Naphthalen-1-yl­methanol

Nazarenko, A.Y.

doi:10.1107/S2414314620016466

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 12| December 2020| x201646

https://doi.org/10.1107/S2414314620016466

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Naphthalen-1-ylmethanol

Alexander Y. Nazarenko ^a ^*

^aChemistry Department, State University of New York, College at Buffalo, 1300 Elmwood Ave, Buffalo, NY 14222-1095, USA
^*Correspondence e-mail: nazareay@buffalostate.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 December 2020; accepted 19 December 2020; online 22 December 2020)

Apart from the OH group, the molecule of the title compound, C₁₁H₁₀O, is almost planar with all carbon atoms located within 0.03 Å of their mean plane. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds, generating infinite chains running parallel to the [100] direction.

Keywords: crystal structure; 1-naphthalenemethanol; hydrogen bond.

CCDC reference: 2051428

Structure description

The title compound, C₁₁H₁₀O, was first prepared by reduction of the corresponding naphthylamide (West, 1920 ) and by Grignard reaction involving formaldehyde (Ziegler, 1921 ). It is available commercially.

The title compound (Fig. 1) exhibits standard bond lengths and angles. Apart from the OH group, the molecule is almost planar: all carbon atoms are located within 0.03 Å of their mean plane and all aromatic hydrogen atoms are also within 0.04 Å of the same plane. Atom O1 is displaced from the mean plane of the other non-hydrogen atoms (r.m.s. deviation = 0.029 Å) by −1.260 (1) Å.

Figure 1
The molecular structure of the title compound with 50% displacement elipsoids.

In the crystal, the 1-naphthalenemethanol molecules are linked by O1—H1⋯O1ⁱ hydrogen bonds (Table 1, Fig. 2), generating infinite C(2) chains propagating parallel to the [100] direction: adjacent molecules in a chain are related by a-glide symmetry. Similar chains were observed in 1-naphthaleneethanol (Garozzo & Nazarenko, 2016 ). Additional C—H⋯C(ar) contacts involving the H4 hydrogen atom and C5 and C4 carbon atoms of another chain help to assemble the chains into a weakly bound layer lying parallel to the (010) plane (Fig. 2). These layers are held together by van der Waals forces, forming a molecular crystal.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.90 (2)	1.87 (2)	2.7504 (8)	166 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Figure 2
Packing of 1-naphthalenemethanol molecules viewed along the [010] vector. Hydrogen bonds are red, contacts shorter than sum of van der Waals radii are blue. Highlighted hydrogen atoms: H1 (pale blue), H4 (yellow), H8 (green).

Difference electron density maps (Fig. 3) show visible positive density at all covalent bonds and at the lone pair area of the oxygen atom. This effect comes from the limitations of the independent atom model; it results, among other shortcomings, in inflated R values and uncertainties of bonding parameters. Application of the Hirshfeld atom refinement with HARt (Fugel et al., 2018 ) to the same dataset yields a lower R(F) of 0.036 and significantly lower uncertainties for the bond lengths and angles.

Figure 3
Difference map in the plane of the naphthalene ring system (left lower corner: lone pair area of hydroxyl group).

Synthesis and crystallization

The title compound is commercially available from Aldrich. Recrystallization from ethanol solution yields needle-like crystals, which were used in the current study.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O
M_r	158.19
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	4.9306 (1), 15.7882 (5), 21.0651 (6)
V (Å³)	1639.82 (8)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.58 × 0.12 × 0.1

Data collection
Diffractometer	Bruker PHOTON-100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.797, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	38547, 2860, 2146
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.747

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.144, 1.04
No. of reflections	2860
No. of parameters	149
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.14
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2051428

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016466/hb4373sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016466/hb4373Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620016466/hb4373Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314620016466/hb4373Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Naphthalen-1-ylmethanol top

Crystal data top

C₁₁H₁₀O	D_x = 1.282 Mg m⁻³
M_r = 158.19	Melting point: 333 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 4.9306 (1) Å	Cell parameters from 9897 reflections
b = 15.7882 (5) Å	θ = 3.2–32.0°
c = 21.0651 (6) Å	µ = 0.08 mm⁻¹
V = 1639.82 (8) Å³	T = 173 K
Z = 8	Needle, colourless
F(000) = 672	0.58 × 0.12 × 0.1 mm

Data collection top

Bruker PHOTON-100 CMOS diffractometer	2860 independent reflections
Radiation source: sealedtube	2146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 10.8 pixels mm^-1	θ_max = 32.1°, θ_min = 3.2°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −23→23
T_min = 0.797, T_max = 0.862	l = −31→31
38547 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	All H-atom parameters refined
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0706P)² + 0.4678P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2860 reflections	Δρ_max = 0.35 e Å⁻³
149 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.64002 (18)	0.45528 (6)	0.27894 (4)	0.0398 (2)
H1	0.788 (5)	0.4551 (11)	0.2541 (10)	0.068 (5)*
C1	0.5128 (2)	0.39728 (7)	0.38094 (5)	0.0288 (2)
C2	0.3861 (2)	0.43905 (7)	0.42978 (5)	0.0330 (2)
H2	0.441 (3)	0.4976 (9)	0.4386 (7)	0.041 (4)*
C3	0.1852 (3)	0.39961 (8)	0.46739 (6)	0.0352 (3)
H3	0.102 (3)	0.4281 (10)	0.5013 (8)	0.045 (4)*
C4	0.1114 (2)	0.31785 (7)	0.45523 (5)	0.0325 (2)
H4	−0.027 (3)	0.2898 (9)	0.4812 (7)	0.042 (4)*
C5	0.2393 (2)	0.27146 (7)	0.40600 (5)	0.0276 (2)
C6	0.1723 (3)	0.18527 (7)	0.39480 (6)	0.0344 (3)
H6	0.027 (3)	0.1588 (9)	0.4205 (7)	0.044 (4)*
C7	0.3045 (3)	0.13985 (8)	0.34904 (6)	0.0388 (3)
H7	0.259 (4)	0.0829 (11)	0.3412 (8)	0.050 (4)*
C8	0.5083 (3)	0.17819 (8)	0.31230 (6)	0.0390 (3)
H8	0.607 (3)	0.1454 (10)	0.2784 (8)	0.050 (4)*
C9	0.5750 (2)	0.26132 (8)	0.32101 (5)	0.0336 (3)
H9	0.714 (3)	0.2873 (10)	0.2953 (7)	0.046 (4)*
C10	0.4438 (2)	0.31084 (7)	0.36840 (5)	0.0268 (2)
C11	0.7284 (2)	0.44171 (8)	0.34298 (6)	0.0349 (3)
H11A	0.777 (3)	0.4958 (10)	0.3634 (7)	0.041 (4)*
H11B	0.902 (3)	0.4052 (9)	0.3427 (7)	0.039 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0254 (4)	0.0620 (6)	0.0319 (4)	−0.0028 (4)	−0.0007 (3)	0.0145 (4)
C1	0.0253 (5)	0.0341 (5)	0.0268 (5)	−0.0015 (4)	−0.0036 (4)	0.0049 (4)
C2	0.0366 (6)	0.0322 (5)	0.0302 (5)	0.0010 (4)	−0.0043 (4)	0.0021 (4)
C3	0.0399 (6)	0.0387 (6)	0.0270 (5)	0.0087 (5)	0.0027 (4)	0.0012 (4)
C4	0.0319 (5)	0.0382 (6)	0.0274 (5)	0.0040 (4)	0.0043 (4)	0.0070 (4)
C5	0.0258 (5)	0.0323 (5)	0.0248 (5)	0.0015 (4)	−0.0012 (4)	0.0056 (4)
C6	0.0354 (6)	0.0333 (5)	0.0343 (6)	−0.0024 (4)	−0.0009 (4)	0.0059 (4)
C7	0.0451 (7)	0.0328 (6)	0.0384 (6)	−0.0006 (5)	−0.0041 (5)	−0.0004 (5)
C8	0.0408 (6)	0.0422 (6)	0.0339 (6)	0.0070 (5)	0.0014 (5)	−0.0049 (5)
C9	0.0285 (5)	0.0433 (6)	0.0290 (5)	0.0017 (4)	0.0020 (4)	0.0011 (4)
C10	0.0231 (4)	0.0330 (5)	0.0242 (4)	0.0014 (4)	−0.0023 (3)	0.0039 (4)
C11	0.0285 (5)	0.0441 (6)	0.0320 (5)	−0.0072 (5)	−0.0046 (4)	0.0072 (5)

Geometric parameters (Å, º) top

O1—H1	0.90 (2)	C5—C10	1.4252 (14)
O1—C11	1.4338 (14)	C6—H6	0.989 (17)
C1—C2	1.3724 (16)	C6—C7	1.3669 (18)
C1—C10	1.4310 (15)	C7—H7	0.940 (17)
C1—C11	1.5039 (16)	C7—C8	1.4054 (19)
C2—H2	0.980 (15)	C8—H8	1.006 (17)
C2—C3	1.4131 (17)	C8—C9	1.3653 (18)
C3—H3	0.939 (16)	C9—H9	0.965 (16)
C3—C4	1.3654 (17)	C9—C10	1.4232 (16)
C4—H4	0.981 (15)	C11—H11A	0.986 (16)
C4—C5	1.4174 (15)	C11—H11B	1.032 (16)
C5—C6	1.4201 (16)

C11—O1—H1	107.5 (14)	C6—C7—H7	120.8 (11)
C2—C1—C10	119.25 (10)	C6—C7—C8	120.22 (11)
C2—C1—C11	119.75 (10)	C8—C7—H7	119.0 (11)
C10—C1—C11	120.97 (10)	C7—C8—H8	121.0 (9)
C1—C2—H2	118.0 (9)	C9—C8—C7	120.80 (11)
C1—C2—C3	121.85 (11)	C9—C8—H8	118.2 (9)
C3—C2—H2	120.1 (9)	C8—C9—H9	120.3 (9)
C2—C3—H3	121.5 (10)	C8—C9—C10	120.87 (11)
C4—C3—C2	119.88 (11)	C10—C9—H9	118.8 (10)
C4—C3—H3	118.6 (10)	C5—C10—C1	118.78 (10)
C3—C4—H4	120.5 (9)	C9—C10—C1	123.06 (10)
C3—C4—C5	120.48 (11)	C9—C10—C5	118.14 (10)
C5—C4—H4	119.0 (9)	O1—C11—C1	110.79 (9)
C4—C5—C6	120.88 (10)	O1—C11—H11A	110.7 (9)
C4—C5—C10	119.74 (10)	O1—C11—H11B	109.3 (8)
C6—C5—C10	119.36 (10)	C1—C11—H11A	110.1 (9)
C5—C6—H6	118.8 (9)	C1—C11—H11B	109.2 (9)
C7—C6—C5	120.60 (11)	H11A—C11—H11B	106.5 (13)
C7—C6—H6	120.6 (9)

C1—C2—C3—C4	−0.39 (18)	C6—C5—C10—C9	−0.45 (15)
C2—C1—C10—C5	1.81 (15)	C6—C7—C8—C9	−0.9 (2)
C2—C1—C10—C9	−176.55 (10)	C7—C8—C9—C10	1.34 (19)
C2—C1—C11—O1	−113.15 (12)	C8—C9—C10—C1	177.73 (11)
C2—C3—C4—C5	1.44 (17)	C8—C9—C10—C5	−0.64 (17)
C3—C4—C5—C6	177.24 (11)	C10—C1—C2—C3	−1.25 (17)
C3—C4—C5—C10	−0.83 (16)	C10—C1—C11—O1	69.09 (14)
C4—C5—C6—C7	−177.20 (11)	C10—C5—C6—C7	0.88 (17)
C4—C5—C10—C1	−0.80 (15)	C11—C1—C2—C3	−179.05 (10)
C4—C5—C10—C9	177.65 (10)	C11—C1—C10—C5	179.58 (9)
C5—C6—C7—C8	−0.22 (19)	C11—C1—C10—C9	1.22 (16)
C6—C5—C10—C1	−178.90 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.90 (2)	1.87 (2)	2.7504 (8)	166 (2)

Symmetry code: (i) x+1/2, y, −z+1/2.

Acknowledgements

Financial support from the State University of New York for acquisition and maintenance of the X-ray diffractometer is gratefully acknowledged.

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