(E)-1-(Naphthalen-1-yl)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one

Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Khalid A Alamry; Seik Weng Ng

doi:10.1107/S1600536811035124

. 2011 Sep 3;67(Pt 10):o2550. doi: 10.1107/S1600536811035124

(E)-1-(Naphthalen-1-yl)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one

Abdullah M Asiri ^a,^b, Abdulrahman O Al-Youbi ^a, Hassan M Faidallah ^a, Khalid A Alamry ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3201529 PMID: 22064894

Abstract

In the title molecule, C₂₂H₁₆N₂O, the phenyl ring is twisted slightly with respect to the plane of the central pyrazole ring [dihedral angle = 14.8 (2)°]; the central ring is connected to the naphthyl ring through a —CH=CH—C(=O)— fragment, whose C=C double bond has an E configuration. The pyrazole ring and naphthalene ring system are twisted by 46.3 (1)°. Weak intermolecular C—H⋯O hydrogen bonds link the molecules, forming supramolecular chains running along the a axis. The crystal studied was a non-merohedral twin with a component ratio of 0.544 (2):0.456 (2).

Related literature

For related structures; see: Diánez & López-Castro (1990 ▶); Jones et al. (1984 ▶). For the synthesis, see: Finar (1961 ▶); Finar & Lord (1959 ▶); Jones et al. (1984 ▶).

Experimental

Crystal data

C₂₂H₁₆N₂O
M _r = 324.37
Monoclinic,
a = 5.8457 (6) Å
b = 10.322 (2) Å
c = 26.626 (2) Å
β = 92.322 (9)°
V = 1605.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.980, T _max = 0.992
3824 measured reflections
3825 independent reflections
2494 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.140
S = 0.96
3825 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 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 datablock(s) global, I. DOI: 10.1107/S1600536811035124/xu5313sup1.cif

e-67-o2550-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035124/xu5313Isup2.hkl

e-67-o2550-Isup2.hkl^{(187.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035124/xu5313Isup3.cml

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
C9—H9⋯O1ⁱ	0.95	2.46	3.397 (4)	167

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The hydrogen of the acetyl group of 1-acetylnaphthalene (as well as that of similar ketones) is relatively acidic, and can be abstracted by a strong base. In the present study, the resulting carbanion is used for carbon-carbon double-bond synthesis to extend the nature of the substitutent at the 4-position of 1-phenylpyrazole-4-carboxaldehyde by using a similar procedure for synthesizing the 1-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one (Finar, 1961; Finar & Lord, 1959). In the C₂₂H₁₆N₂O molecule (Scheme I), the phenyl ring is slightly twisted with respect to the central pyrazole; the central ring is connected to the naphthyl ring through the –CH–CH–C(═O)– fragment, whose C–C double-bond is of an E-configuration (Fig. 1). The pyrazole and naphthalene rings are twisted by 46.3 (1) °. There are only few crystal structure reports of 4-substituted 1-phenylpyrazoles (Diánez López-Castro, 1990; Jones et al., 1984).

Experimental

1-Phenylpyrazole-4-carboxaldehyde (0.01 mol) in ethanol (20 ml) was added to a 1-acetylnaphthalene (0.01 mol) in dissolved in 20% ethanolic potassium hydroxide (20 ml). The mixture was stirred for 6 h. The mixture was then poured into water (200 ml). The precipitated product was collected by filtration, washed with water, dried and recrystallized from ethanol; m.p. 389–391 K.