4-[4-(3-Methoxy­benzamido)phen­oxy]-N-methyl­picolinamide

Na-Na Meng; Ting-Ting Huang; De-Kuan Li; Wen-Xin Zhang; Luo-Ting Yu

doi:10.1107/S1600536809055688

. 2010 Jan 30;66(Pt 2):o476. doi: 10.1107/S1600536809055688

4-[4-(3-Methoxybenzamido)phenoxy]-N-methylpicolinamide

Na-Na Meng ^a, Ting-Ting Huang ^a, De-Kuan Li ^b, Wen-Xin Zhang ^c, Luo-Ting Yu ^a,^*

PMCID: PMC2979880 PMID: 21579885

Abstract

In the title compound, C₂₁H₁₉N₃O₄, the central benzene ring makes dihedral angles of 78.54 (6) and 75.30 (6)° with the pyridine and 3-methoxyphenyl rings, respectively. An intramolecular N—H⋯N interaction occurs, generating an S(?). The crystal packing shows intermolecular N—H⋯O hydrogen-bonding interactions between the N—H groups and the O atoms of the 3-methoxyphenyl ring and the carbonyl groups of the amide functions. Intermolecular C—H⋯O interactions are also present.

Related literature

For related compounds and their biological activity, see: Khire et al. (2004 ▶); Dominguez et al. (2007 ▶).

Experimental

Crystal data

C₂₁H₁₉N₃O₄
M _r = 377.39
Triclinic,
a = 5.0915 (10) Å
b = 8.3251 (17) Å
c = 11.611 (2) Å
α = 71.29 (3)°
β = 87.74 (3)°
γ = 76.10 (3)°
V = 452.14 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.34 × 0.29 × 0.19 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.968, T _max = 0.982
3733 measured reflections
2108 independent reflections
1811 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.085
S = 1.10
2108 reflections
263 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055688/om2308sup1.cif

e-66-0o476-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055688/om2308Isup2.hkl

e-66-0o476-Isup2.hkl^{(103.6KB, 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—H1N⋯O2ⁱ	0.89 (3)	2.08 (3)	2.918 (2)	155 (3)
N3—H3N⋯O1ⁱⁱ	0.85 (3)	2.38 (3)	3.148 (3)	151 (2)
N3—H3N⋯N2	0.85 (3)	2.33 (3)	2.681 (3)	105 (2)
C7—H7B⋯O4ⁱⁱⁱ	0.98	2.55	3.475 (3)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The project was sponsored by the Scientific Research Foundation for Returned Overseas Chinese Scholars (No. 20071108–18–14), State Education Ministry. We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

Sorafenib is of great importance owing to its antitumor properties (Khire et al., 2004; Dominguez et al., 2007). The title compound, as one of its derivatives, possessed even better in vitro anticancer activity against both two tumor cell lines (HCT116 and HEPG2). As a potent antitumor drug, we report here its crystal structure.

In the title molecule, C₂₁H₁₉N₃O₄, (Fig.1), the phenyl ring makes dihedral angles of 78.54 (6)° and 75.30 (6)° with the pyridine ring and the 3-methoxyphenyl ring, respectively. In the crystal structure, intermolecular N—H···O hydrogen-bonding interactions between the N—H and O atoms of 3-methoxyphenyl ring and carbonyl groups of the amide functionalities form an infinite three-dimensional structure (Table 1 and Fig. 2).

Experimental

To the suspension of anhydrous potassium carbonate (1.635 g,12.5 mmol) and 4-(4-aminophenoxy)-N-methylpicolinamide (1.22 g, 5 mmol) in 11.4 ml THF was added dropwise 3-methoxybenzoyl chloride(1.28 g,7.5 mmol). After being stirred at room temperature for 2 h, the mixture was extracted with 90 ml EA and 30 ml water for three times and the combined organic layers were dried over anhydrous Na₂SO₄. Then the solution was concentrated under vacuum, and the residue was recrystallized from ethanol to give the title compound. Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of ethanol.