PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1366.
Published online 2008 October 4. doi:  10.1107/S1600536808031504
PMCID: PMC2959619

(2,3,7,8,12,13,17,18-Octa­ethyl­por­phin­ato)(trifluoro­methane­sulfonato)iron(III)

Abstract

The title compound, [Fe(CF3O3S)(C36H44N4)], is an iron(III) porphyrin complex with the trifluoro­methane­sulfonate anion as an axial ligand. The Fe atom is displaced by 0.219 (2) Å toward the trifluoro­methane­sulfonate anion from the 24-atom mean plane of the porphyrin, resulting in a distorted FeN4O square-based pyramidal geometry. One ethyl­ene group is disordered over two orientations in a 0.502 (6):0.498 (6) ratio.

Related literature

For the structures of other related porphyrin (‘picket-fence’, tetra­phenyl­porphyrin) derivatives, see: González & Wilson (1994 [triangle]); Gismelseed et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1366-scheme1.jpg

Experimental

Crystal data

  • [Fe(CF3O3S)(C36H44N4)]
  • M r = 737.67
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1366-efi1.jpg
  • a = 12.2180 (14) Å
  • b = 12.7994 (15) Å
  • c = 13.8028 (16) Å
  • α = 96.324 (5)°
  • β = 115.007 (5)°
  • γ = 111.721 (6)°
  • V = 1723.8 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.56 mm−1
  • T = 100 (2) K
  • 0.52 × 0.36 × 0.35 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.760, T max = 0.829
  • 17956 measured reflections
  • 6731 independent reflections
  • 6207 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.107
  • S = 1.04
  • 6731 reflections
  • 452 parameters
  • 26 restraints
  • H-atom parameters constrained
  • Δρmax = 1.02 e Å−3
  • Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031504/hb2808sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031504/hb2808Isup2.hkl

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

Acknowledgments

The authors thank the National Institutes of Health (GM 064476) for support of this research. The authors also thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer and computers used in this work.

supplementary crystallographic information

Comment

Many iron porphyrin complexes have been synthesized as models for the study of the important roles that heme enzymes play in biological processes. In this paper, we report the first structure of the title compound, (I), five-coordinate (trifluoromethanesulfonato)(octaethylporphinato)iron(III). Other trifluoromethanesulfonato iron porphyrin derivatives have been reported previously: The (TpivPP)Fe(OSO2CF3)(H2O) compound is six-coordinate at Fe, and the (TPP)Fe(OSO2CF3) is five coordinate at Fe (González & Wilson 1994 and Gismelseed et al. 1990).

The molecular structure of (I) is shown in Fig. 1. The porphyrin core of the compound is moderately ruffled. The iron atom is displaced by 0.219 (2) Å from the 24-atom mean porphyrin plane toward the trifluoromethanesulfonate anion. The trifluoromethanesulfonate anion binds to the iron center through one of its sulfonato oxygen atoms. The Fe—O distance of 2.0392 (14) Å is longer than those of the five-coordinate tetraphenylporphyrin derivative [1.946 (6) Å - 2.022 (3) Å] (González & Wilson 1994) and the six-coordinate picket-fence porphyrin derivative [2.188 (5) Å) (Gismelseed et al., 1990). The Fe—Np distances are 1.9979 (17) Å - 2.0001 (17) Å (Table 1). The bond angle of the Fe—O—S linkage is 129.34 (8) °.

Experimental

To a toluene solution (20 ml) of (octaethylporphinato)FeCl (0.015 g, 0.024 mmol) (purchased from Mid-Century Chemical Inc.) under N2 was added silver trifluoromethanesulfonate (0.0068 g, 0.026 mmol) (purchased from Aldrich Chemical Company and used as received). The resulting mixture was stirred for 2 h and filtered into a clean Schlenk tube under N2. A red powder was obtained after removal of the solvent under vacuum. A suitable black prism of (I) was grown by slow evaporation of a dichloromethane-hexane (1:1 v/v) solution of the complex at room temperature under N2.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å for aromatic carbons, 0.98 Å for methylene carbons and 0.99 Å for methyl carbons. One ethylene group (C31—C32) is disordered and is modeled in two orientations, with occupancies refined to 0.502 (6) and 0.498 (6) for the unprimed and primed atoms, respectively.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 35% probability level. H atoms and the minor disorder component are omitted for clarity.

Crystal data

[Fe(CF3O3S)(C36H44N4)]Z = 2
Mr = 737.67F(000) = 774
Triclinic, P1Dx = 1.421 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.2180 (14) ÅCell parameters from 7756 reflections
b = 12.7994 (15) Åθ = 2.3–28.3°
c = 13.8028 (16) ŵ = 0.56 mm1
α = 96.324 (5)°T = 100 K
β = 115.007 (5)°Prism, black
γ = 111.721 (6)°0.52 × 0.36 × 0.35 mm
V = 1723.8 (4) Å3

Data collection

Bruker APEX CCD diffractometer6731 independent reflections
Radiation source: fine-focus sealed tube6207 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)h = −15→15
Tmin = 0.760, Tmax = 0.829k = −15→15
17956 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.058P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
6731 reflections(Δ/σ)max = 0.001
452 parametersΔρmax = 1.02 e Å3
26 restraintsΔρmin = −0.65 e Å3

Special details

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. Restraints on the positional and displacement parameters of the disordered atoms were required.

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

xyzUiso*/UeqOcc. (<1)
Fe10.41603 (3)0.34987 (2)0.31778 (2)0.01775 (10)
N10.44180 (17)0.27844 (15)0.44231 (13)0.0200 (3)
N20.59488 (17)0.49255 (14)0.42231 (13)0.0204 (3)
N30.37474 (16)0.43983 (14)0.20913 (13)0.0189 (3)
N40.22023 (16)0.22759 (14)0.23117 (13)0.0192 (3)
C10.3569 (2)0.16671 (18)0.43492 (16)0.0205 (4)
C20.4213 (2)0.13718 (19)0.53472 (17)0.0224 (4)
C30.5444 (2)0.23325 (19)0.60530 (16)0.0226 (4)
C40.5575 (2)0.32002 (18)0.54697 (16)0.0214 (4)
C50.6719 (2)0.42714 (19)0.58778 (16)0.0229 (4)
H50.74330.44850.66260.028*
C60.6912 (2)0.50594 (18)0.52876 (16)0.0223 (4)
C70.8168 (2)0.61118 (18)0.56848 (17)0.0259 (4)
C80.7974 (2)0.66287 (18)0.48569 (18)0.0268 (4)
C90.6592 (2)0.58940 (17)0.39561 (17)0.0223 (4)
C100.5988 (2)0.61321 (17)0.29676 (17)0.0223 (4)
H100.65310.68250.28760.027*
C110.4660 (2)0.54473 (17)0.21018 (16)0.0193 (4)
C120.4026 (2)0.57402 (18)0.11033 (17)0.0219 (4)
C130.2715 (2)0.4872 (2)0.04836 (18)0.0270 (4)
C140.2548 (2)0.40375 (18)0.10955 (17)0.0224 (4)
C150.1357 (2)0.30184 (19)0.07331 (17)0.0239 (4)
H150.05880.28730.00410.029*
C160.1192 (2)0.21942 (18)0.12914 (16)0.0203 (4)
C17−0.0046 (2)0.11087 (18)0.08721 (16)0.0202 (4)
C180.0227 (2)0.05058 (17)0.16272 (16)0.0205 (4)
C190.1613 (2)0.12371 (17)0.25172 (16)0.0197 (4)
C200.2268 (2)0.09456 (18)0.34568 (17)0.0210 (4)
H200.17840.01870.34910.025*
C210.3620 (2)0.02166 (19)0.55482 (18)0.0261 (4)
H21A0.43720.00660.60460.031*
H21B0.3057−0.04310.48200.031*
C220.2749 (2)0.0183 (2)0.6080 (2)0.0328 (5)
H22A0.32980.08180.68040.049*
H22B0.2410−0.05850.62010.049*
H22C0.19770.02950.55780.049*
C230.6511 (2)0.2489 (2)0.72072 (17)0.0266 (4)
H23A0.60570.20230.75740.032*
H23B0.69970.33350.76660.032*
C240.7551 (2)0.2103 (2)0.71934 (19)0.0307 (5)
H24A0.70980.12430.68340.046*
H24B0.82760.23120.79680.046*
H24C0.79450.25060.67700.046*
C250.9460 (2)0.6459 (2)0.67638 (19)0.0323 (5)
H25A0.92420.62990.73630.039*
H25B1.00620.73200.69990.039*
C261.0208 (2)0.5775 (2)0.6629 (2)0.0402 (6)
H26A0.95930.49210.63450.060*
H26B1.10010.59680.73600.060*
H26C1.05100.59960.60930.060*
C270.8991 (2)0.7701 (2)0.4815 (2)0.0386 (6)
H27A0.97220.82060.55940.046*
H27B0.85360.81660.44630.046*
C280.9625 (3)0.7402 (3)0.4163 (3)0.0550 (8)
H28A1.01710.70270.45570.083*
H28B1.02100.81300.41020.083*
H28C0.89040.68560.34070.083*
C290.4719 (2)0.68032 (18)0.08217 (18)0.0238 (4)
H29A0.53820.74800.15250.029*
H29B0.40300.70210.03300.029*
C300.5464 (2)0.6586 (2)0.0229 (2)0.0305 (5)
H30A0.61390.63600.07070.046*
H30B0.59230.73130.00900.046*
H30C0.48050.5948−0.04910.046*
C310.1635 (2)0.4765 (2)−0.06200 (19)0.0410 (6)
H31A0.07600.4415−0.06260.049*0.502 (6)
H31B0.18240.5577−0.06570.049*0.502 (6)
H31C0.12180.3954−0.11330.049*0.498 (6)
H31D0.20790.5320−0.09390.049*0.498 (6)
C320.1439 (5)0.4092 (4)−0.1630 (3)0.0315 (12)0.502 (6)
H32A0.22320.4498−0.17150.047*0.502 (6)
H32B0.06210.4013−0.22790.047*0.502 (6)
H32C0.13300.3303−0.15880.047*0.502 (6)
C32'0.0532 (4)0.4962 (4)−0.0675 (4)0.0309 (12)0.498 (6)
H32D−0.00910.4857−0.14570.046*0.498 (6)
H32E0.08930.5770−0.02030.046*0.498 (6)
H32F0.00400.4393−0.04030.046*0.498 (6)
C33−0.1365 (2)0.07843 (18)−0.01692 (17)0.0218 (4)
H33A−0.1968−0.0077−0.04080.026*
H33B−0.11820.0952−0.07840.026*
C34−0.2093 (2)0.1466 (2)0.00162 (19)0.0288 (5)
H34A−0.22870.12950.06170.043*
H34B−0.29490.1223−0.06820.043*
H34C−0.15100.23190.02330.043*
C35−0.0705 (2)−0.06856 (18)0.15773 (18)0.0238 (4)
H35A−0.0177−0.11220.18540.029*
H35B−0.1420−0.11440.07820.029*
C36−0.1385 (2)−0.0610 (2)0.2272 (2)0.0322 (5)
H36A−0.0684−0.01450.30580.048*
H36B−0.1947−0.14110.22330.048*
H36C−0.1960−0.02270.19710.048*
S1A0.53812 (5)0.18176 (4)0.27122 (4)0.02140 (13)
O1A0.48331 (14)0.26554 (12)0.23952 (11)0.0226 (3)
O2A0.43782 (16)0.06943 (13)0.25787 (13)0.0294 (3)
O3A0.66892 (16)0.23466 (15)0.37091 (13)0.0323 (4)
C1A0.5698 (2)0.1493 (2)0.15635 (19)0.0280 (5)
F1A0.6203 (2)0.07312 (17)0.16842 (14)0.0545 (5)
F2A0.65782 (14)0.24699 (14)0.15333 (12)0.0415 (4)
F3A0.45686 (14)0.10225 (12)0.05638 (10)0.0338 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.01791 (16)0.01937 (16)0.01339 (15)0.00727 (12)0.00684 (12)0.00551 (11)
N10.0201 (8)0.0239 (8)0.0152 (8)0.0098 (7)0.0086 (7)0.0058 (7)
N20.0217 (8)0.0208 (8)0.0151 (8)0.0093 (7)0.0072 (7)0.0044 (6)
N30.0185 (8)0.0204 (8)0.0160 (8)0.0079 (7)0.0082 (6)0.0054 (6)
N40.0201 (8)0.0222 (8)0.0160 (8)0.0092 (7)0.0098 (7)0.0074 (6)
C10.0255 (10)0.0251 (10)0.0185 (9)0.0142 (8)0.0144 (8)0.0097 (8)
C20.0281 (10)0.0291 (11)0.0189 (9)0.0173 (9)0.0148 (8)0.0111 (8)
C30.0279 (10)0.0306 (11)0.0167 (9)0.0173 (9)0.0134 (8)0.0099 (8)
C40.0251 (10)0.0285 (10)0.0153 (9)0.0154 (9)0.0114 (8)0.0077 (8)
C50.0244 (10)0.0287 (11)0.0130 (9)0.0135 (9)0.0067 (8)0.0043 (8)
C60.0243 (10)0.0235 (10)0.0150 (9)0.0115 (8)0.0072 (8)0.0018 (8)
C70.0265 (11)0.0207 (10)0.0190 (10)0.0090 (8)0.0052 (8)−0.0001 (8)
C80.0251 (10)0.0190 (10)0.0234 (10)0.0071 (8)0.0055 (9)0.0020 (8)
C90.0227 (10)0.0186 (9)0.0201 (10)0.0084 (8)0.0081 (8)0.0030 (8)
C100.0240 (10)0.0169 (9)0.0231 (10)0.0075 (8)0.0112 (8)0.0061 (8)
C110.0227 (10)0.0182 (9)0.0188 (9)0.0100 (8)0.0114 (8)0.0056 (7)
C120.0245 (10)0.0241 (10)0.0209 (10)0.0122 (8)0.0132 (8)0.0091 (8)
C130.0243 (10)0.0314 (11)0.0235 (10)0.0104 (9)0.0112 (9)0.0151 (9)
C140.0207 (10)0.0271 (10)0.0189 (9)0.0104 (8)0.0094 (8)0.0104 (8)
C150.0186 (9)0.0305 (11)0.0169 (9)0.0090 (8)0.0057 (8)0.0100 (8)
C160.0188 (9)0.0240 (10)0.0177 (9)0.0089 (8)0.0098 (8)0.0061 (8)
C170.0194 (9)0.0236 (10)0.0180 (9)0.0090 (8)0.0107 (8)0.0053 (8)
C180.0210 (10)0.0223 (10)0.0188 (9)0.0082 (8)0.0124 (8)0.0050 (8)
C190.0215 (9)0.0222 (9)0.0178 (9)0.0097 (8)0.0122 (8)0.0060 (8)
C200.0248 (10)0.0217 (9)0.0211 (10)0.0110 (8)0.0146 (8)0.0091 (8)
C210.0331 (11)0.0296 (11)0.0226 (10)0.0177 (9)0.0156 (9)0.0135 (9)
C220.0366 (12)0.0290 (11)0.0352 (12)0.0112 (10)0.0236 (11)0.0097 (10)
C230.0325 (11)0.0338 (11)0.0162 (10)0.0180 (10)0.0116 (9)0.0104 (8)
C240.0302 (11)0.0394 (13)0.0224 (10)0.0194 (10)0.0099 (9)0.0107 (9)
C250.0268 (11)0.0248 (11)0.0220 (11)0.0045 (9)0.0006 (9)0.0027 (9)
C260.0268 (12)0.0499 (15)0.0345 (13)0.0161 (11)0.0085 (10)0.0159 (11)
C270.0256 (11)0.0225 (11)0.0374 (13)0.0014 (9)−0.0008 (10)0.0092 (10)
C280.0390 (15)0.0484 (16)0.0609 (19)0.0043 (13)0.0232 (14)0.0250 (15)
C290.0262 (10)0.0225 (10)0.0231 (10)0.0107 (8)0.0123 (8)0.0107 (8)
C300.0347 (12)0.0292 (11)0.0370 (12)0.0151 (10)0.0237 (10)0.0177 (10)
C310.0256 (11)0.0444 (14)0.0335 (12)0.0043 (10)0.0054 (10)0.0271 (11)
C320.032 (2)0.036 (2)0.022 (2)0.017 (2)0.0099 (18)0.0087 (18)
C32'0.027 (2)0.032 (2)0.033 (2)0.0138 (19)0.0125 (19)0.0150 (19)
C330.0181 (9)0.0234 (10)0.0192 (9)0.0071 (8)0.0080 (8)0.0051 (8)
C340.0228 (10)0.0283 (11)0.0281 (11)0.0120 (9)0.0081 (9)0.0037 (9)
C350.0248 (10)0.0207 (10)0.0234 (10)0.0070 (8)0.0132 (8)0.0060 (8)
C360.0341 (12)0.0297 (11)0.0364 (12)0.0097 (10)0.0249 (11)0.0104 (10)
S1A0.0230 (3)0.0241 (3)0.0178 (2)0.0112 (2)0.0105 (2)0.00716 (19)
O1A0.0287 (7)0.0248 (7)0.0194 (7)0.0143 (6)0.0143 (6)0.0084 (6)
O2A0.0342 (8)0.0261 (8)0.0283 (8)0.0117 (7)0.0171 (7)0.0123 (6)
O3A0.0264 (8)0.0429 (9)0.0215 (8)0.0160 (7)0.0075 (6)0.0087 (7)
C1A0.0326 (11)0.0331 (12)0.0265 (11)0.0190 (10)0.0178 (9)0.0105 (9)
F1A0.0885 (13)0.0807 (12)0.0476 (9)0.0708 (11)0.0473 (9)0.0348 (9)
F2A0.0325 (7)0.0558 (9)0.0351 (8)0.0123 (7)0.0227 (6)0.0157 (7)
F3A0.0429 (8)0.0323 (7)0.0198 (6)0.0137 (6)0.0146 (6)0.0046 (5)

Geometric parameters (Å, °)

Fe1—N11.9979 (17)C23—H23B0.9900
Fe1—N21.9981 (17)C24—H24A0.9800
Fe1—N31.9999 (16)C24—H24B0.9800
Fe1—N42.0001 (17)C24—H24C0.9800
Fe1—O1A2.0392 (14)C25—C261.529 (4)
N1—C11.383 (3)C25—H25A0.9900
N1—C41.384 (2)C25—H25B0.9900
N2—C61.381 (3)C26—H26A0.9800
N2—C91.383 (3)C26—H26B0.9800
N3—C141.381 (2)C26—H26C0.9800
N3—C111.386 (2)C27—C281.512 (4)
N4—C191.383 (2)C27—H27A0.9900
N4—C161.386 (2)C27—H27B0.9900
C1—C201.380 (3)C28—H28A0.9800
C1—C21.442 (3)C28—H28B0.9800
C2—C31.361 (3)C28—H28C0.9800
C2—C211.502 (3)C29—C301.529 (3)
C3—C41.443 (3)C29—H29A0.9900
C3—C231.502 (3)C29—H29B0.9900
C4—C51.377 (3)C30—H30A0.9800
C5—C61.380 (3)C30—H30B0.9800
C5—H50.9500C30—H30C0.9800
C6—C71.437 (3)C31—C321.430 (3)
C7—C81.361 (3)C31—C32'1.433 (3)
C7—C251.502 (3)C31—H31A0.9900
C8—C91.440 (3)C31—H31B0.9900
C8—C271.500 (3)C31—H31C0.9900
C9—C101.381 (3)C31—H31D0.9900
C10—C111.380 (3)C32—H32A0.9800
C10—H100.9500C32—H32B0.9800
C11—C121.437 (3)C32—H32C0.9800
C12—C131.359 (3)C32'—H32D0.9800
C12—C291.504 (3)C32'—H32E0.9800
C13—C141.442 (3)C32'—H32F0.9800
C13—C311.484 (3)C33—C341.529 (3)
C14—C151.380 (3)C33—H33A0.9900
C15—C161.379 (3)C33—H33B0.9900
C15—H150.9500C34—H34A0.9800
C16—C171.443 (3)C34—H34B0.9800
C17—C181.366 (3)C34—H34C0.9800
C17—C331.500 (3)C35—C361.527 (3)
C18—C191.438 (3)C35—H35A0.9900
C18—C351.501 (3)C35—H35B0.9900
C19—C201.383 (3)C36—H36A0.9800
C20—H200.9500C36—H36B0.9800
C21—C221.519 (3)C36—H36C0.9800
C21—H21A0.9900S1A—O3A1.4284 (16)
C21—H21B0.9900S1A—O2A1.4316 (16)
C22—H22A0.9800S1A—O1A1.4755 (15)
C22—H22B0.9800S1A—C1A1.825 (2)
C22—H22C0.9800C1A—F1A1.324 (3)
C23—C241.531 (3)C1A—F3A1.328 (3)
C23—H23A0.9900C1A—F2A1.333 (3)
N1—Fe1—N289.36 (7)H24A—C24—H24B109.5
N1—Fe1—N3167.25 (7)C23—C24—H24C109.5
N2—Fe1—N389.17 (7)H24A—C24—H24C109.5
N1—Fe1—N489.01 (7)H24B—C24—H24C109.5
N2—Fe1—N4165.89 (7)C7—C25—C26111.46 (19)
N3—Fe1—N489.34 (7)C7—C25—H25A109.3
N1—Fe1—O1A97.97 (6)C26—C25—H25A109.3
N2—Fe1—O1A97.48 (6)C7—C25—H25B109.3
N3—Fe1—O1A94.78 (6)C26—C25—H25B109.3
N4—Fe1—O1A96.63 (6)H25A—C25—H25B108.0
C1—N1—C4104.98 (16)C25—C26—H26A109.5
C1—N1—Fe1126.65 (13)C25—C26—H26B109.5
C4—N1—Fe1127.49 (14)H26A—C26—H26B109.5
C6—N2—C9104.94 (16)C25—C26—H26C109.5
C6—N2—Fe1127.33 (14)H26A—C26—H26C109.5
C9—N2—Fe1126.74 (13)H26B—C26—H26C109.5
C14—N3—C11104.97 (16)C8—C27—C28113.3 (2)
C14—N3—Fe1127.55 (13)C8—C27—H27A108.9
C11—N3—Fe1126.99 (13)C28—C27—H27A108.9
C19—N4—C16104.82 (16)C8—C27—H27B108.9
C19—N4—Fe1127.04 (13)C28—C27—H27B108.9
C16—N4—Fe1127.53 (13)H27A—C27—H27B107.7
C20—C1—N1124.70 (18)C27—C28—H28A109.5
C20—C1—C2124.55 (19)C27—C28—H28B109.5
N1—C1—C2110.73 (18)H28A—C28—H28B109.5
C3—C2—C1106.82 (18)C27—C28—H28C109.5
C3—C2—C21127.42 (19)H28A—C28—H28C109.5
C1—C2—C21125.76 (19)H28B—C28—H28C109.5
C2—C3—C4106.78 (17)C12—C29—C30112.86 (17)
C2—C3—C23128.31 (19)C12—C29—H29A109.0
C4—C3—C23124.89 (19)C30—C29—H29A109.0
C5—C4—N1124.71 (18)C12—C29—H29B109.0
C5—C4—C3124.58 (19)C30—C29—H29B109.0
N1—C4—C3110.65 (18)H29A—C29—H29B107.8
C4—C5—C6125.30 (19)C29—C30—H30A109.5
C4—C5—H5117.4C29—C30—H30B109.5
C6—C5—H5117.4H30A—C30—H30B109.5
C5—C6—N2124.88 (19)C29—C30—H30C109.5
C5—C6—C7124.30 (19)H30A—C30—H30C109.5
N2—C6—C7110.78 (18)H30B—C30—H30C109.5
C8—C7—C6106.90 (18)C32—C31—C13118.9 (2)
C8—C7—C25128.4 (2)C32'—C31—C13119.5 (2)
C6—C7—C25124.4 (2)C32—C31—H31A107.6
C7—C8—C9106.67 (19)C13—C31—H31A107.6
C7—C8—C27128.4 (2)C32—C31—H31B107.6
C9—C8—C27124.8 (2)C13—C31—H31B107.6
C10—C9—N2124.71 (18)H31A—C31—H31B107.0
C10—C9—C8124.58 (19)C32'—C31—H31C106.4
N2—C9—C8110.71 (18)C13—C31—H31C107.9
C11—C10—C9125.40 (19)C32'—C31—H31D107.7
C11—C10—H10117.3C13—C31—H31D107.7
C9—C10—H10117.3H31C—C31—H31D107.0
C10—C11—N3124.51 (18)H31C—C32—H31D82.8
C10—C11—C12124.67 (18)C31—C32—H32A109.5
N3—C11—C12110.80 (17)C31—C32—H32B109.5
C13—C12—C11106.66 (18)H32A—C32—H32B109.5
C13—C12—C29127.99 (19)C31—C32—H32C109.5
C11—C12—C29125.35 (18)H32A—C32—H32C109.5
C12—C13—C14107.08 (18)H32B—C32—H32C109.5
C12—C13—C31127.9 (2)C31—C32'—H32D109.5
C14—C13—C31125.07 (19)C31—C32'—H32E109.5
C15—C14—N3124.81 (18)H32D—C32'—H32E109.5
C15—C14—C13124.70 (19)C31—C32'—H32F109.5
N3—C14—C13110.49 (17)H32D—C32'—H32F109.5
C16—C15—C14125.43 (19)H32E—C32'—H32F109.5
C16—C15—H15117.3C17—C33—C34112.30 (17)
C14—C15—H15117.3C17—C33—H33A109.1
C15—C16—N4124.71 (18)C34—C33—H33A109.1
C15—C16—C17124.46 (18)C17—C33—H33B109.1
N4—C16—C17110.80 (17)C34—C33—H33B109.1
C18—C17—C16106.55 (17)H33A—C33—H33B107.9
C18—C17—C33128.90 (18)C33—C34—H34A109.5
C16—C17—C33124.49 (18)C33—C34—H34B109.5
C17—C18—C19106.85 (17)H34A—C34—H34B109.5
C17—C18—C35128.19 (18)C33—C34—H34C109.5
C19—C18—C35124.96 (18)H34A—C34—H34C109.5
C20—C19—N4124.46 (18)H34B—C34—H34C109.5
C20—C19—C18124.60 (19)C18—C35—C36113.27 (17)
N4—C19—C18110.94 (17)C18—C35—H35A108.9
C1—C20—C19125.27 (19)C36—C35—H35A108.9
C1—C20—H20117.4C18—C35—H35B108.9
C19—C20—H20117.4C36—C35—H35B108.9
C2—C21—C22113.67 (18)H35A—C35—H35B107.7
C2—C21—H21A108.8C35—C36—H36A109.5
C22—C21—H21A108.8C35—C36—H36B109.5
C2—C21—H21B108.8H36A—C36—H36B109.5
C22—C21—H21B108.8C35—C36—H36C109.5
H21A—C21—H21B107.7H36A—C36—H36C109.5
C21—C22—H22A109.5H36B—C36—H36C109.5
C21—C22—H22B109.5O3A—S1A—O2A117.97 (10)
H22A—C22—H22B109.5O3A—S1A—O1A114.00 (9)
C21—C22—H22C109.5O2A—S1A—O1A113.34 (9)
H22A—C22—H22C109.5O3A—S1A—C1A104.86 (10)
H22B—C22—H22C109.5O2A—S1A—C1A103.69 (10)
C3—C23—C24113.37 (17)O1A—S1A—C1A100.22 (9)
C3—C23—H23A108.9S1A—O1A—Fe1129.34 (8)
C24—C23—H23A108.9F1A—C1A—F3A107.70 (18)
C3—C23—H23B108.9F1A—C1A—F2A108.25 (19)
C24—C23—H23B108.9F3A—C1A—F2A106.79 (18)
H23A—C23—H23B107.7F1A—C1A—S1A110.29 (15)
C23—C24—H24A109.5F3A—C1A—S1A112.07 (15)
C23—C24—H24B109.5F2A—C1A—S1A111.55 (15)
N2—Fe1—N1—C1−176.28 (16)Fe1—N3—C11—C10−9.3 (3)
N3—Fe1—N1—C1100.3 (3)C14—N3—C11—C12−0.2 (2)
N4—Fe1—N1—C117.74 (16)Fe1—N3—C11—C12172.20 (13)
O1A—Fe1—N1—C1−78.82 (16)C10—C11—C12—C13−177.9 (2)
N2—Fe1—N1—C4−8.70 (16)N3—C11—C12—C130.5 (2)
N3—Fe1—N1—C4−92.1 (3)C10—C11—C12—C292.8 (3)
N4—Fe1—N1—C4−174.68 (16)N3—C11—C12—C29−178.71 (18)
O1A—Fe1—N1—C488.77 (16)C11—C12—C13—C14−0.6 (2)
N1—Fe1—N2—C69.46 (17)C29—C12—C13—C14178.6 (2)
N3—Fe1—N2—C6176.80 (17)C11—C12—C13—C31179.8 (2)
N4—Fe1—N2—C692.8 (3)C29—C12—C13—C31−0.9 (4)
O1A—Fe1—N2—C6−88.49 (17)C11—N3—C14—C15179.5 (2)
N1—Fe1—N2—C9176.31 (17)Fe1—N3—C14—C157.1 (3)
N3—Fe1—N2—C9−16.36 (17)C11—N3—C14—C13−0.2 (2)
N4—Fe1—N2—C9−100.3 (3)Fe1—N3—C14—C13−172.55 (14)
O1A—Fe1—N2—C978.35 (17)C12—C13—C14—C15−179.1 (2)
N1—Fe1—N3—C14−90.9 (3)C31—C13—C14—C150.4 (4)
N2—Fe1—N3—C14−174.27 (17)C12—C13—C14—N30.5 (2)
N4—Fe1—N3—C14−8.30 (17)C31—C13—C14—N3−179.9 (2)
O1A—Fe1—N3—C1488.29 (17)N3—C14—C15—C16−1.7 (4)
N1—Fe1—N3—C1198.4 (3)C13—C14—C15—C16178.0 (2)
N2—Fe1—N3—C1115.00 (16)C14—C15—C16—N40.6 (3)
N4—Fe1—N3—C11−179.04 (16)C14—C15—C16—C17−177.2 (2)
O1A—Fe1—N3—C11−82.44 (16)C19—N4—C16—C15−176.66 (19)
N1—Fe1—N4—C19−15.57 (16)Fe1—N4—C16—C15−5.1 (3)
N2—Fe1—N4—C19−99.0 (3)C19—N4—C16—C171.4 (2)
N3—Fe1—N4—C19177.07 (16)Fe1—N4—C16—C17172.91 (13)
O1A—Fe1—N4—C1982.34 (16)C15—C16—C17—C18176.11 (19)
N1—Fe1—N4—C16174.72 (17)N4—C16—C17—C18−1.9 (2)
N2—Fe1—N4—C1691.3 (3)C15—C16—C17—C33−6.5 (3)
N3—Fe1—N4—C167.36 (16)N4—C16—C17—C33175.49 (17)
O1A—Fe1—N4—C16−87.37 (16)C16—C17—C18—C191.6 (2)
C4—N1—C1—C20177.06 (18)C33—C17—C18—C19−175.66 (19)
Fe1—N1—C1—C20−13.1 (3)C16—C17—C18—C35−178.72 (19)
C4—N1—C1—C2−1.3 (2)C33—C17—C18—C354.0 (3)
Fe1—N1—C1—C2168.54 (13)C16—N4—C19—C20179.99 (18)
C20—C1—C2—C3−176.16 (19)Fe1—N4—C19—C208.4 (3)
N1—C1—C2—C32.2 (2)C16—N4—C19—C18−0.4 (2)
C20—C1—C2—C214.0 (3)Fe1—N4—C19—C18−171.93 (13)
N1—C1—C2—C21−177.66 (18)C17—C18—C19—C20178.81 (19)
C1—C2—C3—C4−2.1 (2)C35—C18—C19—C20−0.9 (3)
C21—C2—C3—C4177.77 (19)C17—C18—C19—N4−0.8 (2)
C1—C2—C3—C23179.52 (19)C35—C18—C19—N4179.49 (17)
C21—C2—C3—C23−0.6 (3)N1—C1—C20—C19−1.2 (3)
C1—N1—C4—C5177.24 (19)C2—C1—C20—C19176.93 (19)
Fe1—N1—C4—C57.5 (3)N4—C19—C20—C13.7 (3)
C1—N1—C4—C30.0 (2)C18—C19—C20—C1−175.94 (19)
Fe1—N1—C4—C3−169.74 (13)C3—C2—C21—C2291.9 (3)
C2—C3—C4—C5−175.89 (19)C1—C2—C21—C22−88.3 (3)
C23—C3—C4—C52.6 (3)C2—C3—C23—C2490.5 (3)
C2—C3—C4—N11.4 (2)C4—C3—C23—C24−87.6 (3)
C23—C3—C4—N1179.85 (18)C8—C7—C25—C26−93.2 (3)
N1—C4—C5—C6−3.6 (3)C6—C7—C25—C2679.7 (3)
C3—C4—C5—C6173.3 (2)C7—C8—C27—C2896.3 (3)
C4—C5—C6—N24.5 (3)C9—C8—C27—C28−79.0 (3)
C4—C5—C6—C7−173.1 (2)C13—C12—C29—C30−93.5 (3)
C9—N2—C6—C5−178.31 (19)C11—C12—C29—C3085.6 (2)
Fe1—N2—C6—C5−9.2 (3)C12—C13—C31—C3292.8 (4)
C9—N2—C6—C7−0.5 (2)C14—C13—C31—C32−86.7 (3)
Fe1—N2—C6—C7168.65 (14)C12—C13—C31—C32'−108.5 (3)
C5—C6—C7—C8177.9 (2)C14—C13—C31—C32'72.0 (4)
N2—C6—C7—C80.0 (2)C18—C17—C33—C34101.2 (2)
C5—C6—C7—C253.7 (3)C16—C17—C33—C34−75.7 (2)
N2—C6—C7—C25−174.2 (2)C17—C18—C35—C36−97.2 (2)
C6—C7—C8—C90.5 (2)C19—C18—C35—C3682.4 (3)
C25—C7—C8—C9174.3 (2)O3A—S1A—O1A—Fe1−69.33 (13)
C6—C7—C8—C27−175.5 (2)O2A—S1A—O1A—Fe169.37 (13)
C25—C7—C8—C27−1.7 (4)C1A—S1A—O1A—Fe1179.23 (11)
C6—N2—C9—C10−178.53 (19)N1—Fe1—O1A—S1A−2.03 (12)
Fe1—N2—C9—C1012.3 (3)N2—Fe1—O1A—S1A88.37 (12)
C6—N2—C9—C80.8 (2)N3—Fe1—O1A—S1A178.16 (11)
Fe1—N2—C9—C8−168.44 (14)N4—Fe1—O1A—S1A−91.95 (12)
C7—C8—C9—C10178.5 (2)O3A—S1A—C1A—F1A61.84 (19)
C27—C8—C9—C10−5.3 (3)O2A—S1A—C1A—F1A−62.50 (18)
C7—C8—C9—N2−0.8 (2)O1A—S1A—C1A—F1A−179.77 (16)
C27—C8—C9—N2175.4 (2)O3A—S1A—C1A—F3A−178.18 (15)
N2—C9—C10—C110.1 (3)O2A—S1A—C1A—F3A57.48 (17)
C8—C9—C10—C11−179.1 (2)O1A—S1A—C1A—F3A−59.79 (17)
C9—C10—C11—N3−1.7 (3)O3A—S1A—C1A—F2A−58.49 (18)
C9—C10—C11—C12176.6 (2)O2A—S1A—C1A—F2A177.17 (15)
C14—N3—C11—C10178.29 (19)O1A—S1A—C1A—F2A59.90 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2808).

References

  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gismelseed, A., Bominaar, E. L., Bill, E., Trautwein, A. X., Winkler, H., Nasri, H., Doppelt, P., Mandon, D., Fischer, J. & Weiss, R. (1990). Inorg. Chem.29, 2741–2749.
  • González, J. A. & Wilson, L. J. (1994). Inorg. Chem.33, 1543–1553.
  • Sheldrick, G. M. (2007). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography