Crystal structure of di­ethyl­ammonium dioxido{Z)-N-[(pyri­din-2-yl)car­bon­yl­azan­idyl]pyri­dine-2-car­box­imid­ato}vana­date(1−) monohydrate

Mondal, B.

doi:10.1107/S2056989024001166

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Volume 80| Part 3| March 2024| Pages 277-280

https://doi.org/10.1107/S2056989024001166

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Crystal structure of diethylammonium dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1−) monohydrate

Bipul Mondal ^a ^*

^aDepartment of Chemistry, Ramakrishna Mission Vivekananda Centenary College, Rahara, Kolkata-700118, West Bengal, India
^*Correspondence e-mail: dbmd79@gmail.com

Edited by S. P. Kelley, University of Missouri-Columbia, USA (Received 9 November 2023; accepted 3 February 2024; online 8 February 2024)

The title compound, (C₄H₁₂N)[V(C₁₂H₈N₄O₂)O₂]·H₂O, was synthesized via aerial oxidation on refluxing picolinohydrazide with ethyl picolinate followed by addition of V^IVO(acac)₂ and diethylamine in methanol. It crystallizes in the triclinic crystal system in space group P $[\overline{1}]$ . In the complex anion, the dioxidovanadium(V) moiety exhibits a distorted square-pyramidal geometry. In the crystal, extensive hydrogen bonding links the water molecule to two complex anions and one diethylammonium ion. One of the CH₂ groups in the diethylamine is disordered over two sets of sites in a 0.7:0.3 ratio.

Keywords: crystal structure; dioxidovanadium(V); O,N,O -donor Schiff-base; hydrogen bond.

CCDC reference: 2294358

1. Chemical context

Vanadium, a biologically important trace element with the +V oxidation state, has received considerable attention among the three (viz., +III, +IV and +V) physiologically important oxidation states. In this oxidation state, vanadium exists in three different motifs, viz., VO³⁺, V₂O₃⁴⁺ and VO₂⁺. The formation and stability of these three motifs depends upon the nature of the solvent, the pH of the reaction medium and basicity of the donor atoms of the ligand(s), with a preference for N, O-donor ligands because of the hard acidic nature of V^V. It is evident from the literature (Mondal et al., 2010 , 2008 ) that the vanadium complexes containing VO₂⁺ motifs are formed in basic media. Vanadium compounds show the catalytic cycle of haloperoxidase activity has been suggested to proceed through hydrogen-bonding interactions (Colpas et al., 1996 ; Messerschimdt & Wever, 1996 ; Weyand et al., 1999 ; Isupov et al., 2000 ). In the presence of appropriate hydrogen-bond donors, hydrogen bonding is a general feature of vanadium(IV) and vanadium(V) complexes (Mondal et al., 2010; Plass, 1997 , 1998 ; Plass & Yozgatli, 2003 ; Pohlmann & Plass, 2001 ; Pohlmann et al., 2005 ; Vergopoulos et al., 1993 ; Sutradhar et al., 2006 ). In general, these examples lead to the formation of hydrogen-bonded molecular assemblies ranging from simple dimers to three-dimensional networks.

In this work, an ionic compound of dioxidovanadium(V) containing a symmetric N-(pyridine-2-ylcarbamoyl)picolinamide (Shao et al., 1999 ) ligand (H₂L) bound to vanadium through NNO in an asymmetric fashion, was synthesized in the presence of diethylamine in good yield and characterized by X-ray crystallography. The title compound may be used for antidiabetic drug development (Jia et al., 2017 ).

2. Structural commentary

The solid-state molecular structure was confirmed by single-crystal X-ray characterization. The title compound crystallizes in the triclinic crystal system, space group P $[\overline{1}]$ . The asymmetric unit (Fig. 1a) comprises a diethylammonium cation, a complex dioxidovanadium(V) and a water molecule, which is interlinked between the two ionic parts of the compound through hydrogen bonding (Fig. 1b). The anionic part of the compound consists of one crystallographically independent V⁵⁺ ion, two oxido ligands and one NNO donor ligand with coordination sphere of the VO₃N₂ type (Fig. 1a). The V⁵⁺ ion is coordinated by two oxygen (O1 and O2) atoms (oxido ligands), one nitrogen (N1) atom of the pyridine ring, one deprotonated amide nitrogen (N2) atom and a deprotonated amide-oxygen (O3) through enolization (Fig. 2) of the ligand. The five-coordinate V⁵⁺ ion has a distorted square-pyramidal geometry with one of the two oxido oxygen atoms (O1) at the apex. The extent of distortion from a perfect square-pyramidal geometry can be quantified by the structural index parameter (τ = 0.35), as determined from the equation τ = (β - α)/60 (where β and α are the two largest L—M—L angles), which is 0 for an idealized square pyramid and 1 for a trigonal bipyramid (Nair et al., 2018 ; Ghosh et al., 2022 ). The square plane consists of one nitrogen atom from the pyridine ring (N1), one deprotonated amide nitrogen (N2), one enolate oxygen (O3) and one oxido oxygen (O2) atom of the ligands. The vanadium atom is located 0.555 (4) Å above the equatorial plane and displaced towards the axial O1 atom. Selected bonds involving the V atom are given in Table 1. The V—O1 bond is longer than V—O2, probably due to the involvement of O1 in a hydrogen bond with the water hydrogen atom H5C (Table 2). Among the three V—O bonds, the longest is the V—O3 bond length due to the absence of a V—O π-bond (Mondal et al., 2010; Jia et al., 2017). In the absence of diethylamine, the formation of neutral dioxido complex has been reported in which the uncoordinated pyridine atom N4 is protonated (Jia et al., 2017), but in this case the protonation of the diethylamine moiety (pK_a = 10.98) is probably due to its higher basicity than pyridine (pK_a = 5.23).

Table 1
Selected bond lengths (Å)

V1—O2	1.6107 (15)	V1—N2	2.0385 (15)
V1—O3	1.9461 (14)	V1—N1	2.1170 (15)
V1—O1	1.6310 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O5	0.95 (3)	1.92 (3)	2.848 (3)	165 (3)
N5—H5B⋯N3ⁱ	0.85 (3)	2.08 (3)	2.918 (3)	171 (3)
O5—H5C⋯O1	0.85	1.94	2.776 (3)	169
O5—H5D⋯O4ⁱⁱ	0.85	1.99	2.838 (2)	178
C2—H2⋯O2ⁱⁱⁱ	0.93	2.48	3.277 (3)	143
C14—H14A⋯O4ⁱ	0.97	2.57	3.172 (3)	121
C15A—H15A⋯N4ⁱ	0.97	2.59	3.233 (5)	124
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 1
(a) The molecular structure with the atom-numbering scheme and ellipsoids drawn at the 50% probability level and (b) the intramolecular hydrogen bond.

Figure 2
The keto–enol tautomeric forms of the ligand.

3. Supramolecular features

The oxygen (O5) atom of water acts as a hydrogen-bond donor with an acceptor oxido group (O1) of the dioxidovanadium(V) complex in the same asymmetric unit (O5—H5C⋯O1) and a symmetry-related amide oxygen (O4) atom in a neighbouring asymmetric unit (O5—H5D⋯O4) (Table 2). The O5 atom also acts as a hydrogen-bond acceptor for the amine H5A atom (N5—H5A⋯O5). Another amine hydrogen (H5B) is hydrogen bonded with the N3 atom (N5—H5B⋯N3) of an adjacent complex. Two C—H⋯O and one C—H⋯N interactions are also observed. These hydrogen bonds within the same and different asymmetric units enhance the crystal packing of the compounds (Figs. 1b and 3). The mono-periodic constructs are packed perpendicular to the bc plane, giving rise to an overall three-dimensional packing arrangement (Fig. 4).

Figure 3
The hydrogen bonding in adjacent asymmetric units.

Figure 4
The three-dimensional packing arrangement of the components of the title compound.

4. Database survey

Mondal et al. (2010) reported numerous ionic dioxidovanadium(V) compounds with O,N,O donor ligands in presence of different types of bases. Jia et al. (2017) also reported a neutral dioxidovanadium(V) compound with the same ligand.

5. Synthesis and crystallization

To a solution of picolinohydrazide (0.137 g, 1 mmol) in methanol (25 ml) was added ethyl picolinate (0.151 g, 1 mmol). The solution was heated under reflux for 3 h. The reaction mixture was cooled to room temperature and a methanolic solution (20 ml) of [V^IVO(acac)₂] (0.265 g, 1 mmol) was added with stirring. After stirring for 2 h, a methanolic solution (10 ml) of diethylamine (1 ml) was added with continuous stirring. The solution immediately turned yellow and the reaction mixture was then refluxed for 1 h. The reaction mixture was then kept for slow evaporation at room temperature. A yellow X-ray quality crystalline compound was obtained, which was filtered, washed with methanol and dried over silica gel (fused). Yield: 0.34 g (82%). Crystals of the complex were obtained after 4-days on slow evaporation at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. N-bound H atoms were refined with U_i_so(H) = 1.2U_eq(N). C-bound H atoms and water H atoms were placed at calculated positions (C—H = 0.93–0.97 Å, O—H = 0.85 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C-methyl,O). Initially, residual electron density ws noted near to C15. The part command was used to locate the two positions of C15 (i.e., C15A, in PART 1; and C15B, in PART 2). The site occupancie are 0.7 and 0.3, respectively. Subsequently, an isotropic refinement was done and finally, an anisotropic refinement is performed.

Table 3
Experimental details

Crystal data
Chemical formula	(C₄H₁₂N)[V(C₁₂H₈N₄O₂)O₂]·H₂O
M_r	415.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	7.6850 (4), 9.4135 (4), 13.9147 (7)
α, β, γ (°)	105.609 (2), 101.103 (2), 96.253 (2)
V (Å³)	937.50 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.57
Crystal size (mm)	0.32 × 0.18 × 0.03

Data collection
Diffractometer	Bruker D8 Quest with Photon II area detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.670, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	61285, 5048, 3852
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.110, 1.06
No. of reflections	5048
No. of parameters	274
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.39
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2294358

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024001166/ev2002sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024001166/ev2002Isup2.hkl

checkCIF report

Computing details top

Diethylammonium dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1-) monohydrate top

Crystal data top

(C₄H₁₂N)[V(C₁₂H₈N₄O₂)O₂]·H₂O	Z = 2
M_r = 415.32	F(000) = 432
Triclinic, P1	D_x = 1.471 Mg m⁻³
a = 7.6850 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4135 (4) Å	Cell parameters from 9990 reflections
c = 13.9147 (7) Å	θ = 2.3–30.2°
α = 105.609 (2)°	µ = 0.57 mm⁻¹
β = 101.103 (2)°	T = 298 K
γ = 96.253 (2)°	BLOCK, yellow
V = 937.50 (8) Å³	0.32 × 0.18 × 0.03 mm

Data collection top

Bruker D8 Quest with Photon II area detector diffractometer	3852 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.081
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 29.1°, θ_min = 2.3°
T_min = 0.670, T_max = 0.747	h = −10→10
61285 measured reflections	k = −12→12
5048 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.045P)² + 0.4439P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5048 reflections	Δρ_max = 0.43 e Å⁻³
274 parameters	Δρ_min = −0.39 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)
V1	0.58085 (4)	0.29537 (3)	0.78356 (3)	0.03307 (10)
N4	0.0021 (2)	−0.1100 (2)	0.63830 (14)	0.0431 (4)
O2	0.5724 (2)	0.42364 (17)	0.88516 (12)	0.0518 (4)
O3	0.32784 (18)	0.22542 (14)	0.71551 (11)	0.0394 (3)
N3	0.36076 (19)	−0.00629 (16)	0.73136 (13)	0.0332 (3)
C1	0.9836 (3)	0.3489 (2)	0.88556 (17)	0.0419 (5)
H1	0.979921	0.446045	0.882458	0.050*
O1	0.6564 (2)	0.36927 (18)	0.70301 (13)	0.0528 (4)
C2	1.1439 (3)	0.3148 (3)	0.92898 (18)	0.0487 (5)
H2	1.246761	0.387685	0.955215	0.058*
O5	0.8727 (2)	0.6487 (2)	0.7639 (2)	0.0755 (6)
H5C	0.799539	0.566441	0.738019	0.113*
H5D	0.806183	0.714430	0.777364	0.113*
N2	0.53498 (19)	0.07461 (16)	0.77552 (12)	0.0316 (3)
C4	0.9945 (3)	0.0640 (2)	0.89249 (17)	0.0415 (4)
H4	0.996177	−0.034329	0.893312	0.050*
N5	1.2242 (3)	0.6901 (2)	0.72745 (16)	0.0484 (5)
H5A	1.107 (4)	0.694 (3)	0.740 (2)	0.058*
H5B	1.276 (4)	0.777 (3)	0.732 (2)	0.058*
C3	1.1493 (3)	0.1707 (3)	0.93290 (18)	0.0493 (5)
H3	1.256060	0.145211	0.962437	0.059*
O4	0.64803 (19)	−0.13258 (15)	0.80366 (14)	0.0497 (4)
N1	0.8323 (2)	0.24697 (17)	0.84751 (12)	0.0325 (3)
C5	0.8380 (2)	0.1063 (2)	0.85105 (14)	0.0313 (4)
C7	0.2627 (2)	0.08519 (19)	0.70259 (14)	0.0311 (4)
C6	0.6610 (2)	0.00098 (19)	0.80739 (15)	0.0330 (4)
C14	1.3191 (3)	0.6392 (3)	0.8113 (2)	0.0598 (7)
H14A	1.442548	0.635076	0.805965	0.072*
H14B	1.261482	0.539255	0.805202	0.072*
C13	1.3170 (4)	0.7421 (4)	0.9123 (2)	0.0828 (10)
H13A	1.371411	0.841452	0.917594	0.124*
H13B	1.383288	0.709304	0.965860	0.124*
H13C	1.194956	0.742057	0.918946	0.124*
C15A	1.1933 (5)	0.5973 (5)	0.6175 (4)	0.0527 (10)	0.7
H15A	1.112883	0.639100	0.573984	0.063*	0.7
H15B	1.137207	0.496051	0.609451	0.063*	0.7
C16A	1.3721 (7)	0.5944 (7)	0.5852 (5)	0.0695 (13)	0.7
H16A	1.349650	0.557036	0.511873	0.104*	0.7
H16B	1.438875	0.530498	0.615382	0.104*	0.7
H16C	1.440214	0.693958	0.608190	0.104*	0.7
C8	0.0699 (2)	0.0330 (2)	0.65164 (14)	0.0326 (4)
C9	−0.0329 (3)	0.1301 (2)	0.61863 (16)	0.0421 (5)
H9	0.017119	0.229460	0.630326	0.050*
C10	−0.2108 (3)	0.0772 (3)	0.56808 (19)	0.0534 (6)
H10	−0.282243	0.140321	0.544890	0.064*
C11	−0.2801 (3)	−0.0687 (3)	0.55262 (19)	0.0554 (6)
H11	−0.398965	−0.107782	0.517707	0.067*
C12	−0.1699 (3)	−0.1567 (3)	0.58996 (19)	0.0526 (6)
H12	−0.219043	−0.255526	0.580788	0.063*
C15B	1.279 (3)	0.5710 (13)	0.6404 (12)	0.102 (6)	0.3
H15C	1.399256	0.553432	0.665826	0.123*	0.3
H15D	1.196845	0.477106	0.621828	0.123*	0.3
C16B	1.276 (3)	0.6182 (19)	0.5559 (13)	0.116 (6)	0.3
H16D	1.270778	0.533969	0.497547	0.173*	0.3
H16E	1.383543	0.688974	0.567037	0.173*	0.3
H16F	1.172786	0.664919	0.543386	0.173*	0.3

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.03157 (16)	0.02325 (15)	0.04138 (19)	0.00202 (11)	0.00358 (13)	0.00908 (12)
N4	0.0319 (8)	0.0415 (9)	0.0525 (11)	−0.0027 (7)	0.0019 (7)	0.0175 (8)
O2	0.0457 (8)	0.0400 (8)	0.0543 (9)	0.0124 (7)	−0.0010 (7)	−0.0046 (7)
O3	0.0345 (7)	0.0278 (6)	0.0520 (8)	0.0024 (5)	−0.0009 (6)	0.0141 (6)
N3	0.0249 (7)	0.0277 (7)	0.0438 (9)	−0.0003 (6)	0.0023 (6)	0.0111 (6)
C1	0.0354 (10)	0.0326 (9)	0.0495 (12)	−0.0043 (8)	0.0055 (9)	0.0056 (9)
O1	0.0511 (9)	0.0474 (9)	0.0672 (11)	0.0019 (7)	0.0118 (8)	0.0329 (8)
C2	0.0319 (10)	0.0489 (12)	0.0526 (13)	−0.0062 (9)	0.0018 (9)	0.0049 (10)
O5	0.0432 (9)	0.0467 (10)	0.146 (2)	0.0060 (8)	0.0276 (11)	0.0400 (12)
N2	0.0239 (7)	0.0261 (7)	0.0422 (9)	0.0002 (5)	0.0031 (6)	0.0106 (6)
C4	0.0325 (9)	0.0428 (11)	0.0485 (12)	0.0072 (8)	0.0035 (8)	0.0163 (9)
N5	0.0555 (12)	0.0325 (9)	0.0583 (12)	0.0029 (8)	0.0163 (10)	0.0151 (9)
C3	0.0294 (10)	0.0594 (14)	0.0536 (13)	0.0053 (9)	−0.0009 (9)	0.0162 (11)
O4	0.0362 (7)	0.0312 (7)	0.0835 (12)	0.0050 (6)	0.0057 (7)	0.0260 (7)
N1	0.0288 (7)	0.0288 (7)	0.0371 (8)	0.0010 (6)	0.0065 (6)	0.0076 (6)
C5	0.0283 (8)	0.0318 (9)	0.0339 (9)	0.0043 (7)	0.0067 (7)	0.0108 (7)
C7	0.0306 (8)	0.0289 (8)	0.0324 (9)	0.0018 (7)	0.0058 (7)	0.0090 (7)
C6	0.0320 (9)	0.0262 (8)	0.0399 (10)	0.0035 (7)	0.0040 (7)	0.0119 (7)
C14	0.0450 (12)	0.0587 (15)	0.098 (2)	0.0169 (11)	0.0232 (13)	0.0522 (15)
C13	0.072 (2)	0.124 (3)	0.0664 (19)	0.0195 (19)	0.0103 (15)	0.054 (2)
C15A	0.049 (2)	0.041 (2)	0.059 (3)	0.0063 (15)	0.0060 (18)	0.0045 (17)
C16A	0.066 (3)	0.077 (3)	0.065 (3)	0.019 (2)	0.023 (2)	0.011 (2)
C8	0.0296 (8)	0.0355 (9)	0.0317 (9)	0.0034 (7)	0.0066 (7)	0.0095 (7)
C9	0.0372 (10)	0.0438 (11)	0.0438 (11)	0.0103 (8)	0.0046 (8)	0.0127 (9)
C10	0.0353 (11)	0.0700 (16)	0.0564 (14)	0.0171 (11)	0.0032 (10)	0.0232 (12)
C11	0.0260 (9)	0.0803 (17)	0.0554 (14)	0.0011 (10)	0.0004 (9)	0.0221 (13)
C12	0.0344 (11)	0.0547 (13)	0.0609 (15)	−0.0099 (9)	0.0015 (10)	0.0178 (11)
C15B	0.179 (19)	0.039 (5)	0.083 (10)	0.028 (9)	0.019 (12)	0.013 (6)
C16B	0.137 (17)	0.088 (10)	0.111 (14)	0.029 (11)	0.046 (13)	−0.005 (9)

Geometric parameters (Å, º) top

V1—O2	1.6107 (15)	C4—C5	1.378 (3)
V1—O3	1.9461 (14)	N5—C14	1.473 (3)
V1—O1	1.6310 (16)	N5—C15A	1.502 (5)
V1—N2	2.0385 (15)	N5—C15B	1.573 (16)
V1—N1	2.1170 (15)	O4—C6	1.237 (2)
N4—C8	1.340 (2)	N1—C5	1.343 (2)
N4—C12	1.329 (3)	C5—C6	1.506 (2)
O3—C7	1.311 (2)	C7—C8	1.480 (2)
N3—N2	1.400 (2)	C14—C13	1.481 (4)
N3—C7	1.296 (2)	C15A—C16A	1.526 (7)
C1—C2	1.375 (3)	C8—C9	1.383 (3)
C1—N1	1.342 (2)	C9—C10	1.380 (3)
C2—C3	1.377 (3)	C10—C11	1.362 (4)
N2—C6	1.327 (2)	C11—C12	1.374 (3)
C4—C3	1.385 (3)	C15B—C16B	1.36 (2)

O2—V1—O3	102.55 (7)	C1—N1—V1	123.69 (13)
O2—V1—O1	110.64 (9)	C1—N1—C5	118.88 (16)
O2—V1—N2	121.01 (8)	C5—N1—V1	117.43 (12)
O2—V1—N1	95.14 (7)	C4—C5—C6	123.33 (17)
O3—V1—N2	74.82 (5)	N1—C5—C4	121.92 (17)
O3—V1—N1	148.99 (6)	N1—C5—C6	114.75 (15)
O1—V1—O3	102.22 (7)	O3—C7—C8	117.03 (15)
O1—V1—N2	127.77 (8)	N3—C7—O3	122.55 (16)
O1—V1—N1	94.92 (7)	N3—C7—C8	120.41 (16)
N2—V1—N1	74.24 (6)	N2—C6—C5	109.38 (15)
C12—N4—C8	116.92 (18)	O4—C6—N2	129.15 (17)
C7—O3—V1	117.29 (11)	O4—C6—C5	121.47 (16)
C7—N3—N2	106.98 (14)	N5—C14—C13	110.7 (2)
N1—C1—C2	122.3 (2)	N5—C15A—C16A	109.9 (3)
C1—C2—C3	118.8 (2)	N4—C8—C7	117.44 (16)
N3—N2—V1	118.33 (10)	N4—C8—C9	122.41 (18)
C6—N2—V1	124.19 (12)	C9—C8—C7	120.14 (17)
C6—N2—N3	117.46 (14)	C10—C9—C8	119.0 (2)
C5—C4—C3	118.71 (19)	C11—C10—C9	119.1 (2)
C14—N5—C15A	120.9 (2)	C10—C11—C12	118.2 (2)
C14—N5—C15B	94.6 (6)	N4—C12—C11	124.4 (2)
C2—C3—C4	119.43 (19)	C16B—C15B—N5	111.2 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O5	0.95 (3)	1.92 (3)	2.848 (3)	165 (3)
N5—H5B···N3ⁱ	0.85 (3)	2.08 (3)	2.918 (3)	171 (3)
O5—H5C···O1	0.85	1.94	2.776 (3)	169
O5—H5D···O4ⁱⁱ	0.85	1.99	2.838 (2)	178
C2—H2···O2ⁱⁱⁱ	0.93	2.48	3.277 (3)	143
C14—H14A···O4ⁱ	0.97	2.57	3.172 (3)	121
C15A—H15A···N4ⁱ	0.97	2.59	3.233 (5)	124

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

Acknowledgements

The author thanks Dr Pabitra Baran Chatterjee for the single-crystal X-ray crystallographic data collection and analysis, and is also grateful to the college authorities for providing research facilities.

Funding information

Funding for this research was provided by: The Science and Engineering Research Board (SERB), New Delhi, India (file No. EEQ/2019/000292).

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