5-Methyl-N′-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbon­yl)-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

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

doi:10.1107/S2414314618004248

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 3| March 2018| x180424

https://doi.org/10.1107/S2414314618004248

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5-Methyl-N′-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl)-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

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

^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, Damietta University, Egypt, ^eChemistry Department, Faculty of Science, Jazan University, Jazan 2079, Saudi Arabia, ^fChemical Industries Division, National Research Centre, Dokki 12622, Giza, Egypt, and ^gSchool 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 March 2018; accepted 12 March 2018; online 15 March 2018)

The asymmetric unit of the title compound, C₂₀H₁₈N₈O₂, comprises one complete molecule and a half molecule completed by crystallographic twofold symmetry leading to Z = 12. The dihedral angles between the planes of the linked phenyl and methyltriazolyl groups are 69.48 (5) and 44.85 (9)° for the first molecule and 42.88 (9)° for the second. The conformations of the diformyl hydrazyl groups of the molecules are similar as indicated by C—N—N—C torsion angles of −83.4 (2) and −86.4 (3)°. In the crystal, neighbouring molecules are linked by pairs of N—H⋯O hydrogen bonds to form independent columns propagating parallel to the c-axis direction.

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

CCDC reference: 1829173

Structure description

N,N′-Diacylhydrazines are precursors for heterocycles such as 1,3,4-oxadiazoles (Abdel-Wahab et al., 2017 ). Treatment of acid hydrazides with an oxidizing agent gives N,N′-diacylhydrazines (Nikolić et al., 2017 ; Mogilaiah et al., 2003 ; Prakash et al., 1997 ). As part of our studies in this area, we now describe the crystal structure of the title compound.

The asymmetric unit comprises one and a half molecules (Fig. 1). The second molecule is completed by crystallographic twofold symmetry. The dihedral angles between the planes of the linked phenyl and methyltriazolyl groups are 69.48 (5)° and 44.85 (9)° for the first molecule and 42.88 (9)° for the second. The conformations of the diformyl hydrazyl groups of the two molecules are similar as indicated by the C—N—N—C torsion angles of −83.4 (2)° and −86.4 (3)°. The dihedral angle between the C7 and C13 triazole rings in the first molecule is 63.65 (10) and the equivalent angle between the symmetry-related C27 rings in the second molecule is 61.80 (4)°.

Figure 1
The molecular structure showing 50% displacement ellipsoids. Primed and unlabelled atoms are generated by the symmetry operation 1 − x, y, $[{1\over 2}]$ − z.

Neighbouring molecules in the crystal structure are linked by pairs of N—H⋯O hydrogen bonds (Table 1), forming columns parallel to the c-axis direction The two types of molecule form separate columns that alternate along the a-axis direction (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.86	2.24	2.9412 (19)	139
N5—H5A⋯O2ⁱⁱ	0.86	2.23	2.9395 (19)	140
N12—H12⋯O3ⁱⁱⁱ	0.86	2.28	3.098 (2)	158
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z-{\script{1\over 2}}]$ .

Figure 2
A segment of the crystal structure viewed down the b axis showing N—H⋯O hydrogen-bonding contacts leading to [001] chains.

Synthesis and crystallization

The synthesis of the title compound has already been reported (Abdel-Wahab et al., 2017). Yellow needles of the title compound were recrystallized from dimethylformamide solution (yield = 72%; m.p. 279–280°C).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₈O₂
M_r	402.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	61.5399 (18), 11.8988 (4), 8.2661 (3)
β (°)	93.301 (3)
V (Å³)	6042.8 (3)
Z	12
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.17 × 0.08

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	0.583, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	28646, 7636, 5320
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.162, 1.06
No. of reflections	7636
No. of parameters	410
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1829173

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004248/hb4215sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004248/hb4215Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618004248/hb4215Isup3.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 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

5-Methyl-N'-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl)-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide top

Crystal data top

C₂₀H₁₈N₈O₂	F(000) = 2520
M_r = 402.42	D_x = 1.327 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 61.5399 (18) Å	Cell parameters from 7925 reflections
b = 11.8988 (4) Å	θ = 3.3–29.3°
c = 8.2661 (3) Å	µ = 0.09 mm⁻¹
β = 93.301 (3)°	T = 296 K
V = 6042.8 (3) Å³	Needle, yellow
Z = 12	0.36 × 0.17 × 0.08 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	5320 reflections with I > 2σ(I)
ω scans	R_int = 0.025
Absorption correction: gaussian (CrysAlis PRO, Rigaku OD, 2015)	θ_max = 29.9°, θ_min = 3.0°
T_min = 0.583, T_max = 1.000	h = −86→79
28646 measured reflections	k = −16→16
7636 independent reflections	l = −11→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0711P)² + 3.1965P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.162	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.27 e Å⁻³
7636 reflections	Δρ_min = −0.24 e Å⁻³
410 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00114 (19)
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. Aromatic C—H distances were set to 0.93\%A 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\%A with U(iso) set to 1.5 times the U_eq for the C atoms to which they are bonded. The N—H bond was set to 0.86 Å and U_iso(H) set to 1.2 times U_eq (N).

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

	x	y	z	U_iso*/U_eq
C1	0.22978 (2)	0.37333 (15)	0.7766 (2)	0.0463 (4)
C2	0.21677 (3)	0.44007 (18)	0.6775 (3)	0.0629 (5)
H2	0.222337	0.504302	0.630957	0.075*
C3	0.19509 (3)	0.4103 (2)	0.6476 (3)	0.0772 (7)
H3	0.186076	0.454780	0.579953	0.093*
C4	0.18692 (3)	0.3164 (2)	0.7165 (3)	0.0738 (6)
H4	0.172289	0.298191	0.698205	0.089*
C5	0.20016 (3)	0.2491 (2)	0.8123 (3)	0.0787 (7)
H5	0.194609	0.184275	0.857403	0.094*
C6	0.22191 (3)	0.27693 (19)	0.8426 (3)	0.0682 (6)
H6	0.231025	0.230779	0.906967	0.082*
C7	0.27078 (2)	0.36356 (13)	0.7642 (2)	0.0403 (3)
C8	0.28629 (2)	0.43569 (13)	0.83050 (19)	0.0398 (3)
C9	0.27244 (3)	0.26166 (16)	0.6632 (3)	0.0596 (5)
H9A	0.258973	0.220841	0.661961	0.089*
H9B	0.284030	0.214962	0.707488	0.089*
H9C	0.275385	0.283020	0.554648	0.089*
C10	0.30996 (2)	0.43355 (14)	0.81230 (19)	0.0400 (3)
C11	0.35563 (2)	0.43823 (14)	1.00094 (19)	0.0410 (4)
C12	0.37925 (2)	0.44678 (14)	0.98102 (19)	0.0405 (3)
C13	0.39533 (2)	0.37223 (14)	1.03065 (19)	0.0405 (3)
C14	0.39412 (3)	0.26250 (15)	1.1149 (2)	0.0547 (4)
H14A	0.406393	0.217129	1.090101	0.082*
H14B	0.380918	0.224675	1.079264	0.082*
H14C	0.394262	0.274683	1.229725	0.082*
C15	0.43574 (3)	0.38279 (15)	0.9912 (2)	0.0496 (4)
C16	0.44469 (3)	0.3415 (2)	1.1341 (3)	0.0709 (6)
H16	0.436481	0.337511	1.224957	0.085*
C17	0.46606 (4)	0.3057 (3)	1.1423 (4)	0.0966 (9)
H17	0.472198	0.276129	1.238498	0.116*
C18	0.47825 (4)	0.3137 (3)	1.0095 (5)	0.0988 (9)
H18	0.492634	0.289331	1.015520	0.119*
C19	0.46925 (4)	0.3576 (3)	0.8671 (4)	0.0924 (9)
H19	0.477671	0.364003	0.777621	0.111*
C20	0.44778 (3)	0.3923 (2)	0.8559 (3)	0.0682 (6)
H20	0.441576	0.421280	0.759477	0.082*
C21	0.60369 (3)	0.87144 (15)	0.2703 (2)	0.0499 (4)
C22	0.61242 (3)	0.77039 (17)	0.3228 (3)	0.0573 (5)
H22	0.603357	0.711174	0.348183	0.069*
C23	0.63484 (3)	0.7577 (2)	0.3373 (3)	0.0714 (6)
H23	0.640836	0.689795	0.373190	0.086*
C24	0.64812 (3)	0.8442 (2)	0.2995 (4)	0.0905 (8)
H24	0.663156	0.835202	0.309213	0.109*
C25	0.63926 (3)	0.9448 (2)	0.2467 (5)	0.1052 (11)
H25	0.648369	1.003664	0.220610	0.126*
C26	0.61691 (3)	0.95940 (19)	0.2322 (4)	0.0810 (8)
H26	0.610951	1.027625	0.197199	0.097*
C27	0.56458 (2)	0.86275 (14)	0.3473 (2)	0.0426 (4)
C28	0.54653 (2)	0.91029 (14)	0.2699 (2)	0.0431 (4)
C29	0.56739 (3)	0.79950 (18)	0.5004 (2)	0.0601 (5)
H29A	0.567458	0.720405	0.477553	0.090*
H29B	0.555601	0.816576	0.567532	0.090*
H29C	0.580926	0.820337	0.555824	0.090*
C30	0.52413 (2)	0.91587 (15)	0.3236 (2)	0.0453 (4)
N1	0.25201 (2)	0.40700 (12)	0.81303 (18)	0.0450 (3)
N2	0.25575 (2)	0.50136 (14)	0.9052 (2)	0.0619 (5)
N3	0.27670 (2)	0.51714 (14)	0.9151 (2)	0.0565 (4)
N4	0.32124 (2)	0.50774 (13)	0.90749 (17)	0.0466 (3)
H4A	0.314472	0.552915	0.968324	0.056*
N5	0.34366 (2)	0.51120 (13)	0.90730 (18)	0.0468 (3)
H5A	0.349965	0.559343	0.848150	0.056*
N6	0.38802 (2)	0.53479 (13)	0.90331 (19)	0.0511 (4)
N7	0.40897 (2)	0.52009 (13)	0.9023 (2)	0.0536 (4)
N8	0.41358 (2)	0.42055 (12)	0.97963 (17)	0.0442 (3)
N9	0.58066 (2)	0.88693 (12)	0.24842 (18)	0.0469 (3)
N10	0.57279 (2)	0.94466 (15)	0.1149 (2)	0.0624 (5)
N11	0.55203 (2)	0.95812 (15)	0.12926 (19)	0.0578 (4)
N12	0.51107 (2)	0.98835 (14)	0.23792 (18)	0.0525 (4)
H12	0.516383	1.033741	0.169530	0.063*
O1	0.31841 (2)	0.37162 (11)	0.71613 (15)	0.0521 (3)
O2	0.34779 (2)	0.37352 (11)	1.09605 (15)	0.0516 (3)
O3	0.51812 (2)	0.86215 (12)	0.43867 (16)	0.0587 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0314 (7)	0.0552 (10)	0.0526 (10)	−0.0040 (7)	0.0047 (7)	−0.0018 (8)
C2	0.0383 (9)	0.0689 (12)	0.0812 (14)	−0.0015 (8)	0.0024 (9)	0.0135 (11)
C3	0.0394 (10)	0.0916 (16)	0.0993 (18)	0.0040 (10)	−0.0081 (10)	0.0130 (14)
C4	0.0346 (9)	0.0895 (16)	0.0970 (17)	−0.0123 (10)	0.0010 (10)	−0.0048 (14)
C5	0.0546 (12)	0.0879 (16)	0.0931 (17)	−0.0294 (11)	0.0001 (11)	0.0166 (13)
C6	0.0505 (10)	0.0772 (14)	0.0755 (14)	−0.0169 (10)	−0.0081 (9)	0.0221 (11)
C7	0.0336 (7)	0.0433 (8)	0.0439 (9)	0.0005 (6)	0.0009 (6)	0.0035 (7)
C8	0.0317 (7)	0.0466 (8)	0.0413 (8)	0.0007 (6)	0.0023 (6)	−0.0003 (7)
C9	0.0502 (10)	0.0512 (10)	0.0772 (14)	−0.0021 (8)	0.0016 (9)	−0.0140 (9)
C10	0.0330 (7)	0.0472 (8)	0.0399 (8)	0.0024 (6)	0.0025 (6)	0.0050 (7)
C11	0.0337 (7)	0.0514 (9)	0.0379 (8)	−0.0059 (7)	0.0032 (6)	−0.0044 (7)
C12	0.0325 (7)	0.0501 (9)	0.0389 (8)	−0.0047 (6)	0.0016 (6)	0.0018 (7)
C13	0.0343 (7)	0.0482 (9)	0.0392 (8)	−0.0029 (6)	0.0030 (6)	−0.0029 (7)
C14	0.0502 (10)	0.0510 (10)	0.0634 (12)	0.0016 (8)	0.0080 (8)	0.0086 (9)
C15	0.0332 (8)	0.0532 (10)	0.0629 (11)	0.0023 (7)	0.0063 (7)	−0.0082 (8)
C16	0.0448 (10)	0.0916 (16)	0.0760 (15)	0.0142 (10)	0.0014 (10)	0.0094 (12)
C17	0.0512 (12)	0.117 (2)	0.120 (2)	0.0285 (14)	−0.0035 (14)	0.0139 (18)
C18	0.0447 (12)	0.105 (2)	0.147 (3)	0.0245 (13)	0.0095 (15)	−0.017 (2)
C19	0.0521 (12)	0.112 (2)	0.116 (2)	0.0062 (13)	0.0330 (14)	−0.0272 (18)
C20	0.0500 (10)	0.0825 (14)	0.0735 (14)	−0.0001 (10)	0.0175 (10)	−0.0121 (11)
C21	0.0314 (7)	0.0540 (10)	0.0641 (11)	0.0051 (7)	0.0016 (7)	−0.0039 (8)
C22	0.0462 (9)	0.0574 (11)	0.0679 (12)	0.0101 (8)	−0.0002 (8)	0.0007 (9)
C23	0.0505 (11)	0.0766 (14)	0.0860 (16)	0.0242 (10)	−0.0061 (10)	−0.0014 (12)
C24	0.0347 (10)	0.0980 (18)	0.138 (2)	0.0130 (11)	−0.0053 (12)	−0.0087 (17)
C25	0.0391 (11)	0.0823 (17)	0.195 (3)	−0.0061 (11)	0.0125 (15)	0.0065 (19)
C26	0.0388 (10)	0.0608 (12)	0.144 (2)	0.0033 (9)	0.0096 (12)	0.0089 (14)
C27	0.0355 (7)	0.0455 (8)	0.0471 (9)	−0.0008 (6)	0.0045 (7)	−0.0002 (7)
C28	0.0320 (7)	0.0529 (9)	0.0445 (9)	−0.0021 (7)	0.0036 (6)	0.0050 (7)
C29	0.0586 (11)	0.0672 (12)	0.0548 (11)	0.0111 (9)	0.0057 (9)	0.0127 (9)
C30	0.0321 (7)	0.0576 (10)	0.0465 (9)	−0.0072 (7)	0.0048 (7)	−0.0007 (8)
N1	0.0315 (6)	0.0494 (8)	0.0542 (8)	−0.0036 (6)	0.0034 (6)	−0.0026 (6)
N2	0.0357 (7)	0.0674 (10)	0.0834 (12)	−0.0037 (7)	0.0106 (7)	−0.0255 (9)
N3	0.0338 (7)	0.0651 (9)	0.0712 (11)	−0.0041 (6)	0.0081 (7)	−0.0212 (8)
N4	0.0272 (6)	0.0632 (9)	0.0496 (8)	−0.0012 (6)	0.0034 (6)	−0.0075 (7)
N5	0.0265 (6)	0.0646 (9)	0.0494 (8)	−0.0048 (6)	0.0024 (6)	0.0076 (7)
N6	0.0341 (7)	0.0573 (9)	0.0622 (10)	−0.0013 (6)	0.0047 (6)	0.0124 (7)
N7	0.0339 (7)	0.0572 (9)	0.0702 (10)	−0.0026 (6)	0.0076 (7)	0.0125 (8)
N8	0.0332 (6)	0.0499 (8)	0.0495 (8)	−0.0001 (6)	0.0040 (6)	0.0014 (6)
N9	0.0321 (6)	0.0553 (8)	0.0535 (8)	0.0055 (6)	0.0039 (6)	0.0077 (7)
N10	0.0353 (7)	0.0872 (12)	0.0656 (10)	0.0123 (7)	0.0118 (7)	0.0286 (9)
N11	0.0325 (7)	0.0834 (11)	0.0582 (10)	0.0094 (7)	0.0094 (6)	0.0211 (8)
N12	0.0261 (6)	0.0760 (10)	0.0563 (9)	0.0002 (6)	0.0091 (6)	0.0088 (8)
O1	0.0395 (6)	0.0617 (8)	0.0555 (7)	0.0077 (5)	0.0056 (5)	−0.0080 (6)
O2	0.0408 (6)	0.0638 (8)	0.0507 (7)	−0.0097 (5)	0.0077 (5)	0.0071 (6)
O3	0.0441 (6)	0.0733 (9)	0.0598 (8)	−0.0107 (6)	0.0123 (6)	0.0114 (7)

Geometric parameters (Å, º) top

C1—C2	1.366 (3)	C18—C19	1.375 (4)
C1—C6	1.371 (3)	C18—H18	0.9300
C1—N1	1.4403 (19)	C19—C20	1.383 (3)
C2—C3	1.389 (3)	C19—H19	0.9300
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.364 (3)	C21—C26	1.373 (3)
C3—H3	0.9300	C21—C22	1.377 (3)
C4—C5	1.363 (3)	C21—N9	1.4302 (19)
C4—H4	0.9300	C22—C23	1.386 (3)
C5—C6	1.387 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.362 (4)
C6—H6	0.9300	C23—H23	0.9300
C7—N1	1.3486 (19)	C24—C25	1.377 (4)
C7—C8	1.374 (2)	C24—H24	0.9300
C7—C9	1.479 (2)	C25—C26	1.384 (3)
C8—N3	1.351 (2)	C25—H25	0.9300
C8—C10	1.474 (2)	C26—H26	0.9300
C9—H9A	0.9600	C27—N9	1.350 (2)
C9—H9B	0.9600	C27—C28	1.372 (2)
C9—H9C	0.9600	C27—C29	1.474 (2)
C10—O1	1.2217 (19)	C28—N11	1.355 (2)
C10—N4	1.348 (2)	C28—C30	1.474 (2)
C11—O2	1.2195 (19)	C29—H29A	0.9600
C11—N5	1.353 (2)	C29—H29B	0.9600
C11—C12	1.476 (2)	C29—H29C	0.9600
C12—N6	1.357 (2)	C30—O3	1.221 (2)
C12—C13	1.374 (2)	C30—N12	1.351 (2)
C13—N8	1.3505 (19)	N1—N2	1.369 (2)
C13—C14	1.484 (2)	N2—N3	1.3003 (19)
C14—H14A	0.9600	N4—N5	1.3802 (17)
C14—H14B	0.9600	N4—H4A	0.8600
C14—H14C	0.9600	N5—H5A	0.8600
C15—C16	1.366 (3)	N6—N7	1.3019 (18)
C15—C20	1.382 (3)	N7—N8	1.368 (2)
C15—N8	1.434 (2)	N9—N10	1.365 (2)
C16—C17	1.380 (3)	N10—N11	1.2994 (18)
C16—H16	0.9300	N12—N12ⁱ	1.388 (2)
C17—C18	1.368 (4)	N12—H12	0.8600
C17—H17	0.9300

C2—C1—C6	121.10 (17)	C20—C19—H19	119.8
C2—C1—N1	118.70 (15)	C15—C20—C19	118.5 (2)
C6—C1—N1	120.19 (16)	C15—C20—H20	120.8
C1—C2—C3	118.84 (19)	C19—C20—H20	120.8
C1—C2—H2	120.6	C26—C21—C22	120.80 (17)
C3—C2—H2	120.6	C26—C21—N9	117.95 (16)
C4—C3—C2	120.5 (2)	C22—C21—N9	121.21 (16)
C4—C3—H3	119.7	C21—C22—C23	119.38 (19)
C2—C3—H3	119.7	C21—C22—H22	120.3
C5—C4—C3	120.11 (19)	C23—C22—H22	120.3
C5—C4—H4	119.9	C24—C23—C22	120.4 (2)
C3—C4—H4	119.9	C24—C23—H23	119.8
C4—C5—C6	120.2 (2)	C22—C23—H23	119.8
C4—C5—H5	119.9	C23—C24—C25	119.84 (19)
C6—C5—H5	119.9	C23—C24—H24	120.1
C1—C6—C5	119.2 (2)	C25—C24—H24	120.1
C1—C6—H6	120.4	C24—C25—C26	120.7 (2)
C5—C6—H6	120.4	C24—C25—H25	119.7
N1—C7—C8	103.20 (14)	C26—C25—H25	119.7
N1—C7—C9	124.85 (14)	C21—C26—C25	118.9 (2)
C8—C7—C9	131.95 (14)	C21—C26—H26	120.5
N3—C8—C7	109.91 (13)	C25—C26—H26	120.5
N3—C8—C10	121.97 (14)	N9—C27—C28	103.39 (14)
C7—C8—C10	128.07 (14)	N9—C27—C29	125.11 (15)
C7—C9—H9A	109.5	C28—C27—C29	131.50 (15)
C7—C9—H9B	109.5	N11—C28—C27	109.76 (13)
H9A—C9—H9B	109.5	N11—C28—C30	121.58 (15)
C7—C9—H9C	109.5	C27—C28—C30	128.64 (15)
H9A—C9—H9C	109.5	C27—C29—H29A	109.5
H9B—C9—H9C	109.5	C27—C29—H29B	109.5
O1—C10—N4	123.41 (14)	H29A—C29—H29B	109.5
O1—C10—C8	122.48 (15)	C27—C29—H29C	109.5
N4—C10—C8	114.08 (14)	H29A—C29—H29C	109.5
O2—C11—N5	123.48 (14)	H29B—C29—H29C	109.5
O2—C11—C12	122.96 (15)	O3—C30—N12	123.03 (15)
N5—C11—C12	113.53 (14)	O3—C30—C28	122.77 (16)
N6—C12—C13	109.89 (13)	N12—C30—C28	114.16 (14)
N6—C12—C11	121.82 (14)	C7—N1—N2	111.19 (12)
C13—C12—C11	128.28 (15)	C7—N1—C1	130.57 (14)
N8—C13—C12	103.27 (14)	N2—N1—C1	118.15 (13)
N8—C13—C14	125.91 (14)	N3—N2—N1	106.73 (13)
C12—C13—C14	130.79 (14)	N2—N3—C8	108.97 (14)
C13—C14—H14A	109.5	C10—N4—N5	120.00 (13)
C13—C14—H14B	109.5	C10—N4—H4A	120.0
H14A—C14—H14B	109.5	N5—N4—H4A	120.0
C13—C14—H14C	109.5	C11—N5—N4	119.44 (13)
H14A—C14—H14C	109.5	C11—N5—H5A	120.3
H14B—C14—H14C	109.5	N4—N5—H5A	120.3
C16—C15—C20	121.42 (18)	N7—N6—C12	108.70 (14)
C16—C15—N8	120.36 (16)	N6—N7—N8	106.98 (13)
C20—C15—N8	118.19 (18)	C13—N8—N7	111.16 (13)
C15—C16—C17	119.3 (2)	C13—N8—C15	130.57 (15)
C15—C16—H16	120.4	N7—N8—C15	118.25 (13)
C17—C16—H16	120.4	C27—N9—N10	111.01 (13)
C18—C17—C16	120.3 (3)	C27—N9—C21	130.64 (15)
C18—C17—H17	119.8	N10—N9—C21	118.03 (14)
C16—C17—H17	119.8	N11—N10—N9	107.05 (13)
C17—C18—C19	120.1 (2)	N10—N11—C28	108.78 (14)
C17—C18—H18	120.0	C30—N12—N12ⁱ	118.92 (14)
C19—C18—H18	120.0	C30—N12—H12	120.5
C18—C19—C20	120.5 (2)	N12ⁱ—N12—H12	120.5
C18—C19—H19	119.8

C10—N4—N5—C11	−83.4 (2)	C30—N12—N12ⁱ—C30ⁱ	−86.4 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱⁱ	0.86	2.24	2.9412 (19)	139
N5—H5A···O2ⁱⁱⁱ	0.86	2.23	2.9395 (19)	140
N12—H12···O3^iv	0.86	2.28	3.098 (2)	158

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

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.

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