N,N,N′,N′-Tetra­kis(2-hydroxy­ethyl)terephthalamide

Zhi-Qiang Wang; Chen Xu; Ying-Fei Li; Fei-Fei Cen; Yu-Qing Zhang

doi:10.1107/S1600536808041573

. 2008 Dec 20;65(Pt 1):o166. doi: 10.1107/S1600536808041573

N,N,N′,N′-Tetrakis(2-hydroxyethyl)terephthalamide

Zhi-Qiang Wang ^a,^*, Chen Xu ^a, Ying-Fei Li ^b, Fei-Fei Cen ^b, Yu-Qing Zhang ^b

PMCID: PMC2968077 PMID: 21581622

Abstract

The molecule of the title compound, C₁₆H₂₄N₂O₆, which lies on a crystallographic inversion centre in the centre of the benzene ring, adopts an anti conformation in terms of the relative orientation of two amide carbonyl groups. One pair of the 2-hydroxyethyl groups is partially disordered with site occupancy factors of 0.811 (2) and 0.189 (2). The dihedral angle between the amide group and central benzene ring is 67.0 (2)°. Two O—H⋯O and one bifurcated O—H⋯(O,O) hydrogen bonds are present, resulting in a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background, see: Katoono et al. (2006 ▶); Tosin et al. (2005 ▶); Yin et al. (2005 ▶).

Experimental

Crystal data

C₁₆H₂₄N₂O₆
M _r = 340.37
Orthorhombic,
a = 10.3244 (12) Å
b = 12.5378 (14) Å
c = 12.8384 (15) Å
V = 1661.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.29 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.961, T _max = 0.976
11505 measured reflections
1550 independent reflections
1273 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.126
S = 1.06
1550 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536808041573/rn2054sup1.cif

e-65-0o166-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041573/rn2054Isup2.hkl

e-65-0o166-Isup2.hkl^{(76.5KB, 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
O2—H2A⋯O3ⁱ	0.82	1.91	2.723 (9)	169
O2—H2A⋯O3′ⁱ	0.82	1.90	2.675 (10)	157
O3′—H3′⋯O2ⁱⁱ	0.82	2.31	2.675 (3)	108
O3—H3D⋯O1ⁱⁱⁱ	0.82	2.00	2.810 (2)	170

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

Acknowledgments

This work was supported by the Doctoral Foundation of Luoyang Normal University.

supplementary crystallographic information

Comment

Terephthalamide derivatives are important compounds in molecular recognition and supramolecular chemistry (Yin et al., 2005; Tosin et al.,2005; Katoono et al.,2006). Although numerous tetrasubstituted terephthalamides have been investigated, only a few tetrakis(alkyl)terephthalamides are known. In order to further the study of such compounds, we report the crystal structure of the title compound.

A view of the molecular structure of the title compound is given in Fig.1. Molecules of the title compound lie across crystallographic inversion centres and adopt the anti-conformation. The bond distances and angles are normal (Allen et al., 1987). One set of the 2-hydroxyethyl groups is disordered with site occupancy factors of ca 0.811 (2) and 0.189 (2). The dihedral angle between the amide plane (C4,O1,N1) and phenyl planes (C1—C3,C1A—C3A) is 67.0 (2)°. The structural study shows the presence of four different intermolecular O—H···O hydrogen bonds (Table 1), resulting in a three-dimensional supramolecular architecture (Fig. 2).

Experimental

To a solution of diethanolamine (2 mmol) in dry chloroform (5 ml), at 273 K, was added dropwise a solution of terephthalyl chloride (2 mmol) in dry chloroform (25 ml). Then, the mixture stirred at room temperature for 24hr, removal of solvent resulted in a yellow powder that was recrystallized from methanol-DMF solution at room temperature to give the desired product as colourless crystals suitable for single-crystal X-ray diffraction.