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Volume 69 
Part 9 
Page o1442  
September 2013  

Received 16 June 2013
Accepted 26 July 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.044
wR = 0.113
Data-to-parameter ratio = 12.2
Details
Open access

N'-[(E)-2-Chlorobenzylidene]thiophene-2-carbohydrazide

aDepartment of Chemistry, An-Najah National University, Nablus, Palestinian Territories,bDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan,cDepartment of Chemistry, Hashemite University, PO Box 150459, Zarqa 13115, Jordan,dLCAE-URAC18, Faculté des Sciences, Université Mohammed Ier, Oujda-60000, Morocco, and eLaboratoire LCM, Faculté des Sciences, Université Mohammed Ier, Oujda-60000, Morocco
Correspondence e-mail: hadsal2003@yahoo.com

There are two independent molecules in the asymmetric unit of the title compound, C12H9ClN2OS, a Schiff base derived from hydrazide, in which the dihedral angles between the thiophene and benzene rings are 3.6 (3) and 7.3 (3)°. In the crystal, the two independent molecules are arranged about an approximate non-crystallographic inversion center and are connected by two N-H...O hydrogen bonds. Weak C-H...Cl contacts are also present. Conversely, there are neither significant aromatic stacking interactions nor contacts involving S atoms.

Related literature

For applications of Schiff bases, see: Cimerman et al. (1997[Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.]); Ren et al. (2002[Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.]). For related structures, see: Warad et al. (2009[Warad, I., Al-Nuri, M., Al-Resayes, S., Al-Farhan, K. & Ghazzali, M. (2009). Acta Cryst. E65, o1597.]); Jiang (2010[Jiang, J.-H. (2010). Acta Cryst. E66, o923.], 2011[Jiang, J.-H. (2011). Acta Cryst. E67, o50.]); Li & Jian (2010[Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399.]); Li & Meng (2010[Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN2OS

  • Mr = 264.72

  • Orthorhombic, P n a 21

  • a = 24.9465 (15) Å

  • b = 4.3709 (3) Å

  • c = 21.8091 (13) Å

  • V = 2378.0 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.870, Tmax = 0.954

  • 9965 measured reflections

  • 3845 independent reflections

  • 3341 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.113

  • S = 1.08

  • 3845 reflections

  • 316 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O1i 0.84 (4) 2.02 (5) 2.856 (4) 175 (4)
N1-H1A...O2ii 0.77 (4) 2.09 (4) 2.845 (5) 166 (5)
C10-H10A...Cl2iii 0.93 2.93 3.758 (5) 149
Symmetry codes: (i) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z]; (ii) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z]; (iii) [-x+1, -y+2, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2481 ).


Acknowledgements

The project was supported by AN-Najah National University. The X-ray structural work was done at Hamdi Mango Center for Scientific Research at The University of Jordan, Amman 11942, Jordan.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.  [CrossRef] [ChemPort] [ISI]
Jiang, J.-H. (2010). Acta Cryst. E66, o923.  [CrossRef] [details]
Jiang, J.-H. (2011). Acta Cryst. E67, o50.  [CrossRef] [details]
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399.  [CSD] [CrossRef] [details]
Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685.  [CSD] [CrossRef] [details]
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Warad, I., Al-Nuri, M., Al-Resayes, S., Al-Farhan, K. & Ghazzali, M. (2009). Acta Cryst. E65, o1597.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1442  [ doi:10.1107/S1600536813020850 ]

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