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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 [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.165
Data-to-parameter ratio = 13.7
Details
Open access

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

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-H...O hydrogen bonds. In the main molecules, the benzene rings form a dihedral angle of 15.59 (13)° a;nd two intramolecular O-H...N hydrogen bonds influence the molecular conformation. In the crystal structure, weak intermolecular C-H...O 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[Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.]). For the bioactivity of carbonohydrazide derivatives, see: Loncle et al. (2004[Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067-1071.]); Li et al. (2004[Li, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem. 43, 5174-5176.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N4O3·C3H7NO

  • Mr = 399.45

  • Monoclinic, P 21 /c

  • a = 16.6372 (15) Å

  • b = 7.5880 (9) Å

  • c = 16.2967 (14) Å

  • [beta] = 94.472 (1)°

  • V = 2051.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.979

  • 10277 measured reflections

  • 3596 independent reflections

  • 1712 reflections with I > 2[sigma](I)

  • Rint = 0.059

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

  • wR(F2) = 0.165

  • S = 1.04

  • 3596 reflections

  • 263 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12-C17 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O4 0.86 2.02 2.805 (3) 151
N3-H3...O4 0.86 2.09 2.858 (4) 148
O2-H2A...N2 0.82 1.83 2.548 (3) 145
O3-H3A...N4 0.82 1.83 2.546 (3) 145
C6-H6...O1i 0.93 2.57 3.241 (4) 129
C10-H10A...Cgii 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[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: 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.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067-1071.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.  [CrossRef] [details]


Acta Cryst (2010). E66, o2645  [ doi:10.1107/S1600536810037517 ]

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