2-(4-Pyridylmeth­oxy)phenol

Abstract

In the crystal structure of the title compound, C₁₂H₁₁NO₂, inversion-related mol­ecules are linked into dimers by pairs of O—H⋯N hydrogen bonds between the hydr­oxy group and the pyridyl ring. In addition, a π–π inter­action [with a centroid–centroid distance of 3.78 (1) Å] is found between the two pyridyl rings of the dimer. The benzene ring forms a dihedral angle of 71.6 (1)° with the pyridine ring

Related literature

For details of the synthesis, see Gao et al. (2004 ▶).

Experimental

Crystal data

• C₁₂H₁₁NO₂

• M _r = 201.22

• Orthorhombic,

• a = 11.800 (3) Å

• b = 9.114 (4) Å

• c = 19.041 (7) Å

• V = 2047.7 (13) ų

• Z = 8

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 291 K

• 0.37 × 0.35 × 0.20 mm

Data collection

• Rigaku R-AXIS RAPID diffractometer

• Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.968, T _max = 0.983

• 14969 measured reflections

• 1802 independent reflections

• 1139 reflections with I > 2σ(I)

• R _int = 0.083

Refinement

• R[F ² > 2σ(F ²)] = 0.059

• wR(F ²) = 0.145

• S = 1.03

• 1802 reflections

• 137 parameters

• H-atom parameters constrained

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.13 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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

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
O2—H2A⋯N1i	0.82	1.95	2.714 (3)	155

Symmetry code: (i) .

supplementary crystallographic information

Comment

In the title compound, the 2-(pyridin-4-ylmethoxy)phenol ligand, all bonds and angles are in normal region. The benzene ring forms a dihedral angle of 71.6 (1)° with the pyridine rings (Figure 1).

In the crystal structure, the intramolecular O—H···O hydrogen bonds are found between adjacent hydroxys and O atoms. After then, the intermolecular O—H···N hydrogen bonds and π—π interactions (3.78 (1)° A) link molecules into dimer (Figure 2, Table 1).

Experimental

The 2-(Pyridin-4-ylmethoxy)phenol was synthesized by the reaction of o-benzenediol and 4-chloromethylpyridine hydrochloride under nitrogen atmosphere and alkaline condition (Gao et al., 2004). Colourless block crystals of title compound were obtained by slow evaporation of an methanol solution after several days.

Refinement

H atoms bound to C atoms and the H atoms of the hydroxy groups were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene), O—H = 0.82 Å and with U_iso(H) = 1.2U_eq(C), U_iso(H) = 1.5U_eq(O).

Figures

Fig. 1.

The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.

Fig. 2.

A dimer view, forming by hydrogen bonds and π—π interactions. Green dashed lines indicate the hydrogen bonds, blue dashed lines indicate the π—π interactions.

Crystal data

C12H11NO2	F(000) = 848
Mr = 201.22	Dx = 1.305 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9420 reflections
a = 11.800 (3) Å	θ = 3.0–27.4°
b = 9.114 (4) Å	µ = 0.09 mm−1
c = 19.041 (7) Å	T = 291 K
V = 2047.7 (13) Å3	Block, colorless
Z = 8	0.37 × 0.35 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1802 independent reflections
Radiation source: fine-focus sealed tube	1139 reflections with I > 2σ(I)
graphite	Rint = 0.083
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→12
Tmin = 0.968, Tmax = 0.983	k = −10→10
14969 measured reflections	l = −22→22

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.2741P] where P = (Fo2 + 2Fc2)/3
1802 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0611 (2)	−0.0878 (3)	0.41781 (16)	0.0667 (8)
H1	0.0138	−0.0732	0.3794	0.080*
C2	0.0381 (2)	−0.1961 (3)	0.46523 (17)	0.0704 (8)
H2	−0.0256	−0.2541	0.4577	0.085*
C3	0.1917 (2)	−0.1394 (3)	0.53017 (15)	0.0682 (8)
H3	0.2377	−0.1565	0.5690	0.082*
C4	0.2214 (2)	−0.0278 (3)	0.48491 (15)	0.0640 (7)
H4	0.2859	0.0280	0.4934	0.077*
C5	0.1553 (2)	0.0002 (3)	0.42746 (14)	0.0555 (7)
C6	0.1845 (2)	0.1187 (3)	0.37560 (15)	0.0683 (8)
H6A	0.2593	0.1576	0.3856	0.082*
H6B	0.1849	0.0789	0.3284	0.082*
C7	0.1055 (2)	0.3409 (3)	0.33056 (13)	0.0520 (7)
C8	0.1831 (2)	0.3476 (3)	0.27619 (14)	0.0617 (7)
H8	0.2389	0.2761	0.2721	0.074*
C9	0.1775 (2)	0.4614 (3)	0.22763 (14)	0.0666 (8)
H9	0.2288	0.4653	0.1906	0.080*
C10	0.0966 (2)	0.5674 (3)	0.23453 (15)	0.0683 (8)
H10	0.0934	0.6441	0.2024	0.082*
C11	0.0199 (2)	0.5614 (3)	0.28856 (15)	0.0674 (8)
H11	−0.0347	0.6345	0.2927	0.081*
C12	0.0226 (2)	0.4485 (3)	0.33687 (14)	0.0573 (7)
N1	0.1011 (2)	−0.2237 (2)	0.52130 (12)	0.0647 (6)
O1	0.10215 (15)	0.23246 (18)	0.38082 (9)	0.0601 (5)
O2	−0.05674 (18)	0.4472 (2)	0.38861 (11)	0.0786 (7)
H2A	−0.0530	0.3694	0.4101	0.118*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0637 (17)	0.0617 (18)	0.0747 (18)	0.0019 (15)	−0.0105 (14)	0.0120 (16)
C2	0.0573 (18)	0.0585 (19)	0.095 (2)	−0.0047 (14)	−0.0003 (17)	0.0094 (17)
C3	0.075 (2)	0.0643 (19)	0.0654 (18)	0.0133 (17)	−0.0043 (15)	0.0045 (15)
C4	0.0631 (17)	0.0499 (16)	0.0790 (19)	−0.0027 (14)	−0.0037 (16)	−0.0003 (15)
C5	0.0557 (15)	0.0437 (15)	0.0670 (17)	0.0100 (13)	0.0081 (14)	0.0017 (13)
C6	0.0689 (18)	0.0535 (17)	0.083 (2)	0.0132 (15)	0.0134 (15)	0.0154 (15)
C7	0.0568 (15)	0.0428 (14)	0.0564 (15)	−0.0058 (13)	−0.0043 (13)	0.0051 (12)
C8	0.0640 (17)	0.0532 (16)	0.0679 (17)	−0.0038 (13)	−0.0007 (14)	0.0006 (14)
C9	0.0764 (19)	0.0660 (18)	0.0573 (16)	−0.0129 (16)	−0.0033 (14)	0.0084 (15)
C10	0.0752 (19)	0.0616 (18)	0.0681 (19)	−0.0076 (16)	−0.0171 (16)	0.0177 (15)
C11	0.0686 (18)	0.0556 (17)	0.078 (2)	0.0034 (14)	−0.0133 (16)	0.0130 (15)
C12	0.0576 (16)	0.0490 (16)	0.0652 (17)	0.0019 (14)	−0.0038 (14)	0.0020 (13)
N1	0.0634 (14)	0.0528 (14)	0.0778 (16)	0.0094 (12)	0.0135 (13)	0.0104 (12)
O1	0.0650 (12)	0.0450 (10)	0.0703 (12)	0.0096 (9)	0.0098 (9)	0.0095 (9)
O2	0.0792 (14)	0.0630 (14)	0.0936 (15)	0.0222 (11)	0.0211 (12)	0.0206 (11)

Geometric parameters (Å, °)

C1—C2	1.365 (4)	C7—O1	1.376 (3)
C1—C5	1.384 (4)	C7—C8	1.383 (3)
C1—H1	0.9300	C7—C12	1.390 (3)
C2—N1	1.325 (3)	C8—C9	1.391 (4)
C2—H2	0.9300	C8—H8	0.9300
C3—N1	1.327 (3)	C9—C10	1.365 (4)
C3—C4	1.378 (4)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.371 (4)
C4—C5	1.367 (4)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.381 (4)
C5—C6	1.503 (4)	C11—H11	0.9300
C6—O1	1.424 (3)	C12—O2	1.359 (3)
C6—H6A	0.9700	O2—H2A	0.8200
C6—H6B	0.9700
C2—C1—C5	119.4 (3)	O1—C7—C8	124.8 (2)
C2—C1—H1	120.3	O1—C7—C12	115.2 (2)
C5—C1—H1	120.3	C8—C7—C12	119.9 (2)
N1—C2—C1	124.0 (3)	C7—C8—C9	120.0 (3)
N1—C2—H2	118.0	C7—C8—H8	120.0
C1—C2—H2	118.0	C9—C8—H8	120.0
N1—C3—C4	123.5 (3)	C10—C9—C8	119.8 (3)
N1—C3—H3	118.3	C10—C9—H9	120.1
C4—C3—H3	118.3	C8—C9—H9	120.1
C5—C4—C3	119.6 (3)	C9—C10—C11	120.4 (3)
C5—C4—H4	120.2	C9—C10—H10	119.8
C3—C4—H4	120.2	C11—C10—H10	119.8
C4—C5—C1	117.1 (3)	C10—C11—C12	120.9 (3)
C4—C5—C6	122.0 (3)	C10—C11—H11	119.5
C1—C5—C6	120.9 (3)	C12—C11—H11	119.5
O1—C6—C5	108.7 (2)	O2—C12—C11	118.3 (2)
O1—C6—H6A	109.9	O2—C12—C7	122.7 (2)
C5—C6—H6A	109.9	C11—C12—C7	119.0 (3)
O1—C6—H6B	109.9	C2—N1—C3	116.4 (2)
C5—C6—H6B	109.9	C7—O1—C6	117.04 (19)
H6A—C6—H6B	108.3	C12—O2—H2A	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1i	0.82	1.95	2.714 (3)	155

Symmetry codes: (i) −x, −y, −z+1.