(E)-3-(4-Fluoro­phen­yl)-1-[1-(4-fluoro­phen­yl)-5-methyl-1H-1,2,3-triazol-4-yl]prop-2-en-1-one

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314617018417

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x171841

https://doi.org/10.1107/S2414314617018417

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(E)-3-(4-Fluorophenyl)-1-[1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]prop-2-en-1-one

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ‡

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 23 December 2017; accepted 23 December 2017; online 9 January 2018)

The asymmetric unit of the title compound, C₁₈H₁₃F₂N₃O, comprises two molecules with similar conformations. In the crystal, weak C—H⋯F interactions form chains of molecules and the chains are stacked to form layers parallel to (101).

Keywords: crystal structure; triazole.

CCDC reference: 1813278

Structure description

The asymmetric unit comprises two molecules of C₁₈H₁₃F₂N₃O (Fig. 1) with similar conformations (r.m.s. overlay fit = 0.180 Å). In the C1 molecule, the dihedral angles between the triazole ring and the adjacent and remote fluorobenzene rings are 39.63 (11) and 17.88 (11)°, respectively. Equivalent values for the C19 molecule are 34.67 (10) and 16.55 (11)°, respectively.

Figure 1
An ORTEP representation of the two unique molecules showing 50% probability ellipsoids.

In the crystal, very weak C—H⋯F interactions link the molecules into chains (Table 1, Fig. 2) and the chains are stacked to form layers parallel to (101) (Fig. 3). Weak aromatic π–π stacking is also observed [shortest centroid–centroid separation = 3.7332 (12) Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯F1ⁱ	0.93	2.73	3.418 (2)	132
C35—H35⋯F2ⁱⁱ	0.93	2.70	3.608 (2)	164
C2—H2⋯F3ⁱⁱⁱ	0.93	2.65	3.395 (2)	137
C17—H17⋯F4^iv	0.93	2.62	3.546 (2)	178
Symmetry codes: (i) x+1, y-1, z; (ii) x, y+1, z+1; (iii) x-1, y+1, z; (iv) x, y-1, z-1.

Figure 2
Intermolecular C—H⋯F interactions forming chains.

Figure 3
Crystal packing showing layers parallel to (101).

Synthesis and crystallization

1-[1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]ethanone, 4-fluorobenzaldehyde and sodium hydroxide (10%) were mixed in ethanol at 20–25°C for 4 h. Yellow plates (m.p. 167–168°C) were obtained following recrystallization from dimethylformamide solution of the solid obtained after work-up.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₃F₂N₃O
M_r	325.31
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.1891 (4), 14.1804 (6), 14.5050 (6)
α, β, γ (°)	68.075 (4), 84.220 (4), 74.627 (4)
V (Å³)	1506.65 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.21 × 0.10

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.503, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	26379, 7530, 4890
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.05
No. of reflections	7530
No. of parameters	435
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS2013 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1813278

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617018417/hb4197sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617018417/hb4197Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617018417/hb4197Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

(E)-3-(4-Fluorophenyl)-1-[1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]prop-2-en-1-one top

Crystal data top

C₁₈H₁₃F₂N₃O	Z = 4
M_r = 325.31	F(000) = 672
Triclinic, P1	D_x = 1.434 Mg m⁻³
a = 8.1891 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1804 (6) Å	Cell parameters from 6895 reflections
c = 14.5050 (6) Å	θ = 4.2–27.7°
α = 68.075 (4)°	µ = 0.11 mm⁻¹
β = 84.220 (4)°	T = 296 K
γ = 74.627 (4)°	Plate, yellow
V = 1506.65 (13) Å³	0.33 × 0.21 × 0.10 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	4890 reflections with I > 2σ(I)
ω scans	R_int = 0.029
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	θ_max = 29.8°, θ_min = 3.0°
T_min = 0.503, T_max = 1.000	h = −11→11
26379 measured reflections	k = −19→19
7530 independent reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0477P)² + 0.4741P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
7530 reflections	Δρ_max = 0.14 e Å⁻³
435 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Special details top

Experimental. Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the U_eq for the atoms to which they are bonded.

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

	x	y	z	U_iso*/U_eq
C1	0.2075 (3)	0.01266 (16)	0.03379 (16)	0.0604 (5)
C2	0.2384 (3)	0.05994 (16)	−0.06481 (16)	0.0667 (6)
H2	0.2281	0.1319	−0.0926	0.080*
C3	0.2854 (3)	−0.00171 (14)	−0.12258 (14)	0.0574 (5)
H3	0.3067	0.0286	−0.1901	0.069*
C4	0.3003 (2)	−0.10814 (13)	−0.07944 (13)	0.0451 (4)
C5	0.2665 (3)	−0.15357 (15)	0.02006 (14)	0.0589 (5)
H5	0.2756	−0.2254	0.0484	0.071*
C6	0.2191 (3)	−0.09221 (17)	0.07755 (15)	0.0645 (6)
H6	0.1956	−0.1218	0.1448	0.077*
C7	0.5744 (2)	−0.10855 (15)	−0.24935 (15)	0.0554 (5)
H7A	0.5199	−0.0457	−0.3017	0.083*
H7B	0.6744	−0.1441	−0.2748	0.083*
H7C	0.6049	−0.0907	−0.1968	0.083*
C8	0.4564 (2)	−0.17840 (12)	−0.21012 (12)	0.0407 (4)
C9	0.4406 (2)	−0.26215 (13)	−0.23169 (13)	0.0434 (4)
C10	0.5329 (2)	−0.30726 (13)	−0.30344 (13)	0.0459 (4)
C11	0.5127 (2)	−0.41066 (14)	−0.29353 (14)	0.0484 (4)
H11	0.4446	−0.4428	−0.2426	0.058*
C12	0.5872 (2)	−0.45986 (13)	−0.35404 (13)	0.0466 (4)
H12	0.6513	−0.4247	−0.4056	0.056*
C13	0.5791 (2)	−0.56363 (13)	−0.34807 (13)	0.0452 (4)
C14	0.4970 (3)	−0.62760 (15)	−0.27110 (14)	0.0562 (5)
H14	0.4438	−0.6037	−0.2214	0.067*
C15	0.4930 (3)	−0.72559 (16)	−0.26704 (16)	0.0636 (5)
H15	0.4386	−0.7682	−0.2152	0.076*
C16	0.5715 (3)	−0.75854 (15)	−0.34159 (17)	0.0614 (5)
C17	0.6531 (3)	−0.69911 (16)	−0.41866 (16)	0.0638 (5)
H17	0.7049	−0.7236	−0.4682	0.077*
C18	0.6566 (3)	−0.60140 (15)	−0.42123 (14)	0.0549 (5)
H18	0.7123	−0.5599	−0.4733	0.066*
C19	1.2425 (2)	−0.66173 (15)	0.01546 (14)	0.0517 (4)
C20	1.3283 (3)	−0.59030 (17)	0.01026 (15)	0.0616 (5)
H20	1.4229	−0.5834	−0.0306	0.074*
C21	1.2736 (3)	−0.52812 (16)	0.06637 (14)	0.0586 (5)
H21	1.3317	−0.4792	0.0641	0.070*
C22	1.1323 (2)	−0.53858 (13)	0.12588 (12)	0.0414 (4)
C23	1.0451 (2)	−0.61035 (13)	0.12862 (13)	0.0470 (4)
H23	0.9485	−0.6164	0.1678	0.056*
C24	1.1016 (2)	−0.67331 (15)	0.07298 (14)	0.0534 (5)
H24	1.0446	−0.7226	0.0747	0.064*
C25	0.9663 (3)	−0.58167 (13)	0.34081 (14)	0.0547 (5)
H25A	0.8549	−0.5847	0.3290	0.082*
H25B	0.9730	−0.5846	0.4076	0.082*
H25C	1.0483	−0.6400	0.3318	0.082*
C26	1.0016 (2)	−0.48221 (13)	0.26976 (12)	0.0413 (4)
C27	0.9802 (2)	−0.38655 (13)	0.27927 (13)	0.0463 (4)
C28	0.9078 (2)	−0.35116 (13)	0.36098 (13)	0.0478 (4)
C29	0.9169 (3)	−0.24485 (14)	0.34965 (14)	0.0526 (4)
H29	0.9774	−0.2092	0.2962	0.063*
C30	0.8435 (2)	−0.19792 (14)	0.41170 (13)	0.0494 (4)
H30	0.7826	−0.2348	0.4641	0.059*
C31	0.8486 (2)	−0.09345 (13)	0.40616 (13)	0.0468 (4)
C32	0.9495 (3)	−0.03399 (15)	0.33795 (15)	0.0558 (5)
H32	1.0171	−0.0611	0.2938	0.067*
C33	0.9505 (3)	0.06391 (16)	0.33501 (16)	0.0609 (5)
H33	1.0179	0.1031	0.2895	0.073*
C34	0.8501 (3)	0.10242 (14)	0.40055 (16)	0.0572 (5)
C35	0.7489 (3)	0.04812 (15)	0.46811 (16)	0.0614 (5)
H35	0.6812	0.0765	0.5114	0.074*
C36	0.7492 (3)	−0.05020 (14)	0.47070 (14)	0.0556 (5)
H36	0.6811	−0.0884	0.5168	0.067*
N1	0.34173 (18)	−0.17422 (11)	−0.13693 (11)	0.0452 (3)
N2	0.2574 (2)	−0.25153 (13)	−0.11516 (13)	0.0586 (4)
N3	0.3186 (2)	−0.30441 (12)	−0.17205 (12)	0.0549 (4)
N4	1.07488 (19)	−0.46919 (11)	0.17951 (10)	0.0453 (3)
N5	1.0991 (2)	−0.36974 (12)	0.13550 (11)	0.0628 (5)
N6	1.0419 (2)	−0.32099 (12)	0.19610 (12)	0.0606 (4)
O1	0.62385 (19)	−0.26083 (11)	−0.36626 (10)	0.0658 (4)
O2	0.84447 (19)	−0.40717 (10)	0.43345 (10)	0.0636 (4)
F1	0.1592 (2)	0.07284 (11)	0.09065 (10)	0.0896 (4)
F2	0.5683 (2)	−0.85579 (10)	−0.33684 (12)	0.0940 (5)
F3	1.29847 (17)	−0.72282 (11)	−0.04006 (10)	0.0808 (4)
F4	0.85150 (19)	0.19891 (9)	0.39781 (11)	0.0828 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0705 (13)	0.0620 (12)	0.0615 (12)	−0.0169 (10)	0.0053 (10)	−0.0377 (11)
C2	0.0948 (16)	0.0473 (11)	0.0667 (13)	−0.0239 (11)	0.0071 (12)	−0.0275 (10)
C3	0.0817 (14)	0.0459 (10)	0.0473 (10)	−0.0225 (10)	0.0058 (10)	−0.0167 (9)
C4	0.0502 (10)	0.0429 (9)	0.0470 (10)	−0.0160 (7)	0.0068 (8)	−0.0202 (8)
C5	0.0767 (14)	0.0467 (10)	0.0513 (11)	−0.0178 (9)	0.0158 (10)	−0.0177 (9)
C6	0.0807 (15)	0.0627 (13)	0.0494 (11)	−0.0168 (11)	0.0130 (10)	−0.0232 (10)
C7	0.0626 (12)	0.0536 (11)	0.0584 (11)	−0.0315 (9)	0.0137 (9)	−0.0214 (9)
C8	0.0446 (9)	0.0378 (8)	0.0396 (8)	−0.0150 (7)	0.0058 (7)	−0.0119 (7)
C9	0.0486 (10)	0.0383 (9)	0.0441 (9)	−0.0165 (7)	0.0061 (7)	−0.0135 (7)
C10	0.0508 (10)	0.0415 (9)	0.0459 (9)	−0.0147 (8)	0.0056 (8)	−0.0154 (8)
C11	0.0548 (10)	0.0448 (10)	0.0503 (10)	−0.0186 (8)	0.0080 (8)	−0.0201 (8)
C12	0.0534 (10)	0.0427 (9)	0.0441 (9)	−0.0136 (8)	0.0024 (8)	−0.0154 (8)
C13	0.0494 (10)	0.0434 (9)	0.0434 (9)	−0.0112 (7)	0.0010 (8)	−0.0167 (8)
C14	0.0694 (13)	0.0512 (11)	0.0520 (11)	−0.0205 (9)	0.0122 (9)	−0.0222 (9)
C15	0.0754 (14)	0.0521 (11)	0.0656 (13)	−0.0279 (10)	0.0132 (11)	−0.0191 (10)
C16	0.0702 (13)	0.0431 (10)	0.0762 (14)	−0.0150 (9)	−0.0031 (11)	−0.0260 (10)
C17	0.0777 (14)	0.0532 (11)	0.0676 (13)	−0.0141 (10)	0.0098 (11)	−0.0339 (11)
C18	0.0654 (12)	0.0490 (10)	0.0509 (10)	−0.0154 (9)	0.0099 (9)	−0.0205 (9)
C19	0.0542 (11)	0.0545 (11)	0.0509 (10)	−0.0130 (9)	0.0063 (9)	−0.0260 (9)
C20	0.0556 (11)	0.0835 (15)	0.0582 (12)	−0.0335 (11)	0.0210 (9)	−0.0338 (11)
C21	0.0649 (12)	0.0717 (13)	0.0562 (11)	−0.0410 (10)	0.0155 (10)	−0.0293 (10)
C22	0.0491 (9)	0.0405 (9)	0.0368 (8)	−0.0168 (7)	0.0013 (7)	−0.0127 (7)
C23	0.0494 (10)	0.0464 (10)	0.0497 (10)	−0.0193 (8)	0.0099 (8)	−0.0197 (8)
C24	0.0593 (11)	0.0508 (10)	0.0608 (11)	−0.0248 (9)	0.0106 (9)	−0.0272 (9)
C25	0.0724 (13)	0.0399 (9)	0.0494 (10)	−0.0208 (9)	0.0156 (9)	−0.0126 (8)
C26	0.0470 (9)	0.0380 (9)	0.0384 (8)	−0.0143 (7)	0.0024 (7)	−0.0112 (7)
C27	0.0602 (11)	0.0378 (9)	0.0424 (9)	−0.0185 (8)	0.0013 (8)	−0.0121 (7)
C28	0.0579 (11)	0.0399 (9)	0.0460 (10)	−0.0137 (8)	0.0012 (8)	−0.0151 (8)
C29	0.0681 (12)	0.0442 (10)	0.0484 (10)	−0.0203 (9)	0.0048 (9)	−0.0167 (8)
C30	0.0587 (11)	0.0440 (10)	0.0459 (10)	−0.0146 (8)	0.0020 (8)	−0.0159 (8)
C31	0.0558 (10)	0.0409 (9)	0.0444 (9)	−0.0111 (8)	−0.0017 (8)	−0.0163 (8)
C32	0.0642 (12)	0.0547 (11)	0.0561 (11)	−0.0203 (9)	0.0095 (9)	−0.0271 (9)
C33	0.0696 (13)	0.0536 (11)	0.0655 (13)	−0.0276 (10)	0.0049 (10)	−0.0211 (10)
C34	0.0723 (13)	0.0405 (10)	0.0627 (12)	−0.0126 (9)	−0.0131 (10)	−0.0205 (9)
C35	0.0789 (14)	0.0496 (11)	0.0587 (12)	−0.0101 (10)	0.0024 (10)	−0.0275 (10)
C36	0.0706 (13)	0.0474 (10)	0.0488 (10)	−0.0163 (9)	0.0077 (9)	−0.0184 (9)
N1	0.0529 (8)	0.0399 (7)	0.0481 (8)	−0.0206 (6)	0.0114 (7)	−0.0185 (7)
N2	0.0677 (10)	0.0558 (9)	0.0683 (10)	−0.0358 (8)	0.0276 (8)	−0.0333 (9)
N3	0.0636 (10)	0.0495 (9)	0.0645 (10)	−0.0296 (7)	0.0232 (8)	−0.0301 (8)
N4	0.0620 (9)	0.0388 (7)	0.0398 (7)	−0.0238 (7)	0.0061 (7)	−0.0132 (6)
N5	0.1073 (14)	0.0463 (9)	0.0442 (9)	−0.0409 (9)	0.0165 (9)	−0.0161 (7)
N6	0.0997 (13)	0.0444 (9)	0.0451 (9)	−0.0340 (9)	0.0108 (9)	−0.0162 (7)
O1	0.0836 (10)	0.0560 (8)	0.0648 (9)	−0.0332 (7)	0.0338 (8)	−0.0273 (7)
O2	0.0879 (10)	0.0489 (8)	0.0548 (8)	−0.0250 (7)	0.0209 (7)	−0.0193 (7)
F1	0.1226 (12)	0.0847 (9)	0.0852 (9)	−0.0274 (8)	0.0181 (8)	−0.0605 (8)
F2	0.1197 (12)	0.0538 (7)	0.1244 (12)	−0.0332 (8)	0.0155 (9)	−0.0458 (8)
F3	0.0878 (9)	0.0880 (9)	0.0915 (9)	−0.0308 (7)	0.0328 (7)	−0.0623 (8)
F4	0.1129 (11)	0.0499 (7)	0.0981 (10)	−0.0264 (7)	−0.0075 (8)	−0.0345 (7)

Geometric parameters (Å, º) top

C1—F1	1.359 (2)	C19—C24	1.363 (3)
C1—C6	1.362 (3)	C20—C21	1.376 (3)
C1—C2	1.364 (3)	C20—H20	0.9300
C2—C3	1.385 (3)	C21—C22	1.378 (2)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.377 (2)	C22—C23	1.377 (2)
C3—H3	0.9300	C22—N4	1.431 (2)
C4—C5	1.376 (3)	C23—C24	1.381 (2)
C4—N1	1.430 (2)	C23—H23	0.9300
C5—C6	1.379 (3)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.485 (2)
C6—H6	0.9300	C25—H25A	0.9600
C7—C8	1.488 (2)	C25—H25B	0.9600
C7—H7A	0.9600	C25—H25C	0.9600
C7—H7B	0.9600	C26—N4	1.352 (2)
C7—H7C	0.9600	C26—C27	1.378 (2)
C8—N1	1.353 (2)	C27—N6	1.365 (2)
C8—C9	1.375 (2)	C27—C28	1.467 (2)
C9—N3	1.365 (2)	C28—O2	1.220 (2)
C9—C10	1.465 (2)	C28—C29	1.476 (2)
C10—O1	1.222 (2)	C29—C30	1.319 (2)
C10—C11	1.471 (2)	C29—H29	0.9300
C11—C12	1.324 (2)	C30—C31	1.465 (2)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.460 (2)	C31—C36	1.388 (2)
C12—H12	0.9300	C31—C32	1.398 (3)
C13—C18	1.387 (2)	C32—C33	1.375 (3)
C13—C14	1.392 (2)	C32—H32	0.9300
C14—C15	1.378 (3)	C33—C34	1.367 (3)
C14—H14	0.9300	C33—H33	0.9300
C15—C16	1.371 (3)	C34—F4	1.357 (2)
C15—H15	0.9300	C34—C35	1.361 (3)
C16—C17	1.360 (3)	C35—C36	1.380 (3)
C16—F2	1.362 (2)	C35—H35	0.9300
C17—C18	1.380 (3)	C36—H36	0.9300
C17—H17	0.9300	N1—N2	1.3701 (19)
C18—H18	0.9300	N2—N3	1.294 (2)
C19—C20	1.355 (3)	N4—N5	1.3735 (19)
C19—F3	1.358 (2)	N5—N6	1.292 (2)

F1—C1—C6	118.35 (19)	C21—C20—H20	120.5
F1—C1—C2	118.77 (19)	C20—C21—C22	119.83 (17)
C6—C1—C2	122.86 (18)	C20—C21—H21	120.1
C1—C2—C3	118.45 (19)	C22—C21—H21	120.1
C1—C2—H2	120.8	C23—C22—C21	120.20 (16)
C3—C2—H2	120.8	C23—C22—N4	121.59 (15)
C4—C3—C2	119.59 (18)	C21—C22—N4	118.11 (15)
C4—C3—H3	120.2	C22—C23—C24	119.75 (16)
C2—C3—H3	120.2	C22—C23—H23	120.1
C5—C4—C3	120.70 (17)	C24—C23—H23	120.1
C5—C4—N1	117.69 (15)	C19—C24—C23	118.68 (17)
C3—C4—N1	121.52 (16)	C19—C24—H24	120.7
C4—C5—C6	119.75 (18)	C23—C24—H24	120.7
C4—C5—H5	120.1	C26—C25—H25A	109.5
C6—C5—H5	120.1	C26—C25—H25B	109.5
C1—C6—C5	118.65 (19)	H25A—C25—H25B	109.5
C1—C6—H6	120.7	C26—C25—H25C	109.5
C5—C6—H6	120.7	H25A—C25—H25C	109.5
C8—C7—H7A	109.5	H25B—C25—H25C	109.5
C8—C7—H7B	109.5	N4—C26—C27	103.98 (14)
H7A—C7—H7B	109.5	N4—C26—C25	125.31 (15)
C8—C7—H7C	109.5	C27—C26—C25	130.60 (16)
H7A—C7—H7C	109.5	N6—C27—C26	108.92 (15)
H7B—C7—H7C	109.5	N6—C27—C28	120.75 (15)
N1—C8—C9	103.99 (14)	C26—C27—C28	130.32 (15)
N1—C8—C7	124.74 (15)	O2—C28—C27	121.35 (15)
C9—C8—C7	131.19 (15)	O2—C28—C29	122.77 (17)
N3—C9—C8	109.02 (15)	C27—C28—C29	115.88 (15)
N3—C9—C10	120.88 (15)	C30—C29—C28	123.18 (17)
C8—C9—C10	130.09 (15)	C30—C29—H29	118.4
O1—C10—C9	120.54 (15)	C28—C29—H29	118.4
O1—C10—C11	122.96 (16)	C29—C30—C31	126.38 (17)
C9—C10—C11	116.48 (15)	C29—C30—H30	116.8
C12—C11—C10	122.81 (16)	C31—C30—H30	116.8
C12—C11—H11	118.6	C36—C31—C32	117.71 (16)
C10—C11—H11	118.6	C36—C31—C30	119.36 (16)
C11—C12—C13	126.70 (17)	C32—C31—C30	122.93 (16)
C11—C12—H12	116.7	C33—C32—C31	121.17 (18)
C13—C12—H12	116.7	C33—C32—H32	119.4
C18—C13—C14	117.89 (16)	C31—C32—H32	119.4
C18—C13—C12	119.41 (16)	C34—C33—C32	118.52 (19)
C14—C13—C12	122.69 (16)	C34—C33—H33	120.7
C15—C14—C13	121.32 (18)	C32—C33—H33	120.7
C15—C14—H14	119.3	F4—C34—C35	118.76 (19)
C13—C14—H14	119.3	F4—C34—C33	118.50 (19)
C16—C15—C14	118.13 (19)	C35—C34—C33	122.74 (17)
C16—C15—H15	120.9	C34—C35—C36	118.30 (19)
C14—C15—H15	120.9	C34—C35—H35	120.8
C17—C16—F2	119.13 (19)	C36—C35—H35	120.8
C17—C16—C15	122.97 (18)	C35—C36—C31	121.56 (18)
F2—C16—C15	117.90 (19)	C35—C36—H36	119.2
C16—C17—C18	118.12 (19)	C31—C36—H36	119.2
C16—C17—H17	120.9	C8—N1—N2	110.51 (13)
C18—C17—H17	120.9	C8—N1—C4	132.05 (14)
C17—C18—C13	121.57 (18)	N2—N1—C4	117.40 (13)
C17—C18—H18	119.2	N3—N2—N1	107.40 (13)
C13—C18—H18	119.2	N2—N3—C9	109.07 (14)
C20—C19—F3	118.33 (16)	C26—N4—N5	110.53 (14)
C20—C19—C24	122.52 (17)	C26—N4—C22	132.38 (14)
F3—C19—C24	119.15 (17)	N5—N4—C22	117.07 (13)
C19—C20—C21	119.01 (17)	N6—N5—N4	107.30 (13)
C19—C20—H20	120.5	N5—N6—C27	109.27 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···F1ⁱ	0.93	2.73	3.418 (2)	132
C35—H35···F2ⁱⁱ	0.93	2.70	3.608 (2)	164
C2—H2···F3ⁱⁱⁱ	0.93	2.65	3.395 (2)	137
C17—H17···F4^iv	0.93	2.62	3.546 (2)	178

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

Footnotes

‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.

Funding information

The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.

References

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