N′-(3,4-Dimeth­oxy­benzyl­idene)-3,5-dihy­droxy­benzohydrazide methanol monosolvate

Zhang, Q.-H.; Zhou, L.-D.; Li, C.-X.; Huang, S.-S.; Zhang, B.-J.

doi:10.1107/S1600536811029850

Volume 67
Part 8
Page o2189
August 2011

Received 12 July 2011
Accepted 23 July 2011
Online 30 July 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.162
Data-to-parameter ratio = 12.6
Details

N'-(3,4-Dimethoxybenzylidene)-3,5-dihydroxybenzohydrazide methanol monosolvate

Qi-Hui Zhang,^a ^* Lian-Di Zhou,^b Chuan-Xun Li,^c Shan-Shan Huang ^c and Bao-Jing Zhang ^c

^aCollege of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, People's Republic of China,^bDepartment of Immunology, Basic Medical College, Chongqing Medical University, Chongqing 400016, People's Republic of China, and ^cSchool of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
Correspondence e-mail: zhangqh11@126.com

In the title compound, C₁₆H₁₆N₂O₅·CH₄O, the two benzene rings in the Schiff base molecule form a dihedral angle of 17.1 (1)°. In the crystal, intermolecular O-HO hydrogen bonds link the components into corrugated sheets parallel to the (101) plane.

Related literature

For the crystal structures of related Schiff base compounds, see: Deng et al. (2009); Huang et al. (2008). For antibacterial and antitumor activities of Schiff base complexes, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002).

Experimental

Crystal data

C₁₆H₁₆N₂O₅·CH₄O
M_r = 348.35
Monoclinic, P 2₁ /c
a = 12.467 (3) Å
b = 12.201 (3) Å
c = 11.149 (3) Å
= 91.191 (3)°
V = 1695.5 (7) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
8351 measured reflections
2984 independent reflections
1794 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.162
S = 1.00
2984 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.68 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O6	0.82	1.92	2.728 (3)	168
O1-H1O5ⁱ	0.82	1.93	2.742 (3)	172
O6-H6O4ⁱⁱ	0.82	2.19	2.973 (4)	161
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5134 ).

Acknowledgements

This project was supported by the Fundamental Research Funds for the Central Universities (project No. CDJRC10220006).

References

Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100-6106.
Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721.
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410-411.
Huang, S. S., Diao, Y. P. & Kang, T. G. (2008). Z. Kristallogr. New Cryst. Struct. 223, 167-168.
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds