1-(4-Amino-3,5-dichloro­phen­yl)ethanol

Peng Liu; Jian-Feng Wu; Ping-An Wang; Wei He; Hai-Bo Wang

doi:10.1107/S1600536811024196

. 2011 Jun 30;67(Pt 7):o1839. doi: 10.1107/S1600536811024196

1-(4-Amino-3,5-dichlorophenyl)ethanol

Peng Liu ^a,^*, Jian-Feng Wu ^a, Ping-An Wang ^a, Wei He ^a, Hai-Bo Wang ^a

PMCID: PMC3151868 PMID: 21837206

Abstract

The asymmetric unit of the title compound, C₈H₉Cl₂NO, contains two crystallographically independent molecules which are connected via an N—H⋯O hydrogen bond . There is aromatic π–π stacking in the crystal, with a centroid–centroid distance between benzene rings of 3.48 (2)Å. The crystal packing is stabilized by intermolecular hydrogen bonds.

Related literature

For the synthetic use of the title compound and related compounds, see: Judkins et al. (1991 ▶); Ehrhardt (1990 ▶); Kelser (2007 ▶); Lu (2001 ▶); Pri-Bar et al. (1990 ▶); Shukrallah et al. (2004 ▶).

Experimental

Crystal data

C₈H₉Cl₂NO
M _r = 206.06
Monoclinic,
a = 16.472 (2) Å
b = 16.110 (2) Å
c = 14.6756 (19) Å
β = 107.049 (2)°
V = 3723.2 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.15 × 0.13 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.909, T _max = 0.950
9273 measured reflections
3279 independent reflections
2855 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.128
S = 1.06
3279 reflections
277 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010) ▶.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024196/zk2012sup1.cif

e-67-o1839-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024196/zk2012Isup2.hkl

e-67-o1839-Isup2.hkl^{(160.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024196/zk2012Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H13⋯O2ⁱ	0.82 (3)	2.17 (3)	2.927 (3)	154 (3)
O1—H16⋯N1ⁱⁱ	0.83 (3)	2.12 (3)	2.941 (3)	169 (3)
O2—H18⋯N2ⁱⁱⁱ	0.79 (3)	2.13 (3)	2.912 (3)	172 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the Natural Science Foundation of China (grant No. 20802092,21072228, 81001398) for financial support.

supplementary crystallographic information

Comment

We report here the crystal structure of the title compound 1-(4-amino-3, 5-dichlorophenyl) ethanol (I), a typical secondary aromatic alcohol and an important organic building block (Fig. 1). Bond lengths and angles are within normal ranges. As part of our ongoing studies of the secondary aromatic alcohol, the title compound was synthesized and characterized by X-ray diffraction. The asymmetric unit of the title compound (I) contains two crystallographically independent molecules in which both molecules are connected via N—H···O hydrogen bonds. The dihedral angle between the two benzene rings is 60.49°. The packing of molecules in the crystal structure is stabilized by intermolecular O—H···N hydrogen bonds.

Experimental

1-(4-amino-3,5-dichlorophenyl)ethanone (1.03 g,5 mmol) was dissolved in anhydrous methanol(25 ml) at room temperature, followed by addition of NaBH4(0.227 g, 6 mmol). The mixture was stirred vigorously at room temperature until TLC showed no ethanone. The solvent was evaporated to dryness under reduced pressure to obtain a crude product, which was purified by a flash column chromatography (n-hexane/EtOAc 8:1) to afford pure colorless compound in 89.6% yield. Then, the title compound (40 mg,0.19 mmol) was dissolved in ethyl acetate/n-hexane (7:3,15 ml). Colorless crystals were isolated after several days.