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

Kim, H.; Kang, S.K.

doi:10.1107/S1600536814016857

organic compounds

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Volume 70| Part 9| September 2014| Page o947

doi:10.1107/S1600536814016857

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

Haneol Kim ^a and Sung Kwon Kang ^a ^*

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 19 July 2014; accepted 21 July 2014; online 1 August 2014)

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.

Keywords: crystal structure; phenyl(pyridin-2-yl)methanol; hydrogen bonding.

CCDC reference: 1015307

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₁NO
M_r = 185.22
Orthorhombic, P n a 2₁
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

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
7290 measured reflections
2245 independent reflections
1190 reflections with I > 2σ(I)
R_int = 0.055

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 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

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) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

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).

Supporting information

CCDC reference: 1015307

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016857/su2760sup1.cif

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

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

checkCIF report

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

	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).

Phenyl(pyridin-2-yl)methanol top

Crystal data top

C₁₂H₁₁NO	F(000) = 392
M_r = 185.22	D_x = 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 top

Bruker SMART CCD area-detector diffractometer	R_int = 0.055
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 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 top

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(F_o²) + (0.0303P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
2245 reflections	Δρ_max = 0.09 e Å⁻³
131 parameters	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₂H₁₁NO	V = 984.27 (19) Å³
M_r = 185.22	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.4385 (8) Å	µ = 0.08 mm⁻¹
b = 14.3429 (16) Å	T = 296 K
c = 9.2255 (10) Å	0.3 × 0.26 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1190 reflections with I > 2σ(I)
7290 measured reflections	R_int = 0.055
2245 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.09 e Å⁻³
2245 reflections	Δρ_min = −0.12 e Å⁻³
131 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

This work was supported by research funding of Chungnam National University.

References

Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Frassoldati, A., Pinel, C. & Besson, M. (2013). Catal. Today, 203, 133–138. Web of Science CrossRef CAS Google Scholar
Lash, T. D., Pokharel, K., Serling, J. M., Yant, V. R. & Ferrence, G. M. (2007). Org. Lett. 9, 2863–2866. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lucchesi, C., Inasaki, T., Miyamura, H., Matsubara, R. & Kobayashi, S. (2008). Adv. Synth. Catal. 350, 1996–2000. Web of Science CrossRef CAS Google Scholar
Miyamura, H., Matsubara, R. & Kobayashi, S. (2008). Chem. Commun. pp. 2031–2033. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szajna, E., Dobrowolski, P., Fuller, A. L., Srif, A. M. & Berreau, L. M. (2004). Inorg. Chem. 43, 3988–3997. Web of Science CSD CrossRef PubMed CAS Google Scholar
Tao, X., Li, W., Ma, X., Li, X., Fan, W., Xie, X., Ayad, T., Ratovelomanana-Vidal, V. & Zhang, Z. (2012). J. Org. Chem. 77, 612–616. Web of Science CrossRef CAS PubMed Google Scholar