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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009072

Crystal structure and Hirshfeld surface analysis of 2,5-di­methyl-1H-benzo[d]imidazole

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Achrafe Oulhaj,a,b Jihad Sebhaoui,c Gamal Al Ati,a Fares Hezam Al-Ostoot,d* Joel T. Mague,e El Mokhtar Essassi,a Adam Duongb and Karim Chkiratea*

aLaboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University in Rabat, Morocco, bLaboratory of Glycochemistry and Agro-resources of Amiens, UR 7378, 10, Baudelocque Street, 80039 Amiens Cedex, University of Picardy Jules Verne, France, cLife and Health Sciences Laboratory, Faculty of Medicine and Pharmacy, Université Abdelmalek Essaâdi, Tangier, Morocco, dDepartment of Biochemistry, Faculty of Education & Science, Albaydha University, Albaydha, Yemen, and eDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: [email protected], [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 20 August 2026; accepted 31 August 2026; online 8 September 2026)

The title mol­ecule, C9H10N2, exhibits whole-mol­ecule disorder in a 0.849 (4)/0.151 (4) ratio. The bicyclic portion is planar. In the crystal, a layer structure parallel to the ac plane is generated by N—H⋯N hydrogen bonds and C—H⋯π(ring) inter­actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H, C⋯H/H⋯C and N⋯H/H⋯N inter­actions.

CCDC reference: 2584534

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1. Chemical context

Nitro­gen-based structures have attracted more attention in recent years due to their inter­esting properties in structural and inorganic chemistry (Al Ati et al. 2025View full citation; Ksama et al. 2025View full citation; Oufkir et al. 2026View full citation; Azgaou et al. 2026View full citation; Arzine et al. 2026View full citation). The family of benzimidazole derivatives is important in medicinal chemistry because of their wide range of pharmacological applications such as anti­bacterial (Chkirate et al., 2020View full citation) and anti­oxidant (Chkirate et al., 2023View full citation) activity. In particular, 2-methyl­benzimidazole is an anti-inflammatory and analgesic agent (Gaba et al., 2010View full citation). Given the wide range of therapeutic applications for such compounds, and in continuation of the work already carried out for the synthesis of the compounds resulting from benzimidazole, a similar approach gave the title compound, 2,5-dimethyl-1H-benzo[d]imidazole C9H10N2 (I)[link]. Besides the synthesis, we also report the mol­ecular and crystal structures along with a Hirshfeld surface analysis.

[Scheme 1]

2. Structural commentary

There is whole-mol­ecule disorder in which the two orientations of the mol­ecule [refined ratio = 0.849 (4)/0.151 (4)] are related by a 180° rotation about the long axis and a translation of approximately 0.8 Å perpendicular to this axis in the plane of the mol­ecule (Fig. 1[link]). The subsequent discussion refers to the major component of the disorder. The bicyclic portion of the mol­ecule is planar to within 0.012 (5) Å (r.m.s deviation of the nine fitted atoms is 0.0074 Å). Given the disorder, all bond lengths and bond angles appear as expected for the formulation given.

[Figure 1]
Figure 1
Perspective view of the title mol­ecule with labeling scheme and 50% probability ellipsoids. The minor component of the whole-mol­ecule disorder is depicted by the green skeleton and green labels.

3. Supra­molecular features

In the crystal, N2—H2⋯N1i hydrogen bonds form chains of mol­ecules extending along the a-axis direction, which are linked by C9—H9B⋯Cg2iii inter­actions (Table 1[link]) to form corrugated layers of mol­ecules parallel to the ac plane (Fig. 2[link]). The layers are connected along the b-axis direction by C8—H8C···Cg1ii inter­actions (Table 1[link] and Fig. 3[link]). There are no π–π stacking inter­actions present as confirmed by the Hirshfeld surface analysis showing C⋯C contacts to be only 0.8% of the total when only the major orientation was considered and only 0.6% of the total when both orientations were taken together.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C6/C1/N2/C7 and C1–C6 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯N1i 0.88 1.95 2.801 (6) 162
C8—H8C⋯Cg1ii 0.98 2.97 3.941 (8) 172
C9—H9B⋯Cg2iii 0.98 2.57 3.478 (10) 153
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation.
[Figure 2]
Figure 2
A portion of one layer of the major orientation viewed along the b-axis direction with N—H⋯N hydrogen bonds and C—H⋯π(ring) inter­actions depicted, respectively, by blue and green dashed lines. Hydrogen atoms not involved in these inter­actions are omitted for clarity.
[Figure 3]
Figure 3
Packing of the major orientation projected on (101) with N—H⋯N hydrogen bonds depicted by blue dashed lines. The intra­layer C—H⋯π(ring) inter­actions are depicted by green dashed lines while those joining the layers are depicted by pink dashed lines. Hydrogen atoms not involved in these inter­actions are omitted for clarity.

4. Hirshfeld surface analysis

The CrystalExplorer program (Turner et al., 2017View full citation) was used to investigate and visualize the inter­molecular inter­actions of the title mol­ecule. The Hirshfeld surface for both orientations of the title mol­ecule plotted over dnorm in the range −0.6407 to 0.9694 a.u. is shown in Fig. 4[link]a while that for the major orientation only and plotted over the range −0.6203 to 1.1594 a.u. is shown in Fig. 4[link]b. In both instances, several neighboring mol­ecules are included. Only the N—H⋯N hydrogen bonds indicated in Fig. 4[link]a by red dashed lines; in Fig. 4[link]b, one of the C—H⋯π(ring) inter­actions is also depicted by two red dashed lines in the upper part of the figure. The electrostatic potential using the STO-3G basis set at the Hartree–Fock level of theory and mapped on the Hirshfeld surface for the major orientation over the range of ± 0.05 a.u. clearly shows the positions of close inter­molecular contacts in the compound (Fig. 5[link]). The positive electrostatic potential (blue region) over the surface indicates hydrogen donor potential, whereas the hydrogen bond acceptors are represented by negative electrostatic potential (red region).

[Figure 4]
Figure 4
(a) View of the three-dimensional Hirshfeld surface of both orientations of the title compound taken together, plotted over dnorm in the range −0.6407 to 0.9694 a.u. (b) View of the three-dimensional Hirshfeld surface of the major orientation of the title compound plotted over dnorm in the range −0.6203 to 1.1594 a.u.
[Figure 5]
Figure 5
View of the three-dimensional Hirshfeld surface of the major orientation of the title compound plotted over the electrostatic potential in the range −0.0500 to 0.0500 a.u. using the STO-3G basis set at the Hartree–Fock level of theory.

The two-dimensional fingerprint plots (McKinnon et al., 2007View full citation) for both orientations of the mol­ecule taken together are presented in Fig. 6[link], while the corresponding ones for the major orientation only are given in Fig. 7[link]. All inter­molecular contacts are shown in Fig. 6[link]a and 7a with those showing H⋯H contacts in Fig. 6[link]b and 7b. The C⋯H/H⋯C contacts are given in Fig. 6[link]c and 7c and the N⋯H/H⋯N contacts in Fig. 6[link]d and 7d. In Fig. 6[link], the H⋯H, C⋯H/H⋯C and N⋯H/H⋯N contacts contribute 64.9%, 26.1% and 8.3% of the total inter­molecular inter­actions, respectively, while in Fig. 7[link] the contributions are 56.5%, 25.4% and 16.7%, respectively. The fact that the H⋯H contacts contribute the most is because the periphery of the mol­ecule consists largely of hydrogen atoms and, for both orientations, more of these contacts must be taken into account in the calculation of the surface area. Furthermore, because the atoms in the two orientations of the mol­ecule are located quite close together, there will be many small differences in the lengths of the inter­molecular contacts, which leads to rather diffuse graphs for the three specific inter­actions, as is clearly visible in Fig. 6[link]b–6d. For the major orientation only, the majority of the C⋯H/H⋯C contacts (Fig. 7[link]c) can be attributed to the C—H⋯π(ring) inter­actions while the pair of sharp peaks in Fig. 7[link]d appearing at de + di ≃ 2.1 Å clearly represents the N—H⋯N hydrogen bonds.

[Figure 6]
Figure 6
The full two-dimensional fingerprint plots for both orientations of the title compound taken together, showing (a) all inter­actions, and those delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) N⋯H/H⋯N inter­actions. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.
[Figure 7]
Figure 7
The full two-dimensional fingerprint plots for the major orientation of the title compound showing (a) all inter­actions, and those delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) N⋯H/H⋯N inter­actions. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD version 6.01, updated May 2026; Groom et al., 2016View full citation) with the 5-substituted-1H-benzimidazole fragment (Fig. 8[link], R = C, R′ = any atom or group) yielded 43 hits from which 27 examples were retained after elimination of protonated and polymeric structures as well as some duplicate entries. These are listed in Table 2[link]. In most instances, the benzimidazole moiety is planar to within 0.02 Å, the only exceptions being AWIVEI, RIVWEB and XOWDOE where the maximum deviation of an atom in the bicyclic unit is 0.04, 0.03 and 0.04 Å, respectively. In MUSMOF, the benzimidazole moiety has crystallographically-imposed m symmetry. As in the title mol­ecule, most structures do not involve any π–πstacking inter­actions in the crystal. Exceptions are AGIVEU where neighboring five-membered rings show offset π-stacking, AWIVEI and YOTJUN where benzimidazole moieties π-stack across inversion centers, DUJLIE, TUBZEY and YOTJUN01 with the five-membered ring π-stacked with a neighboring pendant phenyl ring, TUBVOE where the five-membered ring inter­acts with the heterocyclic ring of a neighboring iso­quinoline unit, VUWGUT where the six-membered ring of the benzimidazole inter­acts with a pendant five-membered ring and ARUQUD which involves the π–π stacking of the five-membered ring of one benzimidazole with the six-membered ring of an adjacent one.

Table 2
Results of database survey

REFCODE R R′ Reference
AGIVEU COOEt p-anis­yl Yeong et al. (2018View full citation)
AWIVEI morpholino­meth­yl (3-cyclo­propyl­ureido)-1H-pyrazol-4-yl Howard et al. (2009View full citation)
CINTIG benzo­yl 2-hy­droxy-4-di­ethyl­amino­phen­yl Bal et al. (2024View full citation)
DUJLIE Me 2-hy­droxy-3-methyl­phen­yl Eltayeb et al. (2009aView full citation)
FIPJIZ01 (3,5-di­chloro-2-hy­droxy­phen­yl)-1H-benzo[d]imidazol-2-yl 3,5-di­chloro-2-hy­droxy­phen­yl Geng et al. (2014View full citation)
HONLUT 5-methyl-7-nitro-1H-benzo[d]imidazol-2-yl pyridin-2-yl White et al. (2014View full citation)
JOHCUG 1,5-diisopropyl-6-oxo-1,2,5,6-tetra­hydro-1,2,4,5-tetra­zin-3-yl H Seber et al. (2014View full citation)
LOWNAP morpholino­benzo[d]thia­zol-2-yl pyridin-2-yl White & Fellowes (2019View full citation)
MUSMOF tri­fluoro­meth­yl 2-(5-(tri­fluoro­meth­yl)-1H-benzo[d]imidazol-2-yl)pyridin-6-yl Fares et al. (2020View full citation)
OPUCUA Me (5-methyl­isoxazol-3-yl)meth­yl Idrissi et al. (2021View full citation)
PIDJODa benzo­yl NHCOOMe Chen & Lu (2013View full citation)
PIDJUJb benzo­yl NHCOOMe Chen & Lu (2013View full citation)
PIDKAQc benzo­yl NHCOOMe Chen & Lu (2013View full citation)
PIDKEUd benzo­yl NHCOOMe Chen & Lu (2013View full citation)
RALSUT Me {[3-bromo-1-(methyl­sulfon­yl)-1H-indol-2-yl]meth­yl}thio Ravishankar et al. (2005View full citation)
RIFDAM COOEt H Ding et al. (2005View full citation)
RIVWEB (4-methyl­piperazin-1-yl)-1H-benzo[d]imidazol-2-yl 2-methyl-4-dimethylamino­phen­yl White et al. (2018View full citation)
SAGQEW benzo­yl NHCOOMe Caira et al. (1998View full citation)
TUBVOE (4-methyl­piperazin-1-yl)-1H-benzo[d]imidazol-2-yl isoquinolin-1-yl White et al. (2019aView full citation)
TUBZEY (3-fluoro-6-morpholino-2-nitro­phen­yl)carbamo­yl pyridin-2-yl White et al. (2019bView full citation)
VEVPOD benzo­yl NHCOOMe Chen et al. (2012View full citation)
VUWGUT 1-(3,4,5-tri­meth­oxy­phen­yl)-1H-1,2,4-triazol-3-yl H Deb et al. (2024View full citation)
WOBKEF (3,5-di­bromo-2-hy­droxy­phen­yl)-1H-benzo[d]imidazol-2-yl 3,5-di­bromo-2-hy­droxy­phen­yl Geng et al. (2014View full citation)
XOWDOE 2-amino­pyridin-3-yl (furan-2-ylmeth­yl)carbamo­yl Jose et al. (2015View full citation)
YOTJUN Me 2-hy­droxy-3-methyl­phen­yl Xiao et al. (2009View full citation)
YOTJUN01 Me 2-hy­droxy-3-methyl­phen­yl Eltayeb et al. (2009bView full citation)
ARUQUD Me 2-hy­droxy­phen­yl Kubicki (2025View full citation)
Notes: (a) n-hexa­noic acid solvate; (b) n-penta­noic acid solvate; (c) n-butanoic acid solvate; (d) acetic acid solvate.
[Figure 8]
Figure 8
The search fragment used for the database survey.

6. Synthesis and crystallization

A mixture of 3.36 g (0.02 mol) de­hydro­acetic acid and 4.88 g (0.04 mol) 4-methy-o-phenyl­enedi­amine in 80 mL of xylene was refluxed for two hours at 411 K. When the starting reagents had completely reacted, the solution was chromatographed on a silica gel column (chloro­form/ether: 60:40 v/v). The product was recrystallized from ethanol to give colorless, plate-like crystals of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.44 (s, 3H, CH3 position 5) ; 2.70 (s, 3H, CH3 position 2); 7.12 (d, 1H, CH, J = 7.5Hz); 7.42 (s, 1H, NH); 7.43 (s, 1H, CH); 7.54 (dd, 1H, CH), J = 7.5Hz). 13C NMR (75 MHz, DMSO-d6) δ ppm: 14.0 (CH3); 21.3 (CH3); 115.1–125.8 (CHarom); 132.7–152.9 (Cq).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Following location of the minor orientation of the mol­ecule, the refinement was continued with the minor orientation restrained to have a comparable geometry to that of the major orientation using a SAME 0.002 N1 > C9 instruction. In addition, the displacement ellipsoids for the atoms of the minor component were linked to those of the major component with pair-wise EADP instructions while atoms N2, N2A, C7 and C7A were additionally restrained using ISOR 0.008. Hydrogen atoms were placed in idealized positions and included as riding contributions with isotropic displacement parameters tied to those of the attached atoms.

Table 3
Experimental details

Crystal data
Chemical formula C9H10N2
Mr 146.19
Crystal system, space group Orthorhombic, Pna21
Temperature (K) 125
a, b, c (Å) 10.011 (3), 13.047 (4), 6.0600 (19)
V (Å3) 791.5 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.26 × 0.23 × 0.05
 
Data collection
Diffractometer Bruker D8 QUEST PHOTON 3 diffractometer
Absorption correction Numerical (SADABS;Krause et al., 2015View full citation)
Tmin, Tmax 0.98, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections 5699, 1599, 1106
Rint 0.062
(sin θ/λ)max (Å−1) 0.624
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.206, 1.09
No. of reflections 1599
No. of parameters 134
No. of restraints 54
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.16, −0.31
Absolute structure Flack x determined using 373 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013View full citation)
Absolute structure parameter 0.0 (10)
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 SHELXTL (Sheldrick, 2008View full citation).

Supporting information

CCDC reference: 2584534

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989026009072/vm2334sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009072/vm2334Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026009072/vm2334Isup3.cml

checkCIF report


Computing details top

2,5-Dimethyl-1H-benzo[d]imidazole top
Crystal data top
C9H10N2Dx = 1.227 Mg m−3
Mr = 146.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2151 reflections
a = 10.011 (3) Åθ = 2.6–26.0°
b = 13.047 (4) ŵ = 0.08 mm−1
c = 6.0600 (19) ÅT = 125 K
V = 791.5 (4) Å3Plate, colourless
Z = 40.26 × 0.23 × 0.05 mm
F(000) = 312
Data collection top
Bruker D8 QUEST PHOTON 3
diffractometer		1599 independent reflections
Radiation source: fine-focus sealed tube1106 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 7.3910 pixels mm-1θmax = 26.3°, θmin = 2.6°
ω scansh = −12→12
Absorption correction: numerical
(SADABS;Krause et al., 2015)		k = −16→15
Tmin = 0.98, Tmax = 1.00l = −7→7
5699 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.206 w = 1/[σ2(Fo2) + (0.102P)2 + 0.2624P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1599 reflectionsΔρmax = 0.16 e Å−3
134 parametersΔρmin = −0.31 e Å−3
54 restraintsAbsolute structure: Flack x determined using 373 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dualAbsolute structure parameter: 0.0 (10)
Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 80 sec/frame was used.

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. Hydrogen atoms were included as riding contributions in idealized positions with isotropic displacement parameters tied to those of the attached atoms. There is "whole molecule" disorder involving a rotation of the molecule about its long axis by 180° and a small translation perpendicular to this axis and in the plane of the molecule. The two orientations are in the ratio 0.849 (4)/0.151 (4) and were refined with restraints that their geometries be comparable.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.5960 (4)0.2625 (4)0.2831 (14)0.0399 (12)0.849 (4)
N20.8194 (4)0.2688 (3)0.2997 (15)0.0361 (11)0.849 (4)
H20.9032590.2578860.2629910.043*0.849 (4)
C10.7759 (5)0.3254 (4)0.4778 (15)0.0377 (13)0.849 (4)
C20.8377 (5)0.3791 (5)0.6458 (16)0.0445 (14)0.849 (4)
H2A0.9324150.3827500.6518820.053*0.849 (4)
C30.7621 (7)0.4274 (8)0.804 (2)0.0471 (15)0.849 (4)
C40.6207 (6)0.4219 (5)0.7911 (16)0.0474 (14)0.849 (4)
H40.5681290.4557580.8993530.057*0.849 (4)
C50.5584 (6)0.3687 (5)0.6253 (16)0.0485 (15)0.849 (4)
H50.4637200.3646780.6201030.058*0.849 (4)
C60.6351 (5)0.3208 (4)0.4655 (15)0.0371 (13)0.849 (4)
C70.7095 (5)0.2323 (4)0.1895 (16)0.0365 (13)0.849 (4)
C80.8233 (7)0.4886 (6)0.9896 (18)0.0632 (19)0.849 (4)
H8A0.7697700.4797041.1235930.095*0.849 (4)
H8B0.9145900.4644471.0166960.095*0.849 (4)
H8C0.8253740.5612510.9490210.095*0.849 (4)
C90.7184 (6)0.1664 (6)−0.0064 (18)0.0479 (16)0.849 (4)
H9A0.6360700.126263−0.0206660.072*0.849 (4)
H9B0.7303020.208950−0.1381960.072*0.849 (4)
H9C0.7947050.1198870.0089450.072*0.849 (4)
N1A0.8890 (16)0.2654 (19)0.300 (3)0.0399 (12)0.151 (4)
N2A0.6658 (15)0.2699 (18)0.327 (3)0.0361 (11)0.151 (4)
H2B0.5814800.2580240.2943580.043*0.151 (4)
C1A0.7116 (13)0.327 (2)0.502 (4)0.0377 (13)0.151 (4)
C2A0.6526 (15)0.382 (2)0.671 (3)0.0445 (14)0.151 (4)
H2C0.5580580.3863110.6803230.053*0.151 (4)
C3A0.731 (2)0.431 (5)0.825 (7)0.0471 (15)0.151 (4)
C4A0.8718 (18)0.423 (2)0.810 (4)0.0474 (14)0.151 (4)
H4A0.9262040.4596900.9114260.057*0.151 (4)
C5A0.9307 (15)0.363 (2)0.653 (3)0.0485 (15)0.151 (4)
H5A1.0241730.3498710.6566220.058*0.151 (4)
C6A0.8522 (14)0.320 (2)0.488 (3)0.0371 (13)0.151 (4)
C7A0.7743 (17)0.235 (2)0.211 (4)0.0365 (13)0.151 (4)
C8A0.672 (2)0.490 (3)1.017 (4)0.0632 (19)0.151 (4)
H8D0.6991380.4566591.1554590.095*0.151 (4)
H8E0.7049250.5602731.0144620.095*0.151 (4)
H8F0.5744020.4895581.0062540.095*0.151 (4)
C9A0.763 (3)0.176 (4)0.005 (6)0.0479 (16)0.151 (4)
H9D0.7347160.1059560.0382080.072*0.151 (4)
H9E0.6972970.208692−0.0921480.072*0.151 (4)
H9F0.8501820.174415−0.0696400.072*0.151 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.028 (2)0.058 (3)0.033 (2)0.004 (2)0.009 (3)0.001 (2)
N20.0151 (19)0.055 (3)0.038 (2)0.0013 (17)0.010 (2)0.007 (2)
C10.035 (3)0.043 (3)0.036 (3)0.002 (3)−0.004 (3)0.008 (2)
C20.040 (3)0.049 (3)0.045 (3)−0.007 (3)−0.004 (3)0.010 (3)
C30.058 (4)0.047 (3)0.037 (3)0.001 (4)−0.003 (3)0.003 (3)
C40.054 (3)0.049 (3)0.039 (3)0.005 (3)0.007 (3)0.003 (3)
C50.041 (3)0.065 (4)0.039 (3)−0.001 (3)0.007 (3)0.000 (3)
C60.034 (3)0.044 (3)0.033 (3)0.004 (2)0.004 (3)0.009 (3)
C70.028 (3)0.050 (3)0.032 (2)−0.001 (3)0.007 (3)0.009 (2)
C80.082 (5)0.061 (4)0.046 (4)−0.011 (3)−0.009 (4)0.001 (3)
C90.044 (4)0.061 (4)0.039 (3)−0.003 (4)0.012 (4)0.000 (3)
N1A0.028 (2)0.058 (3)0.033 (2)0.004 (2)0.009 (3)0.001 (2)
N2A0.0151 (19)0.055 (3)0.038 (2)0.0013 (17)0.010 (2)0.007 (2)
C1A0.035 (3)0.043 (3)0.036 (3)0.002 (3)−0.004 (3)0.008 (2)
C2A0.040 (3)0.049 (3)0.045 (3)−0.007 (3)−0.004 (3)0.010 (3)
C3A0.058 (4)0.047 (3)0.037 (3)0.001 (4)−0.003 (3)0.003 (3)
C4A0.054 (3)0.049 (3)0.039 (3)0.005 (3)0.007 (3)0.003 (3)
C5A0.041 (3)0.065 (4)0.039 (3)−0.001 (3)0.007 (3)0.000 (3)
C6A0.034 (3)0.044 (3)0.033 (3)0.004 (2)0.004 (3)0.009 (3)
C7A0.028 (3)0.050 (3)0.032 (2)−0.001 (3)0.007 (3)0.009 (2)
C8A0.082 (5)0.061 (4)0.046 (4)−0.011 (3)−0.009 (4)0.001 (3)
C9A0.044 (4)0.061 (4)0.039 (3)−0.003 (4)0.012 (4)0.000 (3)
Geometric parameters (Å, º) top
N1—C71.330 (6)N1A—C7A1.330 (7)
N1—C61.398 (8)N1A—C6A1.397 (8)
N2—C71.372 (6)N2A—C7A1.372 (7)
N2—C11.378 (8)N2A—C1A1.379 (8)
N2—H20.8800N2A—H2B0.8800
C1—C21.383 (8)C1A—C2A1.383 (9)
C1—C61.413 (8)C1A—C6A1.413 (8)
C2—C31.375 (9)C2A—C3A1.375 (9)
C2—H2A0.9500C2A—H2C0.9500
C3—C41.419 (9)C3A—C4A1.420 (9)
C3—C81.509 (10)C3A—C8A1.509 (10)
C4—C51.371 (9)C4A—C5A1.371 (9)
C4—H40.9500C4A—H4A0.9500
C5—C61.385 (8)C5A—C6A1.385 (8)
C5—H50.9500C5A—H5A0.9500
C7—C91.469 (8)C7A—C9A1.469 (9)
C8—H8A0.9800C8A—H8D0.9800
C8—H8B0.9800C8A—H8E0.9800
C8—H8C0.9800C8A—H8F0.9800
C9—H9A0.9800C9A—H9D0.9800
C9—H9B0.9800C9A—H9E0.9800
C9—H9C0.9800C9A—H9F0.9800
C7—N1—C6105.0 (4)C7A—N1A—C6A104.9 (5)
C7—N2—C1108.3 (4)C7A—N2A—C1A108.2 (5)
C7—N2—H2125.9C7A—N2A—H2B125.9
C1—N2—H2125.9C1A—N2A—H2B125.9
N2—C1—C2135.0 (5)N2A—C1A—C2A135.3 (6)
N2—C1—C6104.5 (5)N2A—C1A—C6A104.5 (6)
C2—C1—C6120.5 (5)C2A—C1A—C6A120.2 (6)
C3—C2—C1120.0 (5)C3A—C2A—C1A120.1 (6)
C3—C2—H2A120.0C3A—C2A—H2C119.9
C1—C2—H2A120.0C1A—C2A—H2C119.9
C2—C3—C4119.2 (6)C2A—C3A—C4A119.1 (7)
C2—C3—C8122.5 (6)C2A—C3A—C8A122.5 (8)
C4—C3—C8118.3 (6)C4A—C3A—C8A118.2 (8)
C5—C4—C3121.3 (6)C5A—C4A—C3A121.1 (7)
C5—C4—H4119.3C5A—C4A—H4A119.5
C3—C4—H4119.3C3A—C4A—H4A119.5
C4—C5—C6119.3 (5)C4A—C5A—C6A119.1 (7)
C4—C5—H5120.4C4A—C5A—H5A120.5
C6—C5—H5120.4C6A—C5A—H5A120.5
C5—C6—N1130.0 (5)C5A—C6A—N1A130.1 (6)
C5—C6—C1119.8 (5)C5A—C6A—C1A119.8 (6)
N1—C6—C1110.2 (5)N1A—C6A—C1A110.1 (5)
N1—C7—N2112.0 (5)N1A—C7A—N2A112.0 (5)
N1—C7—C9124.7 (5)N1A—C7A—C9A124.5 (6)
N2—C7—C9123.2 (5)N2A—C7A—C9A123.4 (6)
C3—C8—H8A109.4C3A—C8A—H8D109.5
C3—C8—H8B109.5C3A—C8A—H8E109.3
H8A—C8—H8B109.5H8D—C8A—H8E109.5
C3—C8—H8C109.5C3A—C8A—H8F109.6
H8A—C8—H8C109.5H8D—C8A—H8F109.5
H8B—C8—H8C109.5H8E—C8A—H8F109.5
C7—C9—H9A109.5C7A—C9A—H9D109.3
C7—C9—H9B109.5C7A—C9A—H9E109.5
H9A—C9—H9B109.5H9D—C9A—H9E109.5
C7—C9—H9C109.4C7A—C9A—H9F109.6
H9A—C9—H9C109.5H9D—C9A—H9F109.5
H9B—C9—H9C109.5H9E—C9A—H9F109.5
C7—N2—C1—C2179.6 (7)C7A—N2A—C1A—C2A179 (4)
C7—N2—C1—C6−0.4 (6)C7A—N2A—C1A—C6A−2 (4)
N2—C1—C2—C3−179.0 (8)N2A—C1A—C2A—C3A179 (5)
C6—C1—C2—C30.9 (11)C6A—C1A—C2A—C3A1 (6)
C1—C2—C3—C4−0.6 (14)C1A—C2A—C3A—C4A−1 (8)
C1—C2—C3—C8−179.1 (8)C1A—C2A—C3A—C8A−178 (4)
C2—C3—C4—C50.7 (14)C2A—C3A—C4A—C5A−3 (7)
C8—C3—C4—C5179.2 (7)C8A—C3A—C4A—C5A173 (4)
C3—C4—C5—C6−1.1 (11)C3A—C4A—C5A—C6A9 (5)
C4—C5—C6—N1179.7 (6)C4A—C5A—C6A—N1A173 (3)
C4—C5—C6—C11.4 (9)C4A—C5A—C6A—C1A−9 (4)
C7—N1—C6—C5−178.0 (6)C7A—N1A—C6A—C5A174 (3)
C7—N1—C6—C10.4 (6)C7A—N1A—C6A—C1A−4 (3)
N2—C1—C6—C5178.6 (5)N2A—C1A—C6A—C5A−174 (3)
C2—C1—C6—C5−1.3 (9)C2A—C1A—C6A—C5A4 (5)
N2—C1—C6—N10.0 (6)N2A—C1A—C6A—N1A4 (4)
C2—C1—C6—N1−180.0 (5)C2A—C1A—C6A—N1A−177 (3)
C6—N1—C7—N2−0.7 (6)C6A—N1A—C7A—N2A2 (4)
C6—N1—C7—C9178.4 (6)C6A—N1A—C7A—C9A178 (4)
C1—N2—C7—N10.7 (6)C1A—N2A—C7A—N1A0 (4)
C1—N2—C7—C9−178.4 (6)C1A—N2A—C7A—C9A−176 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1/C6/C1/N2/C7 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.881.952.801 (6)162
C8—H8C···Cg1ii0.982.973.941 (8)172
C9—H9B···Cg2iii0.982.573.478 (10)153
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x+3/2, −y+1/2, z; (iii) x, y, z−1.
Results of database survey top
REFCODERR'Reference
AGIVEUCOOEtp-anisylYeong et al. (2018)
AWEIVEImorpholinomethyl(3-cyclopropylureido)-1H-pyrazol-4-ylHoward et al. (2009)
CINTIGbenzoyl2-hydroxy-4-diethylaminophenylBal et al. (2024)
DUJLIEMe2-hydroxy-3-methylphenylEltayeb et al. (2009a)
FIPJIZ01(3,5-dichloro-2-hydroxyphenyl)-1H-benzo[d]imidazol-2-yl3,5-dichloro-2-hydroxyphenylGeng et al. (2014)
HONLUT5-methyl-7-nitro-1H-benzo[d]imidazol-2-ylpyridin-2-ylWhite et al. (2014)
JOHCUG1,5-diisopropyl-6-oxo-1,2,5,6-tetrahydro-1,2,4,5-tetrazin-3-ylHSeber et al. (2014)
LOWNAPmorpholinobenzo[d]thiazol-2-ylpyridin-2-ylWhite & Fellowes, 2019)
MUSMOFtrifluoromethyl2-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyridin-6-ylFares et al. (2020)
OPUCUAMe(5-methylisoxazol-3-yl)methylIdrissi et al. (2021)
PIDJODabenzoylNHCOOMeChen & Lu (2013)
PIDJUJbbenzoylNHCOOMeChen & Lu (2013)
PIDKAQcbenzoylNHCOOMeChen & Lu (2013)
PIDKEUdbenzoylNHCOOMeChen & Lu (2013)
RALSUTMe{[3-bromo-1-(methylsulfonyl)-1H-indol-2-yl]methyl}thioRavishankar et al. (2005)
RIFDAMCOOEtHDing et al. (2005)
RIVWEB(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl2-methyl-4-dimethyaminophenylWhite et al. (2018)
SAGQEWbenzoylNHCOOMeCaira et al. (1998)
TUBVOE(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-ylisoquinolin-1-ylWhite et al. (2019a)
TUBZEY(3-fluoro-6-morpholino-2-nitrophenyl)carbamoylpyridin-2-ylWhite et al. (2019b)
VEVPODbenzoylNHCOOMeChen et al. (2012)
VUWGUT1-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-3-ylHDeb et al. (2024)
WOBKEF(3,5-dibromo-2-hydroxyphenyl)-1H-benzo[d]imidazol-2-yl3,5-dibromo-2-hydroxyphenylGeng et al. (2014)
XOWDOE2-aminopyridin-3-yl(furan-2-ylmethyl)carbamoylJose et al. (2015)
YOTJUNMe2-hydroxy-3-methylphenylXiao et al. (2009)
YOTJUN01Me2-hydroxy-3-methylphenylEltayeb et al. (2009b)
ARUQUDMe2-hydroxyphenylKubicki (2025)
Notes: (a) n-hexanoic acid solvate; (b) n-pentanoic acid solvate; (c) n-butanoic acid solvate; (d) acetic acid solvate.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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