Synthesis, crystal structure, Hirshfeld surface and crystal void analysis of 4-fluoro­benzo[c][1,2,5]selena­diazol-1-ium chloride

Gurbanov, A.V.; Hökelek, T.; Mammadova, G.Z.; Hasanov, K.I.; Javadzade, T.A.; Belay, A.N.

doi:10.1107/S2056989025001379

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ISSN: 2056-9890

Volume 81| Part 3| March 2025|

https://doi.org/10.1107/S2056989025001379

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Synthesis, crystal structure, Hirshfeld surface and crystal void analysis of 4-fluorobenzo[c][1,2,5]selenadiazol-1-ium chloride

Atash V. Gurbanov,^a Tuncer Hökelek,^b Gunay Z. Mammadova,^c Khudayar I. Hasanov,^d Tahir A. Javadzade ^e and Alebel N. Belay ^f ^*

^aExcellence Center, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^bHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^cDepartment of Chemistry, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan, ^dAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, Azerbaijan, ^eDepartment of Chemistry and Chemical Engineering, Khazar University, Mahzati Str. 41, AZ 1096 Baku, Azerbaijan, and ^fDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: alebel.nibret@bdu.edu.et

Edited by M. Weil, Vienna University of Technology, Austria (Received 6 January 2025; accepted 14 February 2025; online 20 February 2025)

The asymmetric unit of the title salt, C₆H₄FN₂Se⁺·Cl⁻, contains one planar 4-fluorobenzo[c][1,2,5]selenadiazol-1-ium molecular cation and a chloride anion. In the crystal, intermolecular N—H⋯Cl hydrogen bonds link the 4-fluorobenzo[c][1,2,5]selenadiazol-1-ium molecules, which are arranged in parallel layers along (104), to the chloride anions. The cationic layers, in turn, are stacked along [001]. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯Cl/Cl⋯H (22.6%), H⋯F/F⋯H (13.9%), H⋯N/N⋯H (11.9%), H⋯C/C⋯H (10.2%) and H⋯H (7.7%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 44.80 Å³ and 5.91%, showing that there is no large cavity in the crystal packing.

Keywords: crystal structure; non-covalent interactions; chalcogen bond; organic–inorganic salt.

CCDC reference: 2424642

1. Chemical context

Replacement of the H atom at the R—H⋯Nu synthon (Nu = nucleophile) with a group 16 element can lead to the formation of a chalcogen bond (ChB), which is a non-covalent interaction between the electron-density-deficient side (so-called σ- or π-hole) of a covalently bonded chalcogen atom (Ch = O, S, Se or Te) and a nucleophilic (Nu) region in the same (intramolecular) or another (intermolecular) molecular entity so that R—Ch⋯Nu [R = Ch, Pn (pnictogen), metal, etc.; Nu = lone pair possessing Ha (halogen), Ch, Pn or metal atom, anion, π-system, radical, etc.] can be formed (Aliyeva et al., 2024 ). Similarly to hydrogen, halogen or pnictogen bonds, as well as to π-interactions (Abdelhamid et al., 2011 ; Gurbanov et al., 2018 ), the chalcogen bond is also of importance for the development of new catalysts based on metal complexes, or sensors, molecular switches, etc. Following the concept of resonance-assisted hydrogen bonds (Maharramov et al., 2010 ; Mahmudov et al., 2011 ), a resonance-assisted chalcogen bond is usually treated as a chalcogen bond strengthened by conjugation in a π-system due to electron (charge) delocalization or favourable rearrangement of charge distribution in the molecular system (Gurbanov et al., 2020 ). Like charge-assisted hydrogen bonds (Mac Leod et al., 2012 ; Martins et al., 2017 ; Mizar et al., 2012 ), the Ch⋯Nu bond can be strengthened by using an anion instead of traditional nucleophiles bearing a lone pair, which may lead to charge-assisted chalcogen-bonding (Guseinov et al., 2022 ).

In the context given above, we have isolated the charge-assisted and chalcogen-bonded title salt, (C₆H₄FN₂Se)⁺Cl⁻, and studied its molecular and crystal structures together with a Hirshfeld surface and crystal voids analysis.

2. Structural commentary

The asymmetric unit of the title compound contains one 4-fluorobenzo[c][1,2,5]selenadiazol-1-ium cationic molecule and a chloride anion (Fig. 1). The 4-fluorobenzo[c][1,2,5]selenadiazol-1-ium molecule is almost planar, where the planar A (C1–C6) and B (Se/N1/N2/C1/C2) rings are oriented at a dihedral angle of A/B = 0.64 (6)°. Atom F1 is 0.0063 (18) Å out of the least-squares plane of ring A. All bond lengths and angles in the molecule are normal.

Figure 1
The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the crystal, intermolecular N—H⋯Cl hydrogen bonds link the molecular cations, which are arranged into parallel layers along (104), and chloride ions (Table 1). The cationic layers, in turn, are stacked along [001 (Fig. 2a). The closest Se⋯Cl separations of 2.883 (2) and 3.030 (2) Å are shorter than the sum of the van der Waals radii (ΣrvdW (Se⋯Cl) = 3.65 Å) and therefore can be considered as charge-assisted chalcogen bonds, which aggregate the title compound into a supramolecular dimer, with the σ-hole angles ∠N1—Se1⋯Cl1 and ∠N1—Se1⋯Cl1 of 171.69 (7)° and 177.19 (7)° (Fig. 2b). Neither π–π nor C—H⋯π(ring) interactions are observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯Cl1ⁱ	0.85	2.23	3.056 (3)	163
Symmetry code: (i) .

Figure 2
(a) Crystal packing diagram viewed down the a axis with intermolecular N—H⋯Cl hydrogen bonds shown as dashed lines; (b) intermolecular charge-assisted chalcogen bonds shown as dashed blue lines.

4. Hirshfeld surface analysis

A Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out to visualize the intermolecular interactions in the crystal of the title compound using CrystalExplorer (Spackman et al., 2021 ). In the three-dimensional Hirshfeld surface plotted over d_norm (Fig. 3a), the contact distances equal to the sum of van der Waals radii are shown by the white surfaces, whereas distances shorter and longer than the van der Waals radii are shown in red and blue, respectively (Venkatesan et al., 2016 ), where the bright-red spots indicate their roles as the respective donors and/or acceptors. Planar stacking arrangements and the presence of aromatic stacking interactions such as C—H⋯π and π–π interactions are visualized by shape-index. In the HS plotted over shape-index, the C—H⋯π interactions are represented as red π-holes, which are related to the electron ring interactions between the CH groups with the centroid of the aromatic rings of neighbouring molecules. On the other hand, π–π stacking interactions are visualized by the presence of adjacent red and blue triangles. Fig. 3b clearly suggests that there are neither C—H⋯π nor π–π interactions present.

Figure 3
(a) View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm and (b) Hirshfeld surface of the title compound plotted over shape-index.

The overall two-dimensional fingerprint plot, Fig. 4a, and those delineated into H⋯Cl/Cl⋯H, H⋯F/F⋯H, H⋯N/N⋯H, H⋯C/C⋯H, H⋯H, C⋯Cl/Cl⋯C, Cl⋯Se/Se⋯Cl, F⋯Se/Se⋯F, H⋯Se/Se⋯H, F⋯C/C⋯F, C⋯N/N⋯C, N⋯Se/Se⋯N, C⋯Se/Se⋯C, F⋯Cl/Cl⋯F, N⋯N, C⋯C, Se⋯Se and F⋯N/N⋯F (McKinnon et al., 2007 ) are illustrated in Fig. 4b–s, respectively, together with their relative contributions to the Hirshfeld surface. The most important interaction is H⋯Cl/Cl⋯H (Fig. 4b), contributing 22.6% to the HS, and viewed as a pair of spikes at d_e + d_i = 2.06 Å. The H⋯F/F⋯H (Table 2 and Fig. 4c) and H⋯N/N⋯H (Fig. 4d) contacts contribute 13.9% and 11.9%, respectively, to the HS and are viewed as pairs of spikes at d_e + d_i = 2.42 Å and d_e + d_i = 2.72 Å, respectively. In the absence of C—H⋯π interactions, the H⋯C/C⋯H contacts (Fig. 4e), contributing 10.2% to the HS, are reflected at d_e + d_i = 3.28 Å. The H⋯H interactions (Fig. 4f) contribute 7.7% to the HS, and are viewed at d_e = d_i = 1.22 Å. The C⋯Cl/Cl⋯C contacts (Fig. 4g) with a 6.3% contribution to the HS, have an arrow-shaped distribution of points, and they are viewed at d_e = d_i = 1.84 Å. The pair of spikes of the Cl⋯Se/Se⋯Cl contacts (Fig. 4h) with 5.4% contribution to the HS are seen at d_e + d_i = 3.00 Å. Finally, the F⋯Se/Se⋯F (Fig. 4i), H⋯Se/Se⋯H (Fig. 4j), F⋯C/C⋯F (Fig. 4k), C⋯N/N⋯C (Fig. 4l), N⋯Se/Se⋯N (Fig. 4m), C⋯Se/Se⋯C (Fig. 4n), F⋯Cl/Cl⋯F (Fig. 4o), N⋯N (Fig. 4p), C⋯C (Fig. 4q), Se⋯Se (Fig. 4r) and F⋯N/N⋯F (Fig. 4s) contacts with 3.9%, 3.7%, 3.4%, 3.4%, 2.1%, 1.4%, 1.2%, 1.1%, 1.1%, 0.5% ad 0.2% contributions, respectively, to the HS make very small contributions.

Table 2
Selected interatomic distances (Å)

N2⋯Cl1ⁱ	3.056 (3)	F1⋯N1	2.800 (3)
H2N⋯Cl1ⁱ	2.23	H5⋯F1ⁱⁱ	2.56
Symmetry codes: (i) ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯Cl/Cl⋯H, (c) H⋯F/F⋯H, (d) H⋯N/N⋯H, (e) H⋯C/C⋯H, (f) H⋯H, (g) C⋯Cl/Cl⋯C, (h) Cl⋯Se/Se⋯Cl, (i) F⋯Se/Se⋯F, (j) H⋯Se/Se⋯H, (k) F⋯C/C⋯F, (l) C⋯N/N⋯C, (m) N⋯Se/Se⋯N, (n) C⋯Se/Se⋯C, (o) F⋯Cl/Cl⋯F, (p) N⋯N, (q) C⋯C, (r) Se⋯Se and (s) F⋯N/N⋯F interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

The nearest neighbour coordination environment of a molecule can be determined from the colour patches on the HS based on how close to other molecules they are. The HS representations of contact patches plotted onto the surface are shown for the H⋯Cl/Cl⋯H, H⋯F/F⋯H, H⋯N/N⋯H and H⋯C/C⋯H interactions in Fig. 5a–d.

Figure 5
The Hirshfeld surface representations with the function d_norm plotted onto the surface for (a) H⋯Cl/Cl⋯H, (b) H⋯F/F⋯H, (c) H⋯N/N⋯H and (d) H⋯C/C⋯H interactions.

The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯Cl/Cl⋯H, H⋯F/F⋯H, H⋯N/N⋯H and H⋯C/C⋯H interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

5. Crystal voids

If the crystal packing does not result in significant voids, then the molecules are tightly packed and the applied external mechanical force may not easily break the crystal. Thus, the strength of the crystal packing is important for determining the response to an applied mechanical force. To check the mechanical stability of the crystal, a void analysis was performed by adding up the electron densities of the spherically symmetric atoms contained in the asymmetric unit (Turner et al., 2011 ; Irrou et al., 2022 ). The volume of the crystal voids (Fig. 6a,b) and the percentage of free space in the unit cell were calculated to be 44.80 Å³ and 5.91%, respectively. Thus, the crystal packing appears compact and the mechanical stability should be substantial.

Figure 6
Graphical views of voids in the crystal packing of the title compound (a) along the a axis and (b) along the b axis.

6. Database survey

A survey of the Cambridge Structural Database (CSD; version 5.45, update of September 2024; Groom et al., 2016 ) found two molecules that are similar to the title compound, viz. (rac)-4-methyl-4-nitro-2,1,3-benzoselena-diazol-5(4H)-one, C₇H₅N₃O₃Se (CSD refcode JURLAJ; Tian et al., 1993 ) and 5-nitro-2,1,3-benzoselenadiazole, C₆H₃N₃O₂Se (CSD refcode DOBWUO; Aliyeva et al., 2024). In contrast to the four-membered Se₂Cl₂ ring defined through charge-assisted chalcogen bonds in the crystal packing of the title compound, there is an Se₂N₂ supramolecular synthon with intermolecular chalcogen bonds in JURLAJ and DOBWUO.

7. Synthesis and crystallization

3-Fluorobenzene-1,2-diamine (10 mmol) and selenium dioxide (10 mmol) were dissolved in 25 ml of dichloromethane and stirred for 1 h at ambient temperature, and further refluxed for 1 h. After cooling to room temperature, the solvent was evaporated under reduced pressure to give the reaction product. The title compound was obtained by slow evaporation of a water–acetone (1:3 v:v) solution of the reaction product at pH = 2 (adjusted by addition of HCl), and analysed by single-crystal X-ray analysis, elemental analysis, ESI-MS and NMR measurements. Yield: 87% (based on SeO₂), yellow powder soluble in methanol, ethanol and DMSO. Analysis calculated for C₆H₄ClFN₂Se (M_r = 237.53): C, 30.34; H, 1.70; N, 11.79. Found: C, 30.29; H, 1.67; N, 11.76. ESI-MS (positive ion mode), m/z: 238.4 [M + H]^{+. 1}H NMR (CDCl₃), δ: 6.77–7.92 (3H, Ar–H). ¹³C NMR (CDCl₃), 110.91, 119.58, 128.96, 151.29, 155.67 and 161.93.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The N- and C-bond hydrogen atom positions were calculated geometrically at distances of 0.85 Å and 0.93 Å (for aromatic CH) and refined using a riding model by applying the constraint of U_iso(H) = 1.2U_eq(C, N).

Table 3
Experimental details

Crystal data
Chemical formula	C₆H₄FN₂Se⁺·Cl⁻
M_r	237.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.889 (4), 7.250 (5), 15.183 (10)
β (°)	90.90 (3)
V (Å³)	758.2 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	5.25
Crystal size (mm)	0.34 × 0.23 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.252, 0.498
No. of measured, independent and observed [I > 2σ(I)] reflections	9806, 1768, 1528
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.055, 1.07
No. of reflections	1768
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.41
Computer programs: APEX4 and SAINT (Bruker, 2020 ), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ), SHELXTL (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2424642

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025001379/wm5748sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025001379/wm5748Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025001379/wm5748Isup3.cml

checkCIF report

Computing details top

4-Fluorobenzo[c][1,2,5]selenadiazol-1-ium chloride top

Crystal data top

C₆H₄FN₂Se⁺·Cl⁻	F(000) = 456
M_r = 237.52	D_x = 2.081 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.889 (4) Å	Cell parameters from 3456 reflections
b = 7.250 (5) Å	θ = 3.0–27.8°
c = 15.183 (10) Å	µ = 5.25 mm⁻¹
β = 90.90 (3)°	T = 296 K
V = 758.2 (9) Å³	Plate, yellow
Z = 4	0.34 × 0.23 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	1528 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.046
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 27.9°, θ_min = 3.0°
T_min = 0.252, T_max = 0.498	h = −8→9
9806 measured reflections	k = −8→9
1768 independent reflections	l = −19→19

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)] = 0.025	Hydrogen site location: mixed
wR(F²) = 0.055	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0085P)² + 0.4749P] where P = (F_o² + 2F_c²)/3
1768 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.27 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
Se1	0.22554 (3)	0.60768 (4)	0.44282 (2)	0.03658 (9)
Cl1	0.10964 (9)	0.22691 (9)	0.45729 (5)	0.04730 (16)
F1	0.7896 (2)	0.5196 (3)	0.29631 (12)	0.0683 (5)
N1	0.4403 (3)	0.5410 (3)	0.38754 (13)	0.0369 (4)
N2	0.2954 (3)	0.8495 (3)	0.42793 (13)	0.0369 (4)
H2N	0.224535	0.941205	0.440922	0.044*
C1	0.5393 (3)	0.6891 (4)	0.36440 (14)	0.0341 (5)
C2	0.4619 (3)	0.8681 (3)	0.38569 (14)	0.0345 (5)
C3	0.5575 (3)	1.0345 (4)	0.36309 (16)	0.0430 (6)
H3	0.506553	1.149204	0.377483	0.052*
C4	0.7274 (4)	1.0179 (5)	0.31933 (17)	0.0502 (7)
H4	0.794289	1.124494	0.304325	0.060*
C5	0.8070 (4)	0.8445 (5)	0.29559 (18)	0.0521 (7)
H5	0.922383	0.840209	0.264667	0.063*
C6	0.7178 (3)	0.6873 (4)	0.31723 (16)	0.0434 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.03476 (13)	0.02831 (14)	0.04693 (14)	0.00279 (9)	0.00965 (8)	−0.00143 (11)
Cl1	0.0487 (3)	0.0279 (3)	0.0659 (4)	0.0022 (2)	0.0187 (3)	−0.0004 (3)
F1	0.0536 (9)	0.0656 (14)	0.0865 (12)	0.0207 (9)	0.0249 (8)	−0.0028 (11)
N1	0.0354 (9)	0.0326 (12)	0.0427 (10)	0.0062 (8)	0.0051 (8)	−0.0022 (9)
N2	0.0378 (9)	0.0262 (12)	0.0469 (11)	0.0033 (8)	0.0091 (8)	−0.0032 (9)
C1	0.0312 (10)	0.0345 (14)	0.0367 (11)	0.0027 (9)	0.0008 (8)	−0.0027 (10)
C2	0.0354 (11)	0.0332 (14)	0.0347 (11)	−0.0019 (9)	−0.0008 (8)	−0.0001 (10)
C3	0.0460 (12)	0.0352 (15)	0.0477 (13)	−0.0055 (11)	−0.0009 (10)	0.0023 (12)
C4	0.0463 (13)	0.053 (2)	0.0509 (15)	−0.0145 (12)	0.0026 (11)	0.0094 (13)
C5	0.0367 (12)	0.066 (2)	0.0536 (15)	−0.0020 (12)	0.0100 (10)	0.0076 (15)
C6	0.0359 (11)	0.0482 (18)	0.0462 (14)	0.0078 (11)	0.0066 (10)	−0.0006 (12)

Geometric parameters (Å, º) top

Se1—N1	1.779 (2)	C2—C3	1.419 (4)
Se1—N2	1.833 (2)	C3—C4	1.360 (4)
F1—C6	1.352 (4)	C3—H3	0.9300
N1—C1	1.322 (3)	C4—C5	1.420 (5)
N2—C2	1.330 (3)	C4—H4	0.9300
N2—H2N	0.8500	C5—C6	1.339 (4)
C1—C6	1.433 (3)	C5—H5	0.9300
C1—C2	1.442 (4)

N2···Cl1ⁱ	3.056 (3)	F1···N1	2.800 (3)
H2N···Cl1ⁱ	2.23	H5···F1ⁱⁱ	2.56

N1—Se1—N2	88.83 (10)	C4—C3—H3	121.7
C1—N1—Se1	109.94 (18)	C2—C3—H3	121.7
C2—N2—Se1	112.75 (17)	C3—C4—C5	122.8 (3)
C2—N2—H2N	122.4	C3—C4—H4	118.6
Se1—N2—H2N	124.5	C5—C4—H4	118.6
N1—C1—C6	125.1 (2)	C6—C5—C4	120.7 (2)
N1—C1—C2	118.5 (2)	C6—C5—H5	119.6
C6—C1—C2	116.3 (2)	C4—C5—H5	119.6
N2—C2—C3	127.6 (2)	C5—C6—F1	122.5 (2)
N2—C2—C1	110.0 (2)	C5—C6—C1	121.1 (3)
C3—C2—C1	122.5 (2)	F1—C6—C1	116.5 (3)
C4—C3—C2	116.7 (3)

N2—Se1—N1—C1	0.14 (16)	N2—C2—C3—C4	−179.8 (2)
N1—Se1—N2—C2	0.13 (17)	C1—C2—C3—C4	0.4 (3)
Se1—N1—C1—C6	−178.75 (19)	C2—C3—C4—C5	0.8 (4)
Se1—N1—C1—C2	−0.4 (3)	C3—C4—C5—C6	−1.2 (4)
Se1—N2—C2—C3	179.83 (19)	C4—C5—C6—F1	−179.6 (2)
Se1—N2—C2—C1	−0.3 (2)	C4—C5—C6—C1	0.4 (4)
N1—C1—C2—N2	0.5 (3)	N1—C1—C6—C5	179.2 (2)
C6—C1—C2—N2	179.0 (2)	C2—C1—C6—C5	0.8 (4)
N1—C1—C2—C3	−179.7 (2)	N1—C1—C6—F1	−0.9 (4)
C6—C1—C2—C3	−1.2 (3)	C2—C1—C6—F1	−179.31 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl1ⁱ	0.85	2.23	3.056 (3)	163

Symmetry code: (i) x, y+1, z.

Acknowledgements

The author's contributions are as follows. Conceptualization, AVG, TH and ANB; synthesis, AVG and GZM; X-ray analysis, AVG; writing (review and editing of the manuscript) AVG and TH; funding acquisition, AVG, GZM, KIH and TAJ; supervision, AVG, TH and ANB.

Funding information

This work has been supported by Baku State University, Azerbaijan Medical University and Khazar University in Azerbaijan. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

References

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