3-Isobutyl-5,5-di­phenyl­imidazolidine-2,4-dione

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

doi:10.1107/S2414314622005983

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 6| June 2022| x220598

https://doi.org/10.1107/S2414314622005983

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access

3-Isobutyl-5,5-diphenylimidazolidine-2,4-dione

Walid Guerrab,^a Abderrazzak El Moutaouakil Ala Allah,^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

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 2 June 2022; accepted 3 June 2022; online 10 June 2022)

The imidazolidine ring in the title molecule, C₁₉H₂₀N₂O₂, is slightly `ruffled'. In the crystal, a layer structure is generated by N—H⋯O and C—H⋯O hydrogen bonds plus C—H⋯π(ring) interactions.

Keywords: crystal structure; imidazolidinedione; hydrogen bond; C—H⋯π(ring) interaction.

CCDC reference: 2176804

Structure description

Imidazolidin-2,4-dione, also known as hydantoin, is an important nucleus found in numerous natural products and in several clinically important medicines. One of the best known examples of such a derivative is phenytoine, 5,5-diphenylimidazolidine-2,4-dione, a drug widely prescribed as an anticonvulsant agent and for the treatment of many other diseases including HIV (Weichet, 1974 ; Havera & Strycker, 1976 ; Khodair et al., 1997 ; Thenmozhiyal et al., 2004 ).

Given the wide range of therapeutic applications for such compounds, and in a continuation of our work in this area (Ramli et al., 2017a ,b ; Akrad et al. 2017 ; Guerrab et al. 2019 , 2020a ,b , 2021 , 2022 ), the title compound (Fig. 1) was prepared and its crystal structure is reported here.

Figure 1
The title molecule with the labelling scheme and 50% probability ellipsoids.

The two phenyl rings (C4–C9 and C10–C15) are disposed on either side of the five-membered ring and make dihedral angles of 68.42 (3) and 73.04 (3)°, respectively, with the mean plane of the latter ring. The five-membered ring is slightly `ruffled' with deviations from the mean plane ranging from 0.206 (5) Å (N2) to −0.218 (5) Å (C3) (r.m.s. deviation = 0.0155 Å). The isobutyl group is rotated well out of the mean plane of the five-membered ring, as indicated by the C2—N1—C16—C17 torsion angle of 72.64 (10)°. In the crystal, inversion dimers are formed by pairs of N2—H2⋯O2 hydrogen bonds (Table 1) with the dimers connected by C8—H8⋯O1 hydrogen bonds, forming chains of molecules extending parallel to (10 $[\overline{1}]$ ) (Fig. 2 and Table 2). The chains are connected into layers parallel to the ac plane by C7—H7⋯Cg1 interactions (Table 1 and Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the five-membered ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.91 (1)	1.95 (1)	2.8512 (9)	174 (1)
C7—H7⋯Cg1ⁱⁱ	0.95	2.99	3.9308 (13)	170
C8—H8⋯O1ⁱⁱⁱ	0.95	2.46	3.4069 (13)	172
Symmetry codes: (i) ; (ii) x+1, y, z; (iii) .

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₂
M_r	308.37
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	8.9747 (7), 9.7306 (7), 11.8780 (8)
α, β, γ (°)	104.676 (3), 96.334 (3), 112.243 (3)
V (Å³)	903.81 (12)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.46 × 0.41 × 0.13

Data collection
Diffractometer	Bruker D8 QUEST PHOTON 3 diffractometer
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.93, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	42215, 6214, 5222
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.128, 1.05
No. of reflections	6214
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.19
Computer programs: APEX4 and SAINT (Bruker, 2021 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Figure 2
A portion of one layer viewed along the b-axis direction with N—H⋯O and C—H⋯O hydrogen bonds depicted, respectively, by violet and black dashed lines. C—H⋯π(ring) interactions are depicted by green dashed lines and non-interacting hydrogen atoms are omitted for clarity.

Figure 3
Packing viewed along the c-axis direction with intermolecular interactions depicted as in Fig. 2

and non-interacting hydrogen atoms omitted for clarity.

Synthesis and crystallization

To a solution of 5,5-diphenylimidazolidine-2,4-dione (500 mg, 1.98 mmol), one equivalent of isobutyl bromide (246.88 mL, 1.98 mmol) in absolute dimethylformamide (DMF, 15 ml) was added and the resulting solution heated under reflux for 3 h in the presence of 1.1 equivalents of K₂CO₃ (301.31 mg, 2.18 mmol). The reaction mixture was filtered while hot, and the solvent evaporated under reduced pressure. The residue obtained was dried and recrystallized from an ethanol solution to yield colourless prism-like crystals (Guerrab et al., 2018 )

Refinement

Crystal data, data collection and structure refinement details are presented in Table 2. A small amount of residual density, well removed from the main molecule and which could not be satisfactorily modelled by a plausible solvent molecule disordered across a centre of symmetry was removed with PLATON SQUEEZE (Spek, 2015 ). Three reflections affected by the beamstop were omitted from the final refinement.

Structural data

CCDC reference: 2176804

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314622005983/tk4078sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622005983/tk4078Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622005983/tk4078Isup3.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: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Isobutyl-5,5-diphenylimidazolidine-2,4-dione top

Crystal data top

C₁₉H₂₀N₂O₂	Z = 2
M_r = 308.37	F(000) = 328
Triclinic, P1	D_x = 1.133 Mg m⁻³
a = 8.9747 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7306 (7) Å	Cell parameters from 9909 reflections
c = 11.8780 (8) Å	θ = 2.5–31.9°
α = 104.676 (3)°	µ = 0.07 mm⁻¹
β = 96.334 (3)°	T = 150 K
γ = 112.243 (3)°	Thick plate, colourless
V = 903.81 (12) Å³	0.46 × 0.41 × 0.13 mm

Data collection top

Bruker D8 QUEST PHOTON 3 diffractometer	6214 independent reflections
Radiation source: fine-focus sealed tube	5222 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 7.3910 pixels mm^-1	θ_max = 32.5°, θ_min = 2.5°
φ and ω scans	h = −13→13
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −14→14
T_min = 0.93, T_max = 0.99	l = −17→17
42215 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)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0689P)² + 0.1685P] where P = (F_o² + 2F_c²)/3
6214 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 9 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX3. The scan time was 5 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 - 1.00 Å) and were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. That attached to nitrogen was placed in a location derived from a difference map and refined with a DFIX 0.91 0.01 instruction. A small amount of residual density, well-removed from the main molecule and which could not be satisfactorily modeled by a plausible solvent molecule disordered across a center of symmetry was removed with PLATON SQUEEZE (Spek, 2015). Three reflections affected by the beamstop were omitted from the final refinement.

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

	x	y	z	U_iso*/U_eq
O1	0.74629 (9)	0.64608 (8)	0.94977 (5)	0.02535 (14)
O2	0.51349 (8)	0.68712 (7)	0.60449 (5)	0.02359 (14)
N1	0.63385 (9)	0.70411 (8)	0.79418 (6)	0.01786 (13)
N2	0.62040 (9)	0.51465 (8)	0.63706 (6)	0.01972 (14)
H2	0.5822 (15)	0.4472 (13)	0.5613 (8)	0.030*
C1	0.68961 (10)	0.48254 (9)	0.73985 (7)	0.01730 (14)
C2	0.69602 (10)	0.61866 (9)	0.84376 (7)	0.01818 (15)
C3	0.58232 (10)	0.63811 (9)	0.66914 (7)	0.01764 (15)
C4	0.86580 (10)	0.49751 (9)	0.74187 (7)	0.01831 (15)
C5	0.95614 (12)	0.56243 (11)	0.66554 (8)	0.02490 (17)
H5	0.908433	0.598669	0.610614	0.030*
C6	1.11659 (13)	0.57417 (12)	0.66981 (9)	0.0306 (2)
H6	1.177780	0.617680	0.617333	0.037*
C7	1.18692 (12)	0.52243 (12)	0.75054 (10)	0.0305 (2)
H7	1.295578	0.529077	0.752362	0.037*
C8	1.09899 (11)	0.46090 (11)	0.82877 (9)	0.02727 (18)
H8	1.148247	0.427406	0.885034	0.033*
C9	0.93872 (11)	0.44843 (10)	0.82459 (8)	0.02205 (16)
H9	0.878635	0.406433	0.878110	0.026*
C10	0.57204 (10)	0.32284 (9)	0.74399 (7)	0.01842 (15)
C11	0.45908 (11)	0.30670 (10)	0.81674 (8)	0.02336 (17)
H11	0.459215	0.397322	0.870843	0.028*
C12	0.34570 (12)	0.15808 (12)	0.81053 (9)	0.02819 (19)
H12	0.268623	0.147944	0.860092	0.034*
C13	0.34519 (12)	0.02510 (11)	0.73224 (9)	0.02882 (19)
H13	0.267373	−0.075954	0.727691	0.035*
C14	0.45904 (13)	0.04021 (11)	0.66037 (9)	0.02807 (19)
H14	0.459695	−0.050708	0.607264	0.034*
C15	0.57189 (11)	0.18826 (10)	0.66618 (8)	0.02336 (17)
H15	0.649371	0.197963	0.616936	0.028*
C16	0.61826 (10)	0.84333 (9)	0.86303 (7)	0.01963 (15)
H16A	0.564388	0.820207	0.928583	0.024*
H16B	0.545921	0.868521	0.810459	0.024*
C17	0.78453 (11)	0.98600 (10)	0.91629 (8)	0.02349 (17)
H17	0.854577	0.961276	0.972365	0.028*
C18	0.75511 (15)	1.12407 (11)	0.98774 (10)	0.0339 (2)
H18A	0.689042	1.151726	0.933699	0.051*
H18B	0.861657	1.214255	1.026831	0.051*
H18C	0.695748	1.094763	1.048519	0.051*
C19	0.87543 (13)	1.02639 (13)	0.81979 (11)	0.0353 (2)
H19A	0.899177	0.938670	0.778900	0.053*
H19B	0.979417	1.120428	0.856671	0.053*
H19C	0.806095	1.046019	0.761788	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0371 (4)	0.0246 (3)	0.0156 (3)	0.0173 (3)	0.0006 (2)	0.0042 (2)
O2	0.0304 (3)	0.0223 (3)	0.0201 (3)	0.0158 (2)	−0.0010 (2)	0.0056 (2)
N1	0.0219 (3)	0.0160 (3)	0.0157 (3)	0.0104 (2)	0.0007 (2)	0.0029 (2)
N2	0.0279 (3)	0.0191 (3)	0.0142 (3)	0.0143 (3)	0.0004 (2)	0.0036 (2)
C1	0.0225 (3)	0.0167 (3)	0.0143 (3)	0.0110 (3)	0.0017 (3)	0.0046 (2)
C2	0.0218 (3)	0.0165 (3)	0.0170 (3)	0.0099 (3)	0.0027 (3)	0.0046 (3)
C3	0.0195 (3)	0.0165 (3)	0.0165 (3)	0.0083 (3)	0.0016 (3)	0.0045 (3)
C4	0.0213 (3)	0.0159 (3)	0.0178 (3)	0.0095 (3)	0.0019 (3)	0.0041 (3)
C5	0.0286 (4)	0.0262 (4)	0.0242 (4)	0.0135 (3)	0.0073 (3)	0.0115 (3)
C6	0.0283 (4)	0.0324 (5)	0.0332 (5)	0.0124 (4)	0.0119 (4)	0.0128 (4)
C7	0.0218 (4)	0.0295 (4)	0.0395 (5)	0.0114 (3)	0.0058 (4)	0.0097 (4)
C8	0.0235 (4)	0.0257 (4)	0.0329 (4)	0.0117 (3)	0.0001 (3)	0.0106 (3)
C9	0.0231 (4)	0.0214 (4)	0.0227 (4)	0.0102 (3)	0.0022 (3)	0.0087 (3)
C10	0.0213 (3)	0.0174 (3)	0.0176 (3)	0.0104 (3)	0.0015 (3)	0.0050 (3)
C11	0.0256 (4)	0.0228 (4)	0.0246 (4)	0.0133 (3)	0.0069 (3)	0.0071 (3)
C12	0.0261 (4)	0.0289 (4)	0.0311 (4)	0.0109 (3)	0.0088 (3)	0.0122 (4)
C13	0.0293 (4)	0.0214 (4)	0.0303 (4)	0.0058 (3)	0.0018 (3)	0.0094 (3)
C14	0.0344 (5)	0.0177 (4)	0.0270 (4)	0.0099 (3)	0.0018 (3)	0.0029 (3)
C15	0.0287 (4)	0.0190 (4)	0.0212 (4)	0.0112 (3)	0.0048 (3)	0.0030 (3)
C16	0.0211 (3)	0.0162 (3)	0.0212 (3)	0.0103 (3)	0.0024 (3)	0.0025 (3)
C17	0.0223 (4)	0.0167 (3)	0.0269 (4)	0.0078 (3)	−0.0009 (3)	0.0030 (3)
C18	0.0423 (5)	0.0190 (4)	0.0335 (5)	0.0128 (4)	0.0026 (4)	−0.0001 (3)
C19	0.0294 (5)	0.0288 (5)	0.0462 (6)	0.0090 (4)	0.0126 (4)	0.0132 (4)

Geometric parameters (Å, º) top

O1—C2	1.2139 (10)	C10—C15	1.3980 (11)
O2—C3	1.2259 (9)	C11—C12	1.3956 (13)
N1—C2	1.3698 (10)	C11—H11	0.9500
N1—C3	1.4045 (10)	C12—C13	1.3870 (14)
N1—C16	1.4598 (10)	C12—H12	0.9500
N2—C3	1.3465 (10)	C13—C14	1.3916 (15)
N2—C1	1.4652 (10)	C13—H13	0.9500
N2—H2	0.906 (8)	C14—C15	1.3913 (13)
C1—C4	1.5289 (11)	C14—H14	0.9500
C1—C10	1.5295 (11)	C15—H15	0.9500
C1—C2	1.5425 (11)	C16—C17	1.5273 (12)
C4—C5	1.3939 (12)	C16—H16A	0.9900
C4—C9	1.3979 (11)	C16—H16B	0.9900
C5—C6	1.3948 (13)	C17—C19	1.5250 (14)
C5—H5	0.9500	C17—C18	1.5282 (13)
C6—C7	1.3868 (14)	C17—H17	1.0000
C6—H6	0.9500	C18—H18A	0.9800
C7—C8	1.3895 (15)	C18—H18B	0.9800
C7—H7	0.9500	C18—H18C	0.9800
C8—C9	1.3911 (12)	C19—H19A	0.9800
C8—H8	0.9500	C19—H19B	0.9800
C9—H9	0.9500	C19—H19C	0.9800
C10—C11	1.3930 (12)

C2—N1—C3	111.47 (6)	C10—C11—C12	120.34 (8)
C2—N1—C16	124.21 (7)	C10—C11—H11	119.8
C3—N1—C16	124.29 (6)	C12—C11—H11	119.8
C3—N2—C1	112.87 (6)	C13—C12—C11	120.22 (9)
C3—N2—H2	120.9 (8)	C13—C12—H12	119.9
C1—N2—H2	124.6 (8)	C11—C12—H12	119.9
N2—C1—C4	112.60 (7)	C12—C13—C14	119.79 (9)
N2—C1—C10	109.66 (6)	C12—C13—H13	120.1
C4—C1—C10	112.73 (6)	C14—C13—H13	120.1
N2—C1—C2	100.71 (6)	C15—C14—C13	120.09 (9)
C4—C1—C2	108.58 (6)	C15—C14—H14	120.0
C10—C1—C2	111.97 (6)	C13—C14—H14	120.0
O1—C2—N1	125.93 (7)	C14—C15—C10	120.44 (8)
O1—C2—C1	126.97 (7)	C14—C15—H15	119.8
N1—C2—C1	107.10 (6)	C10—C15—H15	119.8
O2—C3—N2	128.11 (7)	N1—C16—C17	112.91 (7)
O2—C3—N1	124.19 (7)	N1—C16—H16A	109.0
N2—C3—N1	107.69 (6)	C17—C16—H16A	109.0
C5—C4—C9	119.56 (8)	N1—C16—H16B	109.0
C5—C4—C1	121.55 (7)	C17—C16—H16B	109.0
C9—C4—C1	118.87 (7)	H16A—C16—H16B	107.8
C4—C5—C6	119.99 (8)	C19—C17—C16	111.65 (8)
C4—C5—H5	120.0	C19—C17—C18	111.13 (8)
C6—C5—H5	120.0	C16—C17—C18	108.81 (8)
C7—C6—C5	120.10 (9)	C19—C17—H17	108.4
C7—C6—H6	120.0	C16—C17—H17	108.4
C5—C6—H6	120.0	C18—C17—H17	108.4
C6—C7—C8	120.22 (9)	C17—C18—H18A	109.5
C6—C7—H7	119.9	C17—C18—H18B	109.5
C8—C7—H7	119.9	H18A—C18—H18B	109.5
C7—C8—C9	119.90 (8)	C17—C18—H18C	109.5
C7—C8—H8	120.1	H18A—C18—H18C	109.5
C9—C8—H8	120.1	H18B—C18—H18C	109.5
C8—C9—C4	120.21 (8)	C17—C19—H19A	109.5
C8—C9—H9	119.9	C17—C19—H19B	109.5
C4—C9—H9	119.9	H19A—C19—H19B	109.5
C11—C10—C15	119.12 (8)	C17—C19—H19C	109.5
C11—C10—C1	122.52 (7)	H19A—C19—H19C	109.5
C15—C10—C1	118.25 (7)	H19B—C19—H19C	109.5

C3—N2—C1—C4	−118.52 (8)	C1—C4—C5—C6	−179.97 (8)
C3—N2—C1—C10	115.10 (8)	C4—C5—C6—C7	−0.49 (15)
C3—N2—C1—C2	−3.05 (9)	C5—C6—C7—C8	−0.99 (15)
C3—N1—C2—O1	−178.32 (8)	C6—C7—C8—C9	1.21 (15)
C16—N1—C2—O1	−0.15 (14)	C7—C8—C9—C4	0.04 (14)
C3—N1—C2—C1	1.65 (9)	C5—C4—C9—C8	−1.51 (13)
C16—N1—C2—C1	179.81 (7)	C1—C4—C9—C8	−179.85 (8)
N2—C1—C2—O1	−179.29 (9)	N2—C1—C10—C11	−97.67 (9)
C4—C1—C2—O1	−60.86 (11)	C4—C1—C10—C11	136.02 (8)
C10—C1—C2—O1	64.25 (11)	C2—C1—C10—C11	13.23 (10)
N2—C1—C2—N1	0.74 (8)	N2—C1—C10—C15	78.35 (9)
C4—C1—C2—N1	119.18 (7)	C4—C1—C10—C15	−47.96 (9)
C10—C1—C2—N1	−115.71 (7)	C2—C1—C10—C15	−170.75 (7)
C1—N2—C3—O2	−174.97 (8)	C15—C10—C11—C12	−0.97 (13)
C1—N2—C3—N1	4.19 (9)	C1—C10—C11—C12	175.01 (8)
C2—N1—C3—O2	175.58 (8)	C10—C11—C12—C13	0.34 (14)
C16—N1—C3—O2	−2.58 (13)	C11—C12—C13—C14	0.48 (15)
C2—N1—C3—N2	−3.61 (9)	C12—C13—C14—C15	−0.65 (15)
C16—N1—C3—N2	178.23 (7)	C13—C14—C15—C10	0.00 (14)
N2—C1—C4—C5	10.83 (11)	C11—C10—C15—C14	0.81 (13)
C10—C1—C4—C5	135.55 (8)	C1—C10—C15—C14	−175.35 (8)
C2—C1—C4—C5	−99.79 (9)	C2—N1—C16—C17	72.64 (10)
N2—C1—C4—C9	−170.85 (7)	C3—N1—C16—C17	−109.43 (9)
C10—C1—C4—C9	−46.14 (10)	N1—C16—C17—C19	57.80 (10)
C2—C1—C4—C9	78.52 (9)	N1—C16—C17—C18	−179.18 (7)
C9—C4—C5—C6	1.73 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the five-membered ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.91 (1)	1.95 (1)	2.8512 (9)	174 (1)
C7—H7···Cg1ⁱⁱ	0.95	2.99	3.9308 (13)	170
C8—H8···O1ⁱⁱⁱ	0.95	2.46	3.4069 (13)	172

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

Footnotes

‡Additional correspondence author, e-mail: y.ramli@um5r.ac.ma.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. Author contributions are as follows. Conceptualization, YR; methodology, WG and AS; investigation, WG, AEMAA; writing (original draft), JMT and YR; writing (review and editing of the manuscript), YR; formal analysis, AS and YR; supervision, YR; crystal-structure determination and validation, JTM.

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