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

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

doi:10.1107/S1600536814013075

. 2014 Jun 11;70(Pt 7):o763–o764. doi: 10.1107/S1600536814013075

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

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

PMCID: PMC4120579 PMID: 25161555

Abstract

In the title compound, C₂₁H₂₃ClN₂O, the dihedral angle between the benzene rings is 83.2 (6)°, while the mean plane of the pyrazole ring [r.m.s. deviation = 0.043 (1) Å] makes dihedral angles of 3.4 (3) and 86.2 (1)° with the benzene rings. In the crystal, a pair of weak C—H⋯O interactions between the benzene ring and the propan-1-one group link the molecules into an inversion dimer with an R ₂ ²(16) graph-set motif. In addition, a weak π–π stacking interaction [centroid–centroid distance = 3.959 (4) Å] connects the dimers into a tape running along [201].

Related literature

For the biological activity of pyrazolines, see: Taylor et al. (1992 ▶); Lombardino & Otterness (1977 ▶); Manna et al. (2005 ▶); Samshuddin et al. (2012a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For a related structure, see: Narayana et al., (2014 ▶). graphic file with name e-70-0o763-scheme1.jpg

Experimental

Crystal data

C₂₁H₂₃ClN₂O
M _r = 354.86
Triclinic,
a = 6.6042 (3) Å
b = 10.1188 (9) Å
c = 14.4806 (12) Å
α = 98.444 (7)°
β = 90.650 (6)°
γ = 106.542 (6)°
V = 916.13 (12) Å³
Z = 2
Cu Kα radiation
μ = 1.92 mm⁻¹
T = 173 K
0.36 × 0.28 × 0.16 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.583, T _max = 0.736
5565 measured reflections
3519 independent reflections
3170 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.133
S = 1.05
3519 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO (Agilent, 2012 ▶); 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 (Dolomanov et al., 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013075/is5364sup1.cif

e-70-0o763-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013075/is5364Isup2.hkl

e-70-0o763-Isup2.hkl^{(193.1KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814013075/is5364Isup3.cml

CCDC reference: 1006823

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
C11—H11⋯O1ⁱ	0.95	2.51	3.419 (2)	161

Open in a new tab

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

Pyrazolines are important nitrogen containing five-membered heterocyclic compounds. Pyrazoline derivatives possess important biological activities, including antitumor (Taylor et al., 1992), immunosuppressive (Lombardino & Otterness, 1977), anticancer (Manna et al., 2005), antimicrobial, analgesic and antioxidant activities (Samshuddin et al., 2012a,b).

In the title compound, the dihedral angle between the benzene rings is 83.2 (6)°, while the pyrazole ring is separated from each of the benzene rings by 3.4 (3)° (C16–C21) and 86.2 (1)° (C7–C12), respectively (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, a weak C—H···O intermolecular interaction between the benzene ring and the propan-1-one group is observed forming dimers in an R₂²(16) ring-set motif (Fig. 2). In addition, a weak π–π intermolecular stacking interaction [Cg3···Cg3 (1 - x, 2 - y, 1 - z) = 3.959 (4) Å; Cg3: C16–C21] is present and influences the crystal packing.

S2. Experimental

To a mixture of (2E)-1-(4-chlorophenyl)-3-[4-(propan-2-yl)phenyl] prop-2-en-1-one (2.85 g, 0.01 mol) and hydrazine hydrate (0.5 mL, 0.01 mol) in 20 mL propionic acid was refluxed for 8 h (Fig. 3). The reaction mixture was cooled and poured into 50 mL ice-cold water. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method. (m.p.: 365–367 K).