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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m209.
Published online 2007 December 18. doi:  10.1107/S1600536807066536
PMCID: PMC2915138

Benzyl 5-ferrocenyl-3-(4-methyl­phen­yl)-2-pyrazoline-1-dithio­carboxyl­ate

Abstract

In the title compound, [Fe(C5H5)(C23H21N2S2)], the cyclo­penta­dienyl rings of the ferrocenyl unit deviate slightly from the eclipsed form. In the pyrazoline ring, the N atom bonded to S-benzyl dithio­carbazate exhibits unconventional sp 2-hybrid character in order to form an extended conjugated system. The pyrazoline ring displays an envelope conformation. The mol­ecules are linked into chains along the b axis via C—H(...)S inter­molecular hydrogen bonds.

Related literature

For related literature, see: Fahrni et al. (2003 [triangle]); Huang & Katzenellenbogen (2000 [triangle]); Huang et al. (1998 [triangle]); Liu et al. (2007 [triangle]); Rivett et al. (1979 [triangle]); Shi et al. (2004 [triangle]); Sun et al. (2004 [triangle]); Wiley et al. (1958 [triangle]); Wilkinson et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m209-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C23H21N2S2)]
  • M r = 510.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m209-efi1.jpg
  • a = 9.178 (1) Å
  • b = 10.468 (2) Å
  • c = 13.216 (2) Å
  • α = 99.37 (1)°
  • β = 101.55 (2)°
  • γ = 96.12 (1)°
  • V = 1214.6 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.81 mm−1
  • T = 296 (2) K
  • 0.33 × 0.31 × 0.28 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.776, T max = 0.805
  • 10742 measured reflections
  • 5528 independent reflections
  • 5035 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.088
  • S = 0.99
  • 5528 reflections
  • 299 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Bruker, 2002 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066536/pv2048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066536/pv2048Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Yangzhou University (No. 2006XJJ03) for financial support of this work.

supplementary crystallographic information

Comment

Pyrazoline derivatives are an important class of conjugated fluorescent dyes emitting blue fluorescence and have been extensively applied in the industry due to the high fluorescence quantum yield (Wilkinson et al., 1990; Rivett et al., 1979). For example, pyrazolines have been widely used as optical brightening agents for textiles, paper and fabrics and as a hole-conveying medium in photoconductive materials (Sun et al., 2004; Huang & Katzenellenbogen, 2000; Wiley et al., 1958). We found that ferrocene derivatives have good properties of fluorescence and coordination chemistry with many metal ions (Huang et al., 1998; Shi et al., 2004). Continuing our research (Liu et al., 2007) we report the synthesis and structure of the title compound, (I).

In the structure of (I), the substituted ring (Cps) and unsubstituted ring (Cp) of the ferrocenyl moiety are slightly deprived from eclipsed form, with the five pseudo-torsion angles in the range 10.5 (2) — 10.9 (3)°. The distances from central Fe(II) ion to Cps center [Cg(1)] and to Cp center [Cg(2)] are 1.651 (3) Å and 1.656 (2) Å, respectively. The angle Cg(1)–Fe–Cg(2) is 177.9 (3)° and the central Fe(II) ion is located almost in the middle of the two cyclopentadiene rings which are not parallel because their dihedral angle is 2.3 (4)° (Fig. 1).

In the pyrazolinyl ring, the C=N and C–N bond lengths are in agreement with those found in similar structures (Fahrni et al., 2003). However, the N–N bond length is longer than those found in the above-cited structures. But the bond distance of C21–N1 is shorter than a C–N single bond and slight longer than a C=N double bond. It might contribute to unclassical sp2-hybrid N1 atom which is evident from the sum of the three angles around the N1 atom being 360° (Table 1) and that atoms C21, N1, N2 and C13 are co-planar. Furthemore, atoms S2, C21, N1, N2, C13 along with adjacent phenyl ring result in a large cojugated system.

In its packing diagram, the molecules of (I) are linked into two invers chains via C— H···S intermolecular hydrogen-bonds with C···S distance 3.583 (3) Å and C26—H26···S2 angle 142°, along the b axis (Fig. 2, Table 2).

Experimental

The title compound was synthesized by refluxing an absolute ethanol solution of 1-(4-methylphenyl)-3-ferrocenylprop-2-en-1-one (3.30 g, 10 mmol) and S-benzyldithiocarbazate (1.98 g, 10 mmol) for 24 h. After refrigeration (278 K) of the solution for 10 h, yellow pricipite separated out and recrystallized from a mixture of 1,2-dichloroethane and petroleum ether (5:1 volume ratio) (3.1 g, yield 61%). The yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution at 278 K.

Refinement

All H atoms were fixed geometrically at ideal positions and allowed to ride on the parent atoms with C—H distances 0.96, 0.97, 0.98 and 0.93 Å for CH3, CH2, CH and aromatic CH groups, respectively, and with Uiso(H) values of 1.2 and 1.5 times Ueq(C) for the nonmethyl and methyl groups, respectively.

Figures

Fig. 1.
The molecular structure of (I); displacement ellipsoids are drawn at 50% probability level.
Fig. 2.
Packing diagram of (I), C—H···S inter-molecular hydrogen bonds shown as dashed lines. The H atoms not involved in hyydrogen bonding have been omitted.

Crystal data

[Fe(C5H5)(C23H21N2S2)]Z = 2
Mr = 510.50F000 = 532.0
Triclinic, P1Dx = 1.396 Mg m3
Hall symbol: - P 1Melting point: 345(2) K
a = 9.178 (1) ÅMo Kα radiation λ = 0.71073 Å
b = 10.468 (2) ÅCell parameters from 7052 reflections
c = 13.216 (2) Åθ = 2.3–27.6º
α = 99.37 (1)ºµ = 0.81 mm1
β = 101.55 (2)ºT = 296 (2) K
γ = 96.12 (1)ºBlock, yellow
V = 1214.6 (3) Å30.33 × 0.31 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer5528 independent reflections
Radiation source: fine-focus sealed tube5035 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.019
T = 296(2) Kθmax = 27.7º
[var phi] and ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2002)h = −10→10
Tmin = 0.776, Tmax = 0.805k = −12→12
10742 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0552P)2 + 0.4985P] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.007
5528 reflectionsΔρmax = 0.44 e Å3
299 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. Analysis calculated for C18H16N4OS2: C 65.87, H 5.13, N 5.49%; found: C 65.82, H 5.11, N 5.51%. IR (KBr, cm-1): ν(C=N), ν(S=C) and ν(N–N) 1559 (m), 1245 (s) and 1037 (w) cm-1. 1H NMR (600 MHz, CDCl3,δ, p.p.m.): 7.23–7.76 (m, 9H, ArH), 6.04 (broad, 1H, CH), 4.50–4.47 (d, 1H, CH2), 4.41–4.39 (d, 1H, CH2), 4.15 (s, 5H, C5H5), 4.03 (s, 1H, C5H4), 4.12 (s, 1H, C5H4), 4.19 (s, 1H, C5H4), 4.71 (s, 1H, C5H4), 3.72 (s, 2H, ArCH2), 2.41 (s, 3H, CH3) p.p.m..
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)

xyzUiso*/Ueq
Fe10.56551 (3)−0.22018 (2)0.364537 (18)0.02183 (10)
S10.64012 (5)0.30267 (4)0.12369 (4)0.02864 (13)
S20.72753 (5)0.03133 (4)0.06920 (3)0.02501 (12)
N10.52328 (15)0.09334 (13)0.17619 (11)0.0209 (3)
N20.43248 (16)0.18040 (13)0.21361 (11)0.0219 (3)
C50.3598 (2)−0.28594 (18)0.38988 (16)0.0310 (4)
H50.2866−0.23470.40340.037*
C40.4760 (2)−0.31695 (18)0.46642 (16)0.0322 (4)
H40.4920−0.28970.53880.039*
C30.5633 (2)−0.39647 (18)0.41353 (16)0.0342 (4)
H30.6465−0.43050.44520.041*
C20.5017 (2)−0.41532 (18)0.30377 (16)0.0351 (4)
H20.5376−0.46370.25090.042*
C10.3750 (2)−0.34678 (18)0.28908 (16)0.0324 (4)
H10.3133−0.34270.22500.039*
C60.6003 (2)−0.01980 (17)0.39096 (14)0.0262 (4)
H60.53850.03570.41750.031*
C70.7219 (2)−0.06716 (19)0.45157 (15)0.0340 (4)
H70.7534−0.04830.52450.041*
C80.7865 (2)−0.1481 (2)0.38121 (17)0.0365 (5)
H80.8680−0.19170.40010.044*
C90.7059 (2)−0.15140 (18)0.27690 (15)0.0287 (4)
H90.7257−0.19720.21580.034*
C100.58923 (19)−0.07210 (16)0.28218 (13)0.0218 (3)
C110.47914 (18)−0.04276 (16)0.19133 (13)0.0212 (3)
H110.4742−0.10630.12710.025*
C120.32107 (19)−0.03292 (16)0.21151 (14)0.0230 (4)
H12A0.2439−0.07460.15000.028*
H12B0.3063−0.07250.27080.028*
C130.31983 (18)0.11285 (16)0.23500 (12)0.0211 (3)
C140.20317 (18)0.17603 (17)0.27623 (13)0.0219 (3)
C150.0737 (2)0.10168 (18)0.28749 (14)0.0271 (4)
H150.06070.01110.26770.033*
C16−0.0357 (2)0.16144 (19)0.32793 (14)0.0309 (4)
H16−0.12120.11030.33490.037*
C17−0.0196 (2)0.2960 (2)0.35799 (14)0.0309 (4)
C180.1102 (2)0.37050 (18)0.34690 (14)0.0296 (4)
H180.12300.46110.36710.036*
C190.2197 (2)0.31208 (17)0.30645 (14)0.0260 (4)
H190.30480.36350.29930.031*
C20−0.1389 (2)0.3607 (3)0.40227 (19)0.0483 (6)
H20A−0.23640.31530.36580.072*
H20B−0.13130.45020.39340.072*
H20C−0.12460.35760.47580.072*
C210.62648 (18)0.13289 (16)0.12474 (13)0.0210 (3)
C220.7966 (2)0.32849 (18)0.06058 (17)0.0356 (5)
H22A0.88410.29760.09780.043*
H22B0.77060.2810−0.01150.043*
C230.8295 (2)0.47341 (17)0.06311 (14)0.0263 (4)
C280.7407 (2)0.5341 (2)−0.00745 (16)0.0370 (5)
H280.65660.4858−0.05490.044*
C270.7770 (3)0.6667 (2)−0.00738 (18)0.0442 (5)
H270.71810.7062−0.05570.053*
C260.8997 (2)0.73954 (19)0.06398 (19)0.0405 (5)
H260.92460.82790.06360.049*
C250.9849 (2)0.6807 (2)0.13578 (19)0.0408 (5)
H251.06640.73000.18530.049*
C240.9504 (2)0.54858 (19)0.13486 (17)0.0344 (4)
H241.00970.50980.18340.041*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.02452 (15)0.02086 (15)0.02275 (15)0.00548 (10)0.00666 (11)0.00855 (10)
S10.0313 (2)0.0201 (2)0.0413 (3)0.00543 (17)0.0205 (2)0.00872 (19)
S20.0281 (2)0.0247 (2)0.0256 (2)0.00900 (17)0.01053 (18)0.00548 (17)
N10.0250 (7)0.0185 (7)0.0220 (7)0.0066 (5)0.0085 (6)0.0057 (5)
N20.0242 (7)0.0224 (7)0.0221 (7)0.0077 (6)0.0085 (6)0.0064 (6)
C50.0291 (9)0.0274 (9)0.0412 (11)0.0029 (7)0.0142 (8)0.0125 (8)
C40.0403 (11)0.0297 (10)0.0319 (10)0.0035 (8)0.0138 (8)0.0148 (8)
C30.0408 (11)0.0239 (9)0.0443 (12)0.0099 (8)0.0121 (9)0.0180 (8)
C20.0442 (11)0.0213 (9)0.0415 (11)0.0056 (8)0.0147 (9)0.0040 (8)
C10.0332 (10)0.0254 (9)0.0361 (11)−0.0019 (8)0.0038 (8)0.0075 (8)
C60.0326 (9)0.0209 (8)0.0240 (9)0.0000 (7)0.0053 (7)0.0049 (7)
C70.0351 (10)0.0348 (10)0.0268 (10)−0.0067 (8)−0.0032 (8)0.0108 (8)
C80.0236 (9)0.0423 (11)0.0481 (12)0.0062 (8)0.0046 (8)0.0248 (10)
C90.0270 (9)0.0308 (10)0.0356 (10)0.0082 (7)0.0144 (8)0.0153 (8)
C100.0239 (8)0.0201 (8)0.0239 (9)0.0021 (6)0.0076 (7)0.0092 (7)
C110.0268 (9)0.0172 (8)0.0205 (8)0.0040 (6)0.0059 (7)0.0049 (6)
C120.0229 (8)0.0213 (8)0.0254 (9)0.0027 (6)0.0045 (7)0.0071 (7)
C130.0228 (8)0.0230 (8)0.0175 (8)0.0027 (7)0.0024 (6)0.0070 (6)
C140.0220 (8)0.0265 (9)0.0182 (8)0.0054 (7)0.0035 (6)0.0069 (7)
C150.0267 (9)0.0270 (9)0.0270 (9)0.0011 (7)0.0051 (7)0.0059 (7)
C160.0214 (9)0.0424 (11)0.0280 (9)−0.0021 (8)0.0073 (7)0.0060 (8)
C170.0268 (9)0.0444 (11)0.0221 (9)0.0080 (8)0.0075 (7)0.0032 (8)
C180.0331 (10)0.0283 (9)0.0277 (9)0.0078 (8)0.0082 (8)0.0020 (7)
C190.0250 (9)0.0260 (9)0.0287 (9)0.0034 (7)0.0084 (7)0.0074 (7)
C200.0334 (11)0.0616 (15)0.0477 (13)0.0092 (10)0.0175 (10)−0.0079 (11)
C210.0222 (8)0.0217 (8)0.0190 (8)0.0035 (6)0.0030 (6)0.0054 (6)
C220.0384 (11)0.0265 (10)0.0497 (12)0.0037 (8)0.0282 (9)0.0076 (9)
C230.0271 (9)0.0252 (9)0.0320 (10)0.0048 (7)0.0171 (8)0.0077 (7)
C280.0345 (10)0.0428 (12)0.0327 (11)0.0070 (9)0.0050 (8)0.0066 (9)
C270.0503 (13)0.0474 (13)0.0487 (13)0.0257 (11)0.0184 (10)0.0276 (10)
C260.0370 (11)0.0266 (10)0.0701 (15)0.0109 (8)0.0301 (11)0.0178 (10)
C250.0266 (10)0.0321 (11)0.0620 (14)0.0017 (8)0.0098 (9)0.0055 (10)
C240.0290 (10)0.0342 (10)0.0439 (11)0.0074 (8)0.0086 (8)0.0159 (9)

Geometric parameters (Å, °)

Fe1—C82.0428 (19)C10—C111.502 (2)
Fe1—C22.0452 (19)C11—C121.538 (2)
Fe1—C12.0460 (19)C11—H110.9800
Fe1—C92.0474 (18)C12—C131.509 (2)
Fe1—C62.0488 (17)C12—H12A0.9700
Fe1—C72.0487 (19)C12—H12B0.9700
Fe1—C52.0493 (18)C13—C141.466 (2)
Fe1—C102.0510 (16)C14—C151.397 (2)
Fe1—C32.0521 (18)C14—C191.398 (2)
Fe1—C42.0549 (18)C15—C161.388 (3)
S1—C211.7708 (17)C15—H150.9300
S1—C221.8167 (18)C16—C171.383 (3)
S2—C211.6608 (17)C16—H160.9300
N1—C211.340 (2)C17—C181.399 (3)
N1—N21.3964 (19)C17—C201.512 (3)
N1—C111.495 (2)C18—C191.382 (3)
N2—C131.294 (2)C18—H180.9300
C5—C11.420 (3)C19—H190.9300
C5—C41.419 (3)C20—H20A0.9600
C5—H50.9300C20—H20B0.9600
C4—C31.414 (3)C20—H20C0.9600
C4—H40.9300C22—C231.508 (2)
C3—C21.420 (3)C22—H22A0.9700
C3—H30.9300C22—H22B0.9700
C2—C11.428 (3)C23—C241.378 (3)
C2—H20.9300C23—C281.392 (3)
C1—H10.9300C28—C271.392 (3)
C6—C71.422 (3)C28—H280.9300
C6—C101.432 (2)C27—C261.377 (3)
C6—H60.9300C27—H270.9300
C7—C81.416 (3)C26—C251.374 (3)
C7—H70.9300C26—H260.9300
C8—C91.421 (3)C25—C241.383 (3)
C8—H80.9300C25—H250.9300
C9—C101.429 (2)C24—H240.9300
C9—H90.9300
C8—Fe1—C2116.95 (9)C6—C7—Fe169.69 (10)
C8—Fe1—C1151.92 (9)C8—C7—H7126.1
C2—Fe1—C140.85 (8)C6—C7—H7126.1
C8—Fe1—C940.66 (8)Fe1—C7—H7126.3
C2—Fe1—C9106.49 (8)C7—C8—C9108.51 (17)
C1—Fe1—C9118.79 (8)C7—C8—Fe169.98 (11)
C8—Fe1—C668.20 (8)C9—C8—Fe169.85 (10)
C2—Fe1—C6166.18 (8)C7—C8—H8125.7
C1—Fe1—C6129.18 (7)C9—C8—H8125.7
C9—Fe1—C668.42 (7)Fe1—C8—H8126.0
C8—Fe1—C740.49 (9)C8—C9—C10108.07 (17)
C2—Fe1—C7151.03 (8)C8—C9—Fe169.49 (11)
C1—Fe1—C7166.78 (8)C10—C9—Fe169.73 (9)
C9—Fe1—C768.41 (8)C8—C9—H9126.0
C6—Fe1—C740.62 (8)C10—C9—H9126.0
C8—Fe1—C5164.95 (8)Fe1—C9—H9126.4
C2—Fe1—C568.37 (8)C9—C10—C6107.23 (15)
C1—Fe1—C540.57 (8)C9—C10—C11127.04 (15)
C9—Fe1—C5153.95 (8)C6—C10—C11125.67 (15)
C6—Fe1—C5110.18 (7)C9—C10—Fe169.46 (9)
C7—Fe1—C5128.59 (8)C6—C10—Fe169.47 (9)
C8—Fe1—C1068.59 (7)C11—C10—Fe1128.36 (11)
C2—Fe1—C10127.05 (8)N1—C11—C10109.61 (13)
C1—Fe1—C10108.77 (7)N1—C11—C12100.44 (12)
C9—Fe1—C1040.81 (7)C10—C11—C12114.22 (14)
C6—Fe1—C1040.88 (7)N1—C11—H11110.7
C7—Fe1—C1068.72 (7)C10—C11—H11110.7
C5—Fe1—C10120.71 (7)C12—C11—H11110.7
C8—Fe1—C3106.16 (8)C13—C12—C11102.75 (13)
C2—Fe1—C340.56 (8)C13—C12—H12A111.2
C1—Fe1—C368.31 (8)C11—C12—H12A111.2
C9—Fe1—C3125.60 (8)C13—C12—H12B111.2
C6—Fe1—C3152.81 (8)C11—C12—H12B111.2
C7—Fe1—C3117.78 (8)H12A—C12—H12B109.1
C5—Fe1—C368.04 (8)N2—C13—C14121.50 (15)
C10—Fe1—C3164.02 (8)N2—C13—C12113.60 (15)
C8—Fe1—C4126.35 (8)C14—C13—C12124.88 (14)
C2—Fe1—C468.10 (8)C15—C14—C19118.43 (16)
C1—Fe1—C468.15 (8)C15—C14—C13120.79 (15)
C9—Fe1—C4163.37 (8)C19—C14—C13120.77 (15)
C6—Fe1—C4120.38 (8)C16—C15—C14120.77 (17)
C7—Fe1—C4108.22 (8)C16—C15—H15119.6
C5—Fe1—C440.46 (8)C14—C15—H15119.6
C10—Fe1—C4154.75 (7)C17—C16—C15120.92 (17)
C3—Fe1—C440.27 (8)C17—C16—H16119.5
C21—S1—C22101.89 (8)C15—C16—H16119.5
C21—N1—N2120.26 (13)C16—C17—C18118.34 (17)
C21—N1—C11127.22 (14)C16—C17—C20120.75 (18)
N2—N1—C11112.25 (12)C18—C17—C20120.91 (19)
C13—N2—N1108.02 (13)C19—C18—C17121.25 (17)
C1—C5—C4108.06 (17)C19—C18—H18119.4
C1—C5—Fe169.59 (11)C17—C18—H18119.4
C4—C5—Fe169.98 (11)C18—C19—C14120.30 (16)
C1—C5—H5126.0C18—C19—H19119.9
C4—C5—H5126.0C14—C19—H19119.9
Fe1—C5—H5126.0C17—C20—H20A109.5
C3—C4—C5108.19 (17)C17—C20—H20B109.5
C3—C4—Fe169.76 (10)H20A—C20—H20B109.5
C5—C4—Fe169.56 (10)C17—C20—H20C109.5
C3—C4—H4125.9H20A—C20—H20C109.5
C5—C4—H4125.9H20B—C20—H20C109.5
Fe1—C4—H4126.4N1—C21—S2122.65 (13)
C4—C3—C2108.20 (17)N1—C21—S1112.19 (12)
C4—C3—Fe169.97 (10)S2—C21—S1125.16 (10)
C2—C3—Fe169.46 (10)C23—C22—S1107.43 (12)
C4—C3—H3125.9C23—C22—H22A110.2
C2—C3—H3125.9S1—C22—H22A110.2
Fe1—C3—H3126.2C23—C22—H22B110.2
C3—C2—C1107.78 (18)S1—C22—H22B110.2
C3—C2—Fe169.98 (11)H22A—C22—H22B108.5
C1—C2—Fe169.60 (10)C24—C23—C28118.41 (17)
C3—C2—H2126.1C24—C23—C22120.43 (17)
C1—C2—H2126.1C28—C23—C22121.16 (18)
Fe1—C2—H2125.9C23—C28—C27120.40 (19)
C5—C1—C2107.77 (18)C23—C28—H28119.8
C5—C1—Fe169.84 (11)C27—C28—H28119.8
C2—C1—Fe169.54 (11)C26—C27—C28120.19 (19)
C5—C1—H1126.1C26—C27—H27119.9
C2—C1—H1126.1C28—C27—H27119.9
Fe1—C1—H1126.1C25—C26—C27119.51 (18)
C7—C6—C10108.33 (16)C25—C26—H26120.2
C7—C6—Fe169.69 (10)C27—C26—H26120.2
C10—C6—Fe169.64 (9)C26—C25—C24120.4 (2)
C7—C6—H6125.8C26—C25—H25119.8
C10—C6—H6125.8C24—C25—H25119.8
Fe1—C6—H6126.4C23—C24—C25121.06 (19)
C8—C7—C6107.85 (17)C23—C24—H24119.5
C8—C7—Fe169.53 (11)C25—C24—H24119.5
C21—N1—N2—C13163.81 (15)C1—Fe1—C7—C6−43.9 (4)
C11—N1—N2—C13−10.50 (18)C9—Fe1—C7—C681.61 (12)
C8—Fe1—C5—C1−151.8 (3)C5—Fe1—C7—C6−75.37 (13)
C2—Fe1—C5—C1−38.01 (11)C10—Fe1—C7—C637.61 (10)
C9—Fe1—C5—C145.3 (2)C3—Fe1—C7—C6−158.46 (11)
C6—Fe1—C5—C1127.27 (11)C4—Fe1—C7—C6−115.72 (12)
C7—Fe1—C5—C1169.42 (11)C6—C7—C8—C90.0 (2)
C10—Fe1—C5—C183.21 (12)Fe1—C7—C8—C959.42 (13)
C3—Fe1—C5—C1−81.85 (12)C6—C7—C8—Fe1−59.37 (13)
C4—Fe1—C5—C1−119.19 (16)C2—Fe1—C8—C7−156.34 (11)
C8—Fe1—C5—C4−32.6 (3)C1—Fe1—C8—C7171.85 (15)
C2—Fe1—C5—C481.18 (12)C9—Fe1—C8—C7119.58 (16)
C1—Fe1—C5—C4119.19 (16)C6—Fe1—C8—C737.76 (11)
C9—Fe1—C5—C4164.52 (16)C5—Fe1—C8—C7−49.0 (3)
C6—Fe1—C5—C4−113.54 (12)C10—Fe1—C8—C781.88 (12)
C7—Fe1—C5—C4−71.39 (14)C3—Fe1—C8—C7−114.07 (12)
C10—Fe1—C5—C4−157.60 (11)C4—Fe1—C8—C7−74.70 (14)
C3—Fe1—C5—C437.34 (12)C2—Fe1—C8—C984.08 (13)
C1—C5—C4—C30.1 (2)C1—Fe1—C8—C952.3 (2)
Fe1—C5—C4—C3−59.26 (13)C6—Fe1—C8—C9−81.83 (12)
C1—C5—C4—Fe159.39 (12)C7—Fe1—C8—C9−119.58 (16)
C8—Fe1—C4—C3−70.49 (15)C5—Fe1—C8—C9−168.6 (3)
C2—Fe1—C4—C337.61 (12)C10—Fe1—C8—C9−37.70 (11)
C1—Fe1—C4—C381.79 (13)C3—Fe1—C8—C9126.35 (12)
C9—Fe1—C4—C3−36.3 (3)C4—Fe1—C8—C9165.72 (11)
C6—Fe1—C4—C3−154.57 (12)C7—C8—C9—C10−0.2 (2)
C7—Fe1—C4—C3−111.74 (13)Fe1—C8—C9—C1059.26 (12)
C5—Fe1—C4—C3119.51 (17)C7—C8—C9—Fe1−59.50 (13)
C10—Fe1—C4—C3169.66 (15)C2—Fe1—C9—C8−112.38 (13)
C8—Fe1—C4—C5170.00 (12)C1—Fe1—C9—C8−154.87 (12)
C2—Fe1—C4—C5−81.90 (13)C6—Fe1—C9—C881.23 (13)
C1—Fe1—C4—C5−37.72 (11)C7—Fe1—C9—C837.40 (12)
C9—Fe1—C4—C5−155.8 (2)C5—Fe1—C9—C8173.27 (16)
C6—Fe1—C4—C585.92 (13)C10—Fe1—C9—C8119.41 (16)
C7—Fe1—C4—C5128.75 (12)C3—Fe1—C9—C8−72.06 (15)
C10—Fe1—C4—C550.2 (2)C4—Fe1—C9—C8−44.0 (3)
C3—Fe1—C4—C5−119.51 (17)C8—Fe1—C9—C10−119.41 (16)
C5—C4—C3—C20.0 (2)C2—Fe1—C9—C10128.21 (11)
Fe1—C4—C3—C2−59.13 (13)C1—Fe1—C9—C1085.72 (12)
C5—C4—C3—Fe159.14 (13)C6—Fe1—C9—C10−38.18 (10)
C8—Fe1—C3—C4127.78 (12)C7—Fe1—C9—C10−82.01 (11)
C2—Fe1—C3—C4−119.45 (17)C5—Fe1—C9—C1053.9 (2)
C1—Fe1—C3—C4−81.37 (13)C3—Fe1—C9—C10168.53 (10)
C9—Fe1—C3—C4167.97 (11)C4—Fe1—C9—C10−163.4 (2)
C6—Fe1—C3—C454.2 (2)C8—C9—C10—C60.34 (19)
C7—Fe1—C3—C485.70 (13)Fe1—C9—C10—C659.45 (11)
C5—Fe1—C3—C4−37.51 (12)C8—C9—C10—C11177.69 (16)
C10—Fe1—C3—C4−163.8 (2)Fe1—C9—C10—C11−123.19 (16)
C8—Fe1—C3—C2−112.77 (13)C8—C9—C10—Fe1−59.12 (12)
C1—Fe1—C3—C238.08 (12)C7—C6—C10—C9−0.31 (19)
C9—Fe1—C3—C2−72.58 (14)Fe1—C6—C10—C9−59.44 (11)
C6—Fe1—C3—C2173.60 (15)C7—C6—C10—C11−177.71 (15)
C7—Fe1—C3—C2−154.85 (12)Fe1—C6—C10—C11123.15 (16)
C5—Fe1—C3—C281.94 (13)C7—C6—C10—Fe159.14 (12)
C10—Fe1—C3—C2−44.4 (3)C8—Fe1—C10—C937.56 (12)
C4—Fe1—C3—C2119.45 (17)C2—Fe1—C10—C9−70.73 (14)
C4—C3—C2—C1−0.1 (2)C1—Fe1—C10—C9−112.63 (12)
Fe1—C3—C2—C1−59.58 (13)C6—Fe1—C10—C9118.56 (15)
C4—C3—C2—Fe159.45 (13)C7—Fe1—C10—C981.19 (12)
C8—Fe1—C2—C383.47 (13)C5—Fe1—C10—C9−155.64 (11)
C1—Fe1—C2—C3−118.83 (17)C3—Fe1—C10—C9−36.0 (3)
C9—Fe1—C2—C3125.99 (12)C4—Fe1—C10—C9168.95 (16)
C6—Fe1—C2—C3−167.7 (3)C8—Fe1—C10—C6−81.00 (12)
C7—Fe1—C2—C350.9 (2)C2—Fe1—C10—C6170.70 (11)
C5—Fe1—C2—C3−81.07 (12)C1—Fe1—C10—C6128.81 (11)
C10—Fe1—C2—C3166.04 (11)C9—Fe1—C10—C6−118.56 (15)
C4—Fe1—C2—C3−37.35 (12)C7—Fe1—C10—C6−37.37 (11)
C8—Fe1—C2—C1−157.71 (12)C5—Fe1—C10—C685.80 (12)
C9—Fe1—C2—C1−115.19 (12)C3—Fe1—C10—C6−154.5 (3)
C6—Fe1—C2—C1−48.9 (4)C4—Fe1—C10—C650.4 (2)
C7—Fe1—C2—C1169.74 (15)C8—Fe1—C10—C11159.15 (17)
C5—Fe1—C2—C137.75 (12)C2—Fe1—C10—C1150.85 (18)
C10—Fe1—C2—C1−75.14 (14)C1—Fe1—C10—C118.96 (17)
C3—Fe1—C2—C1118.83 (17)C9—Fe1—C10—C11121.59 (19)
C4—Fe1—C2—C181.48 (12)C6—Fe1—C10—C11−119.85 (19)
C4—C5—C1—C2−0.2 (2)C7—Fe1—C10—C11−157.23 (17)
Fe1—C5—C1—C259.43 (13)C5—Fe1—C10—C11−34.05 (18)
C4—C5—C1—Fe1−59.63 (13)C3—Fe1—C10—C1185.6 (3)
C3—C2—C1—C50.2 (2)C4—Fe1—C10—C11−69.5 (2)
Fe1—C2—C1—C5−59.62 (12)C21—N1—C11—C1082.3 (2)
C3—C2—C1—Fe159.82 (13)N2—N1—C11—C10−103.92 (15)
C8—Fe1—C1—C5164.87 (15)C21—N1—C11—C12−157.18 (16)
C2—Fe1—C1—C5118.94 (16)N2—N1—C11—C1216.65 (16)
C9—Fe1—C1—C5−159.12 (11)C9—C10—C11—N1−104.11 (18)
C6—Fe1—C1—C5−74.48 (14)C6—C10—C11—N172.8 (2)
C7—Fe1—C1—C5−38.9 (4)Fe1—C10—C11—N1163.79 (12)
C10—Fe1—C1—C5−115.62 (11)C9—C10—C11—C12144.09 (17)
C3—Fe1—C1—C581.13 (12)C6—C10—C11—C12−39.0 (2)
C4—Fe1—C1—C537.62 (11)Fe1—C10—C11—C1252.0 (2)
C8—Fe1—C1—C245.9 (2)N1—C11—C12—C13−15.48 (15)
C9—Fe1—C1—C281.94 (13)C10—C11—C12—C13101.72 (15)
C6—Fe1—C1—C2166.58 (11)N1—N2—C13—C14179.95 (14)
C7—Fe1—C1—C2−157.8 (3)N1—N2—C13—C12−1.10 (19)
C5—Fe1—C1—C2−118.94 (16)C11—C12—C13—N211.39 (18)
C10—Fe1—C1—C2125.44 (12)C11—C12—C13—C14−169.70 (15)
C3—Fe1—C1—C2−37.81 (12)N2—C13—C14—C15172.56 (16)
C4—Fe1—C1—C2−81.33 (12)C12—C13—C14—C15−6.3 (2)
C8—Fe1—C6—C7−37.65 (12)N2—C13—C14—C19−8.2 (2)
C2—Fe1—C6—C7−152.3 (3)C12—C13—C14—C19172.93 (16)
C1—Fe1—C6—C7168.21 (12)C19—C14—C15—C16−0.1 (3)
C9—Fe1—C6—C7−81.56 (12)C13—C14—C15—C16179.08 (16)
C5—Fe1—C6—C7126.32 (12)C14—C15—C16—C170.1 (3)
C10—Fe1—C6—C7−119.67 (16)C15—C16—C17—C18−0.2 (3)
C3—Fe1—C6—C745.3 (2)C15—C16—C17—C20−179.84 (18)
C4—Fe1—C6—C782.72 (13)C16—C17—C18—C190.3 (3)
C8—Fe1—C6—C1082.03 (11)C20—C17—C18—C19−179.98 (18)
C2—Fe1—C6—C10−32.7 (4)C17—C18—C19—C14−0.4 (3)
C1—Fe1—C6—C10−72.12 (13)C15—C14—C19—C180.3 (3)
C9—Fe1—C6—C1038.12 (10)C13—C14—C19—C18−178.90 (16)
C7—Fe1—C6—C10119.67 (16)N2—N1—C21—S2−174.50 (11)
C5—Fe1—C6—C10−114.01 (11)C11—N1—C21—S2−1.1 (2)
C3—Fe1—C6—C10164.99 (15)N2—N1—C21—S15.40 (19)
C4—Fe1—C6—C10−157.61 (10)C11—N1—C21—S1178.78 (12)
C10—C6—C7—C80.2 (2)C22—S1—C21—N1175.13 (13)
Fe1—C6—C7—C859.27 (13)C22—S1—C21—S2−4.97 (14)
C10—C6—C7—Fe1−59.11 (12)C21—S1—C22—C23−175.12 (14)
C2—Fe1—C7—C847.6 (2)S1—C22—C23—C24102.92 (18)
C1—Fe1—C7—C8−163.0 (3)S1—C22—C23—C28−78.0 (2)
C9—Fe1—C7—C8−37.54 (11)C24—C23—C28—C272.2 (3)
C6—Fe1—C7—C8−119.15 (16)C22—C23—C28—C27−176.87 (18)
C5—Fe1—C7—C8165.48 (11)C23—C28—C27—C26−1.2 (3)
C10—Fe1—C7—C8−81.54 (12)C28—C27—C26—C25−0.7 (3)
C3—Fe1—C7—C882.39 (13)C27—C26—C25—C241.7 (3)
C4—Fe1—C7—C8125.13 (12)C28—C23—C24—C25−1.2 (3)
C8—Fe1—C7—C6119.15 (16)C22—C23—C24—C25177.82 (18)
C2—Fe1—C7—C6166.76 (15)C26—C25—C24—C23−0.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2048).

References

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