(E)-N′-(2,5-Dimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Wang, S.-Y.; Yuan, L.; Xu, L.; Zhang, Z.; Diao, Y.-P.; Lv, D.-C.

doi:10.1107/S1600536809015165

Volume 65
Part 5
Page o1154
May 2009

Received 15 April 2009
Accepted 23 April 2009
Online 30 April 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.050
wR = 0.149
Data-to-parameter ratio = 13.1
Details

(E)-N'-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate

Shou-Yu Wang,^a Liang Yuan,^b Liang Xu,^c Zhen Zhang,^a Yun-Peng Diao ^a,^c ^* and De-Cheng Lv ^a ^*

^aDepartment of Orthopaedics, The First Affiliated Hospital of Dalian Medical University, Dalian 116011, People's Republic of China,^bDepartment of Orthopaedics, The Second Affiliated Hospital of Dalian Medical University, Dalian 116011, People's Republic of China, and ^cCollege of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600, People's Republic of China
Correspondence e-mail: lixiaokuan@126.com, diaoyiwen@126.com

The two molecules in the asymmetric unit of the title compound, C₂₀H₁₉N₃O₄·CH₄O, are paired via O-H(O,N), N-HO, and C-HO hydrogen bonds. The molecular skeleton of the acetohydrazide molecule is close to planar; the benzene and quinoline mean planes form a dihedral angle of 3.9 (3)°. The crystal packing exhibits weak intermolecular C-HO hydrogen bonds and [pi] - [pi] interactions, indicated by short distances of 3.668 (3) Å, between the centroids of N-containing six-membered rings from neighbouring acetohydrazide molecules.

Related literature

For applications of 8-hydroxyquinoline and its derivatives, see: Park et al. (2006); Karmakar et al. (2007). For a related structure, see Wen et al. (2005).

Experimental

Crystal data

C₂₀H₁₉N₃O₄·CH₄O
M_r = 397.42
Triclinic, $[P \overline 1]$
a = 9.4199 (12) Å
b = 10.8652 (14) Å
c = 11.1721 (14) Å
= 93.268 (1)°
= 112.816 (2)°
= 107.859 (3)°
V = 982.8 (2) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.979, T_max = 0.985
5196 measured reflections
3456 independent reflections
2363 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.149
S = 1.03
3456 reflections
263 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H5AO1	0.82	2.53	2.996 (3)	117
O5-H5AN1	0.82	2.06	2.782 (3)	147
N2-H2O5	0.86	2.01	2.856 (3)	166
C12-H12O5	0.93	2.51	3.305 (3)	144
C3-H3O2ⁱ	0.93	2.60	3.220 (3)	125
C20-H20AO2ⁱⁱ	0.96	2.59	3.511 (5)	160
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, z.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: CV2552 ).

References

Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). CrystEngComm, 9, 379-389.
Park, K. M., Moon, S. T., Kang, Y. J., Kim, H. J., Seo, J. & Lee, S. S. (2006). Inorg. Chem. Commun. 9, 671-674.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045-o2046.

organic compounds