1-[3-(4-Chloro­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Hoong-Kun Fun; Ching Kheng Quah; S Samshuddin; B Narayana; B K Sarojini

doi:10.1107/S1600536812009439

. 2012 Mar 10;68(Pt 4):o1023. doi: 10.1107/S1600536812009439

1-[3-(4-Chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, S Samshuddin ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3343987 PMID: 22589896

Abstract

In the title compound, C₁₈H₁₇ClN₂O₂, the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, molecules are linked via bifurcated (C,C)–H⋯O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For general background to and the biological activity of the title compound, see: Samshuddin et al. (2011 ▶); Sarojini et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C₁₈H₁₇ClN₂O₂
M _r = 328.79
Monoclinic,
a = 9.3473 (4) Å
b = 9.4418 (4) Å
c = 19.7840 (7) Å
β = 113.830 (2)°
V = 1597.19 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.39 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.908, T _max = 0.958
21450 measured reflections
5715 independent reflections
4900 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.109
S = 1.08
5715 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.26 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/S1600536812009439/bv2200sup1.cif

e-68-o1023-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009439/bv2200Isup2.hkl

e-68-o1023-Isup2.hkl^{(279.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009439/bv2200Isup3.cml

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

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

Cg1 is the centroid of C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2ⁱ	0.95	2.55	3.4993 (14)	174
C16—H16B⋯O2ⁱⁱ	0.98	2.59	3.5275 (12)	161
C16—H16C⋯Cg1ⁱⁱⁱ	0.98	2.69	3.5333 (10)	145

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

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC for financial assistance through an SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

supplementary crystallographic information

Comment

Pyrazolines are know for exhibiting biological properties such as antibacterial, antifungal, antioxidant and analgesic activities (Samshuddin et al., 2011; Sarojini et al., 2010). In continuation of our work on synthesis of pyrazoline derivatives (Fun et al., 2010), the title compound (I) is prepared and its crystal structure is reported.

In the title molecule (Fig. 1), the two benzene rings (C1-C6 and C10-C15) form dihedral angles of 6.69 (6) and 74.88 (5)°, respectively, with the 4,5-dihydro-1H-pyrazole ring (N1/N2/C7-C9). The benzene rings form a dihedral angle of 76.67 (5)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with a related structures (Fun et al., 2010).

In the crystal structure, Fig. 2, molecules are linked via intermolecular bifurcated C5–H5A···O2 and C16–H16B···O2 hydrogen bonds (Table 1) into one-dimensional chains along [010]. The crystal structure is further consolidated by C16–H16C···Cg1ⁱⁱⁱ (Table 1) interactions, where Cg1 is the centroid of C10-C15 benzene ring.

Experimental

A mixture of (2E)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (2.72 g, 0.01 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 25 ml acetic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single crystals were grown from dimethylformamide (DMF) by slow evaporation method and yield of the compound was 82% (m.p. : 409 K).