In the title compound, [Fe(C
12H
8N
2)
3](C
4O
4)·8H
2O or [Fe(phen)
3]sq·8H
2O, where phen is 1,10-phenanthroline and sq is the squarate dianion (C
4O
4)
2−, the Fe
II centre has a distorted octahedral coordination geometry comprising six N atoms from the three bidentate chelating phen ligands. An extensive three-dimensional network of O
water—H
O, O
water—H
O
water and C—H
O hydrogen-bonding interactions is responsible for crystal stabilization.
Supporting information
CCDC reference: 277227
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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)·8H2O | F(000) = 1776 |
Mr = 852.63 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5187 reflections |
a = 10.9285 (6) Å | θ = 1.7–27.8° |
b = 21.3431 (7) Å | µ = 0.46 mm−1 |
c = 16.8988 (8) Å | T = 297 K |
β = 98.804 (4)° | Plate, red |
V = 3895.4 (3) Å3 | 0.31 × 0.25 × 0.19 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 8612 independent reflections |
Radiation source: fine-focus sealed tube | 5723 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 1.6° |
ω scans | h = −13→14 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −27→27 |
Tmin = 0.734, Tmax = 0.932 | l = −21→21 |
42766 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H 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 reflections | Δρmax = 0.28 e Å−3 |
583 parameters | Δρmin = −0.40 e Å−3 |
25 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3344 (2) | 0.22086 (11) | 0.94575 (13) | 0.0491 (5) | |
H1 | 0.2886 | 0.2517 | 0.9156 | 0.059* | |
C2 | 0.3111 (2) | 0.20920 (13) | 1.02306 (14) | 0.0611 (6) | |
H2 | 0.2497 | 0.2316 | 1.0433 | 0.073* | |
C3 | 0.3775 (3) | 0.16530 (14) | 1.06872 (15) | 0.0685 (7) | |
H3 | 0.3615 | 0.1571 | 1.1202 | 0.082* | |
C4 | 0.4711 (2) | 0.13215 (12) | 1.03793 (14) | 0.0601 (6) | |
C5 | 0.5492 (3) | 0.08535 (15) | 1.08055 (17) | 0.0821 (9) | |
H5 | 0.5400 | 0.0758 | 1.1330 | 0.098* | |
C6 | 0.6353 (3) | 0.05505 (15) | 1.04633 (17) | 0.0822 (9) | |
H6 | 0.6854 | 0.0254 | 1.0759 | 0.099* | |
C7 | 0.6518 (2) | 0.06738 (11) | 0.96529 (15) | 0.0578 (6) | |
C8 | 0.7405 (2) | 0.03784 (12) | 0.92542 (17) | 0.0663 (7) | |
H8 | 0.7928 | 0.0073 | 0.9512 | 0.080* | |
C9 | 0.7483 (2) | 0.05457 (11) | 0.84895 (15) | 0.0585 (6) | |
H9 | 0.8070 | 0.0358 | 0.8222 | 0.070* | |
C10 | 0.66867 (19) | 0.09996 (10) | 0.81014 (14) | 0.0493 (5) | |
H10 | 0.6754 | 0.1104 | 0.7576 | 0.059* | |
C11 | 0.57649 (19) | 0.11274 (10) | 0.92268 (12) | 0.0452 (5) | |
C12 | 0.48709 (19) | 0.14546 (10) | 0.95944 (12) | 0.0458 (5) | |
C13 | 0.22761 (18) | 0.26333 (10) | 0.73763 (13) | 0.0483 (5) | |
H13 | 0.1899 | 0.2249 | 0.7241 | 0.058* | |
C14 | 0.1583 (2) | 0.31764 (11) | 0.72133 (15) | 0.0559 (6) | |
H14 | 0.0761 | 0.3149 | 0.6971 | 0.067* | |
C15 | 0.2093 (2) | 0.37477 (11) | 0.74042 (14) | 0.0531 (5) | |
H15 | 0.1625 | 0.4111 | 0.7305 | 0.064* | |
C16 | 0.33425 (19) | 0.37784 (9) | 0.77533 (12) | 0.0445 (4) | |
C17 | 0.4003 (2) | 0.43505 (10) | 0.79635 (14) | 0.0555 (5) | |
H17 | 0.3583 | 0.4730 | 0.7897 | 0.067* | |
C18 | 0.5213 (2) | 0.43477 (10) | 0.82536 (15) | 0.0561 (6) | |
H18 | 0.5621 | 0.4727 | 0.8370 | 0.067* | |
C19 | 0.5897 (2) | 0.37743 (10) | 0.83892 (12) | 0.0471 (5) | |
C20 | 0.7159 (2) | 0.37344 (11) | 0.87166 (14) | 0.0543 (5) | |
H20 | 0.7624 | 0.4096 | 0.8841 | 0.065* | |
C21 | 0.7686 (2) | 0.31586 (12) | 0.88477 (15) | 0.0590 (6) | |
H21 | 0.8517 | 0.3126 | 0.9068 | 0.071* | |
C22 | 0.69939 (18) | 0.26209 (11) | 0.86547 (13) | 0.0498 (5) | |
H22 | 0.7381 | 0.2234 | 0.8745 | 0.060* | |
C23 | 0.52638 (17) | 0.32112 (9) | 0.82152 (11) | 0.0386 (4) | |
C24 | 0.39834 (18) | 0.32152 (9) | 0.78847 (11) | 0.0385 (4) | |
C25 | 0.58742 (19) | 0.21882 (11) | 0.66050 (13) | 0.0499 (5) | |
H25 | 0.6365 | 0.2485 | 0.6907 | 0.060* | |
C26 | 0.6063 (2) | 0.20793 (13) | 0.58212 (14) | 0.0619 (6) | |
H26 | 0.6672 | 0.2299 | 0.5608 | 0.074* | |
C27 | 0.5354 (3) | 0.16508 (14) | 0.53695 (15) | 0.0677 (7) | |
H27 | 0.5487 | 0.1571 | 0.4848 | 0.081* | |
C28 | 0.4420 (2) | 0.13279 (11) | 0.56859 (13) | 0.0556 (6) | |
C29 | 0.3584 (3) | 0.08803 (13) | 0.52634 (15) | 0.0693 (7) | |
H29 | 0.3657 | 0.0782 | 0.4736 | 0.083* | |
C30 | 0.2698 (2) | 0.05979 (12) | 0.56079 (15) | 0.0630 (6) | |
H30 | 0.2158 | 0.0318 | 0.5312 | 0.076* | |
C31 | 0.2576 (2) | 0.07231 (9) | 0.64215 (14) | 0.0491 (5) | |
C32 | 0.1694 (2) | 0.04452 (10) | 0.68286 (16) | 0.0587 (6) | |
H32 | 0.1130 | 0.0158 | 0.6569 | 0.070* | |
C33 | 0.1668 (2) | 0.05979 (11) | 0.76071 (17) | 0.0617 (6) | |
H33 | 0.1080 | 0.0417 | 0.7881 | 0.074* | |
C34 | 0.2520 (2) | 0.10245 (10) | 0.79951 (15) | 0.0530 (5) | |
H34 | 0.2491 | 0.1119 | 0.8529 | 0.064* | |
C35 | 0.33943 (18) | 0.11517 (9) | 0.68519 (12) | 0.0420 (4) | |
C36 | 0.42994 (18) | 0.14625 (9) | 0.64790 (12) | 0.0432 (4) | |
C37 | 0.8632 (2) | 0.08495 (11) | 0.63575 (15) | 0.0561 (6) | |
C38 | 0.8991 (2) | 0.14814 (11) | 0.66219 (14) | 0.0576 (6) | |
C39 | 0.9576 (2) | 0.15746 (11) | 0.59251 (14) | 0.0562 (5) | |
C40 | 0.91917 (19) | 0.09514 (10) | 0.56355 (13) | 0.0477 (5) | |
N1 | 0.41973 (15) | 0.18965 (8) | 0.91332 (10) | 0.0420 (4) | |
N2 | 0.50220 (15) | 0.18863 (8) | 0.69413 (10) | 0.0408 (4) | |
N3 | 0.33754 (15) | 0.13031 (7) | 0.76332 (10) | 0.0419 (4) | |
N4 | 0.57940 (14) | 0.26340 (7) | 0.83441 (9) | 0.0397 (4) | |
N5 | 0.58338 (15) | 0.12883 (7) | 0.84551 (10) | 0.0411 (4) | |
N6 | 0.34573 (14) | 0.26396 (7) | 0.77179 (9) | 0.0387 (3) | |
O1 | 0.8115 (2) | 0.03966 (9) | 0.66285 (13) | 0.0851 (6) | |
O2 | 0.92904 (16) | 0.06266 (7) | 0.50370 (10) | 0.0609 (4) | |
O3 | 1.0200 (2) | 0.20095 (8) | 0.56762 (13) | 0.0839 (6) | |
O4 | 0.8848 (2) | 0.18132 (9) | 0.72229 (12) | 0.0810 (6) | |
O5 | 1.0081 (2) | −0.03433 (10) | 0.89716 (15) | 0.0931 (7) | |
O6 | 1.0955 (2) | −0.08269 (9) | 0.76703 (12) | 0.0777 (5) | |
O7 | 1.06292 (19) | 0.06723 (8) | 0.37953 (11) | 0.0666 (5) | |
O8 | 1.10008 (19) | 0.19476 (8) | 0.42302 (13) | 0.0708 (5) | |
O9 | 0.8793 (4) | 0.30815 (16) | 0.5277 (2) | 0.1258 (10) | |
O10 | 0.8240 (2) | 0.30343 (10) | 0.68316 (16) | 0.0877 (6) | |
O11 | 1.0097 (3) | 0.18597 (10) | 0.87431 (16) | 0.1172 (10) | |
O12 | 0.0861 (3) | 0.08040 (12) | 0.96385 (16) | 0.1091 (8) | |
Fe1 | 0.46192 (2) | 0.194212 (12) | 0.803680 (16) | 0.03605 (9) | |
H5A | 0.992 (2) | −0.0607 (10) | 0.9312 (12) | 0.054* | |
H5B | 1.040 (2) | −0.0554 (10) | 0.8636 (11) | 0.054* | |
H6A | 1.0504 (19) | −0.0846 (11) | 0.7204 (11) | 0.054* | |
H6B | 1.124 (2) | −0.1216 (8) | 0.7751 (13) | 0.054* | |
H7A | 1.110 (2) | 0.0390 (10) | 0.3715 (14) | 0.054* | |
H7B | 1.030 (2) | 0.0628 (11) | 0.4200 (12) | 0.054* | |
H8A | 1.080 (2) | 0.1943 (10) | 0.4694 (10) | 0.054* | |
H8B | 1.093 (2) | 0.1591 (8) | 0.4048 (13) | 0.054* | |
H10A | 0.858 (2) | 0.2701 (9) | 0.7012 (13) | 0.054* | |
H10B | 0.829 (2) | 0.3083 (11) | 0.6337 (10) | 0.054* | |
H11A | 0.975 (2) | 0.1864 (10) | 0.8248 (10) | 0.054* | |
H11B | 1.041 (2) | 0.2204 (9) | 0.8838 (13) | 0.054* | |
H12A | 0.061 (2) | 0.0489 (8) | 0.9377 (14) | 0.054* | |
H12B | 0.0242 (19) | 0.1070 (9) | 0.9524 (15) | 0.054* | |
H9B | 0.940 (5) | 0.282 (3) | 0.545 (5) | 0.31 (5)* | |
H9A | 0.915 (6) | 0.334 (3) | 0.500 (4) | 0.26 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0499 (12) | 0.0571 (12) | 0.0422 (12) | 0.0022 (9) | 0.0129 (9) | −0.0061 (10) |
C2 | 0.0598 (14) | 0.0823 (16) | 0.0446 (13) | 0.0055 (12) | 0.0186 (11) | −0.0081 (12) |
C3 | 0.0754 (17) | 0.0943 (19) | 0.0397 (13) | 0.0024 (15) | 0.0214 (12) | 0.0042 (13) |
C4 | 0.0682 (15) | 0.0743 (15) | 0.0387 (12) | 0.0024 (12) | 0.0107 (11) | 0.0070 (11) |
C5 | 0.098 (2) | 0.103 (2) | 0.0472 (15) | 0.0227 (18) | 0.0174 (14) | 0.0277 (15) |
C6 | 0.096 (2) | 0.092 (2) | 0.0576 (17) | 0.0272 (17) | 0.0099 (15) | 0.0292 (15) |
C7 | 0.0593 (14) | 0.0605 (13) | 0.0523 (14) | 0.0135 (11) | 0.0042 (11) | 0.0122 (11) |
C8 | 0.0654 (15) | 0.0611 (14) | 0.0703 (18) | 0.0193 (12) | 0.0031 (13) | 0.0109 (13) |
C9 | 0.0539 (13) | 0.0602 (14) | 0.0617 (16) | 0.0146 (11) | 0.0098 (11) | −0.0041 (12) |
C10 | 0.0484 (12) | 0.0504 (11) | 0.0501 (13) | 0.0083 (9) | 0.0105 (9) | −0.0046 (10) |
C11 | 0.0466 (11) | 0.0487 (11) | 0.0399 (11) | 0.0015 (9) | 0.0055 (8) | 0.0016 (9) |
C12 | 0.0483 (11) | 0.0515 (11) | 0.0377 (11) | −0.0004 (9) | 0.0066 (9) | 0.0020 (9) |
C13 | 0.0376 (10) | 0.0549 (12) | 0.0511 (13) | −0.0003 (9) | 0.0030 (9) | 0.0004 (10) |
C14 | 0.0371 (11) | 0.0676 (15) | 0.0612 (15) | 0.0073 (10) | 0.0022 (10) | 0.0046 (11) |
C15 | 0.0504 (12) | 0.0562 (13) | 0.0535 (14) | 0.0113 (10) | 0.0106 (10) | 0.0061 (10) |
C16 | 0.0505 (11) | 0.0465 (11) | 0.0375 (11) | 0.0058 (9) | 0.0094 (9) | 0.0028 (9) |
C17 | 0.0697 (15) | 0.0414 (11) | 0.0560 (14) | 0.0022 (10) | 0.0117 (11) | 0.0004 (10) |
C18 | 0.0670 (15) | 0.0417 (11) | 0.0593 (14) | −0.0084 (10) | 0.0081 (11) | −0.0011 (10) |
C19 | 0.0542 (12) | 0.0473 (11) | 0.0397 (12) | −0.0097 (9) | 0.0067 (9) | −0.0011 (9) |
C20 | 0.0529 (13) | 0.0567 (13) | 0.0520 (14) | −0.0168 (10) | 0.0040 (10) | −0.0047 (10) |
C21 | 0.0429 (12) | 0.0729 (16) | 0.0581 (15) | −0.0110 (11) | −0.0015 (10) | −0.0053 (12) |
C22 | 0.0378 (10) | 0.0560 (12) | 0.0533 (13) | −0.0013 (9) | −0.0004 (9) | −0.0029 (10) |
C23 | 0.0399 (10) | 0.0450 (10) | 0.0313 (10) | −0.0028 (8) | 0.0066 (8) | −0.0020 (8) |
C24 | 0.0420 (10) | 0.0435 (10) | 0.0305 (10) | 0.0012 (8) | 0.0073 (8) | 0.0000 (7) |
C25 | 0.0463 (11) | 0.0626 (13) | 0.0418 (12) | −0.0029 (10) | 0.0100 (9) | 0.0062 (10) |
C26 | 0.0595 (14) | 0.0845 (17) | 0.0446 (13) | 0.0006 (13) | 0.0172 (11) | 0.0099 (12) |
C27 | 0.0775 (17) | 0.0931 (19) | 0.0349 (12) | 0.0075 (15) | 0.0159 (12) | 0.0021 (13) |
C28 | 0.0660 (15) | 0.0652 (14) | 0.0341 (12) | 0.0066 (11) | 0.0028 (10) | −0.0015 (10) |
C29 | 0.0893 (19) | 0.0733 (16) | 0.0406 (13) | 0.0024 (14) | −0.0049 (13) | −0.0143 (12) |
C30 | 0.0743 (17) | 0.0577 (13) | 0.0495 (14) | −0.0010 (12) | −0.0146 (12) | −0.0094 (11) |
C31 | 0.0516 (12) | 0.0393 (10) | 0.0515 (13) | 0.0051 (9) | −0.0074 (9) | −0.0024 (9) |
C32 | 0.0527 (13) | 0.0426 (11) | 0.0757 (18) | −0.0058 (9) | −0.0060 (12) | −0.0037 (11) |
C33 | 0.0570 (14) | 0.0502 (12) | 0.0789 (18) | −0.0144 (11) | 0.0137 (12) | 0.0008 (12) |
C34 | 0.0538 (13) | 0.0490 (12) | 0.0582 (14) | −0.0092 (10) | 0.0151 (10) | −0.0002 (10) |
C35 | 0.0450 (11) | 0.0376 (9) | 0.0416 (11) | 0.0051 (8) | 0.0000 (8) | −0.0015 (8) |
C36 | 0.0456 (11) | 0.0471 (10) | 0.0353 (11) | 0.0043 (8) | 0.0013 (8) | 0.0004 (8) |
C37 | 0.0596 (14) | 0.0550 (13) | 0.0554 (14) | 0.0064 (10) | 0.0143 (11) | 0.0030 (11) |
C38 | 0.0661 (15) | 0.0578 (13) | 0.0472 (13) | 0.0091 (11) | 0.0036 (11) | −0.0006 (11) |
C39 | 0.0620 (14) | 0.0526 (13) | 0.0529 (14) | −0.0009 (10) | 0.0049 (11) | 0.0003 (10) |
C40 | 0.0475 (11) | 0.0463 (11) | 0.0486 (12) | 0.0040 (9) | 0.0053 (9) | 0.0024 (9) |
N1 | 0.0415 (9) | 0.0462 (9) | 0.0381 (9) | −0.0006 (7) | 0.0058 (7) | −0.0032 (7) |
N2 | 0.0387 (8) | 0.0459 (9) | 0.0376 (9) | 0.0013 (7) | 0.0054 (7) | 0.0017 (7) |
N3 | 0.0430 (9) | 0.0409 (8) | 0.0420 (10) | −0.0006 (7) | 0.0068 (7) | −0.0007 (7) |
N4 | 0.0389 (8) | 0.0448 (8) | 0.0350 (9) | 0.0004 (7) | 0.0041 (7) | −0.0003 (7) |
N5 | 0.0432 (9) | 0.0434 (9) | 0.0373 (9) | 0.0011 (7) | 0.0079 (7) | −0.0013 (7) |
N6 | 0.0367 (8) | 0.0436 (8) | 0.0355 (9) | −0.0028 (7) | 0.0045 (6) | −0.0018 (7) |
O1 | 0.1122 (16) | 0.0663 (11) | 0.0884 (15) | −0.0131 (11) | 0.0528 (13) | 0.0028 (10) |
O2 | 0.0709 (11) | 0.0558 (9) | 0.0574 (10) | 0.0011 (8) | 0.0144 (8) | −0.0070 (8) |
O3 | 0.1099 (16) | 0.0608 (11) | 0.0865 (15) | −0.0258 (10) | 0.0326 (12) | −0.0070 (10) |
O4 | 0.1127 (16) | 0.0756 (12) | 0.0556 (11) | 0.0096 (11) | 0.0156 (11) | −0.0126 (9) |
O5 | 0.1196 (19) | 0.0806 (15) | 0.0850 (17) | 0.0105 (13) | 0.0342 (14) | −0.0044 (12) |
O6 | 0.1090 (16) | 0.0534 (10) | 0.0704 (13) | 0.0032 (10) | 0.0124 (11) | 0.0011 (9) |
O7 | 0.0891 (14) | 0.0585 (10) | 0.0544 (11) | −0.0093 (9) | 0.0180 (9) | 0.0011 (9) |
O8 | 0.0801 (12) | 0.0551 (10) | 0.0804 (14) | −0.0135 (9) | 0.0223 (10) | −0.0007 (10) |
O9 | 0.175 (3) | 0.108 (2) | 0.100 (2) | 0.001 (2) | 0.036 (2) | 0.0071 (16) |
O10 | 0.1004 (17) | 0.0679 (12) | 0.0972 (17) | −0.0174 (11) | 0.0222 (14) | −0.0086 (12) |
O11 | 0.187 (3) | 0.0608 (12) | 0.0837 (17) | 0.0043 (14) | −0.0429 (17) | −0.0050 (12) |
O12 | 0.142 (2) | 0.0836 (16) | 0.0943 (19) | −0.0146 (15) | −0.0042 (17) | 0.0058 (14) |
Fe1 | 0.03569 (14) | 0.03935 (14) | 0.03331 (15) | −0.00076 (12) | 0.00589 (10) | −0.00136 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.330 (3) | C26—C27 | 1.356 (4) |
C1—C2 | 1.391 (3) | C26—H26 | 0.93 |
C1—H1 | 0.93 | C27—C28 | 1.403 (4) |
C2—C3 | 1.353 (4) | C27—H27 | 0.93 |
C2—H2 | 0.93 | C28—C36 | 1.396 (3) |
C3—C4 | 1.407 (4) | C28—C29 | 1.434 (3) |
C3—H3 | 0.93 | C29—C30 | 1.347 (4) |
C4—C12 | 1.393 (3) | C29—H29 | 0.93 |
C4—C5 | 1.434 (4) | C30—C31 | 1.427 (3) |
C5—C6 | 1.344 (4) | C30—H30 | 0.93 |
C5—H5 | 0.93 | C31—C32 | 1.399 (3) |
C6—C7 | 1.433 (4) | C31—C35 | 1.402 (3) |
C6—H6 | 0.93 | C32—C33 | 1.360 (4) |
C7—C11 | 1.397 (3) | C32—H32 | 0.93 |
C7—C8 | 1.411 (3) | C33—C34 | 1.393 (3) |
C8—C9 | 1.356 (4) | C33—H33 | 0.93 |
C8—H8 | 0.93 | C34—N3 | 1.333 (3) |
C9—C10 | 1.397 (3) | C34—H34 | 0.93 |
C9—H9 | 0.93 | C35—N3 | 1.363 (3) |
C10—N5 | 1.333 (2) | C35—C36 | 1.416 (3) |
C10—H10 | 0.93 | C36—N2 | 1.365 (3) |
C11—N5 | 1.362 (3) | C37—O1 | 1.242 (3) |
C11—C12 | 1.419 (3) | C37—C38 | 1.456 (3) |
C12—N1 | 1.365 (3) | C37—C40 | 1.462 (3) |
C13—N6 | 1.331 (2) | C38—O4 | 1.267 (3) |
C13—C14 | 1.389 (3) | C38—C39 | 1.437 (3) |
C13—H13 | 0.93 | C39—O3 | 1.262 (3) |
C14—C15 | 1.359 (3) | C39—C40 | 1.457 (3) |
C14—H14 | 0.93 | C40—O2 | 1.244 (3) |
C15—C16 | 1.403 (3) | N1—Fe1 | 1.9791 (16) |
C15—H15 | 0.93 | N2—Fe1 | 1.9710 (16) |
C16—C24 | 1.392 (3) | N3—Fe1 | 1.9721 (16) |
C16—C17 | 1.435 (3) | N4—Fe1 | 1.9735 (16) |
C17—C18 | 1.338 (3) | N5—Fe1 | 1.9803 (16) |
C17—H17 | 0.93 | N6—Fe1 | 1.9773 (16) |
C18—C19 | 1.434 (3) | O5—H5A | 0.840 (15) |
C18—H18 | 0.93 | O5—H5B | 0.843 (15) |
C19—C23 | 1.396 (3) | O6—H6A | 0.864 (15) |
C19—C20 | 1.407 (3) | O6—H6B | 0.891 (15) |
C20—C21 | 1.361 (3) | O7—H7A | 0.817 (15) |
C20—H20 | 0.93 | O7—H7B | 0.824 (15) |
C21—C22 | 1.386 (3) | O8—H8A | 0.847 (15) |
C21—H21 | 0.93 | O8—H8B | 0.820 (15) |
C22—N4 | 1.336 (2) | O9—H9B | 0.89 (2) |
C22—H22 | 0.93 | O9—H9A | 0.86 (2) |
C23—N4 | 1.365 (2) | O10—H10A | 0.837 (15) |
C23—C24 | 1.425 (3) | O10—H10B | 0.851 (15) |
C24—N6 | 1.367 (2) | O11—H11A | 0.865 (16) |
C25—N2 | 1.329 (3) | O11—H11B | 0.817 (15) |
C25—C26 | 1.391 (3) | O12—H12A | 0.828 (15) |
C25—H25 | 0.93 | O12—H12B | 0.882 (15) |
| | | |
N1—C1—C2 | 122.6 (2) | C36—C28—C27 | 116.5 (2) |
N1—C1—H1 | 118.7 | C36—C28—C29 | 117.9 (2) |
C2—C1—H1 | 118.7 | C27—C28—C29 | 125.6 (2) |
C3—C2—C1 | 120.0 (2) | C30—C29—C28 | 121.9 (2) |
C3—C2—H2 | 120.0 | C30—C29—H29 | 119.1 |
C1—C2—H2 | 120.0 | C28—C29—H29 | 119.1 |
C2—C3—C4 | 119.6 (2) | C29—C30—C31 | 120.8 (2) |
C2—C3—H3 | 120.2 | C29—C30—H30 | 119.6 |
C4—C3—H3 | 120.2 | C31—C30—H30 | 119.6 |
C12—C4—C3 | 117.0 (2) | C32—C31—C35 | 117.0 (2) |
C12—C4—C5 | 118.0 (2) | C32—C31—C30 | 124.6 (2) |
C3—C4—C5 | 125.1 (2) | C35—C31—C30 | 118.4 (2) |
C6—C5—C4 | 121.4 (2) | C33—C32—C31 | 119.5 (2) |
C6—C5—H5 | 119.3 | C33—C32—H32 | 120.3 |
C4—C5—H5 | 119.3 | C31—C32—H32 | 120.3 |
C5—C6—C7 | 121.4 (2) | C32—C33—C34 | 120.0 (2) |
C5—C6—H6 | 119.3 | C32—C33—H33 | 120.0 |
C7—C6—H6 | 119.3 | C34—C33—H33 | 120.0 |
C11—C7—C8 | 117.2 (2) | N3—C34—C33 | 122.8 (2) |
C11—C7—C6 | 118.0 (2) | N3—C34—H34 | 118.6 |
C8—C7—C6 | 124.8 (2) | C33—C34—H34 | 118.6 |
C9—C8—C7 | 119.1 (2) | N3—C35—C31 | 123.66 (19) |
C9—C8—H8 | 120.5 | N3—C35—C36 | 115.81 (18) |
C7—C8—H8 | 120.5 | C31—C35—C36 | 120.53 (19) |
C8—C9—C10 | 120.3 (2) | N2—C36—C28 | 123.7 (2) |
C8—C9—H9 | 119.9 | N2—C36—C35 | 115.97 (17) |
C10—C9—H9 | 119.9 | C28—C36—C35 | 120.4 (2) |
N5—C10—C9 | 122.6 (2) | O1—C37—C38 | 136.4 (2) |
N5—C10—H10 | 118.7 | O1—C37—C40 | 134.1 (2) |
C9—C10—H10 | 118.7 | C38—C37—C40 | 89.48 (18) |
N5—C11—C7 | 123.64 (19) | O4—C38—C39 | 134.8 (2) |
N5—C11—C12 | 115.96 (18) | O4—C38—C37 | 134.7 (2) |
C7—C11—C12 | 120.40 (19) | C39—C38—C37 | 90.54 (19) |
N1—C12—C4 | 123.3 (2) | O3—C39—C38 | 134.9 (2) |
N1—C12—C11 | 115.93 (18) | O3—C39—C40 | 134.6 (2) |
C4—C12—C11 | 120.7 (2) | C38—C39—C40 | 90.44 (19) |
N6—C13—C14 | 122.7 (2) | O2—C40—C39 | 136.5 (2) |
N6—C13—H13 | 118.6 | O2—C40—C37 | 134.0 (2) |
C14—C13—H13 | 118.6 | C39—C40—C37 | 89.50 (18) |
C15—C14—C13 | 120.7 (2) | C1—N1—C12 | 117.48 (18) |
C15—C14—H14 | 119.7 | C1—N1—Fe1 | 129.75 (15) |
C13—C14—H14 | 119.7 | C12—N1—Fe1 | 112.71 (13) |
C14—C15—C16 | 118.6 (2) | C25—N2—C36 | 117.28 (18) |
C14—C15—H15 | 120.7 | C25—N2—Fe1 | 130.09 (15) |
C16—C15—H15 | 120.7 | C36—N2—Fe1 | 112.63 (13) |
C24—C16—C15 | 117.40 (19) | C34—N3—C35 | 117.04 (18) |
C24—C16—C17 | 118.26 (19) | C34—N3—Fe1 | 130.13 (15) |
C15—C16—C17 | 124.3 (2) | C35—N3—Fe1 | 112.78 (13) |
C18—C17—C16 | 121.2 (2) | C22—N4—C23 | 116.67 (17) |
C18—C17—H17 | 119.4 | C22—N4—Fe1 | 130.36 (14) |
C16—C17—H17 | 119.4 | C23—N4—Fe1 | 112.97 (12) |
C17—C18—C19 | 121.6 (2) | C10—N5—C11 | 117.24 (18) |
C17—C18—H18 | 119.2 | C10—N5—Fe1 | 129.97 (15) |
C19—C18—H18 | 119.2 | C11—N5—Fe1 | 112.78 (13) |
C23—C19—C20 | 117.09 (19) | C13—N6—C24 | 116.60 (17) |
C23—C19—C18 | 118.12 (19) | C13—N6—Fe1 | 130.57 (14) |
C20—C19—C18 | 124.7 (2) | C24—N6—Fe1 | 112.83 (12) |
C21—C20—C19 | 118.9 (2) | H5A—O5—H5B | 105 (2) |
C21—C20—H20 | 120.5 | H6A—O6—H6B | 103.7 (18) |
C19—C20—H20 | 120.5 | H7A—O7—H7B | 115 (2) |
C20—C21—C22 | 120.5 (2) | H8A—O8—H8B | 108.2 (19) |
C20—C21—H21 | 119.8 | H9B—O9—H9A | 102 (3) |
C22—C21—H21 | 119.8 | H10A—O10—H10B | 112 (2) |
N4—C22—C21 | 122.9 (2) | H11A—O11—H11B | 106.9 (19) |
N4—C22—H22 | 118.6 | H12A—O12—H12B | 103 (2) |
C21—C22—H22 | 118.6 | N2—Fe1—N3 | 82.80 (7) |
N4—C23—C19 | 123.98 (18) | N2—Fe1—N4 | 93.58 (7) |
N4—C23—C24 | 115.81 (16) | N3—Fe1—N4 | 174.11 (7) |
C19—C23—C24 | 120.22 (18) | N2—Fe1—N6 | 90.91 (7) |
N6—C24—C16 | 123.89 (18) | N3—Fe1—N6 | 92.67 (6) |
N6—C24—C23 | 115.61 (16) | N4—Fe1—N6 | 82.71 (6) |
C16—C24—C23 | 120.50 (18) | N2—Fe1—N1 | 173.69 (7) |
N2—C25—C26 | 122.8 (2) | N3—Fe1—N1 | 92.45 (7) |
N2—C25—H25 | 118.6 | N4—Fe1—N1 | 91.48 (7) |
C26—C25—H25 | 118.6 | N6—Fe1—N1 | 93.46 (7) |
C27—C26—C25 | 119.6 (2) | N2—Fe1—N5 | 93.37 (7) |
C27—C26—H26 | 120.2 | N3—Fe1—N5 | 91.43 (7) |
C25—C26—H26 | 120.2 | N4—Fe1—N5 | 93.43 (7) |
C26—C27—C28 | 120.2 (2) | N6—Fe1—N5 | 174.41 (7) |
C26—C27—H27 | 119.9 | N1—Fe1—N5 | 82.57 (7) |
C28—C27—H27 | 119.9 | | |
| | | |
N1—C1—C2—C3 | 1.0 (4) | C38—C37—C40—O2 | −178.8 (3) |
C1—C2—C3—C4 | 0.7 (4) | O1—C37—C40—C39 | −175.9 (3) |
C2—C3—C4—C12 | −2.1 (4) | C38—C37—C40—C39 | 1.71 (18) |
C2—C3—C4—C5 | 179.0 (3) | C2—C1—N1—C12 | −1.1 (3) |
C12—C4—C5—C6 | 0.0 (5) | C2—C1—N1—Fe1 | 175.80 (17) |
C3—C4—C5—C6 | 178.9 (3) | C4—C12—N1—C1 | −0.4 (3) |
C4—C5—C6—C7 | −1.0 (5) | C11—C12—N1—C1 | 179.48 (19) |
C5—C6—C7—C11 | 0.9 (5) | C4—C12—N1—Fe1 | −177.87 (18) |
C5—C6—C7—C8 | 179.6 (3) | C11—C12—N1—Fe1 | 2.0 (2) |
C11—C7—C8—C9 | 0.0 (4) | C26—C25—N2—C36 | −1.3 (3) |
C6—C7—C8—C9 | −178.7 (3) | C26—C25—N2—Fe1 | 178.06 (17) |
C7—C8—C9—C10 | −0.7 (4) | C28—C36—N2—C25 | 0.8 (3) |
C8—C9—C10—N5 | 0.5 (4) | C35—C36—N2—C25 | −179.56 (18) |
C8—C7—C11—N5 | 1.0 (4) | C28—C36—N2—Fe1 | −178.68 (17) |
C6—C7—C11—N5 | 179.8 (2) | C35—C36—N2—Fe1 | 1.0 (2) |
C8—C7—C11—C12 | −178.5 (2) | C33—C34—N3—C35 | −0.3 (3) |
C6—C7—C11—C12 | 0.3 (4) | C33—C34—N3—Fe1 | 177.02 (17) |
C3—C4—C12—N1 | 2.0 (4) | C31—C35—N3—C34 | −0.3 (3) |
C5—C4—C12—N1 | −179.0 (2) | C36—C35—N3—C34 | 179.01 (18) |
C3—C4—C12—C11 | −177.9 (2) | C31—C35—N3—Fe1 | −178.07 (15) |
C5—C4—C12—C11 | 1.1 (4) | C36—C35—N3—Fe1 | 1.2 (2) |
N5—C11—C12—N1 | −0.7 (3) | C21—C22—N4—C23 | 0.5 (3) |
C7—C11—C12—N1 | 178.8 (2) | C21—C22—N4—Fe1 | −179.08 (17) |
N5—C11—C12—C4 | 179.2 (2) | C19—C23—N4—C22 | −0.1 (3) |
C7—C11—C12—C4 | −1.3 (3) | C24—C23—N4—C22 | −179.93 (17) |
N6—C13—C14—C15 | −0.3 (4) | C19—C23—N4—Fe1 | 179.50 (15) |
C13—C14—C15—C16 | 1.4 (3) | C24—C23—N4—Fe1 | −0.3 (2) |
C14—C15—C16—C24 | −0.2 (3) | C9—C10—N5—C11 | 0.5 (3) |
C14—C15—C16—C17 | 178.2 (2) | C9—C10—N5—Fe1 | 179.64 (16) |
C24—C16—C17—C18 | 2.2 (3) | C7—C11—N5—C10 | −1.2 (3) |
C15—C16—C17—C18 | −176.2 (2) | C12—C11—N5—C10 | 178.35 (18) |
C16—C17—C18—C19 | −1.8 (4) | C7—C11—N5—Fe1 | 179.49 (18) |
C17—C18—C19—C23 | −0.5 (3) | C12—C11—N5—Fe1 | −1.0 (2) |
C17—C18—C19—C20 | −177.8 (2) | C14—C13—N6—C24 | −1.9 (3) |
C23—C19—C20—C21 | −0.2 (3) | C14—C13—N6—Fe1 | 178.08 (16) |
C18—C19—C20—C21 | 177.1 (2) | C16—C24—N6—C13 | 3.2 (3) |
C19—C20—C21—C22 | 0.6 (4) | C23—C24—N6—C13 | −177.15 (17) |
C20—C21—C22—N4 | −0.7 (4) | C16—C24—N6—Fe1 | −176.78 (15) |
C20—C19—C23—N4 | 0.0 (3) | C23—C24—N6—Fe1 | 2.9 (2) |
C18—C19—C23—N4 | −177.52 (18) | C25—N2—Fe1—N3 | −179.60 (19) |
C20—C19—C23—C24 | 179.81 (18) | C36—N2—Fe1—N3 | −0.26 (13) |
C18—C19—C23—C24 | 2.3 (3) | C25—N2—Fe1—N4 | 5.07 (19) |
C15—C16—C24—N6 | −2.2 (3) | C36—N2—Fe1—N4 | −175.59 (13) |
C17—C16—C24—N6 | 179.31 (18) | C25—N2—Fe1—N6 | 87.82 (19) |
C15—C16—C24—C23 | 178.15 (18) | C36—N2—Fe1—N6 | −92.83 (13) |
C17—C16—C24—C23 | −0.4 (3) | C25—N2—Fe1—N5 | −88.58 (19) |
N4—C23—C24—N6 | −1.8 (2) | C36—N2—Fe1—N5 | 90.76 (13) |
C19—C23—C24—N6 | 178.45 (17) | C34—N3—Fe1—N2 | −177.9 (2) |
N4—C23—C24—C16 | 177.94 (17) | C35—N3—Fe1—N2 | −0.54 (13) |
C19—C23—C24—C16 | −1.9 (3) | C34—N3—Fe1—N6 | −87.36 (19) |
N2—C25—C26—C27 | 0.3 (4) | C35—N3—Fe1—N6 | 90.04 (13) |
C25—C26—C27—C28 | 1.2 (4) | C34—N3—Fe1—N1 | 6.23 (19) |
C26—C27—C28—C36 | −1.6 (4) | C35—N3—Fe1—N1 | −176.38 (13) |
C26—C27—C28—C29 | 177.9 (2) | C34—N3—Fe1—N5 | 88.85 (19) |
C36—C28—C29—C30 | 0.6 (4) | C35—N3—Fe1—N5 | −93.76 (14) |
C27—C28—C29—C30 | −178.9 (3) | C22—N4—Fe1—N2 | −88.52 (18) |
C28—C29—C30—C31 | −1.6 (4) | C23—N4—Fe1—N2 | 91.91 (13) |
C29—C30—C31—C32 | −179.1 (2) | C22—N4—Fe1—N6 | −178.98 (19) |
C29—C30—C31—C35 | 0.6 (3) | C23—N4—Fe1—N6 | 1.45 (13) |
C35—C31—C32—C33 | −0.1 (3) | C22—N4—Fe1—N1 | 87.72 (18) |
C30—C31—C32—C33 | 179.7 (2) | C23—N4—Fe1—N1 | −91.85 (13) |
C31—C32—C33—C34 | −0.5 (4) | C22—N4—Fe1—N5 | 5.08 (19) |
C32—C33—C34—N3 | 0.7 (4) | C23—N4—Fe1—N5 | −174.49 (13) |
C32—C31—C35—N3 | 0.5 (3) | C13—N6—Fe1—N2 | 84.18 (18) |
C30—C31—C35—N3 | −179.27 (19) | C24—N6—Fe1—N2 | −95.88 (13) |
C32—C31—C35—C36 | −178.80 (19) | C13—N6—Fe1—N3 | 1.34 (19) |
C30—C31—C35—C36 | 1.4 (3) | C24—N6—Fe1—N3 | −178.71 (13) |
C27—C28—C36—N2 | 0.7 (3) | C13—N6—Fe1—N4 | 177.67 (19) |
C29—C28—C36—N2 | −178.9 (2) | C24—N6—Fe1—N4 | −2.38 (12) |
C27—C28—C36—C35 | −179.0 (2) | C13—N6—Fe1—N1 | −91.27 (18) |
C29—C28—C36—C35 | 1.4 (3) | C24—N6—Fe1—N1 | 88.67 (13) |
N3—C35—C36—N2 | −1.5 (3) | C1—N1—Fe1—N3 | −87.91 (18) |
C31—C35—C36—N2 | 177.82 (17) | C12—N1—Fe1—N3 | 89.14 (14) |
N3—C35—C36—C28 | 178.19 (18) | C1—N1—Fe1—N4 | 87.70 (18) |
C31—C35—C36—C28 | −2.5 (3) | C12—N1—Fe1—N4 | −95.25 (14) |
O1—C37—C38—O4 | −4.1 (5) | C1—N1—Fe1—N6 | 4.91 (19) |
C40—C37—C38—O4 | 178.4 (3) | C12—N1—Fe1—N6 | −178.03 (14) |
O1—C37—C38—C39 | 175.8 (3) | C1—N1—Fe1—N5 | −179.04 (19) |
C40—C37—C38—C39 | −1.73 (18) | C12—N1—Fe1—N5 | −1.98 (13) |
O4—C38—C39—O3 | 3.5 (5) | C10—N5—Fe1—N2 | 7.25 (19) |
C37—C38—C39—O3 | −176.3 (3) | C11—N5—Fe1—N2 | −173.54 (14) |
O4—C38—C39—C40 | −178.4 (3) | C10—N5—Fe1—N3 | 90.11 (18) |
C37—C38—C39—C40 | 1.74 (18) | C11—N5—Fe1—N3 | −90.67 (14) |
O3—C39—C40—O2 | −3.1 (5) | C10—N5—Fe1—N4 | −86.55 (18) |
C38—C39—C40—O2 | 178.8 (3) | C11—N5—Fe1—N4 | 92.66 (14) |
O3—C39—C40—C37 | 176.4 (3) | C10—N5—Fe1—N1 | −177.60 (19) |
C38—C39—C40—C37 | −1.73 (18) | C11—N5—Fe1—N1 | 1.61 (14) |
O1—C37—C40—O2 | 3.6 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O12i | 0.84 (2) | 2.13 (2) | 2.878 (4) | 149 (2) |
O5—H5B···O6 | 0.84 (2) | 1.91 (2) | 2.731 (3) | 163 (2) |
O6—H6A···O7ii | 0.86 (2) | 1.97 (2) | 2.816 (3) | 166 (2) |
O6—H6B···O10iii | 0.89 (2) | 1.81 (2) | 2.677 (3) | 166 (2) |
O7—H7A···O1ii | 0.82 (2) | 2.01 (2) | 2.811 (3) | 166 (3) |
O7—H7B···O2 | 0.82 (2) | 1.92 (2) | 2.737 (2) | 169 (2) |
O8—H8A···O3 | 0.85 (2) | 1.88 (2) | 2.722 (3) | 173 (2) |
O8—H8B···O7 | 0.82 (2) | 2.02 (2) | 2.832 (3) | 169 (2) |
O9—H9B···O3 | 0.89 (2) | 1.94 (3) | 2.782 (4) | 157 (7) |
O9—H9A···O11iv | 0.86 (2) | 2.53 (6) | 3.147 (5) | 129 (6) |
O10—H10A···O4 | 0.84 (2) | 1.94 (2) | 2.745 (3) | 160 (2) |
O10—H10B···O9 | 0.85 (2) | 1.95 (2) | 2.786 (4) | 165 (2) |
O11—H11A···O4 | 0.87 (2) | 1.86 (2) | 2.720 (3) | 173 (2) |
O11—H11B···O8v | 0.82 (2) | 2.00 (2) | 2.808 (3) | 170 (2) |
O12—H12A···O5vi | 0.83 (2) | 1.96 (2) | 2.775 (4) | 168 (2) |
O12—H12B···O11vi | 0.88 (2) | 2.13 (2) | 2.771 (3) | 129 (2) |
C20—H20···O2v | 0.93 | 2.57 | 3.267 (3) | 132 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+2, −y, −z+1; (iii) −x+2, y−1/2, −z+3/2; (iv) x, −y+1/2, z−1/2; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z. |