organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

2-(5-Methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-5-phenyl-1,3,4-oxa­diazole

CROSSMARK_Color_square_no_text.svg

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, dChemistry Department, Faculty of Science, Jazan University, Jazan 2079, Saudi Arabia, eChemical Industries Division, National Research Centre, Dokki 12622, Giza, Egypt, and fSchool 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 20 June 2018; accepted 5 July 2018; online 10 July 2018)

The asymmetric unit of the title compound, C17H13N5O, comprises four independent mol­ecules (AD). The respective inter­planar angles between the phen­yl/oxa­diazole/methyl­triazole/phenyl rings for the four independent mol­ecules are A 8.8 (2), 13.0 (2), 22.5 (2)°; B 6.3 (2), 8.9 (2), 29.0 (1)°; C 4.0 (2), 10.0 (2), 24.5 (2)°; D 3.5 (2), 10.1 (2), 27.2 (2)°. In the crystal, mol­ecules form two separate stacks parallel to the b-axis direction: one consists of A and D mol­ecules, and the other of B and C mol­ecules. Aromatic ππ stacking is observed within each stack, with the shortest centroid–centroid separation being 3.552 (2) Å.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The synthesis of heterocycles containing triazole and oxa­diazole moieties is of inter­est because of their biological activities (Bonandi et al., 2017[Bonandi, E., Christodoulou, M. S., Fumagalli, G., Perdicchia, D., Rastelli, G. & Passarella, D. (2017). Drug Discov. Today, 22, 1572-1581.]; Kumar & Kaur, 2014[Kumar, V. & Kaur, K. (2014). Nat. Prod. J. 4, 115-130.]; Li et al., 2011[Li, Z., Zhan, P. & Liu, X. (2011). Mini Rev. Med. Chem. 11, 1130-1142.]; Rajak et al., 2011[Rajak, H., Singour, P., Kharya, M. D. & Mishra, P. (2011). Chem. Biol. Drug Des. 77, 152-158.]). As part of our studies in this area, we now report the synthesis and structure of the title compound.

The asymmetric unit comprises four independent mol­ecules [A (C1–C17), B (C18–C34), C (C35–C51), D (C52–C68)] of C17H13N5O (Fig. 1[link]). The mol­ecule consists of a phen­yl/oxa­diazole/methyl­triazole/phenyl ring system. The respective dihedral angles between the rings for the four independent mol­ecules are (A) 8.8 (2), 13.0 (2), 22.5 (2)°; (B) 6.3 (2), 8.9 (2), 29.0 (1)°; (C) 4.0 (2), 10.0 (2), 24.5 (2)°; (D) 3.5 (2), 10.1 (2), 27.2 (2)°.

[Figure 1]
Figure 1
The mol­ecular structure showing 50% probability.

In the crystal, the mol­ecules stack parallel to the b-axis direction (Fig. 2[link]). Two types of stack are observed with each composed of two of the four independent mol­ecules (A and D in one stack; B and C in the other stack). Aromatic ππ stacking is observed within each stack, with the shortest centroid–centroid separation being 3.552 (2) Å.

[Figure 2]
Figure 2
Crystal packing viewed down the b axis.

Synthesis and crystallization

The title compound was synthesized according to the literature procedure (Abdel-Wahab et al., 2017[Abdel-Wahab, B. F., Alotaibi, M. H. & El-Hiti, G. A. (2017). Lett. Org. Chem. 14, 591-596.]) and recrystallized from di­methyl­formamide solution to give colourless needles.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. This structure has a strong b/2 subcell containing two mol­ecules in the asymmetric unit but refinements based on this model led to unrealistic displacement parameters for the atoms of the phenyl ring bound to the triazole ring and much poorer residuals.

Table 1
Experimental details

Crystal data
Chemical formula C17H13N5O
Mr 303.32
Crystal system, space group Orthorhombic, Pca21
Temperature (K) 296
a, b, c (Å) 23.5234 (10), 10.5928 (4), 23.4895 (13)
V3) 5853.1 (5)
Z 16
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.32 × 0.05 × 0.04
 
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 Ltd, Yarnton, England.])
Tmin, Tmax 0.785, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 30253, 13074, 8134
Rint 0.030
(sin θ/λ)max−1) 0.701
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.145, 1.06
No. of reflections 13074
No. of parameters 833
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.17, −0.23
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).

Structural data


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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (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).

2-(5-Methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-5-phenyl-1,3,4-oxadiazole top
Crystal data top
C17H13N5ODx = 1.377 Mg m3
Mr = 303.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 5718 reflections
a = 23.5234 (10) Åθ = 3.3–28.5°
b = 10.5928 (4) ŵ = 0.09 mm1
c = 23.4895 (13) ÅT = 296 K
V = 5853.1 (5) Å3Needle, colourless
Z = 160.32 × 0.05 × 0.04 mm
F(000) = 2528
Data collection top
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
diffractometer
8134 reflections with I > 2σ(I)
ω scansRint = 0.030
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
θmax = 29.9°, θmin = 1.7°
Tmin = 0.785, Tmax = 1.000h = 2432
30253 measured reflectionsk = 1411
13074 independent reflectionsl = 2924
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0658P)2 + 0.057P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.17 e Å3
13074 reflectionsΔρmin = 0.23 e Å3
833 parametersAbsolute structure: Flack x determined using 2598 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.8 (10)
Primary atom site location: structure-invariant direct methods
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
xyzUiso*/Ueq
C10.15453 (13)0.9158 (3)0.44268 (15)0.0452 (8)
C20.16709 (15)0.9197 (3)0.38489 (16)0.0547 (9)
H20.1515300.8597490.3605310.066*
C30.20253 (19)1.0122 (3)0.3634 (3)0.0600 (13)
H30.2110751.0136230.3247500.072*
C40.22509 (15)1.1015 (3)0.39882 (18)0.0578 (9)
H40.2481491.1649480.3841290.069*
C50.21360 (16)1.0975 (3)0.45629 (17)0.0598 (10)
H50.2297311.1568620.4805570.072*
C60.17805 (19)1.0049 (3)0.4780 (3)0.0520 (12)
H60.1700541.0031840.5167390.062*
C70.11797 (13)0.8203 (3)0.46695 (16)0.0461 (8)
C80.05922 (13)0.6669 (3)0.46898 (15)0.0451 (7)
C90.02246 (14)0.5691 (3)0.44694 (15)0.0464 (8)
C100.01729 (19)0.4988 (3)0.4756 (2)0.0432 (10)
C110.03517 (17)0.5073 (3)0.5365 (2)0.0631 (12)
H11A0.0183790.4392000.5576230.095*
H11B0.0227870.5863720.5521600.095*
H11C0.0758330.5017140.5389450.095*
C120.08230 (13)0.3268 (3)0.43811 (16)0.0467 (8)
C130.10952 (15)0.2921 (4)0.38813 (19)0.0600 (9)
H130.1000510.3309460.3539010.072*
C140.15079 (16)0.1995 (3)0.3896 (2)0.0693 (11)
H140.1686740.1751190.3560720.083*
C150.16581 (16)0.1428 (3)0.4403 (2)0.0687 (11)
H150.1941430.0815730.4412250.082*
C160.13844 (17)0.1778 (4)0.4889 (2)0.0724 (11)
H160.1486210.1404620.5232040.087*
C170.09617 (17)0.2671 (3)0.48822 (19)0.0648 (10)
H170.0769320.2871090.5216000.078*
C180.40400 (13)0.1692 (3)0.20211 (15)0.0434 (8)
C190.42839 (19)0.2608 (3)0.1662 (3)0.0513 (12)
H190.4207830.2604920.1273970.062*
C200.46340 (15)0.3502 (3)0.18924 (17)0.0543 (9)
H200.4792590.4114220.1657060.065*
C210.47569 (14)0.3516 (3)0.24661 (17)0.0546 (9)
H210.4994620.4133870.2615870.066*
C220.4525 (2)0.2605 (3)0.2817 (2)0.0576 (13)
H220.4609110.2604550.3204120.069*
C230.41690 (15)0.1700 (3)0.25959 (16)0.0528 (8)
H230.4014070.1088550.2833990.063*
C240.36559 (14)0.0761 (3)0.17737 (16)0.0449 (7)
C250.30607 (13)0.0736 (3)0.17456 (15)0.0451 (8)
C260.26856 (13)0.1719 (3)0.19583 (14)0.0434 (7)
C270.23683 (18)0.2559 (3)0.1644 (2)0.0426 (10)
C280.23507 (17)0.2785 (3)0.10223 (19)0.0587 (10)
H28A0.2019650.2387740.0864210.088*
H28B0.2685530.2437370.0849000.088*
H28C0.2335630.3676610.0950590.088*
C290.16562 (13)0.4180 (3)0.20044 (15)0.0455 (8)
C300.13170 (14)0.4274 (3)0.15289 (18)0.0597 (9)
H300.1348690.3688920.1235320.072*
C310.09275 (16)0.5253 (4)0.1494 (2)0.0708 (11)
H310.0706420.5343880.1168130.085*
C320.08655 (17)0.6091 (4)0.1937 (2)0.0732 (13)
H320.0598300.6736630.1915410.088*
C330.11999 (16)0.5965 (4)0.2406 (2)0.0730 (11)
H330.1157260.6528500.2707060.088*
C340.15999 (17)0.5019 (3)0.2445 (2)0.0603 (11)
H340.1828890.4950590.2766710.072*
C350.40286 (13)0.3321 (3)0.20455 (16)0.0481 (8)
C360.4292 (2)0.2426 (3)0.1694 (3)0.0595 (13)
H360.4231270.2438460.1302610.071*
C370.46404 (17)0.1534 (3)0.19299 (18)0.0618 (10)
H370.4814980.0938600.1697390.074*
C380.47345 (15)0.1508 (3)0.25056 (18)0.0607 (9)
H380.4967110.0889680.2662590.073*
C390.4484 (2)0.2399 (4)0.2851 (3)0.0622 (13)
H390.4553250.2386680.3241060.075*
C400.41348 (16)0.3305 (3)0.26249 (17)0.0590 (9)
H400.3969070.3906820.2860340.071*
C410.36506 (14)0.4259 (3)0.17931 (16)0.0484 (8)
C420.30688 (14)0.5791 (3)0.17682 (17)0.0492 (8)
C430.27125 (14)0.6785 (3)0.19846 (15)0.0461 (8)
C440.23184 (19)0.7498 (3)0.1694 (2)0.0476 (11)
C450.21333 (18)0.7428 (3)0.1096 (2)0.0669 (12)
H45A0.1727050.7503320.1076900.100*
H45B0.2247200.6632010.0936580.100*
H45C0.2305140.8101610.0883320.100*
C460.16706 (13)0.9221 (3)0.20848 (16)0.0469 (8)
C470.15412 (16)0.9841 (3)0.1592 (2)0.0620 (10)
H470.1740950.9657790.1260700.074*
C480.11147 (17)1.0742 (3)0.1582 (2)0.0674 (10)
H480.1017941.1135530.1242100.081*
C490.08361 (16)1.1052 (4)0.2073 (2)0.0673 (11)
H490.0554131.1667380.2069080.081*
C500.09739 (16)1.0451 (3)0.2572 (2)0.0670 (10)
H500.0786571.0667110.2907170.080*
C510.13889 (15)0.9528 (3)0.25809 (19)0.0583 (9)
H510.1477840.9116800.2919050.070*
C520.65410 (13)0.4155 (3)0.05930 (16)0.0466 (8)
C530.66535 (15)0.4163 (3)0.11737 (17)0.0555 (9)
H530.6487620.3559970.1408710.067*
C540.70110 (19)0.5064 (3)0.1403 (3)0.0603 (13)
H540.7087710.5062260.1791300.072*
C550.72531 (14)0.5962 (3)0.10589 (19)0.0597 (9)
H550.7483790.6583620.1216200.072*
C560.71551 (15)0.5944 (3)0.04802 (18)0.0592 (10)
H560.7331700.6533680.0246290.071*
C570.67922 (19)0.5045 (3)0.0245 (3)0.0511 (12)
H570.6719610.5044670.0144060.061*
C580.61569 (13)0.3242 (3)0.03402 (16)0.0468 (8)
C590.55618 (14)0.1736 (3)0.03043 (16)0.0469 (8)
C600.51907 (14)0.0751 (3)0.05139 (15)0.0478 (8)
C610.48725 (19)0.0095 (3)0.0205 (2)0.0455 (11)
C620.48588 (18)0.0312 (4)0.04252 (19)0.0633 (10)
H62A0.4531250.0096660.0584630.095*
H62B0.5196920.0029590.0594430.095*
H62C0.4839550.1202020.0500360.095*
C630.41686 (13)0.1732 (3)0.05550 (15)0.0467 (8)
C640.41034 (15)0.2563 (3)0.1005 (2)0.0572 (10)
H640.4328330.2488680.1328850.069*
C650.37000 (17)0.3502 (4)0.0965 (2)0.0755 (12)
H650.3649050.4058100.1267500.091*
C660.33719 (17)0.3627 (4)0.0484 (2)0.0742 (12)
H660.3103040.4268600.0459610.089*
C670.34430 (16)0.2802 (4)0.0041 (2)0.0695 (11)
H670.3225490.2895540.0287410.083*
C680.38317 (14)0.1841 (3)0.00753 (18)0.0586 (9)
H680.3868350.1265740.0221660.070*
N10.10785 (14)0.7962 (3)0.51957 (13)0.0561 (7)
N20.06963 (14)0.6961 (3)0.52138 (14)0.0570 (8)
N30.02346 (13)0.5340 (3)0.39151 (13)0.0540 (7)
N40.01326 (13)0.4438 (3)0.38410 (13)0.0547 (7)
N50.03861 (11)0.4211 (2)0.43539 (12)0.0463 (6)
N60.35325 (15)0.0603 (3)0.12444 (14)0.0583 (8)
N70.31322 (15)0.0395 (3)0.12258 (13)0.0576 (8)
N80.25813 (14)0.1867 (3)0.25203 (14)0.0567 (8)
N90.22086 (13)0.2761 (3)0.25810 (14)0.0562 (8)
N100.20740 (11)0.3194 (2)0.20498 (12)0.0444 (6)
N110.35356 (15)0.4434 (3)0.12637 (14)0.0583 (8)
N120.31466 (14)0.5453 (3)0.12471 (14)0.0579 (8)
N130.27303 (13)0.7150 (3)0.25429 (14)0.0579 (7)
N140.23577 (14)0.8041 (3)0.26178 (14)0.0592 (8)
N150.21067 (11)0.8276 (2)0.21034 (12)0.0473 (6)
N160.60203 (15)0.3104 (3)0.01853 (14)0.0614 (8)
N170.56280 (16)0.2118 (3)0.02124 (15)0.0636 (8)
N180.50895 (13)0.0576 (3)0.10765 (13)0.0564 (8)
N190.47243 (14)0.0334 (3)0.11341 (14)0.0590 (8)
N200.45830 (11)0.0750 (2)0.06031 (12)0.0458 (6)
O10.08810 (12)0.7411 (2)0.43137 (16)0.0479 (8)
O20.33694 (12)0.00500 (18)0.21168 (15)0.0438 (7)
O30.33675 (12)0.5077 (2)0.21364 (16)0.0488 (8)
O40.58785 (12)0.2398 (2)0.06883 (17)0.0508 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0471 (16)0.0483 (16)0.040 (2)0.0061 (15)0.0015 (14)0.0016 (14)
C20.070 (2)0.0546 (18)0.039 (2)0.0100 (18)0.0023 (18)0.0047 (16)
C30.070 (3)0.065 (2)0.045 (3)0.007 (2)0.005 (2)0.0009 (18)
C40.063 (2)0.0518 (18)0.058 (3)0.0016 (17)0.0029 (19)0.0005 (18)
C50.065 (2)0.060 (2)0.055 (3)0.0040 (18)0.0038 (19)0.0146 (18)
C60.057 (3)0.058 (2)0.041 (3)0.0008 (16)0.004 (2)0.0060 (15)
C70.0493 (17)0.0539 (17)0.0350 (19)0.0049 (15)0.0008 (15)0.0036 (15)
C80.0474 (17)0.0533 (17)0.0347 (19)0.0020 (15)0.0019 (14)0.0044 (15)
C90.0470 (17)0.0567 (18)0.0355 (19)0.0043 (16)0.0000 (14)0.0052 (15)
C100.047 (2)0.049 (2)0.034 (3)0.0049 (14)0.001 (2)0.0023 (14)
C110.072 (3)0.078 (2)0.039 (2)0.0130 (19)0.011 (2)0.0045 (18)
C120.0450 (16)0.0460 (16)0.049 (2)0.0049 (14)0.0018 (15)0.0008 (16)
C130.068 (2)0.065 (2)0.048 (2)0.002 (2)0.0012 (19)0.0030 (19)
C140.070 (2)0.068 (2)0.070 (3)0.005 (2)0.010 (2)0.009 (2)
C150.060 (2)0.058 (2)0.088 (4)0.0032 (18)0.001 (2)0.001 (2)
C160.074 (3)0.073 (2)0.070 (3)0.012 (2)0.009 (2)0.013 (2)
C170.075 (2)0.071 (2)0.048 (2)0.012 (2)0.005 (2)0.0105 (19)
C180.0455 (16)0.0434 (16)0.041 (2)0.0040 (14)0.0033 (14)0.0009 (14)
C190.055 (3)0.057 (2)0.042 (3)0.0018 (17)0.003 (2)0.0043 (16)
C200.0559 (19)0.0516 (18)0.055 (3)0.0036 (17)0.0036 (17)0.0083 (16)
C210.0559 (19)0.0527 (18)0.055 (3)0.0019 (16)0.0085 (17)0.0029 (17)
C220.076 (3)0.057 (2)0.040 (3)0.0055 (19)0.005 (2)0.0024 (16)
C230.064 (2)0.0546 (18)0.040 (2)0.0058 (17)0.0012 (18)0.0019 (16)
C240.0492 (17)0.0488 (16)0.037 (2)0.0044 (15)0.0043 (15)0.0007 (15)
C250.0464 (17)0.0495 (16)0.039 (2)0.0022 (15)0.0029 (15)0.0092 (15)
C260.0456 (17)0.0485 (16)0.0362 (19)0.0023 (15)0.0001 (13)0.0043 (14)
C270.041 (2)0.050 (2)0.037 (3)0.0025 (13)0.0020 (19)0.0041 (13)
C280.066 (2)0.073 (2)0.037 (2)0.009 (2)0.0042 (19)0.0055 (19)
C290.0436 (17)0.0474 (17)0.045 (2)0.0040 (15)0.0007 (14)0.0060 (15)
C300.058 (2)0.064 (2)0.056 (2)0.0050 (18)0.0021 (19)0.0057 (18)
C310.053 (2)0.087 (3)0.073 (3)0.009 (2)0.008 (2)0.023 (2)
C320.060 (2)0.066 (2)0.094 (4)0.015 (2)0.005 (2)0.010 (2)
C330.075 (3)0.066 (2)0.078 (3)0.008 (2)0.009 (2)0.006 (2)
C340.063 (2)0.061 (2)0.057 (3)0.0027 (18)0.005 (2)0.0031 (18)
C350.0471 (17)0.0541 (18)0.043 (2)0.0056 (16)0.0034 (15)0.0005 (15)
C360.065 (3)0.068 (3)0.046 (3)0.0060 (19)0.006 (3)0.0043 (18)
C370.066 (2)0.057 (2)0.062 (3)0.0025 (19)0.008 (2)0.0117 (18)
C380.059 (2)0.064 (2)0.060 (3)0.0057 (18)0.0015 (19)0.000 (2)
C390.071 (3)0.073 (3)0.042 (3)0.006 (2)0.002 (2)0.0026 (18)
C400.064 (2)0.069 (2)0.044 (2)0.0074 (19)0.0025 (19)0.0036 (18)
C410.0469 (17)0.0578 (18)0.041 (2)0.0078 (16)0.0089 (16)0.0008 (16)
C420.0464 (17)0.0577 (18)0.043 (2)0.0097 (16)0.0011 (16)0.0114 (16)
C430.0475 (17)0.0549 (17)0.0359 (19)0.0087 (16)0.0033 (14)0.0042 (14)
C440.047 (2)0.056 (2)0.041 (3)0.0081 (14)0.005 (2)0.0049 (14)
C450.076 (3)0.084 (3)0.041 (3)0.011 (2)0.014 (2)0.0049 (18)
C460.0467 (17)0.0492 (17)0.045 (2)0.0080 (15)0.0003 (15)0.0032 (16)
C470.067 (2)0.071 (2)0.048 (2)0.004 (2)0.0023 (19)0.0092 (19)
C480.074 (2)0.067 (2)0.061 (3)0.006 (2)0.004 (2)0.014 (2)
C490.063 (2)0.063 (2)0.076 (3)0.0016 (19)0.000 (2)0.002 (2)
C500.069 (2)0.071 (2)0.061 (3)0.003 (2)0.011 (2)0.004 (2)
C510.065 (2)0.062 (2)0.048 (2)0.0070 (19)0.0007 (19)0.0044 (19)
C520.0448 (16)0.0499 (16)0.045 (2)0.0055 (15)0.0059 (15)0.0028 (15)
C530.061 (2)0.0590 (19)0.046 (2)0.0052 (18)0.0055 (18)0.0062 (17)
C540.057 (3)0.075 (3)0.049 (3)0.0029 (19)0.004 (2)0.0025 (18)
C550.0567 (19)0.0580 (19)0.065 (3)0.0056 (17)0.0029 (19)0.0012 (19)
C560.062 (2)0.059 (2)0.056 (3)0.0018 (18)0.0084 (19)0.0121 (18)
C570.055 (3)0.053 (2)0.045 (3)0.0045 (15)0.002 (3)0.0065 (15)
C580.0488 (17)0.0506 (17)0.041 (2)0.0022 (15)0.0045 (16)0.0031 (15)
C590.0511 (17)0.0526 (17)0.037 (2)0.0032 (15)0.0009 (15)0.0018 (15)
C600.0512 (18)0.0527 (18)0.039 (2)0.0043 (16)0.0006 (15)0.0028 (15)
C610.051 (2)0.049 (2)0.036 (3)0.0059 (14)0.001 (2)0.0017 (14)
C620.069 (2)0.082 (2)0.039 (2)0.009 (2)0.001 (2)0.005 (2)
C630.0464 (17)0.0486 (16)0.045 (2)0.0052 (15)0.0022 (15)0.0029 (15)
C640.061 (2)0.062 (2)0.048 (3)0.0018 (17)0.0001 (19)0.0036 (17)
C650.080 (3)0.070 (2)0.076 (3)0.011 (2)0.010 (2)0.012 (2)
C660.065 (2)0.072 (2)0.086 (4)0.013 (2)0.002 (2)0.011 (2)
C670.061 (2)0.079 (2)0.069 (3)0.002 (2)0.015 (2)0.015 (2)
C680.060 (2)0.063 (2)0.053 (2)0.0006 (18)0.0072 (18)0.0007 (18)
N10.0617 (18)0.0669 (18)0.0396 (19)0.0076 (16)0.0013 (15)0.0039 (15)
N20.0631 (18)0.069 (2)0.039 (2)0.0070 (17)0.0022 (15)0.0054 (16)
N30.0639 (18)0.0613 (15)0.0368 (17)0.0045 (15)0.0075 (15)0.0008 (15)
N40.0659 (18)0.0618 (17)0.0364 (17)0.0039 (15)0.0109 (15)0.0025 (14)
N50.0514 (14)0.0530 (14)0.0345 (16)0.0020 (13)0.0066 (12)0.0011 (12)
N60.0688 (19)0.0645 (18)0.0416 (19)0.0125 (16)0.0006 (16)0.0010 (15)
N70.070 (2)0.0676 (17)0.0351 (19)0.0126 (17)0.0023 (16)0.0016 (15)
N80.0671 (18)0.0622 (17)0.0407 (19)0.0112 (16)0.0004 (15)0.0070 (15)
N90.0655 (19)0.0654 (16)0.0376 (18)0.0096 (16)0.0000 (15)0.0083 (15)
N100.0487 (14)0.0488 (14)0.0358 (16)0.0018 (12)0.0028 (12)0.0047 (11)
N110.0624 (18)0.0703 (19)0.0421 (19)0.0001 (16)0.0025 (16)0.0059 (16)
N120.0637 (19)0.0715 (19)0.039 (2)0.0013 (17)0.0024 (15)0.0058 (16)
N130.0640 (19)0.0661 (16)0.0437 (19)0.0027 (16)0.0076 (16)0.0054 (16)
N140.0690 (19)0.0721 (19)0.0365 (18)0.0070 (16)0.0085 (16)0.0020 (16)
N150.0527 (15)0.0557 (14)0.0336 (16)0.0058 (13)0.0057 (12)0.0056 (13)
N160.070 (2)0.071 (2)0.043 (2)0.0083 (17)0.0021 (16)0.0052 (16)
N170.076 (2)0.0679 (18)0.047 (2)0.0125 (19)0.0030 (18)0.0011 (17)
N180.0692 (18)0.0623 (17)0.0378 (18)0.0144 (16)0.0024 (15)0.0036 (15)
N190.078 (2)0.0635 (16)0.0353 (18)0.0113 (17)0.0039 (16)0.0051 (16)
N200.0520 (15)0.0517 (14)0.0336 (16)0.0013 (13)0.0032 (12)0.0031 (12)
O10.0485 (17)0.0560 (15)0.039 (2)0.0030 (10)0.0006 (15)0.0016 (11)
O20.0532 (18)0.0482 (15)0.0301 (17)0.0039 (10)0.0031 (14)0.0023 (10)
O30.0542 (18)0.0588 (16)0.0335 (18)0.0014 (11)0.0026 (15)0.0049 (11)
O40.0514 (18)0.0556 (15)0.045 (2)0.0032 (11)0.0007 (15)0.0012 (11)
Geometric parameters (Å, º) top
C1—C61.373 (5)C37—H370.9300
C1—C21.390 (5)C38—C391.377 (6)
C1—C71.445 (4)C38—H380.9300
C2—C31.382 (5)C39—C401.371 (6)
C2—H20.9300C39—H390.9300
C3—C41.367 (6)C40—H400.9300
C3—H30.9300C41—N111.286 (5)
C4—C51.377 (5)C41—O31.358 (4)
C4—H40.9300C42—N121.288 (5)
C5—C61.385 (5)C42—O31.347 (5)
C5—H50.9300C42—C431.438 (5)
C6—H60.9300C43—N131.368 (5)
C7—N11.284 (4)C43—C441.377 (5)
C7—O11.377 (4)C44—N151.360 (6)
C8—N21.292 (4)C44—C451.474 (8)
C8—O11.364 (5)C45—H45A0.9600
C8—C91.446 (5)C45—H45B0.9600
C9—N31.354 (4)C45—H45C0.9600
C9—C101.372 (5)C46—C471.365 (5)
C10—N51.349 (5)C46—C511.379 (5)
C10—C111.494 (7)C46—N151.434 (4)
C11—H11A0.9600C47—C481.385 (5)
C11—H11B0.9600C47—H470.9300
C11—H11C0.9600C48—C491.366 (6)
C12—C171.376 (5)C48—H480.9300
C12—C131.387 (5)C49—C501.373 (6)
C12—N51.435 (4)C49—H490.9300
C13—C141.381 (5)C50—C511.382 (5)
C13—H130.9300C50—H500.9300
C14—C151.379 (6)C51—H510.9300
C14—H140.9300C52—C571.380 (5)
C15—C161.362 (6)C52—C531.390 (5)
C15—H150.9300C52—C581.451 (5)
C16—C171.372 (5)C53—C541.381 (6)
C16—H160.9300C53—H530.9300
C17—H170.9300C54—C551.372 (6)
C18—C231.384 (5)C54—H540.9300
C18—C191.407 (5)C55—C561.379 (5)
C18—C241.458 (4)C55—H550.9300
C19—C201.366 (5)C56—C571.393 (5)
C19—H190.9300C56—H560.9300
C20—C211.378 (5)C57—H570.9300
C20—H200.9300C58—N161.284 (4)
C21—C221.382 (6)C58—O41.377 (5)
C21—H210.9300C59—N171.288 (5)
C22—C231.375 (6)C59—O41.364 (5)
C22—H220.9300C59—C601.447 (5)
C23—H230.9300C60—N181.355 (5)
C24—N61.288 (4)C60—C611.375 (5)
C24—O21.357 (4)C61—N201.349 (5)
C25—N71.285 (4)C61—C621.499 (7)
C25—O21.348 (4)C62—H62A0.9600
C25—C261.453 (4)C62—H62B0.9600
C26—N81.352 (4)C62—H62C0.9600
C26—C271.376 (5)C63—C681.382 (5)
C27—N101.357 (5)C63—C641.384 (5)
C27—C281.481 (7)C63—N201.430 (4)
C28—H28A0.9600C64—C651.378 (5)
C28—H28B0.9600C64—H640.9300
C28—H28C0.9600C65—C661.375 (6)
C29—C341.372 (5)C65—H650.9300
C29—C301.376 (5)C66—C671.370 (6)
C29—N101.438 (4)C66—H660.9300
C30—C311.386 (5)C67—C681.371 (5)
C30—H300.9300C67—H670.9300
C31—C321.375 (6)C68—H680.9300
C31—H310.9300N1—N21.391 (5)
C32—C331.362 (6)N3—N41.300 (4)
C32—H320.9300N4—N51.366 (4)
C33—C341.378 (5)N6—N71.416 (5)
C33—H330.9300N8—N91.299 (4)
C34—H340.9300N9—N101.367 (4)
C35—C401.384 (5)N11—N121.416 (5)
C35—C361.403 (6)N13—N141.300 (4)
C35—C411.460 (5)N14—N151.368 (4)
C36—C371.367 (6)N16—N171.395 (5)
C36—H360.9300N18—N191.299 (4)
C37—C381.370 (5)N19—N201.364 (4)
C6—C1—C2118.9 (3)C39—C40—H40120.0
C6—C1—C7118.9 (4)C35—C40—H40120.0
C2—C1—C7122.2 (3)N11—C41—O3112.3 (3)
C3—C2—C1120.4 (4)N11—C41—C35128.2 (3)
C3—C2—H2119.8O3—C41—C35119.5 (3)
C1—C2—H2119.8N12—C42—O3112.3 (3)
C4—C3—C2120.2 (5)N12—C42—C43128.5 (3)
C4—C3—H3119.9O3—C42—C43119.2 (3)
C2—C3—H3119.9N13—C43—C44109.9 (4)
C3—C4—C5119.9 (4)N13—C43—C42121.8 (3)
C3—C4—H4120.0C44—C43—C42128.2 (4)
C5—C4—H4120.0N15—C44—C43103.2 (4)
C4—C5—C6120.1 (4)N15—C44—C45126.6 (4)
C4—C5—H5120.0C43—C44—C45130.1 (4)
C6—C5—H5120.0C44—C45—H45A109.5
C1—C6—C5120.5 (5)C44—C45—H45B109.5
C1—C6—H6119.7H45A—C45—H45B109.5
C5—C6—H6119.7C44—C45—H45C109.5
N1—C7—O1111.6 (3)H45A—C45—H45C109.5
N1—C7—C1129.0 (3)H45B—C45—H45C109.5
O1—C7—C1119.4 (3)C47—C46—C51119.7 (3)
N2—C8—O1112.6 (3)C47—C46—N15121.4 (3)
N2—C8—C9128.7 (3)C51—C46—N15118.8 (3)
O1—C8—C9118.6 (3)C46—C47—C48120.5 (4)
N3—C9—C10109.5 (3)C46—C47—H47119.8
N3—C9—C8122.1 (3)C48—C47—H47119.8
C10—C9—C8128.4 (4)C49—C48—C47120.0 (4)
N5—C10—C9103.9 (4)C49—C48—H48120.0
N5—C10—C11127.0 (4)C47—C48—H48120.0
C9—C10—C11129.0 (4)C48—C49—C50119.7 (4)
C10—C11—H11A109.5C48—C49—H49120.1
C10—C11—H11B109.5C50—C49—H49120.1
H11A—C11—H11B109.5C49—C50—C51120.5 (4)
C10—C11—H11C109.5C49—C50—H50119.8
H11A—C11—H11C109.5C51—C50—H50119.8
H11B—C11—H11C109.5C46—C51—C50119.6 (4)
C17—C12—C13119.5 (3)C46—C51—H51120.2
C17—C12—N5121.9 (3)C50—C51—H51120.2
C13—C12—N5118.5 (3)C57—C52—C53119.7 (4)
C14—C13—C12119.4 (4)C57—C52—C58118.7 (4)
C14—C13—H13120.3C53—C52—C58121.6 (3)
C12—C13—H13120.3C54—C53—C52120.2 (4)
C15—C14—C13120.8 (4)C54—C53—H53119.9
C15—C14—H14119.6C52—C53—H53119.9
C13—C14—H14119.6C55—C54—C53120.1 (5)
C16—C15—C14118.9 (4)C55—C54—H54119.9
C16—C15—H15120.6C53—C54—H54119.9
C14—C15—H15120.6C54—C55—C56120.1 (4)
C15—C16—C17121.4 (4)C54—C55—H55119.9
C15—C16—H16119.3C56—C55—H55119.9
C17—C16—H16119.3C55—C56—C57120.2 (4)
C16—C17—C12119.9 (4)C55—C56—H56119.9
C16—C17—H17120.1C57—C56—H56119.9
C12—C17—H17120.1C52—C57—C56119.6 (5)
C23—C18—C19119.4 (3)C52—C57—H57120.2
C23—C18—C24121.9 (3)C56—C57—H57120.2
C19—C18—C24118.7 (4)N16—C58—O4112.2 (3)
C20—C19—C18119.2 (5)N16—C58—C52128.7 (3)
C20—C19—H19120.4O4—C58—C52119.1 (3)
C18—C19—H19120.4N17—C59—O4113.3 (3)
C19—C20—C21121.3 (4)N17—C59—C60128.3 (3)
C19—C20—H20119.3O4—C59—C60118.4 (3)
C21—C20—H20119.3N18—C60—C61109.3 (3)
C20—C21—C22119.6 (4)N18—C60—C59122.4 (3)
C20—C21—H21120.2C61—C60—C59128.2 (4)
C22—C21—H21120.2N20—C61—C60104.1 (4)
C23—C22—C21120.1 (5)N20—C61—C62126.5 (4)
C23—C22—H22119.9C60—C61—C62129.3 (4)
C21—C22—H22119.9C61—C62—H62A109.5
C22—C23—C18120.5 (4)C61—C62—H62B109.5
C22—C23—H23119.8H62A—C62—H62B109.5
C18—C23—H23119.8C61—C62—H62C109.5
N6—C24—O2112.3 (3)H62A—C62—H62C109.5
N6—C24—C18127.8 (3)H62B—C62—H62C109.5
O2—C24—C18119.9 (3)C68—C63—C64120.4 (3)
N7—C25—O2113.1 (3)C68—C63—N20121.1 (3)
N7—C25—C26127.5 (3)C64—C63—N20118.5 (3)
O2—C25—C26119.4 (3)C65—C64—C63118.9 (4)
N8—C26—C27110.5 (3)C65—C64—H64120.5
N8—C26—C25121.9 (3)C63—C64—H64120.5
C27—C26—C25127.4 (3)C66—C65—C64120.8 (4)
N10—C27—C26102.8 (4)C66—C65—H65119.6
N10—C27—C28126.8 (3)C64—C65—H65119.6
C26—C27—C28130.5 (4)C67—C66—C65119.7 (4)
C27—C28—H28A109.5C67—C66—H66120.2
C27—C28—H28B109.5C65—C66—H66120.2
H28A—C28—H28B109.5C66—C67—C68120.7 (4)
C27—C28—H28C109.5C66—C67—H67119.7
H28A—C28—H28C109.5C68—C67—H67119.7
H28B—C28—H28C109.5C67—C68—C63119.5 (4)
C34—C29—C30120.7 (3)C67—C68—H68120.2
C34—C29—N10118.7 (3)C63—C68—H68120.2
C30—C29—N10120.6 (3)C7—N1—N2107.5 (3)
C29—C30—C31119.0 (4)C8—N2—N1106.0 (3)
C29—C30—H30120.5N4—N3—C9108.6 (3)
C31—C30—H30120.5N3—N4—N5107.5 (3)
C32—C31—C30120.5 (4)C10—N5—N4110.4 (3)
C32—C31—H31119.7C10—N5—C12131.3 (3)
C30—C31—H31119.7N4—N5—C12118.3 (3)
C33—C32—C31119.2 (4)C24—N6—N7106.1 (3)
C33—C32—H32120.4C25—N7—N6105.5 (3)
C31—C32—H32120.4N9—N8—C26108.3 (3)
C32—C33—C34121.3 (4)N8—N9—N10107.5 (3)
C32—C33—H33119.3C27—N10—N9110.9 (3)
C34—C33—H33119.3C27—N10—C29131.1 (3)
C29—C34—C33119.2 (4)N9—N10—C29118.0 (3)
C29—C34—H34120.4C41—N11—N12105.8 (3)
C33—C34—H34120.4C42—N12—N11106.1 (3)
C40—C35—C36119.4 (4)N14—N13—C43108.3 (3)
C40—C35—C41121.2 (3)N13—N14—N15107.7 (3)
C36—C35—C41119.4 (4)C44—N15—N14110.9 (3)
C37—C36—C35119.5 (5)C44—N15—C46131.5 (3)
C37—C36—H36120.2N14—N15—C46117.6 (3)
C35—C36—H36120.2C58—N16—N17107.1 (3)
C36—C37—C38120.7 (4)C59—N17—N16105.8 (3)
C36—C37—H37119.6N19—N18—C60108.6 (3)
C38—C37—H37119.6N18—N19—N20107.8 (3)
C37—C38—C39119.9 (4)C61—N20—N19110.2 (3)
C37—C38—H38120.0C61—N20—C63131.6 (3)
C39—C38—H38120.0N19—N20—C63118.2 (3)
C40—C39—C38120.5 (5)C8—O1—C7102.2 (4)
C40—C39—H39119.8C25—O2—C24103.0 (3)
C38—C39—H39119.8C42—O3—C41103.5 (4)
C39—C40—C35119.9 (4)C59—O4—C58101.6 (4)
 

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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