3-(Pyridin-4-ylmeth­oxy)phenol

Han, L.; Zang, H.; Sun, D.

doi:10.1107/S1600536810045800

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3147

https://doi.org/10.1107/S1600536810045800

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3-(Pyridin-4-ylmethoxy)phenol

Liying Han,^a Hu Zang ^b ^* and Dajun Sun ^c

^aDepartment of Gynecology, The Second Hospital of Jilin University, Changchun 130041, People's Republic of China, ^bDepartment of Orthopedics, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China, and ^cDepartment of Vascular Surgery, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China
^*Correspondence e-mail: huzang2010@yahoo.cn

(Received 6 November 2010; accepted 8 November 2010; online 13 November 2010)

In the title compound, C₁₂H₁₁NO₂, the phenolic ring is inclined at an angle of 32.70 (1)° with respect to the pyridine ring. In the crystal, intermolecular O—H⋯N hydrogen bonds link the molecules into C(11) chains along [001].

Related literature

For a related structure, see: Yumoto et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₁NO₂
M_r = 201.22
Monoclinic, P 2₁ /n
a = 6.6551 (6) Å
b = 9.1160 (8) Å
c = 17.0039 (15) Å
β = 100.501 (1)°
V = 1014.31 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.930, T_max = 0.980
5411 measured reflections
1981 independent reflections
1310 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.091
S = 0.89
1981 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.95 (2)	1.75 (2)	2.6991 (17)	174 (2)
Symmetry code: (i) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045800/ng5062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045800/ng5062Isup2.hkl

checkCIF report

Comment top

Pyridine and its derivatives represent one of the most active classes of compounds possessing a wide application of biological activities, such as stent in intestinal or biliary fields. During the past years, considerable efforts have been paid to demonstrate the efficacy of pyridine derivatives including antibacterial, antifungal, herbicidal, insecticidal and other biological activities. A new pyridine derivatives molecule is synthesized, with the aim of studying its single-crystal structure.

The title molecule (Fig. 1) consists of a phenol moiety (O1/C1—C6) and a methoxy moiety (O2/C7) attached to a pyridine ring (N1/C8—C12). The pyridine ring is inclined at an angle of 32.70 (1)° with the phenol ring. Bond lengths and angles are within normal ranges, and comparable to closely related structures (Yumoto et al., 2008). In the crystal structure, the crystal packing is consolidated by intermolecular O1—H1A···N1 hydrogen bonds linking the molecules into one linear structure.

Related literature top

For a related structure, see: Yumoto et al. (2008).

Experimental top

A mixture of 1,3-dihydroxybenzene (1.1 g, 10 mmol), 4-chloromethlpyridine hydrochloride (1.64 g, 10 mmol), and NaOH (1.6 g, 40 mmol) in acetonitrile (50 ml) was refluxed under nitrogen with stirring for 24 h. After cooling to room temperature, the reactant was filtered, and the residue was washed with acetonitrile several times. The mixed filtrate was slowly evaporated and colorless crystals were obtained.

Structure description top

For a related structure, see: Yumoto et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level.

3-(Pyridin-4-ylmethoxy)phenol top

Crystal data top

C₁₂H₁₁NO₂	F(000) = 424
M_r = 201.22	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1981 reflections
a = 6.6551 (6) Å	θ = 1.9–28.3°
b = 9.1160 (8) Å	µ = 0.09 mm⁻¹
c = 17.0039 (15) Å	T = 293 K
β = 100.501 (1)°	Block, colorless
V = 1014.31 (16) Å³	0.28 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	1981 independent reflections
Radiation source: fine-focus sealed tube	1310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
φ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.930, T_max = 0.980	k = −9→11
5411 measured reflections	l = −15→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0212P)²] where P = (F_o² + 2F_c²)/3
1981 reflections	(Δ/σ)_max = 0.001
140 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₂H₁₁NO₂	V = 1014.31 (16) Å³
M_r = 201.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6551 (6) Å	µ = 0.09 mm⁻¹
b = 9.1160 (8) Å	T = 293 K
c = 17.0039 (15) Å	0.28 × 0.24 × 0.22 mm
β = 100.501 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	1981 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1310 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.980	R_int = 0.098
5411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.14 e Å⁻³
1981 reflections	Δρ_min = −0.18 e Å⁻³
140 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
N1	0.7272 (2)	0.82817 (15)	1.01329 (9)	0.0343 (4)
O1	−0.50233 (18)	0.67160 (13)	0.65242 (7)	0.0385 (3)
O2	0.13905 (16)	0.82363 (12)	0.78584 (7)	0.0357 (3)
H1A	−0.601 (3)	0.678 (2)	0.6047 (13)	0.073 (7)*
C7	0.3149 (2)	0.91479 (18)	0.79342 (10)	0.0317 (4)
H7A	0.2748	1.0170	0.7939	0.038*
H7B	0.3829	0.8995	0.7482	0.038*
C6	−0.1795 (2)	0.75328 (18)	0.71613 (9)	0.0296 (4)
H6	−0.1743	0.6758	0.7520	0.036*
C5	−0.0183 (2)	0.85103 (18)	0.72303 (9)	0.0295 (4)
C12	0.3904 (2)	0.81807 (17)	0.93485 (10)	0.0320 (4)
H12	0.2540	0.7921	0.9316	0.038*
C8	0.4572 (2)	0.87800 (17)	0.86953 (10)	0.0271 (4)
C11	0.5288 (3)	0.79727 (18)	1.00500 (11)	0.0345 (4)
H11	0.4809	0.7596	1.0489	0.041*
C1	−0.3484 (2)	0.77025 (19)	0.65603 (10)	0.0305 (4)
C2	−0.3563 (3)	0.88767 (19)	0.60343 (10)	0.0356 (4)
H2	−0.4703	0.9013	0.5635	0.043*
C9	0.6626 (2)	0.90938 (18)	0.87728 (10)	0.0313 (4)
H9	0.7143	0.9480	0.8344	0.038*
C4	−0.0223 (2)	0.96653 (18)	0.67026 (10)	0.0348 (4)
H4	0.0871	1.0313	0.6743	0.042*
C3	−0.1947 (2)	0.98324 (19)	0.61087 (10)	0.0384 (5)
H3	−0.2005	1.0613	0.5753	0.046*
C10	0.7902 (2)	0.88286 (18)	0.94908 (10)	0.0346 (4)
H10	0.9283	0.9043	0.9532	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0290 (8)	0.0365 (9)	0.0345 (9)	0.0046 (6)	−0.0018 (7)	−0.0058 (7)
O1	0.0276 (7)	0.0540 (8)	0.0305 (7)	−0.0094 (6)	−0.0038 (6)	0.0043 (6)
O2	0.0296 (7)	0.0405 (7)	0.0315 (7)	−0.0063 (5)	−0.0091 (5)	0.0046 (5)
C7	0.0266 (9)	0.0371 (10)	0.0304 (10)	−0.0015 (8)	0.0025 (8)	−0.0030 (8)
C6	0.0292 (9)	0.0352 (10)	0.0231 (9)	0.0006 (8)	0.0014 (8)	0.0026 (8)
C5	0.0266 (9)	0.0365 (10)	0.0231 (9)	0.0017 (8)	−0.0012 (7)	−0.0033 (8)
C12	0.0228 (9)	0.0375 (11)	0.0345 (10)	0.0018 (7)	0.0020 (8)	−0.0024 (8)
C8	0.0237 (9)	0.0280 (9)	0.0283 (9)	0.0033 (7)	0.0012 (7)	−0.0063 (7)
C11	0.0329 (10)	0.0388 (11)	0.0315 (10)	0.0025 (8)	0.0050 (8)	−0.0018 (8)
C1	0.0252 (9)	0.0401 (11)	0.0255 (9)	−0.0006 (8)	0.0029 (7)	−0.0043 (8)
C2	0.0312 (10)	0.0406 (11)	0.0307 (10)	0.0036 (8)	−0.0061 (8)	0.0026 (8)
C9	0.0287 (10)	0.0328 (10)	0.0323 (10)	0.0001 (7)	0.0055 (8)	−0.0063 (8)
C4	0.0325 (10)	0.0324 (10)	0.0364 (11)	−0.0041 (8)	−0.0016 (8)	0.0018 (8)
C3	0.0422 (11)	0.0319 (10)	0.0367 (11)	−0.0006 (8)	−0.0046 (9)	0.0057 (8)
C10	0.0243 (9)	0.0358 (10)	0.0419 (12)	0.0003 (8)	0.0015 (8)	−0.0112 (9)

Geometric parameters (Å, º) top

N1—C11	1.332 (2)	C12—C8	1.382 (2)
N1—C10	1.335 (2)	C12—H12	0.9300
O1—C1	1.3560 (19)	C8—C9	1.379 (2)
O1—H1A	0.95 (2)	C11—H11	0.9300
O2—C5	1.3756 (17)	C1—C2	1.390 (2)
O2—C7	1.4218 (18)	C2—C3	1.372 (2)
C7—C8	1.496 (2)	C2—H2	0.9300
C7—H7A	0.9700	C9—C10	1.375 (2)
C7—H7B	0.9700	C9—H9	0.9300
C6—C5	1.383 (2)	C4—C3	1.392 (2)
C6—C1	1.383 (2)	C4—H4	0.9300
C6—H6	0.9300	C3—H3	0.9300
C5—C4	1.381 (2)	C10—H10	0.9300
C12—C11	1.381 (2)

C11—N1—C10	116.44 (15)	N1—C11—C12	123.70 (17)
C1—O1—H1A	113.5 (12)	N1—C11—H11	118.2
C5—O2—C7	117.50 (13)	C12—C11—H11	118.2
O2—C7—C8	109.17 (13)	O1—C1—C6	117.70 (16)
O2—C7—H7A	109.8	O1—C1—C2	122.82 (15)
C8—C7—H7A	109.8	C6—C1—C2	119.46 (16)
O2—C7—H7B	109.8	C3—C2—C1	119.52 (16)
C8—C7—H7B	109.8	C3—C2—H2	120.2
H7A—C7—H7B	108.3	C1—C2—H2	120.2
C5—C6—C1	120.27 (16)	C10—C9—C8	119.27 (16)
C5—C6—H6	119.9	C10—C9—H9	120.4
C1—C6—H6	119.9	C8—C9—H9	120.4
O2—C5—C4	124.39 (15)	C5—C4—C3	118.06 (16)
O2—C5—C6	114.70 (15)	C5—C4—H4	121.0
C4—C5—C6	120.91 (15)	C3—C4—H4	121.0
C11—C12—C8	119.11 (15)	C2—C3—C4	121.76 (17)
C11—C12—H12	120.4	C2—C3—H3	119.1
C8—C12—H12	120.4	C4—C3—H3	119.1
C9—C8—C12	117.64 (15)	N1—C10—C9	123.82 (16)
C9—C8—C7	119.78 (15)	N1—C10—H10	118.1
C12—C8—C7	122.54 (14)	C9—C10—H10	118.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.95 (2)	1.75 (2)	2.6991 (17)	174 (2)

Symmetry code: (i) x−3/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NO₂
M_r	201.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.6551 (6), 9.1160 (8), 17.0039 (15)
β (°)	100.501 (1)
V (Å³)	1014.31 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.930, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5411, 1981, 1310
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.091, 0.89
No. of reflections	1981
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.95 (2)	1.75 (2)	2.6991 (17)	174 (2)

Symmetry code: (i) x−3/2, −y+3/2, z−1/2.

Acknowledgements

The authors thank The China–Japan Union Hospital of Jilin University for supporting this work.

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. VUniversity of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yumoto, K., Irie, M. & Matsuda, K. (2008). Org. Lett. 10, 2051–2054. Web of Science CSD CrossRef PubMed CAS Google Scholar