Crystal structure and Hirshfeld surface analysis of 2,2,2-tri­fluoro-1-(7-methyl­imidazo[1,2-a]pyridin-3-yl)ethan-1-one

Guseinov, F.I.; Kobrakov, K.I.; Ugrak, B.I.; Atioğlu, Z.; Akkurt, M.; Bhattarai, A.

doi:10.1107/S2056989021012676

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ISSN: 2056-9890

Volume 78| Part 1| January 2022| Pages 12-17

https://doi.org/10.1107/S2056989021012676

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Crystal structure and Hirshfeld surface analysis of 2,2,2-trifluoro-1-(7-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one

Firudin I. Guseinov,^a,^b Konstantin I. Kobrakov,^a Bogdan I. Ugrak,^b Zeliha Atioğlu,^c Mehmet Akkurt ^d and Ajaya Bhattarai ^e ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation, ^cDepartment of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Turkey, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: bkajaya@yahoo.com

Edited by A. V. Yatsenko, Moscow State University, Russia (Received 11 November 2021; accepted 29 November 2021; online 1 January 2022)

The bicyclic imidazo[1,2-a]pyridine core in the molecule of the title compound, C₁₀H₇F₃N₂O, is planar within 0.004 (1) Å. In the crystal, the molecules are linked by pairs of C—H⋯N and C—H⋯O hydrogen bonds, forming strips. These strips are connected by the F⋯F contacts into layers, which are further joined by π–π stacking interactions. The Hirshfeld surface analysis and fingerprint plots reveal that molecular packing is governed by F⋯H/H⋯F (31.6%), H⋯H (16.8%), C⋯H/H⋯C (13.8%) and O⋯H/H⋯O (8.5%) contacts.

Keywords: crystal structure; imidazo[1,2-a]pyridine; hydrogen bonds; F⋯F contacts; Hirshfeld surface analysis.

CCDC reference: 2124974

1. Chemical context

The imidazo[1,2-a]pyridine synthon is one of the important fused bicyclic 5–6 heterocycles and it is recognized as a `drug prejudice' scaffold because of its wide range of applications in medicinal chemistry (Bagdi et al., 2015 ). This synthon is also useful in coordination chemistry and catalysis because of its coordination ability and non-covalent donor–acceptor bonding (Guseinov et al., 2022 ; Ma et al., 2020 , 2021 ; Mahmudov et al., 2020 , 2021 ). Synthesis of this synthon from easily available chemicals is desirable due to its importance in the various branches of chemistry (Bagdi et al., 2015). Along with this, intermolecular interactions organize molecular architectures, which play a crucial role in synthesis, catalysis, micellization, etc. (Gurbanov et al., 2020a ,b ; Kopylovich et al., 2011 ; Ma et al., 2017a ,b ). The non-covalent bond–acceptor ability of both nitrogen atoms in the imidazo[1,2-a]pyridine synthon can be used in crystal engineering and in the design of dyes and other materials (Maharramov et al., 2018 ; Mizar et al., 2012 ; Shixaliyev et al., 2014 ; Shikhaliyev et al., 2018 , 2019 ). Herein, we report a one-pot synthesis of 2,2,2-trifluoro-1-(7-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one (I) from (E/Z)-3-bromo-1,1,1-trifluoro-4-isopropoxybut-3-en-2-one and 4-methylpyridin-2-amine, which provides multiple intermolecular non-covalent interactions.

2. Structural commentary

In the molecule of the title compound (Fig. 1), the fused bicyclic imidazo[1,2-a]pyridine core is planar within 0.004 (1) Å, with a dihedral angle of 0.34 (6)° between the mean planes of the five- and six-membered rings. The C2—C1—C8—C9 and N2—C1—C8—O1 torsion angles of 1.04 (18) and 1.14 (19)°, respectively, show that the ethanone group lies near the plane of the bicycle. The bond lengths N1—C2, C2—C1 and C1—C8 of 1.3367 (16), 1.3987 (16) and 1.4247 (16) Å, respectively, indicate strong π-conjugation in the N1–O1 chain.

Figure 1
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, the molecules are linked by pairs of C—H⋯N and C—H⋯O hydrogen bonds into strips elongated along the [210] direction (Figs. 2 and 3, Table 1). These strips are joined into layers parallel to (1 $[\overline{2}]$ 2) by F⋯F contacts (Figs. 3–5 , Table 2). The layers are connected by F⋯H contacts (Fig. 5, Table 2) and π–π interactions with a shortest intercentroid separation of 3.6395 (7) Å [Cg1⋯Cg1(1 − x, 1 − y, 1 − z); Cg1 is the centroid of the imidazole ring].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1ⁱ	0.95	2.48	3.4139 (16)	167
C7—H7⋯O1ⁱⁱ	0.95	2.30	3.1464 (14)	147
Symmetry codes: (i) ; (ii) .

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

Contact	Distance	Symmetry operation
O1⋯C3	3.1574 (15)	1 + x, y, z
F1⋯H10B	2.86	1 + x, y, −1 + z
F3⋯F1	2.9074 (11)	2 − x, 1 − y, −z
H10C⋯O1	2.83	1 − x, 2 − y, 1 − z
F2⋯H10A	2.64	x, y, −1 + z
H2⋯F2	2.80	1 − x, 1 − y, −z
C3⋯N1	3.3055 (16)	1 − x, 1 − y, 1 − z

Figure 2
A general view of the C—H⋯O and C—H⋯N hydrogen bonds and π–π stacking interactions in the title compound, depicted by dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted. [Symmetry codes: (i) −x, −y + 1, −z + 1; (ii) −x + 2, −y + 2, −z + 1; (iii) x + 1, y, z; (iv) −1 + x, y, z.]

Figure 3
Packing diagram of the title compound, viewed down the a axis showing the C—H⋯O and C—H⋯N hydrogen bonds and the F⋯F and π–π stacking interactions. Hydrogen atoms not involved in hydrogen bonding are omitted.

Figure 4
Packing diagram of the title compound, viewed down the b axis showing the C—H⋯O and C—H⋯N hydrogen bonds and the F⋯F and π–π stacking interactions. Hydrogen atoms not involved in hydrogen bonding are omitted.

Figure 5
Packing diagram of the title compound, viewed down the c axis showing the C—H⋯O and C—H⋯N hydrogen bonds and the F⋯F and π–π stacking interactions. Hydrogen atoms not involved in hydrogen bonding are omitted.

To visualize the intermolecular interactions in the title compound, the 3D Hirshfeld surfaces and two-dimensional fingerprint plots were computed using Crystal Explorer 17 (Turner et al., 2017 ). The Hirshfeld surface plotted over d_norm in the range −0.3137 to 1.1314 a.u. is shown in Fig. 6. The intense red spots with negative d_norm values represent C—H⋯O and C—H⋯N hydrogen bonds. Pale red spots correspond to π–π interactions, which are also seen in the shape-index surface (Fig. 7) generated in the range −1 to 1 Å, where they are indicated by adjacent red and blue triangles. The Hirshfeld surface mapped over the electrostatic potential is shown in Fig. 8, where the hydrogen-bond acceptors are represented as red regions. The overall two-dimensional fingerprint plot, and those delineated into F⋯H/H⋯F (31.6%), H⋯H (16.8%), C⋯H/H⋯C (13.8%) and O⋯H/H⋯O (8.5%) contacts are illustrated in Fig. 9. Other minor contributions to the Hirshfeld surface are from N⋯H/H⋯N (7.7%), F⋯F (6.1%), O⋯C/C⋯O (4.2%), N⋯C/C⋯N (3.8%), C⋯C (2.4%), F⋯C/C⋯F (1.7%), F⋯N/N⋯F (1.4%), N⋯N (1.1%) and O⋯N/N⋯O (0.9%) contacts.

Figure 6
Hirshfeld surface of the title molecule mapped over d_norm.

Figure 7
Hirshfeld surface of the title compound plotted over shape-index.

Figure 8
View of the three-dimensional Hirshfeld surface of the title molecule plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. calculated at the Hartree–Fock level of theory using the STO-3 G basis set. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms, corresponding to positive and negative potentials, respectively.

Figure 9
(a) The overall two-dimensional fingerprint plot and those delineated into (b) F⋯H/H⋯F, (c) H⋯H, (d) C⋯H/H⋯C and (e) O⋯H/H⋯O interactions.

4. Database survey

The most closely related compounds containing a similar imidazo[1,2-a]pyridine skeleton, but with different substituents on the amide N atom are: N-t-butyl-2-(phenylethynyl)imidazo[1,2-a]pyridin-3-amine (XOWVOX; Tber et al., 2019 ), 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine (KOXGEM; Khamees et al., 2019 ), N-t-butyl-2-(2-nitrophenyl)imidazo[1,2-a]pyridin-3-amine (PILGAV01; Dhanalakshmi et al., 2019 ), 2-(4-methoxyphenyl)-6-nitroimidazo[1,2-a]pyridine-3-carbaldehyde (DABTEI; Koudad et al., 2015 ), 2-(ethylsulfinyl)imidazo[1,2-a]pyridine-3-sulfonamide (ZAPJAD; Gong et al., 2012 ) and 2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbonitrile (ULEGOI; Fun et al., 2011 ). In the crystal of XOWVOX, molecules are linked by N—H⋯H hydrogen bonds, forming chains along the c-axis direction. The chains are linked by C—H⋯π interactions, forming slabs parallel to the ac plane. In the structure of KOXGEM, an intramolecular C—H⋯N hydrogen bond forms an S(5) ring motif. In the crystal, a short H⋯H contact links adjacent molecules into centrosymmetric dimers. The dimers are joined by weak C—H⋯π and slipped π–π stacking interactions, forming layers parallel to (110), which are connected into a three-dimensional network by short Br⋯H contacts. In the crystal of PILGAV01, N—H⋯N hydrogen bonds link the molecules into [010] chains. The cohesion of the crystal structure of DABTEI is ensured by C—H⋯N and C—H⋯O hydrogen bonds, forming layers parallel to the ac plane. In ZAPJAD, the supramolecular structure is defined by two kinds of intermolecular hydrogen bonds. Pairs of N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers and N—H⋯O hydrogen bonds link the dimers into tubular chains running along the a-axis direction. In the crystal of ULEGOI, molecules are linked into chains through pairs of C—H⋯N interactions, forming R₂²(12) and R₂²(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.

5. Synthesis and crystallization

A mixture of (E/Z)-3-bromo-1,1,1-trifluoro-4-isopropoxybut-3-en-2-one (0.522 mg, 2 mmol) and 4-methylpyridin-2-amine (0.216 mg, 2 mmol) in dry isopropyl alcohol (15 mL) was refluxed for 4 h. Then the solvent was removed on a rotary evaporator under reduced pressure. The residue was recrystallized from methanol. Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution. Colourless solid (yield 94%), m.p. 405–406 K. Analysis calculated for C₁₀H₇F₃N₂O (M = 228.17): C 52.64, H 3.09, N 12.28; found: C 52.55, H 3.07, N 12.19%. ¹H NMR (300 MHz, CDCl₃) δ 2.48 (3H, CH₃), 7.32–8.60 (3H, Ar), 9.32 (1H, CH). ¹³C NMR (75 MHz, CDCl₃) δ 174.45, 150.22, 141.32, 135.67, 131.04, 123.55, 118.66, 118.21, 116.32 and 21.56. ESI–MS: m/z: 229.18 [M + H]⁺.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were positioned geometrically (C—H = 0.95–0.98 Å) and refined as riding, with U_iso(H) = 1.2U_eq(C) for CH hydrogen atoms and U_iso(H) = 1.5U_eq(C) for CH₃ hydrogen atoms.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₀H₇F₃N₂O
M_r	228.18
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	5.4384 (1), 8.8298 (2), 10.0744 (2)
α, β, γ (°)	102.501 (2), 96.764 (2), 91.415 (2)
V (Å³)	468.39 (2)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	1.30
Crystal size (mm)	0.15 × 0.06 × 0.02

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ )
T_min, T_max	0.323, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14165, 2006, 1927
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.09
No. of reflections	2006
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2124974

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021012676/yk2161sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021012676/yk2161Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021012676/yk2161Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2,2,2-Trifluoro-1-(7-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one top

Crystal data top

C₁₀H₇F₃N₂O	Z = 2
M_r = 228.18	F(000) = 232
Triclinic, P1	D_x = 1.618 Mg m⁻³
a = 5.4384 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.8298 (2) Å	Cell parameters from 11472 reflections
c = 10.0744 (2) Å	θ = 4.5–79.1°
α = 102.501 (2)°	µ = 1.30 mm⁻¹
β = 96.764 (2)°	T = 100 K
γ = 91.415 (2)°	Block, colorless
V = 468.39 (2) Å³	0.15 × 0.06 × 0.02 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2006 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1927 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.050
Detector resolution: 10.0000 pixels mm^-1	θ_max = 79.5°, θ_min = 4.5°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −11→10
T_min = 0.323, T_max = 1.000	l = −12→12
14165 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0617P)² + 0.1479P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.37 e Å⁻³
2006 reflections	Δρ_min = −0.26 e Å⁻³
147 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0061 (14)
Primary atom site location: dual

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
F3	0.83669 (15)	0.51338 (8)	0.12281 (8)	0.0298 (2)
F1	1.03655 (15)	0.72062 (9)	0.10632 (8)	0.0306 (2)
F2	0.63947 (16)	0.69737 (10)	0.05569 (8)	0.0352 (2)
O1	0.94235 (16)	0.85798 (10)	0.34833 (9)	0.0231 (2)
N2	0.53525 (17)	0.75163 (11)	0.47862 (10)	0.0178 (2)
N1	0.25848 (19)	0.55184 (12)	0.38082 (11)	0.0224 (2)
C3	0.3285 (2)	0.66590 (13)	0.49404 (12)	0.0195 (3)
C7	0.6410 (2)	0.87311 (13)	0.57981 (12)	0.0199 (3)
H7	0.783693	0.930322	0.567582	0.024*
C6	0.5364 (2)	0.90977 (14)	0.69840 (12)	0.0214 (3)
H6	0.608051	0.993640	0.769395	0.026*
C4	0.2206 (2)	0.70392 (14)	0.61568 (13)	0.0214 (3)
H4	0.077951	0.646052	0.626999	0.026*
C5	0.3224 (2)	0.82541 (14)	0.71850 (13)	0.0211 (3)
C2	0.4210 (2)	0.56623 (14)	0.29402 (12)	0.0210 (3)
H2	0.416403	0.500889	0.205342	0.025*
C1	0.5986 (2)	0.68799 (13)	0.34799 (12)	0.0191 (3)
C9	0.8297 (2)	0.66755 (14)	0.14284 (13)	0.0231 (3)
C8	0.7991 (2)	0.74800 (13)	0.29223 (12)	0.0190 (3)
C10	0.2118 (2)	0.87010 (16)	0.85047 (13)	0.0267 (3)
H10A	0.336148	0.863035	0.927312	0.040*
H10B	0.068569	0.799545	0.848113	0.040*
H10C	0.158430	0.976875	0.862058	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F3	0.0391 (5)	0.0189 (4)	0.0298 (4)	−0.0012 (3)	0.0086 (3)	−0.0001 (3)
F1	0.0318 (4)	0.0315 (4)	0.0291 (4)	−0.0052 (3)	0.0120 (3)	0.0047 (3)
F2	0.0349 (5)	0.0452 (5)	0.0241 (4)	0.0054 (4)	−0.0037 (3)	0.0081 (3)
O1	0.0223 (4)	0.0190 (4)	0.0270 (4)	−0.0048 (3)	0.0026 (3)	0.0037 (3)
N2	0.0161 (5)	0.0153 (5)	0.0222 (5)	−0.0015 (3)	0.0010 (4)	0.0058 (4)
N1	0.0197 (5)	0.0184 (5)	0.0280 (5)	−0.0036 (4)	0.0008 (4)	0.0044 (4)
C3	0.0158 (5)	0.0162 (5)	0.0272 (6)	−0.0019 (4)	0.0002 (4)	0.0079 (4)
C7	0.0180 (5)	0.0167 (5)	0.0241 (6)	−0.0029 (4)	−0.0006 (4)	0.0051 (4)
C6	0.0208 (6)	0.0192 (6)	0.0231 (6)	−0.0002 (4)	−0.0002 (4)	0.0044 (4)
C4	0.0177 (5)	0.0206 (6)	0.0282 (6)	−0.0006 (4)	0.0026 (4)	0.0110 (5)
C5	0.0201 (6)	0.0203 (6)	0.0250 (6)	0.0029 (4)	0.0023 (4)	0.0098 (5)
C2	0.0196 (6)	0.0180 (6)	0.0240 (6)	−0.0017 (4)	0.0000 (4)	0.0034 (4)
C1	0.0191 (6)	0.0167 (5)	0.0213 (6)	−0.0006 (4)	0.0008 (4)	0.0046 (4)
C9	0.0228 (6)	0.0225 (6)	0.0244 (6)	−0.0014 (4)	0.0025 (5)	0.0065 (5)
C8	0.0186 (5)	0.0162 (5)	0.0227 (6)	0.0010 (4)	0.0009 (4)	0.0063 (4)
C10	0.0278 (6)	0.0282 (7)	0.0264 (6)	0.0017 (5)	0.0054 (5)	0.0097 (5)

Geometric parameters (Å, º) top

F3—C9	1.3345 (14)	C6—H6	0.9500
F1—C9	1.3292 (14)	C6—C5	1.4245 (17)
F2—C9	1.3453 (14)	C4—H4	0.9500
O1—C8	1.2208 (15)	C4—C5	1.3728 (18)
N2—C3	1.3827 (14)	C5—C10	1.5028 (17)
N2—C7	1.3706 (15)	C2—H2	0.9500
N2—C1	1.4011 (15)	C2—C1	1.3987 (16)
N1—C3	1.3571 (16)	C1—C8	1.4247 (16)
N1—C2	1.3367 (16)	C9—C8	1.5489 (17)
C3—C4	1.3997 (17)	C10—H10A	0.9800
C7—H7	0.9500	C10—H10B	0.9800
C7—C6	1.3629 (17)	C10—H10C	0.9800

C3—N2—C1	106.60 (10)	N1—C2—C1	112.65 (11)
C7—N2—C3	122.01 (10)	C1—C2—H2	123.7
C7—N2—C1	131.39 (10)	N2—C1—C8	123.53 (11)
C2—N1—C3	105.23 (10)	C2—C1—N2	104.25 (10)
N2—C3—C4	119.63 (11)	C2—C1—C8	132.19 (11)
N1—C3—N2	111.28 (10)	F3—C9—F2	106.95 (10)
N1—C3—C4	129.10 (11)	F3—C9—C8	113.36 (9)
N2—C7—H7	120.8	F1—C9—F3	107.82 (10)
C6—C7—N2	118.35 (11)	F1—C9—F2	107.29 (10)
C6—C7—H7	120.8	F1—C9—C8	110.72 (10)
C7—C6—H6	119.2	F2—C9—C8	110.45 (10)
C7—C6—C5	121.61 (11)	O1—C8—C1	126.81 (11)
C5—C6—H6	119.2	O1—C8—C9	117.43 (10)
C3—C4—H4	120.2	C1—C8—C9	115.72 (10)
C5—C4—C3	119.55 (11)	C5—C10—H10A	109.5
C5—C4—H4	120.2	C5—C10—H10B	109.5
C6—C5—C10	119.98 (11)	C5—C10—H10C	109.5
C4—C5—C6	118.86 (11)	H10A—C10—H10B	109.5
C4—C5—C10	121.17 (11)	H10A—C10—H10C	109.5
N1—C2—H2	123.7	H10B—C10—H10C	109.5

F3—C9—C8—O1	130.29 (11)	C3—N1—C2—C1	0.16 (13)
F3—C9—C8—C1	−51.85 (14)	C3—C4—C5—C6	−0.07 (16)
F1—C9—C8—O1	8.98 (15)	C3—C4—C5—C10	179.86 (10)
F1—C9—C8—C1	−173.16 (10)	C7—N2—C3—N1	−179.78 (10)
F2—C9—C8—O1	−109.71 (12)	C7—N2—C3—C4	0.59 (16)
F2—C9—C8—C1	68.15 (13)	C7—N2—C1—C2	179.87 (11)
N2—C3—C4—C5	−0.35 (17)	C7—N2—C1—C8	−2.02 (19)
N2—C7—C6—C5	−0.07 (17)	C7—C6—C5—C4	0.29 (17)
N2—C1—C8—O1	1.14 (19)	C7—C6—C5—C10	−179.65 (10)
N2—C1—C8—C9	−176.48 (9)	C2—N1—C3—N2	−0.18 (13)
N1—C3—C4—C5	−179.91 (11)	C2—N1—C3—C4	179.41 (11)
N1—C2—C1—N2	−0.09 (13)	C2—C1—C8—O1	178.67 (12)
N1—C2—C1—C8	−177.96 (12)	C2—C1—C8—C9	1.04 (18)
C3—N2—C7—C6	−0.37 (16)	C1—N2—C3—N1	0.13 (13)
C3—N2—C1—C2	−0.03 (12)	C1—N2—C3—C4	−179.50 (9)
C3—N2—C1—C8	178.08 (10)	C1—N2—C7—C6	179.75 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3	0.95	2.53	2.9876 (14)	110
C4—H4···N1ⁱ	0.95	2.48	3.4139 (16)	167
C7—H7···O1	0.95	2.43	2.9864 (14)	117
C7—H7···O1ⁱⁱ	0.95	2.30	3.1464 (14)	147

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

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

Contact	Distance	Symmetry operation
O1···C3	3.1574 (15)	1 + x, y, z
F1···H10B	2.86	1 + x, y, -1 + z
F3···F1	2.9074 (11)	2 - x, 1 - y, -z
H10C···O1	2.83	1 - x, 2 - y, 1 - z
F2···H10A	2.64	x, y, -1 + z
H2···F2	2.80	1 - x, 1 - y, -z
C3···N1	3.3055 (16)	1 - x, 1 - y, 1 - z

Acknowledgements

The author's contributions are as follows. Conceptualization, FIG, MA and AB; synthesis, FIG and KIK; X-ray analysis, BIU, ZA and MA; writing (review and editing of the manuscript), FIG, ZA, MA and AB.

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