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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 9| September 2026| Pages 1077-1081
https://doi.org/10.1107/S2056989026008492

Synthesis, crystal structure and Hirshfeld surface analysis of 1-[(1-benzyl-1H-1,2,3-triazol-4-yl)meth­yl]-3-(2-oxo-2-phenyl­eth­yl)-1,3-di­hydro-2H-benzimidazol-2-one

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Asmaa Saber,a,b Mohamed Srhir,b Daouda Ballo,c Tuncer Hökelek,d Joel T. Mague,e El Mokhtar Essassib and Nada Kheira Sebbarb*

aHigher Institute of Nursing Professions and Health Techniques Rabat, Morocco, bLaboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center, Pharmacochemistry, Competence Center, Mohammed V University in Rabat, Faculty of Sciences, Av. Ibn Battouta, BP 1014, Rabat, Morocco, cLaboratory of Constitution and Reaction of Matter (LCRM), UFR SSMT, Félix Houphouët Boigny University, 22 BP 582 Abidjan 22, Republic of Côte d'Ivoire, dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye, and eDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 July 2026; accepted 17 August 2026; online 20 August 2026)

In the title mol­ecule, C25H21N5O2, the benzyl­triazole moiety and the phenyl portion of the 3-(2-oxo-2-phenyl­eth­yl) group are disordered over two sets of sites. In the crystal, layers of mol­ecules parallel to the ab plane are generated by C—H⋯O and C—H⋯N hydrogen bonds, enclosing R22(10) and R22(16) ring motifs, and C—H⋯π(ring) inter­actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (41.3%), H⋯C/C⋯H (31.1%), H⋯O/O⋯H (13.2%) and H⋯N/N⋯H (10.7%) inter­actions.

CCDC reference: 2581766

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1. Chemical context

Benzimidazole is an important nitro­gen-containing heterocyclic compound. Owing to its unique structural and electronic properties, this bicyclic system is relevant in medicinal chemistry for the development of biologically active compounds. Numerous benzimidazole derivatives have demonstrated a broad spectrum of pharmacological activities, including anti­microbial, anti­viral, anti­parasitic, anti­cancer, anti-inflammatory, anti­oxidant, anti­histaminic, anti­ulcer and anti­diabetic effects, making this heterocycle an important structural motif in many therapeutic agents (Ansari & Lal, 2009View full citation; Navarrete-Vazquez et al., 2001View full citation; Luo et al., 2011View full citation; Hranjec et al., 2006View full citation, 2011View full citation; Ramla et al., 2007View full citation; Saber et al., 2018View full citation; Solominova et al., 2004View full citation). Among these derivatives, benzimidazol-2-ones have received particular attention because of their diverse biological properties, notably their activity as progesterone receptor antagonists and their promising therapeutic potential (Wang et al., 2011View full citation).

In a continuation of our studies on benzimidazole-based heterocycles incorporating a 1,2,3-triazole ring (Saber et al., 2021View full citation; El Atrassi et al., 2024View full citation), we synthesized a new triazole-functionalized benzimidazol-2-one derivative through the copper-catalyzed azide–alkyne cyclo­addition (CuAAC), a widely used click chemistry strategy. The reaction between 1-(prop-2-yn-1-yl)-3-(2-oxo-2-phenyl­eth­yl)-1,3-di­hydro-2H-benzimidazol-2-one and benzyl azide was carried out in a water/ethanol (1:1, v/v) mixture using copper(II) sulfate and sodium ascorbate as the catalytic system. Under these conditions, the title compound, C25H21N5O2, was obtained regioselectively in excellent yield (87%; Fig. 1[link]). To gain further insight into its solid-state organization, the mol­ecular and crystal structures were determined by single-crystal X-ray diffraction, and the crystal packing was subsequently investigated by Hirshfeld surface analysis to identify the inter­molecular inter­actions governing the crystal stability.

[Scheme 1]
[Figure 1]
Figure 1
Synthesis scheme to obtain the title compound.

2. Structural commentary

The mol­ecular structure is shown in Fig. 2[link]. The benzimidazole unit is essentially planar with N1 and C7 being furthest from the least-squares plane at 0.0213 (14) and −0.0174 (15) Å, respectively (root-mean-square deviation = 0.0100 Å). The carbonyl group is slightly bent out of this plane as O1 is positioned −0.043 (2) Å from it. The benzyl­triazole substituent is disordered over two sets of nearly equally occupied sites, with the dihedral angle between the two orientations of the triazole ring being 64.7 (2)°. The dihedral angle between the mean planes of the benzimidazole unit and the C17/N3/N4/N5/C18 triazole ring is 68.69 (15)° while that between the latter ring plane and the mean plane of the C21–C25 ring is 75.05 (19)°. The corresponding angles for the minor component of this disorder are 77.36 (15) and 88.4 (2)°. The C10–C15 phenyl ring is also disordered over two sets of sites, with the dihedral angle between the mean planes of the benzimidazole unit and the major component of this disorder group being 83.07 (19)°. The dihedral angle between the two orientations of the C10–C15 phenyl ring is 18.4 (6)°.

[Figure 2]
Figure 2
The title mol­ecule with displacement ellipsoids drawn at the 50% probability level. Only the major components of disorder are shown.

3. Supra­molecular features

In the crystal, C8—H8A⋯O1 and C22—H22⋯N3 hydrogen bonds (Table 1[link]) form inversion dimers (Fig. 3[link]), enclosing R22(10) and R22(16) ring motifs (Etter et al., 1990View full citation), which are connected into chains extending parallel to the a-axis direction by inversion-related C18—H18⋯Cg5 inter­actions (Table 1[link], Fig. 4[link]). The chains are linked along the b-axis direction by C16—H16B⋯Cg4 and C19—H19A⋯Cg6 inter­actions (Table 1[link]), forming layers parallel to the ab plane (Figs. 4[link] and 5[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg4, Cg5 and Cg6 are the centroids of the C1–C6, C10–C15 and C20–C25 benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8A⋯O1i 0.99 2.37 3.190 (3) 140
C16—H16B⋯Cg4ii 0.99 2.69 3.384 (14) 128
C18—H18⋯Cg5i 0.95 2.88 3.700 (5) 146
C19—H19A⋯Cg6iii 0.99 2.71 3.678 (5) 166
C22—H22⋯N3iv 0.95 2.53 3.224 (5) 130
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation.
[Figure 3]
Figure 3
A portion of one hydrogen-bonded chain viewed along the b-axis direction with C—H⋯O and C—H⋯N hydrogen bonds depicted, respectively, by black and light-blue dashed lines. Only the major components of disorder are shown, and hydrogen atoms not involved in these inter­actions are omitted for clarity.
[Figure 4]
Figure 4
C—H⋯π(ring) inter­actions (green dashed lines) together with C—H⋯O and C—H⋯N hydrogen-bonding inter­actions form layers parallel to the ab plane.
[Figure 5]
Figure 5
Packing plot in a view along the a axis showing the supra­molecular layers packed in an alternating mode along the c axis.

The inter­molecular inter­actions in the crystal were visualized by carrying out a Hirshfeld surface (HS) analysis using CrystalExplorer (Spackman et al., 2021View full citation). It is noted that only the major components of the positionally disordered atoms were taken into account for the analysis. Fig. 6[link] shows the Hirshfeld surface with several neighboring mol­ecules in the crystal. The white surface indicates contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter (in close contact) or longer (distinct contacts) than the van der Waals radii, respectively. The red spots indicate their roles as the respective donors and/or acceptors atoms in hydrogen-bonding, as discussed above. The C—H⋯π(ring) inter­actions are shown in Fig. 7[link]a and 7b by the presence of red π-holes.

[Figure 6]
Figure 6
View of the three-dimensional Hirshfeld surface for mol­ecule plotted over dnorm.
[Figure 7]
Figure 7
The shape-index surface showing two orientations for C—H⋯π(ring) inter­actions.

The overall two-dimensional fingerprint plot is shown in Fig. 8[link]a, and those delineated into various contact types are illustrated in Fig. 8[link]b–h. H⋯H, H⋯C/C⋯H, H⋯O/O⋯H and H⋯N/N⋯H contacts make the most significant contributions to the HS, at 41.3%, 31.1%, 13.2% and 10.7%, respectively.

[Figure 8]
Figure 8
The two-dimensional fingerprint plots of the title compound (I)[link], showing (a) all inter­actions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) H⋯N/N⋯H, (f) C⋯N/N⋯C, (g) C⋯O/O⋯C and (h) C⋯C inter­actions. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

A search of the Cambridge Structural Database (CSD, update July 2026; Groom et al., 2016View full citation) revealed the presence of several structures closely related with the title compound, which are shown schematically in Fig. 9[link]. These include I with R1 = R2 = –C6H5 (refcode PAZFOO; Adardour et al., 2017View full citation), II with R1 = –C(CH2)=CH2, R2 = –(CH2)9CH3 (ETAJOB; Saber et al., 2021View full citation), and III with R1 = –CH2—(C2HN3)—(CH2)7CH3, R2 = –(CH2)7CH3 (YIVWUZ; Zouhair et al., 2023View full citation). A comparison of these structures highlights the versatility of the benzimidazol-2-one-1,2,3-triazole moiety, which tolerates a wide range of substituents at the N1 and N2 positions. In particular, variations in the alkyl or aryl substituents (R1, R2) significantly influence the crystal packing, inter­molecular inter­actions, and hydrogen-bonding motifs, without altering the general conformation of the heterocyclic core. Such structural adaptability makes this scaffold a valuable platform for further mol­ecular modification and pharmacological optimization.

[Figure 9]
Figure 9
Schematic representation of closely related structures obtained from a database search.

5. Synthesis and crystallization

A 1 mmol solution of 1-(prop-2-yn-1-yl)-3-(2-oxo-2-phenyl­eth­yl)-1,3-di­hydro-2H-benzimidazol-2-one and 1.5 mmol of 1-(azido­meth­yl)benzene were dissolved in 15 ml of ethanol. This solution was added to 0.5 mmol of CuSO4 and 1 mmol of sodium ascorbate, dissolved in 15 ml of distilled water. The reaction mixture was stirred for 24 h at room temperature and then monitored by TLC until completion of the reaction. After filtration and concentration of the solution under reduced pressure, the residue was chromatographed on a silica gel column using an ethyl acetate/hexane (2:8 v/v) mixture as the eluent. The solid obtained on concentration of the eluate was filtered off, washed with water, dried, and then recrystallized from ethanol (87% yield).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. C-bound H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and included as riding with isotropic displacement parameters 1.2–1.5 times those of the parent atoms. The benzyl triazole substituent is disordered over two resolved sets of sites in a 0.5049 (14)/0.4951 (14) ratio, and the C10–C15 phenyl ring in a 0.568 (7)/0.432 (7) ratio.

Table 2
Experimental details

Crystal data
Chemical formula C25H21N5O2
Mr 423.47
Crystal system, space group Monoclinic, P21/n
Temperature (K) 125
a, b, c (Å) 18.6129 (17), 4.9782 (5), 22.691 (2)
β (°) 99.479 (3)
V (Å3) 2073.8 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.36 × 0.21 × 0.10
 
Data collection
Diffractometer Bruker D8 QUEST PHOTON 3 diffractometer
Absorption correction Multi-scan (TWINABS; Sheldrick, 2009View full citation)
Tmin, Tmax 0.97, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections 63938, 8059, 6008
Rint 0.045
(sin θ/λ)max (Å−1) 0.667
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.134, 1.03
No. of reflections 8059
No. of parameters 301
No. of restraints 24
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.29
Computer programs: APEX4 and SAINT (Bruker, 2021View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation), DIAMOND (Brandenburg & Putz, 2012View full citation) and publCIF (Westrip, 2010View full citation).

Supporting information

CCDC reference: 2581766

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989026008492/wm5807sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008492/wm5807Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026008492/wm5807Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989026008492/wm5807Isup4.cml

checkCIF report


Computing details top

1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-3-(2-oxo-2-phenylethyl)-1,3-dihydro-2H-benzimidazol-2-one top
Crystal data top
C25H21N5O2F(000) = 888
Mr = 423.47Dx = 1.356 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 18.6129 (17) ÅCell parameters from 9948 reflections
b = 4.9782 (5) Åθ = 2.5–28.2°
c = 22.691 (2) ŵ = 0.09 mm−1
β = 99.479 (3)°T = 125 K
V = 2073.8 (3) Å3Column, colourless
Z = 40.36 × 0.21 × 0.10 mm
Data collection top
Bruker D8 QUEST PHOTON 3
diffractometer		8059 independent reflections
Radiation source: fine-focus sealed tube6008 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 7.3910 pixels mm-1θmax = 28.3°, θmin = 2.2°
φ and ω scansh = −24→24
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2009)		k = 0→6
Tmin = 0.97, Tmax = 0.99l = 0→30
63938 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0462P)2 + 1.2404P]
where P = (Fo2 + 2Fc2)/3
8059 reflections(Δ/σ)max < 0.001
301 parametersΔρmax = 0.27 e Å−3
24 restraintsΔρmin = −0.29 e Å−3
Special details top

Experimental. The diffraction data were obtained from 8 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was 25 sec/frame. Analysis of 1004 reflections having I/σ(I) > 20 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about a. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The substituent attached to N2 is disordered over two resolved sites in a 0.5049 (14)/0.4951 (14) ratio while the C10···C15 phenyl group is disordered over two closely spaced sites in a 0.568 (7)/0.432 (7) ratio. The disordered phenyl rings were refined as rigid hexagons while the remaider of the disordered atoms were refined with restraints making their geometries comparable. The model was refined as a 2-component twin. One reflection affected by the beamstop was omitted from the final refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.59464 (8)0.5795 (3)0.49188 (7)0.0374 (4)
O20.46510 (9)0.4659 (4)0.34829 (9)0.0562 (5)
N10.57999 (8)0.2455 (4)0.41899 (7)0.0263 (4)
N20.67885 (9)0.4979 (3)0.42825 (7)0.0266 (4)
C10.68187 (10)0.3221 (4)0.38105 (8)0.0237 (4)
C20.73333 (11)0.2867 (4)0.34421 (9)0.0274 (4)
H20.7762550.3930230.3484200.033*
C30.71942 (11)0.0889 (5)0.30084 (9)0.0308 (5)
H30.7537570.0589810.2748550.037*
C40.65664 (11)−0.0668 (5)0.29429 (9)0.0294 (5)
H40.648729−0.1987640.2636690.035*
C50.60504 (10)−0.0331 (4)0.33180 (9)0.0258 (4)
H50.562432−0.1410340.3279370.031*
C60.61884 (10)0.1642 (4)0.37471 (8)0.0233 (4)
C70.61522 (11)0.4566 (5)0.45099 (9)0.0274 (4)
C80.50801 (10)0.1541 (5)0.42476 (9)0.0281 (5)
H8A0.4974400.2048700.4646390.034*
H8B0.506213−0.0442530.4217560.034*
C90.45034 (11)0.2735 (5)0.37696 (10)0.0317 (5)
C100.37482 (13)0.1625 (9)0.3687 (5)0.0282 (6)0.568 (7)
C110.3235 (3)0.2743 (11)0.3240 (4)0.0384 (10)0.568 (7)
H110.3350880.4307380.3035640.046*0.568 (7)
C120.2551 (2)0.1571 (14)0.3093 (3)0.0496 (8)0.568 (7)
H120.2199550.2335200.2787760.060*0.568 (7)
C130.23804 (17)−0.0718 (12)0.3393 (3)0.0496 (16)0.568 (7)
H130.191294−0.1518960.3291900.059*0.568 (7)
C140.2894 (3)−0.1836 (10)0.3839 (3)0.0445 (12)0.568 (7)
H140.277765−0.3400960.4043920.053*0.568 (7)
C150.3578 (2)−0.0665 (10)0.3986 (3)0.0373 (10)0.568 (7)
H150.392899−0.1428810.4291810.045*0.568 (7)
C10A0.37745 (16)0.1405 (13)0.3662 (6)0.0282 (6)0.432 (7)
C11A0.3257 (4)0.2316 (17)0.3192 (6)0.0384 (10)0.432 (7)
H11A0.3396780.3476190.2898960.046*0.432 (7)
C12A0.2534 (3)0.153 (2)0.3152 (4)0.0496 (8)0.432 (7)
H12A0.2179740.2150970.2831180.060*0.432 (7)
C13A0.23286 (17)−0.0170 (18)0.3582 (4)0.0496 (16)0.432 (7)
H13A0.183453−0.0707910.3553980.059*0.432 (7)
C14A0.2847 (4)−0.1081 (15)0.4051 (3)0.0445 (12)0.432 (7)
H14A0.270635−0.2241580.4344570.053*0.432 (7)
C15A0.3569 (3)−0.0294 (14)0.4091 (5)0.0373 (10)0.432 (7)
H15A0.392339−0.0916380.4412360.045*0.432 (7)
C160.7310 (6)0.7033 (9)0.4515 (8)0.0310 (7)0.5049 (14)
H16A0.7060180.8375590.4731580.037*0.5049 (14)
H16B0.7471080.7961820.4173520.037*0.5049 (14)
C170.7965 (2)0.6045 (8)0.4922 (2)0.0282 (5)0.5049 (14)
N30.83961 (19)0.3988 (8)0.48012 (15)0.0435 (8)0.5049 (14)
N40.8876 (2)0.3476 (8)0.5290 (2)0.0527 (13)0.5049 (14)
N50.87433 (17)0.5196 (7)0.57097 (14)0.0355 (6)0.5049 (14)
C180.8187 (2)0.6813 (8)0.55005 (17)0.0349 (7)0.5049 (14)
H180.7987660.8205320.5710270.042*0.5049 (14)
C190.9184 (2)0.5069 (10)0.63041 (18)0.0472 (9)0.5049 (14)
H19A0.9412530.3272020.6358610.057*0.5049 (14)
H19B0.8858080.5264090.6605270.057*0.5049 (14)
C200.97723 (16)0.7168 (7)0.64224 (15)0.0338 (11)0.5049 (14)
C211.02722 (18)0.7422 (7)0.60332 (13)0.0410 (10)0.5049 (14)
H211.0229820.6323580.5686910.049*0.5049 (14)
C221.08340 (17)0.9284 (8)0.61508 (15)0.0463 (10)0.5049 (14)
H221.1175620.9458340.5884790.056*0.5049 (14)
C231.0896 (2)1.0892 (9)0.66575 (18)0.0479 (15)0.5049 (14)
H231.1279941.2164560.6737820.057*0.5049 (14)
C241.0396 (2)1.0637 (9)0.70467 (16)0.0442 (14)0.5049 (14)
H241.0438481.1736020.7392980.053*0.5049 (14)
C250.98343 (17)0.8775 (8)0.69291 (14)0.0420 (10)0.5049 (14)
H250.9492670.8601270.7195110.050*0.5049 (14)
C16A0.7324 (6)0.7019 (9)0.4493 (8)0.0310 (7)0.4951 (14)
H16C0.7107600.8360500.4733640.037*0.4951 (14)
H16D0.7470890.7956380.4146500.037*0.4951 (14)
C17A0.7975 (2)0.5787 (9)0.48617 (19)0.0282 (5)0.4951 (14)
N3A0.80361 (19)0.3171 (8)0.50294 (16)0.0435 (8)0.4951 (14)
N4A0.8704 (2)0.2774 (9)0.53272 (19)0.0527 (13)0.4951 (14)
N5A0.90525 (17)0.5125 (8)0.53429 (15)0.0355 (6)0.4951 (14)
C18A0.8623 (2)0.7036 (8)0.50613 (18)0.0349 (7)0.4951 (14)
H18A0.8742690.8867630.5010800.042*0.4951 (14)
C19A0.9810 (2)0.5279 (11)0.5637 (2)0.0472 (9)0.4951 (14)
H19C1.0110230.5943460.5346030.057*0.4951 (14)
H19D0.9980820.3447380.5759010.057*0.4951 (14)
C20A0.99296 (19)0.7077 (7)0.61788 (13)0.0338 (11)0.4951 (14)
C21A0.94870 (16)0.6821 (7)0.66129 (15)0.0410 (10)0.4951 (14)
H21A0.9091140.5592700.6556190.049*0.4951 (14)
C22A0.96238 (19)0.8363 (9)0.71299 (14)0.0463 (10)0.4951 (14)
H22A0.9321320.8188550.7426580.056*0.4951 (14)
C23A1.0203 (2)1.0161 (9)0.72129 (16)0.0479 (15)0.4951 (14)
H23A1.0296491.1215150.7566220.057*0.4951 (14)
C24A1.0646 (2)1.0417 (9)0.67788 (18)0.0442 (14)0.4951 (14)
H24A1.1041471.1645920.6835470.053*0.4951 (14)
C25A1.05088 (17)0.8875 (8)0.62617 (14)0.0420 (10)0.4951 (14)
H25A1.0811290.9050100.5965080.050*0.4951 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0361 (8)0.0431 (10)0.0337 (8)0.0072 (8)0.0074 (7)−0.0104 (8)
O20.0307 (9)0.0607 (13)0.0737 (13)−0.0057 (9)−0.0014 (8)0.0361 (11)
N10.0212 (8)0.0335 (10)0.0245 (8)0.0018 (8)0.0044 (6)−0.0023 (8)
N20.0260 (8)0.0261 (9)0.0273 (8)0.0014 (8)0.0036 (7)−0.0015 (7)
C10.0264 (10)0.0226 (10)0.0212 (9)0.0018 (8)0.0014 (7)0.0028 (8)
C20.0284 (10)0.0262 (11)0.0286 (10)−0.0029 (9)0.0072 (8)0.0027 (9)
C30.0334 (11)0.0339 (12)0.0270 (10)0.0016 (10)0.0107 (8)0.0010 (10)
C40.0325 (11)0.0301 (11)0.0259 (10)0.0023 (10)0.0051 (8)−0.0029 (9)
C50.0235 (9)0.0266 (11)0.0268 (10)0.0000 (9)0.0026 (8)0.0000 (9)
C60.0211 (9)0.0258 (10)0.0229 (9)0.0049 (8)0.0031 (7)0.0051 (8)
C70.0255 (10)0.0305 (11)0.0251 (10)0.0054 (9)0.0010 (8)0.0008 (9)
C80.0227 (9)0.0323 (12)0.0301 (10)0.0022 (9)0.0064 (8)0.0030 (10)
C90.0267 (10)0.0333 (12)0.0351 (11)0.0017 (9)0.0049 (9)0.0049 (10)
C100.0256 (10)0.0294 (13)0.0302 (12)0.0021 (10)0.0062 (9)−0.0050 (12)
C110.0337 (12)0.042 (2)0.0383 (18)−0.0026 (14)0.0013 (11)0.000 (2)
C120.0315 (12)0.0591 (18)0.0536 (19)−0.0047 (13)−0.0066 (12)−0.0023 (15)
C130.0318 (15)0.057 (3)0.059 (4)−0.0149 (18)0.0058 (18)−0.014 (3)
C140.0415 (17)0.038 (3)0.057 (4)−0.011 (2)0.017 (2)−0.009 (2)
C150.0321 (12)0.0388 (19)0.042 (3)−0.0047 (12)0.0075 (13)0.0009 (17)
C10A0.0256 (10)0.0294 (13)0.0302 (12)0.0021 (10)0.0062 (9)−0.0050 (12)
C11A0.0337 (12)0.042 (2)0.0383 (18)−0.0026 (14)0.0013 (11)0.000 (2)
C12A0.0315 (12)0.0591 (18)0.0536 (19)−0.0047 (13)−0.0066 (12)−0.0023 (15)
C13A0.0318 (15)0.057 (3)0.059 (4)−0.0149 (18)0.0058 (18)−0.014 (3)
C14A0.0415 (17)0.038 (3)0.057 (4)−0.011 (2)0.017 (2)−0.009 (2)
C15A0.0321 (12)0.0388 (19)0.042 (3)−0.0047 (12)0.0075 (13)0.0009 (17)
C160.0321 (11)0.0259 (11)0.0332 (14)−0.0001 (9)−0.0005 (10)−0.0036 (10)
C170.0290 (11)0.0252 (12)0.0302 (12)−0.0008 (10)0.0039 (10)−0.0031 (10)
N30.0352 (18)0.044 (2)0.047 (2)0.0072 (15)−0.0079 (13)−0.0031 (16)
N40.044 (2)0.051 (3)0.0549 (16)0.014 (2)−0.0151 (15)−0.0090 (17)
N50.0311 (15)0.0365 (15)0.0357 (15)−0.0001 (13)−0.0043 (10)−0.0069 (14)
C180.0340 (16)0.0297 (16)0.0390 (17)0.0012 (14)−0.0003 (13)−0.0024 (15)
C190.0358 (18)0.055 (2)0.0441 (19)0.0007 (17)−0.0118 (15)−0.0084 (19)
C200.025 (2)0.0375 (17)0.037 (3)0.0010 (17)−0.0018 (19)−0.001 (2)
C210.032 (2)0.043 (2)0.046 (2)−0.0036 (19)0.0001 (17)−0.0064 (19)
C220.036 (2)0.055 (3)0.046 (2)0.0001 (19)0.0008 (17)−0.001 (2)
C230.038 (3)0.047 (3)0.051 (3)0.003 (2)−0.013 (2)0.001 (2)
C240.036 (3)0.041 (2)0.050 (3)0.003 (2)−0.008 (2)−0.010 (3)
C250.0287 (19)0.052 (3)0.043 (2)0.0044 (19)0.0006 (16)0.002 (2)
C16A0.0321 (11)0.0259 (11)0.0332 (14)−0.0001 (9)−0.0005 (10)−0.0036 (10)
C17A0.0290 (11)0.0252 (12)0.0302 (12)−0.0008 (10)0.0039 (10)−0.0031 (10)
N3A0.0352 (18)0.044 (2)0.047 (2)0.0072 (15)−0.0079 (13)−0.0031 (16)
N4A0.044 (2)0.051 (3)0.0549 (16)0.014 (2)−0.0151 (15)−0.0090 (17)
N5A0.0311 (15)0.0365 (15)0.0357 (15)−0.0001 (13)−0.0043 (10)−0.0069 (14)
C18A0.0340 (16)0.0297 (16)0.0390 (17)0.0012 (14)−0.0003 (13)−0.0024 (15)
C19A0.0358 (18)0.055 (2)0.0441 (19)0.0007 (17)−0.0118 (15)−0.0084 (19)
C20A0.025 (2)0.0375 (17)0.037 (3)0.0010 (17)−0.0018 (19)−0.001 (2)
C21A0.032 (2)0.043 (2)0.046 (2)−0.0036 (19)0.0001 (17)−0.0064 (19)
C22A0.036 (2)0.055 (3)0.046 (2)0.0001 (19)0.0008 (17)−0.001 (2)
C23A0.038 (3)0.047 (3)0.051 (3)0.003 (2)−0.013 (2)0.001 (2)
C24A0.036 (3)0.041 (2)0.050 (3)0.003 (2)−0.008 (2)−0.010 (3)
C25A0.0287 (19)0.052 (3)0.043 (2)0.0044 (19)0.0006 (16)0.002 (2)
Geometric parameters (Å, º) top
O1—C71.224 (2)C16—H16A0.9900
O2—C91.214 (3)C16—H16B0.9900
N1—C71.380 (3)C17—N31.357 (4)
N1—C61.391 (2)C17—C181.363 (5)
N1—C81.441 (2)N3—N41.329 (4)
N2—C71.383 (3)N4—N51.334 (5)
N2—C11.391 (2)N5—C181.336 (4)
N2—C161.448 (3)N5—C191.460 (4)
N2—C16A1.448 (3)C18—H180.9500
C1—C21.382 (3)C19—C201.506 (4)
C1—C61.400 (3)C19—H19A0.9900
C2—C31.386 (3)C19—H19B0.9900
C2—H20.9500C20—C211.3900
C3—C41.390 (3)C20—C251.3900
C3—H30.9500C21—C221.3900
C4—C51.394 (3)C21—H210.9500
C4—H40.9500C22—C231.3900
C5—C61.377 (3)C22—H220.9500
C5—H50.9500C23—C241.3900
C8—C91.516 (3)C23—H230.9500
C8—H8A0.9900C24—C251.3900
C8—H8B0.9900C24—H240.9500
C9—C10A1.493 (2)C25—H250.9500
C9—C101.493 (2)C16A—C17A1.488 (3)
C10—C111.3900C16A—H16C0.9900
C10—C151.3900C16A—H16D0.9900
C11—C121.3900C17A—N3A1.356 (5)
C11—H110.9500C17A—C18A1.366 (5)
C12—C131.3900N3A—N4A1.328 (4)
C12—H120.9500N4A—N5A1.336 (5)
C13—C141.3900N5A—C18A1.335 (4)
C13—H130.9500N5A—C19A1.459 (4)
C14—C151.3900C18A—H18A0.9500
C14—H140.9500C19A—C20A1.507 (4)
C15—H150.9500C19A—H19C0.9900
C10A—C11A1.3900C19A—H19D0.9900
C10A—C15A1.3900C20A—C21A1.3900
C11A—C12A1.3900C20A—C25A1.3900
C11A—H11A0.9500C21A—C22A1.3900
C12A—C13A1.3900C21A—H21A0.9500
C12A—H12A0.9500C22A—C23A1.3900
C13A—C14A1.3900C22A—H22A0.9500
C13A—H13A0.9500C23A—C24A1.3900
C14A—C15A1.3900C23A—H23A0.9500
C14A—H14A0.9500C24A—C25A1.3900
C15A—H15A0.9500C24A—H24A0.9500
C16—C171.488 (3)C25A—H25A0.9500
C7—N1—C6110.06 (16)N2—C16—H16B108.5
C7—N1—C8124.12 (17)C17—C16—H16B108.5
C6—N1—C8125.12 (17)H16A—C16—H16B107.5
C7—N2—C1109.86 (17)N3—C17—C18108.1 (3)
C7—N2—C16122.2 (9)N3—C17—C16125.1 (7)
C1—N2—C16127.9 (9)C18—C17—C16126.4 (7)
C7—N2—C16A124.5 (9)N4—N3—C17108.3 (3)
C1—N2—C16A125.6 (9)N3—N4—N5107.1 (3)
C2—C1—N2131.72 (19)N4—N5—C18110.9 (3)
C2—C1—C6121.25 (18)N4—N5—C19119.3 (3)
N2—C1—C6107.02 (17)C18—N5—C19129.7 (4)
C1—C2—C3116.93 (19)N5—C18—C17105.5 (3)
C1—C2—H2121.5N5—C18—H18127.2
C3—C2—H2121.5C17—C18—H18127.2
C2—C3—C4121.85 (19)N5—C19—C20114.6 (4)
C2—C3—H3119.1N5—C19—H19A108.6
C4—C3—H3119.1C20—C19—H19A108.6
C3—C4—C5121.3 (2)N5—C19—H19B108.6
C3—C4—H4119.4C20—C19—H19B108.6
C5—C4—H4119.4H19A—C19—H19B107.6
C6—C5—C4116.76 (19)C21—C20—C25120.0
C6—C5—H5121.6C21—C20—C19119.6 (3)
C4—C5—H5121.6C25—C20—C19120.4 (3)
C5—C6—N1131.26 (18)C22—C21—C20120.0
C5—C6—C1121.92 (18)C22—C21—H21120.0
N1—C6—C1106.80 (17)C20—C21—H21120.0
O1—C7—N1126.75 (19)C23—C22—C21120.0
O1—C7—N2127.1 (2)C23—C22—H22120.0
N1—C7—N2106.17 (17)C21—C22—H22120.0
N1—C8—C9111.74 (17)C22—C23—C24120.0
N1—C8—H8A109.3C22—C23—H23120.0
C9—C8—H8A109.3C24—C23—H23120.0
N1—C8—H8B109.3C25—C24—C23120.0
C9—C8—H8B109.3C25—C24—H24120.0
H8A—C8—H8B107.9C23—C24—H24120.0
O2—C9—C10A122.8 (5)C24—C25—C20120.0
O2—C9—C10121.1 (4)C24—C25—H25120.0
O2—C9—C8119.78 (19)C20—C25—H25120.0
C10A—C9—C8117.4 (4)N2—C16A—C17A110.4 (3)
C10—C9—C8119.0 (4)N2—C16A—H16C109.6
C11—C10—C15120.0C17A—C16A—H16C109.6
C11—C10—C9117.6 (5)N2—C16A—H16D109.6
C15—C10—C9121.9 (5)C17A—C16A—H16D109.6
C10—C11—C12120.0H16C—C16A—H16D108.1
C10—C11—H11120.0N3A—C17A—C18A108.4 (3)
C12—C11—H11120.0N3A—C17A—C16A125.2 (4)
C13—C12—C11120.0C18A—C17A—C16A126.3 (4)
C13—C12—H12120.0N4A—N3A—C17A108.3 (3)
C11—C12—H12120.0N3A—N4A—N5A107.0 (3)
C12—C13—C14120.0C18A—N5A—N4A111.2 (3)
C12—C13—H13120.0C18A—N5A—C19A129.7 (4)
C14—C13—H13120.0N4A—N5A—C19A119.1 (3)
C13—C14—C15120.0N5A—C18A—C17A105.1 (3)
C13—C14—H14120.0N5A—C18A—H18A127.5
C15—C14—H14120.0C17A—C18A—H18A127.5
C14—C15—C10120.0N5A—C19A—C20A114.0 (3)
C14—C15—H15120.0N5A—C19A—H19C108.8
C10—C15—H15120.0C20A—C19A—H19C108.8
C11A—C10A—C15A120.0N5A—C19A—H19D108.8
C11A—C10A—C9118.5 (7)C20A—C19A—H19D108.8
C15A—C10A—C9120.1 (8)H19C—C19A—H19D107.7
C10A—C11A—C12A120.0C21A—C20A—C25A120.0
C10A—C11A—H11A120.0C21A—C20A—C19A119.9 (3)
C12A—C11A—H11A120.0C25A—C20A—C19A120.0 (3)
C13A—C12A—C11A120.0C22A—C21A—C20A120.0
C13A—C12A—H12A120.0C22A—C21A—H21A120.0
C11A—C12A—H12A120.0C20A—C21A—H21A120.0
C12A—C13A—C14A120.0C21A—C22A—C23A120.0
C12A—C13A—H13A120.0C21A—C22A—H22A120.0
C14A—C13A—H13A120.0C23A—C22A—H22A120.0
C15A—C14A—C13A120.0C24A—C23A—C22A120.0
C15A—C14A—H14A120.0C24A—C23A—H23A120.0
C13A—C14A—H14A120.0C22A—C23A—H23A120.0
C14A—C15A—C10A120.0C23A—C24A—C25A120.0
C14A—C15A—H15A120.0C23A—C24A—H24A120.0
C10A—C15A—H15A120.0C25A—C24A—H24A120.0
N2—C16—C17115.1 (3)C24A—C25A—C20A120.0
N2—C16—H16A108.5C24A—C25A—H25A120.0
C17—C16—H16A108.5C20A—C25A—H25A120.0
C7—N2—C1—C2179.6 (2)C11A—C12A—C13A—C14A0.0
C16—N2—C1—C21.3 (4)C12A—C13A—C14A—C15A0.0
C16A—N2—C1—C21.9 (4)C13A—C14A—C15A—C10A0.0
C7—N2—C1—C6−0.8 (2)C11A—C10A—C15A—C14A0.0
C16—N2—C1—C6−179.1 (3)C9—C10A—C15A—C14A166.5 (7)
C16A—N2—C1—C6−178.4 (3)C7—N2—C16—C17101.9 (12)
N2—C1—C2—C3179.8 (2)C1—N2—C16—C17−80.1 (15)
C6—C1—C2—C30.2 (3)N2—C16—C17—N350.9 (18)
C1—C2—C3—C40.2 (3)N2—C16—C17—C18−121.0 (10)
C2—C3—C4—C5−0.9 (3)C18—C17—N3—N40.05 (10)
C3—C4—C5—C61.1 (3)C16—C17—N3—N4−173.1 (9)
C4—C5—C6—N1−178.8 (2)C17—N3—N4—N50.02 (10)
C4—C5—C6—C1−0.7 (3)N3—N4—N5—C18−0.08 (19)
C7—N1—C6—C5−179.1 (2)N3—N4—N5—C19178.9 (4)
C8—N1—C6—C5−8.4 (3)N4—N5—C18—C170.1 (2)
C7—N1—C6—C12.6 (2)C19—N5—C18—C17−178.8 (4)
C8—N1—C6—C1173.32 (18)N3—C17—C18—N5−0.09 (18)
C2—C1—C6—C50.1 (3)C16—C17—C18—N5172.9 (8)
N2—C1—C6—C5−179.59 (17)N4—N5—C19—C20101.2 (4)
C2—C1—C6—N1178.60 (18)C18—N5—C19—C20−80.0 (5)
N2—C1—C6—N1−1.1 (2)N5—C19—C20—C21−54.1 (5)
C6—N1—C7—O1177.9 (2)N5—C19—C20—C25128.3 (4)
C8—N1—C7—O17.1 (3)C25—C20—C21—C220.0
C6—N1—C7—N2−3.1 (2)C19—C20—C21—C22−177.6 (4)
C8—N1—C7—N2−173.90 (17)C20—C21—C22—C230.0
C1—N2—C7—O1−178.6 (2)C21—C22—C23—C240.0
C16—N2—C7—O1−0.3 (4)C22—C23—C24—C250.0
C16A—N2—C7—O1−1.0 (5)C23—C24—C25—C200.0
C1—N2—C7—N12.4 (2)C21—C20—C25—C240.0
C16—N2—C7—N1−179.2 (3)C19—C20—C25—C24177.6 (4)
C16A—N2—C7—N1−180.0 (4)C7—N2—C16A—C17A105.0 (12)
C7—N1—C8—C996.7 (2)C1—N2—C16A—C17A−77.8 (15)
C6—N1—C8—C9−72.8 (3)N2—C16A—C17A—N3A−6 (2)
N1—C8—C9—O2−15.4 (3)N2—C16A—C17A—C18A170.2 (7)
N1—C8—C9—C10A162.8 (5)C18A—C17A—N3A—N4A0.02 (10)
N1—C8—C9—C10168.5 (4)C16A—C17A—N3A—N4A176.8 (12)
O2—C9—C10—C114.7 (5)C17A—N3A—N4A—N5A−0.03 (10)
C8—C9—C10—C11−179.3 (3)N3A—N4A—N5A—C18A0.02 (19)
O2—C9—C10—C15176.3 (4)N3A—N4A—N5A—C19A−179.0 (4)
C8—C9—C10—C15−7.6 (7)N4A—N5A—C18A—C17A0.0 (2)
C15—C10—C11—C120.0C19A—N5A—C18A—C17A178.9 (4)
C9—C10—C11—C12171.8 (6)N3A—C17A—C18A—N5A−0.01 (18)
C10—C11—C12—C130.0C16A—C17A—C18A—N5A−176.7 (11)
C11—C12—C13—C140.0C18A—N5A—C19A—C20A65.1 (6)
C12—C13—C14—C150.0N4A—N5A—C19A—C20A−116.0 (4)
C13—C14—C15—C100.0N5A—C19A—C20A—C21A48.6 (5)
C11—C10—C15—C140.0N5A—C19A—C20A—C25A−135.3 (4)
C9—C10—C15—C14−171.5 (7)C25A—C20A—C21A—C22A0.0
O2—C9—C10A—C11A3.6 (7)C19A—C20A—C21A—C22A176.1 (4)
C8—C9—C10A—C11A−174.6 (4)C20A—C21A—C22A—C23A0.0
O2—C9—C10A—C15A−163.1 (4)C21A—C22A—C23A—C24A0.0
C8—C9—C10A—C15A18.7 (7)C22A—C23A—C24A—C25A0.0
C15A—C10A—C11A—C12A0.0C23A—C24A—C25A—C20A0.0
C9—C10A—C11A—C12A−166.8 (8)C21A—C20A—C25A—C24A0.0
C10A—C11A—C12A—C13A0.0C19A—C20A—C25A—C24A−176.1 (4)
Hydrogen-bond geometry (Å, º) top
Cg4, Cg5 and Cg6 are the centroids of the C1–C6, C10–C15 and C20–C25 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.992.373.190 (3)140
C16—H16B···Cg4ii0.992.693.384 (14)128
C18—H18···Cg5i0.952.883.700 (5)146
C19—H19A···Cg6iii0.992.713.678 (5)166
C22—H22···N3iv0.952.533.224 (5)130
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+2, −y+1, −z+1.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

References

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Volume 82| Part 9| September 2026| Pages 1077-1081
https://doi.org/10.1107/S2056989026008492