2-[(4-Bromo­benzyl­idene)amino]­ethanol

Moodley, V.; Van Zyl, W.E.

doi:10.1107/S1600536812048155

Volume 68
Part 12
Page o3477
December 2012

Received 18 October 2012
Accepted 23 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R = 0.025
wR = 0.059
Data-to-parameter ratio = 14.6
Details

2-[(4-Bromobenzylidene)amino]ethanol

Vashen Moodley ^a and Werner E. Van Zyl ^a ^*

^aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
Correspondence e-mail: vanzylw@ukzn.ac.za

In the crystal structure of the title compound, C₉H₁₀BrNO, molecules are linked via O-HN hydrogen bonds of a moderate strength between the hydroxy groups and the imine N atoms. These hydrogen bonds, as well as the planes of the bromophenyl rings, are situated in alternating planes parallel to (013) and (0-13). In addition, there are weak C-H [pi] interactions in the structure.

Related literature

For previous work on the preparation of imine-based ligands, by our group, see: Williams et al. (2007). For related structures and their preparation, see: Elslager et al. (1956); Vennila et al. (2010); Jafarpour et al. (2011). For imines, see: Morrison et al. (1987); Tidwell (2007) and for their biological activity, see: Solomon & Lowery (1993); Fioravanti et al. (1995); Mallikarjun & Sangamesh (1997); Samadhiya & Halve (2001); Gerdemann et al. (2002); Veverková & Toma (2008); Khan et al. (2009). For classification of hydrogen bonds, see: Gilli & Gilli (2009).

Experimental

Crystal data

C₉H₁₀BrNO
M_r = 228.09
Monoclinic, C c
a = 22.349 (4) Å
b = 6.0328 (10) Å
c = 7.3673 (12) Å
= 107.980 (3)°
V = 944.8 (3) Å³
Z = 4
Mo K radiation
= 4.30 mm^-1
T = 173 K
0.36 × 0.15 × 0.02 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) T_min = 0.305, T_max = 0.919
3713 measured reflections
1651 independent reflections
1550 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.059
S = 1.00
1651 reflections
113 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.71 e Å^-3
_min = -0.45 e Å^-3
Absolute structure: Flack (1983), 788 Friedel pairs
Flack parameter: 0.022 (12)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.97 (3)	1.83 (3)	2.791 (4)	172 (4)
C2-H2Cg1ⁱⁱ	0.95	2.83	3.58 (3)	137
C5-H5Cg1ⁱⁱⁱ	0.95	2.79	3.512 (3)	134
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2276 ).

Acknowledgements

The authors thank the National Research Foundation (NRF) and UKZN for financial support.

References

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