research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009394

Crystal structure and Hirshfeld surface analysis of 1,2-bis­­[5-(4-fluoro­phen­yl)-1,3-oxazol-2-yl]benzene

crossmark logo
Viktoriya V. Dyakonenko,a,b* Anna M. Shaposhnyk,a Rodion Yu. Iliashenko,c Andrey O. Doroshenkoc and Alexander V. Kyrychenkoa,c

aInstitute of Functional Materials Chemistry, SSI "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Nauki Ave 60, Kharkiv 61001, Ukraine, bV. I. Vernadskii Institute of General and Inorganic Chemistry of, National Academy of Sciences of Ukraine, Prospect Palladina 32/34, Kyiv 03680, Ukraine, and cV. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine
*Correspondence e-mail: [email protected]

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 21 August 2026; accepted 8 September 2026; online 11 September 2026)

The title compound, C24H14F2N2O2, was studied by single-crystal and powder X-ray diffraction methods. The title compound crystallizes in the monoclinic space group P21/c with one mol­ecule in the asymmetric unit. The two chemically equivalent substituents adopt different orientations relative to the central benzene ring. The dihedral angles between the central benzene and oxazole rings are 2.4 (2) and 57.6 (2)°, while those between the oxazole and terminal 4-fluoro­phenyl rings are 13.3 (2) and 2.5 (2)°, respectively. In the crystal, inversion-related mol­ecules form dimers through π–π stacking between oxazole rings [centroid-to-centroid distance = 3.587 (3) Å] and C—H⋯N hydrogen bonds. The dimers are further connected by C—H⋯N inter­actions into layers parallel to (100). Hirshfeld surface analysis indicates that C⋯H/H⋯C (30.2%), H⋯H (21.8%) and F⋯H/H⋯F (18.0%) contacts make the largest contributions to the crystal packing.

CCDC reference: 2586503

Similar articles

1. Chemical context

The title compound belongs to a series of sterically hindered ortho analogues of the well-known scintillator dye 1,4-bis­(5-phenyl-1,3-oxazol-2-yl)benzene (POPOP; Ambats & Marsh, 1965View full citation). The approximately planar mol­ecular structure of POPOP promotes extended π-conjugation and efficient fluorescence, accounting for its use in plastic and liquid scintillators (Ott et al., 1957View full citation). In ortho-POPOP, however, the two oxazolyl moieties occupy adjacent positions on the central benzene ring. Steric repulsion between these substituents results in pronounced mol­ecular non-planarity both in the crystal and in solution (Doroshenko et al., 1994View full citation, 1997View full citation, 2000aView full citation, 2002aView full citation,bView full citation). The resulting decrease in π-conjugation produces a hypsochromic shift of the absorption spectrum (Doroshenko, 2002aView full citation). Partial flattening in the electronically excited state restores conjugation and gives rise to bathochromically shifted fluorescence and a large Stokes shift (Doroshenko et al., 1996View full citation, 2000bView full citation; Doroshenko, 1999View full citation; Iliashenko et al., 2011View full citation).

A characteristic feature of crystalline ortho-POPOP derivatives is that the two chemically equivalent oxazolyl substituents may adopt considerably different orientations relative to the central benzene ring (Doroshenko et al., 1994View full citation). The mol­ecular conformation can be described in terms of a relatively planar three-ring benzene–oxazole–phenyl fragment and a two-ring oxazole–phenyl fragment that is strongly inclined to the central benzene ring. A closely related compound is the mono­fluoro-substituted derivative 5-(4-ufloro­phen­yl)-2-[2-(5-phenyl-1,3-oxazol-2-yl)phen­yl]-1,3-oxa­zole (2; Ilyashenko et al., 2010View full citation). In its crystal structure, the fluorine atom is disordered between the two terminal phenyl rings, with refined occupancies of 0.627 (3) and 0.373 (3).

[Scheme 1]

The title compound, 1,2-bis­(5-(4-fluoro­phen­yl)-1,3-oxazol-2-yl)benzene (1), is the corresponding di­fluoro-substituted ortho-POPOP derivative, in which both terminal phenyl rings bear a para-fluoro substituent. The present study reports its mol­ecular and crystal structure and Hirshfeld surface analysis.

2. Structural commentary

The mol­ecular structure of the title compond 1 is shown in Fig. 1[link]. The asymmetric unit contains one crystallographically independent mol­ecule (Z′ = 1). The mol­ecule consists of a central benzene ring bearing two 5-(4-fluoro­phen­yl)-1,3-oxazol-2-yl moieties at adjacent ortho-positions.

[Figure 1]
Figure 1
The mol­ecular structure of 1, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

The dihedral angles between the least-squares plane of the central benzene ring (C10–C15) and those of the oxazole rings O1/N1/C7–C9 and O2/N2/C16–C18 are 2.4 (2) and 57.6 (2)°, respectively. The corresponding dihedral angles between the oxazole rings and the terminal 4-fluoro­phenyl rings C1–C6 and C19–C24 are 13.4 (2) and 2.5 (2)°, respectively. Consequently, one moiety forms an approximately planar benzene–oxazole–4-fluoro­phenyl fragment, with only a slight rotation of the terminal 4-fluoro­phenyl ring. In the second moiety, the oxazole and 4-fluoro­phenyl rings are essentially coplanar, whereas their mean plane is strongly inclined to that of the central benzene ring. Thus, although the two substituents are chemically equivalent, they adopt different orientations relative to the central benzene ring in the crystal. Similar differences in the orientations of chemically equivalent substituents have been observed in other crystalline ortho-POPOP derivatives (Doroshenko et al., 1994View full citation, 1997View full citation, 2000aView full citation, 2002bView full citation).

3. Supra­molecular features

In the crystal, inversion-related mol­ecules form dimers consolidated π–π stacking inter­actions between the O1/N1/C7–C9 oxazole rings (Fig. 2[link]). The centroid-to-centroid distance Cg1⋯Cg1iv is 3.587 (3) Å, with a perpendicular distance of 3.456 Å and a shift of 0.962 Å [Cg1 is the centroid of the O1/N1/C7–C9 ring; symmetry code: (iv) 1 − x, 1 − y, 1 – z]. The dimers are additionally consolidated by pairs of C24—H24⋯N1iv hydrogen bonds (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯F2i 0.93 2.70 3.470 (5) 141
C8—H8⋯N2ii 0.93 2.56 3.489 (6) 176
C23—H23⋯F1iii 0.93 2.82 3.559 (5) 137
C24—H24⋯N1iv 0.93 2.54 3.449 (5) 168
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation.
[Figure 2]
Figure 2
A centrosymmetric dimer of 1 formed by π–π stacking and C—H⋯N hydrogen bonds. The inter­molecular inter­actions are shown as dashed lines. [Symmetry code: (iv) 1 − x, 1 − y, 1 − z.]

The inversion-related dimers are connected by C8—H8⋯N2ii hydrogen bonds, forming chains extending parallel to [010]. Together, the C—H⋯N hydrogen bonds and π–π inter­actions generate layers parallel to (100), as shown in Fig. 3[link]. The terminal fluorine atoms are directed towards the inter­layer region. Weak C5—H5⋯F2i contacts are observed between adjacent layers along the a-axis direction (Table 1[link]) and may contribute to the consolidation of the crystal packing (Thalladi et al., 1998View full citation). A further weak C23—H23⋯F1iii contact occurs within the layers (Table 1[link]).

[Figure 3]
Figure 3
Crystal packing of 1 showing the C—H⋯N hydrogen-bonded layers parallel to (100).

4. Powder X-ray diffraction

The powder diffraction pattern of 1 was recorded using a Rigaku SmartLab powder diffractometer at room temperature (Cu Kα radiation, Bragg–Brentano geometry, θ–θ scanning, Ni filter, 3° < 2θ < 60°, Δ2θ = 0.01°). The Rietveld refinement of the obtained pattern (Fig. 4[link]) was carried out using the FullProf and WinPLOTR programs (Rodríguez-Carvajal & Roisnel, 1998View full citation), with data from the external NIST SRM 640 standard used for the calculation of the instrumental profile function and the single-crystal structure used as the structural model for refinement. A minor preferred orientation effect along the [110] direction was revealed during the refinement and taken into account. The crystallite size obtained from the refinement was approximately 99 nm, indicating relatively large crystallites and no pronounced nanocrystalline character of the sample. The main results of the Rietveld refinement are summarized in Table 2[link]. The experimental powder X-ray diffraction pattern is in good agreement with the theoretical pattern calculated from the single-crystal structure data.

Table 2
Experimental data of the X-ray powder diffraction study performed at 293 K

Crystal system, space group Monoclinic, P21/c
a (Å) 13.7470 (5)
b (Å) 16.9219 (4)
c (Å) 8.4473 (1)
β (°) 104.432 (2)
V (Å3) 1903.04 (8)
Dx, Mg m−3 1.397
Apparent crystallite size (nm) 99
   
Refinement  
Rp 0.0590
Rwp 0.0942
Rexp  0.0147
Rb 0.0592
Rf 0.0561
[Figure 4]
Figure 4
Final Rietveld plot of compound 1. Observed data points are indicated by red dots, the best-fit profile (upper trace) and the difference pattern (lower trace) are shown as solid lines. The vertical bars correspond to the positions of the Bragg peaks.

5. Hirshfeld surface analysis and fingerprint plots

A Hirshfeld surface analysis was performed using CrystalExplorer21 (Spackman et al., 2021View full citation) to examine the inter­molecular contacts in the crystal of 1. The Hirshfeld surface mapped over dnorm (Spackman & Jayatilaka, 2009View full citation) is shown in Fig. 5[link], while the corresponding two-dimensional fingerprint plots (McKinnon et al., 2007View full citation) are presented in Fig. 6[link]. The red spots on the dnorm surface correspond to the C—H⋯N contacts described above.

[Figure 5]
Figure 5
Three-dimensional Hirshfeld surface of compound 1 mapped over dnorm.
[Figure 6]
Figure 6
Two-dimensional fingerprint plots for compound 1 showing (a) all inter­molecular contacts and the plots delineated into contributions from (b) C⋯H/H⋯C, (c) H⋯H, (d) F⋯H/H⋯F, (e) N⋯H/H⋯N, (f) C⋯C contacts. The qu­anti­ties de and di represent the distances from a point on the Hirshfeld surface to the nearest atom outside and inside the surface, respectively.

The decomposed fingerprint plots show that C⋯H/H⋯C contacts make the largest contribution to the Hirshfeld surface, accounting for 30.2%, followed by H⋯H contacts (21.8%) and F⋯H/H⋯F contacts (18.0%). The relatively high contribution of F⋯H/H⋯F contacts reflects the frequent close approaches between the fluorine atoms and hydrogen atoms of neighbouring mol­ecules. These include the weak inter­layer C5—H5⋯F2i and intra­layer C23—H23⋯F1iii contacts described above. Thus, contacts involving fluorine atoms contribute to the mol­ecular association both within and between the layers.

The N⋯H/H⋯N contacts account for 8.1% of the Hirshfeld surface and are consistent with the C—H⋯N inter­actions described in the Supra­molecular features section. The C⋯C contacts contribute 5.4% to the Hirshfeld surface and support the presence of π–π stacking inter­actions between inversion-related oxazole rings.

Smaller contributions arise from O⋯H/H⋯O and O⋯N/N⋯O contacts, each accounting for 2.9%, as well as from N⋯C/C⋯N (1.5%), F⋯F (1.4%), O⋯C/C⋯O (1.0%) and F⋯C/C⋯F (0.8%) contacts. These minor contributions represent other weak contacts present in the crystal packing.

6. Database survey

An expanded substructure search of the Cambridge Structural Database (CSD, Version 6.01, updated February 2026; Groom et al., 2016View full citation), based on the ortho-disubstituted central benzene core and related five-membered O,N-heterocycles, gave ten entries. Three hits corresponding to bis­(imidazole) derivatives (GUVNET, GUVNET01 and SODQEJ) were excluded because they do not contain oxazole or oxa­diazole rings. The remaining seven entries correspond to six unique related crystal structures, since PODZEN and PODZEN10 describe the same crystallographic model.

The closest bis­(1,3-oxazole) analogues are the unsubstituted ortho-POPOP mol­ecule (PODZEN/PODZEN10; Doroshenko et al., 1994View full citation) and its mono­fluoro derivative (SUZVEP; Ilyashenko et al., 2010View full citation). Three unsymmetrical analogues containing one 1,3-oxazole and one 1,3,4-oxa­diazole ring were also found: NODYOU (Doroshenko et al., 1997View full citation), EDEFIC (Doroshenko et al., 2000aView full citation) and HUGJUO (Doroshenko et al., 2002bView full citation). The more distant bis­(1,3,4-oxa­diazole) analogue SEQREN was reported by Yang et al. (2010View full citation).

All these structures adopt non-planar mol­ecular geometries in which the two substituents have different orientations relative to the central benzene ring. In PODZEN/PODZEN10, the dihedral angles between the plane of the central benzene ring and the planes of the two oxazole rings are 10.3 and 66.9°, respectively. The corresponding published values for SUZVEP are 10.7 and 64.1° (Ilyashenko et al., 2010View full citation). In the title compound, these angles are 2.37 and 57.60°, indicating somewhat smaller twisting of both oxazole rings relative to the central benzene ring, although the difference between the orientations of the two oxazole moieties, characteristic of the ortho-POPOP framework, is retained.

7. Synthesis and crystallization

The title compound 1 was synthesized by the reported procedure (Doroshenko et al., 1994View full citation) using phthaloyl dichloride and 4-F-substituted ω-amino-aceto­phenone hydro­chloride (Ilyashenko et al., 2010View full citation). A solution of phthaloyl dichloride (0.025 mol, ∼3.6 mL) in 20 mL of benzene was mixed with 9.5 g (0.05 mol) 4-F-ω-amino­aceto­phenone hydro­chloride in 30 mL of water. The reaction mixture was basified dropwise with concentrated aqueous sodium carbonate with continuous stirring to keep it weakly alkaline and the mixture was stirred for 1 h. Then the resulting precipitate was filtered off, washed with water and air-dried at room temperature. The obtained inter­mediate was dissolved in 80 ml of concentrated sulfuric acid, stirred 30 min at room temperature, and then for an additional 30 min at 328 K. The reaction mixture was cooled, poured onto ice, the product was filtered off, thoroughly washed with water until the washings were neutral, air-dried and finally recrystallized from ethanol. Yield: 5.9 g (58%); colorless crystals.

Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a concentrated solution of 1 in propan-2-ol.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The H atoms were placed in calculated positions (C—H = 0.93 Å) and refined using a riding model with Uiso(H) = 1.2Ueq of the carrier atom.

Table 3
Experimental details

Crystal data
Chemical formula C24H14F2N2O2
Mr 400.37
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 13.767 (8), 16.914 (11), 8.447 (5)
β (°) 104.423 (13)
V (Å3) 1904.9 (19)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.3 × 0.2 × 0.1
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015View full citation)
Tmin, Tmax 0.617, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 10872, 3740, 1446
Rint 0.110
(sin θ/λ)max (Å−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.151, 0.91
No. of reflections 3740
No. of parameters 272
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.20, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2008View full citation), SHELXT2018/2 (Sheldrick, 2015aView full citation), SHELXL2019/3 (Sheldrick, 2015bView full citation) and OLEX2 (Dolomanov et al., 2009View full citation).

Supporting information

CCDC reference: 2586503

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009394/ex2105sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009394/ex2105Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026009394/ex2105Isup3.cml

checkCIF report


Computing details top

1,2-Bis[5-(4-fluorophenyl)-1,3-oxazol-2-yl]benzene top
Crystal data top
C24H14F2N2O2F(000) = 824
Mr = 400.37Dx = 1.396 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.767 (8) ÅCell parameters from 633 reflections
b = 16.914 (11) Åθ = 2.4–22.8°
c = 8.447 (5) ŵ = 0.10 mm−1
β = 104.423 (13)°T = 296 K
V = 1904.9 (19) Å3Block, colourless
Z = 40.3 × 0.2 × 0.1 mm
Data collection top
Bruker APEXII CCD
diffractometer		1446 reflections with I > 2σ(I)
φ and ω scansRint = 0.110
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		θmax = 26.0°, θmin = 1.5°
Tmin = 0.617, Tmax = 0.746h = −16→16
10872 measured reflectionsk = −20→20
3740 independent reflectionsl = −8→10
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.076 w = 1/[σ2(Fo2) + (0.045P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.151(Δ/σ)max < 0.001
S = 0.91Δρmax = 0.20 e Å−3
3740 reflectionsΔρmin = −0.19 e Å−3
272 parametersExtinction correction: SHELXL2019/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0043 (8)
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.

Refinement. Using Olex2 (Dolomanov et al., 2009), the structure was solved with the SHELXT (Sheldrick, 2015a) structure solution program using Intrinsic Phasing and refined with the SHELXL (Sheldrick, 2015b) refinement package. Full-matrix least squares refinement against F2 in anisotropic approximation was used for non-hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.0504 (2)0.4923 (2)−0.1473 (3)0.1238 (14)
F2−0.06623 (16)0.61801 (17)0.4548 (3)0.0916 (10)
O10.47053 (18)0.58652 (15)0.3229 (3)0.0414 (7)
O20.39878 (17)0.68355 (14)0.5272 (3)0.0409 (7)
N10.6035 (2)0.5080 (2)0.3606 (4)0.0538 (10)
N20.4544 (2)0.7954 (2)0.4465 (4)0.0585 (10)
C10.3414 (3)0.5178 (3)0.1210 (5)0.0474 (11)
C20.2666 (3)0.5654 (3)0.1507 (5)0.0583 (13)
H20.2826160.6039930.2313390.070*
C30.1670 (3)0.5564 (3)0.0611 (6)0.0762 (16)
H30.1158740.5875020.0820730.091*
C40.1481 (4)0.5002 (4)−0.0581 (6)0.0791 (17)
C50.2189 (4)0.4515 (3)−0.0906 (6)0.0819 (18)
H50.2021420.413168−0.1717790.098*
C60.3169 (3)0.4603 (3)0.0002 (5)0.0675 (14)
H60.3667230.427564−0.0199250.081*
C70.4445 (3)0.5227 (2)0.2193 (5)0.0399 (10)
C80.5244 (3)0.4759 (2)0.2423 (5)0.0551 (12)
H80.5269460.4285830.1874020.066*
C90.5673 (3)0.5719 (2)0.4056 (5)0.0386 (10)
C100.6219 (3)0.6282 (2)0.5302 (4)0.0360 (10)
C110.7223 (3)0.6099 (2)0.6003 (5)0.0517 (12)
H110.7495810.5640280.5684700.062*
C120.7819 (3)0.6586 (3)0.7162 (5)0.0623 (14)
H120.8483430.6452150.7632270.075*
C130.7421 (3)0.7271 (3)0.7613 (5)0.0643 (14)
H130.7821820.7606070.8377730.077*
C140.6433 (3)0.7465 (3)0.6938 (5)0.0555 (12)
H140.6172860.7926810.7266340.067*
C150.5814 (3)0.6980 (2)0.5770 (5)0.0392 (10)
C160.4786 (3)0.7270 (2)0.5112 (5)0.0400 (10)
C170.3507 (3)0.7967 (3)0.4137 (5)0.0591 (13)
H170.3106740.8385830.3643570.071*
C180.3158 (3)0.7298 (2)0.4625 (5)0.0438 (11)
C190.2165 (3)0.6990 (2)0.4603 (5)0.0447 (11)
C200.1319 (3)0.7432 (3)0.3893 (6)0.0688 (14)
H200.1391120.7920990.3430750.083*
C210.0372 (3)0.7154 (3)0.3868 (6)0.0789 (16)
H21−0.0194040.7449900.3390410.095*
C220.0282 (3)0.6444 (3)0.4549 (6)0.0614 (13)
C230.1077 (3)0.5980 (3)0.5230 (5)0.0606 (13)
H230.0989470.5490310.5674570.073*
C240.2030 (3)0.6262 (3)0.5245 (5)0.0501 (11)
H240.2587740.5951310.5698520.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0618 (19)0.213 (4)0.087 (2)−0.037 (2)0.0004 (17)−0.033 (2)
F20.0395 (15)0.121 (3)0.114 (2)−0.0090 (16)0.0200 (15)−0.004 (2)
O10.0399 (16)0.0409 (17)0.0429 (17)−0.0019 (14)0.0093 (13)−0.0034 (14)
O20.0350 (15)0.0380 (16)0.0513 (18)0.0020 (14)0.0137 (13)0.0023 (14)
N10.048 (2)0.048 (2)0.065 (3)0.0102 (19)0.014 (2)−0.004 (2)
N20.050 (2)0.047 (2)0.082 (3)−0.0011 (19)0.021 (2)0.007 (2)
C10.045 (3)0.055 (3)0.045 (3)−0.008 (2)0.016 (2)−0.006 (2)
C20.046 (3)0.080 (4)0.049 (3)−0.009 (3)0.013 (2)−0.012 (3)
C30.050 (3)0.106 (5)0.072 (4)−0.003 (3)0.013 (3)−0.006 (3)
C40.052 (4)0.128 (6)0.052 (3)−0.031 (3)0.005 (3)−0.012 (3)
C50.066 (4)0.121 (5)0.058 (4)−0.026 (4)0.016 (3)−0.032 (3)
C60.063 (3)0.080 (4)0.061 (3)−0.014 (3)0.017 (3)−0.016 (3)
C70.046 (3)0.038 (3)0.036 (3)−0.008 (2)0.011 (2)−0.005 (2)
C80.059 (3)0.042 (3)0.066 (3)0.001 (3)0.017 (3)−0.014 (2)
C90.037 (2)0.040 (3)0.039 (3)0.001 (2)0.012 (2)0.010 (2)
C100.033 (2)0.040 (2)0.036 (2)−0.002 (2)0.0108 (19)0.006 (2)
C110.037 (2)0.050 (3)0.069 (3)0.002 (2)0.015 (2)0.008 (3)
C120.034 (3)0.083 (4)0.064 (3)−0.012 (3)0.002 (2)0.008 (3)
C130.047 (3)0.076 (4)0.067 (3)−0.018 (3)0.009 (2)−0.020 (3)
C140.052 (3)0.058 (3)0.057 (3)−0.007 (2)0.014 (2)−0.011 (2)
C150.036 (2)0.047 (3)0.036 (2)−0.003 (2)0.012 (2)0.003 (2)
C160.043 (3)0.034 (3)0.046 (3)−0.008 (2)0.016 (2)−0.007 (2)
C170.053 (3)0.049 (3)0.076 (3)0.013 (2)0.018 (3)0.014 (3)
C180.043 (3)0.044 (3)0.044 (3)0.002 (2)0.010 (2)0.005 (2)
C190.043 (3)0.046 (3)0.045 (3)0.008 (2)0.012 (2)0.002 (2)
C200.048 (3)0.062 (3)0.096 (4)0.011 (3)0.017 (3)0.026 (3)
C210.037 (3)0.087 (4)0.110 (4)0.019 (3)0.014 (3)0.017 (4)
C220.036 (3)0.078 (4)0.071 (4)−0.002 (3)0.013 (2)−0.002 (3)
C230.054 (3)0.063 (3)0.066 (3)−0.007 (3)0.016 (3)0.004 (3)
C240.032 (2)0.058 (3)0.057 (3)0.008 (2)0.005 (2)−0.001 (2)
Geometric parameters (Å, º) top
F1—C41.374 (5)C10—C111.396 (4)
F2—C221.375 (5)C10—C151.404 (5)
O1—C71.379 (4)C11—H110.9300
O1—C91.365 (4)C11—C121.382 (5)
O2—C161.356 (4)C12—H120.9300
O2—C181.380 (4)C12—C131.376 (6)
N1—C81.392 (5)C13—H130.9300
N1—C91.286 (4)C13—C141.377 (5)
N2—C161.288 (5)C14—H140.9300
N2—C171.386 (5)C14—C151.397 (5)
C1—C21.378 (5)C15—C161.470 (5)
C1—C61.388 (5)C17—H170.9300
C1—C71.458 (5)C17—C181.334 (5)
C2—H20.9300C18—C191.459 (5)
C2—C31.401 (5)C19—C201.388 (5)
C3—H30.9300C19—C241.376 (5)
C3—C41.362 (6)C20—H200.9300
C4—C51.356 (6)C20—C211.382 (6)
C5—H50.9300C21—H210.9300
C5—C61.383 (5)C21—C221.349 (6)
C6—H60.9300C22—C231.352 (5)
C7—C81.329 (5)C23—H230.9300
C8—H80.9300C23—C241.394 (5)
C9—C101.479 (5)C24—H240.9300
C9—O1—C7104.4 (3)C13—C12—C11119.4 (4)
C16—O2—C18105.4 (3)C13—C12—H12120.3
C9—N1—C8104.4 (3)C12—C13—H13119.8
C16—N2—C17104.0 (3)C12—C13—C14120.4 (4)
C2—C1—C6119.2 (4)C14—C13—H13119.8
C2—C1—C7121.9 (4)C13—C14—H14119.4
C6—C1—C7118.9 (4)C13—C14—C15121.2 (4)
C1—C2—H2119.5C15—C14—H14119.4
C1—C2—C3120.9 (4)C10—C15—C16125.9 (3)
C3—C2—H2119.5C14—C15—C10118.5 (4)
C2—C3—H3121.4C14—C15—C16115.6 (4)
C4—C3—C2117.1 (5)O2—C16—C15120.6 (3)
C4—C3—H3121.4N2—C16—O2113.6 (3)
C3—C4—F1117.0 (5)N2—C16—C15125.6 (4)
C5—C4—F1119.0 (5)N2—C17—H17124.5
C5—C4—C3124.0 (5)C18—C17—N2111.0 (4)
C4—C5—H5120.9C18—C17—H17124.5
C4—C5—C6118.2 (5)O2—C18—C19118.9 (4)
C6—C5—H5120.9C17—C18—O2106.1 (4)
C1—C6—H6119.7C17—C18—C19135.0 (4)
C5—C6—C1120.5 (5)C20—C19—C18119.7 (4)
C5—C6—H6119.7C24—C19—C18122.1 (4)
O1—C7—C1117.9 (4)C24—C19—C20118.2 (4)
C8—C7—O1107.4 (3)C19—C20—H20119.7
C8—C7—C1134.5 (4)C21—C20—C19120.6 (4)
N1—C8—H8125.0C21—C20—H20119.7
C7—C8—N1110.1 (4)C20—C21—H21120.6
C7—C8—H8125.0C22—C21—C20118.9 (4)
O1—C9—C10120.4 (3)C22—C21—H21120.6
N1—C9—O1113.7 (3)C21—C22—F2118.4 (4)
N1—C9—C10125.9 (4)C21—C22—C23123.2 (4)
C11—C10—C9115.6 (4)C23—C22—F2118.4 (5)
C11—C10—C15119.2 (4)C22—C23—H23121.1
C15—C10—C9125.1 (3)C22—C23—C24117.8 (4)
C10—C11—H11119.4C24—C23—H23121.1
C12—C11—C10121.2 (4)C19—C24—C23121.4 (4)
C12—C11—H11119.4C19—C24—H24119.3
C11—C12—H12120.3C23—C24—H24119.3
F1—C4—C5—C6179.9 (4)C9—C10—C15—C14−178.3 (4)
F2—C22—C23—C24−179.0 (4)C9—C10—C15—C160.1 (6)
O1—C7—C8—N10.0 (5)C10—C11—C12—C13−1.1 (6)
O1—C9—C10—C11−176.3 (3)C10—C15—C16—O261.0 (5)
O1—C9—C10—C151.6 (6)C10—C15—C16—N2−124.5 (5)
O2—C18—C19—C20−177.2 (4)C11—C10—C15—C14−0.5 (6)
O2—C18—C19—C241.8 (6)C11—C10—C15—C16177.9 (4)
N1—C9—C10—C111.7 (6)C11—C12—C13—C141.1 (7)
N1—C9—C10—C15179.6 (4)C12—C13—C14—C15−0.8 (7)
N2—C17—C18—O2−0.5 (5)C13—C14—C15—C100.5 (6)
N2—C17—C18—C19179.7 (4)C13—C14—C15—C16−178.1 (4)
C1—C2—C3—C4−1.5 (7)C14—C15—C16—O2−120.5 (4)
C1—C7—C8—N1−175.8 (4)C14—C15—C16—N254.0 (6)
C2—C1—C6—C50.7 (7)C15—C10—C11—C120.8 (6)
C2—C1—C7—O1−12.4 (6)C16—O2—C18—C17−0.3 (4)
C2—C1—C7—C8163.0 (5)C16—O2—C18—C19179.5 (3)
C2—C3—C4—F1−179.1 (4)C16—N2—C17—C181.2 (5)
C2—C3—C4—C52.2 (8)C17—N2—C16—O2−1.4 (5)
C3—C4—C5—C6−1.4 (9)C17—N2—C16—C15−176.2 (4)
C4—C5—C6—C1−0.1 (7)C17—C18—C19—C202.4 (8)
C6—C1—C2—C30.1 (7)C17—C18—C19—C24−178.5 (5)
C6—C1—C7—O1171.3 (4)C18—O2—C16—N21.1 (4)
C6—C1—C7—C8−13.3 (7)C18—O2—C16—C15176.2 (3)
C7—O1—C9—N11.9 (4)C18—C19—C20—C21−179.6 (4)
C7—O1—C9—C10−179.9 (3)C18—C19—C24—C23179.2 (4)
C7—C1—C2—C3−176.2 (4)C19—C20—C21—C220.2 (8)
C7—C1—C6—C5177.1 (4)C20—C19—C24—C23−1.7 (6)
C8—N1—C9—O1−1.9 (5)C20—C21—C22—F2178.6 (4)
C8—N1—C9—C10−179.9 (4)C20—C21—C22—C23−1.4 (8)
C9—O1—C7—C1175.5 (3)C21—C22—C23—C241.0 (7)
C9—O1—C7—C8−1.0 (4)C22—C23—C24—C190.6 (6)
C9—N1—C8—C71.1 (5)C24—C19—C20—C211.3 (7)
C9—C10—C11—C12178.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F2i0.932.703.470 (5)141
C8—H8···N2ii0.932.563.489 (6)176
C23—H23···F1iii0.932.823.559 (5)137
C24—H24···N1iv0.932.543.449 (5)168
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1.
Experimental data of the X-ray powder diffraction study performed at 293 K top
Crystal system, space groupMonoclinic, P21/c
a (Å)13.7470 (5)
b (Å)16.9219 (4)
c (Å)8.4473 (1)
β (°)104.432 (2)
V (Å3)1903.04 (8)
Dx, Mg m-31.397
Apparent crystallite size (nm)99
Refinement
Rp0.0590
Rwp0.0942
Rexp0.0147
Rb0.0592
Rf0.0561
 

Funding information

Funding for this research was provided by: National Academy of Science of Ukraine (grant No. 0125U000623 to V. V. Dyakonenko, A. M. Shaposhnyk, A. V. Kyrychenko).

References

Return to citationAmbats, I. & Marsh, R. E. (1965). Acta Cryst. 19, 942–948.  CrossRef CAS IUCr Journals Web of Science Google Scholar
 Return to citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 Return to citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 Return to citationDoroshenko, A. (1999). Chem. Phys. Rep. 18, 873-879.  Google Scholar
 Return to citationDoroshenko, A. O. (2002a). Theor. Exp. Chem. 38, 135–155.  CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Baumer, V. N., Kirichenko, A. V., Shershukov, V. M. & Tolmachev, A. V. (1997). Chem. Heterocycl. Compd. 33, 1341–1349.  CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Baumer, V. N., Verezubova, A. A. & Ptyagina, L. M. (2002b). J. Mol. Struct. 609, 29–37.  Web of Science CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Kirichenko, A. V., Mitina, V. G. & Ponomaryov, O. A. (1996). J. Photochem. Photobiol. Chem. 94, 15–26.  CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Kyrychenko, A. V., Baumer, V. N., Verezubova, A. A. & Ptyagina, L. M. (2000a). J. Mol. Struct. 524, 289–296.  CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Kyrychenko, A. V. & Waluk, J. (2000b). J. Fluoresc. 10, 41–48.  CrossRef CAS Google Scholar
 Return to citationDoroshenko, A. O., Patsenker, L. D., Baumer, V. N., Chepeleva, L. V., Van'Kevich, A. V., Kirichenko, A. V., Yarmolenko, S. N., Scherschukov, V. M., Mitina, V. G. & Ponomaryov, O. A. (1994). Mol. Eng. 3, 353–363.  CrossRef CAS Google Scholar
 Return to citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CrossRef IUCr Journals Google Scholar
 Return to citationIliashenko, R., Zozulia, O. & Doroshenko, A. (2011). Centr. Eur. J. Chem. 9, 962-971.  CAS Google Scholar
 Return to citationIlyashenko, R., Wera, M., Błażejowski, J. & Doroshenko, A. (2010). Acta Cryst. E66, o2379–o2380.  CrossRef IUCr Journals Google Scholar
 Return to citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
 Return to citationMcKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816.  Web of Science CrossRef Google Scholar
 Return to citationOtt, D. G., Hayes, F. N., Hansbury, E. & Kerr, V. N. (1957). J. Am. Chem. Soc. 79, 5448–5454.  CrossRef CAS Google Scholar
 Return to citationRodríguez-Carvajal, J. & Roisnel, T. (1998). IUCr Newsletter 20, 35–36.  Google Scholar
 Return to citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 Return to citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 Return to citationSpackman, M. A. & Jayatilaka, D. (2009). CrystEngComm 11, 19–32.  Web of Science CrossRef CAS Google Scholar
 Return to citationSpackman, 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
 Return to citationThalladi, V. R., Weiss, H.-C., Bläser, D., Boese, R., Nangia, A. & Desiraju, G. R. (1998). J. Am. Chem. Soc. 120, 8702–8710.  Web of Science CSD CrossRef CAS Google Scholar
 Return to citationYang, C.-C., Hsu, C.-J., Chou, P.-T., Cheng, H.-C., Su, Y. O. & Leung, M.-K. (2010). J. Phys. Chem. B 114, 756–768.  CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009394