1-(4-Benz­yloxy-5-meth­oxy-2-nitro­phen­yl)ethanone

Lei Gao; Li-hua Guo; Rui Liu; Dan-hua Que; Hong-fei Ma

doi:10.1107/S1600536809011532

. 2009 Apr 8;65(Pt 5):o1005. doi: 10.1107/S1600536809011532

1-(4-Benzyloxy-5-methoxy-2-nitrophenyl)ethanone

Lei Gao ^a, Li-hua Guo ^a, Rui Liu ^a, Dan-hua Que ^a, Hong-fei Ma ^a,^*

PMCID: PMC2977694 PMID: 21583830

Abstract

In the molecule of the title compound, C₁₆H₁₅NO₅, the aromatic rings are oriented at a dihedral angle of 74.89 (3)°. Intramolecular C—H⋯O interactions result in the formation of a seven-membered ring. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules into chains along the b axis.

Related literature

The title compound is an important pharmaceutical intermediate. For general background, see: Mizuta et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₅NO₅
M _r = 301.29
Orthorhombic,
a = 13.390 (3) Å
b = 10.465 (2) Å
c = 20.768 (4) Å
V = 2910.1 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.980, T _max = 0.990
2634 measured reflections
2634 independent reflections
1446 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.223
S = 1.06
2634 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011532/hk2654sup1.cif

e-65-o1005-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011532/hk2654Isup2.hkl

e-65-o1005-Isup2.hkl^{(129.4KB, 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
C4—H4A⋯O3ⁱ	0.93	2.58	3.466 (5)	158
C16—H16C⋯O4	0.96	2.35	2.899 (5)	115

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound contains nitro, acetyl and methoxy groups, which can react with different groups to prepare various functional organic compounds as a fine organic intermediate. We report herein its crystal structure.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C8-C13) are, of course, planar and they are oriented at a dihedral angle of 74.89 (3)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a seven-membered ring C (O4/N/C10/C11/C15/C16/H16C) having twisted conformation.

In the crystal structure, weak intermolecular C-H···O interactions (Table 1) link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, 1-(4-benzyloxy-5-methoxy-2-nitro- phenyl)ethanone (20.0 g, 66.4 mmol) were dissolved in DMF (50 ml). Then, the solution was poured into ice water (100 ml). The crystalline product was isolated by filtration, washed with water (600 ml). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.