1-(1H-Imidazo[4,5-f][1,10]phenan­throlin-2-yl)naphthalen-2-ol

Xiu-Yan Wang; Shuai Ma; Yu He

doi:10.1107/S1600536811005861

. 2011 Feb 26;67(Pt 3):o725. doi: 10.1107/S1600536811005861

1-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol

Xiu-Yan Wang ^a,^*, Shuai Ma ^a, Yu He ^a

PMCID: PMC3052124 PMID: 21522467

Abstract

In the title molecule, C₂₃H₁₄N₄O, the dihedral angle between the pyridine rings of the phenanthroline unit is 4.43 (8)° and the dihedral angle formed by the nine essentially planar [maximum deviation 0.0389 (16)Å] non-H atoms of the benzimidazole unit and the naphthalene ring system is 74.22 (5)°. In the crystal, molecules are linked by intermolecular N—H⋯N and O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the coordination chemistry of 1,10-phenanthroline derivatives, see: Wang et al. (2010 ▶). For the synthetic procedure, see: Steck & Day (1943 ▶).

Experimental

Crystal data

C₂₃H₁₄N₄O
M _r = 362.38
Tetragonal,
a = 22.5800 (4) Å
c = 13.7196 (5) Å
V = 6995.0 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.21 × 0.18 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.41, T _max = 0.72
18374 measured reflections
3433 independent reflections
3153 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.081
S = 1.06
3433 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ▶), 1629 Friedel pairs
Flack parameter: 0.0 (13)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005861/lh5209sup1.cif

e-67-0o725-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005861/lh5209Isup2.hkl

e-67-0o725-Isup2.hkl^{(165.2KB, 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
N4—H4⋯N2ⁱ	0.86	2.17	2.9361 (19)	149
N4—H4⋯N1ⁱ	0.86	2.50	3.191 (2)	138
O1—H1⋯N3ⁱⁱ	0.82	2.01	2.7203 (17)	145

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

Acknowledgments

The authors thank the Key Laboratory of Preparation and Applications of Environmentally Friendly Materials and the Institute Foundation of Siping City (No. 2009011) for supporting this work.

supplementary crystallographic information

Comment

1,10-Phenanthroline and its derivatives, are potentially important chelating ligands with excellent coordinating abilities and have been extensively used to build supramolecular architectures (Wang et al., 2010). We report herein the synthesis and crystal structure of the title compound

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the pyridine rings of the phenanthroline unit [N2/C4-C8 and N1/C1/C2/C3/C11/C23] is 4.43 (8)Å and the dihedral angle formed by the nine essentially planar non-hydrogen atoms of the benzimidazole unit [C3/C4/C8-C12; maximum deviation 0.0389 (16)Å for C4] and the naphthalene ring system is 74.22 (5)°. In the crystal, molecules are linked by intermolecular N—H···N and O—H···N hydrogen bonds to form a three-dimensional network.

Experimental

The title compound was synthesized according to the literature method of Steck & Day (1943). We carried out the following reaction but the unreacted title compound was found in the reaction vessel. A mixture of Bi(NO₃)₃^.5H₂O (0.5 mmol) and L (0.5 mmol) in 10 mL distilled water was heated at 463 K in a Teflon-lined stainless steel autoclave for three days. The reaction system was then slowly cooled to room temperature. Pale yellow crystals suitable for single crystal X-ray diffraction analysis were collected from the final reaction system.