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

Aamer Saeed; Shahid Hussain; Aliya Ibrar; Michael Bolte

doi:10.1107/S1600536809020509

. 2009 Jun 6;65(Pt 7):o1470. doi: 10.1107/S1600536809020509

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

Aamer Saeed ^a,^*, Shahid Hussain ^a, Aliya Ibrar ^a, Michael Bolte ^b

PMCID: PMC2969324 PMID: 21582773

Abstract

In the title compound, C₁₆H₁₆BrNO₄, the dihedral between the planes of the aromatic rings is 7.74 (18)°. The amide group is tilted with respect to the bromo- and methoxy-substituted aromatic rings by 36.3 (8) and 35.2 (8)°, respectively. The meta-methoxy groups are essentially in-plane with the aromatic ring [dihedral angles CH₃—O—C—C = −4.6 (4) and −2.5 (4)°]. The para-methoxy group is markedly displaced from the ring plane [dihedral angle CH₃—O—C—C = −72.5 (4)°]. The crystal packing is stabilized by N—H⋯O hydrogen bonds linking the molecules into chains running along the b axis.

Related literature

For related structures and general background, see: Saeed et al. (2009 ▶). For conformations of aromatic methoxy groups, see: Vande Velde et al. (2006 ▶).

Experimental

Crystal data

C₁₆H₁₆BrNO₄
M _r = 366.21
Orthorhombic,
a = 13.3085 (8) Å
b = 4.9953 (3) Å
c = 23.4061 (12) Å
V = 1556.04 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 173 K
0.37 × 0.34 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan [MULABS (Spek, 2009 ▶; Blessing, 1995 ▶)] T _min = 0.418, T _max = 0.600
11994 measured reflections
3028 independent reflections
2748 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.076
S = 0.99
3028 reflections
207 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1405 Friedel pairs
Flack parameter: 0.001 (8)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020509/zl2213sup1.cif

e-65-o1470-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020509/zl2213Isup2.hkl

e-65-o1470-Isup2.hkl^{(148.6KB, 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⋯O1ⁱ	0.85 (4)	2.06 (4)	2.821 (3)	149 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AI gratefully acknowledges a research scholarship from the HEC, Islamabad, Pakistan, under the HEC Indigenous PhD Scholarship 5000 Scheme.

supplementary crystallographic information

Comment

The background to this study has been described in an earlier paper on N-(2-chlorophenyl)-4-chlorobenzamide (Saeed et al., 2009). As part of our work on the structure of benzanilides and related compounds, we report here the structure of the title compound, Fig. 1.

In the title compound, C₁₆H₁₆BrNO₄, the dihedral angle between the aromatic rings is 7.74 (18)°. The amide moiety is tilted against the bromo and methoxy substituted aromatic rings by 36.3 (8)° and 35.2 (8)°, respectively. The meta methoxy groups are essentially in plane with the aromatic ring [dihedral angles CH₃—O—C—C = -4.6 (4)° and -2.5 (4)°], the methoxy group in para position is markedly displaced from the ring plane [dihedral angle CH₃—O—C—C = -72.5 (4)°]. This can be attributed to a combination of resonance effects, which lead for aromatic methoxy groups to being coplanar with an aromatic ring, and steric interactions, which prohibit a coplanar arrangement when more than two methoxy groups are present per benzene moiety (Vande Velde et al., 2006). The crystal packing is stabilized by N—H···O hydrogen bonds linking the molecules to chains running along the b axis (Fig. 2).

Experimental

3,4,5-Trimethoxybenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 3-bromoaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (81%) as colourless needles. Anal. calcd. for C₁₆H₁₆BrNO₄: C, 52.48; H, 4.40; N, 3.82%; found: C, 52.51; H, 4.36; N, 3.87