Crystal structure of phen­yl(pyridin-2-yl)methanol

Abstract

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 mol­ecules 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 _r = 185.22

• Orthorhombic,

• a = 7.4385 (8) Å

• b = 14.3429 (16) Å

• c = 9.2255 (10) Å

• V = 984.27 (19) ų

• 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

• Δρ_max = 0.09 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

CCDC reference: 1015307

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

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) .

supplementary crystallographic information

S1. Experimental

To a solution of 2-benzoylpyridine (5.0 g, 0.027 mol) in EtOH (60 ml) was added NaBH₄ (3.13 g, 0.083 mol) slowly at room temperature. The solution was stirred gently for 1 h. After adding 60 ml H₂O, this solution was heated at 363 K for 15 min. After cooling, the product was extracted with AcOEt (50 ml). The solvent was evaporated under reduced pressure to leave a pale green oil. Colourless crystals of the title compound were obtained by slow evaporation of a solution in EtOH at room temperature.

S2. Refinement

Atom H8 of the OH group was located in a difference Fourier map and freely refined. C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.93 - 0.98 Å with U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

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

Fig. 2.

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).

Crystal data

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

Data collection

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

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

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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

Hydrogen-bond geometry (Å, º)

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) −x+1, −y+1, z−1/2.