N,N,N′,N′-Tetra­kis(2-hy­droxy-5-methyl­benz­yl)ethane-1,2-diamine dimethyl­formamide disolvate

Nuan-Sheng Wang; Yong-Tao Wang; Xiu-Kai Guo; Tian-Duo Li

doi:10.1107/S1600536811017934

. 2011 May 20;67(Pt 6):o1438. doi: 10.1107/S1600536811017934

N,N,N′,N′-Tetrakis(2-hydroxy-5-methylbenzyl)ethane-1,2-diamine dimethylformamide disolvate

Nuan-Sheng Wang ^a, Yong-Tao Wang ^a, Xiu-Kai Guo ^b, Tian-Duo Li ^a,^*

PMCID: PMC3120359 PMID: 21754816

Abstract

The title compound, C₃₄H₄₀N₂O₄·2C₃H₇NO, was synthesized by the Mannich condensation of ethanediamine, formaldehyde and p-cresol. In the crystal, the tetraphenol molecule is arranged around an inversion center. The molecule and the dimethylformamide solvate are linked through an O—H⋯O hydrogen bond. An intramolecular O—H⋯N hydrogen bond occurs in the tetraphenol molecule, which may influence the molecular confomation. Futhermore, C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.7081 (14) Å] stabilize the crystal packing, building a three-dimensional network.

Related literature

For applications of the title compound, see: Liu et al. (2007 ▶); Tshuva et al. (2000 ▶); For related structures, see: Hou et al. (2010 ▶); Higham et al. (2006 ▶); Farrell et al. (2007 ▶).

Experimental

Crystal data

C₃₄H₄₀N₂O₄·2C₃H₇NO
M _r = 686.87
Monoclinic,
a = 11.574 (2) Å
b = 6.3557 (12) Å
c = 26.343 (5) Å
β = 94.939 (3)°
V = 1930.7 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEX diffractometer
9607 measured reflections
3569 independent reflections
2667 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.154
S = 1.07
3569 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017934/dn2686sup1.cif

e-67-o1438-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017934/dn2686Isup2.hkl

e-67-o1438-Isup2.hkl^{(175KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017934/dn2686Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811017934/dn2686Isup4.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
O1—H1⋯N1	0.82	1.98	2.705 (2)	147
O2—H2⋯O3	0.82	1.87	2.690 (2)	177
C18—H18⋯O3ⁱ	0.93	2.56	3.368 (3)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Shandong Province Higher Educational Science and Technology Program for financial support (J09LB03).

supplementary crystallographic information

Comment

Multidentate aminophenol are of interest as metallochelators and as ligands for bioinorganic modeling, catalysis, and medical imaging.(Higham et al., 2006; Farrell et al., 2007). Some of them in combination with metals are used as active catalysts for alkenes polymerization (Tshuva et al., 2000) and initiators in the ring-openingpolymerization of lactones (Liu et al., 2007). Herein, we report the crystal structure of the title compound, 'C₃₄H₄₀N₂O₄.(C₃H₇NO)₂'.

The N, N'-Tetrakis(2-hydroxy-5-methylbenzyl)-1, 2-ethanediamine molecule is arranged around inversion center located in the middle of the CH₂-CH₂ bond. The DMF solvate is linked to this molecule through O-H···O hydrogen bonds (Fig. 1). There is also a weak intramolecular O-H···N interactions which might influence the conformation of the molecule (Table 1) (Hou et al., 2010).

The occurence of weak C-H···O interactions (Table 1) and π-π stacking between the symmetry related C1—C6 phenyl rings (Centroid to centroid distance of 3.7081 (14)Å, interplanar distance of 3.6891 (8)° and slippage of 0.375Å) result in the formation of a three dimensional network (Fig. 2)

Experimental

The title compound was prepared by mixing ethylenediamine (1.0 mmol), paraformaldehyde (4.0 mmol) and p-cresol (10 mmol) were heated to 90°C and stirred for 18 h. This reaction requires no solvent nor inert atmosphere. At the end of the reaction, 10ml of ethanol was added to the mixtures to remove the unreacted p-cresol, then sonicated 10 minutes. Finally a white precipitate product was collected by filtration in 56% yield.