K. Ha
Dec 1, 2010
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C33H42N4O6, monoclinic, P21/n (no. 14), a = 15.575(1) Å, b = 11.9097(9) Å, c = 17.449(1) Å, * = 94.692(2)°, V = 3225.7 Å, Z = 4, Rgt(F) = 0.055, wRref(F) = 0.155, T = 200 K. Source of material Tris(2-aminoethyl)amine (0.7395 g, 5.057 mmol) and 3-ethoxysalicylaldehyde (2.5291 g, 15.220 mmol) in EtOH (30 ml) were stirred for 3 h at room temparature. After removal of the undissolved by filtration, the solvent of the filtrate was evaporated and the residue was recrystallized from a mixture of acetone/pentane at –85 °C, to give a yellow solid (2.6697 g). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from an ether solution. Experimental details All hydrogen atoms were localized from difference Fourier maps and refined with isotropic displacement parameters. Discussion The title compound is a polydentate tripodal Schiff base, which can act as a tribasic hexaor heptadentate ligand, that is, the N3O3 or N4O3 donor atoms can coordinate to a metal ion or metal ions. The molecule except the ethoxy groups reveals an approximate three-fold axis, when viewed down the apical amine N atom (N4) through the plane formed by the atoms C9, C20 and C31. In the crystal structure, two ethoxy groups are located approximately parallel to their respective carrier benzene rings, whereas the other one is not. The N—C bond lengths and the C–N–C bond angles indicate that the apical N4 atom is sp-hybridized (d(N4—C) = 1.464(3) 1.467(3) Å; ∠C–N4–C = 110.9(2)° 111.7(2)°) and the other imine N atoms (N1, N2, N3) are sp-hybridized (d(N=C) = 1.274(3) 1.279(3) Å and d(N—C) = 1.455(3) 1.468(3) Å; ∠C–N–C = 119.0(2)° 119.8(2)°). The compound displays strong intramolecular O–H···N hydrogen bonds between the hydroxy O atoms and the imine N atoms with d(O···N) = 2.572(2) 2.594(2) Å thus forming a nearly planar six-membered ring. There are also weak intermolecular C–H···O hydrogen bonds with d(C···O) = 3.244(3) 3.524(3) Å. Moreover, several intraand inter-molecular --interactions between the adjacent benzene rings are present. For Cg1 (the centroid of ring C12-C17) and Cg2 (ring C23-C28), the centroid-centroid distance is 4.646(1) Å and the dihedral angle between the ring planes is 52.1(1)°. Z. Kristallogr. NCS 225 (2010) 697-698 / DOI 10.1524/ncrs.2010.0306 697 © by Oldenbourg Wissenschaftsverlag, München Crystal: yellow block, size 0.16 × 0.24 × 0.34 mm Wavelength: Mo K+ radiation (0.71073 Å) .: 0.84 cm−1 Diffractometer, scan mode: Bruker SMART 1000 CCD, #/% 2,max: 56.56° N(hkl)measured, N(hkl)unique: 23550, 7991 Criterion for Iobs, N(hkl)gt: Iobs > 2 )(Iobs), 3873 N(param)refined: 557 Programs: SHELXS-97, SHELXL-97 [1], ORTEP-III [2], PLATON [3] Table 1. Data collection and handling. H(1O) 4e 0.449(2) −0.032(2) 0.080(2) 0.076(8) H(3O) 4e 0.658(2) 0.284(3) 0.282(2) 0.11(1) H(5O) 4e 0.411(2) −0.032(3) 0.419(2) 0.10(1) H(4) 4e 0.184(2) 0.226(2) 0.039(1) 0.049(7) H(5) 4e 0.273(2) 0.365(2) 0.108(1) 0.063(7) H(6) 4e 0.415(1) 0.319(2) 0.149(1) 0.051(7) H(7) 4e 0.536(1) 0.190(2) 0.166(1) 0.045(6) H(8A) 4e 0.653(2) −0.002(2) 0.100(2) 0.066(8) H(8B) 4e 0.652(1) 0.084(2) 0.171(1) 0.052(7) H(9A) 4e 0.590(1) −0.143(2) 0.183(1) 0.049(6) H(9B) 4e 0.695(2) −0.119(2) 0.206(1) 0.068(7) H(10A) 4e 0.147(2) 0.105(2) −0.055(2) 0.074(9) H(10B) 4e 0.107(2) 0.067(2) 0.022(2) 0.074(9) H(11A) 4e 0.151(2) −0.085(2) −0.105(2) 0.10(1) H(11B) 4e 0.051(2) −0.047(2) −0.084(2) 0.066(8) H(11C) 4e 0.106(2) −0.124(2) −0.029(2) 0.067(9) H(15) 4e 0.192(2) 0.296(2) 0.403(1) 0.055(7) H(16) 4e 0.195(1) 0.266(2) 0.265(1) 0.045(6) Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso