Crystal structure of 3-(4-methyl­phen­yl)-1-phenyl-5-[(E)-2-phenyl­ethen­yl]-1H-pyrazole

Farook Adam; Sharath Poojary Charishma; Basrur Ramya Prabhu; Seranthimata Samshuddin; Nadiah Ameram

doi:10.1107/S2056989015022811

. 2015 Dec 6;71(Pt 12):o1020. doi: 10.1107/S2056989015022811

Crystal structure of 3-(4-methylphenyl)-1-phenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole

Farook Adam ^a,^*, Sharath Poojary Charishma ^b, Basrur Ramya Prabhu ^b, Seranthimata Samshuddin ^b, Nadiah Ameram ^a

PMCID: PMC4719956 PMID: 26870475

Abstract

In the title compound, C₂₄H₂₀N₂, the dihedral angles between the pyrazole ring and the pendant phenyl, toluoyl and phenylethenyl rings are 41.50 (8), 4.41 (8) and 31.07 (8)°, respectively. In the crystal, inversion dimers linked by a π–π stacking interactions between the phenylethenyl rings are observed [centroid–centroid separation = 3.5857 (9) Å].

Keywords: crystal structure, pyrazole, π–π stacking interactions

Related literature

For background to pyrazoles, see: Samshuddin et al. (2012 ▸); Sarojini et al. (2010 ▸); For related crystal structures, see: Jasinski et al. (2012 ▸); Baktır et al. (2011 ▸).

Experimental

Crystal data

C₂₄H₂₀N₂
M _r = 336.42
Monoclinic,
a = 9.6470 (8) Å
b = 14.1077 (12) Å
c = 14.0062 (12) Å
β = 104.891 (1)°
V = 1842.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.38 × 0.24 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.915, T _max = 0.963
32138 measured reflections
5495 independent reflections
4226 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.167
S = 1.04
5495 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015022811/hb7552sup1.cif

e-71-o1020-sup1.cif^{(1.1MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022811/hb7552Isup2.hkl

e-71-o1020-Isup2.hkl^{(437.2KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015022811/hb7552Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015022811/hb7552fig1.tif

A view of the molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(2.5MB, tif)}

a . DOI: 10.1107/S2056989015022811/hb7552fig2.tif

A view along the a axis of the crystal packing of the title compound.

CCDC reference: 1439397

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

SS thanks Alva’s Education Foundation, Moodbidri, for the research facilities. The authors are thankful for RU Research grant 1001/PKIMIA/811269.

supplementary crystallographic information

S1. Comment

Pyrazoles are well known as important structural units in a wide variety of biologically active natural products as well as useful synthetic intermediates (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines were utilized in industries as scintillation solutes and as fluorescent agents. The crystal structures of some pyrazolines viz., 3,5-bis(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, 3,5-bis(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (Baktir et al., 2011) have been reported. In view of the importance of pyrazolines, the title compound (I) is prepared and its crystal structure is reported.

S2. Experimental

A mixture of (2E,4E)-1-(4-methylphenyl)-5-phenylpenta-2,4-dien-1-one (2.48 g, 0.01 mol) and phenylhydrazine (1.08 g,0.01 mol) in 30 ml acetic acid was refluxed for 10 h. The reaction mixture was cooled and poured into 500 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Colourless blocks were grown from acetone solution by slow evaporation; m. p. 471–474 K. Yield: 63%.