1-(4-Chloro­phen­yl)-3-(2,4-dichloro­benzo­yl)thio­urea

Khawar Rauf, M.; Bolte, M.; Badshah, A.

doi:10.1107/S160053680900004X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o260

doi:10.1107/S160053680900004X

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1-(4-Chlorophenyl)-3-(2,4-dichlorobenzoyl)thiourea

M. Khawar Rauf,^a ^* Michael Bolte ^b and Amin Badshah ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J.-W.-Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: khawar_rauf@hotmail.com

(Received 3 December 2008; accepted 1 January 2009; online 8 January 2009)

The title compound, C₁₄H₉Cl₃N₂OS, has bond lengths and angles which are quite typical for thiourea compounds of this class. The molecule exists in the solid state in its thione form with typical thiourea C=S and C=O bond lengths, as well as shortened C—N bonds. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. Intermolecular N—H⋯S hydrogen bonds link the molecules to form centrosymmetric dimers.

Related literature

For thiourea derivatives with biological activities, see: Baily et al. (1996 ); Koch (2001 ); Maryanoff et al. (1986 ); Namgun et al. (2001 ); Patil & Chedekel (1984 ); Upadlgaya & Srivastava (1982 ); Wegner et al. (1986 ); Krishnamurthy et al. (1999 ). For related structures, see: Khawar Rauf et al. (2006a ,b ,c , 2007 ). For standard bond-length data, see: Allen (2002 ).

Experimental

Crystal data

C₁₄H₉Cl₃N₂OS
M_r = 359.65
Triclinic, $[P \overline 1]$
a = 5.9674 (6) Å
b = 9.6577 (9) Å
c = 13.9585 (13) Å
α = 92.919 (6)°
β = 98.005 (7)°
γ = 101.330 (8)°
V = 778.54 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 173 (2) K
0.37 × 0.34 × 0.33 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.776, T_max = 0.797
10758 measured reflections
3418 independent reflections
3154 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.02
3418 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.84 (2)	2.71 (2)	3.4273 (12)	144.3 (16)
N2—H2⋯O1	0.81 (2)	2.06 (2)	2.7098 (16)	136.4 (19)
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900004X/rk2121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900004X/rk2121Isup2.hkl

checkCIF report

Comment top

N-substituted and N,N'-disubstituted thiourea derivatives are very useful starting materials for the synthesis of a wide range of aliphatic macromolecular and heterocyclic compounds. Benzothiazoles have been prepared from arylthioureas in the presence of bromine (Patil & Chedekel, 1984) and condensation of thiourea with α-halocarbonyl compounds form 2-aminothiazoles (Baily et al., 1996). The 2-methyl-aminothiazolines have been synthesized by cyclization of N-(2-hydroxyethyl)-N'-methylthioureas (Namgun et al., 2001). Thioureas are efficient guanylating agents (Maryanoff et al., 1986). The N,N-dialkyl-N-aroylthioureas have been effectively used for the extraction of Ni, Pd and Pt metals (Koch, 2001). Aliphatic and acylthioureas are well known for their fungicidal, antiviral, pesticidal and plant-growth regulating activities (Upadlgaya & Srivastava, 1982; Wegner et al., 1986). Symmetrical and unsymmetrical thioureas have shown antifungal activity against the plant pathogens Pyricularia oryzae and Drechslera oryzae (Krishnamurthy et al., 1999). We are interested in the synthesis of these thioureas as intermediates in the synthesis of novel guanidines and heterocyclic compounds for the systematic study of bioactivity and complexation behaviour and we present here the crystal structure of the title compound. The title compound (Fig. 1) shows the typical thiourea C═S and C═O double bonds as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar, as reflected by the torsion angles C2—N1—C1—O1 = 9.0 (2)° and N2—C2—N1—C1 = 5.5 (2)°. This is associated with the expected typical thiourea intramolecular N—H···O hydrogen bond (Table). The dihedral angle formed by the two benzene ring planes is 9.35 (9)°. Bond lengths and angles can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database ver. 5.28 (Allen, 2002) and Khawar Rauf et al., 2006a,b,c, 2007. Intermolecular N—H···S hydrogen bonds (Table, Fig. 2), link the molecules to dimers. The Cl atoms are not involved in any type of hydrogen bonds.

Related literature top

For thiourea derivatives with biological activities, see: Baily et al. (1996); Koch (2001); Maryanoff et al. (1986); Namgun et al. (2001); Patil & Chedekel (1984); Upadlgaya & Srivastava (1982); Wegner et al. (1986); Krishnamurthy et al. (1999). For related structures, see: Khawar Rauf et al. (2006a,b,c, 2007). For standard bond-length data, see: Allen (2002).

Experimental top

Freshly prepared 2,4-dichlorobenzoyl isothiocyanate (2.3 g, 10 mmol) was stirred in acetone (40 ml) for 20 min. Neat 4-chloroaniline (1.3 g, 10 mmol) was then added and the resulting mixture was stirred for 1.5 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol–1,1-dichloromethane (1:10 v/v) to give fine crystals of title compound, with an overall yield of 90%. Full spectroscopic and physical characterization will be reported elsewhere.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as a small spheres of arbitrary radius.
	Fig. 2. Packing diagram of the title compound with view onto the bc plane. Hydrogen bonds are shown as dashed lines.

1-(4-Chlorophenyl)-3-(2,4-dichlorobenzoyl)thiourea top

Crystal data top

C₁₄H₉Cl₃N₂OS	Z = 2
M_r = 359.65	F(000) = 364
Triclinic, P1	D_x = 1.534 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9674 (6) Å	Cell parameters from 8758 reflections
b = 9.6577 (9) Å	θ = 3.7–27.1°
c = 13.9585 (13) Å	µ = 0.72 mm⁻¹
α = 92.919 (6)°	T = 173 K
β = 98.005 (7)°	Block, colourless
γ = 101.330 (8)°	0.37 × 0.34 × 0.33 mm
V = 778.54 (13) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	3418 independent reflections
Radiation source: fine-focus sealed tube	3154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.1°, θ_min = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −7→7
T_min = 0.776, T_max = 0.797	k = −12→12
10758 measured reflections	l = −16→17

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0411P)² + 0.3093P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3418 reflections	Δρ_max = 0.35 e Å⁻³
199 parameters	Δρ_min = −0.30 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: 0.032 (3)

Crystal data top

C₁₄H₉Cl₃N₂OS	γ = 101.330 (8)°
M_r = 359.65	V = 778.54 (13) Å³
Triclinic, P1	Z = 2
a = 5.9674 (6) Å	Mo Kα radiation
b = 9.6577 (9) Å	µ = 0.72 mm⁻¹
c = 13.9585 (13) Å	T = 173 K
α = 92.919 (6)°	0.37 × 0.34 × 0.33 mm
β = 98.005 (7)°

Data collection top

Stoe IPDS II two-circle diffractometer	3418 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3154 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.797	R_int = 0.037
10758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.35 e Å⁻³
3418 reflections	Δρ_min = −0.30 e Å⁻³
199 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > σ(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
S1	0.67492 (6)	0.98619 (3)	0.38939 (2)	0.02427 (11)
Cl1	1.21954 (7)	0.58845 (5)	0.63698 (3)	0.03934 (12)
Cl2	1.28238 (9)	0.84274 (6)	0.99473 (3)	0.05304 (15)
Cl3	−0.25621 (7)	0.63336 (6)	0.06553 (3)	0.04618 (14)
O1	0.69489 (18)	0.58953 (10)	0.55419 (8)	0.0271 (2)
N1	0.7744 (2)	0.82647 (12)	0.53113 (8)	0.0217 (2)
H1	0.870 (3)	0.901 (2)	0.5518 (14)	0.031 (5)*
N2	0.48353 (19)	0.71427 (12)	0.40789 (8)	0.0214 (2)
H2	0.488 (3)	0.644 (2)	0.4369 (15)	0.036 (5)*
C1	0.7879 (2)	0.71114 (13)	0.58426 (10)	0.0198 (2)
C2	0.6359 (2)	0.83297 (13)	0.44250 (9)	0.0194 (2)
C11	0.9208 (2)	0.74977 (13)	0.68462 (10)	0.0211 (3)
C12	1.1140 (2)	0.69336 (14)	0.71709 (11)	0.0253 (3)
C13	1.2283 (3)	0.72390 (16)	0.81191 (11)	0.0319 (3)
H13	1.3614	0.6870	0.8331	0.038*
C14	1.1437 (3)	0.80951 (17)	0.87478 (11)	0.0332 (3)
C15	0.9539 (3)	0.86812 (18)	0.84524 (12)	0.0357 (3)
H15	0.8995	0.9269	0.8895	0.043*
C16	0.8441 (3)	0.83931 (16)	0.74932 (11)	0.0294 (3)
H16	0.7162	0.8808	0.7277	0.035*
C21	0.3125 (2)	0.70259 (13)	0.32315 (9)	0.0202 (3)
C22	0.1340 (2)	0.77684 (15)	0.32197 (11)	0.0266 (3)
H22	0.1311	0.8405	0.3757	0.032*
C23	−0.0402 (2)	0.75754 (16)	0.24188 (11)	0.0290 (3)
H23	−0.1616	0.8083	0.2401	0.035*
C24	−0.0327 (2)	0.66248 (16)	0.16468 (10)	0.0274 (3)
C25	0.1444 (3)	0.58874 (16)	0.16452 (10)	0.0288 (3)
H25	0.1471	0.5253	0.1106	0.035*
C26	0.3185 (2)	0.60921 (14)	0.24475 (10)	0.0246 (3)
H26	0.4411	0.5594	0.2459	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02479 (18)	0.01930 (16)	0.02596 (18)	−0.00011 (12)	−0.00124 (13)	0.00791 (12)
Cl1	0.0333 (2)	0.0460 (2)	0.0449 (2)	0.02251 (17)	0.00655 (16)	0.00362 (17)
Cl2	0.0557 (3)	0.0652 (3)	0.0274 (2)	−0.0014 (2)	−0.01264 (18)	0.00720 (19)
Cl3	0.0303 (2)	0.0761 (3)	0.0284 (2)	0.01286 (19)	−0.00926 (15)	−0.00085 (19)
O1	0.0275 (5)	0.0176 (4)	0.0327 (5)	0.0013 (4)	−0.0038 (4)	0.0041 (4)
N1	0.0221 (5)	0.0163 (5)	0.0228 (6)	−0.0012 (4)	−0.0029 (4)	0.0031 (4)
N2	0.0222 (5)	0.0169 (5)	0.0227 (5)	0.0015 (4)	−0.0022 (4)	0.0040 (4)
C1	0.0160 (6)	0.0204 (6)	0.0232 (6)	0.0038 (4)	0.0026 (5)	0.0045 (5)
C2	0.0186 (6)	0.0194 (6)	0.0199 (6)	0.0037 (4)	0.0015 (5)	0.0021 (4)
C11	0.0196 (6)	0.0194 (6)	0.0231 (6)	0.0015 (4)	0.0014 (5)	0.0058 (5)
C12	0.0209 (6)	0.0251 (6)	0.0299 (7)	0.0046 (5)	0.0026 (5)	0.0080 (5)
C13	0.0233 (7)	0.0353 (8)	0.0351 (8)	0.0031 (6)	−0.0031 (6)	0.0145 (6)
C14	0.0335 (8)	0.0365 (8)	0.0232 (7)	−0.0036 (6)	−0.0039 (6)	0.0085 (6)
C15	0.0420 (9)	0.0382 (8)	0.0263 (7)	0.0090 (7)	0.0032 (6)	0.0003 (6)
C16	0.0299 (7)	0.0315 (7)	0.0277 (7)	0.0105 (6)	0.0013 (6)	0.0028 (6)
C21	0.0189 (6)	0.0185 (6)	0.0209 (6)	0.0002 (4)	−0.0002 (5)	0.0045 (5)
C22	0.0251 (7)	0.0249 (6)	0.0289 (7)	0.0066 (5)	0.0006 (5)	−0.0020 (5)
C23	0.0217 (6)	0.0325 (7)	0.0330 (7)	0.0092 (5)	−0.0001 (6)	0.0028 (6)
C24	0.0216 (6)	0.0364 (7)	0.0217 (6)	0.0025 (5)	−0.0014 (5)	0.0051 (5)
C25	0.0298 (7)	0.0346 (7)	0.0211 (6)	0.0066 (6)	0.0022 (5)	−0.0014 (5)
C26	0.0232 (6)	0.0265 (6)	0.0246 (7)	0.0073 (5)	0.0020 (5)	0.0029 (5)

Geometric parameters (Å, º) top

S1—C2	1.6786 (13)	C13—H13	0.9500
Cl1—C12	1.7336 (15)	C14—C15	1.385 (2)
Cl2—C14	1.7454 (16)	C15—C16	1.395 (2)
Cl3—C24	1.7529 (14)	C15—H15	0.9500
O1—C1	1.2217 (16)	C16—H16	0.9500
N1—C1	1.3784 (16)	C21—C26	1.3912 (19)
N1—C2	1.4003 (17)	C21—C22	1.3947 (19)
N1—H1	0.84 (2)	C22—C23	1.394 (2)
N2—C2	1.3365 (17)	C22—H22	0.9500
N2—C21	1.4348 (16)	C23—C24	1.391 (2)
N2—H2	0.81 (2)	C23—H23	0.9500
C1—C11	1.5004 (18)	C24—C25	1.385 (2)
C11—C12	1.3993 (19)	C25—C26	1.395 (2)
C11—C16	1.401 (2)	C25—H25	0.9500
C12—C13	1.391 (2)	C26—H26	0.9500
C13—C14	1.387 (2)

C1—N1—C2	128.79 (11)	C14—C15—C16	118.83 (15)
C1—N1—H1	115.9 (13)	C14—C15—H15	120.6
C2—N1—H1	115.1 (13)	C16—C15—H15	120.6
C2—N2—C21	124.59 (11)	C15—C16—C11	120.59 (14)
C2—N2—H2	117.6 (14)	C15—C16—H16	119.7
C21—N2—H2	117.8 (14)	C11—C16—H16	119.7
O1—C1—N1	123.60 (12)	C26—C21—C22	120.47 (12)
O1—C1—C11	122.92 (12)	C26—C21—N2	119.04 (12)
N1—C1—C11	113.44 (11)	C22—C21—N2	120.35 (12)
N2—C2—N1	115.97 (11)	C23—C22—C21	119.97 (13)
N2—C2—S1	125.98 (10)	C23—C22—H22	120.0
N1—C2—S1	118.06 (9)	C21—C22—H22	120.0
C12—C11—C16	118.82 (13)	C24—C23—C22	118.73 (13)
C12—C11—C1	121.64 (12)	C24—C23—H23	120.6
C16—C11—C1	119.48 (12)	C22—C23—H23	120.6
C13—C12—C11	121.15 (14)	C25—C24—C23	121.94 (13)
C13—C12—Cl1	119.15 (11)	C25—C24—Cl3	119.11 (11)
C11—C12—Cl1	119.66 (11)	C23—C24—Cl3	118.95 (11)
C14—C13—C12	118.49 (14)	C24—C25—C26	118.95 (13)
C14—C13—H13	120.8	C24—C25—H25	120.5
C12—C13—H13	120.8	C26—C25—H25	120.5
C15—C14—C13	122.07 (14)	C21—C26—C25	119.93 (13)
C15—C14—Cl2	119.67 (13)	C21—C26—H26	120.0
C13—C14—Cl2	118.26 (12)	C25—C26—H26	120.0

C2—N1—C1—O1	9.0 (2)	C13—C14—C15—C16	0.3 (2)
C2—N1—C1—C11	−168.72 (12)	Cl2—C14—C15—C16	−179.43 (12)
C21—N2—C2—N1	174.17 (12)	C14—C15—C16—C11	1.6 (2)
C21—N2—C2—S1	−6.02 (19)	C12—C11—C16—C15	−2.0 (2)
C1—N1—C2—N2	5.5 (2)	C1—C11—C16—C15	175.05 (13)
C1—N1—C2—S1	−174.29 (11)	C2—N2—C21—C26	118.68 (15)
O1—C1—C11—C12	59.43 (18)	C2—N2—C21—C22	−65.50 (18)
N1—C1—C11—C12	−122.82 (13)	C26—C21—C22—C23	0.1 (2)
O1—C1—C11—C16	−117.54 (15)	N2—C21—C22—C23	−175.68 (13)
N1—C1—C11—C16	60.22 (16)	C21—C22—C23—C24	0.7 (2)
C16—C11—C12—C13	0.5 (2)	C22—C23—C24—C25	−1.1 (2)
C1—C11—C12—C13	−176.50 (12)	C22—C23—C24—Cl3	177.91 (11)
C16—C11—C12—Cl1	−177.26 (11)	C23—C24—C25—C26	0.8 (2)
C1—C11—C12—Cl1	5.75 (17)	Cl3—C24—C25—C26	−178.21 (11)
C11—C12—C13—C14	1.4 (2)	C22—C21—C26—C25	−0.4 (2)
Cl1—C12—C13—C14	179.14 (11)	N2—C21—C26—C25	175.42 (12)
C12—C13—C14—C15	−1.8 (2)	C24—C25—C26—C21	−0.1 (2)
C12—C13—C14—Cl2	177.96 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.84 (2)	2.71 (2)	3.4273 (12)	144.3 (16)
N2—H2···O1	0.81 (2)	2.06 (2)	2.7098 (16)	136.4 (19)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Cl₃N₂OS
M_r	359.65
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.9674 (6), 9.6577 (9), 13.9585 (13)
α, β, γ (°)	92.919 (6), 98.005 (7), 101.330 (8)
V (Å³)	778.54 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.37 × 0.34 × 0.33

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.776, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	10758, 3418, 3154
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.02
No. of reflections	3418
No. of parameters	199
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.84 (2)	2.71 (2)	3.4273 (12)	144.3 (16)
N2—H2···O1	0.81 (2)	2.06 (2)	2.7098 (16)	136.4 (19)

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

MKR is grateful to the HEC, Pakistan, for financial support for a PhD programme under scholarship No. ILC-0363104.

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