3-[(E)-3-(4-Meth­oxy­phen­yl)prop-2-eno­yl]-1-(4-methyl­phen­yl)-5-phenyl-1H-pyrazole-4-carbonitrile

Hatem A Abdel-Aziz; Ahmed Bari; Seik Weng Ng

doi:10.1107/S1600536811005770

. 2011 Feb 23;67(Pt 3):o694. doi: 10.1107/S1600536811005770

3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5-phenyl-1H-pyrazole-4-carbonitrile

Hatem A Abdel-Aziz ^a, Ahmed Bari ^a, Seik Weng Ng ^b,^*

PMCID: PMC3052011 PMID: 21522439

Abstract

In the title compound, C₂₇H₂₁N₃O₂, the non-H atoms of the methoxyphenylacryloyl substitutent of the pyrazolyl ring are almost co-planar (r.m.s. deviation = 0.070 Å), and the mean plane is twisted by 18.7 (1)° with respect to the pyrazolyl ring. The phenyl and tolyl substituents are aligned at 48.9 (1) and 44.5 (1)° with respect to the pyrazolyl ring. Weak intermolecular C—H⋯O and C—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₂₇H₂₁N₃O₂
M _r = 419.47
Triclinic,
a = 10.9995 (7) Å
b = 11.0531 (8) Å
c = 11.4381 (8) Å
α = 95.113 (6)°
β = 111.582 (6)°
γ = 118.219 (7)°
V = 1079.13 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.984, T _max = 0.996
8250 measured reflections
4779 independent reflections
3346 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.133
S = 1.05
4779 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005770/xu5162sup1.cif

e-67-0o694-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005770/xu5162Isup2.hkl

e-67-0o694-Isup2.hkl^{(234.1KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.59	3.350 (3)	137
C22—H22⋯N3ⁱⁱ	0.95	2.61	3.487 (3)	154
C25—H25⋯O2ⁱⁱⁱ	0.95	2.56	3.484 (3)	164

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

Acknowledgments

We thank King Saud University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have reported the antitumor activity of aryl-pyrazoles against CaCo-2 and HEP-2 cell lines (Abdel-Aziz et al., 2010). Among these is the title compound (Scheme I), whose biological properties will be reported elsewhere (Abdel-Aziz et al., 2011). The compound has methoxyphenylacryloyl, phenyl and tolyl substituents in the pyrazolyl ring. The methoxyphenylacryloyl substituent is twisted by 18.7 (1)° with respect to the pyrazolyl ring; the phenyl and tolyl substituents are aligned at 48.9 (1)° and 44.5 (1)° with respect to the five-membered ring (Fig. 1).

Experimental

The synthesis will be reported elsewhere (Abdel-Aziz et al., 2011). 3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile (10 mmol) was reacted with 4-methoxybenzaldehyde (10 mmol) in presence of sodium ethoxide solution (prepared by dissolving 0.23 g sodium metal in 50 ml absolute ethanol). The compound was recrystallized from an ethanol-DMF (3:1) mixture.