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
CCDC reference: 629829
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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-1
H-pyrazol-4-
ylidene)(phenyl)methyl]naphthylamido-
κ2N,
O}iron(II)
top
Crystal data top
[Fe(C27H20N3O)2] | F(000) = 1792 |
Mr = 860.77 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2528 reflections |
a = 13.1106 (9) Å | θ = 2.3–19.0° |
b = 19.6822 (13) Å | µ = 0.40 mm−1 |
c = 16.8314 (11) Å | T = 292 K |
β = 96.627 (2)° | Block, red |
V = 4314.2 (5) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 9368 independent reflections |
Radiation source: fine-focus sealed tube | 4102 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.123 |
ω scans | θmax = 27.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −16→16 |
Tmin = 0.924, Tmax = 0.961 | k = −25→25 |
31464 measured reflections | l = −21→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.74448 (4) | 0.07434 (2) | 0.12871 (3) | 0.03701 (17) | |
C1 | 0.7740 (3) | −0.06643 (18) | 0.1495 (2) | 0.0468 (10) | |
C2 | 0.8805 (3) | −0.07211 (19) | 0.1578 (2) | 0.0499 (10) | |
C3 | 0.9444 (4) | −0.0436 (2) | 0.1030 (3) | 0.0650 (13) | |
H3 | 0.9140 | −0.0190 | 0.0594 | 0.078* | |
C4 | 1.0479 (4) | −0.0514 (2) | 0.1125 (3) | 0.0798 (15) | |
H4 | 1.0873 | −0.0320 | 0.0760 | 0.096* | |
C5 | 1.0950 (4) | −0.0884 (3) | 0.1771 (4) | 0.0889 (17) | |
H5 | 1.1658 | −0.0943 | 0.1827 | 0.107* | |
C6 | 1.0403 (5) | −0.1152 (2) | 0.2307 (3) | 0.0856 (17) | |
H6 | 1.0742 | −0.1389 | 0.2736 | 0.103* | |
C7 | 0.9300 (4) | −0.1089 (2) | 0.2247 (3) | 0.0583 (12) | |
C8 | 0.8725 (4) | −0.1383 (2) | 0.2788 (3) | 0.0706 (14) | |
H8 | 0.9051 | −0.1617 | 0.3226 | 0.085* | |
C9 | 0.7679 (5) | −0.1334 (2) | 0.2686 (3) | 0.0805 (16) | |
H9 | 0.7297 | −0.1544 | 0.3050 | 0.097* | |
C10 | 0.7173 (4) | −0.0969 (2) | 0.2035 (3) | 0.0644 (13) | |
H10 | 0.6461 | −0.0934 | 0.1971 | 0.077* | |
C11 | 0.6823 (3) | −0.1139 (2) | −0.0012 (2) | 0.0462 (10) | |
C12 | 0.7485 (3) | −0.1418 (2) | −0.0467 (3) | 0.0621 (12) | |
H12 | 0.8013 | −0.1151 | −0.0622 | 0.074* | |
C13 | 0.7414 (4) | −0.2078 (3) | −0.0710 (3) | 0.0792 (15) | |
H13 | 0.7872 | −0.2243 | −0.1046 | 0.095* | |
C14 | 0.6702 (5) | −0.2491 (3) | −0.0473 (3) | 0.0886 (17) | |
H14 | 0.6677 | −0.2945 | −0.0627 | 0.106* | |
C15 | 0.6002 (5) | −0.2235 (3) | 0.0002 (3) | 0.108 (2) | |
H15 | 0.5494 | −0.2515 | 0.0165 | 0.129* | |
C16 | 0.6060 (4) | −0.1558 (2) | 0.0237 (3) | 0.0822 (16) | |
H16 | 0.5591 | −0.1383 | 0.0558 | 0.099* | |
C17 | 0.6851 (3) | −0.04055 (19) | 0.0192 (2) | 0.0443 (10) | |
C18 | 0.6488 (3) | 0.00769 (19) | −0.0391 (2) | 0.0446 (10) | |
C19 | 0.5916 (3) | −0.0009 (2) | −0.1163 (2) | 0.0575 (12) | |
C20 | 0.6680 (3) | 0.0789 (2) | −0.0323 (2) | 0.0452 (10) | |
C21 | 0.5434 (4) | −0.0637 (2) | −0.1528 (3) | 0.0952 (19) | |
H21A | 0.5017 | −0.0524 | −0.2016 | 0.143* | |
H21B | 0.5013 | −0.0842 | −0.1163 | 0.143* | |
H21C | 0.5960 | −0.0950 | −0.1638 | 0.143* | |
C22 | 0.6171 (3) | 0.1764 (2) | −0.1273 (2) | 0.0545 (11) | |
C23 | 0.5442 (3) | 0.1934 (2) | −0.1906 (2) | 0.0640 (13) | |
H23 | 0.5029 | 0.1600 | −0.2169 | 0.077* | |
C24 | 0.5337 (4) | 0.2603 (3) | −0.2139 (3) | 0.0786 (15) | |
H24 | 0.4855 | 0.2719 | −0.2566 | 0.094* | |
C25 | 0.5926 (4) | 0.3095 (3) | −0.1754 (3) | 0.0897 (17) | |
H25 | 0.5841 | 0.3546 | −0.1912 | 0.108* | |
C26 | 0.6643 (5) | 0.2925 (3) | −0.1136 (3) | 0.103 (2) | |
H26 | 0.7054 | 0.3261 | −0.0877 | 0.124* | |
C27 | 0.6766 (4) | 0.2258 (2) | −0.0889 (3) | 0.0826 (16) | |
H27 | 0.7253 | 0.2146 | −0.0463 | 0.099* | |
C28 | 0.8958 (3) | 0.18260 (19) | 0.1158 (2) | 0.0471 (10) | |
C29 | 0.9658 (3) | 0.1679 (2) | 0.0629 (3) | 0.0617 (12) | |
H29 | 0.9967 | 0.1253 | 0.0638 | 0.074* | |
C30 | 0.9904 (4) | 0.2166 (3) | 0.0081 (3) | 0.0724 (14) | |
H30 | 1.0355 | 0.2053 | −0.0286 | 0.087* | |
C31 | 0.9501 (4) | 0.2798 (2) | 0.0070 (3) | 0.0690 (13) | |
H31 | 0.9713 | 0.3123 | −0.0277 | 0.083* | |
C32 | 0.8751 (3) | 0.2970 (2) | 0.0591 (2) | 0.0514 (11) | |
C33 | 0.8281 (4) | 0.3617 (2) | 0.0582 (3) | 0.0620 (12) | |
H33 | 0.8474 | 0.3949 | 0.0236 | 0.074* | |
C34 | 0.7574 (4) | 0.3760 (2) | 0.1055 (3) | 0.0705 (14) | |
H34 | 0.7279 | 0.4190 | 0.1038 | 0.085* | |
C35 | 0.7263 (4) | 0.3273 (2) | 0.1580 (3) | 0.0721 (14) | |
H35 | 0.6747 | 0.3372 | 0.1898 | 0.087* | |
C36 | 0.7732 (3) | 0.2642 (2) | 0.1623 (3) | 0.0569 (11) | |
H36 | 0.7545 | 0.2325 | 0.1990 | 0.068* | |
C37 | 0.8465 (3) | 0.24718 (19) | 0.1139 (2) | 0.0420 (10) | |
C38 | 0.9208 (3) | 0.11656 (18) | 0.2359 (2) | 0.0413 (9) | |
C39 | 1.0283 (3) | 0.1450 (2) | 0.2551 (2) | 0.0489 (10) | |
C40 | 1.0448 (4) | 0.2025 (2) | 0.3020 (2) | 0.0668 (13) | |
H40 | 0.9886 | 0.2269 | 0.3155 | 0.080* | |
C41 | 1.1423 (5) | 0.2247 (3) | 0.3293 (3) | 0.0866 (17) | |
H41 | 1.1527 | 0.2640 | 0.3599 | 0.104* | |
C42 | 1.2209 (5) | 0.1879 (4) | 0.3102 (3) | 0.101 (2) | |
H42 | 1.2871 | 0.2016 | 0.3292 | 0.121* | |
C43 | 1.2088 (4) | 0.1306 (4) | 0.2636 (3) | 0.102 (2) | |
H43 | 1.2661 | 0.1068 | 0.2509 | 0.122* | |
C44 | 1.1114 (4) | 0.1084 (3) | 0.2357 (3) | 0.0758 (15) | |
H44 | 1.1021 | 0.0696 | 0.2043 | 0.091* | |
C45 | 0.8864 (3) | 0.07278 (18) | 0.2931 (2) | 0.0388 (9) | |
C46 | 0.7831 (3) | 0.05152 (17) | 0.2908 (2) | 0.0406 (9) | |
C47 | 0.9352 (3) | 0.04780 (19) | 0.3672 (2) | 0.0421 (10) | |
C48 | 1.0431 (3) | 0.0485 (2) | 0.4026 (2) | 0.0658 (13) | |
H48A | 1.0483 | 0.0300 | 0.4557 | 0.099* | |
H48B | 1.0681 | 0.0944 | 0.4049 | 0.099* | |
H48C | 1.0835 | 0.0217 | 0.3703 | 0.099* | |
C49 | 0.6892 (3) | −0.01284 (18) | 0.3921 (2) | 0.0415 (9) | |
C50 | 0.5961 (3) | −0.0179 (2) | 0.3462 (2) | 0.0578 (12) | |
H50 | 0.5875 | 0.0005 | 0.2949 | 0.069* | |
C51 | 0.5128 (3) | −0.0510 (2) | 0.3766 (3) | 0.0659 (13) | |
H51 | 0.4496 | −0.0546 | 0.3455 | 0.079* | |
C52 | 0.5258 (3) | −0.0779 (2) | 0.4524 (3) | 0.0643 (12) | |
H52 | 0.4721 | −0.1001 | 0.4731 | 0.077* | |
C53 | 0.6201 (4) | −0.0714 (2) | 0.4972 (3) | 0.0691 (13) | |
H53 | 0.6293 | −0.0890 | 0.5488 | 0.083* | |
C54 | 0.7023 (3) | −0.0392 (2) | 0.4669 (2) | 0.0547 (11) | |
H54 | 0.7657 | −0.0359 | 0.4978 | 0.066* | |
N1 | 0.7264 (3) | −0.02024 (14) | 0.09027 (18) | 0.0507 (9) | |
N2 | 0.8629 (2) | 0.13230 (14) | 0.16902 (17) | 0.0443 (8) | |
N3 | 0.8700 (2) | 0.01598 (15) | 0.40757 (17) | 0.0474 (8) | |
N4 | 0.7735 (2) | 0.01907 (15) | 0.36137 (17) | 0.0445 (8) | |
N5 | 0.6258 (2) | 0.10654 (16) | −0.10337 (18) | 0.0508 (9) | |
N6 | 0.5767 (3) | 0.05711 (18) | −0.1540 (2) | 0.0652 (11) | |
O1 | 0.70704 (19) | 0.05938 (12) | 0.23508 (14) | 0.0486 (7) | |
O2 | 0.7136 (2) | 0.11377 (12) | 0.02527 (14) | 0.0565 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0476 (3) | 0.0338 (3) | 0.0272 (3) | −0.0032 (3) | −0.0063 (2) | 0.0049 (2) |
C1 | 0.063 (3) | 0.032 (2) | 0.043 (2) | 0.004 (2) | −0.009 (2) | 0.0000 (19) |
C2 | 0.071 (3) | 0.039 (2) | 0.038 (2) | 0.008 (2) | −0.002 (2) | 0.002 (2) |
C3 | 0.086 (4) | 0.055 (3) | 0.049 (3) | 0.004 (3) | −0.010 (3) | 0.004 (2) |
C4 | 0.068 (4) | 0.090 (4) | 0.082 (4) | 0.003 (3) | 0.011 (3) | 0.012 (3) |
C5 | 0.064 (4) | 0.098 (4) | 0.103 (5) | 0.020 (3) | 0.001 (3) | 0.010 (4) |
C6 | 0.098 (5) | 0.073 (4) | 0.077 (4) | 0.023 (3) | −0.025 (3) | 0.013 (3) |
C7 | 0.080 (4) | 0.043 (3) | 0.049 (3) | 0.010 (2) | −0.005 (3) | 0.002 (2) |
C8 | 0.095 (4) | 0.065 (3) | 0.050 (3) | 0.019 (3) | −0.001 (3) | 0.015 (2) |
C9 | 0.128 (5) | 0.052 (3) | 0.064 (3) | 0.010 (3) | 0.024 (3) | 0.017 (3) |
C10 | 0.087 (4) | 0.042 (3) | 0.064 (3) | 0.005 (2) | 0.007 (3) | 0.005 (2) |
C11 | 0.053 (3) | 0.043 (3) | 0.042 (2) | −0.001 (2) | 0.002 (2) | 0.000 (2) |
C12 | 0.051 (3) | 0.059 (3) | 0.079 (3) | −0.006 (2) | 0.021 (2) | −0.014 (3) |
C13 | 0.087 (4) | 0.068 (4) | 0.087 (4) | 0.002 (3) | 0.028 (3) | −0.024 (3) |
C14 | 0.137 (5) | 0.055 (3) | 0.079 (4) | −0.014 (3) | 0.031 (4) | −0.018 (3) |
C15 | 0.173 (6) | 0.062 (4) | 0.098 (5) | −0.053 (4) | 0.054 (4) | −0.018 (3) |
C16 | 0.103 (4) | 0.066 (3) | 0.085 (4) | −0.024 (3) | 0.043 (3) | −0.023 (3) |
C17 | 0.042 (2) | 0.044 (2) | 0.046 (3) | −0.0026 (19) | 0.002 (2) | −0.001 (2) |
C18 | 0.049 (3) | 0.046 (2) | 0.036 (2) | 0.000 (2) | −0.0063 (19) | 0.0005 (19) |
C19 | 0.058 (3) | 0.056 (3) | 0.052 (3) | 0.007 (2) | −0.021 (2) | −0.005 (2) |
C20 | 0.047 (2) | 0.054 (3) | 0.033 (2) | 0.003 (2) | −0.0023 (18) | 0.007 (2) |
C21 | 0.125 (5) | 0.061 (3) | 0.082 (4) | 0.006 (3) | −0.065 (3) | −0.011 (3) |
C22 | 0.061 (3) | 0.064 (3) | 0.037 (2) | 0.000 (2) | −0.002 (2) | 0.015 (2) |
C23 | 0.061 (3) | 0.070 (3) | 0.058 (3) | −0.001 (2) | −0.007 (2) | 0.022 (2) |
C24 | 0.085 (4) | 0.082 (4) | 0.065 (3) | 0.006 (3) | −0.010 (3) | 0.037 (3) |
C25 | 0.120 (5) | 0.058 (3) | 0.085 (4) | −0.003 (3) | −0.009 (4) | 0.030 (3) |
C26 | 0.145 (6) | 0.069 (4) | 0.084 (4) | −0.031 (3) | −0.034 (4) | 0.032 (3) |
C27 | 0.108 (4) | 0.066 (3) | 0.065 (3) | −0.019 (3) | −0.025 (3) | 0.021 (3) |
C28 | 0.057 (3) | 0.043 (2) | 0.039 (2) | −0.006 (2) | −0.010 (2) | 0.0035 (19) |
C29 | 0.078 (3) | 0.055 (3) | 0.053 (3) | 0.004 (2) | 0.012 (3) | 0.007 (2) |
C30 | 0.076 (4) | 0.078 (4) | 0.069 (3) | −0.001 (3) | 0.032 (3) | 0.010 (3) |
C31 | 0.085 (4) | 0.065 (3) | 0.060 (3) | −0.011 (3) | 0.019 (3) | 0.013 (3) |
C32 | 0.063 (3) | 0.044 (3) | 0.045 (3) | −0.013 (2) | −0.005 (2) | 0.010 (2) |
C33 | 0.066 (3) | 0.055 (3) | 0.064 (3) | −0.005 (3) | 0.003 (3) | 0.013 (2) |
C34 | 0.069 (4) | 0.042 (3) | 0.098 (4) | 0.006 (2) | 0.001 (3) | 0.012 (3) |
C35 | 0.070 (3) | 0.062 (3) | 0.085 (4) | 0.011 (3) | 0.008 (3) | 0.003 (3) |
C36 | 0.059 (3) | 0.055 (3) | 0.056 (3) | −0.005 (2) | 0.002 (2) | 0.012 (2) |
C37 | 0.040 (2) | 0.046 (2) | 0.039 (2) | −0.0051 (19) | −0.0002 (19) | 0.0043 (19) |
C38 | 0.045 (2) | 0.037 (2) | 0.041 (2) | −0.0009 (18) | 0.0038 (19) | −0.0030 (18) |
C39 | 0.057 (3) | 0.057 (3) | 0.031 (2) | −0.003 (2) | −0.003 (2) | 0.002 (2) |
C40 | 0.076 (4) | 0.061 (3) | 0.059 (3) | −0.015 (3) | −0.011 (3) | 0.009 (2) |
C41 | 0.078 (4) | 0.091 (4) | 0.087 (4) | −0.029 (4) | −0.007 (3) | 0.008 (3) |
C42 | 0.067 (4) | 0.160 (7) | 0.072 (4) | −0.044 (4) | −0.006 (3) | 0.021 (4) |
C43 | 0.058 (4) | 0.180 (7) | 0.069 (4) | −0.004 (4) | 0.014 (3) | 0.005 (4) |
C44 | 0.049 (3) | 0.119 (4) | 0.061 (3) | 0.004 (3) | 0.011 (2) | −0.021 (3) |
C45 | 0.035 (2) | 0.044 (2) | 0.036 (2) | −0.0019 (19) | −0.0024 (17) | 0.0032 (19) |
C46 | 0.054 (3) | 0.036 (2) | 0.030 (2) | 0.0040 (19) | −0.0024 (19) | 0.0018 (17) |
C47 | 0.038 (2) | 0.050 (2) | 0.037 (2) | −0.0055 (19) | −0.0014 (19) | 0.0052 (19) |
C48 | 0.058 (3) | 0.085 (3) | 0.050 (3) | −0.002 (2) | −0.012 (2) | 0.016 (2) |
C49 | 0.040 (2) | 0.044 (2) | 0.040 (2) | −0.0051 (19) | 0.0001 (19) | 0.0038 (19) |
C50 | 0.051 (3) | 0.071 (3) | 0.050 (3) | −0.005 (2) | 0.000 (2) | 0.013 (2) |
C51 | 0.049 (3) | 0.079 (3) | 0.070 (3) | −0.005 (2) | 0.005 (2) | 0.004 (3) |
C52 | 0.057 (3) | 0.072 (3) | 0.065 (3) | −0.005 (3) | 0.015 (3) | 0.014 (3) |
C53 | 0.094 (4) | 0.064 (3) | 0.049 (3) | −0.002 (3) | 0.005 (3) | 0.012 (2) |
C54 | 0.050 (3) | 0.062 (3) | 0.050 (3) | −0.007 (2) | 0.000 (2) | 0.012 (2) |
N1 | 0.069 (2) | 0.0349 (18) | 0.044 (2) | 0.0060 (16) | −0.0106 (18) | 0.0004 (15) |
N2 | 0.048 (2) | 0.0422 (19) | 0.0405 (19) | −0.0039 (16) | −0.0021 (16) | 0.0092 (15) |
N3 | 0.049 (2) | 0.054 (2) | 0.0351 (19) | −0.0014 (17) | −0.0089 (16) | 0.0042 (16) |
N4 | 0.049 (2) | 0.0444 (19) | 0.0365 (19) | −0.0008 (16) | −0.0083 (16) | 0.0067 (15) |
N5 | 0.060 (2) | 0.053 (2) | 0.0362 (19) | 0.0028 (18) | −0.0096 (17) | 0.0093 (17) |
N6 | 0.079 (3) | 0.058 (2) | 0.050 (2) | 0.006 (2) | −0.0272 (19) | −0.0012 (19) |
O1 | 0.0513 (17) | 0.0541 (17) | 0.0371 (15) | 0.0006 (13) | −0.0091 (13) | 0.0111 (12) |
O2 | 0.079 (2) | 0.0489 (16) | 0.0368 (16) | −0.0123 (15) | −0.0144 (14) | 0.0060 (13) |
Geometric parameters (Å, º) top
Fe1—O2 | 1.907 (2) | C27—H27 | 0.9300 |
Fe1—O1 | 1.933 (2) | C28—C29 | 1.381 (5) |
Fe1—N1 | 1.976 (3) | C28—C37 | 1.425 (5) |
Fe1—N2 | 1.982 (3) | C28—N2 | 1.434 (4) |
C1—C10 | 1.376 (5) | C29—C30 | 1.392 (5) |
C1—C2 | 1.392 (5) | C29—H29 | 0.9300 |
C1—N1 | 1.437 (4) | C30—C31 | 1.350 (6) |
C2—C7 | 1.429 (5) | C30—H30 | 0.9300 |
C2—C3 | 1.430 (5) | C31—C32 | 1.432 (6) |
C3—C4 | 1.356 (6) | C31—H31 | 0.9300 |
C3—H3 | 0.9300 | C32—C33 | 1.413 (5) |
C4—C5 | 1.391 (6) | C32—C37 | 1.427 (5) |
C4—H4 | 0.9300 | C33—C34 | 1.320 (5) |
C5—C6 | 1.324 (6) | C33—H33 | 0.9300 |
C5—H5 | 0.9300 | C34—C35 | 1.396 (6) |
C6—C7 | 1.444 (6) | C34—H34 | 0.9300 |
C6—H6 | 0.9300 | C35—C36 | 1.385 (5) |
C7—C8 | 1.375 (6) | C35—H35 | 0.9300 |
C8—C9 | 1.365 (6) | C36—C37 | 1.370 (5) |
C8—H8 | 0.9300 | C36—H36 | 0.9300 |
C9—C10 | 1.412 (6) | C38—N2 | 1.320 (4) |
C9—H9 | 0.9300 | C38—C45 | 1.404 (5) |
C10—H10 | 0.9300 | C38—C39 | 1.516 (5) |
C11—C12 | 1.339 (5) | C39—C44 | 1.376 (5) |
C11—C16 | 1.397 (5) | C39—C40 | 1.383 (5) |
C11—C17 | 1.483 (5) | C40—C41 | 1.379 (6) |
C12—C13 | 1.362 (5) | C40—H40 | 0.9300 |
C12—H12 | 0.9300 | C41—C42 | 1.330 (7) |
C13—C14 | 1.333 (6) | C41—H41 | 0.9300 |
C13—H13 | 0.9300 | C42—C43 | 1.372 (7) |
C14—C15 | 1.381 (7) | C42—H42 | 0.9300 |
C14—H14 | 0.9300 | C43—C44 | 1.380 (6) |
C15—C16 | 1.390 (6) | C43—H43 | 0.9300 |
C15—H15 | 0.9300 | C44—H44 | 0.9300 |
C16—H16 | 0.9300 | C45—C46 | 1.414 (5) |
C17—N1 | 1.316 (4) | C45—C47 | 1.423 (5) |
C17—C18 | 1.408 (5) | C46—O1 | 1.297 (4) |
C18—C20 | 1.427 (5) | C46—N4 | 1.367 (4) |
C18—C19 | 1.434 (5) | C47—N3 | 1.310 (4) |
C19—N6 | 1.310 (5) | C47—C48 | 1.471 (5) |
C19—C21 | 1.488 (5) | C48—H48A | 0.9600 |
C20—O2 | 1.277 (4) | C48—H48B | 0.9600 |
C20—N5 | 1.372 (4) | C48—H48C | 0.9600 |
C21—H21A | 0.9600 | C49—C54 | 1.354 (5) |
C21—H21B | 0.9600 | C49—C50 | 1.371 (5) |
C21—H21C | 0.9600 | C49—N4 | 1.420 (4) |
C22—C27 | 1.362 (5) | C50—C51 | 1.418 (5) |
C22—C23 | 1.388 (5) | C50—H50 | 0.9300 |
C22—N5 | 1.433 (5) | C51—C52 | 1.372 (5) |
C23—C24 | 1.376 (5) | C51—H51 | 0.9300 |
C23—H23 | 0.9300 | C52—C53 | 1.378 (6) |
C24—C25 | 1.356 (6) | C52—H52 | 0.9300 |
C24—H24 | 0.9300 | C53—C54 | 1.396 (5) |
C25—C26 | 1.361 (6) | C53—H53 | 0.9300 |
C25—H25 | 0.9300 | C54—H54 | 0.9300 |
C26—C27 | 1.381 (6) | N3—N4 | 1.408 (4) |
C26—H26 | 0.9300 | N5—N6 | 1.400 (4) |
| | | |
O2—Fe1—O1 | 149.08 (11) | C30—C29—H29 | 119.8 |
O2—Fe1—N1 | 94.56 (12) | C31—C30—C29 | 121.5 (4) |
O1—Fe1—N1 | 97.24 (11) | C31—C30—H30 | 119.2 |
O2—Fe1—N2 | 98.85 (12) | C29—C30—H30 | 119.2 |
O1—Fe1—N2 | 92.48 (11) | C30—C31—C32 | 120.4 (4) |
N1—Fe1—N2 | 135.56 (13) | C30—C31—H31 | 119.8 |
C10—C1—C2 | 120.7 (4) | C32—C31—H31 | 119.8 |
C10—C1—N1 | 120.6 (4) | C33—C32—C37 | 118.6 (4) |
C2—C1—N1 | 118.1 (4) | C33—C32—C31 | 122.5 (4) |
C1—C2—C7 | 118.6 (4) | C37—C32—C31 | 118.9 (4) |
C1—C2—C3 | 124.0 (4) | C34—C33—C32 | 121.4 (4) |
C7—C2—C3 | 117.4 (4) | C34—C33—H33 | 119.3 |
C4—C3—C2 | 122.1 (4) | C32—C33—H33 | 119.3 |
C4—C3—H3 | 118.9 | C33—C34—C35 | 120.8 (4) |
C2—C3—H3 | 118.9 | C33—C34—H34 | 119.6 |
C3—C4—C5 | 119.9 (5) | C35—C34—H34 | 119.6 |
C3—C4—H4 | 120.0 | C36—C35—C34 | 119.2 (4) |
C5—C4—H4 | 120.0 | C36—C35—H35 | 120.4 |
C6—C5—C4 | 120.9 (5) | C34—C35—H35 | 120.4 |
C6—C5—H5 | 119.5 | C37—C36—C35 | 121.7 (4) |
C4—C5—H5 | 119.5 | C37—C36—H36 | 119.2 |
C5—C6—C7 | 122.3 (5) | C35—C36—H36 | 119.2 |
C5—C6—H6 | 118.8 | C36—C37—C28 | 123.5 (4) |
C7—C6—H6 | 118.8 | C36—C37—C32 | 118.1 (4) |
C8—C7—C2 | 120.1 (4) | C28—C37—C32 | 118.4 (4) |
C8—C7—C6 | 122.6 (4) | N2—C38—C45 | 122.0 (3) |
C2—C7—C6 | 117.3 (4) | N2—C38—C39 | 121.6 (3) |
C9—C8—C7 | 120.4 (4) | C45—C38—C39 | 116.4 (3) |
C9—C8—H8 | 119.8 | C44—C39—C40 | 119.2 (4) |
C7—C8—H8 | 119.8 | C44—C39—C38 | 119.9 (4) |
C8—C9—C10 | 120.6 (5) | C40—C39—C38 | 120.3 (4) |
C8—C9—H9 | 119.7 | C41—C40—C39 | 121.9 (5) |
C10—C9—H9 | 119.7 | C41—C40—H40 | 119.1 |
C1—C10—C9 | 119.6 (5) | C39—C40—H40 | 119.1 |
C1—C10—H10 | 120.2 | C42—C41—C40 | 117.5 (6) |
C9—C10—H10 | 120.2 | C42—C41—H41 | 121.3 |
C12—C11—C16 | 117.6 (4) | C40—C41—H41 | 121.3 |
C12—C11—C17 | 122.1 (4) | C41—C42—C43 | 123.0 (6) |
C16—C11—C17 | 120.3 (4) | C41—C42—H42 | 118.5 |
C11—C12—C13 | 122.5 (4) | C43—C42—H42 | 118.5 |
C11—C12—H12 | 118.8 | C42—C43—C44 | 119.7 (6) |
C13—C12—H12 | 118.8 | C42—C43—H43 | 120.1 |
C14—C13—C12 | 121.2 (5) | C44—C43—H43 | 120.1 |
C14—C13—H13 | 119.4 | C39—C44—C43 | 118.8 (5) |
C12—C13—H13 | 119.4 | C39—C44—H44 | 120.6 |
C13—C14—C15 | 119.1 (5) | C43—C44—H44 | 120.6 |
C13—C14—H14 | 120.5 | C38—C45—C46 | 123.1 (3) |
C15—C14—H14 | 120.5 | C38—C45—C47 | 131.7 (3) |
C14—C15—C16 | 119.8 (5) | C46—C45—C47 | 104.7 (3) |
C14—C15—H15 | 120.1 | O1—C46—N4 | 122.9 (3) |
C16—C15—H15 | 120.1 | O1—C46—C45 | 129.6 (3) |
C15—C16—C11 | 119.9 (5) | N4—C46—C45 | 107.4 (3) |
C15—C16—H16 | 120.1 | N3—C47—C45 | 111.5 (3) |
C11—C16—H16 | 120.1 | N3—C47—C48 | 116.7 (3) |
N1—C17—C18 | 119.9 (3) | C45—C47—C48 | 131.7 (4) |
N1—C17—C11 | 120.2 (3) | C47—C48—H48A | 109.5 |
C18—C17—C11 | 119.8 (3) | C47—C48—H48B | 109.5 |
C17—C18—C20 | 124.3 (3) | H48A—C48—H48B | 109.5 |
C17—C18—C19 | 130.7 (4) | C47—C48—H48C | 109.5 |
C20—C18—C19 | 104.9 (3) | H48A—C48—H48C | 109.5 |
N6—C19—C18 | 111.7 (3) | H48B—C48—H48C | 109.5 |
N6—C19—C21 | 119.5 (3) | C54—C49—C50 | 120.4 (4) |
C18—C19—C21 | 128.6 (4) | C54—C49—N4 | 119.2 (3) |
O2—C20—N5 | 123.7 (3) | C50—C49—N4 | 120.4 (3) |
O2—C20—C18 | 130.7 (3) | C49—C50—C51 | 120.1 (4) |
N5—C20—C18 | 105.6 (3) | C49—C50—H50 | 119.9 |
C19—C21—H21A | 109.5 | C51—C50—H50 | 119.9 |
C19—C21—H21B | 109.5 | C52—C51—C50 | 119.7 (4) |
H21A—C21—H21B | 109.5 | C52—C51—H51 | 120.2 |
C19—C21—H21C | 109.5 | C50—C51—H51 | 120.2 |
H21A—C21—H21C | 109.5 | C51—C52—C53 | 118.7 (4) |
H21B—C21—H21C | 109.5 | C51—C52—H52 | 120.6 |
C27—C22—C23 | 119.8 (4) | C53—C52—H52 | 120.6 |
C27—C22—N5 | 121.9 (4) | C52—C53—C54 | 121.6 (4) |
C23—C22—N5 | 118.2 (4) | C52—C53—H53 | 119.2 |
C24—C23—C22 | 119.1 (4) | C54—C53—H53 | 119.2 |
C24—C23—H23 | 120.4 | C49—C54—C53 | 119.5 (4) |
C22—C23—H23 | 120.4 | C49—C54—H54 | 120.2 |
C25—C24—C23 | 121.0 (4) | C53—C54—H54 | 120.2 |
C25—C24—H24 | 119.5 | C17—N1—C1 | 122.5 (3) |
C23—C24—H24 | 119.5 | C17—N1—Fe1 | 127.2 (3) |
C24—C25—C26 | 119.7 (5) | C1—N1—Fe1 | 110.0 (2) |
C24—C25—H25 | 120.2 | C38—N2—C28 | 120.7 (3) |
C26—C25—H25 | 120.2 | C38—N2—Fe1 | 120.5 (2) |
C25—C26—C27 | 120.7 (5) | C28—N2—Fe1 | 117.6 (2) |
C25—C26—H26 | 119.7 | C47—N3—N4 | 106.9 (3) |
C27—C26—H26 | 119.7 | C46—N4—N3 | 109.4 (3) |
C22—C27—C26 | 119.7 (4) | C46—N4—C49 | 132.6 (3) |
C22—C27—H27 | 120.1 | N3—N4—C49 | 117.9 (3) |
C26—C27—H27 | 120.1 | C20—N5—N6 | 111.5 (3) |
C29—C28—C37 | 120.4 (4) | C20—N5—C22 | 129.5 (3) |
C29—C28—N2 | 121.9 (4) | N6—N5—C22 | 118.6 (3) |
C37—C28—N2 | 117.4 (4) | C19—N6—N5 | 106.1 (3) |
C28—C29—C30 | 120.3 (4) | C46—O1—Fe1 | 115.6 (2) |
C28—C29—H29 | 119.8 | C20—O2—Fe1 | 120.3 (2) |
| | | |
C10—C1—C2—C7 | −1.4 (6) | C38—C39—C44—C43 | −171.0 (4) |
N1—C1—C2—C7 | 169.8 (3) | C42—C43—C44—C39 | 0.4 (8) |
C10—C1—C2—C3 | 178.1 (4) | N2—C38—C45—C46 | −11.1 (6) |
N1—C1—C2—C3 | −10.7 (6) | C39—C38—C45—C46 | 168.8 (3) |
C1—C2—C3—C4 | −178.8 (4) | N2—C38—C45—C47 | 178.4 (4) |
C7—C2—C3—C4 | 0.7 (6) | C39—C38—C45—C47 | −1.7 (6) |
C2—C3—C4—C5 | 0.4 (7) | C38—C45—C46—O1 | 9.6 (6) |
C3—C4—C5—C6 | −1.3 (8) | C47—C45—C46—O1 | −177.7 (4) |
C4—C5—C6—C7 | 1.2 (8) | C38—C45—C46—N4 | −170.2 (3) |
C1—C2—C7—C8 | 0.5 (6) | C47—C45—C46—N4 | 2.5 (4) |
C3—C2—C7—C8 | −179.0 (4) | C38—C45—C47—N3 | 170.5 (4) |
C1—C2—C7—C6 | 178.7 (4) | C46—C45—C47—N3 | −1.3 (4) |
C3—C2—C7—C6 | −0.9 (5) | C38—C45—C47—C48 | −13.2 (7) |
C5—C6—C7—C8 | 178.1 (5) | C46—C45—C47—C48 | 175.0 (4) |
C5—C6—C7—C2 | 0.0 (7) | C54—C49—C50—C51 | −0.2 (6) |
C2—C7—C8—C9 | 0.9 (7) | N4—C49—C50—C51 | 178.7 (3) |
C6—C7—C8—C9 | −177.2 (4) | C49—C50—C51—C52 | 0.1 (6) |
C7—C8—C9—C10 | −1.4 (7) | C50—C51—C52—C53 | 0.4 (7) |
C2—C1—C10—C9 | 0.9 (6) | C51—C52—C53—C54 | −0.9 (7) |
N1—C1—C10—C9 | −170.1 (3) | C50—C49—C54—C53 | −0.3 (6) |
C8—C9—C10—C1 | 0.5 (7) | N4—C49—C54—C53 | −179.2 (4) |
C16—C11—C12—C13 | 2.3 (7) | C52—C53—C54—C49 | 0.9 (7) |
C17—C11—C12—C13 | −174.7 (4) | C18—C17—N1—C1 | −173.6 (4) |
C11—C12—C13—C14 | −3.1 (8) | C11—C17—N1—C1 | 2.7 (6) |
C12—C13—C14—C15 | 2.4 (9) | C18—C17—N1—Fe1 | 0.5 (6) |
C13—C14—C15—C16 | −1.0 (9) | C11—C17—N1—Fe1 | 176.9 (3) |
C14—C15—C16—C11 | 0.2 (8) | C10—C1—N1—C17 | −89.8 (5) |
C12—C11—C16—C15 | −0.9 (7) | C2—C1—N1—C17 | 99.0 (4) |
C17—C11—C16—C15 | 176.2 (4) | C10—C1—N1—Fe1 | 95.2 (4) |
C12—C11—C17—N1 | −101.8 (5) | C2—C1—N1—Fe1 | −76.0 (4) |
C16—C11—C17—N1 | 81.3 (5) | O2—Fe1—N1—C17 | −12.3 (4) |
C12—C11—C17—C18 | 74.6 (5) | O1—Fe1—N1—C17 | 139.1 (3) |
C16—C11—C17—C18 | −102.4 (5) | N2—Fe1—N1—C17 | −119.9 (3) |
N1—C17—C18—C20 | 10.8 (6) | O2—Fe1—N1—C1 | 162.5 (3) |
C11—C17—C18—C20 | −165.5 (4) | O1—Fe1—N1—C1 | −46.2 (3) |
N1—C17—C18—C19 | −172.3 (4) | N2—Fe1—N1—C1 | 54.9 (3) |
C11—C17—C18—C19 | 11.3 (7) | C45—C38—N2—C28 | 173.4 (3) |
C17—C18—C19—N6 | −177.1 (4) | C39—C38—N2—C28 | −6.5 (5) |
C20—C18—C19—N6 | 0.3 (5) | C45—C38—N2—Fe1 | −19.6 (5) |
C17—C18—C19—C21 | 8.2 (8) | C39—C38—N2—Fe1 | 160.5 (3) |
C20—C18—C19—C21 | −174.5 (5) | C29—C28—N2—C38 | 79.9 (5) |
C17—C18—C20—O2 | −4.4 (7) | C37—C28—N2—C38 | −105.8 (4) |
C19—C18—C20—O2 | 178.0 (4) | C29—C28—N2—Fe1 | −87.5 (4) |
C17—C18—C20—N5 | 175.9 (4) | C37—C28—N2—Fe1 | 86.8 (3) |
C19—C18—C20—N5 | −1.7 (4) | O2—Fe1—N2—C38 | −169.5 (3) |
C27—C22—C23—C24 | 0.4 (7) | O1—Fe1—N2—C38 | 39.4 (3) |
N5—C22—C23—C24 | 179.2 (4) | N1—Fe1—N2—C38 | −63.6 (3) |
C22—C23—C24—C25 | −0.7 (8) | O2—Fe1—N2—C28 | −2.1 (3) |
C23—C24—C25—C26 | 1.0 (9) | O1—Fe1—N2—C28 | −153.2 (3) |
C24—C25—C26—C27 | −0.9 (9) | N1—Fe1—N2—C28 | 103.8 (3) |
C23—C22—C27—C26 | −0.3 (8) | C45—C47—N3—N4 | −0.5 (4) |
N5—C22—C27—C26 | −179.1 (5) | C48—C47—N3—N4 | −177.4 (3) |
C25—C26—C27—C22 | 0.6 (9) | O1—C46—N4—N3 | 177.3 (3) |
C37—C28—C29—C30 | 1.2 (6) | C45—C46—N4—N3 | −2.9 (4) |
N2—C28—C29—C30 | 175.3 (4) | O1—C46—N4—C49 | 0.7 (6) |
C28—C29—C30—C31 | 2.6 (7) | C45—C46—N4—C49 | −179.5 (3) |
C29—C30—C31—C32 | −4.4 (7) | C47—N3—N4—C46 | 2.1 (4) |
C30—C31—C32—C33 | −177.7 (4) | C47—N3—N4—C49 | 179.3 (3) |
C30—C31—C32—C37 | 2.3 (6) | C54—C49—N4—C46 | −177.7 (4) |
C37—C32—C33—C34 | −1.5 (6) | C50—C49—N4—C46 | 3.4 (6) |
C31—C32—C33—C34 | 178.5 (4) | C54—C49—N4—N3 | 6.0 (5) |
C32—C33—C34—C35 | −0.2 (7) | C50—C49—N4—N3 | −172.9 (3) |
C33—C34—C35—C36 | 2.3 (7) | O2—C20—N5—N6 | −177.2 (4) |
C34—C35—C36—C37 | −2.7 (7) | C18—C20—N5—N6 | 2.5 (4) |
C35—C36—C37—C28 | −179.3 (4) | O2—C20—N5—C22 | −4.1 (7) |
C35—C36—C37—C32 | 1.0 (6) | C18—C20—N5—C22 | 175.6 (4) |
C29—C28—C37—C36 | 177.2 (4) | C27—C22—N5—C20 | 19.1 (7) |
N2—C28—C37—C36 | 2.8 (5) | C23—C22—N5—C20 | −159.7 (4) |
C29—C28—C37—C32 | −3.1 (5) | C27—C22—N5—N6 | −168.2 (4) |
N2—C28—C37—C32 | −177.5 (3) | C23—C22—N5—N6 | 13.0 (6) |
C33—C32—C37—C36 | 1.1 (5) | C18—C19—N6—N5 | 1.2 (5) |
C31—C32—C37—C36 | −178.9 (4) | C21—C19—N6—N5 | 176.6 (4) |
C33—C32—C37—C28 | −178.6 (3) | C20—N5—N6—C19 | −2.4 (5) |
C31—C32—C37—C28 | 1.4 (5) | C22—N5—N6—C19 | −176.3 (4) |
N2—C38—C39—C44 | −94.0 (5) | N4—C46—O1—Fe1 | −157.6 (3) |
C45—C38—C39—C44 | 86.0 (5) | C45—C46—O1—Fe1 | 22.7 (5) |
N2—C38—C39—C40 | 95.2 (5) | O2—Fe1—O1—C46 | −150.5 (2) |
C45—C38—C39—C40 | −84.7 (4) | N1—Fe1—O1—C46 | 97.9 (2) |
C44—C39—C40—C41 | 0.6 (6) | N2—Fe1—O1—C46 | −38.6 (2) |
C38—C39—C40—C41 | 171.4 (4) | N5—C20—O2—Fe1 | 167.0 (3) |
C39—C40—C41—C42 | −1.3 (7) | C18—C20—O2—Fe1 | −12.6 (6) |
C40—C41—C42—C43 | 1.6 (9) | O1—Fe1—O2—C20 | −95.2 (3) |
C41—C42—C43—C44 | −1.1 (9) | N1—Fe1—O2—C20 | 17.1 (3) |
C40—C39—C44—C43 | −0.1 (7) | N2—Fe1—O2—C20 | 154.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27···O2 | 0.93 | 2.34 | 2.928 (5) | 121 |
C50—H50···O1 | 0.93 | 2.28 | 2.924 (5) | 126 |
C48—H48A···N3i | 0.96 | 2.59 | 3.504 (5) | 160 |
Symmetry code: (i) −x+2, −y, −z+1. |