Tetra­ammonium bis­(metforminium) di-μ6-oxido-tetra-μ3-oxido-tetra­deca-μ2-oxido-octa­oxidodeca­vanadium(V) hexa­hydrate

Polito-Lucas, J.A.; Núñez-Ávila, J.A.; Bernès, S.; Pérez-Benítez, A.

doi:10.1107/S2414314621006349

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 6| June 2021| x210634

https://doi.org/10.1107/S2414314621006349

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Tetraammonium bis(metforminium) di-μ₆-oxido-tetra-μ₃-oxido-tetradeca-μ₂-oxido-octaoxidodecavanadium(V) hexahydrate

J. Alberto Polito-Lucas,^a José A. Núñez-Ávila,^a Sylvain Bernès ^a ^* and Aarón Pérez-Benítez ^b

^aInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico, and ^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico
^*Correspondence e-mail: sylvain_bernes@hotmail.com

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 10 June 2021; accepted 18 June 2021; online 25 June 2021)

The title compound, (NH₄)₄(C₄H₁₂N₅)₂[V₁₀O₂₈]·6H₂O, crystallizes with the decavanadate anion placed on an inversion centre in space group P $[\overline{1}]$ . This anion is surrounded by a first shell of ammonium cations and water molecules, forming efficient N—H⋯O and O—H⋯O hydrogen bonds. A second shell includes metforminium monocations with a twisted geometry, also forming numerous intermolecular hydrogen bonds. The complex three-dimensional network of non-covalent interactions affords a crystal structure in which the cations and anions are densely packed.

Keywords: crystal structure; metformin; decavanadate; hydrogen bond.

CCDC reference: 2090930

Structure description

Metformin hydrochloride (Metf·HCl: 1,1-dimethylbiguanide hydrochloride; Niranjana Devi et al., 2017 ) is the first-line therapy for type 2 diabetes. On the other hand, some anionic or cationic vanadium species, such as vanadate and vanadyl, have also been shown to be useful in the treatment of human diabetes (Domingo & Gómez, 2016 ). Based on this background, several groups belonging to the Autonomous University of Puebla are involved in the synthesis of compounds including both metformin and oxidovanadate derivatives, with the hope of achieving synergistic effects (Sánchez-Lombardo et al., 2014 ). The associated chemical crystallography is rather complex, because due to its basic character metformin can be found in various states of protonation (neutral, cationic or dicationic forms), while the degree of condensation for the vanadate moiety strongly depends on the pH of the reaction medium. Finally, most of these compounds are crystallized with a number of water molecules, which is unpredictable. The compound reported here includes one (V₁₀O₂₈)⁶⁻ anion, four ammonium cations, two metforminium(1+) cations HMetf⁺, and six water molecules (Fig. 1).

Figure 1
The molecular entities in the structure of the title compound, with displacement ellipsoids for non-H atoms at the 50% probability level. Cations and water molecules in the asymmetric unit are labelled.

The (V₁₀O₂₈)⁶⁻ anion is situated on an inversion centre in space group P $[\overline{1}]$ , and approaches the expected D_2h symmetry, which has been extensively reported (Bošnjaković-Pavlović et al., 2011 ). The negative charges are balanced by four NH₄⁺ and two HMetf⁺ cations. The high resolution of the measured diffraction data (d_min = 0.56 Å) unequivocally establishes that there is no protonation of the decavanadate. The HMetf⁺ monocation has its charge located mainly on N2. Furthermore, this cation is characterized by a dihedral angle of 54.85 (5)° between planes C2–C4/N3–N5 and C1/N1–N3. This twisted geometry is observed in several other compounds of metforminium(1+). Indeed, metformin and its cations HMetf⁺ and H₂Metf²⁺ are highly flexible entities: the twist angle for 93 structures recovered from the CSD (Groom et al., 2016 ) varies from 1 to 85°.

In the crystal structure, anions and cations are well distributed, in such a way that the repulsive Coulombic forces between the highly charged anions are minimized. The decavanadate anion, the cations, and the crystal water molecules engage in an extensive network of hydrogen bonds (Table 1). All N—H and O—H groups present in the asymmetric unit serve as donor groups. The two strongest hydrogen bonds are formed between the anion and one ammonium [N6—H6A⋯O8^v; symmetry code: (v) −x + 1, −y + 2, −z + 1], as well as between the anion and a water molecule (O17—H17A⋯O13; Fig. 2). As a consequence of the large number of hydrogen bonds, ions and molecules are packed in an efficient way (Fig. 3), as reflected in the quite high Kitaigorodskii packing index of 0.743 (Kitaigorodskii, 1965 ; Spek, 2009 ). The mean atomic volume for non-H atoms is 16.5 Å³ for the title compound, similar to those calculated for previously reported structures in this series (Sánchez-Lombardo et al., 2014). This indicates that in this family of ionic compounds, the lattice energy can be optimized through the inclusion of a suitable number of water molecules.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O10ⁱ	0.818 (19)	2.080 (19)	2.8981 (12)	178 (2)
N1—H1B⋯O6	0.76 (2)	2.71 (2)	3.4507 (15)	163.9 (19)
N2—H2A⋯O12ⁱⁱ	0.854 (18)	2.112 (18)	2.9457 (12)	165.4 (17)
N2—H2B⋯O15ⁱⁱⁱ	0.849 (19)	2.072 (19)	2.9164 (16)	172.9 (17)
N4—H4D⋯O9ⁱⁱⁱ	0.912 (19)	2.423 (19)	3.2993 (14)	161.1 (16)
N4—H4E⋯O16^iv	0.736 (19)	2.269 (19)	2.9686 (16)	159.2 (19)
N6—H6A⋯O8^v	0.882 (19)	1.865 (19)	2.7463 (13)	176.7 (17)
N6—H6B⋯O17ⁱ	0.874 (18)	1.921 (19)	2.7871 (13)	170.7 (17)
N6—H6C⋯O7	0.808 (19)	1.990 (19)	2.7922 (11)	172.2 (18)
N6—H6D⋯O2ⁱ	0.873 (19)	2.074 (19)	2.8541 (13)	148.3 (16)
N7—H7A⋯O16	0.835 (18)	2.083 (18)	2.8810 (14)	159.8 (17)
N7—H7B⋯O4^vi	0.880 (18)	2.056 (18)	2.8627 (12)	152.1 (16)
N7—H7C⋯O1^vii	0.843 (19)	2.072 (19)	2.9050 (12)	169.7 (17)
N7—H7D⋯O11^viii	0.873 (18)	1.928 (18)	2.7957 (12)	172.1 (16)
O15—H15A⋯O12	0.81 (2)	2.38 (2)	3.1833 (16)	171 (2)
O15—H15B⋯O17^ix	0.78 (2)	2.03 (2)	2.8046 (18)	177 (3)
O16—H16A⋯O15^vi	0.80 (2)	2.05 (2)	2.8477 (18)	176 (2)
O16—H16B⋯O5^x	0.83 (2)	2.23 (2)	2.8937 (13)	137 (2)
O17—H17A⋯O13	0.85 (1)	1.87 (2)	2.7130 (12)	172 (2)
O17—H17B⋯N3	0.82 (2)	2.07 (2)	2.8830 (15)	170 (2)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) x, y+1, z; (v) ; (vi) ; (vii) ; (viii) ; (ix) x+1, y, z; (x) .

Figure 2
Main interactions between the (V₁₀O₂₈)⁶⁻ anion (polyhedral representation) and the cations and water molecules. The strongest hydrogen bonds are represented as magenta dashed bonds (entries 7 and 19 in Table 1

), while secondary hydrogen bonds are represented with thin black dashed lines.

Figure 3
Part of the crystal structure of the title salt, viewed along [010]. Colour code: pale-blue polyhedra: (V₁₀O₂₈)⁶⁻ anions; orange: ammonium; blue: metforminium(1+); red: water.

Synthesis and crystallization

Good-quality single crystals of the title compound were obtained during the reaction between ammonium metavanadate (NH₄VO₃, 1.117 g, 9.5 mmol; Pérez-Benítez & Bernès, 2018 ) and metformin hydrochloride (Metf·HCl, 0.497 g, 3 mmol; Niranjana Devi et al., 2017) in 100 ml of distilled water and 6 ml of acetic acid 5% v/v. In a typical procedure, the ammonium metavanadate was dissolved by heating in a water bath and then metformin hydrochloride was added and stirred until its dissolution. The water bath was removed and once the mixture cooled down to room temperature, the acetic acid was added. The homogeneous solution was slowly evaporated during several days at ambient conditions, which allowed the separation of reaction by-products by fractional crystallization, being the main products [H₂Metf]₃(V₁₀O₂₈)·8H₂O and [H₂Metf]₂[NH₄]₂(V₁₀O₂₈)·10H₂O (CCDC-993916 and 993917, with yields of ca 53 and 24%, respectively; Sánchez-Lombardo et al., 2014) and the title compound, [HMetf]₂[NH₄]₄(V₁₀O₂₈)·6H₂O (ca. 5% yield). These yields are poorly reproducible, and no powder diffraction was performed on the solid phases obtained by fractional crystallization to check their purity. Therefore, we cannot rule out the presence of other crystallized compounds in this reaction.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	(NH₄)₄(C₄H₁₂N₅)₂[V₁₀O₂₈]·6H₂O
M_r	1398.03
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	295
a, b, c (Å)	9.7965 (2), 10.1010 (2), 13.0974 (3)
α, β, γ (°)	81.081 (2), 70.906 (2), 63.321 (2)
V (Å³)	1094.30 (5)
Z	1
Radiation type	Ag Kα, λ = 0.56083 Å
μ (mm⁻¹)	1.10
Crystal size (mm)	0.26 × 0.26 × 0.19

Data collection
Diffractometer	Stoe Stadivari
Absorption correction	Multi-scan (X-AREA; Stoe & Cie, 2020 )
T_min, T_max	0.426, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	94693, 11269, 9224
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.851

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.078, 1.06
No. of reflections	11269
No. of parameters	361
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.95
Computer programs: X-AREA (Stoe & Cie, 2020), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2090930

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621006349/im4012sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621006349/im4012Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2020); cell refinement: X-AREA (Stoe & Cie, 2020); data reduction: X-AREA (Stoe & Cie, 2020); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Tetraammonium bis(metforminium) di-µ₆-oxido-tetra-µ₃-oxido-tetradeca-µ₂-oxido-octaoxidodecavanadium(V) hexahydrate top

Crystal data top

(NH₄)₄(C₄H₁₂N₅)₂[V₁₀O₂₈]·6H₂O	Z = 1
M_r = 1398.03	F(000) = 700
Triclinic, P1	D_x = 2.121 Mg m⁻³
a = 9.7965 (2) Å	Ag Kα radiation, λ = 0.56083 Å
b = 10.1010 (2) Å	Cell parameters from 131899 reflections
c = 13.0974 (3) Å	θ = 2.2–33.7°
α = 81.081 (2)°	µ = 1.10 mm⁻¹
β = 70.906 (2)°	T = 295 K
γ = 63.321 (2)°	Tetrahedron, gold
V = 1094.30 (5) Å³	0.26 × 0.26 × 0.19 mm

Data collection top

Stoe Stadivari diffractometer	11269 independent reflections
Radiation source: Sealed X-ray tube, Axo Astix-f Microfocus source	9224 reflections with I > 2σ(I)
Graded multilayer mirror monochromator	R_int = 0.030
Detector resolution: 5.81 pixels mm^-1	θ_max = 28.5°, θ_min = 2.2°
ω scans	h = −16→16
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2020)	k = −17→17
T_min = 0.426, T_max = 0.907	l = −22→21
94693 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0487P)² + 0.0305P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
11269 reflections	Δρ_max = 0.47 e Å⁻³
361 parameters	Δρ_min = −0.95 e Å⁻³
9 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0048 (9)
Primary atom site location: dual

Special details top

Refinement. All H atoms, with exception of the methyl groups in the HMetf⁺ cation, were refined with free coordinates and isotropic displacement parameters calculated as U_iso(H) = 1.2 or 1.5×U_eq(carrier atom). The geometry for the three water molecules was restrained, with target bond lengths O—H = 0.85 (2) Å and H···H separations of 1.34 (2) Å. Methyl H atoms were included using a riding model with U_iso(H) = 1.5×U_eq(carrier atom).

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

	x	y	z	U_iso*/U_eq
V1	0.39655 (2)	0.84689 (2)	0.38300 (2)	0.02229 (4)
V2	0.22257 (2)	0.64431 (2)	0.44890 (2)	0.02011 (3)
V3	0.44412 (2)	0.63696 (2)	0.58069 (2)	0.01697 (3)
V4	0.72567 (2)	0.57810 (2)	0.36227 (2)	0.01973 (3)
V5	0.50248 (2)	0.59053 (2)	0.23433 (2)	0.02221 (4)
O1	0.33595 (10)	1.02437 (8)	0.37493 (7)	0.03200 (16)
O2	0.04039 (9)	0.66456 (10)	0.48094 (7)	0.02993 (15)
O3	0.43043 (9)	0.62643 (8)	0.71288 (5)	0.02402 (13)
O4	0.90793 (9)	0.55609 (9)	0.33301 (7)	0.02955 (15)
O5	0.52329 (11)	0.57067 (11)	0.11007 (6)	0.03517 (18)
O6	0.20204 (8)	0.83200 (8)	0.43086 (6)	0.02483 (13)
O7	0.38555 (9)	0.81825 (7)	0.54386 (6)	0.02400 (13)
O8	0.61636 (8)	0.77845 (7)	0.36354 (6)	0.02343 (12)
O9	0.43593 (9)	0.79045 (8)	0.24684 (6)	0.02459 (13)
O10	0.24430 (7)	0.63107 (7)	0.59608 (5)	0.01873 (11)
O11	0.66939 (8)	0.57599 (7)	0.52504 (5)	0.01927 (11)
O12	0.71111 (8)	0.55367 (8)	0.23235 (5)	0.02325 (12)
O13	0.29624 (8)	0.60661 (8)	0.30286 (5)	0.02357 (12)
O14	0.52088 (7)	0.40515 (7)	0.58287 (5)	0.01779 (10)
C1	0.06586 (13)	1.15154 (12)	0.16742 (9)	0.03002 (19)
C2	0.26523 (13)	1.04792 (11)	0.00500 (8)	0.02878 (18)
C3	0.2491 (2)	0.8359 (2)	−0.04832 (12)	0.0567 (5)
H3A	0.301998	0.759308	−0.002811	0.085*
H3B	0.268909	0.794033	−0.115518	0.085*
H3C	0.136312	0.880514	−0.012978	0.085*
C4	0.42436 (17)	0.94509 (16)	−0.17351 (10)	0.0408 (3)
H4A	0.377248	1.032108	−0.214239	0.061*
H4B	0.453653	0.858445	−0.212180	0.061*
H4C	0.517801	0.943143	−0.163104	0.061*
N1	0.02667 (15)	1.12792 (15)	0.27388 (9)	0.0428 (3)
H1A	−0.050 (2)	1.197 (2)	0.3093 (15)	0.051*
H1B	0.078 (2)	1.055 (2)	0.2967 (16)	0.051*
N2	−0.00914 (13)	1.28620 (12)	0.13003 (9)	0.0373 (2)
H2A	−0.089 (2)	1.355 (2)	0.1705 (14)	0.045*
H2B	0.000 (2)	1.299 (2)	0.0630 (15)	0.045*
N3	0.17233 (12)	1.03435 (10)	0.10395 (7)	0.03244 (19)
N4	0.32345 (14)	1.14908 (13)	−0.02036 (10)	0.0388 (2)
H4D	0.381 (2)	1.154 (2)	−0.0901 (15)	0.047*
H4E	0.301 (2)	1.201 (2)	0.0224 (15)	0.047*
N5	0.30971 (13)	0.94745 (11)	−0.06891 (7)	0.03350 (19)
N6	0.18645 (12)	1.10848 (11)	0.61533 (8)	0.02925 (17)
H6A	0.252 (2)	1.143 (2)	0.6196 (14)	0.044*
H6B	0.110 (2)	1.130 (2)	0.6764 (15)	0.044*
H6C	0.238 (2)	1.022 (2)	0.5989 (14)	0.044*
H6D	0.143 (2)	1.156 (2)	0.5644 (15)	0.044*
N7	0.22214 (11)	0.34134 (10)	0.33362 (8)	0.02681 (15)
H7A	0.258 (2)	0.3611 (19)	0.2689 (15)	0.040*
H7B	0.117 (2)	0.3902 (19)	0.3535 (13)	0.040*
H7C	0.247 (2)	0.250 (2)	0.3412 (14)	0.040*
H7D	0.265 (2)	0.3602 (19)	0.3754 (14)	0.040*
O15	0.99461 (17)	0.64089 (15)	0.09649 (9)	0.0543 (3)
H15A	0.924 (2)	0.621 (3)	0.1371 (18)	0.081*
H15B	1.021 (3)	0.683 (3)	0.1260 (19)	0.081*
O16	0.28519 (14)	0.39198 (12)	0.10371 (8)	0.0451 (2)
H16A	0.204 (2)	0.464 (2)	0.1036 (18)	0.068*
H16B	0.365 (2)	0.405 (2)	0.0658 (17)	0.068*
O17	0.07918 (11)	0.80032 (11)	0.20277 (7)	0.03818 (19)
H17A	0.152 (2)	0.7348 (19)	0.2284 (15)	0.057*
H17B	0.114 (2)	0.8621 (19)	0.1780 (16)	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.02379 (7)	0.01451 (6)	0.02375 (7)	−0.00547 (5)	−0.00600 (5)	0.00227 (4)
V2	0.01597 (6)	0.02161 (7)	0.02045 (6)	−0.00631 (5)	−0.00604 (5)	0.00221 (5)
V3	0.01774 (6)	0.01375 (6)	0.01733 (6)	−0.00493 (4)	−0.00428 (4)	−0.00203 (4)
V4	0.01655 (6)	0.01890 (6)	0.02113 (6)	−0.00737 (5)	−0.00352 (5)	0.00193 (4)
V5	0.02394 (7)	0.02343 (7)	0.01623 (6)	−0.00812 (5)	−0.00540 (5)	0.00068 (5)
O1	0.0359 (4)	0.0162 (3)	0.0350 (4)	−0.0073 (3)	−0.0061 (3)	0.0027 (2)
O2	0.0196 (3)	0.0363 (4)	0.0325 (4)	−0.0114 (3)	−0.0096 (3)	0.0059 (3)
O3	0.0284 (3)	0.0222 (3)	0.0195 (3)	−0.0088 (2)	−0.0060 (2)	−0.0034 (2)
O4	0.0198 (3)	0.0333 (4)	0.0332 (4)	−0.0122 (3)	−0.0063 (3)	0.0058 (3)
O5	0.0416 (4)	0.0430 (5)	0.0189 (3)	−0.0167 (4)	−0.0084 (3)	−0.0002 (3)
O6	0.0202 (3)	0.0191 (3)	0.0278 (3)	−0.0038 (2)	−0.0057 (2)	0.0022 (2)
O7	0.0275 (3)	0.0148 (3)	0.0256 (3)	−0.0063 (2)	−0.0059 (2)	−0.0018 (2)
O8	0.0232 (3)	0.0187 (3)	0.0275 (3)	−0.0099 (2)	−0.0063 (2)	0.0027 (2)
O9	0.0254 (3)	0.0218 (3)	0.0227 (3)	−0.0078 (2)	−0.0077 (2)	0.0043 (2)
O10	0.0164 (2)	0.0165 (2)	0.0186 (2)	−0.00421 (19)	−0.00313 (19)	−0.00076 (18)
O11	0.0192 (3)	0.0188 (3)	0.0201 (3)	−0.0082 (2)	−0.0060 (2)	−0.00041 (19)
O12	0.0210 (3)	0.0247 (3)	0.0184 (3)	−0.0073 (2)	−0.0024 (2)	−0.0001 (2)
O13	0.0234 (3)	0.0266 (3)	0.0214 (3)	−0.0103 (2)	−0.0088 (2)	0.0018 (2)
O14	0.0169 (2)	0.0156 (2)	0.0186 (2)	−0.0056 (2)	−0.00443 (19)	−0.00012 (18)
C1	0.0266 (4)	0.0305 (5)	0.0278 (4)	−0.0078 (4)	−0.0042 (3)	−0.0085 (3)
C2	0.0271 (4)	0.0238 (4)	0.0266 (4)	−0.0051 (3)	−0.0037 (3)	−0.0035 (3)
C3	0.0736 (11)	0.0555 (9)	0.0407 (7)	−0.0432 (8)	0.0149 (7)	−0.0195 (6)
C4	0.0440 (6)	0.0412 (6)	0.0261 (5)	−0.0177 (5)	0.0048 (4)	−0.0050 (4)
N1	0.0390 (5)	0.0437 (6)	0.0251 (4)	−0.0017 (5)	−0.0030 (4)	−0.0092 (4)
N2	0.0353 (5)	0.0281 (4)	0.0343 (5)	−0.0034 (4)	−0.0039 (4)	−0.0079 (3)
N3	0.0342 (4)	0.0260 (4)	0.0234 (4)	−0.0058 (3)	0.0004 (3)	−0.0048 (3)
N4	0.0403 (5)	0.0346 (5)	0.0367 (5)	−0.0174 (4)	0.0002 (4)	−0.0080 (4)
N5	0.0390 (5)	0.0300 (4)	0.0237 (4)	−0.0148 (4)	0.0032 (3)	−0.0059 (3)
N6	0.0284 (4)	0.0227 (4)	0.0323 (4)	−0.0077 (3)	−0.0070 (3)	−0.0029 (3)
N7	0.0254 (4)	0.0237 (4)	0.0315 (4)	−0.0102 (3)	−0.0087 (3)	−0.0008 (3)
O15	0.0633 (7)	0.0591 (7)	0.0337 (5)	−0.0251 (6)	−0.0099 (5)	0.0053 (4)
O16	0.0503 (6)	0.0430 (5)	0.0348 (4)	−0.0206 (4)	−0.0042 (4)	0.0031 (4)
O17	0.0328 (4)	0.0406 (5)	0.0318 (4)	−0.0107 (4)	−0.0091 (3)	0.0082 (3)

Geometric parameters (Å, º) top

V1—O1	1.6137 (7)	V5—O14ⁱ	2.3350 (6)
V1—O9	1.8226 (7)	C1—N2	1.3271 (16)
V1—O6	1.8689 (8)	C1—N1	1.3332 (15)
V1—O8	1.8811 (7)	C1—N3	1.3451 (13)
V1—O7	2.0554 (7)	C2—N4	1.3318 (16)
V1—O14ⁱ	2.3173 (6)	C2—N5	1.3374 (13)
V1—V5	3.0663 (2)	C2—N3	1.3460 (14)
V1—V2	3.0755 (2)	C3—N5	1.4474 (18)
V1—V3	3.1011 (2)	C3—H3A	0.9600
V1—V4	3.1042 (2)	C3—H3B	0.9600
V2—O2	1.6161 (8)	C3—H3C	0.9600
V2—O6	1.8001 (7)	C4—N5	1.4554 (14)
V2—O13	1.8440 (7)	C4—H4A	0.9600
V2—O10	1.9854 (7)	C4—H4B	0.9600
V2—O11ⁱ	2.0185 (7)	C4—H4C	0.9600
V2—O14ⁱ	2.2343 (6)	N1—H1A	0.818 (19)
V2—V4ⁱ	3.0815 (2)	N1—H1B	0.76 (2)
V3—O3	1.6825 (7)	N2—H2A	0.854 (18)
V3—O7	1.6968 (7)	N2—H2B	0.849 (19)
V3—O11	1.9098 (7)	N4—H4D	0.912 (19)
V3—O10	1.9284 (7)	N4—H4E	0.736 (19)
V3—O14	2.1121 (6)	N6—H6A	0.882 (19)
V3—O14ⁱ	2.1349 (6)	N6—H6B	0.874 (18)
V3—V5ⁱ	3.0737 (2)	N6—H6C	0.808 (19)
V4—O4	1.6145 (7)	N6—H6D	0.873 (19)
V4—O8	1.8153 (7)	N7—H7A	0.835 (18)
V4—O12	1.8158 (7)	N7—H7B	0.880 (18)
V4—O10ⁱ	2.0094 (7)	N7—H7C	0.843 (19)
V4—O11	2.0192 (6)	N7—H7D	0.873 (18)
V4—O14ⁱ	2.2168 (6)	O15—H15A	0.812 (16)
V4—V5	3.1128 (2)	O15—H15B	0.778 (16)
V5—O5	1.6055 (8)	O16—H16A	0.804 (15)
V5—O9	1.8385 (7)	O16—H16B	0.830 (15)
V5—O13	1.8649 (7)	O17—H17A	0.850 (14)
V5—O12	1.8978 (7)	O17—H17B	0.820 (15)
V5—O3ⁱ	2.0607 (7)

O1—V1—O9	104.84 (4)	O12—V4—V1	84.23 (2)
O1—V1—O6	101.04 (4)	O10ⁱ—V4—V1	124.447 (19)
O9—V1—O6	92.16 (3)	O11—V4—V1	87.655 (19)
O1—V1—O8	102.51 (4)	O14ⁱ—V4—V1	48.162 (16)
O9—V1—O8	91.10 (3)	V2ⁱ—V4—V1	120.184 (6)
O6—V1—O8	154.52 (3)	O4—V4—V5	136.16 (3)
O1—V1—O7	98.71 (4)	O8—V4—V5	84.21 (2)
O9—V1—O7	156.44 (3)	O12—V4—V5	33.88 (2)
O6—V1—O7	83.85 (3)	O10ⁱ—V4—V5	87.47 (2)
O8—V1—O7	83.12 (3)	O11—V4—V5	124.45 (2)
O1—V1—O14ⁱ	172.87 (4)	O14ⁱ—V4—V5	48.462 (16)
O9—V1—O14ⁱ	82.28 (3)	V2ⁱ—V4—V5	119.451 (6)
O6—V1—O14ⁱ	78.35 (3)	V1—V4—V5	59.105 (6)
O8—V1—O14ⁱ	77.07 (3)	O5—V5—O9	104.08 (4)
O7—V1—O14ⁱ	74.17 (2)	O5—V5—O13	102.38 (4)
O1—V1—V5	138.11 (3)	O9—V5—O13	91.70 (3)
O9—V1—V5	33.28 (2)	O5—V5—O12	102.89 (4)
O6—V1—V5	84.42 (2)	O9—V5—O12	90.47 (3)
O8—V1—V5	84.55 (2)	O13—V5—O12	153.29 (3)
O7—V1—V5	123.18 (2)	O5—V5—O3ⁱ	100.16 (4)
O14ⁱ—V1—V5	49.017 (16)	O9—V5—O3ⁱ	155.75 (3)
O1—V1—V2	133.39 (3)	O13—V5—O3ⁱ	83.71 (3)
O9—V1—V2	83.40 (3)	O12—V5—O3ⁱ	83.45 (3)
O6—V1—V2	32.35 (2)	O5—V5—O14ⁱ	174.46 (4)
O8—V1—V2	123.42 (2)	O9—V5—O14ⁱ	81.46 (3)
O7—V1—V2	80.88 (2)	O13—V5—O14ⁱ	77.01 (3)
O14ⁱ—V1—V2	46.362 (16)	O12—V5—O14ⁱ	77.00 (3)
V5—V1—V2	61.310 (6)	O3ⁱ—V5—O14ⁱ	74.30 (2)
O1—V1—V3	129.40 (3)	O5—V5—V1	137.01 (4)
O9—V1—V3	125.76 (2)	O9—V5—V1	32.96 (2)
O6—V1—V3	79.55 (2)	O13—V5—V1	83.39 (2)
O8—V1—V3	78.07 (2)	O12—V5—V1	84.06 (2)
O7—V1—V3	30.690 (19)	O3ⁱ—V5—V1	122.825 (19)
O14ⁱ—V1—V3	43.479 (15)	O14ⁱ—V5—V1	48.521 (15)
V5—V1—V3	92.496 (6)	O5—V5—V3ⁱ	131.12 (4)
V2—V1—V3	61.458 (5)	O9—V5—V3ⁱ	124.81 (2)
O1—V1—V4	134.70 (3)	O13—V5—V3ⁱ	78.32 (2)
O9—V1—V4	81.46 (2)	O12—V5—V3ⁱ	78.62 (2)
O6—V1—V4	123.80 (2)	O3ⁱ—V5—V3ⁱ	30.960 (18)
O8—V1—V4	32.23 (2)	O14ⁱ—V5—V3ⁱ	43.346 (15)
O7—V1—V4	81.57 (2)	V1—V5—V3ⁱ	91.865 (6)
O14ⁱ—V1—V4	45.455 (15)	O5—V5—V4	135.05 (4)
V5—V1—V4	60.588 (6)	O9—V5—V4	80.99 (2)
V2—V1—V4	91.644 (6)	O13—V5—V4	122.29 (2)
V3—V1—V4	61.402 (5)	O12—V5—V4	32.23 (2)
O2—V2—O6	103.19 (4)	O3ⁱ—V5—V4	81.44 (2)
O2—V2—O13	102.93 (4)	O14ⁱ—V5—V4	45.285 (16)
O6—V2—O13	94.22 (3)	V1—V5—V4	60.308 (5)
O2—V2—O10	99.24 (4)	V3ⁱ—V5—V4	61.383 (5)
O6—V2—O10	92.09 (3)	V3—O3—V5ⁱ	109.98 (3)
O13—V2—O10	154.87 (3)	V2—O6—V1	113.89 (4)
O2—V2—O11ⁱ	98.97 (4)	V3—O7—V1	111.12 (3)
O6—V2—O11ⁱ	156.53 (3)	V4—O8—V1	114.22 (4)
O13—V2—O11ⁱ	88.24 (3)	V1—O9—V5	113.76 (4)
O10—V2—O11ⁱ	76.68 (3)	V3—O10—V2	107.49 (3)
O2—V2—O14ⁱ	173.66 (3)	V3—O10—V4ⁱ	106.61 (3)
O6—V2—O14ⁱ	82.01 (3)	V2—O10—V4ⁱ	100.95 (3)
O13—V2—O14ⁱ	80.07 (3)	V3—O11—V2ⁱ	107.71 (3)
O10—V2—O14ⁱ	76.76 (3)	V3—O11—V4	107.45 (3)
O11ⁱ—V2—O14ⁱ	75.42 (3)	V2ⁱ—O11—V4	99.49 (3)
O2—V2—V1	136.83 (3)	V4—O12—V5	113.89 (3)
O6—V2—V1	33.75 (2)	V2—O13—V5	115.19 (4)
O13—V2—V1	83.44 (2)	V3—O14—V3ⁱ	102.04 (3)
O10—V2—V1	88.47 (2)	V3—O14—V4ⁱ	93.65 (2)
O11ⁱ—V2—V1	124.06 (2)	V3ⁱ—O14—V4ⁱ	93.42 (2)
O14ⁱ—V2—V1	48.643 (16)	V3—O14—V2ⁱ	93.73 (2)
O2—V2—V4ⁱ	89.10 (3)	V3ⁱ—O14—V2ⁱ	92.47 (2)
O6—V2—V4ⁱ	131.89 (3)	V4ⁱ—O14—V2ⁱ	169.39 (3)
O13—V2—V4ⁱ	128.50 (2)	V3—O14—V1ⁱ	169.74 (3)
O10—V2—V4ⁱ	39.806 (19)	V3ⁱ—O14—V1ⁱ	88.20 (2)
O11ⁱ—V2—V4ⁱ	40.263 (18)	V4ⁱ—O14—V1ⁱ	86.38 (2)
O14ⁱ—V2—V4ⁱ	84.694 (17)	V2ⁱ—O14—V1ⁱ	84.99 (2)
V1—V2—V4ⁱ	120.428 (6)	V3—O14—V5ⁱ	87.30 (2)
O3—V3—O7	107.11 (4)	V3ⁱ—O14—V5ⁱ	170.66 (3)
O3—V3—O11	97.73 (3)	V4ⁱ—O14—V5ⁱ	86.25 (2)
O7—V3—O11	97.83 (3)	V2ⁱ—O14—V5ⁱ	86.50 (2)
O3—V3—O10	97.47 (3)	V1ⁱ—O14—V5ⁱ	82.46 (2)
O7—V3—O10	96.04 (3)	N2—C1—N1	118.43 (10)
O11—V3—O10	155.39 (3)	N2—C1—N3	123.86 (10)
O3—V3—O14	88.41 (3)	N1—C1—N3	117.57 (11)
O7—V3—O14	164.44 (3)	N4—C2—N5	118.72 (10)
O11—V3—O14	80.64 (3)	N4—C2—N3	123.49 (10)
O10—V3—O14	80.55 (3)	N5—C2—N3	117.62 (10)
O3—V3—O14ⁱ	166.38 (3)	N5—C3—H3A	109.5
O7—V3—O14ⁱ	86.51 (3)	N5—C3—H3B	109.5
O11—V3—O14ⁱ	80.29 (3)	H3A—C3—H3B	109.5
O10—V3—O14ⁱ	80.39 (3)	N5—C3—H3C	109.5
O14—V3—O14ⁱ	77.96 (3)	H3A—C3—H3C	109.5
O3—V3—V5ⁱ	39.06 (2)	H3B—C3—H3C	109.5
O7—V3—V5ⁱ	146.17 (2)	N5—C4—H4A	109.5
O11—V3—V5ⁱ	89.66 (2)	N5—C4—H4B	109.5
O10—V3—V5ⁱ	90.04 (2)	H4A—C4—H4B	109.5
O14—V3—V5ⁱ	49.358 (17)	N5—C4—H4C	109.5
O14ⁱ—V3—V5ⁱ	127.319 (17)	H4A—C4—H4C	109.5
O3—V3—V1	145.30 (3)	H4B—C4—H4C	109.5
O7—V3—V1	38.19 (2)	C1—N1—H1A	115.0 (14)
O11—V3—V1	89.69 (2)	C1—N1—H1B	119.0 (15)
O10—V3—V1	88.75 (2)	H1A—N1—H1B	126 (2)
O14—V3—V1	126.279 (18)	C1—N2—H2A	122.6 (12)
O14ⁱ—V3—V1	48.321 (17)	C1—N2—H2B	119.7 (12)
V5ⁱ—V3—V1	175.629 (6)	H2A—N2—H2B	114.9 (17)
O4—V4—O8	102.13 (4)	C1—N3—C2	122.59 (10)
O4—V4—O12	102.49 (4)	C2—N4—H4D	118.1 (12)
O8—V4—O12	95.66 (3)	C2—N4—H4E	117.1 (15)
O4—V4—O10ⁱ	99.74 (4)	H4D—N4—H4E	124.7 (19)
O8—V4—O10ⁱ	155.62 (3)	C2—N5—C3	122.03 (10)
O12—V4—O10ⁱ	89.99 (3)	C2—N5—C4	120.63 (11)
O4—V4—O11	99.12 (4)	C3—N5—C4	117.34 (10)
O8—V4—O11	89.83 (3)	H6A—N6—H6B	106.4 (16)
O12—V4—O11	156.02 (3)	H6A—N6—H6C	108.3 (17)
O10ⁱ—V4—O11	76.13 (3)	H6B—N6—H6C	117.5 (17)
O4—V4—O14ⁱ	174.28 (3)	H6A—N6—H6D	109.4 (17)
O8—V4—O14ⁱ	81.05 (3)	H6B—N6—H6D	107.1 (16)
O12—V4—O14ⁱ	81.78 (3)	H6C—N6—H6D	108.0 (17)
O10ⁱ—V4—O14ⁱ	76.30 (2)	H7A—N7—H7B	109.0 (16)
O11—V4—O14ⁱ	76.03 (3)	H7A—N7—H7C	109.8 (16)
O4—V4—V2ⁱ	89.60 (3)	H7B—N7—H7C	109.4 (16)
O8—V4—V2ⁱ	130.07 (2)	H7A—N7—H7D	112.0 (16)
O12—V4—V2ⁱ	129.23 (2)	H7B—N7—H7D	111.8 (15)
O10ⁱ—V4—V2ⁱ	39.240 (19)	H7C—N7—H7D	104.8 (16)
O11—V4—V2ⁱ	40.246 (19)	H15A—O15—H15B	112 (2)
O14ⁱ—V4—V2ⁱ	84.733 (17)	H16A—O16—H16B	112 (2)
O4—V4—V1	135.49 (3)	H17A—O17—H17B	102.5 (18)
O8—V4—V1	33.55 (2)

O7—V3—O3—V5ⁱ	179.48 (4)	V3—V1—O9—V5	2.25 (5)
O11—V3—O3—V5ⁱ	−79.82 (4)	V4—V1—O9—V5	47.45 (3)
O10—V3—O3—V5ⁱ	80.77 (4)	O5—V5—O9—V1	178.29 (5)
O14—V3—O3—V5ⁱ	0.51 (4)	O13—V5—O9—V1	75.08 (4)
O14ⁱ—V3—O3—V5ⁱ	0.80 (16)	O12—V5—O9—V1	−78.29 (4)
V1—V3—O3—V5ⁱ	179.443 (13)	O3ⁱ—V5—O9—V1	−3.32 (11)
O2—V2—O6—V1	−175.89 (4)	O14ⁱ—V5—O9—V1	−1.51 (4)
O13—V2—O6—V1	−71.55 (4)	V3ⁱ—V5—O9—V1	−1.85 (5)
O10—V2—O6—V1	84.11 (4)	V4—V5—O9—V1	−47.36 (3)
O11ⁱ—V2—O6—V1	23.77 (10)	O4—V4—O12—V5	−174.54 (4)
O14ⁱ—V2—O6—V1	7.80 (4)	O8—V4—O12—V5	−70.76 (4)
V4ⁱ—V2—O6—V1	83.24 (4)	O10ⁱ—V4—O12—V5	85.48 (4)
O1—V1—O6—V2	179.64 (4)	O11—V4—O12—V5	31.67 (9)
O9—V1—O6—V2	74.06 (4)	O14ⁱ—V4—O12—V5	9.32 (4)
O8—V1—O6—V2	−23.07 (10)	V2ⁱ—V4—O12—V5	85.57 (4)
O7—V1—O6—V2	−82.65 (4)	V1—V4—O12—V5	−39.17 (3)
O14ⁱ—V1—O6—V2	−7.60 (4)	O5—V5—O12—V4	176.70 (5)
V5—V1—O6—V2	41.65 (4)	O9—V5—O12—V4	72.14 (4)
V3—V1—O6—V2	−51.93 (3)	O13—V5—O12—V4	−22.59 (9)
V4—V1—O6—V2	−7.11 (5)	O3ⁱ—V5—O12—V4	−84.33 (4)
O3—V3—O7—V1	−179.96 (4)	O14ⁱ—V5—O12—V4	−8.99 (3)
O11—V3—O7—V1	79.41 (4)	V1—V5—O12—V4	39.76 (3)
O10—V3—O7—V1	−80.21 (4)	V3ⁱ—V5—O12—V4	−53.35 (3)
O14—V3—O7—V1	−3.81 (14)	O2—V2—O13—V5	175.65 (4)
O14ⁱ—V3—O7—V1	−0.27 (4)	O6—V2—O13—V5	71.08 (4)
V5ⁱ—V3—O7—V1	−179.378 (13)	O10—V2—O13—V5	−33.02 (10)
O4—V4—O8—V1	174.69 (4)	O11ⁱ—V2—O13—V5	−85.55 (4)
O12—V4—O8—V1	70.60 (4)	O14ⁱ—V2—O13—V5	−10.04 (4)
O10ⁱ—V4—O8—V1	−32.00 (10)	V1—V2—O13—V5	39.04 (3)
O11—V4—O8—V1	−86.02 (4)	V4ⁱ—V2—O13—V5	−85.02 (4)
O14ⁱ—V4—O8—V1	−10.14 (4)	O5—V5—O13—V2	−175.94 (5)
V2ⁱ—V4—O8—V1	−85.43 (4)	O9—V5—O13—V2	−71.13 (4)
V5—V4—O8—V1	38.66 (3)	O12—V5—O13—V2	23.31 (10)
O1—V1—O8—V4	−177.47 (4)	O3ⁱ—V5—O13—V2	85.00 (4)
O9—V1—O8—V4	−72.00 (4)	O14ⁱ—V5—O13—V2	9.71 (4)
O6—V1—O8—V4	25.37 (10)	V1—V5—O13—V2	−39.18 (3)
O7—V1—O8—V4	85.10 (4)	V3ⁱ—V5—O13—V2	54.11 (3)
O14ⁱ—V1—O8—V4	9.83 (3)	V4—V5—O13—V2	9.28 (5)
V5—V1—O8—V4	−39.33 (3)	N2—C1—N3—C2	30.11 (19)
V2—V1—O8—V4	10.82 (5)	N1—C1—N3—C2	−154.27 (13)
V3—V1—O8—V4	54.39 (3)	N4—C2—N3—C1	34.71 (19)
O1—V1—O9—V5	−178.43 (4)	N5—C2—N3—C1	−150.09 (12)
O6—V1—O9—V5	−76.42 (4)	N4—C2—N5—C3	−178.69 (15)
O8—V1—O9—V5	78.31 (4)	N3—C2—N5—C3	5.88 (19)
O7—V1—O9—V5	3.13 (11)	N4—C2—N5—C4	2.39 (18)
O14ⁱ—V1—O9—V5	1.52 (4)	N3—C2—N5—C4	−173.04 (12)
V2—V1—O9—V5	−45.22 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O10ⁱⁱ	0.818 (19)	2.080 (19)	2.8981 (12)	178 (2)
N1—H1B···O6	0.76 (2)	2.71 (2)	3.4507 (15)	163.9 (19)
N2—H2A···O12ⁱⁱⁱ	0.854 (18)	2.112 (18)	2.9457 (12)	165.4 (17)
N2—H2B···O15^iv	0.849 (19)	2.072 (19)	2.9164 (16)	172.9 (17)
N4—H4D···O9^iv	0.912 (19)	2.423 (19)	3.2993 (14)	161.1 (16)
N4—H4E···O16^v	0.736 (19)	2.269 (19)	2.9686 (16)	159.2 (19)
N6—H6A···O8^vi	0.882 (19)	1.865 (19)	2.7463 (13)	176.7 (17)
N6—H6B···O17ⁱⁱ	0.874 (18)	1.921 (19)	2.7871 (13)	170.7 (17)
N6—H6C···O7	0.808 (19)	1.990 (19)	2.7922 (11)	172.2 (18)
N6—H6D···O2ⁱⁱ	0.873 (19)	2.074 (19)	2.8541 (13)	148.3 (16)
N7—H7A···O16	0.835 (18)	2.083 (18)	2.8810 (14)	159.8 (17)
N7—H7B···O2^vii	0.880 (18)	2.367 (17)	2.9194 (12)	121.1 (14)
N7—H7B···O4^viii	0.880 (18)	2.056 (18)	2.8627 (12)	152.1 (16)
N7—H7C···O1^ix	0.843 (19)	2.072 (19)	2.9050 (12)	169.7 (17)
N7—H7D···O11ⁱ	0.873 (18)	1.928 (18)	2.7957 (12)	172.1 (16)
O15—H15A···O4	0.81 (2)	2.52 (2)	3.0266 (14)	122 (2)
O15—H15A···O12	0.81 (2)	2.38 (2)	3.1833 (16)	171 (2)
O15—H15B···O17^x	0.78 (2)	2.03 (2)	2.8046 (18)	177 (3)
O16—H16A···O15^viii	0.80 (2)	2.05 (2)	2.8477 (18)	176 (2)
O16—H16B···O5^xi	0.83 (2)	2.23 (2)	2.8937 (13)	137 (2)
O17—H17A···O13	0.85 (1)	1.87 (2)	2.7130 (12)	172 (2)
O17—H17B···N3	0.82 (2)	2.07 (2)	2.8830 (15)	170 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y+1, z; (iv) −x+1, −y+2, −z; (v) x, y+1, z; (vi) −x+1, −y+2, −z+1; (vii) −x, −y+1, −z+1; (viii) x−1, y, z; (ix) x, y−1, z; (x) x+1, y, z; (xi) −x+1, −y+1, −z.

Acknowledgements

APB thanks Rosa Elena Arroyo-Carmona for carrying out the fractional crystallization of the title compound. X-ray data were collected remotely, during the current pandemic, as part of a course. We thank the Comisión para el seguimiento y evaluación de la pandemia COVID-19 (BUAP, Puebla), who allowed one of us to switch the diffractometer on and off.

Funding information

Funding for this research was provided by: Consejo Nacional de Ciencia y Tecnología [grant No. 268178; CVU No. 869373 (JANA); CVU No. 861219 (JAPL)].

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