1-Ethenyl-2-(methyl­sulfan­yl)-4,4-diphenyl-4,5-di­hydro-1H-imidazol-5-one (Thio­phenytoin analogue): synthesis, structure and Hirshfeld surface analysis

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

doi:10.1107/S2056989026002616

research communications

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ISSN: 2056-9890

Volume 82| Part 4| April 2026| Pages 366-370

https://doi.org/10.1107/S2056989026002616

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1-Ethenyl-2-(methylsulfanyl)-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one (Thiophenytoin analogue): synthesis, structure and Hirshfeld surface analysis

Abderrazzak El Moutaouakil Ala Allah,^a Chiara Massera,^b Joel T. Mague,^c Abdulsalam Alsubari ^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, ^cDepartment of Chemistry, Tulane University New Orleans, LA, 70118, USA, and ^dLaboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21 September University, Yemen
^*Correspondence e-mail: [email protected], [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 6 March 2026; accepted 11 March 2026; online 17 March 2026)

The title molecule, C₁₈H₁₆N₂OS, exhibits a slight ‘ruffling' of the imidazolone ring, and the lone pair on the tricoordinate nitrogen atom is involved in N→C π-bonding within the ring. Both the methyl group bonded to sulfur and the vinyl substituent lie very close to the plane of the five-membered ring. In the crystal, C—H⋯O hydrogen bonds form inversion dimers, which are linked into chains extending along the b-axis direction by C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that H⋯H interactions account for more than half of the intermolecular contacts, with C—H⋯π(ring) interactions contributing a further quarter of the total.

Keywords: crystal structure; dihydroimidazolone; sulfanyl; Hirshfeld surface.

CCDC reference: 2536800

1. Chemical context

Heterocycles incorporating both sulfur and nitrogen atoms constitute a class of compounds of great interest in organic and medicinal chemistry, owing to the richness of their physicochemical properties and the diversity of their biological activities (El Moutaouakil Ala Allah et al., 2024a ; Ettahiri et al., 2024 ; Guerrab et al., 2025 ). Among them, thiohydantoin, a sulfur-containing heterocycle structurally related to hydantoin and characterized by the presence of a thioxo (C=S) group, has emerged as a privileged scaffold in medicinal chemistry (Gupta et al., 2025 ). Its distinctive electronic and structural features enable a wide range of chemical modifications and promote strong interactions with various biological targets (El Moutaouakil Ala Allah et al., 2024b ). Consequently, numerous thiohydantoin derivatives have demonstrated significant pharmacological activities, including antidiabetic (Ala Allah et al., 2025c ), anticancer (Mezoughi et al., 2021 ), and antimicrobial effects (El Moutaouakil Ala Allah et al., 2024c ). In addition, some derivatives have shown promising performance as corrosion inhibitors (Ala Allah et al., 2024 ; AlObaid et al., 2024 ; El Moutaouakil Ala Allah et al., 2024d ). In a continuation of our research on thiohydantoin derivatives (Ramli et al., 2017 ; Guerrab et al., 2023a,,b , 2022 ; El Moutaouakil Ala Allah et al., 2024e ), we report herein the synthesis of 2-(methylthio)-5,5-diphenyl-3-vinyl-3,5-dihydro-4H-imidazol-4-one (Fig. 1) via an E2 elimination from 3-(2-bromoethyl)-2-(methylthio)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one, a secondary halide, under conditions promoting unimolecular elimination in the presence of diethylamine [(Et)₂NH] as the base and DMF as the solvent.

Figure 1
Perspective view of the title molecule with labeling scheme and 30% probability ellipsoids.

2. Structural commentary

The dihydroimidazolone ring is essentially planar, with a maximum deviation of 0.035 (1) Å from the mean plane (r.m.s. deviation of the fitted atoms = 0.001 Å). Atom C3 lies 0.035 (1) Å on one side of this plane, while C2 is displaced by 0.034 (1) Å on the opposite side. This slight out-of-plane displacement gives the ring a slight `ruffled' conformation. The mean planes of the C7–C12 and C13–C18 rings are inclined to that of the dihydroimidazolone ring by 70.15 (9) and 66.01 (8)^o, respectively. Atoms C4 and C6 both lie close to the plane of the dihydroimidazolone ring, as indicated by the C4—S1—C1—N2 and the C2—N1—C5—C6 torsion angles of −3.4 (2) and −1.8 (3)^o, respectively. The sum of the bond angles about N1 is 360^o within experimental error, indicating that its lone pair is involved in N→C π-bonding. Although all the bonds to N1 are shorter than expected for formal single bonds, the N1—C2 distance of 1.387 (2) Å is the shortest, suggesting that the lone-pair interaction is strongest in this bond.

3. Supramolecular features

In the crystal, inversion dimers are generated by weak C15—H15⋯O1ⁱⁱ hydrogen bonds and these are connected into chains extending along the b-axis direction by C4—H4B⋯Cg3ⁱ interactions (Table 1; Cg3 is the centroid of the C13-C18 benzene ring). The chains pack with normal van der Waals contacts (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯Cg3ⁱ	0.96	2.90	3.815 (2)	160
C15—H15⋯O1ⁱⁱ	0.93	2.53	3.434 (2)	166
Symmetry codes: (i) ; (ii) .

Figure 2
Packing viewed along the a-axis direction with C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions depicted, respectively, by black and green dashed lines. Hydrogen atoms not involved in these interactions are omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to January 2026; Groom et al., 2016 ) with the search fragment shown in Fig. 3 (R = R′) gave nine hits, all of which are similar to the title compound. One group has R = R′ = Me (YEYYUA; El Moutaouakil Ala Allah et al., 2023 ), Et (HOPQAI; El Moutaouakil Ala Allah et al., 2024a), n-Pr (RIJZIW; Akrad et al., 2018 ) and benzyl (RAHGUF; Akrad et al., 2017 ). In the second group, the nitrogen and sulfur atoms are part of an exocyclic ring fused to the dihydroimidazolone ring, with R,R′ = –CH₂CH₂– (DIYRAE; Karolak-Wojciechowska et al., 1985 ), –CH(CO₂Et)CH₂– (FURFED; Karolak-Wojciechowska & Kieć-Kononowicz, 1987 ), –(CH₂)₃– (IMTHZN; Kieć-Kononowicz et al., 1981 and IMTHZN01; Guerrab et al., 2019 ) and –(CH₂)₂O(CH₂)₂O(CH₂)₂O(CH₂)₂– (LIGWOR; Guerrab et al., 2023b). In all cases, the sum of the angles about the tri-coordinate nitrogen atom in the five-membered ring is 360^o within experimental error, indicating participation of the nitrogen lone pair N→C π-bonding. With the exception of DIYRAE, the N—C bond to the carbonyl carbon is the shortest of the three bonds involving this nitrogen atom, as in the title compound; the corresponding distances range from 1.362 (2) Å in FURFED to 1.380 (2) Å in RAHGUF. In DIYRAE, the N—C bond to the carbonyl carbon is 1.383 (11) Å, whereas the other endocyclic N—C bond is 1.363 (11) Å. The reason for this variation is unclear; however, the associated standard uncertainties are relatively large, so the difference may not be significant. In all examples, the S—C bond corresponding to C4—S1 in the title molecule lies close to the mean plane of the five-membered ring. The largest torsion angle (corresponding to the C4—S1—C1—N2 angle in the title molecule) is C5—S1—C1—N1 in FURFED [−17.41 (15)^o]. This is likely due to the constraints imposed by the ring attached to the dihydroimidazolone moiety. For R = Et, n-Pr and benzyl (Fig. 3), the carbon bonded to the nitrogen atom lies in the plane of the dihydroimidazolone moiety, but the rest of the substituent is rotated well out of this plane. In the remaining derivatives, a similar twist is observed, but only to the extent allowed by the geometry of the pendant ring.

Figure 3
The search fragment used in the database survey.

5. Hirshfeld surface analysis

The Hirshfeld surface analysis of the intermolecular interactions in the crystal of the title molecule was performed with CrystalExplorer (Spackman et al., 2021 ). Descriptions of the plots obtained and their interpretations have been previously published (Tan et al., 2019 ). Fig. 4a shows the d_norm surface with several neighboring molecules included. In the lower right of the figure, one of the inversion dimers formed by the C—H⋯O hydrogen bond listed in Table 1 (red dashed lines) is shown. In the upper right of the figure, the S—CH₃ group forms a C—H⋯π(ring) interaction with the phenyl group directly beneath it. Fig. 4b shows the Hirshfeld surface mapped over the shape-index function; the absence of orange triangle motifs indicates that significant π–π stacking interactions are not present. Fig. 5 presents the two-dimensional fingerprint plots for all interactions (a) and those limited to specific interaction types. Fig. 5b shows that H⋯H interactions comprise 54.5% of the total, consistent with the molecule's periphery being dominated by hydrogen atoms. Next, contributing 25.8% of the total, are the C⋯H/H⋯C interactions (Fig. 5c). These appear as diffuse regions with a superimposed pair of blunt peaks. The peaks can be ascribed to the C—H⋯π(ring) interactions (Table 1), whereas the diffuse regions represent a range of van der Waals contacts. The C—H⋯O hydrogen bonds are reflected in the O⋯H/H⋯O interactions, which appear as a pair of relatively sharp peaks in Fig. 5d and comprise 6.7% of the total. Finally, the S⋯H/H⋯S interactions, which account for 6.6% of the total, appear in Fig. 5e as a pair of blunt peaks with a superimposed pair of sharper peaks. Although this might suggest C—H⋯S hydrogen bonding, the d_e + d_i distance of ≃ 3.1 Å indicates that it is simply a normal van der Waals contact.

Figure 4
The Hirshfeld d_norm surface (a) and the Hirshfeld surface mapped over shape-index (b) showing several added neighboring molecules.

Figure 5
Two-dimensional fingerprint plots showing all intermolecular contacts (a) and those limited to H⋯H contacts (b), C⋯H/H⋯C contacts (c), O⋯H/H⋯O contacts (d) and S⋯H/H⋯S contacts (e).

6. Synthesis and crystallization

To a solution of 2-(methylthio)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one (1) (0.5 g, 1.2 mmol) in DMF (10 mL), half an equivalent of 1,2-dibromoethane (2) (0.6 mmol) was added in the presence of K₂CO₃ (1.8 mmol) and a catalytic amount of benzyltributylammonium bromide (BTBA, 10%). The reaction mixture was stirred at room temperature for 4h, as described in our previous work (El Moutaouakil Ala Allah et al., 2023; El Moutaouakil Ala Allah et al., 2025b ; El Moutaouakil Ala Allah et al., 2024c; El Moutaouakil Ala Allah et al., 2025a ). The resulting compound (3) was subsequently refluxed in DMF in the presence of diethylamine, affording 2-(methylthio)-5,5-diphenyl-3-vinyl-3,5-dihydro-4H-imidazol-4-one (4) via an elimination reaction (Fig. 6).

Figure 6
Synthesis of the title compound.

2-(Methylthio)-5,5-diphenyl-3-vinyl-3,5-dihydro-4H-imidazol-4-one (4) Yield = 68%; m.p. = 391–393K; Appearance: White powder; FT-IR (ATR, cm⁻¹): 3062 (C—H Ar), 2985 (–CH₃), 2852 (C—H Aliphatic), 1728 (C=O); ¹H NMR (500 MHz, CDCl₃): δ ppm 1.24 2.72 (s, 3H, S—CH₃), 5.54 (dd, 2H, –CH₂), 6.80 (m, 1H, CH), 7.20–7.30 (m, 10H, Ar H); ¹³C NMR (125 MHz, CDCl₃); 14.18 (S—CH₃), 76.20 (C—2Ph), 118.22 (–CH₂), 130.14 (CH), 124.20, 126.23, 128.40, 140.62 (C—Ar), 162.57 (C=N), 178.12 (C=O).

7. Refinement details

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 0.93 to 0.99 Å and U_iso(H) set to 1.2–1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂OS
M_r	308.39
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	295
a, b, c (Å)	8.9481 (3), 9.0321 (2), 10.6253 (3)
α, β, γ (°)	81.333 (1), 69.520 (1), 82.227 (1)
V (Å³)	792.11 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker D8 Venture PhotonIII
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.723, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	29667, 3209, 2950
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.04
No. of reflections	3209
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.41
Computer programs: APEX5 (and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ), WinGX (Farrugia, 2012 ), publCIF (Westrip, 2010 ) and enCIFer (Allen et al., 2004 ).

Supporting information

CCDC reference: 2536800

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002616/vm2326sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002616/vm2326Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026002616/vm2326Isup3.cml

checkCIF report

Computing details top

1-Ethenyl-2-(methylsulfanyl)-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one top

Crystal data top

C₁₈H₁₆N₂OS	Z = 2
M_r = 308.39	F(000) = 324
Triclinic, P1	D_x = 1.293 Mg m⁻³
a = 8.9481 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0321 (2) Å	Cell parameters from 1561 reflections
c = 10.6253 (3) Å	θ = 2.1–26.0°
α = 81.333 (1)°	µ = 0.21 mm⁻¹
β = 69.520 (1)°	T = 295 K
γ = 82.227 (1)°	Prismatic, colourless
V = 792.11 (4) Å³	0.20 × 0.18 × 0.17 mm

Data collection top

Bruker D8 Venture PhotonIII diffractometer	3209 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
phi & ω scan	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→10
T_min = 0.723, T_max = 0.745	k = −11→10
29667 measured reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.055P)² + 0.2157P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3209 reflections	Δρ_max = 0.23 e Å⁻³
212 parameters	Δρ_min = −0.41 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.

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

	x	y	z	U_iso*/U_eq
N1	0.30806 (14)	0.53530 (14)	0.15287 (12)	0.0456 (3)
N2	0.41715 (14)	0.49764 (13)	0.32000 (12)	0.0437 (3)
O1	0.21905 (14)	0.78849 (13)	0.15425 (12)	0.0576 (3)
S1	0.42204 (5)	0.24750 (4)	0.20897 (5)	0.05768 (16)
C1	0.38291 (16)	0.43747 (16)	0.23382 (14)	0.0438 (3)
C2	0.28861 (16)	0.67747 (16)	0.19379 (14)	0.0441 (3)
C3	0.37180 (16)	0.66082 (15)	0.30036 (13)	0.0403 (3)
C4	0.5259 (3)	0.1856 (2)	0.3269 (2)	0.0708 (5)
H4A	0.611516	0.247781	0.309316	0.106*
H4B	0.569044	0.083047	0.317336	0.106*
H4C	0.452827	0.192825	0.417262	0.106*
C5	0.2620 (2)	0.4928 (2)	0.04959 (16)	0.0565 (4)
C6	0.1893 (3)	0.5785 (3)	−0.0238 (2)	0.0745 (5)
C7	0.25522 (16)	0.71697 (16)	0.43112 (14)	0.0437 (3)
C8	0.1613 (2)	0.6187 (2)	0.53057 (18)	0.0634 (4)
H8	0.169625	0.517770	0.518152	0.076*
C9	0.0550 (2)	0.6700 (3)	0.6487 (2)	0.0846 (6)
H9	−0.007131	0.602963	0.715446	0.101*
C10	0.0403 (2)	0.8174 (3)	0.6681 (2)	0.0848 (7)
H10	−0.031074	0.850703	0.748042	0.102*
C11	0.1310 (2)	0.9168 (3)	0.5695 (2)	0.0788 (6)
H11	0.120184	1.017900	0.582140	0.095*
C12	0.2388 (2)	0.8667 (2)	0.45097 (19)	0.0614 (4)
H12	0.300294	0.934462	0.384488	0.074*
C13	0.52751 (16)	0.73904 (15)	0.24654 (13)	0.0401 (3)
C14	0.56481 (18)	0.84435 (17)	0.13351 (15)	0.0482 (3)
H14	0.491099	0.874571	0.088924	0.058*
C15	0.7120 (2)	0.90521 (19)	0.08628 (17)	0.0578 (4)
H15	0.736437	0.975100	0.009807	0.069*
C16	0.82111 (19)	0.86263 (19)	0.15194 (19)	0.0597 (4)
H16	0.919585	0.902990	0.120003	0.072*
C17	0.7836 (2)	0.7593 (2)	0.26591 (19)	0.0612 (4)
H17	0.856806	0.730985	0.311200	0.073*
C18	0.63817 (19)	0.69766 (18)	0.31316 (16)	0.0525 (4)
H18	0.614243	0.628148	0.389912	0.063*
H6A	0.169 (3)	0.530 (3)	−0.092 (2)	0.090 (7)*
H6B	0.151 (3)	0.684 (3)	−0.007 (3)	0.103 (8)*
H5	0.293 (3)	0.386 (3)	0.034 (3)	0.103 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0450 (6)	0.0517 (7)	0.0435 (6)	−0.0105 (5)	−0.0168 (5)	−0.0055 (5)
N2	0.0481 (6)	0.0381 (6)	0.0467 (6)	−0.0065 (5)	−0.0182 (5)	−0.0020 (5)
O1	0.0607 (7)	0.0557 (6)	0.0628 (7)	−0.0048 (5)	−0.0336 (5)	0.0049 (5)
S1	0.0605 (3)	0.0467 (2)	0.0703 (3)	−0.00652 (17)	−0.0231 (2)	−0.01581 (18)
C1	0.0400 (7)	0.0441 (7)	0.0459 (7)	−0.0090 (5)	−0.0112 (6)	−0.0040 (6)
C2	0.0416 (7)	0.0508 (8)	0.0410 (7)	−0.0099 (6)	−0.0157 (6)	0.0015 (6)
C3	0.0446 (7)	0.0379 (6)	0.0406 (7)	−0.0057 (5)	−0.0181 (6)	0.0001 (5)
C4	0.0841 (13)	0.0495 (9)	0.0846 (13)	0.0050 (9)	−0.0378 (11)	−0.0119 (9)
C5	0.0525 (9)	0.0746 (11)	0.0476 (8)	−0.0166 (8)	−0.0166 (7)	−0.0137 (7)
C6	0.0723 (12)	0.1042 (17)	0.0591 (11)	−0.0116 (11)	−0.0334 (9)	−0.0147 (11)
C7	0.0401 (7)	0.0504 (8)	0.0422 (7)	−0.0038 (6)	−0.0170 (6)	−0.0022 (6)
C8	0.0548 (9)	0.0658 (10)	0.0592 (10)	−0.0092 (8)	−0.0089 (8)	0.0032 (8)
C9	0.0618 (11)	0.1100 (18)	0.0605 (11)	−0.0099 (11)	0.0017 (9)	0.0029 (11)
C10	0.0556 (11)	0.130 (2)	0.0620 (11)	0.0081 (12)	−0.0082 (9)	−0.0347 (12)
C11	0.0651 (11)	0.0857 (14)	0.0867 (14)	0.0062 (10)	−0.0188 (10)	−0.0414 (12)
C12	0.0581 (9)	0.0581 (9)	0.0646 (10)	−0.0058 (7)	−0.0128 (8)	−0.0154 (8)
C13	0.0427 (7)	0.0388 (6)	0.0394 (6)	−0.0043 (5)	−0.0138 (5)	−0.0060 (5)
C14	0.0512 (8)	0.0468 (8)	0.0465 (7)	−0.0069 (6)	−0.0178 (6)	0.0004 (6)
C15	0.0584 (9)	0.0523 (9)	0.0549 (9)	−0.0137 (7)	−0.0101 (7)	0.0039 (7)
C16	0.0462 (8)	0.0554 (9)	0.0734 (11)	−0.0132 (7)	−0.0123 (8)	−0.0062 (8)
C17	0.0512 (9)	0.0627 (10)	0.0768 (11)	−0.0098 (7)	−0.0312 (8)	−0.0013 (8)
C18	0.0529 (8)	0.0545 (8)	0.0538 (8)	−0.0114 (7)	−0.0247 (7)	0.0047 (7)

Geometric parameters (Å, º) top

N1—C2	1.3868 (19)	C8—C9	1.384 (3)
N1—C1	1.4082 (19)	C8—H8	0.9300
N1—C5	1.4170 (19)	C9—C10	1.360 (3)
N2—C1	1.2724 (18)	C9—H9	0.9300
N2—C3	1.4782 (17)	C10—C11	1.371 (4)
O1—C2	1.2068 (18)	C10—H10	0.9300
S1—C1	1.7452 (14)	C11—C12	1.387 (3)
S1—C4	1.792 (2)	C11—H11	0.9300
C2—C3	1.5386 (18)	C12—H12	0.9300
C3—C7	1.5267 (19)	C13—C14	1.385 (2)
C3—C13	1.5344 (18)	C13—C18	1.390 (2)
C4—H4A	0.9600	C14—C15	1.392 (2)
C4—H4B	0.9600	C14—H14	0.9300
C4—H4C	0.9600	C15—C16	1.372 (2)
C5—C6	1.291 (3)	C15—H15	0.9300
C5—H5	0.99 (3)	C16—C17	1.382 (3)
C6—H6A	0.98 (2)	C16—H16	0.9300
C6—H6B	0.99 (3)	C17—C18	1.382 (2)
C7—C12	1.381 (2)	C17—H17	0.9300
C7—C8	1.381 (2)	C18—H18	0.9300

C2—N1—C1	107.34 (11)	C7—C8—H8	119.9
C2—N1—C5	127.43 (14)	C9—C8—H8	119.9
C1—N1—C5	125.23 (14)	C10—C9—C8	120.7 (2)
C1—N2—C3	107.02 (11)	C10—C9—H9	119.6
C1—S1—C4	98.78 (8)	C8—C9—H9	119.6
N2—C1—N1	115.82 (13)	C9—C10—C11	119.80 (18)
N2—C1—S1	125.42 (11)	C9—C10—H10	120.1
N1—C1—S1	118.76 (11)	C11—C10—H10	120.1
O1—C2—N1	126.56 (13)	C10—C11—C12	120.1 (2)
O1—C2—C3	128.33 (14)	C10—C11—H11	120.0
N1—C2—C3	105.10 (11)	C12—C11—H11	120.0
N2—C3—C7	111.22 (11)	C7—C12—C11	120.39 (18)
N2—C3—C13	107.03 (11)	C7—C12—H12	119.8
C7—C3—C13	112.69 (11)	C11—C12—H12	119.8
N2—C3—C2	104.32 (11)	C14—C13—C18	118.84 (13)
C7—C3—C2	109.81 (11)	C14—C13—C3	123.49 (12)
C13—C3—C2	111.43 (11)	C18—C13—C3	117.64 (12)
S1—C4—H4A	109.5	C13—C14—C15	120.39 (14)
S1—C4—H4B	109.5	C13—C14—H14	119.8
H4A—C4—H4B	109.5	C15—C14—H14	119.8
S1—C4—H4C	109.5	C16—C15—C14	120.35 (15)
H4A—C4—H4C	109.5	C16—C15—H15	119.8
H4B—C4—H4C	109.5	C14—C15—H15	119.8
C6—C5—N1	126.82 (19)	C15—C16—C17	119.49 (15)
C6—C5—H5	119.8 (15)	C15—C16—H16	120.3
N1—C5—H5	113.4 (15)	C17—C16—H16	120.3
C5—C6—H6A	115.8 (14)	C18—C17—C16	120.60 (15)
C5—C6—H6B	121.4 (15)	C18—C17—H17	119.7
H6A—C6—H6B	123 (2)	C16—C17—H17	119.7
C12—C7—C8	118.82 (15)	C17—C18—C13	120.31 (14)
C12—C7—C3	120.90 (13)	C17—C18—H18	119.8
C8—C7—C3	120.26 (14)	C13—C18—H18	119.8
C7—C8—C9	120.17 (19)

C3—N2—C1—N1	−3.01 (16)	N2—C3—C7—C8	−23.74 (18)
C3—N2—C1—S1	176.66 (10)	C13—C3—C7—C8	−143.93 (14)
C2—N1—C1—N2	−1.21 (16)	C2—C3—C7—C8	91.21 (16)
C5—N1—C1—N2	178.98 (13)	C12—C7—C8—C9	−1.1 (3)
C2—N1—C1—S1	179.09 (9)	C3—C7—C8—C9	−179.58 (16)
C5—N1—C1—S1	−0.71 (19)	C7—C8—C9—C10	0.5 (3)
C4—S1—C1—N2	−3.39 (15)	C8—C9—C10—C11	0.4 (3)
C4—S1—C1—N1	176.27 (12)	C9—C10—C11—C12	−0.8 (3)
C1—N1—C2—O1	−174.50 (14)	C8—C7—C12—C11	0.7 (3)
C5—N1—C2—O1	5.3 (2)	C3—C7—C12—C11	179.19 (16)
C1—N1—C2—C3	4.63 (14)	C10—C11—C12—C7	0.2 (3)
C5—N1—C2—C3	−175.57 (13)	N2—C3—C13—C14	130.00 (14)
C1—N2—C3—C7	123.87 (12)	C7—C3—C13—C14	−107.43 (15)
C1—N2—C3—C13	−112.64 (12)	C2—C3—C13—C14	16.55 (18)
C1—N2—C3—C2	5.56 (14)	N2—C3—C13—C18	−47.95 (16)
O1—C2—C3—N2	172.92 (14)	C7—C3—C13—C18	74.61 (16)
N1—C2—C3—N2	−6.19 (13)	C2—C3—C13—C18	−161.41 (13)
O1—C2—C3—C7	53.65 (19)	C18—C13—C14—C15	1.2 (2)
N1—C2—C3—C7	−125.46 (12)	C3—C13—C14—C15	−176.70 (14)
O1—C2—C3—C13	−71.94 (18)	C13—C14—C15—C16	−0.6 (2)
N1—C2—C3—C13	108.96 (12)	C14—C15—C16—C17	−0.3 (3)
C2—N1—C5—C6	−1.8 (3)	C15—C16—C17—C18	0.7 (3)
C1—N1—C5—C6	177.93 (17)	C16—C17—C18—C13	−0.1 (3)
N2—C3—C7—C12	157.80 (14)	C14—C13—C18—C17	−0.9 (2)
C13—C3—C7—C12	37.61 (18)	C3—C13—C18—C17	177.16 (15)
C2—C3—C7—C12	−87.25 (16)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···Cg3ⁱ	0.96	2.90	3.815 (2)	160
C15—H15···O1ⁱⁱ	0.93	2.53	3.434 (2)	166

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z.

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; 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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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Ethenyl-2-(methyl­sulfan­yl)-4,4-di­phenyl-4,5-di­hydro-1H-imidazol-5-one (Thio­phenytoin analogue): synthesis, structure and Hirshfeld surface analysis

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Synthesis and crystallization

7. Refinement details

Supporting information

Acknowledgements

References

research communications

1-Ethenyl-2-(methylsulfanyl)-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one (Thiophenytoin analogue): synthesis, structure and Hirshfeld surface analysis

3. Supramolecular features