supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m373-m374    [ doi:10.1107/S1600536809007363 ]

Bis(ferrocenecarbaldehyde thiosemicarbazonato-[kappa]2N1,S)zinc

M. R. Vikneswaran, S. G. Teoh, I. A. Razak and H.-K. Fun

Abstract top

In the title compound, [Fe2Zn(C5H5)2(C7H7N3S)2], the Cp rings of each ferrocene residue have a nearly eclipsed conformation. The two thiosemicarbazone ligands each coordinate the Zn atom in a bidentate mode via the N and S atoms, thereby defining a distorted tetrahedral environment. N-H...S, N-H...N, C-H...S and C-H...N intra- and intermolecular interactions connect the molecules into a two-dimensional array parallel to (010).

Comment top

Thiosemicarbazones and their metal complexes have been attracting considerable interest due to their biological activities, such as anti-tumor (Quiroga et al., 1998), anti-viral (Genova et al., 2004), anti-fungal and anti-bacterial properties (Melha, 2008). Herein, we report the crystal structure of the zinc(II) complex formed with formylferrocene thiosemicarbazone, (I).

The average Fe—Cring distances in (I) (Fig. 1) are as expected for a ferrocene derivative [Fe—Cp1(C5—C9) = 2.043 (2) Å, Fe—Cp2(C10—C14) = 2.050 (2) Å, Fe—Cp3(C15—C19) = 2.046 (2) Å and Fe—Cp4(C20—C24) = 2.044 (2) Å] and are within the range of the values in the structures reported by Palenik (1970) and Haaland & Sikson (1968). The torsion angle for a ring-center, a ring-C atom, the corresponding C atom on the opposite ring and its ring center defines the angle of twist of the Cp rings (Palenik, 1970). The average twist angles are 5.4 and 7.7° for Cp1/Cp2 and Cp3/Cp4, respectively, indicating both Cp rings adopt nearly eclipsed conformations. Each of the Cp1/Cp2 and Cp3/Cp4 pairs are nearly parallel [dihedral angle for Cp1/Cp2 = 0.68 (13)° and 1.02 (13)° for Cp3/Cp4] and co-planar [maximum deviation for Cp1 is 0.006 (2)Å for atom C5; for Cp2 is 0.002 (2)Å for atom C13; for Cp3 is 0.005 (2)Å for both atoms C15 and C16; and for Cp4 is 0.004 (3)Å for both atoms C20 and C21].

Each of the two thiosemicarbazone ligands is bidentately coordinated to Zn(II) via the N and S atoms thus forming a distorted tetrahedral environment. The angles around Zn atom ranges from 86.58 (4) to 131.68 (4)°. These chelating ligands form two five membered rings, Zn1S1C1N1N2 and Zn1S2C2N3N4, which are planar with maximum deviation of 0.011 (1) and 0.014 (1) Å, respectively for the Zn atom. The two five-membered rings form a dihedral angle of 77.75 (5)°. Distorted tetrahedral coordination for Zn(II) was also reported by Li et al. (2004) and Latheef et al. (2007). Bond lengths involving the thiosemicarbazone moieties are generally comparable to the corresponding values reported by Latheef et al. (2007) with the exception of C1—N2 which is shorter and N1—N2, Zn1—S2 and C2—S2 which are longer. This observation is probably due to atoms N2 and S2 being involved in intermolecular interactions (Table 1).

The crystal structure is stabilized by N—H···S, N—H···N, C—H···S and C—H···N intermolecular interactions (Table 1). These interactions link the molecules into 2-D arrays parallel to the ac plane (Fig. 2). The crystal structure is further stabilized by the N—H···π and C—H···π interactions (Table 1).

Related literature top

For general background, see: Quiroga et al. (1998); Genova et al. (2004); Melha (2008). For related structures, see: Palenik (1970); Haaland & Sikson (1968); Li et al. (2004); Latheef et al. (2007). For the synthesis, see: Mariño et al. (2006). For the stability of the temperature controller, see: Cosier & Glazer (1986). Cg1, Cg2, Cg3, and Cg4 are the centroids of C20–C24, C15–C19, Zn1,S2,C2,N4,N3 and Zn1,S1,C1,N2,N1 rings, respectively.

Experimental top

Formylferrocene thiosemicarbazone was prepared as described by Mariño et al. (2006). Zn(CH3COO)2.2H2O(0.21 g,1 mmol) dissolved in methanol (60 ml) was added dropwise at room temperature to a mixture of formylferrocene thiosemicarbazone (0.28 g, 1 mmol) and KOH (0.12 g, 2 mmol) in absolute methanol (15 ml). Amorphous orange solids separated out immediately. The suspension was stirred under reflux for 4 h and filtered. After several days, brown crystals were obtained from the filtrate.

Refinement top

All the H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq (C) The N-bound H atoms were located from a difference Fourier map and refined isotropically with N-H = 0.779 (15) - 0.90 (3) Å.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SMART (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom numbering scheme. Intramolecular contacts are drawn as dashed lines.
[Figure 2] Fig. 2. The crystal packing for (I), viewed down the b axis. H atoms excepting for those involved in intermolecular interactions (shown as dashed lines) are omitted for clarity.
Bis(ferrocenecarbaldehyde thiosemicarbazonato-κ2N,S)zinc(II) top
Crystal data top
[Fe2Zn(C5H5)2(C7H7N3S)2]F(000) = 1296
Mr = 637.68Dx = 1.696 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9980 reflections
a = 10.8483 (2) Åθ = 2.4–34.0°
b = 14.7547 (2) ŵ = 2.29 mm−1
c = 16.1686 (2) ÅT = 100 K
β = 105.252 (1)°Plate, brown
V = 2496.85 (6) Å30.58 × 0.19 × 0.08 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		11266 independent reflections
Radiation source: sealed tube7721 reflections with I > 2σ(I)
graphiteRint = 0.052
π and ω scansθmax = 35.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −17→16
Tmin = 0.348, Tmax = 0.840k = −21→23
61395 measured reflectionsl = −26→26
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.010H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3689P]
where P = (Fo2 + 2Fc2)/3
11266 reflections(Δ/σ)max = 0.002
332 parametersΔρmax = 0.99 e Å−3
1 restraintΔρmin = −0.64 e Å−3
Crystal data top
[Fe2Zn(C5H5)2(C7H7N3S)2]V = 2496.85 (6) Å3
Mr = 637.68Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.8483 (2) ŵ = 2.29 mm−1
b = 14.7547 (2) ÅT = 100 K
c = 16.1686 (2) Å0.58 × 0.19 × 0.08 mm
β = 105.252 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		11266 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		7721 reflections with I > 2σ(I)
Tmin = 0.348, Tmax = 0.840Rint = 0.052
61395 measured reflectionsθmax = 35.4°
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.010Δρmax = 0.99 e Å−3
S = 1.06Δρmin = −0.64 e Å−3
11266 reflectionsAbsolute structure: ?
332 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Zn10.360473 (19)0.818097 (14)0.175658 (12)0.01591 (5)
Fe10.60392 (3)0.553115 (18)0.319621 (17)0.02062 (7)
Fe20.65545 (3)0.713991 (19)−0.064830 (17)0.02060 (7)
S10.33717 (5)0.96352 (3)0.21462 (3)0.02417 (11)
S20.19130 (4)0.72073 (3)0.14688 (3)0.02045 (10)
N60.13760 (17)0.62297 (12)0.00529 (11)0.0229 (3)
C10.48096 (17)0.96209 (12)0.29426 (11)0.0173 (3)
C20.21813 (17)0.68618 (12)0.04915 (11)0.0179 (3)
C30.62251 (17)0.75580 (12)0.28741 (11)0.0190 (3)
H3A0.69670.77180.32860.023*
C40.47629 (17)0.81122 (12)0.02822 (12)0.0188 (3)
H4A0.53040.85390.06160.023*
C50.61764 (18)0.66613 (12)0.25081 (12)0.0198 (4)
C60.72976 (19)0.61046 (13)0.26228 (13)0.0252 (4)
H6A0.81760.62860.29070.030*
C70.6908 (2)0.52516 (14)0.22429 (15)0.0304 (5)
H7A0.74710.47350.22310.037*
C80.5564 (2)0.52614 (14)0.19008 (13)0.0263 (4)
H8A0.50410.47520.16160.032*
C90.50977 (19)0.61241 (13)0.20639 (12)0.0232 (4)
H9A0.42030.63190.19030.028*
C100.5945 (3)0.59366 (17)0.43946 (14)0.0393 (6)
H10A0.60080.65630.46040.047*
C110.6971 (3)0.53416 (18)0.44599 (15)0.0451 (7)
H11A0.78720.54780.47270.054*
C120.6479 (2)0.44998 (17)0.40671 (16)0.0417 (6)
H12A0.69770.39560.40230.050*
C130.5132 (2)0.45957 (15)0.37643 (14)0.0343 (5)
H13A0.45330.41300.34680.041*
C140.4806 (3)0.54866 (16)0.39660 (15)0.0358 (5)
H14A0.39430.57440.38300.043*
C150.50287 (17)0.78963 (13)−0.05250 (11)0.0187 (3)
C160.58907 (19)0.84334 (14)−0.08659 (13)0.0236 (4)
H16A0.63380.8981−0.06040.028*
C170.5977 (2)0.80355 (14)−0.16440 (13)0.0266 (4)
H17A0.65000.8257−0.20120.032*
C180.5194 (2)0.72454 (14)−0.17923 (12)0.0251 (4)
H18A0.50890.6831−0.22800.030*
C190.46084 (18)0.71495 (13)−0.11123 (12)0.0211 (4)
H19A0.40250.6663−0.10490.025*
C200.8388 (2)0.71997 (17)0.01123 (15)0.0353 (5)
H20A0.88800.77520.03080.042*
C210.7588 (2)0.67432 (18)0.05388 (15)0.0408 (6)
H21A0.74290.69210.10860.049*
C220.7063 (2)0.59671 (17)0.00334 (17)0.0416 (6)
H22A0.64780.55210.01710.050*
C230.7539 (2)0.59651 (16)−0.06984 (16)0.0370 (5)
H23A0.73350.5518−0.11620.044*
C240.8343 (2)0.67154 (17)−0.06532 (16)0.0362 (5)
H24A0.87980.6880−0.10810.043*
N50.50939 (17)1.03882 (12)0.34266 (11)0.0241 (4)
N10.53245 (14)0.81584 (10)0.26777 (9)0.0164 (3)
N20.56360 (14)0.89628 (10)0.31495 (9)0.0169 (3)
N30.38768 (14)0.77964 (10)0.06093 (9)0.0176 (3)
N40.30745 (14)0.71515 (10)0.01374 (9)0.0179 (3)
H1N60.0846 (18)0.6050 (15)0.0255 (13)0.020 (6)*
H2N50.471 (2)1.0838 (18)0.3241 (16)0.032 (7)*
H1N50.592 (3)1.0432 (18)0.3714 (17)0.046 (8)*
H2N60.136 (3)0.6177 (19)−0.0447 (18)0.045 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01686 (10)0.01601 (10)0.01412 (9)−0.00136 (7)0.00276 (7)−0.00117 (7)
Fe10.01956 (13)0.01766 (13)0.02229 (13)−0.00241 (9)0.00134 (10)0.00225 (10)
Fe20.01781 (13)0.02438 (15)0.02068 (13)0.00488 (10)0.00698 (10)0.00279 (10)
S10.0223 (2)0.0179 (2)0.0268 (2)0.00339 (16)−0.00326 (18)−0.00247 (17)
S20.0205 (2)0.0233 (2)0.0188 (2)−0.00489 (16)0.00733 (16)−0.00330 (16)
N60.0226 (8)0.0281 (9)0.0190 (8)−0.0077 (6)0.0074 (6)−0.0042 (6)
C10.0178 (8)0.0184 (8)0.0156 (8)−0.0025 (6)0.0044 (6)−0.0005 (6)
C20.0167 (8)0.0192 (8)0.0165 (8)0.0009 (6)0.0023 (6)0.0002 (6)
C30.0178 (8)0.0175 (8)0.0206 (8)−0.0004 (6)0.0029 (6)0.0006 (6)
C40.0169 (8)0.0201 (9)0.0193 (8)−0.0004 (6)0.0047 (6)−0.0005 (6)
C50.0218 (9)0.0166 (8)0.0211 (8)0.0008 (6)0.0058 (7)0.0017 (6)
C60.0218 (9)0.0191 (9)0.0357 (11)0.0018 (7)0.0093 (8)0.0012 (8)
C70.0336 (11)0.0206 (10)0.0405 (12)0.0054 (8)0.0159 (9)−0.0009 (9)
C80.0331 (11)0.0208 (9)0.0244 (9)0.0007 (8)0.0062 (8)−0.0024 (7)
C90.0249 (9)0.0193 (9)0.0219 (9)0.0023 (7)−0.0003 (7)0.0008 (7)
C100.0569 (16)0.0370 (13)0.0239 (10)−0.0202 (11)0.0103 (10)−0.0027 (9)
C110.0459 (14)0.0475 (15)0.0301 (12)−0.0216 (12)−0.0109 (10)0.0161 (10)
C120.0434 (14)0.0312 (12)0.0421 (13)−0.0072 (10)−0.0038 (11)0.0179 (10)
C130.0407 (13)0.0312 (12)0.0301 (11)−0.0168 (9)0.0075 (9)0.0017 (9)
C140.0429 (14)0.0394 (13)0.0291 (11)−0.0129 (10)0.0164 (10)−0.0049 (9)
C150.0176 (8)0.0209 (9)0.0178 (8)0.0028 (6)0.0047 (6)0.0010 (6)
C160.0253 (10)0.0223 (9)0.0246 (9)0.0011 (7)0.0092 (7)0.0038 (7)
C170.0330 (11)0.0286 (11)0.0214 (9)0.0044 (8)0.0127 (8)0.0060 (8)
C180.0295 (10)0.0263 (10)0.0192 (9)0.0063 (8)0.0060 (7)0.0001 (7)
C190.0187 (9)0.0226 (9)0.0211 (9)0.0027 (7)0.0034 (7)−0.0005 (7)
C200.0236 (11)0.0426 (14)0.0359 (12)0.0096 (9)0.0011 (9)−0.0089 (10)
C210.0372 (13)0.0574 (16)0.0257 (11)0.0294 (11)0.0044 (9)0.0097 (10)
C220.0325 (12)0.0380 (14)0.0522 (15)0.0138 (10)0.0074 (11)0.0195 (11)
C230.0306 (12)0.0331 (12)0.0440 (13)0.0138 (9)0.0044 (10)−0.0020 (10)
C240.0204 (10)0.0505 (15)0.0383 (12)0.0101 (9)0.0089 (9)−0.0074 (10)
N50.0223 (8)0.0179 (8)0.0286 (9)0.0011 (6)0.0006 (7)−0.0042 (6)
N10.0187 (7)0.0146 (7)0.0154 (6)−0.0017 (5)0.0039 (5)0.0001 (5)
N20.0187 (7)0.0145 (7)0.0176 (7)−0.0002 (5)0.0050 (5)−0.0001 (5)
N30.0179 (7)0.0167 (7)0.0174 (7)−0.0010 (5)0.0033 (5)−0.0011 (5)
N40.0176 (7)0.0193 (7)0.0159 (7)−0.0021 (5)0.0029 (5)−0.0008 (5)
Geometric parameters (Å, °) top
Zn1—N32.0342 (16)C6—C71.415 (3)
Zn1—N12.0586 (14)C6—H6A0.9800
Zn1—S12.2690 (5)C7—C81.417 (3)
Zn1—S22.2802 (5)C7—H7A0.9800
Fe1—C62.026 (2)C8—C91.420 (3)
Fe1—C52.0317 (18)C8—H8A0.9800
Fe1—C122.043 (2)C9—H9A0.9800
Fe1—C92.0436 (18)C10—C111.399 (4)
Fe1—C112.046 (2)C10—C141.414 (3)
Fe1—C132.048 (2)C10—H10A0.9800
Fe1—C72.049 (2)C11—C121.433 (3)
Fe1—C142.054 (2)C11—H11A0.9800
Fe1—C102.056 (2)C12—C131.420 (3)
Fe1—C82.060 (2)C12—H12A0.9800
Fe2—C212.037 (2)C13—C141.421 (3)
Fe2—C162.038 (2)C13—H13A0.9800
Fe2—C242.040 (2)C14—H14A0.9800
Fe2—C192.0461 (18)C15—C161.441 (3)
Fe2—C202.046 (2)C15—C191.448 (3)
Fe2—C182.0465 (19)C16—C171.414 (3)
Fe2—C222.048 (2)C16—H16A0.9800
Fe2—C232.049 (2)C17—C181.425 (3)
Fe2—C152.0491 (18)C17—H17A0.9800
Fe2—C172.049 (2)C18—C191.414 (3)
S1—C11.7421 (17)C18—H18A0.9800
S2—C21.7560 (19)C19—H19A0.9800
N6—C21.345 (2)C20—C211.413 (4)
N6—H1N60.779 (15)C20—C241.419 (3)
N6—H2N60.81 (3)C20—H20A0.9800
C1—N21.304 (2)C21—C221.435 (4)
C1—N51.365 (2)C21—H21A0.9800
C2—N41.320 (2)C22—C231.410 (4)
C3—N11.295 (2)C22—H22A0.9800
C3—C51.445 (3)C23—C241.399 (4)
C3—H3A0.9300C23—H23A0.9800
C4—N31.299 (2)C24—H24A0.9800
C4—C151.444 (3)N5—H2N50.80 (3)
C4—H4A0.9300N5—H1N50.90 (3)
C5—C61.439 (3)N1—N21.403 (2)
C5—C91.439 (3)N3—N41.377 (2)
N3—Zn1—N1109.51 (6)C7—C6—H6A126.1
N3—Zn1—S1124.78 (5)C5—C6—H6A126.1
N1—Zn1—S187.73 (4)Fe1—C6—H6A126.1
N3—Zn1—S286.58 (4)C6—C7—C8108.63 (18)
N1—Zn1—S2131.68 (4)C6—C7—Fe168.81 (12)
S1—Zn1—S2120.66 (2)C8—C7—Fe170.23 (12)
C6—Fe1—C541.53 (8)C6—C7—H7A125.7
C6—Fe1—C12124.29 (10)C8—C7—H7A125.7
C5—Fe1—C12162.08 (9)Fe1—C7—H7A125.7
C6—Fe1—C969.48 (8)C7—C8—C9108.46 (18)
C5—Fe1—C941.36 (7)C7—C8—Fe169.41 (12)
C12—Fe1—C9155.16 (9)C9—C8—Fe169.14 (11)
C6—Fe1—C11107.38 (9)C7—C8—H8A125.8
C5—Fe1—C11124.81 (9)C9—C8—H8A125.8
C12—Fe1—C1141.02 (10)Fe1—C8—H8A125.8
C9—Fe1—C11162.19 (10)C8—C9—C5107.70 (17)
C6—Fe1—C13161.43 (9)C8—C9—Fe170.38 (11)
C5—Fe1—C13155.78 (9)C5—C9—Fe168.88 (10)
C12—Fe1—C1340.64 (10)C8—C9—H9A126.1
C9—Fe1—C13120.30 (9)C5—C9—H9A126.1
C11—Fe1—C1368.25 (9)Fe1—C9—H9A126.1
C6—Fe1—C740.64 (8)C11—C10—C14108.5 (2)
C5—Fe1—C768.82 (8)C11—C10—Fe169.70 (14)
C12—Fe1—C7107.36 (11)C14—C10—Fe169.82 (13)
C9—Fe1—C768.45 (8)C11—C10—H10A125.7
C11—Fe1—C7121.29 (11)C14—C10—H10A125.7
C13—Fe1—C7124.91 (9)Fe1—C10—H10A125.7
C6—Fe1—C14156.25 (9)C10—C11—C12108.3 (2)
C5—Fe1—C14120.75 (9)C10—C11—Fe170.41 (13)
C12—Fe1—C1468.26 (11)C12—C11—Fe169.35 (13)
C9—Fe1—C14107.75 (10)C10—C11—H11A125.8
C11—Fe1—C1467.67 (11)C12—C11—H11A125.8
C13—Fe1—C1440.55 (10)Fe1—C11—H11A125.8
C7—Fe1—C14162.02 (9)C13—C12—C11107.2 (2)
C6—Fe1—C10121.07 (9)C13—C12—Fe169.87 (13)
C5—Fe1—C10107.83 (9)C11—C12—Fe169.64 (13)
C12—Fe1—C1068.13 (11)C13—C12—H12A126.4
C9—Fe1—C10125.65 (10)C11—C12—H12A126.4
C11—Fe1—C1039.88 (11)Fe1—C12—H12A126.4
C13—Fe1—C1067.95 (9)C12—C13—C14108.0 (2)
C7—Fe1—C10156.08 (10)C12—C13—Fe169.49 (13)
C14—Fe1—C1040.24 (9)C14—C13—Fe169.97 (13)
C6—Fe1—C868.53 (8)C12—C13—H13A126.0
C5—Fe1—C868.69 (8)C14—C13—H13A126.0
C12—Fe1—C8120.50 (10)Fe1—C13—H13A126.0
C9—Fe1—C840.48 (8)C10—C14—C13108.0 (2)
C11—Fe1—C8156.15 (11)C10—C14—Fe169.95 (14)
C13—Fe1—C8107.73 (9)C13—C14—Fe169.49 (14)
C7—Fe1—C840.36 (9)C10—C14—H14A126.0
C14—Fe1—C8125.53 (9)C13—C14—H14A126.0
C10—Fe1—C8162.43 (10)Fe1—C14—H14A126.0
C21—Fe2—C16120.90 (9)C16—C15—C4121.88 (17)
C21—Fe2—C2468.13 (10)C16—C15—C19106.97 (17)
C16—Fe2—C24125.45 (10)C4—C15—C19131.09 (18)
C21—Fe2—C19127.32 (10)C16—C15—Fe268.92 (11)
C16—Fe2—C1969.30 (8)C4—C15—Fe2124.50 (13)
C24—Fe2—C19153.00 (9)C19—C15—Fe269.19 (10)
C21—Fe2—C2040.49 (11)C17—C16—C15108.26 (18)
C16—Fe2—C20107.86 (9)C17—C16—Fe270.21 (12)
C24—Fe2—C2040.63 (9)C15—C16—Fe269.78 (11)
C19—Fe2—C20164.97 (9)C17—C16—H16A125.9
C21—Fe2—C18163.86 (11)C15—C16—H16A125.9
C16—Fe2—C1868.57 (8)Fe2—C16—H16A125.9
C24—Fe2—C18118.71 (9)C16—C17—C18108.26 (19)
C19—Fe2—C1840.42 (8)C16—C17—Fe269.31 (11)
C20—Fe2—C18153.60 (10)C18—C17—Fe269.53 (11)
C21—Fe2—C2241.12 (11)C16—C17—H17A125.9
C16—Fe2—C22156.54 (10)C18—C17—H17A125.9
C24—Fe2—C2267.73 (10)Fe2—C17—H17A125.9
C19—Fe2—C22108.00 (9)C19—C18—C17108.71 (18)
C20—Fe2—C2268.37 (10)C19—C18—Fe269.77 (10)
C18—Fe2—C22125.37 (10)C17—C18—Fe269.75 (11)
C21—Fe2—C2368.33 (10)C19—C18—H18A125.6
C16—Fe2—C23161.78 (10)C17—C18—H18A125.6
C24—Fe2—C2340.01 (10)Fe2—C18—H18A125.6
C19—Fe2—C23119.33 (9)C18—C19—C15107.79 (17)
C20—Fe2—C2368.03 (9)C18—C19—Fe269.80 (11)
C18—Fe2—C23106.76 (9)C15—C19—Fe269.41 (10)
C22—Fe2—C2340.27 (10)C18—C19—H19A126.1
C21—Fe2—C15108.85 (8)C15—C19—H19A126.1
C16—Fe2—C1541.30 (8)Fe2—C19—H19A126.1
C24—Fe2—C15163.88 (9)C21—C20—C24107.5 (2)
C19—Fe2—C1541.40 (7)C21—C20—Fe269.41 (13)
C20—Fe2—C15126.89 (8)C24—C20—Fe269.46 (13)
C18—Fe2—C1568.74 (8)C21—C20—H20A126.2
C22—Fe2—C15121.20 (9)C24—C20—H20A126.2
C23—Fe2—C15155.18 (9)Fe2—C20—H20A126.2
C21—Fe2—C17154.70 (10)C20—C21—C22107.8 (2)
C16—Fe2—C1740.47 (8)C20—C21—Fe270.10 (13)
C24—Fe2—C17106.82 (10)C22—C21—Fe269.84 (13)
C19—Fe2—C1768.58 (8)C20—C21—H21A126.1
C20—Fe2—C17119.49 (10)C22—C21—H21A126.1
C18—Fe2—C1740.72 (8)Fe2—C21—H21A126.1
C22—Fe2—C17162.00 (10)C23—C22—C21107.5 (2)
C23—Fe2—C17124.70 (9)C23—C22—Fe269.90 (13)
C15—Fe2—C1768.74 (8)C21—C22—Fe269.05 (13)
C1—S1—Zn192.88 (6)C23—C22—H22A126.2
C2—S2—Zn192.95 (6)C21—C22—H22A126.2
C2—N6—H1N6117.6 (16)Fe2—C22—H22A126.2
C2—N6—H2N6116 (2)C24—C23—C22108.4 (2)
H1N6—N6—H2N6124 (3)C24—C23—Fe269.67 (13)
N2—C1—N5115.74 (16)C22—C23—Fe269.82 (13)
N2—C1—S1128.32 (14)C24—C23—H23A125.8
N5—C1—S1115.92 (14)C22—C23—H23A125.8
N4—C2—N6116.42 (17)Fe2—C23—H23A125.8
N4—C2—S2127.65 (14)C23—C24—C20108.8 (2)
N6—C2—S2115.93 (15)C23—C24—Fe270.32 (13)
N1—C3—C5125.60 (16)C20—C24—Fe269.91 (13)
N1—C3—H3A117.2C23—C24—H24A125.6
C5—C3—H3A117.2C20—C24—H24A125.6
N3—C4—C15129.32 (17)Fe2—C24—H24A125.6
N3—C4—H4A115.3C1—N5—H2N5117.2 (18)
C15—C4—H4A115.3C1—N5—H1N5113.6 (18)
C6—C5—C9107.38 (16)H2N5—N5—H1N5119 (3)
C6—C5—C3122.10 (17)C3—N1—N2112.77 (14)
C9—C5—C3130.25 (17)C3—N1—Zn1132.08 (12)
C6—C5—Fe169.03 (11)N2—N1—Zn1114.99 (10)
C9—C5—Fe169.77 (11)C1—N2—N1116.06 (14)
C3—C5—Fe1121.83 (14)C4—N3—N4116.73 (15)
C7—C6—C5107.82 (17)C4—N3—Zn1124.85 (12)
C7—C6—Fe170.56 (12)N4—N3—Zn1118.42 (12)
C5—C6—Fe169.44 (11)C2—N4—N3114.37 (15)
N3—Zn1—S1—C1−113.37 (8)C18—Fe2—C15—C16−81.30 (12)
N1—Zn1—S1—C1−1.08 (8)C22—Fe2—C15—C16159.32 (13)
S2—Zn1—S1—C1137.52 (6)C23—Fe2—C15—C16−165.3 (2)
N3—Zn1—S2—C21.28 (7)C17—Fe2—C15—C16−37.46 (12)
N1—Zn1—S2—C2−111.96 (8)C21—Fe2—C15—C40.75 (19)
S1—Zn1—S2—C2130.25 (6)C16—Fe2—C15—C4−114.9 (2)
Zn1—S1—C1—N21.38 (18)C24—Fe2—C15—C4−75.6 (4)
Zn1—S1—C1—N5−176.84 (14)C19—Fe2—C15—C4126.3 (2)
Zn1—S2—C2—N4−1.36 (17)C20—Fe2—C15—C4−40.8 (2)
Zn1—S2—C2—N6178.92 (14)C18—Fe2—C15—C4163.75 (18)
N1—C3—C5—C6166.79 (19)C22—Fe2—C15—C444.4 (2)
N1—C3—C5—C9−19.9 (3)C23—Fe2—C15—C479.7 (3)
N1—C3—C5—Fe1−109.40 (19)C17—Fe2—C15—C4−152.41 (18)
C12—Fe1—C5—C643.1 (4)C21—Fe2—C15—C19−125.54 (13)
C9—Fe1—C5—C6−118.84 (16)C16—Fe2—C15—C19118.76 (15)
C11—Fe1—C5—C676.33 (16)C24—Fe2—C15—C19158.1 (3)
C13—Fe1—C5—C6−167.21 (19)C20—Fe2—C15—C19−167.09 (13)
C7—Fe1—C5—C6−37.81 (12)C18—Fe2—C15—C1937.45 (11)
C14—Fe1—C5—C6159.16 (12)C22—Fe2—C15—C19−81.92 (14)
C10—Fe1—C5—C6117.03 (13)C23—Fe2—C15—C19−46.6 (2)
C8—Fe1—C5—C6−81.26 (12)C17—Fe2—C15—C1981.30 (12)
C6—Fe1—C5—C9118.84 (16)C4—C15—C16—C17178.27 (17)
C12—Fe1—C5—C9161.9 (3)C19—C15—C16—C170.9 (2)
C11—Fe1—C5—C9−164.83 (15)Fe2—C15—C16—C1759.90 (14)
C13—Fe1—C5—C9−48.4 (2)C4—C15—C16—Fe2118.36 (17)
C7—Fe1—C5—C981.02 (13)C19—C15—C16—Fe2−58.96 (12)
C14—Fe1—C5—C9−82.01 (14)C21—Fe2—C16—C17157.19 (14)
C10—Fe1—C5—C9−124.13 (13)C24—Fe2—C16—C1773.31 (16)
C8—Fe1—C5—C937.58 (12)C19—Fe2—C16—C17−80.87 (13)
C6—Fe1—C5—C3−115.6 (2)C20—Fe2—C16—C17114.77 (14)
C12—Fe1—C5—C3−72.5 (4)C18—Fe2—C16—C17−37.42 (13)
C9—Fe1—C5—C3125.6 (2)C22—Fe2—C16—C17−168.5 (2)
C11—Fe1—C5—C3−39.3 (2)C23—Fe2—C16—C1740.9 (3)
C13—Fe1—C5—C377.2 (3)C15—Fe2—C16—C17−119.17 (17)
C7—Fe1—C5—C3−153.41 (18)C21—Fe2—C16—C15−83.64 (14)
C14—Fe1—C5—C343.56 (18)C24—Fe2—C16—C15−167.52 (12)
C10—Fe1—C5—C31.44 (18)C19—Fe2—C16—C1538.30 (11)
C8—Fe1—C5—C3163.15 (18)C20—Fe2—C16—C15−126.06 (12)
C9—C5—C6—C70.9 (2)C18—Fe2—C16—C1581.76 (12)
C3—C5—C6—C7175.62 (18)C22—Fe2—C16—C15−49.4 (3)
Fe1—C5—C6—C760.40 (15)C23—Fe2—C16—C15160.1 (3)
C9—C5—C6—Fe1−59.46 (13)C17—Fe2—C16—C15119.17 (17)
C3—C5—C6—Fe1115.23 (18)C15—C16—C17—C18−0.8 (2)
C5—Fe1—C6—C7−118.62 (17)Fe2—C16—C17—C1858.79 (14)
C12—Fe1—C6—C776.12 (16)C15—C16—C17—Fe2−59.63 (13)
C9—Fe1—C6—C7−80.45 (13)C21—Fe2—C17—C16−51.1 (3)
C11—Fe1—C6—C7118.10 (14)C24—Fe2—C17—C16−125.39 (13)
C13—Fe1—C6—C744.8 (3)C19—Fe2—C17—C1682.81 (13)
C14—Fe1—C6—C7−168.0 (2)C20—Fe2—C17—C16−83.12 (14)
C10—Fe1—C6—C7159.49 (14)C18—Fe2—C17—C16119.90 (18)
C8—Fe1—C6—C7−36.96 (12)C22—Fe2—C17—C16165.1 (3)
C12—Fe1—C6—C5−165.26 (13)C23—Fe2—C17—C16−165.58 (13)
C9—Fe1—C6—C538.17 (11)C15—Fe2—C17—C1638.20 (12)
C11—Fe1—C6—C5−123.29 (13)C21—Fe2—C17—C18−171.0 (2)
C13—Fe1—C6—C5163.4 (2)C16—Fe2—C17—C18−119.90 (18)
C7—Fe1—C6—C5118.62 (17)C24—Fe2—C17—C18114.71 (13)
C14—Fe1—C6—C5−49.4 (3)C19—Fe2—C17—C18−37.09 (12)
C10—Fe1—C6—C5−81.89 (15)C20—Fe2—C17—C18156.98 (12)
C8—Fe1—C6—C581.66 (12)C22—Fe2—C17—C1845.2 (4)
C5—C6—C7—C8−0.6 (2)C23—Fe2—C17—C1874.52 (15)
Fe1—C6—C7—C859.10 (16)C15—Fe2—C17—C18−81.70 (13)
C5—C6—C7—Fe1−59.69 (14)C16—C17—C18—C190.4 (2)
C5—Fe1—C7—C638.62 (12)Fe2—C17—C18—C1959.06 (13)
C12—Fe1—C7—C6−122.82 (13)C16—C17—C18—Fe2−58.65 (14)
C9—Fe1—C7—C683.19 (13)C21—Fe2—C18—C1946.1 (4)
C11—Fe1—C7—C6−80.12 (14)C16—Fe2—C18—C19−82.83 (12)
C13—Fe1—C7—C6−164.12 (12)C24—Fe2—C18—C19157.47 (13)
C14—Fe1—C7—C6164.3 (3)C20—Fe2—C18—C19−169.99 (18)
C10—Fe1—C7—C6−47.7 (3)C22—Fe2—C18—C1975.58 (15)
C8—Fe1—C7—C6120.23 (17)C23—Fe2—C18—C19115.81 (13)
C6—Fe1—C7—C8−120.23 (17)C15—Fe2—C18—C19−38.33 (11)
C5—Fe1—C7—C8−81.61 (13)C17—Fe2—C18—C19−120.03 (17)
C12—Fe1—C7—C8116.96 (13)C21—Fe2—C18—C17166.1 (3)
C9—Fe1—C7—C8−37.04 (12)C16—Fe2—C18—C1737.19 (12)
C11—Fe1—C7—C8159.65 (13)C24—Fe2—C18—C17−82.50 (15)
C13—Fe1—C7—C875.65 (15)C19—Fe2—C18—C17120.03 (17)
C14—Fe1—C7—C844.0 (4)C20—Fe2—C18—C17−50.0 (2)
C10—Fe1—C7—C8−168.0 (2)C22—Fe2—C18—C17−164.39 (14)
C6—C7—C8—C90.0 (3)C23—Fe2—C18—C17−124.16 (13)
Fe1—C7—C8—C958.24 (15)C15—Fe2—C18—C1781.69 (13)
C6—C7—C8—Fe1−58.23 (16)C17—C18—C19—C150.2 (2)
C6—Fe1—C8—C737.20 (12)Fe2—C18—C19—C1559.23 (12)
C5—Fe1—C8—C781.97 (13)C17—C18—C19—Fe2−59.05 (14)
C12—Fe1—C8—C7−80.89 (15)C16—C15—C19—C18−0.7 (2)
C9—Fe1—C8—C7120.34 (18)C4—C15—C19—C18−177.67 (18)
C11—Fe1—C8—C7−47.3 (3)Fe2—C15—C19—C18−59.48 (13)
C13—Fe1—C8—C7−123.47 (14)C16—C15—C19—Fe258.78 (12)
C14—Fe1—C8—C7−164.71 (13)C4—C15—C19—Fe2−118.2 (2)
C10—Fe1—C8—C7163.7 (3)C21—Fe2—C19—C18−165.41 (13)
C6—Fe1—C8—C9−83.13 (13)C16—Fe2—C19—C1880.86 (12)
C5—Fe1—C8—C9−38.37 (12)C24—Fe2—C19—C18−47.8 (2)
C12—Fe1—C8—C9158.78 (13)C20—Fe2—C19—C18162.7 (3)
C11—Fe1—C8—C9−167.6 (2)C22—Fe2—C19—C18−123.86 (13)
C13—Fe1—C8—C9116.19 (14)C23—Fe2—C19—C18−81.39 (14)
C7—Fe1—C8—C9−120.34 (18)C15—Fe2—C19—C18119.07 (16)
C14—Fe1—C8—C974.95 (16)C17—Fe2—C19—C1837.36 (12)
C10—Fe1—C8—C943.4 (3)C21—Fe2—C19—C1575.51 (15)
C7—C8—C9—C50.6 (2)C16—Fe2—C19—C15−38.21 (11)
Fe1—C8—C9—C558.98 (13)C24—Fe2—C19—C15−166.82 (19)
C7—C8—C9—Fe1−58.41 (15)C20—Fe2—C19—C1543.6 (4)
C6—C5—C9—C8−0.9 (2)C18—Fe2—C19—C15−119.07 (16)
C3—C5—C9—C8−175.03 (19)C22—Fe2—C19—C15117.07 (13)
Fe1—C5—C9—C8−59.92 (14)C23—Fe2—C19—C15159.53 (12)
C6—C5—C9—Fe158.99 (13)C17—Fe2—C19—C15−81.72 (12)
C3—C5—C9—Fe1−115.1 (2)C16—Fe2—C20—C21116.97 (15)
C6—Fe1—C9—C880.60 (13)C24—Fe2—C20—C21−119.0 (2)
C5—Fe1—C9—C8118.93 (17)C19—Fe2—C20—C2140.4 (4)
C12—Fe1—C9—C8−47.9 (3)C18—Fe2—C20—C21−165.40 (18)
C11—Fe1—C9—C8163.6 (3)C22—Fe2—C20—C21−38.40 (15)
C13—Fe1—C9—C8−81.87 (15)C23—Fe2—C20—C21−81.92 (16)
C7—Fe1—C9—C836.93 (13)C15—Fe2—C20—C2175.13 (17)
C14—Fe1—C9—C8−124.39 (13)C17—Fe2—C20—C21159.59 (14)
C10—Fe1—C9—C8−165.21 (13)C21—Fe2—C20—C24119.0 (2)
C6—Fe1—C9—C5−38.33 (11)C16—Fe2—C20—C24−124.07 (15)
C12—Fe1—C9—C5−166.9 (2)C19—Fe2—C20—C24159.3 (3)
C11—Fe1—C9—C544.6 (4)C18—Fe2—C20—C24−46.4 (3)
C13—Fe1—C9—C5159.20 (12)C22—Fe2—C20—C2480.56 (17)
C7—Fe1—C9—C5−82.00 (13)C23—Fe2—C20—C2437.04 (15)
C14—Fe1—C9—C5116.68 (12)C15—Fe2—C20—C24−165.91 (14)
C10—Fe1—C9—C575.86 (15)C17—Fe2—C20—C24−81.45 (17)
C8—Fe1—C9—C5−118.93 (17)C24—C20—C21—C220.7 (2)
C6—Fe1—C10—C11−79.78 (16)Fe2—C20—C21—C2259.94 (15)
C5—Fe1—C10—C11−123.38 (14)C24—C20—C21—Fe2−59.23 (15)
C12—Fe1—C10—C1138.04 (14)C16—Fe2—C21—C20−81.35 (15)
C9—Fe1—C10—C11−165.68 (13)C24—Fe2—C21—C2037.87 (14)
C13—Fe1—C10—C1182.02 (15)C19—Fe2—C21—C20−167.81 (13)
C7—Fe1—C10—C11−45.5 (3)C18—Fe2—C21—C20156.2 (3)
C14—Fe1—C10—C11119.8 (2)C22—Fe2—C21—C20118.6 (2)
C8—Fe1—C10—C11161.0 (3)C23—Fe2—C21—C2081.10 (15)
C6—Fe1—C10—C14160.43 (14)C15—Fe2—C21—C20−125.23 (13)
C5—Fe1—C10—C14116.83 (15)C17—Fe2—C21—C20−45.3 (3)
C12—Fe1—C10—C14−81.74 (16)C16—Fe2—C21—C22160.06 (14)
C9—Fe1—C10—C1474.53 (17)C24—Fe2—C21—C22−80.72 (16)
C11—Fe1—C10—C14−119.8 (2)C19—Fe2—C21—C2273.60 (17)
C13—Fe1—C10—C14−37.76 (15)C20—Fe2—C21—C22−118.6 (2)
C7—Fe1—C10—C14−165.3 (2)C18—Fe2—C21—C2237.6 (4)
C8—Fe1—C10—C1441.2 (4)C23—Fe2—C21—C22−37.50 (15)
C14—C10—C11—C120.0 (3)C15—Fe2—C21—C22116.18 (14)
Fe1—C10—C11—C12−59.19 (17)C17—Fe2—C21—C22−163.9 (2)
C14—C10—C11—Fe159.21 (16)C20—C21—C22—C23−0.6 (2)
C6—Fe1—C11—C10117.96 (14)Fe2—C21—C22—C2359.54 (15)
C5—Fe1—C11—C1075.50 (16)C20—C21—C22—Fe2−60.10 (15)
C12—Fe1—C11—C10−119.4 (2)C21—Fe2—C22—C23−118.9 (2)
C9—Fe1—C11—C1041.1 (4)C16—Fe2—C22—C23−166.2 (2)
C13—Fe1—C11—C10−81.20 (15)C24—Fe2—C22—C23−37.15 (14)
C7—Fe1—C11—C10160.21 (13)C19—Fe2—C22—C23114.41 (14)
C14—Fe1—C11—C10−37.31 (14)C20—Fe2—C22—C23−81.10 (15)
C8—Fe1—C11—C10−165.9 (2)C18—Fe2—C22—C2373.08 (17)
C6—Fe1—C11—C12−122.66 (16)C15—Fe2—C22—C23157.92 (13)
C5—Fe1—C11—C12−165.12 (15)C17—Fe2—C22—C2338.5 (4)
C9—Fe1—C11—C12160.5 (3)C16—Fe2—C22—C21−47.3 (3)
C13—Fe1—C11—C1238.17 (16)C24—Fe2—C22—C2181.78 (16)
C7—Fe1—C11—C12−80.41 (18)C19—Fe2—C22—C21−126.66 (15)
C14—Fe1—C11—C1282.07 (17)C20—Fe2—C22—C2137.83 (14)
C10—Fe1—C11—C12119.4 (2)C18—Fe2—C22—C21−167.99 (14)
C8—Fe1—C11—C12−46.6 (3)C23—Fe2—C22—C21118.9 (2)
C10—C11—C12—C13−0.2 (3)C15—Fe2—C22—C21−83.15 (16)
Fe1—C11—C12—C13−60.04 (16)C17—Fe2—C22—C21157.4 (3)
C10—C11—C12—Fe159.86 (17)C21—C22—C23—C240.2 (2)
C6—Fe1—C12—C13−165.28 (13)Fe2—C22—C23—C2459.20 (16)
C5—Fe1—C12—C13161.5 (3)C21—C22—C23—Fe2−59.00 (14)
C9—Fe1—C12—C13−47.7 (3)C21—Fe2—C23—C24−81.36 (16)
C11—Fe1—C12—C13118.2 (2)C16—Fe2—C23—C2442.7 (3)
C7—Fe1—C12—C13−123.80 (15)C19—Fe2—C23—C24156.97 (14)
C14—Fe1—C12—C1337.68 (14)C20—Fe2—C23—C24−37.59 (15)
C10—Fe1—C12—C1381.17 (16)C18—Fe2—C23—C24114.93 (15)
C8—Fe1—C12—C13−81.74 (17)C22—Fe2—C23—C24−119.6 (2)
C6—Fe1—C12—C1176.5 (2)C15—Fe2—C23—C24−169.61 (18)
C5—Fe1—C12—C1143.3 (4)C17—Fe2—C23—C2473.89 (17)
C9—Fe1—C12—C11−165.9 (2)C21—Fe2—C23—C2238.26 (15)
C13—Fe1—C12—C11−118.2 (2)C16—Fe2—C23—C22162.4 (3)
C7—Fe1—C12—C11118.01 (17)C24—Fe2—C23—C22119.6 (2)
C14—Fe1—C12—C11−80.51 (18)C19—Fe2—C23—C22−83.41 (16)
C10—Fe1—C12—C11−37.02 (17)C20—Fe2—C23—C2282.03 (16)
C8—Fe1—C12—C11160.07 (16)C18—Fe2—C23—C22−125.44 (15)
C11—C12—C13—C140.3 (3)C15—Fe2—C23—C22−50.0 (3)
Fe1—C12—C13—C14−59.62 (16)C17—Fe2—C23—C22−166.48 (14)
C11—C12—C13—Fe159.89 (16)C22—C23—C24—C200.2 (3)
C6—Fe1—C13—C1241.2 (3)Fe2—C23—C24—C2059.54 (15)
C5—Fe1—C13—C12−166.20 (19)C22—C23—C24—Fe2−59.29 (15)
C9—Fe1—C13—C12158.90 (15)C21—C20—C24—C23−0.6 (2)
C11—Fe1—C13—C12−38.52 (17)Fe2—C20—C24—C23−59.79 (16)
C7—Fe1—C13—C1275.27 (17)C21—C20—C24—Fe259.19 (15)
C14—Fe1—C13—C12−119.1 (2)C21—Fe2—C24—C2381.92 (17)
C10—Fe1—C13—C12−81.65 (17)C16—Fe2—C24—C23−164.90 (14)
C8—Fe1—C13—C12116.47 (15)C19—Fe2—C24—C23−48.7 (3)
C6—Fe1—C13—C14160.4 (2)C20—Fe2—C24—C23119.7 (2)
C5—Fe1—C13—C14−47.1 (3)C18—Fe2—C24—C23−81.88 (16)
C12—Fe1—C13—C14119.1 (2)C22—Fe2—C24—C2337.39 (15)
C9—Fe1—C13—C14−81.96 (15)C15—Fe2—C24—C23164.2 (3)
C11—Fe1—C13—C1480.62 (16)C17—Fe2—C24—C23−124.39 (15)
C7—Fe1—C13—C14−165.59 (14)C21—Fe2—C24—C20−37.75 (16)
C10—Fe1—C13—C1437.48 (15)C16—Fe2—C24—C2075.43 (18)
C8—Fe1—C13—C14−124.39 (14)C19—Fe2—C24—C20−168.37 (18)
C11—C10—C14—C130.2 (3)C18—Fe2—C24—C20158.45 (14)
Fe1—C10—C14—C1359.29 (16)C22—Fe2—C24—C20−82.28 (17)
C11—C10—C14—Fe1−59.14 (17)C23—Fe2—C24—C20−119.7 (2)
C12—C13—C14—C10−0.3 (3)C15—Fe2—C24—C2044.5 (4)
Fe1—C13—C14—C10−59.58 (16)C17—Fe2—C24—C20115.94 (16)
C12—C13—C14—Fe159.32 (17)C5—C3—N1—N2178.99 (17)
C6—Fe1—C14—C10−45.4 (3)C5—C3—N1—Zn1−6.0 (3)
C5—Fe1—C14—C10−81.29 (17)N3—Zn1—N1—C3−47.56 (19)
C12—Fe1—C14—C1081.40 (16)S1—Zn1—N1—C3−173.83 (17)
C9—Fe1—C14—C10−124.68 (15)S2—Zn1—N1—C355.77 (19)
C11—Fe1—C14—C1036.99 (15)N3—Zn1—N1—N2127.37 (11)
C13—Fe1—C14—C10119.2 (2)S1—Zn1—N1—N21.10 (11)
C7—Fe1—C14—C10160.6 (3)S2—Zn1—N1—N2−129.30 (10)
C8—Fe1—C14—C10−165.85 (14)N5—C1—N2—N1177.48 (16)
C6—Fe1—C14—C13−164.60 (19)S1—C1—N2—N1−0.7 (3)
C5—Fe1—C14—C13159.54 (12)C3—N1—N2—C1175.39 (17)
C12—Fe1—C14—C13−37.77 (14)Zn1—N1—N2—C1−0.54 (19)
C9—Fe1—C14—C13116.15 (14)C15—C4—N3—N41.1 (3)
C11—Fe1—C14—C13−82.18 (15)C15—C4—N3—Zn1−179.14 (14)
C7—Fe1—C14—C1341.4 (4)N1—Zn1—N3—C4−48.03 (16)
C10—Fe1—C14—C13−119.2 (2)S1—Zn1—N3—C453.21 (16)
C8—Fe1—C14—C1374.98 (17)S2—Zn1—N3—C4178.69 (15)
N3—C4—C15—C16167.78 (18)N1—Zn1—N3—N4131.69 (12)
N3—C4—C15—C19−15.6 (3)S1—Zn1—N3—N4−127.08 (11)
N3—C4—C15—Fe2−107.2 (2)S2—Zn1—N3—N4−1.59 (12)
C21—Fe2—C15—C16115.70 (13)N6—C2—N4—N3−179.90 (15)
C24—Fe2—C15—C1639.4 (4)S2—C2—N4—N30.4 (2)
C19—Fe2—C15—C16−118.76 (15)C4—N3—N4—C2−179.13 (16)
C20—Fe2—C15—C1674.16 (15)Zn1—N3—N4—C21.13 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H2N5···S2i0.80 (3)2.80 (2)3.4880 (19)146 (2)
N6—H2N6···N2ii0.81 (3)2.21 (3)2.983 (2)161 (3)
C7—H7A···N2iii0.982.563.465 (3)153
C9—H9A···S20.982.733.697 (2)168
C17—H17A···S2iv0.982.703.479 (2)137
C19—H19A···N40.982.512.936 (2)106
N5—H1N5···Cg1v0.90 (3)2.85 (3)3.515 (2)132 (2)
C6—H6A···Cg2vi0.982.803.755 (2)164
C9—H9A···Cg30.982.473.247 (2)135
C10—H10A···Cg3vi0.982.933.674 (3)134
C24—H24A···Cg4iv0.982.833.629 (2)139
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+3/2, y+1/2, −z+1/2; (vi) x+1/2, −y+3/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H2N5···S2i0.80 (3)2.80 (2)3.4880 (19)146 (2)
N6—H2N6···N2ii0.81 (3)2.21 (3)2.983 (2)161 (3)
C7—H7A···N2iii0.982.563.465 (3)153
C9—H9A···S20.982.733.697 (2)168
C17—H17A···S2iv0.982.703.479 (2)137
C19—H19A···N40.982.512.936 (2)106
N5—H1N5···Cg1v0.90 (3)2.85 (3)3.515 (2)132 (2)
C6—H6A···Cg2vi0.982.803.755 (2)164
C10—H10A···Cg3vi0.982.933.674 (3)134
C24—H24A···Cg4iv0.982.833.629 (2)139
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+3/2, y+1/2, −z+1/2; (vi) x+1/2, −y+3/2, z+1/2.
Acknowledgements top

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312.

references
References top

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.

Genova, P., Varadinova, T., Matesanz, A. I., Marinova, D. & Souza, P. (2004). Toxicol. Appl. Pharm. 197, 107–112.

Haaland, A. & Sikson, J. E. (1968). Chem. Commun. pp. 88–89.

Latheef, L., Manoj, E. & Kurup, M. R. P. (2007). Polyhedron, 26, 4107–4113.

Li, X., Cui, X.-G., Liu, X.-G. & Li, X.-F. (2004). Acta Cryst. E60, m307–m308.

Mariño, M., Gayoso, E., Antelo, J. M., Adrio, L. A., Fernández, J. J. & Vila, J. M. (2006). Polyhedron, 25, 1449–1456.

Melha, K. S. A. (2008). J. Enz. Inhib. Med. Chem. 23, 493–503.

Palenik, J. (1970). Inorg. Chem. 9, 2424–2430.

Quiroga, A. G. M., Pérez, J., López-Solera, I., Montero, E. I., Masaguer, J. R., Alonso, C. & Navarro-Ranninger, C. (1998). J. Inorg. Biochem. 69, 275–281.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.