10-(2-Pyrid­yloxy)phenanthren-9-ol

C A M A Huq; S Sivakumar; M NizamMohideen

doi:10.1107/S1600536810033489

. 2010 Aug 28;66(Pt 9):o2462. doi: 10.1107/S1600536810033489

10-(2-Pyridyloxy)phenanthren-9-ol

C A M A Huq ^a, S Sivakumar ^a, M NizamMohideen ^b,^*

PMCID: PMC3008099 PMID: 21588781

Abstract

In the title compound, C₁₉H₁₃NO₂, the pyridyl ring makes a dihedral angle of 87.04 (6)° with the plane of the phenanthrene ring system. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of heterocyclic compounds containing a pyridine ring, see: Amr & Abdulla (2006 ▶); Borgna et al. (1993 ▶); Goda et al. (2004 ▶); Kamal et al. (2007 ▶). For related structures, see: Krivopalov & Shkurko (2005 ▶); Li & Flood (2008 ▶); Meudtner & Hecht (2008 ▶); Richardson et al. (2008 ▶); Schweinfurth et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₃NO₂
M _r = 287.30
Monoclinic,
a = 8.9379 (6) Å
b = 8.6433 (10) Å
c = 18.389 (3) Å
β = 96.088 (8)°
V = 1412.6 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 293 K
0.3 × 0.25 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
2530 measured reflections
2384 independent reflections
1828 reflections with I > 2σ(I)
R _int = 0.036
2 standard reflections every 200 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.158
S = 1.07
2384 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033489/lx2166sup1.cif

e-66-o2462-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033489/lx2166Isup2.hkl

e-66-o2462-Isup2.hkl^{(114.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the N1/C1–C5 and C6/C7/C12/C13/C18/C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.59	3.475 (3)	159
C10—H10⋯Cg1ⁱⁱ	0.93	2.86	3.691 (3)	150
C15—H15⋯Cg2ⁱⁱⁱ	0.93	2.80	3.537 (3)	137

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

Acknowledgments

The authors thank the Management of The New College (Autonomous), Chennai, India, for providing the necessary facilities.

supplementary crystallographic information

Comment

Heterocyclic compounds containing the pyridine ring are reported to possess a diverse range of biological activities such as antimicrobial, antitumor and anti–inflammatory (Amr & Abdulla, 2006; Borgna et al., 1993; Goda et al., 2004; Kamal et al., 2007) properties. Pyridyl functionalized 1,2,3–triazoles have begun attracting significant attention in a range of areas including anion recognition (Li & Flood, 2008), stimuli responsive foldamers (Meudtner & Hecht, 2008), drug discovery (Krivopalov & Shkurko, 2005) and coordination chemistry (Richardson et al., 2008; Schweinfurth et al., 2008). Against this background the structure of the title compound was determined by X–ray diffraction. Here we report the crystal structure of the title compound (Fig. 1).

The phenanthrene plane is essentially planar, with a mean deviation of 0.011 (2) |%A from the least-squares plane defined by the fourteen constituent atoms. The dihedral angle formed by the phenanthrene plane and the pyridyl ring is 87.04 (6)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the pyidyl H atom and the oxygen of the hydroxyl group, with a C3—H3···O2ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by two intermolecular C—H···π interactions; the first one between the benzene H atom of the phenanthrene unit and the pyridyl ring, with a C10—H10···Cg1, the second one between the benzene H atom of the phenanthrene unit and the central benzene ring of a neighbouring molecule, with a C15—H15···Cg2 (Table 1; Cg1 and Cg2 are the centroids of the N1/C1—C5 pyridyl ring and the C6/C7/C12/C13/C18/C19 benzene ring, respectively).

Experimental

To a solution of 2–pyridyl magnesium bromide in dry THF at 273° under nitrogen atomsphere, solution of phenanthren-9,10-dione in dry THF was added dropwise. After the addition, the mixture was stirred at room temp under nitrogen atmosphere for 3 h. After the completion of reaction as evidenced by TLC, the reaction was quenched with saturated solution of ammonium chloride and the mixture was extracted into diethyl ether. The organic layer was concentrated at reduced pressure. The residue was purified by coloumn chromotography (hexane-ethyl acetate, 9:1 v/v) to afford the title compound as a pale yellow solid (yield 75%, m.p. 418° K). Single crystals suitable for X–ray diffraction was recrystallized from mixture of dichlromehane-hexane (8: 2 v/v) as solvent.