3-(Pyridin-4-ylmeth-oxy)phenol.

In the title compound, C(12)H(11)NO(2), the phenolic ring is inclined at an angle of 32.70 (1)° with respect to the pyridine ring. In the crystal, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into C(11) chains along [001].

Related literature

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

Experimental

Crystal data

C12H11NO2

M = 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) 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[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

Δρmax = 0.14 e Å−3

Δρmin = −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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045800/ng5062Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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

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.

	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*

	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)

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

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)

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) .