2-Phenyl-1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthrene

Hong-Min Xi

doi:10.1107/S1600536808029759

. 2008 Sep 20;64(Pt 10):o1981. doi: 10.1107/S1600536808029759

2-Phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene

Hong-Min Xi ^a,^*

PMCID: PMC2959488 PMID: 21201181

Abstract

There are two molecules in the asymmetric unit of the title compound, C₁₉H₁₂N₄. One is almost planar [dihedral angle between the fused-ring system and the phenyl ring = 2.16 (13)°] and one is somewhat twisted [dihedral angle = 13.30 (14)°]. In the crystal, the molecules are linked by N—H⋯N hydrogen bonds to result in chains.

Related literature

For related literature, see Zhang et al. (2008 ▶); Yin (2008 ▶).

Experimental

Crystal data

C₁₉H₁₂N₄
M _r = 296.33
Monoclinic,
a = 12.3326 (15) Å
b = 12.2334 (15) Å
c = 19.885 (2) Å
β = 104.010 (2)°
V = 2910.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.24 × 0.21 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.981, T _max = 0.982
23942 measured reflections
5721 independent reflections
2627 reflections with I > 2σ(I)
R _int = 0.089

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.167
S = 0.97
5721 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536808029759/bt2790sup1.cif

e-64-o1981-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029759/bt2790Isup2.hkl

e-64-o1981-Isup2.hkl^{(274.4KB, 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
N3—H3A⋯N6ⁱ	0.86	2.09	2.932 (4)	165
N8—H8A⋯N2ⁱ	0.86	2.12	2.948 (3)	163

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks Beihua University for supporting this work.

supplementary crystallographic information

Comment

1,10-Phenanthroline and its derivatives are widely utilized as ligands in metal complexes (Zhang et al., 2008). I report here the crystal structure of the title compound, which was synthesized from 1,10-phenanthroline-5,6-dione. In this compound, all the bond lengths are within normal ranges (Yin, 2008). The asymmetric unit consists of two independent molecules (Fig. 1), which are connected by N—H···N hydrogen bonds to form a one-dimensional chain (Table 1).

Experimental

1,10-Phenanthroline-5,6-dione (1.5 mmol) and benzaldehyde (1.5 mmol) were dissolved in CH₃COOHCH₃COONH₄ (1:1) solution (30 ml). The mixture was refluxed for 3 h under argon, after cooling, this mixture was diluted with water and neutralized with concentrated aqueous ammonia, immediately resulting a yellow precipitate, which was washed with water, acetone and diethyl ether respectively. Crystals of the title compound were obtained by recrystallization from dichloromethane.