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

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

doi:10.1107/S1600536812044078

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1439

doi:10.1107/S1600536812044078

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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

(Received 17 October 2012; accepted 24 October 2012; online 3 November 2012)

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

[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
β = 91.028 (2)°
V = 1337.34 (6) Å³
Z = 4
Cu Kα radiation
μ = 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 > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(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
Δρ_max = 0.90 e Å⁻³
Δρ_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⋯S1^iv	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); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044078/sj5273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044078/sj5273Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For the biological activities of related ferrocene compounds, see: Ornelas (2011). For related structures, see: Li & Du (2011); Vikneswaran et al. (2010a,b).

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: 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).

Figures top

	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.

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

Crystal data top

[Fe(C₅H₅)(C₈H₁₁N₄S)]	F(000) = 656
M_r = 316.21	D_x = 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

Data collection top

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	R_int = 0.044
ω scans	θ_max = 74.6°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −7→8
T_min = 0.435, T_max = 1.000	k = −15→16
8219 measured reflections	l = −16→19

Refinement top

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(F_o²) + (0.1061P)² + 0.0547P] where P = (F_o² + 2F_c²)/3
2654 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₈H₁₁N₄S)]	V = 1337.34 (6) Å³
M_r = 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)°

Data collection top

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)
T_min = 0.435, T_max = 1.000	R_int = 0.044
8219 measured reflections

Refinement top

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	Δρ_max = 0.90 e Å⁻³
2654 reflections	Δρ_min = −0.53 e Å⁻³
185 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···S1^iv	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)]
M_r	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)
T_min, T_max	0.435, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8219, 2654, 2199
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···S1^iv	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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