Crystal structure of 3-(4-hy­droxy­phen­yl)-2-[(E)-2-phenyl­ethen­yl]quinazolin-4(3H)-one

Mierina, I.; Stepanovs, D.; Kuginyte, J.; Janichev, A.; Jure, M.

doi:10.1107/S2056989016004473

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ISSN: 2056-9890

Volume 72| Part 4| April 2016| Pages 522-525

https://doi.org/10.1107/S2056989016004473

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Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

Inese Mierina,^a Dmitrijs Stepanovs,^b,^a ^* Jolita Kuginyte,^c,^a Artur Janichev ^b,^a and Mara Jure ^a ^*

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Str. P. Valdena 3/7, Riga, LV 1048, Latvia, ^bLatvian Institute of Organic Synthesis, Str. Aizkraukles 21, Riga, LV 1006, Latvia, and ^cInstitute of Synthetic Chemistry, Kaunas University of Technology, Str. K. Barsausko 59, Kaunas, LT 51423, Lithuania
^*Correspondence e-mail: d_stepanovs@osi.lv, mara@ktf.rtu.lv

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 March 2016; accepted 15 March 2016; online 22 March 2016)

The title compound, C₂₂H₁₆N₂O₂ {systematic name: 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one}, consists of a substituted 2-[(E)-2-arylethenyl]-3-arylquinazolin-4(3H)-one skeleton. The substituents at the ethylene fragment are located in trans positions. The phenyl ring is inclined to the quinazolone ring by 26.44 (19)°, while the 4-hydroxyphenyl ring is inclined to the quinazolone ring by 81.25 (8)°. The phenyl ring and the 4-hydroxyphenyl ring are inclined to one another by 78.28 (2)°. In the crystal, molecules are connected via O—H⋯O hydrogen bonds, forming a helix along the a-axis direction. The helices are linked by C—H⋯π interactions, forming slabs parallel to (001).

Keywords: crystal structure; 2,3-disubstituted quinazolin-4(3H)-one; styrylquinazolinone conjugation system; hydrogen bonding.

CCDC reference: 1468806

1. Chemical context

Compounds containing the 2-[(E)-2-arylethenyl]-3-arylquinazolin-4(3H)-one core are well known for their broad biological activities. These compounds demonstrate antibiotic effect in vivo against methicillin-resistant Staphylococcus aureus (Bouley et al., 2015 ; Chang et al., 2014 ) and antileishmanial activity (Birhan et al., 2014 ). 2-Styryl functionalized quinazolinones are applicable as anticancer agents against human cell lines (Kamal et al., 2013 ; 2012 ; 2010a ,b ) and anticonvulsants (Das et al., 2014 ). Analogues of the title compound are Hsp90 inhibitors with in vitro anti-tumor activity (Park et al., 2007 ), as well as suppressants of the ubiquitin ligase activity of a human polypeptide (Erez & Nakache, 2011 ), GluN2D-containing NMDA receptors (Hansen & Traynelis, 2011 ) and c-KIT expression (Wang et al., 2013 ). Compounds with such a structure are good modulators of both γ-secretase (Fischer et al., 2011 ) and Rho C activity (Sun et al., 2003 ), as well as AMPA receptor antagonists (Chenard et al., 2001 ; 1999 ; Welch & DeVries, 1998 ). Piriqualone (the 2-hetarylvinyl analogue of the above mentioned compounds) has been used as a sedative–hypnotic drug (Kumar et al., 2015 ).

2. Structural commentary

The title compound 1, Fig. 1, consists of a substituted 2-[(E)-2-arylethenyl]-3-arylquinazolin-4(3H)-one skeleton. The substituents at the ethylene fragment are located in trans-positions. Unlike the structure reported by Nosova et al. (2012 ), where the conjugation system of styrylquinazolinone is practically planar, in compound 1 the 2-phenyleth-(E)-enyl substituent is twisted with respect to the plane of the quinazolone ring. The phenyl (C21–C26) and the 4-hydroxyphenyl (C12–C17) rings are inclined to one another by 78.2 (2)°, and to the quinazolone ring (N1/N2/C2/C4–C10) by 26.44 (19) and 81.25 (8)°, respectively. A similar styrylquinazolinone conjugation system geometry has been found in structures reported previously (Trashakhova et al., 2011 ; Ovchinnikova et al., 2014 ).

Figure 1
The molecular structure of compound 1, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal of 1, molecules are connected via O—H⋯O hydrogen bonds forming a 2₁ helix, with graph set C(3), propagating along the a-axis direction (Table 1 and Fig. 2). This is similar to the crystal packing reported for the structure of diltiazem acetylsalicilate hydrate (Stepanovs et al., 2016 ). In 1, the helices are linked via C—H⋯π interactions, forming slabs lying parallel to the ab plane (Table 1 and Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C12–C17 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O11ⁱ	0.82	1.84	2.654 (5)	172
C4—H4⋯Cg4ⁱⁱ	0.94	2.96	3.829 (5)	157
C16—H16⋯Cg3ⁱ	0.94	2.95	3.646 (5)	133
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+2, -z+1]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, -z+1]$ .

Figure 2
A fragment of the crystal structure of compound 1, showing the helix-like hydrogen-bonded chain propagating along the a-axis direction.

Figure 3
A view along the a axis of the crystal packing of compound 1. The hydrogen bonds are shown as dashed lines and the C—H⋯π interactions (see Table 1

) are represented as thin black lines.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37; Groom & Allen, 2014 ) for substructure S1 (Fig. 4) gave 137 hits, while a search for substructure S2 (2-arylvinyl 3-aryl quinazolin-4(3H)-one skeleton, Fig. 4) gave only three hits: Nosova et al. (2012); Trashakhova et al. (2011); Ovchinnikova et al. (2014). However, none of the characterized single crystals contains a hydrogen-bond donor/acceptor in the aryl substituent at position 3 of the quinazolinone unit and information on intermolecular interactions of such structures is still missing. The only example containing a carboxylic functionality at the 3-aryl substituent of quinazolin-4(3H)-one was analysed as a complex with Staphylococcus aureus at the PBP2a binding site (Bouley et al., 2015).

Figure 4
Substructures used for the Database survey.

5. Synthesis and crystallization

The title compound 1 was synthesized applying two pathways starting from 2-methyl (2) or 2-styryl (3) benzoxazin-4-one (methods A and B, respectively, Fig. 5).

Figure 5
Synthesis of the title compound, 1.

Method A

2-Methyl benzoxazin-4-one (2) (0.263 g, 1.6 mmol) and 4-aminophenol (4) (0.175 g, 1.6 mmol) in glacial acetic acid (2 ml) were refluxed for 7 h, then poured into crushed ice (50 ml) and filtered. Compound 5 was obtained as a greyish solid. Its spectroscopic data corresponded to those in the literature (Marinho & Proença, 2015 ). The crude product 5, without further purification, was subjected to condensation with benzaldehyde analogously to a known method (Krastina et al., 2014 ): 3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one (5) (0.276 g, 1.1 mmol), benzaldehyde (0.27 g, 2.53 mol) and acetanhydride (0.5 ml) in acetic acid (4 ml) were refluxed for 8 h, poured into crushed ice (50 ml), filtered and air-dried. The mixture containing compounds 1 and 6 (0.25 g) was refluxed for 7 h in NaOH/methanol (5%, 5 ml), poured into crushed ice (50 ml), acidified with conc. hydrochloric acid and filtered. The target compound 1 was obtained as a white solid with 53% (0.197 g) yield over two steps.

Method B

The title compound 1 was obtained as a by-product during the synthesis of 2-cinnamamido-N-(4-hydroxyphenyl)benzamide: benzoxazin-4-one 3 (1.00 g, 4 mmol) and 4-aminophenol (4) (0.44 g, 4 mmol) were refluxed in toluene (5 ml) for 3 h, then the mixture was filtered. The title compound was isolated by crystallization from ethanol.

Single crystals suitable for X-ray analysis were obtained by slow evaporation from ethanol at room temperature (m.p. > 523 K).

Spectroscopic data: IR (KBr), ν, cm⁻¹: 3300 (OH), 1655 (CON), 1150, 1515, 1470, 1450, 1340, 1225, 970, 775, 965. ¹H NMR (300 MHz, DMSO-d₆), δ (p.p.m.): 9.91 (1H, s, OH), 8.12 (1H, d, J = 7.8 Hz, H-5), 7.91–7.83 (2H, m, H-b, H-6/7), 7.76 (1H, d, J = 7.8 Hz, H-8), 7.52 (1H, t, J = 7.8 Hz, H-6/7), 7.41–7.33 (5H, m, Ph), 7.23 (2H, d, J = 8.6 Hz, H-1′), 6.94 (2H, d, J = 8.6 Hz, H-2′), 6.42 (1H, d, J = 15.4 Hz, H-a). ¹³C NMR (75 MHz, DMSO-d₆), δ (p.p.m.): 161.5, 157.8, 152.0, 147.4, 138.6, 134.9, 134.7, 129.9, 129.8, 129.1, 127.9, 127.4, 127.1, 126.52, 126.47, 120.6, 120.2, 116.1. HRMS. Calculated [M+H]⁺, m/z: 341.1285. C₂₂H₁₆N₂O₂. Found, m/z: 341.1282.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned geometrically and refined as riding on their parent atoms: C—H = 0.93 − 0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms. The H atom of the hydroxyl group was included in the position identified from a difference Fourier map and was then refined as riding: O—H = 0.82 Å with U_iso(H) = 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₂
M_r	340.37
Crystal system, space group	Orthorhombic, P2₁nb
Temperature (K)	173
a, b, c (Å)	5.3469 (2), 16.5139 (6), 19.8885 (10)
V (Å³)	1756.12 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.18 × 0.09

Data collection
Diffractometer	Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections	3862, 3862, 2236
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.139, 1.03
No. of reflections	3862
No. of parameters	236
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19
Computer programs: KappaCCD Server Software (Nonius, 1997 ), DENZO and SCALEPACK (Otwinowski & Minor, 1997 ), SIR2011 (Burla et al., 2012 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), SHELXL2015 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1468806

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989016004473/su5288sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016004473/su5288Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004473/su5288Isup3.cml

checkCIF report

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2015 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-(4-Hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one top

Crystal data top

C₂₂H₁₆N₂O₂	D_x = 1.287 Mg m⁻³
M_r = 340.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁nb	Cell parameters from 6856 reflections
a = 5.3469 (2) Å	θ = 1.0–27.5°
b = 16.5139 (6) Å	µ = 0.08 mm⁻¹
c = 19.8885 (10) Å	T = 173 K
V = 1756.12 (13) Å³	Plate, colorless
Z = 4	0.22 × 0.18 × 0.09 mm
F(000) = 712

Data collection top

Nonius KappaCCD diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.2°
φ and ω scan	h = −6→6
3862 measured reflections	k = −21→21
3862 independent reflections	l = −25→25

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)] = 0.068	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0478P)² + 0.3939P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3862 reflections	Δρ_max = 0.17 e Å⁻³
236 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint

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
N1	0.6956 (7)	0.7742 (2)	0.45545 (18)	0.0333 (9)
C2	0.8449 (8)	0.7044 (3)	0.4584 (2)	0.0317 (10)
N3	0.8479 (7)	0.6500 (2)	0.41192 (18)	0.0372 (9)
C4	0.6912 (9)	0.6013 (3)	0.3061 (2)	0.0436 (12)
H4	0.7956	0.5564	0.3096	0.052*
C5	0.5358 (9)	0.6089 (3)	0.2518 (2)	0.0476 (13)
H5	0.5349	0.5690	0.2188	0.057*
C6	0.3791 (11)	0.6756 (3)	0.2457 (3)	0.0564 (15)
H6	0.2738	0.6801	0.2086	0.068*
C7	0.3795 (12)	0.7346 (3)	0.2939 (3)	0.0588 (15)
H7	0.2750	0.7793	0.2895	0.071*
C8	0.5362 (10)	0.7885 (3)	0.4018 (3)	0.0435 (12)
C9	0.6946 (8)	0.6604 (3)	0.3564 (2)	0.0337 (11)
C10	0.5376 (9)	0.7278 (3)	0.3501 (2)	0.0372 (11)
O11	0.4054 (7)	0.8506 (2)	0.40120 (19)	0.0653 (12)
C12	0.7042 (8)	0.8360 (3)	0.5076 (2)	0.0315 (10)
C13	0.5181 (8)	0.8382 (3)	0.5557 (2)	0.0354 (11)
H13	0.3953	0.7983	0.5563	0.042*
C14	0.5143 (9)	0.8993 (3)	0.6027 (2)	0.0372 (11)
H14	0.3905	0.9002	0.6356	0.045*
C15	0.6941 (8)	0.9595 (3)	0.6013 (2)	0.0309 (10)
C16	0.8821 (8)	0.9566 (3)	0.5533 (2)	0.0344 (11)
H16	1.0059	0.9962	0.5528	0.041*
C17	0.8859 (8)	0.8951 (3)	0.5064 (2)	0.0339 (11)
H17	1.0110	0.8936	0.4739	0.041*
O18	0.6763 (7)	1.01968 (18)	0.64797 (15)	0.0426 (8)
H18	0.7583	1.0589	0.6356	0.064*
C19	0.9961 (7)	0.6928 (3)	0.5188 (2)	0.0338 (11)
H19	0.9602	0.7230	0.5570	0.041*
C20	1.1845 (8)	0.6398 (3)	0.5204 (2)	0.0341 (10)
H20	1.2220	0.6133	0.4804	0.041*
C21	1.3390 (9)	0.6191 (3)	0.5794 (2)	0.0361 (11)
C22	1.2883 (9)	0.6474 (3)	0.6437 (2)	0.0435 (12)
H22	1.1527	0.6816	0.6508	0.052*
C23	1.4371 (8)	0.6252 (3)	0.6973 (3)	0.0498 (15)
H23	1.4006	0.6441	0.7402	0.060*
C24	1.6404 (9)	0.5748 (3)	0.6875 (3)	0.0512 (14)
H24	1.7421	0.5605	0.7235	0.061*
C25	1.6909 (10)	0.5460 (3)	0.6243 (3)	0.0496 (13)
H25	1.8265	0.5117	0.6176	0.060*
C26	1.5421 (9)	0.5676 (3)	0.5706 (2)	0.0399 (12)
H26	1.5779	0.5475	0.5280	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0351 (19)	0.030 (2)	0.035 (2)	0.0014 (17)	−0.0054 (19)	−0.0034 (17)
C2	0.031 (2)	0.027 (2)	0.037 (3)	0.003 (2)	−0.004 (2)	−0.002 (2)
N3	0.041 (2)	0.033 (2)	0.037 (2)	0.0064 (18)	−0.0066 (19)	−0.0067 (19)
C4	0.050 (3)	0.038 (3)	0.042 (3)	0.003 (2)	−0.001 (3)	−0.007 (2)
C5	0.052 (3)	0.051 (4)	0.040 (3)	−0.011 (3)	−0.001 (3)	−0.013 (3)
C6	0.066 (3)	0.065 (4)	0.038 (3)	−0.002 (3)	−0.017 (3)	−0.007 (3)
C7	0.067 (3)	0.059 (4)	0.050 (3)	0.012 (3)	−0.021 (3)	−0.003 (3)
C8	0.045 (3)	0.041 (3)	0.043 (3)	0.004 (3)	−0.012 (3)	−0.001 (2)
C9	0.036 (2)	0.034 (3)	0.031 (3)	−0.001 (2)	−0.004 (2)	−0.002 (2)
C10	0.044 (2)	0.038 (3)	0.030 (3)	0.004 (2)	−0.006 (2)	−0.001 (2)
O11	0.081 (3)	0.055 (3)	0.060 (3)	0.029 (2)	−0.030 (2)	−0.010 (2)
C12	0.031 (2)	0.031 (3)	0.032 (3)	0.003 (2)	−0.003 (2)	−0.003 (2)
C13	0.036 (2)	0.029 (3)	0.041 (3)	−0.009 (2)	−0.001 (2)	0.004 (2)
C14	0.039 (2)	0.037 (3)	0.036 (3)	−0.002 (2)	0.006 (2)	0.003 (2)
C15	0.040 (2)	0.027 (3)	0.026 (2)	−0.003 (2)	−0.003 (2)	0.001 (2)
C16	0.034 (2)	0.033 (3)	0.036 (3)	−0.007 (2)	0.001 (2)	0.000 (2)
C17	0.032 (2)	0.036 (3)	0.034 (3)	−0.001 (2)	0.004 (2)	0.001 (2)
O18	0.062 (2)	0.0355 (19)	0.0304 (17)	−0.0100 (17)	0.0041 (16)	−0.0058 (16)
C19	0.038 (2)	0.029 (3)	0.034 (3)	−0.002 (2)	−0.006 (2)	−0.002 (2)
C20	0.040 (2)	0.027 (2)	0.035 (3)	−0.002 (2)	−0.005 (2)	0.000 (2)
C21	0.037 (2)	0.030 (3)	0.041 (3)	−0.007 (2)	−0.012 (2)	0.001 (2)
C22	0.041 (3)	0.045 (3)	0.044 (3)	−0.003 (2)	−0.008 (2)	−0.004 (3)
C23	0.054 (3)	0.060 (4)	0.036 (3)	−0.010 (3)	−0.009 (2)	0.002 (3)
C24	0.047 (3)	0.060 (4)	0.047 (4)	−0.009 (3)	−0.018 (2)	0.011 (3)
C25	0.038 (3)	0.051 (3)	0.059 (4)	0.001 (2)	−0.007 (3)	0.016 (3)
C26	0.039 (2)	0.040 (3)	0.041 (3)	−0.001 (2)	−0.003 (2)	0.003 (2)

Geometric parameters (Å, º) top

N1—C8	1.385 (6)	C14—H14	0.9300
N1—C2	1.404 (5)	C15—O18	1.364 (5)
N1—C12	1.455 (5)	C15—C16	1.387 (6)
C2—N3	1.289 (5)	C16—C17	1.379 (6)
C2—C19	1.459 (6)	C16—H16	0.9300
N3—C9	1.385 (5)	C17—H17	0.9300
C4—C5	1.368 (7)	O18—H18	0.8200
C4—C9	1.398 (6)	C19—C20	1.335 (6)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.390 (7)	C20—C21	1.475 (6)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.367 (7)	C21—C22	1.389 (6)
C6—H6	0.9300	C21—C26	1.390 (6)
C7—C10	1.406 (7)	C22—C23	1.379 (6)
C7—H7	0.9300	C22—H22	0.9300
C8—O11	1.241 (6)	C23—C24	1.382 (7)
C8—C10	1.436 (6)	C23—H23	0.9300
C9—C10	1.400 (6)	C24—C25	1.370 (7)
C12—C17	1.378 (6)	C24—H24	0.9300
C12—C13	1.381 (6)	C25—C26	1.378 (7)
C13—C14	1.377 (6)	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C14—C15	1.383 (6)

C8—N1—C2	121.5 (4)	C15—C14—H14	119.9
C8—N1—C12	116.7 (4)	O18—C15—C14	117.4 (4)
C2—N1—C12	121.8 (3)	O18—C15—C16	123.0 (4)
N3—C2—N1	123.3 (4)	C14—C15—C16	119.6 (4)
N3—C2—C19	119.4 (4)	C17—C16—C15	120.1 (4)
N1—C2—C19	117.3 (4)	C17—C16—H16	119.9
C2—N3—C9	118.6 (4)	C15—C16—H16	119.9
C5—C4—C9	120.6 (5)	C12—C17—C16	120.0 (4)
C5—C4—H4	119.7	C12—C17—H17	120.0
C9—C4—H4	119.7	C16—C17—H17	120.0
C4—C5—C6	120.6 (5)	C15—O18—H18	109.5
C4—C5—H5	119.7	C20—C19—C2	121.6 (4)
C6—C5—H5	119.7	C20—C19—H19	119.2
C7—C6—C5	120.2 (5)	C2—C19—H19	119.2
C7—C6—H6	119.9	C19—C20—C21	126.5 (4)
C5—C6—H6	119.9	C19—C20—H20	116.8
C6—C7—C10	120.1 (5)	C21—C20—H20	116.8
C6—C7—H7	119.9	C22—C21—C26	118.3 (4)
C10—C7—H7	119.9	C22—C21—C20	123.1 (4)
O11—C8—N1	119.7 (5)	C26—C21—C20	118.7 (4)
O11—C8—C10	124.9 (5)	C23—C22—C21	120.6 (5)
N1—C8—C10	115.5 (4)	C23—C22—H22	119.7
N3—C9—C4	119.4 (4)	C21—C22—H22	119.7
N3—C9—C10	121.7 (4)	C22—C23—C24	120.3 (5)
C4—C9—C10	118.9 (4)	C22—C23—H23	119.9
C9—C10—C7	119.7 (4)	C24—C23—H23	119.9
C9—C10—C8	119.5 (4)	C25—C24—C23	119.6 (5)
C7—C10—C8	120.7 (5)	C25—C24—H24	120.2
C17—C12—C13	120.1 (4)	C23—C24—H24	120.2
C17—C12—N1	120.4 (4)	C24—C25—C26	120.4 (5)
C13—C12—N1	119.3 (4)	C24—C25—H25	119.8
C14—C13—C12	120.1 (4)	C26—C25—H25	119.8
C14—C13—H13	120.0	C25—C26—C21	120.8 (5)
C12—C13—H13	120.0	C25—C26—H26	119.6
C13—C14—C15	120.1 (4)	C21—C26—H26	119.6
C13—C14—H14	119.9

C8—N1—C2—N3	1.2 (7)	C8—N1—C12—C17	−95.4 (5)
C12—N1—C2—N3	−177.5 (4)	C2—N1—C12—C17	83.3 (5)
C8—N1—C2—C19	−176.7 (4)	C8—N1—C12—C13	80.1 (5)
C12—N1—C2—C19	4.7 (6)	C2—N1—C12—C13	−101.2 (5)
N1—C2—N3—C9	−0.6 (6)	C17—C12—C13—C14	−0.3 (6)
C19—C2—N3—C9	177.1 (4)	N1—C12—C13—C14	−175.8 (4)
C9—C4—C5—C6	0.2 (8)	C12—C13—C14—C15	1.1 (7)
C4—C5—C6—C7	0.2 (9)	C13—C14—C15—O18	178.2 (4)
C5—C6—C7—C10	−0.3 (9)	C13—C14—C15—C16	−1.8 (7)
C2—N1—C8—O11	179.4 (5)	O18—C15—C16—C17	−178.4 (4)
C12—N1—C8—O11	−1.9 (7)	C14—C15—C16—C17	1.6 (7)
C2—N1—C8—C10	−0.7 (6)	C13—C12—C17—C16	0.1 (6)
C12—N1—C8—C10	178.0 (4)	N1—C12—C17—C16	175.5 (4)
C2—N3—C9—C4	−178.7 (4)	C15—C16—C17—C12	−0.7 (7)
C2—N3—C9—C10	−0.3 (6)	N3—C2—C19—C20	17.8 (7)
C5—C4—C9—N3	178.0 (4)	N1—C2—C19—C20	−164.3 (4)
C5—C4—C9—C10	−0.5 (7)	C2—C19—C20—C21	−175.8 (4)
N3—C9—C10—C7	−178.0 (5)	C19—C20—C21—C22	6.9 (7)
C4—C9—C10—C7	0.4 (7)	C19—C20—C21—C26	−174.5 (4)
N3—C9—C10—C8	0.7 (7)	C26—C21—C22—C23	0.4 (7)
C4—C9—C10—C8	179.1 (4)	C20—C21—C22—C23	179.0 (4)
C6—C7—C10—C9	0.0 (8)	C21—C22—C23—C24	0.5 (7)
C6—C7—C10—C8	−178.7 (5)	C22—C23—C24—C25	−1.0 (7)
O11—C8—C10—C9	179.8 (5)	C23—C24—C25—C26	0.6 (8)
N1—C8—C10—C9	−0.2 (6)	C24—C25—C26—C21	0.3 (7)
O11—C8—C10—C7	−1.6 (8)	C22—C21—C26—C25	−0.8 (7)
N1—C8—C10—C7	178.5 (5)	C20—C21—C26—C25	−179.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C12–C17 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11ⁱ	0.82	1.84	2.654 (5)	172
C4—H4···Cg4ⁱⁱ	0.94	2.96	3.829 (5)	157
C16—H16···Cg3ⁱ	0.94	2.95	3.646 (5)	133

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

Acknowledgements

The authors thank the Latvian–Lithuanian–Taiwanese co-project W1935//LV-LT-TW/2015/2 for financial support. JK is grateful for an ERASMUS+ mobility grant for the opportunity of a traineeship at RTU.

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