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Volume 69 
Part 8 
Page o1333  
August 2013  

Received 8 June 2013
Accepted 18 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.004 Å
R = 0.068
wR = 0.193
Data-to-parameter ratio = 17.9
Details
Open access

A triclinic polymorph of (E)-2-(4-isobutylphenyl)-N'-[1-(4-nitrophenyl)ethylidene]propanohydrazide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India,bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore, 570 006, India, and cDepartment of Physics, St Philomena's College, Mysore, 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

The asymmetric unit of the triclinic polymorph of the title compound, C21H25N3O3, consists of two molecules, whereas for the monoclinic polymorph Z' = 1 [Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445.]). Acta Cryst. E65, o445]. The two molecules exhibit an E configuration with respect to the C=N bond. The molecules are linked into dimers by N-H...O and C-H...O hydrogen bonds forming R22(8) ring motifs. In addition, [pi]-[pi] interactions occur between nitrophenyl groups [minimum centroid-centroid distance 3.940 (2) Å], stacking the molecules along the ac plane.

Related literature

For the structure of the monoclinic polymorph of the title compound, see: Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the pharmacological activity of hydrazones, see: Bedia et al. (2006[Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.]); Rollas et al. (2002[Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.]); Terzioglu & Gursoy (2003[Terzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781-786.]).

[Scheme 1]

Experimental

Crystal data
  • C21H25N3O3

  • Mr = 367.44

  • Triclinic, [P \overline 1]

  • a = 12.201 (5) Å

  • b = 13.429 (5) Å

  • c = 13.932 (5) Å

  • [alpha] = 90.470 (7)°

  • [beta] = 110.099 (6)°

  • [gamma] = 107.321 (6)°

  • V = 2030.9 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.23 × 0.22 × 0.22 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 21740 measured reflections

  • 8844 independent reflections

  • 4673 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.193

  • S = 1.02

  • 8844 reflections

  • 495 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1A...O1Bi 0.86 2.14 2.977 (3) 165
N1B-H1B...O1Aii 0.86 2.15 2.919 (3) 149
C15A-H15C...O1Bi 0.96 2.41 3.252 (4) 147
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2579 ).


Acknowledgements

SMK thanks UGC-BRS and the University of Mysore for awarding a fellowship. MPS acknowledges the University Grants Commission, New Delhi, India.

References

Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445.  [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, Oxfordshire, England.
Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Terzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781-786.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1333  [ doi:10.1107/S1600536813019892 ]

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