metal-organic compounds
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). For related structures, see: Li & Du (2011); Vikneswaran et al. (2010a,b).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell 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).
Supporting information
10.1107/S1600536812044078/sj5273sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044078/sj5273Isup2.hkl
Thiocarbonohydrazide was refluxed with an equimolar amount of 1-acetylferrocene for 3 h in ethanol to give an orange yellow solution. The volume was reduced under vacum and on cooling gave the title compound as a very stable orange-yellow solid. This was recrystallized from dichloromethane under slow evaporation to obtain suitable orange crystals.
All the C—H H-atoms were positioned with idealized geometry with C—H = 0.93 Å for Cp, & C—H = 0.96 Å for methyl groups. H-atoms were refined as riding with Uiso(H) = Ueq(C), where k = 1.2 for Cp and 1.5 for methyl H-atoms.
All H atoms bound to N were located in a difference Fourier map and refined freely with N—H = 0.85 (5)—1.04 (4) Å, Uiso(H) = 1.2 Ueq(N).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).Fig. 1. The molecular structure of (I) with 50% displacement ellipsoids. | |
Fig. 2. Unit cell packing diagram showing intermolecular hydrogen bonds, drawn using dashed lines. |
[Fe(C5H5)(C8H11N4S)] | F(000) = 656 |
Mr = 316.21 | Dx = 1.571 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2yab | Cell parameters from 3298 reflections |
a = 6.4560 (2) Å | θ = 2.8–74.4° |
b = 13.0664 (3) Å | µ = 10.47 mm−1 |
c = 15.8559 (4) Å | T = 296 K |
β = 91.028 (2)° | Prismatic, orange |
V = 1337.34 (6) Å3 | 0.21 × 0.12 × 0.06 mm |
Z = 4 |
Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer | 2654 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2199 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.044 |
ω scans | θmax = 74.6°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −7→8 |
Tmin = 0.435, Tmax = 1.000 | k = −15→16 |
8219 measured reflections | l = −16→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1061P)2 + 0.0547P] where P = (Fo2 + 2Fc2)/3 |
2654 reflections | (Δ/σ)max = 0.001 |
185 parameters | Δρmax = 0.90 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
[Fe(C5H5)(C8H11N4S)] | V = 1337.34 (6) Å3 |
Mr = 316.21 | Z = 4 |
Monoclinic, P21/a | Cu Kα radiation |
a = 6.4560 (2) Å | µ = 10.47 mm−1 |
b = 13.0664 (3) Å | T = 296 K |
c = 15.8559 (4) Å | 0.21 × 0.12 × 0.06 mm |
β = 91.028 (2)° |
Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer | 2654 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 2199 reflections with I > 2σ(I) |
Tmin = 0.435, Tmax = 1.000 | Rint = 0.044 |
8219 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.90 e Å−3 |
2654 reflections | Δρmin = −0.53 e Å−3 |
185 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.25938 (7) | 0.50404 (3) | 0.15149 (3) | 0.0371 (2) | |
S1 | 0.17096 (16) | 0.37123 (7) | 0.62411 (5) | 0.0523 (3) | |
N1 | 0.1806 (4) | 0.38168 (19) | 0.37809 (17) | 0.0384 (6) | |
N2 | 0.2477 (5) | 0.3779 (2) | 0.46126 (18) | 0.0415 (6) | |
N3 | −0.0929 (5) | 0.3759 (2) | 0.49333 (19) | 0.0456 (7) | |
N4 | −0.2709 (5) | 0.3764 (3) | 0.5435 (2) | 0.0506 (7) | |
C1 | 0.2337 (5) | 0.3837 (2) | 0.2332 (2) | 0.0399 (7) | |
C2 | 0.3377 (6) | 0.3530 (3) | 0.1576 (2) | 0.0461 (8) | |
H2 | 0.4784 | 0.3251 | 0.1548 | 0.055* | |
C3 | 0.2023 (7) | 0.3694 (3) | 0.0887 (2) | 0.0531 (9) | |
H3 | 0.2333 | 0.3557 | 0.0295 | 0.064* | |
C4 | 0.0139 (6) | 0.4114 (3) | 0.1191 (2) | 0.0524 (9) | |
H4 | −0.1070 | 0.4311 | 0.0845 | 0.063* | |
C5 | 0.0333 (5) | 0.4206 (3) | 0.2077 (2) | 0.0456 (7) | |
H5 | −0.0724 | 0.4476 | 0.2453 | 0.055* | |
C6 | 0.4169 (8) | 0.6184 (3) | 0.2136 (3) | 0.0606 (11) | |
H6 | 0.4752 | 0.6149 | 0.2710 | 0.073* | |
C7 | 0.5197 (7) | 0.5906 (3) | 0.1381 (3) | 0.0609 (10) | |
H7 | 0.6617 | 0.5647 | 0.1345 | 0.073* | |
C8 | 0.3836 (7) | 0.6080 (3) | 0.0701 (3) | 0.0567 (9) | |
H8 | 0.4130 | 0.5963 | 0.0105 | 0.068* | |
C9 | 0.1983 (7) | 0.6459 (3) | 0.1024 (3) | 0.0595 (10) | |
H9 | 0.0750 | 0.6646 | 0.0688 | 0.071* | |
C10 | 0.2169 (8) | 0.6521 (3) | 0.1906 (3) | 0.0614 (10) | |
H10 | 0.1104 | 0.6763 | 0.2292 | 0.074* | |
C11 | 0.3164 (5) | 0.3790 (2) | 0.3196 (2) | 0.0389 (7) | |
C12 | 0.5448 (6) | 0.3701 (3) | 0.3352 (2) | 0.0512 (8) | |
H12A | 0.5964 | 0.4328 | 0.3592 | 0.077* | |
H12B | 0.6125 | 0.3570 | 0.2829 | 0.077* | |
H12C | 0.5722 | 0.3148 | 0.3737 | 0.077* | |
C13 | 0.1014 (5) | 0.3755 (2) | 0.5219 (2) | 0.0385 (7) | |
H4A | −0.273 (6) | 0.318 (3) | 0.569 (3) | 0.046* | |
H3N | −0.116 (6) | 0.380 (3) | 0.428 (3) | 0.046* | |
H4B | −0.250 (6) | 0.426 (3) | 0.583 (3) | 0.046* | |
H2N | 0.375 (7) | 0.378 (3) | 0.476 (3) | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0375 (3) | 0.0404 (3) | 0.0333 (3) | −0.00125 (18) | 0.0015 (2) | −0.00105 (17) |
S1 | 0.0663 (6) | 0.0548 (5) | 0.0357 (4) | 0.0002 (4) | −0.0060 (4) | −0.0019 (3) |
N1 | 0.0401 (14) | 0.0415 (13) | 0.0337 (12) | 0.0000 (10) | −0.0007 (10) | 0.0027 (10) |
N2 | 0.0377 (15) | 0.0476 (16) | 0.0391 (14) | 0.0008 (11) | −0.0026 (11) | 0.0017 (11) |
N3 | 0.0402 (16) | 0.0554 (17) | 0.0412 (15) | −0.0007 (12) | 0.0024 (11) | 0.0054 (12) |
N4 | 0.0487 (18) | 0.0489 (17) | 0.0547 (19) | −0.0019 (13) | 0.0149 (14) | 0.0061 (14) |
C1 | 0.0407 (17) | 0.0364 (15) | 0.0428 (17) | −0.0035 (12) | 0.0067 (13) | 0.0007 (12) |
C2 | 0.0477 (19) | 0.0410 (16) | 0.0501 (19) | −0.0010 (14) | 0.0126 (15) | −0.0041 (14) |
C3 | 0.065 (2) | 0.052 (2) | 0.0422 (18) | −0.0127 (17) | 0.0075 (16) | −0.0104 (15) |
C4 | 0.0442 (19) | 0.068 (2) | 0.0451 (19) | −0.0142 (16) | −0.0050 (15) | −0.0037 (16) |
C5 | 0.0351 (16) | 0.0561 (19) | 0.0456 (18) | −0.0076 (14) | 0.0023 (13) | −0.0026 (15) |
C6 | 0.083 (3) | 0.048 (2) | 0.051 (2) | −0.0168 (18) | −0.017 (2) | 0.0041 (15) |
C7 | 0.047 (2) | 0.051 (2) | 0.085 (3) | −0.0084 (16) | 0.0028 (19) | 0.007 (2) |
C8 | 0.073 (3) | 0.052 (2) | 0.0451 (18) | −0.0113 (18) | 0.0085 (17) | 0.0073 (15) |
C9 | 0.069 (3) | 0.051 (2) | 0.058 (2) | 0.0077 (18) | −0.0071 (19) | 0.0122 (17) |
C10 | 0.082 (3) | 0.0412 (18) | 0.061 (2) | 0.0059 (18) | 0.011 (2) | −0.0030 (16) |
C11 | 0.0378 (16) | 0.0328 (14) | 0.0462 (17) | −0.0005 (11) | 0.0052 (13) | 0.0050 (12) |
C12 | 0.0387 (18) | 0.060 (2) | 0.055 (2) | 0.0031 (15) | 0.0037 (15) | 0.0093 (16) |
C13 | 0.0471 (18) | 0.0295 (13) | 0.0389 (15) | 0.0005 (12) | 0.0007 (13) | 0.0011 (11) |
Fe1—C2 | 2.040 (3) | C1—C11 | 1.463 (5) |
Fe1—C5 | 2.040 (3) | C2—C3 | 1.403 (6) |
Fe1—C7 | 2.040 (4) | C2—H2 | 0.9800 |
Fe1—C1 | 2.046 (3) | C3—C4 | 1.426 (6) |
Fe1—C9 | 2.046 (4) | C3—H3 | 0.9800 |
Fe1—C8 | 2.047 (4) | C4—C5 | 1.414 (5) |
Fe1—C6 | 2.050 (4) | C4—H4 | 0.9800 |
Fe1—C3 | 2.052 (4) | C5—H5 | 0.9800 |
Fe1—C10 | 2.052 (4) | C6—C10 | 1.405 (7) |
Fe1—C4 | 2.052 (4) | C6—C7 | 1.427 (6) |
S1—C13 | 1.674 (3) | C6—H6 | 0.9800 |
N1—C11 | 1.288 (4) | C7—C8 | 1.396 (7) |
N1—N2 | 1.381 (4) | C7—H7 | 0.9800 |
N2—C13 | 1.360 (4) | C8—C9 | 1.400 (6) |
N2—H2N | 0.85 (5) | C8—H8 | 0.9800 |
N3—C13 | 1.326 (5) | C9—C10 | 1.405 (6) |
N3—N4 | 1.409 (4) | C9—H9 | 0.9800 |
N3—H3N | 1.04 (4) | C10—H10 | 0.9800 |
N4—H4A | 0.86 (4) | C11—C12 | 1.495 (5) |
N4—H4B | 0.91 (4) | C12—H12A | 0.9600 |
C1—C5 | 1.431 (5) | C12—H12B | 0.9600 |
C1—C2 | 1.442 (4) | C12—H12C | 0.9600 |
C2—Fe1—C5 | 68.93 (14) | C3—C2—H2 | 125.9 |
C2—Fe1—C7 | 109.73 (16) | C1—C2—H2 | 125.9 |
C5—Fe1—C7 | 159.92 (18) | Fe1—C2—H2 | 125.9 |
C2—Fe1—C1 | 41.34 (12) | C2—C3—C4 | 108.7 (3) |
C5—Fe1—C1 | 41.02 (14) | C2—C3—Fe1 | 69.5 (2) |
C7—Fe1—C1 | 124.65 (17) | C4—C3—Fe1 | 69.7 (2) |
C2—Fe1—C9 | 160.19 (17) | C2—C3—H3 | 125.7 |
C5—Fe1—C9 | 121.08 (17) | C4—C3—H3 | 125.7 |
C7—Fe1—C9 | 67.13 (18) | Fe1—C3—H3 | 125.7 |
C1—Fe1—C9 | 156.89 (16) | C5—C4—C3 | 107.9 (3) |
C2—Fe1—C8 | 124.93 (15) | C5—C4—Fe1 | 69.3 (2) |
C5—Fe1—C8 | 157.19 (17) | C3—C4—Fe1 | 69.6 (2) |
C7—Fe1—C8 | 39.95 (18) | C5—C4—H4 | 126.1 |
C1—Fe1—C8 | 161.13 (17) | C3—C4—H4 | 126.1 |
C9—Fe1—C8 | 40.00 (18) | Fe1—C4—H4 | 126.1 |
C2—Fe1—C6 | 124.23 (17) | C4—C5—C1 | 108.4 (3) |
C5—Fe1—C6 | 122.18 (16) | C4—C5—Fe1 | 70.3 (2) |
C7—Fe1—C6 | 40.82 (19) | C1—C5—Fe1 | 69.71 (18) |
C1—Fe1—C6 | 107.53 (15) | C4—C5—H5 | 125.8 |
C9—Fe1—C6 | 67.21 (17) | C1—C5—H5 | 125.8 |
C8—Fe1—C6 | 67.80 (17) | Fe1—C5—H5 | 125.8 |
C2—Fe1—C3 | 40.11 (17) | C10—C6—C7 | 107.5 (4) |
C5—Fe1—C3 | 68.27 (15) | C10—C6—Fe1 | 70.0 (2) |
C7—Fe1—C3 | 124.49 (17) | C7—C6—Fe1 | 69.2 (2) |
C1—Fe1—C3 | 68.43 (14) | C10—C6—H6 | 126.2 |
C9—Fe1—C3 | 124.11 (19) | C7—C6—H6 | 126.2 |
C8—Fe1—C3 | 109.42 (16) | Fe1—C6—H6 | 126.2 |
C6—Fe1—C3 | 160.33 (19) | C8—C7—C6 | 108.1 (4) |
C2—Fe1—C10 | 158.85 (17) | C8—C7—Fe1 | 70.3 (2) |
C5—Fe1—C10 | 105.76 (17) | C6—C7—Fe1 | 69.9 (2) |
C7—Fe1—C10 | 67.87 (18) | C8—C7—H7 | 126.0 |
C1—Fe1—C10 | 121.34 (15) | C6—C7—H7 | 126.0 |
C9—Fe1—C10 | 40.09 (18) | Fe1—C7—H7 | 126.0 |
C8—Fe1—C10 | 67.71 (16) | C7—C8—C9 | 107.8 (4) |
C6—Fe1—C10 | 40.07 (19) | C7—C8—Fe1 | 69.8 (2) |
C3—Fe1—C10 | 158.7 (2) | C9—C8—Fe1 | 70.0 (2) |
C2—Fe1—C4 | 68.34 (16) | C7—C8—H8 | 126.1 |
C5—Fe1—C4 | 40.43 (14) | C9—C8—H8 | 126.1 |
C7—Fe1—C4 | 159.19 (19) | Fe1—C8—H8 | 126.1 |
C1—Fe1—C4 | 68.56 (15) | C8—C9—C10 | 109.0 (4) |
C9—Fe1—C4 | 107.24 (18) | C8—C9—Fe1 | 70.0 (2) |
C8—Fe1—C4 | 122.89 (17) | C10—C9—Fe1 | 70.2 (2) |
C6—Fe1—C4 | 157.60 (18) | C8—C9—H9 | 125.5 |
C3—Fe1—C4 | 40.67 (16) | C10—C9—H9 | 125.5 |
C10—Fe1—C4 | 121.69 (19) | Fe1—C9—H9 | 125.5 |
C11—N1—N2 | 118.7 (3) | C9—C10—C6 | 107.6 (4) |
C13—N2—N1 | 117.8 (3) | C9—C10—Fe1 | 69.7 (2) |
C13—N2—H2N | 119 (3) | C6—C10—Fe1 | 69.9 (2) |
N1—N2—H2N | 123 (3) | C9—C10—H10 | 126.2 |
C13—N3—N4 | 125.7 (3) | C6—C10—H10 | 126.2 |
C13—N3—H3N | 117 (2) | Fe1—C10—H10 | 126.2 |
N4—N3—H3N | 117 (2) | N1—C11—C1 | 115.6 (3) |
N3—N4—H4A | 107 (3) | N1—C11—C12 | 124.4 (3) |
N3—N4—H4B | 106 (3) | C1—C11—C12 | 120.1 (3) |
H4A—N4—H4B | 108 (4) | C11—C12—H12A | 109.5 |
C5—C1—C2 | 106.9 (3) | C11—C12—H12B | 109.5 |
C5—C1—C11 | 126.3 (3) | H12A—C12—H12B | 109.5 |
C2—C1—C11 | 126.8 (3) | C11—C12—H12C | 109.5 |
C5—C1—Fe1 | 69.27 (19) | H12A—C12—H12C | 109.5 |
C2—C1—Fe1 | 69.11 (19) | H12B—C12—H12C | 109.5 |
C11—C1—Fe1 | 126.4 (2) | N3—C13—N2 | 115.0 (3) |
C3—C2—C1 | 108.1 (3) | N3—C13—S1 | 124.5 (3) |
C3—C2—Fe1 | 70.4 (2) | N2—C13—S1 | 120.5 (3) |
C1—C2—Fe1 | 69.55 (18) | ||
C11—N1—N2—C13 | −176.7 (3) | C4—Fe1—C5—C1 | 119.4 (3) |
C2—Fe1—C1—C5 | −118.5 (3) | C2—Fe1—C6—C10 | −160.6 (2) |
C7—Fe1—C1—C5 | 160.9 (2) | C5—Fe1—C6—C10 | −75.5 (3) |
C9—Fe1—C1—C5 | 46.4 (5) | C7—Fe1—C6—C10 | 118.7 (4) |
C8—Fe1—C1—C5 | −168.3 (4) | C1—Fe1—C6—C10 | −118.2 (3) |
C6—Fe1—C1—C5 | 119.2 (2) | C9—Fe1—C6—C10 | 37.8 (3) |
C3—Fe1—C1—C5 | −81.2 (2) | C8—Fe1—C6—C10 | 81.3 (3) |
C10—Fe1—C1—C5 | 77.6 (3) | C3—Fe1—C6—C10 | 167.0 (4) |
C4—Fe1—C1—C5 | −37.4 (2) | C4—Fe1—C6—C10 | −42.0 (5) |
C5—Fe1—C1—C2 | 118.5 (3) | C2—Fe1—C6—C7 | 80.6 (3) |
C7—Fe1—C1—C2 | −80.6 (3) | C5—Fe1—C6—C7 | 165.7 (2) |
C9—Fe1—C1—C2 | 164.9 (4) | C1—Fe1—C6—C7 | 123.1 (3) |
C8—Fe1—C1—C2 | −49.8 (5) | C9—Fe1—C6—C7 | −80.9 (3) |
C6—Fe1—C1—C2 | −122.3 (2) | C8—Fe1—C6—C7 | −37.4 (3) |
C3—Fe1—C1—C2 | 37.3 (2) | C3—Fe1—C6—C7 | 48.3 (6) |
C10—Fe1—C1—C2 | −163.9 (2) | C10—Fe1—C6—C7 | −118.7 (4) |
C4—Fe1—C1—C2 | 81.1 (2) | C4—Fe1—C6—C7 | −160.7 (4) |
C2—Fe1—C1—C11 | 121.0 (4) | C10—C6—C7—C8 | 0.4 (4) |
C5—Fe1—C1—C11 | −120.5 (4) | Fe1—C6—C7—C8 | 60.2 (3) |
C7—Fe1—C1—C11 | 40.4 (4) | C10—C6—C7—Fe1 | −59.8 (3) |
C9—Fe1—C1—C11 | −74.1 (5) | C2—Fe1—C7—C8 | 121.3 (3) |
C8—Fe1—C1—C11 | 71.2 (6) | C5—Fe1—C7—C8 | −156.3 (4) |
C6—Fe1—C1—C11 | −1.3 (3) | C1—Fe1—C7—C8 | 165.1 (2) |
C3—Fe1—C1—C11 | 158.3 (3) | C9—Fe1—C7—C8 | −37.7 (3) |
C10—Fe1—C1—C11 | −42.9 (4) | C6—Fe1—C7—C8 | −118.8 (4) |
C4—Fe1—C1—C11 | −157.9 (3) | C3—Fe1—C7—C8 | 78.9 (3) |
C5—C1—C2—C3 | −0.9 (4) | C10—Fe1—C7—C8 | −81.3 (3) |
C11—C1—C2—C3 | 179.4 (3) | C4—Fe1—C7—C8 | 40.5 (6) |
Fe1—C1—C2—C3 | −60.1 (2) | C2—Fe1—C7—C6 | −119.9 (3) |
C5—C1—C2—Fe1 | 59.2 (2) | C5—Fe1—C7—C6 | −37.5 (6) |
C11—C1—C2—Fe1 | −120.5 (3) | C1—Fe1—C7—C6 | −76.1 (3) |
C5—Fe1—C2—C3 | 80.9 (2) | C9—Fe1—C7—C6 | 81.1 (3) |
C7—Fe1—C2—C3 | −120.5 (3) | C8—Fe1—C7—C6 | 118.8 (4) |
C1—Fe1—C2—C3 | 119.0 (3) | C3—Fe1—C7—C6 | −162.3 (2) |
C9—Fe1—C2—C3 | −43.4 (5) | C10—Fe1—C7—C6 | 37.5 (3) |
C8—Fe1—C2—C3 | −78.5 (3) | C4—Fe1—C7—C6 | 159.3 (4) |
C6—Fe1—C2—C3 | −163.8 (2) | C6—C7—C8—C9 | −0.1 (5) |
C10—Fe1—C2—C3 | 160.0 (4) | Fe1—C7—C8—C9 | 59.9 (3) |
C4—Fe1—C2—C3 | 37.3 (2) | C6—C7—C8—Fe1 | −60.0 (3) |
C5—Fe1—C2—C1 | −38.2 (2) | C2—Fe1—C8—C7 | −78.9 (3) |
C7—Fe1—C2—C1 | 120.4 (2) | C5—Fe1—C8—C7 | 159.1 (4) |
C9—Fe1—C2—C1 | −162.4 (5) | C1—Fe1—C8—C7 | −40.9 (6) |
C8—Fe1—C2—C1 | 162.5 (2) | C9—Fe1—C8—C7 | 118.7 (4) |
C6—Fe1—C2—C1 | 77.2 (3) | C6—Fe1—C8—C7 | 38.2 (3) |
C3—Fe1—C2—C1 | −119.0 (3) | C3—Fe1—C8—C7 | −120.9 (3) |
C10—Fe1—C2—C1 | 40.9 (5) | C10—Fe1—C8—C7 | 81.7 (3) |
C4—Fe1—C2—C1 | −81.7 (2) | C4—Fe1—C8—C7 | −164.1 (3) |
C1—C2—C3—C4 | 0.7 (4) | C2—Fe1—C8—C9 | 162.3 (3) |
Fe1—C2—C3—C4 | −58.8 (3) | C5—Fe1—C8—C9 | 40.4 (5) |
C1—C2—C3—Fe1 | 59.5 (2) | C7—Fe1—C8—C9 | −118.7 (4) |
C5—Fe1—C3—C2 | −82.7 (2) | C1—Fe1—C8—C9 | −159.7 (4) |
C7—Fe1—C3—C2 | 79.7 (3) | C6—Fe1—C8—C9 | −80.5 (3) |
C1—Fe1—C3—C2 | −38.4 (2) | C3—Fe1—C8—C9 | 120.3 (3) |
C9—Fe1—C3—C2 | 163.7 (2) | C10—Fe1—C8—C9 | −37.1 (3) |
C8—Fe1—C3—C2 | 121.6 (2) | C4—Fe1—C8—C9 | 77.2 (3) |
C6—Fe1—C3—C2 | 43.3 (5) | C7—C8—C9—C10 | −0.2 (5) |
C10—Fe1—C3—C2 | −160.1 (4) | Fe1—C8—C9—C10 | 59.5 (3) |
C4—Fe1—C3—C2 | −120.2 (3) | C7—C8—C9—Fe1 | −59.8 (3) |
C2—Fe1—C3—C4 | 120.2 (3) | C2—Fe1—C9—C8 | −47.2 (6) |
C5—Fe1—C3—C4 | 37.5 (2) | C5—Fe1—C9—C8 | −163.0 (2) |
C7—Fe1—C3—C4 | −160.2 (2) | C7—Fe1—C9—C8 | 37.7 (3) |
C1—Fe1—C3—C4 | 81.8 (2) | C1—Fe1—C9—C8 | 163.4 (4) |
C9—Fe1—C3—C4 | −76.2 (3) | C6—Fe1—C9—C8 | 82.1 (3) |
C8—Fe1—C3—C4 | −118.2 (2) | C3—Fe1—C9—C8 | −79.5 (3) |
C6—Fe1—C3—C4 | 163.5 (4) | C10—Fe1—C9—C8 | 120.0 (4) |
C10—Fe1—C3—C4 | −39.9 (5) | C4—Fe1—C9—C8 | −121.0 (3) |
C2—C3—C4—C5 | −0.3 (4) | C2—Fe1—C9—C10 | −167.2 (4) |
Fe1—C3—C4—C5 | −59.0 (3) | C5—Fe1—C9—C10 | 77.1 (3) |
C2—C3—C4—Fe1 | 58.7 (3) | C7—Fe1—C9—C10 | −82.3 (3) |
C2—Fe1—C4—C5 | 82.5 (2) | C1—Fe1—C9—C10 | 43.4 (5) |
C7—Fe1—C4—C5 | 171.2 (4) | C8—Fe1—C9—C10 | −120.0 (4) |
C1—Fe1—C4—C5 | 37.9 (2) | C6—Fe1—C9—C10 | −37.8 (3) |
C9—Fe1—C4—C5 | −118.0 (2) | C3—Fe1—C9—C10 | 160.5 (3) |
C8—Fe1—C4—C5 | −159.0 (2) | C4—Fe1—C9—C10 | 119.0 (3) |
C6—Fe1—C4—C5 | −46.2 (5) | C8—C9—C10—C6 | 0.5 (5) |
C3—Fe1—C4—C5 | 119.3 (3) | Fe1—C9—C10—C6 | 59.9 (3) |
C10—Fe1—C4—C5 | −76.6 (3) | C8—C9—C10—Fe1 | −59.4 (3) |
C2—Fe1—C4—C3 | −36.8 (2) | C7—C6—C10—C9 | −0.5 (4) |
C5—Fe1—C4—C3 | −119.3 (3) | Fe1—C6—C10—C9 | −59.8 (3) |
C7—Fe1—C4—C3 | 51.9 (5) | C7—C6—C10—Fe1 | 59.3 (3) |
C1—Fe1—C4—C3 | −81.4 (2) | C2—Fe1—C10—C9 | 168.0 (4) |
C9—Fe1—C4—C3 | 122.7 (3) | C5—Fe1—C10—C9 | −119.8 (3) |
C8—Fe1—C4—C3 | 81.7 (3) | C7—Fe1—C10—C9 | 80.3 (3) |
C6—Fe1—C4—C3 | −165.5 (4) | C1—Fe1—C10—C9 | −161.6 (3) |
C10—Fe1—C4—C3 | 164.1 (2) | C8—Fe1—C10—C9 | 37.0 (3) |
C3—C4—C5—C1 | −0.3 (4) | C6—Fe1—C10—C9 | 118.5 (4) |
Fe1—C4—C5—C1 | −59.5 (2) | C3—Fe1—C10—C9 | −49.4 (6) |
C3—C4—C5—Fe1 | 59.2 (3) | C4—Fe1—C10—C9 | −78.9 (3) |
C2—C1—C5—C4 | 0.7 (4) | C2—Fe1—C10—C6 | 49.4 (5) |
C11—C1—C5—C4 | −179.6 (3) | C5—Fe1—C10—C6 | 121.6 (3) |
Fe1—C1—C5—C4 | 59.8 (2) | C7—Fe1—C10—C6 | −38.2 (3) |
C2—C1—C5—Fe1 | −59.1 (2) | C1—Fe1—C10—C6 | 79.9 (3) |
C11—C1—C5—Fe1 | 120.6 (3) | C9—Fe1—C10—C6 | −118.5 (4) |
C2—Fe1—C5—C4 | −80.9 (2) | C8—Fe1—C10—C6 | −81.5 (3) |
C7—Fe1—C5—C4 | −170.9 (4) | C3—Fe1—C10—C6 | −168.0 (4) |
C1—Fe1—C5—C4 | −119.4 (3) | C4—Fe1—C10—C6 | 162.6 (2) |
C9—Fe1—C5—C4 | 80.0 (3) | N2—N1—C11—C1 | −179.7 (3) |
C8—Fe1—C5—C4 | 50.9 (5) | N2—N1—C11—C12 | 1.1 (4) |
C6—Fe1—C5—C4 | 161.1 (2) | C5—C1—C11—N1 | 19.8 (5) |
C3—Fe1—C5—C4 | −37.7 (2) | C2—C1—C11—N1 | −160.5 (3) |
C10—Fe1—C5—C4 | 120.7 (3) | Fe1—C1—C11—N1 | 109.6 (3) |
C2—Fe1—C5—C1 | 38.5 (2) | C5—C1—C11—C12 | −161.0 (3) |
C7—Fe1—C5—C1 | −51.5 (5) | C2—C1—C11—C12 | 18.6 (5) |
C9—Fe1—C5—C1 | −160.6 (2) | Fe1—C1—C11—C12 | −71.3 (4) |
C8—Fe1—C5—C1 | 170.3 (4) | N4—N3—C13—N2 | −178.3 (3) |
C6—Fe1—C5—C1 | −79.6 (3) | N4—N3—C13—S1 | 2.3 (4) |
C3—Fe1—C5—C1 | 81.7 (2) | N1—N2—C13—N3 | 0.8 (4) |
C10—Fe1—C5—C1 | −119.9 (2) | N1—N2—C13—S1 | −179.8 (2) |
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−1/2, −y+1/2, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C8H11N4S)] |
Mr | 316.21 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 296 |
a, b, c (Å) | 6.4560 (2), 13.0664 (3), 15.8559 (4) |
β (°) | 91.028 (2) |
V (Å3) | 1337.34 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 10.47 |
Crystal size (mm) | 0.21 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.435, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8219, 2654, 2199 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.155, 1.06 |
No. of reflections | 2654 |
No. of parameters | 185 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.90, −0.53 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).
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) | 147.4 |
N3—H3N···N1 | 1.04 (4) | 2.09 (4) | 2.565 (4) | 105 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1. |
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Functionalized ferrocene based organometallic compounds have gained much interest in different areas of applied research especially for their use as anti-tumor agents (Ornelas, 2011). Here we report the crystal structure of the title compound, which is closely related to the reported ferrocene derivatives N'-(4-hydroxybenzylidene)ferrocene-1-carbohydrazide (Li & Du, 2011), ferrocene-1-carbaldehyde thiosemicarbazone (Vikneswaran et al., 2010a) & ferrocene-1-carbaldehyde 4-ethylthiosemicarbazone (Vikneswaran et al., 2010b).
In the title compound, the distances of the Fe1 atom from the centroids of each Cp ring are 1.649 (3) Å Cp1 (C1—C5) & 1.661 (5) Å Cp2 (C5—C10). The dihedral angle between the mean planes of the two Cp rings is 1.95 (2)° and the rings are approximately eclipsed. The mean plane of (ethylidene)thiocarbonohydrazide is twisted 21.78 (1)°, 19.97 (1)° with respect to the Cp1 & Cp2. In the crystal structure intermolecular N—H···(N/S) & C—H···S hydrogen bonding interactions (Table. 1, Fig. 2) stack the molecules in an inverse fashions along the b axis.