2-{(E)-[(4-Anilinophen­yl)imino]­meth­yl}-4-[(E)-(4-meth­oxy­phen­yl)diazen­yl]phenol

Faizi, M.S.H.; Dege, N.; Goleva, K.

doi:10.1107/S241431461700548X

organic compounds

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ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170548

https://doi.org/10.1107/S241431461700548X

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2-{(E)-[(4-Anilinophenyl)imino]methyl}-4-[(E)-(4-methoxyphenyl)diazenyl]phenol

Md. Serajul Haque Faizi,^a Necmi Dege ^b and Kateryna Goleva ^c ^*

^aDepartment of Chemistry, College of Science, Sultan Qaboos University, PO Box 36 Al-Khod 123, Muscat, Sultanate of Oman, ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and ^cDepartment of Chemistry, Taras Shevchenko National University of Kyiv, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: ekaterina_goleva@list.ru

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 19 February 2017; accepted 11 April 2017; online 21 April 2017)

In the title Schiff base compound, C₂₆H₂₂N₄O₂, the hydroxy group forms a intramolecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N and N=N bonds is E. The 4-methoxybenzene ring and the p-phenylenediamine ring are inclined to the phenol ring by 11.61 (17) and 46.04 (17)°, respectively. The terminal N-phenyl ring is inclined to the p-phenylenediamine ring by 50.72 (17)°. In the crystal, adjacent molecules are linked by C—H⋯O hydrogen bonds, involving the p-phenylenediamine ring and the phenol ring, forming chains along [001]. The chains are linked by a number of C—H⋯π interactions, forming slabs propagating parallel to (100).

Keywords: crystal structure; azo compounds; diazenyl; phenylamino; imino; Schiff base; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1543490

Structure description

Azo compounds have received much attention in fundamental and applied chemistry (Nishihara, 2004 ; Ispir, 2009 ). The well known applications of azo dyes in acid–base indicators and chemical sensors and as electron-transfer catalysts have attracted the interest of many investigators (Tunçel & Serin, 2006 ). The versatile applications of azo compounds in various fields include dyeing textile fibres, colouring different materials, plastics, biological medical studies, lasers, liquid crystalline displays, electro-optical devices and ink-jet printers in high-technology areas (Gregory, 1991 ). The conversion from the trans to the cis form in azo compounds can lead to photochromism. Photochromic compounds are of great interest for the control and measurement of radiation intensity, optical computers and display systems (Dürr & Bouas-Laurent, 1990 ), and for potential applications in molecular electronic devices (Martin et al., 1995 ). Schiff bases often exhibit various biological activities including antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975 ). 2-Hydroxy salicylaldimine compounds can undergo enol–imine/keto–amine tautomerization by H-atom transfer from the hydroxyl oxygen to the imine nitrogen, probably via intramolecular hydrogen bonding (Khedr et al., 2005 ). The present work is part of an ongoing structural study of Schiff bases and their utilization in the synthesis of new organic and polynuclear coordination compounds (Faizi & Hussain, 2014 ; Faizi et al., 2016 ). We report herein, on the synthesis and crystal structure of a new Schiff base compound.

There are very few examples of similar compounds in the literature although some metal complexes of similar ligands have been reported (Khandar & Rezvani, 1998 ; Cariati et al. 2004 ). One very similar compound, used as a chemosensor for the detection of fluoride and cyanide ions, has been described (Udhayakumari et al. 2015 ), but no crystal structure has been reported. Similar azo Schiff base compounds have been synthesized and used for second-order non-linearity (Jalali-Heravi et al. 1999 ), and for non-linear optical properties (Qian, et al. 2004 ). Azo-azomethine compounds have been synthesized and used as fluorescent dyes and for the synthesis of Co^II and Cu^II complexes (Kurtoglu et al. 2014 ).

The molecular structure of the title compound is illustrated in Fig. 1. The conformation about the azomethine N2=C13 bond [1.286 (4) Å] is E, and the C10—N2—C13—C14 torsion angle is 170.3 (3). The molecule is non-planar, with ring B (C7–C12) being inclined to rings A (C1–C6), C (C14–C19) and D (C20–C25) by 50.72 (17), 46.04 (17) and 52.12 (17)°, respectively, while the dihedral angles A/C, A/D and C/D are 8.15 (17), 3.56 (17) and 11.61 (17)°, respectively. The N3—C16 and N4—C20 bond lengths of 1.426 (5) and 1.424 (5) Å, respectively, indicate single-bond character, whereas the N3=N4 bond length of 1.252 (4) Å confirms the double-bond character, with an E conformation about the N3=N4 bond.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 40% probability level. The intramolecular O—H⋯N hydrogen bond (see Table 1

) is shown as a dashed line.

Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O—H⋯N in phenol–imine and N—H⋯O in keto–amine tautomers. The present analysis shows that the title compound exists in the phenol–imine form (Fig. 1). It exhibits an intramolecular O— H⋯N hydrogen bond, which generates an S(6) ring motif (Fig. 1 and Table 1). This intramolecular O—H⋯N hydrogen bond has been detected previously in salicylaldehyde derivatives (Faizi et al., 2017 ). The C19—O1 [1.347 (4) Å] bond length is in agreement with the values reported for similar compounds, viz. (E)-2-{[(4-anilinophenyl)- imino]methyl}phenol (Faizi et al., 2015 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of rings A (C1–C6), B (C7–C12), C (C14–C19) and D (C20–C25), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N2	0.84	1.81	2.559 (4)	147
C9—H9⋯O1ⁱ	0.95	2.45	3.307 (5)	150
C3—H3⋯Cg1ⁱⁱ	0.95	2.83	3.509 (4)	129
C6—H6⋯Cg1ⁱⁱⁱ	0.95	2.87	3.556 (4)	130
C8—H8⋯Cg2^iv	0.95	2.80	3.538 (4)	135
C11—H11⋯Cg2^v	0.95	2.73	3.441 (4)	132
C15—H15⋯Cg3ⁱⁱⁱ	0.95	2.89	3.584 (4)	131
C18—H18⋯Cg3ⁱⁱ	0.95	2.80	3.474 (4)	129
C22—H22⋯Cg4ⁱⁱⁱ	0.95	2.79	3.536 (4)	136
C25—H25⋯Cg4ⁱⁱ	0.95	2.60	3.373 (4)	138
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x, -y, z+{\script{1\over 2}}]$ ; (v) $[x, -y+1, z-{\script{1\over 2}}]$ .

In the crystal, molecules are connected by C—H⋯O hydrogen bonds, generating chains extending along the c-axis direction; Table 1 and Fig. 2. The chains are linked via a number of C—H⋯π interactions, forming slabs lying parallel to the bc plane; see Table 1 and Fig. 3.

Figure 2
A view along the b axis of the C—H⋯O hydrogen-bonded chain in the crystal of the title compound. The hydrogen bonds are shown as dashed lines; see Table 1

for details).

Figure 3
A view along the c axis of the crystal packing of the title compound. The C—H⋯π interactions (see Table 1

) are indicated by the double-headed blue arrows.

Synthesis and crystallization

Synthesis of 5-(4-methoxyphenylazo)salicyaldehyde (L): To a solution of p-methoxyaniline in water (5 ml, 0.05 mol) 6 ml of 37% aq. HCl was slowly added at 0–5° C with stirring. 20 ml of 20% aq. NaNO₂ solution was added to the mixture and the resulting solution was stirred for 1 h, which gave a bright-yellow solution. Salicylaldehyde (5 ml, 0.05 mol) was dissolved in a solution comprising 18 g Na₂CO₃ and 150 ml H₂O and the resulting solution was added dropwise to the bright-yellow solution over a period of 1 h. After stirring for 4 h, the reaction mixture was neutralized with HCl, yielding a brown crude solid that was filtered and recrystallized from ethanol to afford a pure yellow product.

Synthesis of the title compound: 100 mg (1 mmol) of N-phenyl-p-phenylenediamine were dissolved in 10 ml of absolute ethanol. To this solution, 52 mg (1 mmol) of (L) in 5 ml of absolute ethanol was added dropwise under stirring. The mixture was stirred for 10 min, two drops of glacial acetic acid were then added and the mixture was refluxed for a further 2 h. The resulting light-brown precipitate was recovered by filtration, washed several times with small portions of EtOH and then with diethyl ether to give the title compound (yield 120 mg, 86%). Yellow needle-like crystals of the title compound were obtained within 3 d by slow evaporation of a solution in MeOH.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₄O₂
M_r	422.47
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	47.514 (8), 7.1015 (11), 6.1289 (10)
β (°)	96.037 (9)
V (Å³)	2056.6 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003 )
T_min, T_max	0.953, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11961, 3631, 2747
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.092, 1.01
No. of reflections	3631
No. of parameters	292
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Computer programs: SMART and SAINT (Bruker, 2003), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and DIAMOND (Brandenberg & Putz, 2006 ).

Structural data

CCDC reference: 1543490

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431461700548X/su4134sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700548X/su4134Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700548X/su4134Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

2-{(E)-[(4-Anilinophenyl)imino]methyl}-4-[(E)-(4-methoxyphenyl)diazenyl]phenol top

Crystal data top

C₂₆H₂₂N₄O₂	F(000) = 888
M_r = 422.47	D_x = 1.361 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 47.514 (8) Å	Cell parameters from 3571 reflections
b = 7.1015 (11) Å	θ = 2.9–24.3°
c = 6.1289 (10) Å	µ = 0.09 mm⁻¹
β = 96.037 (9)°	T = 100 K
V = 2056.6 (6) Å³	Needle, yellow
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3631 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
/w–scans	θ_max = 25.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −56→56
T_min = 0.953, T_max = 0.981	k = −8→8
11961 measured reflections	l = −7→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0395P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3631 reflections	Δρ_max = 0.20 e Å⁻³
292 parameters	Δρ_min = −0.21 e Å⁻³
2 restraints	Extinction correction: (SHELXL2016; Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (6)

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
O2	0.28294 (6)	0.2453 (3)	0.6349 (4)	0.0227 (7)
O1	0.50798 (5)	0.1833 (4)	0.0205 (4)	0.0264 (7)
H1B	0.522153	0.205011	0.110889	0.040*
N2	0.53540 (7)	0.2769 (4)	0.3861 (5)	0.0198 (8)
N3	0.40918 (6)	0.2985 (4)	0.4118 (5)	0.0212 (8)
N4	0.38790 (6)	0.2203 (4)	0.3130 (5)	0.0218 (8)
N1	0.63876 (6)	0.2375 (4)	0.9183 (6)	0.0233 (8)
H1A	0.637112	0.227085	1.059477	0.028*
C23	0.30982 (8)	0.2495 (5)	0.5727 (6)	0.0189 (9)
C10	0.56120 (8)	0.2689 (5)	0.5255 (6)	0.0174 (9)
C14	0.48504 (8)	0.2851 (5)	0.3316 (7)	0.0177 (9)
C24	0.31294 (8)	0.1601 (5)	0.3748 (6)	0.0178 (9)
H24	0.297072	0.102594	0.293763	0.021*
C1	0.66649 (8)	0.2465 (5)	0.8587 (7)	0.0202 (10)
C16	0.43388 (8)	0.2748 (5)	0.3011 (7)	0.0194 (9)
C22	0.33303 (7)	0.3314 (5)	0.6933 (6)	0.0189 (9)
H22	0.330948	0.391784	0.828941	0.023*
C8	0.58894 (8)	0.1733 (5)	0.8577 (7)	0.0204 (9)
H8	0.590094	0.115840	0.998308	0.025*
C18	0.45831 (8)	0.1758 (5)	−0.0035 (7)	0.0198 (10)
H18	0.457845	0.129159	−0.149129	0.024*
C25	0.33910 (8)	0.1549 (5)	0.2963 (6)	0.0202 (10)
H25	0.341187	0.094179	0.160816	0.024*
C12	0.61148 (8)	0.3222 (5)	0.5708 (6)	0.0192 (9)
H12	0.628009	0.369191	0.514943	0.023*
C11	0.58566 (7)	0.3329 (5)	0.4447 (6)	0.0199 (9)
H11	0.584655	0.384689	0.301109	0.024*
C19	0.48417 (7)	0.2153 (5)	0.1163 (6)	0.0184 (10)
C2	0.67385 (8)	0.1688 (5)	0.6654 (6)	0.0203 (9)
H2	0.659660	0.114073	0.564225	0.024*
C7	0.61336 (8)	0.2431 (5)	0.7787 (6)	0.0188 (9)
C9	0.56306 (8)	0.1873 (5)	0.7325 (7)	0.0206 (9)
H9	0.546485	0.140993	0.788315	0.025*
C21	0.35935 (8)	0.3240 (5)	0.6135 (7)	0.0217 (10)
H21	0.375353	0.378276	0.696228	0.026*
C20	0.36240 (8)	0.2382 (5)	0.4144 (6)	0.0183 (10)
C3	0.70172 (8)	0.1701 (5)	0.6184 (7)	0.0240 (10)
H3	0.706527	0.117276	0.484792	0.029*
C13	0.51190 (8)	0.3059 (5)	0.4672 (7)	0.0180 (9)
H13	0.512070	0.341299	0.616818	0.022*
C6	0.68741 (8)	0.3266 (5)	1.0056 (6)	0.0231 (10)
H6	0.682584	0.381772	1.137828	0.028*
C15	0.45950 (7)	0.3168 (5)	0.4183 (6)	0.0175 (9)
H15	0.459738	0.368589	0.561428	0.021*
C17	0.43349 (9)	0.2041 (5)	0.0877 (7)	0.0210 (10)
H17	0.415930	0.175520	0.005503	0.025*
C26	0.27780 (9)	0.3453 (5)	0.8274 (7)	0.0298 (10)
H26A	0.289393	0.291821	0.954070	0.045*
H26B	0.257743	0.334788	0.849766	0.045*
H26C	0.282725	0.478167	0.811095	0.045*
C5	0.71541 (8)	0.3256 (5)	0.9584 (7)	0.0252 (10)
H5	0.729705	0.378741	1.060064	0.030*
C4	0.72263 (8)	0.2483 (5)	0.7655 (7)	0.0260 (10)
H4	0.741771	0.248696	0.733733	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0167 (15)	0.0279 (16)	0.0236 (17)	−0.0008 (12)	0.0037 (12)	−0.0043 (13)
O1	0.0178 (16)	0.0369 (17)	0.0247 (17)	−0.0002 (13)	0.0039 (13)	−0.0030 (13)
N2	0.0162 (19)	0.0168 (19)	0.027 (2)	0.0002 (14)	0.0037 (16)	−0.0008 (14)
N3	0.0147 (19)	0.0253 (19)	0.024 (2)	0.0007 (14)	0.0020 (16)	0.0010 (14)
N4	0.016 (2)	0.0204 (18)	0.029 (2)	0.0003 (14)	0.0028 (16)	0.0015 (15)
N1	0.0173 (19)	0.034 (2)	0.018 (2)	0.0021 (14)	0.0000 (14)	0.0018 (15)
C23	0.015 (2)	0.017 (2)	0.025 (3)	0.0003 (16)	0.0027 (18)	0.0072 (18)
C10	0.017 (2)	0.018 (2)	0.018 (2)	0.0013 (17)	0.0019 (17)	−0.0023 (17)
C14	0.016 (2)	0.015 (2)	0.022 (3)	−0.0010 (16)	0.0020 (17)	0.0032 (17)
C24	0.017 (2)	0.018 (2)	0.018 (2)	−0.0024 (16)	−0.0021 (17)	−0.0002 (17)
C1	0.018 (2)	0.015 (2)	0.027 (3)	−0.0002 (17)	−0.0003 (19)	0.0050 (18)
C16	0.018 (2)	0.017 (2)	0.023 (2)	0.0019 (17)	0.0027 (18)	0.0045 (18)
C22	0.020 (2)	0.021 (2)	0.016 (2)	0.0012 (17)	0.0021 (18)	0.0003 (17)
C8	0.023 (2)	0.021 (2)	0.017 (2)	0.0011 (17)	0.0020 (18)	0.0018 (18)
C18	0.023 (2)	0.019 (2)	0.017 (2)	0.0013 (17)	0.0023 (19)	0.0009 (17)
C25	0.024 (2)	0.016 (2)	0.021 (2)	0.0025 (16)	0.0027 (19)	0.0005 (17)
C12	0.017 (2)	0.018 (2)	0.024 (3)	0.0010 (16)	0.0051 (17)	−0.0010 (18)
C11	0.022 (2)	0.018 (2)	0.021 (2)	0.0016 (17)	0.0042 (19)	0.0009 (17)
C19	0.016 (2)	0.021 (2)	0.019 (2)	0.0012 (17)	0.0048 (18)	0.0025 (17)
C2	0.021 (2)	0.018 (2)	0.021 (3)	0.0006 (17)	−0.0023 (18)	−0.0014 (17)
C7	0.016 (2)	0.018 (2)	0.022 (2)	0.0002 (17)	0.0023 (18)	−0.0044 (17)
C9	0.016 (2)	0.020 (2)	0.027 (3)	−0.0002 (16)	0.0077 (18)	−0.0040 (17)
C21	0.016 (2)	0.017 (2)	0.031 (3)	−0.0001 (16)	−0.0037 (18)	0.0009 (19)
C20	0.014 (2)	0.019 (2)	0.023 (3)	0.0013 (16)	0.0024 (18)	0.0000 (17)
C3	0.024 (2)	0.022 (2)	0.026 (3)	0.0062 (17)	0.0027 (19)	0.0012 (18)
C13	0.021 (2)	0.019 (2)	0.014 (2)	0.0004 (16)	0.0018 (17)	0.0015 (16)
C6	0.025 (3)	0.021 (2)	0.024 (3)	0.0073 (17)	0.0001 (19)	−0.0008 (17)
C15	0.020 (2)	0.019 (2)	0.013 (2)	0.0000 (17)	−0.0008 (17)	−0.0013 (16)
C17	0.020 (2)	0.021 (2)	0.022 (3)	−0.0017 (17)	0.0001 (18)	0.0027 (18)
C26	0.020 (2)	0.041 (3)	0.029 (3)	0.0015 (18)	0.0068 (18)	−0.006 (2)
C5	0.019 (2)	0.018 (2)	0.037 (3)	−0.0011 (16)	−0.003 (2)	0.001 (2)
C4	0.018 (2)	0.022 (2)	0.037 (3)	0.0027 (17)	0.000 (2)	0.0044 (19)

Geometric parameters (Å, º) top

O2—C23	1.371 (4)	C8—H8	0.9500
O2—C26	1.420 (5)	C18—C17	1.372 (5)
O1—C19	1.347 (4)	C18—C19	1.392 (5)
O1—H1B	0.8400	C18—H18	0.9500
N2—C13	1.286 (4)	C25—C20	1.390 (5)
N2—C10	1.420 (4)	C25—H25	0.9500
N3—N4	1.252 (4)	C12—C11	1.382 (5)
N3—C16	1.426 (5)	C12—C7	1.386 (6)
N4—C20	1.424 (5)	C12—H12	0.9500
N1—C7	1.405 (5)	C11—H11	0.9500
N1—C1	1.405 (5)	C2—C3	1.385 (5)
N1—H1A	0.8800	C2—H2	0.9500
C23—C22	1.389 (5)	C9—H9	0.9500
C23—C24	1.391 (5)	C21—C20	1.385 (6)
C10—C11	1.387 (5)	C21—H21	0.9500
C10—C9	1.389 (5)	C3—C4	1.385 (6)
C14—C15	1.393 (5)	C3—H3	0.9500
C14—C19	1.406 (6)	C13—H13	0.9500
C14—C13	1.455 (5)	C6—C5	1.391 (5)
C24—C25	1.380 (5)	C6—H6	0.9500
C24—H24	0.9500	C15—H15	0.9500
C1—C2	1.385 (5)	C17—H17	0.9500
C1—C6	1.390 (5)	C26—H26A	0.9800
C16—C15	1.380 (5)	C26—H26B	0.9800
C16—C17	1.399 (6)	C26—H26C	0.9800
C22—C21	1.391 (4)	C5—C4	1.379 (6)
C22—H22	0.9500	C5—H5	0.9500
C8—C9	1.383 (5)	C4—H4	0.9500
C8—C7	1.394 (5)

C23—O2—C26	117.8 (3)	O1—C19—C14	121.7 (3)
C19—O1—H1B	109.5	C18—C19—C14	120.2 (3)
C13—N2—C10	120.3 (3)	C1—C2—C3	120.6 (4)
N4—N3—C16	112.4 (3)	C1—C2—H2	119.7
N3—N4—C20	115.5 (3)	C3—C2—H2	119.7
C7—N1—C1	127.5 (4)	C12—C7—C8	119.2 (4)
C7—N1—H1A	116.2	C12—C7—N1	122.7 (4)
C1—N1—H1A	116.2	C8—C7—N1	118.1 (4)
O2—C23—C22	124.9 (4)	C8—C9—C10	120.3 (4)
O2—C23—C24	114.9 (3)	C8—C9—H9	119.9
C22—C23—C24	120.3 (4)	C10—C9—H9	119.9
C11—C10—C9	119.2 (4)	C20—C21—C22	120.5 (4)
C11—C10—N2	118.4 (3)	C20—C21—H21	119.7
C9—C10—N2	122.3 (3)	C22—C21—H21	119.7
C15—C14—C19	118.3 (4)	C21—C20—C25	119.6 (4)
C15—C14—C13	120.8 (4)	C21—C20—N4	126.6 (3)
C19—C14—C13	120.6 (4)	C25—C20—N4	113.7 (3)
C25—C24—C23	119.9 (3)	C2—C3—C4	120.2 (4)
C25—C24—H24	120.1	C2—C3—H3	119.9
C23—C24—H24	120.1	C4—C3—H3	119.9
C2—C1—C6	119.3 (4)	N2—C13—C14	120.5 (4)
C2—C1—N1	122.2 (4)	N2—C13—H13	119.7
C6—C1—N1	118.5 (4)	C14—C13—H13	119.7
C15—C16—C17	119.3 (4)	C5—C6—C1	119.9 (4)
C15—C16—N3	116.9 (4)	C5—C6—H6	120.1
C17—C16—N3	123.8 (3)	C1—C6—H6	120.1
C23—C22—C21	119.4 (4)	C16—C15—C14	121.5 (4)
C23—C22—H22	120.3	C16—C15—H15	119.3
C21—C22—H22	120.3	C14—C15—H15	119.3
C9—C8—C7	120.4 (4)	C18—C17—C16	120.4 (4)
C9—C8—H8	119.8	C18—C17—H17	119.8
C7—C8—H8	119.8	C16—C17—H17	119.8
C17—C18—C19	120.3 (4)	O2—C26—H26A	109.5
C17—C18—H18	119.9	O2—C26—H26B	109.5
C19—C18—H18	119.9	H26A—C26—H26B	109.5
C24—C25—C20	120.3 (4)	O2—C26—H26C	109.5
C24—C25—H25	119.8	H26A—C26—H26C	109.5
C20—C25—H25	119.8	H26B—C26—H26C	109.5
C11—C12—C7	120.3 (4)	C4—C5—C6	120.6 (4)
C11—C12—H12	119.9	C4—C5—H5	119.7
C7—C12—H12	119.9	C6—C5—H5	119.7
C12—C11—C10	120.6 (4)	C5—C4—C3	119.5 (4)
C12—C11—H11	119.7	C5—C4—H4	120.3
C10—C11—H11	119.7	C3—C4—H4	120.3
O1—C19—C18	118.1 (4)

C16—N3—N4—C20	180.0 (3)	C1—N1—C7—C12	−23.0 (6)
C26—O2—C23—C22	5.6 (5)	C1—N1—C7—C8	159.8 (3)
C26—O2—C23—C24	−175.7 (3)	C7—C8—C9—C10	0.8 (6)
C13—N2—C10—C11	−147.4 (3)	C11—C10—C9—C8	1.1 (6)
C13—N2—C10—C9	37.3 (6)	N2—C10—C9—C8	176.4 (4)
O2—C23—C24—C25	−179.8 (3)	C23—C22—C21—C20	0.8 (5)
C22—C23—C24—C25	−0.9 (6)	C22—C21—C20—C25	−1.6 (6)
C7—N1—C1—C2	−34.1 (6)	C22—C21—C20—N4	180.0 (3)
C7—N1—C1—C6	149.8 (4)	C24—C25—C20—C21	1.0 (5)
N4—N3—C16—C15	−165.6 (3)	C24—C25—C20—N4	179.7 (3)
N4—N3—C16—C17	11.3 (5)	N3—N4—C20—C21	−3.5 (5)
O2—C23—C22—C21	179.1 (3)	N3—N4—C20—C25	178.0 (3)
C24—C23—C22—C21	0.4 (5)	C1—C2—C3—C4	0.5 (5)
C23—C24—C25—C20	0.2 (5)	C10—N2—C13—C14	−170.3 (3)
C7—C12—C11—C10	1.5 (5)	C15—C14—C13—N2	−179.8 (3)
C9—C10—C11—C12	−2.3 (5)	C19—C14—C13—N2	6.2 (6)
N2—C10—C11—C12	−177.7 (3)	C2—C1—C6—C5	−0.8 (5)
C17—C18—C19—O1	179.3 (3)	N1—C1—C6—C5	175.4 (3)
C17—C18—C19—C14	−0.2 (5)	C17—C16—C15—C14	−2.0 (6)
C15—C14—C19—O1	179.2 (3)	N3—C16—C15—C14	175.1 (3)
C13—C14—C19—O1	−6.7 (5)	C19—C14—C15—C16	2.5 (5)
C15—C14—C19—C18	−1.3 (5)	C13—C14—C15—C16	−171.6 (3)
C13—C14—C19—C18	172.8 (4)	C19—C18—C17—C16	0.7 (5)
C6—C1—C2—C3	0.1 (5)	C15—C16—C17—C18	0.4 (5)
N1—C1—C2—C3	−176.0 (3)	N3—C16—C17—C18	−176.5 (3)
C11—C12—C7—C8	0.5 (5)	C1—C6—C5—C4	0.9 (5)
C11—C12—C7—N1	−176.6 (3)	C6—C5—C4—C3	−0.4 (6)
C9—C8—C7—C12	−1.7 (6)	C2—C3—C4—C5	−0.4 (6)
C9—C8—C7—N1	175.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of rings A (C1–C6), B (C7–C12), C (C14–C19) and D (C20–C25), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N2	0.84	1.81	2.559 (4)	147
C9—H9···O1ⁱ	0.95	2.45	3.307 (5)	150
C3—H3···Cg1ⁱⁱ	0.95	2.83	3.509 (4)	129
C6—H6···Cg1ⁱⁱⁱ	0.95	2.87	3.556 (4)	130
C8—H8···Cg2^iv	0.95	2.80	3.538 (4)	135
C11—H11···Cg2^v	0.95	2.73	3.441 (4)	132
C15—H15···Cg3ⁱⁱⁱ	0.95	2.89	3.584 (4)	131
C18—H18···Cg3ⁱⁱ	0.95	2.80	3.474 (4)	129
C22—H22···Cg4ⁱⁱⁱ	0.95	2.79	3.536 (4)	136
C25—H25···Cg4ⁱⁱ	0.95	2.60	3.373 (4)	138

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

Acknowledgements

The authors are grateful to Drs Igor Fritsky and Graham Smith for valuable discussions.

Funding information

Funding for this research was provided by: Department of Chemistry, Taras Shevchenko National University of Kyiv.

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