2,2′-(1,10-Phenanthrolin-2-ylimino)di­ethanol

Xia Jin; Jin Min Li

doi:10.1107/S1600536809004929

. 2009 Feb 18;65(Pt 3):o541. doi: 10.1107/S1600536809004929

2,2′-(1,10-Phenanthrolin-2-ylimino)diethanol

Xia Jin ^a, Jin Min Li ^a,^*

PMCID: PMC2968642 PMID: 21582200

Abstract

In the title compound, C₁₆H₁₇N₃O₂, symmetry-related molecules are linked into one-dimensional chains along the a axis by a combination of intermolecular O—H⋯N and O—H⋯O hydrogen bonds and weak π–π stacking interactions with a centroid–centroid distance of 3.5494 (12) Å.

Related literature

For recent crystal structure reports on the complexes formed with derivatives of 1,10-phenanthroline, see for example: Li et al. (2008 ▶) and Zhang et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O₂
M _r = 283.33
Monoclinic,
a = 4.8480 (10) Å
b = 14.854 (3) Å
c = 18.858 (4) Å
β = 93.523 (3)°
V = 1355.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.54 × 0.32 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.951, T _max = 0.982
7520 measured reflections
2765 independent reflections
2149 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.132
S = 1.03
2765 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004929/lh2772sup1.cif

e-65-0o541-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004929/lh2772Isup2.hkl

e-65-0o541-Isup2.hkl^{(135.8KB, 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—H5⋯O1ⁱ	0.91	1.91	2.8254 (17)	177
O1—H4⋯N1ⁱⁱ	0.83	2.08	2.8676 (18)	158

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

supplementary crystallographic information

Comment

Derivatives of 1,10-phenanthroline play a vital role in a modern coordination chemistry and a number of complexes have been published with these types of compounds as ligands [see for example the recent publications by Li et al. (2008) and Zhang et al. (2008)]. An interest in designing new derivatives led to the synthesis the title compound, (I), and its crystal structure is reported herein.

The molecular structure of (I) is shown in Fig. 1. In the crystal structure, intermolecular O—H···N and O—H···O hydrogen bonds (see Table 1) connect symmetry related molecules to form 1-D chains along the a axis (see Fig. 2). In addition, within these chain there are weak π-π stacking interactions between symmetry related pyridyl rings, with the relevant distances being Cg1···Cg2ⁱⁱⁱ = 3.5494 (12) Å, Cg1···Cg2ⁱⁱⁱ_perp = 3.464 Å and α = 1.48° [symmetry code (iii) 1+x, y, z; Cg1 and Cg2 are the centroids of the C6C7C10-C12/N1 and C1—C5/N2 rings, respectively; Cg1···Cg2ⁱⁱⁱ_perp is the perpendicular distance from ring Cg1 to ring Cg2ⁱⁱⁱ; α is the dihedral angle between ring plane Cg1 and ring plane Cg2ⁱⁱⁱ].

Experimental

2-Diethanolamine-1,10-phenanthroline (0.0523 g, 0.185 mmol) was dissolved into 10 ml methanol and the yellow single crystals were obtained after the solution had been allowed to stand at room temperature for one week.