Synthesis and crystal structure of bis­(2-aminobenzimidazolium) catena-[metavanadate(V)]

Jabborova, K.; Ashurov, J.; Tojiboev, A.; Daminova, S.

doi:10.1107/S2056989024005528

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ISSN: 2056-9890

Volume 80| Part 7| July 2024| Pages 751-754

https://doi.org/10.1107/S2056989024005528

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Synthesis and crystal structure of bis(2-aminobenzimidazolium) catena-[metavanadate(V)]

Kholida Jabborova,^a ^* Jamshid Ashurov,^b Akmaljon Tojiboev ^c and Shahlo Daminova ^d,^e

^aInstitute of General and Inorganic Chemistry, Academy of Sciences of Uzbekistan, 100170, M. Ulugbek Str 77a, Tashkent, Uzbekistan, ^bInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, 100125, M. Ulugbek Str 83, Tashkent, Uzbekistan, ^cUniversity of Geological Sciences, Olimlar Street, 64, Mirzo Ulugbek district, Tashkent, Uzbekistan, ^dNational University of Uzbekistan named after Mirzo Ulugbek, University Street 4, Tashkent 100174, Uzbekistan, and ^eUzbekistan–Japan Innovation Center of Youth, University Street 2B, Tashkent, 100095, Uzbekistan
^*Correspondence e-mail: jabborova0707@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 8 May 2024; accepted 10 June 2024; online 18 June 2024)

The structure of polymeric catena-poly[2-aminobenzimidazolium [[dioxidovanadium(V)]-μ-oxido]], {(C₇H₈N₃)₂[V₂O₆]}_n, has monoclinic symmetry. The title compound is of interest with respect to anticancer activity. In the crystal structure, infinite linear zigzag vanadate (V₂O₆)²⁻ chains, constructed from corner-sharing VO₄ tetrahedra and that run parallel to the a axis, are present. Two different protonated 2-aminobenzimidazole molecules are located between the (V₂O₆)^2– chains and form classical N—H⋯O hydrogen bonds with the vanadate oxygen atoms, which contribute to the cohesion of the structure.

Keywords: crystal structure; 2-aminobenzimidazole; hybrid vanadate; hydrogen bonding.

CCDC reference: 2291372

1. Chemical context

In recent years, vanadate compounds have attracted attention in various fields due to their various compositions and interesting structures (Smith et al., 2012 ; Wutkowski et al., 2009 ; Wang et al., 2007 ). This is partly due to the ability of vanadium to adopt tetrahedral [VO₄], square-pyramidal [VO₅], trigonal–bipyramidal [VO₅] or octahedral [VO₆] coordination environments together with possible stable oxidation states of +III, +IV and +V. Interestingly, all major vanadate compounds known to date containing cage-, shell-, belt-, barrel-, or basket-shaped entities are structurally related to the layer structure of vanadium pentoxide (Ishaque Khan et al., 2000 ). These compounds have many practical pharmacological applications, ranging from anticancer agents to antifungal agents and, more recently, as insulin mimetics (Singh et al., 2014 ; Abakumova et al., 2012 ; Amin et al., 2000 ) where they interact with several points in the cell-signaling pathway associated with the hormone insulin (Amin et al., 2000; Srivastava & Mehdi, 2005 ). Studies have also indicated that vanadate compounds interact directly with glucose transporters located on the cell surface (Hiromura et al., 2007 ; Makinen & Brady, 2002 ). Furthermore, vanadium has been found to have important interactions in DNA repair systems, making it a useful target for many oncological/pharmacological studies (Abakumova et al., 2012; Kostova, 2009 ). Given the structural dependence on functions and application, a deeper study of the molecular and crystal structures of such complexes is warranted. In this context, we describe the synthesis and structural features of the polymeric title compound {(C₇H₈N₃)₂ (V₂O₆)}_n.

2. Structural commentary

The asymmetric unit comprises two 2-aminobenzimidazolium cations (denoted A and B) and two V and six O atoms of the polymeric metavanadate anion (Fig. 1). The cationic molecules are almost planar (root-mean-square deviation for A = 0.0127 Å and for B = 0.0064 Å), and their N—C bond-length distributions are similar to those in related compounds (Aliabadi et al., 2021 ; Ruzieva et al., 2022 ). The linear zigzag metavanadate (V₂O₆)^2– chain runs parallel to the a axis and is constructed from corner-sharing VO₄ tetrahedra (Fig. 2). Typical for such chains, the bridging O atoms (O3 and O4) have considerably longer V—O bonds than the terminal O atoms (O1 and O2 for the V1O₄ tetrahedron and O5 and O6 for the V2O₄ tetrahedron; Table 1). The corresponding V—O and V=O bond lengths are similar to those reported for related hybrid metavanadate compounds (Smith et al., 2012; Wutkowski et al., 2009; Wang et al., 2007; Tyrselova et al., 1996 ).

Table 1
Selected bond lengths (Å)

V1—O1	1.6300 (14)	V2—O6	1.6317 (14)
V1—O2	1.6534 (14)	V2—O5	1.6521 (14)
V1—O3	1.8061 (15)	V2—O3	1.8049 (14)
V1—O4ⁱ	1.8280 (14)	V2—O4	1.8118 (14)
Symmetry code: (i) .

Figure 1
The asymmetric unit of the title compound with the labeling scheme and displacement ellipsoids drawn at the 50% probability level. Dotted lines indicate N—H⋯O hydrogen-bonding interactions.

Figure 2
The metavanadate chain with the two different tetrahedra in polyhedral representation.

3. Supramolecular features

The crystal packing exhibits an intricate network of classical intermolecular N—H⋯O hydrogen bonds between the NH and NH₂ groups of the cations and all oxygen atoms of the metavanadate chain (Fig. 3, Table 2). Additional short contacts (Fig. 4) between the vanadate O6 atom and the centroid of the N1B/C1B/N2B/C7B/C2B ring (V2—O6⋯Cg4(−1 + x, y, z) = 3.8768 (16) Å) consolidate the tri-periodic network structure.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3B—H3BA⋯O6	0.88	1.97	2.830	169 (2)
N1A—H1A⋯O2	0.87	1.85	2.722	174 (2)
N1B—H1B⋯O5	0.88	1.91	2.774	171 (2)
N3A—H3AA⋯O1	0.87	1.97	2.837	169 (2)
N2A—H2A⋯O4ⁱⁱ	0.87	1.93	2.798	177 (2)
N2B—H2B⋯O2ⁱⁱⁱ	0.87	2.44	3.123	137 (2)
N2B—H2B⋯O3^iv	0.87	2.26	2.960	138 (2)
N3B—H3BB⋯O3^iv	0.87	2.18	2.938	145 (2)
N3B—H3BB⋯O6^v	0.87	2.41	2.887	115 (2)
N3A—H3AB⋯O5ⁱⁱ	0.88	1.90	2.779	175 (2)
Symmetry codes: (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) ; (iv) ; (v) .

Figure 3
View of the crystal structure of the title compound along the a axis, showing N—H⋯O hydrogen bonds drawn as blue dotted lines.

Figure 4
V2—O6⋯Cg4 interactions in the crystal structure of the title compound.

4. Database survey

A search in the Cambridge Structural Database (CSD, version 5.43, update of November 2022; Groom et al., 2016 ) revealed four hybrid compounds with protonated 2-aminobenzimidazole moieties, two with gallium (WURVAJ, WURVEN; Aliabadi et al., 2021) and two with lanthanum (JARVOQ, WEGRAF; Ruzieva et al., 2022). A search for the metavanadate moiety with linear zigzag chains similar to that in the title structure gave the following hits: CEHQEN and CEHQIR, for which dipole moments were calculated using iterative Hirshfeld partial atomic charges (Smith et al., 2012); (H₃NCH₂CH₂NH₃)(V₂O₆) (FUDLOF02; Ishaque Khan et al., 2000); 1,6-hexanediammonium metavanadate (KOYJAJ; Tyršelová & Pavelčík, 1992 ); 3-aza-1,5-pentamethylenediammonium metavanadate (KUGGUO; Roman et al., 1992 ); [Cu(H₂O)(C₅H₁₄N₂)₂](VO₃)₂ (POYNAT; Wutkowski et al., 2009); catena-poly[N,N′-bis(2-ammonioethyl)oxamide [dioxidovanadate-μ-oxido-dioxidovanadate-μ-oxido]] (TIGBUH; Wang et al., 2007); catena-poly[2,2′,2′′-nitrilotris(ethanaminium) [tri-μ-oxido-tris[dioxidovanadate(V)]] monohydrate] (VIPRET; Chang et al., 2013 ); {piperazinediium poly[trioxovanadate], {(C₄H₁₂N₂)(VO₃)₂} (ZITSEA; Tyrselova et al., 1996); catena[bis[tris(2-ammonioethyl)amine]hexakis(μ₂-oxo)dodecaoxohexavanadium trihydrate] (IMATOG; Li et al., 2009 ); catena-[pentakis(cyclohexylammonium) pentakis(μ₂-oxo)decaoxopentavanadium(V)] (NACFON; Wang et al., 2004 ).

5. Synthesis and crystallization

All reagents for synthesis and analysis were commercially available and purchased from Sigma Aldrich and used as received without further purification. Chemically pure vanadyl acetylacetonate, 2-aminobenzimidazole, and 96% vol ethanol were used. Vanadyl acetylacetonate (0.0265 g, 1 mmol) dissolved in 5 ml of EtOH and 2-aminobenzimidazole (0.0133 g, 1 mmol) dissolved in 5 ml of EtOH were mixed with constant stirring until the color of the solution turned to green. The stirring was continued for three hours. The resulting green solution was then allowed to cool to room temperature and green crystals were grown over seven days via slow evaporation of the mother liquor. Selected IR bands (KBr pellet, cm⁻¹): 3447 (N—H), 1647 (C=N), 868 (V=O), 898 (V—O), 943 (O=V=O), 655 (V—O—V).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms bound to C atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.95 Å and with U_iso(H) = 1.2U_eq(C). H atoms bound to N atoms were discernible in difference-Fourier maps and were refined with N—H bond length restraints of 0.86 (2) Å.

Table 3
Experimental details

Crystal data
Chemical formula	(C₇H₈N₃)₂[V₂O₆]
M_r	466.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	4.8817 (1), 16.8263 (2), 22.4354 (2)
β (°)	90.675 (1)
V (Å³)	1842.74 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	8.93
Crystal size (mm)	0.28 × 0.24 × 0.18

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.349, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17440, 3540, 3413
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.084, 1.07
No. of reflections	3540
No. of parameters	286
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.44
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2291372

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024005528/wm5720sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024005528/wm5720Isup3.hkl

checkCIF report

Computing details top

catena-Poly[2-aminobenzimidazolium [[dioxidovanadium(V)]-µ-oxido]] top

Crystal data top

(C₇H₈N₃)₂[V₂O₆]	F(000) = 944
M_r = 466.21	D_x = 1.680 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 4.8817 (1) Å	Cell parameters from 11386 reflections
b = 16.8263 (2) Å	θ = 3.3–71.2°
c = 22.4354 (2) Å	µ = 8.93 mm⁻¹
β = 90.675 (1)°	T = 100 K
V = 1842.74 (5) Å³	Block, green
Z = 4	0.28 × 0.24 × 0.18 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	3413 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 71.5°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −5→5
T_min = 0.349, T_max = 1.000	k = −20→20
17440 measured reflections	l = −27→27
3540 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0486P)² + 1.0444P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.38 e Å⁻³
3540 reflections	Δρ_min = −0.44 e Å⁻³
286 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
8 restraints	Extinction coefficient: 0.00059 (12)

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
V2	−0.28372 (6)	0.46447 (2)	0.35937 (2)	0.01360 (11)
V1	0.24874 (6)	0.34781 (2)	0.33048 (2)	0.01340 (11)
O4	−0.5361 (3)	0.42994 (8)	0.30547 (6)	0.0165 (3)
O6	−0.4298 (3)	0.48306 (8)	0.42291 (6)	0.0194 (3)
O3	−0.0282 (3)	0.38899 (8)	0.37331 (6)	0.0175 (3)
O2	0.4310 (3)	0.28954 (8)	0.37509 (6)	0.0182 (3)
O5	−0.1386 (3)	0.54667 (8)	0.33474 (6)	0.0194 (3)
O1	0.1365 (3)	0.29770 (8)	0.27302 (6)	0.0213 (3)
N2B	0.1986 (3)	0.68245 (10)	0.51241 (7)	0.0161 (3)
N1B	0.0739 (3)	0.64665 (10)	0.42202 (7)	0.0165 (3)
N1A	0.6212 (4)	0.14345 (10)	0.34384 (7)	0.0175 (3)
N3B	−0.1562 (4)	0.58715 (10)	0.50284 (7)	0.0190 (3)
N3A	0.3272 (4)	0.13954 (10)	0.25959 (8)	0.0209 (4)
N2A	0.6531 (4)	0.03991 (10)	0.28485 (7)	0.0176 (3)
C2A	0.8201 (4)	0.09402 (11)	0.36893 (9)	0.0170 (4)
C1B	0.0284 (4)	0.63523 (11)	0.48039 (8)	0.0154 (4)
C1A	0.5216 (4)	0.10926 (12)	0.29382 (9)	0.0176 (4)
C2B	0.2814 (4)	0.70255 (11)	0.41573 (8)	0.0158 (4)
C7B	0.3623 (4)	0.72532 (11)	0.47309 (8)	0.0155 (4)
C7A	0.8420 (4)	0.02816 (12)	0.33111 (9)	0.0171 (4)
C3B	0.4005 (4)	0.73529 (12)	0.36553 (9)	0.0201 (4)
H3B	0.343148	0.720517	0.326468	0.024*
C6B	0.5667 (4)	0.78067 (12)	0.48278 (9)	0.0181 (4)
H6B	0.621111	0.796047	0.521905	0.022*
C3A	0.9760 (4)	0.10065 (12)	0.42048 (9)	0.0212 (4)
H3A	0.957695	0.144818	0.446506	0.025*
C5B	0.6896 (4)	0.81295 (12)	0.43252 (9)	0.0210 (4)
H5B	0.832215	0.850884	0.437509	0.025*
C4B	0.6082 (4)	0.79089 (12)	0.37508 (9)	0.0221 (4)
H4B	0.695992	0.814193	0.341798	0.027*
C4A	1.1607 (5)	0.03984 (13)	0.43252 (10)	0.0248 (5)
H4A	1.271173	0.042284	0.467625	0.030*
C6A	1.0281 (4)	−0.03202 (12)	0.34269 (10)	0.0213 (4)
H6A	1.045994	−0.076194	0.316655	0.026*
C5A	1.1874 (4)	−0.02505 (13)	0.39392 (10)	0.0242 (4)
H5A	1.317900	−0.065244	0.403102	0.029*
H3BA	−0.259 (4)	0.5555 (12)	0.4812 (9)	0.023 (6)*
H2B	0.217 (5)	0.6788 (16)	0.5508 (5)	0.026 (7)*
H3AA	0.251 (5)	0.1857 (9)	0.2664 (12)	0.031 (7)*
H2A	0.619 (5)	0.0069 (13)	0.2558 (9)	0.029 (7)*
H3BB	−0.160 (5)	0.5797 (17)	0.5413 (5)	0.034 (7)*
H3AB	0.263 (5)	0.1129 (14)	0.2288 (8)	0.027 (7)*
H1B	−0.004 (5)	0.6193 (15)	0.3933 (9)	0.036 (7)*
H1A	0.566 (5)	0.1897 (9)	0.3563 (12)	0.035 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V2	0.01470 (19)	0.01364 (18)	0.01242 (17)	−0.00046 (11)	−0.00200 (12)	0.00155 (11)
V1	0.01604 (19)	0.01193 (17)	0.01219 (17)	−0.00065 (11)	−0.00225 (12)	0.00014 (11)
O4	0.0192 (7)	0.0153 (7)	0.0150 (6)	−0.0008 (5)	−0.0029 (5)	0.0023 (5)
O6	0.0199 (7)	0.0207 (7)	0.0174 (7)	−0.0005 (5)	0.0004 (5)	0.0001 (5)
O3	0.0172 (7)	0.0192 (7)	0.0160 (6)	0.0011 (5)	−0.0027 (5)	0.0011 (5)
O2	0.0226 (7)	0.0155 (7)	0.0166 (6)	0.0018 (5)	−0.0009 (5)	0.0001 (5)
O5	0.0227 (7)	0.0195 (7)	0.0159 (7)	−0.0033 (5)	−0.0033 (5)	0.0026 (5)
O1	0.0268 (8)	0.0190 (7)	0.0181 (7)	−0.0018 (6)	−0.0043 (6)	−0.0015 (5)
N2B	0.0208 (8)	0.0151 (8)	0.0124 (7)	−0.0007 (6)	−0.0026 (6)	0.0011 (6)
N1B	0.0185 (8)	0.0177 (8)	0.0133 (8)	−0.0022 (6)	−0.0008 (6)	−0.0012 (6)
N1A	0.0224 (9)	0.0134 (8)	0.0165 (8)	0.0013 (6)	−0.0017 (7)	−0.0042 (6)
N3B	0.0218 (9)	0.0186 (8)	0.0165 (8)	−0.0027 (7)	0.0006 (7)	0.0002 (7)
N3A	0.0291 (10)	0.0164 (8)	0.0171 (8)	0.0017 (7)	−0.0044 (7)	−0.0037 (7)
N2A	0.0225 (9)	0.0141 (8)	0.0162 (8)	−0.0013 (6)	−0.0004 (7)	−0.0035 (6)
C2A	0.0166 (9)	0.0150 (9)	0.0195 (9)	−0.0016 (7)	0.0008 (7)	0.0005 (7)
C1B	0.0174 (9)	0.0133 (9)	0.0155 (9)	0.0042 (7)	−0.0017 (7)	−0.0001 (7)
C1A	0.0206 (10)	0.0164 (9)	0.0159 (9)	−0.0030 (7)	0.0022 (7)	−0.0001 (7)
C2B	0.0166 (9)	0.0141 (9)	0.0168 (9)	0.0016 (7)	−0.0008 (7)	−0.0005 (7)
C7B	0.0165 (9)	0.0147 (9)	0.0152 (9)	0.0028 (7)	0.0001 (7)	0.0011 (7)
C7A	0.0184 (10)	0.0168 (9)	0.0161 (9)	−0.0024 (7)	0.0038 (7)	−0.0006 (7)
C3B	0.0258 (11)	0.0198 (10)	0.0148 (9)	0.0014 (8)	0.0022 (8)	0.0003 (7)
C6B	0.0181 (10)	0.0168 (9)	0.0194 (10)	0.0015 (7)	−0.0039 (7)	−0.0003 (7)
C3A	0.0212 (10)	0.0203 (10)	0.0220 (10)	−0.0012 (8)	−0.0013 (8)	−0.0035 (8)
C5B	0.0171 (10)	0.0178 (10)	0.0282 (10)	−0.0004 (8)	−0.0006 (8)	0.0020 (8)
C4B	0.0242 (11)	0.0203 (10)	0.0221 (10)	0.0015 (8)	0.0060 (8)	0.0043 (8)
C4A	0.0223 (11)	0.0260 (11)	0.0261 (11)	−0.0008 (8)	−0.0047 (9)	0.0012 (8)
C6A	0.0220 (10)	0.0164 (10)	0.0256 (10)	0.0000 (7)	0.0043 (8)	−0.0007 (8)
C5A	0.0202 (10)	0.0199 (10)	0.0326 (12)	0.0027 (8)	0.0008 (9)	0.0053 (9)

Geometric parameters (Å, º) top

V1—O1	1.6300 (14)	N2A—C1A	1.348 (3)
V1—O2	1.6534 (14)	N2A—C7A	1.394 (3)
V1—O3	1.8061 (15)	N2A—H2A	0.871 (10)
V1—O4ⁱ	1.8280 (14)	C2A—C3A	1.381 (3)
V2—O6	1.6317 (14)	C2A—C7A	1.401 (3)
V2—O5	1.6521 (14)	C2B—C3B	1.387 (3)
V2—O3	1.8049 (14)	C2B—C7B	1.395 (3)
V2—O4	1.8118 (14)	C7B—C6B	1.380 (3)
V2—V1ⁱⁱ	3.0736 (4)	C7A—C6A	1.383 (3)
N2B—C1B	1.351 (3)	C3B—C4B	1.394 (3)
N2B—C7B	1.398 (2)	C3B—H3B	0.9500
N2B—H2B	0.866 (10)	C6B—C5B	1.394 (3)
N1B—C1B	1.345 (3)	C6B—H6B	0.9500
N1B—C2B	1.391 (3)	C3A—C4A	1.388 (3)
N1B—H1B	0.873 (10)	C3A—H3A	0.9500
N1A—C1A	1.347 (3)	C5B—C4B	1.394 (3)
N1A—C2A	1.393 (3)	C5B—H5B	0.9500
N1A—H1A	0.871 (10)	C4B—H4B	0.9500
N3B—C1B	1.315 (3)	C4A—C5A	1.401 (3)
N3B—H3BA	0.874 (10)	C4A—H4A	0.9500
N3B—H3BB	0.873 (10)	C6A—C5A	1.385 (3)
N3A—C1A	1.316 (3)	C6A—H6A	0.9500
N3A—H3AA	0.875 (10)	C5A—H5A	0.9500
N3A—H3AB	0.877 (10)

O6—V2—O5	108.98 (7)	N1B—C1B—N2B	109.04 (17)
O6—V2—O3	106.96 (7)	N3A—C1A—N1A	124.85 (18)
O5—V2—O3	110.42 (7)	N3A—C1A—N2A	126.10 (18)
O6—V2—O4	110.11 (7)	N1A—C1A—N2A	109.05 (17)
O5—V2—O4	109.64 (7)	C3B—C2B—N1B	131.57 (18)
O3—V2—O4	110.68 (6)	C3B—C2B—C7B	121.52 (18)
O1—V1—O2	110.21 (7)	N1B—C2B—C7B	106.90 (16)
O1—V1—O3	111.87 (7)	C6B—C7B—C2B	121.79 (18)
O2—V1—O3	107.84 (6)	C6B—C7B—N2B	131.79 (18)
O1—V1—O4ⁱ	109.71 (7)	C2B—C7B—N2B	106.42 (16)
O2—V1—O4ⁱ	109.10 (7)	C6A—C7A—N2A	132.15 (18)
O3—V1—O4ⁱ	108.04 (6)	C6A—C7A—C2A	121.32 (19)
V2—O4—V1ⁱⁱ	115.22 (7)	N2A—C7A—C2A	106.53 (17)
V2—O3—V1	134.26 (8)	C2B—C3B—C4B	116.91 (19)
C1B—N2B—C7B	108.71 (16)	C2B—C3B—H3B	121.5
C1B—N2B—H2B	122.9 (18)	C4B—C3B—H3B	121.5
C7B—N2B—H2B	127.5 (18)	C7B—C6B—C5B	116.93 (18)
C1B—N1B—C2B	108.93 (16)	C7B—C6B—H6B	121.5
C1B—N1B—H1B	124.6 (19)	C5B—C6B—H6B	121.5
C2B—N1B—H1B	126.2 (19)	C2A—C3A—C4A	116.97 (19)
C1A—N1A—C2A	108.96 (16)	C2A—C3A—H3A	121.5
C1A—N1A—H1A	122.5 (19)	C4A—C3A—H3A	121.5
C2A—N1A—H1A	128.5 (19)	C6B—C5B—C4B	121.54 (19)
C1B—N3B—H3BA	123.6 (16)	C6B—C5B—H5B	119.2
C1B—N3B—H3BB	119.4 (19)	C4B—C5B—H5B	119.2
H3BA—N3B—H3BB	116 (3)	C3B—C4B—C5B	121.30 (18)
C1A—N3A—H3AA	123.1 (18)	C3B—C4B—H4B	119.4
C1A—N3A—H3AB	120.6 (18)	C5B—C4B—H4B	119.4
H3AA—N3A—H3AB	116 (2)	C3A—C4A—C5A	121.3 (2)
C1A—N2A—C7A	108.88 (16)	C3A—C4A—H4A	119.4
C1A—N2A—H2A	125.2 (18)	C5A—C4A—H4A	119.4
C7A—N2A—H2A	125.9 (18)	C7A—C6A—C5A	117.07 (19)
C3A—C2A—N1A	131.68 (18)	C7A—C6A—H6A	121.5
C3A—C2A—C7A	121.74 (19)	C5A—C6A—H6A	121.5
N1A—C2A—C7A	106.57 (17)	C6A—C5A—C4A	121.6 (2)
N3B—C1B—N1B	125.63 (18)	C6A—C5A—H5A	119.2
N3B—C1B—N2B	125.31 (18)	C4A—C5A—H5A	119.2

O6—V2—O4—V1ⁱⁱ	−51.54 (10)	C3B—C2B—C7B—N2B	178.79 (18)
O5—V2—O4—V1ⁱⁱ	−171.43 (7)	N1B—C2B—C7B—N2B	−0.4 (2)
O3—V2—O4—V1ⁱⁱ	66.52 (9)	C1B—N2B—C7B—C6B	−179.8 (2)
O6—V2—O3—V1	−168.95 (10)	C1B—N2B—C7B—C2B	0.6 (2)
O5—V2—O3—V1	−50.50 (13)	C1A—N2A—C7A—C6A	−179.1 (2)
O4—V2—O3—V1	71.09 (12)	C1A—N2A—C7A—C2A	−0.1 (2)
V1ⁱⁱ—V2—O3—V1	100.81 (10)	C3A—C2A—C7A—C6A	−2.3 (3)
O1—V1—O3—V2	−67.14 (13)	N1A—C2A—C7A—C6A	178.54 (17)
O2—V1—O3—V2	171.52 (10)	C3A—C2A—C7A—N2A	178.57 (17)
O4ⁱ—V1—O3—V2	53.72 (12)	N1A—C2A—C7A—N2A	−0.6 (2)
V2ⁱ—V1—O3—V2	86.44 (11)	N1B—C2B—C3B—C4B	−179.92 (19)
C1A—N1A—C2A—C3A	−177.9 (2)	C7B—C2B—C3B—C4B	1.2 (3)
C1A—N1A—C2A—C7A	1.1 (2)	C2B—C7B—C6B—C5B	−0.1 (3)
C2B—N1B—C1B—N3B	179.08 (18)	N2B—C7B—C6B—C5B	−179.57 (19)
C2B—N1B—C1B—N2B	0.5 (2)	N1A—C2A—C3A—C4A	−179.6 (2)
C7B—N2B—C1B—N3B	−179.32 (18)	C7A—C2A—C3A—C4A	1.5 (3)
C7B—N2B—C1B—N1B	−0.7 (2)	C7B—C6B—C5B—C4B	0.6 (3)
C2A—N1A—C1A—N3A	178.88 (18)	C2B—C3B—C4B—C5B	−0.7 (3)
C2A—N1A—C1A—N2A	−1.2 (2)	C6B—C5B—C4B—C3B	−0.2 (3)
C7A—N2A—C1A—N3A	−179.26 (19)	C2A—C3A—C4A—C5A	0.2 (3)
C7A—N2A—C1A—N1A	0.8 (2)	N2A—C7A—C6A—C5A	−179.8 (2)
C1B—N1B—C2B—C3B	−179.1 (2)	C2A—C7A—C6A—C5A	1.3 (3)
C1B—N1B—C2B—C7B	0.0 (2)	C7A—C6A—C5A—C4A	0.3 (3)
C3B—C2B—C7B—C6B	−0.8 (3)	C3A—C4A—C5A—C6A	−1.0 (3)
N1B—C2B—C7B—C6B	−179.98 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3B—H3BA···O6	0.88	1.97	2.830	169 (2)
N1A—H1A···O2	0.87	1.85	2.722	174 (2)
N1B—H1B···O5	0.88	1.91	2.774	171 (2)
N3A—H3AA···O1	0.87	1.97	2.837	169 (2)
N2A—H2A···O4ⁱⁱⁱ	0.87	1.93	2.798	177 (2)
N2B—H2B···O2^iv	0.87	2.44	3.123	137 (2)
N2B—H2B···O3^v	0.87	2.26	2.960	138 (2)
N3B—H3BB···O3^v	0.87	2.18	2.938	145 (2)
N3B—H3BB···O6^vi	0.87	2.41	2.887	115 (2)
N3A—H3AB···O5ⁱⁱⁱ	0.88	1.90	2.779	175 (2)

Symmetry codes: (iii) −x, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) −x−1, −y+1, −z+1.

Acknowledgements

The authors acknowledge support from the MIRAI FUND (JICA) and technical equipment support provided by the Institute of Bioorganic Chemistry of Academy Sciences of Uzbekistan.

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