[3-(5-Nitro-2-fur­yl)-1-phenyl-1H-pyrazol-4-yl](phen­yl)methanone

Jia Hao Goh; Hoong-Kun Fun; Nithinchandra; B Kalluraya; N Satheesh Rai

doi:10.1107/S1600536810015199

. 2010 Apr 30;66(Pt 5):o1229–o1230. doi: 10.1107/S1600536810015199

[3-(5-Nitro-2-furyl)-1-phenyl-1H-pyrazol-4-yl](phenyl)methanone

Jia Hao Goh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, Nithinchandra ^b, B Kalluraya ^b, N Satheesh Rai ^b

PMCID: PMC2979013 PMID: 21579253

Abstract

In the title pyrazole compound, C₂₀H₁₃N₃O₄, an intramolecular C—H⋯O hydrogen bond generates a seven-membered ring, producing an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum deviations of 0.002 (1) and 0.007 (1) Å, respectively] are coplanar with each other, forming a dihedral angle of 3.06 (10)°. The pyrazole ring forms dihedral angles of 8.51 (9) and 56.81 (9)° with the two benzene rings. The nitro group is coplanar with the attached furan ring, as indicated by the dihedral angle of 2.5 (3)°. In the crystal packing, intermolecular C—H⋯O hydrogen bonds link adjacent molecules into two-molecule-wide chains along the a axis. The crystal packing is further stabilized by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.4441 (10) Å].

Related literature

For general background to and applications of the title compound, see: Kalluraya et al. (1994 ▶); Rai & Kalluraya (2006 ▶); Rai et al. (2008 ▶); Sridhar & Perumal (2003 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For closely related structures, see: Goh et al. (2009a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₀H₁₃N₃O₄
M _r = 359.33
Monoclinic,
a = 11.2946 (12) Å
b = 6.9755 (8) Å
c = 22.7064 (18) Å
β = 115.015 (4)°
V = 1621.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.24 × 0.15 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.976, T _max = 0.992
17931 measured reflections
4725 independent reflections
2991 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.129
S = 1.02
4725 reflections
296 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015199/tk2653sup1.cif

e-66-o1229-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015199/tk2653Isup2.hkl

e-66-o1229-Isup2.hkl^{(231.5KB, hkl)}

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

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

Cg1 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.98 (2)	2.45 (2)	3.190 (3)	131.8 (17)
C11—H11A⋯O2	0.98 (3)	2.23 (3)	2.950 (3)	130 (2)
C14—H14A⋯O3ⁱⁱ	0.96 (2)	2.43 (2)	3.379 (3)	169.3 (17)
C18—H18A⋯Cg1ⁱⁱⁱ	0.96 (2)	2.96 (2)	3.671 (2)	132.0 (16)

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Pyrazole derivatives are in general well-known nitrogen-containing heterocyclic compounds and various procedures have been developed for their synthesis (Rai & Kalluraya, 2006). The chemistry of pyrazole derivatives has been the subject of much interest due to their importance for various applications, and their widespread potential and proven biological and pharmacological activities (Rai et al., 2008). Steroids containing pyrazole moiety are of interest as psychopharmacological agents. Some alkyl- and aryl- substituted pyrazoles have sharply pronounced sedative action on the central nervous system. Certain alkyl pyrazoles show significant bacteriostatic, bacteriocidal, fungicidal, analgesic and anti-pyretic activities (Sridhar & Perumal, 2003). In continuation of our studies on 1,3-dipolar cyclo-addition reactions of sydnones with dipolarophiles carrying a nitrofuran or a nitrothiophene moiety (Kalluraya et al., 1994), we herein report the crystal structure of the title pyrazole compound.

In the title compound, Fig. 1, an intramolecular C11—H11A···O2 hydrogen bond (Table 1) generates a seven-membered ring, producing an S(7) ring motif (Bernstein et al., 1995). The furan (C10-C13/O1) and pyrazole (C8/C9/N2/N1/C14) rings are essentially planar, with maximum deviations of 0.002 (1) and -0.007 (1) Å, respectively, at atoms C12 and N2. These two rings are coplanar to one another, as indicated by the dihedral angle formed between them of 3.06 (10)°. The pyrazole ring is inclined at dihedral angles of 56.81 (9) and 8.51 (9)°, respectively, with the C1-C6 and C15-C20 benzene rings. The nitro group is coplanar with the attached furan ring, making a dihedral angle of 2.5 (3)°. The bond lengths and angles agree well with those closely related pyrazole structures (Goh et al., 2009a,b).

In the crystal packing, intermolecular C2—H2A···O4 and C14—H14A···O3 hydrogen bonds (Table 1) link adjacent molecules into two-molecule-wide chains along the a axis (Fig. 2). The crystal packing is further stabilized by weak intermolecular C18—H18A···Cg1 (Table 1) and Cg2···Cg2 interactions [Cg2···Cg2ⁱ = 3.4441 (10) Å where Cg1 and Cg2 are the centroids of the C15-C20 benzene and pyrazole rings, respectively].

Experimental

3-Phenylsydnone (0.01 mol) and 1-phenyl-3-(5-nitro-2-furyl)-2-propyn-1-one (0.01 mol) were dissolved in dry xylene (10 ml) and refluxed for 4 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product obtained was purified by recrystallization from a mixture of ethanol and DMF. The solid obtained was collected by filtration, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of ethanol and DMF by slow evaporation.