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

Samshuddin, S.; Butcher, R.J.; Yıldırım, S.O.; Akkurt, M.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S160053681105255X

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 (C-C) = 0.002 Å
Disorder in main residue
R = 0.055
wR = 0.176
Data-to-parameter ratio = 21.0
Details

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

S. Samshuddin,^a Ray J. Butcher,^b Sema Ozturk Yildirim,^c Mehmet Akkurt,^d ^* B. Narayana ^a and H. S. Yathirajan ^e

^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-HO hydrogen bonds, forming R₂²(8) ring motifs. C-HO, C-HN and C-H [pi] interactions also occur.

Related literature

For background to the biological activity of semicarbazones, see: Beraldo et al. (2002); Teixeira et al. (2003); Du et al. (2004); Kucukguzel et al. (2006); Beraldo & Gambino (2004). For related structures, see: Naik & Palenik (1974); Wang et al. (2004); Yathirajan et al. (2006); Sarojini et al. (2007).

Experimental

Crystal data

C₁₁H₁₃N₃O
M_r = 203.24
Monoclinic, C 2/c
a = 15.1094 (8) Å
b = 24.4445 (11) Å
c = 7.0368 (4) Å
= 109.908 (6)°
V = 2443.7 (2) Å³
Z = 8
Mo K radiation
= 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 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.987, T_max = 1.000
12712 measured reflections
3528 independent reflections
2748 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.176
S = 1.05
3528 reflections
168 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N2-H2BO1ⁱ	0.88	2.12	2.9785 (15)	166
N3-H3BO1ⁱⁱ	0.88	2.08	2.9434 (14)	168
C10-H10AO1ⁱ	0.98	2.51	3.2384 (17)	131
C10-H10BN1ⁱⁱⁱ	0.98	2.58	3.4566 (19)	148
C4B-H4BACg1^iv	0.95	2.86	3.618 (5)	138
C4A-H4AACg1^iv	0.95	2.76	3.590 (5)	146
C4A-H4AACg2^iv	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Beraldo, H., Sinisterra, R. D., Teixeira, L. R., Vieira, R. P. & Doretto, M. C. (2002). Biochem. Biophys. Res. Commun. 296, 241-246.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahin, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353-359.
Naik, D. V. & Palenik, G. J. (1974). Acta Cryst. B30, 2396-2401.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Teixeira, L. R., Sinisterra, R. D., Vieira, R. P., Doretto, M. C. & Beraldo, H. (2003). J. Incl. Phenom. Macro. Chem. 47, 77-82.
Wang, J.-L., Jia, Y.-J. & Yu, M. (2004). Acta Cryst. E60, o662-o663.
Yathirajan, H. S., Bindya, S., Narayana, B., Sarojini, B. K. & Bolte, M. (2006). Acta Cryst. E62, o5925-o5926.

organic compounds