Crystal structure of bis­[cis-di­aqua­bis­(phen­an­thro­line)cobalt(II)] bis­(citrato)germanate(IV) dinitrate

Buchko, O.; Dyakonenko, V.; Martsinko, E.; Chebanenko, E.

doi:10.1107/S205698902100846X

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ISSN: 2056-9890

Volume 77| Part 9| September 2021| Pages 950-954

https://doi.org/10.1107/S205698902100846X

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Crystal structure of bis[cis-diaquabis(phenanthroline)cobalt(II)] bis(citrato)germanate(IV) dinitrate

Olha Buchko,^a Viktoriya Dyakonenko,^b ^* Elena Martsinko ^a and Elena Chebanenko ^a

^aI.I. Mechnikov Odessa National University, 2, Dvoryanskaya str., Odessa, 65082, Ukraine, and ^bSSI "Institute for Single Crystals", National Academy of Sciences of Ukraine, Naukyi Ave. 60, Kharkiv 61001, Ukraine
^*Correspondence e-mail: vika@xray.isc.kharkov.com

Edited by M. Zeller, Purdue University, USA (Received 8 July 2021; accepted 14 August 2021; online 20 August 2021)

The asymmetric unit of the title compound, [Co(C₁₂H₈N₂)₂(H₂O)₂]₂[Ge(C₆H₅O₇)₂](NO₃)₂, features two complex [(C₁₂H₈N₂)₂(H₂O)₂Co]²⁺ cations, two NO₃⁻ anions as well as one centrosymmetric [(C₆H₅O₇)₂Ge]²⁻ anion. Two HCit ligands (Cit = citrate, C₆H₄O₇) each coordinate via three different oxygen atoms (hydroxylate, α-carboxylate, β-carboxylate) to the Ge atom, forming a slightly distorted octahedron. The coordination polyhedron of the Co atom is also octahedral, formed by coordination of four nitrogen atoms from two phenanthroline molecules and two water oxygen atoms. In the crystal, the cations and anions are linked by hydrogen bonds and form layers parallel to the bc plane. The structure exhibits disorder of the NO₃⁻ anion [disorder ratio 0.688 (9) to 0.312 (9)]. There are also highly disordered solvent molecules (presumably water and/or ethanol) in the crystal structure; explicit refinement of these molecules was not possible, and the content of the voids was instead taken into account using reverse Fourier transform methods [SQUEEZE procedure in PLATON; Spek (2015 ). Acta Cryst. C71, 9–18]. The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s).

Keywords: crystal structure; bis(citrato)germanate; 3d metal salt; cobalt.

CCDC reference: 2103184

1. Chemical context

Citric acid (H₄Cit) is an essential component of the Krebs cycle and a universal intermediate in plant and animal metabolism. Its biocompatibility, hydrophilicity and general safety make citric acid a common component in foodstuffs, beverages, pharmaceuticals, cosmetics, etc (Nangare et al., 2021 ). Recently, Varbanets and co-workers have reported that germanium coordination compounds with citric acid combined with a second metal and ligand, such as Co and 1,10-phenanthroline (phen), show high antihypoxic, cerebroprotective properties and have an activation effect on enzymes (Lukianchuk et al., 2019 ; Gudzenko et al., 2019a ,b ). Complex compounds have been obtained through reactions in the system GeO₂–H₄Cit–CoX₂–phen–C₂H₅OH–H₂O (X = Cl, CH₃COO). The authors reported that the anion of the cobalt salt (chloride and acetate) affects the composition and structure of the complex and results in the formation of cation–anionic compounds such as [Co(phen)₃][Ge(HCit)₂]·2H₂O (Seifullina et al., 2017a ) or [Co(H₂O)₂(phen)₂]₂[Ge(Cit)₂]·4H₂O (Martsinko et al., 2018a ,b ). A bis(citrato)germanate anion with HCit₃ ligands tridentately coordinated to germanium are implemented in the structure [Co(phen)₃][Ge(HCit)₂]·2H₂O. In the [Co(phen)₃]²⁺ cation, the cobalt atom binds to three phenanthroline molecules. In [Co(H₂O)₂(phen)₂]₂[Ge(Cit)₂]·4H₂O, on the other hand, cobalt(II) combines with only two molecules of 1,10-phenanthroline and the oxygen atoms of two coordinated water molecules to complete the octahedral metal coordination. In this compound, the third carboxylic group of the citric acid is deprotonated, which leads to a change of the charge of the anion and of the molar Co:Ge ratio, while the coordination polyhedron of the germanium atom remains the same: distorted octahedral, formed by six oxygen atoms of three types of oxygen atoms from two tridentate chelating citrate ligands.

In the present work, we report the synthesis and structural analysis of a new complex, [Co(H₂O)₂(phen)₂]₂[Ge(HCit)₂(NO₃)₂], which was synthesized by changing the anion of the initial cobalt(II) salt to nitrate. This study is important for establishing the effect that the anion of the 3d metal salt has on the composition and structure of heterometal bis(citrato)germanates with 1,10-phenanthroline, as well as for the creation of new bioactive compounds.

2. Structural commentary

The title compound is a salt (Fig. 1), with a complex Co-based cation and two types of anions – the complex anion Ge(HCit)₂ and nitrate. The Ge atom occupies a special position on an inversion centre [the coordinates are (0.5, 1.0, 0.5)] so only half of the complex anion is located in the asymmetric unit. The charge of the two [Co(H₂O)₂(phen)₂]²⁺ cations are compensated by one Ge complex dianion and two nitrate anions.

Figure 1
The molecular structure of [Co(H₂O)₂(phen)₂]₂[Ge(HCit)₂(NO₃)₂] [symmetry code: (i)1 − x, 2 − y, 1 − z].

The coordination polyhedron of the Ge atom is a distorted octahedron formed by oxygen atoms of three types: hydroxyl (O3), α-carboxylate (O1) and β-carboxylate (O4) of two HCit³⁻ ligands. The Ge—O bond lengths are consequently not equivalent. The Ge1—O3 hydroxyl bond [1.813 (2) Å] is shorter than the bonds with the carboxylate oxygen atoms. In addition, the Ge—O1 bond with the α-carboxylate oxygen atom is shorter than the Ge–O4 bond with the β-carboxylate oxygen atom [1.914 (3) Å and 1.959 (3) Å, respectively]. The values of O—Ge—O bond angles lie in the 87.6 (1)–92.4 (1)° range (Table 1). The structure of the complex germanate anion is in a good agreement with those of similar complexes containing citratogermanates previously described (Martsinko et al., 2013 , 2018a,b; Seifullina et al., 2017a,b , 2019 ).

Table 1
Selected geometric parameters (Å, °)

Ge1—O1	1.914 (3)	Co1—N1	2.136 (3)
Ge1—O3	1.813 (2)	Co1—N2	2.123 (3)
Ge1—O4	1.959 (3)	Co1—N3	2.157 (4)
Co1—O8	2.083 (3)	Co1—N4	2.159 (3)
Co1—O9	2.100 (3)

O1—Ge1—O4ⁱ	90.92 (12)	O8—Co1—N4	92.07 (14)
O1—Ge1—O4	89.08 (12)	O9—Co1—N2	91.13 (13)
O3—Ge1—O1ⁱ	92.43 (11)	O9—Co1—N3	88.06 (13)
O3—Ge1—O1	87.58 (11)	O9—Co1—N4	92.60 (13)
O3—Ge1—O4ⁱ	89.40 (11)	N1—Co1—N3	96.18 (12)
O3—Ge1—O4	90.60 (11)	N1—Co1—N4	98.61 (12)
O8—Co1—O9	86.92 (13)	N2—Co1—N1	78.06 (12)
O8—Co1—N1	90.75 (13)	N2—Co1—N3	94.13 (14)
O8—Co1—N2	96.54 (14)	N3—Co1—N4	77.58 (13)
Symmetry code: (i) .

The coordination of the organic ligands to the Ge atom forms five- and six-membered metallocycles. The Ge1–O3–C2–C3–C4–O4 six-membered ring adopts a half-chair conformation [the C2 and O3 atoms deviate by 0.277 (4) and −0.657 (3) Å, respectively, from the mean plane though atoms Ge1, C3, C4 and O4, which is planar within 0.01 Å]. The Ge1—O1—C1—C2—O3 five-membered ring adopts an envelope conformation. Atom O3 deviates by 0.527 (3) Å from the mean plane of the remaining ring atoms (planar within 0.03 Å).

The coordination polyhedron of the Co atom is a distorted octahedron, which is formed by nitrogen atoms of two phenanthroline molecules and oxygen atoms of two water molecules. The Co—N and Co—O bond lengths lie in the ranges 2.120 (3)–2.160 (3) and 2.083 (3)–2.098 (3) Å, respectively, while the N—Co—N, O—Co—N and O—Co—O angles are in the range 77.6 (1)–98.6 (1)° (Table 1).

3. Supramolecular features

In the crystal, the water molecules of the [Co(H₂O)₂(phen)₂]²⁺ cation are linked to the [Ge(HCit)₂]²⁻ and NO₃⁻ anions by intermolecular O—H⋯O hydrogen bonds (Table 2); these supramolecular clusters form layers parallel to the bc plane (Fig. 2). Voids with a volume of 149 Å³ containing 49 electrons were found between adjacent layers. The content appears to be a combination of water and ethanol solvent molecules with more than twofold disorder. Refinement of these molecules was not possible, and the content of the voids was instead taken into account using reverse Fourier transform methods (SQUEEZE procedure; Spek, 2015).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O10ⁱⁱ	0.82	1.88	2.600 (12)	146
O8—H8A⋯O2	0.84 (2)	1.88 (2)	2.709 (4)	168 (5)
O9—H9A⋯O5ⁱⁱⁱ	0.82 (2)	1.96 (2)	2.701 (4)	150 (4)
O9—H9B⋯O10	0.82 (2)	1.99 (3)	2.789 (15)	166 (6)
Symmetry codes: (ii) x+1, y+1, z; (iii) .

Figure 2
The crystal packing of [Co(H₂O)₂(phen)₂]₂[Ge(HCit)₂(NO₃)₂] viewed along the b axis.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, update November 2020; Groom et al., 2016 ) for the Ge(HCit)₂²⁻ anion yielded 15 structures containing this anion (Seiler et al., 2005 ; Seifullina et al., 2006 , 2007 , 2015 , 2016 , 2017a,b; Martsinko et al., 2011 , 2013, 2018a,b). In these structures, the Ge—O bond lengths for the hydroxyl, α-carboxylate and β-carboxylate oxygen atoms are in the ranges 1.793–1.840, 1.881–1.914 and 1.904–1.955 Å, respectively.

A search for the [Co(H₂O)₂(phen)₂]²⁺ cation yielded six structures (Batsanov et al., 2011 ; Yang et al., 2003 ; Bulut et al., 2003 ; Abdelhak et al., 2006 ; Das et al., 2013 ; Fu et al., 2003 ). The Co—O bond lengths in the coordination polyhedron vary between 2.073 and 2.140 Å while the Co—N bond lengths range from within 2.118 to 2.164 Å.

No structures containing any combination of [Co(H₂O)₂(phen)₂]²⁺ cations and [Ge(HCit)₂]²⁻ anions were found in the CSD.

5. Synthesis and crystallization

A suspension of germanium(IV) oxide (0.0523 g, 0.5 mmol, GeO₂, 99.99%, Aldrich) and citric acid (0.21 g, 1 mmol, H₄Cit·H₂O, ≥99%, Aldrich) in 100 mL of hot distilled water was stirred to dissolve the reagents completely and slowly evaporated at 323 K to a volume of 20 mL. After cooling the mixture to room temperature, 20 mL of a 95% ethanol solution containing 1,10-phenanthroline (0.18 g, 1 mmol, phen, 99%, Aldrich) and cobalt(II) nitrate hexahydrate [0.146 g, 0.5 mmol, Co(NO₃)₂·6H₂O, ≥99%, Aldrich] were added (Fig. 3). Pink crystals suitable for X-ray analysis were obtained in two days, yield: 63%.

Figure 3
Two-step synthesis of [Co(H₂O)₂(phen)₂]₂[Ge(HCit)₂(NO₃)₂].

During the study of the thermal stability of the synthesized complex (Q-1500D PerkinElmer), it was established that its decomposition starts with an endothermic peak in the range of 393–423 K (peak 413 K). The corresponding weight loss of 1.5% indicates that the complex includes molecules of solvation. Therefore, crystals were dried at 423 K for 30 min to remove solvate molecules prior to the yield calculation and for elemental analysis.

Analysis calculated for C₆₀H₅₀Co₂GeN₁₀O₂₄ (1485.57) in %: C 48.47, H 3.37, Co 7.94, Ge 4.49, N 9.42; found C 48.25, H 3.26, Co 7.88, Ge 4.35, N 9.40 (ICP optical emission spectrometer Optima 2000 DV PerkinElmer and Elemental Analyzer CE-440).

IR (ν_max, cm⁻¹, spectrometer Frontier PerkinElmer, KBr): 3228 ν(OH), 3062, 2917 ν(C—H), 1743 ν(C=O), 1668 ν_as(COO⁻), 1613 δ(H₂O), 1587, 1519, 1428 ν(C—C_Ar), 1410 ν_s(COO⁻), 1367 ν(C—N), 1089 ν(C—O), 1198, 1148, 915, 856 δ(C—H), 641 ν(Ge—O), 554 ν(Co—O), 425 ν(Co—N).

The IR spectrum of the complex contains absorption bands for ν(C=O), ν_as(COO⁻) and ν_s(COO⁻), which indicate the presence of non-equivalent coordinated and free carboxyl groups in the complex. A ν(C—O) absorption band at 1089 cm⁻¹ evidences that the alcoholic OH groups of the citrate ligands are deprotonated and involved in coordination. The presence of Ge—O stretching vibrations suggests that the carboxylate and hydroxyl groups are bonded to germanium. Absorption bands assigned to the ν(C—N) heterocycle, the ν(C—C) phenanthroline ring vibrations and deformation vibrations δ(C—H) of the aromatic rings are also found in the IR spectrum. The compound contains coordinated water molecules, as indicated by the H₂O deformation vibrations at 1613 cm⁻¹.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Carbon-bound and carboxylic acid H atoms were added in calculated positions with C—H bond lengths of 0.93 Å for C—H, 0.97 Å for CH₂ and 0.82 Å for O—H bonds. Carboxylic acid H atoms were allowed to rotate but not to tip to best fit the experimental electron density. Water hydrogen atoms of the metal complex were located from difference-Fourier maps of electron density and their positions were refined with restraints of 0.84 (2) Å for O—H bond distances and 1.36 (2) Å for H⋯H distances. The position of one water H atom (H9A) was further restrained based on hydrogen bonding considerations. U_iso(H) were set to xU_eq(C,O), where x = 1.5 for hydroxyl groups and water molecules and 1.2 for all other H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₈N₂)₂(H₂O)₂]₂[Ge(C₆H₅O₇)₂]NO₃
M_r	1485.55
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	294
a, b, c (Å)	10.6719 (5), 11.8089 (4), 14.0901 (7)
α, β, γ (°)	105.697 (4), 94.026 (4), 104.815 (4)
V (Å³)	1633.98 (13)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.05
Crystal size (mm)	0.5 × 0.4 × 0.2

Data collection
Diffractometer	Rigaku Oxford Diffraction Xcalibur, Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.167, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14229, 7497, 4949
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.192, 0.98
No. of reflections	7497
No. of parameters	489
No. of restraints	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.87
Computer programs: CrysAlis PRO (Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2018/3 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

The structure exhibits disorder of the NO₃⁻ anion. All N—O bond distances were restrained to be similar to each other (within a standard deviation of 0.02 Å) and the distance between oxygen atoms O10B and O11B was restrained to a target value of 2.200 (4) Å. U^ij values of nitrate atoms closer to each other than 2 Å were restrained to be similar to each other (within a standard deviation of 0.02 Å²). Subject to these conditions, the disorder ratio refined to 0.688 (9):0.312 (9).

There are also highly disordered solvent molecules (presumably water and/or ethanol) in the crystal structure; explicit refinement of these molecules was not possible, and the content of the voids was instead taken into account using reverse Fourier transform methods (SQUEEZE; Spek, 2015) as implemented in the program PLATON (Spek, 2020 ). The voids with a volume of 149 Å³ contain 49 electrons.

Supporting information

CCDC reference: 2103184

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902100846X/zl5018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902100846X/zl5018Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[cis-diaquabis(phenanthroline)cobalt(II)] bis(citrato)germanate(IV) dinitrate top

Crystal data top

[Co(C₁₂H₈N₂)₂(H₂O)₂]₂[Ge(C₆H₅O₇)₂](NO₃)₂	Z = 1
M_r = 1485.55	F(000) = 758
Triclinic, P1	D_x = 1.510 Mg m⁻³
a = 10.6719 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8089 (4) Å	Cell parameters from 3558 reflections
c = 14.0901 (7) Å	θ = 3.6–26.0°
α = 105.697 (4)°	µ = 1.05 mm⁻¹
β = 94.026 (4)°	T = 294 K
γ = 104.815 (4)°	Block, colourless
V = 1633.98 (13) Å³	0.5 × 0.4 × 0.2 mm

Data collection top

Rigaku Oxford Diffraction Xcalibur, Sapphire3 diffractometer	7497 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4949 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 16.1827 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −13→15
T_min = 0.167, T_max = 1.000	l = −17→18
14229 measured reflections

Refinement top

Refinement on F²	131 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.092P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
7497 reflections	Δρ_max = 1.09 e Å⁻³
489 parameters	Δρ_min = −0.87 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ge1	0.500000	1.000000	0.500000	0.03675 (17)
Co1	0.33663 (5)	0.61981 (4)	0.77746 (4)	0.04432 (18)
O1	0.5174 (3)	0.9298 (2)	0.6060 (2)	0.0458 (6)
O2	0.6415 (3)	0.8220 (3)	0.6500 (2)	0.0586 (8)
O3	0.6711 (2)	1.0110 (2)	0.4908 (2)	0.0425 (6)
O4	0.4470 (3)	0.8345 (2)	0.4052 (2)	0.0491 (7)
O5	0.4742 (3)	0.6620 (2)	0.3179 (2)	0.0542 (7)
O6	0.8227 (3)	1.0894 (3)	0.7076 (3)	0.0752 (10)
O7	1.0212 (3)	1.0937 (4)	0.6678 (3)	0.0905 (12)
H7A	1.046289	1.134511	0.726375	0.136*
O8	0.5332 (3)	0.6796 (3)	0.7618 (3)	0.0618 (8)
H8A	0.574 (5)	0.717 (5)	0.725 (4)	0.093*
H8B	0.588 (4)	0.655 (5)	0.791 (4)	0.093*
O9	0.3742 (4)	0.4581 (3)	0.7902 (3)	0.0634 (8)
H9A	0.415 (4)	0.437 (4)	0.745 (3)	0.095*
H9B	0.306 (3)	0.407 (4)	0.789 (4)	0.095*
O10	0.1634 (11)	0.2778 (14)	0.8150 (6)	0.079 (2)	0.688 (9)
O10B	0.186 (3)	0.285 (3)	0.8413 (15)	0.105 (6)	0.312 (9)
O11	0.1943 (13)	0.3850 (8)	0.9768 (7)	0.145 (4)	0.688 (9)
O11B	0.287 (2)	0.3400 (17)	0.9953 (13)	0.154 (6)	0.312 (9)
O12	0.0517 (10)	0.2005 (10)	0.9183 (8)	0.157 (4)	0.688 (9)
O12B	0.072 (2)	0.304 (2)	0.9734 (17)	0.151 (5)	0.312 (9)
N1	0.3167 (3)	0.7994 (3)	0.7946 (2)	0.0457 (7)
N2	0.3626 (4)	0.6943 (3)	0.9350 (2)	0.0506 (8)
N3	0.1305 (3)	0.5296 (3)	0.7653 (3)	0.0479 (8)
N4	0.2778 (3)	0.5440 (3)	0.6181 (2)	0.0461 (8)
N5	0.1351 (12)	0.2883 (9)	0.9041 (7)	0.102 (3)	0.688 (9)
N5B	0.180 (2)	0.319 (3)	0.9359 (18)	0.124 (4)	0.312 (9)
C1	0.6179 (4)	0.8863 (3)	0.6003 (3)	0.0447 (9)
C2	0.7002 (4)	0.9130 (3)	0.5205 (3)	0.0397 (8)
C3	0.6587 (4)	0.7976 (4)	0.4312 (3)	0.0454 (9)
H3A	0.715808	0.809487	0.381935	0.054*
H3B	0.672611	0.729839	0.452798	0.054*
C4	0.5174 (4)	0.7610 (3)	0.3810 (3)	0.0394 (8)
C5	0.8460 (4)	0.9469 (4)	0.5569 (3)	0.0525 (10)
H5A	0.867066	0.874970	0.566046	0.063*
H5B	0.893737	0.970051	0.505709	0.063*
C6	0.8925 (5)	1.0500 (4)	0.6529 (4)	0.0632 (12)
C7	0.3017 (4)	0.8521 (4)	0.7247 (3)	0.0541 (10)
H7	0.299949	0.808312	0.658670	0.065*
C8	0.2886 (5)	0.9685 (5)	0.7449 (5)	0.0770 (16)
H8	0.277307	1.002198	0.693535	0.092*
C9	0.2924 (6)	1.0338 (5)	0.8411 (5)	0.0803 (17)
H9	0.282433	1.112360	0.855452	0.096*
C10	0.3110 (6)	0.9843 (4)	0.9186 (4)	0.0690 (14)
C11	0.3231 (4)	0.8637 (4)	0.8909 (3)	0.0497 (10)
C12	0.3176 (7)	1.0460 (5)	1.0206 (5)	0.092 (2)
H12	0.309794	1.125379	1.039407	0.110*
C13	0.3359 (7)	0.9894 (5)	1.0937 (4)	0.0885 (18)
H13	0.337511	1.030144	1.160419	0.106*
C14	0.3519 (5)	0.8692 (4)	1.0659 (4)	0.0666 (13)
C15	0.3463 (4)	0.8074 (4)	0.9668 (3)	0.0486 (9)
C16	0.3762 (6)	0.8107 (5)	1.1371 (4)	0.0761 (15)
H16	0.379325	0.848450	1.204675	0.091*
C17	0.3953 (6)	0.6961 (6)	1.1045 (4)	0.0787 (15)
H17	0.412778	0.655870	1.149965	0.094*
C18	0.3882 (5)	0.6420 (5)	1.0041 (4)	0.0684 (13)
H18	0.401944	0.564997	0.983189	0.082*
C19	0.0581 (5)	0.5253 (4)	0.8367 (4)	0.0620 (12)
H19	0.093641	0.575016	0.901218	0.074*
C20	−0.0684 (5)	0.4500 (5)	0.8195 (5)	0.0702 (13)
H20	−0.116577	0.450418	0.871997	0.084*
C21	−0.1230 (5)	0.3757 (5)	0.7271 (5)	0.0674 (13)
H21	−0.208339	0.324658	0.715527	0.081*
C22	−0.0488 (4)	0.3766 (4)	0.6486 (4)	0.0531 (10)
C23	0.0781 (4)	0.4572 (3)	0.6715 (3)	0.0440 (9)
C24	−0.0971 (5)	0.3013 (4)	0.5461 (4)	0.0644 (13)
H24	−0.180876	0.246614	0.530428	0.077*
C25	−0.0238 (5)	0.3089 (4)	0.4742 (4)	0.0634 (12)
H25	−0.057055	0.259283	0.409219	0.076*
C26	0.1055 (4)	0.3925 (4)	0.4953 (3)	0.0508 (10)
C27	0.1561 (4)	0.4645 (3)	0.5929 (3)	0.0436 (9)
C28	0.1845 (5)	0.4073 (4)	0.4225 (4)	0.0593 (12)
H28	0.154207	0.361152	0.356240	0.071*
C29	0.3026 (5)	0.4868 (4)	0.4473 (4)	0.0642 (12)
H29	0.355017	0.497089	0.398522	0.077*
C30	0.3479 (5)	0.5546 (4)	0.5458 (3)	0.0555 (10)
H30	0.431305	0.610072	0.561765	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ge1	0.0349 (3)	0.0352 (3)	0.0442 (3)	0.0129 (2)	0.0064 (2)	0.0156 (2)
Co1	0.0491 (3)	0.0407 (3)	0.0417 (3)	0.0123 (2)	0.0033 (2)	0.0112 (2)
O1	0.0451 (15)	0.0529 (15)	0.0486 (16)	0.0186 (13)	0.0101 (13)	0.0250 (12)
O2	0.0620 (19)	0.0699 (19)	0.065 (2)	0.0305 (16)	0.0121 (16)	0.0419 (16)
O3	0.0422 (15)	0.0426 (14)	0.0503 (16)	0.0154 (12)	0.0083 (12)	0.0230 (12)
O4	0.0410 (14)	0.0452 (15)	0.0594 (18)	0.0166 (12)	−0.0003 (13)	0.0106 (12)
O5	0.0590 (18)	0.0459 (15)	0.0540 (18)	0.0197 (14)	0.0005 (14)	0.0068 (13)
O6	0.061 (2)	0.080 (2)	0.073 (2)	0.0225 (18)	0.0113 (19)	0.0010 (18)
O7	0.052 (2)	0.111 (3)	0.084 (3)	0.016 (2)	−0.008 (2)	−0.001 (2)
O8	0.0465 (18)	0.072 (2)	0.069 (2)	0.0075 (16)	−0.0001 (16)	0.0349 (16)
O9	0.071 (2)	0.0506 (17)	0.079 (2)	0.0247 (16)	0.0242 (19)	0.0254 (16)
O10	0.093 (5)	0.080 (4)	0.061 (4)	0.019 (4)	−0.013 (4)	0.026 (4)
O10B	0.157 (11)	0.077 (7)	0.070 (9)	0.009 (9)	−0.009 (9)	0.034 (8)
O11	0.212 (9)	0.093 (5)	0.091 (5)	0.002 (5)	−0.003 (6)	0.012 (4)
O11B	0.175 (12)	0.088 (9)	0.159 (11)	0.000 (9)	−0.015 (10)	0.015 (8)
O12	0.169 (7)	0.153 (7)	0.123 (7)	−0.016 (6)	0.035 (6)	0.053 (6)
O12B	0.167 (10)	0.141 (10)	0.122 (9)	0.011 (9)	0.058 (8)	0.025 (8)
N1	0.0435 (18)	0.0484 (18)	0.0450 (19)	0.0124 (15)	0.0061 (15)	0.0143 (14)
N2	0.061 (2)	0.0498 (19)	0.044 (2)	0.0171 (17)	0.0063 (17)	0.0185 (15)
N3	0.0477 (19)	0.0493 (18)	0.049 (2)	0.0128 (15)	0.0088 (16)	0.0196 (15)
N4	0.0485 (19)	0.0437 (17)	0.0434 (19)	0.0106 (15)	0.0007 (15)	0.0125 (13)
N5	0.151 (7)	0.087 (5)	0.070 (5)	0.029 (5)	0.001 (5)	0.036 (4)
N5B	0.164 (8)	0.104 (7)	0.092 (8)	0.012 (7)	0.015 (7)	0.036 (7)
C1	0.040 (2)	0.041 (2)	0.054 (2)	0.0126 (17)	0.0013 (18)	0.0151 (17)
C2	0.0343 (18)	0.0420 (19)	0.048 (2)	0.0176 (16)	0.0053 (16)	0.0163 (16)
C3	0.041 (2)	0.050 (2)	0.050 (2)	0.0176 (18)	0.0082 (18)	0.0178 (17)
C4	0.045 (2)	0.0319 (17)	0.041 (2)	0.0123 (16)	0.0027 (16)	0.0090 (14)
C5	0.041 (2)	0.056 (2)	0.059 (3)	0.0181 (19)	−0.0031 (19)	0.0122 (19)
C6	0.051 (3)	0.065 (3)	0.066 (3)	0.014 (2)	−0.005 (2)	0.014 (2)
C7	0.051 (2)	0.063 (3)	0.058 (3)	0.017 (2)	0.006 (2)	0.033 (2)
C8	0.080 (4)	0.089 (4)	0.093 (4)	0.038 (3)	0.023 (3)	0.061 (3)
C9	0.102 (4)	0.067 (3)	0.098 (4)	0.047 (3)	0.031 (4)	0.042 (3)
C10	0.079 (4)	0.056 (3)	0.079 (4)	0.031 (3)	0.019 (3)	0.018 (2)
C11	0.050 (2)	0.045 (2)	0.052 (2)	0.0158 (19)	0.0063 (19)	0.0102 (17)
C12	0.126 (6)	0.064 (3)	0.085 (4)	0.042 (4)	0.024 (4)	0.006 (3)
C13	0.110 (5)	0.080 (4)	0.062 (4)	0.030 (3)	0.020 (3)	−0.004 (3)
C14	0.074 (3)	0.065 (3)	0.055 (3)	0.016 (3)	0.005 (3)	0.013 (2)
C15	0.052 (2)	0.047 (2)	0.041 (2)	0.0083 (18)	0.0039 (18)	0.0119 (16)
C16	0.074 (3)	0.096 (4)	0.050 (3)	0.016 (3)	0.004 (3)	0.016 (3)
C17	0.081 (4)	0.107 (4)	0.058 (3)	0.026 (3)	0.002 (3)	0.043 (3)
C18	0.084 (4)	0.077 (3)	0.050 (3)	0.030 (3)	−0.002 (3)	0.025 (2)
C19	0.057 (3)	0.063 (3)	0.068 (3)	0.015 (2)	0.015 (2)	0.024 (2)
C20	0.059 (3)	0.079 (3)	0.083 (4)	0.019 (3)	0.024 (3)	0.038 (3)
C21	0.044 (3)	0.066 (3)	0.100 (4)	0.008 (2)	0.013 (3)	0.044 (3)
C22	0.044 (2)	0.046 (2)	0.073 (3)	0.0119 (18)	0.000 (2)	0.026 (2)
C23	0.040 (2)	0.0384 (19)	0.057 (2)	0.0131 (16)	0.0001 (18)	0.0189 (16)
C24	0.047 (3)	0.049 (2)	0.089 (4)	0.004 (2)	−0.013 (3)	0.021 (2)
C25	0.065 (3)	0.051 (2)	0.062 (3)	0.013 (2)	−0.017 (2)	0.007 (2)
C26	0.055 (2)	0.043 (2)	0.051 (2)	0.0136 (18)	−0.010 (2)	0.0129 (17)
C27	0.043 (2)	0.0398 (19)	0.050 (2)	0.0133 (16)	−0.0026 (18)	0.0167 (16)
C28	0.065 (3)	0.058 (3)	0.047 (3)	0.020 (2)	−0.009 (2)	0.0059 (19)
C29	0.078 (3)	0.070 (3)	0.050 (3)	0.026 (3)	0.014 (2)	0.021 (2)
C30	0.054 (3)	0.059 (3)	0.048 (3)	0.008 (2)	0.010 (2)	0.0139 (19)

Geometric parameters (Å, º) top

Ge1—O1ⁱ	1.914 (3)	C5—H5A	0.9700
Ge1—O1	1.914 (3)	C5—H5B	0.9700
Ge1—O3ⁱ	1.813 (2)	C5—C6	1.505 (6)
Ge1—O3	1.813 (2)	C7—H7	0.9300
Ge1—O4ⁱ	1.959 (3)	C7—C8	1.372 (6)
Ge1—O4	1.959 (3)	C8—H8	0.9300
Co1—O8	2.083 (3)	C8—C9	1.357 (8)
Co1—O9	2.100 (3)	C9—H9	0.9300
Co1—N1	2.136 (3)	C9—C10	1.396 (7)
Co1—N2	2.123 (3)	C10—C11	1.414 (6)
Co1—N3	2.157 (4)	C10—C12	1.411 (8)
Co1—N4	2.159 (3)	C11—C15	1.442 (6)
O1—C1	1.301 (4)	C12—H12	0.9300
O2—C1	1.221 (4)	C12—C13	1.399 (9)
O3—C2	1.429 (4)	C13—H13	0.9300
O4—C4	1.282 (4)	C13—C14	1.425 (7)
O5—C4	1.214 (4)	C14—C15	1.378 (6)
O6—C6	1.196 (5)	C14—C16	1.408 (7)
O7—H7A	0.8200	C16—H16	0.9300
O7—C6	1.317 (6)	C16—C17	1.378 (7)
O8—H8A	0.839 (19)	C17—H17	0.9300
O8—H8B	0.846 (19)	C17—C18	1.374 (7)
O9—H9A	0.821 (17)	C18—H18	0.9300
O9—H9B	0.815 (19)	C19—H19	0.9300
O10—N5	1.292 (10)	C19—C20	1.376 (7)
O10B—N5B	1.294 (14)	C20—H20	0.9300
O11—N5	1.288 (10)	C20—C21	1.348 (8)
O11B—N5B	1.292 (14)	C21—H21	0.9300
O12—N5	1.253 (10)	C21—C22	1.405 (7)
O12B—N5B	1.295 (14)	C22—C23	1.399 (6)
N1—C7	1.321 (5)	C22—C24	1.452 (7)
N1—C11	1.351 (5)	C23—C27	1.440 (5)
N2—C15	1.349 (5)	C24—H24	0.9300
N2—C18	1.334 (5)	C24—C25	1.331 (7)
N3—C19	1.314 (5)	C25—H25	0.9300
N3—C23	1.353 (5)	C25—C26	1.433 (7)
N4—C27	1.351 (5)	C26—C27	1.391 (6)
N4—C30	1.321 (5)	C26—C28	1.392 (6)
C1—C2	1.524 (5)	C28—H28	0.9300
C2—C3	1.524 (5)	C28—C29	1.322 (7)
C2—C5	1.518 (5)	C29—H29	0.9300
C3—H3A	0.9700	C29—C30	1.381 (6)
C3—H3B	0.9700	C30—H30	0.9300
C3—C4	1.521 (5)

O1ⁱ—Ge1—O1	180.0	C6—C5—C2	114.2 (3)
O1ⁱ—Ge1—O4ⁱ	89.08 (12)	C6—C5—H5A	108.7
O1—Ge1—O4ⁱ	90.92 (12)	C6—C5—H5B	108.7
O1ⁱ—Ge1—O4	90.92 (12)	O6—C6—O7	124.1 (5)
O1—Ge1—O4	89.08 (12)	O6—C6—C5	125.0 (4)
O3—Ge1—O1ⁱ	92.43 (11)	O7—C6—C5	110.9 (4)
O3ⁱ—Ge1—O1ⁱ	87.57 (11)	N1—C7—H7	118.5
O3—Ge1—O1	87.58 (11)	N1—C7—C8	123.0 (5)
O3ⁱ—Ge1—O1	92.43 (11)	C8—C7—H7	118.5
O3ⁱ—Ge1—O3	180.0	C7—C8—H8	120.5
O3ⁱ—Ge1—O4ⁱ	90.60 (11)	C9—C8—C7	119.0 (5)
O3—Ge1—O4ⁱ	89.40 (11)	C9—C8—H8	120.5
O3ⁱ—Ge1—O4	89.40 (11)	C8—C9—H9	119.6
O3—Ge1—O4	90.60 (11)	C8—C9—C10	120.8 (4)
O4—Ge1—O4ⁱ	180.0	C10—C9—H9	119.6
O8—Co1—O9	86.92 (13)	C9—C10—C11	116.4 (5)
O8—Co1—N1	90.75 (13)	C9—C10—C12	124.6 (5)
O8—Co1—N2	96.54 (14)	C12—C10—C11	119.0 (5)
O8—Co1—N3	168.28 (14)	N1—C11—C10	121.9 (4)
O8—Co1—N4	92.07 (14)	N1—C11—C15	118.3 (3)
O9—Co1—N1	168.62 (14)	C10—C11—C15	119.8 (4)
O9—Co1—N2	91.13 (13)	C10—C12—H12	119.6
O9—Co1—N3	88.06 (13)	C13—C12—C10	120.9 (5)
O9—Co1—N4	92.60 (13)	C13—C12—H12	119.6
N1—Co1—N3	96.18 (12)	C12—C13—H13	120.0
N1—Co1—N4	98.61 (12)	C12—C13—C14	120.0 (5)
N2—Co1—N1	78.06 (12)	C14—C13—H13	120.0
N2—Co1—N3	94.13 (14)	C15—C14—C13	120.1 (5)
N2—Co1—N4	170.78 (13)	C15—C14—C16	117.9 (4)
N3—Co1—N4	77.58 (13)	C16—C14—C13	122.0 (5)
C1—O1—Ge1	109.6 (2)	N2—C15—C11	116.4 (4)
C2—O3—Ge1	107.7 (2)	N2—C15—C14	123.4 (4)
C4—O4—Ge1	127.8 (3)	C14—C15—C11	120.2 (4)
C6—O7—H7A	109.5	C14—C16—H16	120.7
Co1—O8—H8A	134 (3)	C17—C16—C14	118.5 (5)
Co1—O8—H8B	118 (3)	C17—C16—H16	120.7
H8A—O8—H8B	107 (3)	C16—C17—H17	120.3
Co1—O9—H9A	106 (3)	C18—C17—C16	119.3 (5)
Co1—O9—H9B	110 (4)	C18—C17—H17	120.3
H9A—O9—H9B	114 (3)	N2—C18—C17	123.3 (5)
C7—N1—Co1	128.3 (3)	N2—C18—H18	118.3
C7—N1—C11	118.9 (4)	C17—C18—H18	118.3
C11—N1—Co1	112.8 (3)	N3—C19—H19	118.7
C15—N2—Co1	114.3 (3)	N3—C19—C20	122.5 (5)
C18—N2—Co1	128.2 (3)	C20—C19—H19	118.7
C18—N2—C15	117.5 (4)	C19—C20—H20	119.7
C19—N3—Co1	128.8 (3)	C21—C20—C19	120.5 (5)
C19—N3—C23	118.5 (4)	C21—C20—H20	119.7
C23—N3—Co1	112.2 (3)	C20—C21—H21	120.5
C27—N4—Co1	112.8 (3)	C20—C21—C22	118.9 (4)
C30—N4—Co1	129.2 (3)	C22—C21—H21	120.5
C30—N4—C27	117.6 (4)	C21—C22—C24	124.0 (4)
O11—N5—O10	120.7 (11)	C23—C22—C21	117.3 (4)
O12—N5—O10	118.2 (10)	C23—C22—C24	118.7 (4)
O12—N5—O11	121.1 (10)	N3—C23—C22	122.3 (4)
O10B—N5B—O12B	124 (3)	N3—C23—C27	118.4 (3)
O11B—N5B—O10B	116.8 (15)	C22—C23—C27	119.3 (4)
O11B—N5B—O12B	117 (2)	C22—C24—H24	119.3
O1—C1—C2	115.1 (3)	C25—C24—C22	121.3 (4)
O2—C1—O1	123.4 (4)	C25—C24—H24	119.3
O2—C1—C2	121.4 (3)	C24—C25—H25	119.5
O3—C2—C1	109.2 (3)	C24—C25—C26	121.0 (4)
O3—C2—C3	108.5 (3)	C26—C25—H25	119.5
O3—C2—C5	109.4 (3)	C27—C26—C25	119.4 (4)
C3—C2—C1	106.9 (3)	C27—C26—C28	117.2 (4)
C5—C2—C1	112.1 (3)	C28—C26—C25	123.4 (4)
C5—C2—C3	110.6 (3)	N4—C27—C23	117.3 (3)
C2—C3—H3A	108.3	N4—C27—C26	122.4 (4)
C2—C3—H3B	108.3	C26—C27—C23	120.2 (4)
H3A—C3—H3B	107.4	C26—C28—H28	119.9
C4—C3—C2	115.8 (3)	C29—C28—C26	120.1 (4)
C4—C3—H3A	108.3	C29—C28—H28	119.9
C4—C3—H3B	108.3	C28—C29—H29	120.0
O4—C4—C3	119.9 (3)	C28—C29—C30	119.9 (5)
O5—C4—O4	121.5 (4)	C30—C29—H29	120.0
O5—C4—C3	118.6 (3)	N4—C30—C29	122.7 (4)
C2—C5—H5A	108.7	N4—C30—H30	118.7
C2—C5—H5B	108.7	C29—C30—H30	118.7
H5A—C5—H5B	107.6

Ge1—O1—C1—O2	−169.8 (3)	C9—C10—C11—C15	178.3 (5)
Ge1—O1—C1—C2	5.7 (4)	C9—C10—C12—C13	179.6 (6)
Ge1—O3—C2—C1	−32.7 (3)	C10—C11—C15—N2	−177.1 (4)
Ge1—O3—C2—C3	83.5 (3)	C10—C11—C15—C14	2.3 (7)
Ge1—O3—C2—C5	−155.8 (3)	C10—C12—C13—C14	1.9 (11)
Ge1—O4—C4—O5	−177.0 (3)	C11—N1—C7—C8	−1.9 (7)
Ge1—O4—C4—C3	2.6 (5)	C11—C10—C12—C13	0.0 (10)
Co1—N1—C7—C8	179.4 (4)	C12—C10—C11—N1	179.5 (5)
Co1—N1—C11—C10	−179.4 (4)	C12—C10—C11—C15	−2.0 (8)
Co1—N1—C11—C15	2.1 (5)	C12—C13—C14—C15	−1.6 (10)
Co1—N2—C15—C11	−4.1 (5)	C12—C13—C14—C16	177.2 (6)
Co1—N2—C15—C14	176.5 (4)	C13—C14—C15—N2	178.9 (5)
Co1—N2—C18—C17	−175.9 (4)	C13—C14—C15—C11	−0.4 (8)
Co1—N3—C19—C20	−170.6 (3)	C13—C14—C16—C17	−177.7 (6)
Co1—N3—C23—C22	170.9 (3)	C14—C16—C17—C18	−0.9 (9)
Co1—N3—C23—C27	−9.5 (4)	C15—N2—C18—C17	1.7 (8)
Co1—N4—C27—C23	9.6 (4)	C15—C14—C16—C17	1.1 (9)
Co1—N4—C27—C26	−171.0 (3)	C16—C14—C15—N2	0.1 (8)
Co1—N4—C30—C29	170.5 (3)	C16—C14—C15—C11	−179.3 (5)
O1ⁱ—Ge1—O3—C2	−149.9 (2)	C16—C17—C18—N2	−0.5 (9)
O1—Ge1—O3—C2	30.1 (2)	C18—N2—C15—C11	178.0 (4)
O1—C1—C2—O3	17.6 (4)	C18—N2—C15—C14	−1.5 (7)
O1—C1—C2—C3	−99.6 (4)	C19—N3—C23—C22	−1.4 (5)
O1—C1—C2—C5	139.1 (3)	C19—N3—C23—C27	178.2 (3)
O2—C1—C2—O3	−166.8 (4)	C19—C20—C21—C22	−0.2 (7)
O2—C1—C2—C3	76.0 (5)	C20—C21—C22—C23	−1.0 (6)
O2—C1—C2—C5	−45.3 (5)	C20—C21—C22—C24	−179.7 (4)
O3—C2—C3—C4	−54.0 (4)	C21—C22—C23—N3	1.8 (6)
O3—C2—C5—C6	68.0 (5)	C21—C22—C23—C27	−177.8 (3)
O4—Ge1—O3—C2	−59.0 (2)	C21—C22—C24—C25	177.8 (4)
O4ⁱ—Ge1—O3—C2	121.0 (2)	C22—C23—C27—N4	179.6 (3)
N1—C7—C8—C9	0.7 (8)	C22—C23—C27—C26	0.2 (5)
N1—C11—C15—N2	1.4 (6)	C22—C24—C25—C26	−0.3 (7)
N1—C11—C15—C14	−179.2 (4)	C23—N3—C19—C20	0.1 (6)
N3—C19—C20—C21	0.7 (8)	C23—C22—C24—C25	−0.9 (6)
N3—C23—C27—N4	0.0 (5)	C24—C22—C23—N3	−179.4 (3)
N3—C23—C27—C26	−179.4 (3)	C24—C22—C23—C27	1.0 (5)
C1—C2—C3—C4	63.7 (4)	C24—C25—C26—C27	1.5 (6)
C1—C2—C5—C6	−53.3 (5)	C24—C25—C26—C28	−177.7 (4)
C2—C3—C4—O4	9.6 (5)	C25—C26—C27—N4	179.2 (3)
C2—C3—C4—O5	−170.7 (3)	C25—C26—C27—C23	−1.4 (5)
C2—C5—C6—O6	13.3 (7)	C25—C26—C28—C29	179.5 (4)
C2—C5—C6—O7	−165.2 (4)	C26—C28—C29—C30	0.5 (7)
C3—C2—C5—C6	−172.5 (4)	C27—N4—C30—C29	−1.1 (6)
C5—C2—C3—C4	−174.0 (3)	C27—C26—C28—C29	0.3 (6)
C7—N1—C11—C10	1.6 (6)	C28—C26—C27—N4	−1.6 (5)
C7—N1—C11—C15	−176.9 (4)	C28—C26—C27—C23	177.8 (3)
C7—C8—C9—C10	0.8 (9)	C28—C29—C30—N4	−0.1 (7)
C8—C9—C10—C11	−1.0 (9)	C30—N4—C27—C23	−177.4 (3)
C8—C9—C10—C12	179.3 (6)	C30—N4—C27—C26	2.0 (5)
C9—C10—C11—N1	−0.2 (7)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O10ⁱⁱ	0.82	1.88	2.600 (12)	146
O8—H8A···O2	0.84 (2)	1.88 (2)	2.709 (4)	168 (5)
O9—H9A···O5ⁱⁱⁱ	0.82 (2)	1.96 (2)	2.701 (4)	150 (4)
O9—H9B···O10	0.82 (2)	1.99 (3)	2.789 (15)	166 (6)

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

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