N-[3-(Dimethyl­amino)­prop­yl]-N′-(2-hy­droxy-5-methyl­phen­yl)oxamide

Yong-Jun Zheng; Kang Zheng; Zhi-Yong Wu; Yantuan Li

doi:10.1107/S1600536812007957

. 2012 Feb 29;68(Pt 3):o895. doi: 10.1107/S1600536812007957

N-[3-(Dimethylamino)propyl]-N′-(2-hydroxy-5-methylphenyl)oxamide

Yong-Jun Zheng ^a, Kang Zheng ^a, Zhi-Yong Wu ^b, Yantuan Li ^a,^*

PMCID: PMC3297941 PMID: 22412744

Abstract

In the title compound, C₁₄H₂₁N₃O₃, the oxamide group has a transoid conformation. In the crystal, the molecules are connected by N—H⋯O and O—H⋯N hydrogen bonds into a double chain running along the b axis.

Related literature

For the use of N,N′-bis(substituted)oxamides in the synthesis of nuclear complexes, see: Ojima & Nonoyama (1988 ▶); Ruiz et al. (1999 ▶). For related compounds, see: Han et al. (2007 ▶); Martinez et al. (1998 ▶); Yue et al. (2012 ▶).

Experimental

Crystal data

C₁₄H₂₁N₃O₃
M _r = 279.34
Monoclinic,
a = 11.542 (2) Å
b = 10.304 (2) Å
c = 13.860 (3) Å
β = 109.16 (3)°
V = 1557.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.27 × 0.24 × 0.17 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.977, T _max = 0.986
7686 measured reflections
3099 independent reflections
2093 reflections with I > 2σ(I)
R _int = 0.022
Standard reflections: 0

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.151
S = 1.02
3099 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 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: XP (Siemens, 1994 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007957/bt5821sup1.cif

e-68-0o895-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007957/bt5821Isup2.hkl

e-68-0o895-Isup2.hkl^{(149KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007957/bt5821Isup3.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
N2—H2⋯O2ⁱ	0.92 (3)	2.13 (3)	2.945 (2)	147 (2)
O1—H1A⋯N3ⁱⁱ	0.90 (2)	1.76 (2)	2.654 (2)	168 (3)

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

Acknowledgments

This project was supported by the Natural Science Foundation of China (grant No. 21071133) and the Natural Science Foundation of Qingdao City.

supplementary crystallographic information

Comment

N,N'-bis(substituented)oxamides as multiatom bridging ligands has played an important role in designing and synthesizing polymetallic systems (Ojima & Nonoyama, 1988; Ruiz et al., 1999). Due to the difficulties of synthesis only few dissymmetrical bis-substituented-oxamide ligand has been reported. In order to provide more examples of such ligand, quite recently, we reported the structure of (3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate (Yue et al.,2012). In continuation of our earlier work, the title compound was synthesized and its structure is reported here.

As shown in Fig. 1, the title compound has a trans-conformation of the oxamide group. The whole compound likes the alphabet `L'. The benzene ring is almost coplanar to the oxamide group [11.44 (9)°], just like that in the compound of N,N'-bis(2-Hydroxyphenyl)oxamide (Martinez et al., 1998). However, the plane through the other substituent group, aminopropyl, is perpendicular to the oxamide plane [83.49 (12)°]. The torsion angle of C9—N2—C10—C11 is 106.7 (2)° (Table 1). And the conformation for the C10—C11 bond is gauche. While in the compound 2-(N'-[3-(Dimethylammonio)propyl)oxamido]benzoate (Han et al., 2007), the corresponding angle is 151.3 (3)° and the conformation is anti.

A centrosymmetric dimer of a pair of the compounds is formed via the hydrogen bonds of the oxamide groups (Fig. 2, Table 2). These dimers are further assembled to a chain parallel to the b-axis through the hydrogen bonds between the phenolic hydroxyl groups and the tertiary amino groups.

Experimental

All reagents were of AR grade and obtained commercially without further purification. The title compound was prepared according to the method proposed by Han et al. (2007). A tetrahydrofuran (THF) solution (8 ml) of ethyl oxalyl chloride (1.11 ml, 10 mmol) was added dropwise into a THF solution (50 ml) of 2-amino-4-methylphenol (1.23 g, 10 mmol) with continuous stirring. The mixture was stirred quickly for 1 h and became clear. Then 20 ml ethanol was further added and the mixture was added dropwise into the solution (10 ml) of 3-dimethylamino-propylamine (1.02 g, 10 mmol) with stirring and kept the temperature at 273 K for 9 h. The title compound was precipitated as a white powder and washed with ethanol for several times and dried under vacuum. Yield: 1.83 g (66%). Colourless crystals of compound with the suitable size for X-ray analysis were obtained from an ethanol/water (1:1) mixture by slow evaporation for one week at room temperature.

Anal. Calcd. for C₁₄H₂₁N₃O₃ (%): C, 60.20; H, 7.58; N, 15.04. Found: C, 60.33; H, 7.65; N, 15.00.