1-{3-(4-Methyl­phen­yl)-5-[5-(2-nitro­phen­yl)furan-2-yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone

N Vinutha; S Madan Kumar; B S Vidyashree Jois; Kalluraya Balakrishna; N K Lokanath; D Revannasiddaiah

doi:10.1107/S1600536813024690

. 2013 Sep 12;69(Pt 10):o1528. doi: 10.1107/S1600536813024690

1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone

N Vinutha ^a, S Madan Kumar ^a, B S Vidyashree Jois ^b, Kalluraya Balakrishna ^b, N K Lokanath ^a, D Revannasiddaiah ^a,^*

PMCID: PMC3790397 PMID: 24098216

Abstract

In the title compound, C₂₂H₁₉N₃O₄, the dihedral angle between the furan and pyrazole rings is 82.73 (19)° while the dihedral angles between the furan and pyrazole rings and their attached benzene rings are 31.93 (18) and 1.88 (18)°, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R ₂ ²(16) loops. In addition, weak C—H⋯π and aromatic π–π stacking [minimum centroid–centroid distance = 3.5374 (17) Å] interactions are observed.

Related literature

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008 ▶); Husain et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₁₉N₃O₄
M _r = 389.40
Triclinic,
a = 7.6235 (3) Å
b = 10.5652 (4) Å
c = 13.1177 (4) Å
α = 103.344 (2)°
β = 95.025 (2)°
γ = 108.221 (2)°
V = 961.78 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.842, T _max = 0.854
10640 measured reflections
3083 independent reflections
2186 reflections with I > 2σ(I)
R _int = 0.138

Refinement

R[F ² > 2σ(F ²)] = 0.084
wR(F ²) = 0.242
S = 1.06
3083 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024690/hb7133sup1.cif

e-69-o1528-sup1.cif^{(28.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024690/hb7133Isup2.hkl

e-69-o1528-Isup2.hkl^{(151.3KB, hkl)}

Click here for additional data file.^{(7.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813024690/hb7133Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg4 is the centroid of the C23–C28 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O19ⁱ	0.93	2.56	3.462 (4)	162
C18—H18C⋯Cg4ⁱⁱ	0.96	2.69	3.595 (4)	158

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

Acknowledgments

The authors thank the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC, New Delhi, for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

supplementary crystallographic information

1. Comment

The ongoing work in our lab for synthesizing pyrozoline derivatives resulted the title molecule. Similar compounds are used for the preparation of drugs in the pharmacological industries (Amir et al., 2008; Husain et al., 2008).

In the title compound (Fig. 1), the pyrazole ring makes a dihedral angle of 82.73 (19) °, 88.84 (18) ° and 1.88 (18) ° with furan, nitrophenyl and terminal methylphenyl rings, respectively. The furan ring makes a dihedral angle of 82.35 (18) ° and 31.93 (18) ° with methyl phenyl and nitrophenyl rings, respectively. The dihedral angle between terminal nitrophenyl and methylphenyl ring is 88.23 (17) °.

The title molecules are linked to one another with C14—H14···O19 intermolecular hydrogen bonds with R₂²(16) ring motif (Fig. 2 and Table 1). In addition, short contacts C—H···π (Cg4) with distance 3.595 (4) Å (angle 158 °) [-x, -y, z - 1]. And π···π between Cg2 and Cg1 with distance 3.5374 (17) ° [x,y,z] and between Cg2 and Cg4 with a distance 3.641 (2) ° [x - 1, -y, z - 1] were observed, where Cg1:O11/C10/C14/C13/C12, Cg2:N16/N20/C21/C22/C15 and Cg4:C23/C24/C25/C26/C27/C28.

2. Experimental

A mixture of 4-methylphenyl-3-[5-(2-nitrophenyl)furan-2-yl]prop-2-en-1-one (10 mmol), hydrazine hydrate (50 mmol) and glacial acetic acid (40 ml) were refluxed for 24 h. The resulting mixture was poured into water (100 ml) and allowed to stand. The precipitate that formed was separated by filtration, washed with cold water and then recrystallized from mixed DMF-ethanol solvents to yield brown blocks.