2-(4-Isobutyl­phen­yl)-N′-[(3Z)-2-oxoindolin-3-yl­idene]propano­hydrazide

Mohamed, S.K.; Akkurt, M.; Albayati, M.R.; Singh, K.; Potgieter, H.

doi:10.1107/S160053681201269X

Volume 68
Part 4
Pages o1222-o1223
April 2012

Received 21 March 2012
Accepted 23 March 2012
Online 28 March 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R = 0.067
wR = 0.182
Data-to-parameter ratio = 20.2
Details

2-(4-Isobutylphenyl)-N'-[(3Z)-2-oxoindolin-3-ylidene]propanohydrazide

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Mustafa R. Albayati,^a Kuldip Singh ^c and Herman Potgieter ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cDepartment of Chemistry, University of Leicester, Leicester, England, and ^dSchool of Research, Enterprise & Innovation, Manchester Metropolitan University, Manchester M1 5GD, England
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₂₁H₂₃N₃O₂, the indolin-2-one group is essentially planar, with a maximum deviation of 0.016 (2) Å for the N atom, and makes a dihedral angle of 84.38 (14)° with the benzene ring. The =N-N(H)-C(=O)-C- torsion angle is 0.9 (3)°. In the crystal, molecules are linked into a three-dimensional network via N-HO and C-HO hydrogen bonds. In addition, a C-H [pi] interaction was observed.

Related literature

For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002). For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007). For some of our studies on the synthesis of biologically active compounds, see: Mohamed et al. (2012a,b); Soliman et al. (2012). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₁H₂₃N₃O₂
M_r = 349.42
Monoclinic, C 2/c
a = 30.366 (14) Å
b = 7.383 (3) Å
c = 21.904 (10) Å
= 130.311 (8)°
V = 3745 (3) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 150 K
0.35 × 0.21 × 0.10 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.992
15933 measured reflections
4494 independent reflections
2050 reflections with I > 2(I)
R_int = 0.096

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.182
S = 0.89
4494 reflections
223 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C6-C8 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	1.91	2.740 (4)	163
N3-H3AO2ⁱⁱ	0.86	2.16	2.965 (4)	155
C5-H5O2ⁱⁱ	0.93	2.30	3.218 (3)	172
C11-H11BCg1ⁱⁱⁱ	0.96	2.77	3.703 (4)	164
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5199 ).

Acknowledgements

MRA gratefully thanks the Iraqi Goverment for the financial support to perform this study. Manchester Metropolitan University is acknowledged for facilitating this collaboration.

References

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organic compounds