3-Methyl-2-(methyl­sulfan­yl)-5,5-diphenyl-3,5-di­hydro-4H-imidazol-4-one

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

doi:10.1107/S2414314623002080

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 3| March 2023| x230208

https://doi.org/10.1107/S2414314623002080

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access

3-Methyl-2-(methylsulfanyl)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one

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

^aLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21 September University, Yemen, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: alsubaripharmaco@21umas.edu.ye, y.ramli@um5r.ac.ma

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 2 March 2023; accepted 3 March 2023; online 10 March 2023)

This article is part of a collection of articles to commemorate the founding of the African Crystallographic Association and the 75th anniversary of the IUCr.

In the title molecule, C₁₇H₁₆N₂OS, the dihydroimidazolone ring is slightly puckered and the methylsulfanyl group is nearly coplanar with it. In the crystal, two sets of C—H⋯O hydrogen bonds form corrugated layers of molecules parallel to the ac plane. The layers pack with normal van der Waals contacts between them.

Keywords: crystal structure; hydrogen bond; dihydroimidazolone; alkylation.

CCDC reference: 2246179

Structure description

Imidazole and its derivatives display various biological effects such as insecticides, herbicides and fungicides (Tutino et al., 2009 ; Wu et al., 2023 ; Takle et al., 2006 ). Our team has been working on these derivatives for some years to evaluate their biological activities (e.g. Guerrab et al., 2022a ,b ) and corrosion inhibition activities (e.g. Nabah et al., 2020 ). In a continuation of our recent work focused on the synthesis and biological evaluation of phenytoin derivatives (e.g. Guerrab et al., 2023 ), we report here the crystal structure of the title compound (Fig. 1).

Figure 1
The title molecule with the atom-labeling scheme and 50% probability ellipsoids.

The molecule adopts the conformation typical for this class of molecule with the phenyl groups projecting out above and below the plane of the dihydroimidazolone ring. The latter ring is slightly puckered [C1 and C2 deviate by −0.0122 (7) and 0.0121 (7) Å, respectively, from the mean plane] and the mean planes of the C4–C9 and C10–C15 rings are inclined to its mean plane by 72.32 (5) and 67.03 (3)°, respectively. The terminal carbon atom of the methylsulfanyl group lies close to the mean plane of the dihydroimidazolone ring, as indicated by the C17—S1—C3—N2 torsion angle of −2.75 (13)°. In the crystal, C7—H7⋯O1 hydrogen bonds (Table 1) form chains of molecules extending along the a-axis direction. These are linked by C15—H15⋯O1 hydrogen bonds, forming corrugated layers of molecules parallel to the ac plane (Table 1 and Fig. 2). The layers pack along the b-axis direction with normal van de Waals contacts (Fig. 3) between them.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.95	2.55	3.390 (2)	148
C15—H15⋯O1ⁱⁱ	0.95	2.59	3.3797 (17)	140
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
A portion of one layer viewed along the b-axis direction with C—H⋯O hydrogen bonds depicted by dashed lines. Non-interacting hydrogen atoms are omitted for clarity.

Figure 3
Packing viewed along the a-axis direction giving end views of parts of four layers with C—H⋯O hydrogen bonds depicted by dashed lines. Non-interacting hydrogen atoms are omitted for clarity.

Synthesis and crystallization

Thiohydantoin (1000 mg, 3.73 mmol) was placed in a flask with K₂CO₃ (1030 mg, 7.46 mmol) in 20 ml of absolute dimethylformamide (DMF), and two equivalents of iodomethane (0.5 ml, 1160 mg) were added. The solution was left stirring for 2 h at room temperature. The reaction mixture was filtered, and the solvent was distilled off under reduced pressure. The residue obtained was recrystallized from methanol solution to yield colorless, plate-like single crystals (Akrad et al., 2018 ).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂OS
M_r	296.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	8.4129 (1), 22.9217 (4), 8.6719 (1)
β (°)	117.417 (1)
V (Å³)	1484.44 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.93
Crystal size (mm)	0.20 × 0.06 × 0.03

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 3 CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.85, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	37955, 2930, 2733
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.04
No. of reflections	2930
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24
Computer programs: APEX4 and SAINT (Bruker, 2021 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2246179

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314623002080/vm4058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002080/vm4058Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623002080/vm4058Isup3.cml

checkCIF report

Computing details top

Data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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

Crystal data top

C₁₇H₁₆N₂OS	F(000) = 624
M_r = 296.38	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.4129 (1) Å	Cell parameters from 9855 reflections
b = 22.9217 (4) Å	θ = 3.9–72.4°
c = 8.6719 (1) Å	µ = 1.93 mm⁻¹
β = 117.417 (1)°	T = 150 K
V = 1484.44 (4) Å³	Plate, colourless
Z = 4	0.20 × 0.06 × 0.03 mm

Data collection top

Bruker D8 VENTURE PHOTON 3 CPAD diffractometer	2930 independent reflections
Radiation source: INCOATEC IµS micro—-focus source	2733 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 7.3910 pixels mm^-1	θ_max = 72.4°, θ_min = 3.9°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −28→28
T_min = 0.85, T_max = 0.94	l = −10→10
37955 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.040P)² + 0.6009P] where P = (F_o² + 2F_c²)/3
2930 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 15 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was θ-dependent and ranged from 5 to 15 sec/frame.

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
S1	0.72407 (4)	0.53586 (2)	1.16914 (4)	0.02823 (11)
O1	0.54051 (12)	0.71912 (4)	0.82460 (12)	0.0271 (2)
N1	0.61671 (14)	0.63912 (5)	1.00499 (13)	0.0236 (2)
N2	0.70761 (14)	0.57313 (4)	0.86599 (13)	0.0217 (2)
C1	0.64968 (16)	0.62639 (5)	0.75658 (15)	0.0202 (2)
C2	0.59464 (16)	0.66941 (5)	0.86029 (16)	0.0216 (2)
C3	0.68352 (15)	0.58379 (5)	0.99846 (15)	0.0216 (2)
C4	0.80769 (16)	0.64949 (5)	0.73319 (16)	0.0219 (3)
C5	0.92075 (18)	0.69236 (6)	0.84133 (18)	0.0305 (3)
H5	0.896928	0.709387	0.928442	0.037*
C6	1.0688 (2)	0.71050 (7)	0.8226 (2)	0.0369 (3)
H6	1.145882	0.739664	0.897666	0.044*
C7	1.10450 (18)	0.68648 (7)	0.69606 (19)	0.0346 (3)
H7	1.205289	0.699222	0.683353	0.041*
C8	0.99264 (19)	0.64370 (6)	0.58764 (18)	0.0321 (3)
H8	1.016772	0.626991	0.500337	0.039*
C9	0.84503 (17)	0.62513 (6)	0.60624 (17)	0.0260 (3)
H9	0.769091	0.595615	0.531833	0.031*
C10	0.48418 (16)	0.61446 (5)	0.58351 (15)	0.0209 (2)
C11	0.39872 (18)	0.56066 (6)	0.54725 (17)	0.0273 (3)
H11	0.443592	0.530142	0.630553	0.033*
C12	0.24745 (19)	0.55132 (6)	0.38914 (19)	0.0337 (3)
H12	0.190002	0.514342	0.364685	0.040*
C13	0.18031 (17)	0.59563 (6)	0.26740 (17)	0.0301 (3)
H13	0.076931	0.589203	0.159682	0.036*
C14	0.26501 (17)	0.64947 (6)	0.30376 (17)	0.0277 (3)
H14	0.218962	0.680058	0.220802	0.033*
C15	0.41649 (17)	0.65893 (6)	0.46046 (16)	0.0249 (3)
H15	0.474305	0.695842	0.484019	0.030*
C16	0.5778 (2)	0.66282 (7)	1.13960 (19)	0.0364 (3)
H16A	0.690265	0.671538	1.243296	0.055*
H16B	0.509363	0.634189	1.168803	0.055*
H16C	0.507500	0.698691	1.097364	0.055*
C17	0.7916 (2)	0.47276 (6)	1.0905 (2)	0.0348 (3)
H17A	0.700908	0.464056	0.971597	0.052*
H17B	0.804208	0.439295	1.165589	0.052*
H17C	0.906603	0.480549	1.091373	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03234 (19)	0.03103 (18)	0.02251 (17)	0.00075 (12)	0.01364 (14)	0.00651 (12)
O1	0.0333 (5)	0.0212 (4)	0.0296 (5)	0.0024 (4)	0.0169 (4)	−0.0003 (4)
N1	0.0283 (5)	0.0254 (5)	0.0210 (5)	0.0013 (4)	0.0146 (4)	−0.0003 (4)
N2	0.0236 (5)	0.0217 (5)	0.0209 (5)	0.0003 (4)	0.0112 (4)	0.0020 (4)
C1	0.0232 (6)	0.0197 (5)	0.0202 (6)	0.0001 (4)	0.0120 (5)	0.0006 (4)
C2	0.0207 (6)	0.0239 (6)	0.0210 (6)	−0.0026 (5)	0.0102 (5)	−0.0018 (5)
C3	0.0201 (6)	0.0240 (6)	0.0206 (6)	−0.0016 (4)	0.0092 (5)	0.0011 (5)
C4	0.0213 (6)	0.0249 (6)	0.0199 (6)	0.0016 (4)	0.0098 (5)	0.0046 (5)
C5	0.0308 (7)	0.0374 (7)	0.0256 (6)	−0.0069 (6)	0.0150 (6)	−0.0020 (5)
C6	0.0305 (7)	0.0444 (8)	0.0340 (8)	−0.0126 (6)	0.0132 (6)	0.0001 (6)
C7	0.0235 (6)	0.0466 (8)	0.0359 (8)	0.0009 (6)	0.0157 (6)	0.0139 (6)
C8	0.0300 (7)	0.0418 (8)	0.0312 (7)	0.0081 (6)	0.0199 (6)	0.0080 (6)
C9	0.0262 (6)	0.0292 (6)	0.0250 (6)	0.0030 (5)	0.0137 (5)	0.0022 (5)
C10	0.0216 (6)	0.0239 (6)	0.0208 (6)	0.0007 (4)	0.0130 (5)	−0.0014 (4)
C11	0.0279 (6)	0.0237 (6)	0.0297 (7)	−0.0007 (5)	0.0129 (5)	0.0006 (5)
C12	0.0295 (7)	0.0294 (7)	0.0371 (8)	−0.0057 (5)	0.0111 (6)	−0.0065 (6)
C13	0.0231 (6)	0.0398 (7)	0.0250 (6)	0.0013 (5)	0.0090 (5)	−0.0068 (5)
C14	0.0274 (7)	0.0334 (7)	0.0229 (6)	0.0056 (5)	0.0122 (5)	0.0030 (5)
C15	0.0280 (6)	0.0246 (6)	0.0245 (6)	−0.0005 (5)	0.0141 (5)	0.0003 (5)
C16	0.0501 (9)	0.0395 (8)	0.0285 (7)	0.0082 (6)	0.0257 (7)	−0.0008 (6)
C17	0.0381 (8)	0.0278 (7)	0.0356 (8)	0.0051 (6)	0.0145 (6)	0.0074 (6)

Geometric parameters (Å, º) top

S1—C3	1.7461 (12)	C8—H8	0.9500
S1—C17	1.7995 (15)	C9—H9	0.9500
O1—C2	1.2130 (15)	C10—C11	1.3887 (17)
N1—C2	1.3699 (16)	C10—C15	1.3937 (17)
N1—C3	1.3991 (16)	C11—C12	1.3922 (19)
N1—C16	1.4550 (16)	C11—H11	0.9500
N2—C3	1.2786 (16)	C12—C13	1.384 (2)
N2—C1	1.4840 (15)	C12—H12	0.9500
C1—C4	1.5287 (16)	C13—C14	1.387 (2)
C1—C10	1.5302 (16)	C13—H13	0.9500
C1—C2	1.5426 (16)	C14—C15	1.3867 (19)
C4—C5	1.3888 (18)	C14—H14	0.9500
C4—C9	1.3932 (18)	C15—H15	0.9500
C5—C6	1.391 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.379 (2)	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C7—C8	1.384 (2)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C8—C9	1.3907 (19)

C3—S1—C17	99.02 (6)	C8—C9—H9	119.8
C2—N1—C3	108.05 (10)	C4—C9—H9	119.8
C2—N1—C16	124.06 (11)	C11—C10—C15	119.33 (12)
C3—N1—C16	127.88 (11)	C11—C10—C1	121.54 (11)
C3—N2—C1	106.02 (10)	C15—C10—C1	119.12 (11)
N2—C1—C4	108.67 (9)	C10—C11—C12	120.18 (12)
N2—C1—C10	111.27 (9)	C10—C11—H11	119.9
C4—C1—C10	112.70 (10)	C12—C11—H11	119.9
N2—C1—C2	104.57 (9)	C13—C12—C11	120.34 (13)
C4—C1—C2	111.64 (10)	C13—C12—H12	119.8
C10—C1—C2	107.71 (9)	C11—C12—H12	119.8
O1—C2—N1	125.90 (11)	C12—C13—C14	119.54 (12)
O1—C2—C1	129.05 (11)	C12—C13—H13	120.2
N1—C2—C1	105.04 (10)	C14—C13—H13	120.2
N2—C3—N1	116.26 (11)	C15—C14—C13	120.41 (12)
N2—C3—S1	126.26 (10)	C15—C14—H14	119.8
N1—C3—S1	117.47 (9)	C13—C14—H14	119.8
C5—C4—C9	118.93 (12)	C14—C15—C10	120.20 (12)
C5—C4—C1	121.51 (11)	C14—C15—H15	119.9
C9—C4—C1	119.49 (11)	C10—C15—H15	119.9
C4—C5—C6	120.28 (13)	N1—C16—H16A	109.5
C4—C5—H5	119.9	N1—C16—H16B	109.5
C6—C5—H5	119.9	H16A—C16—H16B	109.5
C7—C6—C5	120.55 (14)	N1—C16—H16C	109.5
C7—C6—H6	119.7	H16A—C16—H16C	109.5
C5—C6—H6	119.7	H16B—C16—H16C	109.5
C6—C7—C8	119.62 (13)	S1—C17—H17A	109.5
C6—C7—H7	120.2	S1—C17—H17B	109.5
C8—C7—H7	120.2	H17A—C17—H17B	109.5
C7—C8—C9	120.14 (13)	S1—C17—H17C	109.5
C7—C8—H8	119.9	H17A—C17—H17C	109.5
C9—C8—H8	119.9	H17B—C17—H17C	109.5
C8—C9—C4	120.49 (13)

C3—N2—C1—C4	121.22 (11)	C10—C1—C4—C9	−41.41 (15)
C3—N2—C1—C10	−114.13 (11)	C2—C1—C4—C9	−162.79 (11)
C3—N2—C1—C2	1.88 (12)	C9—C4—C5—C6	0.0 (2)
C3—N1—C2—O1	−179.29 (12)	C1—C4—C5—C6	176.77 (12)
C16—N1—C2—O1	−0.1 (2)	C4—C5—C6—C7	0.4 (2)
C3—N1—C2—C1	1.68 (12)	C5—C6—C7—C8	−0.4 (2)
C16—N1—C2—C1	−179.13 (12)	C6—C7—C8—C9	0.1 (2)
N2—C1—C2—O1	178.84 (12)	C7—C8—C9—C4	0.3 (2)
C4—C1—C2—O1	61.52 (16)	C5—C4—C9—C8	−0.33 (19)
C10—C1—C2—O1	−62.70 (16)	C1—C4—C9—C8	−177.20 (12)
N2—C1—C2—N1	−2.18 (12)	N2—C1—C10—C11	4.07 (15)
C4—C1—C2—N1	−119.50 (11)	C4—C1—C10—C11	126.43 (12)
C10—C1—C2—N1	116.28 (10)	C2—C1—C10—C11	−109.99 (12)
C1—N2—C3—N1	−0.95 (14)	N2—C1—C10—C15	−176.77 (10)
C1—N2—C3—S1	178.44 (9)	C4—C1—C10—C15	−54.41 (14)
C2—N1—C3—N2	−0.54 (15)	C2—C1—C10—C15	69.17 (13)
C16—N1—C3—N2	−179.68 (13)	C15—C10—C11—C12	0.28 (19)
C2—N1—C3—S1	−179.98 (8)	C1—C10—C11—C12	179.44 (12)
C16—N1—C3—S1	0.87 (18)	C10—C11—C12—C13	−0.4 (2)
C17—S1—C3—N2	−2.75 (13)	C11—C12—C13—C14	0.1 (2)
C17—S1—C3—N1	176.63 (10)	C12—C13—C14—C15	0.3 (2)
N2—C1—C4—C5	−94.40 (14)	C13—C14—C15—C10	−0.50 (19)
C10—C1—C4—C5	141.79 (12)	C11—C10—C15—C14	0.19 (18)
C2—C1—C4—C5	20.42 (16)	C1—C10—C15—C14	−178.99 (11)
N2—C1—C4—C9	82.39 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.95	2.55	3.390 (2)	148
C15—H15···O1ⁱⁱ	0.95	2.59	3.3797 (17)	140

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

Acknowledgements

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

Funding information

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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