3-(Pyridin-4-ylmeth­oxy)phenol

Abstract

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,

• a = 6.6551 (6) Å

• b = 9.1160 (8) Å

• c = 17.0039 (15) Å

• β = 100.501 (1)°

• V = 1014.31 (16) ų

• 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[F ² > 2σ(F ²)] = 0.041

• wR(F ²) = 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

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.

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
O1—H1A⋯N1i	0.95 (2)	1.75 (2)	2.6991 (17)	174 (2)

Symmetry code: (i) .

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, U_iso = 1.2U_eq (C) for aromatic and 0.97 Å, U_iso = 1.2U_eq (C) for CH2 atoms. H atoms bonded to O atoms were located in a difference Fourier map.

Figures

Fig. 1.

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

Crystal data

C12H11NO2	F(000) = 424
Mr = 201.22	Dx = 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

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

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)] = 0.041	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(Fo2) + (0.0212P)2] where P = (Fo2 + 2Fc2)/3
1981 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 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
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 (Ų)

	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, °)

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, °)

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 codes: (i) x−3/2, −y+3/2, z−1/2.