N-(4-Bromo­phen­yl)-3,4,5-trimeth­oxy­benzamide

Wen Gu; Chao Qiao

doi:10.1107/S1600536812018946

. 2012 May 5;68(Pt 6):o1658. doi: 10.1107/S1600536812018946

N-(4-Bromophenyl)-3,4,5-trimethoxybenzamide

Wen Gu ^a,^*, Chao Qiao ^a

PMCID: PMC3379256 PMID: 22719454

Abstract

In the title compound, C₁₆H₁₆BrNO₄, the dihedral angle between the two aromatic rings is 67.51 (25)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds involving the N—H and C=O groups of the amide function, leading to a chain along [-101].

Related literature

For the synthesis and biological activity of 3,4,5-trimethoxybenzamide derivatives, see: Buettner et al. (2009 ▶); Pellicani et al. (2012 ▶). For related structures, see: Saeed & Flörke (2009 ▶); Saeed et al. (2008 ▶); Choi et al. (2010 ▶). graphic file with name e-68-o1658-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆BrNO₄
M _r = 366.21
Monoclinic,
a = 9.5860 (19) Å
b = 26.010 (5) Å
c = 7.1390 (14) Å
β = 112.04 (3)°
V = 1649.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.51 mm⁻¹
T = 293 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 = 0.634, T _max = 0.788
3194 measured reflections
1616 independent reflections
1206 reflections with I > 2σ(I)
R _int = 0.064
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.094
S = 1.00
1616 reflections
199 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 91 Friedel pairs
Flack parameter: 0.010 (17)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018946/kp2410sup1.cif

e-68-o1658-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018946/kp2410Isup2.hkl

e-68-o1658-Isup2.hkl^{(79.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018946/kp2410Isup3.cml

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
N—H0A⋯O4ⁱ	0.86	2.19	2.909 (9)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was supported by a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). The authors thank Professor H. Q. Wang of the Center for Testing and Analysis, Nanjing University, for the collection of the X-ray diffraction data.

supplementary crystallographic information

Comment

As a part of our ongoing research on the synthesis and biological activities of 3,4,5-trimethoxy-benzamide derivatives, the title compound (I) was synthesised and its crystal structure was determined (Fig. 1). In the crystal packing N-H···O hydrogen bond generates a chain along [101] (Table 1).

Experimental

To a solution of 3,4,5-Trimethoxybenzoyl chloride (1.15 g, 5 mmol) in benzene (20 mL) was added 4-bromoaniline (0.95 g, 5.5 mmol) and triethylamine (0.56 g, 5.5 mmol). The mixture was stirred at room temperature for 12 h. After cooling, the reaction mixture was filtered to remove precipitate, and the filtrate was evaporated in vacuo to afford a white solid, which was recrystalised in EtOH to give the title compound (I) as a colourless prisms (1.5 g, 82%). Single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol solution at room temperature over 7 d.