4-(1,3-Diphenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole

Hoong-Kun Fun; Tze Shyang Chia; Shridhar Malladi; Arun M Isloor; Kammasandra N Shivananda

doi:10.1107/S1600536811039869

. 2011 Oct 5;67(Pt 11):o2822–o2823. doi: 10.1107/S1600536811039869

4-(1,3-Diphenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Shridhar Malladi ^b, Arun M Isloor ^b, Kammasandra N Shivananda ^c

PMCID: PMC3247563 PMID: 22219868

Abstract

The title compound, C₃₀H₂₄N₄, contains two pyrazole rings and four phenyl rings. The pyrazole rings are essentially planar, with maximum deviations of 0.003 (1) and 0.066 (1) Å and make a dihedral angle of 73.43 (6)°. The two pyrazole rings make dihedral angles of 40.08 (6), 9.28 (6), 15.78 (8) and 17.25 (7)° with their attached phenyl rings. In the crystal, there are no significant intermolecular hydrogen-bonding interactions. The crystal structure is stabilized by C—H⋯π interactions.

Related literature

For the pharmacological activity of substituted 2-pyrazolines, see: Sahu et al. (2008 ▶); Farghaly et al. (1990 ▶); Adnan et al. (2005 ▶); Budakoti et al. (2008 ▶); Yar et al. (2007 ▶); Palaska et al. (1996 ▶); Jia et al. (2004 ▶). For the experimental preparation, see: Bratenko et al. (2001 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₃₀H₂₄N₄
M _r = 440.53
Monoclinic,
a = 10.7841 (5) Å
b = 11.0582 (6) Å
c = 21.4820 (9) Å
β = 113.359 (2)°
V = 2351.82 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.56 × 0.54 × 0.36 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.974
22465 measured reflections
7042 independent reflections
5057 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.01
7042 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 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 datablock(s) global, I. DOI: 10.1107/S1600536811039869/kj2190sup1.cif

e-67-o2822-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039869/kj2190Isup2.hkl

e-67-o2822-Isup2.hkl^{(344.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039869/kj2190Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cg1ⁱ	0.97	2.95	3.6999 (15)	135

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Structure Determination of kDa Outer Membrane Proteins From S.typhi by X-ray Protein Crystallography grant (No. 1001/PSKBP/8630013). AMI thanks Professor Sandeep Sanchethi, Director, National Institute of Technology-Karnataka, India, for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India for the Young Scientist award.

supplementary crystallographic information

Comment

Pyrazolines are nitrogen-containing five-membered heterocyclic compounds and have received considerable attention in recent years due to their varied biological and pharmacological activities. Various substituted 2-pyrazolines have been associated with diverse pharmacological activities such as analgesic (Sahu et al., 2008), anti-inflammatory (Farghaly et al., 1990), anti-microbial (Adnan et al., 2005), anti-amoebic (Budakoti et al., 2008), anti-tubercular (Yar et al., 2007), anti-depressant (Palaska et al., 1996) and anti-coagulant (Jia et al., 2004) properties. Based on the above biological activities exhibited by the pyrazolines, we have synthesized the title compound to study its crystal structure.

The molecular structure of the title compound, shown in Fig. 1, contains two pyrazole (N1,N2/C10,C11,C24) and (N3,N4/C7–C9) rings and four phenyl (C1–C6), (C12–C17), (C18–C23) and (C25–C30) rings. The pyrazole rings are essentially planar with maximum deviation of 0.003 (1) Å for atom C10 and 0.066 (1) Å for atom C9. The two pyrazole (N1,N2/C10,C11,C24:N3,N4/C7–C9) rings make dihedral angles of 40.08 (6), 9.28 (6), 15.78 (8) and 17.25 (7)° with their attached phenyl (C12–C17/C18–C23):(C1–C6/C25–C30) rings respectively. The dihedral angle between the two pyrazole, (N1,N2/C10,C11,C24: N3,N4/C7–C9), rings is 73.43 (6)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2010; Fun et al., 2011).

There are no significant intermolecular hydrogen bond interactions in the crystal structure. The structure is stabilized by C8—H8A···Cg1 (Table 1) interactions where Cg1 is the centroid of the C1–C6 ring.

Experimental

A mixture of (2E)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-1-phenylprop- 2-en-1-one (0.35 g, 1.0 mmol) and phenylhydrazine (0.162 g, 1.5 mmol) was refluxed in glacial acetic acid for 4 h. The mixture was then cooled to room temperature and the resulting solid was filtered and dried to get title compound. Yield: 0.22 g, 50%. M. p. 467–469 K (Bratenko et al., 2001).