5H-Imidazo[4,5-f][1,10]phenanthroline

Shao-Wei Tong; Wen-Dong Song; Dong-Liang Miao; Jing-Bo An

doi:10.1107/S1600536812016595

. 2012 Apr 21;68(Pt 5):o1448. doi: 10.1107/S1600536812016595

5H-Imidazo[4,5-f][1,10]phenanthroline

Shao-Wei Tong ^a, Wen-Dong Song ^b,^*, Dong-Liang Miao ^a, Jing-Bo An ^a

PMCID: PMC3344565 PMID: 22590327

Abstract

The title molecule, C₁₃H₈N₄, is is essentially planar [r.m.s. deviation for all non-H atoms = 0.025 (3) Å]. In the crystal, molecules are connected through one weak bifurcated N—H⋯(N,N) hydrogen bond and three π–π stacking interactions between pyridine and imidazole rings [centroid–centroid distance = 3.631 (8) Å] and between pyridine and benzene rings [centroid–centroid distances = 3.675 (5) and 3.666 (2) Å].

Related literature

For our previous work based on 1,10-phenanthroline as anauxiliary ligand, see: Song et al. (2009 ▶); Hao et al. (2008 ▶). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999 ▶).

Experimental

Crystal data

C₁₃H₈N₄
M _r = 220.23
Orthorhombic,
a = 14.569 (2) Å
b = 7.8623 (12) Å
c = 17.042 (3) Å
V = 1952.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.980, T _max = 0.985
5772 measured reflections
1756 independent reflections
1025 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.123
S = 1.00
1756 reflections
186 parameters
All H-atom parameters refined
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812016595/bx2404sup1.cif

e-68-o1448-sup1.cif^{(14.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016595/bx2404Isup2.hkl

e-68-o1448-Isup2.hkl^{(86.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016595/bx2404Isup3.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
N3—H8⋯N1ⁱ	0.92 (3)	2.47 (3)	3.104 (3)	126 (2)
N3—H8⋯N2ⁱ	0.92 (3)	2.18 (3)	3.017 (3)	150 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge the Public Science and Technology Research Funds Projects of Ocean (grant No. 2000905021), the Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121) and the Guangdong Province Key Project in the Field of Social Development [grant No. A2009011–007(c)].

supplementary crystallographic information

Comment

(1,10)phenanthroline is widely used to synthetize metal-complex as a auxiliary ligand. In our laboratory earlier studies, we have successfully obtained some metal-complex with (1,10)phenanthroline.We report here the crystal structure of the title compound, Fig. 1. The title compound, is essentially planar (r.m.s. deviation for all non-H atoms = 0.025 (3)Å). In the crystal the molecules are connected through one weak bifurcated N—H···N hydrogen bonds, Fig. 2, Table 1 and π-π stacking interactions between pyridine and imidazole rings [distance centroid – centroid 3.631 (8) Å] and between pyridine and benzene rings [distance centroid–centroid 3.675 (5); 3.666 (2) Å] respectively.

Experimental

Imidazo(4,5-f)(1,10)phenanthroline was purchased from Jinan Henghua science and technology limited company and recristallized of an alkaline solution.