7	2.4 (8)	Bi1—N2—C8—C9	−175.9 (6)
C5—N1—C1—C2	1.1 (11)	C12—N2—C8—C13	177.3 (7)
Bi1—N1—C1—C2	179.0 (6)	Bi1—N2—C8—C13	3.1 (9)
C5—N1—C1—C6	−179.2 (6)	Bi1—O7—C14—O8	−164.6 (8)
Bi1—N1—C1—C6	−1.3 (9)	Bi1—O7—C14—C12	16.9 (10)
N1—C5—C7—O4	177.7 (9)	Bi1—O5—C13—O6	169.5 (7)
C4—C5—C7—O4	0.5 (13)	Bi1—O5—C13—C8	−8.4 (10)
N1—C5—C7—O3	−4.0 (11)	N2—C8—C13—O6	−174.6 (8)
C4—C5—C7—O3	178.8 (8)	C9—C8—C13—O6	4.4 (13)
C4—C3—C2—C1	0.4 (16)	N2—C8—C13—O5	3.3 (11)
N1—C1—C2—C3	−0.2 (14)	C9—C8—C13—O5	−177.7 (8)
C6—C1—C2—C3	−179.8 (9)	C8—N2—C12—C11	1.8 (12)
N1—C5—C4—C3	2.6 (13)	Bi1—N2—C12—C11	175.9 (6)
C7—C5—C4—C3	179.5 (9)	C8—N2—C12—C14	−176.5 (7)
C2—C3—C4—C5	−1.5 (15)	Bi1—N2—C12—C14	−2.4 (9)
N4—C15—C16—N5	−2.3 (13)	O8—C14—C12—N2	171.6 (9)
N3—C15—C16—N5	179.7 (9)	O7—C14—C12—N2	−9.8 (11)
N4—C15—C16—C17	179.0 (9)	O8—C14—C12—C11	−6.6 (14)
N3—C15—C16—C17	1.0 (12)	O7—C14—C12—C11	172.0 (8)
N4—C15—N3—C19	−179.6 (9)	N2—C8—C9—C10	0.8 (13)
C16—C15—N3—C19	−1.5 (13)	C13—C8—C9—C10	−178.1 (8)
N5—C16—C17—C18	−179.2 (11)	N2—C12—C11—C10	−1.0 (13)
C15—C16—C17—C18	−0.6 (15)	C14—C12—C11—C10	177.1 (8)
C15—N3—C19—C18	1.4 (15)	C12—C11—C10—C9	0.2 (13)
N3—C19—C18—C17	−0.9 (17)	C8—C9—C10—C11	−0.1 (13)
C16—C17—C18—C19	0.6 (17)	O3—Bi1—O1—C6	−2.0 (7)
O4—C7—O3—Bi1	−178.0 (9)	O5—Bi1—O1—C6	−77.3 (6)
C5—C7—O3—Bi1	3.8 (11)	N2—Bi1—O1—C6	−110.2 (6)
O5—Bi1—O3—C7	68.1 (7)	O7—Bi1—O1—C6	124.4 (6)
N2—Bi1—O3—C7	135.2 (8)	N1—Bi1—O1—C6	−1.9 (5)
O7—Bi1—O3—C7	−155.3 (8)	O9—Bi1—O1—C6	68.3 (6)
N1—Bi1—O3—C7	−1.9 (7)	O1i—Bi1—O1—C6	−155.5 (7)
O9—Bi1—O3—C7	−74.1 (7)	O3—Bi1—O1—Bi1i	153.5 (2)
O1i—Bi1—O3—C7	120.6 (7)	O5—Bi1—O1—Bi1i	78.3 (2)
O1—Bi1—O3—C7	−1.8 (8)	N2—Bi1—O1—Bi1i	45.4 (4)
O3—Bi1—O7—C14	−91.9 (7)	O7—Bi1—O1—Bi1i	−80.0 (4)
O5—Bi1—O7—C14	−21.3 (8)	N1—Bi1—O1—Bi1i	153.6 (3)
N2—Bi1—O7—C14	−13.0 (6)	O9—Bi1—O1—Bi1i	−136.2 (3)
N1—Bi1—O7—C14	−125.7 (6)	O1i—Bi1—O1—Bi1i	0.0
O9—Bi1—O7—C14	−173.6 (7)	Bi1i—O1—C6—O2	28.4 (11)
O1i—Bi1—O7—C14	57.8 (7)	Bi1—O1—C6—O2	−179.9 (7)
O1—Bi1—O7—C14	129.2 (6)	Bi1i—O1—C6—C1	−149.8 (5)
O3—Bi1—O5—C13	80.5 (6)	Bi1—O1—C6—C1	2.0 (8)
N2—Bi1—O5—C13	7.2 (6)	N1—C1—C6—O2	−178.8 (8)
O7—Bi1—O5—C13	15.4 (7)	C2—C1—C6—O2	0.9 (12)
N1—Bi1—O5—C13	146.3 (7)	N1—C1—C6—O1	−0.6 (10)
O9—Bi1—O5—C13	150.0 (6)	C2—C1—C6—O1	179.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O11ii	0.87 (14)	2.02 (14)	2.797 (10)	148 (12)
N4—H4A···O2iii	0.86	2.11	2.924 (9)	158
N4—H4B···O6ii	0.86	1.97	2.830 (10)	178
N5—H5A···O3iv	0.86	2.53	3.216 (10)	138
N5—H5B···O6ii	0.86	2.11	2.972 (10)	176
O9—H9A···O8v	0.81 (7)	2.07 (12)	2.746 (10)	141 (15)
O9—H9B···O11vi	0.84 (8)	1.99 (10)	2.771 (11)	155 (15)
O10—H10A···O5	0.94 (8)	1.96 (8)	2.862 (9)	160 (11)
O10—H10B···O7vii	0.80 (8)	2.21 (8)	2.972 (10)	160 (13)
O11—H11A···O4iv	0.89 (8)	2.01 (13)	2.717 (11)	136 (14)
O11—H11B···O10viii	0.92 (9)	1.96 (9)	2.836 (12)	158 (13)
C11—H11···O8ix	0.93	2.26	3.050 (10)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O11i	0.87 (14)	2.02 (14)	2.797 (10)	148 (12)
N4—H4A⋯O2ii	0.86	2.11	2.924 (9)	158
N4—H4B⋯O6i	0.86	1.97	2.830 (10)	178
N5—H5A⋯O3iii	0.86	2.53	3.216 (10)	138
N5—H5B⋯O6i	0.86	2.11	2.972 (10)	176
O9—H9A⋯O8iv	0.81 (7)	2.07 (12)	2.746 (10)	141 (15)
O9—H9B⋯O11v	0.84 (8)	1.99 (10)	2.771 (11)	155 (15)
O10—H10A⋯O5	0.94 (8)	1.96 (8)	2.862 (9)	160 (11)
O10—H10B⋯O7vi	0.80 (8)	2.21 (8)	2.972 (10)	160 (13)
O11—H11A⋯O4iii	0.89 (8)	2.01 (13)	2.717 (11)	136 (14)
O11—H11B⋯O10vii	0.92 (9)	1.96 (9)	2.836 (12)	158 (13)
C11—H11⋯O8viii	0.93	2.26	3.050 (10)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .