3,4,5-Trimeth­oxy-N-(2-methoxy­phen­yl)benzamide

Aamer Saeed; Ulrich Flörke

doi:10.1107/S1600536809027974

. 2009 Jul 22;65(Pt 8):o1948. doi: 10.1107/S1600536809027974

3,4,5-Trimethoxy-N-(2-methoxyphenyl)benzamide

Aamer Saeed ^a,^*, Ulrich Flörke ^b

PMCID: PMC2977507 PMID: 21583628

Abstract

In the title molecule, C₁₇H₁₉NO₅, the amide plane is oriented at an angle of 41.5 (3)° with respect to the 2-methoxybenzene ring. The three methoxy groups lie almost in the plane of the aromatic rings to which they are attached [C—O—C—C torsion angles of of 0.7 (4), −13.4 (4) and 3.1 (4)°], whereas the methoxy group at the 4-position of the 3,4,5-trimethoxybenzene ring is nearly perpendicularly oriented [C—O—C—C torsion angle of 103.9 (3)°]. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along [001].

Related literature

The background of this work has been described in our earlier paper (Saeed et al. 2008 ▶). For a related structure, see: Parra et al. (2001 ▶).

Experimental

Crystal data

C₁₇H₁₉NO₅
M _r = 317.33
Orthorhombic,
a = 7.409 (2) Å
b = 22.522 (6) Å
c = 9.681 (3) Å
V = 1615.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.50 × 0.44 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.953, T _max = 0.981
13253 measured reflections
2050 independent reflections
1902 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.126
S = 1.13
2050 reflections
216 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027974/wm2245sup1.cif

e-65-o1948-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027974/wm2245Isup2.hkl

e-65-o1948-Isup2.hkl^{(100.9KB, 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	0.895 (10)	2.182 (14)	3.066 (4)	169 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AS gratefully acknowledges a reasearch grant from Quaid-i-Azam University, Islamabad, under the URF project.

supplementary crystallographic information

Comment

The background of this work has been described in our earlier paper (Saeed et al. 2008).

The molecular structure of the title compound (Fig. 1) is similar to that of ICULOH (Parra et al., 2001), but with 3,4,5-methoxy substitution of the benzamide ring. Methoxy groups O2, O3 and O5 lie almost in plane of the corresponding aromatic rings with torsion angles C8–O2–C7–C6 of 0.7 (4)°, C15–O3–C11–C10 of -13.4 (4)° and C17–O5–C13–C14 of 3.1 (4)°, respectively, whereas the O4-group is nearly perpendicular oriented with C16–O4–C12–C13 of 103.9 (3)°. The two aromatic planes make a dihedral angle of 67.66 (9)° and the angle between the amide group and the 2-methoxy benzene ring is 41.5 (3)°. In the cystal structure, intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the [001] direction (Fig. 2).

Experimental

3,4,5-Trimethoxybenzoyl chloride (1 mmol) in CHCl₃ was treated with 2-methoxyaniline (3.5 mmol) under a nitrogen atmosphere at reflux conditions for 5 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with 1 M aq HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in methanol afforded the title compound (84%) as white needles: Anal. calc. for C₁₇H₁₉NO₅: C 64.34, H 6.03, N 4.41%; found: C 64.31, H 6.09, N 4.34%