1-[(E)-1-(2-Carb­oxy-6-methyl­phen­yl)diazen-1-ium-2-yl]naphthalen-2-olate

Benabila, N.; Brihi, O.; Chetioui, S.; Djukic, J.-P.

doi:10.1107/S2414314625011484

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 12| December 2025| x251148

https://doi.org/10.1107/S2414314625011484

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1-[(E)-1-(2-Carboxy-6-methylphenyl)diazen-1-ium-2-yl]naphthalen-2-olate

Nabila Benabila,^a ^* Ouarda Brihi,^b Souheyla Chetioui ^c,^d ^* and Jean-Pierre Djukic ^e

^aLaboratory of Therapeutic Organic Substances and Sustainable Processes (LTOCSP), University of M'sila, University Pole, Road Bourdj Bou Arreiridj, 28000 M'sila, Algeria, ^bLaboratoire de Cristallographie, Département de Physique, Université des Frères Mentouri-Constantine, 25000 Constantine, Algeria, ^cVEHDD Laboratory. University of M'sila, University Pole, Road Bourdj Bou Arreiridj, 28000 M'sila, Algeria, ^dResearch Unit for Chemistry of the Environment and Molecular Structural, University of Constantine 1, Constantine 25000, Algeria, and ^eLaboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex, France
^*Correspondence e-mail: [email protected], [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 11 December 2025; accepted 20 December 2025; online 24 December 2025)

The title compound, C₁₈H₁₄N₂O₃, crystallizes with two zwitterionic molecules (A and B) in the asymmetric unit, each featuring an intramolecular N—H⋯O hydrogen bond. In the extended structure, A + A and B + B carboxylic-acid inversion dimers linked by pairwise O—H⋯O hydrogen bonds arise, which generate R²₂(8) loops in each case. The dimers are linked by weak C—H⋯π and π–π stacking interactions.

Keywords: azo compound; 2-naphthol; crystal structure.

CCDC reference: 2517770

Structure description

Azo compounds are crucial in dyes, pigments, and innovative materials (Wang et al., 2003 ). As part of our studies in this area, we now describe the structure of the title compond, C₁₈H₁₄N₂O₃ (I), which crystallizes in the triclinic space group P $[\overline{1}]$ with two molecules (A and B) in the asymmetric unit (Fig. 1), in which nominal transfer of the hydrogen atom of the OH group to the N atom of the azo group has occurred to form a zwitterion in both molecules (Xu et al., 2010 ). Intramolecular N2—H2N⋯O1 and N4—H4N⋯O4 hydrogen bonds arise within the zwitterions (Table 1). The dihedral angles between the benzene and naphthalene ring systems are 11.19 (9)° in A and 10.62 (9)° in B. The N=N bond lengths in the azo group [1.309 (2) Å in A and 1.311 (2) Å in B] are similar to those found in related structures, for example 1-(3-acetylphenyl)-2-(2-oxidonaphthalen-1-yl) diazen-1-ium (Bougueria et al.., 2013 ) and 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene] naphthalen-2(1H)-one (Akkache et al., 2024 ). For molecule A, the C10—N1 [1.333 (2) Å] bond length is as expected for a C=N double bond and the C1—C10 and C9—C10 bond lengths are almost the same [1.457 (2) and 1.459 (2) Å, respectively]. However, the C1—C10—N1 bond angle [116.26 (13)°] is notably smaller than C9—C10—N1 [123.54 (14)°] possibly due to steric repulsion between N1 and O1.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg5 are the centroids of the C1–C6 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.88	1.86	2.5567 (17)	135
O3—H3A⋯O2ⁱ	0.84	1.81	2.6480 (17)	173
N4—H4N⋯O4	0.88	1.86	2.5519 (18)	134
O6—H6A⋯O5ⁱⁱ	0.84	1.81	2.6430 (18)	169
C17—H17C⋯Cg5ⁱⁱⁱ	0.98	2.81	3.6782 (18)	148
C35—H35C⋯Cg1^iv	0.98	2.70	3.5948 (18)	152
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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

In the crystal, the A and B molecules are linked by pairs of O—H⋯O hydrogen bonds associated with the carboxylic acid groups (Fig. 2, Table 1) to form A + A and B + B inversion dimers enclosing R₂²(8) loops in each case. The packing is consolidated by weak C—H⋯π interactions (Table 1) and aromatic π–π stacking, the shortest centroid–centroid separation being 3.6672 (10) Å between the C11–C16 and C19/C24–C28 rings.

Figure 2
A packing diagram for (I) viewed along the c-axis direction (projection onto the ab plane), showing the O—H⋯O hydrogen bonds as black dashed lines.

The intermolecular interactions in (I) were further investigated and visualized using CrystalExplorer (Spackman et al.., 2021 ). Fig. 3 shows the Hirshfeld surface for molecule A and Fig. 4 illustrates the two-dimensional fingerprint plots for molecule A encompassing all intermolecular interactions and the different contact types. The most significant contributions are H⋯H (40.7%), O⋯H/H⋯O (23.2%), C⋯H/H⋯C (20.8%) and C⋯C (8.7%) contacts. The Hirshfeld surface for molecule B is almost identical in appearance and the corresponding contact percentages are 39.4%, 25.5%, 20.7% and 8.3%, respectively.

Figure 3
View of the three-dimensional Hirshfeld surface for molecule A over d_norm in the range of −0.73 to 1.45 a.u, showing the intense red spots associated with the carboxylic acid inversion dimer.

Figure 4
(a) The full two-dimensional fingerprint plot calculated for molecule A and those delineated into (b) H⋯H contacts, (c) O⋯H/H⋯O contacts, (d) C⋯H/H⋯C contacts and (e) C⋯C contacts.

Synthesis and crystallization

The title compound was synthesized according to a reported method (Wang et al., 2003). The crude azo dye was recrystallized from hot ethanol solution in 80% yield and single crystals suitable for X-ray analysis were obtained by dissolving the compound in a minimum amount of tetrahydrofuran and water (1/1 v/v) at room temperature followed by slow evaporation.

Refinement

Crystallographic data and refinement parameters for the title compound are given in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.31
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	7.7505 (4), 11.8612 (7), 16.2866 (9)
α, β, γ (°)	83.111 (1), 79.292 (1), 84.218 (1)
V (Å³)	1455.81 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.653, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	23441, 8414, 5800
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.157, 1.04
No. of reflections	8414
No. of parameters	419
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.34
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick 2015a ), SHELXL2014 (Sheldrick 2015b ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2517770

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314625011484/hb4550sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314625011484/hb4550Isup3.cml

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625011484/hb4550Isup4.hkl

checkCIF report

Computing details top

(E)-1-(2-Carboxy-6-methylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium top

Crystal data top

C₁₈H₁₄N₂O₃	Z = 4
M_r = 306.31	F(000) = 640
Triclinic, P1	D_x = 1.398 Mg m⁻³
a = 7.7505 (4) Å	Mo Kα radiation, λ = 0.7107 Å
b = 11.8612 (7) Å	Cell parameters from 8371 reflections
c = 16.2866 (9) Å	θ = 2.3–29.9°
α = 83.111 (1)°	µ = 0.10 mm⁻¹
β = 79.292 (1)°	T = 173 K
γ = 84.218 (1)°	Block, red
V = 1455.81 (14) Å³	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	8414 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.0226 pixels mm^-1	θ_max = 30.0°, θ_min = 1.3°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −16→16
T_min = 0.653, T_max = 0.746	l = −22→22
23441 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.157	w = 1/[σ²(F_o²) + (0.0758P)² + 0.5416P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
8414 reflections	Δρ_max = 0.54 e Å⁻³
419 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
O1	0.38498 (18)	0.87201 (11)	0.39238 (7)	0.0344 (4)
O2	0.43533 (17)	0.86654 (10)	0.00964 (7)	0.0306 (4)
O3	0.62784 (15)	0.93350 (10)	0.07536 (7)	0.0278 (3)
N1	0.36970 (17)	0.88290 (11)	0.21732 (8)	0.0210 (3)
N2	0.46912 (17)	0.79838 (11)	0.24785 (8)	0.0218 (3)
C1	0.18485 (19)	1.05409 (13)	0.22892 (10)	0.0205 (4)
C2	0.1720 (2)	1.06406 (15)	0.14327 (10)	0.0261 (5)
C3	0.0828 (2)	1.15847 (16)	0.10777 (11)	0.0315 (5)
C4	0.0047 (2)	1.24658 (16)	0.15611 (12)	0.0345 (5)
O4	0.23104 (19)	0.50791 (12)	0.10738 (8)	0.0380 (4)
O5	0.22532 (16)	0.48158 (11)	0.48780 (8)	0.0320 (4)
C5	0.0109 (2)	1.23640 (15)	0.24043 (11)	0.0296 (5)
O6	0.03996 (15)	0.39734 (10)	0.42839 (8)	0.0298 (3)
C6	0.0985 (2)	1.14012 (14)	0.27841 (10)	0.0234 (4)
C7	0.1027 (2)	1.12783 (15)	0.36725 (10)	0.0280 (5)
C8	0.1932 (2)	1.03958 (15)	0.40481 (11)	0.0297 (5)
C9	0.2944 (2)	0.95199 (14)	0.35711 (10)	0.0251 (4)
C10	0.2868 (2)	0.95937 (13)	0.26776 (9)	0.0200 (4)
C11	0.55681 (19)	0.71804 (13)	0.19467 (9)	0.0201 (4)
C12	0.6230 (2)	0.61409 (13)	0.23267 (10)	0.0224 (4)
C13	0.7000 (2)	0.53091 (14)	0.18083 (11)	0.0282 (5)
C14	0.7088 (3)	0.54803 (15)	0.09399 (11)	0.0317 (5)
C15	0.6457 (2)	0.65149 (14)	0.05738 (10)	0.0281 (5)
C16	0.5745 (2)	0.73871 (13)	0.10678 (10)	0.0225 (4)
C17	0.6097 (2)	0.59299 (15)	0.32641 (10)	0.0290 (5)
C18	0.5367 (2)	0.85371 (13)	0.06156 (9)	0.0229 (4)
N3	0.21643 (17)	0.51973 (11)	0.28291 (8)	0.0214 (3)
N4	0.29368 (17)	0.42655 (11)	0.25216 (8)	0.0230 (4)
C19	0.05156 (19)	0.69943 (13)	0.27119 (9)	0.0200 (4)
C20	0.0364 (2)	0.70934 (14)	0.35725 (10)	0.0252 (5)
C21	−0.0629 (2)	0.80025 (15)	0.39276 (11)	0.0301 (5)
C22	−0.1516 (2)	0.88391 (15)	0.34388 (12)	0.0309 (5)
C23	−0.1325 (2)	0.87698 (14)	0.25871 (11)	0.0270 (5)
C24	−0.0298 (2)	0.78662 (13)	0.22098 (10)	0.0228 (4)
C25	−0.0049 (2)	0.78090 (15)	0.13164 (11)	0.0293 (5)
C26	0.0838 (3)	0.69271 (16)	0.09449 (11)	0.0332 (5)
C27	0.1578 (2)	0.59493 (15)	0.14226 (10)	0.0274 (5)
C28	0.14551 (19)	0.60074 (13)	0.23229 (9)	0.0203 (4)
C29	0.3755 (2)	0.34388 (13)	0.30435 (9)	0.0211 (4)
C30	0.4950 (2)	0.26046 (14)	0.26575 (10)	0.0238 (4)
C31	0.5887 (2)	0.18429 (15)	0.31662 (11)	0.0295 (5)
C32	0.5685 (2)	0.19012 (16)	0.40255 (11)	0.0329 (5)
C33	0.4463 (2)	0.27065 (15)	0.44036 (10)	0.0291 (5)
C34	0.3452 (2)	0.34531 (13)	0.39205 (10)	0.0228 (4)
C35	0.5201 (2)	0.25318 (15)	0.17265 (10)	0.0289 (5)
C36	0.1952 (2)	0.41597 (13)	0.43802 (9)	0.0232 (4)
H2	0.22515	1.00542	0.10968	0.0313*
H2N	0.48081	0.79203	0.30097	0.0261*
H3	0.07416	1.16391	0.04998	0.0377*
H3A	0.60056	0.99462	0.04723	0.0416*
H4	−0.05205	1.31281	0.13065	0.0414*
H5	−0.04471	1.29505	0.27348	0.0355*
H7	0.03934	1.18407	0.40058	0.0336*
H8	0.19046	1.03473	0.46368	0.0356*
H13	0.74770	0.46065	0.20522	0.0338*
H14	0.75797	0.48889	0.06012	0.0381*
H15	0.65084	0.66315	−0.00174	0.0337*
H17A	0.65978	0.51569	0.34135	0.0435*
H17B	0.48567	0.60117	0.35334	0.0435*
H17C	0.67494	0.64834	0.34567	0.0435*
H4N	0.29410	0.41611	0.19953	0.0277*
H6A	−0.03481	0.44257	0.45454	0.0447*
H20	0.09483	0.65309	0.39134	0.0303*
H21	−0.07122	0.80622	0.45104	0.0361*
H22	−0.22375	0.94450	0.36909	0.0371*
H23	−0.18988	0.93441	0.22505	0.0324*
H25	−0.05344	0.84233	0.09776	0.0352*
H26	0.09873	0.69423	0.03515	0.0398*
H31	0.66866	0.12670	0.29178	0.0354*
H32	0.63793	0.13929	0.43535	0.0395*
H33	0.43175	0.27479	0.49917	0.0350*
H35A	0.60926	0.19113	0.15721	0.0433*
H35B	0.55890	0.32531	0.14245	0.0433*
H35C	0.40830	0.23836	0.15765	0.0433*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0439 (7)	0.0352 (7)	0.0232 (6)	0.0110 (6)	−0.0105 (5)	−0.0040 (5)
O2	0.0385 (7)	0.0277 (6)	0.0262 (6)	0.0018 (5)	−0.0117 (5)	0.0002 (5)
O3	0.0306 (6)	0.0207 (6)	0.0309 (6)	−0.0006 (5)	−0.0065 (5)	0.0021 (5)
N1	0.0206 (6)	0.0195 (6)	0.0218 (6)	0.0015 (5)	−0.0028 (5)	−0.0021 (5)
N2	0.0251 (6)	0.0205 (6)	0.0183 (6)	0.0046 (5)	−0.0035 (5)	−0.0025 (5)
C1	0.0187 (7)	0.0191 (7)	0.0228 (7)	−0.0004 (5)	−0.0019 (5)	−0.0018 (5)
C2	0.0267 (8)	0.0262 (8)	0.0241 (8)	0.0039 (7)	−0.0031 (6)	−0.0044 (6)
C3	0.0313 (9)	0.0343 (10)	0.0266 (8)	0.0061 (7)	−0.0064 (7)	0.0003 (7)
C4	0.0317 (9)	0.0295 (9)	0.0394 (10)	0.0096 (7)	−0.0086 (7)	0.0016 (8)
O4	0.0514 (8)	0.0378 (7)	0.0233 (6)	0.0138 (6)	−0.0080 (5)	−0.0096 (5)
O5	0.0361 (7)	0.0323 (7)	0.0280 (6)	0.0059 (5)	−0.0057 (5)	−0.0124 (5)
C5	0.0256 (8)	0.0233 (8)	0.0374 (9)	0.0052 (7)	−0.0017 (7)	−0.0056 (7)
O6	0.0260 (6)	0.0275 (6)	0.0332 (6)	0.0040 (5)	0.0007 (5)	−0.0069 (5)
C6	0.0202 (7)	0.0202 (8)	0.0287 (8)	−0.0003 (6)	−0.0015 (6)	−0.0039 (6)
C7	0.0307 (8)	0.0245 (8)	0.0275 (8)	0.0011 (7)	0.0003 (7)	−0.0092 (6)
C8	0.0370 (9)	0.0298 (9)	0.0219 (8)	0.0020 (7)	−0.0034 (7)	−0.0081 (7)
C9	0.0289 (8)	0.0238 (8)	0.0225 (7)	0.0004 (6)	−0.0040 (6)	−0.0044 (6)
C10	0.0213 (7)	0.0178 (7)	0.0204 (7)	−0.0006 (6)	−0.0029 (5)	−0.0022 (5)
C11	0.0199 (7)	0.0182 (7)	0.0210 (7)	0.0016 (5)	−0.0019 (5)	−0.0031 (5)
C12	0.0240 (7)	0.0189 (7)	0.0235 (7)	−0.0007 (6)	−0.0041 (6)	0.0001 (6)
C13	0.0345 (9)	0.0163 (7)	0.0312 (9)	0.0033 (7)	−0.0041 (7)	0.0010 (6)
C14	0.0413 (10)	0.0213 (8)	0.0302 (9)	0.0047 (7)	−0.0014 (7)	−0.0068 (7)
C15	0.0368 (9)	0.0247 (8)	0.0211 (7)	0.0023 (7)	−0.0025 (6)	−0.0041 (6)
C16	0.0252 (7)	0.0196 (7)	0.0216 (7)	0.0018 (6)	−0.0039 (6)	−0.0015 (6)
C17	0.0360 (9)	0.0255 (8)	0.0243 (8)	0.0009 (7)	−0.0071 (7)	0.0024 (6)
C18	0.0259 (7)	0.0210 (8)	0.0191 (7)	0.0031 (6)	0.0004 (5)	−0.0019 (6)
N3	0.0220 (6)	0.0188 (6)	0.0225 (6)	0.0024 (5)	−0.0029 (5)	−0.0033 (5)
N4	0.0257 (7)	0.0215 (7)	0.0207 (6)	0.0052 (5)	−0.0038 (5)	−0.0037 (5)
C19	0.0188 (7)	0.0170 (7)	0.0234 (7)	−0.0004 (5)	−0.0024 (5)	−0.0020 (5)
C20	0.0301 (8)	0.0204 (8)	0.0245 (8)	0.0025 (6)	−0.0049 (6)	−0.0031 (6)
C21	0.0388 (9)	0.0232 (8)	0.0276 (8)	−0.0001 (7)	−0.0038 (7)	−0.0055 (6)
C22	0.0315 (9)	0.0203 (8)	0.0394 (10)	0.0041 (7)	−0.0023 (7)	−0.0079 (7)
C23	0.0262 (8)	0.0181 (8)	0.0364 (9)	0.0020 (6)	−0.0086 (7)	−0.0004 (6)
C24	0.0216 (7)	0.0197 (7)	0.0272 (8)	−0.0014 (6)	−0.0055 (6)	−0.0014 (6)
C25	0.0324 (9)	0.0273 (9)	0.0279 (8)	0.0029 (7)	−0.0110 (7)	0.0029 (7)
C26	0.0423 (10)	0.0354 (10)	0.0205 (8)	0.0059 (8)	−0.0089 (7)	0.0001 (7)
C27	0.0289 (8)	0.0295 (9)	0.0226 (8)	0.0030 (7)	−0.0041 (6)	−0.0031 (6)
C28	0.0197 (7)	0.0198 (7)	0.0206 (7)	0.0017 (6)	−0.0029 (5)	−0.0024 (5)
C29	0.0219 (7)	0.0192 (7)	0.0209 (7)	0.0034 (6)	−0.0020 (5)	−0.0035 (6)
C30	0.0229 (7)	0.0220 (8)	0.0245 (8)	0.0028 (6)	0.0004 (6)	−0.0049 (6)
C31	0.0281 (8)	0.0261 (9)	0.0310 (9)	0.0100 (7)	−0.0007 (7)	−0.0066 (7)
C32	0.0331 (9)	0.0307 (9)	0.0322 (9)	0.0117 (7)	−0.0079 (7)	−0.0008 (7)
C33	0.0325 (9)	0.0301 (9)	0.0228 (8)	0.0074 (7)	−0.0049 (6)	−0.0029 (6)
C34	0.0240 (7)	0.0205 (7)	0.0221 (7)	0.0050 (6)	−0.0013 (6)	−0.0051 (6)
C35	0.0302 (8)	0.0293 (9)	0.0257 (8)	0.0028 (7)	0.0006 (6)	−0.0098 (7)
C36	0.0280 (8)	0.0202 (7)	0.0186 (7)	0.0053 (6)	−0.0013 (6)	−0.0014 (5)

Geometric parameters (Å, º) top

O1—C9	1.268 (2)	C8—H8	0.9500
O2—C18	1.244 (2)	C13—H13	0.9500
O3—C18	1.300 (2)	C14—H14	0.9500
N1—N2	1.3089 (19)	C15—H15	0.9500
N1—C10	1.333 (2)	C17—H17C	0.9800
N2—C11	1.403 (2)	C17—H17B	0.9800
O3—H3A	0.8400	C17—H17A	0.9800
C1—C2	1.407 (2)	N4—H4N	0.8800
C1—C10	1.457 (2)	C19—C20	1.403 (2)
C1—C6	1.414 (2)	C19—C24	1.412 (2)
C2—C3	1.380 (2)	C19—C28	1.462 (2)
N2—H2N	0.8800	C20—C21	1.381 (2)
C3—C4	1.404 (3)	C21—C22	1.403 (2)
O4—C27	1.270 (2)	C22—C23	1.379 (3)
C4—C5	1.374 (3)	C23—C24	1.402 (2)
C5—C6	1.407 (2)	C24—C25	1.441 (2)
O5—C36	1.255 (2)	C25—C26	1.336 (3)
C6—C7	1.443 (2)	C26—C27	1.447 (3)
O6—C36	1.286 (2)	C27—C28	1.461 (2)
C7—C8	1.349 (2)	C29—C30	1.407 (2)
C8—C9	1.450 (2)	C29—C34	1.406 (2)
C9—C10	1.459 (2)	C30—C35	1.504 (2)
C11—C12	1.405 (2)	C30—C31	1.394 (2)
C11—C16	1.406 (2)	C31—C32	1.388 (2)
C12—C17	1.503 (2)	C32—C33	1.390 (2)
C12—C13	1.392 (2)	C33—C34	1.393 (2)
C13—C14	1.394 (2)	C34—C36	1.498 (2)
C14—C15	1.383 (2)	C20—H20	0.9500
C15—C16	1.394 (2)	C21—H21	0.9500
C16—C18	1.499 (2)	C22—H22	0.9500
C2—H2	0.9500	C23—H23	0.9500
C3—H3	0.9500	C25—H25	0.9500
N3—C28	1.333 (2)	C26—H26	0.9500
N3—N4	1.3110 (18)	C31—H31	0.9500
N4—C29	1.400 (2)	C32—H32	0.9500
C4—H4	0.9500	C33—H33	0.9500
C5—H5	0.9500	C35—H35A	0.9800
O6—H6A	0.8400	C35—H35B	0.9800
C7—H7	0.9500	C35—H35C	0.9800

N2—N1—C10	119.06 (13)	H17B—C17—H17C	109.00
N1—N2—C11	119.05 (12)	C12—C17—H17A	109.00
C18—O3—H3A	109.00	H17A—C17—H17B	109.00
C2—C1—C6	118.73 (14)	N3—N4—H4N	121.00
C2—C1—C10	122.21 (14)	C29—N4—H4N	121.00
C6—C1—C10	119.04 (14)	C20—C19—C24	118.81 (14)
C11—N2—H2N	120.00	C20—C19—C28	122.14 (14)
N1—N2—H2N	120.00	C24—C19—C28	119.04 (13)
C1—C2—C3	120.41 (16)	C19—C20—C21	120.47 (15)
C2—C3—C4	120.73 (16)	C20—C21—C22	120.84 (16)
C3—C4—C5	119.57 (17)	C21—C22—C23	119.06 (16)
C4—C5—C6	120.76 (16)	C22—C23—C24	121.09 (15)
C1—C6—C5	119.68 (15)	C19—C24—C23	119.58 (15)
C1—C6—C7	119.26 (15)	C19—C24—C25	119.12 (14)
C5—C6—C7	121.07 (15)	C23—C24—C25	121.30 (15)
C6—C7—C8	122.53 (16)	C24—C25—C26	122.66 (16)
C7—C8—C9	121.29 (16)	C25—C26—C27	121.74 (16)
C8—C9—C10	117.48 (14)	C26—C27—C28	117.19 (15)
O1—C9—C8	120.79 (15)	O4—C27—C26	121.45 (15)
O1—C9—C10	121.73 (14)	O4—C27—C28	121.36 (15)
N1—C10—C1	116.26 (13)	N3—C28—C19	116.57 (13)
N1—C10—C9	123.54 (14)	N3—C28—C27	123.54 (14)
C1—C10—C9	120.21 (14)	C19—C28—C27	119.89 (14)
C12—C11—C16	120.85 (14)	C30—C29—C34	120.53 (14)
N2—C11—C12	117.39 (13)	N4—C29—C30	117.62 (13)
N2—C11—C16	121.75 (14)	N4—C29—C34	121.81 (14)
C11—C12—C17	121.07 (14)	C29—C30—C35	121.13 (14)
C11—C12—C13	117.90 (14)	C29—C30—C31	117.87 (15)
C13—C12—C17	121.03 (14)	C31—C30—C35	121.01 (15)
C12—C13—C14	121.69 (16)	C30—C31—C32	121.91 (16)
C13—C14—C15	119.71 (16)	C31—C32—C33	119.70 (16)
C14—C15—C16	120.32 (15)	C32—C33—C34	120.01 (15)
C15—C16—C18	116.92 (14)	C33—C34—C36	117.25 (14)
C11—C16—C15	119.33 (14)	C29—C34—C33	119.72 (14)
C11—C16—C18	123.49 (14)	C29—C34—C36	122.73 (14)
O2—C18—O3	123.85 (14)	O5—C36—O6	124.05 (15)
O2—C18—C16	120.62 (14)	O5—C36—C34	119.46 (14)
O3—C18—C16	115.27 (13)	O6—C36—C34	116.23 (13)
C1—C2—H2	120.00	C19—C20—H20	120.00
C3—C2—H2	120.00	C21—C20—H20	120.00
C2—C3—H3	120.00	C20—C21—H21	120.00
C4—C3—H3	120.00	C22—C21—H21	120.00
N4—N3—C28	119.03 (13)	C21—C22—H22	120.00
C3—C4—H4	120.00	C23—C22—H22	120.00
C5—C4—H4	120.00	C22—C23—H23	119.00
N3—N4—C29	118.99 (12)	C24—C23—H23	119.00
C4—C5—H5	120.00	C24—C25—H25	119.00
C6—C5—H5	120.00	C26—C25—H25	119.00
C36—O6—H6A	109.00	C25—C26—H26	119.00
C6—C7—H7	119.00	C27—C26—H26	119.00
C8—C7—H7	119.00	C30—C31—H31	119.00
C7—C8—H8	119.00	C32—C31—H31	119.00
C9—C8—H8	119.00	C31—C32—H32	120.00
C12—C13—H13	119.00	C33—C32—H32	120.00
C14—C13—H13	119.00	C32—C33—H33	120.00
C15—C14—H14	120.00	C34—C33—H33	120.00
C13—C14—H14	120.00	C30—C35—H35A	109.00
C14—C15—H15	120.00	C30—C35—H35B	109.00
C16—C15—H15	120.00	C30—C35—H35C	109.00
C12—C17—H17B	109.00	H35A—C35—H35B	110.00
C12—C17—H17C	109.00	H35A—C35—H35C	109.00
H17A—C17—H17C	109.00	H35B—C35—H35C	109.00

C10—N1—N2—C11	−179.82 (14)	C28—N3—N4—C29	176.97 (14)
N2—N1—C10—C9	−2.7 (2)	N4—N3—C28—C27	−3.8 (2)
N2—N1—C10—C1	177.27 (13)	N4—N3—C28—C19	176.25 (13)
N1—N2—C11—C12	−163.54 (14)	N3—N4—C29—C30	−163.68 (14)
N1—N2—C11—C16	14.9 (2)	N3—N4—C29—C34	14.2 (2)
C6—C1—C2—C3	2.6 (2)	C24—C19—C20—C21	2.9 (2)
C10—C1—C2—C3	−176.15 (15)	C28—C19—C20—C21	−175.81 (15)
C2—C1—C10—N1	0.9 (2)	C20—C19—C28—N3	0.2 (2)
C2—C1—C10—C9	−179.24 (15)	C20—C19—C28—C27	−179.80 (14)
C6—C1—C10—N1	−177.94 (14)	C24—C19—C28—N3	−178.51 (14)
C2—C1—C6—C5	−3.7 (2)	C20—C19—C24—C23	−4.0 (2)
C2—C1—C6—C7	176.68 (15)	C20—C19—C24—C25	175.84 (15)
C10—C1—C6—C5	175.15 (15)	C28—C19—C24—C23	174.73 (14)
C10—C1—C6—C7	−4.5 (2)	C28—C19—C24—C25	−5.5 (2)
C6—C1—C10—C9	2.0 (2)	C24—C19—C28—C27	1.5 (2)
C1—C2—C3—C4	0.6 (2)	C19—C20—C21—C22	0.5 (2)
C2—C3—C4—C5	−2.7 (3)	C20—C21—C22—C23	−2.7 (2)
C3—C4—C5—C6	1.7 (2)	C21—C22—C23—C24	1.5 (2)
C4—C5—C6—C7	−178.81 (16)	C22—C23—C24—C25	−178.01 (15)
C4—C5—C6—C1	1.6 (2)	C22—C23—C24—C19	1.8 (2)
C1—C6—C7—C8	3.2 (2)	C19—C24—C25—C26	4.1 (3)
C5—C6—C7—C8	−176.44 (16)	C23—C24—C25—C26	−176.08 (18)
C6—C7—C8—C9	0.9 (3)	C24—C25—C26—C27	1.5 (3)
C7—C8—C9—O1	177.00 (16)	C25—C26—C27—O4	174.93 (18)
C7—C8—C9—C10	−3.4 (2)	C25—C26—C27—C28	−5.4 (3)
O1—C9—C10—C1	−178.45 (15)	O4—C27—C28—C19	−176.53 (15)
C8—C9—C10—N1	−178.19 (15)	C26—C27—C28—N3	−176.17 (16)
C8—C9—C10—C1	1.9 (2)	C26—C27—C28—C19	3.8 (2)
O1—C9—C10—N1	1.5 (3)	O4—C27—C28—N3	3.5 (2)
N2—C11—C12—C13	175.89 (14)	N4—C29—C30—C31	174.30 (14)
N2—C11—C12—C17	−3.6 (2)	N4—C29—C30—C35	−6.1 (2)
C16—C11—C12—C13	−2.5 (2)	C34—C29—C30—C31	−3.6 (2)
C16—C11—C12—C17	177.99 (14)	C34—C29—C30—C35	176.01 (15)
N2—C11—C16—C15	−173.07 (14)	N4—C29—C34—C33	−171.64 (15)
N2—C11—C16—C18	13.0 (2)	N4—C29—C34—C36	14.8 (2)
C12—C11—C16—C15	5.3 (2)	C30—C29—C34—C33	6.2 (2)
C12—C11—C16—C18	−168.69 (15)	C30—C29—C34—C36	−167.36 (15)
C11—C12—C13—C14	−1.3 (2)	C29—C30—C31—C32	−0.9 (2)
C17—C12—C13—C14	178.15 (17)	C35—C30—C31—C32	179.48 (16)
C12—C13—C14—C15	2.4 (3)	C30—C31—C32—C33	2.8 (3)
C13—C14—C15—C16	0.4 (3)	C31—C32—C33—C34	−0.2 (3)
C14—C15—C16—C11	−4.2 (2)	C32—C33—C34—C29	−4.2 (2)
C14—C15—C16—C18	170.20 (17)	C32—C33—C34—C36	169.68 (15)
C11—C16—C18—O2	−127.69 (17)	C29—C34—C36—O5	−127.72 (17)
C11—C16—C18—O3	58.0 (2)	C29—C34—C36—O6	57.9 (2)
C15—C16—C18—O2	58.2 (2)	C33—C34—C36—O5	58.6 (2)
C15—C16—C18—O3	−116.11 (16)	C33—C34—C36—O6	−115.79 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg5 are the centroids of the C1–C6 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.88	1.86	2.5567 (17)	135
O3—H3A···O2ⁱ	0.84	1.81	2.6480 (17)	173
N4—H4N···O4	0.88	1.86	2.5519 (18)	134
O6—H6A···O5ⁱⁱ	0.84	1.81	2.6430 (18)	169
C17—H17C···Cg5ⁱⁱⁱ	0.98	2.81	3.6782 (18)	148
C35—H35C···Cg1^iv	0.98	2.70	3.5948 (18)	152

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

Acknowledgements

The authors acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate for Scientific Research and Technological Development. Mme Corine Bailly from the University of Strasbourg, France, is thanked for collecting the data.

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