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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 [sigma](C-C) = 0.005 Å
R = 0.025
wR = 0.059
Data-to-parameter ratio = 14.6
Details
Open access

2-[(4-Bromobenzylidene)amino]ethanol

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-H...N 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[Williams, D. B. G., Traut, T., Kriel, F. H. & Van Zyl, W. E. (2007). Inorg. Chem. Commun. 10, 538-542.]). For related structures and their preparation, see: Elslager et al. (1956[Elslager, E. F., Benton, E. L., Short, F. W. & Tendick, F. H. (1956). J. Am. Chem. Soc. 78, 3453-3457.]); Vennila et al. (2010[Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Gunasekaran, B. & Manivannan, V. (2010). Acta Cryst. E66, o316.]); Jafarpour et al. (2011[Jafarpour, M., Rezaeifard, A., Gazkar, S. & Danehchin, M. (2011). Transition Met. Chem. 36, 685-690.]). For imines, see: Morrison et al. (1987[Morrison, R. T. & Boyd, R. N. (1987). Organic Chemistry, 5th ed., pp. 945-946. Boston: Allyn and Bacon Inc.]); Tidwell (2007[Tidwell, T. T. (2007). Angew. Chem. Int. Ed. 46, 2-7.]) and for their biological activity, see: Solomon & Lowery (1993[Solomon, E. I. & Lowery, M. D. (1993). Science, 259, 1575-1581.]); Fioravanti et al. (1995[Fioravanti, R., Biava, M., Porretta, G. C., Landolfi, C., Simonetti, N., Villa, A., Conte, E. & Porta-Puglia, A. (1995). Eur. J. Med. Chem. 30, 123-132.]); Mallikarjun & Sangamesh (1997[Mallikarjun, S. Y. & Sangamesh, A. P. (1997). Transition Met. Chem. 22, 220-224.]); Samadhiya & Halve (2001[Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.]); Gerdemann et al. (2002[Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183-191.]); Veverková & Toma (2008[Veverková, E. & Toma, S. (2008). Chem. Pap. 62, 334-338.]); Khan et al. (2009[Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.]). For classification of hydrogen bonds, see: Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press Inc.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10BrNO

  • Mr = 228.09

  • Monoclinic, C c

  • a = 22.349 (4) Å

  • b = 6.0328 (10) Å

  • c = 7.3673 (12) Å

  • [beta] = 107.980 (3)°

  • V = 944.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.305, Tmax = 0.919

  • 3713 measured reflections

  • 1651 independent reflections

  • 1550 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 788 Friedel pairs

  • Flack parameter: 0.022 (12)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.97 (3) 1.83 (3) 2.791 (4) 172 (4)
C2-H2...Cg1ii 0.95 2.83 3.58 (3) 137
C5-H5...Cg1iii 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[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Elslager, E. F., Benton, E. L., Short, F. W. & Tendick, F. H. (1956). J. Am. Chem. Soc. 78, 3453-3457.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fioravanti, R., Biava, M., Porretta, G. C., Landolfi, C., Simonetti, N., Villa, A., Conte, E. & Porta-Puglia, A. (1995). Eur. J. Med. Chem. 30, 123-132.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183-191.  [ISI] [CrossRef] [PubMed] [ChemPort]
Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press Inc.
Jafarpour, M., Rezaeifard, A., Gazkar, S. & Danehchin, M. (2011). Transition Met. Chem. 36, 685-690.  [ISI] [CrossRef] [ChemPort]
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.  [CrossRef] [PubMed] [ChemPort]
Mallikarjun, S. Y. & Sangamesh, A. P. (1997). Transition Met. Chem. 22, 220-224.
Morrison, R. T. & Boyd, R. N. (1987). Organic Chemistry, 5th ed., pp. 945-946. Boston: Allyn and Bacon Inc.
Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.  [ChemPort]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Solomon, E. I. & Lowery, M. D. (1993). Science, 259, 1575-1581.  [CrossRef] [ChemPort] [PubMed] [ISI]
Tidwell, T. T. (2007). Angew. Chem. Int. Ed. 46, 2-7.
Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Gunasekaran, B. & Manivannan, V. (2010). Acta Cryst. E66, o316.  [CSD] [CrossRef] [details]
Veverková, E. & Toma, S. (2008). Chem. Pap. 62, 334-338.
Williams, D. B. G., Traut, T., Kriel, F. H. & Van Zyl, W. E. (2007). Inorg. Chem. Commun. 10, 538-542.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3477  [ doi:10.1107/S1600536812048155 ]

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