Crystal structure and Hirshfeld surface analysis of 4-(2,6-di­chloro­benz­yl)-6-phenyl­pyridazin-3(2H)-one

El Kali, F.; Kansiz, S.; Daoui, S.; Saddik, R.; Dege, N.; Karrouchi, K.; Benchat, N.

doi:10.1107/S2056989019005139

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ISSN: 2056-9890

Volume 75| Part 5| May 2019| Pages 650-654

https://doi.org/10.1107/S2056989019005139

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Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-phenylpyridazin-3(2H)-one

Fouad El Kali,^a ^* Sevgi Kansiz,^b ^* Said Daoui,^a Rafik Saddik,^c Necmi Dege,^b Khalid Karrouchi ^d and Noureddine Benchat ^a

^aLaboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, University Mohamed Premier, Oujda 60000, Morocco, ^bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, ^cLaboratory of Organic Synthesis, Extraction and Development, Faculty of, Sciences, Hassan II University, Casablanca, Morocco, and ^dLaboratory of Plant Chemistry, Organic and Bioorganic Synthesis, URAC23, Faculty of Science, BP 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco
^*Correspondence e-mail: elkalifouad408@gmail.com, sevgi.kansiz85@gmail.com

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 25 March 2019; accepted 14 April 2019; online 18 April 2019)

The asymmetric unit of the title compound, C₁₇H₁₂Cl₂N₂O, contains one independent molecule. The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules to form inversion dimers with an R₂²(8) ring motif. The dimers are linked by C—H⋯O interactions, forming layers parallel to the bc plane. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H⋯H (31.4%), Cl⋯H/H⋯Cl (19.9%) and C⋯H/H⋯C (19%) contacts.

Keywords: crystal structure; pyridazin; hydrogen bonding; π–π interactions; Hirshfeld surface analysis.

CCDC reference: 1896404

1. Chemical context

Pyridazinone derivatives are biologically active heterocyclic compounds (Akhtar et al., 2016 ). Diverse pyridazinone derivatives have been reported to possess a variety of biological activities (Thakur et al. 2010 ; Asif et al. 2015 ) such as antimicrobial (Sönmez et al. 2006 ), anti-inflammatory (Abouzid et al. 2008 ), analgesic (Gökçe et al. 2009 ), anti-HIV (Livermore et al. 1993 ), antihypertensive (Siddiqui et al. 2011 ), anticonvulsant (Sharma et al. 2014 ), cardiotonic (Wang et al. 2008 ), antihistaminic (Tao et al. 2012 ), antidepressant (Boukharsa et al. 2016 ), glucan synthase inhibitors (Zhou et al. 2011 ), phosphodiesterase (PDE) inhibitors (Ochiai et al. 2012 ) and herbicidal activity (Asif et al. 2013 ). We report herein the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surfaces.

2. Structural commentary

As the molecular structure of the title compound is illustrated in Fig. 1; the asymmetric unit contains one independent molecule. The molecule is not planar, the benzene ring (C12–C17) and the pyridazine ring are twisted relative to each other, making a dihedral angle of 29.96 (2)° and the phenyl ring (C1–C6) is nearly perpendicular to the pyridazine ring with a dihedral angle of 82.38 (11)° (Fig. 1). The C9=O1 bond length is 1.248 (4) Å while the C9—N1 and C11—N2 bond lengths are 1.360 (4) and 1.307 (4) Å, respectively.

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 20% probability level.

3. Supramolecular features

In the crystal, the molecules are linked by a pair of N—H⋯O hydrogen bonds, forming inversion dimers with an $[R_{2}^{2}]$ (8) ring motif (Table 1 and Fig. 2). The dimers are linked by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane (Fig. 2) and by weak π–π [Cg1⋯Cg3 = 3.839 (2) Å; Cg1 and Cg3 are the centroids of the N1–N2/C9-C11 and C12–C17 rings, respectively] interactions, forming a three-dimensional structure (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	2.04	2.839 (4)	155
C2—H2⋯O1ⁱⁱ	0.93	2.66	3.581 (6)	172
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A view along the a axis of the crystal packing of the title compound. Dashed lines denote the N—H⋯O hydrogen bonds (Table 1

) forming an inversion dimer with an $[R_{2}^{2}]$ (8) ring motif. The C—H⋯O interactions are shown as blue dashed lines.

Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds (Table 1

) are shown as dashed lines and the π–π interactions as pink dashed lines.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016 ) for the 4-phenylpyridazin-3(2H)-one skeleton yielded two hits: 4-benzyl-6-p-tolylpyridazin-3(2H)-one (YOTVIN; Oubair et al., 2009 ) and ethyl 3-methyl-6-oxo-5-(3-(trifluoromethyl)phenyl)-1,6-dihydro-1-pyridazineacetate (QANVOR; Xu et al., 2005 ). In YOTVIN, the molecules are connected two by two through N—H⋯O hydrogen bonds with an $[R_{2}^{2}]$ (8) graph-set motif, building a pseudo dimer arranged about the inversion center (Fig. 4). Weak C—H⋯O hydrogen bonds and weak offset π–π stacking interactions stabilize the packing. In QANVOR, the phenyl and pyridazinone rings are approximately coplanar with a dihedral angle of 4.84 (13)° and in the crystal, centrosymmetrically related molecules form dimers through non-classical intermolecular C—H⋯O hydrogen bonds (Fig. 5).

Figure 4
The crystal packing of YOTVIN (Oubair et al., 2009

). The N—H⋯O hydrogen bonds with an $[R_{2}^{2}]$ (8) graph set motif are shown as pink dashed lines.

Figure 5
(a) A view of the dimers linked by C—H⋯O interactions forming layers parallel to the bc plane. (b) A view along the c axis of the crystal packing of QANVOR (Xu et al., 2005

). Dashed lines denote the intermolecular C—H⋯O hydrogen bonds forming centrosymmetric dimers.

5. Hirshfeld surface analysis

The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) were performed with CrystalExplorer17 (Turner et al., 2017 ). In Fig. 6, the mappings of d_norm, shape-index and curvedness for the title compound are shown. Fig. 7 illustrates the Hirshfeld surface of the molecule in the crystal, with the evident hydrogen-bonding interactions indicated by intense red spots.

Figure 6
The Hirshfeld surfaces of the title compound mapped over d_norm, shape-index and curvedness.

Figure 7
d_norm mapped on Hirshfeld surfaces for visualizing the intermolecular interactions of the title compound.

Fig. 8a shows the two-dimensional fingerprint of the sum of the contacts contributing to the Hirshfeld surface represented in normal mode. Two-dimensional fingerprint plots provide information about the major and minor percentage contributions of interatomic contacts in the compound. The blue colour refers to the frequency of occurrence of the (d_i, d_e) pair and the grey colour is the outline of the full fingerprint. The fingerprint plot in Fig. 8b shows that the H⋯H contacts clearly make the most significant contribution to the Hirshfeld surface (31.4%). In addition, Cl⋯H/H⋯Cl, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N contacts contribute 19.9%, 19%, 9.3% and 6.7%, respectively, to the Hirshfeld surface. In particular, the O⋯H/H⋯O contacts indicate the presence of intermolecular N—H⋯O and C—H⋯O interactions. Much weaker Cl⋯C/C⋯Cl (6.1%) and C⋯C (3.7%) contacts also occur.

Figure 8
Two-dimensional fingerprint plots for the title compound, with a d_norm view and the relative contribution of the atom pairs to the Hirshfeld surface.

A view of the molecular electrostatic potential, in the range −0.0500 to 0.0500 a.u. using the 6-31G(d,p) basis set with DFT method, for the title compound is shown in Fig. 9, where the N—H⋯O hydrogen-bond donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.

Figure 9
A view of the molecular electrostatic potential for the title compound in the range −0.0500 to 0.0500 a.u. using the 6–31 G(d,p) basis set by the DFT method.

6. Synthesis and crystallization

To a solution (0.15 g, 1 mmol) of 6-phenyl-4,5-dihydropyridazin-3(2H)-one and (0.18 g, 1 mmol) of 2,6-dichlorobenzaldehyde in 30 ml of ethanol, sodium hydroxide 10% (0.5 g, 3.5 mmol) was added. The solvent evaporated under vacuum, the residue was purified through silica gel column chromatography using hexane/ethyl acetate (7:3 v/v). 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. The nitrogen-bound H atom was located in a difference-Fourier map and refined subject to a DFIX restraint of N—H = 0.86 Å. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₂Cl₂N₂O
M_r	331.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.8511 (6), 12.5544 (15), 21.069 (2)
β (°)	92.666 (8)
V (Å³)	1546.0 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.42
Crystal size (mm)	0.74 × 0.29 × 0.05

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.844, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	8675, 2726, 1196
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.094, 0.88
No. of reflections	2726
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002), SHELXT2017 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), WinGX (Farrugia, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1896404

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005139/dx2016sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005139/dx2016Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019005139/dx2016Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

4-(2,6-Dichlorobenzyl)-6-phenylpyridazin-3(2H)-one top

Crystal data top

C₁₇H₁₂Cl₂N₂O	F(000) = 680
M_r = 331.19	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.8511 (6) Å	Cell parameters from 5578 reflections
b = 12.5544 (15) Å	θ = 1.9–30.8°
c = 21.069 (2) Å	µ = 0.42 mm⁻¹
β = 92.666 (8)°	T = 296 K
V = 1546.0 (3) Å³	Stick, colorless
Z = 4	0.74 × 0.29 × 0.05 mm

Data collection top

Stoe IPDS 2 diffractometer	2726 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1196 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.103
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
rotation method scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
T_min = 0.844, T_max = 0.973	l = −25→25
8675 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0186P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max < 0.001
2726 reflections	Δρ_max = 0.15 e Å⁻³
199 parameters	Δρ_min = −0.20 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	−0.0717 (2)	0.77603 (11)	0.74856 (7)	0.1004 (5)
Cl2	0.5870 (2)	0.47508 (11)	0.76181 (7)	0.1022 (5)
O1	−0.0083 (5)	0.4872 (2)	0.58329 (11)	0.0681 (9)
N1	0.2647 (5)	0.5706 (3)	0.52916 (14)	0.0543 (9)
H1	0.215035	0.536383	0.495963	0.065*
N2	0.4383 (5)	0.6397 (3)	0.52057 (14)	0.0497 (8)
C11	0.5192 (6)	0.6884 (3)	0.57161 (17)	0.0455 (10)
C9	0.1594 (7)	0.5487 (3)	0.58387 (18)	0.0502 (11)
C12	0.7076 (6)	0.7653 (3)	0.56287 (18)	0.0486 (10)
C8	0.2566 (7)	0.6008 (3)	0.63964 (16)	0.0481 (10)
C10	0.4302 (6)	0.6696 (3)	0.63241 (18)	0.0500 (10)
H10	0.492982	0.705353	0.667723	0.060*
C6	0.2580 (7)	0.6252 (4)	0.75974 (16)	0.0496 (10)
C13	0.8619 (7)	0.7518 (3)	0.51557 (18)	0.0547 (11)
H13	0.844994	0.694576	0.487703	0.066*
C1	0.1647 (7)	0.7164 (4)	0.78577 (18)	0.0552 (11)
C5	0.4515 (7)	0.5861 (3)	0.79161 (19)	0.0587 (11)
C7	0.1522 (7)	0.5726 (3)	0.70160 (16)	0.0644 (12)
H7A	−0.008906	0.591153	0.698375	0.077*
H7B	0.162232	0.496083	0.707307	0.077*
C17	0.7339 (7)	0.8532 (4)	0.60200 (19)	0.0635 (12)
H17	0.627740	0.865436	0.632688	0.076*
C14	1.0395 (7)	0.8220 (4)	0.5094 (2)	0.0652 (13)
H14	1.141541	0.812120	0.477372	0.078*
C2	0.2559 (8)	0.7640 (4)	0.8395 (2)	0.0697 (13)
H2	0.188409	0.824841	0.855430	0.084*
C15	1.0671 (8)	0.9066 (4)	0.5503 (2)	0.0699 (13)
H15	1.189954	0.952831	0.546718	0.084*
C4	0.5475 (8)	0.6332 (5)	0.8459 (2)	0.0791 (15)
H4	0.678943	0.604863	0.865828	0.095*
C16	0.9128 (8)	0.9230 (4)	0.5967 (2)	0.0724 (13)
H16	0.929468	0.980734	0.624227	0.087*
C3	0.4477 (9)	0.7215 (5)	0.8698 (2)	0.0859 (16)
H3	0.509354	0.753135	0.906685	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0858 (9)	0.0865 (10)	0.1269 (11)	0.0090 (8)	−0.0179 (8)	0.0212 (9)
Cl2	0.1090 (11)	0.0865 (10)	0.1149 (10)	0.0230 (9)	0.0478 (8)	0.0115 (9)
O1	0.083 (2)	0.074 (2)	0.0473 (16)	−0.0306 (18)	−0.0006 (15)	−0.0049 (16)
N1	0.071 (2)	0.053 (2)	0.039 (2)	−0.007 (2)	−0.0005 (18)	−0.0096 (17)
N2	0.055 (2)	0.052 (2)	0.0420 (19)	−0.0023 (18)	0.0037 (16)	−0.0009 (17)
C11	0.049 (2)	0.053 (3)	0.034 (2)	0.003 (2)	−0.0035 (19)	−0.002 (2)
C9	0.061 (3)	0.048 (3)	0.041 (2)	−0.002 (2)	0.002 (2)	0.001 (2)
C12	0.053 (2)	0.050 (3)	0.043 (2)	−0.004 (2)	−0.001 (2)	0.005 (2)
C8	0.058 (2)	0.056 (3)	0.030 (2)	−0.005 (2)	−0.0010 (19)	−0.003 (2)
C10	0.058 (3)	0.055 (3)	0.037 (2)	−0.011 (2)	−0.002 (2)	−0.002 (2)
C6	0.058 (3)	0.061 (3)	0.031 (2)	−0.016 (2)	0.008 (2)	0.000 (2)
C13	0.057 (2)	0.061 (3)	0.046 (2)	−0.002 (2)	0.004 (2)	0.004 (2)
C1	0.063 (3)	0.061 (3)	0.042 (2)	−0.012 (2)	0.004 (2)	0.003 (2)
C5	0.059 (3)	0.067 (3)	0.051 (3)	−0.001 (2)	0.016 (2)	0.008 (2)
C7	0.082 (3)	0.066 (3)	0.046 (2)	−0.022 (3)	0.010 (2)	−0.004 (2)
C17	0.068 (3)	0.070 (3)	0.053 (3)	−0.016 (3)	0.014 (2)	−0.008 (3)
C14	0.055 (3)	0.076 (4)	0.066 (3)	0.007 (3)	0.016 (2)	0.015 (3)
C2	0.091 (3)	0.066 (3)	0.053 (3)	−0.008 (3)	0.014 (3)	−0.011 (3)
C15	0.066 (3)	0.071 (4)	0.073 (3)	−0.014 (3)	0.010 (3)	0.008 (3)
C4	0.069 (3)	0.114 (5)	0.053 (3)	−0.004 (3)	−0.009 (3)	0.011 (3)
C16	0.082 (3)	0.068 (3)	0.068 (3)	−0.019 (3)	0.012 (3)	−0.008 (3)
C3	0.098 (4)	0.117 (5)	0.043 (3)	−0.020 (4)	0.003 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.729 (4)	C13—C14	1.373 (5)
Cl2—C5	1.735 (4)	C13—H13	0.9300
O1—C9	1.248 (4)	C1—C2	1.366 (5)
N1—N2	1.354 (4)	C5—C4	1.383 (5)
N1—C9	1.360 (4)	C7—H7A	0.9700
N1—H1	0.8600	C7—H7B	0.9700
N2—C11	1.307 (4)	C17—C16	1.373 (5)
C11—C10	1.425 (5)	C17—H17	0.9300
C11—C12	1.483 (5)	C14—C15	1.373 (5)
C9—C8	1.438 (5)	C14—H14	0.9300
C12—C17	1.382 (5)	C2—C3	1.373 (6)
C12—C13	1.386 (5)	C2—H2	0.9300
C8—C10	1.348 (5)	C15—C16	1.377 (6)
C8—C7	1.509 (5)	C15—H15	0.9300
C10—H10	0.9300	C4—C3	1.361 (6)
C6—C5	1.380 (5)	C4—H4	0.9300
C6—C1	1.391 (5)	C16—H16	0.9300
C6—C7	1.500 (5)	C3—H3	0.9300

N2—N1—C9	128.0 (3)	C6—C5—Cl2	119.2 (3)
N2—N1—H1	116.0	C4—C5—Cl2	117.9 (4)
C9—N1—H1	116.0	C6—C7—C8	115.8 (3)
C11—N2—N1	115.8 (3)	C6—C7—H7A	108.3
N2—C11—C10	121.9 (4)	C8—C7—H7A	108.3
N2—C11—C12	116.4 (4)	C6—C7—H7B	108.3
C10—C11—C12	121.7 (3)	C8—C7—H7B	108.3
O1—C9—N1	120.3 (3)	H7A—C7—H7B	107.4
O1—C9—C8	124.7 (4)	C16—C17—C12	121.7 (4)
N1—C9—C8	115.0 (4)	C16—C17—H17	119.1
C17—C12—C13	117.9 (4)	C12—C17—H17	119.1
C17—C12—C11	120.6 (4)	C13—C14—C15	120.3 (4)
C13—C12—C11	121.5 (4)	C13—C14—H14	119.9
C10—C8—C9	118.1 (4)	C15—C14—H14	119.9
C10—C8—C7	125.8 (3)	C1—C2—C3	119.7 (5)
C9—C8—C7	116.1 (4)	C1—C2—H2	120.2
C8—C10—C11	121.2 (3)	C3—C2—H2	120.2
C8—C10—H10	119.4	C14—C15—C16	120.0 (4)
C11—C10—H10	119.4	C14—C15—H15	120.0
C5—C6—C1	115.4 (3)	C16—C15—H15	120.0
C5—C6—C7	122.6 (4)	C3—C4—C5	119.3 (4)
C1—C6—C7	122.0 (4)	C3—C4—H4	120.3
C14—C13—C12	120.7 (4)	C5—C4—H4	120.3
C14—C13—H13	119.6	C17—C16—C15	119.3 (4)
C12—C13—H13	119.6	C17—C16—H16	120.4
C2—C1—C6	122.8 (4)	C15—C16—H16	120.4
C2—C1—Cl1	117.4 (4)	C4—C3—C2	120.0 (4)
C6—C1—Cl1	119.9 (3)	C4—C3—H3	120.0
C6—C5—C4	122.8 (4)	C2—C3—H3	120.0

C9—N1—N2—C11	2.6 (5)	C7—C6—C1—Cl1	−3.3 (5)
N1—N2—C11—C10	0.1 (5)	C1—C6—C5—C4	0.2 (6)
N1—N2—C11—C12	−179.3 (3)	C7—C6—C5—C4	−178.8 (4)
N2—N1—C9—O1	175.7 (3)	C1—C6—C5—Cl2	−178.0 (3)
N2—N1—C9—C8	−4.5 (6)	C7—C6—C5—Cl2	2.9 (5)
N2—C11—C12—C17	149.5 (4)	C5—C6—C7—C8	−83.4 (5)
C10—C11—C12—C17	−29.9 (5)	C1—C6—C7—C8	97.5 (5)
N2—C11—C12—C13	−30.4 (5)	C10—C8—C7—C6	−1.5 (6)
C10—C11—C12—C13	150.1 (4)	C9—C8—C7—C6	178.6 (4)
O1—C9—C8—C10	−176.5 (4)	C13—C12—C17—C16	−3.0 (6)
N1—C9—C8—C10	3.7 (5)	C11—C12—C17—C16	177.1 (4)
O1—C9—C8—C7	3.5 (6)	C12—C13—C14—C15	0.2 (6)
N1—C9—C8—C7	−176.4 (4)	C6—C1—C2—C3	0.1 (6)
C9—C8—C10—C11	−1.5 (6)	Cl1—C1—C2—C3	−178.1 (4)
C7—C8—C10—C11	178.5 (4)	C13—C14—C15—C16	−1.7 (6)
N2—C11—C10—C8	−0.5 (6)	C6—C5—C4—C3	0.6 (7)
C12—C11—C10—C8	179.0 (4)	Cl2—C5—C4—C3	178.8 (4)
C17—C12—C13—C14	2.1 (6)	C12—C17—C16—C15	1.6 (6)
C11—C12—C13—C14	−178.0 (3)	C14—C15—C16—C17	0.9 (7)
C5—C6—C1—C2	−0.6 (6)	C5—C4—C3—C2	−1.1 (7)
C7—C6—C1—C2	178.5 (4)	C1—C2—C3—C4	0.8 (7)
C5—C6—C1—Cl1	177.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.04	2.839 (4)	155
C2—H2···O1ⁱⁱ	0.93	2.66	3.581 (6)	172

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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