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Volume 68 
Part 1 
Pages o76-o77  
January 2012  

Received 5 December 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.055
wR = 0.176
Data-to-parameter ratio = 21.0
Details
Open access

(2E)-2-[(3E)-4-Phenylbut-3-en-2-ylidene]hydrazinecarboxamide

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and, Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C11H13N3O, the phenyl ring is disordered over two sites, with occupancy factors in a 0.520 (17):0.480 (17) ratio. The dihedral angle between the ring planes of the major and minor components of the disordered ring is 12.9 (2)°. In the crystal, molecules are linked by N-H...O hydrogen bonds, forming R22(8) ring motifs. C-H...O, C-H...N and C-H...[pi] interactions also occur.

Related literature

For background to the biological activity of semicarbazones, see: Beraldo et al. (2002[Beraldo, H., Sinisterra, R. D., Teixeira, L. R., Vieira, R. P. & Doretto, M. C. (2002). Biochem. Biophys. Res. Commun. 296, 241-246.]); Teixeira et al. (2003[Teixeira, L. R., Sinisterra, R. D., Vieira, R. P., Doretto, M. C. & Beraldo, H. (2003). J. Incl. Phenom. Macro. Chem. 47, 77-82.]); Du et al. (2004[Du, C. X., Guo, C., Hansell, E., Doyle, P. S., Caffrey, C. R., Holler, T. P., McKerrow, J. H. & Cohen, F. E. (2004). J. Med. Chem. 47, 3212-3219.]); Kucukguzel et al. (2006[Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahin, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353-359.]); Beraldo & Gambino (2004[Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.]). For related structures, see: Naik & Palenik (1974[Naik, D. V. & Palenik, G. J. (1974). Acta Cryst. B30, 2396-2401.]); Wang et al. (2004[Wang, J.-L., Jia, Y.-J. & Yu, M. (2004). Acta Cryst. E60, o662-o663.]); Yathirajan et al. (2006[Yathirajan, H. S., Bindya, S., Narayana, B., Sarojini, B. K. & Bolte, M. (2006). Acta Cryst. E62, o5925-o5926.]); Sarojini et al. (2007[Sarojini, B. K., Narayana, B., Bindya, S., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o2946.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13N3O

  • Mr = 203.24

  • Monoclinic, C 2/c

  • a = 15.1094 (8) Å

  • b = 24.4445 (11) Å

  • c = 7.0368 (4) Å

  • [beta] = 109.908 (6)°

  • V = 2443.7 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 123 K

  • 0.40 × 0.30 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.987, Tmax = 1.000

  • 12712 measured reflections

  • 3528 independent reflections

  • 2748 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.176

  • S = 1.05

  • 3528 reflections

  • 168 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A -C6A and C1B-C6B, respectively.

D-H...A D-H H...A D...A D-H...A
N2-H2B...O1i 0.88 2.12 2.9785 (15) 166
N3-H3B...O1ii 0.88 2.08 2.9434 (14) 168
C10-H10A...O1i 0.98 2.51 3.2384 (17) 131
C10-H10B...N1iii 0.98 2.58 3.4566 (19) 148
C4B-H4BA...Cg1iv 0.95 2.86 3.618 (5) 138
C4A-H4AA...Cg1iv 0.95 2.76 3.590 (5) 146
C4A-H4AA...Cg2iv 0.95 2.93 3.714 (5) 141
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+3]; (ii) [-x+1, y, -z+{\script{7\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]; (iv) [x, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5032 ).


Acknowledgements

BN thanks the UGC for financial assistance through SAP and BSR one-time grants for the purchase of chemicals. HSY thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.  [CrossRef] [PubMed] [ChemPort]
Beraldo, H., Sinisterra, R. D., Teixeira, L. R., Vieira, R. P. & Doretto, M. C. (2002). Biochem. Biophys. Res. Commun. 296, 241-246.  [CrossRef] [PubMed] [ChemPort]
Du, C. X., Guo, C., Hansell, E., Doyle, P. S., Caffrey, C. R., Holler, T. P., McKerrow, J. H. & Cohen, F. E. (2004). J. Med. Chem. 47, 3212-3219.  [ISI] [PubMed]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahin, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353-359.  [ISI] [PubMed]
Naik, D. V. & Palenik, G. J. (1974). Acta Cryst. B30, 2396-2401.  [CrossRef] [details] [ISI]
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sarojini, B. K., Narayana, B., Bindya, S., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o2946.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Teixeira, L. R., Sinisterra, R. D., Vieira, R. P., Doretto, M. C. & Beraldo, H. (2003). J. Incl. Phenom. Macro. Chem. 47, 77-82.  [ChemPort]
Wang, J.-L., Jia, Y.-J. & Yu, M. (2004). Acta Cryst. E60, o662-o663.  [CSD] [CrossRef] [details]
Yathirajan, H. S., Bindya, S., Narayana, B., Sarojini, B. K. & Bolte, M. (2006). Acta Cryst. E62, o5925-o5926.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o76-o77   [ doi:10.1107/S160053681105255X ]

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