(E)-1-(2,4-Dichloro­phen­yl)-3-[3-(4-meth­oxy­phen­yl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one

Hoong-Kun Fun; Ching Kheng Quah; Shridhar Malladi; Raghavendra Hebbar; Arun M Isloor

doi:10.1107/S1600536811044400

. 2011 Oct 29;67(Pt 11):o3105. doi: 10.1107/S1600536811044400

(E)-1-(2,4-Dichlorophenyl)-3-[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Shridhar Malladi ^b, Raghavendra Hebbar ^b, Arun M Isloor ^b

PMCID: PMC3247490 PMID: 22220108

Abstract

In the title molecule, C₂₅H₁₈Cl₂N₂O₂, the dihedral angles between the pyrazole ring and its N- and C-bonded benzene rings are 8.28 (11) and 40.89 (10)°, respectively. The dihedral angle between the benzene rings is 39.03 (11)°. The title molecule exists in a trans conformation with respect to the acyclic C=C bond. In the crystal, molecules are linked into inversion dimers by pairs of intermolecular C—H⋯O hydrogen bonds, generating R ₂ ²(14) loops.

Related literature

For related structures and background references to pyrazole derivatives, see: Fun et al. (2011a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₅H₁₈Cl₂N₂O₂
M _r = 449.31
Monoclinic,
a = 11.5037 (9) Å
b = 9.9197 (8) Å
c = 19.6867 (16) Å
β = 94.986 (2)°
V = 2238.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.42 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.879, T _max = 0.940
24117 measured reflections
6481 independent reflections
3796 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.155
S = 1.02
6481 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.40 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/S1600536811044400/hb6463sup1.cif

e-67-o3105-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044400/hb6463Isup2.hkl

e-67-o3105-Isup2.hkl^{(317.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811044400/hb6463Isup3.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
C11—H11A⋯O1ⁱ	0.93	2.35	3.271 (2)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young scientist award.

supplementary crystallographic information

Comment

As part of our ongoing studies of pyrazole derivatives (Fun et al., 2011a,b), we have synthesized the title compound to study its crystal structure.

In the title molecule (Fig. 1), the benzene (C20-C25) ring and the two phenyl (C1-C6 and C13-C18) rings form dihedral angles of 8.28 (11), 52.12 (11) and 40.89 (10)°, respectively, with the pyrazole ring (N1/N2/C10-C12). The benzene ring also forms dihedral angles of 56.27 (12) and 39.03 (11)° with dichloro-bound phenyl (C1-C6) and methoxy-bound phenyl (C13-C18) rings, respectively. The phenyl rings form a dihedral angle of 87.40 (11)°. The title molecule exists in trans configuration with respect to the acyclic C8═C9 bond [bond length = 1.331 (2) Å]. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b).

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C11–H11A···O1 hydrogen bonds (Table 1), generating fourteen-membered D²₂(14) ring motifs (Bernstein et al., 1995).

Experimental

To a cold, stirred mixture of methanol (20 ml) and sodium hydroxide (12.09 mmol), 2,4-dichloroacetophenone (4.03 mmol) was added. The reaction mixture was stirred for 10 min. 3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazole- 4-carbaldehyde (4.03 mmol) was added to this solution followed by tetrahydrofuran (30 ml). The solution was further stirred for 2 h at 293 K and then at room temperature for 5 h. It was then poured into ice cold water. The resulting solution was neutralized with dil. HCl. The solid that separated out was filtered, washed with water, dried and crystallized from ethanol to yield colourless blocks. Yield: 1.45 g, 80.55 %. M.p. : 447-449 K.