Synthesis, crystal structure and Hirshfeld surface analysis of 3-ethyl-2-(methyl­sulfan­yl)-5,5-diphenyl-3H-imidazol-4(5H)-one (Thio­phenytoin analogue)

El Moutaouakil Ala Allah, A.; Massera, C.; Guerrab, W.; Alsubari, A.; Mague, J.T.; Ramli, Y.

doi:10.1107/S205698902500698X

research communications

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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 801-805

https://doi.org/10.1107/S205698902500698X

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Synthesis, crystal structure and Hirshfeld surface analysis of 3-ethyl-2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one (Thiophenytoin analogue)

Abderrazzak El Moutaouakil Ala Allah,^a Chiara Massera,^b Walid Guerrab,^a Abdulsalam Alsubari,^c ^* Joel T. Mague ^d and Youssef Ramli ^a ^*

^aLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco, ^bDipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A 43124 Parma, Italy, ^cLaboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21September University, Yemen, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: [email protected], [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 30 July 2025; accepted 4 August 2025; online 5 August 2025)

In the title molecule, 3-ethyl-2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one, C₁₈H₁₈N₂OS, the two substituent phenyl rings are inclined of 59.50 (7) and 83.53 (8)° with respect to the plane of the five-membered ring. The S-methyl group lies in this plane while the ethyl group is nearly perpendicular to it. In the crystal, weak C—H⋯O hydrogen bonds form inversion dimers, which pack via conventional van der Waals contacts. A Hirshfeld surface analysis was performed, showing the predominance of H⋯H and C⋯H/H⋯C contacts.

Keywords: crystal structure; thiophenytoin; dihydroimidazolone; methylsulfanyl; Hirshfeld surface.

CCDC reference: 2478215

1. Chemical context

Hydantoin (imidazolidine-2,4-dione) represents a highly valuable and widely utilized heterocyclic scaffold in medicinal chemistry, as demonstrated by its presence in several clinically approved drugs, including phenytoin, nitrofurantoin, and enzalutamide (El Moutaouakil Ala Allah, Guerrab et al., 2024 ). The hydantoin scaffold exhibits a wide range of pharmacological and biological properties, including antibacterial (Allah et al., 2024 ), antiepileptic (El Moutaouakil Ala Allah, Guerrab et al., 2024), antidiabetic (Guerrab et al., 2025 ; El Moutaouakil Ala Allah et al., 2025 ), anticancer (Shankaraiah et al., 2014 ), and anti-inflammatory (Asim Kaplancikli et al., 2012 ) activities. Furthermore, hydantoin derivatives are well known for their broad activity in corrosion prevention (AlObaid et al., 2024 ; Ait Mansour et al., 2025 ), and several of them have demonstrated high corrosion inhibition efficiency (Ettahiri et al., 2025 ; El Kaouahi et al., 2025 ).

As part of our ongoing research on heterocyclic scaffolds (El Moutaouakil Ala Allah, Kariuki et al. 2024 , El Moutaouakil Ala Allah et al., 2025; Guerrab et al., 2022 ), we report the synthesis of 3-ethyl-2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one, 3, via an N-alkylation reaction of 2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one.

2. Structural commentary

The title molecule crystallizes in the monoclinic space group P2₁/n (Fig. 1). The dihedral angles between the mean plane of the five-membered ring and the planes of the C7–C12 and the C13–C18 phenyl rings are 59.50 (7) and 83.53 (8)°, respectively, which is one of the larger differences in the dihedral angles found in related molecules (vide infra). The five-membered ring is planar to within 0.007 (1) Å (r.m.s. deviation of the fitted atoms = 0.001 Å) and the C4—S1 group lies within its plane as the C4—S1—C1—N1 torsion angle is −179.47 (13)°. In contrast, the ethyl group is nearly perpendicular to the aforementioned plane as the C1—N1—C5—C6 torsion angle is 87.81 (19)°.

Figure 1
Perspective view of the title molecule with labeling scheme and 50% probability ellipsoids.

3. Supramolecular features

In the crystal, weak C11—H11⋯O1ⁱ hydrogen bonds (Table 1) form centrosymmetric dimers, which, in turn, pack via conventional van der Waals contacts (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.95	2.49	3.434 (2)	171
Symmetry code: (i) .

Figure 2
Packing viewed along the b-axis direction with C—H⋯O hydrogen bonds depicted by dashed lines and hydrogen atoms not participating in these interactions omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to May 2025 (Groom et al., 2016 ) with the fragment shown in Fig. 3, where R = R′ = no substituent, yielded nine hits. Included molecules have R,R′ = –CH₂CH₂– (DIYRAE; Karolak-Wojciechowska et al., 1985 ), –CH₂CH(COOEt)– (FURFED; Karolak-Wojciechowska & Kieć-Kononowicz, 1987 ), –CH₂CH₂CH₂– (IMTHZN; Kieć-Kononowicz et al., 1981 and IMTHZN01; Guerrab et al., 2019 ), and –CH₂CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₂– (LIGWOR; Guerrab et al., 2023 ) as well as R = R′ = benzyl (RAHGUF; Akrad et al., 2017 ), R = R′ = n-propyl (RIJZIW; Akrad et al., 2018 ), R = R′ = methyl (YEYYUA; El Moutaouakil Ala Allah et al., 2023 ) and R = R′ = ethyl (HOPQAI; El Moutaouakil Ala Allah, Guerrab et al., 2024). The dihedral angles between the planes of the two phenyl rings attached directly to the 4,5-dihydro-1H-imidazol-5-one ring vary over the range 47.89° to 89.59° due to the differing packings resulting from the varied sizes and shapes of the R and R′ substituents. In most instances, the two angles differ by ca. 15° but in LIGWOR they are nearly equal, being 62.10 (11) and 61.35 (11)°. As in the title molecule, the packing in RAHGOF and HOPQAI involves the formation of centrosymmetric dimers through weak C—H⋯O hydrogen bonds, with dimers associated through van der Waals interactions. In all of the other compounds, except for IMTHZN and IMTHZN01, chains of molecules parallel to crystallographic a axis are generated by weak C—H⋯O hydrogen bonds. In the exceptions, the chain is formed by weak C—H⋯N hydrogen bonds and the chains are linked by weak C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions.

Figure 3
The fragment used in the Cambridge Structural Database search.

5. Hirshfeld surface analysis

The d_norm surface and 2-D fingerprint plots for the title molecule were calculated with CrystalExplorer (Spackman et al., 2021 ) and full descriptions of the methods and interpretations of the results have been published by Tan et al. (2019 ). The d_norm surface together with several neighboring molecules is shown in Fig. 4, in which the C—H⋯O hydrogen bonds are shown as red dashed lines passing through the dark red spots on the surface (indicating contacts shorter than the sum of the van der Waals radii). Fig. 5 shows the 2-D fingerprint plots for all intermolecular interactions (a) and those delineated into contacts between specific atom types (b)–(e). The H⋯H contacts (b) account for 57.4% of the total, which is expected as the periphery of the molecule consists largely of hydrogen atoms. Most are bound to phenyl and methyl groups, which are directed outwards from the center of gravity and so will be the first to contact neighboring molecules. It is perhaps surprising that the C⋯H/H⋯C contacts (c), which contribute 25.3% of the total, are more prevalent than the O⋯H/H⋯O contacts (d, 7.2%), despite the latter being the only interactions in the packing that can be regarded as directional (vide supra). However, the geometrical analysis carried out with PLATON (Spek, 2020 ) shows a contact of 2.94 Å between H5B and the centroid Cg of the C7–C12 phenyl ring at −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ . Nevertheless, the C5—H5B⋯Cg1 angle of 127° is quite small for the contact to be considered a definite C—H⋯π(ring) interaction. Several other C⋯H distances approximately equal to the sum of the two van der Waals radii are listed, which can account for this high percentage contribution. As noted, the O⋯H/H⋯O contacts come primarily from the weak C—H⋯O hydrogen bonds described in Table 1. Although the S⋯H/H⋯S interactions contribute almost as much, there does not appear to be any obvious C—H⋯S hydrogen bond.

Figure 4
The Hirshfeld d_norm surface of the title compound with several neighboring molecules. The C—H⋯O hydrogen bonds are depicted by red dashed lines.

Figure 5
The 2-D fingerprint plots showing all intermolecular contacts (a) and those delineated into H⋯H (b), C⋯H/H⋯C (c), O⋯H/H⋯O (d) and S⋯H/H⋯S (e) contacts.

6. Synthesis and crystallization

The title compound was obtained according to the reaction scheme shown in Fig. 6. To a solution of 2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one (1) (0.5 g, 1.7 mmol) in DMF (10 mL), iodoethane (2) (2.10 mmol) was added in the presence of K₂CO₃ (1.8 mmol) and a catalytic amount of BTBA (10%). The reaction mixture was stirred at room temperature for 3 h (El Moutaouakil Ala Allah et al., 2023; Guerrab et al., 2023; El Moutaouakil Ala Allah, Kariuki, Alsubari et al., 2024). After filtration of the inorganic salts, the solvent was evaporated under reduced pressure, and the crude residue was purified by recrystallization from ethanol, affording 3-ethyl-2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one (3) in 96% yield, m.p. = 394–396 K. FT-IR (ATR, ν, cm⁻¹): 3061 (C—H Ar), 2980 (–CH₃), 2854 (C—H Aliphatic), 1726 (C=O); ¹H NMR (500 MHz, CDCl₃): δ ppm 1.24 (t, 3H, N—CH₂—CH₃), 2.70 (s, 3H, S—CH₃), 3.56 (q, 2H, N—CH₂—CH₃), 7.25–7.56 (m, 10H, Ar H); ¹³C NMR (125 MHz, CDCl₃); 12.85 (N—CH₂—CH₃), 14.29 (S—CH₃), 35.96 (N—CH₂—CH₃), 78.47 (C—2Ph); 127.24, 127.73, 128.48, 140.67 (C—Ar), 161.67 (C=N), 180,67 (C=O); HRMS (ESI-MS) (m/z) calculated for C₁₈H₁₈N₂OS 311.1140; found 311.12036.

Figure 6
Synthesis of the title compound.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The carbon-bound H atoms were placed in calculated positions and refined isotropically using the riding model, with C—H distances ranging from 0.95 to 0.99 Å and U_iso(H) set to 1.2–1.5 U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂OS
M_r	310.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	12.6759 (2), 9.2109 (2), 14.1568 (3)
β (°)	105.915 (1)
V (Å³)	1589.54 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.82
Crystal size (mm)	0.19 × 0.15 × 0.14

Data collection
Diffractometer	Bruker D8 Venture PhotonII
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.58, 0.75
No. of measured, independent and observed [I > 2σ(I)] reflections	15894, 3237, 2875
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.05
No. of reflections	3237
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.33
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ), WinGX (Farrugia, 2012 ), publCIF (Westrip, 2010 ) and enCIFer (Allen et al., 2004 ).

Supporting information

CCDC reference: 2478215

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902500698X/vm2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902500698X/vm2316Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902500698X/vm2316Isup3.cml

checkCIF report

Computing details top

3-Ethyl-2-(methylsulfanyl)-5,5-diphenyl-3H-imidazol-4(5H)-one top

Crystal data top

C₁₈H₁₈N₂OS	F(000) = 656
M_r = 310.40	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 12.6759 (2) Å	Cell parameters from 438 reflections
b = 9.2109 (2) Å	θ = 4.2–74.6°
c = 14.1568 (3) Å	µ = 1.82 mm⁻¹
β = 105.915 (1)°	T = 200 K
V = 1589.54 (5) Å³	Prism, colourless
Z = 4	0.19 × 0.15 × 0.14 mm

Data collection top

Bruker D8 Venture PhotonII diffractometer	3237 independent reflections
Radiation source: fine-focus sealed tube	2875 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
phi & ω scan	θ_max = 74.6°, θ_min = 4.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→15
T_min = 0.58, T_max = 0.75	k = −11→10
15894 measured reflections	l = −17→16

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0474P)² + 0.4531P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3237 reflections	Δρ_max = 0.23 e Å⁻³
202 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL-2019/2 (Sheldrick 2019), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0025 (4)

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
S1	0.42759 (4)	1.04706 (4)	0.71077 (3)	0.05142 (16)
O1	0.06602 (8)	0.81371 (11)	0.56610 (8)	0.0416 (3)
N2	0.34143 (9)	0.87359 (12)	0.55450 (8)	0.0325 (3)
N1	0.22587 (10)	0.92996 (13)	0.64679 (8)	0.0356 (3)
C13	0.19033 (10)	0.85995 (14)	0.40490 (9)	0.0292 (3)
C3	0.23515 (10)	0.80042 (14)	0.50922 (9)	0.0287 (3)
C7	0.24828 (10)	0.63546 (14)	0.51131 (9)	0.0295 (3)
C2	0.16102 (11)	0.84460 (14)	0.57434 (10)	0.0317 (3)
C1	0.32858 (11)	0.94226 (14)	0.62915 (10)	0.0337 (3)
C8	0.35072 (11)	0.57087 (15)	0.54165 (10)	0.0337 (3)
H8	0.414523	0.629466	0.562886	0.040*
C18	0.20459 (12)	0.78517 (17)	0.32453 (10)	0.0396 (3)
H18	0.236884	0.691312	0.333256	0.047*
C12	0.15565 (12)	0.54770 (16)	0.48046 (12)	0.0390 (3)
H12	0.085017	0.590867	0.459211	0.047*
C10	0.26845 (13)	0.33415 (16)	0.51073 (11)	0.0416 (3)
H10	0.275616	0.231491	0.510549	0.050*
C9	0.36044 (13)	0.42047 (16)	0.54111 (11)	0.0400 (3)
H9	0.430967	0.376892	0.561814	0.048*
C14	0.14038 (12)	0.99562 (16)	0.39013 (11)	0.0391 (3)
H14	0.128113	1.047293	0.444221	0.047*
C17	0.17226 (13)	0.84580 (19)	0.23138 (11)	0.0454 (4)
H17	0.182748	0.793562	0.176805	0.054*
C11	0.16586 (13)	0.39736 (17)	0.48057 (12)	0.0442 (4)
H11	0.102309	0.338169	0.459910	0.053*
C5	0.18677 (15)	0.99957 (17)	0.72403 (11)	0.0437 (4)
H5B	0.248783	1.009702	0.783927	0.052*
H5A	0.130796	0.936822	0.740302	0.052*
C16	0.12491 (12)	0.98171 (19)	0.21774 (11)	0.0447 (4)
H16	0.103796	1.023941	0.154098	0.054*
C15	0.10842 (14)	1.05583 (18)	0.29694 (13)	0.0477 (4)
H15	0.074882	1.148914	0.287611	0.057*
C6	0.13762 (15)	1.14777 (17)	0.69332 (12)	0.0493 (4)
H6A	0.079291	1.139169	0.631694	0.074*
H6C	0.194766	1.213302	0.683826	0.074*
H6B	0.107005	1.186788	0.744561	0.074*
C4	0.53801 (16)	1.0279 (3)	0.65510 (19)	0.0739 (6)
H4C	0.519234	1.078181	0.591672	0.111*
H4B	0.550231	0.924663	0.644994	0.111*
H4A	0.604906	1.070302	0.698209	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0557 (3)	0.0418 (2)	0.0454 (2)	−0.01332 (17)	−0.00529 (18)	−0.00844 (16)
O1	0.0385 (5)	0.0426 (6)	0.0487 (6)	−0.0066 (4)	0.0205 (4)	−0.0076 (5)
N2	0.0308 (5)	0.0286 (6)	0.0351 (6)	−0.0050 (4)	0.0042 (4)	−0.0001 (5)
N1	0.0449 (6)	0.0318 (6)	0.0299 (6)	−0.0034 (5)	0.0098 (5)	−0.0047 (5)
C13	0.0271 (6)	0.0298 (6)	0.0304 (6)	−0.0048 (5)	0.0075 (5)	0.0000 (5)
C3	0.0279 (6)	0.0279 (6)	0.0299 (6)	−0.0031 (5)	0.0071 (5)	−0.0024 (5)
C7	0.0348 (6)	0.0286 (6)	0.0258 (6)	−0.0027 (5)	0.0096 (5)	−0.0013 (5)
C2	0.0379 (7)	0.0270 (6)	0.0308 (6)	−0.0016 (5)	0.0107 (5)	−0.0002 (5)
C1	0.0385 (7)	0.0264 (6)	0.0312 (7)	−0.0038 (5)	0.0008 (5)	0.0018 (5)
C8	0.0370 (7)	0.0328 (7)	0.0306 (6)	−0.0016 (5)	0.0080 (5)	−0.0013 (5)
C18	0.0423 (8)	0.0423 (8)	0.0350 (7)	0.0047 (6)	0.0121 (6)	−0.0012 (6)
C12	0.0361 (7)	0.0339 (7)	0.0473 (8)	−0.0045 (5)	0.0119 (6)	−0.0053 (6)
C10	0.0604 (9)	0.0275 (7)	0.0385 (7)	−0.0016 (6)	0.0161 (7)	0.0004 (6)
C9	0.0460 (8)	0.0357 (7)	0.0363 (7)	0.0063 (6)	0.0075 (6)	0.0010 (6)
C14	0.0480 (8)	0.0296 (7)	0.0393 (7)	−0.0004 (6)	0.0114 (6)	0.0000 (6)
C17	0.0473 (8)	0.0577 (10)	0.0318 (7)	−0.0036 (7)	0.0120 (6)	−0.0009 (7)
C11	0.0481 (8)	0.0347 (8)	0.0514 (9)	−0.0126 (6)	0.0166 (7)	−0.0069 (7)
C5	0.0641 (10)	0.0384 (8)	0.0314 (7)	−0.0014 (7)	0.0177 (7)	−0.0058 (6)
C16	0.0404 (8)	0.0540 (9)	0.0358 (7)	−0.0114 (7)	0.0037 (6)	0.0126 (7)
C15	0.0531 (9)	0.0372 (8)	0.0500 (9)	0.0012 (7)	0.0093 (7)	0.0116 (7)
C6	0.0661 (10)	0.0375 (8)	0.0469 (9)	−0.0004 (7)	0.0200 (8)	−0.0072 (7)
C4	0.0447 (10)	0.0732 (14)	0.0939 (16)	−0.0214 (9)	0.0023 (10)	−0.0164 (12)

Geometric parameters (Å, º) top

S1—C1	1.7455 (14)	C10—C9	1.379 (2)
S1—C4	1.793 (2)	C10—C11	1.381 (2)
O1—C2	1.2116 (16)	C10—H10	0.9500
N2—C1	1.2797 (18)	C9—H9	0.9500
N2—C3	1.4855 (16)	C14—C15	1.385 (2)
N1—C2	1.3723 (17)	C14—H14	0.9500
N1—C1	1.3960 (19)	C17—C16	1.379 (2)
N1—C5	1.4663 (18)	C17—H17	0.9500
C13—C18	1.3837 (19)	C11—H11	0.9500
C13—C14	1.3906 (19)	C5—C6	1.514 (2)
C13—C3	1.5311 (17)	C5—H5B	0.9900
C3—C7	1.5279 (18)	C5—H5A	0.9900
C3—C2	1.5405 (18)	C16—C15	1.377 (2)
C7—C8	1.3851 (19)	C16—H16	0.9500
C7—C12	1.3934 (19)	C15—H15	0.9500
C8—C9	1.391 (2)	C6—H6A	0.9800
C8—H8	0.9500	C6—H6C	0.9800
C18—C17	1.386 (2)	C6—H6B	0.9800
C18—H18	0.9500	C4—H4C	0.9800
C12—C11	1.391 (2)	C4—H4B	0.9800
C12—H12	0.9500	C4—H4A	0.9800

C1—S1—C4	99.25 (8)	C10—C9—H9	119.8
C1—N2—C3	105.96 (11)	C8—C9—H9	119.8
C2—N1—C1	108.04 (11)	C15—C14—C13	120.35 (14)
C2—N1—C5	123.52 (13)	C15—C14—H14	119.8
C1—N1—C5	128.35 (12)	C13—C14—H14	119.8
C18—C13—C14	118.71 (13)	C16—C17—C18	120.18 (14)
C18—C13—C3	121.15 (12)	C16—C17—H17	119.9
C14—C13—C3	120.01 (12)	C18—C17—H17	119.9
N2—C3—C7	111.21 (10)	C10—C11—C12	119.97 (14)
N2—C3—C13	107.85 (10)	C10—C11—H11	120.0
C7—C3—C13	112.61 (10)	C12—C11—H11	120.0
N2—C3—C2	104.58 (10)	N1—C5—C6	112.13 (12)
C7—C3—C2	109.41 (10)	N1—C5—H5B	109.2
C13—C3—C2	110.90 (10)	C6—C5—H5B	109.2
C8—C7—C12	119.06 (13)	N1—C5—H5A	109.2
C8—C7—C3	121.40 (11)	C6—C5—H5A	109.2
C12—C7—C3	119.53 (12)	H5B—C5—H5A	107.9
O1—C2—N1	125.61 (12)	C15—C16—C17	119.58 (14)
O1—C2—C3	129.32 (12)	C15—C16—H16	120.2
N1—C2—C3	105.07 (11)	C17—C16—H16	120.2
N2—C1—N1	116.34 (12)	C16—C15—C14	120.46 (15)
N2—C1—S1	126.07 (11)	C16—C15—H15	119.8
N1—C1—S1	117.58 (10)	C14—C15—H15	119.8
C7—C8—C9	120.20 (13)	C5—C6—H6A	109.5
C7—C8—H8	119.9	C5—C6—H6C	109.5
C9—C8—H8	119.9	H6A—C6—H6C	109.5
C13—C18—C17	120.69 (14)	C5—C6—H6B	109.5
C13—C18—H18	119.7	H6A—C6—H6B	109.5
C17—C18—H18	119.7	H6C—C6—H6B	109.5
C11—C12—C7	120.47 (14)	S1—C4—H4C	109.5
C11—C12—H12	119.8	S1—C4—H4B	109.5
C7—C12—H12	119.8	H4C—C4—H4B	109.5
C9—C10—C11	119.82 (14)	S1—C4—H4A	109.5
C9—C10—H10	120.1	H4C—C4—H4A	109.5
C11—C10—H10	120.1	H4B—C4—H4A	109.5
C10—C9—C8	120.48 (14)

C1—N2—C3—C7	−117.50 (12)	C3—N2—C1—S1	179.54 (10)
C1—N2—C3—C13	118.57 (12)	C2—N1—C1—N2	−1.10 (16)
C1—N2—C3—C2	0.48 (13)	C5—N1—C1—N2	−177.81 (13)
C18—C13—C3—N2	98.09 (14)	C2—N1—C1—S1	179.61 (9)
C14—C13—C3—N2	−77.78 (14)	C5—N1—C1—S1	2.90 (19)
C18—C13—C3—C7	−24.99 (17)	C4—S1—C1—N2	1.33 (15)
C14—C13—C3—C7	159.15 (12)	C4—S1—C1—N1	−179.47 (13)
C18—C13—C3—C2	−147.96 (12)	C12—C7—C8—C9	0.0 (2)
C14—C13—C3—C2	36.17 (16)	C3—C7—C8—C9	−178.82 (12)
N2—C3—C7—C8	−7.14 (16)	C14—C13—C18—C17	1.6 (2)
C13—C3—C7—C8	114.04 (13)	C3—C13—C18—C17	−174.32 (13)
C2—C3—C7—C8	−122.16 (13)	C8—C7—C12—C11	0.3 (2)
N2—C3—C7—C12	174.01 (12)	C3—C7—C12—C11	179.17 (13)
C13—C3—C7—C12	−64.81 (15)	C11—C10—C9—C8	0.0 (2)
C2—C3—C7—C12	58.99 (15)	C7—C8—C9—C10	−0.2 (2)
C1—N1—C2—O1	−178.57 (13)	C18—C13—C14—C15	−1.7 (2)
C5—N1—C2—O1	−1.7 (2)	C3—C13—C14—C15	174.24 (13)
C1—N1—C2—C3	1.28 (14)	C13—C18—C17—C16	−0.3 (2)
C5—N1—C2—C3	178.18 (12)	C9—C10—C11—C12	0.3 (2)
N2—C3—C2—O1	178.75 (14)	C7—C12—C11—C10	−0.5 (2)
C7—C3—C2—O1	−62.04 (18)	C2—N1—C5—C6	−88.44 (17)
C13—C3—C2—O1	62.76 (18)	C1—N1—C5—C6	87.81 (19)
N2—C3—C2—N1	−1.09 (13)	C18—C17—C16—C15	−1.0 (2)
C7—C3—C2—N1	118.11 (11)	C17—C16—C15—C14	0.9 (2)
C13—C3—C2—N1	−117.09 (11)	C13—C14—C15—C16	0.5 (2)
C3—N2—C1—N1	0.33 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.95	2.49	3.434 (2)	171

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

YR is thankful to the National Center for Scientific and Technical Research of Morocco (CNRST) for its continuous support. CM would like to acknowledge the COMP-R Initiatives, funded by the Departments of Excellence program of the Italian Ministry for University and Research (MUR, 2023–2027). The contributions of the authors are as follows: conceptualization, YR; methodology, AA; investigation, AEMAA and WG; writing (original draft), AEMAA; writing (review and editing of the manuscript), YR; formal analysis, JTM and CM; supervision, YR; crystal structure determination, CM.

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