organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-(4-Pyridylmeth­­oxy)phenol

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 ππ 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[Gao, C.-M., Cao, D. & Zhu, L. (2004). Photogr. Sci. Photochem. 22, 103-107.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11NO2

  • Mr = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.968, Tmax = 0.983

  • 14969 measured reflections

  • 1802 independent reflections

  • 1139 reflections with I > 2σ(I)

  • Rint = 0.083

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.145

  • S = 1.03

  • 1802 reflections

  • 137 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 ππ 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.

Refinement top

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 Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.5Ueq(O).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. A dimer view, forming by hydrogen bonds and ππ interactions. Green dashed lines indicate the hydrogen bonds, blue dashed lines indicate the ππ interactions.
2-(4-Pyridylmethoxy)phenol top
Crystal data top
C12H11NO2F(000) = 848
Mr = 201.22Dx = 1.305 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9420 reflections
a = 11.800 (3) Åθ = 3.0–27.4°
b = 9.114 (4) ŵ = 0.09 mm1
c = 19.041 (7) ÅT = 291 K
V = 2047.7 (13) Å3Block, colorless
Z = 80.37 × 0.35 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1802 independent reflections
Radiation source: fine-focus sealed tube1139 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1412
Tmin = 0.968, Tmax = 0.983k = 1010
14969 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-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 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C12H11NO2V = 2047.7 (13) Å3
Mr = 201.22Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.800 (3) ŵ = 0.09 mm1
b = 9.114 (4) ÅT = 291 K
c = 19.041 (7) Å0.37 × 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)
Tmin = 0.968, Tmax = 0.983Rint = 0.083
14969 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.03Δρmax = 0.15 e Å3
1802 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
C10.0611 (2)0.0878 (3)0.41781 (16)0.0667 (8)
H10.01380.07320.37940.080*
C20.0381 (2)0.1961 (3)0.46523 (17)0.0704 (8)
H20.02560.25410.45770.085*
C30.1917 (2)0.1394 (3)0.53017 (15)0.0682 (8)
H30.23770.15650.56900.082*
C40.2214 (2)0.0278 (3)0.48491 (15)0.0640 (7)
H40.28590.02800.49340.077*
C50.1553 (2)0.0002 (3)0.42746 (14)0.0555 (7)
C60.1845 (2)0.1187 (3)0.37560 (15)0.0683 (8)
H6A0.25930.15760.38560.082*
H6B0.18490.07890.32840.082*
C70.1055 (2)0.3409 (3)0.33056 (13)0.0520 (7)
C80.1831 (2)0.3476 (3)0.27619 (14)0.0617 (7)
H80.23890.27610.27210.074*
C90.1775 (2)0.4614 (3)0.22763 (14)0.0666 (8)
H90.22880.46530.19060.080*
C100.0966 (2)0.5674 (3)0.23453 (15)0.0683 (8)
H100.09340.64410.20240.082*
C110.0199 (2)0.5614 (3)0.28856 (15)0.0674 (8)
H110.03470.63450.29270.081*
C120.0226 (2)0.4485 (3)0.33687 (14)0.0573 (7)
N10.1011 (2)0.2237 (2)0.52130 (12)0.0647 (6)
O10.10215 (15)0.23246 (18)0.38082 (9)0.0601 (5)
O20.05674 (18)0.4472 (2)0.38861 (11)0.0786 (7)
H2A0.05300.36940.41010.118*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0637 (17)0.0617 (18)0.0747 (18)0.0019 (15)0.0105 (14)0.0120 (16)
C20.0573 (18)0.0585 (19)0.095 (2)0.0047 (14)0.0003 (17)0.0094 (17)
C30.075 (2)0.0643 (19)0.0654 (18)0.0133 (17)0.0043 (15)0.0045 (15)
C40.0631 (17)0.0499 (16)0.0790 (19)0.0027 (14)0.0037 (16)0.0003 (15)
C50.0557 (15)0.0437 (15)0.0670 (17)0.0100 (13)0.0081 (14)0.0017 (13)
C60.0689 (18)0.0535 (17)0.083 (2)0.0132 (15)0.0134 (15)0.0154 (15)
C70.0568 (15)0.0428 (14)0.0564 (15)0.0058 (13)0.0043 (13)0.0051 (12)
C80.0640 (17)0.0532 (16)0.0679 (17)0.0038 (13)0.0007 (14)0.0006 (14)
C90.0764 (19)0.0660 (18)0.0573 (16)0.0129 (16)0.0033 (14)0.0084 (15)
C100.0752 (19)0.0616 (18)0.0681 (19)0.0076 (16)0.0171 (16)0.0177 (15)
C110.0686 (18)0.0556 (17)0.078 (2)0.0034 (14)0.0133 (16)0.0130 (15)
C120.0576 (16)0.0490 (16)0.0652 (17)0.0019 (14)0.0038 (14)0.0020 (13)
N10.0634 (14)0.0528 (14)0.0778 (16)0.0094 (12)0.0135 (13)0.0104 (12)
O10.0650 (12)0.0450 (10)0.0703 (12)0.0096 (9)0.0098 (9)0.0095 (9)
O20.0792 (14)0.0630 (14)0.0936 (15)0.0222 (11)0.0211 (12)0.0206 (11)
Geometric parameters (Å, º) top
C1—C21.365 (4)C7—O11.376 (3)
C1—C51.384 (4)C7—C81.383 (3)
C1—H10.9300C7—C121.390 (3)
C2—N11.325 (3)C8—C91.391 (4)
C2—H20.9300C8—H80.9300
C3—N11.327 (3)C9—C101.365 (4)
C3—C41.378 (4)C9—H90.9300
C3—H30.9300C10—C111.371 (4)
C4—C51.367 (4)C10—H100.9300
C4—H40.9300C11—C121.381 (4)
C5—C61.503 (4)C11—H110.9300
C6—O11.424 (3)C12—O21.359 (3)
C6—H6A0.9700O2—H2A0.8200
C6—H6B0.9700
C2—C1—C5119.4 (3)O1—C7—C8124.8 (2)
C2—C1—H1120.3O1—C7—C12115.2 (2)
C5—C1—H1120.3C8—C7—C12119.9 (2)
N1—C2—C1124.0 (3)C7—C8—C9120.0 (3)
N1—C2—H2118.0C7—C8—H8120.0
C1—C2—H2118.0C9—C8—H8120.0
N1—C3—C4123.5 (3)C10—C9—C8119.8 (3)
N1—C3—H3118.3C10—C9—H9120.1
C4—C3—H3118.3C8—C9—H9120.1
C5—C4—C3119.6 (3)C9—C10—C11120.4 (3)
C5—C4—H4120.2C9—C10—H10119.8
C3—C4—H4120.2C11—C10—H10119.8
C4—C5—C1117.1 (3)C10—C11—C12120.9 (3)
C4—C5—C6122.0 (3)C10—C11—H11119.5
C1—C5—C6120.9 (3)C12—C11—H11119.5
O1—C6—C5108.7 (2)O2—C12—C11118.3 (2)
O1—C6—H6A109.9O2—C12—C7122.7 (2)
C5—C6—H6A109.9C11—C12—C7119.0 (3)
O1—C6—H6B109.9C2—N1—C3116.4 (2)
C5—C6—H6B109.9C7—O1—C6117.04 (19)
H6A—C6—H6B108.3C12—O2—H2A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N1i0.821.952.714 (3)155
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H11NO2
Mr201.22
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)291
a, b, c (Å)11.800 (3), 9.114 (4), 19.041 (7)
V3)2047.7 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.37 × 0.35 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.968, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
14969, 1802, 1139
Rint0.083
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.145, 1.03
No. of reflections1802
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O2—H2A···N1i0.821.952.714 (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

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

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ISSN: 2056-9890
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