Crystal structure and Hirshfeld surface analysis of a new benzimidazole compound, 3-{1-[(2-hy­droxyphen­yl)meth­yl]-1H-1,3-benzo­diazol-2-yl}phenol

Bouhidel, Z.; Sahli, K.; Cherouana, A.

doi:10.1107/S2056989023010368

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Volume 80| Part 1| January 2024| Pages 18-21

https://doi.org/10.1107/S2056989023010368

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Crystal structure and Hirshfeld surface analysis of a new benzimidazole compound, 3-{1-[(2-hydroxyphenyl)methyl]-1H-1,3-benzodiazol-2-yl}phenol

Zakaria Bouhidel,^a Kaouther Sahli ^b and Aouatef Cherouana ^a ^*

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (URCHEMS), Département de Chimie, Université Mentouri de Constantine, 25000 Constantine, Algeria, and ^bPharmaceutical Sciences Research Center CRSP, Constantine 25000, Algeria
^*Correspondence e-mail: cherouana.aouatef@umc.edu.dz

Edited by A. Briceno, Venezuelan Institute of Scientific Research, Venezuela (Received 26 September 2023; accepted 1 December 2023; online 1 January 2024)

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.

The title compound, C₂₀H₁₆N₂O₂, is composed of two monosubstituted benzene rings and one benzimidazole unit. The benzimidazole moiety subtends dihedral angles of 46.16 (7) and 77.45 (8)° with the benzene rings, which themselves form a dihedral angle of 54.34 (9)°. The crystal structure features O—H⋯N and O—H⋯O hydrogen-bonding interactions, which together lead to the formation of two-dimensional hydrogen-bonded layers parallel to the (101) plane. In addition, π–π interactions also contribute to the crystal cohesion. Hirshfeld surface analysis indicates that the most significant contacts in the crystal packing are: H⋯H (47.5%), O⋯H/H⋯O (12.4%), N⋯H/H⋯N (6.1%), C⋯H/H⋯C (27.6%) and C⋯C (4.6%).

Keywords: benzimidazole; single crystal; X-ray diffraction; hydrogen bonding; intermolecular interactions; Hirshfeld surface analysis.

CCDC reference: 2311475

1. Chemical context

The benzimidazole unit comprises a phenyl ring fused to an imidazole ring. The first benzimidazole compound was prepared by Hoebrecker (1872 ). Benzimidazole is an important structural core in medicinal chemistry and this class of compounds displays a broad range of biological activities such as antimicrobial, antiviral, anticancer, anti-inflammatory, gastroprotective and analgesic (Spasov et al., 1999 ; Sevak et al., 2002 ; Demirayak et al., 2005 ). The use of benzimidazole derivatives with common drugs employed in the treatment of giardiasis has been reviewed (Harris et al., 2001 ). The coordination behavior of benzimidazole derivatives towards transition-metal ions was explored in order to increase their biological activity (Téllez et al., 2007 ). The present work describes the synthesis, structural characterization and Hirshfeld analysis of a new benzimidazole compound, 3-{1-[(2-hydroxyphenyl)methyl]-1H-1,3-benzodiazol-2-yl}phenol.

2. Structural commentary

The title compound is composed of two monosubstituted benzene rings and one benzimidazole unit (Fig. 1). The benzimidazole moiety subtends dihedral angles of 46.16 (7) and 77.45 (8)° with the benzene rings, which themselves form a dihedral angle of 54.34 (9)°. These angles are in agreement with those observed in similar structures (Quezada-Miriel et al., 2012 ; Shu-Ping Yang et al., 2007 ).

Figure 1
ORTEP view of the title compound with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

The crystal packing of the title compound reveals intermolecular hydrogen bonding, specifically O—H⋯O interactions involving benzene rings and O—H⋯N interaction between the benzimidazole moieties and benzene rings (Table 1). The molecules are self-assembled by intermolecular hydrogen bonds between the hydroxyl groups and the N1 atoms of the benzimidazole moieties, forming hydrogen-bonded ribbons with a C(8) graph-set motif (Etter et al., 1990 ; Bernstein et al., 1995 ) parallel to the (111) plane. The combination of the O—H⋯O and O—H⋯N hydrogen bonds leads to rings with R₄⁴ (18) and R₄⁴(38) graph-set motifs (Fig. 2). Further cohesion of the crystal packing is provided by π–π stacking interactions between C1–C6 benzene rings with centroid–centroid distances of 3.5957 (11) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	2.04	2.861 (2)	173
O2—H2⋯N1ⁱⁱ	0.82	1.89	2.7124 (19)	178
C16—H16⋯N2	0.93	2.55	2.878 (2)	101
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The R₄⁴ (18) and R₄⁴(38) graph-set motifs parallel to the ab plane generated by the combination of O—H⋯O and O—H⋯N hydrogen bonds.

4. Hirshfeld surface analysis

Hirshfeld surface analysis was undertaken in order to better understand the intermolecular interactions within the crystal structure using graphical tools (Spackman & Jayatilaka, 2009 ; Spackman et al., 2021 ). Hirshfeld surface analysis provides a three-dimensional picture of the intermolecular interactions. These interactions can be summarized by using fingerprint plots. The Hirshfeld surface of the title compound mapped over d_norm is shown in Fig. 3. The red spots on the surface indicate the presence of atoms in very close proximity to the outside of the surface, the white means that the atoms are in medium proximity while the blue areas are completely devoid of close contacts. The combination of the 3D Hirshfeld surface and the 2D fingerprint plots (Fig. 4), shows that intermolecular H⋯H contacts make the main contribution, corresponding to 47.5% of the total Hirshfeld surface (McKinnon et al., 2007 ) and that there are short intermolecular H⋯H contacts where d_e = d_i = 1 Å. In the fingerprint plot delineated into C⋯H/H⋯C contacts (27.6% of the total Hirshfeld surface) there are two short spikes. The red spots on the d_norm surface in Fig. 3 are due to the H_O⋯O contacts corresponding to O—H⋯O and O—H⋯N hydrogen bonds. The O⋯H and N⋯H contacts represent 12.4% and 6.1% of the total Hirshfeld surface, respectively, Fig. 5. These contacts are manifested as sharp spikes at d_e + d_i = 1.8 Å for N⋯H and 1.9 Å for O⋯H. Finally, packing cohesion in this structure is also provided by C⋯N and C⋯C interactions, which correspond to π–π stacking interactions.

Figure 3
Hirshfeld surface of the title compound mapped with d_norm.

Figure 4
Two-dimensional fingerprints plots of the title compound, showing H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, N⋯H/H⋯N and C⋯C contacts.

Figure 5
Relative contributions of various interactions to the Hirshfeld surface area of the title compound.

5. Synthesis and crystallization

All chemicals were commercially available, purchased from Sigma-Aldrich, and used as received without purification. 3-Hydroxybenzaldehyde (0.244 g, 2 mmol) and salicylaldehyde (0.244 g, 2 mmol) were added to an ethanolic solution of o-phenylenediamine (0.216 g, 2 mmol). The reaction mixture was stirred for 4 h under reflux at 348 K. The resulting brown solution was cooled in an ice bath. The obtained filtrate was left to evaporate slowly at room temperature, giving after two weeks colorless crystals suitable for single-crystal x-ray diffraction analysis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were located in difference electron-density maps and were treated as riding on their parent atoms with C—H = 0.93 Å, O—H = 0.84 Å and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂O₂
M_r	316.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.6474 (3), 13.2429 (3), 11.4176 (3)
β (°)	99.067 (1)
V (Å³)	1589.79 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.1 × 0.1 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	33506, 4650, 2866
R_int	0.056

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.190, 1.06
No. of reflections	4643
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.30
Computer programs: COLLECT (Nonius, 1999 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2311475

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989023010368/zn2033sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989023010368/zn2033Isup2.cml

checkCIF report

Computing details top

3-{1-[(2-Hydroxyphenyl)methyl]-1H-1,3-benzodiazol-2-yl}phenol top

Crystal data top

C₂₀H₁₆N₂O₂	F(000) = 664
M_r = 316.35	Least Squares Treatment of 25 SET4 setting angles.
Monoclinic, P2₁/n	D_x = 1.322 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.6474 (3) Å	Cell parameters from 33506 reflections
b = 13.2429 (3) Å	θ = 2.4–30.1°
c = 11.4176 (3) Å	µ = 0.09 mm⁻¹
β = 99.067 (1)°	T = 100 K
V = 1589.79 (7) Å³	Prism, colourless
Z = 4	0.1 × 0.1 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	2866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 30.1°, θ_min = 2.4°
ω scans	h = −15→14
33506 measured reflections	k = −17→18
4650 independent reflections	l = −15→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.190	W = 1/[Σ²(FO²) + (0.1027P)² + 0.1399P] WHERE P = (FO² + 2FC²)/3
S = 1.06	(Δ/σ)_max < 0.001
4643 reflections	Δρ_max = 0.50 e Å⁻³
217 parameters	Δρ_min = −0.30 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
O1	0.71485 (14)	0.50588 (12)	0.85134 (15)	0.0674 (6)
O2	0.86823 (12)	0.19463 (10)	0.75574 (10)	0.0484 (4)
N1	0.50090 (14)	0.18753 (11)	1.12414 (12)	0.0415 (4)
N2	0.64015 (13)	0.13212 (10)	1.01162 (12)	0.0365 (4)
C1	0.54208 (16)	0.30396 (13)	0.96699 (14)	0.0393 (5)
C2	0.64184 (18)	0.36170 (13)	0.93853 (15)	0.0434 (5)
C3	0.61480 (19)	0.45154 (14)	0.87656 (16)	0.0470 (6)
C4	0.49058 (19)	0.48277 (14)	0.84368 (16)	0.0496 (6)
C5	0.3922 (2)	0.42579 (16)	0.87286 (17)	0.0524 (6)
C6	0.41675 (19)	0.33701 (15)	0.93432 (16)	0.0475 (6)
C7	0.56219 (15)	0.20898 (13)	1.03474 (14)	0.0376 (5)
C8	0.62905 (16)	0.05631 (12)	1.09273 (15)	0.0386 (5)
C9	0.54146 (16)	0.09200 (13)	1.16216 (15)	0.0405 (5)
C10	0.50993 (19)	0.03349 (15)	1.25517 (17)	0.0504 (6)
C11	0.5675 (2)	−0.05921 (16)	1.27507 (19)	0.0584 (7)
C12	0.6536 (2)	−0.09453 (14)	1.20405 (19)	0.0573 (7)
C13	0.68637 (19)	−0.03791 (14)	1.11183 (17)	0.0485 (6)
C14	0.71836 (15)	0.12707 (14)	0.91676 (14)	0.0389 (5)
C15	0.85421 (16)	0.16113 (12)	0.95674 (14)	0.0353 (5)
C16	0.91028 (19)	0.16091 (16)	1.07445 (16)	0.0500 (6)
C17	1.0337 (2)	0.19263 (17)	1.10898 (18)	0.0565 (7)
C18	1.10283 (19)	0.22691 (18)	1.02536 (18)	0.0561 (7)
C19	1.04917 (17)	0.22814 (16)	0.90709 (17)	0.0505 (6)
C20	0.92539 (16)	0.19490 (12)	0.87220 (14)	0.0364 (5)
H1	0.69016	0.56161	0.82622	0.1010*
H2	0.90990	0.22934	0.71643	0.0730*
H2A	0.72555	0.34062	0.96058	0.0520*
H4	0.47340	0.54263	0.80161	0.0590*
H5	0.30871	0.44742	0.85090	0.0630*
H6	0.34993	0.29882	0.95425	0.0570*
H10	0.45194	0.05650	1.30205	0.0600*
H11	0.54868	−0.09918	1.33701	0.0700*
H12	0.68991	−0.15799	1.21930	0.0690*
H13	0.74390	−0.06162	1.06486	0.0580*
H14A	0.68017	0.16920	0.85120	0.0470*
H14B	0.71891	0.05813	0.88814	0.0470*
H16	0.86349	0.13880	1.13176	0.0600*
H17	1.06999	0.19081	1.18856	0.0680*
H18	1.18584	0.24933	1.04831	0.0670*
H19	1.09626	0.25138	0.85055	0.0610*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0589 (9)	0.0611 (9)	0.0872 (12)	0.0017 (7)	0.0269 (8)	0.0158 (8)
O2	0.0457 (7)	0.0684 (8)	0.0323 (6)	−0.0122 (6)	0.0096 (5)	0.0031 (5)
N1	0.0386 (8)	0.0533 (8)	0.0348 (7)	0.0000 (6)	0.0125 (6)	−0.0014 (6)
N2	0.0342 (7)	0.0432 (7)	0.0342 (7)	−0.0025 (6)	0.0118 (6)	−0.0014 (5)
C1	0.0426 (9)	0.0459 (9)	0.0300 (8)	0.0020 (7)	0.0080 (7)	−0.0044 (6)
C2	0.0446 (10)	0.0482 (9)	0.0383 (9)	0.0035 (8)	0.0092 (8)	−0.0003 (7)
C3	0.0536 (11)	0.0493 (10)	0.0407 (10)	−0.0016 (8)	0.0157 (8)	−0.0028 (7)
C4	0.0579 (12)	0.0499 (10)	0.0395 (10)	0.0095 (9)	0.0034 (8)	0.0003 (8)
C5	0.0495 (11)	0.0612 (11)	0.0446 (10)	0.0083 (9)	0.0012 (8)	−0.0028 (9)
C6	0.0458 (10)	0.0550 (10)	0.0418 (10)	0.0037 (8)	0.0072 (8)	−0.0037 (8)
C7	0.0346 (8)	0.0475 (9)	0.0312 (8)	−0.0019 (7)	0.0068 (6)	−0.0039 (6)
C8	0.0349 (8)	0.0438 (8)	0.0370 (9)	−0.0085 (7)	0.0058 (7)	−0.0033 (7)
C9	0.0365 (9)	0.0489 (9)	0.0371 (9)	−0.0074 (7)	0.0089 (7)	−0.0024 (7)
C10	0.0487 (11)	0.0623 (11)	0.0426 (10)	−0.0139 (9)	0.0146 (8)	0.0028 (8)
C11	0.0643 (13)	0.0582 (12)	0.0519 (12)	−0.0225 (10)	0.0063 (10)	0.0102 (9)
C12	0.0674 (14)	0.0410 (9)	0.0600 (12)	−0.0101 (9)	−0.0006 (10)	0.0029 (9)
C13	0.0506 (11)	0.0445 (9)	0.0505 (11)	−0.0031 (8)	0.0081 (9)	−0.0044 (8)
C14	0.0360 (9)	0.0501 (9)	0.0325 (8)	−0.0039 (7)	0.0117 (7)	−0.0054 (7)
C15	0.0343 (8)	0.0411 (8)	0.0317 (8)	0.0004 (6)	0.0085 (6)	−0.0022 (6)
C16	0.0484 (11)	0.0690 (12)	0.0331 (9)	−0.0117 (9)	0.0076 (8)	0.0055 (8)
C17	0.0517 (12)	0.0776 (14)	0.0362 (10)	−0.0147 (10)	−0.0051 (8)	0.0049 (9)
C18	0.0373 (10)	0.0784 (13)	0.0500 (11)	−0.0128 (9)	−0.0007 (8)	0.0048 (10)
C19	0.0382 (10)	0.0718 (12)	0.0432 (10)	−0.0084 (9)	0.0120 (8)	0.0076 (9)
C20	0.0370 (9)	0.0427 (8)	0.0304 (8)	0.0018 (7)	0.0077 (7)	−0.0008 (6)

Geometric parameters (Å, º) top

O1—C3	1.354 (3)	C14—C15	1.515 (2)
O2—C20	1.372 (2)	C15—C20	1.392 (2)
N1—C7	1.326 (2)	C15—C16	1.382 (2)
N1—C9	1.384 (2)	C16—C17	1.377 (3)
O1—H1	0.8200	C17—C18	1.372 (3)
N2—C7	1.365 (2)	C18—C19	1.381 (3)
N2—C14	1.468 (2)	C19—C20	1.387 (3)
O2—H2	0.8200	C2—H2A	0.9300
N2—C8	1.384 (2)	C4—H4	0.9300
C1—C6	1.398 (3)	C5—H5	0.9300
C1—C2	1.388 (3)	C6—H6	0.9300
C1—C7	1.475 (2)	C10—H10	0.9300
C2—C3	1.391 (3)	C11—H11	0.9300
C3—C4	1.380 (3)	C12—H12	0.9300
C4—C5	1.374 (3)	C13—H13	0.9300
C5—C6	1.373 (3)	C14—H14A	0.9700
C8—C13	1.391 (2)	C14—H14B	0.9700
C8—C9	1.398 (2)	C16—H16	0.9300
C9—C10	1.398 (3)	C17—H17	0.9300
C10—C11	1.375 (3)	C18—H18	0.9300
C11—C12	1.397 (3)	C19—H19	0.9300
C12—C13	1.382 (3)

C7—N1—C9	105.67 (14)	C17—C18—C19	119.99 (19)
C3—O1—H1	109.00	C18—C19—C20	120.34 (18)
C7—N2—C14	127.55 (14)	C15—C20—C19	119.96 (15)
C8—N2—C14	125.38 (14)	O2—C20—C15	117.67 (15)
C7—N2—C8	107.03 (13)	O2—C20—C19	122.37 (15)
C20—O2—H2	109.00	C1—C2—H2A	120.00
C6—C1—C7	117.43 (16)	C3—C2—H2A	120.00
C2—C1—C6	119.90 (16)	C3—C4—H4	120.00
C2—C1—C7	122.65 (15)	C5—C4—H4	120.00
C1—C2—C3	119.05 (17)	C4—C5—H5	120.00
C2—C3—C4	120.49 (18)	C6—C5—H5	120.00
O1—C3—C2	117.14 (18)	C1—C6—H6	120.00
O1—C3—C4	122.37 (17)	C5—C6—H6	120.00
C3—C4—C5	120.27 (18)	C9—C10—H10	121.00
C4—C5—C6	120.21 (19)	C11—C10—H10	121.00
C1—C6—C5	120.08 (18)	C10—C11—H11	119.00
N1—C7—C1	122.56 (15)	C12—C11—H11	119.00
N1—C7—N2	112.15 (15)	C11—C12—H12	119.00
N2—C7—C1	125.24 (14)	C13—C12—H12	119.00
N2—C8—C13	132.39 (16)	C8—C13—H13	122.00
C9—C8—C13	121.99 (16)	C12—C13—H13	122.00
N2—C8—C9	105.62 (14)	N2—C14—H14A	109.00
C8—C9—C10	120.33 (16)	N2—C14—H14B	109.00
N1—C9—C8	109.52 (15)	C15—C14—H14A	109.00
N1—C9—C10	130.13 (16)	C15—C14—H14B	109.00
C9—C10—C11	117.80 (18)	H14A—C14—H14B	108.00
C10—C11—C12	121.29 (19)	C15—C16—H16	119.00
C11—C12—C13	121.90 (18)	C17—C16—H16	119.00
C8—C13—C12	116.69 (18)	C16—C17—H17	120.00
N2—C14—C15	112.94 (13)	C18—C17—H17	120.00
C16—C15—C20	118.44 (16)	C17—C18—H18	120.00
C14—C15—C16	122.54 (15)	C19—C18—H18	120.00
C14—C15—C20	119.02 (14)	C18—C19—H19	120.00
C15—C16—C17	121.63 (18)	C20—C19—H19	120.00
C16—C17—C18	119.63 (19)

C9—N1—C7—N2	0.45 (19)	C3—C4—C5—C6	−0.4 (3)
C9—N1—C7—C1	178.12 (15)	C4—C5—C6—C1	−0.3 (3)
C7—N1—C9—C8	−0.12 (19)	N2—C8—C9—N1	−0.25 (19)
C7—N1—C9—C10	178.39 (19)	N2—C8—C9—C10	−178.92 (16)
C8—N2—C7—N1	−0.62 (19)	C13—C8—C9—N1	179.53 (16)
C8—N2—C7—C1	−178.22 (15)	C13—C8—C9—C10	0.9 (3)
C14—N2—C7—N1	177.32 (15)	N2—C8—C13—C12	179.02 (18)
C14—N2—C7—C1	−0.3 (3)	C9—C8—C13—C12	−0.7 (3)
C7—N2—C8—C9	0.51 (18)	N1—C9—C10—C11	−178.49 (18)
C7—N2—C8—C13	−179.25 (19)	C8—C9—C10—C11	−0.1 (3)
C14—N2—C8—C9	−177.49 (15)	C9—C10—C11—C12	−0.7 (3)
C14—N2—C8—C13	2.8 (3)	C10—C11—C12—C13	0.9 (3)
C7—N2—C14—C15	94.94 (19)	C11—C12—C13—C8	−0.2 (3)
C8—N2—C14—C15	−87.5 (2)	N2—C14—C15—C16	22.2 (2)
C6—C1—C2—C3	−0.6 (3)	N2—C14—C15—C20	−157.17 (15)
C7—C1—C2—C3	−178.60 (16)	C14—C15—C16—C17	−179.68 (19)
C2—C1—C6—C5	0.8 (3)	C20—C15—C16—C17	−0.3 (3)
C7—C1—C6—C5	178.91 (17)	C14—C15—C20—O2	−0.6 (2)
C2—C1—C7—N1	134.27 (18)	C14—C15—C20—C19	178.84 (16)
C2—C1—C7—N2	−48.4 (2)	C16—C15—C20—O2	−179.98 (16)
C6—C1—C7—N1	−43.8 (2)	C16—C15—C20—C19	−0.6 (3)
C6—C1—C7—N2	133.60 (18)	C15—C16—C17—C18	1.0 (3)
C1—C2—C3—O1	179.55 (16)	C16—C17—C18—C19	−0.9 (3)
C1—C2—C3—C4	−0.1 (3)	C17—C18—C19—C20	0.0 (3)
O1—C3—C4—C5	−179.00 (18)	C18—C19—C20—O2	−179.92 (19)
C2—C3—C4—C5	0.6 (3)	C18—C19—C20—C15	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.04	2.861 (2)	173
O2—H2···N1ⁱⁱ	0.82	1.89	2.7124 (19)	178
C16—H16···N2	0.93	2.55	2.878 (2)	101

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

Acknowledgements

The authors acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate-General for Scientific Research and Technological Development for support.

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