1-{(E)-[5-(2-Nitro­phen­yl)furan-2-yl]methyl­idene}-2,2-diphenyl­hydrazine

Flores-Alamo, M.; Cabrera-Vivas, B.M.; Meléndrez-Luevano, R.; Hernández P., J.M.; Ruiz-Azuara, L.

doi:10.1107/S1600536812050246

Volume 69
Part 1
Page o90
January 2013

Received 6 December 2012
Accepted 9 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 13.0
Details

1-{(E)-[5-(2-Nitrophenyl)furan-2-yl]methylidene}-2,2-diphenylhydrazine

Marcos Flores-Alamo,^a ^* Blanca M. Cabrera-Vivas,^b Ruth Meléndrez-Luevano,^b Julio M. Hernández P.^b and Lena Ruiz-Azuara ^a

^aFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico, and ^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico
Correspondence e-mail: mfa@unam.mx

In the title compound, C₂₃H₁₇N₃O₃, the terminal benzene rings are oriented at dihedral angles of 3.67 (7), 76.02 (7) and 16.37 (7)° with respect to the central furan ring. In the crystal, molecules are connected via weak C-HO hydrogen bonds, resulting in a three-dimensional supramolecular array.

Related literature

For applications of hydrazones, see: Robinson (1963); Sztanke et al. (2007); Al-Macrosaur et al. (2007); Kucukguzel et al. (2003); Roma et al. (2000); Smalley et al. (2006); Gemma et al. (2006). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental

Crystal data

C₂₃H₁₇N₃O₃
M_r = 383.4
Monoclinic, C 2/c
a = 11.2439 (2) Å
b = 17.3325 (4) Å
c = 19.7575 (4) Å
= 105.778 (2)°
V = 3705.36 (13) Å³
Z = 8
Cu K radiation
= 0.76 mm^-1
T = 130 K
0.58 × 0.23 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.759, T_max = 0.892
12881 measured reflections
3395 independent reflections
3070 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.097
S = 1.03
3395 reflections
262 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O2ⁱ	0.95	2.48	3.1294 (16)	126
C11-H11O3ⁱⁱ	0.95	2.57	3.4336 (18)	151
C12-H12O3ⁱⁱⁱ	0.95	2.48	3.3786 (18)	158
Symmetry codes: (i) x+1, y, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5663 ).

Acknowledgements

We are grateful for financial support (project No. CAVB-NATG-12, VIEP-BUAP). MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

Al-Macrosaur, L. Q., Dayam, R., Taheri, L., Witvrouw, M., Debyser, Z. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6472-6475.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gemma, S., Kukreja, G., Fattorusso, C., Persico, M., Romano, M. P., Altarelli, M., Savini, L., Campiani, G., Fattorusso, E., Basilico, N., Taramelli, D., Yardley, V. & Butini, S. (2006). Bioorg. Med. Chem. Lett. 6, 5384-5388.
Kucukguzel, S. G., Mazi, A., Sahin, F., Ozturk, S. & Stables, J. (2003). Eur. J. Med. Chem. 38, 1005-1013.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Robinson, B. (1963). Chem. Rev. 63, 373-382.
Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1035.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smalley, T. L. Jr, Peat, A. J., Boucheron, J. A., Dickerson, S., Garrido, D., Preugschat, F., Schweiker, S. L., Thomson, S. A. & Wang, T. Y. (2006). Bioorg. Med. Chem. Lett. 16, 2091-2094.
Sztanke, K., Pasterhak, K., Rzymowska, J., Sztanke, M. & Kandefer-Szerszen, M. (2007). Eur. J. Med. Chem. 43, 404-419.

organic compounds