1,5-Bis­[1-(2-hy­droxy­phen­yl)ethyl­idene]carbonohydrazide dimethyl­formamide monosolvate

Du, L.; Zhang, W.

doi:10.1107/S1600536810037517

Volume 66
Part 10
Page o2645
October 2010

Received 5 September 2010
Accepted 19 September 2010
Online 30 September 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.051
wR = 0.165
Data-to-parameter ratio = 13.7
Details

1,5-Bis[1-(2-hydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide monosolvate

Lingyun Du ^a ^* and Wenkang Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: dulingyun@lcu.edu.cn

In the title compound, C₁₇H₁₈N₄O₃·C₃H₇NO, the main disubstituted urea and solvate molecules are linked by pairs of N-HO hydrogen bonds. In the main molecules, the benzene rings form a dihedral angle of 15.59 (13)° a;nd two intramolecular O-HN hydrogen bonds influence the molecular conformation. In the crystal structure, weak intermolecular C-HO interactions link the hydrogen-bonded pairs into chains along the b axis. The chains associate via C-H [pi] interactions.

Related literature

For a related structure, see: Zukerman-Schpector et al. (2009). For the bioactivity of carbonohydrazide derivatives, see: Loncle et al. (2004); Li et al. (2004).

Experimental

Crystal data

C₁₇H₁₈N₄O₃·C₃H₇NO
M_r = 399.45
Monoclinic, P 2₁ /c
a = 16.6372 (15) Å
b = 7.5880 (9) Å
c = 16.2967 (14) Å
= 94.472 (1)°
V = 2051.1 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.47 × 0.46 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.958, T_max = 0.979
10277 measured reflections
3596 independent reflections
1712 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.165
S = 1.04
3596 reflections
263 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O4	0.86	2.02	2.805 (3)	151
N3-H3O4	0.86	2.09	2.858 (4)	148
O2-H2AN2	0.82	1.83	2.548 (3)	145
O3-H3AN4	0.82	1.83	2.546 (3)	145
C6-H6O1ⁱ	0.93	2.57	3.241 (4)	129
C10-H10ACgⁱⁱ	0.96	2.66	3.536 (4)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: CV2762 ).

Acknowledgements

The authors acknowledge financial support by the Science Foundation of China (grant No. 20877037).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem. 43, 5174-5176.
Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067-1071.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.

organic compounds