Crystal structure and Hirshfeld surface analysis of 6,6′-dimethyl-2,2′-bi­pyridine-1,1′-diium tetra­chlorido­cobaltate(II)

Jagadeesan, S.; Robert, S.D.; Venkatesan, P.; Sundararaj, R.; Soundararajan, K.; Nithianantham, J.J.

doi:10.1107/S2056989024005152

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Volume 80| Part 7| July 2024| Pages 709-712

https://doi.org/10.1107/S2056989024005152

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Crystal structure and Hirshfeld surface analysis of 6,6′-dimethyl-2,2′-bipyridine-1,1′-diium tetrachloridocobaltate(II)

Sivaraman Jagadeesan,^a Swinton Darious Robert,^b Perumal Venkatesan,^a Rajamanikandan Sundararaj,^c Krishnan Soundararajan ^d and Jeeva Jasmine Nithianantham ^e ^*

^aDepartment of Chemistry, Srimad Andavan Arts and Science College (Autonomous), Tiruchirappalli-620005, Tamilnadu, India, ^bPG & Research Department of Chemistry, Bishop Heber College (Autonomous), Tiruchirappalli-620017, Tamilnadu, India, ^cCenter for Drug Discovery, Karpagam Academy of Higher Education, Coimbatore, Tamilnadu, India, ^dDepartment of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam-613403, Thanjavur, Tamilnadu, India, and ^eMolecular Biophysics Unit, Indian Institute of Science, Bangalore, India
^*Correspondence e-mail: iiscjeevajasmine@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 22 April 2024; accepted 30 May 2024; online 11 June 2024)

In the title molecular salt, (C₁₂H₁₄N₂)[CoCl₄], the dihedral angle between the pyridine rings of the cation is 52.46 (9)° and the N—C—C—N torsion angle is −128.78 (14)°, indicating that the ring nitrogen atoms are in anti-clinal conformation. The Cl—Co—Cl bond angles in the anion span the range 105.46 (3)–117.91 (2)°. In the extended structure, the cations and anions are linked by cation-to-anion N—H⋯Cl and C—H⋯Cl interactions, facilitating the formation of R⁴₄(18) and R⁴₄(20) ring motifs. Furthermore, the crystal structure features weak anion-to-cation Cl⋯π interactions [Cl⋯π = 3.4891 (12) and 3.5465 (12) Å]. Hirshfeld two-dimensional fingerprint plots revealed that the most significant interactions are Cl⋯H/H⋯Cl (45.5%), H⋯H (29.0%), Cl⋯C/C⋯Cl (7.8%), Cl⋯N/N⋯Cl (3.5%), Cl⋯Cl (1.4) and Co⋯H (1%) contacts.

Keywords: cobalt complex; substituted bipyridine; Hirshfeld surface analysis; crystal structure.

CCDC reference: 2347766

1. Chemical context

In recent years, non-covalent interactions have played an important role in organic–inorganic hybrid materials that have attracted researchers because of their potential applications in catalysis, energy storage devices, luminescence, photography and drug delivery (Bringley et al., 2005 ; Avila-Montiel et al., 2020 ). Cobalt(II) halide compounds are used as metal catalysts in various organic transformations and possess important fluorescence and magnetic properties (Decaroli et al., 2015 ). As part of our work in this area, we now describe the synthesis, structure and Hirshfeld surface analysis of the title salt, C₁₂H₁₄N₂²⁺·[CoCl₄]^2–, (I).

2. Structural commentary

The asymmetric unit of (I) contains one C₁₂H₁₄N₂²⁺ (DMB²⁺) cation and one [CoCl₄]^2– anion in the triclinic space group P $[\overline{1}]$ (Fig. 1). The pyridine ring nitrogen atoms are protonated, which is confirmed by the widening of the C2—N1—C6 [123.47 (14)°] and C8—C7—N2 [119.92 (14)°] bond angles compared to a value of 118.4° in the neutral compound (Sengül et al., 1998 ). The dihedral angle between the pyridine rings in (I) is 52.46 (9)°, showing that they are substantially twisted with respect to each other. The values for the torsion angles C5—C6—C7—C8 [–127.95 (17)°] and N1—C6—C7—N2 [–128.78 (14)°] indicate that the nitrogen atoms of the pyridine rings exhibit a (–)anti-clinal conformation. The Co—Cl bond lengths in the [CoCl₄]^2– anion range from 2.2600 (6)–2.2997 (7) Å, where Cl1 and Cl4 have a longer distance than Cl2 and Cl3. The average Co—Cl bond length of 2.280 Å is consistent with that of similar complexes (Zhang et al., 2005 ; Jebas & Balasubramanian, 2006 ). The Cl—Co—Cl bond angles are in the range 105.46 (3)–117.91 (2)° with an average bond angle of 111.13 (2)° (Azadbakht et al., 2012 ; Mghandef & Boughzala, 2015 ). The smallest bond angle (Cl2—Co1—Cl3) correlates with the shortest Co—Cl bond lengths but there is no obvious correlation between bond lengths and the largest angle.

Figure 1
The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the extended structure of (I), the components are linked by N1—H1⋯Cl1 and N2—H2⋯Cl4 hydrogen bonds (Table 1), which generate infinite [1 $[\overline{1}]$ 0] chains. Weak C4—H4⋯Cl3 and C9—H9⋯Cl2 hydrogen bonds also occur, so that each chlorine atom accepts one hydrogen bond. Together, the hydrogen bonds generate infinite sheets in which R₄⁴(18) and R₄⁴(20) loops are apparent (Fig. 2). A wavy sheet-like structure of the compound can be seen when the structure is viewed along the ab-axis direction (Fig. 3). The crystal structure also features weak anion⋯π interactions [Co1—Cl2⋯Cg2^iv = 3.5465 (12) Å; Co1—Cl3⋯Cg1^iv = 3.4891 (12) Å, where Cg1 is the centroid of the N1/C2–C6 ring and Cg2 is the centroid of the N2/C7–C11 ring; symmetry code: (iv) 1 + x, y, z] (Degtyarenko & Domasevitch, 2014 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.93 (2)	2.32 (2)	3.2205 (16)	164.5 (18)
N2—H2⋯Cl4ⁱ	0.87 (2)	2.38 (2)	3.2436 (16)	171 (2)
C4—H4⋯Cl3ⁱⁱ	0.93	2.68	3.571 (2)	161
C9—H9⋯Cl2ⁱⁱⁱ	0.93	2.79	3.565 (2)	141
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
A view of the supramolecular architecture of (I), showing the R₄⁴(18) and R₄⁴(20) loops. [Symmetry code: (iv) 1 + x, y, z.]

Figure 3
The wavy sheet-like two-dimensional supramolecular architecture of (I) viewed along the ab direction. The black dotted lines represent hydrogen bonds.

The Hirshfeld surface analysis and its related fingerprint plots were created with Crystal Explorer 17.5 (Turner et al., 2017 ). The Hirshfeld surface of the title salt (Fig. 4) mapped over d_norm within the range −0.43 to 1.17 a.u. shows bright red spots within the locales of D⋯A (D = donor, A = acceptor) interactions, as expected. The two-dimensional fingerprint plots (Fig. 5) show that the most significant contacts are Cl⋯H/H⋯Cl (45.5%), H⋯H (29.0%), C⋯H/H⋯C (11.2%), Cl⋯C/C⋯Cl (7.8%), Cl⋯N/N⋯Cl (3.5%), Cl⋯Cl (1.4%), Co⋯H (1.0%) and C⋯C (0.5%).

Figure 4
A view of the three-dimensional Hirshfeld surface of (I)

mapped over d_norm.

Figure 5
The two-dimensional fingerprint plot for (I) showing all intermolecular interactions and delineated into Cl⋯H/H⋯Cl, H⋯H, C⋯H/H⋯C, Cl⋯C/C⋯Cl, Cl⋯N/N⋯Cl, Cl⋯Cl, Co⋯H and C⋯ contacts.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.44. last update Jun 2023; Groom et al., 2016 ) for the 6,6′-dimethyl-2,2′-bipyridinium ion yielded six entries, viz. CSD refcodes IQUREU (Yoshikawa, 2021 ), IQUREU01 (Yoshikawa et al., 2022 ), KARRAA (Jurowska et al., 2021 ), QUJVUO (Thangavelu et al., 2015 ), UWUKAZ02 (Kobayashi et al., 2014 ) and YABGIS (Chan & Baird, 2004 ). The mean dihedral angle between the pyridine rings of the DMB²⁺ cations in these structures is 38.75 (10)°

5. Synthesis and crystallization

The compound of interest was synthesized by a literature method (Jagadeesan et al., 2013 ) by dissolving 2.00 mmol (0.3682 g) of the ligand in methanol and adding directly 1.00 mmol (0.1289 g) of anhydrous cobaltous chloride. The whole mixture was refluxed for about an hour. A dark-brown solution was obtained. Afterwards, a sufficient amount of chlorine gas was passed through the solution until precipitation occurred. The precipitate was dissolved in aqueous HCl (0.001 M) by warming to 333 K for 30 min and the resulting mixture was kept undisturbed overnight. The resulting precipitate was discarded and the filtrate was kept for a few weeks until dark-blue crystals of (I) appeared (0.067 g).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and were refined using a riding model with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	(C₁₂H₁₄N₂)[CoCl₄]
M_r	386.98
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	301
a, b, c (Å)	6.6419 (16), 7.6512 (19), 15.837 (4)
α, β, γ (°)	99.458 (6), 98.020 (6), 97.046 (6)
V (Å³)	777.3 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.78
Crystal size (mm)	0.21 × 0.11 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.625, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13285, 3890, 3661
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.081, 1.03
No. of reflections	3890
No. of parameters	180
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36
Computer programs: APEX4 and SAINT (Bruker, 2021 ), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2347766

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024005152/hb8095sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024005152/hb8095Isup2.hkl

checkCIF report

Computing details top

6,6'-Dimethyl-2,2'-bipyridine-1,1'-diium tetrachloridocobaltate(II) top

Crystal data top

(C₁₂H₁₄N₂)[CoCl₄]	Z = 2
M_r = 386.98	F(000) = 390
Triclinic, P1	D_x = 1.653 Mg m⁻³
a = 6.6419 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6512 (19) Å	Cell parameters from 9272 reflections
c = 15.837 (4) Å	θ = 2.7–28.6°
α = 99.458 (6)°	µ = 1.78 mm⁻¹
β = 98.020 (6)°	T = 301 K
γ = 97.046 (6)°	Block, blue
V = 777.3 (3) Å³	0.21 × 0.11 × 0.04 mm

Data collection top

Bruker APEXII CCD diffractometer	3661 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.041
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.6°, θ_min = 2.7°
T_min = 0.625, T_max = 0.746	h = −8→8
13285 measured reflections	k = −10→10
3890 independent reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0415P)² + 0.2392P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
3890 reflections	Δρ_max = 0.41 e Å⁻³
180 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints

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
Co1	0.83193 (3)	0.11776 (3)	0.75825 (2)	0.02835 (8)
Cl1	0.50544 (6)	0.08040 (5)	0.79190 (3)	0.03681 (10)
Cl2	1.04301 (7)	0.30332 (6)	0.87001 (3)	0.04763 (12)
Cl3	0.82188 (7)	0.26717 (7)	0.64540 (3)	0.04459 (11)
Cl4	0.91033 (8)	−0.16382 (6)	0.71718 (3)	0.04905 (12)
N1	0.34377 (19)	0.34550 (17)	0.66800 (8)	0.0288 (2)
H1	0.371 (3)	0.276 (3)	0.7098 (14)	0.043*
N2	0.2849 (2)	0.69414 (16)	0.82797 (8)	0.0295 (2)
H2	0.178 (3)	0.719 (3)	0.7963 (14)	0.044*
C1	0.2787 (3)	0.0670 (3)	0.56372 (13)	0.0511 (5)
H1A	0.235167	0.025817	0.502509	0.077*
H1B	0.181069	0.013236	0.594770	0.077*
H1C	0.411174	0.033861	0.580711	0.077*
C2	0.2923 (2)	0.2659 (2)	0.58417 (10)	0.0351 (3)
C3	0.2537 (3)	0.3744 (3)	0.52323 (11)	0.0432 (4)
H3	0.220294	0.323926	0.464580	0.052*
C4	0.2648 (3)	0.5561 (3)	0.54950 (11)	0.0465 (4)
H4	0.239832	0.628226	0.508449	0.056*
C5	0.3130 (3)	0.6328 (2)	0.63697 (11)	0.0386 (3)
H5	0.317851	0.755367	0.655242	0.046*
C6	0.3535 (2)	0.52315 (19)	0.69586 (9)	0.0276 (3)
C7	0.4097 (2)	0.58981 (18)	0.79017 (9)	0.0276 (3)
C8	0.5805 (3)	0.5515 (2)	0.83936 (11)	0.0360 (3)
H8	0.669290	0.481996	0.814006	0.043*
C9	0.6170 (3)	0.6193 (2)	0.92811 (11)	0.0440 (4)
H9	0.731908	0.595592	0.962668	0.053*
C10	0.4840 (3)	0.7213 (2)	0.96494 (10)	0.0441 (4)
H10	0.507794	0.764127	1.024450	0.053*
C11	0.3147 (3)	0.7606 (2)	0.91364 (10)	0.0368 (3)
C12	0.1623 (4)	0.8715 (3)	0.94657 (14)	0.0555 (5)
H12A	0.186823	0.894239	1.008855	0.083*
H12B	0.025769	0.808301	0.925793	0.083*
H12C	0.176477	0.983126	0.926248	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02780 (12)	0.03196 (12)	0.02530 (12)	0.00566 (8)	0.00268 (8)	0.00579 (8)
Cl1	0.03370 (19)	0.03675 (19)	0.0430 (2)	0.00376 (14)	0.01266 (15)	0.01194 (15)
Cl2	0.0492 (2)	0.0456 (2)	0.0389 (2)	−0.00486 (18)	−0.01213 (18)	0.00607 (17)
Cl3	0.0398 (2)	0.0659 (3)	0.0347 (2)	0.00992 (19)	0.00815 (16)	0.02524 (19)
Cl4	0.0507 (3)	0.0430 (2)	0.0507 (3)	0.02070 (19)	0.00004 (19)	−0.00242 (18)
N1	0.0270 (6)	0.0315 (6)	0.0266 (6)	0.0068 (5)	0.0002 (4)	0.0032 (5)
N2	0.0350 (6)	0.0275 (6)	0.0265 (6)	0.0043 (5)	0.0051 (5)	0.0068 (4)
C1	0.0499 (10)	0.0451 (10)	0.0481 (10)	0.0075 (8)	0.0000 (8)	−0.0142 (8)
C2	0.0264 (7)	0.0447 (8)	0.0298 (7)	0.0061 (6)	0.0014 (5)	−0.0034 (6)
C3	0.0377 (8)	0.0659 (11)	0.0241 (7)	0.0080 (8)	0.0028 (6)	0.0040 (7)
C4	0.0482 (10)	0.0668 (12)	0.0301 (8)	0.0134 (9)	0.0054 (7)	0.0224 (8)
C5	0.0462 (9)	0.0390 (8)	0.0343 (8)	0.0109 (7)	0.0058 (7)	0.0149 (6)
C6	0.0266 (6)	0.0315 (7)	0.0253 (6)	0.0063 (5)	0.0031 (5)	0.0062 (5)
C7	0.0312 (7)	0.0250 (6)	0.0257 (6)	0.0018 (5)	0.0020 (5)	0.0061 (5)
C8	0.0353 (8)	0.0330 (7)	0.0371 (8)	0.0045 (6)	−0.0039 (6)	0.0078 (6)
C9	0.0470 (9)	0.0429 (9)	0.0355 (8)	−0.0034 (7)	−0.0117 (7)	0.0117 (7)
C10	0.0619 (11)	0.0393 (8)	0.0247 (7)	−0.0076 (8)	0.0003 (7)	0.0045 (6)
C11	0.0511 (9)	0.0294 (7)	0.0298 (7)	−0.0015 (6)	0.0123 (7)	0.0058 (6)
C12	0.0712 (14)	0.0506 (11)	0.0466 (10)	0.0094 (10)	0.0273 (10)	−0.0002 (8)

Geometric parameters (Å, º) top

Co1—Cl2	2.2600 (6)	C4—C5	1.389 (2)
Co1—Cl3	2.2720 (6)	C4—H4	0.9300
Co1—Cl4	2.2901 (7)	C5—C6	1.374 (2)
Co1—Cl1	2.2997 (7)	C5—H5	0.9300
N1—C2	1.3441 (19)	C6—C7	1.4758 (19)
N1—C6	1.3490 (19)	C7—C8	1.375 (2)
N1—H1	0.93 (2)	C8—C9	1.392 (2)
N2—C11	1.346 (2)	C8—H8	0.9300
N2—C7	1.3511 (19)	C9—C10	1.376 (3)
N2—H2	0.87 (2)	C9—H9	0.9300
C1—C2	1.492 (3)	C10—C11	1.387 (3)
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600	C11—C12	1.492 (3)
C1—H1C	0.9600	C12—H12A	0.9600
C2—C3	1.390 (3)	C12—H12B	0.9600
C3—C4	1.374 (3)	C12—H12C	0.9600
C3—H3	0.9300

Cl2—Co1—Cl3	105.46 (3)	C6—C5—C4	118.36 (16)
Cl2—Co1—Cl4	117.91 (2)	C6—C5—H5	120.8
Cl3—Co1—Cl4	110.39 (2)	C4—C5—H5	120.8
Cl2—Co1—Cl1	108.93 (2)	N1—C6—C5	119.83 (14)
Cl3—Co1—Cl1	107.287 (19)	N1—C6—C7	116.98 (12)
Cl4—Co1—Cl1	106.46 (2)	C5—C6—C7	123.19 (14)
C2—N1—C6	123.47 (14)	N2—C7—C8	119.92 (14)
C2—N1—H1	119.4 (14)	N2—C7—C6	116.93 (13)
C6—N1—H1	117.1 (14)	C8—C7—C6	123.15 (14)
C11—N2—C7	123.32 (14)	C7—C8—C9	118.30 (16)
C11—N2—H2	117.4 (14)	C7—C8—H8	120.9
C7—N2—H2	119.2 (14)	C9—C8—H8	120.9
C2—C1—H1A	109.5	C10—C9—C8	120.32 (16)
C2—C1—H1B	109.5	C10—C9—H9	119.8
H1A—C1—H1B	109.5	C8—C9—H9	119.8
C2—C1—H1C	109.5	C9—C10—C11	120.25 (15)
H1A—C1—H1C	109.5	C9—C10—H10	119.9
H1B—C1—H1C	109.5	C11—C10—H10	119.9
N1—C2—C3	117.74 (15)	N2—C11—C10	117.86 (16)
N1—C2—C1	117.33 (16)	N2—C11—C12	117.45 (17)
C3—C2—C1	124.93 (16)	C10—C11—C12	124.69 (17)
C4—C3—C2	120.12 (15)	C11—C12—H12A	109.5
C4—C3—H3	119.9	C11—C12—H12B	109.5
C2—C3—H3	119.9	H12A—C12—H12B	109.5
C3—C4—C5	120.43 (16)	C11—C12—H12C	109.5
C3—C4—H4	119.8	H12A—C12—H12C	109.5
C5—C4—H4	119.8	H12B—C12—H12C	109.5

C6—N1—C2—C3	2.1 (2)	N1—C6—C7—N2	−128.78 (14)
C6—N1—C2—C1	−177.24 (15)	C5—C6—C7—N2	51.6 (2)
N1—C2—C3—C4	−1.2 (3)	N1—C6—C7—C8	51.7 (2)
C1—C2—C3—C4	178.05 (18)	C5—C6—C7—C8	−127.95 (17)
C2—C3—C4—C5	−0.5 (3)	N2—C7—C8—C9	1.4 (2)
C3—C4—C5—C6	1.4 (3)	C6—C7—C8—C9	−179.06 (15)
C2—N1—C6—C5	−1.2 (2)	C7—C8—C9—C10	0.3 (3)
C2—N1—C6—C7	179.19 (14)	C8—C9—C10—C11	−1.4 (3)
C4—C5—C6—N1	−0.6 (2)	C7—N2—C11—C10	1.0 (2)
C4—C5—C6—C7	178.99 (15)	C7—N2—C11—C12	−179.01 (15)
C11—N2—C7—C8	−2.1 (2)	C9—C10—C11—N2	0.8 (2)
C11—N2—C7—C6	178.36 (14)	C9—C10—C11—C12	−179.26 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.93 (2)	2.32 (2)	3.2205 (16)	164.5 (18)
N2—H2···Cl4ⁱ	0.87 (2)	2.38 (2)	3.2436 (16)	171 (2)
C4—H4···Cl3ⁱⁱ	0.93	2.68	3.571 (2)	161
C9—H9···Cl2ⁱⁱⁱ	0.93	2.79	3.565 (2)	141

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

Acknowledgements

Authors thank the DST–FIST single-crystal X-ray Diffraction Facility at IIT Gandhinagar Project No: SR/FST/CSI-277/2016. They also thank Dr Vijay Thiruvenkatam, Dr Sivapriya Kirubakaran and Miss Delna Johnson (IIT-Gandhinagar) for their support with the data collection.

Funding information

Funding for this research was provided by: UGC-DSK-PDF [award No. F.4-2/2006 (BSR)/CH/18-19/0165(80th List)/18th March 2019 to NJJ]; BHC {grant No. [MRP/1911/2019 (BHC)] to RSD}.

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