2-(4-Pyridylmeth­oxy)phenol

Zhang, Z.; Li, Y.-J.; Gao, X.-M.

doi:10.1107/S1600536809047205

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3160

doi:10.1107/S1600536809047205

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2-(4-Pyridylmethoxy)phenol

Zhi Zhang,^a Yu-Jie Li ^a and Xue-Mei Gao ^a ^*

^aDepartment of Animal Science, Jilin Agricultural Science and Technology College, Jilin 132101, People's Republic of China
^*Correspondence e-mail: zz004@163.com

(Received 13 October 2009; accepted 9 November 2009; online 21 November 2009)

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, P b c a
a = 11.800 (3) Å
b = 9.114 (4) Å
c = 19.041 (7) Å
V = 2047.7 (13) Å³
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[F² > 2σ(F²)] = 0.059
wR(F²) = 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

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) -x, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047205/fj2252sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047205/fj2252Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	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.

2-(4-Pyridylmethoxy)phenol top

Crystal data top

C₁₂H₁₁NO₂	F(000) = 848
M_r = 201.22	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0709P)² + 0.2741P] where P = (F_o² + 2F_c²)/3
1802 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₂H₁₁NO₂	V = 2047.7 (13) Å³
M_r = 201.22	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.800 (3) Å	µ = 0.09 mm⁻¹
b = 9.114 (4) Å	T = 291 K
c = 19.041 (7) Å	0.37 × 0.35 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1802 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1139 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.983	R_int = 0.083
14969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
1802 reflections	Δρ_min = −0.13 e Å⁻³
137 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NO₂
M_r	201.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	11.800 (3), 9.114 (4), 19.041 (7)
V (Å³)	2047.7 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.35 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.968, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14969, 1802, 1139
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.145, 1.03
No. of reflections	1802
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱ	0.82	1.95	2.714 (3)	155.4

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

The authors thank Jilin Agricultural Science and Technology College for supporting this study.

References

Gao, C.-M., Cao, D. & Zhu, L. (2004). Photogr. Sci. Photochem. 22, 103–107. CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar