1-(4-Chloro­phen­yl)-3-(2-meth­oxy­anilino)propan-1-one

Ligia Llovera; Pavel Anzenbacher, Jr; Simón E López; Teresa González

doi:10.1107/S1600536810054449

. 2011 Jan 12;67(Pt 2):o315. doi: 10.1107/S1600536810054449

1-(4-Chlorophenyl)-3-(2-methoxyanilino)propan-1-one

Ligia Llovera ^a, Pavel Anzenbacher Jr ^b, Simón E López ^a, Teresa González ^c,^*

PMCID: PMC3051662 PMID: 21523002

Abstract

In the title compound, C₁₆H₁₆ClNO₂, the molecule adopts a bowed conformation, with a dihedral angle of 39.9 (2)° between the aromatic rings. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, generating C(6) chains propagating in [010]. Very weak aromatic π–π stacking is also observed [centroid–centroid distance = 4.040 (2) Å].

Related literature

For the synthesis of quinoline derivatives, see: Peifer et al. (2007 ▶). For background to the antimicrobial activity of quinolines, see: Yamashkin & Oreshkina (2006 ▶). For further synthetic details, see: Dienys et al. (1977 ▶); Volkov et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₆ClNO₂
M _r = 289.75
Orthorhombic,
a = 7.1690 (6) Å
b = 14.4303 (11) Å
c = 28.667 (3) Å
V = 2965.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.48 × 0.36 × 0.20 mm

Data collection

Rigaku AFC-7S Mercury diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.927, T _max = 0.950
31012 measured reflections
3035 independent reflections
2016 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.077
wR(F ²) = 0.198
S = 1.14
3035 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: CrystalStructure (Rigaku/MSC, 2005) ▶ and SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054449/hb5773sup1.cif

e-67-0o315-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054449/hb5773Isup2.hkl

e-67-0o315-Isup2.hkl^{(149KB, hkl)}

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
C15—H15A⋯O2ⁱ	0.93	2.49	3.414 (4)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Decanato de Investigación y Desarrollo (DID-USB, Caracas) and the FONACIT–MCT (project LAB-97000821) for financial support. LL thanks the Decanato de Estudios de Postgrado (USB, Caracas) for a travel-training fellowship.

supplementary crystallographic information

Comment

The title compound was prepared as an intermediate for the synthesis of 4-aryl-8-methoxy-quinoline under acid conditions (Dienys et al., 1977). The synthesis of the title compound might be obtained through decyclization of piperidol and transamination of the decyclization products (Volkov et al., 2007). These compounds exhibit a broad range of antimicrobial activity and particular, antitubercular activity, antimalarial activity and are also present in antiallergic and antiasthmatic agents (Yamashkin & Oreshkina, 2006). In addition, these compounds could act as drug targets of a large numbers of protein-inhibitor complexes, for example the mitogen-activated protein kinase (Peifer et al., 2007).

The X-ray structure determination showed that compound (I) contains only one organic molecule per asymmetric unit (Fig. 1). The molecule adopts a slightly angular conformation, where the dihedral angle defined by aromatic rings is 39.9 (2)°. respectively. The crystal packing (Fig. 2) of this structure consists of infinite chains which are interconnected through hydrogen bonding interactions of the kind C—H···O (3.415 Å) along the bc plane. The final array (Fig. 3) is sustained by weak interactions of the kind π···π between aromatics rings with distance between centroid to centroid, Cg2···Cg2: 4.040 (2) Å. Where Cg2 is defined by C11/C12/C13/C14/C15/C16 atoms.

Experimental

A solution of 3-(4-chlorophenyl)-N,N-dimethyl-3-oxopropan-1-aminium chloride (0.01 mol) in distilled water (5 ml) was stirred at room temperature in a round bottom flask. After 5 minutes, a solution of 2-methoxy-phenylamine (0.01 mol) and concentrated hydrochloric acid (0.5 ml) in ethanol (10 ml) was added dropwise and the mixture was stirred at room temperature for 12 h to yield yellow blocks of (I). Yield: 79%. M.p. 83–84°C; ¹H NMR (400 MHz, CDCl₃, δ (p.p.m.), J= Hz): 3.27 (t, 2H, J= 6.4), 3.64 (t, 2H, J= 6.4), 3.81 (s, 3H), 4.57 (s, 1H), 6.68 (m, 2H), 6.76 (dd, 1H, J= 8.4, 1.5), 6.88 (td, 1H, J= 7.6, 1.1), 7.42 (d, 2H, J= 8.4), 7.87 (d, 2H, J= 8.4). ¹³C NMR (100 MHz, CDCl₃, δ (p.p.m.)): 38.0 (C9), 38.4 (C8), 55.5 (C7), 109.7 (C3), 109.9 (C6), 116.9 (C4), 121.3 (C5), 129.0 (C13 and C15), 129.5 (C12 and C16), 135.2 (C1), 137.6 (C11), 139.8 (C14), 147.2 (C7), 200.0 (C10). IR (KBr, cm^-1): 3413, 3085, 3061, 2961, 1685, 1074, 792. EI—MS (m/z): 290.37 [M^+•], 292.37 [M^+• +2], 136.07 [M^+• – (4-ClPhCOCH₂)].