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

Ge, R.-B.; Chen, Y.-H.; Wang, F.-T.; Wang, S.-S.; Qian, S.-S.

doi:10.1107/S1600536811052895

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 (C-C) = 0.010 Å
R = 0.051
wR = 0.133
Data-to-parameter ratio = 15.6
Details

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

Rong-Bao Ge,^a Yue-Hu Chen,^a Feng-Ting Wang,^a Shuang-Shuang Wang ^a and Shao-Song Qian ^a ^*

^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-HO hydrogen bonds generating infinite [101] chains. The methanol solvent molecules are connected with the main species by O-HO interactions.

Related literature

For background to bromophenols and their bioactivity, see: Liu et al. (2011). For related structures, see: Palmer et al. (1973); Li et al. (1995); Huang et al. (2006). For structural and theoretical aspects on the keto-enol equilibrium of salicylaldehyde Schiff bases, see: Chatziefthimiou et al. (2006).

Experimental

Crystal data

C₁₆H₁₅Br₂NO₂·CH₄O
M_r = 445.15
Monoclinic, P 2₁ /n
a = 8.752 (6) Å
b = 16.308 (10) Å
c = 13.001 (8) Å
= 104.047 (6)°
V = 1800 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.337, T_max = 0.406
8282 measured reflections
3292 independent reflections
1674 reflections with I > 2(I)
R_int = 0.072

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.133
S = 1.00
3292 reflections
211 parameters
H-atom parameters constrained
_max = 0.62 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	1.93	2.731 (7)	154
O3-H3O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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: 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.
Huang, S.-P., Li, H.-T., Shi, H.-P. & Tan, G.-F. (2006). Acta Cryst. E62, o1541-o1542.
Li, S., Lundquist, K., Soubbotin, N. & Stomberg, R. (1995). Acta Cryst. C51, 2366-2369.
Liu, M., Hansen, P. E. & Lin, X. (2011). Mar. Drugs, 9, 1273-1292.
Palmer, K. J., Wong, R. Y. & Jurd, L. (1973). Acta Cryst. B29, 1509-1514.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.