(E)-1-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-3-(4-nitro­phen­yl)prop-2-en-1-one

El-Hiti, G.A.; Abdel-Wahab, B.F.; Mostafa, M.S.; Khidre, R.E.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618008416

organic compounds

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ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180841

https://doi.org/10.1107/S2414314618008416

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(E)-1-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-3-(4-nitrophenyl)prop-2-en-1-one

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohamed S. Mostafa,^d Rizk E. Khidre,^d,^e Amany S. Hegazy ^f and Benson M. Kariuki ^f ‡

^aDepartment 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 5 June 2018; accepted 6 June 2018; online 15 June 2018)

The title compound, C₁₉H₁₆N₄O₃, crystallizes with two molecules (A and B) in the asymmetric unit. In molecule A, the dihedral angles between the triazole ring and the toluyl and nitrobenzene rings are 62.68 (16) and 10.77 (15)°, respectively. The corresponding data for molecule B are 68.61 (17) and 15.59 (15)°, respectively. In the crystal, the B molecules are linked by C—H⋯N hydrogen bonds to generate [001] chains. Weak C—H⋯π(benzene) and N—O⋯π(triazole) contacts are also present.

Keywords: crystal structure; 1,2,3-triazole; heterocycles.

CCDC reference: 1847818

Structure description

Chalcones and their derivatives can be synthesized by Aldol or Claisen–Schmidt condensation reactions (Ahmad et al., 2016 ; Jung et al., 2017 ; Özdemir et al., 2017 ; Zhuang et al., 2017 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound.

The asymmetric unit comprises two independent molecules, A (containing C1) and B (containing C20) (Fig. 1). For molecule A, the dihedral angles between the triazolyl and toluyl and nitrobenzene rings are 62.68 (16) and 10.77 (15)°, respectively. The corresponding data for molecule B are 68.61 (17) and 15.59 (15)°, respectively. In the crystal (Fig. 2), the B molecules are linked by C—H⋯N hydrogen bonds, generating [001] chains (Table 1). Weak C—H⋯π and N—O⋯π contacts (Table 1, Fig. 2) may help to consolidate the packing.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4 and Cg6 are the centroids of the N2/N3/N4/C11/C10, N6–N8/C30/C29 and C32–C37 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C37—H37⋯N7ⁱ	0.93	2.57	3.470 (4)	164
C36—H36⋯Cg6ⁱ	0.93	3.00	3.646 (4)	128
N1—O1⋯Cg1ⁱⁱ	1.23 (1)	3.30 (1)	3.724 (3)	101 (1)
N5—O4⋯Cg4ⁱⁱⁱ	1.22 (1)	3.26 (1)	3.565 (3)	94 (1)
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) -x+1, -y, -z+1.

Figure 1
The molecular structure showing 50% probability ellipsoids.

Figure 2
Detail of the packing showing short C—H⋯π and N—O⋯π contacts.

Synthesis and crystallization

An equimolar mixture of 1-(1-p-tolyl-1H-1,2,3-triazol-4-yl)ethanone and 4-nitrobenzaldehyde was reacted in aqueous ethanol (90%) containing sodium hydroxide (5%) at room temperature for 4 h. The solid obtained was collected by filtration, successively washed with water and ethanol, then dried. Crystallization of the crude product from dimethylformamide solution gave colourless plates (73%) of the title compound, m.p. 206–208°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₄O₃
M_r	348.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	37.0489 (16), 13.3154 (7), 6.9170 (4)
β (°)	93.771 (4)
V (Å³)	3404.9 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.10 × 0.05

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.674, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	63124, 8971, 3659
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.267, 1.03
No. of reflections	8971
No. of parameters	474
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1847818

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008416/hb4237sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008416/hb4237Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618008416/hb4237Isup3.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: SHELXS (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).

(E)-1-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-3-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₁₆N₄O₃	F(000) = 1456
M_r = 348.36	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 37.0489 (16) Å	Cell parameters from 6548 reflections
b = 13.3154 (7) Å	θ = 3.6–23.5°
c = 6.9170 (4) Å	µ = 0.10 mm⁻¹
β = 93.771 (4)°	T = 298 K
V = 3404.9 (3) Å³	Plate, colourless
Z = 8	0.32 × 0.10 × 0.05 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Atlas diffractometer	3659 reflections with I > 2σ(I)
ω scans	R_int = 0.068
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.8°, θ_min = 0.6°
T_min = 0.674, T_max = 1.000	h = −49→50
63124 measured reflections	k = −16→18
8971 independent reflections	l = −8→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.076	w = 1/[σ²(F_o²) + (0.0948P)² + 1.2738P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.267	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.24 e Å⁻³
8971 reflections	Δρ_min = −0.21 e Å⁻³
474 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (5)
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.

Refinement. Non-hydrogen atoms were refined with anisotropic displacement parameters. All hydrogen atoms were placed in calculated positions and refined using a riding model. 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. Methyl groups were allowed to rotate about the C—C bond and C—H distances were set to 0.96 Å with U(iso) set to 1.5 times the U_eq for the C 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	−0.07838 (7)	0.12435 (19)	−0.2371 (4)	0.0580 (7)
C2	−0.04399 (8)	0.1502 (2)	−0.2812 (5)	0.0627 (8)
H2	−0.039433	0.172105	−0.404890	0.075*
C3	−0.01634 (8)	0.1429 (2)	−0.1384 (5)	0.0599 (7)
H3	0.007096	0.159754	−0.166562	0.072*
C4	−0.02302 (7)	0.11057 (19)	0.0478 (4)	0.0543 (7)
C5	−0.05831 (7)	0.0828 (2)	0.0840 (4)	0.0631 (8)
H5	−0.063094	0.058709	0.205980	0.076*
C6	−0.08603 (8)	0.0902 (2)	−0.0567 (5)	0.0648 (8)
H6	−0.109505	0.072585	−0.030726	0.078*
C7	0.00480 (7)	0.1046 (2)	0.2058 (4)	0.0592 (7)
H7	−0.002538	0.078724	0.321835	0.071*
C8	0.03925 (8)	0.1312 (2)	0.2057 (5)	0.0619 (8)
H8	0.047871	0.158574	0.093852	0.074*
C9	0.06411 (8)	0.1186 (2)	0.3780 (5)	0.0603 (7)
C10	0.10290 (7)	0.1286 (2)	0.3535 (4)	0.0560 (7)
C11	0.13136 (7)	0.1187 (2)	0.4903 (4)	0.0553 (7)
C12	0.13269 (8)	0.0982 (3)	0.7006 (4)	0.0721 (9)
H12A	0.129704	0.027512	0.721556	0.108*
H12B	0.113607	0.134274	0.757428	0.108*
H12C	0.155609	0.119531	0.759303	0.108*
C13	0.19821 (8)	0.1305 (2)	0.4518 (4)	0.0608 (7)
C14	0.21867 (8)	0.2157 (3)	0.4340 (5)	0.0753 (9)
H14	0.208141	0.274356	0.383623	0.090*
C15	0.25505 (9)	0.2132 (3)	0.4920 (5)	0.0826 (10)
H15	0.268888	0.270852	0.479493	0.099*
C16	0.27134 (9)	0.1279 (3)	0.5677 (5)	0.0765 (9)
C17	0.25024 (10)	0.0440 (3)	0.5858 (5)	0.0898 (11)
H17	0.260667	−0.014127	0.638841	0.108*
C18	0.21388 (9)	0.0441 (3)	0.5269 (5)	0.0788 (9)
H18	0.200120	−0.013821	0.537950	0.095*
C19	0.31105 (9)	0.1268 (3)	0.6318 (6)	0.1083 (14)
H19A	0.322354	0.186336	0.586151	0.162*
H19B	0.322231	0.068656	0.579273	0.162*
H19C	0.313852	0.124572	0.770678	0.162*
C20	0.58057 (8)	−0.1266 (2)	0.7190 (5)	0.0632 (8)
C21	0.58744 (8)	−0.0966 (2)	0.5356 (5)	0.0711 (9)
H21	0.610895	−0.081986	0.504159	0.085*
C22	0.55883 (8)	−0.0886 (2)	0.3986 (5)	0.0718 (9)
H22	0.563061	−0.066482	0.274590	0.086*
C23	0.52374 (8)	−0.1128 (2)	0.4423 (5)	0.0603 (7)
C24	0.51790 (8)	−0.1418 (2)	0.6319 (5)	0.0653 (8)
H24	0.494571	−0.156823	0.664967	0.078*
C25	0.54634 (8)	−0.1486 (2)	0.7709 (5)	0.0657 (8)
H25	0.542365	−0.167648	0.897098	0.079*
C26	0.49517 (8)	−0.1071 (2)	0.2878 (5)	0.0658 (8)
H26	0.502228	−0.084686	0.168661	0.079*
C27	0.46064 (8)	−0.1294 (2)	0.2946 (5)	0.0675 (8)
H27	0.452087	−0.151649	0.410576	0.081*
C28	0.43530 (8)	−0.1200 (2)	0.1224 (5)	0.0645 (8)
C29	0.39649 (8)	−0.1240 (2)	0.1530 (4)	0.0591 (7)
C30	0.36728 (8)	−0.1201 (2)	0.0187 (4)	0.0583 (7)
C31	0.36487 (9)	−0.1119 (3)	−0.1951 (4)	0.0731 (9)
H31A	0.341635	−0.135380	−0.245605	0.110*
H31B	0.383516	−0.151866	−0.246773	0.110*
H31C	0.367886	−0.042954	−0.231519	0.110*
C32	0.30061 (8)	−0.1231 (2)	0.0704 (4)	0.0613 (7)
C33	0.27922 (9)	−0.0428 (3)	0.1153 (5)	0.0832 (10)
H33	0.289304	0.013852	0.176028	0.100*
C34	0.24234 (10)	−0.0485 (3)	0.0680 (6)	0.0915 (11)
H34	0.227794	0.005537	0.097475	0.110*
C35	0.22651 (9)	−0.1313 (3)	−0.0210 (5)	0.0820 (10)
C36	0.24885 (8)	−0.2099 (3)	−0.0643 (5)	0.0794 (10)
H36	0.238849	−0.266349	−0.126179	0.095*
C37	0.28570 (8)	−0.2070 (3)	−0.0181 (5)	0.0717 (9)
H37	0.300229	−0.261252	−0.046600	0.086*
C38	0.18607 (9)	−0.1370 (4)	−0.0680 (6)	0.1171 (16)
H38A	0.176022	−0.189193	0.007869	0.176*
H38B	0.181355	−0.151663	−0.203171	0.176*
H38C	0.175199	−0.073923	−0.038342	0.176*
N1	−0.10784 (8)	0.13323 (19)	−0.3873 (4)	0.0706 (7)
N2	0.11600 (7)	0.1475 (2)	0.1767 (4)	0.0681 (7)
N3	0.15105 (7)	0.1491 (2)	0.1965 (4)	0.0724 (7)
N4	0.16083 (6)	0.13206 (18)	0.3880 (3)	0.0604 (6)
N5	0.61118 (8)	−0.13453 (19)	0.8654 (5)	0.0738 (7)
N6	0.38406 (7)	−0.12831 (19)	0.3349 (4)	0.0689 (7)
N7	0.34928 (7)	−0.1266 (2)	0.3210 (4)	0.0726 (7)
N8	0.33869 (6)	−0.12202 (18)	0.1281 (3)	0.0606 (6)
O1	−0.13863 (6)	0.1115 (2)	−0.3461 (4)	0.0946 (8)
O2	−0.10091 (7)	0.1614 (2)	−0.5489 (4)	0.0976 (8)
O3	0.05331 (6)	0.0976 (2)	0.5370 (3)	0.0866 (7)
O4	0.64161 (7)	−0.1192 (2)	0.8154 (4)	0.1034 (9)
O5	0.60489 (7)	−0.1547 (2)	1.0319 (4)	0.1060 (9)
O6	0.44557 (6)	−0.1070 (2)	−0.0403 (4)	0.0931 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0532 (17)	0.0548 (16)	0.0664 (19)	0.0035 (12)	0.0071 (14)	−0.0021 (14)
C2	0.0662 (19)	0.0568 (17)	0.067 (2)	−0.0019 (13)	0.0151 (15)	0.0063 (14)
C3	0.0507 (16)	0.0559 (17)	0.075 (2)	−0.0062 (12)	0.0175 (15)	0.0027 (14)
C4	0.0482 (15)	0.0498 (15)	0.0659 (18)	−0.0015 (11)	0.0124 (13)	−0.0047 (13)
C5	0.0530 (17)	0.0751 (19)	0.0626 (19)	−0.0030 (14)	0.0147 (14)	0.0042 (15)
C6	0.0482 (16)	0.077 (2)	0.070 (2)	−0.0022 (13)	0.0143 (15)	0.0023 (16)
C7	0.0508 (16)	0.0584 (17)	0.0694 (19)	−0.0001 (12)	0.0114 (14)	−0.0065 (14)
C8	0.0569 (18)	0.0591 (18)	0.070 (2)	−0.0041 (12)	0.0063 (14)	0.0004 (14)
C9	0.0517 (17)	0.0634 (18)	0.067 (2)	−0.0047 (12)	0.0086 (14)	−0.0042 (14)
C10	0.0544 (17)	0.0588 (17)	0.0551 (17)	−0.0052 (12)	0.0055 (13)	−0.0021 (13)
C11	0.0522 (16)	0.0640 (17)	0.0509 (16)	−0.0056 (12)	0.0111 (13)	−0.0025 (13)
C12	0.0648 (19)	0.094 (2)	0.0578 (19)	−0.0033 (16)	0.0097 (15)	0.0030 (16)
C13	0.0523 (17)	0.082 (2)	0.0484 (16)	−0.0002 (14)	0.0081 (13)	−0.0001 (14)
C14	0.0531 (18)	0.091 (2)	0.081 (2)	−0.0015 (16)	−0.0004 (15)	0.0130 (18)
C15	0.065 (2)	0.098 (3)	0.086 (2)	−0.0084 (18)	0.0080 (17)	0.012 (2)
C16	0.0585 (19)	0.108 (3)	0.064 (2)	0.0062 (18)	0.0111 (15)	0.0039 (19)
C17	0.072 (2)	0.105 (3)	0.094 (3)	0.019 (2)	0.0116 (19)	0.018 (2)
C18	0.067 (2)	0.082 (2)	0.088 (2)	−0.0019 (17)	0.0091 (17)	0.0082 (19)
C19	0.059 (2)	0.152 (4)	0.113 (3)	0.011 (2)	0.004 (2)	0.006 (3)
C20	0.0609 (19)	0.0534 (17)	0.076 (2)	0.0014 (13)	0.0101 (16)	−0.0024 (15)
C21	0.0543 (18)	0.083 (2)	0.078 (2)	−0.0059 (14)	0.0162 (16)	−0.0006 (17)
C22	0.0600 (19)	0.083 (2)	0.074 (2)	−0.0078 (15)	0.0194 (16)	0.0048 (17)
C23	0.0596 (18)	0.0510 (16)	0.072 (2)	0.0007 (12)	0.0143 (15)	−0.0025 (14)
C24	0.0580 (18)	0.0580 (18)	0.082 (2)	−0.0059 (13)	0.0202 (16)	0.0014 (15)
C25	0.0653 (19)	0.0604 (18)	0.073 (2)	−0.0025 (14)	0.0156 (16)	0.0068 (15)
C26	0.0598 (19)	0.0648 (18)	0.074 (2)	−0.0031 (13)	0.0155 (16)	−0.0007 (15)
C27	0.0639 (19)	0.0631 (19)	0.076 (2)	−0.0044 (13)	0.0108 (16)	0.0025 (15)
C28	0.0620 (19)	0.0643 (18)	0.068 (2)	−0.0047 (13)	0.0123 (16)	−0.0009 (15)
C29	0.0585 (18)	0.0630 (18)	0.0565 (18)	−0.0063 (13)	0.0080 (14)	−0.0006 (13)
C30	0.0619 (18)	0.0612 (17)	0.0533 (17)	−0.0027 (13)	0.0146 (14)	0.0002 (13)
C31	0.072 (2)	0.095 (2)	0.0527 (18)	0.0003 (16)	0.0104 (15)	0.0041 (16)
C32	0.0520 (17)	0.081 (2)	0.0513 (17)	0.0014 (14)	0.0087 (13)	−0.0022 (15)
C33	0.079 (2)	0.093 (2)	0.079 (2)	0.0093 (18)	0.0122 (18)	−0.0109 (19)
C34	0.076 (2)	0.113 (3)	0.087 (3)	0.029 (2)	0.0158 (19)	0.001 (2)
C35	0.062 (2)	0.122 (3)	0.063 (2)	0.006 (2)	0.0097 (16)	0.014 (2)
C36	0.0568 (19)	0.111 (3)	0.070 (2)	−0.0038 (18)	0.0024 (15)	−0.0100 (19)
C37	0.0595 (19)	0.087 (2)	0.069 (2)	0.0032 (16)	0.0077 (15)	−0.0144 (17)
C38	0.049 (2)	0.189 (5)	0.114 (3)	0.009 (2)	0.004 (2)	0.034 (3)
N1	0.0702 (19)	0.0667 (17)	0.075 (2)	0.0048 (12)	0.0063 (15)	−0.0023 (14)
N2	0.0590 (16)	0.0903 (18)	0.0553 (16)	−0.0104 (12)	0.0056 (12)	0.0003 (13)
N3	0.0589 (16)	0.105 (2)	0.0532 (16)	−0.0093 (13)	0.0056 (12)	0.0033 (14)
N4	0.0528 (14)	0.0773 (16)	0.0516 (14)	−0.0035 (11)	0.0064 (11)	0.0016 (12)
N5	0.0654 (18)	0.0686 (17)	0.088 (2)	0.0019 (12)	0.0051 (16)	0.0007 (15)
N6	0.0574 (16)	0.0926 (19)	0.0569 (16)	−0.0143 (12)	0.0045 (12)	−0.0005 (13)
N7	0.0579 (16)	0.109 (2)	0.0514 (15)	−0.0133 (13)	0.0076 (12)	−0.0052 (14)
N8	0.0597 (15)	0.0761 (16)	0.0465 (14)	−0.0053 (11)	0.0082 (11)	−0.0032 (11)
O1	0.0585 (15)	0.124 (2)	0.1007 (19)	−0.0007 (13)	−0.0004 (13)	0.0072 (15)
O2	0.0954 (19)	0.121 (2)	0.0752 (18)	0.0013 (15)	0.0009 (14)	0.0185 (15)
O3	0.0658 (14)	0.127 (2)	0.0683 (15)	−0.0105 (12)	0.0155 (11)	0.0042 (14)
O4	0.0617 (16)	0.134 (2)	0.114 (2)	−0.0016 (13)	0.0062 (14)	0.0149 (17)
O5	0.0969 (19)	0.138 (2)	0.083 (2)	0.0019 (16)	0.0039 (15)	0.0209 (17)
O6	0.0722 (15)	0.137 (2)	0.0726 (16)	−0.0047 (13)	0.0210 (12)	0.0044 (14)

Geometric parameters (Å, º) top

C1—C2	1.373 (4)	C21—H21	0.9300
C1—C6	1.375 (4)	C22—C23	1.392 (4)
C1—N1	1.462 (4)	C22—H22	0.9300
C2—C3	1.379 (4)	C23—C24	1.398 (4)
C2—H2	0.9300	C23—C26	1.456 (4)
C3—C4	1.395 (4)	C24—C25	1.382 (4)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.397 (4)	C25—H25	0.9300
C4—C7	1.454 (4)	C26—C27	1.317 (4)
C5—C6	1.372 (4)	C26—H26	0.9300
C5—H5	0.9300	C27—C28	1.473 (5)
C6—H6	0.9300	C27—H27	0.9300
C7—C8	1.325 (4)	C28—O6	1.223 (4)
C7—H7	0.9300	C28—C29	1.468 (4)
C8—C9	1.467 (4)	C29—N6	1.369 (4)
C8—H8	0.9300	C29—C30	1.380 (4)
C9—O3	1.228 (3)	C30—N8	1.342 (3)
C9—C10	1.464 (4)	C30—C31	1.480 (4)
C10—N2	1.368 (3)	C31—H31A	0.9600
C10—C11	1.376 (4)	C31—H31B	0.9600
C11—N4	1.351 (3)	C31—H31C	0.9600
C11—C12	1.478 (4)	C32—C37	1.372 (4)
C12—H12A	0.9600	C32—C33	1.378 (4)
C12—H12B	0.9600	C32—N8	1.441 (4)
C12—H12C	0.9600	C33—C34	1.386 (5)
C13—C18	1.375 (4)	C33—H33	0.9300
C13—C14	1.375 (4)	C34—C35	1.375 (5)
C13—N4	1.426 (4)	C34—H34	0.9300
C14—C15	1.381 (4)	C35—C36	1.379 (5)
C14—H14	0.9300	C35—C38	1.514 (5)
C15—C16	1.375 (5)	C36—C37	1.382 (4)
C15—H15	0.9300	C36—H36	0.9300
C16—C17	1.373 (5)	C37—H37	0.9300
C16—C19	1.509 (5)	C38—H38A	0.9600
C17—C18	1.381 (5)	C38—H38B	0.9600
C17—H17	0.9300	C38—H38C	0.9600
C18—H18	0.9300	N1—O2	1.222 (3)
C19—H19A	0.9600	N1—O1	1.229 (3)
C19—H19B	0.9600	N2—N3	1.297 (3)
C19—H19C	0.9600	N3—N4	1.369 (3)
C20—C21	1.370 (4)	N5—O4	1.218 (3)
C20—C25	1.372 (4)	N5—O5	1.220 (3)
C20—N5	1.473 (4)	N6—N7	1.286 (3)
C21—C22	1.379 (4)	N7—N8	1.367 (3)

C2—C1—C6	122.3 (3)	C23—C22—H22	119.3
C2—C1—N1	118.8 (3)	C22—C23—C24	118.2 (3)
C6—C1—N1	118.9 (3)	C22—C23—C26	118.2 (3)
C1—C2—C3	118.7 (3)	C24—C23—C26	123.6 (3)
C1—C2—H2	120.7	C25—C24—C23	120.8 (3)
C3—C2—H2	120.7	C25—C24—H24	119.6
C2—C3—C4	121.0 (3)	C23—C24—H24	119.6
C2—C3—H3	119.5	C20—C25—C24	118.7 (3)
C4—C3—H3	119.5	C20—C25—H25	120.7
C3—C4—C5	118.2 (3)	C24—C25—H25	120.7
C3—C4—C7	123.4 (2)	C27—C26—C23	128.5 (3)
C5—C4—C7	118.4 (3)	C27—C26—H26	115.7
C6—C5—C4	121.3 (3)	C23—C26—H26	115.7
C6—C5—H5	119.4	C26—C27—C28	121.4 (3)
C4—C5—H5	119.4	C26—C27—H27	119.3
C5—C6—C1	118.6 (3)	C28—C27—H27	119.3
C5—C6—H6	120.7	O6—C28—C29	120.3 (3)
C1—C6—H6	120.7	O6—C28—C27	122.4 (3)
C8—C7—C4	128.3 (3)	C29—C28—C27	117.3 (3)
C8—C7—H7	115.9	N6—C29—C30	108.9 (2)
C4—C7—H7	115.9	N6—C29—C28	121.7 (3)
C7—C8—C9	121.5 (3)	C30—C29—C28	129.3 (3)
C7—C8—H8	119.3	N8—C30—C29	103.5 (2)
C9—C8—H8	119.3	N8—C30—C31	124.5 (3)
O3—C9—C10	120.3 (3)	C29—C30—C31	132.0 (3)
O3—C9—C8	122.0 (3)	C30—C31—H31A	109.5
C10—C9—C8	117.6 (3)	C30—C31—H31B	109.5
N2—C10—C11	109.3 (2)	H31A—C31—H31B	109.5
N2—C10—C9	121.9 (3)	C30—C31—H31C	109.5
C11—C10—C9	128.7 (3)	H31A—C31—H31C	109.5
N4—C11—C10	103.7 (2)	H31B—C31—H31C	109.5
N4—C11—C12	124.3 (3)	C37—C32—C33	120.8 (3)
C10—C11—C12	132.0 (2)	C37—C32—N8	119.3 (3)
C11—C12—H12A	109.5	C33—C32—N8	119.8 (3)
C11—C12—H12B	109.5	C32—C33—C34	118.5 (3)
H12A—C12—H12B	109.5	C32—C33—H33	120.8
C11—C12—H12C	109.5	C34—C33—H33	120.8
H12A—C12—H12C	109.5	C35—C34—C33	122.3 (3)
H12B—C12—H12C	109.5	C35—C34—H34	118.8
C18—C13—C14	120.2 (3)	C33—C34—H34	118.8
C18—C13—N4	120.4 (3)	C34—C35—C36	117.4 (3)
C14—C13—N4	119.4 (3)	C34—C35—C38	121.6 (4)
C13—C14—C15	119.2 (3)	C36—C35—C38	121.0 (4)
C13—C14—H14	120.4	C35—C36—C37	121.8 (3)
C15—C14—H14	120.4	C35—C36—H36	119.1
C16—C15—C14	121.8 (3)	C37—C36—H36	119.1
C16—C15—H15	119.1	C32—C37—C36	119.2 (3)
C14—C15—H15	119.1	C32—C37—H37	120.4
C17—C16—C15	117.9 (3)	C36—C37—H37	120.4
C17—C16—C19	121.0 (3)	C35—C38—H38A	109.5
C15—C16—C19	121.0 (3)	C35—C38—H38B	109.5
C16—C17—C18	121.5 (3)	H38A—C38—H38B	109.5
C16—C17—H17	119.2	C35—C38—H38C	109.5
C18—C17—H17	119.2	H38A—C38—H38C	109.5
C13—C18—C17	119.4 (3)	H38B—C38—H38C	109.5
C13—C18—H18	120.3	O2—N1—O1	122.6 (3)
C17—C18—H18	120.3	O2—N1—C1	118.9 (3)
C16—C19—H19A	109.5	O1—N1—C1	118.5 (3)
C16—C19—H19B	109.5	N3—N2—C10	108.7 (2)
H19A—C19—H19B	109.5	N2—N3—N4	107.4 (2)
C16—C19—H19C	109.5	C11—N4—N3	110.9 (2)
H19A—C19—H19C	109.5	C11—N4—C13	129.7 (3)
H19B—C19—H19C	109.5	N3—N4—C13	119.4 (2)
C21—C20—C25	122.4 (3)	O4—N5—O5	122.9 (3)
C21—C20—N5	118.4 (3)	O4—N5—C20	118.5 (3)
C25—C20—N5	119.2 (3)	O5—N5—C20	118.6 (3)
C20—C21—C22	118.5 (3)	N7—N6—C29	109.0 (2)
C20—C21—H21	120.7	N6—N7—N8	107.2 (2)
C22—C21—H21	120.7	C30—N8—N7	111.4 (2)
C21—C22—C23	121.3 (3)	C30—N8—C32	129.7 (3)
C21—C22—H22	119.3	N7—N8—C32	118.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg4 and Cg6 are the centroids of the N2/N3/N4/C11/C10, N6–N8/C30/C29 and C32–C37 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···N7ⁱ	0.93	2.57	3.470 (4)	164
C36—H36···Cg6ⁱ	0.93	3.00	3.646 (4)	128
N1—O1···Cg1ⁱⁱ	1.23 (1)	3.30 (1)	3.724 (3)	101 (1)
N5—O4···Cg4ⁱⁱⁱ	1.22 (1)	3.26 (1)	3.565 (3)	94 (1)

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

Footnotes

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

Acknowledgements

The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for their funding of this research.

Funding information

Funding for this research was provided by: King Saud University (Deanship of Scientific Research).

References

Ahmad, M. R., Sastry, V. G., Bano, N. & Anwar, S. (2016). Arab. J. Chem, 9, S931–S935. Google Scholar
Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jung, J. C., Lee, Y., Min, D., Jung, M. & Oh, S. (2017). Molecules, 22, E1872. Web of Science CrossRef Google Scholar
Özdemir, A., Altıntop, M. D., Sever, B., Gençer, H. K., Kapkaç, H. A., Atlı, Ö. & Baysal, M. (2017). Molecules, 22, E2112. Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. Web of Science CrossRef CAS PubMed Google Scholar

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