Poly[[hepta-μ2-aqua-bis­(μ2-pyrazine-2-carboxyl­ato)dibarium] bis­(pyrazine-2-carboxyl­ate)]

Shuai, Q.; Ding, K.-L.; Hu, F.; Yu, P.

doi:10.1107/S1600536811003023

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m283-m284

doi:10.1107/S1600536811003023

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Poly[[hepta-μ₂-aqua-bis(μ₂-pyrazine-2-carboxylato)dibarium] bis(pyrazine-2-carboxylate)]

Qi Shuai,^a ^* Ke-Lian Ding,^a Fan Hu ^b and Ping Yu ^a

^aCollege of Science, Northwest A&F University, Yangling 712100, Shanxi Province, People's Republic of China, and ^bStudents Service, Northwest A&F University, Yangling 712100, Shanxi Province, People's Republic of China
^*Correspondence e-mail: shuaiqi@nwsuaf.edu.cn

(Received 5 December 2010; accepted 23 January 2011; online 29 January 2011)

In the layered title coordination polymer, {[Ba₂(C₅H₃N₂O₂)₂(H₂O)₇](C₅H₃N₂O₂)₂}_n, the coordination geometries around the two independent Ba^II ions can be described as bicapped square-antiprismatic [BaNO₉] arrangements. A two-dimensional polymeric framework with (6,3) topology can be observed in the ac plane, the nodes being provided by Ba^II ions and the connectors being N and O atoms belonging to pyrazine-2-carboxylate ligands and O atoms of bridging water molecules. Non-coordinating pyrazine-2-carboxylate ions are located between the polymeric layers in the crystal and are interconnected through extensive O—H⋯N,O hydrogen bonding.

Related literature

For Ca^II and Sr^II complexes with pyrazine-2-carboxylate as ligand, see: Ptasiewicz-Bak et al. (1998 ). For different modes of coordination for pyrazine-2-carboxylate in polymers, see: Huang et al. (2003 ); Yin et al. (2006 ).

Experimental

Crystal data

[Ba₂(C₅H₃N₂O₂)₂(H₂O)₇](C₅H₃N₂O₂)₂
M_r = 893.17
Monoclinic, P 2₁
a = 7.5652 (10) Å
b = 29.263 (3) Å
c = 7.6067 (10) Å
β = 118.741 (2)°
V = 1476.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 298 K
0.49 × 0.34 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.348, T_max = 0.669
7342 measured reflections
4734 independent reflections
4502 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
4734 reflections
406 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.84 e Å⁻³
Δρ_min = −2.62 e Å⁻³
Absolute structure: Flack (1983 ), 2096 Friedel pairs
Flack parameter: 0.04 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10A⋯O7	0.85	2.23	3.000 (13)	152
O10—H10B⋯O5	0.85	1.92	2.769 (11)	177
O11—H11A⋯O4	0.85	1.88	2.669 (12)	153
O11—H11B⋯O5	0.85	2.04	2.861 (12)	163
O11—H11B⋯N5	0.85	2.62	3.191 (14)	126
O13—H13A⋯N5	0.85	2.14	2.983 (14)	175
O14—H14A⋯O8	0.85	1.87	2.685 (12)	160
O9—H9A⋯O7ⁱ	0.85	1.88	2.677 (12)	155
O9—H9B⋯O5ⁱ	0.85	1.89	2.689 (12)	156
O13—H13B⋯O6ⁱ	0.85	1.93	2.729 (12)	157
O15—H15A⋯O7ⁱ	0.85	2.04	2.860 (12)	161
O15—H15A⋯N7ⁱ	0.85	2.62	3.208 (14)	127
O12—H12A⋯O7ⁱⁱ	0.85	1.96	2.811 (12)	179
O12—H12B⋯O5ⁱⁱ	0.85	2.26	3.018 (12)	149
O14—H14B⋯N7ⁱⁱ	0.85	2.18	3.028 (13)	174
O15—H15B⋯O2ⁱⁱⁱ	0.85	1.90	2.676 (11)	152
Symmetry codes: (i) x+1, y, z; (ii) x, y, z-1; (iii) x, y, z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003023/bh2331sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003023/bh2331Isup2.hkl

checkCIF report

Comment top

Ptasiewicz-Bak et al. obtained monomeric complexes of calcium and strontium [M(C₅H₃N₂O₂)₂(H₂O)₄] (M = Ca^II or Sr^II, Ptasiewicz-Bak et al., 1998), based on 2-pyrazinecarboxylate ligand, which are isostructural.

Here, we report a complex, (I), assembled by alkaline earth metal Ba^II ion with 2-pyrazinecarboxylate as ligand. Different from complexes of calcium and strontium, the formula for the title complex is [Ba₂(C₅H₃N₂O₂)₂(H₂O)₇] (C₅H₃N₂O₂)₂. X-ray single-crystal diffraction analysis indicates the presence of two independent Ba^II ions, two coordinated pyrazine-2-carboxylate ions, seven coordinated water molecules and two isolated pyrazine-2-carboxylate ions in the asymmetric unit. Only one independent Ca^II or Sr^II ions are found in the complexes reported by Ptasiewicz-Bak et al.

In the title complex, the coordination geometries (Fig. 1) around Ba1 and Ba2 centres could be described as bicapped square-antiprismatic [BaNO₉] arrangements with coordination number of 10, where one N and two O atoms come from 2-pyrazinecarboxylate ligands, the rest, seven O atoms, being from seven coordinated water molecules. There are two kinds of pyrizine-2-carboxylate coordination modes, which have been reported previously (Yin et al., 2006; Huang et al., 2003). In (I), only one kind of coordination mode, µ₂ bridging mode, is observed. All the water molecules are coordinated and act as µ₂ bridging ligands. In this case, every six Ba^II ions form metal hexameric rings which share common edges, to construct two-dimensional, infinite networks with (6,3) topology (Fig. 2) parallel to the ac plane. Within the (6,3) topology layer, the nodes are provided by Ba^II and the connectors are N and O atoms which come from 2-pyrazinecarboxylate ions, and O atoms of water molecules. Non coordinating pyrazine-2-carboxylate ions are placed between polymeric layers in the crystal.

Related literature top

For Ca^II and Sr^II complexes with pyrazine-2-carboxylate as ligand, see: Ptasiewicz-Bak et al. (1998). For different modes of coordination for pyrazine-2-carboxylate in polymers, see: Huang et al. (2003); Yin et al. (2006).

Experimental top

A mixture of barium chloride dihydrate (0.0244 g, 0.1 mmol), sodium hydroxide (0.0160 g, 0.4 mmol), 2-pyrazinecarboxylic acid (0.0496 g, 0.4 mmol), and H₂O (3 ml) was placed in a Parr Teflon-lined stainless steel vessel (25 ml). The vessel was sealed and heated to 443.15 K for 6 days. Then, the vessel was cooled to 373.15 K at a rate of 5 K.h^-1 and slowly cooled to room temperature. Colourless, rectangular single crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

	Fig. 1. Coordination environment of Ba^II ions in the title complex. Non-hydrogen atoms are shown as 30% probability ellipsoids. Hydrogen atoms are omitted for clarity.
	Fig. 2. View of one two-dimensional layer structure along b axis in the title complex. Hydrogen atoms are omitted for clarity. Some redundant atoms are omitted for clarity.

Poly[[hepta-µ₂-aqua-bis(µ₂-pyrazine-2-carboxylato)dibarium] bis(pyrazine-2-carboxylate)] top

Crystal data top

[Ba₂(C₅H₃N₂O₂)₂(H₂O)₇](C₅H₃N₂O₂)₂	F(000) = 868
M_r = 893.17	D_x = 2.009 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4314 reflections
a = 7.5652 (10) Å	θ = 2.8–27.6°
b = 29.263 (3) Å	µ = 2.74 mm⁻¹
c = 7.6067 (10) Å	T = 298 K
β = 118.741 (2)°	Block, colourless
V = 1476.5 (3) Å³	0.49 × 0.34 × 0.16 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4734 independent reflections
Radiation source: fine-focus sealed tube	4502 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.4°
ϕ and ω scans	h = −8→6
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −34→32
T_min = 0.348, T_max = 0.669	l = −8→9
7342 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.062P)² + 10.4333P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 1.84 e Å⁻³
4734 reflections	Δρ_min = −2.62 e Å⁻³
406 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.00273 (13)
0 constraints	Absolute structure: Flack (1983), 2096 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)
Secondary atom site location: difference Fourier map

Crystal data top

[Ba₂(C₅H₃N₂O₂)₂(H₂O)₇](C₅H₃N₂O₂)₂	V = 1476.5 (3) Å³
M_r = 893.17	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5652 (10) Å	µ = 2.74 mm⁻¹
b = 29.263 (3) Å	T = 298 K
c = 7.6067 (10) Å	0.49 × 0.34 × 0.16 mm
β = 118.741 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4734 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	4502 reflections with I > 2σ(I)
T_min = 0.348, T_max = 0.669	R_int = 0.036
7342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.062P)² + 10.4333P] where P = (F_o² + 2F_c²)/3
S = 1.02	Δρ_max = 1.84 e Å⁻³
4734 reflections	Δρ_min = −2.62 e Å⁻³
406 parameters	Absolute structure: Flack (1983), 2096 Friedel pairs
1 restraint	Absolute structure parameter: 0.04 (4)

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

	x	y	z	U_iso*/U_eq
Ba1	0.77811 (9)	0.366622 (19)	0.36016 (9)	0.02014 (17)
Ba2	1.10429 (9)	0.394536 (18)	0.03210 (9)	0.01982 (16)
N1	0.8301 (16)	0.2639 (3)	0.3451 (15)	0.026 (2)
N2	0.888 (2)	0.1707 (4)	0.308 (2)	0.043 (3)
N3	1.0849 (15)	0.4975 (4)	0.0828 (17)	0.028 (2)
N4	1.045 (2)	0.5910 (4)	0.137 (2)	0.045 (3)
N5	0.6725 (18)	0.5151 (4)	0.6133 (18)	0.033 (3)
N6	0.5658 (18)	0.6073 (4)	0.610 (2)	0.039 (3)
N7	0.3586 (18)	0.2445 (4)	0.9189 (19)	0.032 (3)
N8	0.400 (2)	0.1538 (4)	0.828 (2)	0.052 (4)
O1	0.8792 (14)	0.3243 (3)	0.0951 (15)	0.034 (2)
O2	0.9048 (17)	0.2671 (3)	−0.0797 (14)	0.039 (2)
O3	0.8422 (13)	0.4370 (3)	0.1352 (14)	0.033 (2)
O4	0.6620 (16)	0.4940 (3)	0.1590 (18)	0.045 (3)
O5	0.4326 (14)	0.4487 (3)	0.6353 (16)	0.040 (2)
O6	0.2265 (14)	0.5026 (4)	0.6485 (15)	0.043 (3)
O7	0.3818 (16)	0.3133 (3)	0.6871 (15)	0.042 (2)
O8	0.4035 (18)	0.2619 (4)	0.4835 (15)	0.051 (3)
O9	1.1777 (11)	0.3806 (3)	0.4331 (11)	0.0267 (17)
H9A	1.2515	0.3573	0.4865	0.032*
H9B	1.2312	0.4040	0.5061	0.032*
O10	0.6963 (12)	0.3775 (3)	0.6959 (12)	0.0278 (18)
H10A	0.6450	0.3534	0.7149	0.033*
H10B	0.6182	0.4000	0.6777	0.033*
O11	0.4867 (12)	0.4342 (3)	0.2934 (13)	0.0288 (19)
H11A	0.5066	0.4577	0.2396	0.035*
H11B	0.4921	0.4421	0.4035	0.035*
O12	0.4417 (12)	0.3857 (3)	−0.0462 (12)	0.031 (2)
H12A	0.4241	0.3637	−0.1259	0.038*
H12B	0.4614	0.4102	−0.0945	0.038*
O13	0.9582 (12)	0.4406 (3)	0.6526 (12)	0.0294 (18)
H13A	0.8706	0.4607	0.6372	0.035*
H13B	1.0541	0.4533	0.6426	0.035*
O14	0.3952 (12)	0.3203 (3)	0.2065 (13)	0.0296 (19)
H14A	0.3838	0.3071	0.3001	0.036*
H14B	0.3806	0.3006	0.1182	0.036*
O15	1.0377 (12)	0.3263 (3)	0.7417 (12)	0.0271 (18)
H15A	1.1486	0.3182	0.7481	0.032*
H15B	0.9823	0.3029	0.7608	0.032*
C1	0.8864 (17)	0.2828 (4)	0.0620 (17)	0.021 (2)
C2	0.874 (2)	0.2485 (4)	0.2049 (19)	0.027 (3)
C3	0.896 (2)	0.2017 (4)	0.184 (2)	0.036 (3)
H3	0.9171	0.1918	0.0790	0.043*
C5	0.847 (3)	0.1868 (6)	0.449 (3)	0.046 (4)
H5	0.8360	0.1666	0.5373	0.056*
C6	0.822 (2)	0.2336 (5)	0.467 (2)	0.036 (3)
H6	0.7979	0.2435	0.5695	0.043*
C7	0.804 (2)	0.4782 (5)	0.1384 (19)	0.030 (3)
C8	0.944 (2)	0.5124 (4)	0.1270 (19)	0.030 (3)
C9	0.923 (2)	0.5590 (5)	0.149 (2)	0.039 (3)
H9	0.8193	0.5685	0.1736	0.047*
C11	1.187 (2)	0.5754 (5)	0.100 (3)	0.041 (4)
H11	1.2768	0.5960	0.0932	0.050*
C12	1.207 (2)	0.5296 (5)	0.071 (2)	0.034 (3)
H12	1.3088	0.5205	0.0432	0.041*
C13	0.3801 (19)	0.4890 (4)	0.640 (2)	0.026 (3)
C14	0.5088 (18)	0.5268 (4)	0.6264 (17)	0.022 (2)
C15	0.461 (2)	0.5730 (5)	0.624 (2)	0.036 (3)
H15	0.3458	0.5801	0.6341	0.043*
C17	0.727 (2)	0.5944 (5)	0.592 (2)	0.036 (3)
H17	0.8058	0.6168	0.5771	0.043*
C18	0.779 (2)	0.5490 (5)	0.595 (2)	0.041 (4)
H18	0.8932	0.5419	0.5840	0.049*
C19	0.396 (2)	0.2731 (4)	0.636 (2)	0.028 (3)
C20	0.3868 (17)	0.2347 (4)	0.7658 (19)	0.026 (3)
C21	0.409 (2)	0.1888 (5)	0.723 (2)	0.038 (3)
H21	0.4321	0.1828	0.6159	0.045*
C23	0.363 (2)	0.1655 (6)	0.977 (2)	0.045 (4)
H23	0.3494	0.1424	1.0533	0.054*
C24	0.346 (2)	0.2099 (5)	1.022 (2)	0.043 (4)
H24	0.3232	0.2159	1.1296	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.0175 (3)	0.0207 (3)	0.0234 (3)	0.0000 (3)	0.0108 (3)	−0.0010 (3)
Ba2	0.0184 (3)	0.0207 (3)	0.0216 (3)	0.0006 (3)	0.0106 (3)	−0.0005 (3)
N1	0.036 (6)	0.013 (5)	0.030 (6)	−0.005 (4)	0.017 (5)	−0.003 (4)
N2	0.053 (8)	0.023 (6)	0.065 (8)	0.011 (5)	0.038 (7)	0.007 (6)
N3	0.029 (6)	0.029 (6)	0.041 (6)	0.006 (5)	0.029 (5)	0.011 (5)
N4	0.053 (8)	0.019 (6)	0.073 (9)	−0.005 (5)	0.039 (7)	0.001 (6)
N5	0.028 (6)	0.032 (6)	0.042 (7)	0.000 (5)	0.018 (5)	0.005 (5)
N6	0.042 (7)	0.015 (6)	0.065 (9)	−0.006 (5)	0.028 (6)	0.002 (5)
N7	0.036 (6)	0.029 (6)	0.038 (6)	0.005 (5)	0.025 (6)	0.006 (5)
N8	0.096 (11)	0.018 (6)	0.049 (8)	0.005 (6)	0.041 (8)	0.007 (6)
O1	0.042 (5)	0.019 (5)	0.053 (6)	−0.002 (4)	0.031 (5)	−0.001 (4)
O2	0.076 (7)	0.021 (5)	0.036 (5)	−0.003 (5)	0.042 (6)	0.001 (4)
O3	0.040 (5)	0.022 (5)	0.055 (6)	0.006 (4)	0.037 (5)	0.010 (4)
O4	0.047 (6)	0.028 (5)	0.082 (8)	0.007 (4)	0.049 (6)	0.007 (5)
O5	0.043 (6)	0.030 (5)	0.060 (6)	−0.002 (4)	0.034 (5)	−0.008 (5)
O6	0.043 (6)	0.035 (6)	0.070 (8)	−0.003 (4)	0.042 (6)	0.001 (5)
O7	0.052 (6)	0.037 (5)	0.046 (6)	0.013 (5)	0.031 (5)	−0.001 (5)
O8	0.092 (9)	0.038 (6)	0.042 (6)	0.002 (6)	0.047 (7)	0.006 (5)
O9	0.020 (4)	0.033 (4)	0.025 (4)	0.000 (3)	0.008 (3)	−0.004 (3)
O10	0.028 (4)	0.027 (5)	0.036 (4)	0.000 (3)	0.022 (4)	0.001 (4)
O11	0.023 (4)	0.027 (5)	0.039 (5)	−0.004 (3)	0.017 (4)	−0.008 (4)
O12	0.041 (5)	0.031 (5)	0.030 (4)	−0.006 (4)	0.024 (4)	0.002 (4)
O13	0.028 (4)	0.025 (4)	0.041 (5)	0.000 (3)	0.021 (4)	0.000 (4)
O14	0.037 (5)	0.016 (4)	0.041 (5)	0.004 (3)	0.023 (4)	0.002 (4)
O15	0.031 (5)	0.020 (4)	0.031 (5)	0.003 (3)	0.016 (4)	−0.002 (3)
C1	0.020 (6)	0.027 (7)	0.018 (6)	−0.009 (5)	0.011 (5)	−0.002 (5)
C2	0.041 (8)	0.021 (6)	0.028 (7)	−0.009 (5)	0.024 (6)	−0.008 (5)
C3	0.070 (10)	0.007 (6)	0.058 (9)	−0.001 (6)	0.052 (9)	0.002 (6)
C5	0.049 (9)	0.037 (9)	0.055 (10)	−0.001 (8)	0.027 (8)	0.014 (8)
C6	0.045 (8)	0.041 (8)	0.023 (7)	0.004 (7)	0.018 (6)	0.005 (6)
C7	0.033 (7)	0.030 (7)	0.032 (7)	0.004 (6)	0.020 (6)	0.006 (6)
C8	0.042 (8)	0.017 (6)	0.029 (7)	0.000 (5)	0.016 (6)	0.001 (5)
C9	0.049 (9)	0.033 (8)	0.049 (9)	−0.002 (6)	0.035 (8)	−0.003 (6)
C11	0.040 (8)	0.029 (8)	0.059 (10)	−0.006 (7)	0.027 (8)	0.013 (7)
C12	0.032 (7)	0.042 (8)	0.035 (8)	0.004 (6)	0.021 (6)	0.002 (6)
C13	0.024 (6)	0.029 (7)	0.030 (7)	−0.009 (5)	0.016 (6)	−0.008 (5)
C14	0.028 (6)	0.016 (6)	0.024 (6)	0.002 (5)	0.015 (5)	0.001 (5)
C15	0.044 (8)	0.027 (7)	0.048 (9)	0.004 (6)	0.033 (7)	0.001 (6)
C17	0.043 (8)	0.021 (7)	0.049 (9)	−0.008 (6)	0.027 (7)	0.006 (6)
C18	0.032 (7)	0.039 (8)	0.063 (10)	−0.011 (6)	0.031 (8)	−0.003 (7)
C19	0.037 (7)	0.029 (7)	0.025 (7)	0.007 (5)	0.020 (6)	0.003 (5)
C20	0.018 (6)	0.025 (7)	0.035 (7)	0.004 (5)	0.011 (5)	0.000 (5)
C21	0.053 (9)	0.025 (7)	0.039 (8)	0.003 (6)	0.025 (7)	0.005 (6)
C23	0.056 (10)	0.042 (9)	0.034 (8)	−0.003 (7)	0.019 (8)	0.010 (7)
C24	0.043 (9)	0.054 (10)	0.037 (8)	0.000 (7)	0.024 (7)	−0.006 (7)

Geometric parameters (Å, º) top

Ba1—O1	2.769 (9)	O9—H9A	0.8500
Ba1—O11	2.821 (8)	O9—H9B	0.8500
Ba1—O9	2.829 (7)	O10—Ba2ⁱⁱⁱ	2.954 (8)
Ba1—O15	2.862 (8)	O10—H10A	0.8500
Ba1—O3	2.865 (8)	O10—H10B	0.8501
Ba1—O14	2.888 (8)	O11—Ba2^iv	2.853 (8)
Ba1—O10	2.920 (7)	O11—H11A	0.8499
Ba1—O13	2.930 (8)	O11—H11B	0.8500
Ba1—O12	2.963 (8)	O12—Ba2^iv	2.898 (8)
Ba1—N1	3.041 (10)	O12—H12A	0.8499
Ba2—O3	2.754 (8)	O12—H12B	0.8501
Ba2—O15ⁱ	2.838 (8)	O13—Ba2ⁱⁱⁱ	2.882 (8)
Ba2—O11ⁱⁱ	2.853 (8)	O13—H13A	0.8499
Ba2—O1	2.853 (8)	O13—H13B	0.8499
Ba2—O9	2.854 (7)	O14—Ba2^iv	2.919 (8)
Ba2—O13ⁱ	2.882 (8)	O14—H14A	0.8499
Ba2—O12ⁱⁱ	2.898 (8)	O14—H14B	0.8501
Ba2—O14ⁱⁱ	2.919 (8)	O15—Ba2ⁱⁱⁱ	2.838 (8)
Ba2—O10ⁱ	2.954 (8)	O15—H15A	0.8500
Ba2—N3	3.050 (11)	O15—H15B	0.8501
N1—C6	1.305 (17)	C1—C2	1.515 (16)
N1—C2	1.336 (16)	C2—C3	1.401 (17)
N2—C3	1.332 (17)	C3—H3	0.9300
N2—C5	1.34 (2)	C5—C6	1.40 (2)
N3—C8	1.334 (17)	C5—H5	0.9300
N3—C12	1.351 (17)	C6—H6	0.9300
N4—C11	1.32 (2)	C7—C8	1.489 (18)
N4—C9	1.349 (18)	C8—C9	1.394 (19)
N5—C18	1.326 (18)	C9—H9	0.9300
N5—C14	1.334 (16)	C11—C12	1.38 (2)
N6—C15	1.317 (17)	C11—H11	0.9300
N6—C17	1.341 (18)	C12—H12	0.9300
N7—C24	1.312 (19)	C13—C14	1.509 (16)
N7—C20	1.313 (16)	C14—C15	1.400 (18)
N8—C21	1.320 (18)	C15—H15	0.9300
N8—C23	1.331 (19)	C17—C18	1.39 (2)
O1—C1	1.246 (14)	C17—H17	0.9300
O2—C1	1.240 (14)	C18—H18	0.9300
O3—C7	1.243 (15)	C19—C20	1.519 (18)
O4—C7	1.248 (16)	C20—C21	1.413 (19)
O5—C13	1.249 (15)	C21—H21	0.9300
O6—C13	1.259 (15)	C23—C24	1.37 (2)
O7—C19	1.260 (16)	C23—H23	0.9300
O8—C19	1.233 (15)	C24—H24	0.9300

O1—Ba1—O11	130.4 (3)	O13ⁱ—Ba2—Ba1ⁱⁱ	115.01 (16)
O1—Ba1—O9	64.2 (2)	O12ⁱⁱ—Ba2—Ba1ⁱⁱ	39.69 (16)
O11—Ba1—O9	127.1 (2)	O14ⁱⁱ—Ba2—Ba1ⁱⁱ	38.27 (16)
O1—Ba1—O15	105.0 (2)	O10ⁱ—Ba2—Ba1ⁱⁱ	150.97 (15)
O11—Ba1—O15	124.6 (2)	N3—Ba2—Ba1ⁱⁱ	102.6 (2)
O9—Ba1—O15	73.3 (2)	Ba1—Ba2—Ba1ⁱⁱ	116.58 (2)
O1—Ba1—O3	72.6 (2)	C6—N1—C2	116.8 (11)
O11—Ba1—O3	74.4 (2)	C6—N1—Ba1	126.5 (9)
O9—Ba1—O3	62.7 (2)	C2—N1—Ba1	116.6 (8)
O15—Ba1—O3	132.2 (3)	C3—N2—C5	115.8 (12)
O1—Ba1—O14	94.0 (2)	C8—N3—C12	116.4 (12)
O11—Ba1—O14	73.3 (2)	C8—N3—Ba2	116.6 (8)
O9—Ba1—O14	156.4 (2)	C12—N3—Ba2	127.0 (8)
O15—Ba1—O14	106.4 (2)	C11—N4—C9	115.5 (12)
O3—Ba1—O14	121.4 (3)	C18—N5—C14	116.8 (13)
O1—Ba1—O10	159.1 (2)	C15—N6—C17	114.2 (11)
O11—Ba1—O10	66.7 (2)	C24—N7—C20	116.9 (13)
O9—Ba1—O10	118.0 (2)	C21—N8—C23	114.0 (13)
O15—Ba1—O10	59.2 (2)	C1—O1—Ba1	129.6 (7)
O3—Ba1—O10	127.8 (2)	C1—O1—Ba2	125.5 (7)
O14—Ba1—O10	79.2 (2)	Ba1—O1—Ba2	101.3 (3)
O1—Ba1—O13	133.9 (2)	C7—O3—Ba2	130.5 (8)
O11—Ba1—O13	69.9 (2)	C7—O3—Ba1	125.3 (8)
O9—Ba1—O13	71.4 (2)	Ba2—O3—Ba1	101.4 (3)
O15—Ba1—O13	72.1 (2)	Ba1—O9—Ba2	99.8 (2)
O3—Ba1—O13	76.8 (2)	Ba1—O9—H9A	111.8
O14—Ba1—O13	131.6 (2)	Ba2—O9—H9A	111.8
O10—Ba1—O13	58.1 (2)	Ba1—O9—H9B	111.8
O1—Ba1—O12	74.0 (3)	Ba2—O9—H9B	111.8
O11—Ba1—O12	58.3 (2)	H9A—O9—H9B	109.6
O9—Ba1—O12	118.6 (2)	Ba1—O10—Ba2ⁱⁱⁱ	101.7 (2)
O15—Ba1—O12	164.2 (2)	Ba1—O10—H10A	111.4
O3—Ba1—O12	63.1 (3)	Ba2ⁱⁱⁱ—O10—H10A	111.4
O14—Ba1—O12	58.4 (2)	Ba1—O10—H10B	111.4
O10—Ba1—O12	117.1 (2)	Ba2ⁱⁱⁱ—O10—H10B	111.4
O13—Ba1—O12	120.4 (2)	H10A—O10—H10B	109.3
O1—Ba1—N1	56.2 (3)	Ba1—O11—Ba2^iv	106.4 (3)
O11—Ba1—N1	142.2 (3)	Ba1—O11—H11A	110.4
O9—Ba1—N1	90.3 (3)	Ba2^iv—O11—H11A	110.4
O15—Ba1—N1	65.9 (2)	Ba1—O11—H11B	110.4
O3—Ba1—N1	128.8 (3)	Ba2^iv—O11—H11B	110.4
O14—Ba1—N1	69.1 (3)	H11A—O11—H11B	108.7
O10—Ba1—N1	103.1 (3)	Ba2^iv—O12—Ba1	101.6 (2)
O13—Ba1—N1	137.6 (3)	Ba2^iv—O12—H12A	111.2
O12—Ba1—N1	102.1 (3)	Ba1—O12—H12A	111.2
O1—Ba1—Ba2	40.06 (17)	Ba2^iv—O12—H12B	111.6
O11—Ba1—Ba2	112.03 (18)	Ba1—O12—H12B	111.6
O9—Ba1—Ba2	40.31 (15)	H12A—O12—H12B	109.3
O15—Ba1—Ba2	110.94 (17)	Ba2ⁱⁱⁱ—O13—Ba1	103.2 (2)
O3—Ba1—Ba2	38.39 (16)	Ba2ⁱⁱⁱ—O13—H13A	111.0
O14—Ba1—Ba2	126.27 (17)	Ba1—O13—H13A	111.0
O10—Ba1—Ba2	154.02 (16)	Ba2ⁱⁱⁱ—O13—H13B	111.2
O13—Ba1—Ba2	96.42 (16)	Ba1—O13—H13B	111.1
O12—Ba1—Ba2	78.79 (15)	H13A—O13—H13B	109.2
N1—Ba1—Ba2	92.6 (2)	Ba1—O14—Ba2^iv	103.0 (2)
O1—Ba1—Ba2^iv	108.1 (2)	Ba1—O14—H14A	111.1
O11—Ba1—Ba2^iv	37.04 (16)	Ba2^iv—O14—H14A	111.1
O9—Ba1—Ba2^iv	153.20 (16)	Ba1—O14—H14B	111.2
O15—Ba1—Ba2^iv	132.27 (17)	Ba2^iv—O14—H14B	111.2
O3—Ba1—Ba2^iv	90.58 (18)	H14A—O14—H14B	109.2
O14—Ba1—Ba2^iv	38.76 (15)	Ba2ⁱⁱⁱ—O15—Ba1	106.1 (2)
O10—Ba1—Ba2^iv	78.88 (15)	Ba2ⁱⁱⁱ—O15—H15A	110.5
O13—Ba1—Ba2^iv	105.87 (16)	Ba1—O15—H15A	110.5
O12—Ba1—Ba2^iv	38.66 (15)	Ba2ⁱⁱⁱ—O15—H15B	110.5
N1—Ba1—Ba2^iv	106.8 (2)	Ba1—O15—H15B	110.5
Ba2—Ba1—Ba2^iv	116.58 (2)	H15A—O15—H15B	108.7
O3—Ba2—O15ⁱ	131.0 (3)	O2—C1—O1	124.8 (11)
O3—Ba2—O11ⁱⁱ	104.2 (2)	O2—C1—C2	116.8 (10)
O15ⁱ—Ba2—O11ⁱⁱ	124.7 (2)	O1—C1—C2	118.4 (10)
O3—Ba2—O1	73.0 (2)	N1—C2—C3	120.7 (11)
O15ⁱ—Ba2—O1	74.1 (2)	N1—C2—C1	118.4 (11)
O11ⁱⁱ—Ba2—O1	131.6 (3)	C3—C2—C1	120.8 (10)
O3—Ba2—O9	63.7 (2)	N2—C3—C2	122.4 (12)
O15ⁱ—Ba2—O9	127.0 (2)	N2—C3—H3	118.8
O11ⁱⁱ—Ba2—O9	72.7 (2)	C2—C3—H3	118.8
O1—Ba2—O9	62.8 (3)	N2—C5—C6	121.3 (14)
O3—Ba2—O13ⁱ	95.3 (2)	N2—C5—H5	119.3
O15ⁱ—Ba2—O13ⁱ	73.2 (2)	C6—C5—H5	119.3
O11ⁱⁱ—Ba2—O13ⁱ	106.2 (2)	N1—C6—C5	122.8 (13)
O1—Ba2—O13ⁱ	122.2 (3)	N1—C6—H6	118.6
O9—Ba2—O13ⁱ	157.1 (2)	C5—C6—H6	118.6
O3—Ba2—O12ⁱⁱ	157.6 (2)	O3—C7—O4	125.7 (12)
O15ⁱ—Ba2—O12ⁱⁱ	67.8 (2)	O3—C7—C8	118.2 (11)
O11ⁱⁱ—Ba2—O12ⁱⁱ	58.8 (2)	O4—C7—C8	116.1 (12)
O1—Ba2—O12ⁱⁱ	128.8 (2)	N3—C8—C9	120.3 (12)
O9—Ba2—O12ⁱⁱ	118.0 (2)	N3—C8—C7	118.1 (11)
O13ⁱ—Ba2—O12ⁱⁱ	77.7 (2)	C9—C8—C7	121.5 (12)
O3—Ba2—O14ⁱⁱ	134.1 (2)	N4—C9—C8	123.2 (13)
O15ⁱ—Ba2—O14ⁱⁱ	69.0 (2)	N4—C9—H9	118.4
O11ⁱⁱ—Ba2—O14ⁱⁱ	72.3 (2)	C8—C9—H9	118.4
O1—Ba2—O14ⁱⁱ	76.6 (2)	N4—C11—C12	122.5 (13)
O9—Ba2—O14ⁱⁱ	72.0 (2)	N4—C11—H11	118.8
O13ⁱ—Ba2—O14ⁱⁱ	130.2 (2)	C12—C11—H11	118.8
O12ⁱⁱ—Ba2—O14ⁱⁱ	58.7 (2)	N3—C12—C11	122.2 (12)
O3—Ba2—O10ⁱ	74.2 (2)	N3—C12—H12	118.9
O15ⁱ—Ba2—O10ⁱ	59.1 (2)	C11—C12—H12	118.9
O11ⁱⁱ—Ba2—O10ⁱ	163.6 (2)	O5—C13—O6	127.8 (12)
O1—Ba2—O10ⁱ	64.2 (2)	O5—C13—C14	117.7 (11)
O9—Ba2—O10ⁱ	119.1 (2)	O6—C13—C14	114.4 (11)
O13ⁱ—Ba2—O10ⁱ	58.3 (2)	N5—C14—C15	119.5 (12)
O12ⁱⁱ—Ba2—O10ⁱ	117.6 (2)	N5—C14—C13	118.1 (11)
O14ⁱⁱ—Ba2—O10ⁱ	120.9 (2)	C15—C14—C13	122.5 (11)
O3—Ba2—N3	55.5 (2)	N6—C15—C14	124.9 (12)
O15ⁱ—Ba2—N3	142.4 (3)	N6—C15—H15	117.6
O11ⁱⁱ—Ba2—N3	66.7 (3)	C14—C15—H15	117.6
O1—Ba2—N3	128.4 (2)	N6—C17—C18	122.2 (12)
O9—Ba2—N3	90.1 (3)	N6—C17—H17	118.9
O13ⁱ—Ba2—N3	69.2 (3)	C18—C17—H17	118.9
O12ⁱⁱ—Ba2—N3	102.4 (3)	N5—C18—C17	122.4 (13)
O14ⁱⁱ—Ba2—N3	138.6 (3)	N5—C18—H18	118.8
O10ⁱ—Ba2—N3	100.5 (3)	C17—C18—H18	118.8
O3—Ba2—Ba1	40.23 (16)	O8—C19—O7	126.1 (12)
O15ⁱ—Ba2—Ba1	112.16 (17)	O8—C19—C20	116.8 (11)
O11ⁱⁱ—Ba2—Ba1	109.98 (17)	O7—C19—C20	116.9 (11)
O1—Ba2—Ba1	38.65 (17)	N7—C20—C21	119.9 (12)
O9—Ba2—Ba1	39.87 (15)	N7—C20—C19	119.6 (11)
O13ⁱ—Ba2—Ba1	127.78 (16)	C21—C20—C19	120.5 (11)
O12ⁱⁱ—Ba2—Ba1	154.19 (16)	N8—C21—C20	123.6 (13)
O14ⁱⁱ—Ba2—Ba1	96.38 (17)	N8—C21—H21	118.2
O10ⁱ—Ba2—Ba1	79.64 (15)	C20—C21—H21	118.2
N3—Ba2—Ba1	92.17 (18)	N8—C23—C24	122.9 (14)
O3—Ba2—Ba1ⁱⁱ	134.1 (2)	N8—C23—H23	118.6
O15ⁱ—Ba2—Ba1ⁱⁱ	91.90 (17)	C24—C23—H23	118.6
O11ⁱⁱ—Ba2—Ba1ⁱⁱ	36.55 (16)	N7—C24—C23	122.6 (14)
O1—Ba2—Ba1ⁱⁱ	112.37 (18)	N7—C24—H24	118.7
O9—Ba2—Ba1ⁱⁱ	78.29 (15)	C23—C24—H24	118.7

O1—Ba1—Ba2—O3	139.0 (4)	O11ⁱⁱ—Ba2—O1—Ba1	67.8 (4)
O11—Ba1—Ba2—O3	11.7 (4)	O9—Ba2—O1—Ba1	42.4 (3)
O9—Ba1—Ba2—O3	−110.2 (4)	O13ⁱ—Ba2—O1—Ba1	−111.8 (3)
O15—Ba1—Ba2—O3	−132.5 (4)	O12ⁱⁱ—Ba2—O1—Ba1	147.6 (2)
O14—Ba1—Ba2—O3	96.6 (4)	O14ⁱⁱ—Ba2—O1—Ba1	118.8 (3)
O10—Ba1—Ba2—O3	−70.1 (5)	O10ⁱ—Ba2—O1—Ba1	−106.6 (3)
O13—Ba1—Ba2—O3	−59.2 (3)	N3—Ba2—O1—Ba1	−23.8 (5)
O12—Ba1—Ba2—O3	60.6 (4)	Ba1ⁱⁱ—Ba2—O1—Ba1	105.1 (2)
N1—Ba1—Ba2—O3	162.4 (4)	O15ⁱ—Ba2—O3—C7	−123.5 (11)
Ba2^iv—Ba1—Ba2—O3	52.2 (3)	O11ⁱⁱ—Ba2—O3—C7	57.0 (12)
O1—Ba1—Ba2—O15ⁱ	10.9 (3)	O1—Ba2—O3—C7	−173.3 (12)
O11—Ba1—Ba2—O15ⁱ	−116.4 (2)	O9—Ba2—O3—C7	119.2 (12)
O9—Ba1—Ba2—O15ⁱ	121.7 (3)	O13ⁱ—Ba2—O3—C7	−51.2 (11)
O15—Ba1—Ba2—O15ⁱ	99.5 (3)	O12ⁱⁱ—Ba2—O3—C7	19.2 (15)
O3—Ba1—Ba2—O15ⁱ	−128.1 (4)	O14ⁱⁱ—Ba2—O3—C7	136.0 (11)
O14—Ba1—Ba2—O15ⁱ	−31.5 (3)	O10ⁱ—Ba2—O3—C7	−106.1 (11)
O10—Ba1—Ba2—O15ⁱ	161.8 (4)	N3—Ba2—O3—C7	9.1 (11)
O13—Ba1—Ba2—O15ⁱ	172.8 (2)	Ba1—Ba2—O3—C7	161.3 (13)
O12—Ba1—Ba2—O15ⁱ	−67.5 (2)	Ba1ⁱⁱ—Ba2—O3—C7	81.7 (12)
N1—Ba1—Ba2—O15ⁱ	34.3 (3)	O15ⁱ—Ba2—O3—Ba1	75.2 (4)
Ba2^iv—Ba1—Ba2—O15ⁱ	−75.88 (18)	O11ⁱⁱ—Ba2—O3—Ba1	−104.3 (3)
O1—Ba1—Ba2—O11ⁱⁱ	−132.5 (4)	O1—Ba2—O3—Ba1	25.4 (3)
O11—Ba1—Ba2—O11ⁱⁱ	100.2 (3)	O9—Ba2—O3—Ba1	−42.1 (3)
O9—Ba1—Ba2—O11ⁱⁱ	−21.7 (3)	O13ⁱ—Ba2—O3—Ba1	147.5 (3)
O15—Ba1—Ba2—O11ⁱⁱ	−43.9 (2)	O12ⁱⁱ—Ba2—O3—Ba1	−142.2 (5)
O3—Ba1—Ba2—O11ⁱⁱ	88.5 (4)	O14ⁱⁱ—Ba2—O3—Ba1	−25.3 (5)
O14—Ba1—Ba2—O11ⁱⁱ	−174.9 (3)	O10ⁱ—Ba2—O3—Ba1	92.6 (3)
O10—Ba1—Ba2—O11ⁱⁱ	18.4 (4)	N3—Ba2—O3—Ba1	−152.2 (4)
O13—Ba1—Ba2—O11ⁱⁱ	29.4 (2)	Ba1ⁱⁱ—Ba2—O3—Ba1	−79.6 (3)
O12—Ba1—Ba2—O11ⁱⁱ	149.1 (2)	O1—Ba1—O3—C7	171.1 (11)
N1—Ba1—Ba2—O11ⁱⁱ	−109.1 (3)	O11—Ba1—O3—C7	28.6 (10)
Ba2^iv—Ba1—Ba2—O11ⁱⁱ	140.71 (17)	O9—Ba1—O3—C7	−119.5 (11)
O11—Ba1—Ba2—O1	−127.3 (4)	O15—Ba1—O3—C7	−94.2 (11)
O9—Ba1—Ba2—O1	110.8 (4)	O14—Ba1—O3—C7	87.2 (11)
O15—Ba1—Ba2—O1	88.6 (3)	O10—Ba1—O3—C7	−14.0 (11)
O3—Ba1—Ba2—O1	−139.0 (4)	O13—Ba1—O3—C7	−43.8 (10)
O14—Ba1—Ba2—O1	−42.4 (4)	O12—Ba1—O3—C7	90.6 (10)
O10—Ba1—Ba2—O1	150.9 (5)	N1—Ba1—O3—C7	174.5 (10)
O13—Ba1—Ba2—O1	161.9 (3)	Ba2—Ba1—O3—C7	−162.6 (12)
O12—Ba1—Ba2—O1	−78.4 (4)	Ba2^iv—Ba1—O3—C7	62.3 (10)
N1—Ba1—Ba2—O1	23.4 (4)	O1—Ba1—O3—Ba2	−26.3 (3)
Ba2^iv—Ba1—Ba2—O1	−86.8 (3)	O11—Ba1—O3—Ba2	−168.8 (3)
O1—Ba1—Ba2—O9	−110.8 (4)	O9—Ba1—O3—Ba2	43.1 (3)
O11—Ba1—Ba2—O9	121.9 (3)	O15—Ba1—O3—Ba2	68.4 (4)
O15—Ba1—Ba2—O9	−22.3 (3)	O14—Ba1—O3—Ba2	−110.2 (3)
O3—Ba1—Ba2—O9	110.2 (4)	O10—Ba1—O3—Ba2	148.6 (2)
O14—Ba1—Ba2—O9	−153.2 (3)	O13—Ba1—O3—Ba2	118.8 (3)
O10—Ba1—Ba2—O9	40.1 (4)	O12—Ba1—O3—Ba2	−106.7 (3)
O13—Ba1—Ba2—O9	51.0 (3)	N1—Ba1—O3—Ba2	−22.9 (5)
O12—Ba1—Ba2—O9	170.8 (3)	Ba2^iv—Ba1—O3—Ba2	−135.1 (2)
N1—Ba1—Ba2—O9	−87.4 (3)	O1—Ba1—O9—Ba2	41.9 (2)
Ba2^iv—Ba1—Ba2—O9	162.4 (3)	O11—Ba1—O9—Ba2	−80.6 (3)
O1—Ba1—Ba2—O13ⁱ	96.4 (4)	O15—Ba1—O9—Ba2	158.3 (3)
O11—Ba1—Ba2—O13ⁱ	−30.9 (3)	O3—Ba1—O9—Ba2	−41.0 (2)
O9—Ba1—Ba2—O13ⁱ	−152.8 (3)	O14—Ba1—O9—Ba2	65.4 (6)
O15—Ba1—Ba2—O13ⁱ	−175.1 (3)	O10—Ba1—O9—Ba2	−161.4 (2)
O3—Ba1—Ba2—O13ⁱ	−42.6 (4)	O13—Ba1—O9—Ba2	−125.4 (3)
O14—Ba1—Ba2—O13ⁱ	54.0 (3)	O12—Ba1—O9—Ba2	−10.3 (4)
O10—Ba1—Ba2—O13ⁱ	−112.8 (4)	N1—Ba1—O9—Ba2	93.6 (3)
O13—Ba1—Ba2—O13ⁱ	−101.8 (3)	Ba2^iv—Ba1—O9—Ba2	−36.9 (5)
O12—Ba1—Ba2—O13ⁱ	18.0 (3)	O3—Ba2—O9—Ba1	42.5 (2)
N1—Ba1—Ba2—O13ⁱ	119.8 (3)	O15ⁱ—Ba2—O9—Ba1	−80.5 (3)
Ba2^iv—Ba1—Ba2—O13ⁱ	9.6 (2)	O11ⁱⁱ—Ba2—O9—Ba1	158.7 (3)
O1—Ba1—Ba2—O12ⁱⁱ	−73.5 (5)	O1—Ba2—O9—Ba1	−41.0 (2)
O11—Ba1—Ba2—O12ⁱⁱ	159.2 (4)	O13ⁱ—Ba2—O9—Ba1	67.9 (6)
O9—Ba1—Ba2—O12ⁱⁱ	37.3 (5)	O12ⁱⁱ—Ba2—O9—Ba1	−162.6 (2)
O15—Ba1—Ba2—O12ⁱⁱ	15.0 (4)	O14ⁱⁱ—Ba2—O9—Ba1	−124.8 (3)
O3—Ba1—Ba2—O12ⁱⁱ	147.5 (5)	O10ⁱ—Ba2—O9—Ba1	−8.9 (3)
O14—Ba1—Ba2—O12ⁱⁱ	−115.9 (4)	N3—Ba2—O9—Ba1	93.2 (3)
O10—Ba1—Ba2—O12ⁱⁱ	77.3 (5)	Ba1ⁱⁱ—Ba2—O9—Ba1	−163.9 (2)
O13—Ba1—Ba2—O12ⁱⁱ	88.3 (4)	O1—Ba1—O10—Ba2ⁱⁱⁱ	86.2 (7)
O12—Ba1—Ba2—O12ⁱⁱ	−151.9 (6)	O11—Ba1—O10—Ba2ⁱⁱⁱ	−125.2 (3)
N1—Ba1—Ba2—O12ⁱⁱ	−50.2 (4)	O9—Ba1—O10—Ba2ⁱⁱⁱ	−4.2 (3)
Ba2^iv—Ba1—Ba2—O12ⁱⁱ	−160.3 (4)	O15—Ba1—O10—Ba2ⁱⁱⁱ	41.9 (2)
O1—Ba1—Ba2—O14ⁱⁱ	−59.0 (3)	O3—Ba1—O10—Ba2ⁱⁱⁱ	−79.9 (3)
O11—Ba1—Ba2—O14ⁱⁱ	173.7 (2)	O14—Ba1—O10—Ba2ⁱⁱⁱ	158.5 (3)
O9—Ba1—Ba2—O14ⁱⁱ	51.8 (3)	O13—Ba1—O10—Ba2ⁱⁱⁱ	−45.2 (2)
O15—Ba1—Ba2—O14ⁱⁱ	29.5 (2)	O12—Ba1—O10—Ba2ⁱⁱⁱ	−155.7 (2)
O3—Ba1—Ba2—O14ⁱⁱ	162.0 (4)	N1—Ba1—O10—Ba2ⁱⁱⁱ	93.2 (3)
O14—Ba1—Ba2—O14ⁱⁱ	−101.4 (3)	Ba2—Ba1—O10—Ba2ⁱⁱⁱ	−32.3 (5)
O10—Ba1—Ba2—O14ⁱⁱ	91.9 (4)	Ba2^iv—Ba1—O10—Ba2ⁱⁱⁱ	−161.9 (2)
O13—Ba1—Ba2—O14ⁱⁱ	102.8 (2)	O1—Ba1—O11—Ba2^iv	63.1 (4)
O12—Ba1—Ba2—O14ⁱⁱ	−137.4 (2)	O9—Ba1—O11—Ba2^iv	148.9 (2)
N1—Ba1—Ba2—O14ⁱⁱ	−35.6 (3)	O15—Ba1—O11—Ba2^iv	−116.3 (3)
Ba2^iv—Ba1—Ba2—O14ⁱⁱ	−145.83 (17)	O3—Ba1—O11—Ba2^iv	112.9 (3)
O1—Ba1—Ba2—O10ⁱ	61.3 (3)	O14—Ba1—O11—Ba2^iv	−17.6 (2)
O11—Ba1—Ba2—O10ⁱ	−66.0 (2)	O10—Ba1—O11—Ba2^iv	−102.8 (3)
O9—Ba1—Ba2—O10ⁱ	172.1 (3)	O13—Ba1—O11—Ba2^iv	−165.8 (3)
O15—Ba1—Ba2—O10ⁱ	149.8 (2)	O12—Ba1—O11—Ba2^iv	45.1 (3)
O3—Ba1—Ba2—O10ⁱ	−77.7 (3)	N1—Ba1—O11—Ba2^iv	−21.6 (6)
O14—Ba1—Ba2—O10ⁱ	18.9 (2)	Ba2—Ba1—O11—Ba2^iv	105.4 (2)
O10—Ba1—Ba2—O10ⁱ	−147.8 (5)	O1—Ba1—O12—Ba2^iv	151.1 (3)
O13—Ba1—Ba2—O10ⁱ	−136.9 (2)	O11—Ba1—O12—Ba2^iv	−43.1 (2)
O12—Ba1—Ba2—O10ⁱ	−17.1 (2)	O9—Ba1—O12—Ba2^iv	−161.2 (2)
N1—Ba1—Ba2—O10ⁱ	84.7 (3)	O15—Ba1—O12—Ba2^iv	62.6 (9)
Ba2^iv—Ba1—Ba2—O10ⁱ	−25.53 (16)	O3—Ba1—O12—Ba2^iv	−130.6 (3)
O1—Ba1—Ba2—N3	161.6 (4)	O14—Ba1—O12—Ba2^iv	45.9 (2)
O11—Ba1—Ba2—N3	34.3 (3)	O10—Ba1—O12—Ba2^iv	−9.8 (4)
O9—Ba1—Ba2—N3	−87.6 (3)	O13—Ba1—O12—Ba2^iv	−77.0 (3)
O15—Ba1—Ba2—N3	−109.9 (3)	N1—Ba1—O12—Ba2^iv	101.8 (3)
O3—Ba1—Ba2—N3	22.6 (4)	Ba2—Ba1—O12—Ba2^iv	−167.9 (2)
O14—Ba1—Ba2—N3	119.2 (3)	O1—Ba1—O13—Ba2ⁱⁱⁱ	−111.2 (3)
O10—Ba1—Ba2—N3	−47.5 (4)	O11—Ba1—O13—Ba2ⁱⁱⁱ	121.5 (3)
O13—Ba1—Ba2—N3	−36.6 (3)	O9—Ba1—O13—Ba2ⁱⁱⁱ	−95.3 (3)
O12—Ba1—Ba2—N3	83.2 (3)	O15—Ba1—O13—Ba2ⁱⁱⁱ	−17.4 (2)
N1—Ba1—Ba2—N3	−175.0 (3)	O3—Ba1—O13—Ba2ⁱⁱⁱ	−160.6 (3)
Ba2^iv—Ba1—Ba2—N3	74.8 (2)	O14—Ba1—O13—Ba2ⁱⁱⁱ	78.9 (3)
O1—Ba1—Ba2—Ba1ⁱⁱ	−93.2 (3)	O10—Ba1—O13—Ba2ⁱⁱⁱ	47.0 (2)
O11—Ba1—Ba2—Ba1ⁱⁱ	139.50 (17)	O12—Ba1—O13—Ba2ⁱⁱⁱ	151.9 (2)
O9—Ba1—Ba2—Ba1ⁱⁱ	17.6 (3)	N1—Ba1—O13—Ba2ⁱⁱⁱ	−26.4 (5)
O15—Ba1—Ba2—Ba1ⁱⁱ	−4.63 (17)	Ba2—Ba1—O13—Ba2ⁱⁱⁱ	−127.36 (19)
O3—Ba1—Ba2—Ba1ⁱⁱ	127.8 (3)	Ba2^iv—Ba1—O13—Ba2ⁱⁱⁱ	112.63 (19)
O14—Ba1—Ba2—Ba1ⁱⁱ	−135.59 (19)	O1—Ba1—O14—Ba2^iv	−114.2 (3)
O10—Ba1—Ba2—Ba1ⁱⁱ	57.7 (4)	O11—Ba1—O14—Ba2^iv	16.9 (2)
O13—Ba1—Ba2—Ba1ⁱⁱ	68.66 (16)	O9—Ba1—O14—Ba2^iv	−135.3 (5)
O12—Ba1—Ba2—Ba1ⁱⁱ	−171.60 (17)	O15—Ba1—O14—Ba2^iv	138.9 (2)
N1—Ba1—Ba2—Ba1ⁱⁱ	−69.8 (2)	O3—Ba1—O14—Ba2^iv	−42.1 (4)
Ba2^iv—Ba1—Ba2—Ba1ⁱⁱ	180.0	O10—Ba1—O14—Ba2^iv	85.7 (3)
O1—Ba1—N1—C6	175.3 (12)	O13—Ba1—O14—Ba2^iv	58.5 (4)
O11—Ba1—N1—C6	−70.4 (12)	O12—Ba1—O14—Ba2^iv	−45.8 (2)
O9—Ba1—N1—C6	117.2 (11)	N1—Ba1—O14—Ba2^iv	−165.7 (4)
O15—Ba1—N1—C6	45.6 (11)	Ba2—Ba1—O14—Ba2^iv	−88.4 (2)
O3—Ba1—N1—C6	171.4 (10)	O1—Ba1—O15—Ba2ⁱⁱⁱ	149.8 (3)
O14—Ba1—N1—C6	−74.5 (11)	O11—Ba1—O15—Ba2ⁱⁱⁱ	−30.7 (4)
O10—Ba1—N1—C6	−1.7 (12)	O9—Ba1—O15—Ba2ⁱⁱⁱ	93.2 (3)
O13—Ba1—N1—C6	55.0 (13)	O3—Ba1—O15—Ba2ⁱⁱⁱ	69.9 (4)
O12—Ba1—N1—C6	−123.5 (11)	O14—Ba1—O15—Ba2ⁱⁱⁱ	−111.3 (3)
Ba2—Ba1—N1—C6	157.4 (11)	O10—Ba1—O15—Ba2ⁱⁱⁱ	−45.1 (2)
Ba2^iv—Ba1—N1—C6	−83.8 (11)	O13—Ba1—O15—Ba2ⁱⁱⁱ	17.9 (2)
O1—Ba1—N1—C2	−1.8 (8)	O12—Ba1—O15—Ba2ⁱⁱⁱ	−126.1 (7)
O11—Ba1—N1—C2	112.5 (9)	N1—Ba1—O15—Ba2ⁱⁱⁱ	−168.7 (4)
O9—Ba1—N1—C2	−59.9 (9)	Ba2—Ba1—O15—Ba2ⁱⁱⁱ	108.1 (2)
O15—Ba1—N1—C2	−131.5 (9)	Ba2^iv—Ba1—O15—Ba2ⁱⁱⁱ	−77.5 (3)
O3—Ba1—N1—C2	−5.7 (10)	Ba1—O1—C1—O2	168.9 (9)
O14—Ba1—N1—C2	108.4 (9)	Ba2—O1—C1—O2	−36.7 (17)
O10—Ba1—N1—C2	−178.8 (9)	Ba1—O1—C1—C2	−11.6 (16)
O13—Ba1—N1—C2	−122.1 (8)	Ba2—O1—C1—C2	142.7 (9)
O12—Ba1—N1—C2	59.4 (9)	C6—N1—C2—C3	4 (2)
Ba2—Ba1—N1—C2	−19.7 (9)	Ba1—N1—C2—C3	−178.6 (11)
Ba2^iv—Ba1—N1—C2	99.1 (9)	C6—N1—C2—C1	−179.5 (12)
O3—Ba2—N3—C8	−2.1 (8)	Ba1—N1—C2—C1	−2.1 (14)
O15ⁱ—Ba2—N3—C8	112.3 (9)	O2—C1—C2—N1	−172.2 (12)
O11ⁱⁱ—Ba2—N3—C8	−130.5 (10)	O1—C1—C2—N1	8.3 (17)
O1—Ba2—N3—C8	−5.0 (11)	O2—C1—C2—C3	4.3 (19)
O9—Ba2—N3—C8	−59.5 (9)	O1—C1—C2—C3	−175.2 (13)
O13ⁱ—Ba2—N3—C8	110.3 (9)	C5—N2—C3—C2	3 (2)
O12ⁱⁱ—Ba2—N3—C8	−178.2 (9)	N1—C2—C3—N2	−4 (2)
O14ⁱⁱ—Ba2—N3—C8	−121.8 (9)	C1—C2—C3—N2	179.2 (13)
O10ⁱ—Ba2—N3—C8	60.2 (9)	C3—N2—C5—C6	−2 (2)
Ba1—Ba2—N3—C8	−19.6 (9)	C2—N1—C6—C5	−3 (2)
Ba1ⁱⁱ—Ba2—N3—C8	−137.5 (9)	Ba1—N1—C6—C5	180.0 (11)
O3—Ba2—N3—C12	175.7 (12)	N2—C5—C6—N1	2 (3)
O15ⁱ—Ba2—N3—C12	−69.9 (12)	Ba2—O3—C7—O4	168.8 (10)
O11ⁱⁱ—Ba2—N3—C12	47.3 (11)	Ba1—O3—C7—O4	−34 (2)
O1—Ba2—N3—C12	172.8 (10)	Ba2—O3—C7—C8	−14.4 (18)
O9—Ba2—N3—C12	118.4 (11)	Ba1—O3—C7—C8	143.0 (9)
O13ⁱ—Ba2—N3—C12	−71.9 (11)	C12—N3—C8—C9	3.1 (19)
O12ⁱⁱ—Ba2—N3—C12	−0.3 (11)	Ba2—N3—C8—C9	−178.9 (10)
O14ⁱⁱ—Ba2—N3—C12	56.0 (12)	C12—N3—C8—C7	179.2 (12)
O10ⁱ—Ba2—N3—C12	−121.9 (11)	Ba2—N3—C8—C7	−2.7 (15)
Ba1—Ba2—N3—C12	158.2 (11)	O3—C7—C8—N3	10.2 (19)
Ba1ⁱⁱ—Ba2—N3—C12	40.4 (11)	O4—C7—C8—N3	−172.7 (12)
O11—Ba1—O1—C1	−125.4 (10)	O3—C7—C8—C9	−173.7 (13)
O9—Ba1—O1—C1	116.7 (11)	O4—C7—C8—C9	3 (2)
O15—Ba1—O1—C1	54.1 (10)	C11—N4—C9—C8	1 (2)
O3—Ba1—O1—C1	−175.8 (11)	N3—C8—C9—N4	−3 (2)
O14—Ba1—O1—C1	−54.1 (10)	C7—C8—C9—N4	−179.0 (14)
O10—Ba1—O1—C1	15.7 (15)	C9—N4—C11—C12	1 (2)
O13—Ba1—O1—C1	133.5 (9)	C8—N3—C12—C11	−1 (2)
O12—Ba1—O1—C1	−109.5 (10)	Ba2—N3—C12—C11	−178.9 (11)
N1—Ba1—O1—C1	7.4 (9)	N4—C11—C12—N3	−1 (3)
Ba2—Ba1—O1—C1	158.9 (12)	C18—N5—C14—C15	−1.2 (19)
Ba2^iv—Ba1—O1—C1	−91.0 (10)	C18—N5—C14—C13	177.9 (13)
O11—Ba1—O1—Ba2	75.7 (4)	O5—C13—C14—N5	−0.9 (18)
O9—Ba1—O1—Ba2	−42.2 (3)	O6—C13—C14—N5	−178.8 (12)
O15—Ba1—O1—Ba2	−104.9 (3)	O5—C13—C14—C15	178.1 (12)
O3—Ba1—O1—Ba2	25.3 (3)	O6—C13—C14—C15	0.2 (19)
O14—Ba1—O1—Ba2	147.0 (3)	C17—N6—C15—C14	1 (2)
O10—Ba1—O1—Ba2	−143.3 (6)	N5—C14—C15—N6	0 (2)
O13—Ba1—O1—Ba2	−25.4 (5)	C13—C14—C15—N6	−178.9 (14)
O12—Ba1—O1—Ba2	91.5 (3)	C15—N6—C17—C18	−2 (2)
N1—Ba1—O1—Ba2	−151.5 (4)	C14—N5—C18—C17	1 (2)
Ba2^iv—Ba1—O1—Ba2	110.1 (2)	N6—C17—C18—N5	1 (3)
O3—Ba2—O1—C1	173.6 (10)	C24—N7—C20—C21	−2 (2)
O15ⁱ—Ba2—O1—C1	30.4 (9)	C24—N7—C20—C19	178.0 (13)
O11ⁱⁱ—Ba2—O1—C1	−92.3 (10)	O8—C19—C20—N7	−173.2 (13)
O9—Ba2—O1—C1	−117.8 (10)	O7—C19—C20—N7	2.0 (19)
O13ⁱ—Ba2—O1—C1	88.1 (10)	O8—C19—C20—C21	7.2 (19)
O12ⁱⁱ—Ba2—O1—C1	−12.5 (11)	O7—C19—C20—C21	−177.6 (13)
O14ⁱⁱ—Ba2—O1—C1	−41.3 (9)	C23—N8—C21—C20	1 (2)
O10ⁱ—Ba2—O1—C1	93.3 (10)	N7—C20—C21—N8	1 (2)
N3—Ba2—O1—C1	176.1 (9)	C19—C20—C21—N8	−179.1 (14)
Ba1—Ba2—O1—C1	−160.1 (11)	C21—N8—C23—C24	−3 (2)
Ba1ⁱⁱ—Ba2—O1—C1	−55.0 (10)	C20—N7—C24—C23	1 (2)
O3—Ba2—O1—Ba1	−26.3 (3)	N8—C23—C24—N7	2 (3)
O15ⁱ—Ba2—O1—Ba1	−169.5 (3)

Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O7	0.85	2.23	3.000 (13)	152
O10—H10B···O5	0.85	1.92	2.769 (11)	177
O11—H11A···O4	0.85	1.88	2.669 (12)	153
O11—H11B···O5	0.85	2.04	2.861 (12)	163
O11—H11B···N5	0.85	2.62	3.191 (14)	126
O13—H13A···N5	0.85	2.14	2.983 (14)	175
O14—H14A···O8	0.85	1.87	2.685 (12)	160
O9—H9A···O7ⁱⁱ	0.85	1.88	2.677 (12)	155
O9—H9B···O5ⁱⁱ	0.85	1.89	2.689 (12)	156
O13—H13B···O6ⁱⁱ	0.85	1.93	2.729 (12)	157
O15—H15A···O7ⁱⁱ	0.85	2.04	2.860 (12)	161
O15—H15A···N7ⁱⁱ	0.85	2.62	3.208 (14)	127
O12—H12A···O7ⁱ	0.85	1.96	2.811 (12)	179
O12—H12B···O5ⁱ	0.85	2.26	3.018 (12)	149
O14—H14B···N7ⁱ	0.85	2.18	3.028 (13)	174
O15—H15B···O2ⁱⁱⁱ	0.85	1.90	2.676 (11)	152

Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Ba₂(C₅H₃N₂O₂)₂(H₂O)₇](C₅H₃N₂O₂)₂
M_r	893.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.5652 (10), 29.263 (3), 7.6067 (10)
β (°)	118.741 (2)
V (Å³)	1476.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.49 × 0.34 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.348, 0.669
No. of measured, independent and observed [I > 2σ(I)] reflections	7342, 4734, 4502
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.02
No. of reflections	4734
No. of parameters	406
No. of restraints	1
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.062P)² + 10.4333P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.84, −2.62
Absolute structure	Flack (1983), 2096 Friedel pairs
Absolute structure parameter	0.04 (4)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O7	0.85	2.23	3.000 (13)	152
O10—H10B···O5	0.85	1.92	2.769 (11)	177
O11—H11A···O4	0.85	1.88	2.669 (12)	153
O11—H11B···O5	0.85	2.04	2.861 (12)	163
O11—H11B···N5	0.85	2.62	3.191 (14)	126
O13—H13A···N5	0.85	2.14	2.983 (14)	175
O14—H14A···O8	0.85	1.87	2.685 (12)	160
O9—H9A···O7ⁱ	0.85	1.88	2.677 (12)	155
O9—H9B···O5ⁱ	0.85	1.89	2.689 (12)	156
O13—H13B···O6ⁱ	0.85	1.93	2.729 (12)	157
O15—H15A···O7ⁱ	0.85	2.04	2.860 (12)	161
O15—H15A···N7ⁱ	0.85	2.62	3.208 (14)	127
O12—H12A···O7ⁱⁱ	0.85	1.96	2.811 (12)	179
O12—H12B···O5ⁱⁱ	0.85	2.26	3.018 (12)	149
O14—H14B···N7ⁱⁱ	0.85	2.18	3.028 (13)	174
O15—H15B···O2ⁱⁱⁱ	0.85	1.90	2.676 (11)	152

Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1; (iii) x, y, z+1.

Acknowledgements

This work was supported by the Scientific Research Foundation of Northwest A&F University (grant No. Z111020828).

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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