(E)-1-(4-Nitro­benzyl­idene)-2,2-diphenyl­hydrazine

Mendoza, A.; Meléndrez-Luevano, R.; Cabrera-Vivas, B.M.; Acoltzi-X, C.; Flores-Alamo, M.

doi:10.1107/S1600536812043681

Volume 68
Part 11
Page o3238
November 2012

Received 17 October 2012
Accepted 22 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 14.8
Details

(E)-1-(4-Nitrobenzylidene)-2,2-diphenylhydrazine

Angel Mendoza,^a ^* Ruth Meléndrez-Luevano,^b Blanca M. Cabrera-Vivas,^b Claudia Acoltzi-X ^b and Marcos Flores-Alamo ^c

^aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico,^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and ^cFacultad de Química, Universidad Nacional Autónoma de México, 04510, México D.F., Mexico
Correspondence e-mail: angel.mendoza.m@gmail.com

The asymmetric unit of the title compound, C₁₉H₁₅N₃O₂, contains two molecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenylhydrazine groups are 86.09 (6) and 83.41 (5)° in the two molecules. The 4-nitrobenzene rings show torsion angles of 4.4 (2) and 10.9 (2)° from the two C=N-N planes. In the crystal, C-H [pi] interactions and C-HO hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.

Related literature

For applications of hydrazones, see: Angell et al. (2006); Vicini et al. (2002); Rollas et al. (2002).

Experimental

Crystal data

C₁₉H₁₅N₃O₂
M_r = 317.34
Triclinic, $[P \overline 1]$
a = 10.8648 (6) Å
b = 11.1477 (6) Å
c = 16.2075 (7) Å
= 72.084 (4)°
= 89.037 (4)°
= 62.084 (6)°
V = 1631.47 (18) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.6 × 0.36 × 0.29 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.963, T_max = 0.98
11850 measured reflections
6432 independent reflections
3566 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.100
S = 0.89
6432 reflections
434 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21-C26, C33-C38 and C8-C13 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3Cg1ⁱ	0.93	2.92	3.4080 (18)	114
C29-H29Cg2ⁱⁱ	0.93	2.80	3.6875 (18)	161
C7-H7Cg2	0.93	2.83	3.4223 (16)	123
C30-H30Cg3ⁱⁱⁱ	0.93	2.84	3.698 (2)	154
C6-H6O2^iv	0.93	2.60	3.342 (3)	138
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y+2, -z; (iv) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6850 ).

Acknowledgements

We are grateful for financial support (project No. CAVB-NAT11-I, VIEP-BUAP).

References

Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829-1841.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.

organic compounds