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

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ISSN: 2414-3146

2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thia­zole

CROSSMARK_Color_square_no_text.svg

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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 13 February 2019; accepted 15 February 2019; online 22 February 2019)

The title compound, C28H23FN6S, comprises phenyl (A), triazolyl (B), thia­zolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings, with twist angles between neighbouring rings pairs A/B, B/C, C/D, D/E and D/F of 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. A short intra­molecular C—H⋯N contact and a weak inter­molecular C—H⋯π inter­action occur. The crystal chosen for data collection was found to be an inversion twin.

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

Structure description

Triazoles act as anti­fungal drugs and plant protection fungicides (Bonandi et al., 2017[Bonandi, E., Christodoulou, M. S., Fumagalli, G., Perdicchia, D., Rastelli, G. & Passarella, D. (2017). Drug Discov. Today, 22, 1572-1581.]). Thia­zoles and pyrazoles are an essential core scaffold in many natural products and have various biological activities (Chhabria et al., 2016[Chhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841-2862.]; Faria et al., 2017[Faria, J. V., Vegi, P. F., Miguita, A. G. C., Dos Santos, M. S., Boechat, N. & Bernardino, A. M. R. (2017). Bioorg. Med. Chem. 25, 5891-5903.]). As part of our studies in these areas, we now describe the synthesis and structure of the title compound.

The mol­ecule of the title compound comprises phenyl (A), triazolyl (B), thia­zolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings (Fig. 1[link]). The twist angles between the planes through neighbouring ring pairs A/B, B/C, C/D, D/E and D/F are 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. The packing is shown in Fig. 2[link]. A short intra­molecular C—H⋯N contact and a weak inter­molecular C—H⋯π inter­action occur (Table 1[link]); the latter involves the phenyl ring bonded to the triazole ring as donor and the tolyl ring as acceptor.

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C22–C27 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8C⋯N4 0.96 2.49 3.135 (5) 125
C2—H2⋯Cg6i 0.93 2.93 3.451 (5) 117
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 50% displacement ellipsoids.
[Figure 2]
Figure 2
The crystal structure viewed down the a-axis direction.

Synthesis and crystallization

The title compound was synthesized from condensation of 5-(4-fluoro­phen­yl)-3-p-tolyl-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide (0.63 g, 2.0 mmol) with 2-bromo-1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethanone (0.56 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The crude product was recrystallized from di­methyl­formamide solution to give colourless crystals (74%), m.p. 241–242°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The crystal studied was refined as a two-component inversion twin.

Table 2
Experimental details

Crystal data
Chemical formula C28H23FN6S
Mr 494.58
Crystal system, space group Orthorhombic, P212121
Temperature (K) 298
a, b, c (Å) 6.4930 (7), 13.8065 (10), 27.539 (2)
V3) 2468.7 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.17
Crystal size (mm) 0.48 × 0.22 × 0.20
 
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.])
Tmin, Tmax 0.989, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections 10497, 5824, 3616
Rint 0.030
(sin θ/λ)max−1) 0.701
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.130, 1.02
No. of reflections 5824
No. of parameters 328
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.16
Absolute structure Refined as an inversion twin.
Absolute structure parameter 0.39 (13)
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXS (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.]), 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: 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).

2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thiazole top
Crystal data top
C28H23FN6SDx = 1.331 Mg m3
Mr = 494.58Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2536 reflections
a = 6.4930 (7) Åθ = 4.5–24.6°
b = 13.8065 (10) ŵ = 0.17 mm1
c = 27.539 (2) ÅT = 298 K
V = 2468.7 (4) Å3Block, colourless
Z = 40.48 × 0.22 × 0.20 mm
F(000) = 1032
Data collection top
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
diffractometer
3616 reflections with I > 2σ(I)
ω scansRint = 0.030
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
θmax = 29.9°, θmin = 3.5°
Tmin = 0.989, Tmax = 0.995h = 86
10497 measured reflectionsk = 1818
5824 independent reflectionsl = 3737
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.4094P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.19 e Å3
5824 reflectionsΔρmin = 0.16 e Å3
328 parametersAbsolute structure: Refined as an inversion twin.
0 restraintsAbsolute structure parameter: 0.39 (13)
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. Refined as a twocomponent inversion twin. All hydrogen atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined using a riding model. Their Uiso values were set to 1.2Ueq(C) or 1.5Ueq(methyl C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4269 (7)1.1919 (3)1.07159 (13)0.0559 (10)
C20.6229 (7)1.1827 (3)1.08958 (15)0.0649 (11)
H20.6789091.1218761.0955620.078*
C30.7347 (7)1.2650 (3)1.09859 (16)0.0717 (12)
H30.8673161.2603341.1111200.086*
C40.6503 (9)1.3551 (3)1.08904 (16)0.0739 (13)
H40.7259431.4107831.0957050.089*
C50.4596 (9)1.3629 (3)1.07019 (19)0.0849 (15)
H50.4049791.4236071.0632860.102*
C60.3460 (8)1.2808 (3)1.06117 (18)0.0797 (13)
H60.2144611.2857811.0480220.096*
C70.3245 (6)1.0401 (2)1.02673 (13)0.0511 (9)
C80.5093 (7)1.0342 (3)0.99548 (16)0.0691 (12)
H8A0.5133881.0892650.9742370.104*
H8B0.6305951.0335041.0154120.104*
H8C0.5038770.9758970.9765040.104*
C90.1463 (6)0.9874 (2)1.02874 (13)0.0516 (9)
C100.0736 (6)0.9082 (3)0.99844 (14)0.0511 (9)
C110.0948 (7)0.8538 (3)1.00637 (14)0.0574 (10)
H110.1828800.8613051.0327280.069*
C120.0915 (6)0.8150 (3)0.93398 (14)0.0544 (10)
C130.3802 (7)0.7884 (2)0.87594 (14)0.0567 (10)
H130.4697530.7832430.9044770.068*
C140.4096 (7)0.6982 (3)0.84381 (16)0.0690 (12)
H14A0.5245320.6592900.8550390.083*
H14B0.4328420.7162230.8102080.083*
C150.2083 (7)0.6445 (3)0.84956 (15)0.0583 (11)
C160.4171 (7)0.8849 (3)0.85139 (13)0.0568 (10)
C170.6006 (8)0.9330 (3)0.85763 (17)0.0816 (14)
H170.7014150.9055840.8772910.098*
C180.6390 (10)1.0206 (4)0.8355 (2)0.0978 (18)
H180.7638441.0524940.8398670.117*
C190.4880 (11)1.0591 (3)0.80716 (18)0.0818 (16)
C200.3074 (10)1.0152 (3)0.79966 (17)0.0804 (15)
H200.2081501.0430640.7796910.097*
C210.2713 (8)0.9269 (3)0.82245 (16)0.0694 (12)
H210.1456710.8959040.8179180.083*
C220.1595 (8)0.5513 (3)0.82755 (15)0.0618 (11)
C230.0365 (8)0.5127 (3)0.83004 (18)0.0740 (13)
H230.1405880.5477750.8451710.089*
C240.0807 (9)0.4226 (3)0.81034 (19)0.0843 (16)
H240.2138840.3981200.8123600.101*
C250.0720 (10)0.3686 (3)0.78763 (17)0.0782 (15)
C260.2671 (9)0.4073 (3)0.78493 (17)0.0820 (15)
H260.3713420.3725810.7696610.098*
C270.3102 (9)0.4974 (3)0.80466 (16)0.0767 (14)
H270.4432030.5219970.8024570.092*
C280.0244 (10)0.2676 (4)0.7685 (2)0.111 (2)
H28A0.1120900.2536750.7413250.166*
H28B0.0482070.2208810.7937030.166*
H28C0.1169800.2646340.7584530.166*
N10.3011 (5)1.1082 (2)1.06182 (12)0.0562 (8)
N20.1185 (6)1.0982 (3)1.08453 (13)0.0734 (10)
N30.0244 (6)1.0233 (3)1.06502 (14)0.0708 (10)
N40.1820 (5)0.8870 (2)0.95596 (11)0.0517 (8)
N50.1641 (5)0.7772 (2)0.89122 (12)0.0595 (8)
N60.0774 (6)0.6892 (2)0.87665 (12)0.0603 (9)
F10.5241 (6)1.1462 (2)0.78531 (12)0.1226 (13)
S10.12603 (17)0.76837 (7)0.96140 (4)0.0631 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (3)0.058 (2)0.056 (2)0.002 (2)0.0014 (19)0.0004 (19)
C20.055 (3)0.065 (2)0.075 (2)0.004 (2)0.000 (2)0.002 (2)
C30.056 (3)0.082 (3)0.077 (3)0.008 (3)0.005 (2)0.008 (3)
C40.086 (4)0.062 (3)0.074 (3)0.012 (3)0.005 (3)0.008 (2)
C50.090 (4)0.058 (3)0.107 (4)0.001 (3)0.010 (3)0.006 (3)
C60.072 (3)0.064 (2)0.103 (3)0.006 (3)0.017 (3)0.006 (3)
C70.045 (2)0.0479 (18)0.060 (2)0.0055 (18)0.0047 (19)0.0081 (17)
C80.056 (3)0.075 (3)0.077 (3)0.006 (2)0.013 (2)0.012 (2)
C90.043 (2)0.0507 (18)0.061 (2)0.0044 (19)0.007 (2)0.0067 (17)
C100.041 (2)0.0488 (18)0.064 (2)0.0031 (18)0.0037 (19)0.0109 (18)
C110.053 (3)0.057 (2)0.062 (2)0.002 (2)0.004 (2)0.0069 (18)
C120.046 (2)0.0502 (19)0.067 (2)0.0020 (19)0.002 (2)0.0155 (19)
C130.049 (2)0.057 (2)0.064 (2)0.009 (2)0.004 (2)0.0047 (18)
C140.065 (3)0.054 (2)0.088 (3)0.002 (2)0.007 (3)0.002 (2)
C150.063 (3)0.049 (2)0.062 (2)0.000 (2)0.006 (2)0.0085 (19)
C160.065 (3)0.053 (2)0.052 (2)0.005 (2)0.003 (2)0.0015 (18)
C170.077 (4)0.087 (3)0.081 (3)0.026 (3)0.010 (3)0.020 (3)
C180.105 (5)0.093 (4)0.096 (4)0.039 (4)0.001 (4)0.016 (3)
C190.124 (5)0.057 (3)0.065 (3)0.014 (3)0.019 (3)0.003 (2)
C200.109 (5)0.061 (3)0.071 (3)0.006 (3)0.002 (3)0.004 (2)
C210.072 (3)0.059 (2)0.077 (3)0.003 (2)0.004 (3)0.001 (2)
C220.070 (3)0.050 (2)0.065 (2)0.005 (2)0.006 (2)0.0065 (19)
C230.074 (4)0.061 (3)0.088 (3)0.003 (2)0.016 (3)0.006 (2)
C240.079 (4)0.068 (3)0.106 (4)0.010 (3)0.032 (3)0.002 (3)
C250.099 (4)0.059 (3)0.077 (3)0.001 (3)0.023 (3)0.000 (2)
C260.097 (4)0.068 (3)0.081 (3)0.000 (3)0.009 (3)0.005 (3)
C270.087 (4)0.066 (3)0.077 (3)0.009 (3)0.008 (3)0.006 (2)
C280.150 (6)0.062 (3)0.120 (4)0.002 (3)0.042 (4)0.017 (3)
N10.048 (2)0.0557 (17)0.0654 (18)0.0025 (16)0.0046 (17)0.0033 (17)
N20.056 (2)0.083 (2)0.081 (2)0.006 (2)0.019 (2)0.016 (2)
N30.056 (2)0.074 (2)0.082 (2)0.0069 (19)0.019 (2)0.009 (2)
N40.0483 (19)0.0456 (15)0.0613 (18)0.0026 (15)0.0022 (16)0.0077 (15)
N50.056 (2)0.0556 (17)0.0673 (19)0.0098 (17)0.0044 (17)0.0025 (16)
N60.062 (2)0.0547 (17)0.0644 (19)0.0076 (18)0.0068 (18)0.0029 (17)
F10.179 (4)0.0690 (17)0.120 (2)0.023 (2)0.030 (2)0.0235 (17)
S10.0522 (6)0.0618 (5)0.0754 (6)0.0127 (5)0.0014 (6)0.0094 (5)
Geometric parameters (Å, º) top
C1—C61.366 (5)C14—H14A0.9700
C1—C21.372 (6)C14—H14B0.9700
C1—N11.440 (5)C15—N61.288 (5)
C2—C31.371 (6)C15—C221.458 (5)
C2—H20.9300C16—C211.367 (6)
C3—C41.385 (6)C16—C171.374 (6)
C3—H30.9300C17—C181.378 (6)
C4—C51.347 (7)C17—H170.9300
C4—H40.9300C18—C191.361 (8)
C5—C61.375 (6)C18—H180.9300
C5—H50.9300C19—C201.336 (8)
C6—H60.9300C19—F11.366 (5)
C7—N11.357 (4)C20—C211.391 (6)
C7—C91.368 (5)C20—H200.9300
C7—C81.479 (6)C21—H210.9300
C8—H8A0.9600C22—C231.381 (6)
C8—H8B0.9600C22—C271.381 (6)
C8—H8C0.9600C23—C241.387 (6)
C9—N31.368 (5)C23—H230.9300
C9—C101.454 (5)C24—C251.389 (7)
C10—C111.344 (5)C24—H240.9300
C10—N41.396 (5)C25—C261.377 (7)
C11—S11.722 (4)C25—C281.522 (6)
C11—H110.9300C26—C271.385 (6)
C12—N41.304 (5)C26—H260.9300
C12—N51.371 (5)C27—H270.9300
C12—S11.726 (4)C28—H28A0.9600
C13—N51.473 (5)C28—H28B0.9600
C13—C161.513 (5)C28—H28C0.9600
C13—C141.540 (5)N1—N21.348 (5)
C13—H130.9800N2—N31.315 (5)
C14—C151.511 (6)N5—N61.398 (4)
C6—C1—C2121.1 (4)C21—C16—C17117.9 (4)
C6—C1—N1117.6 (4)C21—C16—C13121.7 (4)
C2—C1—N1121.3 (4)C17—C16—C13120.4 (4)
C3—C2—C1118.7 (4)C16—C17—C18121.7 (5)
C3—C2—H2120.7C16—C17—H17119.1
C1—C2—H2120.7C18—C17—H17119.1
C2—C3—C4120.1 (4)C19—C18—C17117.8 (5)
C2—C3—H3120.0C19—C18—H18121.1
C4—C3—H3120.0C17—C18—H18121.1
C5—C4—C3120.5 (4)C20—C19—C18123.0 (5)
C5—C4—H4119.7C20—C19—F1118.8 (6)
C3—C4—H4119.7C18—C19—F1118.2 (6)
C4—C5—C6119.8 (5)C19—C20—C21118.3 (5)
C4—C5—H5120.1C19—C20—H20120.8
C6—C5—H5120.1C21—C20—H20120.8
C1—C6—C5119.8 (5)C16—C21—C20121.3 (5)
C1—C6—H6120.1C16—C21—H21119.4
C5—C6—H6120.1C20—C21—H21119.4
N1—C7—C9104.2 (3)C23—C22—C27117.9 (4)
N1—C7—C8122.9 (4)C23—C22—C15121.3 (4)
C9—C7—C8132.9 (4)C27—C22—C15120.8 (4)
C7—C8—H8A109.5C22—C23—C24121.1 (5)
C7—C8—H8B109.5C22—C23—H23119.4
H8A—C8—H8B109.5C24—C23—H23119.4
C7—C8—H8C109.5C23—C24—C25120.6 (5)
H8A—C8—H8C109.5C23—C24—H24119.7
H8B—C8—H8C109.5C25—C24—H24119.7
N3—C9—C7109.1 (3)C26—C25—C24118.2 (4)
N3—C9—C10120.2 (4)C26—C25—C28121.6 (5)
C7—C9—C10130.6 (4)C24—C25—C28120.2 (6)
C11—C10—N4115.4 (3)C25—C26—C27120.9 (5)
C11—C10—C9126.2 (4)C25—C26—H26119.6
N4—C10—C9118.4 (3)C27—C26—H26119.6
C10—C11—S1111.2 (3)C22—C27—C26121.3 (5)
C10—C11—H11124.4C22—C27—H27119.4
S1—C11—H11124.4C26—C27—H27119.4
N4—C12—N5122.3 (4)C25—C28—H28A109.5
N4—C12—S1116.7 (3)C25—C28—H28B109.5
N5—C12—S1121.0 (3)H28A—C28—H28B109.5
N5—C13—C16111.8 (3)C25—C28—H28C109.5
N5—C13—C14101.4 (3)H28A—C28—H28C109.5
C16—C13—C14115.8 (3)H28B—C28—H28C109.5
N5—C13—H13109.2N2—N1—C7110.9 (3)
C16—C13—H13109.2N2—N1—C1119.7 (3)
C14—C13—H13109.2C7—N1—C1128.7 (3)
C15—C14—C13103.3 (4)N3—N2—N1107.5 (3)
C15—C14—H14A111.1N2—N3—C9108.3 (3)
C13—C14—H14A111.1C12—N4—C10108.8 (3)
C15—C14—H14B111.1C12—N5—N6116.0 (3)
C13—C14—H14B111.1C12—N5—C13122.2 (3)
H14A—C14—H14B109.1N6—N5—C13113.1 (3)
N6—C15—C22121.4 (4)C15—N6—N5108.5 (3)
N6—C15—C14113.4 (3)C11—S1—C1287.9 (2)
C22—C15—C14125.3 (4)
Hydrogen-bond geometry (Å, º) top
Cg6 is the centroid of the C22–C27 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8C···N40.962.493.135 (5)125
C2—H2···Cg6i0.932.933.451 (5)117
Symmetry code: (i) x1/2, y+3/2, z+2.
 

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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