1-(4-Fluoro­phen­yl)-5-methyl-N′-{1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]ethyl­idene}-1H-1,2,3-triazole-4-carbohydrazide

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

doi:10.1107/S241431461900261X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190261

https://doi.org/10.1107/S241431461900261X

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1-(4-Fluorophenyl)-5-methyl-N′-{1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]ethylidene}-1H-1,2,3-triazole-4-carbohydrazide

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Emad Yousif,^d Mohammad Hayal Alotaibi,^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, ^dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, ^eNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by O. Blacque, University of Zürich, Switzerland (Received 6 February 2019; accepted 20 February 2019; online 22 February 2019)

The title molecule, C₂₂H₂₁FN₈O, comprises fluorophenyl (A), methyltriazolyl (B), methyltriazolyl (C) and tolyl (D) rings. The twist angles between the planes through neighbouring ring pairs A/B, B/C and C/D are 45.0 (1), 9.4 (1) and 43.2 (1)°, respectively. Intermolecular π–π interactions between rings A and C and between B and D propagate the structure in the [010] direction and weak C—H⋯O interactions also occur.

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

CCDC reference: 1898411

Structure description

Acyl hydrazides are common precursors for the synthesis of various heterocycles and have a wide range of applications such as use in pharmaceuticals, as chemical preservatives for plants, and in the manufacture of polymers (Abdel-Wahab et al., 2017 ; Hassan & Shawky, 2010 ; Sarma et al., 2011 ; Shamsabadi & Chudasama, 2017 ).

The asymmetric unit comprises one molecule of the title compound. The molecule has fluorophenyl (A; C1–C6), methyltriazolyl (B; N1–N3/C7/C8), methyltriazolyl (C; N6–N8/C13/C14) and tolyl (D; C16–C21) rings (Fig. 1). The twist angles between the planes through neighbouring ring pairs A/B, B/C and C/D are 45.0 (1), 9.4 (1) and 43.2 (1)°, respectively. Intermolecular π–π interactions between rings A and C and between B and D with centroid-to-centroid distances in the range 3.774 (3) to 4.075 (3) Å propagate the structure in the [010] direction (Fig. 2). Weak C—H⋯O interactions (Table 1) also occur.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.96	2.48	3.229 (12)	135
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Figure 1
An ORTEP representation of the asymmetric unit showing 50% probability ellipsoids.

Figure 2
A segment of the crystal structure showing intermolecular π–π contacts as green dotted lines and C—H⋯O contacts in red.

Synthesis and crystallization

The title compound was synthesized by condensation of 1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide with 1-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)ethanone in ethanol in the presence of a catalytic amount of glacial acetic acid under reflux for 2 h. The solid obtained was collected by filtration, washed with ethanol, dried and recrystallized from dimethylformamide solution to give colourless crystals (78%), m.p. 241–242°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The geometries of the fluorophenyl and tolyl rings were restrained to be regular hexagons.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₁FN₈O
M_r	432.47
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	12.2574 (10), 7.6912 (8), 22.821 (3)
V (Å³)	2151.5 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.16 × 0.09

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.329, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13165, 3917, 2393
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.178, 1.08
No. of reflections	3917
No. of parameters	272
No. of restraints	2
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23
Computer programs: CrysAlis PRO (Rigaku OD, 2018 $[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1898411

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431461900261X/zq4035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461900261X/zq4035Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461900261X/zq4035Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS (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).

1-(4-Fluorophenyl)-5-methyl-N'-{1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]ethylidene}-1H-1,2,3-triazole-4-carbohydrazide top

Crystal data top

C₂₂H₂₁FN₈O	D_x = 1.335 Mg m⁻³
M_r = 432.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1237 reflections
a = 12.2574 (10) Å	θ = 3.7–22.8°
b = 7.6912 (8) Å	µ = 0.09 mm⁻¹
c = 22.821 (3) Å	T = 293 K
V = 2151.5 (4) Å³	Plate, colourless
Z = 4	0.25 × 0.16 × 0.09 mm
F(000) = 904

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer	2393 reflections with I > 2σ(I)
ω scans	R_int = 0.059
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	θ_max = 25.3°, θ_min = 3.3°
T_min = 0.329, T_max = 1.000	h = −14→14
13165 measured reflections	k = −9→9
3917 independent reflections	l = −27→27

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.062	H-atom parameters not refined
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0857P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3917 reflections	Δρ_max = 0.17 e Å⁻³
272 parameters	Δρ_min = −0.22 e Å⁻³

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 except N–H were placed in calculated positions and refined using a riding model. Bond distances for sp² C–H H atoms were set to 0.93 Å with their U_iso set to 1.2 times U_eq(C). Bond distances for methyl C–H H atoms were set to 0.96 Å and their U_iso set to 1.5 times U_eq(C) with the group free to spin about the C–C bond. The bond distance for the N–H hydrogen was restrained to 0.86 (1) Å and the 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	0.1001 (4)	0.3862 (6)	0.57816 (15)	0.099 (2)
C2	0.0357 (3)	0.3166 (6)	0.5338 (2)	0.0845 (18)
H2	−0.033152	0.272817	0.542505	0.101*
C3	0.0742 (3)	0.3125 (5)	0.47657 (17)	0.0728 (15)
H3	0.031140	0.265995	0.446919	0.087*
C4	0.1771 (3)	0.3780 (5)	0.46362 (15)	0.0656 (16)
C5	0.2415 (3)	0.4476 (5)	0.5079 (2)	0.0768 (17)
H5	0.310362	0.491423	0.499269	0.092*
C6	0.2030 (4)	0.4517 (6)	0.56520 (18)	0.100 (2)
H6	0.246072	0.498247	0.594855	0.120*
C7	0.1671 (4)	0.4180 (6)	0.3554 (3)	0.0631 (14)
C8	0.2445 (5)	0.3941 (6)	0.3136 (3)	0.0690 (16)
C9	0.0536 (4)	0.4855 (8)	0.3510 (3)	0.0775 (16)
H9A	0.035619	0.548120	0.386103	0.116*
H9B	0.003943	0.389995	0.346236	0.116*
H9C	0.047980	0.561882	0.317889	0.116*
C10	0.2357 (5)	0.4209 (8)	0.2504 (3)	0.0759 (17)
C11	0.4198 (5)	0.3741 (8)	0.1336 (3)	0.0767 (17)
C12	0.5277 (6)	0.3532 (16)	0.1639 (4)	0.140 (4)
H12A	0.523474	0.258780	0.191350	0.209*
H12B	0.545407	0.458534	0.184426	0.209*
H12C	0.583298	0.329026	0.135441	0.209*
C13	0.4183 (5)	0.3728 (7)	0.0706 (3)	0.0673 (16)
C14	0.3354 (4)	0.4048 (6)	0.0315 (3)	0.0600 (14)
C15	0.2226 (5)	0.4680 (8)	0.0398 (3)	0.0730 (15)
H15A	0.174259	0.370597	0.044115	0.110*
H15B	0.200989	0.535370	0.006314	0.110*
H15C	0.219163	0.539128	0.074298	0.110*
C16	0.3374 (3)	0.3845 (5)	−0.07862 (13)	0.0619 (15)
C17	0.3995 (3)	0.4562 (5)	−0.12351 (18)	0.0797 (17)
H17	0.468108	0.502043	−0.115472	0.096*
C18	0.3591 (4)	0.4593 (5)	−0.18040 (15)	0.0878 (19)
H18	0.400619	0.507228	−0.210432	0.105*
C19	0.2566 (4)	0.3907 (5)	−0.19241 (14)	0.0851 (19)
C20	0.1945 (3)	0.3191 (5)	−0.14752 (19)	0.0771 (16)
H20	0.125893	0.273217	−0.155560	0.092*
C21	0.2349 (3)	0.3160 (5)	−0.09063 (16)	0.0689 (15)
H21	0.193380	0.268032	−0.060599	0.083*
C22	0.2099 (9)	0.3958 (12)	−0.2541 (4)	0.121 (3)
H22A	0.236919	0.298342	−0.275996	0.181*
H22B	0.231591	0.501791	−0.272951	0.181*
H22C	0.131744	0.390311	−0.252184	0.181*
N1	0.2179 (4)	0.3754 (6)	0.4059 (2)	0.0660 (12)
N2	0.3231 (4)	0.3254 (7)	0.3958 (3)	0.0812 (15)
N3	0.3393 (4)	0.3382 (7)	0.3394 (3)	0.0783 (14)
N4	0.3292 (4)	0.3919 (7)	0.2199 (3)	0.0825 (15)
H4	0.386 (4)	0.375 (9)	0.242 (3)	0.099*
N5	0.3285 (4)	0.3929 (6)	0.1598 (3)	0.0761 (14)
N6	0.5106 (4)	0.3288 (7)	0.0395 (3)	0.0846 (15)
N7	0.4885 (4)	0.3301 (7)	−0.0159 (3)	0.0821 (14)
N8	0.3819 (4)	0.3770 (5)	−0.0218 (2)	0.0641 (12)
O1	0.1518 (4)	0.4662 (7)	0.2271 (2)	0.1086 (16)
F1	0.0628 (5)	0.3904 (9)	0.6317 (2)	0.149 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.110 (6)	0.104 (5)	0.083 (6)	0.032 (4)	−0.008 (5)	0.005 (4)
C2	0.073 (4)	0.082 (4)	0.099 (5)	0.014 (3)	0.001 (4)	0.009 (4)
C3	0.066 (4)	0.065 (3)	0.087 (4)	0.003 (3)	−0.005 (3)	−0.001 (3)
C4	0.058 (3)	0.055 (3)	0.084 (5)	0.007 (2)	−0.012 (3)	0.004 (3)
C5	0.070 (4)	0.072 (3)	0.088 (5)	−0.002 (3)	−0.018 (4)	0.007 (3)
C6	0.115 (7)	0.093 (5)	0.094 (6)	0.012 (4)	−0.029 (5)	−0.007 (4)
C7	0.052 (3)	0.057 (3)	0.080 (4)	−0.009 (2)	−0.007 (3)	−0.001 (3)
C8	0.061 (4)	0.055 (3)	0.091 (5)	−0.007 (2)	−0.009 (3)	−0.005 (3)
C9	0.054 (3)	0.078 (3)	0.101 (5)	0.003 (3)	−0.013 (3)	0.004 (3)
C10	0.065 (4)	0.073 (3)	0.090 (5)	−0.002 (3)	−0.011 (4)	−0.010 (3)
C11	0.058 (4)	0.084 (4)	0.088 (5)	0.001 (3)	−0.005 (3)	0.004 (3)
C12	0.074 (5)	0.232 (11)	0.112 (7)	0.014 (5)	−0.015 (5)	−0.005 (6)
C13	0.051 (3)	0.063 (3)	0.088 (5)	0.000 (2)	0.006 (3)	0.003 (3)
C14	0.047 (3)	0.055 (3)	0.079 (4)	−0.003 (2)	0.008 (3)	0.003 (3)
C15	0.057 (3)	0.074 (3)	0.088 (4)	0.008 (3)	0.011 (3)	0.003 (3)
C16	0.054 (3)	0.048 (3)	0.083 (4)	0.009 (2)	0.013 (3)	0.000 (2)
C17	0.077 (4)	0.070 (4)	0.092 (5)	−0.005 (3)	0.027 (4)	−0.009 (3)
C18	0.103 (5)	0.081 (4)	0.080 (5)	0.001 (4)	0.028 (4)	0.003 (3)
C19	0.098 (5)	0.069 (3)	0.088 (5)	0.020 (3)	0.001 (4)	0.001 (3)
C20	0.070 (4)	0.066 (3)	0.095 (5)	0.015 (3)	−0.007 (4)	−0.001 (3)
C21	0.058 (3)	0.060 (3)	0.088 (4)	0.005 (3)	0.004 (3)	0.008 (3)
C22	0.151 (8)	0.119 (6)	0.091 (6)	0.013 (5)	−0.004 (5)	0.002 (5)
N1	0.055 (3)	0.062 (3)	0.081 (4)	−0.001 (2)	−0.012 (3)	−0.001 (2)
N2	0.054 (3)	0.085 (3)	0.105 (5)	0.011 (2)	−0.005 (3)	0.005 (3)
N3	0.060 (3)	0.081 (3)	0.094 (4)	0.003 (2)	−0.004 (3)	0.005 (3)
N4	0.067 (4)	0.097 (4)	0.084 (4)	−0.002 (3)	−0.006 (3)	0.000 (3)
N5	0.064 (3)	0.079 (3)	0.085 (4)	−0.001 (2)	−0.002 (3)	0.002 (3)
N6	0.058 (3)	0.097 (4)	0.099 (5)	0.008 (3)	−0.002 (3)	0.002 (3)
N7	0.051 (3)	0.093 (3)	0.102 (4)	0.018 (2)	0.010 (3)	0.003 (3)
N8	0.048 (3)	0.060 (3)	0.085 (4)	0.0050 (19)	0.005 (3)	0.002 (2)
O1	0.078 (3)	0.159 (5)	0.089 (3)	0.020 (3)	−0.013 (3)	−0.011 (3)
F1	0.150 (5)	0.216 (6)	0.082 (3)	0.031 (4)	0.018 (3)	−0.001 (3)

Geometric parameters (Å, º) top

C1—F1	1.305 (6)	C13—C14	1.375 (8)
C1—C2	1.3900	C13—N6	1.378 (8)
C1—C6	1.3900	C14—N8	1.360 (8)
C2—C3	1.3900	C14—C15	1.478 (8)
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.3900	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.3900	C16—C17	1.3900
C4—N1	1.410 (6)	C16—C21	1.3900
C5—C6	1.3900	C16—N8	1.408 (6)
C5—H5	0.9300	C17—C18	1.3900
C6—H6	0.9300	C17—H17	0.9300
C7—N1	1.349 (8)	C18—C19	1.3900
C7—C8	1.358 (9)	C18—H18	0.9300
C7—C9	1.489 (8)	C19—C20	1.3900
C8—N3	1.371 (8)	C19—C22	1.519 (9)
C8—C10	1.462 (10)	C20—C21	1.3900
C9—H9A	0.9600	C20—H20	0.9300
C9—H9B	0.9600	C21—H21	0.9300
C9—H9C	0.9600	C22—H22A	0.9600
C10—O1	1.209 (7)	C22—H22B	0.9600
C10—N4	1.358 (8)	C22—H22C	0.9600
C11—N5	1.278 (8)	N1—N2	1.365 (6)
C11—C13	1.438 (9)	N2—N3	1.304 (7)
C11—C12	1.501 (10)	N4—N5	1.373 (8)
C12—H12A	0.9600	N4—H4	0.867 (15)
C12—H12B	0.9600	N6—N7	1.294 (7)
C12—H12C	0.9600	N7—N8	1.362 (7)

F1—C1—C2	119.5 (5)	N8—C14—C15	124.0 (5)
F1—C1—C6	120.5 (5)	C13—C14—C15	131.8 (6)
C2—C1—C6	120.0	C14—C15—H15A	109.5
C3—C2—C1	120.0	C14—C15—H15B	109.5
C3—C2—H2	120.0	H15A—C15—H15B	109.5
C1—C2—H2	120.0	C14—C15—H15C	109.5
C2—C3—C4	120.0	H15A—C15—H15C	109.5
C2—C3—H3	120.0	H15B—C15—H15C	109.5
C4—C3—H3	120.0	C17—C16—C21	120.0
C5—C4—C3	120.0	C17—C16—N8	118.9 (3)
C5—C4—N1	119.0 (3)	C21—C16—N8	121.1 (3)
C3—C4—N1	121.0 (3)	C16—C17—C18	120.0
C6—C5—C4	120.0	C16—C17—H17	120.0
C6—C5—H5	120.0	C18—C17—H17	120.0
C4—C5—H5	120.0	C19—C18—C17	120.0
C5—C6—C1	120.0	C19—C18—H18	120.0
C5—C6—H6	120.0	C17—C18—H18	120.0
C1—C6—H6	120.0	C20—C19—C18	120.0
N1—C7—C8	104.1 (5)	C20—C19—C22	119.1 (5)
N1—C7—C9	125.0 (6)	C18—C19—C22	120.9 (5)
C8—C7—C9	130.8 (6)	C19—C20—C21	120.0
C7—C8—N3	109.4 (6)	C19—C20—H20	120.0
C7—C8—C10	128.5 (6)	C21—C20—H20	120.0
N3—C8—C10	122.1 (6)	C20—C21—C16	120.0
C7—C9—H9A	109.5	C20—C21—H21	120.0
C7—C9—H9B	109.5	C16—C21—H21	120.0
H9A—C9—H9B	109.5	C19—C22—H22A	109.5
C7—C9—H9C	109.5	C19—C22—H22B	109.5
H9A—C9—H9C	109.5	H22A—C22—H22B	109.5
H9B—C9—H9C	109.5	C19—C22—H22C	109.5
O1—C10—N4	122.7 (7)	H22A—C22—H22C	109.5
O1—C10—C8	122.5 (6)	H22B—C22—H22C	109.5
N4—C10—C8	114.8 (6)	C7—N1—N2	111.1 (5)
N5—C11—C13	117.1 (6)	C7—N1—C4	129.1 (4)
N5—C11—C12	124.7 (7)	N2—N1—C4	119.8 (5)
C13—C11—C12	118.2 (6)	N3—N2—N1	106.8 (5)
C11—C12—H12A	109.5	N2—N3—C8	108.6 (5)
C11—C12—H12B	109.5	C10—N4—N5	120.4 (5)
H12A—C12—H12B	109.5	C10—N4—H4	115 (5)
C11—C12—H12C	109.5	N5—N4—H4	125 (5)
H12A—C12—H12C	109.5	C11—N5—N4	117.5 (5)
H12B—C12—H12C	109.5	N7—N6—C13	109.3 (5)
C14—C13—N6	108.4 (6)	N6—N7—N8	107.4 (5)
C14—C13—C11	131.2 (6)	C14—N8—N7	110.9 (5)
N6—C13—C11	120.4 (6)	C14—N8—C16	130.9 (4)
N8—C14—C13	104.0 (5)	N7—N8—C16	118.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.96	2.48	3.229 (12)	135

Symmetry code: (i) x+1/2, −y+1/2, z.

Footnotes

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

Funding information

MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia, for financial support (award No. 020–0180).

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