4-{[1-(4-Bromo­phen­yl)eth­yl]amino­meth­yl}phenol

Karilys Gonzalez Nieves

doi:10.1107/S1600536811028339

. 2011 Jul 23;67(Pt 8):o2110. doi: 10.1107/S1600536811028339

4-{[1-(4-Bromophenyl)ethyl]aminomethyl}phenol

Karilys Gonzalez Nieves ^a,^*

PMCID: PMC3213552 PMID: 22091129

Abstract

The title compound, C₁₅H₁₆BrNO, obtained from a two-step reaction, was prepared for use in transition metal chemistry as a phenolic ligand with bulky substituents. Intermolecular N—H⋯O and O—H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For chirality induction in metal complexes, see: Fan et al. (2010 ▶); Amendola et al. (2010 ▶). For imine reduction, see: Menta & Prabhakar (1995 ▶).

Experimental

Crystal data

C₁₅H₁₆BrNO
M _r = 306.20
Monoclinic,
a = 12.1753 (10) Å
b = 8.1939 (7) Å
c = 14.0326 (11) Å
β = 93.333 (1)°
V = 1397.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 296 K
0.20 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T _min = 0.592, T _max = 0.685
14961 measured reflections
3094 independent reflections
2119 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.077
S = 1.00
3094 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028339/fy2015sup1.cif

e-67-o2110-sup1.cif^{(22KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811028339/fy2015Isup2.cml

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028339/fy2015Isup3.hkl

e-67-o2110-Isup3.hkl^{(151.8KB, hkl)}

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
O1—H1A⋯N1ⁱ	0.82	2.05	2.794 (2)	150
N1—H1⋯O1ⁱⁱ	0.75 (2)	2.40 (2)	3.144 (3)	168 (2)

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

Acknowledgments

This work was supported by the NASA Space Grant (grant No. nnx10am80h). The author thanks Professor R. G. Raptis for providing access to the X-ray diffractometer and also thanks Dr Indranil Chakraborty for his help with the structure refinement.

supplementary crystallographic information

Comment

The title compound was prepared to be used as a ligand in order to induce chirality in transition metal complexes in combination with other bridging ligands. Here, we report the crystal structure of racemic 4-((1-(4-bromophenyl)ethylamino)methyl)phenol. In the crystal structure (Fig. 4), intermolecular hydrogen bonding was observed between N1—H1···O1 and O1—H1A···N1 (Table 1).

Experimental

An excess of racemic 4-bromo-α-methylbenzylamine (0.069 g, 0.45 mmol) was added to a solution of 4-hydroxybenzaldehyde (0.036 g, 0.29 mmol) in ethyl acetate. The solution was stirred overnight at room temperature. The solvent was removed under vacuum to obtain 4-((1-(4-bromophenyl)ethylimino)methyl)phenol as a white solid. The Schiff base was dissolved in anhydrous MeOH and an excess of NaBH₄ was added in several portions to the reaction mixture. After 24 h, water was added to the solution, and stirring was continued for two more hours. Methanol was removed under vacuum and the remaining aqueous phase was extracted three times with ethyl acetate. The combinated organic extracts were dried with magnesium sulfate, and the solvent was removed under vacuum to obtain a white solid. The product was dissolved in acetone and crystals were obtained by vapor diffusion of pentane.