6-Chloro-3-[5-(4-fluoro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl­quinoline

Wan-Sin Loh; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; B Palakshi Reddy

doi:10.1107/S1600536810000218

. 2010 Jan 9;66(Pt 2):o304. doi: 10.1107/S1600536810000218

6-Chloro-3-[5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenylquinoline

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, S Sarveswari ^b, V Vijayakumar ^b, B Palakshi Reddy ^b

PMCID: PMC2979872 PMID: 21579737

Abstract

In the title compound, C₃₁H₂₃ClFN₃, the pyrazole ring forms dihedral angles of 72.75 (7), 18.08 (9) and 86.26 (9)° with the quinoline ring system, the phenyl ring and the fluorophenyl ring, respectively. In the crystal, intermolecular C—H⋯N hydrogen bonds link the molecules into chains propagating along the c axis. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For a related structure and background to quinolines and pyrazolines, see: Loh et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₃₁H₂₃ClFN₃
M _r = 491.97
Monoclinic,
a = 9.4303 (2) Å
b = 28.2155 (6) Å
c = 9.6028 (2) Å
β = 106.636 (1)°
V = 2448.17 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.49 × 0.23 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.914, T _max = 0.973
38888 measured reflections
8947 independent reflections
6981 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.171
S = 1.08
8947 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.25 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 datablocks global, I. DOI: 10.1107/S1600536810000218/hb5303sup1.cif

e-66-0o304-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000218/hb5303Isup2.hkl

e-66-0o304-Isup2.hkl^{(437.6KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the N1/C1/C2/C7–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N1ⁱ	0.93	2.57	3.493 (2)	173
C17—H17A⋯Cg1	0.97	2.86	3.6307 (19)	137
C31—H31B⋯Cg2ⁱⁱ	0.96	2.86	3.584 (2)	133

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks Malaysian government and USM for the award of the post of Assistant Research Officer under Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

As part of our onging studies of substituted pyrazoline derivatives (Loh et al., 2009), we now report the synthesis and structure of the title compound, (I).

The pyrazole ring (C16–C18/N2/N3) in (I) forms dihedral angles of 72.75 (7), 18.08 (9) and 86.26 (9) ° with the quinoline ring system (C1–C9/N1), phenyl (C25–C30) and fluorophenyl (C19–C24) rings, respectively. The quinoline ring system is approximately planar with a maximum deviation of 0.025 (2) Å at atom C9. Bond lengths and angles observed are comparable to a related structure (Loh et al., 2009).

In the crystal packing, intermolecular C15—H15A···N1 hydrogen bonds link the molecules into extended one-dimensional chains along c axis. The crystal structure is further stabilized by C—H···π interactions.

Experimental

A mixture of 1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3-(4-flourophenyl) prop-2-en-1-one (0.001 M) and phenyl hydrazine in (0.007 M) in distilled methanol was refluxed for about 8 h. The resulting mixture was concentrated to remove methanol then poured on to ice and neutralized with diluted HCl. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of chloroform and petroleum ether. The compound was recrystallized from methanol to yield yellow blocks of (I). M. p.: 433–435 K, yield: 60%.