PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1458.
Published online 2010 October 23. doi:  10.1107/S1600536810041024
PMCID: PMC3009112

(Ethanolato)[2,3,7,8,12,13,17,18-octa­ethylporphyrinato(2−)]iron(III)

Abstract

The title compound, [Fe(C2H5O)(C36H44N4)], contains a five-coordinate iron–porphyrin complex with an axial eth­oxy ligand. The iron(III) atom is displaced by 0.504 (2) Å towards the eth­oxy ligand from the 24-atom mean plane of the porphyrin. The average Fe—Np distance is 2.078 (2) Å and the Fe—O distance is 1.8232 (18) Å. The eth­oxy C atoms are disordered in a 0.581 (12):0.419 (12) ratio. The bond angles of the Fe—O—C linkage are 128.6 (3) and 130.4 (3)°, respectively, for the major and minor occupancy C atoms.

Related literature

For the structures of other related five-coordinate octa­ethyl­porphyrin iron(III) alkoxide complexes, see: Kanamori et al. (2005 [triangle]); Hatano & Uno (1990 [triangle]). Iron porphyrin alkoxide complexes can serve as structural models of tyrosinate ligated heme enzyme catalases which catalyze the degradation of hydrogen peroxide to water and oxygen, see: Chelikani et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1458-scheme1.jpg

Experimental

Crystal data

  • [Fe(C2H5O)(C36H44N4)]
  • M r = 633.66
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1458-efi1.jpg
  • a = 10.3918 (13) Å
  • b = 10.4791 (12) Å
  • c = 16.4765 (18) Å
  • α = 106.312 (7)°
  • β = 105.181 (8)°
  • γ = 97.830 (9)°
  • V = 1618.7 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.50 mm−1
  • T = 163 K
  • 0.48 × 0.36 × 0.28 mm

Data collection

  • Siemens P4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.794, T max = 0.872
  • 5868 measured reflections
  • 5540 independent reflections
  • 4779 reflections with I > 2σ(I)
  • R int = 0.041
  • 3 standard reflections every 97 reflections intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.119
  • S = 1.06
  • 5540 reflections
  • 416 parameters
  • 80 restraints
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: XSCANS (Siemens, 1994 [triangle]); cell refinement: XSCANS; data reduction: XSCANS; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810041024/fk2027sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041024/fk2027Isup2.hkl

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

Acknowledgments

The authors are grateful to the National Institutes of Health (GM 064476 to GBR-A) and to the National Science Foundation (CHE-0911537 to GBR-A) for funds to conduct this research, and to 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

We report the structure of the five-coordinate (2,3,7,8,12,13,17,18-octaethylporphyrinato)(ethoxy)iron(III) complex (i.e., (OEP)Fe(OEt)). Iron porphyrin alkoxide complexes can serve as structural models of tyrosinate ligated heme enzyme catalases which catalyze the degradation of hydrogen peroxide to water and oxygen (Chelikani et al. 2004). Other related octaethylporphyrin ferric alkoxide complexes have been synthesized and structurally characterized previously (Kanamori et al. 2005 and Hatano et al. 1990).

The ethoxy ligand was disordered at both carbon positions C37 and C38, and this O—C37—C38 fragment was modeled in two orientations. Occupancies for the disordered group refined to 0.581 (12) and 0.419 (12) for the unprimed and primed atoms, respectively. The molecular structure of (OEP)Fe(OEt) showing the disordered ethoxy group is shown in Figure 1. Selected bond lengths and angles are given in Table 1. The ethoxy group binds to the iron center through the O atom. The iron atom is displaced by 0.504 (2) Å from the 24-atom mean porphyrin plane toward the ethoxy ligand. The Fe—O distance of 1.8232 (13) Å is in the 1.816 (4) Å - 1.926 (3) Å range reported for similar octaethylporphyrin iron alkoxide complexes (Kanamori et al. 2005 and Hatano et al. 1990). The bond angles of the Fe—O—C linkage are 128.6 (3)° (for C37) and 130.4 (3)° (for C37'), respectively.

Experimental

A suitable purple block-shaped crystal was grown unexpectedly by slow evaporation of a dichloromethane-ethanol (1:1) solution of µ-oxo-bis((octaethylporphyrinato)iron(III)) at room temperature under N2 under normal laboratory lighting.

Refinement

H atoms were placed using assumed geometry with C—H(aromatic = 0.95 Å, methylene = 0.99 Å, and methyl = 0.98 Å). Displacement parameters of the H atoms were set to 1.2 (1.5 for methyl) times the isotropic equivalent for the bonded C.

Figures

Fig. 1.
The molecular structure of (OEP)Fe(OEt). Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.

Crystal data

[Fe(C2H5O)(C36H44N4)]Z = 2
Mr = 633.66F(000) = 678
Triclinic, P1Dx = 1.300 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3918 (13) ÅCell parameters from 61 reflections
b = 10.4791 (12) Åθ = 2.7–12.0°
c = 16.4765 (18) ŵ = 0.50 mm1
α = 106.312 (7)°T = 163 K
β = 105.181 (8)°Block, purple
γ = 97.830 (9)°0.48 × 0.36 × 0.28 mm
V = 1618.7 (3) Å3

Data collection

Siemens P4 diffractometer4779 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 25.0°, θmin = 2.1°
ω scansh = −12→12
Absorption correction: ψ scan (North et al., 1968)k = −11→11
Tmin = 0.794, Tmax = 0.872l = −19→18
5868 measured reflections3 standard reflections every 97 reflections
5540 independent reflections intensity decay: 1.0%

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.058P)2 + 1.240P] where P = (Fo2 + 2Fc2)/3
5540 reflections(Δ/σ)max < 0.001
416 parametersΔρmax = 0.80 e Å3
80 restraintsΔρmin = −0.69 e Å3

Special details

Refinement. Restraints: SADI 0.004 C37 C38 C37' C38' SADI 0.004 C37 O1 C37' O1 ISOR 0.008 o1 C37 C37' C38 C38' SIMU 0.008 o1 C37 C37' C38 C38'

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

xyzUiso*/UeqOcc. (<1)
Fe1−0.00859 (3)0.13917 (3)0.25182 (2)0.01500 (12)
O10.10667 (18)0.11689 (18)0.34875 (11)0.0217 (4)
N1−0.1290 (2)−0.0555 (2)0.17747 (13)0.0149 (4)
N2−0.1726 (2)0.1803 (2)0.29610 (14)0.0165 (4)
N30.0484 (2)0.3473 (2)0.27482 (14)0.0178 (4)
N40.0965 (2)0.1113 (2)0.15905 (13)0.0172 (4)
C1−0.0962 (2)−0.1555 (2)0.11728 (16)0.0169 (5)
C2−0.1904 (3)−0.2852 (3)0.09367 (16)0.0184 (5)
C3−0.2814 (2)−0.2613 (3)0.13921 (16)0.0182 (5)
C4−0.2412 (2)−0.1181 (2)0.19182 (16)0.0160 (5)
C5−0.3064 (2)−0.0531 (3)0.24969 (17)0.0183 (5)
H5A−0.3810−0.10860.25600.022*
C6−0.2739 (2)0.0847 (3)0.29919 (16)0.0176 (5)
C7−0.3451 (3)0.1485 (3)0.35864 (16)0.0183 (5)
C8−0.2871 (2)0.2847 (3)0.38977 (16)0.0183 (5)
C9−0.1802 (3)0.3041 (3)0.35071 (16)0.0178 (5)
C10−0.0958 (3)0.4286 (3)0.36501 (17)0.0193 (5)
H10A−0.11220.50740.40270.023*
C110.0098 (3)0.4494 (2)0.32980 (16)0.0181 (5)
C120.0977 (3)0.5803 (3)0.34830 (17)0.0192 (5)
C130.1929 (3)0.5556 (3)0.30630 (17)0.0210 (5)
C140.1604 (3)0.4108 (3)0.25972 (17)0.0185 (5)
C150.2302 (3)0.3439 (3)0.20580 (17)0.0202 (5)
H15A0.30720.39880.20150.024*
C160.1999 (2)0.2062 (3)0.15776 (16)0.0178 (5)
C170.2702 (3)0.1423 (3)0.09768 (16)0.0186 (5)
C180.2061 (3)0.0077 (3)0.06180 (16)0.0187 (5)
C190.0986 (2)−0.0115 (3)0.10084 (16)0.0171 (5)
C200.0103 (3)−0.1341 (3)0.08288 (16)0.0189 (5)
H20A0.0237−0.21210.04270.023*
C21−0.1839 (3)−0.4178 (3)0.03267 (18)0.0245 (6)
H21A−0.1475−0.4008−0.01410.029*
H21B−0.2776−0.47600.00300.029*
C22−0.0940 (3)−0.4932 (3)0.0817 (2)0.0394 (8)
H22A−0.0937−0.58010.03940.059*
H22B−0.1300−0.51080.12790.059*
H22C−0.0003−0.43730.10950.059*
C23−0.4020 (3)−0.3614 (3)0.13609 (18)0.0238 (6)
H23A−0.4249−0.44200.08180.029*
H23B−0.4818−0.31860.13140.029*
C24−0.3786 (3)−0.4091 (3)0.2169 (2)0.0325 (7)
H24A−0.4612−0.47380.21040.049*
H24B−0.3582−0.33030.27090.049*
H24C−0.3014−0.45390.22120.049*
C25−0.4630 (3)0.0755 (3)0.37693 (18)0.0238 (6)
H25A−0.46270.12470.43780.029*
H25B−0.4510−0.01740.37470.029*
C26−0.6005 (3)0.0646 (3)0.3107 (2)0.0316 (7)
H26A−0.67370.01350.32420.047*
H26B−0.60110.01700.25010.047*
H26C−0.61530.15630.31500.047*
C27−0.3249 (3)0.3972 (3)0.45254 (17)0.0221 (6)
H27A−0.24030.46520.49290.027*
H27B−0.36880.35830.48960.027*
C28−0.4215 (3)0.4691 (3)0.4049 (2)0.0322 (7)
H28A−0.43830.54410.44910.048*
H28B−0.50840.40390.36830.048*
H28C−0.38000.50560.36670.048*
C290.0843 (3)0.7159 (3)0.40301 (18)0.0243 (6)
H29A0.17670.77620.43470.029*
H29B0.04240.70270.44840.029*
C30−0.0017 (4)0.7849 (3)0.3473 (2)0.0410 (8)
H30A−0.00970.87140.38610.061*
H30B−0.09300.72530.31520.061*
H30C0.04190.80280.30430.061*
C310.3119 (3)0.6568 (3)0.30812 (19)0.0261 (6)
H31A0.39390.61760.31640.031*
H31B0.33090.74020.36010.031*
C320.2888 (3)0.6967 (3)0.2244 (2)0.0324 (7)
H32A0.37030.76190.22990.049*
H32B0.20980.73880.21680.049*
H32C0.27130.61510.17250.049*
C330.3916 (3)0.2127 (3)0.08191 (17)0.0218 (6)
H33A0.38370.30700.08540.026*
H33B0.39230.16440.02110.026*
C340.5269 (3)0.2175 (3)0.14961 (19)0.0280 (6)
H34A0.60310.26830.13850.042*
H34B0.53830.12430.14350.042*
H34C0.52580.26290.21010.042*
C350.2387 (3)−0.1034 (3)−0.00465 (17)0.0226 (6)
H35A0.2826−0.0629−0.04100.027*
H35B0.1525−0.1687−0.04520.027*
C360.3337 (3)−0.1801 (3)0.04001 (19)0.0288 (6)
H36A0.3506−0.2526−0.00570.043*
H36B0.2908−0.22040.07610.043*
H36C0.4207−0.11660.07830.043*
C370.1180 (8)0.1737 (7)0.4386 (3)0.0313 (15)0.581 (12)
H37A0.03610.13210.45010.038*0.581 (12)
H37B0.12410.27320.45390.038*0.581 (12)
C380.2486 (12)0.1468 (16)0.4969 (9)0.037 (3)0.581 (12)
H38A0.25900.18910.56000.055*0.581 (12)
H38B0.32900.18600.48400.055*0.581 (12)
H38C0.24020.04820.48330.055*0.581 (12)
C37'0.1811 (10)0.2115 (7)0.4323 (4)0.0301 (19)0.419 (12)
H37C0.12540.27570.45250.036*0.419 (12)
H37D0.26490.26470.42920.036*0.419 (12)
C38'0.2198 (19)0.132 (2)0.4987 (13)0.038 (4)0.419 (12)
H38D0.26240.19730.55930.057*0.419 (12)
H38E0.28430.07780.48250.057*0.419 (12)
H38F0.13710.07190.49620.057*0.419 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0155 (2)0.0140 (2)0.0194 (2)0.00698 (14)0.00862 (14)0.00698 (14)
O10.0239 (9)0.0237 (10)0.0201 (9)0.0128 (8)0.0064 (7)0.0081 (7)
N10.0155 (10)0.0147 (10)0.0173 (10)0.0066 (8)0.0070 (8)0.0062 (8)
N20.0160 (10)0.0157 (11)0.0221 (11)0.0078 (8)0.0097 (9)0.0072 (9)
N30.0179 (11)0.0168 (11)0.0237 (11)0.0086 (9)0.0098 (9)0.0093 (9)
N40.0175 (11)0.0176 (11)0.0207 (11)0.0075 (9)0.0094 (9)0.0081 (9)
C10.0181 (12)0.0156 (12)0.0171 (12)0.0062 (10)0.0045 (10)0.0052 (10)
C20.0183 (13)0.0181 (13)0.0176 (12)0.0056 (10)0.0020 (10)0.0068 (10)
C30.0155 (12)0.0194 (13)0.0201 (13)0.0049 (10)0.0039 (10)0.0084 (10)
C40.0154 (12)0.0171 (13)0.0184 (12)0.0060 (10)0.0051 (10)0.0091 (10)
C50.0157 (12)0.0202 (13)0.0239 (13)0.0056 (10)0.0089 (10)0.0116 (11)
C60.0158 (12)0.0224 (13)0.0207 (13)0.0092 (10)0.0082 (10)0.0116 (10)
C70.0177 (13)0.0237 (14)0.0194 (12)0.0109 (11)0.0081 (10)0.0109 (10)
C80.0171 (12)0.0227 (14)0.0192 (13)0.0116 (11)0.0067 (10)0.0090 (10)
C90.0191 (13)0.0191 (13)0.0193 (12)0.0107 (10)0.0078 (10)0.0081 (10)
C100.0230 (13)0.0160 (13)0.0219 (13)0.0118 (11)0.0086 (11)0.0058 (10)
C110.0206 (13)0.0139 (12)0.0211 (13)0.0069 (10)0.0058 (10)0.0071 (10)
C120.0219 (13)0.0172 (13)0.0209 (13)0.0077 (10)0.0057 (10)0.0091 (10)
C130.0222 (14)0.0199 (14)0.0238 (13)0.0068 (11)0.0064 (11)0.0117 (11)
C140.0175 (13)0.0186 (13)0.0228 (13)0.0072 (10)0.0061 (10)0.0106 (10)
C150.0182 (13)0.0218 (14)0.0267 (14)0.0062 (10)0.0105 (11)0.0135 (11)
C160.0145 (12)0.0232 (14)0.0222 (13)0.0089 (10)0.0078 (10)0.0132 (11)
C170.0184 (13)0.0245 (14)0.0200 (13)0.0113 (11)0.0079 (10)0.0131 (11)
C180.0214 (13)0.0226 (14)0.0181 (12)0.0121 (11)0.0074 (10)0.0116 (10)
C190.0187 (12)0.0202 (13)0.0168 (12)0.0113 (10)0.0063 (10)0.0090 (10)
C200.0212 (13)0.0174 (13)0.0200 (13)0.0092 (10)0.0074 (10)0.0062 (10)
C210.0255 (14)0.0189 (14)0.0264 (14)0.0034 (11)0.0111 (12)0.0014 (11)
C220.0398 (18)0.0248 (16)0.050 (2)0.0166 (14)0.0109 (15)0.0055 (14)
C230.0203 (13)0.0201 (14)0.0277 (14)0.0017 (11)0.0069 (11)0.0050 (11)
C240.0316 (16)0.0277 (16)0.0403 (17)0.0008 (13)0.0121 (13)0.0162 (13)
C250.0252 (14)0.0258 (14)0.0262 (14)0.0096 (11)0.0152 (12)0.0090 (11)
C260.0213 (14)0.0356 (17)0.0438 (18)0.0088 (12)0.0149 (13)0.0168 (14)
C270.0269 (14)0.0236 (14)0.0221 (13)0.0124 (11)0.0133 (11)0.0087 (11)
C280.0407 (17)0.0339 (17)0.0325 (16)0.0269 (14)0.0172 (14)0.0130 (13)
C290.0286 (15)0.0154 (13)0.0267 (14)0.0048 (11)0.0082 (12)0.0045 (11)
C300.049 (2)0.0264 (17)0.0412 (18)0.0202 (15)0.0016 (15)0.0072 (14)
C310.0280 (15)0.0197 (14)0.0320 (15)0.0043 (11)0.0109 (12)0.0099 (12)
C320.0340 (16)0.0303 (16)0.0368 (17)0.0048 (13)0.0139 (13)0.0157 (13)
C330.0206 (13)0.0281 (15)0.0247 (14)0.0097 (11)0.0125 (11)0.0140 (11)
C340.0204 (14)0.0388 (17)0.0303 (15)0.0082 (12)0.0102 (12)0.0172 (13)
C350.0257 (14)0.0277 (15)0.0216 (13)0.0126 (12)0.0136 (11)0.0103 (11)
C360.0326 (16)0.0276 (15)0.0323 (15)0.0166 (13)0.0147 (13)0.0103 (12)
C370.035 (3)0.032 (3)0.024 (2)0.013 (2)0.009 (2)0.0019 (19)
C380.036 (5)0.045 (4)0.023 (3)0.008 (4)0.003 (3)0.008 (3)
C37'0.030 (4)0.030 (3)0.025 (3)0.007 (3)0.003 (3)0.007 (2)
C38'0.038 (6)0.040 (5)0.025 (4)0.005 (4)0.001 (4)0.007 (3)

Geometric parameters (Å, °)

Fe1—O11.8232 (18)C23—H23A0.9900
Fe1—N22.074 (2)C23—H23B0.9900
Fe1—N32.078 (2)C24—H24A0.9800
Fe1—N12.080 (2)C24—H24B0.9800
Fe1—N42.080 (2)C24—H24C0.9800
O1—C37'1.394 (5)C25—C261.522 (4)
O1—C371.398 (4)C25—H25A0.9900
N1—C41.367 (3)C25—H25B0.9900
N1—C11.374 (3)C26—H26A0.9800
N2—C61.372 (3)C26—H26B0.9800
N2—C91.381 (3)C26—H26C0.9800
N3—C111.374 (3)C27—C281.522 (4)
N3—C141.376 (3)C27—H27A0.9900
N4—C161.369 (3)C27—H27B0.9900
N4—C191.379 (3)C28—H28A0.9800
C1—C201.389 (3)C28—H28B0.9800
C1—C21.448 (4)C28—H28C0.9800
C2—C31.360 (4)C29—C301.511 (4)
C2—C211.491 (3)C29—H29A0.9900
C3—C41.445 (3)C29—H29B0.9900
C3—C231.500 (3)C30—H30A0.9800
C4—C51.390 (3)C30—H30B0.9800
C5—C61.387 (4)C30—H30C0.9800
C5—H5A0.9500C31—C321.521 (4)
C6—C71.449 (3)C31—H31A0.9900
C7—C81.362 (4)C31—H31B0.9900
C7—C251.499 (4)C32—H32A0.9800
C8—C91.441 (3)C32—H32B0.9800
C8—C271.506 (3)C32—H32C0.9800
C9—C101.390 (4)C33—C341.533 (4)
C10—C111.389 (4)C33—H33A0.9900
C10—H10A0.9500C33—H33B0.9900
C11—C121.444 (4)C34—H34A0.9800
C12—C131.361 (4)C34—H34B0.9800
C12—C291.501 (3)C34—H34C0.9800
C13—C141.441 (4)C35—C361.526 (4)
C13—C311.503 (4)C35—H35A0.9900
C14—C151.391 (4)C35—H35B0.9900
C15—C161.383 (4)C36—H36A0.9800
C15—H15A0.9500C36—H36B0.9800
C16—C171.450 (3)C36—H36C0.9800
C17—C181.361 (4)C37—C381.554 (7)
C17—C331.493 (3)C37—H37A0.9900
C18—C191.446 (3)C37—H37B0.9900
C18—C351.502 (3)C38—H38A0.9800
C19—C201.379 (4)C38—H38B0.9800
C20—H20A0.9500C38—H38C0.9800
C21—C221.522 (4)C37'—C38'1.555 (7)
C21—H21A0.9900C37'—H37C0.9900
C21—H21B0.9900C37'—H37D0.9900
C22—H22A0.9800C38'—H38D0.9800
C22—H22B0.9800C38'—H38E0.9800
C22—H22C0.9800C38'—H38F0.9800
C23—C241.523 (4)
O1—Fe1—N2101.65 (8)C23—C24—H24A109.5
O1—Fe1—N3103.00 (8)C23—C24—H24B109.5
N2—Fe1—N386.77 (8)H24A—C24—H24B109.5
O1—Fe1—N1104.41 (8)C23—C24—H24C109.5
N2—Fe1—N187.11 (8)H24A—C24—H24C109.5
N3—Fe1—N1152.58 (8)H24B—C24—H24C109.5
O1—Fe1—N4104.19 (8)C7—C25—C26112.7 (2)
N2—Fe1—N4154.16 (8)C7—C25—H25A109.1
N3—Fe1—N487.00 (8)C26—C25—H25A109.1
N1—Fe1—N486.97 (8)C7—C25—H25B109.1
C37'—O1—Fe1130.4 (3)C26—C25—H25B109.1
C37—O1—Fe1128.6 (3)H25A—C25—H25B107.8
C4—N1—C1106.0 (2)C25—C26—H26A109.5
C4—N1—Fe1126.34 (16)C25—C26—H26B109.5
C1—N1—Fe1126.48 (16)H26A—C26—H26B109.5
C6—N2—C9105.7 (2)C25—C26—H26C109.5
C6—N2—Fe1125.44 (16)H26A—C26—H26C109.5
C9—N2—Fe1126.34 (16)H26B—C26—H26C109.5
C11—N3—C14105.7 (2)C8—C27—C28113.3 (2)
C11—N3—Fe1126.62 (16)C8—C27—H27A108.9
C14—N3—Fe1125.25 (16)C28—C27—H27A108.9
C16—N4—C19106.0 (2)C8—C27—H27B108.9
C16—N4—Fe1125.94 (17)C28—C27—H27B108.9
C19—N4—Fe1126.59 (16)H27A—C27—H27B107.7
N1—C1—C20124.6 (2)C27—C28—H28A109.5
N1—C1—C2110.2 (2)C27—C28—H28B109.5
C20—C1—C2125.2 (2)H28A—C28—H28B109.5
C3—C2—C1106.6 (2)C27—C28—H28C109.5
C3—C2—C21127.9 (2)H28A—C28—H28C109.5
C1—C2—C21125.5 (2)H28B—C28—H28C109.5
C2—C3—C4106.7 (2)C12—C29—C30112.6 (2)
C2—C3—C23127.8 (2)C12—C29—H29A109.1
C4—C3—C23125.5 (2)C30—C29—H29A109.1
N1—C4—C5124.6 (2)C12—C29—H29B109.1
N1—C4—C3110.5 (2)C30—C29—H29B109.1
C5—C4—C3124.8 (2)H29A—C29—H29B107.8
C6—C5—C4126.7 (2)C29—C30—H30A109.5
C6—C5—H5A116.7C29—C30—H30B109.5
C4—C5—H5A116.7H30A—C30—H30B109.5
N2—C6—C5124.5 (2)C29—C30—H30C109.5
N2—C6—C7110.6 (2)H30A—C30—H30C109.5
C5—C6—C7124.9 (2)H30B—C30—H30C109.5
C8—C7—C6106.4 (2)C13—C31—C32113.9 (2)
C8—C7—C25128.4 (2)C13—C31—H31A108.8
C6—C7—C25125.2 (2)C32—C31—H31A108.8
C7—C8—C9107.1 (2)C13—C31—H31B108.8
C7—C8—C27127.9 (2)C32—C31—H31B108.8
C9—C8—C27124.9 (2)H31A—C31—H31B107.7
N2—C9—C10124.1 (2)C31—C32—H32A109.5
N2—C9—C8110.2 (2)C31—C32—H32B109.5
C10—C9—C8125.6 (2)H32A—C32—H32B109.5
C11—C10—C9126.7 (2)C31—C32—H32C109.5
C11—C10—H10A116.7H32A—C32—H32C109.5
C9—C10—H10A116.7H32B—C32—H32C109.5
N3—C11—C10124.5 (2)C17—C33—C34112.4 (2)
N3—C11—C12110.5 (2)C17—C33—H33A109.1
C10—C11—C12125.0 (2)C34—C33—H33A109.1
C13—C12—C11106.6 (2)C17—C33—H33B109.1
C13—C12—C29127.4 (2)C34—C33—H33B109.1
C11—C12—C29126.0 (2)H33A—C33—H33B107.9
C12—C13—C14106.8 (2)C33—C34—H34A109.5
C12—C13—C31127.8 (2)C33—C34—H34B109.5
C14—C13—C31125.4 (2)H34A—C34—H34B109.5
N3—C14—C15124.4 (2)C33—C34—H34C109.5
N3—C14—C13110.4 (2)H34A—C34—H34C109.5
C15—C14—C13125.2 (2)H34B—C34—H34C109.5
C16—C15—C14127.1 (2)C18—C35—C36112.3 (2)
C16—C15—H15A116.5C18—C35—H35A109.1
C14—C15—H15A116.5C36—C35—H35A109.1
N4—C16—C15124.4 (2)C18—C35—H35B109.1
N4—C16—C17110.5 (2)C36—C35—H35B109.1
C15—C16—C17125.1 (2)H35A—C35—H35B107.9
C18—C17—C16106.5 (2)C35—C36—H36A109.5
C18—C17—C33127.9 (2)C35—C36—H36B109.5
C16—C17—C33125.6 (2)H36A—C36—H36B109.5
C17—C18—C19107.0 (2)C35—C36—H36C109.5
C17—C18—C35128.0 (2)H36A—C36—H36C109.5
C19—C18—C35125.0 (2)H36B—C36—H36C109.5
N4—C19—C20124.5 (2)O1—C37—C38109.0 (7)
N4—C19—C18110.0 (2)O1—C37—H37A109.9
C20—C19—C18125.4 (2)C38—C37—H37A109.9
C19—C20—C1126.9 (2)O1—C37—H37B109.9
C19—C20—H20A116.5C38—C37—H37B109.9
C1—C20—H20A116.5H37A—C37—H37B108.3
C2—C21—C22112.2 (2)C37—C38—H38A109.5
C2—C21—H21A109.2C37—C38—H38B109.5
C22—C21—H21A109.2H38A—C38—H38B109.5
C2—C21—H21B109.2C37—C38—H38C109.5
C22—C21—H21B109.2H38A—C38—H38C109.5
H21A—C21—H21B107.9H38B—C38—H38C109.5
C21—C22—H22A109.5O1—C37'—C38'108.2 (10)
C21—C22—H22B109.5O1—C37'—H37C110.1
H22A—C22—H22B109.5C38'—C37'—H37C110.1
C21—C22—H22C109.5O1—C37'—H37D110.1
H22A—C22—H22C109.5C38'—C37'—H37D110.1
H22B—C22—H22C109.5H37C—C37'—H37D108.4
C3—C23—C24113.9 (2)C37'—C38'—H38D109.5
C3—C23—H23A108.8C37'—C38'—H38E109.5
C24—C23—H23A108.8H38D—C38'—H38E109.5
C3—C23—H23B108.8C37'—C38'—H38F109.5
C24—C23—H23B108.8H38D—C38'—H38F109.5
H23A—C23—H23B107.7H38E—C38'—H38F109.5
N2—Fe1—O1—C37'−69.0 (7)Fe1—N2—C9—C1018.3 (3)
N3—Fe1—O1—C37'20.4 (7)C6—N2—C9—C80.9 (3)
N1—Fe1—O1—C37'−159.0 (7)Fe1—N2—C9—C8−161.78 (16)
N4—Fe1—O1—C37'110.5 (7)C7—C8—C9—N2−0.1 (3)
N2—Fe1—O1—C37−27.4 (5)C27—C8—C9—N2−179.7 (2)
N3—Fe1—O1—C3761.9 (5)C7—C8—C9—C10179.8 (2)
N1—Fe1—O1—C37−117.4 (5)C27—C8—C9—C100.2 (4)
N4—Fe1—O1—C37152.1 (5)N2—C9—C10—C11−1.7 (4)
O1—Fe1—N1—C481.3 (2)C8—C9—C10—C11178.4 (2)
N2—Fe1—N1—C4−20.02 (19)C14—N3—C11—C10−176.7 (2)
N3—Fe1—N1—C4−97.3 (2)Fe1—N3—C11—C10−13.9 (4)
N4—Fe1—N1—C4−174.9 (2)C14—N3—C11—C121.2 (3)
O1—Fe1—N1—C1−84.3 (2)Fe1—N3—C11—C12163.94 (16)
N2—Fe1—N1—C1174.4 (2)C9—C10—C11—N3−0.6 (4)
N3—Fe1—N1—C197.1 (2)C9—C10—C11—C12−178.2 (2)
N4—Fe1—N1—C119.6 (2)N3—C11—C12—C13−2.0 (3)
O1—Fe1—N2—C6−79.7 (2)C10—C11—C12—C13175.8 (2)
N3—Fe1—N2—C6177.6 (2)N3—C11—C12—C29177.7 (2)
N1—Fe1—N2—C624.4 (2)C10—C11—C12—C29−4.5 (4)
N4—Fe1—N2—C6101.3 (2)C11—C12—C13—C142.0 (3)
O1—Fe1—N2—C979.7 (2)C29—C12—C13—C14−177.7 (2)
N3—Fe1—N2—C9−22.9 (2)C11—C12—C13—C31−176.9 (2)
N1—Fe1—N2—C9−176.2 (2)C29—C12—C13—C313.4 (4)
N4—Fe1—N2—C9−99.2 (3)C11—N3—C14—C15−178.9 (2)
O1—Fe1—N3—C11−80.3 (2)Fe1—N3—C14—C1518.0 (3)
N2—Fe1—N3—C1120.9 (2)C11—N3—C14—C130.1 (3)
N1—Fe1—N3—C1198.3 (2)Fe1—N3—C14—C13−163.00 (16)
N4—Fe1—N3—C11175.8 (2)C12—C13—C14—N3−1.3 (3)
O1—Fe1—N3—C1479.2 (2)C31—C13—C14—N3177.6 (2)
N2—Fe1—N3—C14−179.6 (2)C12—C13—C14—C15177.6 (2)
N1—Fe1—N3—C14−102.2 (2)C31—C13—C14—C15−3.4 (4)
N4—Fe1—N3—C14−24.6 (2)N3—C14—C15—C161.1 (4)
O1—Fe1—N4—C16−79.3 (2)C13—C14—C15—C16−177.8 (2)
N2—Fe1—N4—C1699.6 (2)C19—N4—C16—C15178.4 (2)
N3—Fe1—N4—C1623.3 (2)Fe1—N4—C16—C15−14.9 (3)
N1—Fe1—N4—C16176.6 (2)C19—N4—C16—C17−0.3 (3)
O1—Fe1—N4—C1984.8 (2)Fe1—N4—C16—C17166.46 (16)
N2—Fe1—N4—C19−96.3 (2)C14—C15—C16—N4−2.8 (4)
N3—Fe1—N4—C19−172.6 (2)C14—C15—C16—C17175.7 (2)
N1—Fe1—N4—C19−19.3 (2)N4—C16—C17—C180.9 (3)
C4—N1—C1—C20178.3 (2)C15—C16—C17—C18−177.8 (2)
Fe1—N1—C1—C20−13.7 (3)N4—C16—C17—C33−177.4 (2)
C4—N1—C1—C2−0.4 (3)C15—C16—C17—C333.9 (4)
Fe1—N1—C1—C2167.51 (16)C16—C17—C18—C19−1.0 (3)
N1—C1—C2—C31.0 (3)C33—C17—C18—C19177.3 (2)
C20—C1—C2—C3−177.7 (2)C16—C17—C18—C35179.9 (2)
N1—C1—C2—C21−177.7 (2)C33—C17—C18—C35−1.9 (4)
C20—C1—C2—C213.6 (4)C16—N4—C19—C20179.8 (2)
C1—C2—C3—C4−1.1 (3)Fe1—N4—C19—C2013.1 (3)
C21—C2—C3—C4177.5 (2)C16—N4—C19—C18−0.3 (3)
C1—C2—C3—C23178.2 (2)Fe1—N4—C19—C18−166.99 (16)
C21—C2—C3—C23−3.2 (4)C17—C18—C19—N40.9 (3)
C1—N1—C4—C5179.1 (2)C35—C18—C19—N4−180.0 (2)
Fe1—N1—C4—C511.2 (3)C17—C18—C19—C20−179.3 (2)
C1—N1—C4—C3−0.3 (3)C35—C18—C19—C20−0.1 (4)
Fe1—N1—C4—C3−168.24 (16)N4—C19—C20—C11.7 (4)
C2—C3—C4—N10.9 (3)C18—C19—C20—C1−178.2 (2)
C23—C3—C4—N1−178.4 (2)N1—C1—C20—C19−1.4 (4)
C2—C3—C4—C5−178.5 (2)C2—C1—C20—C19177.2 (2)
C23—C3—C4—C52.2 (4)C3—C2—C21—C22−90.1 (3)
N1—C4—C5—C62.8 (4)C1—C2—C21—C2288.4 (3)
C3—C4—C5—C6−177.8 (2)C2—C3—C23—C24103.6 (3)
C9—N2—C6—C5176.4 (2)C4—C3—C23—C24−77.3 (3)
Fe1—N2—C6—C5−20.7 (3)C8—C7—C25—C2689.3 (3)
C9—N2—C6—C7−1.4 (3)C6—C7—C25—C26−87.7 (3)
Fe1—N2—C6—C7161.52 (16)C7—C8—C27—C28−96.2 (3)
C4—C5—C6—N22.3 (4)C9—C8—C27—C2883.3 (3)
C4—C5—C6—C7179.8 (2)C13—C12—C29—C3087.5 (3)
N2—C6—C7—C81.3 (3)C11—C12—C29—C30−92.2 (3)
C5—C6—C7—C8−176.5 (2)C12—C13—C31—C32−102.6 (3)
N2—C6—C7—C25178.9 (2)C14—C13—C31—C3278.7 (3)
C5—C6—C7—C251.1 (4)C18—C17—C33—C34−91.6 (3)
C6—C7—C8—C9−0.7 (3)C16—C17—C33—C3486.4 (3)
C25—C7—C8—C9−178.1 (2)C17—C18—C35—C3694.2 (3)
C6—C7—C8—C27178.9 (2)C19—C18—C35—C36−84.7 (3)
C25—C7—C8—C271.5 (4)Fe1—O1—C37—C38−169.3 (6)
C6—N2—C9—C10−179.0 (2)Fe1—O1—C37'—C38'160.2 (9)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2027).

References

  • Chelikani, P., Fita, I. & Loewen, P. C. (2004). Cell. Mol. Life Sci.61, 192–208. [PubMed]
  • Hatano, K. & Uno, T. (1990). Bull. Chem. Soc. Jpn, 63, 1825–1827.
  • Kanamori, D., Yamada, Y., Onoda, A., Okamura, T., Adachi, S., Yamamoto, H. & Ueyama, N. (2005). Inorg. Chim. Acta, 358, 331–338.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1994). XSCANS Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA.

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