Dibenz­yl({1-[(4-methyl-2-phenyl-4,5-di­hydro-1,3-oxazol-4-yl)meth­yl]-1H-1,2,3-triazol-4-yl}meth­yl)amine

Boukhssas, S.; Aouine, Y.; Faraj, H.; Alami, A.; El Hallaoui, A.; Zouihri, H.

doi:10.1107/S2414314617008604

organic compounds

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ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170860

https://doi.org/10.1107/S2414314617008604

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Dibenzyl({1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amine

Salaheddine Boukhssas,^a Younas Aouine,^b Hassane Faraj,^b Anouar Alami,^b ^* Abdelilah El Hallaoui ^b and Hafid Zouihri ^c

^aFormation Doctorale Molécules Bioactives, Santé et Biotechnologies, Centre d'Études Doctorales Sciences et Technologies, LCO, Faculté des Sciences Dhar El Marhaz, Fès, Morocco, ^bLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université, Sidi Mohammed Ben Abdellah, Fès, Morocco, and ^cLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
^*Correspondence e-mail: anouar.alami@usmba.ac.ma

Edited by J. Simpson, University of Otago, New Zealand (Received 3 June 2017; accepted 9 June 2017; online 13 June 2017)

In the title compound, C₂₈H₂₉N₅O, the molecule adopts an approximate U-shape, a conformation imposed at least in part by an intramolecular π–π contact between the two five-membered rings, which display a centroid-to-centroid separation of 3.6522 (7) Å. The planes of these rings are inclined to one another by 66.12 (5)°. A weak intramolecular C—H⋯·N hydrogen bond is also found. The planes of the phenyl rings of the amine unit are inclined at a dihedral angle of 81.10 (4)°, while that of the 4,5-dihydrooxazole ring makes an angle of 11.74 (8)° with its phenyl substituent. The crystal packing is stabilized by C—H⋯N hydrogen bonds that form chains parallel to the b axis. Several C—H⋯π(ring) contacts are also present.

Keywords: crystal structure; 4,5-dihydrooxazole; triazole; hydrogen bonds.

CCDC reference: 1555146

Structure description

1,2,3-Triazoles are important heterocycles that display a large range of biological activities and are widely employed as pharmaceuticals and agrochemicals. Compounds containing the 1,2,3-triazole moiety are known to exhibit antibacterial (Głowacka, 2009 ; Aufort et al., 2008 ; Demaray et al., 2008 ), antifungal (Chan et al., 2002 ; Jordan et al., 2001 ), anticancer (Kamal et al., 2008 ; Chen et al., 2008 ) and antiviral activity (Zhou et al., 2005 ; Lazrek et al., 2001 ). Isoxazoles are components of a variety of complex biologically active structures and play roles as catalysts, ligands and intermediates in the synthesis of functional compounds (Miller et al., 2009 ; Prasad et al., 2007 ). Isoxazoles also appear in numerous medicinally active compounds and natural products of biological significance.

The molecule of the title compound (Fig. 1) adopts an approximate U-shape, a conformation imposed at least in part by an intramolecular π–π contact between the two five-membered rings, D and E (see Scheme), with a centroid-to-centroid separation of 3.6522 (7) Å. These rings are inclined to one another by 66.12 (5)°. Phenyl rings A and B of the amine unit are inclined at a dihedral angle of 81.10 (4)°; they also make angles of 17.46 (5) and 86.69 (4)°, respectively, with the triazole ring (D). The 4,5-dihydrooxazole ring (E) makes a dihedral angle of 11.74 (8)° with its phenyl substituent (C). The crystal packing is stabilized by C—H⋯N hydrogen bonds, forming chains parallel to the b axis. Adjacent chains are linked by C—H⋯π(ring) hydrogen bonds (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C1–C6, C7–C12 and C13–C18 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯N2	0.97	2.58	3.2757 (16)	129
C23—H23⋯N2ⁱ	0.93	2.45	3.3607 (16)	166
C27—H27B⋯N3	0.97	2.60	3.3456 (17)	134
C2—H2⋯Cg4ⁱⁱ	0.93	2.63	3.56	154
C12—H12⋯Cg5	0.93	2.92	3.7081 (15)	143
C17—H17⋯Cg3ⁱⁱⁱ	0.93	2.84	3.7046 (16)	154
C24—H24B⋯Cg3ⁱ	0.93	2.93	3.8795 (14)	165
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x, -y+1, -z.

Figure 1
The structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Figure 2
A view of the crystal packing along the a axis for the title compound. Hydrogen bonds are drawn as dashed lines.

Synthesis and crystallization

A mixture of 0.65 mmol of 4-azidomethyl-4-methyl-2-phenyl-4,5-dihydrooxazole and 0.65 mmol of N,N-dibenzylprop-2-yn-1-amine in a minimum of toluene was heated under reflux with constant stirring for 72 h. After reaction, the solvent was evaporated under vacuum and the residue was extracted with ether. The organic layer was washed with water, dried with sodium sulfate (Na₂SO₄) and the solvent was removed. The product was purified by column chromatography on silica gel using ether–hexane (1:2 v/v) as eluant to afford the pure product. The purity of the compound was checked by determining its melting point (373–375 K). Suitable single crystals were obtained by recrystallization from chloroform (CHCl₃) (yield 84%). The structure of the product was also investigated by NMR spectroscopy (¹H and ¹³C), MS data and elemental analysis. Analytical data: R_F = 0.51 (ether). Elemental analysis calculated for C₂₈H₂₉N₅O (found): C 74.47 (74.87), H 6.47 (6.18), N 15.51% (15.11%). MS (EI): m/z (relative intensity %) 451 (100%) [M]⁺. Spectroscopic data: ¹H (300.13 MHz, CDCl₃): δ 1.42 (3H, CH₃, s), 3.37–3.47 (4H, dibenzyl, AB, J = 13.47 Hz), 3.66–3.73 [2H, CH₂N(Bn)₂, AB, J = 14.64 Hz], 4.06–4.52 (2H, 4,5-dihydrooxazole, AB, J = 8.92 Hz), 4.45–4.53 (2H, CH₂-triazole, AB, J = 14.10 Hz), 7.18–7.91 (15H_arom), 7.61 (1H⁵_{1,2,3-triazole}, s). ¹³C (75.47 MHz; CDCl₃): δ 25.11 (1C, CH₃), 47.61 [1C, CH₂N(Bn)₂], 57.40 (1C, 4,5-dihydrooxazole), 57.30 (2C, dibenzyl), 70.67 (1C, CH₂-triazole), 74.67 [1C, CH₂(4,5-dihydrooxazole)], 131.94 and 150.32 (2C, C⁴ and C⁵ of 1,2,3-triazole), 124.61–139.50 (18C_arom), 164.56 (1C, C=N of 4,5-dihydrooxazole).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. One reflection (i.e. 002) was found to be affected by the beam stop and was omitted from the final refinement cycles.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₉N₅O
M_r	451.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.8940 (3), 10.1125 (2), 24.8655 (7)
β (°)	95.096 (1)
V (Å³)	2478.04 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.41 × 0.37 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD detector
No. of measured, independent and observed [I > 2σ(I)] reflections	14425, 4561, 3913
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.06
No. of reflections	4561
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20
Computer programs: APEX2 (Bruker, 2005 ), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1555146

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008604/sj4117sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008604/sj4117Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008604/sj4117Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Dibenzyl({1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amine top

Crystal data top

C₂₈H₂₉N₅O	F(000) = 960
M_r = 451.56	D_x = 1.210 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8940 (3) Å	Cell parameters from 412 reflections
b = 10.1125 (2) Å	θ = 1.9–26.4°
c = 24.8655 (7) Å	µ = 0.08 mm⁻¹
β = 95.096 (1)°	T = 296 K
V = 2478.04 (11) Å³	Prism, colourless
Z = 4	0.41 × 0.37 × 0.21 mm

Data collection top

Bruker APEXII CCD detector diffractometer	3913 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 25.5°, θ_min = 2.1°
ω and φ scans	h = −11→11
14425 measured reflections	k = −12→11
4561 independent reflections	l = −30→30

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0524P)² + 0.5133P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4561 reflections	Δρ_max = 0.17 e Å⁻³
308 parameters	Δρ_min = −0.20 e Å⁻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
N1	−0.19432 (10)	0.39663 (9)	0.14326 (4)	0.0260 (2)
N5	0.32594 (11)	0.57568 (10)	0.22306 (4)	0.0319 (3)
N4	0.18147 (11)	0.33879 (10)	0.25538 (4)	0.0292 (2)
N2	0.03788 (11)	0.20795 (10)	0.21388 (4)	0.0336 (3)
N3	0.16377 (11)	0.21560 (10)	0.23540 (5)	0.0355 (3)
O1	0.38824 (10)	0.47298 (10)	0.14862 (4)	0.0412 (2)
C19	−0.14782 (13)	0.30100 (12)	0.10479 (5)	0.0281 (3)
H19A	−0.0572	0.2717	0.1175	0.034*
H19B	−0.1423	0.3445	0.0703	0.034*
C7	−0.18132 (13)	0.58240 (11)	0.08073 (5)	0.0290 (3)
C6	−0.23884 (13)	0.18192 (11)	0.09664 (4)	0.0264 (3)
C28	0.32787 (12)	0.57631 (12)	0.17225 (5)	0.0288 (3)
C5	−0.37929 (13)	0.19406 (12)	0.09226 (5)	0.0310 (3)
H5	−0.4187	0.2758	0.0980	0.037*
C26	0.39945 (13)	0.45638 (13)	0.24346 (5)	0.0310 (3)
C22	−0.02513 (12)	0.32656 (11)	0.21996 (4)	0.0259 (3)
C21	−0.17030 (12)	0.34983 (12)	0.19938 (5)	0.0276 (3)
H21A	−0.2198	0.2678	0.2026	0.033*
H21B	−0.2084	0.4142	0.2227	0.033*
C23	0.06687 (12)	0.41007 (12)	0.24656 (5)	0.0283 (3)
H23	0.0531	0.4974	0.2564	0.034*
C20	−0.13622 (14)	0.52809 (12)	0.13586 (5)	0.0323 (3)
H20A	−0.0380	0.5224	0.1401	0.039*
H20B	−0.1646	0.5876	0.1633	0.039*
C13	0.27476 (12)	0.68248 (13)	0.13586 (5)	0.0303 (3)
C8	−0.31850 (14)	0.58700 (12)	0.06262 (5)	0.0347 (3)
H8	−0.3829	0.5599	0.0854	0.042*
C24	0.31270 (13)	0.37969 (14)	0.28102 (5)	0.0341 (3)
H24A	0.3623	0.3018	0.2942	0.041*
H24B	0.2983	0.4347	0.3120	0.041*
C4	−0.46108 (15)	0.08543 (14)	0.07939 (5)	0.0394 (3)
H4	−0.5550	0.0947	0.0766	0.047*
C18	0.30205 (14)	0.68722 (15)	0.08200 (5)	0.0391 (3)
H18	0.3503	0.6191	0.0674	0.047*
C1	−0.18359 (15)	0.05817 (13)	0.08830 (5)	0.0352 (3)
H1	−0.0898	0.0480	0.0916	0.042*
C14	0.19990 (14)	0.78383 (15)	0.15650 (5)	0.0393 (3)
H14	0.1791	0.7802	0.1922	0.047*
C27	0.42583 (14)	0.38068 (14)	0.19164 (5)	0.0371 (3)
H27A	0.5207	0.3561	0.1919	0.045*
H27B	0.3707	0.3014	0.1878	0.045*
C10	−0.26549 (17)	0.67233 (14)	−0.02277 (6)	0.0452 (4)
H10	−0.2932	0.7012	−0.0575	0.054*
C11	−0.12981 (17)	0.67023 (16)	−0.00493 (6)	0.0489 (4)
H11	−0.0659	0.6992	−0.0276	0.059*
C12	−0.08751 (15)	0.62532 (14)	0.04651 (6)	0.0391 (3)
H12	0.0045	0.6240	0.0581	0.047*
C3	−0.40408 (17)	−0.03654 (14)	0.07068 (6)	0.0441 (4)
H3	−0.4593	−0.1091	0.0618	0.053*
C9	−0.36000 (16)	0.63142 (13)	0.01117 (6)	0.0401 (3)
H9	−0.4519	0.6337	−0.0005	0.048*
C2	−0.26504 (17)	−0.05000 (13)	0.07525 (6)	0.0435 (4)
H2	−0.2261	−0.1319	0.0695	0.052*
C16	0.18507 (16)	0.89492 (17)	0.07129 (6)	0.0497 (4)
H16	0.1560	0.9664	0.0497	0.060*
C25	0.52999 (14)	0.49757 (16)	0.27626 (6)	0.0442 (4)
H25A	0.5862	0.5460	0.2536	0.066*
H25B	0.5776	0.4202	0.2900	0.066*
H25C	0.5085	0.5524	0.3058	0.066*
C15	0.15607 (16)	0.88998 (17)	0.12459 (6)	0.0498 (4)
H15	0.1072	0.9580	0.1390	0.060*
C17	0.25715 (15)	0.79375 (17)	0.05018 (6)	0.0477 (4)
H17	0.2759	0.7969	0.0142	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0284 (6)	0.0251 (5)	0.0246 (5)	−0.0006 (4)	0.0026 (4)	0.0001 (4)
N5	0.0338 (6)	0.0354 (6)	0.0268 (5)	0.0033 (5)	0.0058 (4)	−0.0002 (4)
N4	0.0279 (6)	0.0306 (5)	0.0288 (5)	0.0009 (4)	0.0011 (4)	0.0029 (4)
N2	0.0316 (6)	0.0275 (5)	0.0414 (6)	0.0008 (5)	0.0013 (5)	0.0038 (5)
N3	0.0338 (7)	0.0281 (6)	0.0440 (6)	0.0033 (5)	0.0004 (5)	0.0045 (5)
O1	0.0493 (6)	0.0448 (6)	0.0301 (5)	0.0107 (5)	0.0075 (4)	−0.0069 (4)
C19	0.0292 (7)	0.0306 (6)	0.0251 (6)	0.0014 (5)	0.0060 (5)	0.0013 (5)
C7	0.0336 (7)	0.0210 (6)	0.0323 (6)	−0.0003 (5)	0.0018 (5)	−0.0002 (5)
C6	0.0332 (7)	0.0272 (6)	0.0186 (5)	0.0020 (5)	0.0020 (5)	0.0015 (4)
C28	0.0216 (6)	0.0369 (7)	0.0282 (6)	−0.0032 (5)	0.0046 (5)	−0.0057 (5)
C5	0.0335 (7)	0.0292 (6)	0.0304 (6)	0.0030 (5)	0.0029 (5)	−0.0015 (5)
C26	0.0272 (7)	0.0341 (7)	0.0319 (6)	0.0027 (5)	0.0028 (5)	−0.0006 (5)
C22	0.0280 (7)	0.0266 (6)	0.0239 (6)	0.0004 (5)	0.0058 (5)	0.0038 (5)
C21	0.0272 (7)	0.0304 (6)	0.0259 (6)	−0.0012 (5)	0.0055 (5)	0.0002 (5)
C23	0.0294 (7)	0.0292 (6)	0.0267 (6)	0.0029 (5)	0.0053 (5)	0.0002 (5)
C20	0.0331 (7)	0.0288 (6)	0.0339 (6)	−0.0043 (5)	−0.0024 (5)	0.0004 (5)
C13	0.0228 (7)	0.0418 (7)	0.0260 (6)	−0.0048 (5)	0.0008 (5)	−0.0020 (5)
C8	0.0337 (8)	0.0295 (6)	0.0406 (7)	−0.0034 (5)	0.0021 (6)	0.0046 (5)
C24	0.0300 (7)	0.0418 (7)	0.0297 (6)	0.0017 (6)	−0.0020 (5)	0.0040 (5)
C4	0.0354 (8)	0.0418 (8)	0.0402 (7)	−0.0044 (6)	−0.0016 (6)	−0.0025 (6)
C18	0.0337 (8)	0.0544 (9)	0.0298 (7)	−0.0021 (6)	0.0059 (6)	−0.0015 (6)
C1	0.0382 (8)	0.0335 (7)	0.0332 (7)	0.0102 (6)	0.0001 (6)	0.0001 (5)
C14	0.0388 (8)	0.0524 (8)	0.0259 (6)	0.0086 (7)	−0.0005 (6)	−0.0014 (6)
C27	0.0356 (8)	0.0375 (7)	0.0390 (7)	0.0046 (6)	0.0073 (6)	−0.0026 (6)
C10	0.0648 (11)	0.0400 (8)	0.0302 (7)	0.0137 (7)	0.0013 (7)	0.0018 (6)
C11	0.0555 (10)	0.0525 (9)	0.0420 (8)	0.0123 (8)	0.0221 (7)	0.0104 (7)
C12	0.0330 (8)	0.0393 (7)	0.0458 (8)	0.0049 (6)	0.0086 (6)	0.0061 (6)
C3	0.0579 (10)	0.0327 (7)	0.0400 (7)	−0.0094 (7)	−0.0052 (7)	−0.0052 (6)
C9	0.0419 (8)	0.0323 (7)	0.0439 (8)	0.0012 (6)	−0.0090 (6)	0.0012 (6)
C2	0.0631 (11)	0.0261 (7)	0.0404 (7)	0.0076 (7)	−0.0010 (7)	−0.0045 (6)
C16	0.0428 (9)	0.0608 (10)	0.0436 (8)	0.0033 (8)	−0.0069 (7)	0.0163 (7)
C25	0.0336 (8)	0.0508 (8)	0.0477 (8)	−0.0038 (7)	0.0003 (6)	−0.0022 (7)
C15	0.0480 (9)	0.0576 (10)	0.0421 (8)	0.0170 (8)	−0.0054 (7)	0.0014 (7)
C17	0.0420 (9)	0.0715 (11)	0.0298 (7)	−0.0055 (8)	0.0038 (6)	0.0112 (7)

Geometric parameters (Å, º) top

N1—C19	1.4630 (15)	C13—C18	1.3905 (17)
N1—C20	1.4665 (15)	C8—C9	1.3834 (19)
N1—C21	1.4727 (15)	C8—H8	0.9300
N5—C28	1.2651 (15)	C24—H24A	0.9700
N5—C26	1.4752 (16)	C24—H24B	0.9700
N4—C23	1.3451 (16)	C4—C3	1.381 (2)
N4—N3	1.3467 (15)	C4—H4	0.9300
N4—C24	1.4547 (17)	C18—C17	1.386 (2)
N2—N3	1.3135 (16)	C18—H18	0.9300
N2—C22	1.3664 (16)	C1—C2	1.380 (2)
O1—C28	1.3625 (15)	C1—H1	0.9300
O1—C27	1.4432 (16)	C14—C15	1.382 (2)
C19—C6	1.5065 (17)	C14—H14	0.9300
C19—H19A	0.9700	C27—H27A	0.9700
C19—H19B	0.9700	C27—H27B	0.9700
C7—C12	1.3837 (18)	C10—C11	1.376 (2)
C7—C8	1.3923 (19)	C10—C9	1.378 (2)
C7—C20	1.5069 (17)	C10—H10	0.9300
C6—C1	1.3886 (17)	C11—C12	1.386 (2)
C6—C5	1.3896 (18)	C11—H11	0.9300
C28—C13	1.4708 (18)	C12—H12	0.9300
C5—C4	1.3849 (19)	C3—C2	1.377 (2)
C5—H5	0.9300	C3—H3	0.9300
C26—C25	1.5231 (19)	C9—H9	0.9300
C26—C24	1.5339 (17)	C2—H2	0.9300
C26—C27	1.5409 (17)	C16—C17	1.378 (2)
C22—C23	1.3683 (17)	C16—C15	1.382 (2)
C22—C21	1.4998 (17)	C16—H16	0.9300
C21—H21A	0.9700	C25—H25A	0.9600
C21—H21B	0.9700	C25—H25B	0.9600
C23—H23	0.9300	C25—H25C	0.9600
C20—H20A	0.9700	C15—H15	0.9300
C20—H20B	0.9700	C17—H17	0.9300
C13—C14	1.3891 (19)

C19—N1—C20	111.57 (9)	N4—C24—C26	113.76 (10)
C19—N1—C21	111.94 (9)	N4—C24—H24A	108.8
C20—N1—C21	112.22 (9)	C26—C24—H24A	108.8
C28—N5—C26	107.27 (10)	N4—C24—H24B	108.8
C23—N4—N3	110.82 (10)	C26—C24—H24B	108.8
C23—N4—C24	128.73 (11)	H24A—C24—H24B	107.7
N3—N4—C24	120.42 (10)	C3—C4—C5	120.41 (14)
N3—N2—C22	109.19 (10)	C3—C4—H4	119.8
N2—N3—N4	106.99 (10)	C5—C4—H4	119.8
C28—O1—C27	105.69 (9)	C17—C18—C13	119.78 (14)
N1—C19—C6	113.41 (10)	C17—C18—H18	120.1
N1—C19—H19A	108.9	C13—C18—H18	120.1
C6—C19—H19A	108.9	C2—C1—C6	121.33 (13)
N1—C19—H19B	108.9	C2—C1—H1	119.3
C6—C19—H19B	108.9	C6—C1—H1	119.3
H19A—C19—H19B	107.7	C15—C14—C13	120.77 (13)
C12—C7—C8	118.59 (12)	C15—C14—H14	119.6
C12—C7—C20	120.87 (12)	C13—C14—H14	119.6
C8—C7—C20	120.52 (11)	O1—C27—C26	104.29 (10)
C1—C6—C5	118.17 (12)	O1—C27—H27A	110.9
C1—C6—C19	120.12 (11)	C26—C27—H27A	110.9
C5—C6—C19	121.44 (11)	O1—C27—H27B	110.9
N5—C28—O1	118.22 (12)	C26—C27—H27B	110.9
N5—C28—C13	125.58 (11)	H27A—C27—H27B	108.9
O1—C28—C13	116.16 (10)	C11—C10—C9	119.57 (13)
C4—C5—C6	120.51 (12)	C11—C10—H10	120.2
C4—C5—H5	119.7	C9—C10—H10	120.2
C6—C5—H5	119.7	C10—C11—C12	120.56 (14)
N5—C26—C25	109.22 (11)	C10—C11—H11	119.7
N5—C26—C24	109.72 (10)	C12—C11—H11	119.7
C25—C26—C24	107.82 (11)	C7—C12—C11	120.41 (14)
N5—C26—C27	103.51 (10)	C7—C12—H12	119.8
C25—C26—C27	112.65 (11)	C11—C12—H12	119.8
C24—C26—C27	113.80 (11)	C2—C3—C4	119.62 (13)
N2—C22—C23	107.75 (11)	C2—C3—H3	120.2
N2—C22—C21	122.17 (11)	C4—C3—H3	120.2
C23—C22—C21	130.08 (11)	C10—C9—C8	120.15 (14)
N1—C21—C22	116.28 (9)	C10—C9—H9	119.9
N1—C21—H21A	108.2	C8—C9—H9	119.9
C22—C21—H21A	108.2	C3—C2—C1	119.95 (13)
N1—C21—H21B	108.2	C3—C2—H2	120.0
C22—C21—H21B	108.2	C1—C2—H2	120.0
H21A—C21—H21B	107.4	C17—C16—C15	119.83 (14)
N4—C23—C22	105.25 (11)	C17—C16—H16	120.1
N4—C23—H23	127.4	C15—C16—H16	120.1
C22—C23—H23	127.4	C26—C25—H25A	109.5
N1—C20—C7	110.91 (10)	C26—C25—H25B	109.5
N1—C20—H20A	109.5	H25A—C25—H25B	109.5
C7—C20—H20A	109.5	C26—C25—H25C	109.5
N1—C20—H20B	109.5	H25A—C25—H25C	109.5
C7—C20—H20B	109.5	H25B—C25—H25C	109.5
H20A—C20—H20B	108.0	C16—C15—C14	119.84 (15)
C14—C13—C18	119.08 (13)	C16—C15—H15	120.1
C14—C13—C28	118.97 (11)	C14—C15—H15	120.1
C18—C13—C28	121.90 (12)	C16—C17—C18	120.68 (13)
C9—C8—C7	120.71 (13)	C16—C17—H17	119.7
C9—C8—H8	119.6	C18—C17—H17	119.7
C7—C8—H8	119.6

Hydrogen-bond geometry (Å, º) top

Cg3, Cg4 and Cg5 are the centroids of the C1-C6, C7-C12 and C13-C18 phenyl rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···N2	0.97	2.58	3.2757 (16)	129
C23—H23···N2ⁱ	0.93	2.45	3.3607 (16)	166
C27—H27B···N3	0.97	2.60	3.3456 (17)	134
C2—H2···Cg4ⁱⁱ	0.93	2.63	3.56	154
C12—H12···Cg5	0.93	2.92	3.7081 (15)	143
C17—H17···Cg3ⁱⁱⁱ	0.93	2.84	3.7046 (16)	154
C24—H24B···Cg3ⁱ	0.93	2.93	3.8795 (14)	165

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

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