10-(2-Pyrid-yloxy)phenanthren-9-ol.

In the title compound, C(19)H(13)NO(2), the pyridyl ring makes a dihedral angle of 87.04 (6)° with the plane of the phenanthrene ring system. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

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 = 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

Δρmax = 0.34 e Å−3

Δρmin = −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.

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

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

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

C19H13NO2	F(000) = 600
Mr = 287.30	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.9379 (6) Å	θ = 20–32°
b = 8.6433 (10) Å	µ = 0.71 mm−1
c = 18.389 (3) Å	T = 293 K
β = 96.088 (8)°	Block, yellow
V = 1412.6 (3) Å3	0.3 × 0.25 × 0.2 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.036
Radiation source: fine-focus sealed tube	θmax = 64.9°, θmin = 4.8°
graphite	h = 0→10
ω–2θ scan	k = 0→10
2530 measured reflections	l = −21→21
2384 independent reflections	2 standard reflections every 100 reflections
1828 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0879P)2 + 0.3509P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2384 reflections	Δρmax = 0.34 e Å−3
200 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0161 (14)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.28079 (19)	0.0991 (2)	0.50744 (9)	0.0552 (5)
O1	0.48937 (16)	0.09045 (15)	0.58522 (7)	0.0539 (4)
O2	0.75971 (19)	0.19460 (18)	0.54090 (8)	0.0639 (5)
H2	0.6870	0.1572	0.5161	0.096*
C1	0.1729 (3)	0.1774 (3)	0.46753 (13)	0.0687 (7)
H1	0.0995	0.1213	0.4392	0.082*
C2	0.1638 (3)	0.3354 (3)	0.46580 (14)	0.0734 (7)
H2A	0.0876	0.3854	0.4364	0.088*
C3	0.2706 (3)	0.4179 (3)	0.50877 (13)	0.0675 (7)
H3	0.2666	0.5254	0.5094	0.081*
C4	0.3832 (3)	0.3413 (3)	0.55083 (12)	0.0566 (6)
H4	0.4566	0.3949	0.5803	0.068*
C5	0.3832 (2)	0.1817 (2)	0.54766 (10)	0.0470 (5)
C6	0.5977 (2)	0.1611 (2)	0.63482 (10)	0.0474 (5)
C7	0.5655 (2)	0.1757 (2)	0.70924 (11)	0.0480 (5)
C8	0.4266 (3)	0.1302 (3)	0.73138 (13)	0.0596 (6)
H8	0.3536	0.0884	0.6972	0.072*
C9	0.3968 (3)	0.1465 (3)	0.80255 (14)	0.0690 (7)
H9	0.3042	0.1163	0.8166	0.083*
C10	0.5066 (3)	0.2086 (3)	0.85376 (14)	0.0711 (7)
H10	0.4870	0.2197	0.9021	0.085*
C11	0.6431 (3)	0.2533 (3)	0.83355 (12)	0.0619 (6)
H11	0.7152	0.2934	0.8687	0.074*
C12	0.6769 (2)	0.2399 (2)	0.76057 (11)	0.0493 (5)
C13	0.8179 (2)	0.2907 (2)	0.73679 (11)	0.0501 (5)
C14	0.9345 (3)	0.3569 (3)	0.78452 (13)	0.0637 (6)
H14	0.9197	0.3717	0.8333	0.076*
C15	1.0677 (3)	0.3998 (3)	0.76122 (15)	0.0724 (7)
H15	1.1428	0.4421	0.7942	0.087*
C16	1.0924 (3)	0.3807 (3)	0.68872 (15)	0.0711 (7)
H16	1.1837	0.4107	0.6731	0.085*
C17	0.9837 (3)	0.3184 (3)	0.64021 (13)	0.0610 (6)
H17	1.0013	0.3056	0.5916	0.073*
C18	0.8444 (2)	0.2729 (2)	0.66282 (11)	0.0499 (5)
C19	0.7291 (2)	0.2060 (2)	0.61153 (10)	0.0490 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0622 (11)	0.0553 (11)	0.0456 (10)	0.0030 (9)	−0.0056 (8)	−0.0065 (8)
O1	0.0661 (9)	0.0412 (8)	0.0506 (8)	0.0005 (6)	−0.0119 (7)	−0.0040 (6)
O2	0.0903 (11)	0.0595 (9)	0.0425 (8)	−0.0129 (8)	0.0099 (7)	−0.0048 (7)
C1	0.0683 (14)	0.0799 (17)	0.0541 (13)	0.0067 (13)	−0.0111 (11)	−0.0061 (12)
C2	0.0766 (16)	0.0800 (18)	0.0613 (15)	0.0221 (14)	−0.0028 (12)	0.0118 (13)
C3	0.0822 (16)	0.0522 (14)	0.0689 (15)	0.0120 (12)	0.0120 (13)	0.0076 (11)
C4	0.0687 (14)	0.0476 (12)	0.0531 (12)	0.0002 (10)	0.0046 (10)	−0.0013 (10)
C5	0.0572 (12)	0.0475 (11)	0.0356 (10)	0.0030 (9)	0.0022 (8)	−0.0007 (8)
C6	0.0610 (12)	0.0360 (10)	0.0427 (10)	−0.0001 (9)	−0.0062 (9)	−0.0026 (8)
C7	0.0594 (12)	0.0371 (10)	0.0463 (11)	0.0049 (9)	0.0004 (9)	0.0001 (8)
C8	0.0681 (14)	0.0507 (12)	0.0596 (13)	−0.0014 (11)	0.0040 (11)	−0.0012 (10)
C9	0.0797 (16)	0.0602 (15)	0.0705 (16)	−0.0034 (12)	0.0234 (13)	0.0006 (12)
C10	0.1028 (19)	0.0614 (15)	0.0528 (13)	−0.0004 (14)	0.0252 (13)	−0.0022 (11)
C11	0.0860 (17)	0.0543 (13)	0.0444 (12)	−0.0012 (12)	0.0023 (11)	−0.0055 (10)
C12	0.0646 (13)	0.0387 (10)	0.0431 (11)	0.0052 (9)	−0.0009 (9)	−0.0002 (8)
C13	0.0608 (13)	0.0403 (10)	0.0471 (11)	0.0044 (9)	−0.0051 (9)	−0.0016 (9)
C14	0.0711 (15)	0.0630 (14)	0.0534 (13)	−0.0028 (12)	−0.0099 (11)	−0.0073 (11)
C15	0.0687 (15)	0.0661 (16)	0.0781 (17)	−0.0094 (13)	−0.0118 (13)	−0.0095 (13)
C16	0.0618 (14)	0.0638 (15)	0.0872 (18)	−0.0101 (12)	0.0058 (12)	−0.0036 (14)
C17	0.0701 (14)	0.0528 (13)	0.0607 (13)	−0.0049 (11)	0.0100 (11)	−0.0015 (11)
C18	0.0617 (13)	0.0386 (10)	0.0483 (11)	0.0018 (9)	0.0008 (9)	−0.0011 (8)
C19	0.0679 (13)	0.0386 (11)	0.0401 (11)	0.0022 (9)	0.0028 (9)	−0.0016 (8)

N1—C5	1.323 (3)	C8—H8	0.9300
N1—C1	1.333 (3)	C9—C10	1.394 (4)
O1—C5	1.364 (2)	C9—H9	0.9300
O1—C6	1.398 (2)	C10—C11	1.368 (4)
O2—C19	1.359 (2)	C10—H10	0.9300
O2—H2	0.8200	C11—C12	1.411 (3)
C1—C2	1.368 (4)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.445 (3)
C2—C3	1.372 (4)	C13—C14	1.411 (3)
C2—H2A	0.9300	C13—C18	1.413 (3)
C3—C4	1.373 (3)	C14—C15	1.359 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.381 (3)	C15—C16	1.384 (4)
C4—H4	0.9300	C15—H15	0.9300
C6—C19	1.350 (3)	C16—C17	1.359 (3)
C6—C7	1.434 (3)	C16—H16	0.9300
C7—C8	1.403 (3)	C17—C18	1.410 (3)
C7—C12	1.411 (3)	C17—H17	0.9300
C8—C9	1.370 (3)	C18—C19	1.441 (3)
C5—N1—C1	116.8 (2)	C11—C10—C9	120.6 (2)
C5—O1—C6	118.32 (15)	C11—C10—H10	119.7
C19—O2—H2	109.5	C9—C10—H10	119.7
N1—C1—C2	123.9 (2)	C10—C11—C12	121.5 (2)
N1—C1—H1	118.1	C10—C11—H11	119.3
C2—C1—H1	118.1	C12—C11—H11	119.3
C1—C2—C3	118.0 (2)	C7—C12—C11	117.5 (2)
C1—C2—H2A	121.0	C7—C12—C13	119.54 (19)
C3—C2—H2A	121.0	C11—C12—C13	122.99 (19)
C2—C3—C4	119.8 (2)	C14—C13—C18	117.1 (2)
C2—C3—H3	120.1	C14—C13—C12	123.0 (2)
C4—C3—H3	120.1	C18—C13—C12	119.90 (19)
C3—C4—C5	117.5 (2)	C15—C14—C13	121.9 (2)
C3—C4—H4	121.2	C15—C14—H14	119.0
C5—C4—H4	121.2	C13—C14—H14	119.0
N1—C5—O1	111.97 (18)	C14—C15—C16	120.4 (2)
N1—C5—C4	123.98 (19)	C14—C15—H15	119.8
O1—C5—C4	124.04 (18)	C16—C15—H15	119.8
C19—C6—O1	118.98 (18)	C17—C16—C15	120.2 (2)
C19—C6—C7	123.17 (19)	C17—C16—H16	119.9
O1—C6—C7	117.78 (18)	C15—C16—H16	119.9
C8—C7—C12	119.97 (19)	C16—C17—C18	120.6 (2)
C8—C7—C6	121.70 (19)	C16—C17—H17	119.7
C12—C7—C6	118.32 (19)	C18—C17—H17	119.7
C9—C8—C7	121.1 (2)	C17—C18—C13	119.8 (2)
C9—C8—H8	119.5	C17—C18—C19	120.7 (2)
C7—C8—H8	119.5	C13—C18—C19	119.50 (19)
C8—C9—C10	119.4 (2)	C6—C19—O2	123.53 (19)
C8—C9—H9	120.3	C6—C19—C18	119.55 (18)
C10—C9—H9	120.3	O2—C19—C18	116.91 (18)
C5—N1—C1—C2	0.4 (3)	C10—C11—C12—C7	−1.2 (3)
N1—C1—C2—C3	−1.2 (4)	C10—C11—C12—C13	177.9 (2)
C1—C2—C3—C4	1.0 (4)	C7—C12—C13—C14	179.54 (19)
C2—C3—C4—C5	0.0 (3)	C11—C12—C13—C14	0.5 (3)
C1—N1—C5—O1	−178.97 (18)	C7—C12—C13—C18	−1.3 (3)
C1—N1—C5—C4	0.6 (3)	C11—C12—C13—C18	179.68 (19)
C6—O1—C5—N1	−174.68 (17)	C18—C13—C14—C15	−1.1 (3)
C6—O1—C5—C4	5.7 (3)	C12—C13—C14—C15	178.1 (2)
C3—C4—C5—N1	−0.9 (3)	C13—C14—C15—C16	0.7 (4)
C3—C4—C5—O1	178.70 (18)	C14—C15—C16—C17	−0.3 (4)
C5—O1—C6—C19	−91.9 (2)	C15—C16—C17—C18	0.3 (4)
C5—O1—C6—C7	90.9 (2)	C16—C17—C18—C13	−0.7 (3)
C19—C6—C7—C8	178.89 (19)	C16—C17—C18—C19	−179.7 (2)
O1—C6—C7—C8	−4.0 (3)	C14—C13—C18—C17	1.1 (3)
C19—C6—C7—C12	−0.2 (3)	C12—C13—C18—C17	−178.16 (19)
O1—C6—C7—C12	176.95 (16)	C14—C13—C18—C19	−179.92 (19)
C12—C7—C8—C9	−0.2 (3)	C12—C13—C18—C19	0.8 (3)
C6—C7—C8—C9	−179.3 (2)	O1—C6—C19—O2	3.9 (3)
C7—C8—C9—C10	−0.3 (4)	C7—C6—C19—O2	−179.02 (18)
C8—C9—C10—C11	0.0 (4)	O1—C6—C19—C18	−177.34 (17)
C9—C10—C11—C12	0.7 (4)	C7—C6—C19—C18	−0.2 (3)
C8—C7—C12—C11	0.9 (3)	C17—C18—C19—C6	178.89 (19)
C6—C7—C12—C11	−179.97 (18)	C13—C18—C19—C6	−0.1 (3)
C8—C7—C12—C13	−178.16 (18)	C17—C18—C19—O2	−2.2 (3)
C6—C7—C12—C13	0.9 (3)	C13—C18—C19—O2	178.76 (17)

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

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

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