Crystal structure of poly[μ2-aqua-aqua­(μ2-4-nitro-2,5,6-trioxo-1,2,5,6-tetra­hydro­pyridin-3-olato)hemi-μ4-oxalato-barium(II)]

Alabada, R.; Kovalchukova, O.; Polyakova, I.; Strashnova, S.; Sergienko, V.

doi:10.1107/S2056989015006520

research communications

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages 459-462

https://doi.org/10.1107/S2056989015006520

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Crystal structure of poly[μ₂-aqua-aqua(μ₂-4-nitro-2,5,6-trioxo-1,2,5,6-tetrahydropyridin-3-olato)hemi-μ₄-oxalato-barium(II)]

Rusul Alabada,^a ^* Olga Kovalchukova,^b Irina Polyakova,^c Svetlana Strashnova ^b and Vladimir Sergienko ^c

^aAl Muthanna University, Samawah, Al Mutanna, Iraq, ^bPeoples' Friendship University of Russia, 6 Miklukho-Mallaya, 117198 Moscow, Russian Federation, and ^cKurnakov Institute of General and Inorganic Chemistry RAS, 31 Leninskiy Avenue, 119991 Moscow, Russian Federation
^*Correspondence e-mail: www.chemistry1315@gmail.com

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 24 February 2015; accepted 31 March 2015; online 9 April 2015)

In the title coordination polymer, [Ba(C₅HN₂O₆)(C₂O₄)_0.5(H₂O)₂]_n, the tenfold coordination of the Ba centre consists of four O atoms from the two 4-nitro-2,5,6-trioxo-1,2,5,6-tetrahydropyridin-3-olate (L) anions, three O atoms of two oxalate anions and three water molecules. The Ba—O bond lengths fall in the range 2.698 (3)–2.978 (3) Å. The L ligand chelates two Ba atoms related by a screw axis, leading to formation of fused five- and six-membered chelate rings. Due to the bridging function of the ligands and water molecules, the complex monomers are connected into polymeric two-dimensional layers parallel to the bc plane. Intermolecular O—H⋯O hydrogen bonds link these layers into a three-dimensional supramolecular framework.

Keywords: crystal structure; two-dimensional coordination polymer; barium(II) compound; oxalate.

CCDC reference: 1057170

1. Chemical context

Mixed ligand coordination polymers containing bridging oxalate anions and 1,2-dicarbonyl carbocyclic or heterocyclic compounds exhibit high reactivity and different types of magnetism (Aldoshin, 2008 ; Coronado et al., 2007 ; Kitagawa & Kawata, 2002 ; Kovalchukova & Strashnova, 2014 ; Ohba & Okawa, 2000 ). Such compounds are of chemical interest, since a large number of potential donors available in the ligands predetermine a variety of coordination modes, which afford different geometries and dimensionalities of coordination polymers. Recently, we reported the synthesis, crystal structure and some properties of metal complexes of the 2,3,5,6-tetraoxo-4-nitro-4-idene anion (Kovalchukova et al., 2014, 2014 ; Dinh Do et al., 2013 ). The above-mentioned anion does not replace the water molecules from the inner sphere of the hydrated metal cations [M(H₂O)₆]ⁿ⁺, but can coordinate metal centres like sodium and silver(I). In the present paper, we report the molecular and crystal structure of a mixed-ligand barium complex containing 4-nitro-2,5,6-trioxo-1,2,5,6-tetrahydropyridin-3-olate (L) and oxalate anions as ligands.

2. Structural commentary

In the title compound, [Ba(C₅HN₂O₆)(C₂O₄)_0.5(H₂O)₂]_n, (I) (Fig. 1), the tenfold coordination of the Ba1 atom (Table 1) is formed by the O2, O5, O1 and O2 atoms of two 4-nitro-2,3,5,6-tetraoxopyridine-4-ide anions (L), the O7, O8 and O7A atoms of two oxalate anions, and the O9, O9A and O10 atoms of water molecules. The Ba—O bond lengths fall in the range 2.698 (3)–2.978 (3) Å, which is typical for ten-coordinate barium complexes containing oxalate anions (Viciano-Chumillas et al., 2010 ; Heinl et al., 2002 ; Marinescu et al., 2005 ; Belombe et al., 2003 , 2012 ; Larsson, 2001 ; Bouayad et al., 1995 ; Iveson et al., 2011 ). The L anion has a flattened skeleton. The r.m.s. deviation of the six ring atoms from their mean plane is 0.0256 Å; the O2 and O4 atoms lie in this plane deviating by 0.049 (3) and 0.010 (3) Å, respectively, whereas the O1 and O3 atoms deviate from it by 0.171 (3) and 0.077 (3) Å, respectively. The plane of the nitro group is rotated by 11.9 (8)° with respect to the ring plane. The L ligand chelates two Ba atoms related by a screw axis forming fused chelate rings. The six-membered ring is almost planar (r.m.s. deviation = 0.0353 Å) and the five–membered ring is folded along the O1—O2 line by 19.0°. The geometry of the L anion in the Ba complex is close to that in the compounds studied earlier (Kovalchukova et al., 2014; Dinh Do et al., 2013). All C=O bonds are of the double-bond type [1.200 (5)–1.229 (5) Å]. The monodentate coordination of L via the O atom of a nitro group attached to a benzene ring is in accordance with Venkatasubramanian et al. (1984 ), Harrowfield et al. (1998 ) and Chantrapromma et al. (2002 ). The centrosymmetric oxalate anion connects four Ba atoms closing two almost planar five–membered rings (r.m.s. deviation of rings = 0.0415 Å).

Table 1
Selected bond lengths (Å)

Ba1—O8ⁱ	2.698 (3)	Ba1—O10	2.882 (4)
Ba1—O7	2.728 (3)	Ba1—O1ⁱⁱⁱ	2.889 (3)
Ba1—O9	2.755 (3)	Ba1—O5	2.914 (4)
Ba1—O7ⁱⁱ	2.805 (3)	Ba1—O2	2.931 (3)
Ba1—O9ⁱⁱⁱ	2.860 (3)	Ba1—O2ⁱⁱⁱ	2.978 (3)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
View of (I)

, showing the atom-labelling scheme and 50% probability displacement ellipsoids. [Symmetry codes: (i) −x, y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (ii) −x, −y + 1, −z + 1; (iii) −x, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

3. Supramolecular features

Due to the bridging function of the L ligand and the O9 water molecule, the hydrated complex cations [Ba(L)(H₂O)₂]⁺ form wide zigzag bands running along the screw axes in the b-axis direction (Fig. 2). Oxalate anions connect the bands into thick two-dimensional networks parallel to bc. The networks have corrugated surfaces with terminal O3, O4 and O6 atoms of the L ligand on the `hills' and water molecules in the `hollows'. In the packing (Fig. 3), the `hills' enter the `hollows' of adjacent networks. Two-centre hydrogen bonds O9—H2⋯O3 and O10—H5⋯O4 and three-centre bonds O10—H4⋯(O3,O6) (Table 2) link the networks into a three-dimensional framework. Hydrogen bonds N1—H1⋯O6 and O9—H3⋯O8 link the elements of a band and a network, respectively.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6ⁱ	0.86	2.21	3.052 (5)	166
O9—H2⋯O3ⁱⁱ	0.82	2.10	2.877 (4)	158
O9—H3⋯O8ⁱ	0.82	1.84	2.639 (4)	163
O10—H4⋯O3ⁱⁱ	0.82	2.14	2.828 (5)	141
O10—H4⋯O6ⁱⁱ	0.82	2.30	3.010 (5)	146
O10—H5⋯O4ⁱⁱⁱ	0.82	2.41	3.210 (5)	165
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) x-1, y+1, z.

Figure 2
One-dimensional polymeric chain in (I)

. Oxalato ligands omitted for clarity.

Figure 3
two-dimensional polymeric layer in (I)

viewed approximately along the a axis.

4. Database survey

The synthesis, crystal structure and some properties of metal complexes of the 4-nitro-2,3,5,6-tetraoxo-4-idene anion are described in Kovalchukova et al. (2014) and Dinh Do et al. (2013). Model structures of complexes containing carbocyclic polyoxo compounds are reviewed in Kitagawa & Kawata (2002) and Kovalchukova & Strashnova (2014). Ten coordinated structures of Ba cations with oxalate anions containing other O-donating ligands have been described (Viciano-Chumillas et al., 2010; Marinescu et al., 2005; Belombe et al., 2003, 2012; Larsson, 2001; Bouayad et al., 1995; Iveson et al., 2011). Monodentate coordination via the O atom of a nitro aromatic group is described by Venkatasubramanian et al. (1984), Harrowfield et al. (1998) and Chantrapromma et al. (2002).

5. Synthesis and crystallization

Single crystals of (I) were grown by the slow evaporation of an ethanol solution of a 1:1:1 molar mixture of barium chloride, ammonium oxalate and ammonium 2,3,5,6-tetraoxo-4-nitro-4-inide.

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms of water molecules were localized in a difference map; O—H distances were normalized. The position of the amino H atom was calculated. All H atoms were refined within the riding model, with U_iso(H) = 1.2U_eq of the parent atom. The crystal studied was a twin without superposition of reciprocal lattices. Apparently, an accidental overlapping of reflections of two domains is responsible for increased displacement ellipsoids of some atoms. The U_ij components of atom O5 were restrained to approximate the isotropic behaviour.

Table 3
Experimental details

Crystal data
Chemical formula	[Ba(C₅HN₂O₆)(C₂O₄)_0.5(H₂O)₂]
M_r	804.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.3283 (11), 7.9868 (8), 13.0760 (14)
β (°)	96.419 (2)
V (Å³)	1071.88 (19)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	3.76
Crystal size (mm)	0.16 × 0.12 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.586, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11240, 3410, 2692
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.736

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.093, 1.05
No. of reflections	3410
No. of parameters	172
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.31, −1.67
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP (Johnson & Burnett, 1996 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1057170

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015006520/cv5485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006520/cv5485Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015006520/cv5485Isup3.mol

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP (Johnson & Burnett, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Poly[µ₂-aqua-aqua(m₄-4-nitro-2,5,6-trioxo-1,2,5,6-tetrahydropyridin-3-olato)hemi-µ₆-oxalato-barium(II)] top

Crystal data top

[Ba(C₅HN₂O₆)(C₂O₄)_0.5(H₂O)₂]	F(000) = 764
M_r = 804.92	D_x = 2.494 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3283 (11) Å	Cell parameters from 3977 reflections
b = 7.9868 (8) Å	θ = 3.0–31.4°
c = 13.0760 (14) Å	µ = 3.76 mm⁻¹
β = 96.419 (2)°	T = 296 K
V = 1071.88 (19) Å³	Plate, brown
Z = 2	0.16 × 0.12 × 0.03 mm

Data collection top

Bruker APEXII CCD diffractometer	2692 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.036
φ and ω scans	θ_max = 31.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→14
T_min = 0.586, T_max = 0.746	k = −11→11
11240 measured reflections	l = −19→18
3410 independent reflections

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)] = 0.038	Hydrogen site location: mixed
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0492P)² + 0.9998P] where P = (F_o² + 2F_c²)/3
3410 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 2.31 e Å⁻³
6 restraints	Δρ_min = −1.67 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Ba1	−0.00361 (2)	0.20711 (3)	0.69482 (2)	0.01991 (8)
O1	0.2105 (3)	−0.4097 (4)	0.6917 (3)	0.0343 (8)
O2	0.1678 (3)	−0.0830 (4)	0.6825 (3)	0.0295 (7)
O3	0.6026 (3)	−0.0297 (4)	0.6022 (3)	0.0344 (8)
O4	0.6113 (4)	−0.3626 (5)	0.5935 (4)	0.0489 (10)
O5	0.2660 (4)	0.2124 (5)	0.6490 (5)	0.0711 (16)
O6	0.4673 (4)	0.2379 (4)	0.6424 (4)	0.0446 (10)
O7	−0.0517 (3)	0.5240 (4)	0.6225 (2)	0.0259 (6)
O8	−0.0324 (4)	0.7141 (4)	0.5006 (3)	0.0380 (9)
O9	−0.1222 (3)	−0.0942 (4)	0.6412 (2)	0.0277 (7)
H2	−0.2018	−0.1018	0.6364	0.033*
H3	−0.1064	−0.1457	0.5898	0.033*
O10	−0.2582 (4)	0.2730 (5)	0.5886 (4)	0.0452 (10)
H4	−0.3231	0.2206	0.6007	0.054*
H5	−0.2776	0.3726	0.5862	0.054*
N1	0.4071 (3)	−0.3879 (4)	0.6348 (3)	0.0236 (7)
H1	0.4119	−0.4950	0.6295	0.028*
N2	0.3712 (4)	0.1478 (5)	0.6435 (3)	0.0258 (7)
C1	0.2940 (4)	−0.3217 (5)	0.6640 (3)	0.0211 (8)
C2	0.2754 (4)	−0.1295 (5)	0.6620 (3)	0.0196 (7)
C3	0.3832 (4)	−0.0309 (5)	0.6406 (3)	0.0201 (7)
C4	0.5038 (4)	−0.1026 (5)	0.6192 (3)	0.0217 (8)
C5	0.5130 (4)	−0.2959 (6)	0.6135 (4)	0.0250 (8)
C6	−0.0251 (4)	0.5680 (5)	0.5350 (3)	0.0218 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.02335 (13)	0.01750 (12)	0.01979 (12)	0.00255 (10)	0.00648 (8)	0.00287 (9)
O1	0.0313 (17)	0.0196 (16)	0.056 (2)	−0.0044 (13)	0.0208 (15)	0.0017 (14)
O2	0.0223 (15)	0.0213 (16)	0.048 (2)	0.0046 (12)	0.0156 (13)	0.0036 (13)
O3	0.0191 (15)	0.0244 (17)	0.061 (2)	−0.0021 (13)	0.0110 (14)	0.0034 (15)
O4	0.0296 (18)	0.0305 (19)	0.091 (3)	0.0069 (16)	0.0260 (19)	0.000 (2)
O5	0.037 (2)	0.026 (2)	0.157 (5)	0.0086 (17)	0.038 (3)	0.007 (2)
O6	0.0302 (18)	0.0179 (17)	0.087 (3)	−0.0070 (14)	0.0102 (19)	0.0005 (18)
O7	0.0408 (18)	0.0192 (14)	0.0193 (14)	0.0009 (13)	0.0101 (13)	−0.0011 (11)
O8	0.068 (3)	0.0215 (16)	0.0281 (17)	0.0077 (17)	0.0221 (17)	0.0028 (13)
O9	0.0241 (15)	0.0280 (16)	0.0318 (16)	0.0028 (13)	0.0063 (12)	−0.0083 (13)
O10	0.0294 (18)	0.032 (2)	0.072 (3)	−0.0050 (16)	−0.0021 (18)	0.0092 (18)
N1	0.0228 (17)	0.0139 (15)	0.035 (2)	0.0023 (13)	0.0096 (14)	0.0000 (14)
N2	0.0228 (17)	0.0192 (17)	0.036 (2)	0.0005 (14)	0.0066 (15)	0.0007 (15)
C1	0.0216 (19)	0.0184 (19)	0.0245 (19)	0.0014 (14)	0.0075 (15)	0.0000 (14)
C2	0.0198 (18)	0.0168 (18)	0.0227 (18)	0.0023 (15)	0.0049 (14)	0.0005 (15)
C3	0.0187 (18)	0.0146 (17)	0.027 (2)	−0.0003 (14)	0.0032 (15)	0.0012 (14)
C4	0.0191 (18)	0.0180 (18)	0.028 (2)	−0.0019 (15)	0.0043 (15)	0.0003 (15)
C5	0.0211 (19)	0.024 (2)	0.031 (2)	0.0023 (17)	0.0056 (16)	0.0027 (17)
C6	0.027 (2)	0.0183 (19)	0.0211 (19)	0.0020 (15)	0.0073 (15)	−0.0044 (14)

Geometric parameters (Å, º) top

Ba1—O8ⁱ	2.698 (3)	O7—C6	1.257 (5)
Ba1—O7	2.728 (3)	O7—Ba1ⁱⁱⁱ	2.805 (3)
Ba1—O9	2.755 (3)	O8—C6	1.250 (5)
Ba1—O7ⁱⁱ	2.805 (3)	O8—Ba1ⁱ	2.698 (3)
Ba1—O9ⁱⁱⁱ	2.860 (3)	O9—Ba1ⁱⁱ	2.860 (3)
Ba1—O10	2.882 (4)	O9—H2	0.8200
Ba1—O1ⁱⁱⁱ	2.889 (3)	O9—H3	0.8200
Ba1—O5	2.914 (4)	O10—H4	0.8201
Ba1—O2	2.931 (3)	O10—H5	0.8200
Ba1—O2ⁱⁱⁱ	2.978 (3)	N1—C5	1.372 (5)
O1—C1	1.199 (5)	N1—C1	1.375 (5)
O1—Ba1ⁱⁱ	2.889 (3)	N1—H1	0.8600
O2—C2	1.229 (5)	N2—C3	1.433 (5)
O2—Ba1ⁱⁱ	2.978 (3)	C1—C2	1.547 (6)
O3—C4	1.217 (5)	C2—C3	1.417 (5)
O4—C5	1.202 (5)	C3—C4	1.427 (5)
O5—N2	1.212 (5)	C4—C5	1.549 (6)
O6—N2	1.227 (5)	C6—C6ⁱ	1.546 (8)

O8ⁱ—Ba1—O7	59.61 (9)	O2—Ba1—O2ⁱⁱⁱ	149.14 (6)
O8ⁱ—Ba1—O9	93.86 (10)	C1—O1—Ba1ⁱⁱ	124.3 (3)
O7—Ba1—O9	131.58 (10)	C2—O2—Ba1	144.8 (3)
O8ⁱ—Ba1—O7ⁱⁱ	153.12 (10)	C2—O2—Ba1ⁱⁱ	122.0 (3)
O7—Ba1—O7ⁱⁱ	142.27 (8)	Ba1—O2—Ba1ⁱⁱ	91.81 (8)
O9—Ba1—O7ⁱⁱ	78.67 (9)	N2—O5—Ba1	152.8 (3)
O8ⁱ—Ba1—O9ⁱⁱⁱ	118.77 (10)	C6—O7—Ba1	121.7 (3)
O7—Ba1—O9ⁱⁱⁱ	78.16 (9)	C6—O7—Ba1ⁱⁱⁱ	125.8 (3)
O9—Ba1—O9ⁱⁱⁱ	145.81 (7)	Ba1—O7—Ba1ⁱⁱⁱ	100.18 (9)
O7ⁱⁱ—Ba1—O9ⁱⁱⁱ	67.59 (9)	C6—O8—Ba1ⁱ	123.3 (3)
O8ⁱ—Ba1—O10	73.50 (13)	Ba1—O9—Ba1ⁱⁱ	98.17 (9)
O7—Ba1—O10	62.78 (10)	Ba1—O9—H2	119.8
O9—Ba1—O10	71.41 (10)	Ba1ⁱⁱ—O9—H2	112.6
O7ⁱⁱ—Ba1—O10	126.42 (11)	Ba1—O9—H3	121.6
O9ⁱⁱⁱ—Ba1—O10	125.00 (11)	Ba1ⁱⁱ—O9—H3	102.8
O8ⁱ—Ba1—O1ⁱⁱⁱ	138.61 (12)	H2—O9—H3	100.9
O7—Ba1—O1ⁱⁱⁱ	111.17 (9)	Ba1—O10—H4	122.3
O9—Ba1—O1ⁱⁱⁱ	61.02 (9)	Ba1—O10—H5	113.6
O7ⁱⁱ—Ba1—O1ⁱⁱⁱ	59.07 (10)	H4—O10—H5	107.6
O9ⁱⁱⁱ—Ba1—O1ⁱⁱⁱ	95.40 (9)	C5—N1—C1	124.8 (4)
O10—Ba1—O1ⁱⁱⁱ	67.61 (11)	C5—N1—H1	117.6
O8ⁱ—Ba1—O5	64.24 (16)	C1—N1—H1	117.6
O7—Ba1—O5	93.23 (11)	O5—N2—O6	118.8 (4)
O9—Ba1—O5	111.61 (11)	O5—N2—C3	120.4 (4)
O7ⁱⁱ—Ba1—O5	94.27 (14)	O6—N2—C3	120.8 (4)
O9ⁱⁱⁱ—Ba1—O5	77.39 (14)	O1—C1—N1	121.4 (4)
O10—Ba1—O5	137.72 (16)	O1—C1—C2	119.6 (4)
O1ⁱⁱⁱ—Ba1—O5	152.77 (13)	N1—C1—C2	119.0 (3)
O8ⁱ—Ba1—O2	89.10 (10)	O2—C2—C3	128.6 (4)
O7—Ba1—O2	143.31 (9)	O2—C2—C1	114.2 (4)
O9—Ba1—O2	63.24 (9)	C3—C2—C1	117.1 (3)
O7ⁱⁱ—Ba1—O2	64.40 (9)	C2—C3—C4	122.6 (4)
O9ⁱⁱⁱ—Ba1—O2	104.67 (9)	C2—C3—N2	118.4 (4)
O10—Ba1—O2	129.95 (11)	C4—C3—N2	119.0 (3)
O1ⁱⁱⁱ—Ba1—O2	105.01 (9)	O3—C4—C3	127.7 (4)
O5—Ba1—O2	53.35 (10)	O3—C4—C5	114.3 (4)
O8ⁱ—Ba1—O2ⁱⁱⁱ	121.74 (10)	C3—C4—C5	117.9 (3)
O7—Ba1—O2ⁱⁱⁱ	64.65 (9)	O4—C5—N1	121.2 (4)
O9—Ba1—O2ⁱⁱⁱ	111.41 (8)	O4—C5—C4	120.7 (4)
O7ⁱⁱ—Ba1—O2ⁱⁱⁱ	84.77 (9)	N1—C5—C4	118.0 (3)
O9ⁱⁱⁱ—Ba1—O2ⁱⁱⁱ	61.45 (9)	O8—C6—O7	125.3 (4)
O10—Ba1—O2ⁱⁱⁱ	67.23 (11)	O8—C6—C6ⁱ	117.0 (5)
O1ⁱⁱⁱ—Ba1—O2ⁱⁱⁱ	53.60 (8)	O7—C6—C6ⁱ	117.7 (5)
O5—Ba1—O2ⁱⁱⁱ	135.85 (12)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^iv	0.86	2.21	3.052 (5)	166
O9—H2···O3^v	0.82	2.10	2.877 (4)	158
O9—H3···O8^iv	0.82	1.84	2.639 (4)	163
O10—H4···O3^v	0.82	2.14	2.828 (5)	141
O10—H4···O6^v	0.82	2.30	3.010 (5)	146
O10—H5···O4^vi	0.82	2.41	3.210 (5)	165

Symmetry codes: (iv) x, y−1, z; (v) x−1, y, z; (vi) x−1, y+1, z.

Acknowledgements

The research was supported by the Russian Foundation for Basic Research (grant No. 13-03-00079).

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