In the ionic structure of the title compound, [Fe(C
12H
8N
2)
3](C
9H
5N
4O
2)
2·H
2O, the octahedral tris-chelate [Fe(phen)
3]
2+ dications [Fe—N = 1.9647 (14)–1.9769 (14) Å; phen is 1,10-phenathroline] afford one-dimensional chains by a series of slipped π–π stacking interactions [centroid-to-centroid distances = 3.792 (3) and 3.939 (3) Å]. The 1,1,3,3-tetracyano-2-(2-hydroxyethyl)propenide anions, denoted tcnoetOH
−, reveal an appreciable delocalization of π-electron density, involving the central propenide [C—C = 1.383 (3)–1.401 (2) Å] fragment and four nitrile groups, and this is also supported by density functional theory (DFT) calculations at the B97D/6-311+G(2d,2p) level. Primary noncovalent inter-moiety interactions comprise conventional O—H
O(N) and weak C—H
O(N) hydrogen bonding [O
O(N) = 2.833 (2)–3.289 (5) Å and C
O(N) = 3.132 (2)–3.439 (2) Å]. The double anion
π interaction involving a nitrile group of tcnoetOH
− and two
cis-positioned pyridine rings (`π-pocket') of [Fe(phen)
3]
2+ [N
centroid = 3.212 (2) and 3.418 (2) Å] suggest the relevance of anion
π stackings for charge-diffuse polycyanoanions and common
M-chelate species.
Supporting information
CCDC reference: 964427
Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).
Tris(1,10-phenanthroline-
κ2N,
N')iron(II)
bis[1,1,3,3-tetracyano-2-(2-hydroxyethyl)propenide] monohydrate
top
Crystal data top
[Fe(C12H8N2)3](C9H5N4O2)2·H2O | Z = 2 |
Mr = 1016.82 | F(000) = 1048 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
a = 9.8498 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.9871 (3) Å | Cell parameters from 12148 reflections |
c = 18.8001 (4) Å | θ = 3.7–29.3° |
α = 83.7705 (18)° | µ = 0.38 mm−1 |
β = 89.3525 (18)° | T = 120 K |
γ = 85.6990 (17)° | Prism, red |
V = 2383.97 (9) Å3 | 0.35 × 0.35 × 0.15 mm |
Data collection top
Agilent Xcalibur diffractometer | 10732 independent reflections |
Radiation source: fine-focus sealed tube | 9151 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013) | h = −12→12 |
Tmin = 0.789, Tmax = 0.945 | k = −16→16 |
34906 measured reflections | l = −24→24 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0371P)2 + 2.1221P] where P = (Fo2 + 2Fc2)/3 |
10732 reflections | (Δ/σ)max = 0.001 |
704 parameters | Δρmax = 0.76 e Å−3 |
32 restraints | Δρmin = −0.66 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | Occ. (<1) |
Fe1 | 0.59379 (2) | 0.538465 (18) | 0.251541 (12) | 0.01471 (7) | |
O1 | 0.96427 (12) | 0.02118 (9) | 0.14394 (7) | 0.0240 (3) | |
O2 | 0.92939 (17) | 0.21771 (12) | 0.19213 (9) | 0.0447 (4) | |
H1O | 0.8576 | 0.1981 | 0.1747 | 0.067* | |
O1W | 0.66432 (15) | 0.16739 (12) | 0.15859 (8) | 0.0394 (4) | |
H1W | 0.6624 | 0.1407 | 0.1193 | 0.059* | |
H2W | 0.5834 | 0.1744 | 0.1744 | 0.059* | |
N1 | 0.73687 (13) | 0.60217 (11) | 0.30025 (7) | 0.0159 (3) | |
N2 | 0.55618 (14) | 0.68082 (11) | 0.20557 (7) | 0.0169 (3) | |
N3 | 0.45420 (14) | 0.48096 (11) | 0.19595 (7) | 0.0169 (3) | |
N4 | 0.71209 (13) | 0.50262 (10) | 0.17098 (7) | 0.0160 (3) | |
N5 | 0.46658 (13) | 0.56023 (11) | 0.33122 (7) | 0.0177 (3) | |
N6 | 0.63230 (13) | 0.40115 (11) | 0.30678 (7) | 0.0171 (3) | |
N7 | 0.8041 (2) | −0.26357 (15) | 0.04203 (11) | 0.0450 (5) | |
N8 | 0.7404 (2) | 0.07197 (16) | 0.01265 (11) | 0.0468 (5) | |
N9 | 1.18717 (18) | −0.14473 (13) | 0.27743 (9) | 0.0313 (4) | |
N10 | 1.12569 (16) | −0.32841 (13) | 0.10975 (9) | 0.0291 (4) | |
N11 | 0.0528 (2) | 0.39363 (19) | 0.30337 (14) | 0.0673 (8) | |
N12 | 0.41826 (19) | 0.21370 (16) | 0.24398 (10) | 0.0420 (5) | |
N13 | 0.1539 (3) | 0.0235 (2) | 0.55767 (12) | 0.0620 (7) | |
N14 | −0.0578 (2) | 0.3139 (2) | 0.46717 (11) | 0.0589 (7) | |
C1 | 0.73540 (16) | 0.70693 (13) | 0.28219 (8) | 0.0161 (3) | |
C2 | 0.82943 (17) | 0.55889 (14) | 0.34771 (9) | 0.0193 (3) | |
H2 | 0.8325 | 0.4860 | 0.3609 | 0.023* | |
C3 | 0.92241 (18) | 0.61704 (15) | 0.37890 (9) | 0.0231 (4) | |
H3 | 0.9872 | 0.5834 | 0.4124 | 0.028* | |
C4 | 0.92016 (17) | 0.72225 (15) | 0.36118 (9) | 0.0233 (4) | |
H4 | 0.9827 | 0.7620 | 0.3824 | 0.028* | |
C5 | 0.82392 (17) | 0.77084 (14) | 0.31111 (9) | 0.0196 (3) | |
C6 | 0.81197 (18) | 0.87989 (14) | 0.28742 (10) | 0.0236 (4) | |
H6 | 0.8703 | 0.9244 | 0.3071 | 0.028* | |
C7 | 0.71943 (18) | 0.92068 (14) | 0.23760 (10) | 0.0231 (4) | |
H7 | 0.7144 | 0.9931 | 0.2227 | 0.028* | |
C8 | 0.62858 (17) | 0.85624 (13) | 0.20681 (9) | 0.0201 (3) | |
C9 | 0.53096 (18) | 0.89252 (14) | 0.15422 (10) | 0.0242 (4) | |
H9 | 0.5214 | 0.9640 | 0.1363 | 0.029* | |
C10 | 0.44959 (18) | 0.82320 (15) | 0.12906 (10) | 0.0248 (4) | |
H10 | 0.3833 | 0.8464 | 0.0934 | 0.030* | |
C11 | 0.46460 (17) | 0.71842 (14) | 0.15606 (9) | 0.0212 (3) | |
H11 | 0.4068 | 0.6718 | 0.1382 | 0.025* | |
C12 | 0.63765 (16) | 0.74992 (13) | 0.22994 (8) | 0.0168 (3) | |
C13 | 0.50599 (16) | 0.44094 (12) | 0.13640 (9) | 0.0167 (3) | |
C14 | 0.32206 (17) | 0.47443 (13) | 0.20872 (9) | 0.0203 (3) | |
H14 | 0.2837 | 0.5014 | 0.2501 | 0.024* | |
C15 | 0.23711 (17) | 0.42934 (14) | 0.16361 (10) | 0.0227 (4) | |
H15 | 0.1430 | 0.4265 | 0.1747 | 0.027* | |
C16 | 0.28861 (18) | 0.38940 (14) | 0.10375 (10) | 0.0226 (4) | |
H16 | 0.2310 | 0.3593 | 0.0729 | 0.027* | |
C17 | 0.42813 (17) | 0.39367 (13) | 0.08873 (9) | 0.0193 (3) | |
C18 | 0.49476 (18) | 0.35370 (14) | 0.02829 (10) | 0.0240 (4) | |
H18 | 0.4437 | 0.3206 | −0.0040 | 0.029* | |
C19 | 0.62960 (19) | 0.36249 (14) | 0.01650 (9) | 0.0236 (4) | |
H19 | 0.6720 | 0.3337 | −0.0232 | 0.028* | |
C20 | 0.70943 (17) | 0.41443 (13) | 0.06287 (9) | 0.0192 (3) | |
C21 | 0.84730 (17) | 0.43195 (14) | 0.05105 (9) | 0.0215 (3) | |
H21 | 0.8953 | 0.4063 | 0.0117 | 0.026* | |
C22 | 0.91122 (17) | 0.48700 (14) | 0.09757 (9) | 0.0209 (3) | |
H22 | 1.0031 | 0.5027 | 0.0892 | 0.025* | |
C23 | 0.84133 (17) | 0.51993 (13) | 0.15718 (9) | 0.0189 (3) | |
H23 | 0.8884 | 0.5563 | 0.1892 | 0.023* | |
C24 | 0.64661 (16) | 0.45213 (12) | 0.12285 (8) | 0.0165 (3) | |
C25 | 0.46238 (16) | 0.47442 (14) | 0.37975 (9) | 0.0188 (3) | |
C26 | 0.38477 (17) | 0.64349 (14) | 0.34285 (9) | 0.0223 (4) | |
H26 | 0.3865 | 0.7043 | 0.3100 | 0.027* | |
C27 | 0.29649 (18) | 0.64445 (16) | 0.40179 (10) | 0.0275 (4) | |
H27 | 0.2403 | 0.7054 | 0.4084 | 0.033* | |
C28 | 0.29101 (18) | 0.55802 (17) | 0.44974 (10) | 0.0286 (4) | |
H28 | 0.2305 | 0.5582 | 0.4894 | 0.034* | |
C29 | 0.37585 (18) | 0.46885 (15) | 0.43968 (9) | 0.0239 (4) | |
C30 | 0.3808 (2) | 0.37399 (17) | 0.48643 (10) | 0.0305 (4) | |
H30 | 0.3216 | 0.3685 | 0.5267 | 0.037* | |
C31 | 0.4676 (2) | 0.29228 (16) | 0.47449 (10) | 0.0304 (4) | |
H31 | 0.4689 | 0.2306 | 0.5067 | 0.037* | |
C32 | 0.55820 (19) | 0.29663 (14) | 0.41407 (10) | 0.0240 (4) | |
C33 | 0.6534 (2) | 0.21571 (15) | 0.39900 (10) | 0.0287 (4) | |
H33 | 0.6613 | 0.1524 | 0.4296 | 0.034* | |
C34 | 0.73433 (19) | 0.22933 (14) | 0.33967 (11) | 0.0273 (4) | |
H34 | 0.7996 | 0.1754 | 0.3291 | 0.033* | |
C35 | 0.72123 (17) | 0.32269 (13) | 0.29429 (10) | 0.0210 (3) | |
H35 | 0.7779 | 0.3302 | 0.2531 | 0.025* | |
C36 | 0.55274 (17) | 0.38776 (13) | 0.36669 (9) | 0.0191 (3) | |
C37 | 0.84090 (19) | −0.18682 (16) | 0.05638 (10) | 0.0283 (4) | |
C38 | 0.87932 (18) | −0.08890 (14) | 0.07257 (9) | 0.0220 (4) | |
C39 | 0.8037 (2) | 0.00052 (16) | 0.03914 (10) | 0.0296 (4) | |
C40 | 0.97440 (17) | −0.07576 (13) | 0.12490 (9) | 0.0188 (3) | |
C41 | 1.06695 (17) | −0.15301 (13) | 0.15784 (9) | 0.0197 (3) | |
C42 | 1.09606 (17) | −0.24945 (14) | 0.12995 (9) | 0.0208 (3) | |
C43 | 1.13246 (17) | −0.14552 (13) | 0.22383 (10) | 0.0219 (4) | |
C44 | 1.08005 (19) | 0.07166 (14) | 0.16574 (12) | 0.0292 (4) | |
H44A | 1.1620 | 0.0519 | 0.1379 | 0.035* | |
H44B | 1.0990 | 0.0524 | 0.2173 | 0.035* | |
C45 | 1.0411 (2) | 0.18589 (15) | 0.15097 (13) | 0.0360 (5) | |
H45A | 1.1198 | 0.2250 | 0.1613 | 0.043* | |
H45B | 1.0188 | 0.2026 | 0.0996 | 0.043* | |
C46 | 0.1298 (2) | 0.32366 (18) | 0.31953 (13) | 0.0418 (5) | |
C47 | 0.2262 (2) | 0.23829 (17) | 0.33580 (11) | 0.0325 (4) | |
C48 | 0.3335 (2) | 0.22526 (17) | 0.28522 (12) | 0.0347 (5) | |
C49 | 0.2233 (2) | 0.17089 (18) | 0.39795 (12) | 0.0372 (5) | |
C50 | 0.1305 (2) | 0.17046 (19) | 0.45441 (11) | 0.0370 (5) | |
C51 | 0.0254 (2) | 0.2497 (2) | 0.46010 (11) | 0.0414 (6) | |
C52 | 0.1435 (2) | 0.0892 (2) | 0.51145 (13) | 0.0453 (6) | |
O3A | 0.33382 (17) | 0.09998 (13) | 0.40821 (9) | 0.0309 (4) | 0.858 (3) |
O4A | 0.5220 (4) | −0.0677 (2) | 0.43724 (16) | 0.0944 (12) | 0.858 (3) |
H2OA | 0.6055 | −0.0549 | 0.4359 | 0.142* | 0.858 (3) |
C53A | 0.3222 (3) | 0.0086 (2) | 0.37385 (16) | 0.0421 (6) | 0.858 (3) |
H53A | 0.2827 | 0.0264 | 0.3255 | 0.051* | 0.858 (3) |
H53B | 0.2633 | −0.0392 | 0.4021 | 0.051* | 0.858 (3) |
C54A | 0.4650 (3) | −0.04052 (19) | 0.36923 (14) | 0.0361 (6) | 0.858 (3) |
H54A | 0.4638 | −0.1035 | 0.3439 | 0.043* | 0.858 (3) |
H54B | 0.5223 | 0.0087 | 0.3411 | 0.043* | 0.858 (3) |
O3B | 0.2652 (10) | 0.0665 (5) | 0.3893 (6) | 0.039 (2) | 0.142 (3) |
O4B | 0.4294 (9) | −0.1314 (7) | 0.3724 (5) | 0.027 (2) | 0.142 (3) |
H2OB | 0.3490 | −0.1226 | 0.3558 | 0.041* | 0.142 (3) |
C53B | 0.4007 (12) | 0.0332 (9) | 0.4125 (9) | 0.036 (2) | 0.142 (3) |
H53C | 0.4197 | 0.0713 | 0.4537 | 0.043* | 0.142 (3) |
H53D | 0.4630 | 0.0570 | 0.3734 | 0.043* | 0.142 (3) |
C54B | 0.4413 (19) | −0.0804 (9) | 0.4344 (7) | 0.044 (2) | 0.142 (3) |
H54C | 0.5361 | −0.0894 | 0.4522 | 0.053* | 0.142 (3) |
H54D | 0.3803 | −0.1087 | 0.4727 | 0.053* | 0.142 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01306 (11) | 0.01616 (12) | 0.01518 (11) | −0.00012 (8) | −0.00211 (8) | −0.00338 (9) |
O1 | 0.0212 (6) | 0.0162 (6) | 0.0351 (7) | 0.0002 (5) | −0.0033 (5) | −0.0064 (5) |
O2 | 0.0461 (9) | 0.0316 (8) | 0.0591 (10) | 0.0027 (7) | 0.0069 (8) | −0.0216 (8) |
O1W | 0.0382 (8) | 0.0388 (9) | 0.0381 (8) | 0.0089 (7) | 0.0078 (7) | 0.0009 (7) |
N1 | 0.0150 (6) | 0.0181 (7) | 0.0148 (6) | 0.0009 (5) | −0.0004 (5) | −0.0034 (5) |
N2 | 0.0154 (6) | 0.0196 (7) | 0.0160 (6) | 0.0003 (5) | −0.0017 (5) | −0.0040 (5) |
N3 | 0.0154 (6) | 0.0163 (7) | 0.0189 (7) | −0.0003 (5) | −0.0017 (5) | −0.0022 (5) |
N4 | 0.0156 (6) | 0.0165 (7) | 0.0162 (6) | −0.0010 (5) | −0.0029 (5) | −0.0022 (5) |
N5 | 0.0140 (6) | 0.0214 (7) | 0.0180 (7) | 0.0006 (5) | −0.0028 (5) | −0.0049 (6) |
N6 | 0.0144 (6) | 0.0180 (7) | 0.0194 (7) | −0.0016 (5) | −0.0025 (5) | −0.0040 (5) |
N7 | 0.0437 (11) | 0.0394 (11) | 0.0549 (12) | −0.0014 (9) | −0.0248 (10) | −0.0169 (9) |
N8 | 0.0474 (12) | 0.0452 (12) | 0.0437 (11) | 0.0073 (9) | −0.0179 (9) | 0.0082 (9) |
N9 | 0.0362 (9) | 0.0267 (9) | 0.0314 (9) | 0.0032 (7) | −0.0123 (7) | −0.0065 (7) |
N10 | 0.0251 (8) | 0.0263 (9) | 0.0376 (9) | 0.0025 (6) | −0.0035 (7) | −0.0132 (7) |
N11 | 0.0575 (14) | 0.0568 (15) | 0.0784 (17) | 0.0228 (12) | 0.0378 (13) | 0.0123 (13) |
N12 | 0.0348 (10) | 0.0482 (12) | 0.0390 (10) | 0.0151 (8) | 0.0063 (8) | −0.0004 (9) |
N13 | 0.0802 (17) | 0.0701 (16) | 0.0325 (11) | 0.0194 (13) | 0.0019 (11) | −0.0088 (11) |
N14 | 0.0460 (12) | 0.0965 (19) | 0.0328 (10) | 0.0298 (12) | −0.0027 (9) | −0.0241 (11) |
C1 | 0.0156 (7) | 0.0190 (8) | 0.0142 (7) | −0.0009 (6) | 0.0016 (6) | −0.0036 (6) |
C2 | 0.0179 (8) | 0.0219 (8) | 0.0180 (8) | 0.0024 (6) | −0.0018 (6) | −0.0034 (6) |
C3 | 0.0190 (8) | 0.0303 (10) | 0.0200 (8) | 0.0011 (7) | −0.0058 (7) | −0.0046 (7) |
C4 | 0.0190 (8) | 0.0305 (10) | 0.0224 (8) | −0.0060 (7) | −0.0029 (7) | −0.0082 (7) |
C5 | 0.0171 (8) | 0.0241 (9) | 0.0186 (8) | −0.0030 (6) | 0.0012 (6) | −0.0056 (7) |
C6 | 0.0244 (9) | 0.0220 (9) | 0.0259 (9) | −0.0077 (7) | 0.0024 (7) | −0.0061 (7) |
C7 | 0.0255 (9) | 0.0180 (8) | 0.0261 (9) | −0.0041 (7) | 0.0045 (7) | −0.0021 (7) |
C8 | 0.0208 (8) | 0.0198 (8) | 0.0196 (8) | −0.0008 (6) | 0.0029 (7) | −0.0023 (6) |
C9 | 0.0262 (9) | 0.0199 (9) | 0.0249 (9) | 0.0019 (7) | 0.0008 (7) | 0.0026 (7) |
C10 | 0.0231 (9) | 0.0284 (10) | 0.0213 (8) | 0.0030 (7) | −0.0049 (7) | 0.0022 (7) |
C11 | 0.0195 (8) | 0.0244 (9) | 0.0196 (8) | 0.0007 (7) | −0.0045 (7) | −0.0036 (7) |
C12 | 0.0170 (7) | 0.0194 (8) | 0.0144 (7) | −0.0011 (6) | 0.0011 (6) | −0.0034 (6) |
C13 | 0.0177 (8) | 0.0152 (8) | 0.0170 (7) | −0.0003 (6) | −0.0029 (6) | −0.0012 (6) |
C14 | 0.0163 (8) | 0.0208 (8) | 0.0237 (8) | −0.0001 (6) | −0.0009 (7) | −0.0029 (7) |
C15 | 0.0151 (8) | 0.0233 (9) | 0.0297 (9) | −0.0017 (6) | −0.0047 (7) | −0.0017 (7) |
C16 | 0.0205 (8) | 0.0206 (8) | 0.0273 (9) | −0.0045 (7) | −0.0082 (7) | −0.0030 (7) |
C17 | 0.0196 (8) | 0.0172 (8) | 0.0213 (8) | −0.0030 (6) | −0.0050 (7) | −0.0012 (6) |
C18 | 0.0271 (9) | 0.0244 (9) | 0.0221 (8) | −0.0049 (7) | −0.0056 (7) | −0.0072 (7) |
C19 | 0.0272 (9) | 0.0264 (9) | 0.0185 (8) | −0.0032 (7) | −0.0004 (7) | −0.0073 (7) |
C20 | 0.0211 (8) | 0.0191 (8) | 0.0172 (8) | −0.0014 (6) | −0.0016 (6) | −0.0016 (6) |
C21 | 0.0215 (8) | 0.0267 (9) | 0.0160 (8) | 0.0002 (7) | 0.0016 (6) | −0.0026 (7) |
C22 | 0.0152 (8) | 0.0271 (9) | 0.0197 (8) | −0.0024 (7) | −0.0008 (6) | 0.0006 (7) |
C23 | 0.0172 (8) | 0.0218 (8) | 0.0180 (8) | −0.0024 (6) | −0.0031 (6) | −0.0024 (6) |
C24 | 0.0180 (8) | 0.0153 (8) | 0.0160 (7) | −0.0015 (6) | −0.0037 (6) | −0.0007 (6) |
C25 | 0.0159 (7) | 0.0245 (9) | 0.0173 (8) | −0.0045 (6) | −0.0026 (6) | −0.0050 (7) |
C26 | 0.0183 (8) | 0.0264 (9) | 0.0224 (8) | 0.0028 (7) | −0.0043 (7) | −0.0063 (7) |
C27 | 0.0180 (8) | 0.0378 (11) | 0.0276 (9) | 0.0058 (7) | −0.0018 (7) | −0.0135 (8) |
C28 | 0.0192 (8) | 0.0454 (12) | 0.0228 (9) | −0.0034 (8) | 0.0033 (7) | −0.0107 (8) |
C29 | 0.0188 (8) | 0.0350 (10) | 0.0192 (8) | −0.0070 (7) | −0.0004 (7) | −0.0060 (7) |
C30 | 0.0306 (10) | 0.0422 (12) | 0.0204 (9) | −0.0141 (9) | 0.0049 (8) | −0.0035 (8) |
C31 | 0.0379 (11) | 0.0312 (10) | 0.0228 (9) | −0.0146 (9) | −0.0021 (8) | 0.0029 (8) |
C32 | 0.0265 (9) | 0.0237 (9) | 0.0222 (8) | −0.0069 (7) | −0.0048 (7) | −0.0001 (7) |
C33 | 0.0352 (10) | 0.0197 (9) | 0.0302 (10) | −0.0037 (8) | −0.0083 (8) | 0.0036 (7) |
C34 | 0.0269 (9) | 0.0198 (9) | 0.0347 (10) | 0.0037 (7) | −0.0065 (8) | −0.0031 (8) |
C35 | 0.0185 (8) | 0.0200 (8) | 0.0249 (9) | −0.0002 (6) | −0.0024 (7) | −0.0043 (7) |
C36 | 0.0172 (8) | 0.0224 (8) | 0.0185 (8) | −0.0053 (6) | −0.0030 (6) | −0.0029 (7) |
C37 | 0.0242 (9) | 0.0344 (11) | 0.0268 (9) | 0.0009 (8) | −0.0101 (7) | −0.0069 (8) |
C38 | 0.0216 (8) | 0.0236 (9) | 0.0206 (8) | 0.0001 (7) | −0.0021 (7) | −0.0022 (7) |
C39 | 0.0282 (10) | 0.0352 (11) | 0.0247 (9) | −0.0015 (8) | −0.0054 (8) | 0.0000 (8) |
C40 | 0.0187 (8) | 0.0184 (8) | 0.0195 (8) | −0.0013 (6) | 0.0027 (6) | −0.0036 (6) |
C41 | 0.0193 (8) | 0.0189 (8) | 0.0214 (8) | 0.0003 (6) | −0.0022 (6) | −0.0063 (7) |
C42 | 0.0157 (8) | 0.0239 (9) | 0.0232 (8) | 0.0000 (6) | −0.0028 (6) | −0.0047 (7) |
C43 | 0.0217 (8) | 0.0168 (8) | 0.0276 (9) | 0.0016 (6) | −0.0025 (7) | −0.0052 (7) |
C44 | 0.0249 (9) | 0.0220 (9) | 0.0424 (11) | −0.0049 (7) | −0.0017 (8) | −0.0091 (8) |
C45 | 0.0383 (11) | 0.0217 (10) | 0.0490 (13) | −0.0068 (8) | 0.0068 (10) | −0.0057 (9) |
C46 | 0.0344 (11) | 0.0379 (12) | 0.0513 (14) | 0.0028 (10) | 0.0203 (10) | −0.0030 (10) |
C47 | 0.0240 (9) | 0.0381 (11) | 0.0358 (11) | 0.0039 (8) | 0.0032 (8) | −0.0105 (9) |
C48 | 0.0282 (10) | 0.0373 (12) | 0.0369 (11) | 0.0086 (8) | −0.0015 (9) | −0.0047 (9) |
C49 | 0.0302 (10) | 0.0439 (13) | 0.0373 (11) | 0.0095 (9) | −0.0002 (9) | −0.0121 (10) |
C50 | 0.0315 (11) | 0.0494 (13) | 0.0303 (10) | 0.0051 (9) | 0.0002 (8) | −0.0106 (9) |
C51 | 0.0304 (11) | 0.0708 (17) | 0.0234 (10) | 0.0104 (11) | −0.0012 (8) | −0.0161 (10) |
C52 | 0.0442 (13) | 0.0603 (16) | 0.0316 (12) | 0.0092 (11) | 0.0031 (10) | −0.0149 (11) |
O3A | 0.0271 (9) | 0.0318 (9) | 0.0363 (9) | 0.0006 (7) | −0.0053 (7) | −0.0164 (7) |
O4A | 0.125 (3) | 0.0537 (15) | 0.101 (2) | 0.0385 (17) | −0.075 (2) | −0.0142 (15) |
C53A | 0.0445 (15) | 0.0368 (14) | 0.0493 (16) | −0.0094 (12) | −0.0042 (12) | −0.0190 (12) |
C54A | 0.0388 (13) | 0.0248 (12) | 0.0445 (14) | 0.0119 (10) | −0.0065 (11) | −0.0118 (10) |
O3B | 0.029 (4) | 0.040 (4) | 0.044 (4) | 0.020 (4) | 0.007 (4) | −0.006 (4) |
O4B | 0.029 (5) | 0.024 (5) | 0.027 (5) | 0.005 (4) | −0.009 (4) | 0.002 (4) |
C53B | 0.034 (4) | 0.028 (4) | 0.048 (5) | 0.001 (4) | −0.011 (4) | −0.016 (4) |
C54B | 0.037 (4) | 0.030 (4) | 0.065 (5) | 0.007 (4) | 0.001 (4) | −0.011 (4) |
Geometric parameters (Å, º) top
Fe1—N2 | 1.9647 (14) | C19—H19 | 0.9500 |
Fe1—N1 | 1.9692 (14) | C20—C24 | 1.397 (2) |
Fe1—N5 | 1.9724 (14) | C20—C21 | 1.405 (2) |
Fe1—N3 | 1.9739 (14) | C21—C22 | 1.374 (2) |
Fe1—N4 | 1.9748 (14) | C21—H21 | 0.9500 |
Fe1—N6 | 1.9769 (14) | C22—C23 | 1.398 (2) |
O1—C40 | 1.342 (2) | C22—H22 | 0.9500 |
O1—C44 | 1.442 (2) | C23—H23 | 0.9500 |
O2—C45 | 1.401 (3) | C25—C29 | 1.404 (2) |
O2—H1O | 0.8499 | C25—C36 | 1.423 (2) |
O1W—H1W | 0.8499 | C26—C27 | 1.401 (3) |
O1W—H2W | 0.8500 | C26—H26 | 0.9500 |
N1—C2 | 1.333 (2) | C27—C28 | 1.365 (3) |
N1—C1 | 1.365 (2) | C27—H27 | 0.9500 |
N2—C11 | 1.331 (2) | C28—C29 | 1.405 (3) |
N2—C12 | 1.366 (2) | C28—H28 | 0.9500 |
N3—C14 | 1.328 (2) | C29—C30 | 1.432 (3) |
N3—C13 | 1.363 (2) | C30—C31 | 1.349 (3) |
N4—C23 | 1.327 (2) | C30—H30 | 0.9500 |
N4—C24 | 1.368 (2) | C31—C32 | 1.435 (3) |
N5—C26 | 1.335 (2) | C31—H31 | 0.9500 |
N5—C25 | 1.364 (2) | C32—C36 | 1.400 (2) |
N6—C35 | 1.332 (2) | C32—C33 | 1.405 (3) |
N6—C36 | 1.368 (2) | C33—C34 | 1.367 (3) |
N7—C37 | 1.146 (3) | C33—H33 | 0.9500 |
N8—C39 | 1.148 (3) | C34—C35 | 1.403 (3) |
N9—C43 | 1.150 (2) | C34—H34 | 0.9500 |
N10—C42 | 1.148 (2) | C35—H35 | 0.9500 |
N11—C46 | 1.156 (3) | C37—C38 | 1.418 (3) |
N12—C48 | 1.146 (3) | C38—C40 | 1.398 (2) |
N13—C52 | 1.150 (3) | C38—C39 | 1.421 (3) |
N14—C51 | 1.141 (3) | C40—C41 | 1.401 (2) |
C1—C5 | 1.401 (2) | C41—C42 | 1.418 (2) |
C1—C12 | 1.423 (2) | C41—C43 | 1.421 (2) |
C2—C3 | 1.402 (2) | C44—C45 | 1.501 (3) |
C2—H2 | 0.9500 | C44—H44A | 0.9900 |
C3—C4 | 1.369 (3) | C44—H44B | 0.9900 |
C3—H3 | 0.9500 | C45—H45A | 0.9900 |
C4—C5 | 1.409 (2) | C45—H45B | 0.9900 |
C4—H4 | 0.9500 | C46—C47 | 1.413 (3) |
C5—C6 | 1.434 (2) | C47—C49 | 1.383 (3) |
C6—C7 | 1.352 (3) | C47—C48 | 1.427 (3) |
C6—H6 | 0.9500 | C49—O3A | 1.373 (3) |
C7—C8 | 1.437 (2) | C49—C50 | 1.393 (3) |
C7—H7 | 0.9500 | C49—O3B | 1.413 (5) |
C8—C12 | 1.398 (2) | C50—C51 | 1.415 (3) |
C8—C9 | 1.406 (2) | C50—C52 | 1.420 (3) |
C9—C10 | 1.373 (3) | O3A—C53A | 1.424 (3) |
C9—H9 | 0.9500 | O4A—C54A | 1.401 (3) |
C10—C11 | 1.398 (3) | O4A—H2OA | 0.8500 |
C10—H10 | 0.9500 | C53A—C54A | 1.507 (4) |
C11—H11 | 0.9500 | C53A—H53A | 0.9900 |
C13—C17 | 1.405 (2) | C53A—H53B | 0.9900 |
C13—C24 | 1.421 (2) | C54A—H54A | 0.9900 |
C14—C15 | 1.400 (2) | C54A—H54B | 0.9900 |
C14—H14 | 0.9500 | O3B—C53B | 1.430 (6) |
C15—C16 | 1.366 (3) | O4B—C54B | 1.412 (6) |
C15—H15 | 0.9500 | O4B—H2OB | 0.8500 |
C16—C17 | 1.404 (2) | C53B—C54B | 1.512 (6) |
C16—H16 | 0.9500 | C53B—H53C | 0.9900 |
C17—C18 | 1.432 (2) | C53B—H53D | 0.9900 |
C18—C19 | 1.355 (3) | C54B—H54C | 0.9900 |
C18—H18 | 0.9500 | C54B—H54D | 0.9900 |
C19—C20 | 1.434 (2) | | |
| | | |
N2—Fe1—N1 | 82.92 (6) | N4—C24—C13 | 115.66 (14) |
N2—Fe1—N5 | 93.10 (6) | C20—C24—C13 | 120.43 (14) |
N1—Fe1—N5 | 90.51 (5) | N5—C25—C29 | 123.69 (16) |
N2—Fe1—N3 | 93.84 (6) | N5—C25—C36 | 115.98 (15) |
N1—Fe1—N3 | 175.64 (6) | C29—C25—C36 | 120.33 (16) |
N5—Fe1—N3 | 92.58 (6) | N5—C26—C27 | 122.43 (17) |
N2—Fe1—N4 | 91.09 (6) | N5—C26—H26 | 118.8 |
N1—Fe1—N4 | 94.44 (5) | C27—C26—H26 | 118.8 |
N5—Fe1—N4 | 173.87 (6) | C28—C27—C26 | 120.18 (17) |
N3—Fe1—N4 | 82.68 (6) | C28—C27—H27 | 119.9 |
N2—Fe1—N6 | 174.39 (6) | C26—C27—H27 | 119.9 |
N1—Fe1—N6 | 93.21 (6) | C27—C28—C29 | 119.24 (17) |
N5—Fe1—N6 | 82.85 (6) | C27—C28—H28 | 120.4 |
N3—Fe1—N6 | 90.22 (6) | C29—C28—H28 | 120.4 |
N4—Fe1—N6 | 93.26 (6) | C25—C29—C28 | 117.14 (17) |
C40—O1—C44 | 122.74 (13) | C25—C29—C30 | 118.25 (17) |
C45—O2—H1O | 108.6 | C28—C29—C30 | 124.61 (17) |
H1W—O1W—H2W | 108.4 | C31—C30—C29 | 121.38 (17) |
C2—N1—C1 | 117.44 (14) | C31—C30—H30 | 119.3 |
C2—N1—Fe1 | 129.87 (12) | C29—C30—H30 | 119.3 |
C1—N1—Fe1 | 112.68 (10) | C30—C31—C32 | 121.34 (18) |
C11—N2—C12 | 116.91 (15) | C30—C31—H31 | 119.3 |
C11—N2—Fe1 | 130.04 (12) | C32—C31—H31 | 119.3 |
C12—N2—Fe1 | 113.04 (11) | C36—C32—C33 | 117.18 (17) |
C14—N3—C13 | 117.17 (14) | C36—C32—C31 | 118.22 (17) |
C14—N3—Fe1 | 130.00 (12) | C33—C32—C31 | 124.60 (18) |
C13—N3—Fe1 | 112.81 (11) | C34—C33—C32 | 119.11 (17) |
C23—N4—C24 | 116.92 (14) | C34—C33—H33 | 120.4 |
C23—N4—Fe1 | 130.38 (11) | C32—C33—H33 | 120.4 |
C24—N4—Fe1 | 112.70 (11) | C33—C34—C35 | 120.19 (17) |
C26—N5—C25 | 117.31 (15) | C33—C34—H34 | 119.9 |
C26—N5—Fe1 | 129.92 (13) | C35—C34—H34 | 119.9 |
C25—N5—Fe1 | 112.75 (11) | N6—C35—C34 | 122.46 (17) |
C35—N6—C36 | 117.18 (15) | N6—C35—H35 | 118.8 |
C35—N6—Fe1 | 130.19 (12) | C34—C35—H35 | 118.8 |
C36—N6—Fe1 | 112.63 (11) | N6—C36—C32 | 123.87 (16) |
N1—C1—C5 | 123.90 (15) | N6—C36—C25 | 115.68 (15) |
N1—C1—C12 | 115.83 (14) | C32—C36—C25 | 120.44 (16) |
C5—C1—C12 | 120.27 (15) | N7—C37—C38 | 176.7 (2) |
N1—C2—C3 | 122.34 (16) | C40—C38—C37 | 124.17 (16) |
N1—C2—H2 | 118.8 | C40—C38—C39 | 118.48 (16) |
C3—C2—H2 | 118.8 | C37—C38—C39 | 116.90 (16) |
C4—C3—C2 | 120.18 (16) | N8—C39—C38 | 178.7 (2) |
C4—C3—H3 | 119.9 | O1—C40—C38 | 112.04 (15) |
C2—C3—H3 | 119.9 | O1—C40—C41 | 121.79 (15) |
C3—C4—C5 | 119.16 (16) | C38—C40—C41 | 126.09 (16) |
C3—C4—H4 | 120.4 | C40—C41—C42 | 122.11 (15) |
C5—C4—H4 | 120.4 | C40—C41—C43 | 123.75 (15) |
C1—C5—C4 | 116.97 (16) | C42—C41—C43 | 114.01 (15) |
C1—C5—C6 | 118.36 (15) | N10—C42—C41 | 176.29 (18) |
C4—C5—C6 | 124.67 (16) | N9—C43—C41 | 176.56 (19) |
C7—C6—C5 | 121.37 (16) | O1—C44—C45 | 105.29 (15) |
C7—C6—H6 | 119.3 | O1—C44—H44A | 110.7 |
C5—C6—H6 | 119.3 | C45—C44—H44A | 110.7 |
C6—C7—C8 | 121.09 (16) | O1—C44—H44B | 110.7 |
C6—C7—H7 | 119.5 | C45—C44—H44B | 110.7 |
C8—C7—H7 | 119.5 | H44A—C44—H44B | 108.8 |
C12—C8—C9 | 117.21 (16) | O2—C45—C44 | 112.30 (18) |
C12—C8—C7 | 118.32 (16) | O2—C45—H45A | 109.1 |
C9—C8—C7 | 124.47 (16) | C44—C45—H45A | 109.1 |
C10—C9—C8 | 119.05 (16) | O2—C45—H45B | 109.1 |
C10—C9—H9 | 120.5 | C44—C45—H45B | 109.1 |
C8—C9—H9 | 120.5 | H45A—C45—H45B | 107.9 |
C9—C10—C11 | 119.78 (16) | N11—C46—C47 | 177.2 (3) |
C9—C10—H10 | 120.1 | C49—C47—C46 | 123.68 (19) |
C11—C10—H10 | 120.1 | C49—C47—C48 | 119.72 (19) |
N2—C11—C10 | 123.06 (16) | C46—C47—C48 | 116.6 (2) |
N2—C11—H11 | 118.5 | N12—C48—C47 | 178.8 (3) |
C10—C11—H11 | 118.5 | O3A—C49—C47 | 115.26 (19) |
N2—C12—C8 | 123.98 (15) | O3A—C49—C50 | 115.3 (2) |
N2—C12—C1 | 115.43 (15) | C47—C49—C50 | 129.2 (2) |
C8—C12—C1 | 120.59 (15) | C47—C49—O3B | 114.5 (5) |
N3—C13—C17 | 123.88 (15) | C50—C49—O3B | 107.7 (5) |
N3—C13—C24 | 115.90 (14) | C49—C50—C51 | 123.5 (2) |
C17—C13—C24 | 120.20 (15) | C49—C50—C52 | 119.3 (2) |
N3—C14—C15 | 122.55 (16) | C51—C50—C52 | 117.1 (2) |
N3—C14—H14 | 118.7 | N14—C51—C50 | 177.5 (2) |
C15—C14—H14 | 118.7 | N13—C52—C50 | 179.9 (3) |
C16—C15—C14 | 120.44 (16) | C49—O3A—C53A | 113.68 (18) |
C16—C15—H15 | 119.8 | C54A—O4A—H2OA | 109.2 |
C14—C15—H15 | 119.8 | O3A—C53A—C54A | 105.6 (2) |
C15—C16—C17 | 118.83 (15) | O3A—C53A—H53A | 110.6 |
C15—C16—H16 | 120.6 | C54A—C53A—H53A | 110.6 |
C17—C16—H16 | 120.6 | O3A—C53A—H53B | 110.6 |
C16—C17—C13 | 117.12 (16) | C54A—C53A—H53B | 110.6 |
C16—C17—C18 | 124.29 (15) | H53A—C53A—H53B | 108.7 |
C13—C17—C18 | 118.58 (15) | O4A—C54A—C53A | 111.5 (2) |
C19—C18—C17 | 120.94 (16) | O4A—C54A—H54A | 109.3 |
C19—C18—H18 | 119.5 | C53A—C54A—H54A | 109.3 |
C17—C18—H18 | 119.5 | O4A—C54A—H54B | 109.3 |
C18—C19—C20 | 121.24 (16) | C53A—C54A—H54B | 109.3 |
C18—C19—H19 | 119.4 | H54A—C54A—H54B | 108.0 |
C20—C19—H19 | 119.4 | C49—O3B—C53B | 115.2 (8) |
C24—C20—C21 | 117.46 (15) | C54B—O4B—H2OB | 111.4 |
C24—C20—C19 | 118.53 (15) | O3B—C53B—C54B | 120.9 (11) |
C21—C20—C19 | 124.00 (16) | O3B—C53B—H53C | 107.1 |
C22—C21—C20 | 118.56 (15) | C54B—C53B—H53C | 107.1 |
C22—C21—H21 | 120.7 | O3B—C53B—H53D | 107.1 |
C20—C21—H21 | 120.7 | C54B—C53B—H53D | 107.1 |
C21—C22—C23 | 120.13 (16) | H53C—C53B—H53D | 106.8 |
C21—C22—H22 | 119.9 | O4B—C54B—C53B | 106.2 (10) |
C23—C22—H22 | 119.9 | O4B—C54B—H54C | 110.5 |
N4—C23—C22 | 122.91 (15) | C53B—C54B—H54C | 110.5 |
N4—C23—H23 | 118.5 | O4B—C54B—H54D | 110.5 |
C22—C23—H23 | 118.5 | C53B—C54B—H54D | 110.5 |
N4—C24—C20 | 123.90 (15) | H54C—C54B—H54D | 108.7 |
| | | |
N2—Fe1—N1—C2 | −178.69 (15) | N3—C13—C17—C18 | −179.45 (16) |
N5—Fe1—N1—C2 | 88.25 (15) | C24—C13—C17—C18 | 2.5 (2) |
N4—Fe1—N1—C2 | −88.13 (14) | C16—C17—C18—C19 | 178.68 (18) |
N6—Fe1—N1—C2 | 5.39 (15) | C13—C17—C18—C19 | −1.0 (3) |
N2—Fe1—N1—C1 | 2.84 (11) | C17—C18—C19—C20 | −1.7 (3) |
N5—Fe1—N1—C1 | −90.22 (11) | C18—C19—C20—C24 | 2.9 (3) |
N4—Fe1—N1—C1 | 93.40 (11) | C18—C19—C20—C21 | −175.77 (18) |
N6—Fe1—N1—C1 | −173.08 (11) | C24—C20—C21—C22 | −1.7 (2) |
N1—Fe1—N2—C11 | 178.41 (15) | C19—C20—C21—C22 | 176.98 (17) |
N5—Fe1—N2—C11 | −91.46 (15) | C20—C21—C22—C23 | 3.1 (3) |
N3—Fe1—N2—C11 | 1.33 (15) | C24—N4—C23—C22 | −1.5 (2) |
N4—Fe1—N2—C11 | 84.07 (15) | Fe1—N4—C23—C22 | 178.67 (12) |
N1—Fe1—N2—C12 | −2.24 (11) | C21—C22—C23—N4 | −1.6 (3) |
N5—Fe1—N2—C12 | 87.89 (11) | C23—N4—C24—C20 | 3.0 (2) |
N3—Fe1—N2—C12 | −179.32 (11) | Fe1—N4—C24—C20 | −177.09 (13) |
N4—Fe1—N2—C12 | −96.58 (11) | C23—N4—C24—C13 | −175.88 (15) |
N2—Fe1—N3—C14 | −86.56 (15) | Fe1—N4—C24—C13 | 4.02 (18) |
N5—Fe1—N3—C14 | 6.72 (16) | C21—C20—C24—N4 | −1.5 (2) |
N4—Fe1—N3—C14 | −177.17 (16) | C19—C20—C24—N4 | 179.82 (15) |
N6—Fe1—N3—C14 | 89.57 (15) | C21—C20—C24—C13 | 177.38 (15) |
N2—Fe1—N3—C13 | 94.75 (11) | C19—C20—C24—C13 | −1.3 (2) |
N5—Fe1—N3—C13 | −171.97 (11) | N3—C13—C24—N4 | −0.6 (2) |
N4—Fe1—N3—C13 | 4.13 (11) | C17—C13—C24—N4 | 177.63 (15) |
N6—Fe1—N3—C13 | −89.12 (12) | N3—C13—C24—C20 | −179.53 (15) |
N2—Fe1—N4—C23 | 81.70 (15) | C17—C13—C24—C20 | −1.3 (2) |
N1—Fe1—N4—C23 | −1.28 (15) | C26—N5—C25—C29 | 1.2 (2) |
N3—Fe1—N4—C23 | 175.44 (16) | Fe1—N5—C25—C29 | −177.37 (13) |
N6—Fe1—N4—C23 | −94.76 (15) | C26—N5—C25—C36 | −178.73 (14) |
N2—Fe1—N4—C24 | −98.18 (11) | Fe1—N5—C25—C36 | 2.74 (17) |
N1—Fe1—N4—C24 | 178.84 (11) | C25—N5—C26—C27 | −0.5 (2) |
N3—Fe1—N4—C24 | −4.45 (11) | Fe1—N5—C26—C27 | 177.76 (13) |
N6—Fe1—N4—C24 | 85.36 (11) | N5—C26—C27—C28 | −0.5 (3) |
N2—Fe1—N5—C26 | 2.50 (15) | C26—C27—C28—C29 | 0.7 (3) |
N1—Fe1—N5—C26 | 85.43 (15) | N5—C25—C29—C28 | −0.9 (2) |
N3—Fe1—N5—C26 | −91.49 (15) | C36—C25—C29—C28 | 178.99 (15) |
N6—Fe1—N5—C26 | 178.61 (15) | N5—C25—C29—C30 | 179.70 (15) |
N2—Fe1—N5—C25 | −179.21 (11) | C36—C25—C29—C30 | −0.4 (2) |
N1—Fe1—N5—C25 | −96.28 (11) | C27—C28—C29—C25 | −0.1 (3) |
N3—Fe1—N5—C25 | 86.80 (11) | C27—C28—C29—C30 | 179.28 (17) |
N6—Fe1—N5—C25 | −3.10 (11) | C25—C29—C30—C31 | 1.2 (3) |
N1—Fe1—N6—C35 | −87.10 (15) | C28—C29—C30—C31 | −178.13 (18) |
N5—Fe1—N6—C35 | −177.22 (15) | C29—C30—C31—C32 | −0.5 (3) |
N3—Fe1—N6—C35 | 90.22 (15) | C30—C31—C32—C36 | −1.1 (3) |
N4—Fe1—N6—C35 | 7.53 (15) | C30—C31—C32—C33 | 178.55 (18) |
N1—Fe1—N6—C36 | 93.05 (11) | C36—C32—C33—C34 | −0.3 (3) |
N5—Fe1—N6—C36 | 2.94 (11) | C31—C32—C33—C34 | −179.89 (18) |
N3—Fe1—N6—C36 | −89.63 (11) | C32—C33—C34—C35 | −0.6 (3) |
N4—Fe1—N6—C36 | −172.31 (11) | C36—N6—C35—C34 | 0.3 (2) |
C2—N1—C1—C5 | −0.7 (2) | Fe1—N6—C35—C34 | −179.58 (13) |
Fe1—N1—C1—C5 | 177.95 (13) | C33—C34—C35—N6 | 0.6 (3) |
C2—N1—C1—C12 | 178.36 (14) | C35—N6—C36—C32 | −1.2 (2) |
Fe1—N1—C1—C12 | −2.97 (17) | Fe1—N6—C36—C32 | 178.69 (13) |
C1—N1—C2—C3 | 0.3 (2) | C35—N6—C36—C25 | 177.84 (14) |
Fe1—N1—C2—C3 | −178.13 (12) | Fe1—N6—C36—C25 | −2.29 (17) |
N1—C2—C3—C4 | 0.2 (3) | C33—C32—C36—N6 | 1.2 (3) |
C2—C3—C4—C5 | −0.3 (3) | C31—C32—C36—N6 | −179.17 (15) |
N1—C1—C5—C4 | 0.6 (2) | C33—C32—C36—C25 | −177.78 (15) |
C12—C1—C5—C4 | −178.42 (15) | C31—C32—C36—C25 | 1.9 (2) |
N1—C1—C5—C6 | 179.85 (15) | N5—C25—C36—N6 | −0.3 (2) |
C12—C1—C5—C6 | 0.8 (2) | C29—C25—C36—N6 | 179.81 (14) |
C3—C4—C5—C1 | −0.1 (2) | N5—C25—C36—C32 | 178.76 (15) |
C3—C4—C5—C6 | −179.25 (17) | C29—C25—C36—C32 | −1.1 (2) |
C1—C5—C6—C7 | −1.0 (3) | C44—O1—C40—C38 | −147.72 (17) |
C4—C5—C6—C7 | 178.11 (17) | C44—O1—C40—C41 | 35.1 (2) |
C5—C6—C7—C8 | 0.5 (3) | C37—C38—C40—O1 | −162.11 (17) |
C6—C7—C8—C12 | 0.3 (3) | C39—C38—C40—O1 | 9.9 (2) |
C6—C7—C8—C9 | −179.17 (17) | C37—C38—C40—C41 | 14.9 (3) |
C12—C8—C9—C10 | 0.7 (2) | C39—C38—C40—C41 | −173.01 (17) |
C7—C8—C9—C10 | −179.82 (17) | O1—C40—C41—C42 | −168.39 (16) |
C8—C9—C10—C11 | 0.2 (3) | C38—C40—C41—C42 | 14.8 (3) |
C12—N2—C11—C10 | 0.0 (2) | O1—C40—C41—C43 | 16.1 (3) |
Fe1—N2—C11—C10 | 179.29 (13) | C38—C40—C41—C43 | −160.71 (18) |
C9—C10—C11—N2 | −0.5 (3) | C40—O1—C44—C45 | 155.79 (16) |
C11—N2—C12—C8 | 1.0 (2) | O1—C44—C45—O2 | 63.3 (2) |
Fe1—N2—C12—C8 | −178.44 (13) | C46—C47—C49—O3A | −172.8 (2) |
C11—N2—C12—C1 | −179.29 (14) | C48—C47—C49—O3A | 5.0 (3) |
Fe1—N2—C12—C1 | 1.27 (17) | C46—C47—C49—C50 | 1.0 (4) |
C9—C8—C12—N2 | −1.3 (2) | C48—C47—C49—C50 | 178.8 (2) |
C7—C8—C12—N2 | 179.14 (15) | C46—C47—C49—O3B | 144.3 (5) |
C9—C8—C12—C1 | 178.98 (15) | C48—C47—C49—O3B | −37.8 (5) |
C7—C8—C12—C1 | −0.6 (2) | O3A—C49—C50—C51 | 167.3 (2) |
N1—C1—C12—N2 | 1.1 (2) | C47—C49—C50—C51 | −6.4 (4) |
C5—C1—C12—N2 | −179.74 (14) | O3B—C49—C50—C51 | −151.7 (5) |
N1—C1—C12—C8 | −179.14 (14) | O3A—C49—C50—C52 | −9.9 (3) |
C5—C1—C12—C8 | 0.0 (2) | C47—C49—C50—C52 | 176.3 (2) |
C14—N3—C13—C17 | −0.2 (2) | O3B—C49—C50—C52 | 31.1 (5) |
Fe1—N3—C13—C17 | 178.71 (13) | C47—C49—O3A—C53A | −85.4 (3) |
C14—N3—C13—C24 | 177.99 (15) | C50—C49—O3A—C53A | 99.9 (3) |
Fe1—N3—C13—C24 | −3.13 (18) | O3B—C49—O3A—C53A | 12.9 (7) |
C13—N3—C14—C15 | −0.4 (2) | C49—O3A—C53A—C54A | 161.2 (2) |
Fe1—N3—C14—C15 | −179.04 (13) | O3A—C53A—C54A—O4A | 61.2 (3) |
N3—C14—C15—C16 | 0.2 (3) | O3A—C49—O3B—C53B | 1.4 (8) |
C14—C15—C16—C17 | 0.5 (3) | C47—C49—O3B—C53B | 101.9 (11) |
C15—C16—C17—C13 | −1.0 (2) | C50—C49—O3B—C53B | −107.1 (10) |
C15—C16—C17—C18 | 179.33 (17) | C49—O3B—C53B—C54B | 155.5 (11) |
N3—C13—C17—C16 | 0.9 (2) | O3B—C53B—C54B—O4B | 64.2 (19) |
C24—C13—C17—C16 | −177.22 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O···O1W | 0.85 | 2.01 | 2.833 (2) | 164 |
O1W—H1W···N8 | 0.85 | 2.38 | 3.190 (3) | 160 |
O1W—H2W···N12 | 0.85 | 2.14 | 2.952 (2) | 159 |
O4A—H2OA···N13i | 0.85 | 2.44 | 3.289 (5) | 175 |
O4B—H2OB···N9ii | 0.85 | 2.24 | 3.023 (9) | 154 |
C10—H10···N8iii | 0.95 | 2.45 | 3.376 (3) | 166 |
C15—H15···N11 | 0.95 | 2.57 | 3.189 (3) | 123 |
C19—H19···N10iv | 0.95 | 2.56 | 3.403 (3) | 148 |
C21—H21···N10iv | 0.95 | 2.61 | 3.439 (2) | 146 |
C28—H28···N14v | 0.95 | 2.48 | 3.224 (3) | 135 |
C35—H35···O2 | 0.95 | 2.38 | 3.132 (2) | 136 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y, −z; (v) −x, −y+1, −z+1. |
π–π contacts (Å, °) for (I) topRings A, B and C are labelled according to Fig. 2.
IPD is the interplanar distance (distance from one plane to the neighbouring
centroid), CCD is centre-to-centre distance (distance between ring centroids)
and SA is the slippage angle (angle subtended by the intercentroid vector to
the plane normal); for details, see Janiak (2000). |
Group 1/group 2 | | IPD (Å) | CCD (Å) | SA (°) |
Ring A/ring Aiii | (single stack) | 3.550 (2) | 3.792 (3) | 20.58 (5) |
Ring B/ring Cvi | (double stack) | 3.498 (2) | 3.939 (3) | 27.37 (5) |
Symmetry codes: (iii) -x + 1, -y + 1, -z; (vi) -x + 1, -y + 1, -z + 1. |
Selected bond lengths (Å) and Wiberg bond orders for tcnoetOH- anions from
X-ray data and DFT calculations topThe calculations were performed at the B97D/6-311+G(2d,2p) level of
theory. For details of Wiberg bond-order calculations, see Wiberg
(1968). |
Parameter | Bond length | Wiberg bond order |
N7—C37 | 1.146 (3) | 2.783 |
N8—C39 | 1.148 (3) | 2.767 |
N9—C43 | 1.150 (2) | 2.767 |
N10—C42 | 1.148 (2) | 2.781 |
N11—C46 | 1.156 (3) | 2.785 |
N12—C48 | 1.146 (3) | 2.758 |
N13—C52 | 1.150 (3) | 2.784 |
N14—C51 | 1.141 (3) | 2.788 |
C37—C38 | 1.418 (3) | 1.130 |
C38—C40 | 1.398 (2) | 1.298 |
C38—C39 | 1.421 (3) | 1.132 |
C40—C41 | 1.401 (2) | 1.285 |
C41—C42 | 1.418 (2) | 1.126 |
C41—C43 | 1.421 (2) | 1.138 |
C46—C47 | 1.413 (3) | 1.127 |
C47—C49 | 1.383 (3) | 1.320 |
C47—C48 | 1.427 (3) | 1.128 |
C49—C50 | 1.393 (3) | 1.326 |
C50—C51 | 1.415 (3) | 1.125 |
C50—C52 | 1.420 (3) | 1.125 |