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Volume 68 
Part 12 
Page m1439  
December 2012  

Received 17 October 2012
Accepted 24 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.053
wR = 0.155
Data-to-parameter ratio = 14.3
Details
Open access

1-[(Z)-1-Ferrocenylethylidene]thiocarbonohydrazide

aChemistry Department & Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, Government College University, Faisalabad 38040, Pakistan.
Correspondence e-mail: aasiri2@kau.edu.sa, hafizshafique@hotmail.com

In the title compound, [Fe(C5H5)(C8H11N4S)], the cyclopentadienyl (Cp) rings of the ferrocene unit are close to being eclipsed. They are inclined to one another at an angle of 1.95 (2)° and lie 3.309 (2)Å away from each other. The ethylidenethiocarbonohydrazide fragment is planar, with an r.m.s. deviation of 0.0347 (2) Å from the mean plane of its eight non-H atoms, and makes dihedral angles of 21.78 (1) and 19.97 (1)° with respect to the two Cp rings. The molecule adopts a trans geometry about the C=N double bond. In the crystal, N-H...(N/S) and C-H...S interactions stack the molecules in an inverse fashion along the b axis.

Related literature

For the biological activities of related ferrocene compounds, see: Ornelas (2011[Ornelas, C. (2011). New J. Chem. 35, 1973-1985.]). For related structures, see: Li & Du (2011[Li, X. & Du, L.-Z. (2011). Acta Cryst. E67, m1113.]); Vikneswaran et al. (2010a[Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010a). Acta Cryst. E66, m679.],b[Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010b). Acta Cryst. E66, m697-m698.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C8H11N4S)]

  • Mr = 316.21

  • Monoclinic, P 21 /a

  • a = 6.4560 (2) Å

  • b = 13.0664 (3) Å

  • c = 15.8559 (4) Å

  • [beta] = 91.028 (2)°

  • V = 1337.34 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 10.47 mm-1

  • T = 296 K

  • 0.21 × 0.12 × 0.06 mm

Data collection
  • Agilent SuperNova CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.435, Tmax = 1.000

  • 8219 measured reflections

  • 2654 independent reflections

  • 2199 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.155

  • S = 1.06

  • 2654 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.90 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...N4i 0.85 (5) 2.51 (5) 3.349 (5) 170 (4)
N4-H4A...S1ii 0.86 (4) 2.65 (4) 3.501 (3) 169 (4)
N4-H4B...N1iii 0.91 (4) 2.62 (4) 3.443 (4) 151 (3)
C6-H6...S1iv 0.98 2.81 3.671 (4) 147
N3-H3N...N1 1.04 (4) 2.09 (4) 2.565 (4) 105 (3)
Symmetry codes: (i) x+1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and 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: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5273 ).


Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via Research Group Track of grant No. 3-102/428.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Li, X. & Du, L.-Z. (2011). Acta Cryst. E67, m1113.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Ornelas, C. (2011). New J. Chem. 35, 1973-1985.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010a). Acta Cryst. E66, m679.  [CSD] [CrossRef] [details]
Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010b). Acta Cryst. E66, m697-m698.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, m1439  [ doi:10.1107/S1600536812044078 ]

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