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The title compound (systematic name: μ-oxo-bis­{[4,15-bis­(ethoxy­carbon­yl)-5,14-dimethyl-2,7,13,17-tetra­azatricyclo­[16.4.0.07,12]docosa-3,5,7,9,11,13,15,18(1),19,21-deca­ene-2,17-diido]iron(III)} sesquihydrate), [Fe2(C26H26N4O4)O]·1.5H2O, crystallizes in the monoclinic space group C2/c and has two iron centres which are coordinated by macrocyclic ligands with an N4 donor set. These iron centres are bridged by a μ-oxo ligand, resulting in the formation of a dinuclear complex unit. The μ-oxo ligand inter­acts with a water mol­ecule via strong hydrogen bonds. These solvent mol­ecules aggregate by additional hydrogen bonds, producing a tetra­nuclear aggregate. Towards the outer rim of the cavity formed by the carboxy­ethyl substituents attached to the tetra­aza-annulene systems there are additional solvent mol­ecules. Due to much weaker hydrogen-bond inter­actions, the latter are disordered and have site-occupancy factors less than 1.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004636/hg2003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004636/hg2003Isup2.hkl
Contains datablock I

CCDC reference: 601793

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.131
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 7.72 Ratio
Author Response: All atoms are correctly assigned, the composition of the compound is clear from other analytical data. The reason for this problem are disordered methyl groups which nevertheless could not be resolved.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.17 Ratio
Author Response: All atoms are correctly assigned, the composition of the compound is clear from other analytical data. The reason for this problem are disordered methyl groups which nevertheless could not be resolved.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C17
Author Response: The methyl group C18 is disordered. Unfortunately this disorder could not be resolved.
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O10
Author Response: This is indeed one of the solvate water molecules. H-atoms could not be resolved from Difference Fourier Analysis.
PLAT430_ALERT_2_A Short Inter D...A Contact  O11X   ..  O11X    ..       2.45 Ang.
Author Response: This is caused by the highly disordered water molecule O11 which is only weakly bound and in addition to being disordered thus shows an site occupation factor below 1.
PLAT432_ALERT_2_A Short Inter X...Y Contact  C32X   ..  C32X    ..       2.75 Ang.
Author Response: This effect again is due to disorder of the ethyl group which unfortunately could not be resolved.

Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg.
Author Response: Since the criterion for MoKa is 25.24 deg and the data parameter ratio for I looks alright, I hope this is not a real problem.
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          4
Author Response: Again this is due to the disorder of some of the ethyl substituents which could not be resolved.
PLAT430_ALERT_2_B Short Inter D...A Contact  O10    ..  O11     ..       2.65 Ang.
Author Response: This is caused by the highly disordered water molecule O11 which is only weakly bound and in addition to being disordered thus shows an site occupation factor below 1.

Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.01 Ratio
Author Response: All atoms are correctly assigned, the composition of the compound is clear from other analytical data. The reason for this problem are disordered methyl groups which nevertheless could not be resolved.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17X
Author Response: The methyl group C18 is disordered. Unfortunately this disorder could not be resolved.
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      17.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O11
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O11X
PLAT430_ALERT_2_C Short Inter D...A Contact  O1     ..  O10     ..       2.89 Ang.
Author Response: This is caused by the highly disordered water molecule O11 which is only weakly bound and in addition to being disordered thus shows an site occupation factor below 1.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      31.00 A   3  
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.30 Deg.
              C6X  -C5   -C6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.23 Deg.
              N2   -C8   -FE1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.47 Deg.
              N3   -C13  -FE1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.40 Deg.
              C17  -O4   -C17X    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.38 Deg.
              N6   -C34  -FE2     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.09 Deg.
              N7   -C39  -FE2     1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              O

Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C52 H52 Fe2 N8 O10.5 Atom count from _chemical_formula_moiety:C52 H55 Fe2 N8 O10.5
6 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 20 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (Boer et al., 1984); data reduction: MolEN (Nonius, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.

µ-oxo-bis{[4,15-bis(ethoxycarbonyl)-5,14-dimethyl-2,7,13,17- tetraazatricyclo[16.4.0.07,12]docosa-3,5,7,9,11,13,15,18 (1),19,21-decaene- 2,17-diido]iron(III)} sesquihydrate top
Crystal data top
[Fe2(C26H26N4O4)O]·1.5H2OF(000) = 4448
Mr = 1071.72Dx = 1.385 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 27.322 (6) Åθ = 20.1–27.8°
b = 13.494 (4) ŵ = 0.63 mm1
c = 29.838 (5) ÅT = 213 K
β = 111.26 (2)°Cube, red
V = 10252 (4) Å30.6 × 0.4 × 0.3 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
6718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω/2θ scansh = 032
Absorption correction: ψ scan
(North et al., 1968)
k = 160
Tmin = 0.776, Tmax = 0.830l = 3533
9161 measured reflections3 standard reflections every 600 min
8963 independent reflections intensity decay: 3.6%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0507P)2 + 35.0302P]
where P = (Fo2 + 2Fc2)/3
8963 reflections(Δ/σ)max = 0.004
681 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.52 e Å3
Special details top

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*/UeqOcc. (<1)
Fe10.455878 (18)0.11981 (4)0.363464 (18)0.02613 (14)
Fe20.345151 (18)0.04404 (4)0.282503 (17)0.02348 (13)
O10.40880 (9)0.10002 (18)0.30446 (8)0.0287 (5)
N10.47942 (11)0.0180 (2)0.39148 (10)0.0299 (7)
C10.47211 (14)0.0668 (3)0.42675 (12)0.0320 (8)
C20.50456 (16)0.1576 (3)0.44782 (15)0.0418 (10)
H2A0.48580.21580.43230.050 (5)*
H2B0.51120.16090.48170.050 (5)*
H2C0.53730.15390.44290.050 (5)*
C30.43734 (14)0.0282 (3)0.44852 (12)0.0317 (8)
C40.42105 (16)0.0860 (3)0.48288 (14)0.0393 (9)
O20.40931 (14)0.0512 (2)0.51489 (11)0.0558 (8)
O30.41855 (12)0.1836 (2)0.47378 (10)0.0491 (8)
C50.4070 (2)0.2457 (4)0.50843 (19)0.0659 (15)
H5A0.36960.24620.50210.15 (2)*
H5B0.42530.22170.54090.15 (2)*
C60.4269 (8)0.3538 (9)0.5018 (5)0.060 (5)*0.46 (3)
H6A0.42050.39850.52410.063 (12)*0.46 (3)
H6B0.46390.35170.50770.063 (12)*0.46 (3)
H6C0.40830.37630.46960.063 (12)*0.46 (3)
C6X0.3989 (8)0.3424 (8)0.4914 (4)0.066 (4)*0.54 (3)
H6D0.36810.34500.46250.063 (12)*0.54 (3)
H6E0.39410.38480.51530.063 (12)*0.54 (3)
H6F0.42880.36430.48450.063 (12)*0.54 (3)
C70.41673 (13)0.0674 (3)0.44219 (13)0.0320 (8)
H70.39700.08450.46070.035 (7)*
N20.42203 (11)0.1358 (2)0.41314 (10)0.0298 (7)
C80.40418 (14)0.2339 (3)0.41391 (13)0.0323 (8)
C90.36520 (15)0.2631 (3)0.43082 (14)0.0413 (10)
H90.34810.21630.44280.044 (4)*
C100.35202 (17)0.3624 (3)0.42971 (16)0.0495 (11)
H100.32690.38280.44200.044 (4)*
C110.37628 (17)0.4312 (3)0.41032 (17)0.0515 (12)
H110.36690.49760.40930.044 (4)*
C120.41401 (16)0.4029 (3)0.39252 (16)0.0450 (10)
H120.42960.44980.37910.044 (4)*
C130.42877 (14)0.3046 (3)0.39460 (14)0.0344 (8)
N30.46826 (11)0.2654 (2)0.37936 (11)0.0310 (7)
C140.50674 (14)0.3208 (3)0.37633 (13)0.0339 (8)
H140.50400.38870.38020.035 (7)*
C150.55094 (14)0.2887 (3)0.36793 (13)0.0337 (8)
C160.58724 (18)0.3652 (3)0.36345 (18)0.0528 (12)
O40.57978 (16)0.4520 (3)0.38086 (18)0.0863 (13)
O50.62041 (15)0.3554 (3)0.34659 (17)0.0843 (13)
C170.6168 (7)0.5338 (13)0.3897 (7)0.064 (4)*0.33
H17A0.65190.50630.39890.055 (13)*0.33
H17B0.60960.56930.35980.055 (13)*0.33
C180.6166 (18)0.600 (3)0.4239 (14)0.20 (2)*0.33
H18A0.58180.62590.41620.15 (3)*0.33
H18B0.64030.65350.42490.15 (3)*0.33
H18C0.62770.56790.45470.15 (3)*0.33
C17X0.6038 (4)0.5365 (7)0.3616 (4)0.085 (3)*0.67
H17C0.64050.52350.36720.055 (13)*0.67
H17D0.58500.54600.32740.055 (13)*0.67
C18X0.5987 (7)0.6169 (12)0.3870 (6)0.142 (5)*0.67
H18D0.56210.63200.37860.15 (3)*0.67
H18E0.61620.67260.37950.15 (3)*0.67
H18F0.61410.60290.42080.15 (3)*0.67
C190.56351 (14)0.1871 (3)0.36384 (13)0.0325 (8)
C200.61972 (15)0.1584 (3)0.37214 (16)0.0475 (11)
H20A0.64320.20190.39560.050 (5)*
H20B0.62580.16370.34250.050 (5)*
H20C0.62580.09130.38360.050 (5)*
N40.52804 (11)0.1178 (2)0.35791 (10)0.0294 (7)
C210.53450 (13)0.0183 (3)0.34651 (13)0.0328 (8)
C220.55615 (15)0.0084 (3)0.31257 (15)0.0418 (10)
H220.57250.03930.30030.044 (4)*
C230.55339 (16)0.1051 (3)0.29719 (17)0.0512 (12)
H230.56820.12280.27480.044 (4)*
C240.52890 (16)0.1755 (3)0.31477 (17)0.0497 (11)
H240.52770.24080.30450.044 (4)*
C250.50607 (15)0.1505 (3)0.34748 (15)0.0399 (9)
H250.48870.19850.35850.044 (4)*
C260.50887 (13)0.0540 (3)0.36408 (13)0.0317 (8)
N50.29887 (11)0.1301 (2)0.30736 (10)0.0280 (6)
C270.27784 (13)0.1125 (3)0.34000 (12)0.0292 (8)
C280.23440 (15)0.1776 (3)0.34246 (15)0.0418 (10)
H28A0.24840.22480.36800.051 (5)*
H28B0.20840.13760.34850.051 (5)*
H28C0.21860.21200.31250.051 (5)*
C290.29145 (13)0.0259 (3)0.36951 (12)0.0277 (8)
C300.27606 (14)0.0208 (3)0.41182 (13)0.0345 (9)
O60.26572 (13)0.0907 (2)0.43203 (10)0.0530 (8)
O70.27648 (13)0.0720 (2)0.42814 (10)0.0481 (7)
C310.2684 (2)0.0826 (4)0.47340 (16)0.0542 (12)
H31A0.28290.02540.49350.080 (9)*
H31B0.28700.14100.49010.080 (9)*
C320.2125 (4)0.0918 (9)0.4660 (4)0.071 (4)*0.539 (14)
H32A0.19760.14590.44450.092 (14)*0.539 (14)
H32B0.19470.03150.45240.092 (14)*0.539 (14)
H32C0.20880.10400.49630.092 (14)*0.539 (14)
C32X0.2382 (6)0.1653 (12)0.4724 (5)0.087 (5)*0.461 (14)
H32D0.23540.17420.50330.092 (14)*0.461 (14)
H32E0.25430.22270.46470.092 (14)*0.461 (14)
H32F0.20370.15650.44850.092 (14)*0.461 (14)
C330.31809 (13)0.0560 (3)0.36091 (12)0.0286 (8)
H330.32150.11080.38070.029 (7)*
N60.33886 (10)0.0633 (2)0.32762 (9)0.0245 (6)
C340.35855 (13)0.1543 (3)0.31836 (12)0.0259 (7)
C350.37697 (14)0.2313 (3)0.35113 (13)0.0315 (8)
H350.37750.22480.38230.038 (4)*
C360.39440 (15)0.3174 (3)0.33706 (14)0.0360 (9)
H360.40610.36930.35880.038 (4)*
C370.39470 (15)0.3277 (3)0.29101 (14)0.0367 (9)
H370.40620.38640.28190.038 (4)*
C380.37778 (14)0.2504 (3)0.25874 (13)0.0310 (8)
H380.37870.25670.22800.038 (4)*
C390.35946 (13)0.1634 (3)0.27180 (12)0.0261 (7)
N70.34043 (10)0.0792 (2)0.24262 (10)0.0249 (6)
C400.32261 (13)0.0847 (3)0.19529 (12)0.0262 (7)
H400.32790.14470.18230.029 (7)*
C410.29677 (13)0.0110 (3)0.16235 (12)0.0265 (7)
C420.28416 (14)0.0345 (3)0.11098 (12)0.0311 (8)
O80.26757 (12)0.0217 (2)0.07774 (9)0.0477 (7)
O90.29414 (12)0.1307 (2)0.10434 (9)0.0422 (7)
C430.29166 (18)0.1593 (3)0.05698 (14)0.0466 (11)
H43A0.26440.12160.03290.080 (9)*
H43B0.28280.22910.05180.080 (9)*
C440.3433 (2)0.1409 (4)0.05182 (18)0.0657 (14)
H44A0.35030.07100.05360.109 (13)*
H44B0.34220.16570.02130.109 (13)*
H44C0.37060.17420.07720.109 (13)*
C450.28257 (13)0.0840 (3)0.17507 (12)0.0282 (8)
C460.24108 (15)0.1450 (3)0.13775 (13)0.0384 (9)
H46A0.21440.10190.11720.051 (5)*
H46B0.25690.18130.11890.051 (5)*
H46C0.22560.19050.15350.051 (5)*
N80.30255 (11)0.1152 (2)0.22006 (10)0.0263 (6)
C470.29520 (13)0.2122 (3)0.23481 (13)0.0299 (8)
C480.29926 (14)0.2980 (3)0.21042 (14)0.0346 (8)
H480.30200.29350.18030.038 (4)*
C490.29919 (15)0.3895 (3)0.23075 (15)0.0403 (9)
H490.30130.44650.21400.038 (4)*
C500.29606 (16)0.3974 (3)0.27569 (16)0.0435 (10)
H500.29530.45960.28890.038 (4)*
C510.29405 (15)0.3134 (3)0.30102 (14)0.0370 (9)
H510.29330.31930.33180.038 (4)*
C520.29306 (13)0.2198 (3)0.28127 (12)0.0284 (8)
O100.44529 (18)0.2355 (4)0.24846 (15)0.1080 (17)
O110.4385 (7)0.5757 (12)0.2695 (6)0.096 (5)*0.30
O11X0.4666 (8)0.5359 (16)0.2685 (7)0.078 (5)*0.20
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0197 (2)0.0288 (3)0.0291 (3)0.0002 (2)0.0080 (2)0.0037 (2)
Fe20.0200 (2)0.0271 (3)0.0226 (2)0.0013 (2)0.00675 (19)0.0003 (2)
O10.0220 (12)0.0342 (14)0.0286 (12)0.0030 (10)0.0079 (10)0.0022 (11)
N10.0233 (15)0.0332 (17)0.0319 (16)0.0000 (13)0.0084 (13)0.0027 (13)
C10.0252 (18)0.035 (2)0.0267 (18)0.0034 (16)0.0012 (15)0.0046 (16)
C20.035 (2)0.037 (2)0.044 (2)0.0038 (18)0.0024 (18)0.0026 (18)
C30.0258 (18)0.040 (2)0.0255 (18)0.0029 (16)0.0044 (15)0.0032 (16)
C40.037 (2)0.046 (2)0.029 (2)0.0017 (19)0.0049 (17)0.0036 (18)
O20.075 (2)0.060 (2)0.0438 (17)0.0021 (17)0.0357 (17)0.0012 (15)
O30.069 (2)0.0469 (18)0.0321 (15)0.0167 (15)0.0188 (14)0.0007 (13)
C50.089 (4)0.056 (3)0.058 (3)0.009 (3)0.033 (3)0.020 (3)
C70.0203 (17)0.042 (2)0.0300 (19)0.0020 (16)0.0044 (15)0.0054 (17)
N20.0272 (16)0.0299 (17)0.0316 (16)0.0008 (13)0.0098 (13)0.0019 (13)
C80.0256 (18)0.038 (2)0.0295 (19)0.0024 (16)0.0056 (15)0.0093 (16)
C90.032 (2)0.051 (3)0.041 (2)0.0042 (19)0.0141 (18)0.0090 (19)
C100.038 (2)0.059 (3)0.053 (3)0.013 (2)0.017 (2)0.017 (2)
C110.041 (2)0.039 (2)0.072 (3)0.005 (2)0.017 (2)0.016 (2)
C120.038 (2)0.032 (2)0.064 (3)0.0031 (18)0.019 (2)0.009 (2)
C130.0274 (19)0.036 (2)0.039 (2)0.0003 (16)0.0105 (16)0.0082 (17)
N30.0246 (15)0.0328 (17)0.0349 (16)0.0008 (13)0.0098 (13)0.0043 (13)
C140.035 (2)0.027 (2)0.037 (2)0.0012 (16)0.0106 (17)0.0004 (16)
C150.0286 (19)0.037 (2)0.037 (2)0.0077 (16)0.0128 (16)0.0027 (17)
C160.047 (3)0.042 (3)0.073 (3)0.010 (2)0.026 (2)0.001 (2)
O40.079 (3)0.039 (2)0.157 (4)0.0224 (19)0.063 (3)0.011 (2)
O50.068 (2)0.074 (3)0.141 (4)0.009 (2)0.075 (3)0.010 (2)
C190.0270 (19)0.040 (2)0.0303 (19)0.0024 (17)0.0099 (15)0.0074 (16)
C200.027 (2)0.055 (3)0.059 (3)0.0045 (19)0.0147 (19)0.016 (2)
N40.0220 (15)0.0320 (16)0.0330 (16)0.0011 (13)0.0085 (13)0.0069 (13)
C210.0179 (17)0.039 (2)0.039 (2)0.0013 (15)0.0072 (15)0.0097 (17)
C220.027 (2)0.050 (3)0.053 (2)0.0086 (18)0.0212 (18)0.018 (2)
C230.034 (2)0.060 (3)0.066 (3)0.006 (2)0.027 (2)0.028 (2)
C240.036 (2)0.042 (2)0.072 (3)0.0024 (19)0.022 (2)0.028 (2)
C250.029 (2)0.036 (2)0.053 (2)0.0006 (17)0.0128 (19)0.0104 (19)
C260.0202 (17)0.035 (2)0.037 (2)0.0026 (15)0.0076 (15)0.0063 (16)
N50.0259 (15)0.0301 (16)0.0270 (15)0.0026 (13)0.0085 (12)0.0002 (12)
C270.0211 (17)0.041 (2)0.0249 (17)0.0013 (16)0.0073 (14)0.0058 (16)
C280.034 (2)0.054 (3)0.040 (2)0.0118 (19)0.0171 (18)0.0002 (19)
C290.0239 (17)0.037 (2)0.0233 (17)0.0025 (15)0.0098 (14)0.0026 (15)
C300.0294 (19)0.047 (2)0.0284 (19)0.0012 (17)0.0121 (16)0.0011 (18)
O60.073 (2)0.0555 (19)0.0424 (17)0.0108 (17)0.0347 (16)0.0043 (15)
O70.072 (2)0.0490 (18)0.0364 (15)0.0080 (15)0.0359 (15)0.0015 (13)
C310.071 (3)0.061 (3)0.042 (2)0.013 (3)0.035 (2)0.000 (2)
C330.0241 (17)0.036 (2)0.0236 (17)0.0025 (15)0.0064 (14)0.0017 (15)
N60.0213 (14)0.0298 (16)0.0215 (14)0.0002 (12)0.0065 (12)0.0012 (12)
C340.0217 (17)0.0291 (18)0.0267 (17)0.0027 (14)0.0086 (14)0.0009 (15)
C350.033 (2)0.034 (2)0.0284 (19)0.0014 (16)0.0122 (16)0.0037 (16)
C360.040 (2)0.028 (2)0.038 (2)0.0013 (17)0.0130 (18)0.0078 (17)
C370.040 (2)0.026 (2)0.045 (2)0.0015 (17)0.0160 (18)0.0008 (17)
C380.0305 (19)0.0302 (19)0.0337 (19)0.0025 (16)0.0134 (16)0.0062 (16)
C390.0202 (17)0.0278 (18)0.0279 (18)0.0045 (14)0.0056 (14)0.0026 (15)
N70.0210 (14)0.0298 (15)0.0243 (14)0.0021 (12)0.0088 (12)0.0001 (12)
C400.0225 (17)0.0316 (19)0.0260 (17)0.0076 (15)0.0107 (14)0.0035 (15)
C410.0226 (17)0.0325 (19)0.0238 (17)0.0054 (15)0.0076 (14)0.0017 (14)
C420.0268 (18)0.039 (2)0.0272 (19)0.0075 (16)0.0096 (15)0.0000 (17)
O80.064 (2)0.0514 (18)0.0240 (14)0.0069 (15)0.0120 (13)0.0062 (13)
O90.0629 (19)0.0409 (16)0.0247 (13)0.0040 (14)0.0183 (13)0.0036 (12)
C430.066 (3)0.047 (3)0.028 (2)0.005 (2)0.019 (2)0.0066 (18)
C440.066 (3)0.085 (4)0.053 (3)0.007 (3)0.030 (3)0.002 (3)
C450.0193 (17)0.038 (2)0.0279 (18)0.0033 (15)0.0095 (14)0.0063 (16)
C460.031 (2)0.048 (2)0.031 (2)0.0038 (18)0.0042 (16)0.0021 (18)
N80.0230 (14)0.0287 (16)0.0261 (15)0.0011 (12)0.0077 (12)0.0002 (12)
C470.0201 (17)0.033 (2)0.034 (2)0.0044 (15)0.0069 (15)0.0014 (16)
C480.0288 (19)0.037 (2)0.036 (2)0.0071 (17)0.0101 (16)0.0050 (17)
C490.036 (2)0.031 (2)0.048 (2)0.0061 (17)0.0085 (19)0.0076 (18)
C500.041 (2)0.031 (2)0.054 (3)0.0108 (18)0.013 (2)0.0007 (19)
C510.033 (2)0.037 (2)0.039 (2)0.0071 (17)0.0110 (17)0.0031 (18)
C520.0206 (17)0.035 (2)0.0279 (18)0.0069 (15)0.0067 (14)0.0025 (15)
O100.084 (3)0.162 (5)0.078 (3)0.017 (3)0.029 (2)0.033 (3)
Geometric parameters (Å, º) top
Fe1—O11.784 (2)C20—H20C0.9600
Fe1—N32.020 (3)N4—C211.412 (5)
Fe1—N22.023 (3)C21—C221.393 (5)
Fe1—N42.038 (3)C21—C261.407 (5)
Fe1—N12.045 (3)C22—C231.377 (6)
Fe1—C212.745 (3)C22—H220.9300
Fe1—C262.753 (4)C23—C241.371 (6)
Fe1—C132.851 (4)C23—H230.9300
Fe1—C82.859 (4)C24—C251.377 (6)
Fe1—Fe23.2762 (11)C24—H240.9300
Fe2—O11.788 (2)C25—C261.385 (5)
Fe2—N72.022 (3)C25—H250.9300
Fe2—N62.026 (3)N5—C271.320 (4)
Fe2—N82.043 (3)N5—C521.416 (4)
Fe2—N52.044 (3)C27—C291.429 (5)
Fe2—C522.759 (4)C27—C281.499 (5)
Fe2—C472.762 (4)C28—H28A0.9600
Fe2—C342.857 (4)C28—H28B0.9600
Fe2—C392.860 (4)C28—H28C0.9600
N1—C11.317 (5)C29—C331.397 (5)
N1—C261.424 (4)C29—C301.470 (5)
C1—C31.429 (5)C30—O61.207 (5)
C1—C21.509 (5)C30—O71.342 (5)
C2—H2A0.9600O7—C311.452 (5)
C2—H2B0.9600C31—C32X1.382 (14)
C2—H2C0.9600C31—C321.466 (11)
C3—C71.392 (5)C31—H31A0.9700
C3—C41.480 (5)C31—H31B0.9700
C4—O21.207 (5)C32—H32A0.9600
C4—O31.342 (5)C32—H32B0.9600
O3—C51.452 (5)C32—H32C0.9600
C5—C6X1.390 (11)C32X—H32D0.9600
C5—C61.595 (15)C32X—H32E0.9600
C5—H5A0.9700C32X—H32F0.9600
C5—H5B0.9700C33—N61.314 (4)
C6—H6A0.9600C33—H330.9300
C6—H6B0.9600N6—C341.409 (4)
C6—H6C0.9600C34—C351.390 (5)
C6X—H6D0.9600C34—C391.404 (5)
C6X—H6E0.9600C35—C361.377 (5)
C6X—H6F0.9600C35—H350.9300
C7—N21.311 (5)C36—C371.384 (5)
C7—H70.9300C36—H360.9300
N2—C81.413 (5)C37—C381.381 (5)
C8—C91.391 (5)C37—H370.9300
C8—C131.405 (5)C38—C391.386 (5)
C9—C101.385 (6)C38—H380.9300
C9—H90.9300C39—N71.411 (4)
C10—C111.384 (6)N7—C401.318 (4)
C10—H100.9300C40—C411.397 (5)
C11—C121.374 (6)C40—H400.9300
C11—H110.9300C41—C451.429 (5)
C12—C131.381 (5)C41—C421.478 (5)
C12—H120.9300C42—O81.199 (4)
C13—N31.416 (5)C42—O91.356 (5)
N3—C141.320 (5)O9—C431.443 (4)
C14—C151.388 (5)C43—C441.495 (6)
C14—H140.9300C43—H43A0.9700
C15—C191.430 (5)C43—H43B0.9700
C15—C161.470 (6)C44—H44A0.9600
C16—O51.192 (5)C44—H44B0.9600
C16—O41.327 (6)C44—H44C0.9600
O4—C171.455 (17)C45—N81.322 (4)
O4—C17X1.530 (11)C45—C461.512 (5)
C17—C181.36 (4)C46—H46A0.9600
C17—H17A0.9700C46—H46B0.9600
C17—H17B0.9700C46—H46C0.9600
C18—H18A0.9600N8—C471.419 (5)
C18—H18B0.9600C47—C481.393 (5)
C18—H18C0.9600C47—C521.412 (5)
C17X—C18X1.360 (17)C48—C491.375 (5)
C17X—H17C0.9700C48—H480.9300
C17X—H17D0.9700C49—C501.378 (6)
C18X—H18D0.9600C49—H490.9300
C18X—H18E0.9600C50—C511.374 (6)
C18X—H18F0.9600C50—H500.9300
C19—N41.311 (5)C51—C521.391 (5)
C19—C201.515 (5)C51—H510.9300
C20—H20A0.9600O11—O11X0.95 (2)
C20—H20B0.9600
O1—Fe1—N3112.13 (12)C18—C17—O4116 (2)
O1—Fe1—N2112.42 (11)C18—C17—H17A108.2
N3—Fe1—N278.82 (12)O4—C17—H17A108.2
O1—Fe1—N4106.88 (11)C18—C17—H17B108.2
N3—Fe1—N487.00 (12)O4—C17—H17B108.2
N2—Fe1—N4140.70 (12)H17A—C17—H17B107.3
O1—Fe1—N1105.93 (12)C18X—C17X—O4103.8 (10)
N3—Fe1—N1141.93 (12)C18X—C17X—H17C111.0
N2—Fe1—N187.56 (12)O4—C17X—H17C111.0
N4—Fe1—N181.42 (12)C18X—C17X—H17D111.0
O1—Fe1—C2194.35 (11)O4—C17X—H17D111.0
N3—Fe1—C21116.94 (12)H17C—C17X—H17D109.0
N2—Fe1—C21141.67 (12)N4—C19—C15120.5 (3)
N4—Fe1—C2129.94 (11)N4—C19—C20119.7 (3)
N1—Fe1—C2158.00 (12)C15—C19—C20119.4 (3)
O1—Fe1—C2693.92 (11)C19—C20—H20A109.5
N3—Fe1—C26141.62 (11)C19—C20—H20B109.5
N2—Fe1—C26117.73 (12)H20A—C20—H20B109.5
N4—Fe1—C2657.79 (11)C19—C20—H20C109.5
N1—Fe1—C2630.19 (11)H20A—C20—H20C109.5
C21—Fe1—C2629.66 (11)H20B—C20—H20C109.5
O1—Fe1—C13105.84 (11)C19—N4—C21124.0 (3)
N3—Fe1—C1327.66 (11)C19—N4—Fe1132.0 (3)
N2—Fe1—C1354.97 (12)C21—N4—Fe1104.0 (2)
N4—Fe1—C13114.31 (11)C22—C21—C26119.5 (4)
N1—Fe1—C13137.96 (12)C22—C21—N4122.9 (4)
C21—Fe1—C13144.07 (11)C26—C21—N4116.5 (3)
C26—Fe1—C13160.24 (11)C22—C21—Fe1146.1 (3)
O1—Fe1—C8106.45 (10)C26—C21—Fe175.5 (2)
N3—Fe1—C854.93 (11)N4—C21—Fe146.08 (15)
N2—Fe1—C827.41 (11)C23—C22—C21120.0 (4)
N4—Fe1—C8136.68 (11)C23—C22—H22120.0
N1—Fe1—C8114.63 (11)C21—C22—H22120.0
C21—Fe1—C8159.20 (10)C24—C23—C22120.3 (4)
C26—Fe1—C8144.52 (11)C24—C23—H23119.8
C13—Fe1—C828.49 (11)C22—C23—H23119.8
O1—Fe1—Fe223.52 (7)C23—C24—C25120.7 (4)
N3—Fe1—Fe2120.52 (9)C23—C24—H24119.7
N2—Fe1—Fe291.63 (9)C25—C24—H24119.7
N4—Fe1—Fe2126.71 (8)C24—C25—C26120.2 (4)
N1—Fe1—Fe294.99 (8)C24—C25—H25119.9
C21—Fe1—Fe2106.46 (8)C26—C25—H25119.9
C26—Fe1—Fe294.70 (8)C25—C26—C21119.2 (3)
C13—Fe1—Fe2103.51 (8)C25—C26—N1123.8 (3)
C8—Fe1—Fe293.20 (7)C21—C26—N1116.0 (3)
O1—Fe2—N7114.15 (11)C25—C26—Fe1146.9 (3)
O1—Fe2—N6111.34 (11)C21—C26—Fe174.9 (2)
N7—Fe2—N678.50 (11)N1—C26—Fe146.24 (16)
O1—Fe2—N8107.00 (11)C27—N5—C52124.6 (3)
N7—Fe2—N887.49 (11)C27—N5—Fe2131.1 (3)
N6—Fe2—N8141.63 (11)C52—N5—Fe2104.3 (2)
O1—Fe2—N5105.92 (11)N5—C27—C29121.1 (3)
N7—Fe2—N5139.93 (11)N5—C27—C28119.7 (3)
N6—Fe2—N587.27 (11)C29—C27—C28118.9 (3)
N8—Fe2—N580.85 (11)C27—C28—H28A109.5
O1—Fe2—C5294.03 (11)C27—C28—H28B109.5
N7—Fe2—C52140.96 (11)H28A—C28—H28B109.5
N6—Fe2—C52117.09 (11)C27—C28—H28C109.5
N8—Fe2—C5257.54 (11)H28A—C28—H28C109.5
N5—Fe2—C5229.82 (11)H28B—C28—H28C109.5
O1—Fe2—C4794.29 (11)C33—C29—C27124.8 (3)
N7—Fe2—C47117.29 (11)C33—C29—C30116.8 (3)
N6—Fe2—C47141.65 (11)C27—C29—C30118.4 (3)
N8—Fe2—C4729.83 (11)O6—C30—O7121.4 (3)
N5—Fe2—C4757.65 (11)O6—C30—C29125.7 (4)
C52—Fe2—C4729.63 (10)O7—C30—C29112.8 (3)
O1—Fe2—C34106.45 (10)C30—O7—C31116.5 (3)
N7—Fe2—C3454.67 (10)C32X—C31—O7110.5 (7)
N6—Fe2—C3427.36 (10)C32X—C31—C3249.2 (7)
N8—Fe2—C34137.32 (11)O7—C31—C32111.7 (5)
N5—Fe2—C34114.13 (11)C32X—C31—H31A139.8
C52—Fe2—C34143.69 (10)O7—C31—H31A109.3
C47—Fe2—C34159.25 (10)C32—C31—H31A109.3
O1—Fe2—C39107.47 (10)C32X—C31—H31B63.5
N7—Fe2—C3927.30 (10)O7—C31—H31B109.3
N6—Fe2—C3954.75 (10)C32—C31—H31B109.3
N8—Fe2—C39114.45 (11)H31A—C31—H31B107.9
N5—Fe2—C39136.41 (11)C31—C32—H32A109.5
C52—Fe2—C39158.50 (10)C31—C32—H32B109.5
C47—Fe2—C39143.96 (10)C31—C32—H32C109.5
C34—Fe2—C3928.43 (9)C31—C32X—H32D109.5
O1—Fe2—Fe123.46 (7)C31—C32X—H32E109.5
N7—Fe2—Fe1122.38 (8)C31—C32X—H32F109.5
N6—Fe2—Fe190.65 (8)N6—C33—C29126.5 (3)
N8—Fe2—Fe1126.44 (8)N6—C33—H33116.8
N5—Fe2—Fe194.73 (8)C29—C33—H33116.8
C52—Fe2—Fe194.33 (8)C33—N6—C34120.9 (3)
C47—Fe2—Fe1105.97 (8)C33—N6—Fe2127.8 (2)
C34—Fe2—Fe193.31 (7)C34—N6—Fe2111.3 (2)
C39—Fe2—Fe1105.11 (7)C35—C34—C39120.0 (3)
Fe1—O1—Fe2133.01 (14)C35—C34—N6125.5 (3)
C1—N1—C26124.7 (3)C39—C34—N6114.5 (3)
C1—N1—Fe1131.7 (3)C35—C34—Fe2158.2 (3)
C26—N1—Fe1103.6 (2)C39—C34—Fe275.9 (2)
N1—C1—C3119.9 (3)N6—C34—Fe241.38 (15)
N1—C1—C2120.2 (3)C36—C35—C34119.5 (3)
C3—C1—C2119.6 (3)C36—C35—H35120.2
C1—C2—H2A109.5C34—C35—H35120.2
C1—C2—H2B109.5C35—C36—C37121.0 (3)
H2A—C2—H2B109.5C35—C36—H36119.5
C1—C2—H2C109.5C37—C36—H36119.5
H2A—C2—H2C109.5C38—C37—C36119.7 (4)
H2B—C2—H2C109.5C38—C37—H37120.2
C7—C3—C1125.4 (3)C36—C37—H37120.2
C7—C3—C4112.0 (3)C37—C38—C39120.5 (3)
C1—C3—C4122.6 (3)C37—C38—H38119.8
O2—C4—O3122.2 (4)C39—C38—H38119.8
O2—C4—C3125.2 (4)C38—C39—C34119.3 (3)
O3—C4—C3112.6 (3)C38—C39—N7126.7 (3)
C4—O3—C5115.5 (3)C34—C39—N7114.0 (3)
C6X—C5—O3109.1 (6)C38—C39—Fe2159.7 (2)
C6X—C5—C627.3 (6)C34—C39—Fe275.7 (2)
O3—C5—C6105.5 (6)N7—C39—Fe241.09 (15)
C6X—C5—H5A84.6C40—N7—C39121.7 (3)
O3—C5—H5A110.6C40—N7—Fe2126.6 (2)
C6—C5—H5A110.6C39—N7—Fe2111.6 (2)
C6X—C5—H5B129.4N7—C40—C41127.6 (3)
O3—C5—H5B110.6N7—C40—H40116.2
C6—C5—H5B110.6C41—C40—H40116.2
H5A—C5—H5B108.8C40—C41—C45124.6 (3)
C5—C6—H6A109.5C40—C41—C42116.4 (3)
C5—C6—H6B109.5C45—C41—C42118.9 (3)
C5—C6—H6C109.5O8—C42—O9121.3 (3)
C5—C6X—H6D109.5O8—C42—C41126.8 (4)
C5—C6X—H6E109.5O9—C42—C41111.9 (3)
H6D—C6X—H6E109.5C42—O9—C43117.3 (3)
C5—C6X—H6F109.5O9—C43—C44110.2 (4)
H6D—C6X—H6F109.5O9—C43—H43A109.6
H6E—C6X—H6F109.5C44—C43—H43A109.6
N2—C7—C3127.3 (3)O9—C43—H43B109.6
N2—C7—H7116.3C44—C43—H43B109.6
C3—C7—H7116.3H43A—C43—H43B108.1
C7—N2—C8121.8 (3)C43—C44—H44A109.5
C7—N2—Fe1126.8 (2)C43—C44—H44B109.5
C8—N2—Fe1111.4 (2)H44A—C44—H44B109.5
C9—C8—C13119.9 (4)C43—C44—H44C109.5
C9—C8—N2125.9 (4)H44A—C44—H44C109.5
C13—C8—N2114.2 (3)H44B—C44—H44C109.5
C9—C8—Fe1159.0 (3)N8—C45—C41120.3 (3)
C13—C8—Fe175.4 (2)N8—C45—C46119.8 (3)
N2—C8—Fe141.23 (16)C41—C45—C46119.7 (3)
C10—C9—C8119.5 (4)C45—C46—H46A109.5
C10—C9—H9120.2C45—C46—H46B109.5
C8—C9—H9120.2H46A—C46—H46B109.5
C11—C10—C9120.0 (4)C45—C46—H46C109.5
C11—C10—H10120.0H46A—C46—H46C109.5
C9—C10—H10120.0H46B—C46—H46C109.5
C12—C11—C10121.0 (4)C45—N8—C47123.8 (3)
C12—C11—H11119.5C45—N8—Fe2131.7 (2)
C10—C11—H11119.5C47—N8—Fe2104.4 (2)
C11—C12—C13119.8 (4)C48—C47—C52119.5 (3)
C11—C12—H12120.1C48—C47—N8123.9 (3)
C13—C12—H12120.1C52—C47—N8115.6 (3)
C12—C13—C8119.7 (4)C48—C47—Fe2146.5 (2)
C12—C13—N3126.0 (4)C52—C47—Fe275.0 (2)
C8—C13—N3114.3 (3)N8—C47—Fe245.76 (15)
C12—C13—Fe1158.7 (3)C49—C48—C47120.1 (4)
C8—C13—Fe176.1 (2)C49—C48—H48119.9
N3—C13—Fe141.47 (16)C47—C48—H48119.9
C14—N3—C13121.9 (3)C48—C49—C50120.6 (4)
C14—N3—Fe1127.2 (3)C48—C49—H49119.7
C13—N3—Fe1110.9 (2)C50—C49—H49119.7
N3—C14—C15127.1 (4)C51—C50—C49120.0 (4)
N3—C14—H14116.5C51—C50—H50120.0
C15—C14—H14116.5C49—C50—H50120.0
C14—C15—C19124.4 (3)C50—C51—C52121.0 (4)
C14—C15—C16117.2 (4)C50—C51—H51119.5
C19—C15—C16118.3 (3)C52—C51—H51119.5
O5—C16—O4120.7 (4)C51—C52—C47118.7 (3)
O5—C16—C15127.0 (4)C51—C52—N5124.2 (3)
O4—C16—C15112.3 (4)C47—C52—N5116.2 (3)
C16—O4—C17123.1 (8)C51—C52—Fe2147.7 (3)
C16—O4—C17X111.3 (5)C47—C52—Fe275.3 (2)
C17—O4—C17X30.4 (7)N5—C52—Fe245.89 (15)
 

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