organic compounds
Dibenzyl({1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amine
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
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).
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 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: RF = 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 (15Harom), 7.61 (1H51,2,3-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 (18Carom), 164.56 (1C, C=N of 4,5-dihydrooxazole).
Refinement
Crystal data, data collection and structure . One reflection (i.e. 002) was found to be affected by the beam stop and was omitted from the final cycles.
details are summarized in Table 2
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Structural data
CCDC reference: 1555146
https://doi.org/10.1107/S2414314617008604/sj4117sup1.cif
contains datablock I. DOI: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
Data collection: APEX2 (Bruker, 2005); cell
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).C28H29N5O | F(000) = 960 |
Mr = 451.56 | Dx = 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 |
Bruker APEXII CCD detector diffractometer | 3913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.5°, θmin = 2.1° |
ω and φ scans | h = −11→11 |
14425 measured reflections | k = −12→11 |
4561 independent reflections | l = −30→30 |
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(Fo2) + (0.0524P)2 + 0.5133P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4561 reflections | Δρmax = 0.17 e Å−3 |
308 parameters | Δρmin = −0.20 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
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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