Crystal structure of 3-(di­ethyl­amino)­phenol

James A Golen; Kyle J McDonald; David R Manke

doi:10.1107/S2056989015024226

. 2015 Dec 24;71(Pt 12):o1075. doi: 10.1107/S2056989015024226

Crystal structure of 3-(diethylamino)phenol

James A Golen ^a, Kyle J McDonald ^b, David R Manke ^a,^*

PMCID: PMC4719986 PMID: 26870505

Abstract

The title compound, C₁₀H₁₅NO, has two molecules in the asymmetric unit. Each molecule has a near-planar C₈NO unit excluding H atoms and the terminal methyl groups on the diethylamino groups, with mean deviations from planarity of 0.036 and 0.063 Å. In the crystal, hydrogen bonding leads to four-membered O—H⋯O—H⋯O—H·· rings. No π–π interactions were observed in the structure.

Keywords: crystal structure, hydrogen bonding, phenols

Related literature

For the structure of 3-aminophenol, see: Allen et al. (1997 ▸). For the structure of similar 3-aminophenols, see: Xu et al. (2004 ▸); Suchetan et al. (2014 ▸). For background, see: McDonald et al. (2015 ▸); Mills-Robles et al. (2015 ▸); Nguyen et al. (2015 ▸). graphic file with name e-71-o1075-scheme1.jpg

Experimental

Crystal data

C₁₀H₁₅NO
M _r = 165.23
Orthorhombic,
a = 14.5166 (17) Å
b = 15.9102 (18) Å
c = 16.0527 (18) Å
V = 3707.6 (7) Å³
Z = 16
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 120 K
0.25 × 0.2 × 0.1 mm

Data collection

Bruker D8 Venture CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.679, T _max = 0.753
21122 measured reflections
3398 independent reflections
2633 reflections with I > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.107
S = 1.02
3398 reflections
228 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024226/ff2147sup1.cif

e-71-o1075-sup1.cif^{(663.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024226/ff2147Isup2.hkl

e-71-o1075-Isup2.hkl^{(271.6KB, hkl)}

Click here for additional data file.^{(3.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015024226/ff2147Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015024226/ff2147fig1.tif

Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Click here for additional data file.^{(1.7MB, tif)}

. DOI: 10.1107/S2056989015024226/ff2147fig2.tif

Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

CCDC reference: 1442843

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
O1—H1⋯O1A	0.86 (1)	1.92 (1)	2.7445 (16)	160 (2)
O1A—H1A⋯O1ⁱ	0.86 (1)	1.91 (1)	2.7599 (16)	170 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We greatly acknowledge support from the National Science Foundation (CHE-1429086).

supplementary crystallographic information

S1. Comment

Herein we report the structure of 3-(diethylamino)phenol as part of a continuing collaboration between UMass Darmouth and Massasoit Community College to examine the solid state structure of aromatic alcohols (McDonald et al., 2015; Mills-Robles et al., 2015; Nguyen et al., 2015). Hydrogen bonding in the title compound leads to four-membered O1–H1···O1A–H1A···O1–H1·· rings. The molecules with the greatest structural similarity whose solid state structure have been reported all demonstrate hydrogen bonding with different acceptors. The parent 3-aminophenol (Allen et al., 1997) and 3-(1H-1,2,4-triazol-4-yl)phenol (Xu et al., 2004) both instead demonstrate O–H···N hydrogen bonding. The structure of N-(3-hydroxyphenyl)succinimide possesses O–H···O interactions with carbonyl oxygen atoms (Suchetan et al., 2014) rather than phenol only interactions.

The molecular structure of the title compound has two molecules in the asymmetric unit. Each molecule has a near planar C₈NO unit excluding H atoms and the terminal methyls on the diethylamino groups (C8, C10 and C8A, C10A). This unit for the molecule containing O1 has a mean deviations from planarity of 0.036 Å and the C₈NO unit for molecule containing O1A has a mean deviation from planarity of 0.063 Å. No π-π interactions were observed in the structure. The packing for the title compound indicating hydrogen bonding is shown in Figure 2.

S2. Experimental

Crystals suitable for X-ray diffraction studies were selected from a commercial sample (Aldrich).

S3. Refinement

All non-hydrogen atoms were refined anisotropically (XL) by full matrix least squares on F². Hydrogen atoms H1 and H1A were found from a Fourier difference map, and refined with a fixed distance of 0.86 (0.01) Å and isotropic displacement parameters of 1.50 times U_eq of the parent O atoms. The remaining hydrogen atoms were placed in calculated positions and then refined with a riding model with C–H lengths of 0.95 Å (sp²) and 0.98 Å (sp³) with isotropic displacement parameters set to 1.20 (sp²) and 1.50 (sp³) times U_eq of the parent C atom.