5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio­amide

Bakr F Abdel-Wahab; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813008155

. 2013 Mar 28;69(Pt 4):o619. doi: 10.1107/S1600536813008155

5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide

Bakr F Abdel-Wahab ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3629654 PMID: 23634141

Abstract

In the title compound, C₂₆H₂₃FN₆S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thiourea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intramolecular N—H⋯N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluorobenzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supramolecular chains aligned along [40,10] are consolidated by π–π interactions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].

Related literature

For the biological activity and synthesis of related compounds, see: Abdel-Wahab, Abdel-Latif et al. (2012 ▶). For a related structure, see: Abdel-Wahab, Mohamed et al. (2012 ▶). graphic file with name e-69-0o619-scheme1.jpg

Experimental

Crystal data

C₂₆H₂₃FN₆S
M _r = 470.56
Monoclinic,
a = 6.5449 (5) Å
b = 26.1030 (17) Å
c = 14.3818 (8) Å
β = 100.604 (7)°
V = 2415.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.802, T _max = 1.000
15173 measured reflections
5578 independent reflections
3313 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.162
S = 1.03
5578 reflections
313 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(23.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008155/hg5303sup1.cif

e-69-0o619-sup1.cif^{(23.7KB, cif)}

Click here for additional data file.^{(273.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008155/hg5303Isup2.hkl

e-69-0o619-Isup2.hkl^{(273.1KB, hkl)}

Click here for additional data file.^{(8.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813008155/hg5303Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3⋯N3	0.83 (3)	2.05 (3)	2.568 (3)	120 (2)

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Acknowledgments

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

supplementary crystallographic information

Comment

In connection with studies into the biological studies on related pyrazolines (Abdel-Wahab, Abdel-Latif et al., 2012), the title compound, (I), was investigated.

In (I), Fig. 1, the pyrazole ring has an envelope conformation with the methine-C8 atom being the flap atom. The thiourea group is close to co-planar with the N atoms of this ring [the N3—N2—C7—S1 torsion angle = 176.78 (15)°], which allows for an intramolecular N1—H···N3 hydrogen bond, Table 1, and the connected triazole ring is slightly twisted out of the plane through this ring [N3—C10—C17—N4 is -172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluorobenzene ring as seen in the N2—C8—C11—C12 torsion angle of -18.8 (3)°, and an even greater twist between triazole and attached tolyl ring with the dihedral angle being 58.25 (14)°. The relative dispositions of the terminal substituent in (I) resembles those found in a recently determined structure with pyrazole-p-tolyl and triazole-4-(piperidin-1-yl)phenyl substituents (Abdel-Wahab, Mohamed et al., 2012).

The most prominent feature of the crystal packing is the formation of π—π interactions between the triazole and phenyl rings [inter-centroid distance = 3.7053 (13) Å, angle of inclination = 10.17 (12)° for symmetry operation i: 1 + x, 3/2 - y, 1/2 + z]. These lead to a supramolecular chains, aligned approximately along [1 0 2], and which aggregate in the ac plane with no specific interactions between them, Fig. 2. Layers thus formed stack along the b axis, Fig. 3.

Experimental

The title compound was prepared according to the reported method (Abdel-Wahab, Abdel-Latif et al., 2012). Colourless crystals were obtained from its DMF solution by slow evaporation at room temperature.