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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2026 Sep 3;82(Pt 10):1117–1121. doi: 10.1107/S2056989026008790

Synthesis, crystal structure and Hirshfeld surface analysis of 2-(ethyl­sulfan­yl)-3-(2-methyl­prop­yl)-5,5-diphenyl-4,5-di­hydro-3H-imidazol-4-one

Abderrazzak El Moutaouakil Ala Allah a, Chiara Massera b, Abdulsalam Alsubari c,*, Joel T Mague d, Youssef Ramli a,*
Editor: L Van Meervelte
PMCID: PMC13638012  PMID: 42836234

In the title mol­ecule, the imidazolone ring is essentially planar and the inclinations of the planes of the two attached phenyl groups to its plane are distinctly different. There is a degree of π-delocalization in the ring about the tertiary nitro­gen which involves its lone pair. Directed inter­molecular inter­actions comprise C—H⋯O hydrogen bonds and two sets of C—H⋯π(ring) inter­actions. A Hirshfeld surface analysis was performed.

Keywords: crystal structure, imidazolone, supra­molecular inter­actions, Hirshfeld surface analysis

Abstract

In the title compound, C21H24N2OS, are reported. The imidazolone ring is essentially planar, and the coordination geometry about the N-substituted nitro­gen atom is also nearly planar, consistent with partial π-delocalization involving its lone pair. The two phenyl rings are markedly inclined to the imidazolone plane, with dihedral angles of 74.98 (9) and 59.67 (8)°. In the crystal, weak C—H⋯O and C—H⋯π inter­actions contribute to the three-dimensional packing arrangement. Hirshfeld surface analysis shows that H⋯H contacts dominate the inter­molecular inter­actions, accounting for 68.5% of the surface, followed by C⋯H/H⋯C (19.1%) and O⋯H/H⋯O (6.1%) contacts. A comparison with related structures in the Cambridge Structural Database indicates that the geometric parameters of the heterocyclic core are consistent with those of closely related derivatives.

1. Chemical context

Hydantoin, C3H4N2O2, is a non-aromatic five-membered heterocycle that is regarded as a privileged scaffold of considerable importance in medicinal chemistry (Palkhede et al., 2026 ▸). The significance of the hydantoin core in drug discovery is highlighted by its presence in several clinically used drugs, including phenytoin, nitro­furan­toin, and enzalutamide (Shinde et al., 2026 ▸; El Moutaouakil Ala Allah et al., 2024a ▸). Furthermore, hydantoin derivatives have demonstrated therapeutic potential against a wide range of diseases, exhibiting anti­viral (Sefrji et al., 2026 ▸), anti­diabetic (Guerrab et al., 2025 ▸; El Moutaouakil Ala Allah et al., 2025a ▸), anti­microbial (El Moutaouakil Ala Allah et al., 2024a ▸, 2026a ▸), and anti­epileptic activities (El Moutaouakil Ala Allah et al., 2024b ▸). More recently, the hydantoin scaffold has also emerged as an efficient corrosion inhibitor for steel substrates (Belkheiri et al., 2024 ▸; Dahmani et al., 2025 ▸; Safir et al., 2025 ▸). This work is part of our ongoing research program devoted to the chemistry of hydantoin derivatives (El Moutaouakil Ala Allah et al., 2023 ▸; Guerrab et al., 2022 ▸, 2023 ▸). Herein, we report the chemical synthesis and crystal structure of the title compound, C21H24N2OS, (3).1.

2. Structural commentary

In the title mol­ecule (Fig. 1 ▸), the imidazolone ring is essentially planar, with a maximum deviation from the mean plane of 0.010 (2) Å for C1. Atom C6 lies 0.049 (2) Å from this plane. The coordination about N1 is essentially planar, indicating involvement of its lone pair in N→C π-bonding. This is reflected in the N1—C1 and N1—C2 bond lengths of 1.397 (2) and 1.3749 (19) Å, respectively, which are shorter than a typical Csp2—Nsp3bond but longer than the formal C1=N2 of 1.281 (2) Å. The dihedral angles between the mean plane of the imidazolone ring and those of the C10–C15 and the C16–C21 benzene rings are 74.98 (9) and 59.67 (8)°, respectively. The C4—S1—C1—N1 torsion angle of −178.78 (12)° indicates the α carbon atom of the ethyl group lies essentially in the plane of the imidazolone ring, which is a common feature of the alkyl- or aryl­thio group in this class of compounds. By contrast, the C1—N1—C6—C7 torsion angle is 76.9 (2)°, placing the isobutyl group approximately perpendicular to the imidazolone plane.

Figure 1.

Figure 1

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Perspective view of the title mol­ecule with labeling scheme and 40% probability displacement ellipsoids.

3. Supra­molecular features

The crystal packing features C5—H5C⋯O1ii hydrogen bonds together with C5—H5A⋯Cg2i inter­actions (Table 1 ▸), which generate chains of mol­ecules extending parallel to [10Inline graphic]. These chains are connected by C14—H14⋯Cg3iii inter­actions (Table 1 ▸), forming the three-dimensional crystal packing (Fig. 2 ▸).

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg3 are the centroids of the C10–C15 and C16–C21 benzene rings, respectively.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5A⋯Cg2i 0.98 2.90 3.670 (2) 136
C5—H5C⋯O1ii 0.98 2.57 3.487 (2) 156
C14—H14⋯Cg3iii 0.95 2.79 3.6536 (17) 151
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic.

Figure 2.

Figure 2

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

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to June 2026; Groom et al., 2016 ▸) with the fragment pictured in Fig. 3 ▸ (R = C, R′ = any atom or group) returned 22 hits of which 14 were considered similar to the title mol­ecule. Of the remainder, two had connections between the two phenyl rings and the rest had the substituents on N1 and C1 as part of a ring (e.g. RR′ = –CH2CH2S–, CSD refcode DIYRAE: Karolak-Wojciechowska et al., 1985 ▸), which would markedly affect their conformations and so were considered not to be strictly comparable to the title mol­ecule. Table 2 ▸ lists the 14 hits and the title mol­ecule together with selected structural data for comparison. Since the two phenyl groups are attached to the saturated carbon atom of the imidazolone ring, there is no electronic factor to influence the rotational orientations of these rings. Thus, the inclinations of their mean planes to that of the imidazolone ring will reflect a balance between the intra­molecular and inter­molecular contacts made by the two rings. This can result in the dihedral angles being markedly different, as in EHEGIL, or very nearly the same, as in YEYYUA (Table 2 ▸). In the title mol­ecule, the former is the case. The C2—N1 and C1—N1 bond lengths in the title compound are generally comparable to those observed in the related structures, consistent with a similar degree of π-delocalization. REFVIH is the only notable exception, possibly owing to the influence of the basic di­methyl­amino substituent.

Figure 3.

Figure 3

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The search fragment used in the database survey (R = C, R′ = any atom or group).

Table 2. Results of database search (search fragment shown in Fig. 3 ▸).

Compound R R′ Dihedral angles (°) C2—N1a (Å) C1—N1a (Å) Reference
3 i-Bu SEt 74.98 (9), 59.67 (8) 1.375 (2) 1.397 (2) This work
DACXAL CH2C2H SCH2C2H 68.89 (5), 54.67 (6) 1.3766 (13) 1.4026 (13) El Moutaouakil Ala Allah et al. (2025a ▸)
EHEGIL Et SMe 83.53 (8), 59.50 (7) 1.3724 (18) 1.3959 (19) El Moutaouakil Ala Allah et al. (2025b ▸)
HOPQAI Et SEt 89.59 (6), 54.66 (6) 1.3724 (14) 1.3959 (13) El Moutaouakil Ala Allah et al. (2024c ▸)
RAHGUF CH2Ph SCH2Ph 72.05 (15), 66.59 (15), 69.00 (15), 58.50 (15) 1.375 (2), 1.380 (3) 1.399 (2), 1.402 (2) Akrad et al. (2017 ▸)
REFVIH i-Pr NMe2 66.9 (6), 57.6 (6) 1.321 (12) 1.452 (14) Mazik et al. (1996 ▸)
RIJZIW n-Pr (n-Pr)S 79.23 (6), 69.81 (6) 1.3685 (14) 1.4011 (14) Akrad et al. (2018 ▸)
ROLJAH all­yl S(all­yl) 65.27 (6), 54.82 (6) 1.3738 (14) 1.3990 (14) El Moutaouakil Ala Allah et al. (2024c ▸)
WOVJIE CH2COOEt SMe 69.52 (13), 67.03 (8) 1.371 (3) 1.406 (2) El Moutaouakil Ala Allah et al. (2024b ▸)
YEYYUA Me SMe 72.32 (7), 67.03 (8) 1.3699 (16) 1.3989 (17) El Moutaouakil Ala Allah et al. (2023 ▸)
ZOKBOU Ph b 73.62 (15), 56.82 (15) 1.372 (3) 1.408 (3) Chen et al. (2024 ▸)
ZOKBUA Ph c 71.24 (12), 53.76 (15) 1.389 (3) 1.415 (3) Chen et al. (2024 ▸)
EZOYIF vin­yl SMe 70.15 (9), 66.01 (8) 1.3868 (19) 1.4082 (19) El Moutaouakil Ala Allah et al. (2026b ▸)
OYURAF Ph Ph 65.90 (9), 53.22 (9) 1.390 (3) 1.405 (3) Goswami et al. (2026 ▸)
OYUREJ Ph 4-ClC6H4 76.05 (6), 66.78 (6) 1.3898 (14) 1.4172 (15) Goswami et al. (2026 ▸)
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Notes: (a) Atom labels refer to Fig. 3 ▸; (b) 4-(10H-pheno­thia­zine)phenyl; (c) 10-phenyl-10H-pheno­thia­zin-3-yl.

5. Hirshfeld surface analysis

The Hirshfeld dnorm surface of the title mol­ecule was calculated using CrystalExplorer (Spackman et al., 2021 ▸). The inter­pretation of Hirshfeld surfaces and associated fingerprint plots has been described in detail by Tan et al. (2019 ▸). Fig. 4 ▸ shows the dnorm surface together with two neighboring mol­ecules involved in close C—H⋯O hydrogen bonds (Table 1 ▸ and Fig. 2 ▸). Fig. 5 ▸ shows the two-dimensional fingerprint plots where the H⋯H contacts (Fig. 5 ▸b) account for 68.5% of the inter­molecular contacts, as expected from the hydrogen-rich mol­ecular periphery. The C⋯H/H⋯C inter­actions (Fig. 5 ▸c) contribute 19.1% of the total and are due largely to the two sets of C—H⋯π(ring) inter­actions (Table 1 ▸). The O⋯H/H⋯O contacts (Fig. 5 ▸d) are largely due to the C—H⋯O hydrogen bonds and appear as a pair of sharp peaks with a contribution of 6.1%. All remaining contact types together contribute approximately 6.3%.

Figure 4.

Figure 4

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The dnorm Hirshfeld surface for the title mol­ecule with two neighboring mol­ecules included. The C—H⋯O hydrogen bonds are depicted by dashed lines.

Figure 5.

Figure 5

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Two-dimensional fingerprint plots for the title mol­ecule showing all inter­molecular inter­actions (a) and those delineated into H⋯H (b), C⋯H/H⋯C (c) and O⋯H/H⋯O contacts (d).

6. Synthesis and crystallization

The reaction sequence is shown in Fig. 6 ▸. Thio­hydantoin 1 was obtained by the condensation of benzil with thio­urea according to the reported procedure (Dahmani et al., 2024 ▸). Subsequently, a selective S-alkyl­ation reaction was carried out using a 1 M aqueous sodium hydroxide solution and ethyl iodide, affording compound 2 exclusively. (The reaction was monitored by TLC and showed a single spot corresponding to compound 2.) Thereafter, isobutyl iodide was introduced to perform an N-alkyl­ation reaction, thereby substituting the nitro­gen atom at the N3 position with an isobutyl group, following a procedure similar to that previously reported by our research group (El Moutaouakil Ala Allah et al., 2026a ▸; El Moutaouakil Ala Allah et al., 2024b ▸). The solid obtained upon the synthesis was recrystallized from ethanol solution to afford thick, colorless, plate-like crystals of the title compound 3.

Figure 6.

Figure 6

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Reaction sequence for the synthesis of title compound (3).

Yield: 90%; m.p. = 411–413 K; FT-IR (ATR, cm−1): 3062 (C—H Ar), 2856 (C—H aliphatic), 1724 (C=O); 1H NMR (500 MHz, CDCl3): δ ppm 0.86 [d, 6H, N—CH2—CH(CH3)2], 1.38 (t, 3H, S—CH2—CH3), 1.52 [m, 1H, N—CH2—CH(CH3)2], 3.18 (q, 2H, S—CH2—CH3), 4.52 [d, 2H, N—CH2—CH(CH3)2], 7.22-7.50 (m, 10H, Ar H); 13C NMR (125 MHz, CDCl3): 13.95 (S—CH2—CH3), 20.96 [N—CH2—CH(CH3)2], 24.02 [N—CH2—CH(CH3)2], 24.48 (S—CH2—CH3), 48.56 [N—CH2—CH(CH3)2], 76.42 (C—2Ph), 126.98, 127.34, 128.15, 140.46 (C—Ar), 160.32 (C=N), 178.58 (C=O).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The carbon-bound H atoms were placed in calculated positions and refined using a riding model, with C—H distances ranging from 0.95 to 1.00 Å and Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl groups.

Table 3. Experimental details.

Crystal data
Chemical formula C21H24N2OS
M r 352.48
Crystal system, space group Monoclinic, P21/n
Temperature (K) 200
a, b, c (Å) 12.7849 (4), 10.1770 (4), 14.4793 (5)
β (°) 93.627 (1)
V (Å3) 1880.16 (11)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.18
Crystal size (mm) 0.50 × 0.20 × 0.18
 
Data collection
Diffractometer Bruker D8 Venture PhotonIII
Absorption correction Multi-scan (SADABS; Krause et al., 2015 ▸)
Tmin, Tmax 0.368, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 31797, 4662, 3601
R int 0.084
(sin θ/λ)max (Å−1) 0.667
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.134, 1.05
No. of reflections 4662
No. of parameters 229
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.37, −0.34
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Computer programs: APEX5 and SAINT (Bruker, 2016 ▸), SHELXT2018/2 (Sheldrick, 2015a ▸), SHELXL2019/3 (Sheldrick, 2015b ▸), DIAMOND (Brandenburg & Putz, 2012 ▸), WinGX (Farrugia, 2012 ▸), publCIF (Westrip, 2010 ▸) and enCIFer (Allen et al., 2004 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026008790/vm2335sup1.cif

e-82-01117-sup1.cif (959.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008790/vm2335Isup2.hkl

e-82-01117-Isup2.hkl (371.3KB, hkl)
e-82-01117-Isup3.cml (7.2KB, cml)

Supporting information file. DOI: 10.1107/S2056989026008790/vm2335Isup3.cml

CCDC reference: 2583088

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

Author contributions are as follows. Conceptualization, YR; methodology, AA; investigation, AEMAA; writing (review and editing of the manuscript), YR; formal analysis, JTM and CM; supervision, YR; crystal structure determination, CM.

supplementary crystallographic information

2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Crystal data

C21H24N2OS F(000) = 752
Mr = 352.48 Dx = 1.245 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
a = 12.7849 (4) Å Cell parameters from 876 reflections
b = 10.1770 (4) Å θ = 2.1–28.3°
c = 14.4793 (5) Å µ = 0.18 mm−1
β = 93.627 (1)° T = 200 K
V = 1880.16 (11) Å3 Prismatic, colourless
Z = 4 0.5 × 0.2 × 0.18 mm
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Data collection

Bruker D8 Venture PhotonIII diffractometer 4662 independent reflections
Radiation source: fine-focus sealed tube 3601 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.084
phi & ω scan θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015) h = −15→17
Tmin = 0.368, Tmax = 0.746 k = −13→13
31797 measured reflections l = −17→19
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134 H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0615P)2 + 0.5162P] where P = (Fo2 + 2Fc2)/3
4662 reflections (Δ/σ)max = 0.001
229 parameters Δρmax = 0.37 e Å−3
0 restraints Δρmin = −0.34 e Å−3
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Special details

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.
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.54858 (11) 0.66344 (13) 0.60206 (9) 0.0278 (3)
N2 0.39377 (10) 0.58903 (13) 0.65127 (8) 0.0274 (3)
O1 0.66318 (9) 0.62966 (12) 0.72927 (8) 0.0342 (3)
S1 0.38764 (3) 0.67250 (4) 0.47352 (3) 0.03519 (15)
C1 0.44178 (13) 0.63817 (15) 0.58436 (10) 0.0271 (3)
C2 0.57631 (12) 0.62265 (15) 0.69077 (10) 0.0269 (3)
C3 0.47439 (12) 0.57100 (15) 0.72888 (10) 0.0258 (3)
C4 0.25214 (14) 0.6282 (2) 0.48617 (12) 0.0411 (4)
H4A 0.248702 0.542891 0.518714 0.049*
H4B 0.218197 0.695522 0.523524 0.049*
C5 0.19510 (14) 0.6182 (2) 0.39164 (12) 0.0412 (4)
H5A 0.120318 0.603126 0.398735 0.062*
H5B 0.223838 0.544775 0.357484 0.062*
H5C 0.204193 0.700076 0.357489 0.062*
C6 0.62030 (13) 0.72361 (16) 0.53972 (11) 0.0324 (4)
H6A 0.607960 0.684392 0.477409 0.039*
H6B 0.693230 0.702931 0.562056 0.039*
C7 0.60814 (14) 0.87310 (17) 0.53198 (11) 0.0335 (4)
H7A 0.534360 0.891899 0.508664 0.040*
C8 0.6265 (2) 0.9401 (2) 0.62452 (14) 0.0579 (6)
H8A 0.577319 0.905350 0.667684 0.087*
H8B 0.615534 1.034913 0.617007 0.087*
H8C 0.698502 0.923590 0.648995 0.087*
C9 0.6801 (2) 0.9259 (2) 0.46124 (17) 0.0642 (7)
H9A 0.666652 0.879137 0.402507 0.096*
H9B 0.753260 0.912580 0.483756 0.096*
H9C 0.666918 1.019901 0.451788 0.096*
C10 0.45030 (12) 0.65603 (15) 0.81209 (10) 0.0257 (3)
C11 0.38800 (13) 0.76706 (16) 0.80080 (11) 0.0315 (4)
H11 0.357788 0.789197 0.741197 0.038*
C12 0.36958 (15) 0.84610 (18) 0.87632 (12) 0.0377 (4)
H12 0.326397 0.921698 0.868114 0.045*
C13 0.41353 (15) 0.81557 (18) 0.96311 (12) 0.0379 (4)
H13 0.400307 0.869573 1.014598 0.045*
C14 0.47704 (15) 0.70581 (18) 0.97485 (11) 0.0379 (4)
H14 0.508293 0.685140 1.034349 0.046*
C15 0.49503 (14) 0.62613 (17) 0.89990 (10) 0.0323 (4)
H15 0.538165 0.550538 0.908400 0.039*
C16 0.48008 (12) 0.42469 (15) 0.75309 (9) 0.0252 (3)
C17 0.57366 (13) 0.35568 (17) 0.76168 (10) 0.0302 (4)
H17 0.637946 0.400188 0.754477 0.036*
C18 0.57412 (14) 0.22169 (17) 0.78077 (11) 0.0350 (4)
H18 0.638608 0.175096 0.785975 0.042*
C19 0.48140 (15) 0.15620 (17) 0.79216 (12) 0.0379 (4)
H19 0.481744 0.064505 0.804451 0.046*
C20 0.38766 (14) 0.22508 (18) 0.78555 (13) 0.0386 (4)
H20 0.323665 0.180729 0.794339 0.046*
C21 0.38704 (13) 0.35831 (17) 0.76619 (12) 0.0339 (4)
H21 0.322500 0.404829 0.761809 0.041*
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0326 (7) 0.0267 (7) 0.0245 (6) −0.0009 (5) 0.0045 (5) 0.0011 (5)
N2 0.0309 (7) 0.0293 (7) 0.0217 (6) 0.0022 (5) −0.0012 (5) 0.0019 (5)
O1 0.0283 (6) 0.0370 (7) 0.0371 (6) −0.0009 (5) 0.0003 (5) 0.0014 (5)
S1 0.0438 (3) 0.0392 (3) 0.0220 (2) −0.00504 (18) −0.00225 (17) 0.00514 (16)
C1 0.0353 (9) 0.0224 (8) 0.0233 (7) 0.0021 (6) 0.0003 (6) −0.0016 (6)
C2 0.0308 (8) 0.0235 (8) 0.0265 (7) 0.0025 (6) 0.0027 (6) −0.0020 (6)
C3 0.0276 (8) 0.0285 (8) 0.0212 (7) 0.0017 (6) 0.0005 (6) 0.0012 (6)
C4 0.0395 (10) 0.0547 (12) 0.0287 (8) −0.0013 (8) −0.0010 (7) 0.0025 (8)
C5 0.0389 (10) 0.0498 (11) 0.0342 (9) 0.0050 (8) −0.0029 (7) −0.0003 (8)
C6 0.0378 (9) 0.0303 (9) 0.0302 (8) 0.0005 (7) 0.0112 (7) 0.0009 (6)
C7 0.0380 (9) 0.0304 (9) 0.0323 (8) 0.0002 (7) 0.0051 (7) 0.0024 (7)
C8 0.0931 (17) 0.0360 (11) 0.0438 (11) −0.0006 (11) −0.0015 (11) −0.0059 (9)
C9 0.0847 (17) 0.0424 (12) 0.0696 (15) −0.0062 (11) 0.0369 (13) 0.0097 (10)
C10 0.0269 (8) 0.0272 (8) 0.0232 (7) −0.0014 (6) 0.0023 (6) 0.0007 (6)
C11 0.0342 (9) 0.0318 (9) 0.0284 (7) 0.0037 (7) 0.0019 (6) 0.0014 (6)
C12 0.0426 (10) 0.0323 (9) 0.0385 (9) 0.0065 (7) 0.0055 (8) −0.0023 (7)
C13 0.0483 (11) 0.0348 (10) 0.0314 (8) −0.0024 (8) 0.0087 (7) −0.0057 (7)
C14 0.0505 (11) 0.0393 (10) 0.0237 (7) −0.0003 (8) −0.0006 (7) 0.0005 (7)
C15 0.0400 (9) 0.0315 (9) 0.0251 (7) 0.0030 (7) 0.0002 (6) 0.0016 (6)
C16 0.0306 (8) 0.0260 (8) 0.0187 (6) 0.0012 (6) −0.0002 (6) −0.0004 (5)
C17 0.0306 (8) 0.0342 (9) 0.0262 (7) 0.0026 (7) 0.0045 (6) 0.0005 (6)
C18 0.0397 (10) 0.0335 (9) 0.0319 (8) 0.0089 (7) 0.0028 (7) 0.0015 (7)
C19 0.0513 (11) 0.0274 (9) 0.0348 (9) 0.0002 (8) −0.0002 (8) 0.0008 (7)
C20 0.0373 (10) 0.0351 (10) 0.0428 (9) −0.0073 (7) −0.0028 (7) 0.0050 (7)
C21 0.0299 (9) 0.0334 (9) 0.0379 (9) 0.0009 (7) −0.0016 (7) 0.0034 (7)
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Geometric parameters (Å, º)

N1—C2 1.3749 (19) C9—H9A 0.9800
N1—C1 1.397 (2) C9—H9B 0.9800
N1—C6 1.461 (2) C9—H9C 0.9800
N2—C1 1.281 (2) C10—C11 1.386 (2)
N2—C3 1.4873 (18) C10—C15 1.394 (2)
O1—C2 1.2128 (19) C11—C12 1.390 (2)
S1—C1 1.7426 (15) C11—H11 0.9500
S1—C4 1.8107 (19) C12—C13 1.379 (2)
C2—C3 1.539 (2) C12—H12 0.9500
C3—C16 1.530 (2) C13—C14 1.385 (3)
C3—C10 1.530 (2) C13—H13 0.9500
C4—C5 1.513 (2) C14—C15 1.386 (2)
C4—H4A 0.9900 C14—H14 0.9500
C4—H4B 0.9900 C15—H15 0.9500
C5—H5A 0.9800 C16—C17 1.386 (2)
C5—H5B 0.9800 C16—C21 1.391 (2)
C5—H5C 0.9800 C17—C18 1.391 (2)
C6—C7 1.533 (2) C17—H17 0.9500
C6—H6A 0.9900 C18—C19 1.379 (3)
C6—H6B 0.9900 C18—H18 0.9500
C7—C8 1.509 (3) C19—C20 1.386 (3)
C7—C9 1.518 (3) C19—H19 0.9500
C7—H7A 1.0000 C20—C21 1.384 (2)
C8—H8A 0.9800 C20—H20 0.9500
C8—H8B 0.9800 C21—H21 0.9500
C8—H8C 0.9800
C2—N1—C1 107.87 (13) H8A—C8—H8C 109.5
C2—N1—C6 124.67 (13) H8B—C8—H8C 109.5
C1—N1—C6 127.45 (13) C7—C9—H9A 109.5
C1—N2—C3 106.10 (13) C7—C9—H9B 109.5
C1—S1—C4 100.59 (8) H9A—C9—H9B 109.5
N2—C1—N1 116.28 (13) C7—C9—H9C 109.5
N2—C1—S1 126.40 (12) H9A—C9—H9C 109.5
N1—C1—S1 117.30 (11) H9B—C9—H9C 109.5
O1—C2—N1 125.88 (15) C11—C10—C15 119.01 (14)
O1—C2—C3 128.80 (14) C11—C10—C3 120.71 (13)
N1—C2—C3 105.30 (12) C15—C10—C3 120.21 (14)
N2—C3—C16 108.29 (12) C10—C11—C12 120.25 (15)
N2—C3—C10 111.14 (12) C10—C11—H11 119.9
C16—C3—C10 112.26 (12) C12—C11—H11 119.9
N2—C3—C2 104.42 (11) C13—C12—C11 120.46 (16)
C16—C3—C2 112.66 (12) C13—C12—H12 119.8
C10—C3—C2 107.83 (12) C11—C12—H12 119.8
C5—C4—S1 109.56 (13) C12—C13—C14 119.70 (16)
C5—C4—H4A 109.8 C12—C13—H13 120.1
S1—C4—H4A 109.8 C14—C13—H13 120.1
C5—C4—H4B 109.8 C13—C14—C15 120.06 (15)
S1—C4—H4B 109.8 C13—C14—H14 120.0
H4A—C4—H4B 108.2 C15—C14—H14 120.0
C4—C5—H5A 109.5 C14—C15—C10 120.51 (16)
C4—C5—H5B 109.5 C14—C15—H15 119.7
H5A—C5—H5B 109.5 C10—C15—H15 119.7
C4—C5—H5C 109.5 C17—C16—C21 118.83 (15)
H5A—C5—H5C 109.5 C17—C16—C3 122.81 (14)
H5B—C5—H5C 109.5 C21—C16—C3 118.36 (14)
N1—C6—C7 113.35 (13) C16—C17—C18 120.48 (16)
N1—C6—H6A 108.9 C16—C17—H17 119.8
C7—C6—H6A 108.9 C18—C17—H17 119.8
N1—C6—H6B 108.9 C19—C18—C17 120.31 (16)
C7—C6—H6B 108.9 C19—C18—H18 119.8
H6A—C6—H6B 107.7 C17—C18—H18 119.8
C8—C7—C9 111.88 (18) C18—C19—C20 119.56 (16)
C8—C7—C6 111.99 (15) C18—C19—H19 120.2
C9—C7—C6 109.72 (15) C20—C19—H19 120.2
C8—C7—H7A 107.7 C21—C20—C19 120.19 (16)
C9—C7—H7A 107.7 C21—C20—H20 119.9
C6—C7—H7A 107.7 C19—C20—H20 119.9
C7—C8—H8A 109.5 C20—C21—C16 120.61 (16)
C7—C8—H8B 109.5 C20—C21—H21 119.7
H8A—C8—H8B 109.5 C16—C21—H21 119.7
C7—C8—H8C 109.5
C3—N2—C1—N1 −1.77 (18) C16—C3—C10—C11 −144.20 (15)
C3—N2—C1—S1 176.61 (11) C2—C3—C10—C11 91.13 (17)
C2—N1—C1—N2 2.02 (19) N2—C3—C10—C15 160.33 (14)
C6—N1—C1—N2 −177.34 (14) C16—C3—C10—C15 38.87 (19)
C2—N1—C1—S1 −176.51 (11) C2—C3—C10—C15 −85.80 (17)
C6—N1—C1—S1 4.1 (2) C15—C10—C11—C12 −0.8 (2)
C4—S1—C1—N2 2.86 (17) C3—C10—C11—C12 −177.78 (15)
C4—S1—C1—N1 −178.78 (12) C10—C11—C12—C13 0.4 (3)
C1—N1—C2—O1 −179.99 (15) C11—C12—C13—C14 0.4 (3)
C6—N1—C2—O1 −0.6 (2) C12—C13—C14—C15 −0.9 (3)
C1—N1—C2—C3 −1.22 (16) C13—C14—C15—C10 0.5 (3)
C6—N1—C2—C3 178.16 (13) C11—C10—C15—C14 0.3 (2)
C1—N2—C3—C16 −119.41 (13) C3—C10—C15—C14 177.31 (15)
C1—N2—C3—C10 116.85 (14) N2—C3—C16—C17 130.03 (14)
C1—N2—C3—C2 0.85 (16) C10—C3—C16—C17 −106.90 (16)
O1—C2—C3—N2 179.00 (15) C2—C3—C16—C17 15.06 (19)
N1—C2—C3—N2 0.28 (15) N2—C3—C16—C21 −49.41 (17)
O1—C2—C3—C16 −63.7 (2) C10—C3—C16—C21 73.67 (17)
N1—C2—C3—C16 117.56 (13) C2—C3—C16—C21 −164.37 (13)
O1—C2—C3—C10 60.7 (2) C21—C16—C17—C18 1.6 (2)
N1—C2—C3—C10 −118.01 (13) C3—C16—C17—C18 −177.83 (14)
C1—S1—C4—C5 −166.01 (13) C16—C17—C18—C19 −0.6 (2)
C2—N1—C6—C7 −102.35 (18) C17—C18—C19—C20 −0.8 (3)
C1—N1—C6—C7 76.9 (2) C18—C19—C20—C21 1.0 (3)
N1—C6—C7—C8 58.9 (2) C19—C20—C21—C16 0.0 (3)
N1—C6—C7—C9 −176.20 (16) C17—C16—C21—C20 −1.3 (2)
N2—C3—C10—C11 −22.7 (2) C3—C16—C21—C20 178.12 (15)
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2-(Ethylsulfanyl)-3-(2-methylpropyl)-5,5-diphenyl-4,5-dihydro-3H-imidazol-4-one . Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of the C10–C15 and C16–C21 benzene rings, respectively.

D—H···A D—H H···A D···A D—H···A
C5—H5A···Cg2i 0.98 2.90 3.670 (2) 136
C5—H5C···O1ii 0.98 2.57 3.487 (2) 156
C14—H14···Cg3iii 0.95 2.79 3.6536 (17) 151
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Symmetry codes: (i) x−3/2, −y+1/2, z−3/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+2.

Funding Statement

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).

References

  1. Akrad, R., Guerrab, W., Lazrak, F., Ansar, M. J., Taoufik, F., Mague, J. T. & Ramli, Y. (2018). IUCrData3, x180934.
  2. Akrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData2, x170033.
  3. Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst.37, 335–338.
  4. Belkheiri, A., Dahmani, K., Aribou, Z., Kharbouch, O., Nordine, E., Moutaouakil Ala Allah, A. E., Galai, M., Touhami, M. E., Al-Sadoon, M. K., Al-Maswari, B. M. & Ramli, Y. (2024). Int. J. Electrochem. Sci.19, 100768.
  5. Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
  6. Bruker (2016). APEX5 and SAINT. Bruker AXS, Madison, Wisconsin, USA.
  7. Chen, J., Wang, H., Yu, Y., Liu, J., Zhao, F., Li, W. & Dong, Y. (2024). Chem. Commun.60, 1888–1891. [DOI] [PubMed]
  8. Dahmani, K., Ala Allah, A. E. M., Aribou, Z., Kharbouch, O., Galai, M., Almeer, R., Touhami, M. E., Ramli, Y., Cherkaoui, M., Chaouiki, A. & Ko, Y. G. (2025). Colloids Surf. A Physicochem. Eng. Asp.704, 135376.
  9. Dahmani, K., Allah, A. E. M. A., Ech-chebab, A., Kharbouch, O., Khattabi, M., Galai, M., AlObaid, A. A., Warad, I., Elgendy, A., Touhami, M. E., Ramli, Y. & cherkaoui, M. (2024). J. Mol. Struct.1312, 138612.
  10. El Moutaouakil Ala Allah, A., Aru, M., El Houssni, I., Das, P., Seth, S. K., Massera, C., Alzahrani, A. Y. A. & Ramli, Y. (2026a). J. Mol. Struct.1377, 147193.
  11. El Moutaouakil Ala Allah, A., Guerrab, W., Alsubari, A., Mague, J. T. & Ramli, Y. (2023). IUCrData8, x230208. [DOI] [PMC free article] [PubMed]
  12. El Moutaouakil Ala Allah, A., Guerrab, W., Maatallah, M., Mague, J. T., Talbaoui, A., Alzahrani, A. Y. A. & Ramli, Y. (2024a). J. Mol. Struct.1310, 138324.
  13. El Moutaouakil Ala Allah, A., Kariuki, B. M., Alsubari, A., Al-Sulami, A. I., Allehyani, B. H., Alsulami, W. O., Mague, J. T. & Ramli, Y. (2024b). Acta Cryst. E80, 926–930. [DOI] [PMC free article] [PubMed]
  14. El Moutaouakil Ala Allah, A., Massera, C., Mague, J. T., Alsubari, A. & Ramli, Y. (2026b). Acta Cryst. E82, 366–370. [DOI] [PMC free article] [PubMed]
  15. El Moutaouakil Ala Allah, A., Massera, C., Guerrab, W., Alsubari, A., Mague, J. T. & Ramli, Y. (2025a). Acta Cryst. E81, 801–805. [DOI] [PMC free article] [PubMed]
  16. El Moutaouakil Ala Allah, A., Mortada, S., Tüzün, B., Guerrab, W., Qostal, M., Mague, J. T., Talbaoui, A., Yahya Abdullah Alzahrani, A., Faouzi, M. E. A. & Ramli, Y. (2025b). J. Mol. Struct.1335, 141995.
  17. El Moutaouakil Ala Allah, A., Temel, Y., Guerrab, W., Nchioua, I., Mague, J. T., Talbaoui, A., Alzahrani, A. Y. A. & Ramli, Y. (2024c). J. Mol. Struct.1312, 138572.
  18. Farrugia, L. J. (2012). J. Appl. Cryst.45, 849–854.
  19. Goswami, S. P., Nad, S., Mohapatra, S., Kisan, H. K. & Mukherjee, A. (2026). ChemCatChem18, e01783.
  20. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
  21. Guerrab, W., El Moutaouakil Ala Allah, A., Alsubari, A., Mague, J. T. & Ramli, Y. (2022). IUCrData7, x220598. [DOI] [PMC free article] [PubMed]
  22. Guerrab, W., El Moutaouakil Ala Allah, A., Alsubari, A., Mague, J. T. & Ramli, Y. (2023). IUCrData8, x230060. [DOI] [PMC free article] [PubMed]
  23. Guerrab, W., Mortada, S., El Moutaouakil Ala Allah, A., Demirtaş, G., Mague, J. T., Alzahrani, A. Y. A., AL Mughram, M. H., Faouzi, M. E. A. & Ramli, Y. (2025). J. Mol. Struct.1333, 141802.
  24. Karolak-Wojciechowska, J., Mikołajczyk, M., Zatorski, A., Kiec-Kononowicz, K. & Zejc, A. (1985). Tetrahedron41, 4593–4602.
  25. Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst.48, 3–10. [DOI] [PMC free article] [PubMed]
  26. Mazik, M., Sustmann, R. & Boese, R. (1996). Liebigs Ann. Recl pp. 1665–1671.
  27. Palkhede, J. D., Park, E.-J., Darlami, O. & Shin, D. (2026). Molecules pp. 31. [DOI] [PMC free article] [PubMed]
  28. Safir, E., El Moutaouakil Ala Allah, A., Ettahiri, W., Boutaqqa, O., Alanazi, A. S., Taleb, A., Maatallah, M., Rais, Z., Wiedmer, S. K., Ramli, Y. & Taleb, M. (2025). J. Mol. Struct.1346, 143149.
  29. Sefrji, F. O., Ageeli, A. A., Halawani, N. M., Qurban, J., Abualnaja, M. M., Alsahag, M., Alisaac, A. & Abu-Melha, S. (2026). Arab. J. Sci. Eng.51, 1547–1565.
  30. Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
  31. Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
  32. Shinde, N. V., Patole, V. P., Kumbhare, M. R., Narkhede, H., Satalkar, A. T., Thube, A. V. & Bhosale, S. K. (2026). Futur J. Pharm. Sci.12, 13.
  33. Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst.54, 1006–1011. [DOI] [PMC free article] [PubMed]
  34. Tan, S. L., Jotani, M. M. & Tiekink, E. R. T. (2019). Acta Cryst. E75, 308–318. [DOI] [PMC free article] [PubMed]
  35. Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026008790/vm2335sup1.cif

e-82-01117-sup1.cif (959.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008790/vm2335Isup2.hkl

e-82-01117-Isup2.hkl (371.3KB, hkl)
e-82-01117-Isup3.cml (7.2KB, cml)

Supporting information file. DOI: 10.1107/S2056989026008790/vm2335Isup3.cml

CCDC reference: 2583088

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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