Crystal structure and Hirshfeld surface analysis of 4-(2,6-di­chloro­benz­yl)-6-[(E)-2-phenyl­ethen­yl]pyridazin-3(2H)-one

Daoui, S.; Cinar, E.B.; Dege, N.; Chelfi, T.; El Kalai, F.; Abudunia, A.; Karrouchi, K.; Benchat, N.

doi:10.1107/S205698902001573X

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 77| Part 1| January 2021| Pages 23-27

https://doi.org/10.1107/S205698902001573X

Open

access

Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

Said Daoui,^a Emine Berrin Cinar,^b ^* Necmi Dege,^b Tarik Chelfi,^a Fouad El Kalai,^a Abdulmalik Abudunia,^c ^* Khalid Karrouchi ^d and Noureddine Benchat ^a

^aLaboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohamed 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, Rabat, Morocco
^*Correspondence e-mail: emineberrin.cinar@omu.edu.tr, abdulmalikabudunia@gmail.com

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 19 November 2020; accepted 1 December 2020; online 1 January 2021)

The title pyridazinone derivative, C₁₉H₁₄Cl₂N₂O, an important pharmacophore with a wide variety of biological applications is not planar, the chlorophenyl and pyridazinone rings being almost perpendicular, subtending a dihedral angle of 85.73 (11)°. The phenyl ring of the styryl group is coplanar with the pyridazinone ring [1.47 (12)°]. In the crystal, N—H⋯O hydrogen bonds form inversion dimers with an R₂²(8) ring motif and C—H⋯Cl hydrogen bonds also occur. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (37.9%), C⋯H/H⋯C (18.7%), Cl⋯H/ H⋯Cl (16.4%) and Cl⋯C/C⋯Cl (6.7%) contacts.

Keywords: crystal structure; Hirshfeld surface analysis; pyridazine derivative; pyridazinone.

CCDC reference: 2047452

1. Chemical context

Pyridazines are an important family of six-membered aromatic heterocycles containing two nitrogen atoms. Pyridazinone is an important pharmacophore possessing a wide range of biological activities including antitumor (Bouchmaa et al., 2018 , 2019 ), anti-inflammatory (Boukharsa et al., 2018 ), antihypertensive (Siddiqui et al., 2011 ), antidepressant (Boukharsa et al., 2016 ), anti-HIV (Livermore et al., 1993 ), antihistaminic (Tao et al. 2012 ), analgesic (Gökçe et al., 2009 ) and anticonvulsant (Partap et al., 2018 ) and is used in glucan synthase inhibitors (Zhou et al., 2011 ) and herbicidal agents (Asif et al., 2013 ). The chemistry of pyridazinones has been an interesting field of study for decades and this nitrogen heterocycle has become a scaffold of choice for the development of potential drug candidates (Dubey et al., 2015 ; Thakur et al., 2010 ).

In a continuation of our studies towards the synthesis, molecular structures, Hirshfeld surfaces analysis and DFT studies of new pyridazin-3(2H)-one derivatives (Daoui et al., 2020

, 2021

; El Kalai et al., 2021

), we report herein the crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one.

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The C1–C6 phenyl ring and the pyridazinone ring (N1/N2/C8–C11) are almost perpendicular, subtending a dihedral angle of 85.73 (11)°. The C14–C19 phenyl ring of the styryl group is coplanar with the pyridazinone ring [1.47 (12)°]. The carbonyl group has a C8=O1 bond length of 1.236 (2) Å, and the C8—N1 and C11—N2 bond lengths in the pyridazine ring are 1.357 (3) and 1.305 (2) Å, respectively. The N1—N2 bond length is 1.344 (2) Å.

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, pairs of N—H⋯O hydrogen bonds form inversion dimers with an $[R_{2}^{2}]$ (8) ring motif (Table 1, Fig. 2). C3—H3⋯Cl1 hydrogen bonds are also observed. C—H⋯π interactions between the $[R_{2}^{2}]$ (8) dimer rings and H16 atoms [centroid-to-centroid distance of 3.501 (9) Å; length between dimer ring and C14–C19 ring = 3.569 (12) Å] also occur (Fig. 3). π–π interactions also occur with a centroid–centroid distance Cg1⋯Cg3(−x + 1, −y + 2, −z + 1) of 3.9107 (15) Å where Cg1 and Cg3 are the centroids of the N1/N2/C8–C11 and C14–C19 rings, respectively (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.92	2.772 (2)	171
C3—H3⋯Cl1ⁱⁱ	0.93	2.97	3.824 (3)	153
C7—H7A⋯O1	0.97	2.42	2.803 (2)	103
C13—H13⋯N2	0.93	2.51	2.845 (3)	101
Symmetry codes: (i) ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
View of the crystal structure of the title compound. N—H⋯O hydrogen bonds are represented by red dashed lines and C—H⋯N and C—H⋯O interactions are shown as blue dashed lines.

Figure 3
Packing diagram showing the intermolecular interactions in the title compound (C—H⋯π interactions shown as black dashed lines and π–π interactions as purple dashed lines).

4. Database survey

A survey of the Cambridge Structural Database (CSD version 5.41, update of March 2020; Groom et al., 2016 ) reveals six comparable pyridazine derivatives, 1-(6-benzoyl-2-phenyl-2,3-dihydropyridazin-4-yl)ethanone 1-(4-benzoyl-2-phenyl-2,3-dihydropyridazin-6-yl)ethanone (AQIKOB; Al-Awadi et al., 2011 ), 4-(2′-chloro-6′-fluorophenyl)-2,5-dioxo-8-phenyl-1,2,3,4,5,6-hexahydropyrido(2,3-d)pyridazine (BARQOA; Pita et al., 2000 ), 4-[(2,6-dichlorophenyl)methyl]-6-phenylpyridazin-3(2H)-one (BOBXEY; El Kali, Kansiz et al., 2019 ), ethyl {5-[(3-chlorophenyl)methyl]-6-oxo-3-phenylpyridazin-1(6H)-yl}acetate (FODQUN; El Kalai, Baydere et al., 2019 ), 4-benzyl-2-[2-(4-fluorophenyl)-2-oxoethyl]-6-phenylpyridazin-3(2H)-one (NOLDUQ; Daoui et al., 2019 ) and 4-benzyl-6-p-tolylpyridazin-3(2H)-one (YOTVIN; Oubair et al., 2009 ). Of these, BOBXEY, (II), is very similar to the title compound. The phenyl ring and the pyridazine ring are twisted with respect to each other, making a dihedral angle of 21.76 (18)° and the phenyl ring (C1–C6) of the benzyl group is inclined to the pyridazine ring by 79.61 (19)°. Relevant bond lengths in (II) are C17=O1 = 1.229 (5), C17—N2 = 1.388 (5) Å and C10—N1 =1.299 (4) Å. The N1—N2 bond lengths in (I) and (II) are virtually the same, with values of 1.348 (2) and 1.353 (4) Å, respectively. In the structure of YOTVIN, N—H⋯O bonds are also observed.

5. Hirshfeld surface analysis

A Hirshfeld surface (HS) study of the title compound was undertaken using CrystalExplorer17.5 (Turner et al., 2017 ) to visualize and study the intermolecular contacts. The d_norm surface of the title compound is illustrated in Fig. 4a. The shape-index, a tool for visualizing π–π stacking interactions by the presence of adjacent red and blue triangles is given in Fig. 4b while Fig. 4c shows the curvedness map of the title compound. The absence of prominent red and blue triangles in the shape-index map, as well as the absence of large green regions in the curvedness map, confirms that π–π and C—H⋯π interactions are weak. Fig. 5 shows fingerprint plots that quantitatively summarize the nature and type of intermolecular contacts. The highest contribution to the Hirshfeld surface is from H⋯H contacts (Fig. 5b). Other interactions and their respective contributions are C⋯H/H⋯C (18.7%), Cl⋯H/H⋯Cl (16.4%), Cl⋯C/C⋯Cl (6.7%), O⋯H/H⋯O (6.5%), N⋯H/H⋯N (4.8%), C⋯O/O⋯C (3.3%) and C⋯N/N⋯C (2.5%). The acceptor and donor atoms participating in the hydrogen bond appear as blue (donors) and red regions (acceptors) corresponding to positive and negative potential, respectively, in the HS mapped over the electrostatic potential, in the range −0.099–0.165 a.u., as shown in Fig. 6.

Figure 4
(a) Hirshfeld surface mapped over d_norm for visualizing the intermolecular interactions of the title compound, (b) shape-index map and (c) curvedness map of the title molecule.

Figure 5
Two-dimensional fingerprint plots for the title compound showing the relative contributions of the atom pairs to the Hirshfeld surface.

Figure 6
A view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential.

6. Synthesis and crystallization

To a solution of (E)-6-styryl-4,5-dihydropyridazin-3(2H)-one (0.2 g, 1 mmol) and 2,6-dichlorobenzaldehyde (0.175 g, 1 mmol) in 30 ml of ethanol, sodium ethanoate (0.23 g, 2.8 mmol) was added. The mixture was refluxed for 3 h. The reaction mixture was cooled, diluted with cold water and acidified with concentrated hydrochloric acid. The precipitate was filtered, washed with water, dried and recrystallized from ethanol. Colourless single-crystals were obtained by slow evaporation at room temperature.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were positioned geometrically with C—H distances of 0.93–0.97 Å and refined as riding, with U_iso(H) = 1.2U_eq(C). The N-bound H atom was located in a difference-Fourier map and refined with N—H = 0.86 Å.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₄Cl₂N₂O
M_r	357.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.1306 (5), 10.7019 (6), 15.7749 (7)
β (°)	97.715 (4)
V (Å³)	1694.78 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.39
Crystal size (mm)	0.72 × 0.47 × 0.13

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.796, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	20123, 5828, 2944
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.170, 1.01
No. of reflections	5828
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21
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: 2047452

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902001573X/dx2034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902001573X/dx2034Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902001573X/dx2034Isup3.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).

4-(2,6-Dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one top

Crystal data top

C₁₉H₁₄Cl₂N₂O	F(000) = 736
M_r = 357.22	D_x = 1.400 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1306 (5) Å	Cell parameters from 16480 reflections
b = 10.7019 (6) Å	θ = 1.9–32.4°
c = 15.7749 (7) Å	µ = 0.39 mm⁻¹
β = 97.715 (4)°	T = 296 K
V = 1694.78 (15) Å³	Plate, colorless
Z = 4	0.72 × 0.47 × 0.13 mm

Data collection top

Stoe IPDS 2 diffractometer	5828 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2944 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.047
Detector resolution: 6.67 pixels mm^-1	θ_max = 32.0°, θ_min = 2.3°
rotation method scans	h = −12→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
T_min = 0.796, T_max = 0.937	l = −23→23
20123 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0652P)² + 0.3156P] where P = (F_o² + 2F_c²)/3
5828 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.21 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
Cl2	0.32888 (9)	0.44720 (8)	0.41784 (5)	0.1022 (3)
Cl1	0.06171 (9)	0.57454 (9)	0.67843 (6)	0.1101 (3)
O1	−0.00667 (14)	0.83981 (14)	0.49196 (12)	0.0698 (4)
N2	0.30239 (16)	0.97613 (15)	0.57214 (12)	0.0561 (4)
N1	0.17344 (16)	0.95588 (15)	0.54273 (13)	0.0582 (4)
H1	0.1229	1.0208	0.5381	0.070*
C6	0.19680 (18)	0.50436 (17)	0.55109 (14)	0.0520 (5)
C11	0.37910 (19)	0.87772 (18)	0.58104 (13)	0.0508 (4)
C9	0.2000 (2)	0.73781 (17)	0.53008 (13)	0.0508 (4)
C8	0.11329 (19)	0.84552 (18)	0.51939 (14)	0.0536 (5)
C10	0.32911 (19)	0.75621 (18)	0.56121 (14)	0.0533 (5)
H10	0.3862	0.6880	0.5698	0.064*
C12	0.5217 (2)	0.8968 (2)	0.61209 (14)	0.0568 (5)
H12	0.5752	0.8261	0.6204	0.068*
C7	0.1371 (2)	0.61526 (18)	0.50303 (16)	0.0609 (6)
H7A	0.0433	0.6192	0.5095	0.073*
H7B	0.1431	0.6031	0.4427	0.073*
C14	0.7197 (2)	1.0298 (2)	0.66024 (15)	0.0615 (5)
C13	0.5792 (2)	1.0060 (2)	0.62890 (15)	0.0607 (5)
H13	0.5245	1.0759	0.6199	0.073*
C1	0.1675 (2)	0.4752 (2)	0.63198 (16)	0.0650 (6)
C5	0.2807 (2)	0.4200 (2)	0.51757 (16)	0.0631 (6)
C19	0.7618 (3)	1.1510 (3)	0.67726 (17)	0.0761 (7)
H19	0.7004	1.2159	0.6691	0.091*
C2	0.2149 (3)	0.3694 (3)	0.67623 (18)	0.0840 (8)
H2	0.1934	0.3533	0.7307	0.101*
C15	0.8136 (2)	0.9359 (3)	0.67285 (19)	0.0776 (7)
H15	0.7882	0.8536	0.6611	0.093*
C4	0.3270 (3)	0.3132 (2)	0.5602 (2)	0.0831 (8)
H4	0.3810	0.2579	0.5351	0.100*
C3	0.2937 (3)	0.2891 (3)	0.6385 (2)	0.0897 (9)
H3	0.3249	0.2168	0.6672	0.108*
C18	0.8940 (3)	1.1772 (3)	0.7063 (2)	0.0951 (9)
H18	0.9209	1.2595	0.7168	0.114*
C16	0.9453 (3)	0.9629 (4)	0.7027 (2)	0.0969 (9)
H16	1.0072	0.8984	0.7115	0.116*
C17	0.9850 (3)	1.0827 (4)	0.7194 (2)	0.1007 (10)
H17	1.0736	1.1002	0.7397	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.1168 (6)	0.1083 (6)	0.0881 (5)	0.0366 (5)	0.0379 (5)	0.0082 (4)
Cl1	0.1042 (6)	0.1263 (7)	0.1069 (6)	−0.0057 (5)	0.0406 (5)	−0.0446 (5)
O1	0.0467 (8)	0.0506 (8)	0.1070 (13)	0.0102 (6)	−0.0080 (8)	−0.0061 (8)
N2	0.0479 (9)	0.0427 (9)	0.0767 (12)	0.0047 (7)	0.0040 (8)	−0.0020 (8)
N1	0.0459 (9)	0.0409 (8)	0.0860 (13)	0.0104 (7)	0.0017 (8)	−0.0034 (8)
C6	0.0467 (9)	0.0412 (9)	0.0653 (12)	−0.0024 (8)	−0.0024 (9)	−0.0062 (9)
C11	0.0469 (10)	0.0460 (10)	0.0587 (12)	0.0051 (8)	0.0047 (9)	0.0004 (9)
C9	0.0506 (10)	0.0406 (9)	0.0597 (12)	0.0066 (8)	0.0019 (9)	−0.0011 (8)
C8	0.0486 (10)	0.0434 (10)	0.0671 (13)	0.0070 (8)	0.0014 (9)	−0.0014 (9)
C10	0.0488 (11)	0.0415 (10)	0.0682 (13)	0.0114 (8)	0.0029 (9)	−0.0003 (9)
C12	0.0488 (10)	0.0493 (11)	0.0708 (14)	0.0067 (8)	0.0027 (9)	−0.0009 (9)
C7	0.0519 (11)	0.0451 (10)	0.0813 (15)	0.0073 (9)	−0.0074 (10)	−0.0068 (10)
C14	0.0553 (11)	0.0673 (14)	0.0618 (13)	−0.0049 (10)	0.0073 (10)	−0.0002 (11)
C13	0.0526 (11)	0.0545 (12)	0.0740 (14)	0.0054 (10)	0.0049 (10)	0.0029 (10)
C1	0.0605 (12)	0.0645 (13)	0.0692 (14)	−0.0135 (10)	0.0054 (11)	−0.0135 (11)
C5	0.0652 (13)	0.0512 (11)	0.0716 (14)	0.0087 (10)	0.0042 (11)	−0.0006 (10)
C19	0.0754 (16)	0.0741 (16)	0.0785 (16)	−0.0148 (13)	0.0092 (13)	−0.0052 (13)
C2	0.095 (2)	0.0852 (19)	0.0684 (16)	−0.0303 (16)	−0.0025 (15)	0.0149 (14)
C15	0.0567 (13)	0.0771 (16)	0.0962 (19)	−0.0020 (12)	−0.0002 (12)	0.0039 (14)
C4	0.0901 (18)	0.0569 (14)	0.099 (2)	0.0237 (13)	0.0024 (16)	0.0022 (14)
C3	0.105 (2)	0.0610 (16)	0.097 (2)	0.0033 (15)	−0.0089 (18)	0.0160 (15)
C18	0.098 (2)	0.103 (2)	0.0835 (19)	−0.043 (2)	0.0090 (16)	−0.0134 (17)
C16	0.0554 (14)	0.125 (3)	0.106 (2)	0.0002 (16)	−0.0032 (14)	0.010 (2)
C17	0.0643 (17)	0.141 (3)	0.093 (2)	−0.031 (2)	−0.0051 (15)	−0.002 (2)

Geometric parameters (Å, º) top

Cl2—C5	1.733 (3)	C14—C15	1.379 (3)
Cl1—C1	1.740 (3)	C14—C19	1.380 (3)
O1—C8	1.236 (2)	C14—C13	1.465 (3)
N2—C11	1.305 (2)	C13—H13	0.9300
N2—N1	1.344 (2)	C1—C2	1.382 (4)
N1—C8	1.357 (3)	C5—C4	1.376 (3)
N1—H1	0.8600	C19—C18	1.385 (4)
C6—C1	1.384 (3)	C19—H19	0.9300
C6—C5	1.392 (3)	C2—C3	1.362 (4)
C6—C7	1.492 (3)	C2—H2	0.9300
C11—C10	1.415 (3)	C15—C16	1.384 (4)
C11—C12	1.476 (3)	C15—H15	0.9300
C9—C10	1.349 (3)	C4—C3	1.350 (4)
C9—C8	1.445 (3)	C4—H4	0.9300
C9—C7	1.495 (3)	C3—H3	0.9300
C10—H10	0.9300	C18—C17	1.366 (5)
C12—C13	1.317 (3)	C18—H18	0.9300
C12—H12	0.9300	C16—C17	1.358 (5)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—H17	0.9300

C11—N2—N1	116.38 (17)	C12—C13—H13	116.4
N2—N1—C8	127.90 (16)	C14—C13—H13	116.4
N2—N1—H1	116.1	C2—C1—C6	123.2 (2)
C8—N1—H1	116.1	C2—C1—Cl1	118.7 (2)
C1—C6—C5	114.9 (2)	C6—C1—Cl1	118.08 (19)
C1—C6—C7	121.7 (2)	C4—C5—C6	122.6 (2)
C5—C6—C7	123.3 (2)	C4—C5—Cl2	117.6 (2)
N2—C11—C10	121.83 (18)	C6—C5—Cl2	119.75 (17)
N2—C11—C12	117.79 (18)	C14—C19—C18	121.0 (3)
C10—C11—C12	120.38 (17)	C14—C19—H19	119.5
C10—C9—C8	118.07 (18)	C18—C19—H19	119.5
C10—C9—C7	125.98 (17)	C3—C2—C1	118.7 (3)
C8—C9—C7	115.93 (17)	C3—C2—H2	120.6
O1—C8—N1	121.52 (17)	C1—C2—H2	120.6
O1—C8—C9	123.72 (18)	C14—C15—C16	120.8 (3)
N1—C8—C9	114.76 (17)	C14—C15—H15	119.6
C9—C10—C11	121.03 (17)	C16—C15—H15	119.6
C9—C10—H10	119.5	C3—C4—C5	119.7 (3)
C11—C10—H10	119.5	C3—C4—H4	120.2
C13—C12—C11	125.18 (19)	C5—C4—H4	120.2
C13—C12—H12	117.4	C4—C3—C2	120.9 (3)
C11—C12—H12	117.4	C4—C3—H3	119.6
C6—C7—C9	115.12 (17)	C2—C3—H3	119.6
C6—C7—H7A	108.5	C17—C18—C19	120.2 (3)
C9—C7—H7A	108.5	C17—C18—H18	119.9
C6—C7—H7B	108.5	C19—C18—H18	119.9
C9—C7—H7B	108.5	C17—C16—C15	120.6 (3)
H7A—C7—H7B	107.5	C17—C16—H16	119.7
C15—C14—C19	117.8 (2)	C15—C16—H16	119.7
C15—C14—C13	122.9 (2)	C16—C17—C18	119.5 (3)
C19—C14—C13	119.3 (2)	C16—C17—H17	120.2
C12—C13—C14	127.2 (2)	C18—C17—H17	120.2

C11—N2—N1—C8	−1.5 (3)	C5—C6—C1—C2	−1.3 (3)
N1—N2—C11—C10	−0.3 (3)	C7—C6—C1—C2	176.1 (2)
N1—N2—C11—C12	179.18 (19)	C5—C6—C1—Cl1	−179.26 (16)
N2—N1—C8—O1	−178.9 (2)	C7—C6—C1—Cl1	−1.8 (3)
N2—N1—C8—C9	1.7 (3)	C1—C6—C5—C4	2.4 (3)
C10—C9—C8—O1	−179.6 (2)	C7—C6—C5—C4	−175.0 (2)
C7—C9—C8—O1	1.9 (3)	C1—C6—C5—Cl2	−178.40 (17)
C10—C9—C8—N1	−0.1 (3)	C7—C6—C5—Cl2	4.2 (3)
C7—C9—C8—N1	−178.7 (2)	C15—C14—C19—C18	−0.2 (4)
C8—C9—C10—C11	−1.4 (3)	C13—C14—C19—C18	−179.5 (2)
C7—C9—C10—C11	177.0 (2)	C6—C1—C2—C3	−0.4 (4)
N2—C11—C10—C9	1.7 (3)	Cl1—C1—C2—C3	177.5 (2)
C12—C11—C10—C9	−177.8 (2)	C19—C14—C15—C16	0.9 (4)
N2—C11—C12—C13	−2.5 (3)	C13—C14—C15—C16	−179.9 (3)
C10—C11—C12—C13	177.0 (2)	C6—C5—C4—C3	−1.7 (4)
C1—C6—C7—C9	78.6 (3)	Cl2—C5—C4—C3	179.0 (2)
C5—C6—C7—C9	−104.2 (2)	C5—C4—C3—C2	−0.2 (5)
C10—C9—C7—C6	31.4 (3)	C1—C2—C3—C4	1.2 (4)
C8—C9—C7—C6	−150.2 (2)	C14—C19—C18—C17	−0.7 (4)
C11—C12—C13—C14	179.6 (2)	C14—C15—C16—C17	−0.7 (5)
C15—C14—C13—C12	3.0 (4)	C15—C16—C17—C18	−0.2 (5)
C19—C14—C13—C12	−177.8 (2)	C19—C18—C17—C16	0.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.92	2.772 (2)	171
C3—H3···Cl1ⁱⁱ	0.93	2.97	3.824 (3)	153

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

Funding information

This study was supported by Ondokuz Mayıs University under project No. PYOFEN.1906.19.001.

References

Al-Awadi, N. A., Ibrahim, M. R., Al-Etaibi, A. M. & Elnagdia, M. H. (2011). Arkivoc (ii) pp. 310–321, https://doi.org/10.3998/ark.5550190.0012.225 Google Scholar
Asif, M. (2013). Mini-Rev. Org. Chem. 10, 113–122. Web of Science CrossRef CAS Google Scholar
Bouchmaa, N., Mrid, R. B., Boukharsa, Y., Bouargalne, Y., Nhiri, M., Idir, A., Taoufik, J., Ansar, M. & Zyad, A. (2019). Drug Res (Stuttg), 69, 528–536. Web of Science CAS PubMed Google Scholar
Bouchmaa, N., Tilaoui, M., Boukharsa, Y., Jaâfari, A., Mouse, H. A., Ali Oukerrou, M., Taoufik, J., Ansar, M. & Zyad, A. (2018). Pharm. Chem. J. 51, 893–901. Web of Science CrossRef CAS Google Scholar
Boukharsa, Y., Lakhlili, W., El harti, J., Meddah, B., Tiendrebeogo, R. Y., Taoufik, J., El Abbes Faouzi, M., Ibrahimi, A. & Ansar, M. (2018). J. Mol. Struct. 1153, 119–127. Web of Science CrossRef CAS Google Scholar
Boukharsa, Y., Meddah, B., Tiendrebeogo, R. Y., Ibrahimi, A., Taoufik, J., Cherrah, Y., Benomar, A., Faouzi, M. E. A. & Ansar, M. (2016). Med. Chem. Res. 25, 494–500. Web of Science CrossRef CAS Google Scholar
Daoui, S., Baydere, C., Akman, F., El Kalai, F., Mahi, L., Dege, N., Topcu, Y., Karrouchi, K. & Benchat, N. (2021). J. Mol. Struct. 1225, 129–180. CSD CrossRef Google Scholar
Daoui, S., Baydere, C., Chelfi, T., El Kalai, F., Dege, N., Karrouchi, K. & Benchat, N. (2020). Acta Cryst. E76, 432–437. Web of Science CSD CrossRef IUCr Journals Google Scholar
Daoui, S., Faizi, M. S. H., Kalai, F. E., Saddik, R., Dege, N., Karrouchi, K. & Benchat, N. (2019). Acta Cryst. E75, 1030–1034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dubey, S. & Bhosle, P. A. (2015). Med. Chem. Res. 24, 3579–3598. Web of Science CrossRef CAS Google Scholar
El Kalai, F., Baydere, C., Daoui, S., Saddik, R., Dege, N., Karrouchi, K. & Benchat, N. (2019). Acta Cryst. E75, 892–895. Web of Science CSD CrossRef IUCr Journals Google Scholar
El Kali, F., Kansiz, S., Daoui, S., Saddik, R., Dege, N., Karrouchi, K. & Benchat, N. (2019). Acta Cryst. E75, 650–654. Web of Science CSD CrossRef IUCr Journals Google Scholar
El Kalai, F., Karrouchi, K., Baydere, C., Daoui, S., Allali, M., Dege, N., Benchat, N. & Brandán, S. A. (2021). J. Mol. Struct. 1223, 129–213. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gökçe, M., Utku, S. & Küpeli, E. (2009). Eur. J. Med. Chem. 44, 3760–3764. Web of Science PubMed 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
Livermore, D., Bethell, R. C., Cammack, N., Hancock, A. P., Hann, M. M. & Green, D. (1993). J. Med. Chem. 36, 3784–3794. CSD CrossRef CAS PubMed Web of Science Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oubair, A., Daran, J.-C., Fihi, R., Majidi, L. & Azrour, M. (2009). Acta Cryst. E65, o1350–o1351. Web of Science CSD CrossRef IUCr Journals Google Scholar
Partap, S., Akhtar, M. J., Yar, M. S., Hassan, M. Z. & Siddiqui, A. A. (2018). Bioorg. Chem. 77, 74–83. Web of Science CrossRef CAS PubMed Google Scholar
Pita, B., Sotelo, E., Suárez, M., Raviña, E., Ochoa, E., Verdecia, Y., Novoa, H., Blaton, N., de Ranter, C. & Peeters, O. M. (2000). Tetrahedron, 56, 2473–2479. Web of Science CSD CrossRef CAS 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
Siddiqui, A. A., Mishra, R., Shaharyar, M., Husain, A., Rashid, M. & Pal, P. (2011). Bioorg. Med. Chem. Lett. 21, 1023–1026. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Tao, M., Aimone, L. D., Gruner, J. A., Mathiasen, J. R., Huang, Z., Lyons, J., Raddatz, R. & Hudkins, R. L. (2012). Bioorg. Med. Chem. Lett. 22, 1073–1077. Web of Science CrossRef CAS PubMed Google Scholar
Thakur, A. S., Verma, P. & Chandy, A. (2010). Asian. J. Res. Chem. 3, 265–271. Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17.5. University of Western Australia. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, G., Ting, P. C., Aslanian, R., Cao, J., Kim, D. W., Kuang, R., Lee, J. F., Schwerdt, J., Wu, H., Jason Herr, R., Zych, A. J., Yang, J., Lam, S., Wainhaus, S., Black, T. A., McNicholas, P. M., Xu, Y. & Walker, S. S. (2011). Bioorg. Med. Chem. Lett. 21, 2890–2893. Web of Science CrossRef CAS PubMed 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.