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

Dong-Ming Liu; Xiu-Ying Li; Xiang-Cheng Wang; Chun-Xiang Li; Chun-Bo Liu

doi:10.1107/S1600536809017498

. 2009 May 20;65(Pt 6):o1308. doi: 10.1107/S1600536809017498

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

Dong-Ming Liu ^a, Xiu-Ying Li ^b, Xiang-Cheng Wang ^b, Chun-Xiang Li ^b, Chun-Bo Liu ^b,^*

PMCID: PMC2969696 PMID: 21583165

Abstract

There are two molecules in the asymmetric unit of the title compound, C₁₉H₁₂N₄, with dihedral angles of 2.41 (10) and 10.53 (12)° between the fused ring system and the pendant phenyl ring. In the crystal, molecules are linked into chains by N—H⋯N hydrogen bonds and aromatic π–π stacking interactions [shortest centroid–centroid distance = 3.6176 (16) Å] complete the structure.

Related literature

For the synthesis, see: Steck & Day (1943 ▶); For related structures, see: Che et al. (2008 ▶); Stephenson & Hardie (2006 ▶); Xi (2008 ▶).

Experimental

Crystal data

C₁₉H₁₂N₄
M _r = 296.33
Triclinic,
a = 10.016 (2) Å
b = 12.210 (2) Å
c = 12.415 (3) Å
α = 89.90 (3)°
β = 78.44 (3)°
γ = 77.96 (3)°
V = 1453.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.975, T _max = 0.984
14453 measured reflections
6587 independent reflections
3657 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.156
S = 1.01
6587 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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/S1600536809017498/hb2971sup1.cif

e-65-o1308-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017498/hb2971Isup2.hkl

e-65-o1308-Isup2.hkl^{(315.8KB, 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
N3—H3⋯N5ⁱ	0.86	2.10	2.932 (3)	164
N7—H7⋯N1	0.86	2.12	2.951 (2)	163

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Postdoctoral Foundation of Jiangsu Province (No. 0801010B) for support.

supplementary crystallographic information

Comment

1,10-Phenanthroline (phen) or its derivatives, as an important chelating ligands with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Che, Liu et al., 2008; Stephenson, Hardie et al., 2006). We report here the synthesis and structure of the title compound, namely, C₁₉H₁₂N₄ (I), using the phen derivative 2-Phenyl-1H-1,3,7,8-tetraazacyclopenta- [l]phenanthrene (L).

The asymmetric unit of (I) consists of two independent L molecules (Fig.1). The two phenyl rings are slightly twisted with respect to the fused-ring system [dihedral angles = 1.34 and 1.54 °], which is different from a related compound that has been reported (Xi, 2008). In the crystal structure, N—H···N hydrogen bonds (Table 1) link the molecules into chains along the b axis. The neighbouring chains interact through π-π contact between two L ligands [centroid separation = 3.541 Å], leading to the ultimate supramolecular structure (Fig. 2).

Experimental

The L ligand was synthesized according to the literature method of Steck & Day (1943): a mixture of L, MnCl₂ and water in a molar ratio of 2:1:5000 was sealed in a Teflon-lined autoclave and heated to 413 K for 3 d. Upon cooling and opening the bomb, accidentally, pale yellow blocks of (I) were obtained.