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

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

doi:10.1107/S1600536814013063

. 2014 Jun 11;70(Pt 7):o761–o762. doi: 10.1107/S1600536814013063

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

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

PMCID: PMC4120539 PMID: 25161554

Abstract

In the title compound, C₂₂H₂₅ClN₂O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C—H⋯O hydrogen bonds form centrosymmetric dimers with an R ₂ ²(16) graph-set motif. C—H⋯π interactions link the dimers into columns propagating in [100].

Related literature

For the biological activity of pyrazolines, see: Samshuddin et al. (2012a ▶,b ▶). For related structures, see: Baktır et al. (2011 ▶); Jasinski et al. (2010 ▶); Fun et al. (2012a ▶,b ▶); Samshuddin et al. (2010 ▶, 2012c ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For a related structure, see: Narayana et al., (2014 ▶). graphic file with name e-70-0o761-scheme1.jpg

Experimental

Crystal data

C₂₂H₂₅ClN₂O
M _r = 368.89
Triclinic,
a = 6.8148 (6) Å
b = 11.1115 (9) Å
c = 13.8239 (15) Å
α = 70.935 (9)°
β = 81.420 (8)°
γ = 75.829 (7)°
V = 956.52 (17) Å³
Z = 2
Cu Kα radiation
μ = 1.86 mm⁻¹
T = 173 K
0.48 × 0.24 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.777, T _max = 1.000
6121 measured reflections
3624 independent reflections
3104 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.134
S = 1.03
3624 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 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/S1600536814013063/cv5461sup1.cif

e-70-0o761-sup1.cif^{(28KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013063/cv5461Isup2.hkl

e-70-0o761-Isup2.hkl^{(198.8KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814013063/cv5461Isup3.cml

CCDC reference: 1006822

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

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

Cg is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.95	2.57	3.437 (2)	151
C20—H20A⋯Cg ⁱⁱ	0.99	2.67	3.5079 (19)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

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 are biologically active compounds. They possess activities like antimicrobial, analgesic and antioxidant activities (Samshuddin et al., 2012a,b). The crystal structure of some pyrazoline derivatives viz., 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (Baktır et al., 2011), 3,5-bis(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (Jasinski et al., 2010), 5-(4-bromophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, 1-[5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl] butan-1-one (Fun et al., 2012a,b) and 3,5-bis(4-bromophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, 3,5-bis(4-fluorophenyl)-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole (Samshuddin et al., 2010, 2012c) have been reported. Herein we report the crystal structure of the title compound (I).

In (I) (Fig. 1), the pyrazole ring exhibits an envelope conformation (puckering parameters Q =0.1957 (19)Å, φ = 314.1 (5)°; Cremer & Pople, 1975) with the methine carbon atom as a flap. Bond lengths are in normal ranges and correspond to those observed in the related structures (Baktır et al., 2011; Jasinski et al., 2010; Fun et al., 2012a,b; Samshuddin et al., 2010, 2012c). The two benzene rings are twisted at 3.3 (5)° and 84.6 (5)°, respectively, from the pyrazole mean plane, and are inclined to each other at 81.4 (4)°.

In the crystal, a weak C—H···O intermolecular interaction between the phenyl ring and the butan-1-one group is observed forming dimers in an R₂²[16] ring-set motif (Fig. 2). In addition, weak C—H···π intermolecular stacking interactions (Table 1) are also present and link further these dimers into columns propagated in [100].

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 30 mL butyric acid was refluxed for 10h (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.: 369–371 K).