1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone

B Narayana; Vinutha V Salian; Balladka K Sarojini; Jerry P Jasinski

doi:10.1107/S1600536814013348

. 2014 Jun 14;70(Pt 7):o781. doi: 10.1107/S1600536814013348

1-{3-(4-Chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone

B Narayana ^a, Vinutha V Salian ^a, Balladka K Sarojini ^b, Jerry P Jasinski ^c,^*

PMCID: PMC4120582 PMID: 25161567

Abstract

In the title compound, C₂₀H₂₁ClN₂O, the dihedral angles between the pyrazole ring (r.m.s. deviation = 0.049 Å) and the benzene and chlorobenzene rings are 84.65 (10) and 3.35 (10)°, respectively. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R ₂ ²(16) loops. Weak π–π stacking interactions [centroid–centroid distance = 3.8490 (11) Å] are also observed.

Related literature

For background to pyrazolines, see: Manna et al. (2005 ▶); Samshuddin et al. (2012 ▶). For a related structure, see: Jasinski et al. (2010 ▶). graphic file with name e-70-0o781-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₁ClN₂O
M _r = 340.84
Triclinic,
a = 6.4836 (6) Å
b = 9.6524 (9) Å
c = 14.439 (1) Å
α = 81.178 (7)°
β = 89.720 (7)°
γ = 77.488 (8)°
V = 871.35 (13) Å³
Z = 2
Cu Kα radiation
μ = 2.00 mm⁻¹
T = 173 K
0.44 × 0.22 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.552, T _max = 1.000
5081 measured reflections
3287 independent reflections
2770 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.142
S = 1.03
3287 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013348/hb7234sup1.cif

e-70-0o781-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013348/hb7234Isup2.hkl

e-70-0o781-Isup2.hkl^{(180.4KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814013348/hb7234Isup3.cml

CCDC reference: 1007161

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
C15—H15⋯O1ⁱ	0.95	2.44	3.364 (2)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. VVS thanks the DST for financial assistance through a PURSE grant. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

S1. Comment

Pyrazoline derivatives possess many biological activities such as anticancer (Manna et al., 2005) and antioxidant properties (Samshuddin et al., 2012). As part of our ongoing studies in this area (Jasinski et al., 2010), we now describe the structure of the title compound, C₂₀H₂₁ClN₂O.

The dihedral angle between the mean planes of the phenyl rings is 81.3 (0)° while the pyrazole ring is separated from each of the phenyl rings by 3.3 (5)° (C5–C10) and 84.6 (5)° (C11–C16), respectively (Fig. 1). In the crystal, a weak C—H···O intermolecular interaction between the phenyl ring and the ethanone group is observed forming dimers in an R₂²(16) ring-set motif stacked along the ab plane (Fig. 2). In addition, weak π–π intermolecular stacking interactions (Cg1–Cg3 = 3.8490 (11)Å, x, y, z, Cg1: N1/N2/C2/C3/C4; Cg3: C11–C16) are present.

S2. Experimental

To a mixture of (2E)-1-(4-chlorophenyl)-3-[4-(propan-2-yl) phenyl] prop-2-en-1-one (2.85g, 0.01 mol) and hydrazine hydrate (0.5mL, 0.01 mol) in 25 mL acetic acid was refluxed for 9h (Fig. 3). The reaction mixture was cooled and poured into ice-cold water. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless, irregular, crystals were grown from ethanol solution by the slow evaporation method (m.p.: 389–391 K).