Crystal structure, Hirshfeld surface analysis and inter­action energy calculation of 1-decyl-2,3-di­hydro-1H-benzimidazol-2-one

Ait Elmachkouri, Y.; Saber, A.; Irrou, E.; Amer, B.; Mague, J.T.; Hökelek, T.; Labd Taha, M.; Sebbar, N.K.; Essassi, E.M.

doi:10.1107/S2056989021004291

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 77| Part 5| May 2021| Pages 559-563

https://doi.org/10.1107/S2056989021004291

Open

access

Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one

Younesse Ait Elmachkouri,^a,^b Asmaa Saber,^b Ezaddine Irrou,^a,^b Bushra Amer,^c ^* Joel T. Mague,^d Tuncer Hökelek,^e Mohamed Labd Taha,^a Nada Kheira Sebbar ^a,^b and El Mokhtar Essassi ^b

^aLaboratoire de Chimie Appliquée et Environnement, Equipe de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^cFaculty of Medicine and Health Sciences, Sana'a University, San'a, Yemen, ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ^eDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: Bushraamer2014@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 6 April 2021; accepted 21 April 2021; online 27 April 2021)

The title molecule, C₁₇H₂₆N₂O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydrobenzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)° between the constituent planes. In the crystal, N—H⋯O hydrogen bonds form inversion dimers, which are connected into the three-dimensional structure by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (75.9%), H⋯C/C⋯H (12.5%) and H⋯O/O⋯H (7.0%) interactions. Based on computational chemistry using the CE–B3LYP/6–31 G(d,p) energy model, C—H⋯O hydrogen bond energies are −74.9 (for N—H⋯O) and −42.7 (for C—H⋯O) kJ mol⁻¹.

Keywords: crystal structure; C—H⋯π(ring) interaction; dihydroimidazole; Hirshfeld surface analysis.

CCDC reference: 2079158

1. Chemical context

Benzimidazol-2-one derivatives constitute an important class of heterocyclic systems. They are used as precursors for the preparation of novel N-substituted benzimidazol-2-one derivatives with potential biological and pharmacological properties (Lakhrissi et al., 2008 ; Saber et al., 2019 ; Mamedov et al., 2017 ), including antitumor (Khodarahmi et al., 2005 ), antibacterial (Saber et al., 2020a ; Vira et al., 2010 ), anti-HIV (Barreca et al., 2007 ), and antitrichinellosis (Mavrova et al., 2005 ) activities.

In continuation of our investigations on the synthesis, physico-chemical characterization and biological properties of novel N-substituted benzimidazol-2-one derivatives, we have studied the reaction of 1-bromodecane with 1-isopropenyl-1H-1,3-benzimidazol-2(3H)-one under phase-transfer catalysis conditions (Saber et al., 2020b ; Srhir et al., 2020 ), We report herein the synthesis, and the molecular and crystal structures along with the Hirshfeld surface analysis and the intermolecular interaction energies of the title compound, C₁₇H₂₆N₂O, (I).

2. Structural commentary

The title molecule adopts an L-shaped conformation with the straight n-decyl chain arranged nearly perpendicular to the dihydrobenzimidazole portion, as indicated by the C1—N2—C8—C9 torsion angle of −75.91 (12)° (Fig. 1). The dihydrobenzimidazole portion is not planar, as indicated by the dihedral angle of 1.20 (6)° between the constituent planes.

Figure 1
The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal of (I), inversion dimers are formed by N1—H1⋯O1 hydrogen bonds (Table 1) that are linked into chains extending parallel to the b axis by C8—H8A⋯O1 hydrogen bonds (Table 1, Fig. 2). The alkyl groups extend from both sides of the chain and intercalate with alkyl groups of adjacent chains while linking them together through C17—H17C⋯Cg2 interactions (Table 2, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱⁱ	0.923 (16)	1.932 (16)	2.8393 (12)	167.0 (13)
C8—H8A⋯O1^viii	0.995 (13)	2.573 (13)	3.4648 (12)	149.1 (9)
C17—H17C⋯Cg2^v	1.00 (2)	2.985 (19)	3.6656 (17)	126.0 (14)
Symmetry codes: (ii) ; (v) ; (viii) .

Table 2
Selected interatomic distances (Å)

O1⋯C1ⁱ	3.2784 (12)	H9B⋯H11B	2.53 (2)
O1⋯N1ⁱⁱ	2.8394 (11)	H10A⋯H12A	2.55 (2)
C4⋯O1ⁱⁱⁱ	3.2820 (14)	H10B⋯H12B	2.58 (2)
O1⋯H8B	2.486 (11)	H11A⋯H13A	2.58 (2)
O1⋯H1ⁱⁱ	1.934 (16)	H11A⋯H16A^v	2.43 (2)
O1⋯H8A^iv	2.571 (11)	H11B⋯H13B	2.51 (2)
H4⋯O1ⁱⁱⁱ	2.417 (13)	H12A⋯H14A	2.55 (2)
N1⋯H8A^iv	2.878 (12)	H12A⋯H15A^v	2.57 (2)
N1⋯H8Bⁱ	2.949 (12)	H12B⋯H14B	2.53 (2)
N2⋯H10A	2.843 (14)	H13A⋯H15A	2.55 (2)
C7⋯C7ⁱ	3.2937 (14)	H13A⋯H14A^v	2.52 (2)
C2⋯H17C^v	2.90 (2)	H13B⋯H15B	2.57 (2)
C7⋯H1ⁱⁱ	2.828 (16)	H13B⋯H16B^vii	2.47 (2)
C7⋯H8A^iv	2.774 (11)	H14A⋯H16A	2.51 (2)
H2⋯H9A	2.572 (19)	H14B⋯H16B	2.56 (2)
H2⋯H17A^vi	2.34 (2)	H14B⋯H16B^vii	2.54 (2)
H8B⋯H10B	2.507 (18)	H15A⋯H17A	2.60 (2)
H9A⋯H11A	2.550 (19)	H15B⋯H17B	2.54 (2)
Symmetry codes: (i) ; (ii) ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y+1, z; (v) ; (vi) ; (vii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A portion of one chain viewed along the c-axis direction with N—H⋯O and C—H⋯O hydrogen bonds depicted, respectively, by blue and black dashed lines. H atoms not involved in hydrogen bonding were omitted for clarity.

Figure 3
Packing viewed along the b-axis direction with hydrogen bonds depicted as in Fig. 2

and C—H⋯π(ring) interactions by green dashed lines. H atoms not involved in hydrogen bonding were omitted for clarity.

4. Hirshfeld surface analysis

In order to visualize the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ) was carried out using Crystal Explorer 17.5 (Turner et al., 2017 ). A view of the three-dimensional Hirshfeld surface of (I), plotted over d_norm and the electrostatic potential map are shown in Fig. 4a and b, respectively. The shape-index of the HS reveals that there are no π–π interactions in (I), as shown in Fig. 4c. The overall two-dimensional fingerprint plot, Fig. 5a, and those delineated into H⋯H, H⋯C/C⋯H, H⋯O/O⋯H, H⋯N/N⋯H, C⋯O/O⋯C, N⋯O/O⋯N, C⋯N/N⋯C and C⋯C contacts (McKinnon et al., 2007 ) are illustrated in Fig. 5b–i, respectively, together with their relative contributions to the Hirshfeld surface. The most important interaction is H⋯H (Table 2) contributing 75.9% to the overall crystal packing, which is reflected in Fig. 5b as widely scattered points of high density due to the large hydrogen content of the molecule, with the tip at d_e = d_i = 1.08 Å. In the presence of C—H⋯π interactions, the pair of characteristic wings are seen in the fingerprint plot (Fig. 5c) delineated into H⋯C/C⋯H contacts (12.5% contribution; Table 2), with the tips at d_e + d_i = 2.66 Å. The pair of the scattered points of spikes in the fingerprint plot delineated into H⋯O/O⋯H contacts, Fig. 5d, with a 7.0% contribution to the HS, has a distribution of points with the tips at d_e + d_i = 1.83 Å. The H⋯N/N⋯H contacts, Fig. 5e, with a 2.3% contribution to the HS have the tips at d_e + d_i = 2.92 Å. The C⋯O/O⋯C contacts, Fig. 5f, with a 1.2% contribution to the HS appear as a pair of scattered points of spikes with the tips at d_e + d_i = 3.25 Å. Finally, the N⋯O/O⋯N (Fig. 5g), N⋯C/C⋯N (Fig. 5h) and C⋯C (Fig. 5i) contacts have 0.6%, 0.3% and 0.3% contributions, respectively, to the HS with low-density distributions of points.

Figure 4
(a) View of the three-dimensional Hirshfeld surface of the title compound, plotted over d_norm in the range of −0.5871 to 1.6590 a.u. (b) View of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. (c) Hirshfeld surface of the title compound plotted over shape-index.

Figure 5
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) H⋯N/N⋯H, (f) C⋯O/O⋯C, (g) N⋯O/O⋯N, (h) C⋯N/N⋯C and (i) C⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface contacts.

The Hirshfeld surface representations with the function d_norm plotted onto the surface are shown for the H⋯H, H⋯C/C⋯H and H⋯O/O⋯H interactions in Fig. 6a–c, respectively.

Figure 6
The Hirshfeld surface representations with the function d_norm plotted onto the surface for (a) H⋯H, (b) H⋯C/C⋯H and (c) H⋯O/O⋯H interactions.

The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H, H⋯C/C⋯H and H⋯O/O⋯H interactions suggest that van der Waals interactions play the major role in the crystal packing (Hathwar et al., 2015 ).

5. Interaction energy calculations

The intermolecular interaction energies were calculated using the CE–B3LYP/6–31G(d,p) energy model available in Crystal Explorer 17.5 (Turner et al., 2017), where a cluster of molecules is used by applying crystallographic symmetry operations with respect to a selected central molecule within a default radius of 3.8 Å (Turner et al., 2014 ). The total intermolecular energy (E_tot) is the sum of electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange-repulsion (E_rep) energies (Turner et al., 2015 ) with scale factors of 1.057, 0.740, 0.871 and 0.618, respectively (Mackenzie et al., 2017 ). Hydrogen-bonding interaction energies (in kJ mol⁻¹) were calculated as −91.9 (E_ele), −21.4 (E_pol), −14.5 (E_dis), 82.1 (E_rep) and −74.9 (E_tot) for N1—H1⋯O1 and −9.2 (E_ele), −0.6 (E_pol), −65.8 (E_dis), 39.9 (E_rep) and −42.7 (E_tot) for C8—H8A⋯O1.

6. Database survey

A search of the Cambridge Structural Database (CSD2021, updated to 2 February, 2021; Groom et al., 2016 ) using the fragment below, where X = Y = H, R = (CH₂)₄C, found nine similar structures. These are IJUGIE [X = Y = H, R = (CH₂)₈CH₃; Ouzidan et al., 2011a ], SECBUZ [X = Y = H, R = (CH₂)₁₁CH₃; Belaziz et al., 2012b ], ZANXET [X = Y = H, R = (CH₂)₇CH₃; Belaziz et al., 2012a ], OCAJIN [X = H, Y = Cl, R = (CH₂)₈CH₃; Kandri Rodi et al., 2011 ], ULEDEV [X = H, Y = NO₂, R = (CH₂)₇CH₃; Ouzidan et al., 2011b ], ULEPIL [X = H, Y = NO₂, R = (CH₂)₉CH₃; Ouzidan et al., 2011c ], ULEZAN [X = H, Y = NO₂, R = (CH₂)₈CH₃; Ouzidan et al., 2011d ], QUDJAC [X = NO₂, Y = H, R = (CH₂)₈CH₃; Venkatraman & Fronczek, 2015 ] and YAGQII [X = NO₂, Y = H, R = (CH₂)₉CH₃; Ouzidan et al., 2011e ]. In all of these molecules, the long alkyl substituent has a straight shape rather than being folded back on itself. This is likely driven by packing considerations as straight alkyl chains can efficiently intercalate, thereby minimizing void space in the crystal.

7. Synthesis and crystallization

The title compound was prepared in two steps. In the first step, 1-bromodecane (11.4 mmol) was added to a mixture of 1-isopropenyl-1H-1,3-benzimidazol-2(3H)-one (5.7 mmol), potassium hydroxide (5.7 mmol) and tetra-n-butyl ammonium bromide (0.15 mmol) in CH₂Cl₂ (15 ml). Stirring was continued at room temperature for 48 h. The formed salts were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by recrystallization from ethanol to obtain 1-(prop-1-en-2-yl)-3-decyl-2,3dihydro-1H-benzimidazol-2(3H)-one in 82% yield. In the second step, 1-(prop-1-en-2-yl)-3-decyl-2,3-dihydro-1H-benzimidazol-2-one (7.0 mmol) was dissolved in a mixture of dimethylformamide (DMF; 10 ml) and cold sulfuric acid (15 ml, 50%_wt). The reaction mixture was stirred at room temperature for 12 h. The precipitate obtained was filtered off and washed with water and subsequently dried. The resulting residue was purified by recrystallization from ethanol to obtain colourless crystals in 75% yield.

¹H NMR (300 MHz, DMSO-d₆): 0.87 (t, 3H, CH₃); 1.25–1.67 (m, 16H, CH₂); 2.80–3.04 (m, 2H, CH₂); 6.99–7.12 (m, 4H, H_arom); 10.58 (s,1H, NH). ¹³C NMR (75 MHz, DMSO-d₆): 14.14 (CH₃); 22.70, 26.90, 28.44, 29.31, 29.51, 29.56, 29.74, 31.90, 41.44 (CH₂); 107.84, 108.45, 121.20, 121.65 (CH_arom); 128.52, 129.64 (Cq), 153.43 (C=O).

8. Refinement

Crystal, data collection and refinement details are presented in Table 3. Hydrogen atoms were located in difference-Fourier maps and were freely refined.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₇H₂₆N₂O
M_r	274.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	17.3256 (5), 5.5662 (2), 16.7244 (5)
β (°)	97.433 (1)
V (Å³)	1599.31 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.55
Crystal size (mm)	0.26 × 0.17 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.88, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	11457, 3082, 2857
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.08
No. of reflections	3082
No. of parameters	286
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SAINT (Bruker, 2016), SHELXT/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2079158

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989021004291/wm5606sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021004291/wm5606Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021004291/wm5606Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989021004291/wm5606Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

1-Decyl-2,3-dihydro-1H-benzimidazol-2-one top

Crystal data top

C₁₇H₂₆N₂O	F(000) = 600
M_r = 274.40	D_x = 1.140 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 17.3256 (5) Å	Cell parameters from 9927 reflections
b = 5.5662 (2) Å	θ = 2.6–72.4°
c = 16.7244 (5) Å	µ = 0.55 mm⁻¹
β = 97.433 (1)°	T = 150 K
V = 1599.31 (9) Å³	Parallelepiped, colourless
Z = 4	0.26 × 0.17 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3082 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2857 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 5.6°
ω scans	h = −19→21
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −6→6
T_min = 0.88, T_max = 0.95	l = −20→17
11457 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	All H-atom parameters refined
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0505P)² + 0.3296P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3082 reflections	Δρ_max = 0.19 e Å⁻³
286 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL 2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0415 (17)

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.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.04776 (4)	0.28130 (13)	0.44474 (4)	0.0303 (2)
N1	0.05137 (5)	0.31336 (16)	0.58449 (5)	0.0277 (2)
H1	0.0208 (9)	0.449 (3)	0.5834 (8)	0.049 (4)*
N2	0.11079 (5)	0.00636 (15)	0.53573 (5)	0.0257 (2)
C1	0.11866 (6)	−0.02174 (17)	0.61924 (6)	0.0255 (2)
C2	0.15374 (6)	−0.20007 (19)	0.66878 (7)	0.0303 (3)
H2	0.1796 (8)	−0.337 (3)	0.6474 (8)	0.039 (3)*
C3	0.15165 (7)	−0.1745 (2)	0.75149 (7)	0.0337 (3)
H3	0.1783 (8)	−0.300 (2)	0.7883 (8)	0.042 (4)*
C4	0.11570 (7)	0.0218 (2)	0.78254 (7)	0.0332 (3)
H4	0.1157 (8)	0.039 (2)	0.8423 (8)	0.037 (3)*
C5	0.07947 (6)	0.19953 (19)	0.73228 (6)	0.0302 (3)
H5	0.0528 (7)	0.334 (2)	0.7533 (7)	0.033 (3)*
C6	0.08152 (6)	0.17382 (17)	0.65026 (6)	0.0261 (2)
C7	0.06765 (6)	0.20902 (17)	0.51435 (6)	0.0253 (2)
C8	0.13586 (6)	−0.16239 (18)	0.47772 (6)	0.0284 (3)
H8A	0.1186 (7)	−0.327 (2)	0.4909 (7)	0.031 (3)*
H8B	0.1074 (7)	−0.116 (2)	0.4234 (8)	0.030 (3)*
C9	0.22347 (6)	−0.16205 (19)	0.47500 (7)	0.0308 (3)
H9A	0.2512 (8)	−0.205 (2)	0.5293 (8)	0.035 (3)*
H9B	0.2344 (8)	−0.290 (2)	0.4382 (8)	0.035 (3)*
C10	0.25501 (6)	0.0740 (2)	0.44707 (7)	0.0325 (3)
H10A	0.2498 (8)	0.199 (3)	0.4881 (8)	0.042 (4)*
H10B	0.2229 (8)	0.128 (2)	0.3965 (8)	0.038 (3)*
C11	0.33982 (7)	0.0550 (2)	0.43186 (7)	0.0355 (3)
H11A	0.3717 (8)	−0.020 (2)	0.4812 (8)	0.041 (3)*
H11B	0.3434 (8)	−0.060 (3)	0.3859 (8)	0.042 (4)*
C12	0.37542 (7)	0.2942 (2)	0.41212 (8)	0.0371 (3)
H12A	0.3739 (8)	0.409 (3)	0.4593 (8)	0.044 (4)*
H12B	0.3426 (8)	0.369 (3)	0.3659 (8)	0.040 (3)*
C13	0.45872 (7)	0.2725 (2)	0.39272 (8)	0.0374 (3)
H13A	0.4913 (9)	0.197 (3)	0.4389 (9)	0.045 (4)*
H13B	0.4594 (8)	0.161 (3)	0.3467 (9)	0.044 (4)*
C14	0.49438 (7)	0.5123 (2)	0.37418 (8)	0.0383 (3)
H14A	0.4944 (9)	0.622 (3)	0.4218 (9)	0.050 (4)*
H14B	0.4604 (8)	0.589 (3)	0.3278 (8)	0.042 (4)*
C15	0.57697 (7)	0.4932 (2)	0.35263 (8)	0.0383 (3)
H15A	0.6106 (9)	0.409 (3)	0.3983 (9)	0.047 (4)*
H15B	0.5772 (8)	0.385 (3)	0.3040 (8)	0.044 (4)*
C16	0.61285 (7)	0.7340 (2)	0.33601 (8)	0.0416 (3)
H16A	0.6112 (9)	0.842 (3)	0.3852 (9)	0.054 (4)*
H16B	0.5799 (10)	0.814 (3)	0.2910 (9)	0.053 (4)*
C17	0.69572 (9)	0.7119 (3)	0.31580 (10)	0.0540 (4)
H17A	0.7312 (11)	0.646 (3)	0.3640 (11)	0.072 (5)*
H17B	0.6977 (10)	0.598 (3)	0.2673 (10)	0.066 (5)*
H17C	0.7161 (11)	0.872 (4)	0.3005 (11)	0.076 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0355 (4)	0.0285 (4)	0.0273 (4)	0.0019 (3)	0.0055 (3)	0.0041 (3)
N1	0.0307 (4)	0.0240 (4)	0.0289 (5)	0.0026 (3)	0.0066 (3)	0.0010 (3)
N2	0.0292 (4)	0.0237 (4)	0.0251 (4)	0.0005 (3)	0.0063 (3)	0.0006 (3)
C1	0.0261 (5)	0.0245 (5)	0.0264 (5)	−0.0041 (4)	0.0051 (4)	−0.0002 (4)
C2	0.0343 (5)	0.0253 (5)	0.0315 (6)	0.0005 (4)	0.0049 (4)	0.0011 (4)
C3	0.0391 (6)	0.0307 (6)	0.0307 (6)	−0.0021 (4)	0.0022 (4)	0.0053 (4)
C4	0.0376 (6)	0.0359 (6)	0.0267 (6)	−0.0055 (4)	0.0061 (4)	0.0006 (4)
C5	0.0329 (5)	0.0288 (5)	0.0301 (6)	−0.0031 (4)	0.0087 (4)	−0.0032 (4)
C6	0.0255 (5)	0.0246 (5)	0.0284 (5)	−0.0035 (4)	0.0049 (4)	0.0012 (4)
C7	0.0255 (5)	0.0231 (5)	0.0279 (5)	−0.0033 (4)	0.0061 (4)	0.0011 (4)
C8	0.0337 (5)	0.0235 (5)	0.0288 (5)	−0.0009 (4)	0.0071 (4)	−0.0030 (4)
C9	0.0340 (6)	0.0294 (6)	0.0299 (6)	0.0050 (4)	0.0072 (4)	0.0000 (4)
C10	0.0321 (5)	0.0309 (6)	0.0355 (6)	0.0020 (4)	0.0080 (5)	0.0003 (4)
C11	0.0336 (6)	0.0365 (6)	0.0376 (6)	0.0025 (5)	0.0090 (5)	0.0021 (5)
C12	0.0339 (6)	0.0375 (6)	0.0408 (7)	−0.0002 (5)	0.0081 (5)	0.0009 (5)
C13	0.0347 (6)	0.0385 (6)	0.0399 (7)	0.0005 (5)	0.0086 (5)	0.0020 (5)
C14	0.0355 (6)	0.0377 (7)	0.0423 (7)	−0.0010 (5)	0.0070 (5)	−0.0013 (5)
C15	0.0366 (6)	0.0370 (6)	0.0423 (7)	−0.0022 (5)	0.0081 (5)	−0.0007 (5)
C16	0.0389 (6)	0.0401 (7)	0.0454 (7)	−0.0055 (5)	0.0037 (5)	−0.0002 (5)
C17	0.0432 (7)	0.0588 (9)	0.0612 (9)	−0.0130 (6)	0.0111 (7)	0.0003 (7)

Geometric parameters (Å, º) top

O1—C7	1.2378 (12)	C10—H10A	0.988 (14)
N1—C7	1.3706 (13)	C10—H10B	0.996 (14)
N1—C6	1.3920 (13)	C11—C12	1.5214 (16)
N1—H1	0.923 (16)	C11—H11A	1.021 (14)
N2—C7	1.3747 (13)	C11—H11B	1.009 (14)
N2—C1	1.3944 (13)	C12—C13	1.5245 (16)
N2—C8	1.4564 (12)	C12—H12A	1.017 (14)
C1—C2	1.3823 (14)	C12—H12B	0.989 (14)
C1—C6	1.3981 (14)	C13—C14	1.5197 (16)
C2—C3	1.3958 (16)	C13—H13A	0.990 (15)
C2—H2	0.974 (14)	C13—H13B	0.990 (15)
C3—C4	1.3910 (16)	C14—C15	1.5239 (16)
C3—H3	1.003 (14)	C14—H14A	1.004 (16)
C4—C5	1.3940 (16)	C14—H14B	1.007 (14)
C4—H4	1.004 (13)	C15—C16	1.5182 (17)
C5—C6	1.3841 (15)	C15—H15A	1.014 (15)
C5—H5	0.970 (13)	C15—H15B	1.013 (15)
C8—C9	1.5246 (15)	C16—C17	1.5221 (19)
C8—H8A	0.995 (13)	C16—H16A	1.020 (16)
C8—H8B	1.009 (13)	C16—H16B	0.989 (16)
C9—C10	1.5195 (15)	C17—H17A	1.017 (19)
C9—H9A	1.000 (13)	C17—H17B	1.033 (18)
C9—H9B	0.974 (13)	C17—H17C	1.00 (2)
C10—C11	1.5269 (15)

O1···N2ⁱ	3.2324 (11)	H8B···H10B	2.507 (18)
O1···C1ⁱ	3.2784 (12)	H9A···H11A	2.550 (19)
O1···N1ⁱⁱ	2.8394 (11)	H9B···H11B	2.53 (2)
C4···O1ⁱⁱⁱ	3.2820 (14)	H10A···H12A	2.55 (2)
O1···H8B	2.486 (11)	H10B···H12B	2.58 (2)
O1···H1ⁱⁱ	1.934 (16)	H11A···H13A	2.58 (2)
O1···H8A^iv	2.571 (11)	H11A···H16A^v	2.43 (2)
H4···O1ⁱⁱⁱ	2.417 (13)	H11B···H13B	2.51 (2)
N1···C2^iv	3.4382 (14)	H12A···H14A	2.55 (2)
N1···C8ⁱ	3.3820 (14)	H12A···H15A^v	2.57 (2)
N2···C7ⁱ	3.3206 (14)	H12B···H14B	2.53 (2)
N1···H8A^iv	2.878 (12)	H13A···H15A	2.55 (2)
N1···H8Bⁱ	2.949 (12)	H13A···H14A^v	2.52 (2)
N2···H10A	2.843 (14)	H13B···H15B	2.57 (2)
C7···C8ⁱ	3.5550 (15)	H13B···H16B^vii	2.47 (2)
C7···C7ⁱ	3.2937 (14)	H14A···H16A	2.51 (2)
C2···H17C^v	2.90 (2)	H14B···H16B	2.56 (2)
C7···H1ⁱⁱ	2.828 (16)	H14B···H16B^vii	2.54 (2)
C7···H8A^iv	2.774 (11)	H15A···H17A	2.60 (2)
H2···H9A	2.572 (19)	H15B···H17B	2.54 (2)
H2···H17A^vi	2.34 (2)

C7—N1—C6	110.01 (9)	H10A—C10—H10B	106.7 (11)
C7—N1—H1	120.8 (9)	C12—C11—C10	113.68 (10)
C6—N1—H1	129.0 (9)	C12—C11—H11A	109.9 (8)
C7—N2—C1	109.39 (8)	C10—C11—H11A	109.0 (8)
C7—N2—C8	123.71 (8)	C12—C11—H11B	109.0 (8)
C1—N2—C8	126.57 (8)	C10—C11—H11B	109.0 (8)
C2—C1—N2	131.25 (9)	H11A—C11—H11B	106.0 (11)
C2—C1—C6	121.63 (9)	C11—C12—C13	113.47 (10)
N2—C1—C6	107.11 (8)	C11—C12—H12A	109.2 (8)
C1—C2—C3	117.07 (10)	C13—C12—H12A	109.6 (8)
C1—C2—H2	121.9 (8)	C11—C12—H12B	109.1 (8)
C3—C2—H2	121.0 (8)	C13—C12—H12B	109.3 (8)
C4—C3—C2	121.36 (10)	H12A—C12—H12B	105.9 (11)
C4—C3—H3	120.8 (8)	C14—C13—C12	113.26 (10)
C2—C3—H3	117.9 (8)	C14—C13—H13A	109.1 (8)
C3—C4—C5	121.38 (10)	C12—C13—H13A	109.1 (8)
C3—C4—H4	120.4 (7)	C14—C13—H13B	110.2 (8)
C5—C4—H4	118.3 (7)	C12—C13—H13B	108.7 (8)
C6—C5—C4	117.19 (10)	H13A—C13—H13B	106.1 (12)
C6—C5—H5	120.9 (7)	C13—C14—C15	113.93 (10)
C4—C5—H5	121.9 (7)	C13—C14—H14A	109.3 (9)
C5—C6—N1	132.10 (10)	C15—C14—H14A	109.1 (9)
C5—C6—C1	121.36 (9)	C13—C14—H14B	108.6 (8)
N1—C6—C1	106.55 (9)	C15—C14—H14B	108.7 (8)
O1—C7—N1	127.16 (10)	H14A—C14—H14B	106.9 (12)
O1—C7—N2	125.96 (9)	C16—C15—C14	113.62 (10)
N1—C7—N2	106.88 (8)	C16—C15—H15A	109.7 (9)
N2—C8—C9	113.76 (9)	C14—C15—H15A	108.7 (8)
N2—C8—H8A	108.7 (7)	C16—C15—H15B	109.5 (8)
C9—C8—H8A	109.7 (7)	C14—C15—H15B	109.4 (8)
N2—C8—H8B	106.3 (7)	H15A—C15—H15B	105.7 (12)
C9—C8—H8B	110.2 (7)	C15—C16—C17	112.95 (11)
H8A—C8—H8B	108.0 (10)	C15—C16—H16A	108.4 (9)
C10—C9—C8	114.16 (9)	C17—C16—H16A	110.6 (9)
C10—C9—H9A	109.6 (7)	C15—C16—H16B	109.0 (9)
C8—C9—H9A	109.6 (8)	C17—C16—H16B	109.6 (9)
C10—C9—H9B	109.2 (8)	H16A—C16—H16B	106.0 (13)
C8—C9—H9B	107.1 (8)	C16—C17—H17A	110.1 (11)
H9A—C9—H9B	106.9 (11)	C16—C17—H17B	110.6 (10)
C9—C10—C11	112.56 (9)	H17A—C17—H17B	108.8 (14)
C9—C10—H10A	108.9 (8)	C16—C17—H17C	111.0 (11)
C11—C10—H10A	109.9 (8)	H17A—C17—H17C	109.1 (15)
C9—C10—H10B	109.7 (8)	H17B—C17—H17C	107.1 (14)
C11—C10—H10B	108.8 (8)

C7—N2—C1—C2	177.13 (10)	C6—N1—C7—O1	177.92 (9)
C8—N2—C1—C2	3.56 (17)	C6—N1—C7—N2	−2.09 (11)
C7—N2—C1—C6	−2.02 (11)	C1—N2—C7—O1	−177.48 (9)
C8—N2—C1—C6	−175.60 (9)	C8—N2—C7—O1	−3.68 (15)
N2—C1—C2—C3	179.89 (10)	C1—N2—C7—N1	2.53 (11)
C6—C1—C2—C3	−1.06 (15)	C8—N2—C7—N1	176.33 (8)
C1—C2—C3—C4	0.11 (16)	C7—N2—C8—C9	111.38 (11)
C2—C3—C4—C5	0.78 (17)	C1—N2—C8—C9	−75.91 (12)
C3—C4—C5—C6	−0.69 (16)	N2—C8—C9—C10	−63.87 (12)
C4—C5—C6—N1	179.37 (10)	C8—C9—C10—C11	−170.56 (9)
C4—C5—C6—C1	−0.26 (15)	C9—C10—C11—C12	−174.11 (10)
C7—N1—C6—C5	−178.81 (10)	C10—C11—C12—C13	−177.01 (10)
C7—N1—C6—C1	0.86 (11)	C11—C12—C13—C14	−179.20 (10)
C2—C1—C6—C5	1.17 (15)	C12—C13—C14—C15	−178.58 (10)
N2—C1—C6—C5	−179.58 (9)	C13—C14—C15—C16	−178.72 (11)
C2—C1—C6—N1	−178.55 (9)	C14—C15—C16—C17	179.15 (11)
N2—C1—C6—N1	0.70 (10)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x, y+1, z; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.923 (16)	1.932 (16)	2.8393 (12)	167.0 (13)
C8—H8A···O1^viii	0.995 (13)	2.573 (13)	3.4648 (12)	149.1 (9)
C17—H17C···Cg2^v	1.00 (2)	2.985 (19)	3.6656 (17)	126.0 (14)

Symmetry codes: (ii) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (viii) x, y−1, z.

Acknowledgements

Author contribution are as follows. Conceptualization, AS, MLT, NKS; methodology, BA and YAE; investigation, YAE, IE, JTM and TH; writing (original draft), JTM, TH and NKS; writing (review and editing of the manuscript), YAE and IE; visualization, MLT and EME; resources, EME and AS; supervision, BA and NKS.

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. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

References

Barreca, M. L., Rao, A., De Luca, L., Iraci, N., Monforte, A. M., Maga, G., De Clercq, E., Pannecouque, C., Balzarini, J. & Chimirri, A. (2007). Bioorg. Med. Chem. Lett. 17, 1956–1960. CrossRef PubMed CAS Google Scholar
Belaziz, D., Kandri Rodi, Y., Essassi, E. M. & El Ammari, L. (2012a). Acta Cryst. E68, o1276. CSD CrossRef IUCr Journals Google Scholar
Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012b). Acta Cryst. E68, o3069. CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ, 2, 563–574. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Hirshfeld, H. L. (1977). Theor. Chim. Acta, 44, 129–138. CrossRef CAS Web of Science Google Scholar
Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o3340–o3341. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khodarahmi, G. A., Chen, C. S., Hakimelahi, G. H., Tseng, C. T. & Chern, J. W. (2005). J. Iran. Chem. Soc. 2, 124–134. CrossRef CAS Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Lakhrissi, B., Benksim, A., Massoui, M., Essassi, E. M., Lequart, V., Joly, N., Beaupère, D., Wadouachi, A. & Martin, P. (2008). Carbohydr. Res. 343, 421–433. Web of Science CrossRef PubMed CAS Google Scholar
Mackenzie, C. F., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). IUCrJ, 4, 575–587. Web of Science CrossRef CAS PubMed IUCr Journals Google Scholar
Mamedov, V. A., Zhukova, N. A. & Sinyashin, O. G. (2017). Mendeleev Commun. 27, 1–11. CrossRef CAS Google Scholar
Mavrova, A. T., Anichina, K. K., Vuchev, D. I., Tsenov, J. A., Kondeva, M. S. & Micheva, M. K. (2005). Bioorg. Med. Chem. 13, 5550–5559. CrossRef PubMed CAS Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Essassi, E. M., El Ammari, L., Fronczek, F. R. & Venkatraman, R. (2011d). Acta Cryst. E67, o669. CSD CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011e). Acta Cryst. E67, o2937. CSD CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2011c). Acta Cryst. E67, o613. CSD CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2011b). Acta Cryst. E67, o558. CSD CrossRef IUCr Journals Google Scholar
Saber, A., Sebbar, N. K. & Essassi, E. M. (2019). J. Mar. Chem. Heterocycl. 18, 1–50. Google Scholar
Saber, A., Sebbar, N. K., Hökelek, T., Labd Taha, M., Mague, J. T., Hamou Ahabchane, N. & Essassi, E. M. (2020a). Acta Cryst. E76, 95–101. CSD CrossRef IUCr Journals Google Scholar
Saber, A., Sebbar, N. K., Sert, Y., Alzaqri, N., Hökelek, T., El Ghayati, L., Talbaoui, A., Mague, J. T., Baba, Y. F., Urrutigoîty, M. & Essassi, E. M. (2020b). J. Mol. Struct. 1200, 127174. CSD CrossRef Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Srhir, M., Sebbar, N. K., Hökelek, T., Moussaif, A., Mague, J. T., Hamou Ahabchane, N. & Essassi, E. M. (2020). Acta Cryst. E76, 370–376. CSD CrossRef IUCr Journals Google Scholar
Turner, M. J., Grabowsky, S., Jayatilaka, D. & Spackman, M. A. (2014). J. Phys. Chem. Lett. 5, 4249–4255. Web of Science CrossRef CAS PubMed Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. The University of Western Australia. Google Scholar
Turner, M. J., Thomas, S. P., Shi, M. W., Jayatilaka, D. & Spackman, M. A. (2015). Chem. Commun. 51, 3735–3738. Web of Science CrossRef CAS Google Scholar
Venkatraman, R. & Fronczek, F. R. (2015). CSD Communication (refcode QUDJAC). CCDC, Cambridge, England. Google Scholar
Vira, J. J., Patel, D. R., Bhimani, N. V. & Ajudia, P. A. (2010). Pharma Chem. 2, 178–183. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.