2-Phenyl-4,5-di-p-tolyl-1H-imidazol-3-ium picrate

Solo, P.; Pillay, M.; Arockia doss, M.; William Raja, T.R.

doi:10.1107/S2414314625008776

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 10| October 2025| x250877

https://doi.org/10.1107/S2414314625008776

Open

access

2-Phenyl-4,5-di-p-tolyl-1H-imidazol-3-ium picrate

Peter Solo,^a,^b ^* Michael Pillay,^c M. Arockia doss ^d and Tharsius Raja William Raja ^c,^e

^aDepartment of Chemistry, St. Joseph's College (A), Jakhama, Nagaland, 797001, India, ^bDepartment of Environmental Studies, St. Xavier College, Jalukie, Nagaland, India, ^cDepartment of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, Florida Campus, University of South Africa, Johannesburg 1709, South Africa, ^dSchool of Science and Humanities, St. Joseph University, Emmanuel Educity, Tindivanam-604307, India, and ^ePostgraduate and Research Department of Biotechnology, Bishop Heber College (Autonomous), Tiruchirappalli, Tamil Nadu - 620 017 India
^*Correspondence e-mail: [email protected]

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 26 September 2025; accepted 8 October 2025; online 14 October 2025)

The title molecular salt [systematic name: 4,5-bis(4-methylphenyl)-2-phenyl-1H-imidazol-3-ium 2,4,6-trinitrobenzen-1-olate], C₂₃H₂₁N₂⁺·C₆H₂N₃O₇⁻, was been synthesized by the slow solvent evaporation method in ethanol and crystallizes in the monoclinic space group P2₁. The structure confirms proton transfer from picric acid to the imidazole ring. The crystal structure is consolidated by multiple N—H⋯O and C—H⋯O hydrogen bonding interactions.

Keywords: crystal structure; imidazolium picrate; hydrogen bonding.

CCDC reference: 2493989

Structure description

Picric acid has been used for the isolation and purification of basic compounds like alkaloids in the formation of highly stable and crystalline picrate salts (Maldoni, 1991 ). Imidazole picrates have been used as energetic materials as the ions can decompose or detonate under shock or heat (Gierczyk et al., 2024 ; Mi et al., 2016 ). Imidazolium picrate complexes have sharp and high melting points suitable for energetic materials (Smiglak et al., 2012 ). A number of imidazolium picrates have already been reported (Anandhi et al., 2011 ; Amudha et al., 2017 ).

The structure confirms one proton transfer from picric acid to the pyrimidine-type nitrogen atom of the imidazole ring. The asymmetric unit of the crystal consist of an imidazolium cation and a picrate anion (Fig. 1). The dihedral angles between the picrate ring and the other peripheral rings of the cation are 61.9 (2)° (imidazole ring), 78.5 (2)° (C1–C6), 19.9 (2)° (C10–C15) and 68.5 (2)° (C17–C22). This indicates that all the rings are in different planes and therefore we do not observe π–π stacking interactions. Each imidazolium cation is hydrogen bonded to three picrate anions (Fig. 2). The crystal structure is further consolidated by C—H⋯O hydrogen bonding interactions (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.64	3.107 (5)	115
N2—H2⋯O7ⁱⁱ	0.86	2.18	3.016 (4)	163
N1—H1⋯O5	0.86	1.95	2.727 (5)	149
N1—H1⋯O6	0.86	2.23	2.878 (5)	133
C21—H21⋯O3ⁱⁱⁱ	0.93	2.60	3.450 (7)	153
Symmetry codes: (i) ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+2]$ .

Figure 1
The asymmetric unit of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Crystal packing of the title compound with view onto the ac plane. The four unique hydrogen-bonding interactions in the title compound are shown in magenta.

Synthesis and crystallization

The synthesis of the imidazole derivative, 2-phenyl-4,5-di-p-tolyl-1H-imidazole (5), was achieved by a one pot condensation of 4,4-dimethylbenzil (1) (0.953 g, 0.004 moles), benzaldehyde (2) (0.424 g, 0.004 moles) and ammonium acetate (3) (1.233 g, 0.016 moles) in the presence of ceric ammonium nitrate (CAN, 4) as catalyst with ethanol as solvent (Fig. 3). The reflux reaction was carried out at 95°C for about 4 h and the completion of the reaction was monitored using TLC (hexane:ethyl acetate, 1:1). At the end of the reaction the mixture was poured into ice-cold water and the precipitate was collected. The crude precipitate was purified by recrystallization from 90% ethanol solution. Equimolar amounts of 2-phenyl-4,5-di-p-tolyl-1H-imidazole (5) and picric acid (6) were mixed in 100% ethanol and heated to 120°C. Imidazolium picrate (7) crystals were allowed to grow under slow solvent evaporation.

Figure 3
Reaction scheme for the synthesis of the title compound.

Refinement

Details of crystal data, data collection and refinement are given in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₂₁N₂⁺·C₆H₂N₃O₇⁻
M_r	553.52
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	12.742 (4), 7.705 (2), 13.799 (4)
β (°)	106.104 (9)
V (Å³)	1301.6 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.103
Crystal size (mm)	0.54 × 0.37 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.556, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	34163, 6024, 2712
R_int	0.147
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.110, 0.78
No. of reflections	6024
No. of parameters	373
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
Absolute structure	Flack x determined using 899 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.6 (10)
Computer programs: APEX2 and SAINT (Bruker, 2018 ), OLEX2.solv (Bourhis et al., 2015 ), SHELXL2025/1 (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2493989

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008776/bt4182sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008776/bt4182Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625008776/bt4182Isup3.cml

checkCIF report

Computing details top

4,5-Bis(4-methylphenyl)-2-phenyl-1H-imidazol-3-ium 2,4,6-trinitrobenzen-1-olate top

Crystal data top

C₂₃H₂₁N₂⁺·C₆H₂N₃O₇⁻	F(000) = 576
M_r = 553.52	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 12.742 (4) Å	Cell parameters from 2231 reflections
b = 7.705 (2) Å	θ = 3.1–15.6°
c = 13.799 (4) Å	µ = 0.10 mm⁻¹
β = 106.104 (9)°	T = 296 K
V = 1301.6 (7) Å³	Block, clear orangish orange
Z = 2	0.54 × 0.37 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	2712 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.147
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.2°, θ_min = 1.5°
T_min = 0.556, T_max = 0.746	h = −16→16
34163 measured reflections	k = −10→10
6024 independent reflections	l = −18→18

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0002P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.049	(Δ/σ)_max < 0.001
wR(F²) = 0.110	Δρ_max = 0.19 e Å⁻³
S = 0.78	Δρ_min = −0.22 e Å⁻³
6024 reflections	Extinction correction: SHELXL (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
373 parameters	Extinction coefficient: 0.044 (3)
1 restraint	Absolute structure: Flack x determined using 899 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: iterative	Absolute structure parameter: −0.6 (10)
Hydrogen site location: inferred from neighbouring sites

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. The hydrogen atoms were located in a difference map and refined as riding on their parent atom with U(H)=1.2U_eq(C,N) or with U(H)=1.5U_eq(C_methyl). The methyl groups were allowed to rotate but not to tip. Bond lengths were set to C_aromatic—H=0.93 Å, C_methyl—H=0.96 Å or N—H=0.86 Å. The reflection 113 with a high error/e.s.d. was omitted. The absolute structure could not be reliably determined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.1455 (3)	0.4635 (5)	0.6434 (3)	0.0353 (9)
H2	0.204991	0.472435	0.625931	0.042*
C6	0.0959 (4)	0.3741 (6)	0.4234 (4)	0.0415 (13)
H6	0.162582	0.331685	0.462316	0.050*
C7	0.0462 (4)	0.4459 (6)	0.5787 (4)	0.0368 (11)
N1	−0.0236 (3)	0.4355 (5)	0.6348 (3)	0.0386 (10)
H1	−0.093134	0.423540	0.611141	0.046*
C4	0.0203 (4)	0.4394 (6)	0.4693 (3)	0.0360 (11)
C9	0.0310 (3)	0.4467 (6)	0.7360 (4)	0.0363 (11)
C5	−0.0802 (4)	0.4957 (6)	0.4111 (4)	0.0412 (12)
H5	−0.132117	0.534895	0.441872	0.049*
C8	0.1397 (4)	0.4657 (6)	0.7430 (4)	0.0366 (11)
C19	0.4130 (4)	0.6144 (7)	0.9053 (4)	0.0469 (13)
H19	0.472630	0.677979	0.898547	0.056*
C14	−0.0819 (4)	0.5508 (7)	0.9555 (4)	0.0492 (14)
H14	−0.069251	0.628777	1.008899	0.059*
C17	0.2351 (3)	0.4888 (6)	0.8283 (4)	0.0364 (11)
C21	0.3248 (4)	0.4501 (6)	1.0046 (4)	0.0470 (13)
H21	0.323852	0.403536	1.066524	0.056*
C3	−0.1037 (4)	0.4940 (7)	0.3068 (4)	0.0518 (14)
H3	−0.170721	0.534100	0.267071	0.062*
C20	0.4132 (4)	0.5484 (7)	0.9988 (4)	0.0438 (12)
C10	−0.0321 (3)	0.4392 (6)	0.8110 (3)	0.0366 (11)
C13	−0.1652 (4)	0.4350 (7)	0.9426 (4)	0.0444 (13)
C12	−0.1807 (4)	0.3139 (7)	0.8643 (4)	0.0492 (14)
H12	−0.235320	0.230534	0.855861	0.059*
C11	−0.1149 (4)	0.3177 (6)	0.7992 (4)	0.0446 (13)
H11	−0.126600	0.237484	0.746928	0.054*
C22	0.2380 (4)	0.4186 (6)	0.9218 (4)	0.0432 (12)
H22	0.180566	0.349515	0.928332	0.052*
C18	0.3248 (4)	0.5864 (6)	0.8218 (4)	0.0421 (13)
H18	0.325491	0.633899	0.760009	0.051*
C15	−0.0146 (4)	0.5563 (6)	0.8909 (4)	0.0431 (12)
H15	0.041371	0.637548	0.901175	0.052*
C1	0.0714 (5)	0.3723 (7)	0.3190 (4)	0.0503 (14)
H1A	0.122127	0.330259	0.287650	0.060*
C2	−0.0266 (4)	0.4322 (7)	0.2630 (4)	0.0546 (14)
H2A	−0.042059	0.431438	0.193043	0.066*
C16	−0.2424 (4)	0.4338 (8)	1.0085 (4)	0.0632 (16)
H16A	−0.239347	0.322774	1.040684	0.095*
H16B	−0.315538	0.455267	0.967645	0.095*
H16C	−0.221361	0.522742	1.058898	0.095*
C23	0.5059 (4)	0.5911 (8)	1.0920 (4)	0.0642 (16)
H23A	0.568917	0.522917	1.091822	0.096*
H23B	0.483715	0.565050	1.151483	0.096*
H23C	0.523601	0.712117	1.091616	0.096*
C27	−0.3190 (3)	0.4287 (6)	0.6040 (3)	0.0333 (10)
C30	−0.4345 (3)	0.1636 (6)	0.5786 (3)	0.0369 (12)
H30	−0.450352	0.053799	0.550363	0.044*
O5	−0.2399 (2)	0.5161 (4)	0.5940 (2)	0.0441 (9)
O6	−0.1960 (3)	0.2302 (4)	0.5072 (3)	0.0556 (11)
N5	−0.2878 (3)	0.1788 (5)	0.5019 (3)	0.0398 (10)
C28	−0.3917 (3)	0.4906 (6)	0.6609 (4)	0.0375 (11)
O2	−0.6564 (3)	0.2124 (5)	0.6833 (3)	0.0601 (11)
N3	−0.5892 (3)	0.1346 (6)	0.6499 (3)	0.0466 (11)
O7	−0.3302 (3)	0.0599 (5)	0.4435 (3)	0.0565 (10)
C25	−0.4968 (3)	0.2334 (6)	0.6359 (4)	0.0363 (11)
C26	−0.3495 (3)	0.2567 (6)	0.5636 (4)	0.0330 (11)
O1	−0.5950 (3)	−0.0189 (5)	0.6298 (3)	0.0656 (11)
C29	−0.4759 (4)	0.3960 (6)	0.6778 (4)	0.0380 (12)
H29	−0.518172	0.441016	0.717033	0.046*
N4	−0.3740 (4)	0.6648 (6)	0.7051 (4)	0.0566 (13)
O4	−0.3466 (4)	0.7787 (5)	0.6561 (4)	0.0891 (16)
O3	−0.3909 (4)	0.6874 (6)	0.7847 (4)	0.1012 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.029 (2)	0.047 (2)	0.034 (2)	−0.0015 (17)	0.0146 (19)	0.0012 (19)
C6	0.044 (3)	0.042 (3)	0.043 (4)	−0.002 (2)	0.021 (3)	−0.003 (2)
C7	0.035 (3)	0.041 (3)	0.039 (3)	0.000 (2)	0.018 (3)	−0.001 (2)
N1	0.032 (2)	0.045 (2)	0.041 (3)	−0.0023 (18)	0.015 (2)	0.001 (2)
C4	0.039 (3)	0.036 (2)	0.035 (3)	−0.004 (2)	0.016 (2)	0.000 (2)
C9	0.034 (3)	0.043 (3)	0.033 (3)	−0.003 (2)	0.011 (2)	−0.002 (2)
C5	0.039 (3)	0.043 (3)	0.044 (3)	0.002 (2)	0.015 (3)	−0.001 (2)
C8	0.034 (3)	0.043 (3)	0.035 (3)	−0.002 (2)	0.015 (2)	0.002 (2)
C19	0.032 (3)	0.058 (3)	0.053 (4)	−0.007 (2)	0.015 (3)	−0.006 (3)
C14	0.055 (3)	0.054 (3)	0.049 (4)	−0.003 (3)	0.031 (3)	−0.004 (3)
C17	0.031 (2)	0.042 (3)	0.039 (3)	−0.001 (2)	0.014 (2)	−0.002 (2)
C21	0.049 (3)	0.053 (3)	0.039 (3)	0.003 (3)	0.013 (3)	0.008 (3)
C3	0.052 (3)	0.059 (3)	0.040 (3)	0.004 (3)	0.006 (3)	−0.003 (3)
C20	0.041 (3)	0.051 (3)	0.038 (3)	0.004 (2)	0.009 (3)	−0.006 (3)
C10	0.031 (2)	0.047 (3)	0.034 (3)	0.005 (2)	0.013 (2)	0.003 (2)
C13	0.044 (3)	0.055 (3)	0.042 (3)	0.004 (3)	0.024 (3)	0.006 (3)
C12	0.040 (3)	0.059 (3)	0.053 (4)	−0.008 (2)	0.021 (3)	0.005 (3)
C11	0.042 (3)	0.053 (3)	0.042 (3)	−0.004 (2)	0.016 (3)	−0.001 (3)
C22	0.037 (3)	0.049 (3)	0.046 (3)	−0.005 (2)	0.014 (3)	0.005 (3)
C18	0.038 (3)	0.050 (3)	0.040 (3)	−0.003 (2)	0.014 (3)	0.001 (3)
C15	0.042 (3)	0.050 (3)	0.041 (3)	−0.009 (2)	0.017 (3)	−0.005 (3)
C1	0.058 (4)	0.053 (3)	0.047 (4)	0.005 (3)	0.027 (3)	−0.004 (3)
C2	0.067 (4)	0.063 (3)	0.035 (3)	0.001 (3)	0.017 (3)	−0.008 (3)
C16	0.060 (3)	0.077 (4)	0.067 (4)	0.005 (3)	0.040 (3)	0.012 (3)
C23	0.053 (4)	0.078 (4)	0.053 (4)	0.004 (3)	0.001 (3)	−0.006 (3)
C27	0.030 (2)	0.035 (2)	0.036 (3)	0.004 (2)	0.011 (2)	0.002 (2)
C30	0.031 (3)	0.043 (3)	0.035 (3)	−0.001 (2)	0.007 (2)	−0.003 (2)
O5	0.0352 (18)	0.0435 (19)	0.056 (2)	−0.0024 (15)	0.0174 (18)	−0.0037 (16)
O6	0.039 (2)	0.052 (2)	0.087 (3)	−0.0079 (17)	0.035 (2)	−0.022 (2)
N5	0.036 (2)	0.042 (2)	0.043 (3)	−0.0043 (19)	0.013 (2)	−0.007 (2)
C28	0.036 (3)	0.034 (2)	0.044 (3)	0.001 (2)	0.012 (2)	−0.007 (2)
O2	0.040 (2)	0.072 (3)	0.077 (3)	0.0015 (18)	0.031 (2)	0.003 (2)
N3	0.039 (3)	0.057 (3)	0.046 (3)	−0.007 (2)	0.015 (2)	0.000 (2)
O7	0.042 (2)	0.071 (3)	0.060 (3)	−0.0120 (19)	0.0192 (19)	−0.031 (2)
C25	0.028 (2)	0.043 (3)	0.038 (3)	−0.001 (2)	0.010 (2)	0.001 (2)
C26	0.030 (3)	0.036 (3)	0.035 (3)	0.004 (2)	0.013 (2)	−0.005 (2)
O1	0.064 (2)	0.064 (3)	0.076 (3)	−0.026 (2)	0.032 (2)	−0.017 (2)
C29	0.030 (2)	0.051 (3)	0.036 (3)	0.008 (2)	0.013 (2)	0.000 (2)
N4	0.054 (3)	0.047 (3)	0.076 (4)	0.004 (2)	0.032 (3)	−0.013 (3)
O4	0.107 (4)	0.046 (2)	0.139 (5)	0.001 (2)	0.074 (3)	−0.002 (3)
O3	0.140 (4)	0.090 (3)	0.098 (4)	−0.033 (3)	0.074 (4)	−0.051 (3)

Geometric parameters (Å, º) top

N2—H2	0.8600	C12—H12	0.9300
N2—C7	1.337 (5)	C12—C11	1.389 (6)
N2—C8	1.397 (5)	C11—H11	0.9300
C6—H6	0.9300	C22—H22	0.9300
C6—C4	1.387 (6)	C18—H18	0.9300
C6—C1	1.386 (7)	C15—H15	0.9300
C7—N1	1.333 (5)	C1—H1A	0.9300
C7—C4	1.454 (6)	C1—C2	1.355 (7)
N1—H1	0.8600	C2—H2A	0.9300
N1—C9	1.380 (5)	C16—H16A	0.9600
C4—C5	1.379 (6)	C16—H16B	0.9600
C9—C8	1.369 (6)	C16—H16C	0.9600
C9—C10	1.476 (6)	C23—H23A	0.9600
C5—H5	0.9300	C23—H23B	0.9600
C5—C3	1.387 (7)	C23—H23C	0.9600
C8—C17	1.449 (6)	C27—O5	1.252 (5)
C19—H19	0.9300	C27—C28	1.451 (5)
C19—C20	1.387 (7)	C27—C26	1.448 (6)
C19—C18	1.386 (6)	C30—H30	0.9300
C14—H14	0.9300	C30—C25	1.375 (6)
C14—C13	1.360 (7)	C30—C26	1.363 (6)
C14—C15	1.397 (6)	O6—N5	1.218 (4)
C17—C22	1.389 (6)	N5—O7	1.240 (5)
C17—C18	1.392 (6)	N5—C26	1.440 (5)
C21—H21	0.9300	C28—C29	1.370 (6)
C21—C20	1.378 (6)	C28—N4	1.466 (6)
C21—C22	1.373 (6)	O2—N3	1.234 (5)
C3—H3	0.9300	N3—C25	1.460 (6)
C3—C2	1.374 (7)	N3—O1	1.213 (5)
C20—C23	1.522 (7)	C25—C29	1.375 (6)
C10—C11	1.386 (6)	C29—H29	0.9300
C10—C15	1.395 (6)	N4—O4	1.218 (6)
C13—C12	1.399 (7)	N4—O3	1.188 (6)
C13—C16	1.514 (6)

C7—N2—H2	124.5	C17—C22—H22	119.6
C7—N2—C8	111.1 (3)	C21—C22—C17	120.8 (4)
C8—N2—H2	124.5	C21—C22—H22	119.6
C4—C6—H6	120.2	C19—C18—C17	121.5 (5)
C1—C6—H6	120.2	C19—C18—H18	119.3
C1—C6—C4	119.6 (5)	C17—C18—H18	119.3
N2—C7—C4	126.6 (4)	C14—C15—H15	120.2
N1—C7—N2	106.2 (4)	C10—C15—C14	119.5 (4)
N1—C7—C4	127.2 (4)	C10—C15—H15	120.2
C7—N1—H1	124.7	C6—C1—H1A	120.1
C7—N1—C9	110.7 (4)	C2—C1—C6	119.7 (5)
C9—N1—H1	124.7	C2—C1—H1A	120.1
C6—C4—C7	120.1 (4)	C3—C2—H2A	119.1
C5—C4—C6	119.9 (4)	C1—C2—C3	121.7 (5)
C5—C4—C7	120.1 (4)	C1—C2—H2A	119.1
N1—C9—C10	119.1 (4)	C13—C16—H16A	109.5
C8—C9—N1	107.1 (4)	C13—C16—H16B	109.5
C8—C9—C10	133.8 (5)	C13—C16—H16C	109.5
C4—C5—H5	120.0	H16A—C16—H16B	109.5
C4—C5—C3	120.0 (4)	H16A—C16—H16C	109.5
C3—C5—H5	120.0	H16B—C16—H16C	109.5
N2—C8—C17	122.7 (4)	C20—C23—H23A	109.5
C9—C8—N2	104.9 (4)	C20—C23—H23B	109.5
C9—C8—C17	132.4 (4)	C20—C23—H23C	109.5
C20—C19—H19	119.7	H23A—C23—H23B	109.5
C18—C19—H19	119.7	H23A—C23—H23C	109.5
C18—C19—C20	120.6 (5)	H23B—C23—H23C	109.5
C13—C14—H14	119.0	O5—C27—C28	122.5 (4)
C13—C14—C15	122.1 (5)	O5—C27—C26	126.0 (4)
C15—C14—H14	119.0	C26—C27—C28	111.5 (3)
C22—C17—C8	120.4 (4)	C25—C30—H30	120.3
C22—C17—C18	117.3 (5)	C26—C30—H30	120.3
C18—C17—C8	122.2 (4)	C26—C30—C25	119.5 (4)
C20—C21—H21	119.0	O6—N5—O7	121.1 (4)
C22—C21—H21	119.0	O6—N5—C26	120.1 (4)
C22—C21—C20	122.1 (5)	O7—N5—C26	118.8 (4)
C5—C3—H3	120.5	C27—C28—N4	118.6 (4)
C2—C3—C5	119.0 (5)	C29—C28—C27	124.4 (4)
C2—C3—H3	120.5	C29—C28—N4	116.9 (4)
C19—C20—C23	120.5 (5)	O2—N3—C25	117.7 (4)
C21—C20—C19	117.7 (5)	O1—N3—O2	123.7 (4)
C21—C20—C23	121.7 (5)	O1—N3—C25	118.6 (4)
C11—C10—C9	119.3 (4)	C30—C25—N3	119.2 (4)
C11—C10—C15	118.6 (4)	C29—C25—C30	121.5 (4)
C15—C10—C9	122.0 (4)	C29—C25—N3	119.3 (4)
C14—C13—C12	118.4 (4)	C30—C26—C27	124.2 (4)
C14—C13—C16	122.7 (5)	C30—C26—N5	117.3 (4)
C12—C13—C16	118.9 (5)	N5—C26—C27	118.5 (4)
C13—C12—H12	119.9	C28—C29—C25	118.8 (4)
C11—C12—C13	120.2 (4)	C28—C29—H29	120.6
C11—C12—H12	119.9	C25—C29—H29	120.6
C10—C11—C12	121.0 (5)	O4—N4—C28	117.6 (5)
C10—C11—H11	119.5	O3—N4—C28	118.2 (5)
C12—C11—H11	119.5	O3—N4—O4	124.1 (5)

N2—C7—N1—C9	0.0 (5)	C22—C17—C18—C19	−0.8 (6)
N2—C7—C4—C6	29.4 (7)	C22—C21—C20—C19	−0.8 (7)
N2—C7—C4—C5	−151.6 (4)	C22—C21—C20—C23	176.5 (5)
N2—C8—C17—C22	−151.9 (4)	C18—C19—C20—C21	2.2 (7)
N2—C8—C17—C18	30.7 (7)	C18—C19—C20—C23	−175.2 (5)
C6—C4—C5—C3	−2.8 (7)	C18—C17—C22—C21	2.1 (7)
C6—C1—C2—C3	−0.5 (8)	C15—C14—C13—C12	2.5 (8)
C7—N2—C8—C9	0.5 (5)	C15—C14—C13—C16	−176.6 (4)
C7—N2—C8—C17	−178.0 (4)	C15—C10—C11—C12	1.1 (7)
C7—N1—C9—C8	0.3 (5)	C1—C6—C4—C7	−178.4 (4)
C7—N1—C9—C10	179.6 (4)	C1—C6—C4—C5	2.5 (7)
C7—C4—C5—C3	178.2 (4)	C16—C13—C12—C11	176.5 (5)
N1—C7—C4—C6	−150.7 (5)	C27—C28—C29—C25	−2.3 (7)
N1—C7—C4—C5	28.4 (7)	C27—C28—N4—O4	38.3 (7)
N1—C9—C8—N2	−0.5 (5)	C27—C28—N4—O3	−144.3 (5)
N1—C9—C8—C17	177.9 (5)	C30—C25—C29—C28	0.7 (7)
N1—C9—C10—C11	43.5 (6)	O5—C27—C28—C29	−176.7 (5)
N1—C9—C10—C15	−133.3 (5)	O5—C27—C28—N4	2.4 (7)
C4—C6—C1—C2	−0.9 (7)	O5—C27—C26—C30	178.0 (5)
C4—C7—N1—C9	−180.0 (4)	O5—C27—C26—N5	−3.2 (7)
C4—C5—C3—C2	1.3 (7)	O6—N5—C26—C27	20.9 (6)
C9—C8—C17—C22	30.0 (8)	O6—N5—C26—C30	−160.2 (4)
C9—C8—C17—C18	−147.4 (5)	C28—C27—C26—C30	−1.0 (6)
C9—C10—C11—C12	−175.8 (4)	C28—C27—C26—N5	177.8 (4)
C9—C10—C15—C14	175.5 (4)	O2—N3—C25—C30	−165.4 (4)
C5—C3—C2—C1	0.3 (8)	O2—N3—C25—C29	12.7 (6)
C8—N2—C7—N1	−0.3 (5)	N3—C25—C29—C28	−177.4 (4)
C8—N2—C7—C4	179.7 (4)	O7—N5—C26—C27	−158.8 (4)
C8—C9—C10—C11	−137.5 (5)	O7—N5—C26—C30	20.1 (6)
C8—C9—C10—C15	45.8 (8)	C25—C30—C26—C27	−0.3 (7)
C8—C17—C22—C21	−175.4 (4)	C25—C30—C26—N5	−179.2 (4)
C8—C17—C18—C19	176.8 (4)	C26—C27—C28—C29	2.4 (6)
C14—C13—C12—C11	−2.6 (8)	C26—C27—C28—N4	−178.6 (4)
C20—C19—C18—C17	−1.4 (7)	C26—C30—C25—N3	178.7 (4)
C20—C21—C22—C17	−1.4 (7)	C26—C30—C25—C29	0.6 (7)
C10—C9—C8—N2	−179.6 (5)	O1—N3—C25—C30	15.6 (6)
C10—C9—C8—C17	−1.3 (9)	O1—N3—C25—C29	−166.2 (5)
C13—C14—C15—C10	−0.5 (8)	C29—C28—N4—O4	−142.6 (5)
C13—C12—C11—C10	0.8 (7)	C29—C28—N4—O3	34.8 (7)
C11—C10—C15—C14	−1.3 (7)	N4—C28—C29—C25	178.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.64	3.107 (5)	115
N2—H2···O7ⁱⁱ	0.86	2.18	3.016 (4)	163
N1—H1···O5	0.86	1.95	2.727 (5)	149
N1—H1···O6	0.86	2.23	2.878 (5)	133
C21—H21···O3ⁱⁱⁱ	0.93	2.60	3.450 (7)	153

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

Acknowledgements

The authors are grateful to St. Joseph's College (A) Jakhama and the Department of Life and Consumer Sciences, University of South Africa for all the help received in carrying out the research work. The authors are also grateful to SAIC Tezpur University, India, for the X-ray data collections.

References

Amudha, M., Madhavan, J. & Praveen Kumar, P. (2017). J. Opt. 46, 382–390. CrossRef Google Scholar
Anandhi, S., Shyju, T. S., Srinivasan, T. P. & Gopalakrishnan, R. (2011). J. Cryst. Growth 335, 75–83. Web of Science CrossRef Google Scholar
Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2018). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, 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
Gierczyk, B., Zalas, M. & Otłowski, T. (2024). Molecules 29, 5588. Web of Science CrossRef PubMed Google Scholar
Krause, 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
Maldoni, B. (1991). J. Chem. Educ. 68, 700. CrossRef Web of Science Google Scholar
Mi, Z., Bi, Y., Feng, Y. & Zhang, T. (2016). Z. Anorg. Allge Chem. 642, 317–322. Web of Science CSD CrossRef Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Smiglak, M., Hines, C. C., Reichert, W. M., Vincek, A. S., Katritzky, A. R., Thrasher, J. S., Sun, L., McCrary, P. D., Beasley, P. A., Kelley, S. P. & Rogers, R. D. (2012). New J. Chem. 36, 702–722. Web of Science CSD CrossRef 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.

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 10| October 2025| x250877

https://doi.org/10.1107/S2414314625008776

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

2-Phenyl-4,5-di-p-tolyl-1H-imidazol-3-ium picrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds