6,7-Dimeth­oxy-2,4-di­phenyl­quinoline

M Prabhuswamy; S Madan Kumar; T R Swaroop; K S Rangappa; N K Lokanath

doi:10.1107/S1600536814000725

. 2014 Jan 18;70(Pt 2):o165. doi: 10.1107/S1600536814000725

6,7-Dimethoxy-2,4-diphenylquinoline

M Prabhuswamy ^a, S Madan Kumar ^a, T R Swaroop ^b, K S Rangappa ^a, N K Lokanath ^a,^*

PMCID: PMC3998322 PMID: 24764883

Abstract

In the title structure of the title compound, C₂₃H₁₉NO₂, two conformationally similar molecules (A and B) comprise the asymmetric unit. The dihedral angle between phenyl rings bridged by the quinoline moiety are 76.25 (8)° in molecule A and 70.39 (9)° in molecule B. In the crystal, the independent molecules are connected by C—H⋯O hydrogen bonds and the resulting dimeric aggregates are linked by π–π [inter-centroid distance = 3.7370 (8) Å] and C—H⋯π interactions, forming a three-dimensional architecture.

Related literature

For general background, and the biological and pharmacological properties of quinoline derivatives, see: Michael (2006 ▶). For a related structure, see: Prabhuswamy et al. (2012 ▶).

Experimental

Crystal data

C₂₃H₁₉NO₂
M _r = 341.39
Triclinic,
a = 8.7092 (3) Å
b = 10.5639 (3) Å
c = 20.3400 (7) Å
α = 85.678 (1)°
β = 79.397 (1)°
γ = 80.134 (1)°
V = 1810.33 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.14 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2013 ▶) T _min = 0.868, T _max = 0.917
21904 measured reflections
5877 independent reflections
5181 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.120
S = 1.04
5877 reflections
474 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT-Plus (Bruker, 2013 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814000725/tk5285sup1.cif

e-70-0o165-sup1.cif^{(49.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000725/tk5285Isup2.hkl

e-70-0o165-Isup2.hkl^{(287.7KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814000725/tk5285Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=981089

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg6 and Cg9 are the centroids of the N10B,C7B–C9B,C11B,C12B and C21B–C26B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6A⋯O19B ⁱ	0.93	2.58	3.366 (2)	142
C18B—H18F⋯Cg9ⁱⁱ	0.96	2.93	3.879 (2)	169
C20B—H20D⋯Cg6ⁱⁱⁱ	0.96	2.93	3.59 (18)	127

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

Acknowledgments

Authors thank the IOE X-ray diffractometer facility, University of Mysore, Mysore for collecting data.

supplementary crystallographic information

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

The enaminone (Z)-3((3,4-dimethoxyphenyl)amino)-1,3-diphenylprop-2-en-1-one (5 mmol) was taken in polyphodphoric acid (5 ml) and heated at 140 °C for 5 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 X 20 ml), the combined ethyl acetatelayer was washed with 0.1 N NaOH (2 X 25 ml), followed by brine solution (25 ml). The organic layer was then dried over anhydrous sodium sulfate nd concentrated under reduced pressure to afford the crude product 6,7-dimethoxy-2,4-diphenylquinoline which was purified by coloumn chromatography over silica gel (60–120 mesh) using a hexane:ethyl acetate mixture (9.5:0.5) as eluent. The pure title compound was crystallized in an ethyl acetate-hexane mixture to obtain pale yellow single crystals.

2.2. Refinement

All hydrogen atoms were located geometrically with (C—H = 0.93–0.96) Å and allowed to ride on their parent atoms with U_iso(H) = 1.2U_eq(aromatic C) or 1.5U_iso(methyl C).

3. Results and discussion

Quinolines exhibit physico-chemical activities which are useful in the field of pharmaceuticals and agrochemicals. Their derivatives are also present in a wide variety of natural products involved in several biological activities (Michael, 2006). The crystal structure of the title compound is presented here as a part of our on-going structural studies on quinoline derivatives. The asymmetric unit consists of two symmetry-independent title molecules (A and B) (Fig. 1). The dihedral angle between phenyl ring [C1/C2/C3/C4/C5/C6 (A/B)] and quinoline moiety are 60.44 (7)° (A) and 56.04 (8)° (B). The dihedral angle between phenyl rings bridged by quinoline moiety are 76.25 (8)° (A) and 70.39 (9) ° (B). Also, the quinoline moiety makes a dihedral angle of 29.14 (8)° (A) and 24.64 (8)° (B) with phenyl ring C21/C22/C23/C24/C25/C26 (A/B). The overall geometry of the title compound is similar to the earlier reported structure of 2-(4-chlorophenyl)-6-methyl-4-m-tolyl quinoline (Prabhuswamy et al., 2012).

The molecules are connected by intermolecular hydrogen bonds C6A–H6A···O19B (Fig. 2). The crystal structure is further stabilized by π···π interactions between Cg(6) and Cg(6)ⁱ with a distance of 3.7370 (8) Å [i: 1 - x, 2 - y, -z]. The C—H···π interactions, C18B–H18F···Cg(9) [x, 1 + y, z] and C20B–H20D···Cg(6) [2 - x, 2 - y, z], Table 2, link molecules to stabilize the three-dimensional crystal structure.