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

Gonzalez Nieves, K.

doi:10.1107/S1600536811028339

Volume 67
Part 8
Page o2110
August 2011

Received 4 June 2011
Accepted 14 July 2011
Online 23 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.077
Data-to-parameter ratio = 18.4
Details

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

Karilys Gonzalez Nieves ^a ^*

^aDepartment of Chemistry, University of Puerto Rico, San Juan, PR 00931, Puerto Rico
Correspondence e-mail: karilysgn@yahoo.com

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-HO and O-HN 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, P 2₁ /c
a = 12.1753 (10) Å
b = 8.1939 (7) Å
c = 14.0326 (11) Å
= 93.333 (1)°
V = 1397.6 (2) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.077
S = 1.00
3094 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN1ⁱ	0.82	2.05	2.794 (2)	150
N1-H1O1ⁱⁱ	0.75 (2)	2.40 (2)	3.144 (3)	168 (2)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: FY2015 ).

Acknowledgements

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.

References

Amendola, V., Boiocchi, M., Brega, V., Fabbrizzi, L. & Mosca, L. (2010). Inorg. Chem. 49, 997-1007.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Fan, L. L., Guo, F. S., Yun, L., Lin, Z. J., Herchel, R. & Leng, J. D. (2010). Dalton Trans. 39, 1771-1780.
Menta, G. & Prabhakar, C. (1995). J. Org. Chem. 60, 4638-4640.
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.

organic compounds