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

Asiri, A.M.; Arshad, M.N.; Ishaq, M.; Alamry, K.A.; Shafiq, M.

doi:10.1107/S1600536812044078

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 (C-C) = 0.006 Å
R = 0.053
wR = 0.155
Data-to-parameter ratio = 14.3
Details

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

Abdullah M. Asiri,^a ^* Muhammad Nadeem Arshad,^a Muhammad Ishaq,^b Khalid A. Alamry ^a and Muhammad Shafiq ^c ^*

^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-HS 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). For related structures, see: Li & Du (2011); Vikneswaran et al. (2010a,b).

Experimental

Crystal data

[Fe(C₅H₅)(C₈H₁₁N₄S)]
M_r = 316.21
Monoclinic, P 2₁ /a
a = 6.4560 (2) Å
b = 13.0664 (3) Å
c = 15.8559 (4) Å
= 91.028 (2)°
V = 1337.34 (6) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.435, T_max = 1.000
8219 measured reflections
2654 independent reflections
2199 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(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
_max = 0.90 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NN4ⁱ	0.85 (5)	2.51 (5)	3.349 (5)	170 (4)
N4-H4AS1ⁱⁱ	0.86 (4)	2.65 (4)	3.501 (3)	169 (4)
N4-H4BN1ⁱⁱⁱ	0.91 (4)	2.62 (4)	3.443 (4)	151 (3)
C6-H6S1^iv	0.98	2.81	3.671 (4)	147
N3-H3NN1	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Li, X. & Du, L.-Z. (2011). Acta Cryst. E67, m1113.
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.
Ornelas, C. (2011). New J. Chem. 35, 1973-1985.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010a). Acta Cryst. E66, m679.
Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010b). Acta Cryst. E66, m697-m698.

metal-organic compounds