(E)-1-(3,4-Dimethyl­benzyl­idene)-2,2-diphenyl­hydrazine

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

doi:10.1107/S1600536811015352

Volume 67
Part 6
Page o1287
June 2011

Received 10 April 2011
Accepted 23 April 2011
Online 7 May 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.100
Data-to-parameter ratio = 15.0
Details

(E)-1-(3,4-Dimethylbenzylidene)-2,2-diphenylhydrazine

Angel Mendoza,^a ^* Blanca M. Cabrera-Vivas,^b Ruth Meléndrez-Luevano,^b Juan C. Ramírez ^b and Marcos Flores-Alamo ^c

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

The asymmetric unit of the title compound, C₂₁H₂₀N₂, contain two molecules, both of them showing an E configuration of the C=N bond. The dihedral angles between the phenyl rings in the phenylhydrazone groups are 86.84 (10) and 84.85 (8)° for the two molecules. Intermolecular C-H [pi] interactions are observed in the crystal structure.

Related literature

For applications of hydrazones, see: Angell et al. (2006); Buss et al. (2004); Melnyk et al. (2006); Ranford et al. (1998). For related structures see: Clulow et al. (2008); Mendoza et al. (2010).

Experimental

Crystal data

C₂₁H₂₀N₂
M_r = 300.39
Triclinic, $[P \overline 1]$
a = 9.9375 (5) Å
b = 10.6322 (5) Å
c = 17.5680 (8) Å
= 77.530 (4)°
= 76.480 (4)°
= 77.074 (4)°
V = 1732.60 (14) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 293 K
0.61 × 0.42 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.971, T_max = 0.984
12246 measured reflections
6288 independent reflections
3202 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.100
S = 0.85
6288 reflections
420 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31-C36, C37-C42, C2-C7 and C23-C28 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3Cg1ⁱ	0.93	2.81	3.7152 (18)	166
C6-H6Cg1ⁱⁱ	0.93	2.66	3.5506 (19)	160
C9-H9CCg2ⁱⁱⁱ	0.96	2.97	3.7170 (19)	136
C29-H29BCg3^iv	0.96	3.00	3.931 (2)	165
C41-H41Cg4ⁱ	0.93	2.83	3.590 (2)	139
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+1, -z; (iii) x, y+1, z; (iv) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 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: BT5512 ).

Acknowledgements

The authors are grateful to VIEP-BUAP for the supporting project CAVB-NAT-I10.

References

Angell, S. E., Rogers, C. W., Zhang, Y., Wolf, M. O. & Jones, W. E. Jr (2006). Coord. Chem. Rev. 250, 1829-1841.
Buss, J. L., Greene, B. T. & Torti, F. M. (2004). Curr. Top. Med. Chem. 4, 1623-1635.
Clulow, A. J., Selby, J. D., Cushion, M. G., Schwarz, A. D. & Mountford, P. (2008). Inorg. Chem. 47, 12049-12062.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Melnyk, P., Leroux, V., Serghraert, C. & Grellier, P. (2006). Bioorg. Med. Chem. Lett. 16, 31-35.
Mendoza, A., Cabrera-Vivas, B. M., Meléndrez-Luevano, R., Ramírez, J. C. & Flores-Alamo, M. (2010). Acta Cryst. E66, o2349.
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Ranford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226-1231.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds