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In the title compound, [Fe(C12H8N2)3](C4O4)·8H2O or [Fe(phen)3]sq·8H2O, where phen is 1,10-phenanthroline and sq is the squarate dianion (C4O4)2−, the FeII centre has a distorted octa­hedral coordination geometry comprising six N atoms from the three bidentate chelating phen ligands. An extensive three-dimensional network of Owater—H...O, Owater—H...Owater and C—H...O hydrogen-bonding inter­actions is responsible for crystal stabilization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019550/ci6598sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019550/ci6598Isup2.hkl
Contains datablock I

CCDC reference: 277227

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.113
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H9A .. H12B .. 1.99 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N1 .. 6.38 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N2 .. 5.81 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N3 .. 5.48 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N4 .. 6.61 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N6 .. 5.67 su PLAT417_ALERT_2_C Short Inter D-H..H-D H9B .. H10B .. 2.14 Ang. PLAT731_ALERT_1_C Bond Calc 0.88(6), Rep 0.89(2) ...... 3.00 su-Rat O9 -H9B 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(7), Rep 0.86(2) ...... 3.50 su-Rat O9 -H9A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(6), Rep 0.89(2) ...... 3.00 su-Rat O9 -H9B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(7), Rep 0.86(2) ...... 3.50 su-Rat O9 -H9A 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Tris(1,10-phenanthroline-κ2N,N')iron(II) squarate octahydrate top
Crystal data top
[Fe(C12H8N2)3](C4O4)·8H2OF(000) = 1776
Mr = 852.63Dx = 1.454 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5187 reflections
a = 10.9285 (6) Åθ = 1.7–27.8°
b = 21.3431 (7) ŵ = 0.46 mm1
c = 16.8988 (8) ÅT = 297 K
β = 98.804 (4)°Plate, red
V = 3895.4 (3) Å30.31 × 0.25 × 0.19 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
8612 independent reflections
Radiation source: fine-focus sealed tube5723 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 6.67 pixels mm-1θmax = 27.2°, θmin = 1.6°
ω scansh = 1314
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2727
Tmin = 0.734, Tmax = 0.932l = 2121
42766 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0679P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
8612 reflectionsΔρmax = 0.28 e Å3
583 parametersΔρmin = 0.40 e Å3
25 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (3)
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*/Ueq
C10.3344 (2)0.22086 (11)0.94575 (13)0.0491 (5)
H10.28860.25170.91560.059*
C20.3111 (2)0.20920 (13)1.02306 (14)0.0611 (6)
H20.24970.23161.04330.073*
C30.3775 (3)0.16530 (14)1.06872 (15)0.0685 (7)
H30.36150.15711.12020.082*
C40.4711 (2)0.13215 (12)1.03793 (14)0.0601 (6)
C50.5492 (3)0.08535 (15)1.08055 (17)0.0821 (9)
H50.54000.07581.13300.098*
C60.6353 (3)0.05505 (15)1.04633 (17)0.0822 (9)
H60.68540.02541.07590.099*
C70.6518 (2)0.06738 (11)0.96529 (15)0.0578 (6)
C80.7405 (2)0.03784 (12)0.92542 (17)0.0663 (7)
H80.79280.00730.95120.080*
C90.7483 (2)0.05457 (11)0.84895 (15)0.0585 (6)
H90.80700.03580.82220.070*
C100.66867 (19)0.09996 (10)0.81014 (14)0.0493 (5)
H100.67540.11040.75760.059*
C110.57649 (19)0.11274 (10)0.92268 (12)0.0452 (5)
C120.48709 (19)0.14546 (10)0.95944 (12)0.0458 (5)
C130.22761 (18)0.26333 (10)0.73763 (13)0.0483 (5)
H130.18990.22490.72410.058*
C140.1583 (2)0.31764 (11)0.72133 (15)0.0559 (6)
H140.07610.31490.69710.067*
C150.2093 (2)0.37477 (11)0.74042 (14)0.0531 (5)
H150.16250.41110.73050.064*
C160.33425 (19)0.37784 (9)0.77533 (12)0.0445 (4)
C170.4003 (2)0.43505 (10)0.79635 (14)0.0555 (5)
H170.35830.47300.78970.067*
C180.5213 (2)0.43477 (10)0.82536 (15)0.0561 (6)
H180.56210.47270.83700.067*
C190.5897 (2)0.37743 (10)0.83892 (12)0.0471 (5)
C200.7159 (2)0.37344 (11)0.87166 (14)0.0543 (5)
H200.76240.40960.88410.065*
C210.7686 (2)0.31586 (12)0.88477 (15)0.0590 (6)
H210.85170.31260.90680.071*
C220.69939 (18)0.26209 (11)0.86547 (13)0.0498 (5)
H220.73810.22340.87450.060*
C230.52638 (17)0.32112 (9)0.82152 (11)0.0386 (4)
C240.39834 (18)0.32152 (9)0.78847 (11)0.0385 (4)
C250.58742 (19)0.21882 (11)0.66050 (13)0.0499 (5)
H250.63650.24850.69070.060*
C260.6063 (2)0.20793 (13)0.58212 (14)0.0619 (6)
H260.66720.22990.56080.074*
C270.5354 (3)0.16508 (14)0.53695 (15)0.0677 (7)
H270.54870.15710.48480.081*
C280.4420 (2)0.13279 (11)0.56859 (13)0.0556 (6)
C290.3584 (3)0.08803 (13)0.52634 (15)0.0693 (7)
H290.36570.07820.47360.083*
C300.2698 (2)0.05979 (12)0.56079 (15)0.0630 (6)
H300.21580.03180.53120.076*
C310.2576 (2)0.07231 (9)0.64215 (14)0.0491 (5)
C320.1694 (2)0.04452 (10)0.68286 (16)0.0587 (6)
H320.11300.01580.65690.070*
C330.1668 (2)0.05979 (11)0.76071 (17)0.0617 (6)
H330.10800.04170.78810.074*
C340.2520 (2)0.10245 (10)0.79951 (15)0.0530 (5)
H340.24910.11190.85290.064*
C350.33943 (18)0.11517 (9)0.68519 (12)0.0420 (4)
C360.42994 (18)0.14625 (9)0.64790 (12)0.0432 (4)
C370.8632 (2)0.08495 (11)0.63575 (15)0.0561 (6)
C380.8991 (2)0.14814 (11)0.66219 (14)0.0576 (6)
C390.9576 (2)0.15746 (11)0.59251 (14)0.0562 (5)
C400.91917 (19)0.09514 (10)0.56355 (13)0.0477 (5)
N10.41973 (15)0.18965 (8)0.91332 (10)0.0420 (4)
N20.50220 (15)0.18863 (8)0.69413 (10)0.0408 (4)
N30.33754 (15)0.13031 (7)0.76332 (10)0.0419 (4)
N40.57940 (14)0.26340 (7)0.83441 (9)0.0397 (4)
N50.58338 (15)0.12883 (7)0.84551 (10)0.0411 (4)
N60.34573 (14)0.26396 (7)0.77179 (9)0.0387 (3)
O10.8115 (2)0.03966 (9)0.66285 (13)0.0851 (6)
O20.92904 (16)0.06266 (7)0.50370 (10)0.0609 (4)
O31.0200 (2)0.20095 (8)0.56762 (13)0.0839 (6)
O40.8848 (2)0.18132 (9)0.72229 (12)0.0810 (6)
O51.0081 (2)0.03433 (10)0.89716 (15)0.0931 (7)
O61.0955 (2)0.08269 (9)0.76703 (12)0.0777 (5)
O71.06292 (19)0.06723 (8)0.37953 (11)0.0666 (5)
O81.10008 (19)0.19476 (8)0.42302 (13)0.0708 (5)
O90.8793 (4)0.30815 (16)0.5277 (2)0.1258 (10)
O100.8240 (2)0.30343 (10)0.68316 (16)0.0877 (6)
O111.0097 (3)0.18597 (10)0.87431 (16)0.1172 (10)
O120.0861 (3)0.08040 (12)0.96385 (16)0.1091 (8)
Fe10.46192 (2)0.194212 (12)0.803680 (16)0.03605 (9)
H5A0.992 (2)0.0607 (10)0.9312 (12)0.054*
H5B1.040 (2)0.0554 (10)0.8636 (11)0.054*
H6A1.0504 (19)0.0846 (11)0.7204 (11)0.054*
H6B1.124 (2)0.1216 (8)0.7751 (13)0.054*
H7A1.110 (2)0.0390 (10)0.3715 (14)0.054*
H7B1.030 (2)0.0628 (11)0.4200 (12)0.054*
H8A1.080 (2)0.1943 (10)0.4694 (10)0.054*
H8B1.093 (2)0.1591 (8)0.4048 (13)0.054*
H10A0.858 (2)0.2701 (9)0.7012 (13)0.054*
H10B0.829 (2)0.3083 (11)0.6337 (10)0.054*
H11A0.975 (2)0.1864 (10)0.8248 (10)0.054*
H11B1.041 (2)0.2204 (9)0.8838 (13)0.054*
H12A0.061 (2)0.0489 (8)0.9377 (14)0.054*
H12B0.0242 (19)0.1070 (9)0.9524 (15)0.054*
H9B0.940 (5)0.282 (3)0.545 (5)0.31 (5)*
H9A0.915 (6)0.334 (3)0.500 (4)0.26 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0499 (12)0.0571 (12)0.0422 (12)0.0022 (9)0.0129 (9)0.0061 (10)
C20.0598 (14)0.0823 (16)0.0446 (13)0.0055 (12)0.0186 (11)0.0081 (12)
C30.0754 (17)0.0943 (19)0.0397 (13)0.0024 (15)0.0214 (12)0.0042 (13)
C40.0682 (15)0.0743 (15)0.0387 (12)0.0024 (12)0.0107 (11)0.0070 (11)
C50.098 (2)0.103 (2)0.0472 (15)0.0227 (18)0.0174 (14)0.0277 (15)
C60.096 (2)0.092 (2)0.0576 (17)0.0272 (17)0.0099 (15)0.0292 (15)
C70.0593 (14)0.0605 (13)0.0523 (14)0.0135 (11)0.0042 (11)0.0122 (11)
C80.0654 (15)0.0611 (14)0.0703 (18)0.0193 (12)0.0031 (13)0.0109 (13)
C90.0539 (13)0.0602 (14)0.0617 (16)0.0146 (11)0.0098 (11)0.0041 (12)
C100.0484 (12)0.0504 (11)0.0501 (13)0.0083 (9)0.0105 (9)0.0046 (10)
C110.0466 (11)0.0487 (11)0.0399 (11)0.0015 (9)0.0055 (8)0.0016 (9)
C120.0483 (11)0.0515 (11)0.0377 (11)0.0004 (9)0.0066 (9)0.0020 (9)
C130.0376 (10)0.0549 (12)0.0511 (13)0.0003 (9)0.0030 (9)0.0004 (10)
C140.0371 (11)0.0676 (15)0.0612 (15)0.0073 (10)0.0022 (10)0.0046 (11)
C150.0504 (12)0.0562 (13)0.0535 (14)0.0113 (10)0.0106 (10)0.0061 (10)
C160.0505 (11)0.0465 (11)0.0375 (11)0.0058 (9)0.0094 (9)0.0028 (9)
C170.0697 (15)0.0414 (11)0.0560 (14)0.0022 (10)0.0117 (11)0.0004 (10)
C180.0670 (15)0.0417 (11)0.0593 (14)0.0084 (10)0.0081 (11)0.0011 (10)
C190.0542 (12)0.0473 (11)0.0397 (12)0.0097 (9)0.0067 (9)0.0011 (9)
C200.0529 (13)0.0567 (13)0.0520 (14)0.0168 (10)0.0040 (10)0.0047 (10)
C210.0429 (12)0.0729 (16)0.0581 (15)0.0110 (11)0.0015 (10)0.0053 (12)
C220.0378 (10)0.0560 (12)0.0533 (13)0.0013 (9)0.0004 (9)0.0029 (10)
C230.0399 (10)0.0450 (10)0.0313 (10)0.0028 (8)0.0066 (8)0.0020 (8)
C240.0420 (10)0.0435 (10)0.0305 (10)0.0012 (8)0.0073 (8)0.0000 (7)
C250.0463 (11)0.0626 (13)0.0418 (12)0.0029 (10)0.0100 (9)0.0062 (10)
C260.0595 (14)0.0845 (17)0.0446 (13)0.0006 (13)0.0172 (11)0.0099 (12)
C270.0775 (17)0.0931 (19)0.0349 (12)0.0075 (15)0.0159 (12)0.0021 (13)
C280.0660 (15)0.0652 (14)0.0341 (12)0.0066 (11)0.0028 (10)0.0015 (10)
C290.0893 (19)0.0733 (16)0.0406 (13)0.0024 (14)0.0049 (13)0.0143 (12)
C300.0743 (17)0.0577 (13)0.0495 (14)0.0010 (12)0.0146 (12)0.0094 (11)
C310.0516 (12)0.0393 (10)0.0515 (13)0.0051 (9)0.0074 (9)0.0024 (9)
C320.0527 (13)0.0426 (11)0.0757 (18)0.0058 (9)0.0060 (12)0.0037 (11)
C330.0570 (14)0.0502 (12)0.0789 (18)0.0144 (11)0.0137 (12)0.0008 (12)
C340.0538 (13)0.0490 (12)0.0582 (14)0.0092 (10)0.0151 (10)0.0002 (10)
C350.0450 (11)0.0376 (9)0.0416 (11)0.0051 (8)0.0000 (8)0.0015 (8)
C360.0456 (11)0.0471 (10)0.0353 (11)0.0043 (8)0.0013 (8)0.0004 (8)
C370.0596 (14)0.0550 (13)0.0554 (14)0.0064 (10)0.0143 (11)0.0030 (11)
C380.0661 (15)0.0578 (13)0.0472 (13)0.0091 (11)0.0036 (11)0.0006 (11)
C390.0620 (14)0.0526 (13)0.0529 (14)0.0009 (10)0.0049 (11)0.0003 (10)
C400.0475 (11)0.0463 (11)0.0486 (12)0.0040 (9)0.0053 (9)0.0024 (9)
N10.0415 (9)0.0462 (9)0.0381 (9)0.0006 (7)0.0058 (7)0.0032 (7)
N20.0387 (8)0.0459 (9)0.0376 (9)0.0013 (7)0.0054 (7)0.0017 (7)
N30.0430 (9)0.0409 (8)0.0420 (10)0.0006 (7)0.0068 (7)0.0007 (7)
N40.0389 (8)0.0448 (8)0.0350 (9)0.0004 (7)0.0041 (7)0.0003 (7)
N50.0432 (9)0.0434 (9)0.0373 (9)0.0011 (7)0.0079 (7)0.0013 (7)
N60.0367 (8)0.0436 (8)0.0355 (9)0.0028 (7)0.0045 (6)0.0018 (7)
O10.1122 (16)0.0663 (11)0.0884 (15)0.0131 (11)0.0528 (13)0.0028 (10)
O20.0709 (11)0.0558 (9)0.0574 (10)0.0011 (8)0.0144 (8)0.0070 (8)
O30.1099 (16)0.0608 (11)0.0865 (15)0.0258 (10)0.0326 (12)0.0070 (10)
O40.1127 (16)0.0756 (12)0.0556 (11)0.0096 (11)0.0156 (11)0.0126 (9)
O50.1196 (19)0.0806 (15)0.0850 (17)0.0105 (13)0.0342 (14)0.0044 (12)
O60.1090 (16)0.0534 (10)0.0704 (13)0.0032 (10)0.0124 (11)0.0011 (9)
O70.0891 (14)0.0585 (10)0.0544 (11)0.0093 (9)0.0180 (9)0.0011 (9)
O80.0801 (12)0.0551 (10)0.0804 (14)0.0135 (9)0.0223 (10)0.0007 (10)
O90.175 (3)0.108 (2)0.100 (2)0.001 (2)0.036 (2)0.0071 (16)
O100.1004 (17)0.0679 (12)0.0972 (17)0.0174 (11)0.0222 (14)0.0086 (12)
O110.187 (3)0.0608 (12)0.0837 (17)0.0043 (14)0.0429 (17)0.0050 (12)
O120.142 (2)0.0836 (16)0.0943 (19)0.0146 (15)0.0042 (17)0.0058 (14)
Fe10.03569 (14)0.03935 (14)0.03331 (15)0.00076 (12)0.00589 (10)0.00136 (12)
Geometric parameters (Å, º) top
C1—N11.330 (3)C26—C271.356 (4)
C1—C21.391 (3)C26—H260.93
C1—H10.93C27—C281.403 (4)
C2—C31.353 (4)C27—H270.93
C2—H20.93C28—C361.396 (3)
C3—C41.407 (4)C28—C291.434 (3)
C3—H30.93C29—C301.347 (4)
C4—C121.393 (3)C29—H290.93
C4—C51.434 (4)C30—C311.427 (3)
C5—C61.344 (4)C30—H300.93
C5—H50.93C31—C321.399 (3)
C6—C71.433 (4)C31—C351.402 (3)
C6—H60.93C32—C331.360 (4)
C7—C111.397 (3)C32—H320.93
C7—C81.411 (3)C33—C341.393 (3)
C8—C91.356 (4)C33—H330.93
C8—H80.93C34—N31.333 (3)
C9—C101.397 (3)C34—H340.93
C9—H90.93C35—N31.363 (3)
C10—N51.333 (2)C35—C361.416 (3)
C10—H100.93C36—N21.365 (3)
C11—N51.362 (3)C37—O11.242 (3)
C11—C121.419 (3)C37—C381.456 (3)
C12—N11.365 (3)C37—C401.462 (3)
C13—N61.331 (2)C38—O41.267 (3)
C13—C141.389 (3)C38—C391.437 (3)
C13—H130.93C39—O31.262 (3)
C14—C151.359 (3)C39—C401.457 (3)
C14—H140.93C40—O21.244 (3)
C15—C161.403 (3)N1—Fe11.9791 (16)
C15—H150.93N2—Fe11.9710 (16)
C16—C241.392 (3)N3—Fe11.9721 (16)
C16—C171.435 (3)N4—Fe11.9735 (16)
C17—C181.338 (3)N5—Fe11.9803 (16)
C17—H170.93N6—Fe11.9773 (16)
C18—C191.434 (3)O5—H5A0.840 (15)
C18—H180.93O5—H5B0.843 (15)
C19—C231.396 (3)O6—H6A0.864 (15)
C19—C201.407 (3)O6—H6B0.891 (15)
C20—C211.361 (3)O7—H7A0.817 (15)
C20—H200.93O7—H7B0.824 (15)
C21—C221.386 (3)O8—H8A0.847 (15)
C21—H210.93O8—H8B0.820 (15)
C22—N41.336 (2)O9—H9B0.89 (2)
C22—H220.93O9—H9A0.86 (2)
C23—N41.365 (2)O10—H10A0.837 (15)
C23—C241.425 (3)O10—H10B0.851 (15)
C24—N61.367 (2)O11—H11A0.865 (16)
C25—N21.329 (3)O11—H11B0.817 (15)
C25—C261.391 (3)O12—H12A0.828 (15)
C25—H250.93O12—H12B0.882 (15)
N1—C1—C2122.6 (2)C36—C28—C27116.5 (2)
N1—C1—H1118.7C36—C28—C29117.9 (2)
C2—C1—H1118.7C27—C28—C29125.6 (2)
C3—C2—C1120.0 (2)C30—C29—C28121.9 (2)
C3—C2—H2120.0C30—C29—H29119.1
C1—C2—H2120.0C28—C29—H29119.1
C2—C3—C4119.6 (2)C29—C30—C31120.8 (2)
C2—C3—H3120.2C29—C30—H30119.6
C4—C3—H3120.2C31—C30—H30119.6
C12—C4—C3117.0 (2)C32—C31—C35117.0 (2)
C12—C4—C5118.0 (2)C32—C31—C30124.6 (2)
C3—C4—C5125.1 (2)C35—C31—C30118.4 (2)
C6—C5—C4121.4 (2)C33—C32—C31119.5 (2)
C6—C5—H5119.3C33—C32—H32120.3
C4—C5—H5119.3C31—C32—H32120.3
C5—C6—C7121.4 (2)C32—C33—C34120.0 (2)
C5—C6—H6119.3C32—C33—H33120.0
C7—C6—H6119.3C34—C33—H33120.0
C11—C7—C8117.2 (2)N3—C34—C33122.8 (2)
C11—C7—C6118.0 (2)N3—C34—H34118.6
C8—C7—C6124.8 (2)C33—C34—H34118.6
C9—C8—C7119.1 (2)N3—C35—C31123.66 (19)
C9—C8—H8120.5N3—C35—C36115.81 (18)
C7—C8—H8120.5C31—C35—C36120.53 (19)
C8—C9—C10120.3 (2)N2—C36—C28123.7 (2)
C8—C9—H9119.9N2—C36—C35115.97 (17)
C10—C9—H9119.9C28—C36—C35120.4 (2)
N5—C10—C9122.6 (2)O1—C37—C38136.4 (2)
N5—C10—H10118.7O1—C37—C40134.1 (2)
C9—C10—H10118.7C38—C37—C4089.48 (18)
N5—C11—C7123.64 (19)O4—C38—C39134.8 (2)
N5—C11—C12115.96 (18)O4—C38—C37134.7 (2)
C7—C11—C12120.40 (19)C39—C38—C3790.54 (19)
N1—C12—C4123.3 (2)O3—C39—C38134.9 (2)
N1—C12—C11115.93 (18)O3—C39—C40134.6 (2)
C4—C12—C11120.7 (2)C38—C39—C4090.44 (19)
N6—C13—C14122.7 (2)O2—C40—C39136.5 (2)
N6—C13—H13118.6O2—C40—C37134.0 (2)
C14—C13—H13118.6C39—C40—C3789.50 (18)
C15—C14—C13120.7 (2)C1—N1—C12117.48 (18)
C15—C14—H14119.7C1—N1—Fe1129.75 (15)
C13—C14—H14119.7C12—N1—Fe1112.71 (13)
C14—C15—C16118.6 (2)C25—N2—C36117.28 (18)
C14—C15—H15120.7C25—N2—Fe1130.09 (15)
C16—C15—H15120.7C36—N2—Fe1112.63 (13)
C24—C16—C15117.40 (19)C34—N3—C35117.04 (18)
C24—C16—C17118.26 (19)C34—N3—Fe1130.13 (15)
C15—C16—C17124.3 (2)C35—N3—Fe1112.78 (13)
C18—C17—C16121.2 (2)C22—N4—C23116.67 (17)
C18—C17—H17119.4C22—N4—Fe1130.36 (14)
C16—C17—H17119.4C23—N4—Fe1112.97 (12)
C17—C18—C19121.6 (2)C10—N5—C11117.24 (18)
C17—C18—H18119.2C10—N5—Fe1129.97 (15)
C19—C18—H18119.2C11—N5—Fe1112.78 (13)
C23—C19—C20117.09 (19)C13—N6—C24116.60 (17)
C23—C19—C18118.12 (19)C13—N6—Fe1130.57 (14)
C20—C19—C18124.7 (2)C24—N6—Fe1112.83 (12)
C21—C20—C19118.9 (2)H5A—O5—H5B105 (2)
C21—C20—H20120.5H6A—O6—H6B103.7 (18)
C19—C20—H20120.5H7A—O7—H7B115 (2)
C20—C21—C22120.5 (2)H8A—O8—H8B108.2 (19)
C20—C21—H21119.8H9B—O9—H9A102 (3)
C22—C21—H21119.8H10A—O10—H10B112 (2)
N4—C22—C21122.9 (2)H11A—O11—H11B106.9 (19)
N4—C22—H22118.6H12A—O12—H12B103 (2)
C21—C22—H22118.6N2—Fe1—N382.80 (7)
N4—C23—C19123.98 (18)N2—Fe1—N493.58 (7)
N4—C23—C24115.81 (16)N3—Fe1—N4174.11 (7)
C19—C23—C24120.22 (18)N2—Fe1—N690.91 (7)
N6—C24—C16123.89 (18)N3—Fe1—N692.67 (6)
N6—C24—C23115.61 (16)N4—Fe1—N682.71 (6)
C16—C24—C23120.50 (18)N2—Fe1—N1173.69 (7)
N2—C25—C26122.8 (2)N3—Fe1—N192.45 (7)
N2—C25—H25118.6N4—Fe1—N191.48 (7)
C26—C25—H25118.6N6—Fe1—N193.46 (7)
C27—C26—C25119.6 (2)N2—Fe1—N593.37 (7)
C27—C26—H26120.2N3—Fe1—N591.43 (7)
C25—C26—H26120.2N4—Fe1—N593.43 (7)
C26—C27—C28120.2 (2)N6—Fe1—N5174.41 (7)
C26—C27—H27119.9N1—Fe1—N582.57 (7)
C28—C27—H27119.9
N1—C1—C2—C31.0 (4)C38—C37—C40—O2178.8 (3)
C1—C2—C3—C40.7 (4)O1—C37—C40—C39175.9 (3)
C2—C3—C4—C122.1 (4)C38—C37—C40—C391.71 (18)
C2—C3—C4—C5179.0 (3)C2—C1—N1—C121.1 (3)
C12—C4—C5—C60.0 (5)C2—C1—N1—Fe1175.80 (17)
C3—C4—C5—C6178.9 (3)C4—C12—N1—C10.4 (3)
C4—C5—C6—C71.0 (5)C11—C12—N1—C1179.48 (19)
C5—C6—C7—C110.9 (5)C4—C12—N1—Fe1177.87 (18)
C5—C6—C7—C8179.6 (3)C11—C12—N1—Fe12.0 (2)
C11—C7—C8—C90.0 (4)C26—C25—N2—C361.3 (3)
C6—C7—C8—C9178.7 (3)C26—C25—N2—Fe1178.06 (17)
C7—C8—C9—C100.7 (4)C28—C36—N2—C250.8 (3)
C8—C9—C10—N50.5 (4)C35—C36—N2—C25179.56 (18)
C8—C7—C11—N51.0 (4)C28—C36—N2—Fe1178.68 (17)
C6—C7—C11—N5179.8 (2)C35—C36—N2—Fe11.0 (2)
C8—C7—C11—C12178.5 (2)C33—C34—N3—C350.3 (3)
C6—C7—C11—C120.3 (4)C33—C34—N3—Fe1177.02 (17)
C3—C4—C12—N12.0 (4)C31—C35—N3—C340.3 (3)
C5—C4—C12—N1179.0 (2)C36—C35—N3—C34179.01 (18)
C3—C4—C12—C11177.9 (2)C31—C35—N3—Fe1178.07 (15)
C5—C4—C12—C111.1 (4)C36—C35—N3—Fe11.2 (2)
N5—C11—C12—N10.7 (3)C21—C22—N4—C230.5 (3)
C7—C11—C12—N1178.8 (2)C21—C22—N4—Fe1179.08 (17)
N5—C11—C12—C4179.2 (2)C19—C23—N4—C220.1 (3)
C7—C11—C12—C41.3 (3)C24—C23—N4—C22179.93 (17)
N6—C13—C14—C150.3 (4)C19—C23—N4—Fe1179.50 (15)
C13—C14—C15—C161.4 (3)C24—C23—N4—Fe10.3 (2)
C14—C15—C16—C240.2 (3)C9—C10—N5—C110.5 (3)
C14—C15—C16—C17178.2 (2)C9—C10—N5—Fe1179.64 (16)
C24—C16—C17—C182.2 (3)C7—C11—N5—C101.2 (3)
C15—C16—C17—C18176.2 (2)C12—C11—N5—C10178.35 (18)
C16—C17—C18—C191.8 (4)C7—C11—N5—Fe1179.49 (18)
C17—C18—C19—C230.5 (3)C12—C11—N5—Fe11.0 (2)
C17—C18—C19—C20177.8 (2)C14—C13—N6—C241.9 (3)
C23—C19—C20—C210.2 (3)C14—C13—N6—Fe1178.08 (16)
C18—C19—C20—C21177.1 (2)C16—C24—N6—C133.2 (3)
C19—C20—C21—C220.6 (4)C23—C24—N6—C13177.15 (17)
C20—C21—C22—N40.7 (4)C16—C24—N6—Fe1176.78 (15)
C20—C19—C23—N40.0 (3)C23—C24—N6—Fe12.9 (2)
C18—C19—C23—N4177.52 (18)C25—N2—Fe1—N3179.60 (19)
C20—C19—C23—C24179.81 (18)C36—N2—Fe1—N30.26 (13)
C18—C19—C23—C242.3 (3)C25—N2—Fe1—N45.07 (19)
C15—C16—C24—N62.2 (3)C36—N2—Fe1—N4175.59 (13)
C17—C16—C24—N6179.31 (18)C25—N2—Fe1—N687.82 (19)
C15—C16—C24—C23178.15 (18)C36—N2—Fe1—N692.83 (13)
C17—C16—C24—C230.4 (3)C25—N2—Fe1—N588.58 (19)
N4—C23—C24—N61.8 (2)C36—N2—Fe1—N590.76 (13)
C19—C23—C24—N6178.45 (17)C34—N3—Fe1—N2177.9 (2)
N4—C23—C24—C16177.94 (17)C35—N3—Fe1—N20.54 (13)
C19—C23—C24—C161.9 (3)C34—N3—Fe1—N687.36 (19)
N2—C25—C26—C270.3 (4)C35—N3—Fe1—N690.04 (13)
C25—C26—C27—C281.2 (4)C34—N3—Fe1—N16.23 (19)
C26—C27—C28—C361.6 (4)C35—N3—Fe1—N1176.38 (13)
C26—C27—C28—C29177.9 (2)C34—N3—Fe1—N588.85 (19)
C36—C28—C29—C300.6 (4)C35—N3—Fe1—N593.76 (14)
C27—C28—C29—C30178.9 (3)C22—N4—Fe1—N288.52 (18)
C28—C29—C30—C311.6 (4)C23—N4—Fe1—N291.91 (13)
C29—C30—C31—C32179.1 (2)C22—N4—Fe1—N6178.98 (19)
C29—C30—C31—C350.6 (3)C23—N4—Fe1—N61.45 (13)
C35—C31—C32—C330.1 (3)C22—N4—Fe1—N187.72 (18)
C30—C31—C32—C33179.7 (2)C23—N4—Fe1—N191.85 (13)
C31—C32—C33—C340.5 (4)C22—N4—Fe1—N55.08 (19)
C32—C33—C34—N30.7 (4)C23—N4—Fe1—N5174.49 (13)
C32—C31—C35—N30.5 (3)C13—N6—Fe1—N284.18 (18)
C30—C31—C35—N3179.27 (19)C24—N6—Fe1—N295.88 (13)
C32—C31—C35—C36178.80 (19)C13—N6—Fe1—N31.34 (19)
C30—C31—C35—C361.4 (3)C24—N6—Fe1—N3178.71 (13)
C27—C28—C36—N20.7 (3)C13—N6—Fe1—N4177.67 (19)
C29—C28—C36—N2178.9 (2)C24—N6—Fe1—N42.38 (12)
C27—C28—C36—C35179.0 (2)C13—N6—Fe1—N191.27 (18)
C29—C28—C36—C351.4 (3)C24—N6—Fe1—N188.67 (13)
N3—C35—C36—N21.5 (3)C1—N1—Fe1—N387.91 (18)
C31—C35—C36—N2177.82 (17)C12—N1—Fe1—N389.14 (14)
N3—C35—C36—C28178.19 (18)C1—N1—Fe1—N487.70 (18)
C31—C35—C36—C282.5 (3)C12—N1—Fe1—N495.25 (14)
O1—C37—C38—O44.1 (5)C1—N1—Fe1—N64.91 (19)
C40—C37—C38—O4178.4 (3)C12—N1—Fe1—N6178.03 (14)
O1—C37—C38—C39175.8 (3)C1—N1—Fe1—N5179.04 (19)
C40—C37—C38—C391.73 (18)C12—N1—Fe1—N51.98 (13)
O4—C38—C39—O33.5 (5)C10—N5—Fe1—N27.25 (19)
C37—C38—C39—O3176.3 (3)C11—N5—Fe1—N2173.54 (14)
O4—C38—C39—C40178.4 (3)C10—N5—Fe1—N390.11 (18)
C37—C38—C39—C401.74 (18)C11—N5—Fe1—N390.67 (14)
O3—C39—C40—O23.1 (5)C10—N5—Fe1—N486.55 (18)
C38—C39—C40—O2178.8 (3)C11—N5—Fe1—N492.66 (14)
O3—C39—C40—C37176.4 (3)C10—N5—Fe1—N1177.60 (19)
C38—C39—C40—C371.73 (18)C11—N5—Fe1—N11.61 (14)
O1—C37—C40—O23.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O12i0.84 (2)2.13 (2)2.878 (4)149 (2)
O5—H5B···O60.84 (2)1.91 (2)2.731 (3)163 (2)
O6—H6A···O7ii0.86 (2)1.97 (2)2.816 (3)166 (2)
O6—H6B···O10iii0.89 (2)1.81 (2)2.677 (3)166 (2)
O7—H7A···O1ii0.82 (2)2.01 (2)2.811 (3)166 (3)
O7—H7B···O20.82 (2)1.92 (2)2.737 (2)169 (2)
O8—H8A···O30.85 (2)1.88 (2)2.722 (3)173 (2)
O8—H8B···O70.82 (2)2.02 (2)2.832 (3)169 (2)
O9—H9B···O30.89 (2)1.94 (3)2.782 (4)157 (7)
O9—H9A···O11iv0.86 (2)2.53 (6)3.147 (5)129 (6)
O10—H10A···O40.84 (2)1.94 (2)2.745 (3)160 (2)
O10—H10B···O90.85 (2)1.95 (2)2.786 (4)165 (2)
O11—H11A···O40.87 (2)1.86 (2)2.720 (3)173 (2)
O11—H11B···O8v0.82 (2)2.00 (2)2.808 (3)170 (2)
O12—H12A···O5vi0.83 (2)1.96 (2)2.775 (4)168 (2)
O12—H12B···O11vi0.88 (2)2.13 (2)2.771 (3)129 (2)
C20—H20···O2v0.932.573.267 (3)132
Symmetry codes: (i) x+1, y, z+2; (ii) x+2, y, z+1; (iii) x+2, y1/2, z+3/2; (iv) x, y+1/2, z1/2; (v) x, y+1/2, z+1/2; (vi) x1, y, z.
 

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