1-[(2-Bromo­phen­yl)di­phenyl­meth­yl]-3-(tri­fluorometh­yl)-1H-pyrazole–1-(tri­phenyl­meth­yl)-3-(tri­fluoro­meth­yl)-1H-pyrazole (0.638:0.362)

Guseinov, F.I.; Samigullina, A.I.; Hökelek, T.; Hamidov, S.Z.; Lasri, J.; Hasanov, K.I.; Javadzade, T.A.; Belay, A.N.

doi:10.1107/S2414314625004663

organic compounds

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ISSN: 2414-3146

Volume 10| Part 6| June 2025| x250466

https://doi.org/10.1107/S2414314625004663

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1-[(2-Bromophenyl)diphenylmethyl]-3-(trifluoromethyl)-1H-pyrazole–1-(triphenylmethyl)-3-(trifluoromethyl)-1H-pyrazole (0.638:0.362)

Firudin I. Guseinov,^a,^b Aida I. Samigullina,^b Tuncer Hökelek,^c Sahil Z. Hamidov,^d Jamal Lasri,^e Khudayar I. Hasanov,^f,^g Tahir A. Javadzade ^h and Alebel N. Belay ⁱ ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN. D. Zelinsky Institute of Organic Chemistry, Russian academy of Sciences, 119991 Moscow, Russian Federation, ^cHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^dAzerbaijan Technological University, Shah Ismayil Khatai Avenue 103, AZ2011 Ganja, Azerbaijan, ^eDepartment of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, Jeddah 21589, Saudi Arabia, ^fWestern Caspian University, Istiqlaliyyat Street 31, AZ 1001, Baku, Azerbaijan, ^gAzerbaijan Medical University, Scientific Research Centre (SCR), A. Kasumzade St. 14, AZ1096 Baku, Azerbaijan, ^hDepartment of Chemistry and Chemical Engineering, Khazar University, Mahsati St. 41, AZ1096 Baku, Azerbaijan, and ⁱDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 16 May 2025; accepted 23 May 2025; online 17 June 2025)

In the title compound, 0.638C₂₃H₁₆BrF₃N₂·0.362C₂₃H₁₇F₃N₂, the Br atom has been partially replaced by an H atom by reaction with NaH. In the crystal, pairwise C—H⋯Br hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R²₂(16) ring motifs. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (40.1%), H⋯F/F⋯H (21.4%) and H⋯C/C⋯H (18.9%) interactions.

Keywords: crystal structure; hydrogen bond; pyrazole.

CCDC reference: 2454123

Structure description

Among N-hetercyclic compounds, pyrazole and its derivatives constitute a versatile building block in organic synthesis and possess a wide spectrum of biological activities such as antifungal, antitubeculosis, antimicrobial and anti-inflammatory (Khalilov et al., 2024 ). As part of our ongoing studies in this area, we report herein the synthesis and structure of the title compound, 0.638C₂₃H₁₆BrF₃N₂·0.362C₂₃H₁₇F₃N₂ (I), which crystallized as a co-crystal due to an inadvertent partial reaction of the [(2-bromophenyl)chloromethylene]dibenzene starting material with NaH.

Compound (I) contains pyrazole A (N1/N2/C3–C5) and phenyl B (C7–C12), C (C13–C18) and D (C19–C24) rings (Fig. 1) linked at C6. They are oriented at dihedral angles of A/B = 45.31 (6)°, A/C = 70.94 (6)°, A/D = 86.87 (6)°, B/C = 72.22 (5)°, B/D = 78.29 (6)° and C/D = 74.72 (6)°. The minimum and maximum bond angles at C6 are N2—C6—C13 = 105.75 (13) and C13—C6—C19 = 112.04 (13)°, respectively. Atom C14 is bonded to bromine and hydrogen in a 0.6380 (14):0.3620 (14) ratio (see the refinement section).

Figure 1
The title molecule with atom-numbering scheme and displacement ellipsoids at the 50% probability level.

In the crystal, pairwise C—H⋯Br hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers, enclosing R₂²(16) ring motifs (Fig. 2). Further, there is a weak C—H⋯π interaction (Table 1). No π–π interactions are observed.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Br1ⁱ	0.95	2.90	3.8277 (19)	165
C22—H22⋯Cg2ⁱⁱ	0.95	2.85	3.648 (2)	143
Symmetry codes: (i) ; (ii) .

Figure 2
A partial packing diagram viewed approximately along the a-axis direction. Intermolecular C—H⋯O hydrogen bonds are shown as dashed lines. H atoms not involved in these interactions have been omitted for clarity.

In order to visualize the intermolecular interactions in the crystal of (I), a Hirshfeld surface analysis (Fig. 3) was carried out using CrystalExplorer (Spackman et al., 2021 ). The overall two-dimensional fingerprint plot, Fig. 4a, and those delineated into the different contact types are illustrated in Fig. 4 b–f, respectively.

Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm.

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

Synthesis and crystallization

To a solution of 136 mg (1 mmol) of 3-(trifluoromethyl)-1H-pyrazole in 15 ml of tetrahydrofuran, 40 mg of 60%_wt NaH powder was added with stirring and the mixture was boiled for 5 min. To the resulting solution, 357 mg (1 mmol) of [(2-bromophenyl)chloromethylene]dibenzene, contaminated by (chloromethanetriyl)benzene formed in situ, in 10 ml of tetrahydrofuran was added, and the reaction mixture was boiled for 3 h. The solvent was removed in vacuo and the remaining powder was recrystallized from acetonitrile solution. The title compound was isolated in the form of colorless prisms. yield: 375 mg (82%); m.p. 379–381 K. According to the X-ray data, the bromine atom has been partially replaced by a hydrogen atom through its reaction with the excess of sodium hydride (Rohrbach et al., 2019 ). The refined occupancy values of atoms Br1 and H14 are 0.6380 (14) and 0.3620 (14). In fact, the elemental analysis, ¹H NMR and ¹³C NMR data confirm the partially replacement of Br atom with the H atom in the title compound. Analysis calculated (%) for C₂₃H_16.36Br_0.64F₃N₂: C 64.41, H 3.84, N 6.53; found C 60.40, H 3.82, N 6.51. ¹H NMR (300 MHz, CDCl₃): 6.53–7.72 (4H, 2CF₃CCHCHN, 29H, 5Ph and Ar–Br). ¹³C NMR (75 MHz, CDCl₃): 79.55, 80.35, 102.80, 103.35, 126.48, 127.00, 127.52, 128.00, 128.15, 130.07, 130.13, 130.25, 130.43, 131.38, 131.89, 132.13, 132.46, 133.61, 133.98, 135.89, 136.16, 140.47, 141.50 and 141.68. The synthesis scheme is shown in Fig. 5.

Figure 5
The synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. When refined with full occupancy, the bromine atom showed excessive displacement and the refinement was unstable, so the Br occupancy was allowed to vary and an H atom with the complementary occupancy factor occupying the same position bound to C14 was added to the model to treat the positional disorder. The bromine and hydrogen occupancies refined to 0.6380 (14) and 0.3620 (14), respectively. This is chemically reasonable and can be related to the presence of sodium hydride (see above).

Table 2
Experimental details

Crystal data
Chemical formula	0.64(C₂₃H₁₆BrF₃N₂)·0.36(C₂₃H₁₇F₃N₂)
M_r	428.88
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	8.84082 (17), 9.48683 (18), 11.6797 (2)
α, β, γ (°)	95.3496 (16), 91.0661 (16), 103.5919 (17)
V (Å³)	947.18 (3)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	2.42
Crystal size (mm)	0.46 × 0.25 × 0.16

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2024 $[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.310, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21061, 4105, 4012
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.095, 1.05
No. of reflections	4105
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.29
Computer programs: CrysAlis PRO (Rigaku OD, 2024 $[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ) and SHELXL2019/2 (Sheldrick, 2015b ).

Structural data

CCDC reference: 2454123

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625004663/hb4519sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625004663/hb4519Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625004663/hb4519Isup3.cml

checkCIF report

Computing details top

1-[(2-Bromophenyl)diphenylmethyl]-3-(trifluoromethyl)-1H-pyrazole; 1-(triphenylmethyl)-3-(trifluoromethyl)-1H-pyrazole top

Crystal data top

0.64(C₂₃H₁₆BrF₃N₂)·0.36(C₂₃H₁₇F₃N₂)	Z = 2
M_r = 428.88	F(000) = 436
Triclinic, P1	D_x = 1.504 Mg m⁻³
a = 8.84082 (17) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.48683 (18) Å	Cell parameters from 14043 reflections
c = 11.6797 (2) Å	θ = 3.8–80.4°
α = 95.3496 (16)°	µ = 2.42 mm⁻¹
β = 91.0661 (16)°	T = 100 K
γ = 103.5919 (17)°	Prism, colorless
V = 947.18 (3) Å³	0.46 × 0.25 × 0.16 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4012 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.029
ω scans	θ_max = 80.6°, θ_min = 3.8°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2024)	h = −8→10
T_min = 0.310, T_max = 1.000	k = −12→12
21061 measured reflections	l = −14→14
4105 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0432P)² + 0.888P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4105 reflections	Δρ_max = 0.78 e Å⁻³
263 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

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	Occ. (<1)
Br1	0.04169 (3)	0.46569 (3)	0.70061 (3)	0.02635 (12)	0.6380 (14)
F1	0.11203 (14)	0.91657 (15)	0.49575 (12)	0.0398 (3)
F2	0.26791 (17)	0.89368 (14)	0.36004 (10)	0.0393 (3)
F3	0.35009 (15)	1.03658 (13)	0.51449 (11)	0.0356 (3)
N1	0.32218 (16)	0.78802 (16)	0.63930 (12)	0.0195 (3)
N2	0.35135 (16)	0.65782 (15)	0.65518 (12)	0.0176 (3)
C3	0.3493 (2)	0.57369 (19)	0.55393 (15)	0.0222 (3)
H3	0.367687	0.478646	0.544845	0.027*
C4	0.3158 (2)	0.6514 (2)	0.46736 (15)	0.0237 (4)
H4	0.305721	0.622763	0.386909	0.028*
C5	0.2998 (2)	0.7824 (2)	0.52534 (15)	0.0225 (3)
C6	0.40061 (18)	0.62246 (17)	0.76976 (14)	0.0167 (3)
C7	0.32585 (18)	0.69732 (18)	0.86925 (14)	0.0177 (3)
C8	0.36095 (19)	0.84936 (19)	0.88728 (15)	0.0203 (3)
H8	0.425545	0.905119	0.835485	0.024*
C9	0.3028 (2)	0.9205 (2)	0.97994 (16)	0.0247 (4)
H9	0.325160	1.023968	0.989494	0.030*
C10	0.2121 (2)	0.8406 (2)	1.05844 (16)	0.0273 (4)
H10	0.172152	0.888721	1.121707	0.033*
C11	0.1807 (2)	0.6893 (2)	1.04331 (16)	0.0267 (4)
H11	0.120369	0.633808	1.097367	0.032*
C12	0.2369 (2)	0.6185 (2)	0.94940 (15)	0.0219 (3)
H12	0.214206	0.514998	0.939985	0.026*
C13	0.35039 (19)	0.45490 (18)	0.76648 (14)	0.0186 (3)
C15	0.1532 (2)	0.2253 (2)	0.73370 (16)	0.0260 (4)
H15	0.048461	0.175161	0.713620	0.031*
C16	0.2626 (2)	0.14738 (19)	0.75887 (16)	0.0273 (4)
H16	0.233156	0.044104	0.756042	0.033*
C17	0.4146 (2)	0.22167 (19)	0.78807 (16)	0.0245 (4)
H17	0.489986	0.169482	0.805959	0.029*
C18	0.4572 (2)	0.37302 (18)	0.79125 (14)	0.0200 (3)
H18	0.562283	0.422246	0.810911	0.024*
C19	0.57896 (19)	0.67975 (17)	0.78538 (15)	0.0183 (3)
C20	0.6721 (2)	0.7239 (2)	0.69431 (16)	0.0234 (4)
H20	0.625359	0.721401	0.620015	0.028*
C21	0.8338 (2)	0.7717 (2)	0.71114 (18)	0.0300 (4)
H21	0.896109	0.801274	0.648266	0.036*
C22	0.9034 (2)	0.7763 (2)	0.81901 (18)	0.0286 (4)
H22	1.013382	0.807270	0.830068	0.034*
C23	0.8114 (2)	0.7352 (2)	0.91089 (17)	0.0256 (4)
H23	0.858441	0.739789	0.985367	0.031*
C24	0.6510 (2)	0.68749 (19)	0.89435 (15)	0.0216 (3)
H24	0.589149	0.659670	0.957855	0.026*
C25	0.2586 (2)	0.9072 (2)	0.47476 (16)	0.0269 (4)
C14	0.1967 (2)	0.37605 (19)	0.73785 (15)	0.0214 (3)
H14	0.120377	0.427587	0.720820	0.026*	0.3620 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01588 (16)	0.02709 (17)	0.03626 (19)	0.00369 (11)	0.00152 (11)	0.00758 (12)
F1	0.0296 (6)	0.0501 (8)	0.0494 (8)	0.0226 (5)	0.0046 (5)	0.0198 (6)
F2	0.0574 (8)	0.0450 (7)	0.0225 (6)	0.0226 (6)	0.0014 (5)	0.0120 (5)
F3	0.0403 (7)	0.0283 (6)	0.0396 (7)	0.0086 (5)	−0.0028 (5)	0.0107 (5)
N1	0.0179 (7)	0.0209 (7)	0.0218 (7)	0.0074 (5)	0.0010 (5)	0.0055 (5)
N2	0.0170 (6)	0.0198 (7)	0.0178 (7)	0.0074 (5)	0.0012 (5)	0.0037 (5)
C3	0.0228 (8)	0.0246 (8)	0.0210 (8)	0.0094 (6)	0.0028 (6)	0.0014 (6)
C4	0.0224 (8)	0.0312 (9)	0.0196 (8)	0.0098 (7)	0.0025 (6)	0.0041 (7)
C5	0.0183 (8)	0.0296 (9)	0.0217 (8)	0.0077 (7)	0.0020 (6)	0.0072 (7)
C6	0.0159 (7)	0.0185 (7)	0.0175 (7)	0.0063 (6)	0.0018 (6)	0.0050 (6)
C7	0.0132 (7)	0.0246 (8)	0.0173 (7)	0.0077 (6)	0.0008 (6)	0.0041 (6)
C8	0.0183 (8)	0.0231 (8)	0.0209 (8)	0.0075 (6)	−0.0021 (6)	0.0026 (6)
C9	0.0230 (8)	0.0266 (9)	0.0253 (9)	0.0097 (7)	−0.0034 (7)	−0.0025 (7)
C10	0.0225 (9)	0.0404 (10)	0.0214 (8)	0.0144 (8)	0.0003 (7)	−0.0021 (7)
C11	0.0197 (8)	0.0392 (10)	0.0222 (8)	0.0073 (7)	0.0049 (7)	0.0070 (7)
C12	0.0175 (8)	0.0261 (8)	0.0230 (8)	0.0057 (6)	0.0020 (6)	0.0060 (7)
C13	0.0188 (8)	0.0196 (8)	0.0183 (7)	0.0055 (6)	0.0023 (6)	0.0044 (6)
C15	0.0242 (9)	0.0231 (9)	0.0279 (9)	0.0004 (7)	−0.0020 (7)	0.0030 (7)
C16	0.0345 (10)	0.0181 (8)	0.0290 (9)	0.0048 (7)	−0.0002 (8)	0.0051 (7)
C17	0.0268 (9)	0.0223 (8)	0.0272 (9)	0.0106 (7)	0.0012 (7)	0.0045 (7)
C18	0.0192 (8)	0.0211 (8)	0.0212 (8)	0.0072 (6)	0.0014 (6)	0.0035 (6)
C19	0.0154 (7)	0.0160 (7)	0.0251 (8)	0.0058 (6)	0.0032 (6)	0.0037 (6)
C20	0.0201 (8)	0.0265 (8)	0.0251 (9)	0.0064 (7)	0.0041 (7)	0.0071 (7)
C21	0.0201 (9)	0.0334 (10)	0.0372 (10)	0.0051 (7)	0.0097 (7)	0.0089 (8)
C22	0.0158 (8)	0.0286 (9)	0.0423 (11)	0.0055 (7)	0.0008 (7)	0.0074 (8)
C23	0.0200 (8)	0.0264 (9)	0.0311 (9)	0.0063 (7)	−0.0037 (7)	0.0045 (7)
C24	0.0198 (8)	0.0226 (8)	0.0238 (8)	0.0065 (6)	0.0017 (6)	0.0056 (6)
C25	0.0269 (9)	0.0329 (10)	0.0241 (9)	0.0114 (7)	0.0010 (7)	0.0081 (7)
C14	0.0185 (8)	0.0224 (8)	0.0242 (8)	0.0057 (6)	−0.0003 (6)	0.0045 (6)

Geometric parameters (Å, º) top

Br1—C14	1.8400 (17)	C11—H11	0.9500
F1—C25	1.345 (2)	C12—H12	0.9500
F2—C25	1.340 (2)	C13—C18	1.398 (2)
F3—C25	1.338 (2)	C13—C14	1.406 (2)
N1—C5	1.336 (2)	C15—C14	1.387 (2)
N1—N2	1.3481 (19)	C15—C16	1.391 (3)
N2—C3	1.361 (2)	C15—H15	0.9500
N2—C6	1.491 (2)	C16—C17	1.383 (3)
C3—C4	1.372 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.393 (2)
C4—C5	1.397 (3)	C17—H17	0.9500
C4—H4	0.9500	C18—H18	0.9500
C5—C25	1.487 (2)	C19—C20	1.392 (2)
C6—C13	1.543 (2)	C19—C24	1.400 (2)
C6—C19	1.544 (2)	C20—C21	1.399 (3)
C6—C7	1.545 (2)	C20—H20	0.9500
C7—C12	1.391 (2)	C21—C22	1.384 (3)
C7—C8	1.397 (2)	C21—H21	0.9500
C8—C9	1.392 (2)	C22—C23	1.388 (3)
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.389 (3)	C23—C24	1.388 (2)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.390 (3)	C24—H24	0.9500
C10—H10	0.9500	C14—H14	0.9500
C11—C12	1.393 (3)

C5—N1—N2	103.84 (14)	C14—C15—H15	119.9
N1—N2—C3	112.03 (14)	C16—C15—H15	119.9
N1—N2—C6	122.28 (13)	C17—C16—C15	119.36 (17)
C3—N2—C6	125.20 (14)	C17—C16—H16	120.3
N2—C3—C4	107.44 (15)	C15—C16—H16	120.3
N2—C3—H3	126.3	C16—C17—C18	120.02 (16)
C4—C3—H3	126.3	C16—C17—H17	120.0
C3—C4—C5	103.74 (16)	C18—C17—H17	120.0
C3—C4—H4	128.1	C17—C18—C13	122.20 (16)
C5—C4—H4	128.1	C17—C18—H18	118.9
N1—C5—C4	112.94 (16)	C13—C18—H18	118.9
N1—C5—C25	119.50 (16)	C20—C19—C24	118.32 (16)
C4—C5—C25	127.54 (16)	C20—C19—C6	122.24 (15)
N2—C6—C13	105.75 (13)	C24—C19—C6	119.44 (15)
N2—C6—C19	108.08 (13)	C19—C20—C21	120.63 (17)
C13—C6—C19	112.04 (13)	C19—C20—H20	119.7
N2—C6—C7	111.89 (12)	C21—C20—H20	119.7
C13—C6—C7	111.37 (13)	C22—C21—C20	120.31 (17)
C19—C6—C7	107.72 (13)	C22—C21—H21	119.8
C12—C7—C8	118.19 (15)	C20—C21—H21	119.8
C12—C7—C6	122.00 (15)	C21—C22—C23	119.54 (17)
C8—C7—C6	119.47 (14)	C21—C22—H22	120.2
C9—C8—C7	121.07 (16)	C23—C22—H22	120.2
C9—C8—H8	119.5	C24—C23—C22	120.24 (17)
C7—C8—H8	119.5	C24—C23—H23	119.9
C10—C9—C8	120.16 (17)	C22—C23—H23	119.9
C10—C9—H9	119.9	C23—C24—C19	120.94 (16)
C8—C9—H9	119.9	C23—C24—H24	119.5
C9—C10—C11	119.21 (17)	C19—C24—H24	119.5
C9—C10—H10	120.4	F3—C25—F2	107.32 (15)
C11—C10—H10	120.4	F3—C25—F1	105.90 (16)
C10—C11—C12	120.46 (17)	F2—C25—F1	106.31 (15)
C10—C11—H11	119.8	F3—C25—C5	113.50 (15)
C12—C11—H11	119.8	F2—C25—C5	110.83 (16)
C7—C12—C11	120.86 (17)	F1—C25—C5	112.53 (15)
C7—C12—H12	119.6	C15—C14—C13	122.00 (16)
C11—C12—H12	119.6	C15—C14—Br1	115.78 (13)
C18—C13—C14	116.31 (15)	C13—C14—Br1	122.21 (13)
C18—C13—C6	121.25 (15)	C15—C14—H14	119.0
C14—C13—C6	122.44 (14)	C13—C14—H14	119.0
C14—C15—C16	120.11 (17)	Br1—C14—H14	3.4

C5—N1—N2—C3	0.76 (18)	C19—C6—C13—C14	−171.36 (15)
C5—N1—N2—C6	173.14 (14)	C7—C6—C13—C14	67.9 (2)
N1—N2—C3—C4	−0.6 (2)	C14—C15—C16—C17	0.1 (3)
C6—N2—C3—C4	−172.71 (15)	C15—C16—C17—C18	−0.5 (3)
N2—C3—C4—C5	0.17 (19)	C16—C17—C18—C13	0.5 (3)
N2—N1—C5—C4	−0.65 (19)	C14—C13—C18—C17	−0.1 (3)
N2—N1—C5—C25	177.85 (15)	C6—C13—C18—C17	−179.57 (15)
C3—C4—C5—N1	0.3 (2)	N2—C6—C19—C20	−13.3 (2)
C3—C4—C5—C25	−178.05 (17)	C13—C6—C19—C20	102.79 (18)
N1—N2—C6—C13	154.86 (14)	C7—C6—C19—C20	−134.39 (16)
C3—N2—C6—C13	−33.8 (2)	N2—C6—C19—C24	166.99 (14)
N1—N2—C6—C19	−85.00 (17)	C13—C6—C19—C24	−76.89 (18)
C3—N2—C6—C19	86.35 (18)	C7—C6—C19—C24	45.93 (19)
N1—N2—C6—C7	33.4 (2)	C24—C19—C20—C21	1.3 (3)
C3—N2—C6—C7	−155.22 (15)	C6—C19—C20—C21	−178.38 (16)
N2—C6—C7—C12	123.47 (16)	C19—C20—C21—C22	−0.2 (3)
C13—C6—C7—C12	5.3 (2)	C20—C21—C22—C23	−1.0 (3)
C19—C6—C7—C12	−117.88 (16)	C21—C22—C23—C24	1.1 (3)
N2—C6—C7—C8	−63.35 (19)	C22—C23—C24—C19	0.0 (3)
C13—C6—C7—C8	178.53 (14)	C20—C19—C24—C23	−1.2 (3)
C19—C6—C7—C8	55.31 (18)	C6—C19—C24—C23	178.47 (15)
C12—C7—C8—C9	−2.9 (2)	N1—C5—C25—F3	48.2 (2)
C6—C7—C8—C9	−176.34 (15)	C4—C5—C25—F3	−133.53 (19)
C7—C8—C9—C10	2.0 (3)	N1—C5—C25—F2	169.06 (16)
C8—C9—C10—C11	0.1 (3)	C4—C5—C25—F2	−12.7 (3)
C9—C10—C11—C12	−1.2 (3)	N1—C5—C25—F1	−72.0 (2)
C8—C7—C12—C11	1.8 (2)	C4—C5—C25—F1	106.2 (2)
C6—C7—C12—C11	175.07 (15)	C16—C15—C14—C13	0.4 (3)
C10—C11—C12—C7	0.2 (3)	C16—C15—C14—Br1	179.13 (15)
N2—C6—C13—C18	125.63 (16)	C18—C13—C14—C15	−0.3 (3)
C19—C6—C13—C18	8.1 (2)	C6—C13—C14—C15	179.15 (16)
C7—C6—C13—C18	−112.61 (17)	C18—C13—C14—Br1	−179.04 (13)
N2—C6—C13—C14	−53.84 (19)	C6—C13—C14—Br1	0.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br1ⁱ	0.95	2.90	3.8277 (19)	165
C22—H22···Cg2ⁱⁱ	0.95	2.85	3.648 (2)	143

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

Acknowledgements

The crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic Chemistry, Moscow. This work was supported by the Azerbaijan Technological University (Azerbaijan), Western Caspian University (Azerbaijan), Azerbaijan Medical University (Azerbaijan) and Khazar University (Azerbaijan). TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004). The authors contributions are as follows. Conceptualization, FIG, TH and ANB; synthesis, FIG and SZH; X-ray analysis, AIS; Hirshfeld surface analyses, crystal voids, intermolecular interaction energies and energy frameworks, TH; writing (review and editing of the manuscript), JL, TH and KIH; funding acquisition, KIH and TAJ; supervision, TH and ANB.

References

Khalilov, A. N., Cisterna, J., Cárdenas, A., Tuzun, B., Erkan, S., Gurbanov, A. V. & Brito, I. (2024). J. Mol. Struct. 1313, 138652. Web of Science CSD CrossRef Google Scholar
Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Rohrbach, S., Smith, A. J., Pang, J. H., Poole, D. L., Tuttle, T., Chiba, S. & Murphy, J. A. (2019). Angew. Chem. Int. Ed. 58, 16368–16388. 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
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 10| Part 6| June 2025| x250466

https://doi.org/10.1107/S2414314625004663

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[(2-Bromo­phen­yl)di­phenyl­meth­yl]-3-(tri­fluorometh­yl)-1H-pyrazole–1-(tri­phenyl­meth­yl)-3-(tri­fluoro­meth­yl)-1H-pyrazole (0.638:0.362)

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

1-[(2-Bromophenyl)diphenylmethyl]-3-(trifluoromethyl)-1H-pyrazole–1-(triphenylmethyl)-3-(trifluoromethyl)-1H-pyrazole (0.638:0.362)