metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

Ferrocene-1-carbaldehyde 4-ethyl­thio­semi­carbazone

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 11 May 2010; accepted 17 May 2010; online 22 May 2010)

The asymmetric unit of title compound, [Fe(C5H5)(C9H12N3S)], contains two crystallographically independent mol­ecules, A and B. The two cyclo­penta­dienyl (Cp) rings are parallel to each other in both mol­ecules, forming dihedral angles of 2.3 (3) and 1.0 (3)°, respectively, and adopt an eclipsed conformation. The mean plane of the semicarbazone group is twisted slightly away from the attached Cp ring in both mol­ecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)°. The ethyl group in mol­ecule A is coplanar with the mean plane of the semicarbazone group [C—N—C—C torsion angle = −175.2 (4)°], whereas it is nearly perpendicular in mol­ecule B [C—N—C—C torsion angle = 84.8 (6)°]. In the crystal structure, inter­molecular N—H⋯S hydrogen bonds link the mol­ecules into dimers. These dimers are further linked into chains via inter­molecular C—H⋯S hydrogen bonds. The crystal studied was a non-merohedral twin with a refined ratio of the twin components of 0.265 (2):0.735 (2).

Related literature

For related structures, see: Vikneswaran et al. (2009[Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2009). Acta Cryst. E65, m1524-m1525.], 2010[Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, m679.]). For the preparation of the title compound, see: Casas et al. (2004[Casas, J. S., Castaño, M. V., Cifuentes, M. C., Garcia-Monteagudo, J. C., Sánchez, A., Sordo, J. & Abram, U. (2004). J. Inorg. Biochem. 98, 1009-1016.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C9H12N3S)]

  • Mr = 315.22

  • Triclinic, [P \overline 1]

  • a = 7.4432 (3) Å

  • b = 10.6906 (5) Å

  • c = 18.4616 (9) Å

  • α = 77.975 (3)°

  • β = 83.807 (3)°

  • γ = 78.076 (3)°

  • V = 1402.56 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.21 mm−1

  • T = 100 K

  • 0.29 × 0.16 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.723, Tmax = 0.901

  • 8184 measured reflections

  • 8184 independent reflections

  • 6947 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.170

  • S = 1.07

  • 8184 reflections

  • 362 parameters

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

  • Δρmax = 3.94 e Å−3

  • Δρmin = −1.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2NA⋯S1Ai 0.82 (6) 2.59 (6) 3.387 (4) 164 (5)
N2B—H2NB⋯S1Bii 0.89 (9) 2.55 (9) 3.430 (5) 170 (5)
C4A—H4AA⋯S1Biii 0.98 2.79 3.715 (4) 157
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

As a continuation of our research related to ferrocenyl thiosemicarbazones and its metal complexes, herein we report the crystal structure of formylferrocene 4-ethylthiosemicarbazone.

The asymmetric unit of title compound consists of two crystallographically independent molecules, A and B (Fig. 1). The geometric parameter are comparable to those observed in its closely related structures (Vikneswaran et al., 2009, 2010). The Cp rings of each ferrocene residue are parallel, with dihedral angles of Cp1/Cp2 [C1A–C5A/C6A–C10A] = 2.3 (3)° and Cp3/Cp4 [C1B–C5B/C6B–C10B] = 1.0 (3)°. The Cp rings in both molecules adopt an eclipsed conformation [average torsion angles for C–Cg–Cg–C of 5.89 and 6.14°]. The mean plane of the semicarbazone group is slightly twisted away from the attached Cp rings in both molecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)° respectively. The ethyl group in molecule A is coplanar with the mean plane of semicarbazone group [torsion angle of C12A–N3A–C13A–C14B = -175.2 (4)°] whereas it is nearly perpendicular to the semicarbazone group [torsion angle of C12B–N3B–C13B–C14B = 84.8 (6)°] in molecule B.

In the crystal structure, intermolecular N2A–H2NA···S1A and N2B–H2NB···S1B hydrogen bonds link the molecules into dimers. These dimers are linked into one-dimensional chain via intermolecular C4A–H4AA···S1B hydrogen bonds (Fig. 2, Table 1).

Related literature top

For related structures, see: Vikneswaran et al. (2009, 2010). For the preparation of the title compound, see: Casas et al. (2004). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Formylferrocene 4-ethylthiosemicarbazone was prepared as described by Casas et al. (2004). The single crystals were grown from a CH2Cl2/n-CH6H14 (1:1 v/v) solution at room temperature in the dark.

Refinement top

N bound H-atoms were located from difference Fourier map and refined freely. The rest of H-atoms were placed in calculated positions, with C–H = 0.93–0.98 Å and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). Rotating-group model were applied for methyl group. The highest residual density peak is located 0.88 Å from atom Fe1B and the deepest hole is located 1.32 Å from atom C12B. The crystal studied is a non-merohedral twin with the refined ratio of twin components of 0.265 (2):0.735 (2).

Structure description top

As a continuation of our research related to ferrocenyl thiosemicarbazones and its metal complexes, herein we report the crystal structure of formylferrocene 4-ethylthiosemicarbazone.

The asymmetric unit of title compound consists of two crystallographically independent molecules, A and B (Fig. 1). The geometric parameter are comparable to those observed in its closely related structures (Vikneswaran et al., 2009, 2010). The Cp rings of each ferrocene residue are parallel, with dihedral angles of Cp1/Cp2 [C1A–C5A/C6A–C10A] = 2.3 (3)° and Cp3/Cp4 [C1B–C5B/C6B–C10B] = 1.0 (3)°. The Cp rings in both molecules adopt an eclipsed conformation [average torsion angles for C–Cg–Cg–C of 5.89 and 6.14°]. The mean plane of the semicarbazone group is slightly twisted away from the attached Cp rings in both molecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)° respectively. The ethyl group in molecule A is coplanar with the mean plane of semicarbazone group [torsion angle of C12A–N3A–C13A–C14B = -175.2 (4)°] whereas it is nearly perpendicular to the semicarbazone group [torsion angle of C12B–N3B–C13B–C14B = 84.8 (6)°] in molecule B.

In the crystal structure, intermolecular N2A–H2NA···S1A and N2B–H2NB···S1B hydrogen bonds link the molecules into dimers. These dimers are linked into one-dimensional chain via intermolecular C4A–H4AA···S1B hydrogen bonds (Fig. 2, Table 1).

For related structures, see: Vikneswaran et al. (2009, 2010). For the preparation of the title compound, see: Casas et al. (2004). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the molecules link into 1-D chains. Hydrogen atoms not involved in the hydrogen-bonding (dashed lines) are omitted for clarity.
Ferrocene-1-carbaldehyde 4-ethylthiosemicarbazone top
Crystal data top
[Fe(C5H5)(C9H12N3S)]Z = 4
Mr = 315.22F(000) = 656
Triclinic, P1Dx = 1.493 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4432 (3) ÅCell parameters from 9974 reflections
b = 10.6906 (5) Åθ = 2.3–30.0°
c = 18.4616 (9) ŵ = 1.21 mm1
α = 77.975 (3)°T = 100 K
β = 83.807 (3)°Block, brown
γ = 78.076 (3)°0.29 × 0.16 × 0.09 mm
V = 1402.56 (11) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8184 independent reflections
Radiation source: fine-focus sealed tube6947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 30.1°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1010
Tmin = 0.723, Tmax = 0.901k = 1415
8184 measured reflectionsl = 1125
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0564P)2 + 6.6396P]
where P = (Fo2 + 2Fc2)/3
8184 reflections(Δ/σ)max < 0.001
362 parametersΔρmax = 3.94 e Å3
0 restraintsΔρmin = 1.22 e Å3
Crystal data top
[Fe(C5H5)(C9H12N3S)]γ = 78.076 (3)°
Mr = 315.22V = 1402.56 (11) Å3
Triclinic, P1Z = 4
a = 7.4432 (3) ÅMo Kα radiation
b = 10.6906 (5) ŵ = 1.21 mm1
c = 18.4616 (9) ÅT = 100 K
α = 77.975 (3)°0.29 × 0.16 × 0.09 mm
β = 83.807 (3)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8184 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6947 reflections with I > 2σ(I)
Tmin = 0.723, Tmax = 0.901Rint = 0.000
8184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 3.94 e Å3
8184 reflectionsΔρmin = 1.22 e Å3
362 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > σ(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
xyzUiso*/Ueq
Fe1A0.13896 (8)0.05245 (6)0.63951 (3)0.01124 (13)
S1A0.29669 (15)0.61964 (10)0.42316 (6)0.0175 (2)
N1A0.2762 (5)0.2535 (3)0.5056 (2)0.0145 (7)
N2A0.3209 (5)0.3757 (3)0.4940 (2)0.0150 (7)
N3A0.0898 (5)0.4487 (3)0.4141 (2)0.0140 (7)
C1A0.1290 (6)0.0406 (4)0.6505 (2)0.0171 (8)
H1AA0.20020.09850.61080.021*
C2A0.1151 (6)0.0966 (4)0.6707 (2)0.0174 (8)
H2AA0.17540.14980.64740.021*
C3A0.0008 (6)0.1433 (4)0.7305 (2)0.0201 (9)
H3AA0.03480.23430.75550.024*
C4A0.0590 (7)0.0348 (5)0.7480 (2)0.0211 (9)
H4AA0.14030.03760.78690.025*
C5A0.0221 (6)0.0788 (5)0.6976 (3)0.0203 (9)
H5AA0.00520.16790.69590.024*
C6A0.2245 (5)0.0166 (4)0.5289 (2)0.0137 (7)
H6AA0.14910.03320.48830.016*
C7A0.2465 (6)0.1531 (4)0.5565 (2)0.0151 (8)
H7AA0.18780.21360.53840.018*
C8A0.3655 (6)0.1867 (4)0.6163 (2)0.0168 (8)
H8AA0.40350.27400.64580.020*
C9A0.4196 (5)0.0705 (4)0.6252 (2)0.0154 (8)
H9AA0.50110.06380.66200.018*
C10A0.3323 (5)0.0348 (4)0.5711 (2)0.0123 (7)
C11A0.3566 (5)0.1695 (4)0.5581 (2)0.0146 (8)
H11A0.43040.19470.58790.018*
C12A0.2306 (5)0.4739 (4)0.4442 (2)0.0125 (7)
C13A0.0243 (6)0.5431 (4)0.3617 (2)0.0151 (8)
H13A0.04950.56850.31640.018*
H13B0.07410.62030.38250.018*
C14A0.1810 (6)0.4851 (5)0.3440 (3)0.0223 (9)
H14A0.25220.54660.30730.033*
H14B0.25830.46520.38830.033*
H14C0.13140.40670.32530.033*
Fe1B0.30485 (8)0.46654 (6)0.14382 (3)0.01438 (14)
S1B0.24370 (18)0.06556 (11)0.06872 (7)0.0224 (2)
N1B0.2135 (5)0.2488 (4)0.0132 (2)0.0195 (8)
N2B0.1830 (6)0.1303 (4)0.0031 (2)0.0223 (8)
N3B0.4293 (6)0.1273 (4)0.0817 (2)0.0252 (9)
C1B0.5691 (6)0.3613 (5)0.1531 (2)0.0197 (9)
H1BA0.65110.33010.11270.024*
C2B0.5528 (6)0.4837 (4)0.1738 (3)0.0189 (9)
H2BA0.62300.55160.15070.023*
C3B0.4170 (6)0.4906 (4)0.2346 (3)0.0187 (8)
H3BA0.37810.56350.26090.022*
C4B0.3493 (6)0.3726 (4)0.2500 (2)0.0190 (8)
H4BA0.25390.35020.28870.023*
C5B0.4432 (7)0.2922 (4)0.2007 (3)0.0209 (9)
H5BA0.42310.20520.19870.025*
C6B0.2535 (6)0.5058 (5)0.0337 (2)0.0195 (9)
H6BA0.34130.48320.00720.023*
C7B0.2245 (7)0.6241 (4)0.0616 (3)0.0221 (9)
H7BA0.28950.69670.04330.026*
C8B0.0860 (6)0.6177 (4)0.1209 (3)0.0226 (9)
H8BA0.03910.68500.15060.027*
C9B0.0287 (6)0.4950 (5)0.1302 (3)0.0205 (9)
H9BA0.06480.46380.16720.025*
C10B0.1320 (6)0.4262 (4)0.0763 (2)0.0171 (8)
C11B0.1143 (6)0.2982 (4)0.0654 (3)0.0193 (9)
H11B0.03200.25270.09600.023*
C12B0.2896 (7)0.0721 (5)0.0494 (3)0.0204 (9)
C13B0.5572 (7)0.0852 (5)0.1416 (3)0.0284 (11)
H13C0.58090.00910.13400.034*
H13D0.67310.11220.13980.034*
C14B0.4841 (9)0.1411 (6)0.2179 (3)0.0374 (13)
H14D0.57420.11300.25530.056*
H14E0.45930.23450.22560.056*
H14F0.37270.11090.22080.056*
H2NA0.416 (8)0.390 (5)0.507 (3)0.016 (13)*
H2NB0.073 (12)0.109 (8)0.015 (5)0.07 (3)*
H3NB0.458 (11)0.186 (7)0.053 (4)0.05 (2)*
H3NA0.046 (8)0.384 (6)0.437 (3)0.026 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe1A0.0099 (3)0.0130 (3)0.0111 (3)0.0036 (2)0.0009 (2)0.0015 (2)
S1A0.0198 (5)0.0117 (5)0.0231 (5)0.0066 (4)0.0057 (4)0.0027 (4)
N1A0.0116 (15)0.0160 (17)0.0175 (17)0.0050 (13)0.0004 (13)0.0046 (13)
N2A0.0147 (16)0.0125 (16)0.0189 (17)0.0042 (13)0.0027 (13)0.0028 (13)
N3A0.0161 (16)0.0100 (15)0.0162 (17)0.0061 (13)0.0021 (13)0.0009 (13)
C1A0.0122 (17)0.018 (2)0.020 (2)0.0018 (15)0.0021 (15)0.0048 (16)
C2A0.0162 (18)0.018 (2)0.021 (2)0.0094 (15)0.0027 (16)0.0045 (16)
C3A0.025 (2)0.018 (2)0.016 (2)0.0071 (17)0.0021 (17)0.0007 (16)
C4A0.025 (2)0.028 (2)0.0121 (19)0.0105 (18)0.0030 (16)0.0041 (17)
C5A0.026 (2)0.020 (2)0.018 (2)0.0067 (17)0.0034 (17)0.0086 (17)
C6A0.0102 (17)0.0179 (19)0.0135 (18)0.0039 (14)0.0000 (14)0.0032 (15)
C7A0.0132 (17)0.0169 (19)0.0153 (19)0.0026 (14)0.0007 (14)0.0037 (15)
C8A0.0136 (18)0.0140 (19)0.021 (2)0.0005 (14)0.0020 (15)0.0006 (15)
C9A0.0098 (16)0.018 (2)0.0181 (19)0.0022 (14)0.0029 (14)0.0026 (15)
C10A0.0086 (16)0.0145 (18)0.0136 (18)0.0033 (14)0.0015 (13)0.0023 (14)
C11A0.0114 (17)0.0159 (19)0.0175 (19)0.0048 (14)0.0015 (14)0.0031 (15)
C12A0.0135 (17)0.0125 (18)0.0133 (18)0.0047 (14)0.0006 (14)0.0053 (14)
C13A0.0137 (17)0.0115 (18)0.019 (2)0.0021 (14)0.0043 (15)0.0001 (15)
C14A0.018 (2)0.025 (2)0.026 (2)0.0062 (17)0.0062 (17)0.0051 (18)
Fe1B0.0136 (3)0.0156 (3)0.0144 (3)0.0045 (2)0.0029 (2)0.0013 (2)
S1B0.0350 (6)0.0162 (5)0.0199 (5)0.0113 (4)0.0027 (4)0.0051 (4)
N1B0.0208 (18)0.0182 (18)0.0225 (19)0.0076 (14)0.0043 (15)0.0056 (15)
N2B0.029 (2)0.0195 (19)0.023 (2)0.0120 (16)0.0028 (16)0.0053 (15)
N3B0.0226 (19)0.031 (2)0.029 (2)0.0131 (17)0.0025 (16)0.0129 (18)
C1B0.019 (2)0.024 (2)0.016 (2)0.0011 (17)0.0039 (16)0.0049 (17)
C2B0.0118 (18)0.021 (2)0.024 (2)0.0075 (16)0.0022 (15)0.0016 (17)
C3B0.0182 (19)0.017 (2)0.023 (2)0.0021 (16)0.0045 (16)0.0076 (16)
C4B0.0179 (19)0.021 (2)0.017 (2)0.0045 (16)0.0027 (16)0.0009 (16)
C5B0.026 (2)0.016 (2)0.021 (2)0.0027 (17)0.0045 (17)0.0033 (16)
C6B0.021 (2)0.023 (2)0.0134 (19)0.0066 (17)0.0042 (16)0.0020 (16)
C7B0.031 (2)0.0121 (19)0.022 (2)0.0031 (17)0.0130 (19)0.0039 (16)
C8B0.023 (2)0.015 (2)0.029 (2)0.0032 (17)0.0095 (18)0.0050 (17)
C9B0.0165 (19)0.024 (2)0.021 (2)0.0053 (17)0.0042 (16)0.0028 (17)
C10B0.0169 (19)0.018 (2)0.0171 (19)0.0042 (15)0.0068 (15)0.0019 (16)
C11B0.019 (2)0.022 (2)0.020 (2)0.0095 (17)0.0035 (16)0.0021 (17)
C12B0.025 (2)0.020 (2)0.018 (2)0.0074 (17)0.0062 (17)0.0029 (16)
C13B0.023 (2)0.030 (3)0.035 (3)0.0052 (19)0.003 (2)0.014 (2)
C14B0.041 (3)0.046 (3)0.033 (3)0.018 (3)0.014 (2)0.024 (3)
Geometric parameters (Å, º) top
Fe1A—C2A2.037 (4)Fe1B—C3B2.036 (4)
Fe1A—C3A2.046 (4)Fe1B—C4B2.036 (4)
Fe1A—C1A2.046 (4)Fe1B—C2B2.037 (4)
Fe1A—C8A2.046 (4)Fe1B—C10B2.048 (4)
Fe1A—C9A2.051 (4)Fe1B—C9B2.050 (4)
Fe1A—C10A2.051 (4)Fe1B—C6B2.051 (4)
Fe1A—C5A2.052 (5)Fe1B—C7B2.053 (4)
Fe1A—C7A2.052 (4)Fe1B—C8B2.054 (4)
Fe1A—C6A2.053 (4)Fe1B—C1B2.060 (4)
Fe1A—C4A2.063 (4)Fe1B—C5B2.064 (5)
S1A—C12A1.687 (4)S1B—C12B1.691 (5)
N1A—C11A1.283 (5)N1B—C11B1.285 (6)
N1A—N2A1.383 (5)N1B—N2B1.384 (5)
N2A—C12A1.356 (5)N2B—C12B1.357 (7)
N2A—H2NA0.82 (6)N2B—H2NB0.89 (9)
N3A—C12A1.335 (5)N3B—C12B1.326 (6)
N3A—C13A1.447 (5)N3B—C13B1.461 (7)
N3A—H3NA0.84 (6)N3B—H3NB0.97 (8)
C1A—C5A1.410 (6)C1B—C2B1.417 (7)
C1A—C2A1.421 (6)C1B—C5B1.426 (6)
C1A—H1AA0.9800C1B—H1BA0.9800
C2A—C3A1.418 (6)C2B—C3B1.431 (6)
C2A—H2AA0.9800C2B—H2BA0.9800
C3A—C4A1.425 (7)C3B—C4B1.418 (6)
C3A—H3AA0.9800C3B—H3BA0.9800
C4A—C5A1.433 (7)C4B—C5B1.414 (7)
C4A—H4AA0.9800C4B—H4BA0.9800
C5A—H5AA0.9800C5B—H5BA0.9800
C6A—C7A1.424 (6)C6B—C10B1.431 (6)
C6A—C10A1.430 (5)C6B—C7B1.431 (7)
C6A—H6AA0.9800C6B—H6BA0.9800
C7A—C8A1.429 (6)C7B—C8B1.421 (7)
C7A—H7AA0.9800C7B—H7BA0.9800
C8A—C9A1.428 (6)C8B—C9B1.433 (6)
C8A—H8AA0.9800C8B—H8BA0.9800
C9A—C10A1.434 (6)C9B—C10B1.424 (7)
C9A—H9AA0.9800C9B—H9BA0.9800
C10A—C11A1.456 (6)C10B—C11B1.459 (6)
C11A—H11A0.9300C11B—H11B0.9300
C13A—C14A1.523 (6)C13B—C14B1.522 (8)
C13A—H13A0.9700C13B—H13C0.9700
C13A—H13B0.9700C13B—H13D0.9700
C14A—H14A0.9600C14B—H14D0.9600
C14A—H14B0.9600C14B—H14E0.9600
C14A—H14C0.9600C14B—H14F0.9600
C2A—Fe1A—C3A40.63 (18)C3B—Fe1B—C4B40.76 (18)
C2A—Fe1A—C1A40.72 (17)C3B—Fe1B—C2B41.13 (18)
C3A—Fe1A—C1A68.45 (18)C4B—Fe1B—C2B68.65 (18)
C2A—Fe1A—C8A123.50 (18)C3B—Fe1B—C10B162.68 (18)
C3A—Fe1A—C8A106.06 (18)C4B—Fe1B—C10B125.67 (17)
C1A—Fe1A—C8A161.08 (18)C2B—Fe1B—C10B154.96 (19)
C2A—Fe1A—C9A161.10 (17)C3B—Fe1B—C9B125.40 (19)
C3A—Fe1A—C9A124.71 (18)C4B—Fe1B—C9B108.12 (18)
C1A—Fe1A—C9A157.02 (18)C2B—Fe1B—C9B162.68 (19)
C8A—Fe1A—C9A40.79 (17)C10B—Fe1B—C9B40.67 (19)
C2A—Fe1A—C10A155.75 (17)C3B—Fe1B—C6B155.00 (18)
C3A—Fe1A—C10A162.98 (17)C4B—Fe1B—C6B162.63 (19)
C1A—Fe1A—C10A121.71 (17)C2B—Fe1B—C6B119.64 (18)
C8A—Fe1A—C10A68.66 (16)C10B—Fe1B—C6B40.86 (17)
C9A—Fe1A—C10A40.93 (16)C9B—Fe1B—C6B68.61 (18)
C2A—Fe1A—C5A68.06 (18)C3B—Fe1B—C7B120.00 (18)
C3A—Fe1A—C5A68.28 (19)C4B—Fe1B—C7B155.5 (2)
C1A—Fe1A—C5A40.26 (18)C2B—Fe1B—C7B106.91 (18)
C8A—Fe1A—C5A156.34 (18)C10B—Fe1B—C7B68.64 (18)
C9A—Fe1A—C5A122.29 (18)C9B—Fe1B—C7B68.55 (19)
C10A—Fe1A—C5A109.67 (17)C6B—Fe1B—C7B40.81 (19)
C2A—Fe1A—C7A106.16 (17)C3B—Fe1B—C8B107.44 (19)
C3A—Fe1A—C7A119.01 (18)C4B—Fe1B—C8B121.0 (2)
C1A—Fe1A—C7A124.63 (17)C2B—Fe1B—C8B125.02 (19)
C8A—Fe1A—C7A40.82 (16)C10B—Fe1B—C8B68.52 (18)
C9A—Fe1A—C7A68.53 (17)C9B—Fe1B—C8B40.87 (18)
C10A—Fe1A—C7A68.29 (16)C6B—Fe1B—C8B68.4 (2)
C5A—Fe1A—C7A162.30 (18)C7B—Fe1B—C8B40.5 (2)
C2A—Fe1A—C6A119.68 (17)C3B—Fe1B—C1B68.50 (18)
C3A—Fe1A—C6A154.10 (18)C4B—Fe1B—C1B68.19 (18)
C1A—Fe1A—C6A107.78 (17)C2B—Fe1B—C1B40.47 (18)
C8A—Fe1A—C6A68.80 (17)C10B—Fe1B—C1B120.59 (18)
C9A—Fe1A—C6A68.88 (16)C9B—Fe1B—C1B155.71 (19)
C10A—Fe1A—C6A40.79 (15)C6B—Fe1B—C1B107.35 (19)
C5A—Fe1A—C6A126.39 (18)C7B—Fe1B—C1B125.0 (2)
C7A—Fe1A—C6A40.58 (16)C8B—Fe1B—C1B161.93 (19)
C2A—Fe1A—C4A68.27 (18)C3B—Fe1B—C5B68.25 (18)
C3A—Fe1A—C4A40.57 (18)C4B—Fe1B—C5B40.33 (19)
C1A—Fe1A—C4A68.32 (19)C2B—Fe1B—C5B68.20 (18)
C8A—Fe1A—C4A120.07 (19)C10B—Fe1B—C5B108.19 (18)
C9A—Fe1A—C4A108.26 (18)C9B—Fe1B—C5B121.11 (19)
C10A—Fe1A—C4A126.87 (18)C6B—Fe1B—C5B125.56 (19)
C5A—Fe1A—C4A40.75 (19)C7B—Fe1B—C5B162.4 (2)
C7A—Fe1A—C4A154.51 (18)C8B—Fe1B—C5B156.1 (2)
C6A—Fe1A—C4A163.95 (18)C1B—Fe1B—C5B40.47 (18)
C11A—N1A—N2A115.2 (3)C11B—N1B—N2B116.6 (4)
C12A—N2A—N1A119.4 (3)C12B—N2B—N1B118.6 (4)
C12A—N2A—H2NA115 (4)C12B—N2B—H2NB116 (5)
N1A—N2A—H2NA124 (4)N1B—N2B—H2NB121 (6)
C12A—N3A—C13A124.1 (3)C12B—N3B—C13B126.0 (4)
C12A—N3A—H3NA116 (4)C12B—N3B—H3NB111 (5)
C13A—N3A—H3NA117 (4)C13B—N3B—H3NB121 (5)
C5A—C1A—C2A107.9 (4)C2B—C1B—C5B107.9 (4)
C5A—C1A—Fe1A70.1 (3)C2B—C1B—Fe1B68.9 (2)
C2A—C1A—Fe1A69.3 (2)C5B—C1B—Fe1B69.9 (3)
C5A—C1A—H1AA126.1C2B—C1B—H1BA126.0
C2A—C1A—H1AA126.1C5B—C1B—H1BA126.0
Fe1A—C1A—H1AA126.1Fe1B—C1B—H1BA126.0
C3A—C2A—C1A108.3 (4)C1B—C2B—C3B108.1 (4)
C3A—C2A—Fe1A70.0 (2)C1B—C2B—Fe1B70.6 (2)
C1A—C2A—Fe1A70.0 (2)C3B—C2B—Fe1B69.4 (2)
C3A—C2A—H2AA125.8C1B—C2B—H2BA126.0
C1A—C2A—H2AA125.8C3B—C2B—H2BA126.0
Fe1A—C2A—H2AA125.8Fe1B—C2B—H2BA126.0
C2A—C3A—C4A108.1 (4)C4B—C3B—C2B107.5 (4)
C2A—C3A—Fe1A69.4 (2)C4B—C3B—Fe1B69.6 (2)
C4A—C3A—Fe1A70.4 (2)C2B—C3B—Fe1B69.5 (2)
C2A—C3A—H3AA125.9C4B—C3B—H3BA126.3
C4A—C3A—H3AA125.9C2B—C3B—H3BA126.3
Fe1A—C3A—H3AA125.9Fe1B—C3B—H3BA126.3
C3A—C4A—C5A107.2 (4)C5B—C4B—C3B108.6 (4)
C3A—C4A—Fe1A69.1 (3)C5B—C4B—Fe1B70.9 (3)
C5A—C4A—Fe1A69.2 (3)C3B—C4B—Fe1B69.6 (3)
C3A—C4A—H4AA126.4C5B—C4B—H4BA125.7
C5A—C4A—H4AA126.4C3B—C4B—H4BA125.7
Fe1A—C4A—H4AA126.4Fe1B—C4B—H4BA125.7
C1A—C5A—C4A108.5 (4)C4B—C5B—C1B107.9 (4)
C1A—C5A—Fe1A69.6 (3)C4B—C5B—Fe1B68.8 (3)
C4A—C5A—Fe1A70.0 (3)C1B—C5B—Fe1B69.6 (3)
C1A—C5A—H5AA125.8C4B—C5B—H5BA126.1
C4A—C5A—H5AA125.8C1B—C5B—H5BA126.1
Fe1A—C5A—H5AA125.8Fe1B—C5B—H5BA126.1
C7A—C6A—C10A107.6 (3)C10B—C6B—C7B107.8 (4)
C7A—C6A—Fe1A69.7 (2)C10B—C6B—Fe1B69.5 (2)
C10A—C6A—Fe1A69.5 (2)C7B—C6B—Fe1B69.7 (2)
C7A—C6A—H6AA126.2C10B—C6B—H6BA126.1
C10A—C6A—H6AA126.2C7B—C6B—H6BA126.1
Fe1A—C6A—H6AA126.2Fe1B—C6B—H6BA126.1
C6A—C7A—C8A108.5 (4)C8B—C7B—C6B108.1 (4)
C6A—C7A—Fe1A69.7 (2)C8B—C7B—Fe1B69.8 (3)
C8A—C7A—Fe1A69.4 (3)C6B—C7B—Fe1B69.5 (2)
C6A—C7A—H7AA125.7C8B—C7B—H7BA126.0
C8A—C7A—H7AA125.7C6B—C7B—H7BA126.0
Fe1A—C7A—H7AA125.7Fe1B—C7B—H7BA126.0
C9A—C8A—C7A107.9 (4)C7B—C8B—C9B108.1 (4)
C9A—C8A—Fe1A69.8 (2)C7B—C8B—Fe1B69.7 (3)
C7A—C8A—Fe1A69.8 (2)C9B—C8B—Fe1B69.4 (3)
C9A—C8A—H8AA126.0C7B—C8B—H8BA125.9
C7A—C8A—H8AA126.0C9B—C8B—H8BA125.9
Fe1A—C8A—H8AA126.0Fe1B—C8B—H8BA125.9
C8A—C9A—C10A107.7 (3)C10B—C9B—C8B107.9 (4)
C8A—C9A—Fe1A69.4 (2)C10B—C9B—Fe1B69.6 (2)
C10A—C9A—Fe1A69.6 (2)C8B—C9B—Fe1B69.7 (2)
C8A—C9A—H9AA126.1C10B—C9B—H9BA126.1
C10A—C9A—H9AA126.1C8B—C9B—H9BA126.1
Fe1A—C9A—H9AA126.1Fe1B—C9B—H9BA126.1
C6A—C10A—C9A108.2 (4)C9B—C10B—C6B108.1 (4)
C6A—C10A—C11A125.5 (4)C9B—C10B—C11B126.0 (4)
C9A—C10A—C11A126.2 (4)C6B—C10B—C11B125.9 (4)
C6A—C10A—Fe1A69.7 (2)C9B—C10B—Fe1B69.8 (2)
C9A—C10A—Fe1A69.5 (2)C6B—C10B—Fe1B69.7 (2)
C11A—C10A—Fe1A129.0 (3)C11B—C10B—Fe1B127.2 (3)
N1A—C11A—C10A120.0 (4)N1B—C11B—C10B119.4 (4)
N1A—C11A—H11A120.0N1B—C11B—H11B120.3
C10A—C11A—H11A120.0C10B—C11B—H11B120.3
N3A—C12A—N2A116.8 (4)N3B—C12B—N2B116.3 (4)
N3A—C12A—S1A123.0 (3)N3B—C12B—S1B123.8 (4)
N2A—C12A—S1A120.1 (3)N2B—C12B—S1B119.9 (4)
N3A—C13A—C14A110.0 (3)N3B—C13B—C14B112.6 (4)
N3A—C13A—H13A109.7N3B—C13B—H13C109.1
C14A—C13A—H13A109.7C14B—C13B—H13C109.1
N3A—C13A—H13B109.7N3B—C13B—H13D109.1
C14A—C13A—H13B109.7C14B—C13B—H13D109.1
H13A—C13A—H13B108.2H13C—C13B—H13D107.8
C13A—C14A—H14A109.5C13B—C14B—H14D109.5
C13A—C14A—H14B109.5C13B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C13A—C14A—H14C109.5C13B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C11A—N1A—N2A—C12A174.2 (4)C11B—N1B—N2B—C12B177.4 (4)
C2A—Fe1A—C1A—C5A119.1 (4)C3B—Fe1B—C1B—C2B38.2 (3)
C3A—Fe1A—C1A—C5A81.4 (3)C4B—Fe1B—C1B—C2B82.2 (3)
C8A—Fe1A—C1A—C5A157.8 (5)C10B—Fe1B—C1B—C2B158.2 (3)
C9A—Fe1A—C1A—C5A48.1 (6)C9B—Fe1B—C1B—C2B168.1 (4)
C10A—Fe1A—C1A—C5A83.3 (3)C6B—Fe1B—C1B—C2B115.6 (3)
C7A—Fe1A—C1A—C5A167.4 (3)C7B—Fe1B—C1B—C2B74.1 (3)
C6A—Fe1A—C1A—C5A125.8 (3)C8B—Fe1B—C1B—C2B42.1 (7)
C4A—Fe1A—C1A—C5A37.6 (3)C5B—Fe1B—C1B—C2B119.5 (4)
C3A—Fe1A—C1A—C2A37.6 (3)C3B—Fe1B—C1B—C5B81.3 (3)
C8A—Fe1A—C1A—C2A38.8 (6)C4B—Fe1B—C1B—C5B37.3 (3)
C9A—Fe1A—C1A—C2A167.2 (4)C2B—Fe1B—C1B—C5B119.5 (4)
C10A—Fe1A—C1A—C2A157.7 (3)C10B—Fe1B—C1B—C5B82.3 (3)
C5A—Fe1A—C1A—C2A119.1 (4)C9B—Fe1B—C1B—C5B48.6 (5)
C7A—Fe1A—C1A—C2A73.5 (3)C6B—Fe1B—C1B—C5B124.9 (3)
C6A—Fe1A—C1A—C2A115.1 (3)C7B—Fe1B—C1B—C5B166.4 (3)
C4A—Fe1A—C1A—C2A81.4 (3)C8B—Fe1B—C1B—C5B161.6 (6)
C5A—C1A—C2A—C3A0.0 (5)C5B—C1B—C2B—C3B0.3 (5)
Fe1A—C1A—C2A—C3A59.7 (3)Fe1B—C1B—C2B—C3B59.5 (3)
C5A—C1A—C2A—Fe1A59.7 (3)C5B—C1B—C2B—Fe1B59.3 (3)
C1A—Fe1A—C2A—C3A119.3 (4)C3B—Fe1B—C2B—C1B118.9 (4)
C8A—Fe1A—C2A—C3A74.8 (3)C4B—Fe1B—C2B—C1B81.0 (3)
C9A—Fe1A—C2A—C3A45.2 (7)C10B—Fe1B—C2B—C1B49.0 (5)
C10A—Fe1A—C2A—C3A171.2 (4)C9B—Fe1B—C2B—C1B163.4 (6)
C5A—Fe1A—C2A—C3A81.8 (3)C6B—Fe1B—C2B—C1B82.1 (3)
C7A—Fe1A—C2A—C3A116.0 (3)C7B—Fe1B—C2B—C1B124.6 (3)
C6A—Fe1A—C2A—C3A157.8 (3)C8B—Fe1B—C2B—C1B165.3 (3)
C4A—Fe1A—C2A—C3A37.7 (3)C5B—Fe1B—C2B—C1B37.5 (3)
C3A—Fe1A—C2A—C1A119.3 (4)C4B—Fe1B—C2B—C3B37.9 (3)
C8A—Fe1A—C2A—C1A165.9 (3)C10B—Fe1B—C2B—C3B167.9 (4)
C9A—Fe1A—C2A—C1A164.5 (5)C9B—Fe1B—C2B—C3B44.5 (7)
C10A—Fe1A—C2A—C1A51.9 (5)C6B—Fe1B—C2B—C3B159.0 (3)
C5A—Fe1A—C2A—C1A37.5 (3)C7B—Fe1B—C2B—C3B116.5 (3)
C7A—Fe1A—C2A—C1A124.8 (3)C8B—Fe1B—C2B—C3B75.8 (3)
C6A—Fe1A—C2A—C1A82.9 (3)C1B—Fe1B—C2B—C3B118.9 (4)
C4A—Fe1A—C2A—C1A81.6 (3)C5B—Fe1B—C2B—C3B81.4 (3)
C1A—C2A—C3A—C4A0.3 (5)C1B—C2B—C3B—C4B0.8 (5)
Fe1A—C2A—C3A—C4A60.0 (3)Fe1B—C2B—C3B—C4B59.5 (3)
C1A—C2A—C3A—Fe1A59.7 (3)C1B—C2B—C3B—Fe1B60.3 (3)
C1A—Fe1A—C3A—C2A37.7 (3)C2B—Fe1B—C3B—C4B118.7 (4)
C8A—Fe1A—C3A—C2A123.1 (3)C10B—Fe1B—C3B—C4B43.9 (7)
C9A—Fe1A—C3A—C2A163.8 (3)C9B—Fe1B—C3B—C4B76.1 (3)
C10A—Fe1A—C3A—C2A167.6 (5)C6B—Fe1B—C3B—C4B166.2 (4)
C5A—Fe1A—C3A—C2A81.2 (3)C7B—Fe1B—C3B—C4B159.9 (3)
C7A—Fe1A—C3A—C2A80.9 (3)C8B—Fe1B—C3B—C4B117.6 (3)
C6A—Fe1A—C3A—C2A48.7 (5)C1B—Fe1B—C3B—C4B81.1 (3)
C4A—Fe1A—C3A—C2A119.1 (4)C5B—Fe1B—C3B—C4B37.4 (3)
C2A—Fe1A—C3A—C4A119.1 (4)C4B—Fe1B—C3B—C2B118.7 (4)
C1A—Fe1A—C3A—C4A81.4 (3)C10B—Fe1B—C3B—C2B162.7 (5)
C8A—Fe1A—C3A—C4A117.7 (3)C9B—Fe1B—C3B—C2B165.2 (3)
C9A—Fe1A—C3A—C4A77.1 (3)C6B—Fe1B—C3B—C2B47.4 (5)
C10A—Fe1A—C3A—C4A48.4 (7)C7B—Fe1B—C3B—C2B81.4 (3)
C5A—Fe1A—C3A—C4A37.9 (3)C8B—Fe1B—C3B—C2B123.7 (3)
C7A—Fe1A—C3A—C4A159.9 (3)C1B—Fe1B—C3B—C2B37.6 (3)
C6A—Fe1A—C3A—C4A167.9 (4)C5B—Fe1B—C3B—C2B81.3 (3)
C2A—C3A—C4A—C5A0.4 (5)C2B—C3B—C4B—C5B1.0 (5)
Fe1A—C3A—C4A—C5A58.9 (3)Fe1B—C3B—C4B—C5B60.4 (3)
C2A—C3A—C4A—Fe1A59.3 (3)C2B—C3B—C4B—Fe1B59.4 (3)
C2A—Fe1A—C4A—C3A37.8 (3)C3B—Fe1B—C4B—C5B119.3 (4)
C1A—Fe1A—C4A—C3A81.7 (3)C2B—Fe1B—C4B—C5B81.0 (3)
C8A—Fe1A—C4A—C3A79.4 (3)C10B—Fe1B—C4B—C5B75.4 (3)
C9A—Fe1A—C4A—C3A122.4 (3)C9B—Fe1B—C4B—C5B117.0 (3)
C10A—Fe1A—C4A—C3A164.1 (3)C6B—Fe1B—C4B—C5B40.9 (7)
C5A—Fe1A—C4A—C3A118.9 (4)C7B—Fe1B—C4B—C5B165.1 (4)
C7A—Fe1A—C4A—C3A44.2 (5)C8B—Fe1B—C4B—C5B160.0 (3)
C6A—Fe1A—C4A—C3A160.6 (5)C1B—Fe1B—C4B—C5B37.4 (3)
C2A—Fe1A—C4A—C5A81.2 (3)C2B—Fe1B—C4B—C3B38.3 (3)
C3A—Fe1A—C4A—C5A118.9 (4)C10B—Fe1B—C4B—C3B165.3 (3)
C1A—Fe1A—C4A—C5A37.2 (3)C9B—Fe1B—C4B—C3B123.6 (3)
C8A—Fe1A—C4A—C5A161.7 (3)C6B—Fe1B—C4B—C3B160.2 (6)
C9A—Fe1A—C4A—C5A118.6 (3)C7B—Fe1B—C4B—C3B45.7 (6)
C10A—Fe1A—C4A—C5A77.0 (3)C8B—Fe1B—C4B—C3B80.7 (3)
C7A—Fe1A—C4A—C5A163.1 (4)C1B—Fe1B—C4B—C3B81.9 (3)
C6A—Fe1A—C4A—C5A41.7 (7)C5B—Fe1B—C4B—C3B119.3 (4)
C2A—C1A—C5A—C4A0.2 (5)C3B—C4B—C5B—C1B0.8 (5)
Fe1A—C1A—C5A—C4A59.5 (3)Fe1B—C4B—C5B—C1B58.8 (3)
C2A—C1A—C5A—Fe1A59.2 (3)C3B—C4B—C5B—Fe1B59.6 (3)
C3A—C4A—C5A—C1A0.4 (5)C2B—C1B—C5B—C4B0.3 (5)
Fe1A—C4A—C5A—C1A59.2 (3)Fe1B—C1B—C5B—C4B58.3 (3)
C3A—C4A—C5A—Fe1A58.8 (3)C2B—C1B—C5B—Fe1B58.6 (3)
C2A—Fe1A—C5A—C1A37.9 (3)C3B—Fe1B—C5B—C4B37.8 (3)
C3A—Fe1A—C5A—C1A81.9 (3)C2B—Fe1B—C5B—C4B82.3 (3)
C8A—Fe1A—C5A—C1A162.2 (4)C10B—Fe1B—C5B—C4B124.1 (3)
C9A—Fe1A—C5A—C1A159.9 (3)C9B—Fe1B—C5B—C4B81.4 (3)
C10A—Fe1A—C5A—C1A116.2 (3)C6B—Fe1B—C5B—C4B166.1 (3)
C7A—Fe1A—C5A—C1A36.1 (7)C7B—Fe1B—C5B—C4B159.3 (5)
C6A—Fe1A—C5A—C1A73.5 (3)C8B—Fe1B—C5B—C4B46.3 (6)
C4A—Fe1A—C5A—C1A119.7 (4)C1B—Fe1B—C5B—C4B119.7 (4)
C2A—Fe1A—C5A—C4A81.7 (3)C3B—Fe1B—C5B—C1B81.9 (3)
C3A—Fe1A—C5A—C4A37.8 (3)C4B—Fe1B—C5B—C1B119.7 (4)
C1A—Fe1A—C5A—C4A119.7 (4)C2B—Fe1B—C5B—C1B37.5 (3)
C8A—Fe1A—C5A—C4A42.6 (5)C10B—Fe1B—C5B—C1B116.1 (3)
C9A—Fe1A—C5A—C4A80.5 (3)C9B—Fe1B—C5B—C1B158.9 (3)
C10A—Fe1A—C5A—C4A124.1 (3)C6B—Fe1B—C5B—C1B74.2 (3)
C7A—Fe1A—C5A—C4A155.7 (5)C7B—Fe1B—C5B—C1B39.5 (7)
C6A—Fe1A—C5A—C4A166.8 (2)C8B—Fe1B—C5B—C1B166.0 (4)
C2A—Fe1A—C6A—C7A80.0 (3)C3B—Fe1B—C6B—C10B166.8 (4)
C3A—Fe1A—C6A—C7A45.8 (5)C4B—Fe1B—C6B—C10B44.7 (7)
C1A—Fe1A—C6A—C7A122.9 (2)C2B—Fe1B—C6B—C10B159.3 (3)
C8A—Fe1A—C6A—C7A37.4 (2)C9B—Fe1B—C6B—C10B37.6 (3)
C9A—Fe1A—C6A—C7A81.3 (3)C7B—Fe1B—C6B—C10B119.1 (4)
C10A—Fe1A—C6A—C7A118.9 (3)C8B—Fe1B—C6B—C10B81.7 (3)
C5A—Fe1A—C6A—C7A163.5 (2)C1B—Fe1B—C6B—C10B117.0 (3)
C4A—Fe1A—C6A—C7A163.9 (6)C5B—Fe1B—C6B—C10B76.1 (3)
C2A—Fe1A—C6A—C10A161.1 (2)C3B—Fe1B—C6B—C7B47.7 (6)
C3A—Fe1A—C6A—C10A164.6 (4)C4B—Fe1B—C6B—C7B163.9 (6)
C1A—Fe1A—C6A—C10A118.3 (2)C2B—Fe1B—C6B—C7B81.6 (3)
C8A—Fe1A—C6A—C10A81.5 (3)C10B—Fe1B—C6B—C7B119.1 (4)
C9A—Fe1A—C6A—C10A37.6 (2)C9B—Fe1B—C6B—C7B81.5 (3)
C5A—Fe1A—C6A—C10A77.6 (3)C8B—Fe1B—C6B—C7B37.5 (3)
C7A—Fe1A—C6A—C10A118.9 (3)C1B—Fe1B—C6B—C7B123.9 (3)
C4A—Fe1A—C6A—C10A45.0 (7)C5B—Fe1B—C6B—C7B164.8 (3)
C10A—C6A—C7A—C8A0.7 (5)C10B—C6B—C7B—C8B0.1 (5)
Fe1A—C6A—C7A—C8A58.7 (3)Fe1B—C6B—C7B—C8B59.4 (3)
C10A—C6A—C7A—Fe1A59.4 (3)C10B—C6B—C7B—Fe1B59.2 (3)
C2A—Fe1A—C7A—C6A117.0 (2)C3B—Fe1B—C7B—C8B81.8 (3)
C3A—Fe1A—C7A—C6A159.0 (2)C4B—Fe1B—C7B—C8B49.1 (5)
C1A—Fe1A—C7A—C6A76.4 (3)C2B—Fe1B—C7B—C8B124.6 (3)
C8A—Fe1A—C7A—C6A120.1 (3)C10B—Fe1B—C7B—C8B81.5 (3)
C9A—Fe1A—C7A—C6A82.2 (2)C9B—Fe1B—C7B—C8B37.7 (3)
C10A—Fe1A—C7A—C6A38.0 (2)C6B—Fe1B—C7B—C8B119.4 (4)
C5A—Fe1A—C7A—C6A48.8 (6)C1B—Fe1B—C7B—C8B165.3 (3)
C4A—Fe1A—C7A—C6A169.7 (4)C5B—Fe1B—C7B—C8B164.4 (6)
C2A—Fe1A—C7A—C8A122.9 (3)C3B—Fe1B—C7B—C6B158.8 (3)
C3A—Fe1A—C7A—C8A80.9 (3)C4B—Fe1B—C7B—C6B168.5 (4)
C1A—Fe1A—C7A—C8A163.6 (2)C2B—Fe1B—C7B—C6B116.0 (3)
C9A—Fe1A—C7A—C8A37.9 (2)C10B—Fe1B—C7B—C6B37.9 (3)
C10A—Fe1A—C7A—C8A82.1 (3)C9B—Fe1B—C7B—C6B81.7 (3)
C5A—Fe1A—C7A—C8A168.9 (5)C8B—Fe1B—C7B—C6B119.4 (4)
C6A—Fe1A—C7A—C8A120.1 (3)C1B—Fe1B—C7B—C6B75.3 (3)
C4A—Fe1A—C7A—C8A49.7 (5)C5B—Fe1B—C7B—C6B45.0 (7)
C6A—C7A—C8A—C9A0.7 (5)C6B—C7B—C8B—C9B0.2 (5)
Fe1A—C7A—C8A—C9A59.6 (3)Fe1B—C7B—C8B—C9B59.0 (3)
C6A—C7A—C8A—Fe1A58.9 (3)C6B—C7B—C8B—Fe1B59.2 (3)
C2A—Fe1A—C8A—C9A165.8 (2)C3B—Fe1B—C8B—C7B116.0 (3)
C3A—Fe1A—C8A—C9A125.0 (3)C4B—Fe1B—C8B—C7B158.5 (3)
C1A—Fe1A—C8A—C9A164.8 (5)C2B—Fe1B—C8B—C7B74.1 (3)
C10A—Fe1A—C8A—C9A37.9 (2)C10B—Fe1B—C8B—C7B81.8 (3)
C5A—Fe1A—C8A—C9A52.6 (5)C9B—Fe1B—C8B—C7B119.6 (4)
C7A—Fe1A—C8A—C9A119.0 (4)C6B—Fe1B—C8B—C7B37.8 (3)
C6A—Fe1A—C8A—C9A81.8 (3)C1B—Fe1B—C8B—C7B42.0 (7)
C4A—Fe1A—C8A—C9A83.3 (3)C5B—Fe1B—C8B—C7B168.4 (4)
C2A—Fe1A—C8A—C7A75.2 (3)C3B—Fe1B—C8B—C9B124.4 (3)
C3A—Fe1A—C8A—C7A116.0 (3)C4B—Fe1B—C8B—C9B81.9 (3)
C1A—Fe1A—C8A—C7A45.9 (6)C2B—Fe1B—C8B—C9B166.3 (3)
C9A—Fe1A—C8A—C7A119.0 (4)C10B—Fe1B—C8B—C9B37.7 (3)
C10A—Fe1A—C8A—C7A81.1 (3)C6B—Fe1B—C8B—C9B81.8 (3)
C5A—Fe1A—C8A—C7A171.6 (4)C7B—Fe1B—C8B—C9B119.6 (4)
C6A—Fe1A—C8A—C7A37.2 (2)C1B—Fe1B—C8B—C9B161.6 (5)
C4A—Fe1A—C8A—C7A157.7 (2)C5B—Fe1B—C8B—C9B48.9 (6)
C7A—C8A—C9A—C10A0.4 (5)C7B—C8B—C9B—C10B0.2 (5)
Fe1A—C8A—C9A—C10A59.2 (3)Fe1B—C8B—C9B—C10B59.3 (3)
C7A—C8A—C9A—Fe1A59.6 (3)C7B—C8B—C9B—Fe1B59.2 (3)
C2A—Fe1A—C9A—C8A39.1 (6)C3B—Fe1B—C9B—C10B165.9 (3)
C3A—Fe1A—C9A—C8A73.3 (3)C4B—Fe1B—C9B—C10B124.1 (3)
C1A—Fe1A—C9A—C8A167.5 (4)C2B—Fe1B—C9B—C10B159.6 (6)
C10A—Fe1A—C9A—C8A119.1 (4)C6B—Fe1B—C9B—C10B37.8 (3)
C5A—Fe1A—C9A—C8A157.8 (3)C7B—Fe1B—C9B—C10B81.8 (3)
C7A—Fe1A—C9A—C8A37.9 (2)C8B—Fe1B—C9B—C10B119.1 (4)
C6A—Fe1A—C9A—C8A81.6 (3)C1B—Fe1B—C9B—C10B47.1 (5)
C4A—Fe1A—C9A—C8A115.2 (3)C5B—Fe1B—C9B—C10B81.8 (3)
C2A—Fe1A—C9A—C10A158.2 (5)C3B—Fe1B—C9B—C8B75.0 (3)
C3A—Fe1A—C9A—C10A167.6 (3)C4B—Fe1B—C9B—C8B116.8 (3)
C1A—Fe1A—C9A—C10A48.4 (5)C2B—Fe1B—C9B—C8B40.5 (7)
C8A—Fe1A—C9A—C10A119.1 (4)C10B—Fe1B—C9B—C8B119.1 (4)
C5A—Fe1A—C9A—C10A83.1 (3)C6B—Fe1B—C9B—C8B81.3 (3)
C7A—Fe1A—C9A—C10A81.2 (3)C7B—Fe1B—C9B—C8B37.4 (3)
C6A—Fe1A—C9A—C10A37.5 (2)C1B—Fe1B—C9B—C8B166.2 (4)
C4A—Fe1A—C9A—C10A125.7 (3)C5B—Fe1B—C9B—C8B159.1 (3)
C7A—C6A—C10A—C9A0.5 (5)C8B—C9B—C10B—C6B0.1 (5)
Fe1A—C6A—C10A—C9A59.0 (3)Fe1B—C9B—C10B—C6B59.3 (3)
C7A—C6A—C10A—C11A176.4 (4)C8B—C9B—C10B—C11B178.7 (4)
Fe1A—C6A—C10A—C11A124.1 (4)Fe1B—C9B—C10B—C11B121.9 (4)
C7A—C6A—C10A—Fe1A59.5 (3)C8B—C9B—C10B—Fe1B59.4 (3)
C8A—C9A—C10A—C6A0.1 (5)C7B—C6B—C10B—C9B0.0 (5)
Fe1A—C9A—C10A—C6A59.1 (3)Fe1B—C6B—C10B—C9B59.4 (3)
C8A—C9A—C10A—C11A176.8 (4)C7B—C6B—C10B—C11B178.8 (4)
Fe1A—C9A—C10A—C11A124.0 (4)Fe1B—C6B—C10B—C11B121.8 (4)
C8A—C9A—C10A—Fe1A59.2 (3)C7B—C6B—C10B—Fe1B59.3 (3)
C2A—Fe1A—C10A—C6A43.3 (5)C3B—Fe1B—C10B—C9B41.8 (7)
C3A—Fe1A—C10A—C6A156.7 (6)C4B—Fe1B—C10B—C9B75.6 (3)
C1A—Fe1A—C10A—C6A80.4 (3)C2B—Fe1B—C10B—C9B165.8 (4)
C8A—Fe1A—C10A—C6A81.9 (3)C6B—Fe1B—C10B—C9B119.3 (4)
C9A—Fe1A—C10A—C6A119.6 (3)C7B—Fe1B—C10B—C9B81.5 (3)
C5A—Fe1A—C10A—C6A123.4 (3)C8B—Fe1B—C10B—C9B37.9 (3)
C7A—Fe1A—C10A—C6A37.8 (2)C1B—Fe1B—C10B—C9B159.5 (3)
C4A—Fe1A—C10A—C6A165.8 (3)C5B—Fe1B—C10B—C9B116.9 (3)
C2A—Fe1A—C10A—C9A162.9 (4)C3B—Fe1B—C10B—C6B161.1 (6)
C3A—Fe1A—C10A—C9A37.0 (7)C4B—Fe1B—C10B—C6B165.0 (3)
C1A—Fe1A—C10A—C9A159.9 (3)C2B—Fe1B—C10B—C6B46.5 (5)
C8A—Fe1A—C10A—C9A37.8 (3)C9B—Fe1B—C10B—C6B119.3 (4)
C5A—Fe1A—C10A—C9A117.0 (3)C7B—Fe1B—C10B—C6B37.8 (3)
C7A—Fe1A—C10A—C9A81.8 (3)C8B—Fe1B—C10B—C6B81.4 (3)
C6A—Fe1A—C10A—C9A119.6 (3)C1B—Fe1B—C10B—C6B81.2 (3)
C4A—Fe1A—C10A—C9A74.5 (3)C5B—Fe1B—C10B—C6B123.8 (3)
C2A—Fe1A—C10A—C11A76.5 (6)C3B—Fe1B—C10B—C11B78.6 (8)
C3A—Fe1A—C10A—C11A83.5 (7)C4B—Fe1B—C10B—C11B44.8 (5)
C1A—Fe1A—C10A—C11A39.4 (4)C2B—Fe1B—C10B—C11B73.8 (6)
C8A—Fe1A—C10A—C11A158.3 (4)C9B—Fe1B—C10B—C11B120.4 (5)
C9A—Fe1A—C10A—C11A120.5 (5)C6B—Fe1B—C10B—C11B120.3 (5)
C5A—Fe1A—C10A—C11A3.5 (4)C7B—Fe1B—C10B—C11B158.1 (5)
C7A—Fe1A—C10A—C11A157.6 (4)C8B—Fe1B—C10B—C11B158.3 (5)
C6A—Fe1A—C10A—C11A119.8 (5)C1B—Fe1B—C10B—C11B39.1 (5)
C4A—Fe1A—C10A—C11A46.0 (4)C5B—Fe1B—C10B—C11B3.5 (5)
N2A—N1A—C11A—C10A174.7 (4)N2B—N1B—C11B—C10B176.5 (4)
C6A—C10A—C11A—N1A0.7 (6)C9B—C10B—C11B—N1B178.3 (4)
C9A—C10A—C11A—N1A177.0 (4)C6B—C10B—C11B—N1B0.3 (7)
Fe1A—C10A—C11A—N1A91.0 (5)Fe1B—C10B—C11B—N1B91.0 (5)
C13A—N3A—C12A—N2A178.3 (4)C13B—N3B—C12B—N2B177.3 (5)
C13A—N3A—C12A—S1A1.4 (6)C13B—N3B—C12B—S1B4.3 (7)
N1A—N2A—C12A—N3A6.2 (6)N1B—N2B—C12B—N3B7.1 (6)
N1A—N2A—C12A—S1A174.1 (3)N1B—N2B—C12B—S1B174.4 (3)
C12A—N3A—C13A—C14A175.2 (4)C12B—N3B—C13B—C14B84.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···S1Ai0.82 (6)2.59 (6)3.387 (4)164 (5)
N2B—H2NB···S1Bii0.89 (9)2.55 (9)3.430 (5)170 (5)
C4A—H4AA···S1Biii0.982.793.715 (4)157
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C9H12N3S)]
Mr315.22
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.4432 (3), 10.6906 (5), 18.4616 (9)
α, β, γ (°)77.975 (3), 83.807 (3), 78.076 (3)
V3)1402.56 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.21
Crystal size (mm)0.29 × 0.16 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.723, 0.901
No. of measured, independent and
observed [I > 2σ(I)] reflections
8184, 8184, 6947
Rint0.000
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.170, 1.07
No. of reflections8184
No. of parameters362
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)3.94, 1.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···S1Ai0.82 (6)2.59 (6)3.387 (4)164 (5)
N2B—H2NB···S1Bii0.89 (9)2.55 (9)3.430 (5)170 (5)
C4A—H4AA···S1Biii0.98002.79003.715 (4)157.00
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z; (iii) x, y, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks USM for the award of a USM Fellowship.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCasas, J. S., Castaño, M. V., Cifuentes, M. C., Garcia-Monteagudo, J. C., Sánchez, A., Sordo, J. & Abram, U. (2004). J. Inorg. Biochem. 98, 1009–1016.  Web of Science CrossRef PubMed CAS Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2009). Acta Cryst. E65, m1524–m1525.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationVikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, m679.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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