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Volume 68 
Part 1 
Page o117  
January 2012  

Received 29 November 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
R = 0.051
wR = 0.133
Data-to-parameter ratio = 15.6
Details
Open access

2,3-Dibromo-6-methoxy-4-[(phenethylamino)methylidene]cyclohexa-2,5-dien-1-one methanol monosolvate

aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China
Correspondence e-mail: njuqss@yahoo.com.cn

In the title compound, C16H15Br2NO2·CH4O, the mean planes of the substituted cyclohexa-2,5-dien-1-one and phenyl rings are almost parallel [dihedral angle = 7.84 (4)°]. The crystal packing is stabilized by N-H...O hydrogen bonds generating infinite [101] chains. The methanol solvent molecules are connected with the main species by O-H...O interactions.

Related literature

For background to bromophenols and their bioactivity, see: Liu et al. (2011[Liu, M., Hansen, P. E. & Lin, X. (2011). Mar. Drugs, 9, 1273-1292.]). For related structures, see: Palmer et al. (1973[Palmer, K. J., Wong, R. Y. & Jurd, L. (1973). Acta Cryst. B29, 1509-1514.]); Li et al. (1995[Li, S., Lundquist, K., Soubbotin, N. & Stomberg, R. (1995). Acta Cryst. C51, 2366-2369.]); Huang et al. (2006[Huang, S.-P., Li, H.-T., Shi, H.-P. & Tan, G.-F. (2006). Acta Cryst. E62, o1541-o1542.]). For structural and theoretical aspects on the keto-enol equilibrium of salicylaldehyde Schiff bases, see: Chatziefthimiou et al. (2006[Chatziefthimiou, S. D., Lazarou, Y. G., Hadjoudis, E., Dziembowska, T. & Mavridis, I. M. (2006). J. Phys. Chem. B, 110, 23701.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15Br2NO2·CH4O

  • Mr = 445.15

  • Monoclinic, P 21 /n

  • a = 8.752 (6) Å

  • b = 16.308 (10) Å

  • c = 13.001 (8) Å

  • [beta] = 104.047 (6)°

  • V = 1800 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.52 mm-1

  • T = 296 K

  • 0.25 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.337, Tmax = 0.406

  • 8282 measured reflections

  • 3292 independent reflections

  • 1674 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.133

  • S = 1.00

  • 3292 reflections

  • 211 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 1.93 2.731 (7) 154
O3-H3...O1ii 0.82 2.05 2.786 (8) 150
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2143 ).


Acknowledgements

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation (People's Republic of China).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chatziefthimiou, S. D., Lazarou, Y. G., Hadjoudis, E., Dziembowska, T. & Mavridis, I. M. (2006). J. Phys. Chem. B, 110, 23701.  [CSD] [CrossRef] [PubMed]
Huang, S.-P., Li, H.-T., Shi, H.-P. & Tan, G.-F. (2006). Acta Cryst. E62, o1541-o1542.  [CSD] [CrossRef] [details]
Li, S., Lundquist, K., Soubbotin, N. & Stomberg, R. (1995). Acta Cryst. C51, 2366-2369.  [CrossRef] [details]
Liu, M., Hansen, P. E. & Lin, X. (2011). Mar. Drugs, 9, 1273-1292.  [CrossRef] [ChemPort] [PubMed]
Palmer, K. J., Wong, R. Y. & Jurd, L. (1973). Acta Cryst. B29, 1509-1514.  [CrossRef] [ChemPort] [details] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o117  [ doi:10.1107/S1600536811052895 ]

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