Synthesis and structure of 4,5-diphenyl-1H-imidazol-3-ium thio­cyanate

Bensegueni, M.A.; Cherouana, A.

doi:10.1107/S2056989026005931

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ISSN: 2056-9890

Volume 82| Part 7| July 2026|

https://doi.org/10.1107/S2056989026005931

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Synthesis and structure of 4,5-diphenyl-1H-imidazol-3-ium thiocyanate

Mohamed Abdellatif Bensegueni ^a ^* and Aouatef Cherouana ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, Université Constantine 1 Frères Mentouri, Algeria
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 May 2026; accepted 3 June 2026; online 9 June 2026)

In the title molecular salt, C₁₅H₁₃N₂⁺·SCN⁻, the dihedral angles between the imidazole ring and pendant phenyl groups are 51.61 (14) and 35.47 (15)°. In the crystal, the ions are linked by N—H⋯N and C—H⋯S hydrogen bonds, forming R⁴₂(16) loops. These units are further connected by C—H⋯π and C—S⋯π interactions into a three-dimensional supramolecular network. Hirshfeld surface analysis of the imidazolium cation shows that H⋯H (42.9%), C⋯H/H⋯C (34.9%), N⋯H/H⋯N (10.7%) and H⋯S/S⋯H (6.5%) contacts are the major contributors to the crystal packing.

Keywords: crystal structure; 1H-imidazol-3-ium derivative; hydrogen bonds; Hirshfeld surface analysis.

CCDC reference: 2559579

1. Chemical context

Imidazole derivatives continue to attract attention in structural and supramolecular chemistry because they combine aromatic character, amphoteric behaviour and multiple donor/acceptor sites within a compact heterocyclic framework (Chen, 2016 ). In their neutral form, imidazoles are widely encountered as ligands and functional organic building blocks, whereas protonated imidazolium species are particularly attractive as cationic components of molecular salts, where they can serve as efficient hydrogen-bond donors and promote the formation of extended supramolecular assemblies. Aryl substitution at the 4- and 5-positions further enlarges the π-surface of the heterocycle and can enhance weak intermolecular contacts involving aromatic rings.

A search of the Cambridge Structural Database (CSD, version 6.01 with updates to February 2026; Groom et al., 2016 ) for the 4,5-diarylimidazole skeleton shows that this family is structurally diverse and includes neutral molecules, solvates and ionic derivatives. Representative neutral examples include 4,5-diphenyl-1H-imidazole (Stibrany et al., 2004 ; Kounavi et al., 2012 ), 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (Fridman et al., 2009 ), 4-(4,5-diphenyl-1H-imidazol-2-yl)benzaldehyde (Kimura et al., 2002 ), 2,4,5-triphenyl-4,5-dihydro-1H-imidazole hemihydrate (Huang et al., 2006 ).

Related salts and co-crystals further illustrate the versatility of this heterocyclic platform in the solid state. Examples include 4,5-diphenyl-2-(4-nitrophenyl)-1H-imidazole clathrates with water, acetic acid and dimethyl sulfoxide (Kaftory et al., 1998 ), 2-(3-nitrophenyl)-4,5-diphenyl-1H-imidazol-3-ium nitrate (Zhang, 2009 ), and trans-2-amino-4,5-diphenyl-4,5-dihydroimidazolium nitrate derivatives (Wüstenberg et al., 2023 ). These examples show that protonation of the imidazole ring and association with counter-ions or neutral conformers can generate a rich variety of supramolecular arrangements governed by classical hydrogen bonds and weaker aromatic contacts.

As part of our studies in this area, and in the context of our ongoing research on azole-based compounds (Bensegueni et al., 2009 , 2014 , 2015 , 2020 ), we now report the synthesis and structure of the title molecular salt, C₁₅H₁₃N₂⁺·SCN⁻ (I), in order to analyse how different types of hydrogen bonds cooperate in the consolidation of the crystal packing.

2. Structural commentary

The asymmetric unit of compound (I) consists of one 4,5-biphenylimidazolium cation and one thiocyanate anion. The crystal structure is orthorhombic and crystallizes in the space group P2₁2₁2₁ with a well-defined absolute structure.

The cation is formed by a protonated imidazolium ring substituted at the 4- and 5-positions by two phenyl groups. The imidazolium core, defined by atoms N1/N2/C1/C2/C9, displays bond lengths of 1.319 (4) Å for N1—C1, 1.326 (4) Å for N2—C1, 1.382 (4) Å for N1—C9 and 1.386 (3) Å for N2—C2, which are consistent with charge delocalization within the aromatic imidazolium fragment (Fig. 1). The cation consists of two phenyl rings (A containing C3–C8 and C containing C10–C15) and one imidazole ring (B) (see supplementary figure). The interplanar angles are 51.61 (14)° for A/B, 35.47 (15)° for B/C and 54.80 (12)° for A/C.

Figure 1
The molecular structure of (I) showing displacement ellipsoids drawn at the 50% probability level.

As expected, the thiocyanate anion is essentially linear, with an N3—C16—S1 bond angle of 179.4 (3)°. The corresponding bond distances, N3—C16 = 1.171 (4) Å and C16—S1 = 1.622 (3) Å, are in agreement with the expected geometry of a thiocyanate anion.

3. Supramolecular features

The crystal structure of (I) features three hydrogen bonds involving the thiocyanate anion as the principal acceptor. The N1—H1N⋯N3 and N2—H2⋯N3 hydrogen bonds (Table 1), with H⋯N distances of 1.98 and 2.02 Å, together with the C12—H12⋯S1 contact (H⋯S = 2.93 Å), generate an R₄³(16) ring motif that links two cations and two anions into discrete supramolecular cycles in the crystal packing (Fig. 2). In addition to these classical hydrogen bonds, the structure features three C—H⋯π interactions, with each aromatic ring accepting one such interaction. The C1—H1A⋯Cg3 contact, with a notably short H⋯Cg distance of 2.45 Å, reinforces the R₄³(16) motif (Etter et al., 1990 ). The other two bonds connect adjacent motifs into extended chains (supplementary figure).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/N2/C2/C9, C3–C8 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.86	1.98	2.835 (4)	171
N2—H2⋯N3ⁱⁱ	0.86	2.02	2.862 (3)	168
C12—H12⋯S1ⁱⁱⁱ	0.93	2.93	3.785 (2)	155
C1—H1A⋯Cg3^iv	0.93	2.45	3.330 (3)	158
C6—H6⋯Cg2^v	0.93	2.93	3.581 (4)	128
C7—H7⋯Cg1^vi	0.93	2.91	3.297 (4)	106
Symmetry codes: (i) ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (vi) .

Figure 2
The crystal packing of (I), showing the R₄³(16) hydrogen-bonded ring motifs and the one-dimensional chain generated by N—H⋯N and C—H⋯S interactions.

The crystal packing also features a very weak π–π stacking interaction between the A and B aromatic rings, with a centroid–centroid separation of 4.201 (12) Å, reinforced by a C—S⋯Cg1 contact [3.534 (2) Å, 94.96 (11)°], which links the hydrogen-bonded chains along the a- and c-axis directions and contributes to the three-dimensional supramolecular architecture. Overall, these interactions produce a zigzag one-dimensional arrangement extending along the b axis, which is then assembled into the full three-dimensional network (Fig. 3).

Figure 3
Simplified representation of the crystal packing showing the one-dimensional zigzag chain and its three-dimensional extension in (I).

4. Hirshfeld surface analysis

Hirshfeld surface (HS) analysis and the corresponding two-dimensional fingerprint plots (Fig. 4) were generated using CrystalExplorer 21.5 (Spackman et al., 2021 ) in order to examine the intermolecular interactions governing the crystal packing of the title salt. On the d_norm-mapped Hirshfeld surface (Fig. 6), the most intense red spots are associated with the shortest intermolecular contacts, particularly those involving the thiocyanate anion. These include the N—H⋯N and C—H⋯S hydrogen bonds, as well as the C—S⋯π and C—H⋯π interactions, which play a central role in the cohesion of the ionic assembly.

Figure 4
Hirshfeld surface mapped over d_norm and the associated fingerprint plots for (I), showing the percentage contributions of the different intermolecular contacts.

The two-dimensional fingerprint plots indicate that H⋯H contacts make the largest contribution to the Hirshfeld surface, accounting for 42.9%, as expected from the high proportion of hydrogen atoms in the organic cation and the importance of van der Waals interactions in the crystal packing.

The H⋯C/C⋯H contacts are also significant, contributing 34.9%, and they correspond to C-H⋯π interactions involving the aromatic rings. The H⋯N/N⋯H and H⋯S/S⋯H contacts contribute 10.7% and 6.4%, respectively, reflecting the presence of classical and non-classical hydrogen bonds involving the thiocyanate anion. In addition, the C⋯S/S⋯C contacts represent 1.4%, while the C⋯C contacts account for 1.5% of the surface.

The remaining intermolecular contacts are only minor, confirming that the supramolecular arrangement is governed primarily by hydrogen bonding, van der Waals interactions and aromatic contacts.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 6.01, updated to February 2026; Groom et al., 2016) for structures related to the title compound gave 1676 hits for organic, non-polymeric, error-free single-crystal entries containing the 4,5-diarylimidazole framework. The closest neutral analogues are the polymorphs of 4,5-diphenyl-1H-imidazole [CSD refcodes OCUSUA (Stibrany et al., 2001 ), OCUSUA01 (Stibrany et al., 2004), OCUSUA02 (Batsanov et al., 2004 ), OCUSUA03 (Kounavi et al., 2012), OCUSUA04 (Rheingold, 2013 )], together with related derivatives such as DPDMTH (King & Sengier, 1978 ), FASFAH01 (Fridman et al., 2009), FASFAH02 (Huang, 2016 ) and FOVNIO (Zhang, 2009). More relevant to the present structure are the imidazolium salts GETDIT (Braddock et al., 2006 ) and PASBEQ (Kaftory et al., 1998), which demonstrate that protonated diarylimidazolium species are known, although no thiocyanate salt of a 4,5-biarylimidazolium cation corresponding to the title compound was identified.

6. Synthesis and crystallization

An equimolar aqueous solution of 4,5-biphenylimidazolium and potassium thiocyanate was prepared in 10 ml of water at room temperature. The reaction mixture was stirred and heated at 343 K for 10 min, then left to evaporate slowly at room temperature. After a few weeks, colourless to white transparent single crystals of the title salt suitable for X-ray diffraction were obtained.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed in calculated positions and refined using a riding model, with N—H = 0.86 Å and C—H = 0.93 Å with U_iso(H) = 1.2U_eq(carrier) in all cases.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₂⁺·SCN⁻
M_r	279.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.5328 (3), 12.0855 (5), 18.0627 (8)
V (Å³)	1426.09 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan CrysAlis PRO; Agilent, 2014 ).
T_min, T_max	0.660, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8189, 2428, 2395
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 0.92
No. of reflections	2428
No. of parameters	169
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18
Absolute structure	Flack x determined using 919 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.08 (3)
Computer programs: APEX3 and SAINT (Bruker, 2015 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2559579

Crystal structure: contains datablocks I, import. DOI: https://doi.org/10.1107/S2056989026005931/hb8228sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989026005931/hb8228sup3.docx

Supporting information file. DOI: https://doi.org/10.1107/S2056989026005931/hb8228Isup3.cml

checkCIF report

Computing details top

4,5-Diphenyl-1H-imidazol-3-ium thiocyanate top

Crystal data top

C₁₅H₁₃N₂⁺·SCN⁻	D_x = 1.301 Mg m⁻³
M_r = 279.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 7394 reflections
a = 6.5328 (3) Å	θ = 2.2–27.0°
b = 12.0855 (5) Å	µ = 0.22 mm⁻¹
c = 18.0627 (8) Å	T = 100 K
V = 1426.09 (11) Å³	Block, colourless
Z = 4	0.20 × 0.15 × 0.10 mm
F(000) = 584

Data collection top

Bruker APEXII CCD diffractometer	2395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.018
ω and phi scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan CrysAlis PRO; Agilent, 2014).	h = −7→7
T_min = 0.660, T_max = 1.000	k = −14→13
8189 measured reflections	l = −20→15
2428 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0369P)² + 1.2893P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max = 0.001
S = 0.92	Δρ_max = 0.23 e Å⁻³
2428 reflections	Δρ_min = −0.18 e Å⁻³
169 parameters	Absolute structure: Flack x determined using 919 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
72 restraints	Absolute structure parameter: 0.08 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
N2	0.8116 (4)	0.70567 (18)	0.70220 (12)	0.0231 (5)
H2	0.756811	0.770267	0.704618	0.028*
N1	1.0144 (4)	0.56874 (19)	0.72286 (13)	0.0234 (5)
H1	1.113206	0.529875	0.740612	0.028*
C2	0.7439 (4)	0.6191 (2)	0.65825 (14)	0.0199 (6)
C3	0.5656 (4)	0.6301 (2)	0.60863 (15)	0.0215 (6)
C9	0.8718 (4)	0.5323 (2)	0.67190 (15)	0.0209 (6)
C1	0.9748 (5)	0.6726 (2)	0.73990 (15)	0.0249 (6)
H1A	1.049153	0.715774	0.772989	0.030*
C8	0.4006 (4)	0.6957 (2)	0.62873 (17)	0.0256 (6)
H8	0.401379	0.732630	0.673906	0.031*
C7	0.2342 (5)	0.7063 (3)	0.58137 (18)	0.0325 (7)
H7	0.123673	0.750352	0.594930	0.039*
C10	0.8736 (3)	0.41895 (12)	0.64286 (11)	0.0242 (6)
C11.	0.6950 (3)	0.35642 (16)	0.64335 (12)	0.0364 (7)
H11.	0.576452	0.384955	0.664493	0.044*
C12	0.6937 (3)	0.25123 (16)	0.61222 (14)	0.0594 (10)
H12	0.574200	0.209394	0.612546	0.071*
C13	0.8709 (5)	0.20858 (14)	0.58061 (13)	0.0676 (11)
H13	0.869996	0.138202	0.559791	0.081*
C14	1.0495 (4)	0.27111 (18)	0.58013 (12)	0.0605 (10)
H14	1.168045	0.242569	0.558982	0.073*
C15	1.0508 (3)	0.37629 (16)	0.61125 (12)	0.0387 (7)
H15	1.170301	0.418130	0.610928	0.046*
C4	0.5655 (5)	0.5773 (2)	0.53980 (16)	0.0268 (7)
H4	0.677352	0.534978	0.525256	0.032*
C6	0.2324 (5)	0.6516 (3)	0.51417 (18)	0.0342 (8)
H6	0.119540	0.657535	0.483036	0.041*
C5	0.3983 (5)	0.5883 (2)	0.49340 (17)	0.0326 (8)
H5	0.397810	0.552654	0.447776	0.039*
S1	0.66610 (13)	0.50873 (8)	0.86212 (5)	0.0427 (3)
N3	0.3105 (4)	0.4330 (2)	0.79293 (15)	0.0325 (6)
C16	0.4590 (5)	0.4652 (2)	0.82209 (16)	0.0259 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0267 (13)	0.0186 (11)	0.0241 (12)	0.0019 (10)	−0.0020 (11)	−0.0028 (10)
N1	0.0216 (12)	0.0244 (12)	0.0241 (12)	0.0022 (10)	−0.0042 (10)	0.0027 (10)
C2	0.0238 (14)	0.0168 (13)	0.0191 (13)	−0.0014 (11)	0.0009 (11)	0.0006 (10)
C3	0.0241 (14)	0.0153 (13)	0.0253 (15)	−0.0039 (12)	−0.0020 (11)	0.0042 (11)
C9	0.0215 (14)	0.0224 (14)	0.0188 (13)	−0.0028 (11)	−0.0008 (11)	0.0018 (11)
C1	0.0271 (15)	0.0259 (15)	0.0216 (15)	−0.0032 (13)	−0.0031 (12)	−0.0034 (11)
C8	0.0262 (15)	0.0225 (14)	0.0281 (16)	−0.0019 (12)	0.0033 (12)	0.0034 (12)
C7	0.0231 (15)	0.0324 (17)	0.0420 (18)	0.0015 (13)	−0.0003 (14)	0.0128 (14)
C10	0.0369 (14)	0.0180 (12)	0.0177 (13)	0.0048 (10)	−0.0048 (11)	0.0030 (11)
C11.	0.0415 (16)	0.0238 (13)	0.0439 (18)	−0.0009 (12)	−0.0213 (15)	0.0059 (13)
C12	0.093 (3)	0.0228 (15)	0.062 (2)	−0.0045 (16)	−0.053 (2)	0.0034 (14)
C13	0.142 (3)	0.0260 (17)	0.035 (2)	0.0237 (17)	−0.039 (2)	−0.0085 (15)
C14	0.116 (3)	0.0386 (17)	0.0265 (17)	0.0392 (17)	0.004 (2)	0.0023 (14)
C15	0.0556 (18)	0.0327 (14)	0.0278 (16)	0.0181 (14)	0.0119 (14)	0.0102 (12)
C4	0.0367 (17)	0.0175 (14)	0.0261 (15)	0.0018 (13)	−0.0032 (13)	0.0013 (11)
C6	0.0339 (17)	0.0316 (17)	0.0371 (17)	−0.0091 (14)	−0.0174 (15)	0.0155 (15)
C5	0.050 (2)	0.0197 (15)	0.0280 (16)	−0.0076 (14)	−0.0147 (15)	0.0024 (12)
S1	0.0329 (4)	0.0460 (5)	0.0491 (5)	−0.0121 (4)	−0.0116 (4)	0.0055 (4)
N3	0.0307 (14)	0.0248 (13)	0.0421 (15)	−0.0007 (12)	−0.0094 (13)	0.0036 (12)
C16	0.0318 (17)	0.0205 (14)	0.0254 (15)	0.0029 (13)	0.0010 (13)	0.0069 (11)

Geometric parameters (Å, º) top

N2—C1	1.326 (4)	C10—C15	1.3900
N2—C2	1.386 (3)	C11.—C12	1.3900
N2—H2	0.8600	C11.—H11.	0.9300
N1—C1	1.319 (4)	C12—C13	1.3900
N1—C9	1.382 (4)	C12—H12	0.9300
N1—H1	0.8600	C13—C14	1.3900
C2—C9	1.363 (4)	C13—H13	0.9300
C2—C3	1.476 (4)	C14—C15	1.3900
C3—C8	1.386 (4)	C14—H14	0.9300
C3—C4	1.397 (4)	C15—H15	0.9300
C9—C10	1.468 (3)	C4—C5	1.383 (4)
C1—H1A	0.9300	C4—H4	0.9300
C8—C7	1.389 (4)	C6—C5	1.379 (5)
C8—H8	0.9300	C6—H6	0.9300
C7—C6	1.382 (5)	C5—H5	0.9300
C7—H7	0.9300	S1—C16	1.622 (3)
C10—C11.	1.3900	N3—C16	1.171 (4)

C1—N2—C2	108.9 (2)	C15—C10—C9	119.98 (17)
C1—N2—H2	125.6	C10—C11.—C12	120.0
C2—N2—H2	125.6	C10—C11.—H11.	120.0
C1—N1—C9	109.0 (2)	C12—C11.—H11.	120.0
C1—N1—H1	125.5	C13—C12—C11.	120.0
C9—N1—H1	125.5	C13—C12—H12	120.0
C9—C2—N2	106.3 (2)	C11.—C12—H12	120.0
C9—C2—C3	131.6 (2)	C12—C13—C14	120.0
N2—C2—C3	122.1 (2)	C12—C13—H13	120.0
C8—C3—C4	119.6 (3)	C14—C13—H13	120.0
C8—C3—C2	120.4 (3)	C13—C14—C15	120.0
C4—C3—C2	120.0 (3)	C13—C14—H14	120.0
C2—C9—N1	106.8 (2)	C15—C14—H14	120.0
C2—C9—C10	131.2 (2)	C14—C15—C10	120.0
N1—C9—C10	122.0 (2)	C14—C15—H15	120.0
N1—C1—N2	108.9 (3)	C10—C15—H15	120.0
N1—C1—H1A	125.5	C5—C4—C3	119.7 (3)
N2—C1—H1A	125.5	C5—C4—H4	120.1
C3—C8—C7	120.0 (3)	C3—C4—H4	120.1
C3—C8—H8	120.0	C5—C6—C7	119.8 (3)
C7—C8—H8	120.0	C5—C6—H6	120.1
C6—C7—C8	120.2 (3)	C7—C6—H6	120.1
C6—C7—H7	119.9	C6—C5—C4	120.6 (3)
C8—C7—H7	119.9	C6—C5—H5	119.7
C11.—C10—C15	120.0	C4—C5—H5	119.7
C11.—C10—C9	119.93 (17)	N3—C16—S1	179.4 (3)

C1—N2—C2—C9	0.7 (3)	C2—C9—C10—C11.	−49.5 (4)
C1—N2—C2—C3	−179.2 (2)	N1—C9—C10—C11.	129.8 (2)
C9—C2—C3—C8	145.7 (3)	C2—C9—C10—C15	127.0 (3)
N2—C2—C3—C8	−34.4 (4)	N1—C9—C10—C15	−53.7 (3)
C9—C2—C3—C4	−36.5 (4)	C15—C10—C11.—C12	0.0
N2—C2—C3—C4	143.4 (3)	C9—C10—C11.—C12	176.5 (2)
N2—C2—C9—N1	−0.6 (3)	C10—C11.—C12—C13	0.0
C3—C2—C9—N1	179.2 (3)	C11.—C12—C13—C14	0.0
N2—C2—C9—C10	178.7 (3)	C12—C13—C14—C15	0.0
C3—C2—C9—C10	−1.4 (5)	C13—C14—C15—C10	0.0
C1—N1—C9—C2	0.4 (3)	C11.—C10—C15—C14	0.0
C1—N1—C9—C10	−179.1 (2)	C9—C10—C15—C14	−176.5 (2)
C9—N1—C1—N2	0.1 (3)	C8—C3—C4—C5	−2.0 (4)
C2—N2—C1—N1	−0.5 (3)	C2—C3—C4—C5	−179.7 (2)
C4—C3—C8—C7	1.7 (4)	C8—C7—C6—C5	−1.4 (5)
C2—C3—C8—C7	179.5 (3)	C7—C6—C5—C4	1.2 (5)
C3—C8—C7—C6	0.0 (4)	C3—C4—C5—C6	0.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/N2/C2/C9, C3–C8 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.86	1.98	2.835 (4)	171
N2—H2···N3ⁱⁱ	0.86	2.02	2.862 (3)	168
C12—H12···S1ⁱⁱⁱ	0.93	2.93	3.785 (2)	155
C1—H1A···Cg3^iv	0.93	2.45	3.330 (3)	158
C6—H6···Cg2^v	0.93	2.93	3.581 (4)	128
C7—H7···Cg1^vi	0.93	2.91	3.297 (4)	106

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2; (v) x−1/2, −y+3/2, −z+1; (vi) x−1, y, z.

Acknowledgements

The authors sincerely thank the CRM² laboratory, Nancy, France, for its valuable assistance with the single-crystal X-ray diffraction measurements and data collection and the Direction Générale de la Recherche Scientifique et du Développement Technologique-Algérie. (DGRSDT) for support.

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