Crystal structure of phen-yl(pyridin-2-yl)methanol.

In the title compound, C12H11NO, the pyridine and phenyl rings are inclined to each other by 71.42 (10)°. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into helical chains extending along the c-axis direction.

Related literature

For the synthesis of the title compound and some derivatives, see: Frassoldati et al. (2013 ▶); Tao et al. (2012 ▶). For its use in synthesis, see: Miyamura et al. (2008 ▶); Lucchesi et al. (2008 ▶); Lash et al. (2007 ▶); Szajna et al. (2004 ▶).

Experimental

Crystal data

C12H11NO

M = 185.22

Orthorhombic,

a = 7.4385 (8) Å

b = 14.3429 (16) Å

c = 9.2255 (10) Å

V = 984.27 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.3 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

7290 measured reflections

2245 independent reflections

1190 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.084

S = 0.81

2245 reflections

131 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016857/su2760sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016857/su2760Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016857/su2760Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016857/su2760fig1.tif

Mol­ecular structure of the title mol­ecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814016857/su2760fig2.tif

A view along the a axis of the crystal packing of the title compound, showing mol­ecules linked by O—H⋯N hydrogen bonds (dashed lines; see Table 1 for details).

CCDC reference: 1015307

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H11NO	F(000) = 392
Mr = 185.22	Dx = 1.25 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 973 reflections
a = 7.4385 (8) Å	θ = 2.6–19.7°
b = 14.3429 (16) Å	µ = 0.08 mm−1
c = 9.2255 (10) Å	T = 296 K
V = 984.27 (19) Å3	Block, colourless
Z = 4	0.3 × 0.26 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.055
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −7→9
7290 measured reflections	k = −18→18
2245 independent reflections	l = −11→11
1190 reflections with I > 2σ(I)

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0303P)2] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max < 0.001
2245 reflections	Δρmax = 0.09 e Å−3
131 parameters	Δρmin = −0.12 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.

	x	y	z	Uiso*/Ueq
N1	0.4374 (3)	0.37463 (19)	0.8538 (3)	0.0544 (7)
C2	0.4309 (5)	0.2902 (3)	0.9150 (5)	0.0738 (12)
H2	0.4616	0.2851	1.0124	0.089*
C3	0.3819 (5)	0.2112 (3)	0.8433 (6)	0.0773 (12)
H3	0.3794	0.154	0.8907	0.093*
C4	0.3365 (4)	0.2177 (2)	0.7004 (5)	0.0733 (12)
H4	0.302	0.1651	0.6485	0.088*
C5	0.3426 (4)	0.3039 (2)	0.6344 (4)	0.0582 (9)
H5	0.3119	0.3104	0.5372	0.07*
C6	0.3949 (4)	0.3804 (2)	0.7141 (3)	0.0434 (7)
C7	0.4046 (4)	0.4769 (2)	0.6482 (3)	0.0501 (8)
H7	0.5021	0.5116	0.6949	0.06*
O8	0.4471 (3)	0.46457 (19)	0.5006 (3)	0.0700 (7)
H8	0.474 (5)	0.526 (3)	0.460 (5)	0.111 (16)*
C9	0.2299 (3)	0.52994 (18)	0.6693 (3)	0.0409 (7)
C10	0.0771 (4)	0.5047 (2)	0.5952 (4)	0.0587 (9)
H10	0.0817	0.4549	0.5307	0.07*
C11	−0.0819 (4)	0.5515 (3)	0.6146 (4)	0.0715 (11)
H11	−0.1837	0.5334	0.5633	0.086*
C12	−0.0908 (5)	0.6244 (3)	0.7087 (4)	0.0679 (10)
H12	−0.1989	0.6557	0.7224	0.081*
C13	0.0579 (5)	0.6514 (2)	0.7824 (4)	0.0697 (10)
H13	0.0515	0.7017	0.8459	0.084*
C14	0.2204 (4)	0.6043 (2)	0.7639 (4)	0.0570 (8)
H14	0.3219	0.623	0.8151	0.068*

	U11	U22	U33	U12	U13	U23
N1	0.0530 (17)	0.061 (2)	0.0488 (19)	0.0047 (13)	0.0014 (14)	0.0027 (15)
C2	0.066 (3)	0.084 (3)	0.071 (3)	0.019 (2)	0.008 (2)	0.024 (2)
C3	0.059 (2)	0.059 (3)	0.114 (4)	0.006 (2)	0.015 (2)	0.029 (3)
C4	0.059 (2)	0.049 (2)	0.112 (4)	0.0045 (17)	0.006 (3)	−0.008 (2)
C5	0.056 (2)	0.057 (2)	0.062 (2)	0.0079 (16)	0.0005 (17)	−0.0047 (19)
C6	0.0362 (15)	0.0463 (19)	0.0476 (19)	0.0058 (13)	0.0045 (15)	−0.0004 (15)
C7	0.0500 (18)	0.0578 (19)	0.0426 (19)	−0.0030 (15)	0.0052 (15)	−0.0001 (16)
O8	0.0827 (17)	0.0741 (18)	0.0530 (15)	0.0020 (14)	0.0260 (13)	0.0028 (13)
C9	0.0452 (16)	0.0391 (15)	0.0383 (15)	−0.0036 (14)	0.0017 (14)	0.0062 (14)
C10	0.059 (2)	0.047 (2)	0.069 (2)	−0.0019 (17)	−0.0103 (18)	−0.0040 (17)
C11	0.052 (2)	0.072 (2)	0.090 (3)	0.0003 (19)	−0.009 (2)	0.010 (2)
C12	0.061 (2)	0.071 (2)	0.072 (3)	0.016 (2)	0.011 (2)	0.014 (2)
C13	0.091 (3)	0.057 (2)	0.061 (2)	0.018 (2)	0.004 (2)	−0.005 (2)
C14	0.066 (2)	0.0535 (18)	0.0512 (19)	−0.0022 (16)	−0.0088 (18)	−0.0012 (17)

N1—C6	1.329 (4)	C7—H7	0.98
N1—C2	1.338 (4)	O8—H8	0.98 (5)
C2—C3	1.362 (5)	C9—C10	1.374 (4)
C2—H2	0.93	C9—C14	1.380 (4)
C3—C4	1.364 (5)	C10—C11	1.372 (4)
C3—H3	0.93	C10—H10	0.93
C4—C5	1.379 (5)	C11—C12	1.361 (5)
C4—H4	0.93	C11—H11	0.93
C5—C6	1.376 (4)	C12—C13	1.354 (5)
C5—H5	0.93	C12—H12	0.93
C6—C7	1.514 (4)	C13—C14	1.395 (4)
C7—O8	1.408 (4)	C13—H13	0.93
C7—C9	1.518 (4)	C14—H14	0.93
C6—N1—C2	117.2 (3)	C9—C7—H7	108.8
N1—C2—C3	123.9 (4)	C7—O8—H8	108 (3)
N1—C2—H2	118.1	C10—C9—C14	118.4 (3)
C3—C2—H2	118.1	C10—C9—C7	120.8 (3)
C2—C3—C4	118.6 (4)	C14—C9—C7	120.8 (3)
C2—C3—H3	120.7	C11—C10—C9	121.3 (3)
C4—C3—H3	120.7	C11—C10—H10	119.4
C3—C4—C5	118.7 (4)	C9—C10—H10	119.4
C3—C4—H4	120.7	C12—C11—C10	120.1 (4)
C5—C4—H4	120.7	C12—C11—H11	120
C6—C5—C4	119.2 (3)	C10—C11—H11	120
C6—C5—H5	120.4	C13—C12—C11	120.0 (3)
C4—C5—H5	120.4	C13—C12—H12	120
N1—C6—C5	122.4 (3)	C11—C12—H12	120
N1—C6—C7	115.8 (3)	C12—C13—C14	120.5 (3)
C5—C6—C7	121.8 (3)	C12—C13—H13	119.8
O8—C7—C6	106.5 (3)	C14—C13—H13	119.8
O8—C7—C9	112.3 (2)	C9—C14—C13	119.8 (3)
C6—C7—C9	111.4 (2)	C9—C14—H14	120.1
O8—C7—H7	108.8	C13—C14—H14	120.1
C6—C7—H7	108.8

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···N1i	0.98 (5)	1.85 (5)	2.809 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯N1i	0.98 (5)	1.85 (5)	2.809 (4)	166 (4)

Symmetry code: (i) .