3-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazole-4-carbaldehyde

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

doi:10.1107/S2414314619002177

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190217

https://doi.org/10.1107/S2414314619002177

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3-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazole-4-carbaldehyde

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

^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, ^dPharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, 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 8 February 2019; accepted 10 February 2019; online 19 February 2019)

The asymmetric unit of the title compound, C₂₀H₁₇N₅O, consists of two independent molecules. The molecules comprise tolyl (A), triazolyl (B), pyrazolecarbaldehydyl (C) and phenyl (D) groups. The angles between the planes through neighouring rings A/B, B/C and C/D are 39.1 (1), 6.0 (1) and 12.6 (1)°, respectively, for the first molecule and 46.0 (1), 4.6 (1) and 8.5 (2)°, respectively, for the second. In the crystal, the two independent molecules form dimers linked by four C—H⋯O hydrogen bonds with each O atom accepting two such links.

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

CCDC reference: 1896425

Structure description

1,2,3-Triazoles are biologically active heterocycles (Bonandi et al., 2017 ). Pyrazoles have been used in various pharmacological agents of diverse therapeutic categories (Karrouchi et al., 2018 ). As part of our ongoing studies in this area (Abdel-Wahab et al., 2015 ), we now describe the crystal structure of the title compound.

The asymmetric unit consists of two independent molecules 1 (containing C1) and 2 (containing C21). Each molecule comprises tolyl (A), triazolyl (B), pyrazolecarbaldehydyl (C) and phenyl (D) groups (Fig. 1). The angles between the planes through neighouring rings A/B, B/C and C/D are 39.1 (1), 6.0 (1) and 12.6 (1)°, respectively, for molecule 1 and 46.0 (1), 4.6 (1) and 8.5 (2)°, respectively, for molecule 2. In the crystal, the independent molecules are linked by four C—H⋯O hydrogen bonds (two with O1 and two with O2 as the acceptors) to form dimers (Table 1, Fig. 2). The dimers are arranged in layers parallel to the (101) plane in the extended structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.93	2.54	3.452 (3)	168
C16—H16⋯O2ⁱ	0.93	2.54	3.432 (3)	161
C33—H33⋯O1ⁱ	0.93	2.42	3.329 (3)	165
C36—H36⋯O1ⁱ	0.93	2.41	3.297 (3)	160
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

Figure 2
A view of the crystal structure along [001] showing intermolecular contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized as previously reported (Abdel-Wahab et al., 2015) from the treatment of 5-methyl-4-(1-(2-phenylhydrazono)ethyl)-1-p-tolyl-1H-1,2,3-triazole with phosphorus oxychloride in dimethylformamide (DMF) at 0°C and then at 25°C for 12 h. The resulting mixture was neutralized with ammonium hydroxide solution (5%) and the solid obtained was filtered, dried and recrystallized from DMF solution to give colourless blocks (83%), m.p. 195–196°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₅O
M_r	343.39
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	9.7894 (7), 10.9830 (6), 17.2596 (8)
α, β, γ (°)	93.490 (4), 95.702 (5), 107.729 (6)
V (Å³)	1750.67 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.51 × 0.29 × 0.21

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.988, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	16161, 8348, 4289
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.186, 1.02
No. of reflections	8348
No. of parameters	474
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1896425

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002177/hb4285sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002177/hb4285Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002177/hb4285Isup3.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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

3-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazole-4-carbaldehyde top

Crystal data top

C₂₀H₁₇N₅O	Z = 4
M_r = 343.39	F(000) = 720
Triclinic, P1	D_x = 1.303 Mg m⁻³
a = 9.7894 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9830 (6) Å	Cell parameters from 3321 reflections
c = 17.2596 (8) Å	θ = 3.9–26.0°
α = 93.490 (4)°	µ = 0.09 mm⁻¹
β = 95.702 (5)°	T = 296 K
γ = 107.729 (6)°	Block, colourless
V = 1750.67 (19) Å³	0.51 × 0.29 × 0.21 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	4289 reflections with I > 2σ(I)
ω scans	R_int = 0.033
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	θ_max = 30.0°, θ_min = 1.2°
T_min = 0.988, T_max = 0.993	h = −11→12
16161 measured reflections	k = −14→14
8348 independent reflections	l = −22→18

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.065	w = 1/[σ²(F_o²) + (0.0654P)² + 0.3491P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.186	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.21 e Å⁻³
8348 reflections	Δρ_min = −0.18 e Å⁻³
474 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0073 (12)
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. All hydrogen atoms were placed in calculated positions and refined using a riding model. Bond distances for sp² C—H hydrogen atoms were set to 0.93 Å and their U_iso set to 1.2 times U_eq(C). Bond distances for methyl C—H hydrogen atoms were set to 0.96 Å and their U_iso set to 1.5 times U_eq(C) with the group free to rotate about the C—C bond.

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

	x	y	z	U_iso*/U_eq
C1	0.0712 (4)	−0.3249 (3)	1.28244 (17)	0.1113 (12)
H1A	0.052641	−0.415552	1.284534	0.167*
H1B	−0.016407	−0.304173	1.286566	0.167*
H1C	0.142888	−0.279085	1.324964	0.167*
C2	0.1253 (3)	−0.2870 (2)	1.20609 (15)	0.0772 (8)
C3	0.2465 (3)	−0.3124 (2)	1.18414 (15)	0.0784 (8)
H3	0.292625	−0.356492	1.216383	0.094*
C4	0.3012 (3)	−0.2741 (2)	1.11560 (14)	0.0683 (7)
H4	0.383419	−0.291762	1.102293	0.082*
C5	0.2333 (3)	−0.2101 (2)	1.06756 (13)	0.0606 (6)
C6	0.1083 (3)	−0.1885 (2)	1.08590 (16)	0.0775 (8)
H6	0.059060	−0.149184	1.051878	0.093*
C7	0.0567 (3)	−0.2258 (3)	1.15538 (17)	0.0846 (8)
H7	−0.026400	−0.209094	1.168172	0.101*
C8	0.2966 (3)	−0.0657 (2)	0.95852 (13)	0.0593 (6)
C9	0.3572 (2)	−0.08357 (19)	0.89240 (13)	0.0551 (5)
C10	0.2546 (4)	0.0452 (2)	0.98959 (17)	0.0928 (10)
H10A	0.263488	0.049410	1.045658	0.139*
H10B	0.156385	0.034654	0.969319	0.139*
H10C	0.316988	0.123090	0.973863	0.139*
C11	0.3917 (2)	−0.00234 (19)	0.82856 (13)	0.0541 (5)
C12	0.4634 (2)	−0.01785 (19)	0.76307 (13)	0.0564 (6)
C13	0.4665 (2)	0.0866 (2)	0.72310 (13)	0.0569 (6)
H13	0.506839	0.105062	0.676932	0.068*
C14	0.5234 (3)	−0.1176 (2)	0.74118 (16)	0.0792 (8)
H14	0.514676	−0.183787	0.773318	0.095*
C15	0.3862 (2)	0.2794 (2)	0.74615 (14)	0.0571 (6)
C16	0.4153 (3)	0.3263 (2)	0.67588 (15)	0.0695 (7)
H16	0.444824	0.279264	0.638028	0.083*
C17	0.4001 (3)	0.4442 (3)	0.66179 (18)	0.0809 (8)
H17	0.418989	0.476358	0.613998	0.097*
C18	0.3579 (3)	0.5140 (3)	0.7172 (2)	0.0882 (9)
H18	0.346166	0.592598	0.707025	0.106*
C19	0.3328 (4)	0.4676 (3)	0.7881 (2)	0.1017 (10)
H19	0.306254	0.516093	0.826522	0.122*
C20	0.3465 (3)	0.3496 (2)	0.80313 (17)	0.0830 (8)
H20	0.328967	0.318124	0.851216	0.100*
C21	−0.2941 (4)	0.5864 (3)	0.98610 (19)	0.1168 (13)
H21A	−0.241402	0.636997	1.033160	0.175*
H21B	−0.306369	0.497299	0.991423	0.175*
H21C	−0.387077	0.598747	0.977108	0.175*
C22	−0.2114 (4)	0.6273 (2)	0.91809 (16)	0.0783 (8)
C23	−0.0752 (4)	0.6162 (2)	0.91614 (16)	0.0821 (8)
H23	−0.035778	0.580842	0.956870	0.098*
C24	0.0042 (3)	0.6561 (2)	0.85547 (15)	0.0720 (7)
H24	0.096526	0.648968	0.855653	0.086*
C25	−0.0551 (3)	0.7065 (2)	0.79484 (14)	0.0618 (6)
C26	−0.1919 (3)	0.7160 (2)	0.79411 (16)	0.0765 (7)
H26	−0.232868	0.748106	0.752328	0.092*
C27	−0.2682 (3)	0.6769 (3)	0.85651 (17)	0.0845 (8)
H27	−0.360245	0.684591	0.856511	0.101*
C28	0.0488 (2)	0.8566 (2)	0.69514 (13)	0.0569 (6)
C29	0.1348 (2)	0.8423 (2)	0.63965 (13)	0.0569 (6)
C30	−0.0065 (3)	0.9633 (2)	0.71839 (16)	0.0752 (7)
H30A	−0.097793	0.952025	0.687926	0.113*
H30B	0.061226	1.043504	0.709403	0.113*
H30C	−0.018804	0.963322	0.772884	0.113*
C31	0.1888 (2)	0.92652 (19)	0.57980 (13)	0.0561 (5)
C32	0.2710 (2)	0.9107 (2)	0.51911 (13)	0.0576 (6)
C33	0.2840 (3)	1.0170 (2)	0.47884 (13)	0.0600 (6)
H33	0.331495	1.035272	0.434849	0.072*
C34	0.3304 (3)	0.8080 (2)	0.50072 (15)	0.0704 (7)
H34	0.321107	0.744151	0.534681	0.084*
C35	0.2025 (3)	1.2106 (2)	0.49593 (13)	0.0576 (6)
C36	0.2778 (3)	1.2760 (2)	0.44062 (16)	0.0752 (7)
H36	0.337994	1.241736	0.414163	0.090*
C37	0.2636 (3)	1.3934 (3)	0.42448 (18)	0.0846 (8)
H37	0.312940	1.437398	0.386147	0.102*
C38	0.1782 (3)	1.4455 (3)	0.46404 (18)	0.0845 (8)
H38	0.169949	1.525055	0.453187	0.101*
C39	0.1041 (3)	1.3800 (3)	0.52007 (19)	0.0872 (8)
H39	0.046390	1.415715	0.547634	0.105*
C40	0.1150 (3)	1.2619 (2)	0.53551 (16)	0.0723 (7)
H40	0.063151	1.216867	0.572699	0.087*
N1	0.2891 (2)	−0.17216 (16)	0.99594 (11)	0.0587 (5)
N2	0.3447 (2)	−0.25196 (18)	0.95537 (12)	0.0697 (6)
N3	0.3860 (2)	−0.19775 (18)	0.89270 (12)	0.0686 (6)
N4	0.3537 (2)	0.10420 (16)	0.82772 (11)	0.0574 (5)
N5	0.4016 (2)	0.15758 (16)	0.76206 (10)	0.0547 (5)
N6	0.0278 (2)	0.74817 (17)	0.73213 (11)	0.0614 (5)
N7	0.0988 (2)	0.67146 (19)	0.70172 (13)	0.0741 (6)
N8	0.1638 (2)	0.72915 (18)	0.64519 (12)	0.0719 (6)
N9	0.1551 (2)	1.03480 (17)	0.57660 (11)	0.0605 (5)
N10	0.2162 (2)	1.08935 (16)	0.51417 (11)	0.0580 (5)
O1	0.5843 (3)	−0.12112 (19)	0.68400 (12)	0.1063 (8)
O2	0.3917 (2)	0.80038 (17)	0.44354 (12)	0.0902 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.144 (3)	0.101 (2)	0.074 (2)	0.008 (2)	0.040 (2)	0.0128 (16)
C2	0.096 (2)	0.0605 (15)	0.0641 (16)	0.0059 (14)	0.0200 (15)	0.0026 (12)
C3	0.087 (2)	0.0705 (16)	0.0652 (16)	0.0068 (14)	0.0003 (15)	0.0151 (12)
C4	0.0671 (17)	0.0643 (14)	0.0689 (16)	0.0136 (12)	0.0065 (13)	0.0098 (11)
C5	0.0720 (17)	0.0538 (12)	0.0563 (14)	0.0173 (11)	0.0165 (12)	0.0064 (10)
C6	0.093 (2)	0.0785 (17)	0.0757 (18)	0.0398 (15)	0.0318 (16)	0.0174 (13)
C7	0.101 (2)	0.0785 (17)	0.085 (2)	0.0324 (15)	0.0422 (17)	0.0120 (14)
C8	0.0672 (16)	0.0532 (12)	0.0622 (14)	0.0229 (10)	0.0153 (12)	0.0071 (10)
C9	0.0568 (14)	0.0509 (12)	0.0619 (14)	0.0207 (10)	0.0136 (11)	0.0068 (9)
C10	0.145 (3)	0.0704 (17)	0.087 (2)	0.0547 (17)	0.054 (2)	0.0168 (14)
C11	0.0531 (14)	0.0516 (12)	0.0608 (13)	0.0194 (10)	0.0116 (11)	0.0068 (9)
C12	0.0634 (15)	0.0528 (12)	0.0596 (13)	0.0245 (10)	0.0176 (11)	0.0067 (10)
C13	0.0648 (15)	0.0580 (13)	0.0537 (13)	0.0249 (10)	0.0173 (11)	0.0052 (10)
C14	0.111 (2)	0.0722 (16)	0.0775 (18)	0.0512 (15)	0.0417 (17)	0.0198 (13)
C15	0.0570 (14)	0.0526 (12)	0.0675 (15)	0.0245 (10)	0.0098 (11)	0.0094 (10)
C16	0.0777 (18)	0.0673 (15)	0.0711 (16)	0.0314 (12)	0.0118 (13)	0.0155 (12)
C17	0.080 (2)	0.0735 (17)	0.095 (2)	0.0288 (14)	0.0089 (16)	0.0280 (14)
C18	0.085 (2)	0.0627 (16)	0.126 (3)	0.0344 (14)	0.0134 (19)	0.0214 (16)
C19	0.125 (3)	0.084 (2)	0.125 (3)	0.0628 (19)	0.049 (2)	0.0189 (18)
C20	0.110 (2)	0.0732 (17)	0.0891 (19)	0.0511 (15)	0.0407 (17)	0.0199 (14)
C21	0.173 (4)	0.088 (2)	0.101 (2)	0.036 (2)	0.078 (3)	0.0295 (17)
C22	0.107 (2)	0.0591 (15)	0.0721 (17)	0.0218 (14)	0.0352 (16)	0.0124 (12)
C23	0.111 (3)	0.0705 (16)	0.0643 (16)	0.0251 (15)	0.0124 (16)	0.0208 (12)
C24	0.0776 (18)	0.0693 (15)	0.0713 (16)	0.0234 (13)	0.0105 (14)	0.0207 (12)
C25	0.0690 (17)	0.0595 (13)	0.0603 (14)	0.0218 (11)	0.0141 (12)	0.0132 (10)
C26	0.0767 (19)	0.0902 (18)	0.0752 (17)	0.0375 (14)	0.0216 (15)	0.0259 (14)
C27	0.086 (2)	0.0864 (18)	0.093 (2)	0.0335 (15)	0.0396 (17)	0.0244 (15)
C28	0.0613 (15)	0.0559 (13)	0.0580 (13)	0.0228 (10)	0.0110 (11)	0.0115 (10)
C29	0.0617 (15)	0.0528 (12)	0.0617 (14)	0.0232 (10)	0.0134 (11)	0.0098 (10)
C30	0.096 (2)	0.0646 (15)	0.0789 (17)	0.0362 (13)	0.0351 (15)	0.0152 (12)
C31	0.0607 (14)	0.0505 (12)	0.0582 (13)	0.0176 (10)	0.0120 (11)	0.0061 (9)
C32	0.0596 (15)	0.0556 (12)	0.0606 (14)	0.0200 (10)	0.0143 (11)	0.0064 (10)
C33	0.0641 (15)	0.0590 (13)	0.0598 (14)	0.0196 (11)	0.0207 (12)	0.0057 (10)
C34	0.0821 (19)	0.0619 (14)	0.0759 (17)	0.0289 (12)	0.0279 (15)	0.0102 (12)
C35	0.0623 (15)	0.0531 (12)	0.0598 (14)	0.0205 (10)	0.0099 (11)	0.0076 (10)
C36	0.091 (2)	0.0647 (15)	0.0822 (18)	0.0324 (13)	0.0331 (15)	0.0203 (12)
C37	0.097 (2)	0.0700 (17)	0.095 (2)	0.0297 (15)	0.0285 (17)	0.0278 (14)
C38	0.090 (2)	0.0625 (16)	0.108 (2)	0.0327 (14)	0.0123 (18)	0.0197 (15)
C39	0.089 (2)	0.0835 (19)	0.110 (2)	0.0512 (16)	0.0255 (18)	0.0232 (16)
C40	0.0728 (18)	0.0739 (16)	0.0822 (18)	0.0340 (13)	0.0226 (14)	0.0204 (13)
N1	0.0696 (13)	0.0540 (10)	0.0591 (11)	0.0256 (9)	0.0167 (10)	0.0091 (8)
N2	0.0860 (15)	0.0680 (12)	0.0720 (13)	0.0403 (11)	0.0296 (12)	0.0191 (10)
N3	0.0815 (15)	0.0659 (12)	0.0729 (13)	0.0362 (10)	0.0286 (11)	0.0185 (10)
N4	0.0600 (12)	0.0587 (11)	0.0600 (11)	0.0240 (9)	0.0172 (9)	0.0110 (8)
N5	0.0581 (12)	0.0540 (10)	0.0580 (11)	0.0236 (8)	0.0138 (9)	0.0095 (8)
N6	0.0687 (13)	0.0632 (11)	0.0628 (12)	0.0307 (9)	0.0189 (10)	0.0167 (9)
N7	0.0845 (16)	0.0707 (13)	0.0863 (15)	0.0420 (11)	0.0322 (13)	0.0260 (11)
N8	0.0841 (16)	0.0666 (12)	0.0811 (14)	0.0371 (11)	0.0322 (12)	0.0239 (10)
N9	0.0693 (13)	0.0582 (11)	0.0593 (12)	0.0232 (9)	0.0190 (10)	0.0122 (8)
N10	0.0654 (13)	0.0536 (10)	0.0590 (11)	0.0200 (9)	0.0191 (10)	0.0101 (8)
O1	0.160 (2)	0.1014 (14)	0.0995 (15)	0.0799 (14)	0.0765 (15)	0.0327 (11)
O2	0.1142 (16)	0.0829 (12)	0.0947 (14)	0.0493 (11)	0.0510 (13)	0.0147 (10)

Geometric parameters (Å, º) top

C1—C2	1.504 (3)	C21—H21C	0.9600
C1—H1A	0.9600	C22—C27	1.368 (4)
C1—H1B	0.9600	C22—C23	1.379 (4)
C1—H1C	0.9600	C23—C24	1.380 (3)
C2—C7	1.378 (4)	C23—H23	0.9300
C2—C3	1.380 (4)	C24—C25	1.373 (3)
C3—C4	1.383 (3)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.374 (3)
C4—C5	1.367 (3)	C25—N6	1.431 (3)
C4—H4	0.9300	C26—C27	1.387 (3)
C5—C6	1.378 (3)	C26—H26	0.9300
C5—N1	1.435 (3)	C27—H27	0.9300
C6—C7	1.384 (3)	C28—N6	1.356 (3)
C6—H6	0.9300	C28—C29	1.369 (3)
C7—H7	0.9300	C28—C30	1.483 (3)
C8—N1	1.356 (3)	C29—N8	1.363 (3)
C8—C9	1.368 (3)	C29—C31	1.459 (3)
C8—C10	1.486 (3)	C30—H30A	0.9600
C9—N3	1.367 (3)	C30—H30B	0.9600
C9—C11	1.461 (3)	C30—H30C	0.9600
C10—H10A	0.9600	C31—N9	1.330 (3)
C10—H10B	0.9600	C31—C32	1.416 (3)
C10—H10C	0.9600	C32—C33	1.374 (3)
C11—N4	1.332 (3)	C32—C34	1.450 (3)
C11—C12	1.416 (3)	C33—N10	1.337 (3)
C12—C13	1.369 (3)	C33—H33	0.9300
C12—C14	1.440 (3)	C34—O2	1.216 (3)
C13—N5	1.336 (3)	C34—H34	0.9300
C13—H13	0.9300	C35—C36	1.368 (3)
C14—O1	1.207 (3)	C35—C40	1.372 (3)
C14—H14	0.9300	C35—N10	1.429 (3)
C15—C16	1.368 (3)	C36—C37	1.380 (3)
C15—C20	1.371 (3)	C36—H36	0.9300
C15—N5	1.430 (3)	C37—C38	1.360 (4)
C16—C17	1.381 (3)	C37—H37	0.9300
C16—H16	0.9300	C38—C39	1.373 (4)
C17—C18	1.363 (4)	C38—H38	0.9300
C17—H17	0.9300	C39—C40	1.373 (3)
C18—C19	1.370 (4)	C39—H39	0.9300
C18—H18	0.9300	C40—H40	0.9300
C19—C20	1.380 (4)	N1—N2	1.359 (3)
C19—H19	0.9300	N2—N3	1.306 (2)
C20—H20	0.9300	N4—N5	1.366 (2)
C21—C22	1.505 (3)	N6—N7	1.358 (3)
C21—H21A	0.9600	N7—N8	1.308 (3)
C21—H21B	0.9600	N9—N10	1.366 (2)

C2—C1—H1A	109.5	C22—C23—C24	121.9 (3)
C2—C1—H1B	109.5	C22—C23—H23	119.1
H1A—C1—H1B	109.5	C24—C23—H23	119.1
C2—C1—H1C	109.5	C25—C24—C23	119.0 (3)
H1A—C1—H1C	109.5	C25—C24—H24	120.5
H1B—C1—H1C	109.5	C23—C24—H24	120.5
C7—C2—C3	117.4 (2)	C24—C25—C26	120.6 (2)
C7—C2—C1	121.7 (3)	C24—C25—N6	118.8 (2)
C3—C2—C1	121.0 (3)	C26—C25—N6	120.6 (2)
C2—C3—C4	121.9 (3)	C25—C26—C27	119.1 (3)
C2—C3—H3	119.0	C25—C26—H26	120.4
C4—C3—H3	119.0	C27—C26—H26	120.4
C5—C4—C3	119.4 (3)	C22—C27—C26	121.6 (3)
C5—C4—H4	120.3	C22—C27—H27	119.2
C3—C4—H4	120.3	C26—C27—H27	119.2
C4—C5—C6	120.1 (2)	N6—C28—C29	103.65 (18)
C4—C5—N1	119.3 (2)	N6—C28—C30	124.0 (2)
C6—C5—N1	120.5 (2)	C29—C28—C30	132.2 (2)
C5—C6—C7	119.4 (3)	N8—C29—C28	109.49 (18)
C5—C6—H6	120.3	N8—C29—C31	121.5 (2)
C7—C6—H6	120.3	C28—C29—C31	129.0 (2)
C2—C7—C6	121.6 (3)	C28—C30—H30A	109.5
C2—C7—H7	119.2	C28—C30—H30B	109.5
C6—C7—H7	119.2	H30A—C30—H30B	109.5
N1—C8—C9	104.48 (18)	C28—C30—H30C	109.5
N1—C8—C10	124.7 (2)	H30A—C30—H30C	109.5
C9—C8—C10	130.7 (2)	H30B—C30—H30C	109.5
N3—C9—C8	108.58 (19)	N9—C31—C32	111.11 (18)
N3—C9—C11	121.1 (2)	N9—C31—C29	118.7 (2)
C8—C9—C11	130.3 (2)	C32—C31—C29	130.2 (2)
C8—C10—H10A	109.5	C33—C32—C31	104.39 (19)
C8—C10—H10B	109.5	C33—C32—C34	125.8 (2)
H10A—C10—H10B	109.5	C31—C32—C34	129.8 (2)
C8—C10—H10C	109.5	N10—C33—C32	107.81 (19)
H10A—C10—H10C	109.5	N10—C33—H33	126.1
H10B—C10—H10C	109.5	C32—C33—H33	126.1
N4—C11—C12	110.92 (18)	O2—C34—C32	123.9 (2)
N4—C11—C9	119.4 (2)	O2—C34—H34	118.1
C12—C11—C9	129.7 (2)	C32—C34—H34	118.1
C13—C12—C11	104.52 (18)	C36—C35—C40	120.2 (2)
C13—C12—C14	125.7 (2)	C36—C35—N10	120.5 (2)
C11—C12—C14	129.7 (2)	C40—C35—N10	119.3 (2)
N5—C13—C12	108.00 (19)	C35—C36—C37	119.3 (2)
N5—C13—H13	126.0	C35—C36—H36	120.3
C12—C13—H13	126.0	C37—C36—H36	120.3
O1—C14—C12	124.5 (2)	C38—C37—C36	120.7 (3)
O1—C14—H14	117.7	C38—C37—H37	119.6
C12—C14—H14	117.7	C36—C37—H37	119.6
C16—C15—C20	120.8 (2)	C37—C38—C39	119.7 (3)
C16—C15—N5	120.2 (2)	C37—C38—H38	120.2
C20—C15—N5	119.0 (2)	C39—C38—H38	120.2
C15—C16—C17	119.3 (3)	C38—C39—C40	120.2 (3)
C15—C16—H16	120.4	C38—C39—H39	119.9
C17—C16—H16	120.4	C40—C39—H39	119.9
C18—C17—C16	120.6 (3)	C35—C40—C39	119.8 (2)
C18—C17—H17	119.7	C35—C40—H40	120.1
C16—C17—H17	119.7	C39—C40—H40	120.1
C17—C18—C19	119.6 (3)	C8—N1—N2	110.73 (17)
C17—C18—H18	120.2	C8—N1—C5	130.73 (19)
C19—C18—H18	120.2	N2—N1—C5	118.54 (17)
C18—C19—C20	120.6 (3)	N3—N2—N1	107.00 (17)
C18—C19—H19	119.7	N2—N3—C9	109.21 (18)
C20—C19—H19	119.7	C11—N4—N5	104.88 (17)
C15—C20—C19	119.1 (3)	C13—N5—N4	111.67 (17)
C15—C20—H20	120.4	C13—N5—C15	128.83 (18)
C19—C20—H20	120.4	N4—N5—C15	119.37 (17)
C22—C21—H21A	109.5	C28—N6—N7	111.17 (18)
C22—C21—H21B	109.5	C28—N6—C25	130.08 (19)
H21A—C21—H21B	109.5	N7—N6—C25	118.74 (18)
C22—C21—H21C	109.5	N8—N7—N6	107.05 (18)
H21A—C21—H21C	109.5	N7—N8—C29	108.63 (19)
H21B—C21—H21C	109.5	C31—N9—N10	104.86 (18)
C27—C22—C23	117.8 (2)	C33—N10—N9	111.82 (18)
C27—C22—C21	121.4 (3)	C33—N10—C35	129.31 (19)
C23—C22—C21	120.7 (3)	N9—N10—C35	118.86 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.54	3.452 (3)	168
C16—H16···O2ⁱ	0.93	2.54	3.432 (3)	161
C33—H33···O1ⁱ	0.93	2.42	3.329 (3)	165
C36—H36···O1ⁱ	0.93	2.41	3.297 (3)	160

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

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

Acknowledgements

The authors thank Umm Al-Qura and Cardiff Universities for their ongoing support.

Funding information

Funding for this research was provided by: Deanship of Scientific Research at Umm Al-Qura University (award No. 17-MED-1-03-0007).

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