Ethyl 2-anilino-4-methyl-5-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazole-4-carbon­yl]­thio­phene-3-carboxyl­ate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Yousif, E.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618011069

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 8| August 2018| x181106

https://doi.org/10.1107/S2414314618011069

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Ethyl 2-anilino-4-methyl-5-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]thiophene-3-carboxylate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Emad Yousif,^e Amany S. Hegazy ^f and Benson M. Kariuki ^f ‡

^aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dCenter of Excellence in Integrated Nano-Systems, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, ^eDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, and ^fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 August 2018; accepted 2 August 2018; online 10 August 2018)

The conformation of the title compound, C₂₅H₂₄N₄O₃S, is influenced by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring. The twist angles between the planes through the toluyl, methyltriazole, thiophene and phenyl rings are 60.1 (1), 33.5 (1) and 39.9 (1)°, respectively. In the crystal, molecules are stacked along the a-axis direction with weak aromatic π–π stacking interactions occurring between the thiophene rings [centroid-to-centroid distance = 3.7285 (15) Å].

Keywords: crystal structure; 1,2,3-triazole; thiophene.

CCDC reference: 1859955

Structure description

Substituted 2-aminothiophenes are found in numerous biologically active compounds including olanzapine as an antipsychotic drug and tinoridine as a potent nonsteroidal anti-inflammatory drug (Al-Taisan et al., 2010 ; Huang & Dömling, 2011 ; Wardakhan et al., 2016 ). As part of our studies of similar systems, we now describe the structure of the title compound.

The asymmetric unit comprises one molecule of C₂₅H₂₄N₄O₃S (Fig. 1). An intramolecular N—H⋯O hydrogen bond occurs in the molecule (Table 1) and the twist angles between the planes through the toluyl, methyltriazole, thiophene and phenyl rings are 60.1 (1)°, 33.5 (1)° and 39.9 (1)° respectively. In the crystal, molecules are stacked along the a-axis and π–π type interactions involving thiophene groups of neighbouring molecules with centroid-to-centroid distances of 3.7285 (15) Å are observed (Fig. 2); the pairs are related by a twofold rotation axis.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O2	0.86	2.08	2.704 (3)	129

Figure 1
The molecular structure of the title compound, showing 50% displacement ellipsoids.

Figure 2
A segment of the crystal structure showing thiophene π–π contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized by a literature procedure (Mohamed et al., 2017 ) in 78% yield and recrystallized from dimethylformamide solution as yellow plates, m.p. 472–473 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₂₄N₄O₃S
M_r	460.54
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	293
a, b, c (Å)	8.3287 (7), 13.8956 (9), 20.3124 (15)
β (°)	90.635 (8)
V (Å³)	2350.7 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.23 × 0.15 × 0.04

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.995, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	22546, 5978, 2688
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.182, 1.01
No. of reflections	5978
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1859955

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618011069/hb4250sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618011069/hb4250Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618011069/hb4250Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: SHELXS97 (Sheldrick, 2008); data reduction: SHELXL2018 (Sheldrick, 2015); program(s) used to solve structure: ORTEP-3 for Windows and WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

Ethyl 2-anilino-4-methyl-5-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]thiophene-3-carboxylate top

Crystal data top

C₂₅H₂₄N₄O₃S	F(000) = 968
M_r = 460.54	D_x = 1.301 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.3287 (7) Å	Cell parameters from 3069 reflections
b = 13.8956 (9) Å	θ = 3.9–24.4°
c = 20.3124 (15) Å	µ = 0.17 mm⁻¹
β = 90.635 (8)°	T = 293 K
V = 2350.7 (3) Å³	Plate, yellow
Z = 4	0.23 × 0.15 × 0.04 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	2688 reflections with I > 2σ(I)
ω scans	R_int = 0.075
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.8°, θ_min = 1.5°
T_min = 0.995, T_max = 0.999	h = −8→11
22546 measured reflections	k = −19→18
5978 independent reflections	l = −27→25

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.0677P)² + 0.1629P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5978 reflections	Δρ_max = 0.22 e Å⁻³
302 parameters	Δρ_min = −0.26 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.

Refinement. Non-hydrogen atoms were refined with anisotropic displacement parameters. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C bond. Methylene C—H bonds were fixed at 0.97 Å with displacement parameters 1.2 times U_eq(C). The N—H bond was fixed at 0.86 Å and aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the U_eq for the atoms to which they are bonded.

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

	x	y	z	U_iso*/U_eq
C1	0.2351 (6)	0.5726 (3)	−0.2019 (2)	0.1272 (19)
H1A	0.258516	0.607548	−0.241464	0.191*
H1B	0.121086	0.571410	−0.195501	0.191*
H1C	0.274461	0.507974	−0.205703	0.191*
C2	0.3162 (4)	0.6218 (3)	−0.14350 (19)	0.0806 (11)
C3	0.3240 (4)	0.5779 (3)	−0.08255 (19)	0.0773 (10)
H3	0.280124	0.516873	−0.077300	0.093*
C4	0.3951 (4)	0.6227 (2)	−0.02960 (16)	0.0682 (9)
H4	0.398191	0.592515	0.011252	0.082*
C5	0.4618 (4)	0.7124 (2)	−0.03719 (15)	0.0573 (8)
C6	0.4602 (5)	0.7578 (2)	−0.09710 (16)	0.0738 (10)
H6	0.507335	0.817946	−0.102273	0.089*
C7	0.3861 (5)	0.7112 (3)	−0.15004 (17)	0.0856 (12)
H7	0.383682	0.741238	−0.190945	0.103*
C8	0.3672 (3)	0.9046 (2)	0.02623 (15)	0.0606 (8)
H8A	0.390832	0.931514	−0.016115	0.091*
H8B	0.353249	0.955629	0.057517	0.091*
H8C	0.270483	0.867268	0.023214	0.091*
C9	0.5025 (3)	0.8417 (2)	0.04803 (14)	0.0499 (7)
C10	0.6094 (3)	0.8475 (2)	0.09995 (14)	0.0499 (7)
C11	0.6279 (3)	0.9260 (2)	0.14862 (14)	0.0523 (7)
C12	0.7123 (3)	0.90717 (19)	0.21113 (13)	0.0478 (7)
C13	0.7711 (3)	0.97434 (18)	0.25536 (13)	0.0462 (7)
C14	0.7598 (4)	1.0808 (2)	0.24459 (15)	0.0652 (9)
H14A	0.748681	1.093725	0.198343	0.098*
H14B	0.855405	1.111218	0.261266	0.098*
H14C	0.668146	1.105577	0.267262	0.098*
C15	0.8426 (3)	0.92958 (18)	0.31215 (13)	0.0452 (6)
C16	0.8296 (3)	0.8298 (2)	0.31015 (13)	0.0492 (7)
C17	0.8438 (4)	0.6707 (2)	0.36650 (14)	0.0543 (7)
C18	0.9483 (4)	0.6112 (2)	0.39992 (19)	0.0785 (10)
H18	1.046890	0.634573	0.414740	0.094*
C19	0.9063 (5)	0.5164 (3)	0.4114 (2)	0.1003 (14)
H19	0.976830	0.476175	0.434132	0.120*
C20	0.7604 (6)	0.4812 (3)	0.3894 (2)	0.0944 (12)
H20	0.733104	0.417163	0.396539	0.113*
C21	0.6571 (5)	0.5408 (3)	0.35733 (18)	0.0844 (11)
H21	0.558510	0.517401	0.342538	0.101*
C22	0.6966 (4)	0.6350 (2)	0.34652 (15)	0.0690 (9)
H22	0.623431	0.675404	0.325436	0.083*
C23	0.9240 (3)	0.9763 (2)	0.36794 (14)	0.0500 (7)
C24	0.9832 (5)	1.1200 (3)	0.42540 (19)	0.0979 (14)
H24A	0.942386	1.098416	0.467452	0.117*
H24B	1.096991	1.105427	0.423970	0.117*
C25	0.9584 (6)	1.2224 (3)	0.4184 (2)	0.1055 (15)
H25A	0.993383	1.242598	0.375645	0.158*
H25B	1.019087	1.255818	0.451680	0.158*
H25C	0.846424	1.236812	0.423043	0.158*
N1	0.5376 (3)	0.75785 (17)	0.01888 (11)	0.0533 (6)
N2	0.6622 (3)	0.71189 (17)	0.05061 (13)	0.0659 (7)
N3	0.7040 (3)	0.76756 (18)	0.09930 (13)	0.0638 (7)
N5	0.8863 (3)	0.76760 (15)	0.35745 (11)	0.0556 (6)
H5	0.956005	0.790616	0.384744	0.067*
O1	0.5702 (3)	1.00550 (14)	0.13552 (10)	0.0701 (6)
O2	1.0056 (2)	0.93309 (14)	0.40814 (10)	0.0633 (6)
O3	0.8992 (3)	1.07044 (14)	0.37197 (10)	0.0687 (6)
S1	0.74326 (9)	0.78984 (5)	0.23839 (4)	0.0566 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.128 (4)	0.167 (4)	0.085 (3)	0.025 (3)	−0.044 (3)	−0.059 (3)
C2	0.078 (2)	0.101 (3)	0.062 (2)	0.022 (2)	−0.022 (2)	−0.030 (2)
C3	0.075 (2)	0.089 (2)	0.068 (3)	−0.0077 (18)	−0.005 (2)	−0.024 (2)
C4	0.072 (2)	0.084 (2)	0.049 (2)	−0.0071 (17)	−0.0067 (17)	−0.0090 (17)
C5	0.0613 (18)	0.0681 (19)	0.0421 (18)	0.0094 (15)	−0.0116 (15)	−0.0086 (15)
C6	0.104 (3)	0.069 (2)	0.048 (2)	0.0157 (18)	−0.013 (2)	−0.0028 (16)
C7	0.119 (3)	0.094 (3)	0.043 (2)	0.038 (2)	−0.020 (2)	−0.0071 (19)
C8	0.0534 (17)	0.080 (2)	0.0483 (18)	0.0117 (15)	−0.0090 (15)	−0.0020 (15)
C9	0.0532 (16)	0.0578 (17)	0.0387 (16)	0.0019 (13)	−0.0038 (14)	0.0015 (13)
C10	0.0501 (15)	0.0605 (17)	0.0389 (16)	0.0035 (13)	−0.0093 (14)	−0.0008 (13)
C11	0.0504 (16)	0.0618 (18)	0.0446 (17)	−0.0007 (13)	−0.0066 (14)	0.0028 (14)
C12	0.0482 (15)	0.0560 (16)	0.0389 (16)	0.0013 (12)	−0.0061 (13)	0.0013 (12)
C13	0.0480 (15)	0.0530 (16)	0.0376 (16)	−0.0030 (12)	−0.0030 (13)	0.0003 (12)
C14	0.082 (2)	0.0602 (18)	0.053 (2)	0.0001 (15)	−0.0175 (18)	0.0064 (14)
C15	0.0477 (15)	0.0510 (15)	0.0368 (15)	−0.0009 (12)	−0.0062 (13)	0.0003 (12)
C16	0.0487 (15)	0.0592 (17)	0.0395 (16)	−0.0015 (13)	−0.0062 (13)	0.0043 (13)
C17	0.0642 (18)	0.0537 (16)	0.0450 (18)	−0.0015 (14)	−0.0017 (15)	0.0010 (14)
C18	0.068 (2)	0.067 (2)	0.100 (3)	0.0027 (17)	−0.006 (2)	0.018 (2)
C19	0.092 (3)	0.067 (2)	0.142 (4)	0.015 (2)	0.018 (3)	0.032 (2)
C20	0.114 (3)	0.061 (2)	0.109 (3)	−0.016 (2)	0.035 (3)	−0.006 (2)
C21	0.104 (3)	0.088 (3)	0.061 (2)	−0.035 (2)	0.004 (2)	0.0007 (19)
C22	0.076 (2)	0.082 (2)	0.049 (2)	−0.0230 (18)	−0.0065 (17)	0.0126 (16)
C23	0.0483 (15)	0.0568 (17)	0.0448 (17)	−0.0040 (13)	−0.0046 (14)	0.0015 (14)
C24	0.139 (4)	0.076 (2)	0.078 (3)	−0.012 (2)	−0.051 (3)	−0.016 (2)
C25	0.127 (4)	0.077 (3)	0.113 (4)	−0.010 (2)	−0.020 (3)	−0.027 (2)
N1	0.0560 (14)	0.0644 (15)	0.0391 (14)	0.0047 (11)	−0.0115 (12)	−0.0036 (11)
N2	0.0747 (17)	0.0699 (16)	0.0527 (16)	0.0169 (13)	−0.0218 (14)	−0.0058 (13)
N3	0.0719 (17)	0.0690 (16)	0.0500 (16)	0.0115 (13)	−0.0211 (14)	−0.0087 (13)
N5	0.0644 (15)	0.0574 (14)	0.0446 (14)	−0.0087 (11)	−0.0173 (13)	0.0073 (11)
O1	0.0911 (15)	0.0616 (13)	0.0569 (14)	0.0122 (11)	−0.0263 (12)	−0.0016 (10)
O2	0.0708 (13)	0.0723 (13)	0.0464 (12)	0.0054 (10)	−0.0191 (11)	−0.0015 (10)
O3	0.0939 (16)	0.0550 (13)	0.0565 (14)	−0.0055 (11)	−0.0290 (12)	−0.0054 (10)
S1	0.0691 (5)	0.0553 (4)	0.0451 (5)	−0.0026 (3)	−0.0158 (4)	0.0004 (3)

Geometric parameters (Å, º) top

C1—C2	1.521 (5)	C14—H14B	0.9600
C1—H1A	0.9600	C14—H14C	0.9600
C1—H1B	0.9600	C15—C16	1.391 (4)
C1—H1C	0.9600	C15—C23	1.465 (4)
C2—C7	1.379 (5)	C16—N5	1.373 (3)
C2—C3	1.381 (5)	C16—S1	1.711 (3)
C3—C4	1.372 (4)	C17—C18	1.374 (4)
C3—H3	0.9300	C17—C22	1.379 (4)
C4—C5	1.373 (4)	C17—N5	1.405 (3)
C4—H4	0.9300	C18—C19	1.383 (5)
C5—C6	1.371 (4)	C18—H18	0.9300
C5—N1	1.442 (3)	C19—C20	1.380 (5)
C6—C7	1.394 (5)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.355 (5)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.489 (4)	C21—C22	1.368 (4)
C8—H8A	0.9600	C21—H21	0.9300
C8—H8B	0.9600	C22—H22	0.9300
C8—H8C	0.9600	C23—O2	1.215 (3)
C9—N1	1.341 (3)	C23—O3	1.327 (3)
C9—C10	1.375 (3)	C24—C25	1.445 (5)
C10—N3	1.363 (3)	C24—O3	1.457 (3)
C10—C11	1.479 (4)	C24—H24A	0.9700
C11—O1	1.232 (3)	C24—H24B	0.9700
C11—C12	1.468 (4)	C25—H25A	0.9600
C12—C13	1.381 (4)	C25—H25B	0.9600
C12—S1	1.740 (3)	C25—H25C	0.9600
C13—C15	1.434 (3)	N1—N2	1.373 (3)
C13—C14	1.498 (4)	N2—N3	1.300 (3)
C14—H14A	0.9600	N5—H5	0.8600

C2—C1—H1A	109.5	H14B—C14—H14C	109.5
C2—C1—H1B	109.5	C16—C15—C13	112.1 (2)
H1A—C1—H1B	109.5	C16—C15—C23	120.0 (2)
C2—C1—H1C	109.5	C13—C15—C23	127.9 (2)
H1A—C1—H1C	109.5	N5—C16—C15	125.5 (2)
H1B—C1—H1C	109.5	N5—C16—S1	122.0 (2)
C7—C2—C3	117.9 (3)	C15—C16—S1	112.37 (19)
C7—C2—C1	120.9 (4)	C18—C17—C22	119.0 (3)
C3—C2—C1	121.2 (4)	C18—C17—N5	118.8 (3)
C4—C3—C2	121.2 (4)	C22—C17—N5	122.1 (3)
C4—C3—H3	119.4	C17—C18—C19	119.7 (3)
C2—C3—H3	119.4	C17—C18—H18	120.1
C3—C4—C5	119.7 (3)	C19—C18—H18	120.1
C3—C4—H4	120.1	C20—C19—C18	120.4 (3)
C5—C4—H4	120.1	C20—C19—H19	119.8
C6—C5—C4	121.2 (3)	C18—C19—H19	119.8
C6—C5—N1	119.9 (3)	C21—C20—C19	119.4 (4)
C4—C5—N1	118.9 (3)	C21—C20—H20	120.3
C5—C6—C7	118.1 (3)	C19—C20—H20	120.3
C5—C6—H6	121.0	C20—C21—C22	120.6 (3)
C7—C6—H6	121.0	C20—C21—H21	119.7
C2—C7—C6	121.9 (3)	C22—C21—H21	119.7
C2—C7—H7	119.1	C21—C22—C17	120.8 (3)
C6—C7—H7	119.1	C21—C22—H22	119.6
C9—C8—H8A	109.5	C17—C22—H22	119.6
C9—C8—H8B	109.5	O2—C23—O3	122.1 (2)
H8A—C8—H8B	109.5	O2—C23—C15	123.5 (3)
C9—C8—H8C	109.5	O3—C23—C15	114.4 (2)
H8A—C8—H8C	109.5	C25—C24—O3	108.9 (3)
H8B—C8—H8C	109.5	C25—C24—H24A	109.9
N1—C9—C10	104.3 (2)	O3—C24—H24A	109.9
N1—C9—C8	123.1 (2)	C25—C24—H24B	109.9
C10—C9—C8	132.5 (3)	O3—C24—H24B	109.9
N3—C10—C9	108.3 (2)	H24A—C24—H24B	108.3
N3—C10—C11	123.5 (2)	C24—C25—H25A	109.5
C9—C10—C11	128.1 (2)	C24—C25—H25B	109.5
O1—C11—C12	121.9 (3)	H25A—C25—H25B	109.5
O1—C11—C10	118.6 (2)	C24—C25—H25C	109.5
C12—C11—C10	119.4 (2)	H25A—C25—H25C	109.5
C13—C12—C11	127.2 (2)	H25B—C25—H25C	109.5
C13—C12—S1	112.07 (19)	C9—N1—N2	111.4 (2)
C11—C12—S1	120.7 (2)	C9—N1—C5	129.3 (2)
C12—C13—C15	111.8 (2)	N2—N1—C5	119.3 (2)
C12—C13—C14	123.4 (2)	N3—N2—N1	106.0 (2)
C15—C13—C14	124.8 (2)	N2—N3—C10	110.0 (2)
C13—C14—H14A	109.5	C16—N5—C17	127.6 (2)
C13—C14—H14B	109.5	C16—N5—H5	116.2
H14A—C14—H14B	109.5	C17—N5—H5	116.2
C13—C14—H14C	109.5	C23—O3—C24	116.0 (2)
H14A—C14—H14C	109.5	C16—S1—C12	91.50 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2	0.86	2.08	2.704 (3)	129

Footnotes

‡Additional coressponding author, e-mail: kariukib@cardiff.ac.uk.

Funding information

MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia for financial support (grant No. 20-0180).

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