Crystal structure and Hirshfeld surface analysis of 4-(2-chloro­eth­yl)-5-methyl-1,2-di­hydro­pyrazol-3-one

Naghiyev, F.N.; Khrustalev, V.N.; Akkurt, M.; Dukhnovsky, E.A.; Bhattarai, A.; Khalilov, A.N.; Mamedov, İ.G.

doi:10.1107/S2056989024000835

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ISSN: 2056-9890

Volume 80| Part 2| February 2024| Pages 223-227

https://doi.org/10.1107/S2056989024000835

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Crystal structure and Hirshfeld surface analysis of 4-(2-chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one

Farid N. Naghiyev,^a Victor N. Khrustalev,^b,^c Mehmet Akkurt,^d Evgeny A. Dukhnovsky,^b Ajaya Bhattarai,^e ^* Ali N. Khalilov ^f,^a and İbrahim G. Mamedov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan, ^bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow 117198, Russian Federation, ^cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^eDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal, and ^f"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 15 January 2024; accepted 23 January 2024; online 31 January 2024)

In the crystal of the title compound, C₆H₉ClN₂O, molecular pairs form dimers with an R²₂(8) motif through N—H⋯O hydrogen bonds. These dimers are connect into ribbons parallel to the (100) plane with R⁴₄(10) motifs by N—H⋯O hydrogen bonds along the c-axis direction. In addition, π–π [centroid-to-centroid distance = 3.4635 (9) Å] and C—Cl⋯π interactions between the ribbons form layers parallel to the (100) plane. The three-dimensional consolidation of the crystal structure is also ensured by Cl⋯H and Cl⋯Cl interactions between these layers. According to a Hirshfeld surface study, H⋯H (43.3%), Cl⋯H/H⋯Cl (22.1%) and O⋯H/H⋯O (18.7%) interactions are the most significant contributors to the crystal packing.

Keywords: crystal structure; hydrogen bonds; dimers; pyrazole ring; Hirshfeld surface analysis.

CCDC reference: 2327646

1. Chemical context

Nitrogen-based heterocyclic compounds are an important branch of organic chemistry. These systems have received increasing attention over the past two decades. Synthetic chemistry is growing extensively with recently developed heterocyclic systems for various research and commercial purposes (Maharramov et al., 2021 , 2022 ; Erenler et al., 2022 ; Akkurt et al., 2023 ). These systems have found wide applications in diverse branches of chemistry, including the chemistry of coordination compounds (Gurbanov et al., 2021 ; Mahmoudi et al., 2021 ), drug development (Donmez & Turkyılmaz, 2022 ; Askerova, 2022 ) and material science (Velásquez et al., 2019 ; Afkhami et al., 2019 ). The pyrazole motif is the most widespread five-membered heteroaromatic ring system in nitrogen heterocycles. It is an essential structural motif present in many natural bioactive molecules such as L-α-amino-β-(pyrazolyl-N)-propanoic acid, withasomnine, pyrazofurin, pyrazofurin B, formycin, formycin B, oxoformycin B, nostocine A, fluviols (A, B, C, D and E), pyrazole-3(5)-carboxylic acid, 4-Methyl pyrazole-3(5)-carboxylic acid, 3-n-nonylpyrazole (Khalilov et al., 2022 ; Kumar et al., 2013 ; Sobhi & Faisal, 2023 ). The pyrazole ring incorporating derivatives with various biological activities (Singh et al., 2023 ), such as anticonvulsant, antidiabetic, anti-inflammatory, antioxidant, anticancer, antitubercular, antiulcer activities and other properties has been reviewed recently (Fig. 1).

Figure 1
The biological activities of compounds incorporating the pyrazole motif.

On the other hand, the incorporation of various pharmacophore groups in a pyrazole scaffold has led to the development of best-selling drugs such as ibrutinib, ruxolitinib, axitinib, niraparib and baricitinib (Atalay et al., 2022 ; Alam, 2023 ). Thus, in the framework of our studies in heterocyclic chemistry (Naghiyev et al., 2020 , 2021 , 2022 ), we herein report the crystal structure and Hirshfeld surface analysis of the title compound, 4-(2-chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one, for which the proposed reaction mechanism is shown in Fig. 2.

Figure 2
The proposed reaction mechanism for the formation of the title compound.

2. Structural commentary

In the title compound (Fig. 3), the pyrazoline ring (N1/N2/C3–C5) has an essentially planar conformation [maximum deviation = 0.006 (1) Å for N1]. The C3—C4—C7—C8 and C4—C7—C8—Cl1 torsion angles are 105.67 (19) and 172.38 (11)°, respectively. The geometric parameters of the title compound are normal and comparable to those of related compounds given in the Database survey section.

Figure 3
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecular pairs form dimers with an R₂²(8) motif (Bernstein et al., 1995 ) through N—H⋯O hydrogen bonds (Table 1 and Fig. 4). These dimers are also connected into ribbons parallel to the (100) plane by forming N—H⋯O hydrogen bonds with R₄⁴(10) motifs along the c-axis direction (Figs. 5 and 6). In addition, π–π [Cg1⋯Cg1ⁱ = 3.4635 (9) Å, slippage = 0.511 Å; symmetry code: (i) − x, 1 − y, 1 − z; Cg1 is a centroid of the pyrazole ring (N1/N2/C3–C5)] and C—Cl⋯π [C8—Cl1⋯Cg1ⁱⁱ: C8—Cl1 = 1.8040 (18) Å, Cl1⋯Cg1ⁱⁱ = 3.8386 (8) Å, C8—Cl1⋯Cg1ⁱⁱ = 84.57 (6)°; symmetry code: (ii) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z] interactions between the ribbons form layers parallel to the (100) plane. The three-dimensional consolidation of the crystal structure is also ensured by the Cl⋯H and Cl⋯Cl interactions [(C8)Cl1⋯H6Bⁱⁱⁱ = 3.12 (3) Å, C8—Cl1⋯H6Bⁱⁱⁱ = 135.3 (6)° and (C8)Cl1⋯Cl1^iv = 3.5071 (7) Å, C8—Cl1⋯Cl1^iv = 161.79 (7)°; symmetry codes: (iii) 1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (iv) 1 − x, 1 − y, 2 − z] between these layers (Table 2; Fig. 7).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88 (3)	1.81 (3)	2.6861 (18)	174 (2)
N2—H2⋯O1ⁱⁱ	0.92 (3)	1.75 (3)	2.6772 (17)	177 (2)
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Summary of short interatomic contacts (Å) in the title compound

Cl1⋯H6B	3.12	1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
Cl1⋯Cl1	3.51	1 − x, 1 − y, 2 − z
H1⋯O1	1.80	−x, 2 − y, 1 − z
H6C⋯O1	2.89	−x, 1 − y, 1 − z
O1⋯H2	1.76	x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
H6A⋯H7B	2.60	x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z

Figure 4
View of the N—H⋯O hydrogen bonds of the title compound down the a-axis.

Figure 5
View of the N—H⋯O hydrogen bonds of the title compound down the b-axis.

Figure 6
View of the N—H⋯O hydrogen bonds of the title compound down the c-axis.

Figure 7
View of the π-π- and C—Cl⋯π interactions of the title compound down the b-axis.

To quantify the intermolecular interactions in the crystal, two-dimensional fingerprint plots and Hirshfeld surfaces were produced using Crystal Explorer 17.5 (Spackman et al., 2021 ). Fig. 8 shows the mapping of the Hirshfeld surfaces over d_norm in the range −0.7296 (red) to +1.3271 (blue) a.u. The interactions given in Tables 1 and 2 play a key role in the molecular packing of the title compound. H⋯H is the most significant interatomic contact because it contributes the most to the crystal packing (43.3%, Fig. 9b). Other significant contributions are made by Cl⋯H/H⋯Cl (22.1%, Fig. 9c) and O⋯H/H⋯O (18.7%, Fig. 9d) interactions. The following interactions make minor contributions: Cl⋯C/C⋯Cl (2.4%), C⋯H/H⋯C (2.6%), N⋯H/H⋯N (4.3%), N⋯C/C⋯N (3.4%), Cl⋯N/N⋯Cl (0.7%), and C⋯C (0.7%).

Figure 8
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm, with a fixed colour scale of −0.7296 to +1.3271 a.u.

Figure 9
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) Cl⋯H/H⋯Cl and (d) O⋯H/H⋯O interactions. [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.43, last update November 2022; Groom et al., 2016 ) for the central five-membered ring 2,3-dihydro-1H-pyrazole yielded six compounds related to the title compound, viz. 3-methyl-5-(3-methylphenoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (CSD refcode TERZAV; Archana, et al., 2022 ), N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(ethylsulfanyl)-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide (FERPOL; Priyanka et al., 2022 ), 4-[3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl]-2-methoxyphenol monohydrate (KOXGAI; Duong Khanh et al., 2019 ), 5-chloro-N¹-(5-phenyl-1H-pyrazol-3-yl)benzene-1,2-diamine (CAXZUZ; Yartsev et al., 2017 ), 5-(butylamino)-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde (EYEHEX; Macías et al., 2016 ) and 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile (AFIJOP; Lin et al., 2007 ).

The molecular packing of TERZAV features aromatic π–π stacking and weak C—H⋯π interactions. In the crystal of FERPOL, strong N—H⋯O hydrogen bonds link the molecules into chains that extend parallel to the a-axis. In the crystal of KOXGAI, the molecules are connected into chains running in the b-axis direction by O—H⋯N hydrogen bonding. Parallel chains interact through N—H⋯O hydrogen bonds and π–π stacking of the trisubstituted phenyl rings. In the crystal of CAXZUZ, the A and B molecules are linked by two pairs of N—H⋯N hydrogen bonds, forming A–B dimers. These are further linked by a fifth N—H⋯N hydrogen bond, forming tetramer-like units that stack along the a-axis direction, forming columns, which are in turn linked by C—H⋯π interactions, forming layers parallel to the ac plane. The supramolecular structure of EYEHEX assembly has a three-dimensional arrangement controlled mainly by weak C—H⋯O and C—H⋯π interactions. The crystal structure of AFIJOP is consolidated by two N—H⋯N hydrogen bonds.

5. Synthesis and crystallization

Acetoacetic ether (7.7 mmol), dichloroethane (7.7 mmol) and hydrazine hydrate (15.4 mmol) were dissolved in 40 ml of ethanol and the reaction mixture was refluxed for 4 h. Then the reaction mixture was cooled to room temperature with the formation of white crystals. The crystals were separated by filtration and recrystallized from an ethanol–water mixture (m.p. 499–500 K, yield 78%).

¹H NMR (300 MHz, DMSO-d₆, ppm.): 2.06 (s, 3H, CH₃); 2.64 (t, 2H, CH₂, ^H-HJ₂ = 7.2); 3.49 (s, 2H, 2NH); 3.58 (t, 2H, ClCH₂, ^H-HJ₂ = 7.2). ¹³C NMR (75 MHz, DMSO-d₆, ppm.): 10.28 (CH₃), 26.02 (CH₂), 44.91 (CH₂Cl), 97.63 (C_tert.=), 160.12 (HN—C_tert.=), 162.34 (N—C=O).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The C-bound H atoms were placed in calculated positions (0.95–0.99 Å) and refined as riding with U_iso(H) = 1.2 or 1.5U_eq(C). The N-bound H atoms were located in a difference map and freely refined.

Table 3
Experimental details

Crystal data
Chemical formula	C₆H₉ClN₂O
M_r	160.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.8420 (2), 6.9145 (2), 11.1807 (2)
β (°)	93.618 (2)
V (Å³)	759.36 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.92
Crystal size (mm)	0.20 × 0.12 × 0.06

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.513, 0.750
No. of measured, independent and observed [I > 2σ(I)] reflections	6642, 1532, 1467
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.05
No. of reflections	1532
No. of parameters	127
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.41
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2327646

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024000835/nx2004sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024000835/nx2004Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024000835/nx2004Isup3.cml

checkCIF report

Computing details top

4-(2-Chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one top

Crystal data top

C₆H₉ClN₂O	F(000) = 336
M_r = 160.60	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.8420 (2) Å	Cell parameters from 4592 reflections
b = 6.9145 (2) Å	θ = 4.5–77.6°
c = 11.1807 (2) Å	µ = 3.92 mm⁻¹
β = 93.618 (2)°	T = 100 K
V = 759.36 (3) Å³	Prism, colourless
Z = 4	0.20 × 0.12 × 0.06 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	1467 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.027
ω scans	θ_max = 77.5°, θ_min = 4.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −12→12
T_min = 0.513, T_max = 0.750	k = −8→7
6642 measured reflections	l = −14→8
1532 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.097	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0501P)² + 0.606P] where P = (F_o² + 2F_c²)/3
1532 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.41 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	0.45324 (5)	0.61848 (7)	0.86496 (4)	0.03447 (18)
O1	0.06705 (13)	0.89161 (17)	0.64445 (10)	0.0231 (3)
N1	0.05777 (14)	0.7905 (2)	0.44644 (12)	0.0197 (3)
H1	0.013 (3)	0.890 (4)	0.413 (2)	0.040 (7)*
N2	0.11129 (14)	0.6437 (2)	0.38217 (12)	0.0195 (3)
H2	0.096 (2)	0.636 (3)	0.300 (2)	0.038 (6)*
C3	0.18687 (16)	0.5302 (2)	0.45765 (14)	0.0189 (3)
C4	0.18362 (16)	0.6035 (2)	0.57245 (14)	0.0181 (3)
C5	0.10154 (16)	0.7717 (2)	0.56311 (13)	0.0188 (3)
C6	0.2560 (2)	0.3553 (3)	0.41307 (16)	0.0254 (4)
H6A	0.282 (3)	0.372 (4)	0.331 (3)	0.058 (8)*
H6B	0.338 (3)	0.328 (5)	0.458 (3)	0.065 (9)*
H6C	0.205 (3)	0.250 (5)	0.414 (3)	0.066 (9)*
C7	0.25721 (17)	0.5342 (2)	0.68559 (14)	0.0205 (3)
H7A	0.194 (2)	0.527 (3)	0.7508 (18)	0.021 (5)*
H7B	0.295 (2)	0.406 (3)	0.676 (2)	0.029 (5)*
C8	0.37260 (18)	0.6724 (3)	0.71941 (16)	0.0254 (4)
H8A	0.340 (2)	0.807 (4)	0.724 (2)	0.031 (6)*
H8B	0.443 (2)	0.665 (4)	0.664 (2)	0.037 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0401 (3)	0.0366 (3)	0.0249 (3)	0.00431 (18)	−0.01242 (19)	−0.00157 (17)
O1	0.0374 (7)	0.0209 (6)	0.0110 (5)	0.0082 (5)	0.0007 (5)	−0.0010 (4)
N1	0.0297 (7)	0.0180 (7)	0.0114 (6)	0.0045 (5)	0.0008 (5)	−0.0006 (5)
N2	0.0278 (7)	0.0194 (7)	0.0115 (7)	0.0026 (5)	0.0013 (5)	−0.0028 (5)
C3	0.0237 (7)	0.0179 (7)	0.0153 (7)	−0.0011 (6)	0.0027 (6)	0.0008 (6)
C4	0.0238 (7)	0.0177 (7)	0.0128 (7)	0.0008 (6)	0.0024 (6)	0.0017 (6)
C5	0.0273 (8)	0.0183 (7)	0.0110 (7)	−0.0002 (6)	0.0023 (6)	0.0003 (6)
C6	0.0333 (9)	0.0233 (8)	0.0198 (9)	0.0057 (7)	0.0033 (7)	−0.0036 (7)
C7	0.0280 (8)	0.0192 (8)	0.0144 (8)	0.0036 (6)	0.0015 (6)	0.0016 (6)
C8	0.0264 (8)	0.0315 (9)	0.0180 (8)	0.0006 (7)	−0.0019 (6)	0.0029 (7)

Geometric parameters (Å, º) top

Cl1—C8	1.8040 (18)	C4—C7	1.496 (2)
O1—C5	1.2920 (19)	C6—H6A	0.97 (3)
N1—C5	1.354 (2)	C6—H6B	0.95 (3)
N1—N2	1.3685 (19)	C6—H6C	0.88 (3)
N1—H1	0.88 (3)	C7—C8	1.514 (2)
N2—C3	1.342 (2)	C7—H7A	0.99 (2)
N2—H2	0.92 (3)	C7—H7B	0.97 (2)
C3—C4	1.382 (2)	C8—H8A	0.99 (2)
C3—C6	1.489 (2)	C8—H8B	0.95 (2)
C4—C5	1.416 (2)

C5—N1—N2	108.95 (13)	H6A—C6—H6B	105 (2)
C5—N1—H1	126.8 (17)	C3—C6—H6C	113 (2)
N2—N1—H1	123.6 (17)	H6A—C6—H6C	107 (3)
C3—N2—N1	108.66 (13)	H6B—C6—H6C	107 (3)
C3—N2—H2	129.9 (15)	C4—C7—C8	108.91 (14)
N1—N2—H2	121.4 (15)	C4—C7—H7A	110.2 (12)
N2—C3—C4	108.96 (14)	C8—C7—H7A	110.3 (12)
N2—C3—C6	120.74 (15)	C4—C7—H7B	111.5 (13)
C4—C3—C6	130.29 (15)	C8—C7—H7B	108.6 (13)
C3—C4—C5	106.22 (14)	H7A—C7—H7B	107.3 (18)
C3—C4—C7	128.97 (15)	C7—C8—Cl1	112.04 (12)
C5—C4—C7	124.69 (14)	C7—C8—H8A	111.5 (13)
O1—C5—N1	122.31 (15)	Cl1—C8—H8A	105.7 (13)
O1—C5—C4	130.49 (14)	C7—C8—H8B	111.5 (15)
N1—C5—C4	107.19 (13)	Cl1—C8—H8B	106.1 (15)
C3—C6—H6A	111.6 (17)	H8A—C8—H8B	109.7 (19)
C3—C6—H6B	111.9 (19)

C5—N1—N2—C3	0.98 (18)	N2—N1—C5—C4	−1.24 (18)
N1—N2—C3—C4	−0.30 (18)	C3—C4—C5—O1	179.99 (17)
N1—N2—C3—C6	178.79 (15)	C7—C4—C5—O1	−3.7 (3)
N2—C3—C4—C5	−0.45 (18)	C3—C4—C5—N1	1.04 (18)
C6—C3—C4—C5	−179.43 (17)	C7—C4—C5—N1	177.36 (15)
N2—C3—C4—C7	−176.56 (16)	C3—C4—C7—C8	105.67 (19)
C6—C3—C4—C7	4.5 (3)	C5—C4—C7—C8	−69.8 (2)
N2—N1—C5—O1	179.70 (15)	C4—C7—C8—Cl1	172.38 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (3)	1.81 (3)	2.6861 (18)	174 (2)
N2—H2···O1ⁱⁱ	0.92 (3)	1.75 (3)	2.6772 (17)	177 (2)

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

Summary of short interatomic contacts (Å) in the title compound top

Cl1···H6B	3.12	1 - x, 1/2 + y, 3/2 - z
Cl1···Cl1	3.51	1 - x, 1 - y, 2 - z
H1···O1	1.80	-x, 2 - y, 1 - z
H6C···O1	2.89	-x, 1 - y, 1 - z
O1···H2	1.76	x, 1/2 - y, - 1/2 + z
H6A···H7B	2.60	x, 1/2 - y, - 1/2 + z

Acknowledgements

Authors contributions are as follows. Conceptualization, IGM, ANK and EAD; methodology, AB and MA; investigation, VNK and FNN; writing (original draft), MA, AB and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, IGM and FNN; funding acquisition, VNK, AB and FNN; resources, AB, VNK and MA; supervision, MA and ANK.

Funding information

This paper was supported by Baku State University and the RUDN University Strategic Academic Leadership Program.

References

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