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The FeII atom in the title compound, [Fe(C27H20N3O)2], is N,O-chelated by two deprotonated 3-methyl-4-[(1-naphthyl­amino)(phen­yl)methyl­ene]-1-phenyl-1H-pyrazol-5(4H)-one ligands in a severely distorted tetra­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044667/hb2174sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044667/hb2174Isup2.hkl
Contains datablock I

CCDC reference: 629829

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.060
  • wR factor = 0.145
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.123 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C47 .. 5.60 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 6.89 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C36 - C37 .. 5.55 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C45 - C46 .. 6.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C53 - C54 .. 6.60 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - O1 .. 6.28 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H21A .. H50 .. 2.11 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Bis{N-[(Z)-4-(3-methyl-5-oxo-1-phenyl-1H-pyrazol-4- ylidene)(phenyl)methyl]naphthylamido-κ2N,O}iron(II) top
Crystal data top
[Fe(C27H20N3O)2]F(000) = 1792
Mr = 860.77Dx = 1.325 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2528 reflections
a = 13.1106 (9) Åθ = 2.3–19.0°
b = 19.6822 (13) ŵ = 0.40 mm1
c = 16.8314 (11) ÅT = 292 K
β = 96.627 (2)°Block, red
V = 4314.2 (5) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
9368 independent reflections
Radiation source: fine-focus sealed tube4102 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.123
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1616
Tmin = 0.924, Tmax = 0.961k = 2525
31464 measured reflectionsl = 2118
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0538P)2]
where P = (Fo2 + 2Fc2)/3
9368 reflections(Δ/σ)max = 0.002
570 parametersΔρmax = 0.35 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*/Ueq
Fe10.74448 (4)0.07434 (2)0.12871 (3)0.03701 (17)
C10.7740 (3)0.06643 (18)0.1495 (2)0.0468 (10)
C20.8805 (3)0.07211 (19)0.1578 (2)0.0499 (10)
C30.9444 (4)0.0436 (2)0.1030 (3)0.0650 (13)
H30.91400.01900.05940.078*
C41.0479 (4)0.0514 (2)0.1125 (3)0.0798 (15)
H41.08730.03200.07600.096*
C51.0950 (4)0.0884 (3)0.1771 (4)0.0889 (17)
H51.16580.09430.18270.107*
C61.0403 (5)0.1152 (2)0.2307 (3)0.0856 (17)
H61.07420.13890.27360.103*
C70.9300 (4)0.1089 (2)0.2247 (3)0.0583 (12)
C80.8725 (4)0.1383 (2)0.2788 (3)0.0706 (14)
H80.90510.16170.32260.085*
C90.7679 (5)0.1334 (2)0.2686 (3)0.0805 (16)
H90.72970.15440.30500.097*
C100.7173 (4)0.0969 (2)0.2035 (3)0.0644 (13)
H100.64610.09340.19710.077*
C110.6823 (3)0.1139 (2)0.0012 (2)0.0462 (10)
C120.7485 (3)0.1418 (2)0.0467 (3)0.0621 (12)
H120.80130.11510.06220.074*
C130.7414 (4)0.2078 (3)0.0710 (3)0.0792 (15)
H130.78720.22430.10460.095*
C140.6702 (5)0.2491 (3)0.0473 (3)0.0886 (17)
H140.66770.29450.06270.106*
C150.6002 (5)0.2235 (3)0.0002 (3)0.108 (2)
H150.54940.25150.01650.129*
C160.6060 (4)0.1558 (2)0.0237 (3)0.0822 (16)
H160.55910.13830.05580.099*
C170.6851 (3)0.04055 (19)0.0192 (2)0.0443 (10)
C180.6488 (3)0.00769 (19)0.0391 (2)0.0446 (10)
C190.5916 (3)0.0009 (2)0.1163 (2)0.0575 (12)
C200.6680 (3)0.0789 (2)0.0323 (2)0.0452 (10)
C210.5434 (4)0.0637 (2)0.1528 (3)0.0952 (19)
H21A0.50170.05240.20160.143*
H21B0.50130.08420.11630.143*
H21C0.59600.09500.16380.143*
C220.6171 (3)0.1764 (2)0.1273 (2)0.0545 (11)
C230.5442 (3)0.1934 (2)0.1906 (2)0.0640 (13)
H230.50290.16000.21690.077*
C240.5337 (4)0.2603 (3)0.2139 (3)0.0786 (15)
H240.48550.27190.25660.094*
C250.5926 (4)0.3095 (3)0.1754 (3)0.0897 (17)
H250.58410.35460.19120.108*
C260.6643 (5)0.2925 (3)0.1136 (3)0.103 (2)
H260.70540.32610.08770.124*
C270.6766 (4)0.2258 (2)0.0889 (3)0.0826 (16)
H270.72530.21460.04630.099*
C280.8958 (3)0.18260 (19)0.1158 (2)0.0471 (10)
C290.9658 (3)0.1679 (2)0.0629 (3)0.0617 (12)
H290.99670.12530.06380.074*
C300.9904 (4)0.2166 (3)0.0081 (3)0.0724 (14)
H301.03550.20530.02860.087*
C310.9501 (4)0.2798 (2)0.0070 (3)0.0690 (13)
H310.97130.31230.02770.083*
C320.8751 (3)0.2970 (2)0.0591 (2)0.0514 (11)
C330.8281 (4)0.3617 (2)0.0582 (3)0.0620 (12)
H330.84740.39490.02360.074*
C340.7574 (4)0.3760 (2)0.1055 (3)0.0705 (14)
H340.72790.41900.10380.085*
C350.7263 (4)0.3273 (2)0.1580 (3)0.0721 (14)
H350.67470.33720.18980.087*
C360.7732 (3)0.2642 (2)0.1623 (3)0.0569 (11)
H360.75450.23250.19900.068*
C370.8465 (3)0.24718 (19)0.1139 (2)0.0420 (10)
C380.9208 (3)0.11656 (18)0.2359 (2)0.0413 (9)
C391.0283 (3)0.1450 (2)0.2551 (2)0.0489 (10)
C401.0448 (4)0.2025 (2)0.3020 (2)0.0668 (13)
H400.98860.22690.31550.080*
C411.1423 (5)0.2247 (3)0.3293 (3)0.0866 (17)
H411.15270.26400.35990.104*
C421.2209 (5)0.1879 (4)0.3102 (3)0.101 (2)
H421.28710.20160.32920.121*
C431.2088 (4)0.1306 (4)0.2636 (3)0.102 (2)
H431.26610.10680.25090.122*
C441.1114 (4)0.1084 (3)0.2357 (3)0.0758 (15)
H441.10210.06960.20430.091*
C450.8864 (3)0.07278 (18)0.2931 (2)0.0388 (9)
C460.7831 (3)0.05152 (17)0.2908 (2)0.0406 (9)
C470.9352 (3)0.04780 (19)0.3672 (2)0.0421 (10)
C481.0431 (3)0.0485 (2)0.4026 (2)0.0658 (13)
H48A1.04830.03000.45570.099*
H48B1.06810.09440.40490.099*
H48C1.08350.02170.37030.099*
C490.6892 (3)0.01284 (18)0.3921 (2)0.0415 (9)
C500.5961 (3)0.0179 (2)0.3462 (2)0.0578 (12)
H500.58750.00050.29490.069*
C510.5128 (3)0.0510 (2)0.3766 (3)0.0659 (13)
H510.44960.05460.34550.079*
C520.5258 (3)0.0779 (2)0.4524 (3)0.0643 (12)
H520.47210.10010.47310.077*
C530.6201 (4)0.0714 (2)0.4972 (3)0.0691 (13)
H530.62930.08900.54880.083*
C540.7023 (3)0.0392 (2)0.4669 (2)0.0547 (11)
H540.76570.03590.49780.066*
N10.7264 (3)0.02024 (14)0.09027 (18)0.0507 (9)
N20.8629 (2)0.13230 (14)0.16902 (17)0.0443 (8)
N30.8700 (2)0.01598 (15)0.40757 (17)0.0474 (8)
N40.7735 (2)0.01907 (15)0.36137 (17)0.0445 (8)
N50.6258 (2)0.10654 (16)0.10337 (18)0.0508 (9)
N60.5767 (3)0.05711 (18)0.1540 (2)0.0652 (11)
O10.70704 (19)0.05938 (12)0.23508 (14)0.0486 (7)
O20.7136 (2)0.11377 (12)0.02527 (14)0.0565 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0476 (3)0.0338 (3)0.0272 (3)0.0032 (3)0.0063 (2)0.0049 (2)
C10.063 (3)0.032 (2)0.043 (2)0.004 (2)0.009 (2)0.0000 (19)
C20.071 (3)0.039 (2)0.038 (2)0.008 (2)0.002 (2)0.002 (2)
C30.086 (4)0.055 (3)0.049 (3)0.004 (3)0.010 (3)0.004 (2)
C40.068 (4)0.090 (4)0.082 (4)0.003 (3)0.011 (3)0.012 (3)
C50.064 (4)0.098 (4)0.103 (5)0.020 (3)0.001 (3)0.010 (4)
C60.098 (5)0.073 (4)0.077 (4)0.023 (3)0.025 (3)0.013 (3)
C70.080 (4)0.043 (3)0.049 (3)0.010 (2)0.005 (3)0.002 (2)
C80.095 (4)0.065 (3)0.050 (3)0.019 (3)0.001 (3)0.015 (2)
C90.128 (5)0.052 (3)0.064 (3)0.010 (3)0.024 (3)0.017 (3)
C100.087 (4)0.042 (3)0.064 (3)0.005 (2)0.007 (3)0.005 (2)
C110.053 (3)0.043 (3)0.042 (2)0.001 (2)0.002 (2)0.000 (2)
C120.051 (3)0.059 (3)0.079 (3)0.006 (2)0.021 (2)0.014 (3)
C130.087 (4)0.068 (4)0.087 (4)0.002 (3)0.028 (3)0.024 (3)
C140.137 (5)0.055 (3)0.079 (4)0.014 (3)0.031 (4)0.018 (3)
C150.173 (6)0.062 (4)0.098 (5)0.053 (4)0.054 (4)0.018 (3)
C160.103 (4)0.066 (3)0.085 (4)0.024 (3)0.043 (3)0.023 (3)
C170.042 (2)0.044 (2)0.046 (3)0.0026 (19)0.002 (2)0.001 (2)
C180.049 (3)0.046 (2)0.036 (2)0.000 (2)0.0063 (19)0.0005 (19)
C190.058 (3)0.056 (3)0.052 (3)0.007 (2)0.021 (2)0.005 (2)
C200.047 (2)0.054 (3)0.033 (2)0.003 (2)0.0023 (18)0.007 (2)
C210.125 (5)0.061 (3)0.082 (4)0.006 (3)0.065 (3)0.011 (3)
C220.061 (3)0.064 (3)0.037 (2)0.000 (2)0.002 (2)0.015 (2)
C230.061 (3)0.070 (3)0.058 (3)0.001 (2)0.007 (2)0.022 (2)
C240.085 (4)0.082 (4)0.065 (3)0.006 (3)0.010 (3)0.037 (3)
C250.120 (5)0.058 (3)0.085 (4)0.003 (3)0.009 (4)0.030 (3)
C260.145 (6)0.069 (4)0.084 (4)0.031 (3)0.034 (4)0.032 (3)
C270.108 (4)0.066 (3)0.065 (3)0.019 (3)0.025 (3)0.021 (3)
C280.057 (3)0.043 (2)0.039 (2)0.006 (2)0.010 (2)0.0035 (19)
C290.078 (3)0.055 (3)0.053 (3)0.004 (2)0.012 (3)0.007 (2)
C300.076 (4)0.078 (4)0.069 (3)0.001 (3)0.032 (3)0.010 (3)
C310.085 (4)0.065 (3)0.060 (3)0.011 (3)0.019 (3)0.013 (3)
C320.063 (3)0.044 (3)0.045 (3)0.013 (2)0.005 (2)0.010 (2)
C330.066 (3)0.055 (3)0.064 (3)0.005 (3)0.003 (3)0.013 (2)
C340.069 (4)0.042 (3)0.098 (4)0.006 (2)0.001 (3)0.012 (3)
C350.070 (3)0.062 (3)0.085 (4)0.011 (3)0.008 (3)0.003 (3)
C360.059 (3)0.055 (3)0.056 (3)0.005 (2)0.002 (2)0.012 (2)
C370.040 (2)0.046 (2)0.039 (2)0.0051 (19)0.0002 (19)0.0043 (19)
C380.045 (2)0.037 (2)0.041 (2)0.0009 (18)0.0038 (19)0.0030 (18)
C390.057 (3)0.057 (3)0.031 (2)0.003 (2)0.003 (2)0.002 (2)
C400.076 (4)0.061 (3)0.059 (3)0.015 (3)0.011 (3)0.009 (2)
C410.078 (4)0.091 (4)0.087 (4)0.029 (4)0.007 (3)0.008 (3)
C420.067 (4)0.160 (7)0.072 (4)0.044 (4)0.006 (3)0.021 (4)
C430.058 (4)0.180 (7)0.069 (4)0.004 (4)0.014 (3)0.005 (4)
C440.049 (3)0.119 (4)0.061 (3)0.004 (3)0.011 (2)0.021 (3)
C450.035 (2)0.044 (2)0.036 (2)0.0019 (19)0.0024 (17)0.0032 (19)
C460.054 (3)0.036 (2)0.030 (2)0.0040 (19)0.0024 (19)0.0018 (17)
C470.038 (2)0.050 (2)0.037 (2)0.0055 (19)0.0014 (19)0.0052 (19)
C480.058 (3)0.085 (3)0.050 (3)0.002 (2)0.012 (2)0.016 (2)
C490.040 (2)0.044 (2)0.040 (2)0.0051 (19)0.0001 (19)0.0038 (19)
C500.051 (3)0.071 (3)0.050 (3)0.005 (2)0.000 (2)0.013 (2)
C510.049 (3)0.079 (3)0.070 (3)0.005 (2)0.005 (2)0.004 (3)
C520.057 (3)0.072 (3)0.065 (3)0.005 (3)0.015 (3)0.014 (3)
C530.094 (4)0.064 (3)0.049 (3)0.002 (3)0.005 (3)0.012 (2)
C540.050 (3)0.062 (3)0.050 (3)0.007 (2)0.000 (2)0.012 (2)
N10.069 (2)0.0349 (18)0.044 (2)0.0060 (16)0.0106 (18)0.0004 (15)
N20.048 (2)0.0422 (19)0.0405 (19)0.0039 (16)0.0021 (16)0.0092 (15)
N30.049 (2)0.054 (2)0.0351 (19)0.0014 (17)0.0089 (16)0.0042 (16)
N40.049 (2)0.0444 (19)0.0365 (19)0.0008 (16)0.0083 (16)0.0067 (15)
N50.060 (2)0.053 (2)0.0362 (19)0.0028 (18)0.0096 (17)0.0093 (17)
N60.079 (3)0.058 (2)0.050 (2)0.006 (2)0.0272 (19)0.0012 (19)
O10.0513 (17)0.0541 (17)0.0371 (15)0.0006 (13)0.0091 (13)0.0111 (12)
O20.079 (2)0.0489 (16)0.0368 (16)0.0123 (15)0.0144 (14)0.0060 (13)
Geometric parameters (Å, º) top
Fe1—O21.907 (2)C27—H270.9300
Fe1—O11.933 (2)C28—C291.381 (5)
Fe1—N11.976 (3)C28—C371.425 (5)
Fe1—N21.982 (3)C28—N21.434 (4)
C1—C101.376 (5)C29—C301.392 (5)
C1—C21.392 (5)C29—H290.9300
C1—N11.437 (4)C30—C311.350 (6)
C2—C71.429 (5)C30—H300.9300
C2—C31.430 (5)C31—C321.432 (6)
C3—C41.356 (6)C31—H310.9300
C3—H30.9300C32—C331.413 (5)
C4—C51.391 (6)C32—C371.427 (5)
C4—H40.9300C33—C341.320 (5)
C5—C61.324 (6)C33—H330.9300
C5—H50.9300C34—C351.396 (6)
C6—C71.444 (6)C34—H340.9300
C6—H60.9300C35—C361.385 (5)
C7—C81.375 (6)C35—H350.9300
C8—C91.365 (6)C36—C371.370 (5)
C8—H80.9300C36—H360.9300
C9—C101.412 (6)C38—N21.320 (4)
C9—H90.9300C38—C451.404 (5)
C10—H100.9300C38—C391.516 (5)
C11—C121.339 (5)C39—C441.376 (5)
C11—C161.397 (5)C39—C401.383 (5)
C11—C171.483 (5)C40—C411.379 (6)
C12—C131.362 (5)C40—H400.9300
C12—H120.9300C41—C421.330 (7)
C13—C141.333 (6)C41—H410.9300
C13—H130.9300C42—C431.372 (7)
C14—C151.381 (7)C42—H420.9300
C14—H140.9300C43—C441.380 (6)
C15—C161.390 (6)C43—H430.9300
C15—H150.9300C44—H440.9300
C16—H160.9300C45—C461.414 (5)
C17—N11.316 (4)C45—C471.423 (5)
C17—C181.408 (5)C46—O11.297 (4)
C18—C201.427 (5)C46—N41.367 (4)
C18—C191.434 (5)C47—N31.310 (4)
C19—N61.310 (5)C47—C481.471 (5)
C19—C211.488 (5)C48—H48A0.9600
C20—O21.277 (4)C48—H48B0.9600
C20—N51.372 (4)C48—H48C0.9600
C21—H21A0.9600C49—C541.354 (5)
C21—H21B0.9600C49—C501.371 (5)
C21—H21C0.9600C49—N41.420 (4)
C22—C271.362 (5)C50—C511.418 (5)
C22—C231.388 (5)C50—H500.9300
C22—N51.433 (5)C51—C521.372 (5)
C23—C241.376 (5)C51—H510.9300
C23—H230.9300C52—C531.378 (6)
C24—C251.356 (6)C52—H520.9300
C24—H240.9300C53—C541.396 (5)
C25—C261.361 (6)C53—H530.9300
C25—H250.9300C54—H540.9300
C26—C271.381 (6)N3—N41.408 (4)
C26—H260.9300N5—N61.400 (4)
O2—Fe1—O1149.08 (11)C30—C29—H29119.8
O2—Fe1—N194.56 (12)C31—C30—C29121.5 (4)
O1—Fe1—N197.24 (11)C31—C30—H30119.2
O2—Fe1—N298.85 (12)C29—C30—H30119.2
O1—Fe1—N292.48 (11)C30—C31—C32120.4 (4)
N1—Fe1—N2135.56 (13)C30—C31—H31119.8
C10—C1—C2120.7 (4)C32—C31—H31119.8
C10—C1—N1120.6 (4)C33—C32—C37118.6 (4)
C2—C1—N1118.1 (4)C33—C32—C31122.5 (4)
C1—C2—C7118.6 (4)C37—C32—C31118.9 (4)
C1—C2—C3124.0 (4)C34—C33—C32121.4 (4)
C7—C2—C3117.4 (4)C34—C33—H33119.3
C4—C3—C2122.1 (4)C32—C33—H33119.3
C4—C3—H3118.9C33—C34—C35120.8 (4)
C2—C3—H3118.9C33—C34—H34119.6
C3—C4—C5119.9 (5)C35—C34—H34119.6
C3—C4—H4120.0C36—C35—C34119.2 (4)
C5—C4—H4120.0C36—C35—H35120.4
C6—C5—C4120.9 (5)C34—C35—H35120.4
C6—C5—H5119.5C37—C36—C35121.7 (4)
C4—C5—H5119.5C37—C36—H36119.2
C5—C6—C7122.3 (5)C35—C36—H36119.2
C5—C6—H6118.8C36—C37—C28123.5 (4)
C7—C6—H6118.8C36—C37—C32118.1 (4)
C8—C7—C2120.1 (4)C28—C37—C32118.4 (4)
C8—C7—C6122.6 (4)N2—C38—C45122.0 (3)
C2—C7—C6117.3 (4)N2—C38—C39121.6 (3)
C9—C8—C7120.4 (4)C45—C38—C39116.4 (3)
C9—C8—H8119.8C44—C39—C40119.2 (4)
C7—C8—H8119.8C44—C39—C38119.9 (4)
C8—C9—C10120.6 (5)C40—C39—C38120.3 (4)
C8—C9—H9119.7C41—C40—C39121.9 (5)
C10—C9—H9119.7C41—C40—H40119.1
C1—C10—C9119.6 (5)C39—C40—H40119.1
C1—C10—H10120.2C42—C41—C40117.5 (6)
C9—C10—H10120.2C42—C41—H41121.3
C12—C11—C16117.6 (4)C40—C41—H41121.3
C12—C11—C17122.1 (4)C41—C42—C43123.0 (6)
C16—C11—C17120.3 (4)C41—C42—H42118.5
C11—C12—C13122.5 (4)C43—C42—H42118.5
C11—C12—H12118.8C42—C43—C44119.7 (6)
C13—C12—H12118.8C42—C43—H43120.1
C14—C13—C12121.2 (5)C44—C43—H43120.1
C14—C13—H13119.4C39—C44—C43118.8 (5)
C12—C13—H13119.4C39—C44—H44120.6
C13—C14—C15119.1 (5)C43—C44—H44120.6
C13—C14—H14120.5C38—C45—C46123.1 (3)
C15—C14—H14120.5C38—C45—C47131.7 (3)
C14—C15—C16119.8 (5)C46—C45—C47104.7 (3)
C14—C15—H15120.1O1—C46—N4122.9 (3)
C16—C15—H15120.1O1—C46—C45129.6 (3)
C15—C16—C11119.9 (5)N4—C46—C45107.4 (3)
C15—C16—H16120.1N3—C47—C45111.5 (3)
C11—C16—H16120.1N3—C47—C48116.7 (3)
N1—C17—C18119.9 (3)C45—C47—C48131.7 (4)
N1—C17—C11120.2 (3)C47—C48—H48A109.5
C18—C17—C11119.8 (3)C47—C48—H48B109.5
C17—C18—C20124.3 (3)H48A—C48—H48B109.5
C17—C18—C19130.7 (4)C47—C48—H48C109.5
C20—C18—C19104.9 (3)H48A—C48—H48C109.5
N6—C19—C18111.7 (3)H48B—C48—H48C109.5
N6—C19—C21119.5 (3)C54—C49—C50120.4 (4)
C18—C19—C21128.6 (4)C54—C49—N4119.2 (3)
O2—C20—N5123.7 (3)C50—C49—N4120.4 (3)
O2—C20—C18130.7 (3)C49—C50—C51120.1 (4)
N5—C20—C18105.6 (3)C49—C50—H50119.9
C19—C21—H21A109.5C51—C50—H50119.9
C19—C21—H21B109.5C52—C51—C50119.7 (4)
H21A—C21—H21B109.5C52—C51—H51120.2
C19—C21—H21C109.5C50—C51—H51120.2
H21A—C21—H21C109.5C51—C52—C53118.7 (4)
H21B—C21—H21C109.5C51—C52—H52120.6
C27—C22—C23119.8 (4)C53—C52—H52120.6
C27—C22—N5121.9 (4)C52—C53—C54121.6 (4)
C23—C22—N5118.2 (4)C52—C53—H53119.2
C24—C23—C22119.1 (4)C54—C53—H53119.2
C24—C23—H23120.4C49—C54—C53119.5 (4)
C22—C23—H23120.4C49—C54—H54120.2
C25—C24—C23121.0 (4)C53—C54—H54120.2
C25—C24—H24119.5C17—N1—C1122.5 (3)
C23—C24—H24119.5C17—N1—Fe1127.2 (3)
C24—C25—C26119.7 (5)C1—N1—Fe1110.0 (2)
C24—C25—H25120.2C38—N2—C28120.7 (3)
C26—C25—H25120.2C38—N2—Fe1120.5 (2)
C25—C26—C27120.7 (5)C28—N2—Fe1117.6 (2)
C25—C26—H26119.7C47—N3—N4106.9 (3)
C27—C26—H26119.7C46—N4—N3109.4 (3)
C22—C27—C26119.7 (4)C46—N4—C49132.6 (3)
C22—C27—H27120.1N3—N4—C49117.9 (3)
C26—C27—H27120.1C20—N5—N6111.5 (3)
C29—C28—C37120.4 (4)C20—N5—C22129.5 (3)
C29—C28—N2121.9 (4)N6—N5—C22118.6 (3)
C37—C28—N2117.4 (4)C19—N6—N5106.1 (3)
C28—C29—C30120.3 (4)C46—O1—Fe1115.6 (2)
C28—C29—H29119.8C20—O2—Fe1120.3 (2)
C10—C1—C2—C71.4 (6)C38—C39—C44—C43171.0 (4)
N1—C1—C2—C7169.8 (3)C42—C43—C44—C390.4 (8)
C10—C1—C2—C3178.1 (4)N2—C38—C45—C4611.1 (6)
N1—C1—C2—C310.7 (6)C39—C38—C45—C46168.8 (3)
C1—C2—C3—C4178.8 (4)N2—C38—C45—C47178.4 (4)
C7—C2—C3—C40.7 (6)C39—C38—C45—C471.7 (6)
C2—C3—C4—C50.4 (7)C38—C45—C46—O19.6 (6)
C3—C4—C5—C61.3 (8)C47—C45—C46—O1177.7 (4)
C4—C5—C6—C71.2 (8)C38—C45—C46—N4170.2 (3)
C1—C2—C7—C80.5 (6)C47—C45—C46—N42.5 (4)
C3—C2—C7—C8179.0 (4)C38—C45—C47—N3170.5 (4)
C1—C2—C7—C6178.7 (4)C46—C45—C47—N31.3 (4)
C3—C2—C7—C60.9 (5)C38—C45—C47—C4813.2 (7)
C5—C6—C7—C8178.1 (5)C46—C45—C47—C48175.0 (4)
C5—C6—C7—C20.0 (7)C54—C49—C50—C510.2 (6)
C2—C7—C8—C90.9 (7)N4—C49—C50—C51178.7 (3)
C6—C7—C8—C9177.2 (4)C49—C50—C51—C520.1 (6)
C7—C8—C9—C101.4 (7)C50—C51—C52—C530.4 (7)
C2—C1—C10—C90.9 (6)C51—C52—C53—C540.9 (7)
N1—C1—C10—C9170.1 (3)C50—C49—C54—C530.3 (6)
C8—C9—C10—C10.5 (7)N4—C49—C54—C53179.2 (4)
C16—C11—C12—C132.3 (7)C52—C53—C54—C490.9 (7)
C17—C11—C12—C13174.7 (4)C18—C17—N1—C1173.6 (4)
C11—C12—C13—C143.1 (8)C11—C17—N1—C12.7 (6)
C12—C13—C14—C152.4 (9)C18—C17—N1—Fe10.5 (6)
C13—C14—C15—C161.0 (9)C11—C17—N1—Fe1176.9 (3)
C14—C15—C16—C110.2 (8)C10—C1—N1—C1789.8 (5)
C12—C11—C16—C150.9 (7)C2—C1—N1—C1799.0 (4)
C17—C11—C16—C15176.2 (4)C10—C1—N1—Fe195.2 (4)
C12—C11—C17—N1101.8 (5)C2—C1—N1—Fe176.0 (4)
C16—C11—C17—N181.3 (5)O2—Fe1—N1—C1712.3 (4)
C12—C11—C17—C1874.6 (5)O1—Fe1—N1—C17139.1 (3)
C16—C11—C17—C18102.4 (5)N2—Fe1—N1—C17119.9 (3)
N1—C17—C18—C2010.8 (6)O2—Fe1—N1—C1162.5 (3)
C11—C17—C18—C20165.5 (4)O1—Fe1—N1—C146.2 (3)
N1—C17—C18—C19172.3 (4)N2—Fe1—N1—C154.9 (3)
C11—C17—C18—C1911.3 (7)C45—C38—N2—C28173.4 (3)
C17—C18—C19—N6177.1 (4)C39—C38—N2—C286.5 (5)
C20—C18—C19—N60.3 (5)C45—C38—N2—Fe119.6 (5)
C17—C18—C19—C218.2 (8)C39—C38—N2—Fe1160.5 (3)
C20—C18—C19—C21174.5 (5)C29—C28—N2—C3879.9 (5)
C17—C18—C20—O24.4 (7)C37—C28—N2—C38105.8 (4)
C19—C18—C20—O2178.0 (4)C29—C28—N2—Fe187.5 (4)
C17—C18—C20—N5175.9 (4)C37—C28—N2—Fe186.8 (3)
C19—C18—C20—N51.7 (4)O2—Fe1—N2—C38169.5 (3)
C27—C22—C23—C240.4 (7)O1—Fe1—N2—C3839.4 (3)
N5—C22—C23—C24179.2 (4)N1—Fe1—N2—C3863.6 (3)
C22—C23—C24—C250.7 (8)O2—Fe1—N2—C282.1 (3)
C23—C24—C25—C261.0 (9)O1—Fe1—N2—C28153.2 (3)
C24—C25—C26—C270.9 (9)N1—Fe1—N2—C28103.8 (3)
C23—C22—C27—C260.3 (8)C45—C47—N3—N40.5 (4)
N5—C22—C27—C26179.1 (5)C48—C47—N3—N4177.4 (3)
C25—C26—C27—C220.6 (9)O1—C46—N4—N3177.3 (3)
C37—C28—C29—C301.2 (6)C45—C46—N4—N32.9 (4)
N2—C28—C29—C30175.3 (4)O1—C46—N4—C490.7 (6)
C28—C29—C30—C312.6 (7)C45—C46—N4—C49179.5 (3)
C29—C30—C31—C324.4 (7)C47—N3—N4—C462.1 (4)
C30—C31—C32—C33177.7 (4)C47—N3—N4—C49179.3 (3)
C30—C31—C32—C372.3 (6)C54—C49—N4—C46177.7 (4)
C37—C32—C33—C341.5 (6)C50—C49—N4—C463.4 (6)
C31—C32—C33—C34178.5 (4)C54—C49—N4—N36.0 (5)
C32—C33—C34—C350.2 (7)C50—C49—N4—N3172.9 (3)
C33—C34—C35—C362.3 (7)O2—C20—N5—N6177.2 (4)
C34—C35—C36—C372.7 (7)C18—C20—N5—N62.5 (4)
C35—C36—C37—C28179.3 (4)O2—C20—N5—C224.1 (7)
C35—C36—C37—C321.0 (6)C18—C20—N5—C22175.6 (4)
C29—C28—C37—C36177.2 (4)C27—C22—N5—C2019.1 (7)
N2—C28—C37—C362.8 (5)C23—C22—N5—C20159.7 (4)
C29—C28—C37—C323.1 (5)C27—C22—N5—N6168.2 (4)
N2—C28—C37—C32177.5 (3)C23—C22—N5—N613.0 (6)
C33—C32—C37—C361.1 (5)C18—C19—N6—N51.2 (5)
C31—C32—C37—C36178.9 (4)C21—C19—N6—N5176.6 (4)
C33—C32—C37—C28178.6 (3)C20—N5—N6—C192.4 (5)
C31—C32—C37—C281.4 (5)C22—N5—N6—C19176.3 (4)
N2—C38—C39—C4494.0 (5)N4—C46—O1—Fe1157.6 (3)
C45—C38—C39—C4486.0 (5)C45—C46—O1—Fe122.7 (5)
N2—C38—C39—C4095.2 (5)O2—Fe1—O1—C46150.5 (2)
C45—C38—C39—C4084.7 (4)N1—Fe1—O1—C4697.9 (2)
C44—C39—C40—C410.6 (6)N2—Fe1—O1—C4638.6 (2)
C38—C39—C40—C41171.4 (4)N5—C20—O2—Fe1167.0 (3)
C39—C40—C41—C421.3 (7)C18—C20—O2—Fe112.6 (6)
C40—C41—C42—C431.6 (9)O1—Fe1—O2—C2095.2 (3)
C41—C42—C43—C441.1 (9)N1—Fe1—O2—C2017.1 (3)
C40—C39—C44—C430.1 (7)N2—Fe1—O2—C20154.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···O20.932.342.928 (5)121
C50—H50···O10.932.282.924 (5)126
C48—H48A···N3i0.962.593.504 (5)160
Symmetry code: (i) x+2, y, z+1.
 

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