2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thia­zole

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

doi:10.1107/S2414314619002402

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190240

https://doi.org/10.1107/S2414314619002402

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2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thiazole

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Emad Yousif,^d Mohammad Hayal Alotaibi,^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, ^dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad, 64021, Iraq, ^eNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, 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 13 February 2019; accepted 15 February 2019; online 22 February 2019)

The title compound, C₂₈H₂₃FN₆S, comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings, with twist angles between neighbouring rings pairs A/B, B/C, C/D, D/E and D/F of 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. A short intramolecular C—H⋯N contact and a weak intermolecular C—H⋯π interaction occur. The crystal chosen for data collection was found to be an inversion twin.

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

CCDC reference: 1897508

Structure description

Triazoles act as antifungal drugs and plant protection fungicides (Bonandi et al., 2017 ). Thiazoles and pyrazoles are an essential core scaffold in many natural products and have various biological activities (Chhabria et al., 2016 ; Faria et al., 2017 ). As part of our studies in these areas, we now describe the synthesis and structure of the title compound.

The molecule of the title compound comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings (Fig. 1). The twist angles between the planes through neighbouring ring pairs A/B, B/C, C/D, D/E and D/F are 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. The packing is shown in Fig. 2. A short intramolecular C—H⋯N contact and a weak intermolecular C—H⋯π interaction occur (Table 1); the latter involves the phenyl ring bonded to the triazole ring as donor and the tolyl ring as acceptor.

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯N4	0.96	2.49	3.135 (5)	125
C2—H2⋯Cg6ⁱ	0.93	2.93	3.451 (5)	117
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

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

Figure 2
The crystal structure viewed down the a-axis direction.

Synthesis and crystallization

The title compound was synthesized from condensation of 5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.63 g, 2.0 mmol) with 2-bromo-1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethanone (0.56 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The crude product was recrystallized from dimethylformamide solution to give colourless crystals (74%), m.p. 241–242°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal studied was refined as a two-component inversion twin.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₃FN₆S
M_r	494.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	6.4930 (7), 13.8065 (10), 27.539 (2)
V (Å³)	2468.7 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.48 × 0.22 × 0.20

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	0.989, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	10497, 5824, 3616
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.130, 1.02
No. of reflections	5824
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.39 (13)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1897508

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002402/hb4287sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002402/hb4287Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002402/hb4287Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); 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).

2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thiazole top

Crystal data top

C₂₈H₂₃FN₆S	D_x = 1.331 Mg m⁻³
M_r = 494.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2536 reflections
a = 6.4930 (7) Å	θ = 4.5–24.6°
b = 13.8065 (10) Å	µ = 0.17 mm⁻¹
c = 27.539 (2) Å	T = 298 K
V = 2468.7 (4) Å³	Block, colourless
Z = 4	0.48 × 0.22 × 0.20 mm
F(000) = 1032

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	3616 reflections with I > 2σ(I)
ω scans	R_int = 0.030
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.9°, θ_min = 3.5°
T_min = 0.989, T_max = 0.995	h = −8→6
10497 measured reflections	k = −18→18
5824 independent reflections	l = −37→37

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0443P)² + 0.4094P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.19 e Å⁻³
5824 reflections	Δρ_min = −0.16 e Å⁻³
328 parameters	Absolute structure: Refined as an inversion twin.
0 restraints	Absolute structure parameter: 0.39 (13)
Primary atom site location: structure-invariant direct methods

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. Refined as a twocomponent inversion twin. All hydrogen atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined using a riding model. Their U_iso values were set to 1.2U_eq(C) or 1.5U_eq(methyl C).

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

	x	y	z	U_iso*/U_eq
C1	−0.4269 (7)	1.1919 (3)	1.07159 (13)	0.0559 (10)
C2	−0.6229 (7)	1.1827 (3)	1.08958 (15)	0.0649 (11)
H2	−0.678909	1.121876	1.095562	0.078*
C3	−0.7347 (7)	1.2650 (3)	1.09859 (16)	0.0717 (12)
H3	−0.867316	1.260334	1.111120	0.086*
C4	−0.6503 (9)	1.3551 (3)	1.08904 (16)	0.0739 (13)
H4	−0.725943	1.410783	1.095705	0.089*
C5	−0.4596 (9)	1.3629 (3)	1.07019 (19)	0.0849 (15)
H5	−0.404979	1.423607	1.063286	0.102*
C6	−0.3460 (8)	1.2808 (3)	1.06117 (18)	0.0797 (13)
H6	−0.214461	1.285781	1.048022	0.096*
C7	−0.3245 (6)	1.0401 (2)	1.02673 (13)	0.0511 (9)
C8	−0.5093 (7)	1.0342 (3)	0.99548 (16)	0.0691 (12)
H8A	−0.513388	1.089265	0.974237	0.104*
H8B	−0.630595	1.033504	1.015412	0.104*
H8C	−0.503877	0.975897	0.976504	0.104*
C9	−0.1463 (6)	0.9874 (2)	1.02874 (13)	0.0516 (9)
C10	−0.0736 (6)	0.9082 (3)	0.99844 (14)	0.0511 (9)
C11	0.0948 (7)	0.8538 (3)	1.00637 (14)	0.0574 (10)
H11	0.182880	0.861305	1.032728	0.069*
C12	−0.0915 (6)	0.8150 (3)	0.93398 (14)	0.0544 (10)
C13	−0.3802 (7)	0.7884 (2)	0.87594 (14)	0.0567 (10)
H13	−0.469753	0.783243	0.904477	0.068*
C14	−0.4096 (7)	0.6982 (3)	0.84381 (16)	0.0690 (12)
H14A	−0.524532	0.659290	0.855039	0.083*
H14B	−0.432842	0.716223	0.810208	0.083*
C15	−0.2083 (7)	0.6445 (3)	0.84956 (15)	0.0583 (11)
C16	−0.4171 (7)	0.8849 (3)	0.85139 (13)	0.0568 (10)
C17	−0.6006 (8)	0.9330 (3)	0.85763 (17)	0.0816 (14)
H17	−0.701415	0.905584	0.877291	0.098*
C18	−0.6390 (10)	1.0206 (4)	0.8355 (2)	0.0978 (18)
H18	−0.763844	1.052494	0.839867	0.117*
C19	−0.4880 (11)	1.0591 (3)	0.80716 (18)	0.0818 (16)
C20	−0.3074 (10)	1.0152 (3)	0.79966 (17)	0.0804 (15)
H20	−0.208150	1.043064	0.779691	0.097*
C21	−0.2713 (8)	0.9269 (3)	0.82245 (16)	0.0694 (12)
H21	−0.145671	0.895904	0.817918	0.083*
C22	−0.1595 (8)	0.5513 (3)	0.82755 (15)	0.0618 (11)
C23	0.0365 (8)	0.5127 (3)	0.83004 (18)	0.0740 (13)
H23	0.140588	0.547775	0.845171	0.089*
C24	0.0807 (9)	0.4226 (3)	0.81034 (19)	0.0843 (16)
H24	0.213884	0.398120	0.812360	0.101*
C25	−0.0720 (10)	0.3686 (3)	0.78763 (17)	0.0782 (15)
C26	−0.2671 (9)	0.4073 (3)	0.78493 (17)	0.0820 (15)
H26	−0.371342	0.372581	0.769661	0.098*
C27	−0.3102 (9)	0.4974 (3)	0.80466 (16)	0.0767 (14)
H27	−0.443203	0.521997	0.802457	0.092*
C28	−0.0244 (10)	0.2676 (4)	0.7685 (2)	0.111 (2)
H28A	−0.112090	0.253675	0.741325	0.166*
H28B	−0.048207	0.220881	0.793703	0.166*
H28C	0.116980	0.264634	0.758453	0.166*
N1	−0.3011 (5)	1.1082 (2)	1.06182 (12)	0.0562 (8)
N2	−0.1185 (6)	1.0982 (3)	1.08453 (13)	0.0734 (10)
N3	−0.0244 (6)	1.0233 (3)	1.06502 (14)	0.0708 (10)
N4	−0.1820 (5)	0.8870 (2)	0.95596 (11)	0.0517 (8)
N5	−0.1641 (5)	0.7772 (2)	0.89122 (12)	0.0595 (8)
N6	−0.0774 (6)	0.6892 (2)	0.87665 (12)	0.0603 (9)
F1	−0.5241 (6)	1.1462 (2)	0.78531 (12)	0.1226 (13)
S1	0.12603 (17)	0.76837 (7)	0.96140 (4)	0.0631 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.058 (2)	0.056 (2)	0.002 (2)	−0.0014 (19)	−0.0004 (19)
C2	0.055 (3)	0.065 (2)	0.075 (2)	−0.004 (2)	0.000 (2)	0.002 (2)
C3	0.056 (3)	0.082 (3)	0.077 (3)	0.008 (3)	0.005 (2)	−0.008 (3)
C4	0.086 (4)	0.062 (3)	0.074 (3)	0.012 (3)	−0.005 (3)	−0.008 (2)
C5	0.090 (4)	0.058 (3)	0.107 (4)	−0.001 (3)	0.010 (3)	0.006 (3)
C6	0.072 (3)	0.064 (2)	0.103 (3)	−0.006 (3)	0.017 (3)	0.006 (3)
C7	0.045 (2)	0.0479 (18)	0.060 (2)	−0.0055 (18)	−0.0047 (19)	0.0081 (17)
C8	0.056 (3)	0.075 (3)	0.077 (3)	0.006 (2)	−0.013 (2)	−0.012 (2)
C9	0.043 (2)	0.0507 (18)	0.061 (2)	−0.0044 (19)	−0.007 (2)	0.0067 (17)
C10	0.041 (2)	0.0488 (18)	0.064 (2)	−0.0031 (18)	−0.0037 (19)	0.0109 (18)
C11	0.053 (3)	0.057 (2)	0.062 (2)	0.002 (2)	−0.004 (2)	0.0069 (18)
C12	0.046 (2)	0.0502 (19)	0.067 (2)	0.0020 (19)	0.002 (2)	0.0155 (19)
C13	0.049 (2)	0.057 (2)	0.064 (2)	0.009 (2)	−0.004 (2)	0.0047 (18)
C14	0.065 (3)	0.054 (2)	0.088 (3)	0.002 (2)	−0.007 (3)	−0.002 (2)
C15	0.063 (3)	0.049 (2)	0.062 (2)	0.000 (2)	0.006 (2)	0.0085 (19)
C16	0.065 (3)	0.053 (2)	0.052 (2)	0.005 (2)	−0.003 (2)	−0.0015 (18)
C17	0.077 (4)	0.087 (3)	0.081 (3)	0.026 (3)	0.010 (3)	0.020 (3)
C18	0.105 (5)	0.093 (4)	0.096 (4)	0.039 (4)	0.001 (4)	0.016 (3)
C19	0.124 (5)	0.057 (3)	0.065 (3)	0.014 (3)	−0.019 (3)	0.003 (2)
C20	0.109 (5)	0.061 (3)	0.071 (3)	−0.006 (3)	0.002 (3)	0.004 (2)
C21	0.072 (3)	0.059 (2)	0.077 (3)	0.003 (2)	0.004 (3)	0.001 (2)
C22	0.070 (3)	0.050 (2)	0.065 (2)	0.005 (2)	0.006 (2)	0.0065 (19)
C23	0.074 (4)	0.061 (3)	0.088 (3)	−0.003 (2)	0.016 (3)	−0.006 (2)
C24	0.079 (4)	0.068 (3)	0.106 (4)	0.010 (3)	0.032 (3)	0.002 (3)
C25	0.099 (4)	0.059 (3)	0.077 (3)	−0.001 (3)	0.023 (3)	0.000 (2)
C26	0.097 (4)	0.068 (3)	0.081 (3)	0.000 (3)	−0.009 (3)	−0.005 (3)
C27	0.087 (4)	0.066 (3)	0.077 (3)	0.009 (3)	−0.008 (3)	−0.006 (2)
C28	0.150 (6)	0.062 (3)	0.120 (4)	−0.002 (3)	0.042 (4)	−0.017 (3)
N1	0.048 (2)	0.0557 (17)	0.0654 (18)	−0.0025 (16)	−0.0046 (17)	−0.0033 (17)
N2	0.056 (2)	0.083 (2)	0.081 (2)	0.006 (2)	−0.019 (2)	−0.016 (2)
N3	0.056 (2)	0.074 (2)	0.082 (2)	0.0069 (19)	−0.019 (2)	−0.009 (2)
N4	0.0483 (19)	0.0456 (15)	0.0613 (18)	0.0026 (15)	−0.0022 (16)	0.0077 (15)
N5	0.056 (2)	0.0556 (17)	0.0673 (19)	0.0098 (17)	−0.0044 (17)	−0.0025 (16)
N6	0.062 (2)	0.0547 (17)	0.0644 (19)	0.0076 (18)	0.0068 (18)	0.0029 (17)
F1	0.179 (4)	0.0690 (17)	0.120 (2)	0.023 (2)	−0.030 (2)	0.0235 (17)
S1	0.0522 (6)	0.0618 (5)	0.0754 (6)	0.0127 (5)	−0.0014 (6)	0.0094 (5)

Geometric parameters (Å, º) top

C1—C6	1.366 (5)	C14—H14A	0.9700
C1—C2	1.372 (6)	C14—H14B	0.9700
C1—N1	1.440 (5)	C15—N6	1.288 (5)
C2—C3	1.371 (6)	C15—C22	1.458 (5)
C2—H2	0.9300	C16—C21	1.367 (6)
C3—C4	1.385 (6)	C16—C17	1.374 (6)
C3—H3	0.9300	C17—C18	1.378 (6)
C4—C5	1.347 (7)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.361 (8)
C5—C6	1.375 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.336 (8)
C6—H6	0.9300	C19—F1	1.366 (5)
C7—N1	1.357 (4)	C20—C21	1.391 (6)
C7—C9	1.368 (5)	C20—H20	0.9300
C7—C8	1.479 (6)	C21—H21	0.9300
C8—H8A	0.9600	C22—C23	1.381 (6)
C8—H8B	0.9600	C22—C27	1.381 (6)
C8—H8C	0.9600	C23—C24	1.387 (6)
C9—N3	1.368 (5)	C23—H23	0.9300
C9—C10	1.454 (5)	C24—C25	1.389 (7)
C10—C11	1.344 (5)	C24—H24	0.9300
C10—N4	1.396 (5)	C25—C26	1.377 (7)
C11—S1	1.722 (4)	C25—C28	1.522 (6)
C11—H11	0.9300	C26—C27	1.385 (6)
C12—N4	1.304 (5)	C26—H26	0.9300
C12—N5	1.371 (5)	C27—H27	0.9300
C12—S1	1.726 (4)	C28—H28A	0.9600
C13—N5	1.473 (5)	C28—H28B	0.9600
C13—C16	1.513 (5)	C28—H28C	0.9600
C13—C14	1.540 (5)	N1—N2	1.348 (5)
C13—H13	0.9800	N2—N3	1.315 (5)
C14—C15	1.511 (6)	N5—N6	1.398 (4)

C6—C1—C2	121.1 (4)	C21—C16—C17	117.9 (4)
C6—C1—N1	117.6 (4)	C21—C16—C13	121.7 (4)
C2—C1—N1	121.3 (4)	C17—C16—C13	120.4 (4)
C3—C2—C1	118.7 (4)	C16—C17—C18	121.7 (5)
C3—C2—H2	120.7	C16—C17—H17	119.1
C1—C2—H2	120.7	C18—C17—H17	119.1
C2—C3—C4	120.1 (4)	C19—C18—C17	117.8 (5)
C2—C3—H3	120.0	C19—C18—H18	121.1
C4—C3—H3	120.0	C17—C18—H18	121.1
C5—C4—C3	120.5 (4)	C20—C19—C18	123.0 (5)
C5—C4—H4	119.7	C20—C19—F1	118.8 (6)
C3—C4—H4	119.7	C18—C19—F1	118.2 (6)
C4—C5—C6	119.8 (5)	C19—C20—C21	118.3 (5)
C4—C5—H5	120.1	C19—C20—H20	120.8
C6—C5—H5	120.1	C21—C20—H20	120.8
C1—C6—C5	119.8 (5)	C16—C21—C20	121.3 (5)
C1—C6—H6	120.1	C16—C21—H21	119.4
C5—C6—H6	120.1	C20—C21—H21	119.4
N1—C7—C9	104.2 (3)	C23—C22—C27	117.9 (4)
N1—C7—C8	122.9 (4)	C23—C22—C15	121.3 (4)
C9—C7—C8	132.9 (4)	C27—C22—C15	120.8 (4)
C7—C8—H8A	109.5	C22—C23—C24	121.1 (5)
C7—C8—H8B	109.5	C22—C23—H23	119.4
H8A—C8—H8B	109.5	C24—C23—H23	119.4
C7—C8—H8C	109.5	C23—C24—C25	120.6 (5)
H8A—C8—H8C	109.5	C23—C24—H24	119.7
H8B—C8—H8C	109.5	C25—C24—H24	119.7
N3—C9—C7	109.1 (3)	C26—C25—C24	118.2 (4)
N3—C9—C10	120.2 (4)	C26—C25—C28	121.6 (5)
C7—C9—C10	130.6 (4)	C24—C25—C28	120.2 (6)
C11—C10—N4	115.4 (3)	C25—C26—C27	120.9 (5)
C11—C10—C9	126.2 (4)	C25—C26—H26	119.6
N4—C10—C9	118.4 (3)	C27—C26—H26	119.6
C10—C11—S1	111.2 (3)	C22—C27—C26	121.3 (5)
C10—C11—H11	124.4	C22—C27—H27	119.4
S1—C11—H11	124.4	C26—C27—H27	119.4
N4—C12—N5	122.3 (4)	C25—C28—H28A	109.5
N4—C12—S1	116.7 (3)	C25—C28—H28B	109.5
N5—C12—S1	121.0 (3)	H28A—C28—H28B	109.5
N5—C13—C16	111.8 (3)	C25—C28—H28C	109.5
N5—C13—C14	101.4 (3)	H28A—C28—H28C	109.5
C16—C13—C14	115.8 (3)	H28B—C28—H28C	109.5
N5—C13—H13	109.2	N2—N1—C7	110.9 (3)
C16—C13—H13	109.2	N2—N1—C1	119.7 (3)
C14—C13—H13	109.2	C7—N1—C1	128.7 (3)
C15—C14—C13	103.3 (4)	N3—N2—N1	107.5 (3)
C15—C14—H14A	111.1	N2—N3—C9	108.3 (3)
C13—C14—H14A	111.1	C12—N4—C10	108.8 (3)
C15—C14—H14B	111.1	C12—N5—N6	116.0 (3)
C13—C14—H14B	111.1	C12—N5—C13	122.2 (3)
H14A—C14—H14B	109.1	N6—N5—C13	113.1 (3)
N6—C15—C22	121.4 (4)	C15—N6—N5	108.5 (3)
N6—C15—C14	113.4 (3)	C11—S1—C12	87.9 (2)
C22—C15—C14	125.3 (4)

Hydrogen-bond geometry (Å, º) top

Cg6 is the centroid of the C22–C27 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···N4	0.96	2.49	3.135 (5)	125
C2—H2···Cg6ⁱ	0.93	2.93	3.451 (5)	117

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

Footnotes

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

Funding information

MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia for financial support (award No. 020–0180).

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