1-[(Z)-1-Ferrocenyl-ethyl-idene]thio-carbonohydrazide.

In the title compound, [Fe(C5H5)(C8H11N4S)], the cyclo-penta-dienyl (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 ethyl-idene-thio-carbonohydrazide 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 mol-ecule adopts a trans geometry about the C=N double bond. In the crystal, N-H⋯(N/S) and C-H⋯S inter-actions stack the mol-ecules 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 = 316.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.155

S = 1.06

2654 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.90 e Å−3

Δρmin = −0.53 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044078/sj5273sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[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

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)

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) ; (ii) ; (iii) ; (iv) .