Crystal structure of 1-{3-(4-methyl­phen­yl)-5-[(E)-2-phenyl­ethen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethan-1-one

Farook Adam; Kanathur Smitha; Sharath Poojary Charishma; Seranthimata Samshuddin; Nadiah Ameram

doi:10.1107/S2056989015024792

. 2015 Dec 31;71(Pt 12):o1095–o1096. doi: 10.1107/S2056989015024792

Crystal structure of 1-{3-(4-methylphenyl)-5-[(E)-2-phenylethenyl]-4,5-dihydro-1H-pyrazol-1-yl}ethan-1-one

Farook Adam ^a,^*, Kanathur Smitha ^b, Sharath Poojary Charishma ^b, Seranthimata Samshuddin ^b, Nadiah Ameram ^a

PMCID: PMC4719997 PMID: 26870516

Abstract

The title compound, C₂₀H₂₀N₂O, was studied as a part of our work on pyrazoline derivatives. It represents a trans-isomer. The central pyrazoline ring adopts an envelope conformation with the asymmetric C atom having the largest deviation of 0.107 (1) Å from the mean plane. It forms dihedral angles of 6.2 (1) and 86.4 (1)° with the adjacent p-tolyl and styrene groups, respectively. In the crystal, C—H⋯O interactions link molecules into infinite chains along the c axis.

Keywords: crystal structure, synthesis, pyrazoline, pharmacological properties

Related literature

For background to pyrazoles, see: Samshuddin et al. (2012 ▸); Wiley et al. (1958 ▸); Sarojini et al. (2010 ▸); Lu et al.(1999 ▸). For crystal structures of pyrazoline-derived chalcones, see: Jasinski et al. (2012 ▸); Baktır et al. (2011 ▸). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▸).

Experimental

Crystal data

C₂₀H₂₀N₂O
M _r = 304.38
Orthorhombic,
a = 19.872 (2) Å
b = 20.304 (2) Å
c = 8.2924 (8) Å
V = 3345.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.38 × 0.31 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.914, T _max = 0.960
60332 measured reflections
5482 independent reflections
4234 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.146
S = 1.04
5482 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015024792/ld2138sup1.cif

e-71-o1095-sup1.cif^{(2MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024792/ld2138Isup3.hkl

e-71-o1095-Isup3.hkl^{(436.5KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015024792/ld2138Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015024792/ld2138fig1.tif

The molecular structure of title compound (I) with atom labels and 50% probability displacement ellipsoids.

Click here for additional data file.^{(2MB, tif)}

a . DOI: 10.1107/S2056989015024792/ld2138fig2.tif

The crystal packing of title compound (I) viewed along the a-axis.

CCDC reference: 1444202

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19C⋯O1ⁱ	0.98	2.51	3.4416 (18)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

FA would like to thank University Sains Malaysia for the RU research Grant (No. PKIMIA/846017 and 1001/PKIMIA/811269) which partly supported the work. SS thanks to Alva’s Education Foundation, Moodbidri, for the research facilities.

supplementary crystallographic information

S1. Introduction

Pyrazoline derivatives exhibit numerous pharmacological activities including antioxidant, antiamoebic, anti-inflammatory, analgesic, antimicrobial, anti depressant and anticancer activities (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines were used as scintillation solutes (Wiley et al., 1958) and as fluorescent agents (Lu et al., 1999). The crystal structures of some pyrazolines containing N-alkyl chain viz., 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (Baktir et al., 2011), 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (Jasinski et al., 2012) had 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 hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 6 h·The reaction mixture was cooled and poured into 100 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol.

S2.1. Synthesis and crystallization

Single crystals were grown from ethanol by slow evaporation method. m.p.: 386–390 K. Yield: 71%.

S2.2. Refinement

All H atoms were placed in calculated positions and refined with riding model [U_iso (H) = 1.2 × U_eq(C methylene or methine) or 1.5 × U_eq (C methyl), C—H = 0.95 Å, 0.98 Å, 0.99 Å and 1.00 Å]. A rotating group model (AFIX 137) is applied to methyl groups.

S3. related literature

For background of pyrazoles, see: Samshuddin et al. (2012); Wiley et al. (1958); Sarojini et al. (2010); Lu et al. (1999). For crystal structures of pyrazoline derived chalcone, see: Jasinski et al. (2012); Baktir et al. (2011). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).

S4. Results and discussion

The asymmetric unit of (I) consists of a single crystallographic independent molecule as shown in Fig. 1. The C6/C7/C8/C9 carbon chains adopts a trans configuration with respect to C7—C8 double bond. The pyrazoline ring (N1/N2/C9/C10/C11) adopts an envelope conformation on atom C9 [Q2 = 0.1772 (12) Å and φ2 = 317.3 (4)°] with maximum deviation of 0.107 (1) Å from its mean plane. The p-tolyl ring and styrene group make dihedral angles of 6.19 (7)° and 86.39 (7)° with central pyrazoline ring. In crystal, molecules are connected by weak C—H···O hydrogen bond into one-dimensional chains (Fig. 2), propagating along crystallographic c-axis.