2-(3-Chloro-4-hydroxy­phen­yl)-N-(3,4-dimethoxy­pheneth­yl)acetamide

Rohan A Davis; Peter C Healy

doi:10.1107/S1600536808013299

. 2008 May 10;64(Pt 6):o1057. doi: 10.1107/S1600536808013299

2-(3-Chloro-4-hydroxyphenyl)-N-(3,4-dimethoxyphenethyl)acetamide

Rohan A Davis ^a, Peter C Healy ^a,^*

PMCID: PMC2961350 PMID: 21202576

Abstract

The title compound, C₁₈H₂₀ClNO₄, was synthesized during the generation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide. It crystallizes as discrete molecules linked by intermolecular C(9) chains of N—H⋯O and O—H⋯O hydrogen bonds which in turn combine to form chains of R ₂ ²(20) rings.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Davis et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

C₁₈H₂₀ClNO₄
M _r = 349.80
Monoclinic,
a = 12.329 (3) Å
b = 12.839 (5) Å
c = 11.062 (3) Å
β = 92.18 (2)°
V = 1749.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 K
0.35 × 0.35 × 0.15 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: none
3463 measured reflections
3078 independent reflections
1596 reflections with I > 2σ(I)
R _int = 0.034
3 standard reflections every 150 reflections intensity decay: 0.2%

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.165
S = 0.99
3078 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: MSC/AFC7 Diffractometer Control for Windows (Molecular Structure Corporation, 1999 ▶); cell refinement: MSC/AFC7 Diffractometer Control for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001 ▶); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013299/tk2268sup1.cif

e-64-o1057-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013299/tk2268Isup2.hkl

e-64-o1057-Isup2.hkl^{(151.1KB, 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
N1—H1⋯O14ⁱ	0.91	2.37	3.066 (4)	134
O4—H4⋯O8ⁱ	0.90	1.74	2.616 (4)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge financial support of this work by Griffith University and the Eskitis Institute for Cell and Molecular Therapies.

supplementary crystallographic information

Comment

The title compound (I) was synthesized during the generation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide (Davis et al., 2005, 2007). Compound (I) was shown to display moderate cytotoxicity towards the human melanoma cell line MM96L with 94% inhibition at 100 µg ml^-1 (Davis et al., 2007).

This compound crystallizes as discrete molecules with three planar components: the acetamide group (C7—C8(O8)—N1—C9), the 3-chloro-4-hydroxyphenyl group (C1—C7, O4, Cl3), and the 3,4-dimethoxybenzyl group (C11—C16, C10, O13—C17, O14—C18), Fig. 1. The C9—C10—C11—C16 and C2—C1—C7—C8 torsion angles are -91.8 (4)° and-78.9 (4)° respectively. In the crystal structure the amide (N1) and hydroxy (O4) groups form C(9) chains (Bernstein et al., 1995) of intermolecular N—H···O and O—H···O hydrogen bonds with the methoxy oxygen (O14) and the carbonyl oxygen (O8), respectively (Table 1) which in turn combine to form chains of R₂²(20) rings (Fig. 2).

Experimental

Compound (I) was prepared as previously reported (Davis et al., 2007). Crystals suitable for X-ray diffraction studies were obtained by slow evaporation of a n-hexane/ethyl acetate (1:1) solution of (I); m.p. 421–423 K.