Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chloro­phen­yl)-2-oxoeth­oxy]phen­yl}ethen­yl)-4,5-di­hydro­pyridazin-3(2H)-one

Daoui, S.; Muwafaq, I.; Çınar, E.B.; Abudunia, A.; Dege, N.; Benchat, N.; Karrouchi, K.

doi:10.1107/S205698902101238X

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ISSN: 2056-9890

Volume 78| Part 1| January 2022| Pages 8-11

https://doi.org/10.1107/S205698902101238X

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Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Said Daoui,^a Israa Muwafaq,^b Emine Berrin Çınar,^b ^* Abdulmalik Abudunia,^c ^* Necmi Dege,^b Noureddine Benchat ^a and Khalid Karrouchi ^d

^aLaboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohammed I University, 60000 Oujda, Morocco, ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, 55200, Turkey, ^cDepartment of Pharmacology, Faculty of Clinical Pharmacy, University of Medical and Applied Sciences, Yemen, and ^dLaboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco
^*Correspondence e-mail: emineberrin.cinar@omu.edu.tr, abdulmalikabudunia@gmail.com

Edited by A. V. Yatsenko, Moscow State University, Russia (Received 2 November 2021; accepted 22 November 2021; online 1 January 2022)

The pyridazine ring in the title compound, C₂₀H₁₇ClN₂O₃, adopts a screw-boat conformation. The whole molecule is flattened, the dihedral angles subtended by the least-squares plane of the central aromatic ring with those of the terminal benzene and pyridazine rings being 15.18 (19) and 11.23 (19)°, respectively. In the crystal, the molecules are linked by pairs of N—H⋯O bonds into centrosymmetric dimers and by C—H⋯π contacts into columns. The results of the Hirshfeld surface analysis show that the most prominent interactions are H⋯H, accounting for 36.5% of overall crystal packing, and H⋯O/O⋯H (18.6% contribution) contacts.

Keywords: crystal structure; dihydropyridazin; Hirshfeld surface; hydrogen bonding.

CCDC reference: 2123627

1. Chemical context

Pyridazinone derivatives are a class of nitrogenous heterocyclic compounds that have attracted considerable attention because of their prospective pharmacological and medicinal properties as anti-inflammatory (Boukharsa et al., 2018 ), antitumor (Bouchmaa et al., 2018 , 2019 ), antifungal (Rozada et al., 2020 ), antidepressant (Boukharsa et al., 2016 ), antitubercular, anticonvulsant (Asif et al., 2020 ) and antiviral (El-Shanbaky et al., 2021 ) agents. In addition, pyridazinones demonstrate some interesting physicochemical properties (Daoui et al., 2020a ; El Kalai et al., 2021a ,b ) and some studies have shown that these compounds are good corrosion inhibitors (Chelfi et al., 2020 ). Encouraged by the bioactivity of these compounds and in a continuation of our studies in the field of the synthesis, molecular structures and Hirshfeld surfaces analyses of new pyridazin-3(2H)-one derivatives (Daoui et al., 2020b , 2021 ), we report herein the crystal structure and the results of the Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one.

2. Structural commentary

The molecular structure of the title compound is presented in Fig. 1. The bond lengths in the N1—C15 chain (Table 1) are consistent with an alternation of double and single bonds while those in the amide fragment indicate strong π-conjugation. The N1—N2 distance of 1.406 (4) Å agrees well with the values for related pyridazinones (Daoui, Çınar et al., 2019 ; Daoui, Baydere et al., 2019). The conformation of the dihydropyridazine ring is close to a screw-boat [Θ = 111.9 (6)°, φ = 34.6 (6)°]. The whole molecule is flattened with the largest deviations from the least-squares plane of 0.356 (4) and 0.339 (5) Å being observed for atoms C18 and C19, respectively. The central benzene ring forms dihedral angles of 11.23 (19) and 15.18 (19)° with the planes of the terminal dihydropyridazine and benzene rings, respectively.

Table 1
Selected bond lengths (Å)

C20—O3	1.241 (4)	C16—C17	1.459 (4)
N2—C20	1.333 (5)	C15—C16	1.329 (5)
N1—N2	1.406 (4)	C12—C15	1.470 (4)
N1—C17	1.292 (4)	C7—O1	1.219 (4)

Figure 1
Molecular structure of the title compound showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the crystal, the molecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds, giving rise to an R₂²(8) graph-set motif (Fig. 2a, Table 2). No π–π interactions are present in this structure, but the molecules are connected by weak C—H⋯π contacts into stacks running along the a-axis direction (Fig. 2b,c, Table 2). Other contacts of the C—H⋯O and C—H⋯Cl types further stabilize the crystal structure (Table 2).

Table 2
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.86	2.11	2.891 (4)	151
C4—H4⋯O3ⁱⁱ	0.93	2.44	3.327 (4)	160
C13—H13⋯O1ⁱⁱⁱ	0.93	2.53	3.421 (4)	161
C18—H18A⋯Cl1^iv	0.97	2.94	3.737 (3)	140
C8—H8B⋯Cg3^v	0.97	2.73	3.514 (3)	138
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Figure 2
(a) A view of the crystal packing of the title compound along the c axis. Dashed lines indicate hydrogen bonds. (b) C—H⋯π interactions. (c) A view of the molecular stacks running along the a axis.

4. Hirshfeld surface analysis

In order to visualize and study the intermolecular contacts, a Hirshfeld surface analysis of the title compound was undertaken using Crystal Explorer 17.5 (Turner et al., 2017 ). Fig. 3a shows the 3D surface mapped over d_norm over the range −0.484 (red) to 1.403 (blue) a.u. The pale-red spots on the surface represent short N—H⋯O and C—H⋯O interactions (Table 2). The surfaces mapped over d_e and d_i are presented in Fig. 3b and 3c.

Figure 3
(a) Hirshfeld surfaces of the title molecule mapped over (a) d_norm, (b) d_e and (c) d_i.

The overall two-dimensional fingerprint plot and those delineated into H⋯H, H⋯C/C⋯H, H⋯O/O⋯H, H⋯Cl/Cl⋯H and C⋯C contacts are presented in Fig. 4. H⋯H interactions are the most prominent, accounting for 36.5% of the overall crystal packing. H⋯O/O⋯H contacts, including intermolecular C—H⋯O and N—H⋯O hydrogen bonding, make a 18.6% contribution to the Hirshfeld surface. H⋯C/C⋯H contacts add a 15.4% contribution. The contributions from H⋯Cl/Cl⋯H and C⋯C contacts are 11.2% and 7.6%, respectively.

Figure 4
(a) The overall two-dimensional fingerprint plot, and those delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) H⋯Cl/Cl⋯H and (f) C⋯C interactions.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update March 2020; Groom et al., 2016 ) revealed two structures containing the same pyridazinone fragments as in the title structure but with different substituents, viz. 6-[(E)-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2H)-one (MUCLEE; Daoui, Çınar et al., 2019) and (E)-6-(4-hydroxy-3-methoxyphenyl)ethenyl-4,5-dihydropyridazin-3(2H)-one (LOSSOE; Daoui, Baydere et al., 2019 ). Both these structures exhibit bond lengths in the pyridazine ring and N—H⋯O hydrogen-bonding parameters that are very similar to those observed in the title structure.

6. Synthesis and crystallization

A mixture of (E)-6-(4-hydroxystyryl)-4,5-dihydropyridazin-3(2H)-one (0.5 g, 2.3 mmol), K₂CO₃ (0.79 g, 5.7 mmol) and 2-chloro-1-(4-chlorophenyl)ethan-1-one (0.47 g, 2.5 mmol) in acetone (50 ml) was refluxed overnight. After cooling, the solution was filtered and the solvent removed under reduced pressure. The residue was purified by recrystallization from ethanol to afford single crystals (yield 72%).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were positioned geometrically and treated as riding, with C—H = 0.96 Å for methylene [U_iso(H) = 1.5 U_eq(C)], C—H = 0.93 Å for aromatic [U_iso(H) = 1.2 U_eq(C)] and C—H = 0.98 Å for methine [U_iso (H) = 1.2 U_eq(C)] H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₀H₁₇ClN₂O₃
M_r	368.80
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	7.3514 (4), 11.5539 (7), 41.397 (3)
V (Å³)	3516.2 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.45 × 0.20 × 0.05

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.925, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	19519, 2913, 1682
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.584

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.128, 0.99
No. of reflections	2913
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXT2018/3 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), Mercury (Macrae et al., 2020 ), WinGX (Farrugia, 2012 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2123627

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902101238X/yk2160sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902101238X/yk2160Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902101238X/yk2160Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

6-((E)-2-{4-[2-(4-Chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one top

Crystal data top

C₂₀H₁₇ClN₂O₃	D_x = 1.393 Mg m⁻³
M_r = 368.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 13252 reflections
a = 7.3514 (4) Å	θ = 1.0–25.1°
b = 11.5539 (7) Å	µ = 0.24 mm⁻¹
c = 41.397 (3) Å	T = 296 K
V = 3516.2 (4) Å³	Needle, colorless
Z = 8	0.45 × 0.20 × 0.05 mm
F(000) = 1536

Data collection top

STOE IPDS 2 diffractometer	2913 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1682 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.113
Detector resolution: 6.67 pixels mm^-1	θ_max = 24.5°, θ_min = 2.0°
rotation method scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
T_min = 0.925, T_max = 0.994	l = −48→48
19519 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0518P)²] where P = (F_o² + 2F_c²)/3
2913 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.40565 (17)	0.91913 (10)	0.94188 (2)	0.0775 (4)
O2	0.3849 (3)	0.58839 (19)	0.76710 (5)	0.0548 (6)
O1	0.3725 (4)	0.5145 (2)	0.82642 (5)	0.0652 (7)
O3	0.4691 (5)	0.8576 (2)	0.48754 (6)	0.0901 (11)
N1	0.4362 (5)	0.9053 (3)	0.57229 (6)	0.0583 (9)
N2	0.4339 (5)	0.9186 (3)	0.53853 (6)	0.0627 (9)
H2	0.420683	0.987853	0.531280	0.075*
C9	0.3861 (5)	0.6229 (3)	0.73520 (7)	0.0446 (8)
C12	0.3776 (5)	0.6716 (3)	0.66888 (7)	0.0450 (8)
C7	0.3875 (5)	0.6191 (3)	0.82384 (7)	0.0459 (8)
C14	0.4262 (5)	0.7332 (3)	0.72432 (7)	0.0460 (9)
H14	0.455198	0.791510	0.738937	0.055*
C15	0.3713 (5)	0.6918 (3)	0.63384 (7)	0.0485 (9)
H15	0.336983	0.628939	0.621208	0.058*
C8	0.4077 (5)	0.6746 (3)	0.79090 (7)	0.0463 (8)
H8A	0.316866	0.734746	0.788149	0.056*
H8B	0.527120	0.709594	0.788902	0.056*
C10	0.3420 (5)	0.5366 (3)	0.71335 (8)	0.0493 (9)
H10	0.315275	0.462357	0.720621	0.059*
C6	0.3939 (5)	0.6959 (3)	0.85261 (7)	0.0442 (8)
C13	0.4229 (4)	0.7563 (3)	0.69135 (8)	0.0480 (9)
H13	0.451610	0.830326	0.684145	0.058*
C11	0.3378 (5)	0.5613 (3)	0.68064 (8)	0.0495 (9)
H11	0.307759	0.502891	0.666138	0.059*
C17	0.4022 (5)	0.8025 (3)	0.58300 (7)	0.0480 (9)
C16	0.4088 (5)	0.7891 (3)	0.61803 (8)	0.0513 (9)
H16	0.441662	0.853378	0.630205	0.062*
C5	0.3951 (5)	0.6460 (3)	0.88335 (7)	0.0505 (9)
H5	0.395053	0.565786	0.885305	0.061*
C1	0.3956 (5)	0.8158 (3)	0.85007 (8)	0.0507 (9)
H1	0.393722	0.850303	0.829780	0.061*
C4	0.3965 (5)	0.7130 (3)	0.91071 (8)	0.0546 (10)
H4	0.394802	0.678837	0.931046	0.066*
C3	0.4005 (5)	0.8324 (3)	0.90763 (8)	0.0542 (9)
C2	0.4002 (5)	0.8843 (3)	0.87751 (8)	0.0560 (10)
H2A	0.403021	0.964539	0.875701	0.067*
C18	0.3570 (6)	0.7050 (3)	0.56077 (8)	0.0638 (11)
H18A	0.388487	0.632317	0.571073	0.077*
H18B	0.227071	0.704664	0.556707	0.077*
C20	0.4501 (6)	0.8347 (4)	0.51664 (9)	0.0667 (12)
C19	0.4555 (7)	0.7143 (3)	0.52951 (9)	0.0770 (14)
H19A	0.400668	0.662153	0.513941	0.092*
H19B	0.581099	0.690928	0.532538	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1050 (9)	0.0789 (7)	0.0487 (5)	−0.0053 (7)	−0.0003 (6)	−0.0147 (5)
O2	0.0842 (18)	0.0491 (13)	0.0311 (12)	−0.0041 (14)	−0.0035 (13)	0.0037 (11)
O1	0.102 (2)	0.0493 (16)	0.0440 (14)	−0.0081 (15)	0.0098 (15)	0.0043 (12)
O3	0.168 (3)	0.0733 (19)	0.0293 (15)	−0.019 (2)	0.0040 (16)	0.0027 (13)
N1	0.089 (3)	0.058 (2)	0.0279 (14)	−0.0069 (18)	0.0018 (15)	0.0022 (14)
N2	0.101 (3)	0.0548 (18)	0.0319 (15)	−0.0002 (18)	−0.0013 (16)	0.0067 (15)
C9	0.051 (2)	0.052 (2)	0.0315 (17)	−0.0038 (18)	0.0023 (17)	0.0030 (16)
C12	0.050 (2)	0.051 (2)	0.0340 (17)	−0.0002 (18)	0.0026 (16)	−0.0011 (16)
C7	0.051 (2)	0.050 (2)	0.0368 (18)	−0.0005 (18)	0.0030 (18)	0.0056 (15)
C14	0.054 (2)	0.048 (2)	0.0361 (18)	−0.0049 (18)	−0.0008 (16)	0.0006 (16)
C15	0.057 (2)	0.056 (2)	0.0321 (17)	−0.0005 (19)	0.0012 (18)	−0.0004 (16)
C8	0.056 (2)	0.048 (2)	0.0347 (17)	−0.0009 (19)	0.0018 (17)	0.0015 (16)
C10	0.066 (3)	0.0399 (19)	0.0417 (19)	−0.0040 (17)	0.0017 (17)	0.0058 (16)
C6	0.049 (2)	0.049 (2)	0.0346 (17)	0.0001 (18)	0.0049 (17)	0.0051 (15)
C13	0.054 (2)	0.048 (2)	0.0414 (19)	−0.0020 (19)	0.0011 (17)	0.0063 (16)
C11	0.064 (2)	0.049 (2)	0.0351 (18)	−0.0017 (18)	0.0034 (16)	−0.0031 (17)
C17	0.057 (2)	0.053 (2)	0.0349 (17)	0.0009 (19)	−0.0002 (18)	−0.0021 (16)
C16	0.060 (2)	0.059 (2)	0.0347 (18)	−0.004 (2)	0.0018 (19)	−0.0018 (16)
C5	0.063 (2)	0.047 (2)	0.0409 (19)	−0.0010 (19)	−0.0006 (19)	0.0083 (16)
C1	0.070 (3)	0.047 (2)	0.0348 (18)	0.005 (2)	0.0027 (19)	0.0076 (16)
C4	0.069 (3)	0.058 (2)	0.0367 (19)	−0.003 (2)	−0.0005 (19)	0.0076 (16)
C3	0.060 (2)	0.063 (2)	0.0389 (19)	0.002 (2)	0.0005 (19)	−0.0031 (18)
C2	0.071 (3)	0.047 (2)	0.050 (2)	0.001 (2)	0.002 (2)	0.0007 (18)
C18	0.097 (3)	0.057 (2)	0.037 (2)	−0.008 (2)	0.004 (2)	−0.0009 (18)
C20	0.102 (4)	0.065 (3)	0.034 (2)	−0.011 (2)	0.002 (2)	0.001 (2)
C19	0.126 (4)	0.062 (3)	0.043 (2)	−0.006 (3)	0.011 (2)	−0.001 (2)

Geometric parameters (Å, º) top

C20—O3	1.241 (4)	C10—C11	1.384 (5)
N2—C20	1.333 (5)	C10—H10	0.9300
N1—N2	1.406 (4)	C6—C1	1.389 (5)
N1—C17	1.292 (4)	C6—C5	1.397 (4)
C16—C17	1.459 (4)	C13—H13	0.9300
C15—C16	1.329 (5)	C11—H11	0.9300
C12—C15	1.470 (4)	C17—C18	1.492 (5)
C7—O1	1.219 (4)	C16—H16	0.9300
Cl1—C3	1.737 (3)	C5—C4	1.373 (5)
O2—C9	1.379 (4)	C5—H5	0.9300
O2—C8	1.411 (4)	C1—C2	1.385 (5)
N2—H2	0.8600	C1—H1	0.9300
C9—C14	1.384 (4)	C4—C3	1.386 (5)
C9—C10	1.385 (4)	C4—H4	0.9300
C12—C13	1.391 (4)	C3—C2	1.383 (5)
C12—C11	1.395 (5)	C2—H2A	0.9300
C7—C6	1.486 (4)	C18—C19	1.487 (5)
C7—C8	1.514 (4)	C18—H18A	0.9700
C14—C13	1.391 (4)	C18—H18B	0.9700
C14—H14	0.9300	C20—C19	1.490 (5)
C15—H15	0.9300	C19—H19A	0.9700
C8—H8A	0.9700	C19—H19B	0.9700
C8—H8B	0.9700

C9—O2—C8	117.6 (2)	C12—C11—H11	119.2
C17—N1—N2	116.0 (3)	N1—C17—C16	115.6 (3)
C20—N2—N1	126.5 (3)	N1—C17—C18	121.7 (3)
C20—N2—H2	116.7	C16—C17—C18	122.7 (3)
N1—N2—H2	116.7	C15—C16—C17	124.9 (3)
O2—C9—C14	125.4 (3)	C15—C16—H16	117.5
O2—C9—C10	114.6 (3)	C17—C16—H16	117.5
C14—C9—C10	120.0 (3)	C4—C5—C6	121.2 (3)
C13—C12—C11	117.4 (3)	C4—C5—H5	119.4
C13—C12—C15	123.8 (3)	C6—C5—H5	119.4
C11—C12—C15	118.9 (3)	C2—C1—C6	120.5 (3)
O1—C7—C6	121.7 (3)	C2—C1—H1	119.7
O1—C7—C8	120.5 (3)	C6—C1—H1	119.7
C6—C7—C8	117.8 (3)	C5—C4—C3	119.1 (3)
C9—C14—C13	119.5 (3)	C5—C4—H4	120.5
C9—C14—H14	120.3	C3—C4—H4	120.5
C13—C14—H14	120.3	C2—C3—C4	121.0 (3)
C16—C15—C12	127.9 (3)	C2—C3—Cl1	119.1 (3)
C16—C15—H15	116.1	C4—C3—Cl1	120.0 (3)
C12—C15—H15	116.1	C3—C2—C1	119.4 (3)
O2—C8—C7	108.5 (3)	C3—C2—H2A	120.3
O2—C8—H8A	110.0	C1—C2—H2A	120.3
C7—C8—H8A	110.0	C19—C18—C17	112.0 (3)
O2—C8—H8B	110.0	C19—C18—H18A	109.2
C7—C8—H8B	110.0	C17—C18—H18A	109.2
H8A—C8—H8B	108.4	C19—C18—H18B	109.2
C11—C10—C9	119.7 (3)	C17—C18—H18B	109.2
C11—C10—H10	120.1	H18A—C18—H18B	107.9
C9—C10—H10	120.1	O3—C20—N2	121.0 (4)
C1—C6—C5	118.7 (3)	O3—C20—C19	122.9 (4)
C1—C6—C7	122.4 (3)	N2—C20—C19	116.0 (3)
C5—C6—C7	118.9 (3)	C18—C19—C20	111.4 (3)
C12—C13—C14	121.7 (3)	C18—C19—H19A	109.3
C12—C13—H13	119.1	C20—C19—H19A	109.3
C14—C13—H13	119.1	C18—C19—H19B	109.3
C10—C11—C12	121.7 (3)	C20—C19—H19B	109.3
C10—C11—H11	119.2	H19A—C19—H19B	108.0

C17—N1—N2—C20	−19.7 (6)	N2—N1—C17—C16	178.7 (3)
C8—O2—C9—C14	7.0 (5)	N2—N1—C17—C18	−2.0 (5)
C8—O2—C9—C10	−172.8 (3)	C12—C15—C16—C17	179.1 (4)
O2—C9—C14—C13	179.9 (3)	N1—C17—C16—C15	177.3 (4)
C10—C9—C14—C13	−0.4 (5)	C18—C17—C16—C15	−1.9 (6)
C13—C12—C15—C16	1.2 (6)	C1—C6—C5—C4	0.5 (6)
C11—C12—C15—C16	−178.2 (4)	C7—C6—C5—C4	−178.4 (3)
C9—O2—C8—C7	175.7 (3)	C5—C6—C1—C2	0.6 (6)
O1—C7—C8—O2	6.4 (5)	C7—C6—C1—C2	179.5 (3)
C6—C7—C8—O2	−175.9 (3)	C6—C5—C4—C3	−1.3 (6)
O2—C9—C10—C11	179.6 (3)	C5—C4—C3—C2	1.0 (6)
C14—C9—C10—C11	−0.1 (5)	C5—C4—C3—Cl1	−179.1 (3)
O1—C7—C6—C1	−174.5 (4)	C4—C3—C2—C1	0.1 (6)
C8—C7—C6—C1	7.8 (5)	Cl1—C3—C2—C1	−179.8 (3)
O1—C7—C6—C5	4.4 (6)	C6—C1—C2—C3	−0.9 (6)
C8—C7—C6—C5	−173.3 (3)	N1—C17—C18—C19	33.8 (6)
C11—C12—C13—C14	−0.9 (5)	C16—C17—C18—C19	−147.0 (4)
C15—C12—C13—C14	179.7 (3)	N1—N2—C20—O3	−170.9 (4)
C9—C14—C13—C12	0.9 (5)	N1—N2—C20—C19	5.5 (6)
C9—C10—C11—C12	0.2 (6)	C17—C18—C19—C20	−44.6 (5)
C13—C12—C11—C10	0.3 (5)	O3—C20—C19—C18	−156.4 (4)
C15—C12—C11—C10	179.8 (3)	N2—C20—C19—C18	27.3 (6)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.86	2.11	2.891 (4)	151
C4—H4···O3ⁱⁱ	0.93	2.44	3.327 (4)	160
C13—H13···O1ⁱⁱⁱ	0.93	2.53	3.421 (4)	161
C18—H18A···Cl1^iv	0.97	2.94	3.737 (3)	140
C8—H8B···Cg3^v	0.97	2.73	3.514 (3)	138

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

Acknowledgements

Author contributions are as follows. Conceptualization, SD, IM, EBÇ, AA, ND, NB and KK; synthesis, SD, KK, NB, AA, writing, IM and EBÇ, formal analysis ND and KK, validation IM, EBÇ and ND.

Funding information

Funding for this research was provided by Ondokuz Mayıs University under project No. PYO·FEN.1906.19.001.

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