Journal of the Indian Chemical Society 99 (2022) 100401

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Journal of the Indian Chemical Society

journal homepage: www.journals.elsevier.com/journal-of-the-indian-chemical-society

Synthesis and structure of vanadium (IV) single-stranded dihelicate

involving multi-ring nitrogen-heterocyclic ligand
Tirtha Pada Majhi a, Simon J. Teat b, Nabanita Kundu c, *
a
Department of Chemistry, Bidhannagar College, EB-2, Sector-I, Salt Lake, Kolkata, 700064, India
b
Advanced Light Source, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Mail Stop 2-400, Berkeley, CA, 94720, United States
c
Department of Chemistry, Lady Brabourne College, P-1/2, Suhrawardy Avenue, Kolkata, 700017, India

A R T I C L E I N F O A B S T R A C T

Keywords: 1 The single stranded-helicate Vanadium(IV) complex [V2O2Cl4(L)(H2O)2] (1) involving heterocyclic bis-
N-heterocyclic ligand bidentate ligand viz. 3,3/-dipyridine-2-yl-[1.1/]bi[imidazo[1,5-a]pyridineyl] (L) with biological relevance is
Dihelicate prepared and characterized by X-ray diffraction analysis. The compound lacks molecular center of symmetry
Single stranded
where coordination environments around V(1) and V(2) centres are distorted octahedral (V⋅⋅⋅V# separation of
X-ray diffraction
anion− π interactions
5.827 Å). Structure of the compound in the solid state structure shows anion− π interactions, classical and Carene-
Non-classical H-Bonding H—anion non-classical H-bonding interactions. These interactions play significant roles in shaping the extended
structure of this molecule.

1. Introduction would be of prime importance for environmental [12a,15], medicinal

The programmed self-assembly of discrete helicates has been the
topic of extensive research over the last few decades [1–4] because of
their aesthetic appeal as well as biomimetic relevance [1a-c,3]. The
basic principles of self-organization and molecular recognition [2] can
be understood by the basic mechanistic and energetic findings obtained
from study of formation, properties and structure of the helicates. Such
studies are important for the rational designing of complex architectures
[1,3a,5]. Among various types of ligands that are particularly shown to
be suitable for the formation of different types of helical compounds,
polypyridine derivatives dominate [1b-c, 6–9]. Many transition metals
with polypyridine ligands produce dihelicates. Dihelical chemistry is
mostly dominated by double stranded compounds of the types M2L2 and
triple stranded compounds of the types M2L3 where L is a bis-bidentate
ligand [1b-c,10]. Relatively rare are single-stranded dihelical complexes
involving a single ligand coordinating two metal centres in a helical
structure [11].
Furthermore, there are other potential features associated with the
metal complexes of polypyridine type ligands. Being π-electron defi­
cient, such heteroaromatics in favorable circumstances display moder­
ate to strong interactions with various anions [12]. Such type of
non-covalent interactions are specially relevant for the design of mo­
lecular receptors [12a,12c,12g,12m,13] and transporters [14] which
and biological applications [12a,12k,13a,13b,16] as well as in catalysis
[17].
Recently supramolecular chemistry has unveiled that non-
conventional H-bonds, such as (a) C–H … X (X = O, N, F, Cl) (b) X–H
… π (X = N, O, C, Si & π = double, triple or aromatic) (c) X–H …..M (M as
acceptors, M = Pt, Pd, Cu & X = N, O), M-H …..H (M as donors, M = Os,
Ir), (d) M ….(H–C) (agostic interactions), (e) X–H …...H-M (X = C, N, O,
S, dihydrogen bonding) often play crucial structural and biological roles
[18]. Detailed theoretical studies and experimental evidences on such
weak interactions may provide valuable informations for the develop­
ment of effective systems capable of recognizing different molecules
through non-covalent interactions.
We have synthesized [19,20] a π-electron-deficient N-heterocyclic
ligand (L) having two biologically relevant [21] imidazo[1,5-a]pyridine
parts. The ligand L can act as a bis-bidentate ligand, and its Cu(II)
compound provides a unique example of valence tautomerism in solu­
tion [20]. Herein, we report the synthesis of a oxovanadium(IV) com­
plex (1) with the N-heterocyclic electron deficient ligand (L). The
compound has single stranded dihelical structure. X-ray diffraction
analysis has been done to analyze the compound.

* Corresponding author.
E-mail address: nabanita.kundu@ladybrabourne.com (N. Kundu).

https://doi.org/10.1016/j.jics.2022.100401
Received 26 December 2021; Received in revised form 10 February 2022; Accepted 25 February 2022
Available online 4 March 2022
0019-4522/© 2022 Indian Chemical Society. Published by Elsevier B.V. All rights reserved.
T. Pada Majhi et al. Journal of the Indian Chemical Society 99 (2022) 100401

Table 1 2.2. Crystallography

X-ray crystallographic data for compound 1.
Parameter 1 Crystals of 1 (plate, green crystals, 0.04 × 0.04 × 0.01 mm3 obtained
from 1:1 (v/v) acetonitrile/dichloromethane) were grown by diffusion
Composition C24H20V2Cl4N6O4
Formula wt. 700.16 technique from the solvent combinations as noted above. Crystal was
Crystal system Triclinic mounted on glass fibers and aligned on a Bruker AXS platinum 200 CCD
Space group P-1 diffractometer. For data collection concerning the crystal at low tem­
a, Å 11.655(3) perature, it was coated with paraffin oil and placed in a cold stream of
b, Å 12.587(3)
c, Å 12.681(3)
nitrogen. Intensity data was collected with silicon 111 mono­
α, deg 76.160(4) chromatized synchrotron radiation (λ = 0.77490 Å) at 193(2) K using
β, deg 86.063(5) the ω-rotation scan techniques with narrow frames. The empirical ab­
γ, deg 62.563(4) sorption corrections were carried out using the multi-scan data and the
V, Å3 1601.3(7)
SADABS [23] software. The structure was solved by direct methods [23]
Dcalc, Mgm− 3 1.45
Temp, K 193(2) and least square refinement [anisotropic displacement parameters,
λ, Å 0.77490 hydrogen atoms in the riding model approximation and a weighing
Z 2 scheme of the form w = 1/[σ2(F02) + (aP)2 + bP] for P = (F02 + 2Fc2)/3)]
F(000)/μ mm− 1 704/1.208 was on F2 [23]. Bruker SHELXTL [23] was used both for structure so­
2θmax [ο] 49.29
Reflections Collected/Unique 10088/4181
lutions and refinements. Crystallographic parameters are given in
Rint/GOF on F2 0.054/1.031 Table 1. The positions of all non-hydrogen atoms were refined with
No of parameters 373 anisotropic displacement factors. The water bound hydrogen atoms
R1(F0), wR2(F0) (I ≥ 2σ(I)) 0.0713, 0.1754 could neither be placed nor found and were therefore, omitted during
the refinements. A number of attempts were made to model an area of
disordered solvent all of which failed. It was therefore decide to use
2. Experimental
SQUEEZE [24] to remove this solvent. SQUEEZE indicated that the total
number of electrons in the solvent space in the unit cell was 99 in a
Method of preparation of the ligand L has been described elsewhere
solvent accessible volume of 343 Ang3. The solvent was dichloro­
[19,20]. All reagents were commercially available. Solvents were dried
methane and two molecules would be 84 electrons. The solvent mole­
by standard methods [22]. Elemental (C, H, N, and S) analyses were
cules were not added to the formula. Data reductions were done with
done on a Perkin-Elmer model 2400 Series II CHNS Analyzer. The IR
Bruker SAINT and “Bruker SAINT V7.23a” software packages and
spectra were performed on a Shimadzu model 8400S FT-IR spectrometer
crystallographic diagrams were drawn using “Bruker SHELXTL” at 30%
with samples prepared as KBr pellets.
probability level.
2.1. Synthesis and crystallization
3. Result and discussion

[V2O2Cl4 (L)(H2O)2] 1 3.1. Synthesis

VCl3 (32 mg, 0.2 mmol) was dissolved in acetonitrile (5 mL) and was
carefully added on to a dichloromethane (5 mL) solution of L (39 mg,
0.1 mmol) to form two distinct layers. Diffusion between these two
layers produced green crystalline compound. Yield: 20%. Anal. Calcd for
C25H22N6V2Cl6O4: C, 38.41; H, 2.81; N, 10.75. Found: C, 38.14; H, 2.86;
N, 10.23%. FT-IR (KBr pellet, cm− 1): 3382 (s), 1618 (s), 1585 (sh), 1535
(sh), 1488 (w), 1460 (sh), 1425 (m), 1340 (sh), 1247 (m), 979 (s), 752
(s), 671 (w).
The bis-bidentate mode of the ligand in combination with tetravalent
V(IV)O metal salt with inert counter anions like chloride favors the
formation of relatively rare [11] single-stranded dihelicates [V2O2Cl4(L)
(H2O)2] (1) (Scheme 1). The ligand L has identical halves, each con­
taining three different heterocyclic rings, viz., imidazole (A), isolated
pyridine (B), and fused pyridine (C) rings, which will be designated as
im, py, and azopy rings, respectively, in the following part of this dis­
cussion. IR spectra of the complex contains all the pertinent bands at ca.
1600, 1485, 1461, 1313, 1247, 770 cm− 1 region due to the coordinated
bipyridine type ligands [25]. The complex shows a strong band at 979
cm− 1 due to terminal ν (V = Ot) stretchings [26].

Scheme 1. Protocol followed for the synthesis of Compound 1.

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T. Pada Majhi et al. Journal of the Indian Chemical Society 99 (2022) 100401

Fig. 1. Perspective view of the neutral single stranded helicate V2O2Cl4(L)

(H2O)2 in 1 showing the atomic labeling scheme, shown with 30% probability
displacement ellipsoids for non-H atoms. H atoms have been eliminated
for clarity.

Table 2
Selected Bond Distances (Å) and Angles (deg) for compound 1.
Bond Distances (Å)

V(1)–N(1) 2.162(6) V(2)–N(5) 2.117(6)

V(1)–N(2) 2.112(6) V(2)–N(6) 2.154(6)
V(1)–Cl(1) 2.380(2) V(2)–Cl(3) 2.332(2)
V(1)–Cl(2) 2.352(2) V(2)–Cl(4) 2.253(3)
V(1)–O(1) 1.609(6) V(2)–O(2) 1.779(5)
V(1)—O(1W) 2.239(5) V(2)—O(2W) 2.278(5)
Bond Angles (deg)
Cl(1)—V(1)—Cl(2) 91.81(8) Cl(3)—V(2)—Cl(4) 90.07(10)
Cl(1)—V(1)—N(2) 165.09(17) Cl(3)—V(2)—O(2) 103.23(18)
Cl(1)—V(1)—O(1W) 85.98(16) Cl(3)—V(2)—N(5) 95.56(18)
Cl(1)—V(1)—O(1) 96.2(2) Cl(3)—V(2)—O(2W) 83.09(15)
Cl(1)—V(1)—N(1) 93.57(19) Cl(3)—V(2)—N(6) 161.35(19)
Cl(2)—V(1)—N(2) 93.65(18) Cl(4)—V(2)—O(2) 94.6(2)
Cl(2)—V(1)—O(1W) 83.51(14) Cl(4)—V(2)—N(5) 164.81(19)
Cl(2)—V(1)—O(1) 103.1(2) Cl(4)—V(2)—O(2W) 86.13(17) Fig. 2. Crystal packing in 1 showing hydrogen bonding interactions among
Cl(2)—V(1)—N(1) 157.17(18) Cl(4)—V(2)—N(6) 94.9(2) coordinated water molecules and Cl− anions.
N(2)—V(1)—O(1W) 80.9(2) O(2)—V(2)—N(5) 97.8(3)
N(2)—V(1)—O(1) 96.0(3) O(2)—V(2)—O(2W) 173.6(2)
N(2)—V(1)—N(1) 76.3(2) O(2)—V(2)—N(6) 94.3(2) Å (corresponding values for V(2) are − 0.050, 0.049, 0.0.41, − 0.040 Å),
O(1W)–V(1)—O(1) 172.9(3) N(5)—V(2)—O(2W) 80.6(2) respectively out of the least squares plane through them. The epical sites
O(1W)–V(1)—N(1) 74.8(2) N(5)—V(2)—N(6) 75.5(2) are occupied by terminal oxo ligand.
O(1)—V(1)—N(1) 98.4(3) O(2W)–V(2)—N(6) 79.3(2)
O(1) (O(2)) and O(1W) (O(2W)) atom contributed by a water
molecule. The trans angles in the basal plane Cl(1)-V(1)-N(2), 165.09
3.2. Structure (17)◦ and Cl(2)-V(1)-N(1), 157.17(18)º are much short of linearity and
force the V(1) atom by 0.331 Å out of the least squares basal plane to­
The molecular structure with atomic labeling scheme for compound wards the more tightly held epical oxo atom O(1). The corresponding
1 is displayed in Fig. 1, which provides evidence in favour of its single trans angle Cl(3)-V(2)-N(6), 161.35(19)◦ and Cl(4)-V(2)-N(5), 164.81
stranded dihelical composition. The selected metrical parameters are (19)◦ around V(2) are also short of linearity but less compressed than
shown in Table 2. The compound crystallizes in triclinic space group P-1 around V(1) and accounts for the less shifting of V(2), 0.295 Å towards
and the unit cell accomodates two molecular weight units. The com­ epical O(2). The V–N (2.112(6) - 2.162(6) Å) [27], V–Cl (2.252(2) -
pound lacks molecular center of symmetry. The coordination environ­ 2.380(2) Å) [27], V–OH2 (2.239(5) - 2.278(5) Å) [28] and V(1)–O(1)
ments around both V(1) and V(2) are distorted octahedral where four distances (1.609(6) Å) [27] are in the expected range, while the V(2)–O
basal positions of V(1) being taken up by N(1), N(2) (N(5), N(6) in case (2) bond length (1.779(5) Å) is slightly larger than normally observed in
of V(2)) atoms from the ligand L together with two monodentate chloro V(IV)–O oxo compounds [27]. Due to the severe twist of the ligand
ligands Cl(1), Cl(2) (Cl(3), Cl(4)) and lie − 0.094, 0.096, 0.072, − 0.074 strand about the central inter annular C–C (im-im) bond rigorous strain
has been imposed by the octahedral coordination environments

3
T. Pada Majhi et al. Journal of the Indian Chemical Society 99 (2022) 100401

Table 3 there are some weak hydrogen bonds involving ligand’s C–H bonds and
Hydrogen bonding interactions for 1 [Å and ◦ ]. coordinated chlorine atoms and water molecules. Details of hydrogen
D-H … A d(D-H) d(H … A) d(D …..A) <(DHA) bonding interaction parameters are summarized in Table 3.
The most fascinating feature of this supramolecular species is the
O(1W)–H(1WA) … Cl(1)#1 0.840(10) 2.34(2) 3.149(6) 162(7)
O(1W)–H(1WB)...Cl(4)#2 0.840(10) 2.34(4) 3.059(6) 144(6) presence of intramolecular anion-π interactions involving coordinated
O(2W)–H(2WA) … Cl(3)#2 0.840(10) 2.515(19) 3.347(6) 171(8) chlorine atoms and the π-electron deficient aromatic rings (Fig. 3). The
O(2W)–H(2WB)⋯Cl(2) 0.838(10) 2.49(3) 3.279(6) 157(7) coordinated chlorine atoms Cl(2) and Cl(3) are located 3.434(4) and
C(7)-H(7A) … Cl(3)#3 0.95 2.49 3.349(8) 151.1 3.372(5) Å from the electron deficient im rings (N(4)-C(14)-C(13)-N(5)-
C(18)-H(18A) … Cl(2)#4 0.95 2.81 3.730(8) 163.2
C(17)-H(17A) … O(2W)#4 0.95 2.55 3.384(9) 145.9
C(19)) and (N(2)-C(6)-N(3)-C(11)-C(12)), respectively. These distances
C(21)-H(21A) … Cl(2)#4 0.95 2.73 3.583(8) 149.8 are shorter than mean pyridine-Cl- distance of 3.427 Å [12n] and larger
C(8)-H(8A) … O(1W)#3 0.95 2.60 3.477(9) 153.6 than the values calculated for the model s-triazine—Cl- (3.2 Å) [13b,29]
C(24)-H(24A) … Cl(1)#5 0.95 2.91 3.622(9) 132.5 complex. Unfortunately, no theoretical investigation is yet available for
C(24)-H(24A) … Cl(4) 0.95 2.70 3.306(9) 122.4
the imidazole type ring, which is much less electron deficient than
C(4)-H(4A) … Cl(3)#3 0.95 2.84 3.767(9) 164.5
C(1)-H(1A) … Cl(1) 0.95 2.78 3.364(9) 120.4 s-triazine ring, and less electron deficiency is the reason for longer
C(1)-H(1A) … Cl(4)#6 0.95 2.76 3.452(10) 130.8 ring-anion distances. The anion-π interactions observed in 1 are
C(2)-H(2A) … Cl(4)#6 0.95 2.93 3.518(11) 121.2 enhanced by the fact that the imidazole rings are coordinated to vana­
Symmetry transformations used to generate equivalent atoms. dium ions, which increases their electron deficient behaviour.
#1 -x+1,-y+1,-z+1 #2 -x,-y+2,-z+1 #3 -x+1,-y+2,-z+1 #4 -x,-y+2,-z #5 x-1,
y+1,z #6 x+1,y-1,z. 4. Conclusions

Oxovanadium(IV) complex (1) of the electron deficient N-rich het­

erocyclic ligand (L) has been synthesized. The compound is binuclear
and has single-stranded helical topology. In the solid state the structure
shows multiple anion− π interactions and inter- and intra-molecular
hydrogen bonding interactions among coordinated water molecules
and Cl− anions. These interactions play significant roles in shaping the
extended structure of this molecule in the solid state. The compound also
produces a series of Carene-H—anion nonclassical H-bonding interactions
that reinforce these non-covalent interactions in the molecule.

Declaration of competing interest

The authors declare that they have no known competing financial

interests or personal relationships that could have appeared to influence
the work reported in this paper.

Acknowledgement

The work was supported by the Council of Scientific and Industrial

Research (CSIR), New Delhi. We thank Prof. Muktimoy Chaudhury for
his guidance.

Appendix A. Supplementary data

Fig. 3. Anion-π interactions in compounds 1 between the coordinated Cl− Supplementary data to this article can be found online at https://doi.
anions and im rings. org/10.1016/j.jics.2022.100401.

surrounding the V(IV) centres that allows one of the oxo group to remain
slightly away from the metal centre. The V⋯V separation in this dinu­
clear compound is 5.8271(22) Å. The basal planes surrounding the two
vanadium (IV) centres are nearly orthogonal to each other as observed
by the dihedral angle (84.79(12)◦ ) between them.
As shown in Fig. 2, the coordinated water molecules in 1 are involved
in inter- and intramolecular hydrogen bonding interactions with coor­
dinated chlorine atoms. Although the hydrogen atoms of the water
molecules could not be located in the difference Fourier map, the
presence of hydrogen bonds is revealed from the short O(W)–Cl con­
tacts. Intramolecular hydrogen bonding interaction exists between O
(2W) and Cl(2). Also the coordinated water molecule O(1W) participates
in strong intermolecular hydrogen bonding with Cl(4) atom of symmetry
related adjacent molecule. In effect, the two adjacent complex molecules
form a tetrameric unit. Each of these units is connected to adjacent
tetrameric unit through Cl(1)-O(1W) hydrogen bond to form a staircase
like polymeric network (Fig. 2). The intermolecular V——V separations
in this H-bonded network are 5.7992(36) and 6.2468(29) Å. Finally,
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