6-Chloro-2-(4-meth­oxy­phen­yl)-4-phenyl­quinoline

Saravanan, B.; Thamilarasan, V.; Sengottuvelan, N.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536813023295

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1463

doi:10.1107/S1600536813023295

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6-Chloro-2-(4-methoxyphenyl)-4-phenylquinoline

B. Saravanan,^a V. Thamilarasan,^b N. Sengottuvelan,^b G. Chakkaravarthi ^c ^* and V. Manivannan ^a ^*

^aCentre for Research and Development, PRIST University, Vallam, Thanjavur 613 403, India, ^bDepartment of Chemistry, DDE, Alagappa University, Karaikudi 630 003, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, crystallography2010@gmail.com

(Received 15 August 2013; accepted 19 August 2013; online 23 August 2013)

In the title compound, C₂₂H₁₆ClNO, the quinoline ring system makes dihedral angles of 56.30 (6) and 7.93 (6)°, respectively, with the adjacent phenyl and benzene rings. The dihedral angle between these phenyl and benzene rings is 56.97 (8)°. In the crystal, weak C—H⋯π and π–π [centroid–centroid distances of 3.7699 (9) and 3.8390 (9) Å] interactions link the molecules into a layer parallel to the ab plane.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For a related structure, see: Akkurt et al. (2004 ).

Experimental

Crystal data

C₂₂H₁₆ClNO
M_r = 345.81
Monoclinic, P 2₁ /n
a = 10.5922 (5) Å
b = 8.2883 (3) Å
c = 19.1885 (9) Å
β = 92.988 (3)°
V = 1682.29 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 K
0.40 × 0.36 × 0.34 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.912, T_max = 0.924
12611 measured reflections
4148 independent reflections
3244 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.03
4148 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C10–C15 and C16–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg4ⁱ	0.93	2.63	3.7695 (19)	151
C22—H22B⋯Cg3ⁱⁱ	0.96	2.84	3.613 (3)	138
Symmetry codes: (i) x-1, y, z; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023295/is5297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023295/is5297Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023295/is5297Isup3.cml

checkCIF report

Comment top

The geometric parameters of the title compound (Fig. 1) are within the normal range (Allen et al., 1987) and are comparable with the similar reported structure (Akkurt et al., 2004). The quinoxaline ring system is almost planar [maximum deviation of C3 atom from the mean plane is 0.0345 (16)Å]. The dihedral angle between the phenyl ring (C10–C15) and methoxyphenyl ring (C16–C21) is 56.97 (8)°. The crystal structure exhibit weak C—H···π (Table 1) and π–π [Cg1···Cg2ⁱ distance 3.7699 (9) Å and Cg2···Cg4ⁱⁱ distance 3.8390 (9) Å; (i) -x, 1 - y, 2 - z; (ii) -x, 2 - y, 2 - z; Cg1, Cg2 and Cg4 are the centroids of the rings (C1/C2/C3/C4/C9/N1), (C4–C9) and (C16–C21), respectively] interactions which leads to the of packing of the molecules.

Related literature top

For standard bond lengths, see: Allen et al. (1987). For a related structure, see: Akkurt et al. (2004).

Experimental top

5-Chloro-2-aminobenzophenone (1.86 g, 8.05 mmol) and 4-methoxyacetophenone (1.21 g, 8.05 mmol) in the presence of acetic acid (30 ml) and con. H₂SO₄ (0.5 ml) were stirred under argon at 140 °C for 18 h. After cooling to room temperature, 10% NaOH (100 ml) and dichloromethane (100 ml) were added to the reaction mixture. The organic layer was separated and washed with distilled water (50 ml×5) until a neutral solution was obtained. Later, it was dried over a Na₂SO₄ and evaporated under the natural condition to yield yellow crystals, suitable for X-Ray diffraction. Yield: 55 %.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

6-Chloro-2-(4-methoxyphenyl)-4-phenylquinoline top

Crystal data top

C₂₂H₁₆ClNO	F(000) = 720
M_r = 345.81	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5757 reflections
a = 10.5922 (5) Å	θ = 2.2–27.2°
b = 8.2883 (3) Å	µ = 0.24 mm⁻¹
c = 19.1885 (9) Å	T = 295 K
β = 92.988 (3)°	Block, yellow
V = 1682.29 (13) Å³	0.40 × 0.36 × 0.34 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4148 independent reflections
Radiation source: fine-focus sealed tube	3244 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→14
T_min = 0.912, T_max = 0.924	k = −10→10
12611 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0566P)² + 0.6619P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4148 reflections	Δρ_max = 0.29 e Å⁻³
228 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (2)

Crystal data top

C₂₂H₁₆ClNO	V = 1682.29 (13) Å³
M_r = 345.81	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5922 (5) Å	µ = 0.24 mm⁻¹
b = 8.2883 (3) Å	T = 295 K
c = 19.1885 (9) Å	0.40 × 0.36 × 0.34 mm
β = 92.988 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	4148 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3244 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.924	R_int = 0.034
12611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
4148 reflections	Δρ_min = −0.44 e Å⁻³
228 parameters

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.10650 (13)	0.86173 (17)	0.92160 (8)	0.0315 (3)
C2	0.00131 (14)	0.82128 (18)	0.87652 (8)	0.0344 (3)
H2	0.0020	0.8475	0.8294	0.041*
C3	−0.10138 (14)	0.74421 (18)	0.90118 (8)	0.0325 (3)
C4	−0.09729 (14)	0.69944 (17)	0.97278 (7)	0.0317 (3)
C5	−0.19335 (15)	0.61042 (18)	1.00396 (8)	0.0364 (3)
H5	−0.2641	0.5763	0.9772	0.044*
C6	−0.18207 (15)	0.57495 (19)	1.07298 (9)	0.0384 (3)
C7	−0.07731 (16)	0.6223 (2)	1.11478 (8)	0.0429 (4)
H7	−0.0724	0.5979	1.1621	0.052*
C8	0.01818 (16)	0.7050 (2)	1.08569 (8)	0.0418 (4)
H8	0.0888	0.7354	1.1134	0.050*
C9	0.01122 (14)	0.74491 (18)	1.01414 (7)	0.0334 (3)
C10	−0.21428 (14)	0.71165 (18)	0.85403 (8)	0.0344 (3)
C11	−0.20230 (16)	0.6298 (2)	0.79205 (8)	0.0417 (4)
H11	−0.1237	0.5911	0.7805	0.050*
C12	−0.30662 (19)	0.6052 (2)	0.74711 (9)	0.0527 (5)
H12	−0.2981	0.5497	0.7055	0.063*
C13	−0.42299 (18)	0.6626 (2)	0.76372 (10)	0.0523 (5)
H13	−0.4929	0.6459	0.7333	0.063*
C14	−0.43653 (17)	0.7446 (2)	0.82506 (10)	0.0495 (4)
H14	−0.5154	0.7836	0.8361	0.059*
C15	−0.33255 (16)	0.7688 (2)	0.87029 (9)	0.0420 (4)
H15	−0.3417	0.8238	0.9120	0.050*
C16	0.21525 (14)	0.95295 (17)	0.89617 (8)	0.0323 (3)
C17	0.30751 (16)	1.0092 (2)	0.94365 (8)	0.0403 (4)
H17	0.3017	0.9842	0.9906	0.048*
C18	0.40815 (16)	1.1014 (2)	0.92371 (9)	0.0440 (4)
H18	0.4691	1.1366	0.9569	0.053*
C19	0.41774 (15)	1.14080 (19)	0.85434 (9)	0.0391 (4)
C20	0.32825 (16)	1.0835 (2)	0.80568 (9)	0.0423 (4)
H20	0.3349	1.1082	0.7587	0.051*
C21	0.22887 (15)	0.9899 (2)	0.82607 (8)	0.0382 (3)
H21	0.1701	0.9509	0.7925	0.046*
C22	0.60395 (19)	1.2957 (3)	0.87780 (12)	0.0627 (6)
H22A	0.5638	1.3594	0.9121	0.094*
H22B	0.6622	1.3618	0.8539	0.094*
H22C	0.6487	1.2079	0.9004	0.094*
N1	0.11065 (12)	0.82580 (16)	0.98859 (6)	0.0354 (3)
O1	0.51123 (12)	1.23407 (17)	0.82929 (7)	0.0548 (3)
Cl1	−0.30154 (4)	0.46790 (6)	1.11096 (3)	0.05376 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0295 (7)	0.0299 (7)	0.0352 (7)	0.0002 (6)	0.0024 (6)	−0.0002 (6)
C2	0.0343 (7)	0.0371 (8)	0.0318 (7)	−0.0013 (6)	0.0014 (6)	0.0031 (6)
C3	0.0314 (7)	0.0324 (7)	0.0337 (7)	−0.0014 (6)	0.0006 (6)	−0.0011 (6)
C4	0.0314 (7)	0.0308 (7)	0.0331 (7)	0.0001 (6)	0.0034 (6)	−0.0002 (6)
C5	0.0324 (7)	0.0357 (8)	0.0413 (8)	−0.0020 (6)	0.0037 (6)	−0.0004 (6)
C6	0.0377 (8)	0.0345 (8)	0.0442 (8)	0.0026 (6)	0.0133 (7)	0.0052 (6)
C7	0.0456 (9)	0.0502 (10)	0.0335 (8)	0.0033 (8)	0.0059 (7)	0.0064 (7)
C8	0.0396 (8)	0.0532 (10)	0.0325 (7)	−0.0024 (7)	−0.0003 (6)	0.0026 (7)
C9	0.0316 (7)	0.0351 (7)	0.0336 (7)	0.0008 (6)	0.0030 (6)	−0.0003 (6)
C10	0.0328 (8)	0.0359 (8)	0.0344 (7)	−0.0066 (6)	−0.0002 (6)	0.0045 (6)
C11	0.0393 (9)	0.0485 (9)	0.0374 (8)	−0.0043 (7)	0.0035 (7)	−0.0005 (7)
C12	0.0616 (12)	0.0567 (11)	0.0390 (9)	−0.0115 (9)	−0.0044 (8)	−0.0038 (8)
C13	0.0484 (10)	0.0555 (11)	0.0511 (10)	−0.0127 (9)	−0.0169 (8)	0.0077 (8)
C14	0.0343 (9)	0.0498 (10)	0.0638 (11)	−0.0017 (7)	−0.0044 (8)	0.0068 (9)
C15	0.0375 (8)	0.0448 (9)	0.0435 (9)	−0.0014 (7)	0.0001 (7)	−0.0024 (7)
C16	0.0284 (7)	0.0319 (7)	0.0369 (7)	0.0004 (6)	0.0035 (6)	−0.0008 (6)
C17	0.0405 (9)	0.0459 (9)	0.0346 (7)	−0.0094 (7)	0.0039 (6)	0.0007 (7)
C18	0.0381 (8)	0.0482 (9)	0.0458 (9)	−0.0119 (7)	0.0043 (7)	−0.0055 (7)
C19	0.0349 (8)	0.0357 (8)	0.0481 (9)	−0.0024 (6)	0.0139 (7)	−0.0004 (7)
C20	0.0415 (9)	0.0478 (9)	0.0386 (8)	−0.0002 (7)	0.0111 (7)	0.0035 (7)
C21	0.0339 (8)	0.0437 (9)	0.0368 (8)	−0.0016 (6)	0.0012 (6)	−0.0002 (6)
C22	0.0443 (10)	0.0639 (13)	0.0804 (14)	−0.0197 (9)	0.0077 (10)	0.0101 (11)
N1	0.0310 (6)	0.0405 (7)	0.0345 (6)	−0.0028 (5)	0.0010 (5)	0.0012 (5)
O1	0.0450 (7)	0.0609 (8)	0.0599 (8)	−0.0171 (6)	0.0170 (6)	0.0020 (6)
Cl1	0.0495 (3)	0.0526 (3)	0.0610 (3)	−0.00404 (19)	0.0196 (2)	0.0144 (2)

Geometric parameters (Å, º) top

C1—N1	1.3180 (19)	C12—C13	1.374 (3)
C1—C2	1.415 (2)	C12—H12	0.9300
C1—C16	1.482 (2)	C13—C14	1.373 (3)
C2—C3	1.367 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.381 (2)
C3—C4	1.422 (2)	C14—H14	0.9300
C3—C10	1.486 (2)	C15—H15	0.9300
C4—C9	1.413 (2)	C16—C17	1.382 (2)
C4—C5	1.415 (2)	C16—C21	1.394 (2)
C5—C6	1.356 (2)	C17—C18	1.382 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.391 (2)	C18—C19	1.379 (2)
C6—Cl1	1.7366 (16)	C18—H18	0.9300
C7—C8	1.365 (2)	C19—O1	1.3635 (18)
C7—H7	0.9300	C19—C20	1.380 (2)
C8—C9	1.410 (2)	C20—C21	1.381 (2)
C8—H8	0.9300	C20—H20	0.9300
C9—N1	1.3612 (19)	C21—H21	0.9300
C10—C11	1.381 (2)	C22—O1	1.413 (2)
C10—C15	1.390 (2)	C22—H22A	0.9600
C11—C12	1.381 (2)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600

N1—C1—C2	121.87 (13)	C14—C13—C12	120.35 (16)
N1—C1—C16	116.71 (13)	C14—C13—H13	119.8
C2—C1—C16	121.37 (13)	C12—C13—H13	119.8
C3—C2—C1	120.97 (13)	C13—C14—C15	119.68 (17)
C3—C2—H2	119.5	C13—C14—H14	120.2
C1—C2—H2	119.5	C15—C14—H14	120.2
C2—C3—C4	118.15 (13)	C14—C15—C10	120.54 (16)
C2—C3—C10	120.24 (13)	C14—C15—H15	119.7
C4—C3—C10	121.60 (13)	C10—C15—H15	119.7
C9—C4—C5	118.91 (13)	C17—C16—C21	117.17 (14)
C9—C4—C3	117.13 (13)	C17—C16—C1	119.35 (14)
C5—C4—C3	123.95 (14)	C21—C16—C1	123.45 (14)
C6—C5—C4	119.84 (15)	C18—C17—C16	122.22 (15)
C6—C5—H5	120.1	C18—C17—H17	118.9
C4—C5—H5	120.1	C16—C17—H17	118.9
C5—C6—C7	121.92 (15)	C19—C18—C17	119.66 (15)
C5—C6—Cl1	119.45 (13)	C19—C18—H18	120.2
C7—C6—Cl1	118.63 (13)	C17—C18—H18	120.2
C8—C7—C6	119.46 (15)	O1—C19—C18	124.46 (16)
C8—C7—H7	120.3	O1—C19—C20	116.26 (15)
C6—C7—H7	120.3	C18—C19—C20	119.28 (14)
C7—C8—C9	120.90 (15)	C19—C20—C21	120.57 (15)
C7—C8—H8	119.6	C19—C20—H20	119.7
C9—C8—H8	119.6	C21—C20—H20	119.7
N1—C9—C8	117.64 (14)	C20—C21—C16	121.04 (15)
N1—C9—C4	123.43 (13)	C20—C21—H21	119.5
C8—C9—C4	118.93 (14)	C16—C21—H21	119.5
C11—C10—C15	119.02 (15)	O1—C22—H22A	109.5
C11—C10—C3	120.43 (14)	O1—C22—H22B	109.5
C15—C10—C3	120.50 (14)	H22A—C22—H22B	109.5
C10—C11—C12	120.26 (16)	O1—C22—H22C	109.5
C10—C11—H11	119.9	H22A—C22—H22C	109.5
C12—C11—H11	119.9	H22B—C22—H22C	109.5
C13—C12—C11	120.15 (17)	C1—N1—C9	118.39 (13)
C13—C12—H12	119.9	C19—O1—C22	117.74 (14)
C11—C12—H12	119.9

N1—C1—C2—C3	0.7 (2)	C10—C11—C12—C13	0.2 (3)
C16—C1—C2—C3	−176.68 (14)	C11—C12—C13—C14	−0.1 (3)
C1—C2—C3—C4	−2.7 (2)	C12—C13—C14—C15	−0.2 (3)
C1—C2—C3—C10	176.23 (14)	C13—C14—C15—C10	0.3 (3)
C2—C3—C4—C9	2.8 (2)	C11—C10—C15—C14	−0.2 (2)
C10—C3—C4—C9	−176.10 (14)	C3—C10—C15—C14	177.21 (15)
C2—C3—C4—C5	−175.86 (14)	N1—C1—C16—C17	−6.4 (2)
C10—C3—C4—C5	5.2 (2)	C2—C1—C16—C17	171.08 (15)
C9—C4—C5—C6	2.2 (2)	N1—C1—C16—C21	175.34 (14)
C3—C4—C5—C6	−179.14 (15)	C2—C1—C16—C21	−7.2 (2)
C4—C5—C6—C7	−0.6 (2)	C21—C16—C17—C18	1.4 (2)
C4—C5—C6—Cl1	179.16 (11)	C1—C16—C17—C18	−176.93 (15)
C5—C6—C7—C8	−1.0 (3)	C16—C17—C18—C19	0.6 (3)
Cl1—C6—C7—C8	179.27 (13)	C17—C18—C19—O1	178.35 (16)
C6—C7—C8—C9	0.9 (3)	C17—C18—C19—C20	−1.8 (3)
C7—C8—C9—N1	−179.24 (15)	O1—C19—C20—C21	−179.09 (15)
C7—C8—C9—C4	0.7 (2)	C18—C19—C20—C21	1.0 (3)
C5—C4—C9—N1	177.71 (14)	C19—C20—C21—C16	1.0 (3)
C3—C4—C9—N1	−1.0 (2)	C17—C16—C21—C20	−2.2 (2)
C5—C4—C9—C8	−2.2 (2)	C1—C16—C21—C20	176.10 (14)
C3—C4—C9—C8	179.04 (14)	C2—C1—N1—C9	1.2 (2)
C2—C3—C10—C11	54.3 (2)	C16—C1—N1—C9	178.68 (12)
C4—C3—C10—C11	−126.74 (17)	C8—C9—N1—C1	178.93 (14)
C2—C3—C10—C15	−123.02 (17)	C4—C9—N1—C1	−1.0 (2)
C4—C3—C10—C15	55.9 (2)	C18—C19—O1—C22	−0.6 (3)
C15—C10—C11—C12	−0.1 (2)	C20—C19—O1—C22	179.54 (17)
C3—C10—C11—C12	−177.51 (15)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C10–C15 and C16–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg4ⁱ	0.93	2.63	3.7695 (19)	151
C22—H22B···Cg3ⁱⁱ	0.96	2.84	3.613 (3)	138

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

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C10–C15 and C16–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg4ⁱ	0.93	2.63	3.7695 (19)	151
C22—H22B···Cg3ⁱⁱ	0.96	2.84	3.613 (3)	138

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

Acknowledgements

The authors acknowledge the STIC, Cochin University of Technology, Cochin, for the data collection. VT and NS also acknowledge the UGC [project 40–46/2011 (SR)], New Delhi.

References

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