Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614017070/ov3050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614017070/ov30501sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614017070/ov30502sup3.hkl |
CCDC references: 1015727; 1015728
The 2,2'-bipyridine (bipy) ligand is used extensively in electrochemistry because of its superb redox activity. Anionic homoleptic bipy transition metalates like [Ti(bipy)3]-, [Mn(bipy)3]-, and [Cr(bipy)3]3- were first reported nearly 50 years ago (Uhlig, 1988, and references therein). The first homoleptic bipy ferrate [Fe(bipy)3]- was synthesized in the mid-1960s from both electrochemical (Tanaka & Sato, 1966) and chemical (Hall & Reynolds, 1966; Mahon & Reynolds, 1967) means, followed a few years later by the cobaltate [Co(bipy)2]-, which was generated by electrochemical methods (Dhar & Kurcz, 1974). Despite the long-known existence of these anions, this is first report of their structures by single-crystal X-ray diffraction. We report here the structure of bis[([2.2.2]cryptand)potassium(I)] tris(2,2'-bipyridine)ferrate(–I) anthracene(–I), (I), and ([2.2.2]cryptand)potassium(I) bis(2,2'-bipyridine)cobaltate(–I) anthracene hemisolvate tetrahydrofuran (THF) disolvate, (2).
Details for the synthesis and preliminary characterization of [K(18-crown-6)(THF)2][Fe(bipy)3].3THF (THF is tetrahydrofuran and bipy is 2,2'-bipyridine) can be found elsewhere (Brennessel, 2009). Crystal data for this salt: trigonal, R3, a = 14.9665 (2), c = 48.766 (8) Å, V = 9460 (2) Å3, Z = 6; T = 173 (2) K, 3734 reflections (3014 for [I > 2σ(I)]).
A room-temperature solution of excess bipy in THF was added to a deep-orange room-temperature THF solution of [K([2.2.2]cryptand)][Fe(η4-C14H10)2].0.5THF (Brennessel et al., 2007) that was known to contain an impurity of [K([2.2.2]cryptand)](C14H10). A yield was not determined because of the unknown amount of impurity in the starting material, and this product was only characterized by single-crystal X-ray diffraction. Purple–black plates were grown from a pentane-layered THF solution at 273 K.
A solution of bipy (0.180 g, 1.15 mmol) in tetrahydrofuran (30 ml, 195 K) was added to a deep pink–red solution of [K([2.2.2]cryptand)][Co(η4-C14H10)2].0.5THF (0.500 g, 0.577 mmol; Brennessel et al., 2002) in THF (60 ml, 195 K). The resulting solution was warmed slowly to room temperature, at which point it was deep purple. After the solvent was removed under vacuum, pentane (100 ml) was added with vigorous stirring. The product was filtered, washed with pentane (2 × 20 ml), and dried under vacuum, yielding a purple–black solid (yield 0.362 g, 62%). This product was only characterized by single-crystal X-ray diffraction. Purple–black rods were grown from a pentane-layered THF solution at 273 K.
Crystal data, data collection and structure refinement details are summarized in Table 1. The cocrystallized tetrahydrofuran (THF) solvent molecule (O8/C43–C46) in (2) is located in a pocket that includes its inversion symmetry equivalent. After being modeled as disordered over two general positions, a third orientation could be found from the difference map. Thus, the molecule was modeled as disordered over three positions, with a refined ratio of 0.412 (4):0.387 (3):0.201 (3). Analogous bond lengths and angles among the three positions of the disordered THF molecule and both directions around the ring of the ordered THF molecule (O7/C39–C42) were restrained to be similar. Anistropic displacement parameters for pairs of near isopositional atoms were heavily restrained to be similar. Additionally, anisotropic displacement parameters for all atoms in the two major components of the disorder were restrained to be similar, and separately, the same for all the atoms in the ring of the third component. H atoms were placed geometrically and treated as riding atoms, with methylene C—H = 0.99 Å and sp2 C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq(C).
Both (1) and (2) were synthesized directly from homoleptic bis(anthracene)metalate precursors, [M(η4-C14H10)2]- [M = Fe (Brennessel et al., 2007) and Co (Brennessel et al., 2002; Brennessel & Ellis, 2012)], the former of which is a 17-electron species. In the case of iron, two structures of the homoleptic bipy ferrate were determined. For the first, a solution of [K(18-crown-6)(THF)2][Fe(η4-C14H10)2] was reacted with excess bipy in THF at room temperature, and the crude product was layered with pentane. The resulting purple–black blocks were formulated as [K(18-crown-6)(THF)2][Fe(bipy)3].3THF based on a single-crystal X-ray experiment (Brennessel, 2009). However, due to the severe disorder in the crown ether and cocrystallized THF and the overall poor quality of the structure, a different crystallization was performed. The starting material for the second attempt was a sample of [K([2.2.2]cryptand)][Fe(η4-C14H10)2].0.5THF (Brennessel et al., 2007) that contained a known impurity of anthracene radical anion in the form of [K([2.2.2]cryptand)](C14H10) (the two salts are very difficult to separate). Single crystals were again grown from the crude reaction mixture by diffusion of pentane into a THF solution of the mixture, which resulted in good quality purple–black plates that were formulated as [K([2.2.2]cryptand)]2[Fe(bipy)3][C14H10], (1) (Fig. 1), based on this single-crystal X-ray experiment.
Because the charge assigned to the iron complex in (1) depends on the assignment of the charge on the cocrystallized anthracene species, a close inspection of the latter's bond lengths was required. The addition of an electron to neutral anthracene causes the lengthening of certain bonds and the shortening of others (Rosokha & Kochi, 2006). Fig. 2 shows the bond lengths of the cocrystallized anthracene in (1) along with those from low-temperature structures of known neutral [Cambridge Structural Database (CSD; Version 5.35, update No. 2, Febuary 2014; Allen, 2002) refcode ANTCEN11 (Brock & Dunitz, 1990)] and monoanionic forms (CSD refcode YETPAP; Rosokha & Kochi, 2006). The bond lengths in (1) match more closely with those of anthracene radical anion, and thus the iron complex is formulated as monoanionic.
The geometry of (1) is essentially octahedral, with only the bite angles of the bipy ligands causing the deviation from the perfect octahedron. Because the anion lies on a crystallographic twofold axis, there are two unique bite angles of 82.8 (1) and 81.8 (2)°. An electron count of the ferrate when considered as a mono-negative iron center with three neutral bipy ligands gives a 21-electron complex, which is not consistent with a low valent center with three acceptor ligands (Mitchell & Parish, 1969; Elschenbroich, 2005). Further examination suggests that the bipy ligands should not be considered neutral (see below).
A good indicator of the degree of reduction of coordinated bipy is the length of the bond that links the rings (Radonovich et al., 1982; England et al., 2012). In neutral bipy, this bond length is 1.490 (3) Å (CSD refcode BIPYRL03; Chisholm et al., 1981), in the bipy radical anion it is 1.431 (3) (CSD refcode QUPGAK; Gore-Randall et al., 2009) and 1.429 Å [CSD refcode QUPGEO (Gore-Randall et al., 2009); average of four independent bond lengths], and in the bipy dianion it has been reported as 1.376 (4) (CSD refcode JAXQUU; Bock et al., 1999) and 1.399 (6) Å (CSD refcode QUPGIS; Gore-Randall et al., 2009). The two independent values of this bond length in (1) are 1.431 (4) and 1.411 (6) Å, both which are between the neutral and dianionic extremes and essentially coincide with the average for salts of the monoanion. The two resonance structures that are likely the most important contributions to the overall bonding are shown in Fig. 3. ESR (electron spin resonance) spectroscopy has corroborated this by showing that one electron exists on each ligand without hopping (Motten et al., 1981), further supporting the assignment of a metal center with 18 valence electrons. Recent work by Wieghardt has concluded that (1) is best regarded as an FeII, d6 metal center with three bipy radical anionic ligands for which each unpaired electron is found in a ligand π* orbital (England et al., 2012; Scarborough & Wieghardt, 2011).
The cobalt anion was generated from a low-temperature reaction of [K([2.2.2]cryptand)][Co(η4-C14H10)2].0.5THF (Brennessel et al., 2002) and excess bipy at 195 K. The structure was formulated as [K([2.2.2]cryptand)][Co(bipy)2].0.5C14H10.2THF, (2), based on this single-crystal experiment (Fig. 4). Unlike in the case of (1), the cocrystallized anthracene molecule is neutral, as determined by bond-length comparisons with the neutral and anionic anthracene structures (Fig. 2), and thus the cobalt complex is formulated as monoanionic. The twist angle between the two N—Co—N planes is 38.63 (8)°, which indicates that the geometry is between tetrahedral (90°) and square planar (0°). Quantification using Houser's τ4 index gives a value of 0.36 (Yang et al., 2007), which is consistent with the visually observed distorted square-planar geometry.
Assignment of the exact reduced nature of the bipy ligands in (2) is not clear, however. The C—C bonds that join the pyridine rings in the two independent bipy ligands both refined to 1.405 (3) Å. Given that this bond length for the bipy dianion ranges from ~1.40 to 1.36 Å (Wang et al., 2013) and that for the bipy radical anion is centered around 1.43 Å (Gore-Randall et al., 2009), no obvious conclusion can be drawn. A search of the CSD for transition and inner transition metal complexes containing a minimum of two unsubstituted bipy ligands and whose characteristic bipy C—C bond lengths were in the range of 1.40–1.41 Å yielded exactly five hits. Two of these structures could be eliminated for having too great a range of these bond lengths among bipy ligands in similar environments, and in the other three structures these bond lengths were not discussed in the corresponding articles. Rothwell reported a structure of W(OC6HPh4-2,3,5,6)2(bipy)2 whose characteristic C—C bond lengths are 1.409 (4) and 1.412 (4) Å, and concluded based on structural and 1H and 1H COSY NMR data that the amount of reduction in the bipy ligands is unclear (CSD refcode TAJXAE; Lentz et al., 2003). It seems reasonable to conclude that an unambiguous oxidation state assignment for the Co atom in (2) is not possible without further studies.
Each anthracene molecule in (2) is found in between and is oriented essentially orthogonal to [84.46 (4)°] one bipy ligand on each of the two neighboring cobaltates (Fig. 5), which suggests that aromatic donor–acceptor interactions (Martinez & Iverson, 2012) may have been partly responsible for the packing arrangement. The two closest H(anthracene)···plane(bipy) distances are approximately 2.53 and 2.78 Å.
For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[K(C18H36N2O6)2][Fe(C10H8N2)3](C14H10) | F(000) = 3264 |
Mr = 1533.79 | Dx = 1.277 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.049 (4) Å | Cell parameters from 2362 reflections |
b = 17.067 (3) Å | θ = 2.2–24.0° |
c = 21.543 (3) Å | µ = 0.36 mm−1 |
β = 109.779 (3)° | T = 173 K |
V = 7975 (2) Å3 | Plate, purple–black |
Z = 4 | 0.42 × 0.16 × 0.06 mm |
Siemens SMART CCD platform diffractometer | 4398 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.085 |
ω scans | θmax = 25.1°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2012) | h = −27→27 |
Tmin = 0.637, Tmax = 0.745 | k = −20→19 |
22943 measured reflections | l = −25→22 |
7069 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0515P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
7069 reflections | Δρmax = 0.27 e Å−3 |
474 parameters | Δρmin = −0.39 e Å−3 |
[K(C18H36N2O6)2][Fe(C10H8N2)3](C14H10) | V = 7975 (2) Å3 |
Mr = 1533.79 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.049 (4) Å | µ = 0.36 mm−1 |
b = 17.067 (3) Å | T = 173 K |
c = 21.543 (3) Å | 0.42 × 0.16 × 0.06 mm |
β = 109.779 (3)° |
Siemens SMART CCD platform diffractometer | 7069 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2012) | 4398 reflections with I > 2σ(I) |
Tmin = 0.637, Tmax = 0.745 | Rint = 0.085 |
22943 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.27 e Å−3 |
7069 reflections | Δρmin = −0.39 e Å−3 |
474 parameters |
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. H atoms were placed geometrically and treated as riding atoms: methylene, C—H = 0.99 Å, and sp2, C—H = 0.95 Å, with Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
Fe1 | 1.0000 | 0.16987 (4) | 0.2500 | 0.02605 (18) | |
N1 | 0.92863 (11) | 0.17628 (14) | 0.27964 (12) | 0.0275 (6) | |
C1 | 0.91594 (15) | 0.13244 (19) | 0.32483 (16) | 0.0361 (8) | |
H1A | 0.9440 | 0.0918 | 0.3455 | 0.043* | |
C2 | 0.86458 (15) | 0.1424 (2) | 0.34346 (18) | 0.0422 (9) | |
H2A | 0.8581 | 0.1098 | 0.3763 | 0.051* | |
C3 | 0.82232 (15) | 0.2012 (2) | 0.31311 (18) | 0.0424 (9) | |
H3A | 0.7868 | 0.2098 | 0.3252 | 0.051* | |
C4 | 0.83313 (15) | 0.2458 (2) | 0.26593 (17) | 0.0388 (9) | |
H4A | 0.8048 | 0.2861 | 0.2451 | 0.047* | |
C5 | 0.88563 (14) | 0.23362 (18) | 0.24719 (15) | 0.0299 (8) | |
C6 | 0.89978 (14) | 0.27405 (18) | 0.19592 (16) | 0.0308 (8) | |
C7 | 0.86230 (16) | 0.33191 (19) | 0.15364 (17) | 0.0378 (8) | |
H7A | 0.8257 | 0.3494 | 0.1603 | 0.045* | |
C8 | 0.87866 (16) | 0.36215 (19) | 0.10376 (17) | 0.0412 (9) | |
H8A | 0.8531 | 0.4002 | 0.0752 | 0.049* | |
C9 | 0.93308 (16) | 0.33759 (19) | 0.09411 (17) | 0.0405 (9) | |
H9A | 0.9446 | 0.3578 | 0.0589 | 0.049* | |
C10 | 0.96930 (16) | 0.28303 (19) | 0.13744 (17) | 0.0376 (8) | |
H10A | 1.0068 | 0.2673 | 0.1318 | 0.045* | |
N2 | 0.95456 (11) | 0.25081 (14) | 0.18723 (13) | 0.0287 (6) | |
N3 | 1.03880 (11) | 0.08287 (14) | 0.30923 (12) | 0.0256 (6) | |
C11 | 1.08056 (14) | 0.0868 (2) | 0.37030 (16) | 0.0341 (8) | |
H11A | 1.0930 | 0.1374 | 0.3884 | 0.041* | |
C12 | 1.10648 (15) | 0.0231 (2) | 0.40843 (17) | 0.0384 (9) | |
H12A | 1.1358 | 0.0297 | 0.4514 | 0.046* | |
C13 | 1.08847 (15) | −0.0525 (2) | 0.38227 (17) | 0.0393 (9) | |
H13A | 1.1053 | −0.0979 | 0.4074 | 0.047* | |
C14 | 1.04672 (15) | −0.05885 (19) | 0.32081 (17) | 0.0372 (8) | |
H14A | 1.0339 | −0.1094 | 0.3030 | 0.045* | |
C15 | 1.02156 (13) | 0.00845 (17) | 0.28234 (15) | 0.0287 (7) | |
K1 | 0.62197 (3) | 0.19561 (4) | 0.16333 (3) | 0.03210 (19) | |
N4 | 0.61166 (13) | 0.35212 (16) | 0.09583 (14) | 0.0394 (7) | |
C16 | 0.59914 (17) | 0.4128 (2) | 0.13814 (18) | 0.0482 (10) | |
H16A | 0.5557 | 0.4081 | 0.1360 | 0.058* | |
H16B | 0.6041 | 0.4650 | 0.1204 | 0.058* | |
C17 | 0.64032 (17) | 0.40845 (19) | 0.20933 (18) | 0.0466 (10) | |
H17A | 0.6840 | 0.4126 | 0.2124 | 0.056* | |
H17B | 0.6310 | 0.4524 | 0.2344 | 0.056* | |
O1 | 0.63013 (10) | 0.33560 (12) | 0.23651 (11) | 0.0381 (6) | |
C18 | 0.66935 (15) | 0.3273 (2) | 0.30374 (16) | 0.0391 (9) | |
H18A | 0.6678 | 0.3754 | 0.3288 | 0.047* | |
H18B | 0.7125 | 0.3189 | 0.3059 | 0.047* | |
C19 | 0.64748 (15) | 0.25875 (19) | 0.33271 (16) | 0.0384 (9) | |
H19A | 0.6707 | 0.2555 | 0.3806 | 0.046* | |
H19B | 0.6032 | 0.2649 | 0.3266 | 0.046* | |
O2 | 0.65670 (10) | 0.18887 (12) | 0.30062 (11) | 0.0362 (6) | |
C20 | 0.63833 (16) | 0.12081 (19) | 0.32766 (17) | 0.0402 (9) | |
H20A | 0.5929 | 0.1195 | 0.3153 | 0.048* | |
H20B | 0.6565 | 0.1218 | 0.3764 | 0.048* | |
C21 | 0.66043 (17) | 0.0492 (2) | 0.30083 (17) | 0.0450 (10) | |
H21A | 0.7054 | 0.0537 | 0.3102 | 0.054* | |
H21B | 0.6532 | 0.0022 | 0.3242 | 0.054* | |
C22 | 0.67077 (16) | 0.3681 (2) | 0.08556 (18) | 0.0476 (10) | |
H22A | 0.7017 | 0.3837 | 0.1282 | 0.057* | |
H22B | 0.6651 | 0.4129 | 0.0549 | 0.057* | |
C23 | 0.69555 (17) | 0.2993 (2) | 0.05817 (19) | 0.0537 (11) | |
H23A | 0.6640 | 0.2805 | 0.0171 | 0.064* | |
H23B | 0.7324 | 0.3155 | 0.0476 | 0.064* | |
O3 | 0.71137 (10) | 0.23837 (14) | 0.10594 (11) | 0.0427 (6) | |
C24 | 0.73919 (17) | 0.1734 (2) | 0.0846 (2) | 0.0532 (11) | |
H24A | 0.7755 | 0.1918 | 0.0740 | 0.064* | |
H24B | 0.7093 | 0.1506 | 0.0441 | 0.064* | |
C25 | 0.75859 (16) | 0.1128 (2) | 0.1364 (2) | 0.0498 (10) | |
H25A | 0.7795 | 0.0694 | 0.1218 | 0.060* | |
H25B | 0.7880 | 0.1354 | 0.1772 | 0.060* | |
O4 | 0.70528 (10) | 0.08346 (13) | 0.14907 (12) | 0.0416 (6) | |
C26 | 0.72256 (18) | 0.0212 (2) | 0.1955 (2) | 0.0558 (11) | |
H26A | 0.7495 | 0.0415 | 0.2387 | 0.067* | |
H26B | 0.7459 | −0.0188 | 0.1804 | 0.067* | |
C27 | 0.66597 (18) | −0.0151 (2) | 0.20269 (19) | 0.0537 (11) | |
H27A | 0.6393 | −0.0342 | 0.1589 | 0.064* | |
H27B | 0.6785 | −0.0611 | 0.2322 | 0.064* | |
C28 | 0.56087 (16) | 0.3497 (2) | 0.03156 (18) | 0.0497 (10) | |
H28A | 0.5747 | 0.3201 | −0.0004 | 0.060* | |
H28B | 0.5514 | 0.4038 | 0.0147 | 0.060* | |
C29 | 0.50279 (16) | 0.3123 (2) | 0.03556 (19) | 0.0504 (10) | |
H29A | 0.4891 | 0.3403 | 0.0685 | 0.060* | |
H29B | 0.4695 | 0.3158 | −0.0078 | 0.060* | |
O5 | 0.51514 (9) | 0.23242 (14) | 0.05423 (11) | 0.0426 (6) | |
C30 | 0.46067 (17) | 0.1937 (2) | 0.0546 (2) | 0.0624 (12) | |
H30A | 0.4274 | 0.2016 | 0.0118 | 0.075* | |
H30B | 0.4469 | 0.2159 | 0.0898 | 0.075* | |
C31 | 0.47343 (17) | 0.1081 (2) | 0.0665 (2) | 0.0614 (12) | |
H31A | 0.4345 | 0.0798 | 0.0612 | 0.074* | |
H31B | 0.4910 | 0.0869 | 0.0339 | 0.074* | |
O6 | 0.51560 (10) | 0.09638 (13) | 0.13119 (12) | 0.0472 (7) | |
C32 | 0.52559 (18) | 0.0151 (2) | 0.1464 (2) | 0.0559 (11) | |
H32A | 0.5445 | −0.0097 | 0.1163 | 0.067* | |
H32B | 0.4857 | −0.0111 | 0.1402 | 0.067* | |
C33 | 0.56759 (17) | 0.0055 (2) | 0.21678 (18) | 0.0517 (10) | |
H33A | 0.5487 | 0.0316 | 0.2463 | 0.062* | |
H33B | 0.5714 | −0.0510 | 0.2279 | 0.062* | |
N5 | 0.62967 (13) | 0.03816 (16) | 0.22926 (14) | 0.0413 (7) | |
C34 | 0.68827 (14) | 0.1248 (2) | 0.53918 (16) | 0.0362 (8) | |
H34A | 0.6608 | 0.1356 | 0.5625 | 0.043* | |
C35 | 0.69764 (15) | 0.0479 (2) | 0.52524 (18) | 0.0420 (9) | |
H35A | 0.6762 | 0.0068 | 0.5379 | 0.050* | |
C36 | 0.73900 (15) | 0.0310 (2) | 0.49221 (17) | 0.0414 (9) | |
H36A | 0.7452 | −0.0217 | 0.4819 | 0.050* | |
C37 | 0.77079 (14) | 0.09053 (18) | 0.47444 (16) | 0.0346 (8) | |
H37A | 0.7994 | 0.0777 | 0.4530 | 0.041* | |
C38 | 0.76186 (13) | 0.17007 (19) | 0.48726 (15) | 0.0301 (7) | |
C39 | 0.79295 (13) | 0.23219 (18) | 0.46928 (15) | 0.0305 (8) | |
H39A | 0.8227 | 0.2202 | 0.4491 | 0.037* | |
C40 | 0.78204 (13) | 0.31163 (18) | 0.47990 (15) | 0.0285 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0223 (3) | 0.0244 (4) | 0.0320 (4) | 0.000 | 0.0099 (3) | 0.000 |
N1 | 0.0262 (14) | 0.0241 (15) | 0.0332 (15) | 0.0015 (12) | 0.0116 (12) | 0.0017 (12) |
C1 | 0.037 (2) | 0.0302 (19) | 0.044 (2) | 0.0042 (15) | 0.0175 (17) | 0.0025 (17) |
C2 | 0.041 (2) | 0.043 (2) | 0.052 (2) | 0.0015 (17) | 0.0284 (19) | 0.0028 (18) |
C3 | 0.034 (2) | 0.052 (2) | 0.049 (2) | 0.0055 (18) | 0.0234 (18) | −0.005 (2) |
C4 | 0.0317 (19) | 0.037 (2) | 0.046 (2) | 0.0071 (16) | 0.0111 (17) | −0.0081 (18) |
C5 | 0.0279 (18) | 0.0292 (19) | 0.0315 (19) | 0.0020 (15) | 0.0086 (15) | −0.0032 (15) |
C6 | 0.0317 (18) | 0.0244 (18) | 0.0324 (19) | 0.0020 (14) | 0.0058 (16) | −0.0084 (15) |
C7 | 0.038 (2) | 0.0318 (19) | 0.039 (2) | 0.0078 (17) | 0.0071 (17) | −0.0017 (17) |
C8 | 0.045 (2) | 0.030 (2) | 0.038 (2) | 0.0065 (17) | 0.0004 (18) | 0.0030 (17) |
C9 | 0.052 (2) | 0.0299 (19) | 0.038 (2) | −0.0054 (18) | 0.0131 (18) | 0.0062 (17) |
C10 | 0.039 (2) | 0.035 (2) | 0.041 (2) | −0.0055 (16) | 0.0166 (18) | −0.0003 (18) |
N2 | 0.0271 (14) | 0.0225 (14) | 0.0355 (16) | 0.0007 (12) | 0.0093 (13) | −0.0003 (12) |
N3 | 0.0203 (13) | 0.0270 (15) | 0.0297 (16) | 0.0027 (11) | 0.0086 (12) | −0.0012 (12) |
C11 | 0.0305 (19) | 0.036 (2) | 0.035 (2) | 0.0019 (16) | 0.0110 (17) | −0.0052 (16) |
C12 | 0.0335 (19) | 0.046 (2) | 0.031 (2) | 0.0083 (17) | 0.0053 (16) | −0.0021 (17) |
C13 | 0.039 (2) | 0.042 (2) | 0.036 (2) | 0.0118 (17) | 0.0113 (18) | 0.0075 (17) |
C14 | 0.042 (2) | 0.0253 (19) | 0.043 (2) | 0.0049 (15) | 0.0126 (18) | 0.0011 (16) |
C15 | 0.0275 (18) | 0.0259 (18) | 0.0351 (18) | 0.0030 (14) | 0.0136 (14) | 0.0007 (15) |
K1 | 0.0299 (4) | 0.0327 (4) | 0.0340 (4) | −0.0013 (3) | 0.0113 (3) | −0.0015 (3) |
N4 | 0.0429 (17) | 0.0379 (18) | 0.0377 (17) | −0.0051 (14) | 0.0140 (15) | 0.0075 (14) |
C16 | 0.054 (2) | 0.034 (2) | 0.055 (3) | −0.0016 (18) | 0.018 (2) | 0.0121 (19) |
C17 | 0.061 (3) | 0.031 (2) | 0.050 (3) | −0.0123 (18) | 0.022 (2) | −0.0044 (18) |
O1 | 0.0413 (14) | 0.0304 (13) | 0.0378 (14) | −0.0031 (11) | 0.0072 (11) | −0.0001 (11) |
C18 | 0.0331 (19) | 0.040 (2) | 0.041 (2) | 0.0035 (16) | 0.0080 (17) | −0.0089 (18) |
C19 | 0.037 (2) | 0.042 (2) | 0.032 (2) | 0.0061 (17) | 0.0064 (16) | −0.0046 (17) |
O2 | 0.0427 (14) | 0.0311 (13) | 0.0367 (14) | 0.0031 (10) | 0.0158 (11) | 0.0005 (11) |
C20 | 0.041 (2) | 0.043 (2) | 0.035 (2) | 0.0011 (18) | 0.0117 (17) | 0.0061 (18) |
C21 | 0.055 (2) | 0.035 (2) | 0.041 (2) | 0.0043 (18) | 0.012 (2) | 0.0048 (18) |
C22 | 0.050 (2) | 0.052 (2) | 0.043 (2) | −0.0163 (19) | 0.0172 (19) | 0.0092 (19) |
C23 | 0.043 (2) | 0.079 (3) | 0.044 (2) | −0.019 (2) | 0.022 (2) | 0.000 (2) |
O3 | 0.0427 (14) | 0.0531 (16) | 0.0388 (14) | −0.0025 (12) | 0.0221 (12) | −0.0014 (13) |
C24 | 0.044 (2) | 0.072 (3) | 0.055 (3) | −0.014 (2) | 0.031 (2) | −0.025 (2) |
C25 | 0.034 (2) | 0.059 (3) | 0.058 (3) | −0.0026 (19) | 0.017 (2) | −0.023 (2) |
O4 | 0.0344 (14) | 0.0445 (15) | 0.0473 (15) | 0.0062 (11) | 0.0155 (12) | −0.0059 (12) |
C26 | 0.054 (3) | 0.057 (3) | 0.054 (3) | 0.028 (2) | 0.015 (2) | −0.002 (2) |
C27 | 0.071 (3) | 0.031 (2) | 0.056 (3) | 0.007 (2) | 0.017 (2) | −0.0034 (19) |
C28 | 0.050 (2) | 0.049 (2) | 0.043 (2) | −0.0008 (19) | 0.0074 (19) | 0.0137 (19) |
C29 | 0.039 (2) | 0.051 (3) | 0.052 (2) | 0.0021 (18) | 0.0030 (19) | 0.010 (2) |
O5 | 0.0295 (13) | 0.0450 (15) | 0.0489 (15) | −0.0031 (11) | 0.0075 (11) | 0.0040 (12) |
C30 | 0.031 (2) | 0.063 (3) | 0.076 (3) | −0.008 (2) | −0.003 (2) | 0.010 (2) |
C31 | 0.044 (2) | 0.058 (3) | 0.065 (3) | −0.021 (2) | −0.004 (2) | 0.005 (2) |
O6 | 0.0393 (14) | 0.0421 (15) | 0.0501 (17) | −0.0111 (12) | 0.0021 (13) | 0.0006 (12) |
C32 | 0.054 (3) | 0.042 (2) | 0.064 (3) | −0.0148 (19) | 0.010 (2) | 0.000 (2) |
C33 | 0.057 (3) | 0.038 (2) | 0.058 (3) | −0.0153 (19) | 0.017 (2) | 0.005 (2) |
N5 | 0.0468 (18) | 0.0312 (16) | 0.0440 (19) | −0.0014 (14) | 0.0131 (15) | −0.0018 (14) |
C34 | 0.0230 (18) | 0.044 (2) | 0.039 (2) | 0.0001 (16) | 0.0067 (16) | 0.0086 (18) |
C35 | 0.033 (2) | 0.029 (2) | 0.056 (2) | −0.0039 (16) | 0.0038 (19) | 0.0148 (18) |
C36 | 0.036 (2) | 0.029 (2) | 0.049 (2) | 0.0069 (16) | 0.0022 (18) | −0.0010 (17) |
C37 | 0.0312 (19) | 0.031 (2) | 0.039 (2) | 0.0040 (15) | 0.0085 (16) | −0.0006 (16) |
C38 | 0.0241 (17) | 0.0350 (19) | 0.0259 (18) | 0.0010 (15) | 0.0015 (14) | 0.0037 (15) |
C39 | 0.0252 (17) | 0.037 (2) | 0.0305 (19) | 0.0028 (15) | 0.0107 (15) | 0.0002 (15) |
C40 | 0.0215 (16) | 0.0313 (19) | 0.0266 (18) | 0.0010 (14) | 0.0004 (14) | 0.0051 (14) |
Fe1—N1 | 1.959 (2) | O2—C20 | 1.426 (4) |
Fe1—N1i | 1.959 (2) | C20—C21 | 1.512 (4) |
Fe1—N3i | 1.965 (2) | C20—H20A | 0.9900 |
Fe1—N3 | 1.965 (2) | C20—H20B | 0.9900 |
Fe1—N2i | 1.969 (2) | C21—N5 | 1.475 (4) |
Fe1—N2 | 1.969 (2) | C21—H21A | 0.9900 |
N1—C1 | 1.336 (4) | C21—H21B | 0.9900 |
N1—C5 | 1.400 (4) | C22—C23 | 1.510 (5) |
C1—C2 | 1.383 (4) | C22—H22A | 0.9900 |
C1—H1A | 0.9500 | C22—H22B | 0.9900 |
C2—C3 | 1.398 (5) | C23—O3 | 1.422 (4) |
C2—H2A | 0.9500 | C23—H23A | 0.9900 |
C3—C4 | 1.359 (5) | C23—H23B | 0.9900 |
C3—H3A | 0.9500 | O3—C24 | 1.432 (4) |
C4—C5 | 1.415 (4) | C24—C25 | 1.475 (5) |
C4—H4A | 0.9500 | C24—H24A | 0.9900 |
C5—C6 | 1.431 (4) | C24—H24B | 0.9900 |
C6—N2 | 1.395 (4) | C25—O4 | 1.436 (4) |
C6—C7 | 1.421 (4) | C25—H25A | 0.9900 |
C7—C8 | 1.356 (5) | C25—H25B | 0.9900 |
C7—H7A | 0.9500 | O4—C26 | 1.421 (4) |
C8—C9 | 1.403 (5) | C26—C27 | 1.499 (5) |
C8—H8A | 0.9500 | C26—H26A | 0.9900 |
C9—C10 | 1.381 (4) | C26—H26B | 0.9900 |
C9—H9A | 0.9500 | C27—N5 | 1.476 (4) |
C10—N2 | 1.347 (4) | C27—H27A | 0.9900 |
C10—H10A | 0.9500 | C27—H27B | 0.9900 |
N3—C11 | 1.344 (4) | C28—C29 | 1.511 (5) |
N3—C15 | 1.397 (4) | C28—H28A | 0.9900 |
C11—C12 | 1.372 (4) | C28—H28B | 0.9900 |
C11—H11A | 0.9500 | C29—O5 | 1.423 (4) |
C12—C13 | 1.414 (5) | C29—H29A | 0.9900 |
C12—H12A | 0.9500 | C29—H29B | 0.9900 |
C13—C14 | 1.352 (4) | O5—C30 | 1.422 (4) |
C13—H13A | 0.9500 | C30—C31 | 1.495 (5) |
C14—C15 | 1.420 (4) | C30—H30A | 0.9900 |
C14—H14A | 0.9500 | C30—H30B | 0.9900 |
C15—C15i | 1.411 (6) | C31—O6 | 1.417 (4) |
K1—O2 | 2.793 (2) | C31—H31A | 0.9900 |
K1—O4 | 2.801 (2) | C31—H31B | 0.9900 |
K1—O1 | 2.833 (2) | O6—C32 | 1.426 (4) |
K1—O3 | 2.834 (2) | C32—C33 | 1.507 (5) |
K1—O5 | 2.840 (2) | C32—H32A | 0.9900 |
K1—O6 | 2.865 (2) | C32—H32B | 0.9900 |
K1—N4 | 3.012 (3) | C33—N5 | 1.473 (4) |
K1—N5 | 3.016 (3) | C33—H33A | 0.9900 |
N4—C16 | 1.472 (4) | C33—H33B | 0.9900 |
N4—C22 | 1.478 (4) | C34—C35 | 1.380 (5) |
N4—C28 | 1.481 (4) | C34—C40ii | 1.415 (4) |
C16—C17 | 1.508 (5) | C34—H34A | 0.9500 |
C16—H16A | 0.9900 | C35—C36 | 1.399 (5) |
C16—H16B | 0.9900 | C35—H35A | 0.9500 |
C17—O1 | 1.427 (4) | C36—C37 | 1.380 (4) |
C17—H17A | 0.9900 | C36—H36A | 0.9500 |
C17—H17B | 0.9900 | C37—C38 | 1.414 (4) |
O1—C18 | 1.431 (4) | C37—H37A | 0.9500 |
C18—C19 | 1.491 (4) | C38—C39 | 1.406 (4) |
C18—H18A | 0.9900 | C38—C40ii | 1.451 (4) |
C18—H18B | 0.9900 | C39—C40 | 1.412 (4) |
C19—O2 | 1.430 (4) | C39—H39A | 0.9500 |
C19—H19A | 0.9900 | C40—C34ii | 1.415 (4) |
C19—H19B | 0.9900 | C40—C38ii | 1.451 (4) |
N1—Fe1—N1i | 173.60 (14) | C18—C19—H19B | 109.9 |
N1—Fe1—N3i | 90.34 (10) | H19A—C19—H19B | 108.3 |
N1i—Fe1—N3i | 94.49 (10) | C20—O2—C19 | 111.6 (2) |
N1—Fe1—N3 | 94.49 (10) | C20—O2—K1 | 116.60 (18) |
N1i—Fe1—N3 | 90.35 (10) | C19—O2—K1 | 116.19 (17) |
N3i—Fe1—N3 | 81.82 (15) | O2—C20—C21 | 108.5 (3) |
N1—Fe1—N2i | 92.71 (10) | O2—C20—H20A | 110.0 |
N1i—Fe1—N2i | 82.79 (10) | C21—C20—H20A | 110.0 |
N3i—Fe1—N2i | 174.78 (10) | O2—C20—H20B | 110.0 |
N3—Fe1—N2i | 93.71 (10) | C21—C20—H20B | 110.0 |
N1—Fe1—N2 | 82.79 (10) | H20A—C20—H20B | 108.4 |
N1i—Fe1—N2 | 92.71 (10) | N5—C21—C20 | 113.4 (3) |
N3i—Fe1—N2 | 93.71 (10) | N5—C21—H21A | 108.9 |
N3—Fe1—N2 | 174.78 (10) | C20—C21—H21A | 108.9 |
N2i—Fe1—N2 | 90.87 (14) | N5—C21—H21B | 108.9 |
C1—N1—C5 | 117.6 (3) | C20—C21—H21B | 108.9 |
C1—N1—Fe1 | 128.4 (2) | H21A—C21—H21B | 107.7 |
C5—N1—Fe1 | 114.0 (2) | N4—C22—C23 | 113.9 (3) |
N1—C1—C2 | 124.2 (3) | N4—C22—H22A | 108.8 |
N1—C1—H1A | 117.9 | C23—C22—H22A | 108.8 |
C2—C1—H1A | 117.9 | N4—C22—H22B | 108.8 |
C1—C2—C3 | 118.8 (3) | C23—C22—H22B | 108.8 |
C1—C2—H2A | 120.6 | H22A—C22—H22B | 107.7 |
C3—C2—H2A | 120.6 | O3—C23—C22 | 108.9 (3) |
C4—C3—C2 | 118.5 (3) | O3—C23—H23A | 109.9 |
C4—C3—H3A | 120.7 | C22—C23—H23A | 109.9 |
C2—C3—H3A | 120.7 | O3—C23—H23B | 109.9 |
C3—C4—C5 | 121.5 (3) | C22—C23—H23B | 109.9 |
C3—C4—H4A | 119.3 | H23A—C23—H23B | 108.3 |
C5—C4—H4A | 119.3 | C23—O3—C24 | 111.6 (3) |
N1—C5—C4 | 119.3 (3) | C23—O3—K1 | 117.26 (19) |
N1—C5—C6 | 114.5 (3) | C24—O3—K1 | 114.3 (2) |
C4—C5—C6 | 126.1 (3) | O3—C24—C25 | 110.8 (3) |
N2—C6—C7 | 119.6 (3) | O3—C24—H24A | 109.5 |
N2—C6—C5 | 114.8 (3) | C25—C24—H24A | 109.5 |
C7—C6—C5 | 125.6 (3) | O3—C24—H24B | 109.5 |
C8—C7—C6 | 120.1 (3) | C25—C24—H24B | 109.5 |
C8—C7—H7A | 120.0 | H24A—C24—H24B | 108.1 |
C6—C7—H7A | 120.0 | O4—C25—C24 | 109.2 (3) |
C7—C8—C9 | 120.4 (3) | O4—C25—H25A | 109.8 |
C7—C8—H8A | 119.8 | C24—C25—H25A | 109.8 |
C9—C8—H8A | 119.8 | O4—C25—H25B | 109.8 |
C10—C9—C8 | 117.9 (3) | C24—C25—H25B | 109.8 |
C10—C9—H9A | 121.1 | H25A—C25—H25B | 108.3 |
C8—C9—H9A | 121.1 | C26—O4—C25 | 109.9 (3) |
N2—C10—C9 | 123.7 (3) | C26—O4—K1 | 118.24 (19) |
N2—C10—H10A | 118.1 | C25—O4—K1 | 116.4 (2) |
C9—C10—H10A | 118.1 | O4—C26—C27 | 109.6 (3) |
C10—N2—C6 | 118.3 (3) | O4—C26—H26A | 109.7 |
C10—N2—Fe1 | 127.9 (2) | C27—C26—H26A | 109.7 |
C6—N2—Fe1 | 113.7 (2) | O4—C26—H26B | 109.7 |
C11—N3—C15 | 117.5 (3) | C27—C26—H26B | 109.7 |
C11—N3—Fe1 | 128.0 (2) | H26A—C26—H26B | 108.2 |
C15—N3—Fe1 | 114.50 (19) | N5—C27—C26 | 114.4 (3) |
N3—C11—C12 | 124.7 (3) | N5—C27—H27A | 108.7 |
N3—C11—H11A | 117.7 | C26—C27—H27A | 108.7 |
C12—C11—H11A | 117.7 | N5—C27—H27B | 108.7 |
C11—C12—C13 | 118.4 (3) | C26—C27—H27B | 108.7 |
C11—C12—H12A | 120.8 | H27A—C27—H27B | 107.6 |
C13—C12—H12A | 120.8 | N4—C28—C29 | 113.2 (3) |
C14—C13—C12 | 118.6 (3) | N4—C28—H28A | 108.9 |
C14—C13—H13A | 120.7 | C29—C28—H28A | 108.9 |
C12—C13—H13A | 120.7 | N4—C28—H28B | 108.9 |
C13—C14—C15 | 121.4 (3) | C29—C28—H28B | 108.9 |
C13—C14—H14A | 119.3 | H28A—C28—H28B | 107.8 |
C15—C14—H14A | 119.3 | O5—C29—C28 | 108.9 (3) |
N3—C15—C15i | 114.58 (16) | O5—C29—H29A | 109.9 |
N3—C15—C14 | 119.4 (3) | C28—C29—H29A | 109.9 |
C15i—C15—C14 | 126.03 (19) | O5—C29—H29B | 109.9 |
O2—K1—O4 | 97.27 (7) | C28—C29—H29B | 109.9 |
O2—K1—O1 | 60.28 (6) | H29A—C29—H29B | 108.3 |
O4—K1—O1 | 135.92 (7) | C30—O5—C29 | 110.8 (3) |
O2—K1—O3 | 118.85 (7) | C30—O5—K1 | 114.3 (2) |
O4—K1—O3 | 60.09 (7) | C29—O5—K1 | 118.71 (19) |
O1—K1—O3 | 96.00 (7) | O5—C30—C31 | 109.4 (3) |
O2—K1—O5 | 138.00 (7) | O5—C30—H30A | 109.8 |
O4—K1—O5 | 119.67 (7) | C31—C30—H30A | 109.8 |
O1—K1—O5 | 98.61 (7) | O5—C30—H30B | 109.8 |
O3—K1—O5 | 97.86 (7) | C31—C30—H30B | 109.8 |
O2—K1—O6 | 98.44 (7) | H30A—C30—H30B | 108.2 |
O4—K1—O6 | 97.58 (7) | O6—C31—C30 | 109.6 (3) |
O1—K1—O6 | 121.54 (7) | O6—C31—H31A | 109.8 |
O3—K1—O6 | 137.37 (7) | C30—C31—H31A | 109.8 |
O5—K1—O6 | 59.96 (7) | O6—C31—H31B | 109.8 |
O2—K1—N4 | 119.69 (7) | C30—C31—H31B | 109.8 |
O4—K1—N4 | 119.88 (8) | H31A—C31—H31B | 108.2 |
O1—K1—N4 | 60.02 (7) | C31—O6—C32 | 111.5 (3) |
O3—K1—N4 | 60.74 (7) | C31—O6—K1 | 113.6 (2) |
O5—K1—N4 | 59.97 (7) | C32—O6—K1 | 117.4 (2) |
O6—K1—N4 | 119.09 (7) | O6—C32—C33 | 109.6 (3) |
O2—K1—N5 | 60.96 (7) | O6—C32—H32A | 109.7 |
O4—K1—N5 | 60.63 (8) | C33—C32—H32A | 109.7 |
O1—K1—N5 | 120.46 (8) | O6—C32—H32B | 109.7 |
O3—K1—N5 | 119.95 (8) | C33—C32—H32B | 109.7 |
O5—K1—N5 | 118.89 (7) | H32A—C32—H32B | 108.2 |
O6—K1—N5 | 59.77 (7) | N5—C33—C32 | 113.3 (3) |
N4—K1—N5 | 178.86 (8) | N5—C33—H33A | 108.9 |
C16—N4—C22 | 110.3 (3) | C32—C33—H33A | 108.9 |
C16—N4—C28 | 109.9 (3) | N5—C33—H33B | 108.9 |
C22—N4—C28 | 110.0 (3) | C32—C33—H33B | 108.9 |
C16—N4—K1 | 108.99 (19) | H33A—C33—H33B | 107.7 |
C22—N4—K1 | 108.1 (2) | C33—N5—C21 | 109.4 (3) |
C28—N4—K1 | 109.57 (19) | C33—N5—C27 | 109.8 (3) |
N4—C16—C17 | 114.0 (3) | C21—N5—C27 | 110.4 (3) |
N4—C16—H16A | 108.7 | C33—N5—K1 | 110.6 (2) |
C17—C16—H16A | 108.7 | C21—N5—K1 | 108.03 (19) |
N4—C16—H16B | 108.7 | C27—N5—K1 | 108.5 (2) |
C17—C16—H16B | 108.7 | C35—C34—C40ii | 122.6 (3) |
H16A—C16—H16B | 107.6 | C35—C34—H34A | 118.7 |
O1—C17—C16 | 109.0 (3) | C40ii—C34—H34A | 118.7 |
O1—C17—H17A | 109.9 | C34—C35—C36 | 119.4 (3) |
C16—C17—H17A | 109.9 | C34—C35—H35A | 120.3 |
O1—C17—H17B | 109.9 | C36—C35—H35A | 120.3 |
C16—C17—H17B | 109.9 | C37—C36—C35 | 120.5 (3) |
H17A—C17—H17B | 108.3 | C37—C36—H36A | 119.8 |
C17—O1—C18 | 111.5 (2) | C35—C36—H36A | 119.8 |
C17—O1—K1 | 119.70 (19) | C36—C37—C38 | 121.7 (3) |
C18—O1—K1 | 112.31 (17) | C36—C37—H37A | 119.1 |
O1—C18—C19 | 108.3 (3) | C38—C37—H37A | 119.1 |
O1—C18—H18A | 110.0 | C39—C38—C37 | 123.3 (3) |
C19—C18—H18A | 110.0 | C39—C38—C40ii | 118.5 (3) |
O1—C18—H18B | 110.0 | C37—C38—C40ii | 118.3 (3) |
C19—C18—H18B | 110.0 | C38—C39—C40 | 123.0 (3) |
H18A—C18—H18B | 108.4 | C38—C39—H39A | 118.5 |
O2—C19—C18 | 109.0 (3) | C40—C39—H39A | 118.5 |
O2—C19—H19A | 109.9 | C39—C40—C34ii | 124.0 (3) |
C18—C19—H19A | 109.9 | C39—C40—C38ii | 118.5 (3) |
O2—C19—H19B | 109.9 | C34ii—C40—C38ii | 117.5 (3) |
C5—N1—C1—C2 | −2.9 (5) | K1—O2—C20—C21 | 53.8 (3) |
Fe1—N1—C1—C2 | 178.7 (2) | O2—C20—C21—N5 | −66.6 (4) |
N1—C1—C2—C3 | 0.7 (5) | C16—N4—C22—C23 | 165.0 (3) |
C1—C2—C3—C4 | 0.7 (5) | C28—N4—C22—C23 | −73.7 (4) |
C2—C3—C4—C5 | 0.2 (5) | K1—N4—C22—C23 | 45.9 (3) |
C1—N1—C5—C4 | 3.7 (4) | N4—C22—C23—O3 | −66.0 (4) |
Fe1—N1—C5—C4 | −177.7 (2) | C22—C23—O3—C24 | −176.0 (3) |
C1—N1—C5—C6 | −175.3 (3) | C22—C23—O3—K1 | 49.5 (3) |
Fe1—N1—C5—C6 | 3.3 (3) | C23—O3—C24—C25 | 176.7 (3) |
C3—C4—C5—N1 | −2.4 (5) | K1—O3—C24—C25 | −47.4 (3) |
C3—C4—C5—C6 | 176.4 (3) | O3—C24—C25—O4 | 62.1 (4) |
N1—C5—C6—N2 | −1.0 (4) | C24—C25—O4—C26 | 176.0 (3) |
C4—C5—C6—N2 | −179.9 (3) | C24—C25—O4—K1 | −46.1 (3) |
N1—C5—C6—C7 | 176.8 (3) | C25—O4—C26—C27 | −173.6 (3) |
C4—C5—C6—C7 | −2.1 (5) | K1—O4—C26—C27 | 49.4 (4) |
N2—C6—C7—C8 | 2.4 (5) | O4—C26—C27—N5 | −63.2 (4) |
C5—C6—C7—C8 | −175.4 (3) | C16—N4—C28—C29 | −74.2 (4) |
C6—C7—C8—C9 | −1.0 (5) | C22—N4—C28—C29 | 164.2 (3) |
C7—C8—C9—C10 | −1.0 (5) | K1—N4—C28—C29 | 45.5 (3) |
C8—C9—C10—N2 | 1.7 (5) | N4—C28—C29—O5 | −63.8 (4) |
C9—C10—N2—C6 | −0.4 (5) | C28—C29—O5—C30 | −176.4 (3) |
C9—C10—N2—Fe1 | 177.3 (2) | C28—C29—O5—K1 | 48.3 (4) |
C7—C6—N2—C10 | −1.6 (4) | C29—O5—C30—C31 | 173.3 (3) |
C5—C6—N2—C10 | 176.3 (3) | K1—O5—C30—C31 | −49.3 (4) |
C7—C6—N2—Fe1 | −179.7 (2) | O5—C30—C31—O6 | 66.5 (5) |
C5—C6—N2—Fe1 | −1.7 (3) | C30—C31—O6—C32 | 175.7 (3) |
C15—N3—C11—C12 | −1.3 (5) | C30—C31—O6—K1 | −48.9 (4) |
Fe1—N3—C11—C12 | −178.8 (2) | C31—O6—C32—C33 | −176.6 (3) |
N3—C11—C12—C13 | 0.1 (5) | K1—O6—C32—C33 | 49.8 (4) |
C11—C12—C13—C14 | 0.2 (5) | O6—C32—C33—N5 | −63.4 (4) |
C12—C13—C14—C15 | 0.8 (5) | C32—C33—N5—C21 | 162.2 (3) |
C11—N3—C15—C15i | −178.9 (3) | C32—C33—N5—C27 | −76.5 (4) |
Fe1—N3—C15—C15i | −1.0 (4) | C32—C33—N5—K1 | 43.3 (4) |
C11—N3—C15—C14 | 2.2 (4) | C20—C21—N5—C33 | −77.4 (4) |
Fe1—N3—C15—C14 | −179.9 (2) | C20—C21—N5—C27 | 161.6 (3) |
C13—C14—C15—N3 | −2.0 (5) | C20—C21—N5—K1 | 43.1 (3) |
C13—C14—C15—C15i | 179.2 (4) | C26—C27—N5—C33 | 163.9 (3) |
C22—N4—C16—C17 | −71.3 (4) | C26—C27—N5—C21 | −75.3 (4) |
C28—N4—C16—C17 | 167.2 (3) | C26—C27—N5—K1 | 42.9 (3) |
K1—N4—C16—C17 | 47.2 (3) | C40ii—C34—C35—C36 | 1.4 (5) |
N4—C16—C17—O1 | −62.5 (4) | C34—C35—C36—C37 | 0.8 (5) |
C16—C17—O1—C18 | 178.4 (3) | C35—C36—C37—C38 | −1.6 (5) |
C16—C17—O1—K1 | 44.5 (3) | C36—C37—C38—C39 | −179.3 (3) |
C17—O1—C18—C19 | 168.5 (3) | C36—C37—C38—C40ii | 0.1 (5) |
K1—O1—C18—C19 | −54.0 (3) | C37—C38—C39—C40 | 177.4 (3) |
O1—C18—C19—O2 | 66.2 (3) | C40ii—C38—C39—C40 | −2.0 (5) |
C18—C19—O2—C20 | 178.2 (3) | C38—C39—C40—C34ii | −178.5 (3) |
C18—C19—O2—K1 | −44.7 (3) | C38—C39—C40—C38ii | 2.0 (5) |
C19—O2—C20—C21 | −169.3 (3) |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+3/2, −y+1/2, −z+1. |
[K(C18H36N2O6)][Co(C10H8N2)2]·0.5C14H10·2C4H8O | Z = 2 |
Mr = 1020.20 | F(000) = 1086 |
Triclinic, P1 | Dx = 1.289 Mg m−3 |
a = 10.5981 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.4323 (11) Å | Cell parameters from 3379 reflections |
c = 18.4886 (15) Å | θ = 2.3–25.0° |
α = 99.1054 (13)° | µ = 0.46 mm−1 |
β = 90.8279 (14)° | T = 173 K |
γ = 109.2433 (13)° | Rod, purple-black |
V = 2629.5 (4) Å3 | 0.40 × 0.18 × 0.12 mm |
Siemens SMART CCD platform diffractometer | 7616 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.021 |
ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2012) | h = −12→12 |
Tmin = 0.684, Tmax = 0.745 | k = −17→17 |
26404 measured reflections | l = −22→22 |
9299 independent reflections |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0385P)2 + 0.7396P] where P = (Fo2 + 2Fc2)/3 |
9299 reflections | (Δ/σ)max = 0.002 |
715 parameters | Δρmax = 0.31 e Å−3 |
257 restraints | Δρmin = −0.22 e Å−3 |
[K(C18H36N2O6)][Co(C10H8N2)2]·0.5C14H10·2C4H8O | γ = 109.2433 (13)° |
Mr = 1020.20 | V = 2629.5 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.5981 (8) Å | Mo Kα radiation |
b = 14.4323 (11) Å | µ = 0.46 mm−1 |
c = 18.4886 (15) Å | T = 173 K |
α = 99.1054 (13)° | 0.40 × 0.18 × 0.12 mm |
β = 90.8279 (14)° |
Siemens SMART CCD platform diffractometer | 9299 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2012) | 7616 reflections with I > 2σ(I) |
Tmin = 0.684, Tmax = 0.745 | Rint = 0.021 |
26404 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 257 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.31 e Å−3 |
9299 reflections | Δρmin = −0.22 e Å−3 |
715 parameters |
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. Cocrystallized tetrahydrofuran (THF) solvent molecule O8—C43—C44—C45—C46 in (2) is located in a pocket that includes its inversion symmetry equivalent. After being modeled as disordered over two general positions, a third orientation could be found from the difference map. Thus the molecule was modeled as disordered over three positions, with a refined ratio of 0.412 (4):0.387 (3):0.201 (3). Analogous bond lengths and angles among the three positions of the disordered THF molecule and both directions around the ring of the ordered THF molecule (O7—C39—C40—C41—C42) were restrained to be similar. Anistropic displacement parameters for pairs of near isopositional atoms were heavily restrained to be similar. Additionally, anisotropic displacement parameters for all atoms in the two major components of the disorder were restrained to be similar, and separately, the same for all the atoms in the ring of the third component. H atoms were placed geometrically and treated as riding atoms: methylene, C—H = 0.99 Å, and sp2, C—H = 0.95 Å, with Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co1 | 0.79825 (2) | 0.68786 (2) | 0.27461 (2) | 0.02917 (7) | |
N1 | 0.73827 (14) | 0.76779 (10) | 0.34643 (8) | 0.0316 (3) | |
N2 | 0.94887 (14) | 0.72689 (10) | 0.34143 (7) | 0.0303 (3) | |
N3 | 0.70742 (14) | 0.69375 (10) | 0.18865 (8) | 0.0327 (3) | |
N4 | 0.80414 (14) | 0.56819 (10) | 0.21983 (8) | 0.0327 (3) | |
C1 | 0.61916 (18) | 0.78591 (13) | 0.34510 (10) | 0.0363 (4) | |
H1A | 0.5560 | 0.7523 | 0.3045 | 0.044* | |
C2 | 0.5853 (2) | 0.84865 (14) | 0.39785 (11) | 0.0428 (5) | |
H2A | 0.5015 | 0.8586 | 0.3933 | 0.051* | |
C3 | 0.6766 (2) | 0.89921 (14) | 0.45989 (11) | 0.0467 (5) | |
H3A | 0.6560 | 0.9445 | 0.4970 | 0.056* | |
C4 | 0.7945 (2) | 0.88103 (14) | 0.46467 (10) | 0.0421 (5) | |
H4A | 0.8556 | 0.9129 | 0.5064 | 0.051* | |
C5 | 0.82746 (18) | 0.81573 (12) | 0.40890 (9) | 0.0328 (4) | |
C6 | 0.94642 (18) | 0.79272 (12) | 0.40590 (9) | 0.0327 (4) | |
C7 | 1.0599 (2) | 0.83344 (13) | 0.45681 (10) | 0.0406 (5) | |
H7A | 1.0563 | 0.8768 | 0.5005 | 0.049* | |
C8 | 1.1743 (2) | 0.81149 (14) | 0.44420 (11) | 0.0466 (5) | |
H8A | 1.2505 | 0.8397 | 0.4782 | 0.056* | |
C9 | 1.17644 (19) | 0.74547 (13) | 0.37890 (11) | 0.0407 (4) | |
H9A | 1.2546 | 0.7288 | 0.3684 | 0.049* | |
C10 | 1.06525 (17) | 0.70633 (12) | 0.33152 (10) | 0.0338 (4) | |
H10A | 1.0686 | 0.6616 | 0.2886 | 0.041* | |
C11 | 0.66737 (17) | 0.77004 (14) | 0.17334 (10) | 0.0380 (4) | |
H11A | 0.6849 | 0.8273 | 0.2103 | 0.046* | |
C12 | 0.60390 (19) | 0.76895 (16) | 0.10826 (11) | 0.0474 (5) | |
H12A | 0.5789 | 0.8244 | 0.1008 | 0.057* | |
C13 | 0.57571 (19) | 0.68474 (18) | 0.05212 (11) | 0.0505 (5) | |
H13A | 0.5286 | 0.6813 | 0.0071 | 0.061* | |
C14 | 0.61799 (18) | 0.60868 (16) | 0.06431 (10) | 0.0442 (5) | |
H14A | 0.6006 | 0.5517 | 0.0270 | 0.053* | |
C15 | 0.68694 (16) | 0.61284 (13) | 0.13113 (9) | 0.0350 (4) | |
C16 | 0.74272 (17) | 0.54251 (13) | 0.14845 (10) | 0.0355 (4) | |
C17 | 0.7434 (2) | 0.45519 (15) | 0.10176 (11) | 0.0470 (5) | |
H17A | 0.7040 | 0.4402 | 0.0530 | 0.056* | |
C18 | 0.7995 (2) | 0.39217 (15) | 0.12556 (12) | 0.0529 (6) | |
H18A | 0.8018 | 0.3344 | 0.0936 | 0.064* | |
C19 | 0.85409 (19) | 0.41464 (14) | 0.19876 (12) | 0.0459 (5) | |
H19A | 0.8901 | 0.3704 | 0.2176 | 0.055* | |
C20 | 0.85480 (17) | 0.50058 (12) | 0.24235 (11) | 0.0362 (4) | |
H20A | 0.8928 | 0.5144 | 0.2914 | 0.043* | |
K1 | 0.20912 (4) | 0.21094 (3) | 0.24133 (2) | 0.02954 (9) | |
N5 | 0.10809 (15) | −0.01034 (10) | 0.24458 (8) | 0.0347 (3) | |
N6 | 0.31118 (14) | 0.43454 (10) | 0.23696 (8) | 0.0332 (3) | |
O1 | 0.38212 (12) | 0.12138 (9) | 0.29969 (6) | 0.0385 (3) | |
O2 | 0.46266 (12) | 0.32999 (9) | 0.30661 (7) | 0.0390 (3) | |
O3 | −0.01121 (12) | 0.13026 (9) | 0.32558 (7) | 0.0398 (3) | |
O4 | 0.06812 (12) | 0.33387 (8) | 0.30799 (6) | 0.0368 (3) | |
O5 | 0.10657 (12) | 0.07044 (9) | 0.10631 (6) | 0.0359 (3) | |
O6 | 0.22491 (12) | 0.27768 (9) | 0.10430 (6) | 0.0368 (3) | |
C21 | 0.2210 (2) | −0.04156 (13) | 0.26402 (11) | 0.0421 (5) | |
H21A | 0.2712 | −0.0488 | 0.2199 | 0.051* | |
H21B | 0.1854 | −0.1077 | 0.2790 | 0.051* | |
C22 | 0.3162 (2) | 0.03021 (14) | 0.32510 (11) | 0.0451 (5) | |
H22A | 0.2662 | 0.0428 | 0.3682 | 0.054* | |
H22B | 0.3832 | 0.0014 | 0.3401 | 0.054* | |
C23 | 0.4818 (2) | 0.19048 (15) | 0.35253 (11) | 0.0468 (5) | |
H23A | 0.5462 | 0.1592 | 0.3672 | 0.056* | |
H23B | 0.4393 | 0.2106 | 0.3969 | 0.056* | |
C24 | 0.55316 (19) | 0.27983 (15) | 0.31909 (11) | 0.0449 (5) | |
H24A | 0.6301 | 0.3250 | 0.3526 | 0.054* | |
H24B | 0.5878 | 0.2588 | 0.2721 | 0.054* | |
C25 | 0.52743 (18) | 0.41829 (14) | 0.27688 (11) | 0.0407 (4) | |
H25A | 0.5447 | 0.4001 | 0.2250 | 0.049* | |
H25B | 0.6144 | 0.4563 | 0.3048 | 0.049* | |
C26 | 0.43881 (18) | 0.48103 (13) | 0.28178 (11) | 0.0417 (5) | |
H26A | 0.4195 | 0.4961 | 0.3337 | 0.050* | |
H26B | 0.4879 | 0.5451 | 0.2662 | 0.050* | |
C27 | 0.0074 (2) | −0.03195 (13) | 0.29957 (11) | 0.0426 (5) | |
H27A | 0.0545 | −0.0178 | 0.3488 | 0.051* | |
H27B | −0.0461 | −0.1038 | 0.2891 | 0.051* | |
C28 | −0.08581 (19) | 0.02676 (13) | 0.30119 (11) | 0.0438 (5) | |
H28A | −0.1292 | 0.0171 | 0.2515 | 0.053* | |
H28B | −0.1567 | 0.0035 | 0.3350 | 0.053* | |
C29 | −0.09545 (19) | 0.18865 (14) | 0.33696 (11) | 0.0445 (5) | |
H29A | −0.1607 | 0.1637 | 0.3731 | 0.053* | |
H29B | −0.1459 | 0.1840 | 0.2903 | 0.053* | |
C30 | −0.0116 (2) | 0.29495 (14) | 0.36483 (11) | 0.0459 (5) | |
H30A | −0.0701 | 0.3347 | 0.3798 | 0.055* | |
H30B | 0.0469 | 0.2987 | 0.4082 | 0.055* | |
C31 | 0.14815 (19) | 0.43642 (13) | 0.33177 (10) | 0.0395 (4) | |
H31A | 0.2183 | 0.4417 | 0.3697 | 0.047* | |
H31B | 0.0913 | 0.4744 | 0.3535 | 0.047* | |
C32 | 0.21215 (19) | 0.47878 (13) | 0.26651 (10) | 0.0388 (4) | |
H32A | 0.1413 | 0.4675 | 0.2274 | 0.047* | |
H32B | 0.2565 | 0.5516 | 0.2812 | 0.047* | |
C33 | 0.0463 (2) | −0.06567 (13) | 0.17143 (10) | 0.0403 (4) | |
H33A | −0.0464 | −0.0648 | 0.1664 | 0.048* | |
H33B | 0.0412 | −0.1360 | 0.1678 | 0.048* | |
C34 | 0.12195 (19) | −0.02352 (13) | 0.10919 (10) | 0.0373 (4) | |
H34A | 0.2180 | −0.0149 | 0.1171 | 0.045* | |
H34B | 0.0864 | −0.0696 | 0.0623 | 0.045* | |
C35 | 0.16246 (18) | 0.11078 (13) | 0.04365 (9) | 0.0360 (4) | |
H35A | 0.1185 | 0.0643 | −0.0019 | 0.043* | |
H35B | 0.2594 | 0.1205 | 0.0448 | 0.043* | |
C36 | 0.14135 (18) | 0.20817 (13) | 0.04478 (10) | 0.0366 (4) | |
H36A | 0.1650 | 0.2320 | −0.0022 | 0.044* | |
H36B | 0.0462 | 0.2006 | 0.0515 | 0.044* | |
C37 | 0.21844 (19) | 0.37532 (13) | 0.10715 (10) | 0.0383 (4) | |
H37A | 0.1309 | 0.3773 | 0.1239 | 0.046* | |
H37B | 0.2279 | 0.3939 | 0.0577 | 0.046* | |
C38 | 0.33039 (19) | 0.44715 (13) | 0.15991 (10) | 0.0391 (4) | |
H38A | 0.4159 | 0.4378 | 0.1461 | 0.047* | |
H38B | 0.3375 | 0.5161 | 0.1554 | 0.047* | |
O7 | 0.13286 (14) | 0.74744 (10) | 0.04490 (8) | 0.0533 (4) | |
C39 | 0.0381 (2) | 0.65889 (16) | 0.06289 (14) | 0.0586 (6) | |
H39A | −0.0069 | 0.6124 | 0.0175 | 0.070* | |
H39B | −0.0309 | 0.6756 | 0.0926 | 0.070* | |
C40 | 0.1144 (2) | 0.61194 (16) | 0.10591 (13) | 0.0561 (6) | |
H40A | 0.1400 | 0.5605 | 0.0735 | 0.067* | |
H40B | 0.0610 | 0.5813 | 0.1448 | 0.067* | |
C41 | 0.2363 (2) | 0.69890 (16) | 0.13853 (12) | 0.0544 (5) | |
H41A | 0.2179 | 0.7349 | 0.1851 | 0.065* | |
H41B | 0.3135 | 0.6770 | 0.1475 | 0.065* | |
C42 | 0.26071 (19) | 0.76210 (14) | 0.07959 (12) | 0.0459 (5) | |
H42A | 0.3052 | 0.8332 | 0.1012 | 0.055* | |
H42B | 0.3188 | 0.7418 | 0.0435 | 0.055* | |
O8 | 0.6164 (13) | 0.0464 (13) | 0.1748 (6) | 0.122 (3) | 0.388 (3) |
C43 | 0.5026 (11) | 0.0357 (14) | 0.1278 (10) | 0.076 (4) | 0.388 (3) |
H43A | 0.4318 | 0.0516 | 0.1563 | 0.091* | 0.388 (3) |
H43B | 0.4651 | −0.0329 | 0.0995 | 0.091* | 0.388 (3) |
C44 | 0.5586 (9) | 0.1101 (9) | 0.0777 (9) | 0.085 (4) | 0.388 (3) |
H44A | 0.5752 | 0.1793 | 0.1029 | 0.102* | 0.388 (3) |
H44B | 0.4989 | 0.0962 | 0.0327 | 0.102* | 0.388 (3) |
C45 | 0.6877 (8) | 0.0909 (7) | 0.0610 (4) | 0.0563 (19) | 0.388 (3) |
H45A | 0.6721 | 0.0326 | 0.0215 | 0.068* | 0.388 (3) |
H45B | 0.7544 | 0.1498 | 0.0461 | 0.068* | 0.388 (3) |
C46 | 0.7330 (11) | 0.0711 (14) | 0.1325 (6) | 0.101 (5) | 0.388 (3) |
H46A | 0.7684 | 0.0151 | 0.1238 | 0.121* | 0.388 (3) |
H46B | 0.8044 | 0.1309 | 0.1588 | 0.121* | 0.388 (3) |
O8' | 0.7052 (8) | 0.0335 (7) | 0.1470 (7) | 0.129 (3) | 0.413 (3) |
C43' | 0.5802 (14) | 0.0279 (15) | 0.1804 (10) | 0.100 (4) | 0.413 (3) |
H43C | 0.5978 | 0.0696 | 0.2299 | 0.120* | 0.413 (3) |
H43D | 0.5290 | −0.0417 | 0.1850 | 0.120* | 0.413 (3) |
C44' | 0.5049 (11) | 0.0654 (13) | 0.1309 (10) | 0.081 (4) | 0.413 (3) |
H44C | 0.4523 | 0.1019 | 0.1593 | 0.098* | 0.413 (3) |
H44D | 0.4429 | 0.0096 | 0.0955 | 0.098* | 0.413 (3) |
C45' | 0.6087 (12) | 0.1335 (10) | 0.0917 (10) | 0.121 (5) | 0.413 (3) |
H45C | 0.5816 | 0.1210 | 0.0386 | 0.146* | 0.413 (3) |
H45D | 0.6218 | 0.2040 | 0.1120 | 0.146* | 0.413 (3) |
C46' | 0.7346 (12) | 0.1109 (12) | 0.1037 (10) | 0.138 (5) | 0.413 (3) |
H46C | 0.7661 | 0.0889 | 0.0560 | 0.166* | 0.413 (3) |
H46D | 0.8058 | 0.1711 | 0.1296 | 0.166* | 0.413 (3) |
O8" | 0.5137 (16) | 0.0635 (15) | 0.0627 (9) | 0.136 (7) | 0.199 (3) |
C43" | 0.624 (2) | 0.0295 (16) | 0.0456 (8) | 0.105 (6) | 0.199 (3) |
H43E | 0.6504 | 0.0393 | −0.0045 | 0.126* | 0.199 (3) |
H43F | 0.5990 | −0.0423 | 0.0480 | 0.126* | 0.199 (3) |
C44" | 0.7370 (17) | 0.089 (2) | 0.1009 (14) | 0.136 (6) | 0.199 (3) |
H44E | 0.7987 | 0.1463 | 0.0818 | 0.163* | 0.199 (3) |
H44F | 0.7883 | 0.0473 | 0.1148 | 0.163* | 0.199 (3) |
C45" | 0.6685 (17) | 0.1233 (15) | 0.1652 (9) | 0.117 (7) | 0.199 (3) |
H45E | 0.6451 | 0.0742 | 0.1989 | 0.140* | 0.199 (3) |
H45F | 0.7262 | 0.1885 | 0.1929 | 0.140* | 0.199 (3) |
C46" | 0.5447 (17) | 0.1318 (15) | 0.1305 (9) | 0.079 (5) | 0.199 (3) |
H46E | 0.4697 | 0.1144 | 0.1628 | 0.095* | 0.199 (3) |
H46F | 0.5612 | 0.2006 | 0.1218 | 0.095* | 0.199 (3) |
C47 | 0.34197 (17) | 0.62250 (12) | 0.48693 (9) | 0.0306 (4) | |
H47A | 0.3772 | 0.6821 | 0.4673 | 0.037* | |
C48 | 0.21420 (17) | 0.59539 (13) | 0.50810 (9) | 0.0332 (4) | |
H48A | 0.1608 | 0.6356 | 0.5025 | 0.040* | |
C49 | 0.16054 (17) | 0.50724 (13) | 0.53843 (9) | 0.0334 (4) | |
H49A | 0.0719 | 0.4897 | 0.5539 | 0.040* | |
C50 | 0.23424 (16) | 0.44747 (13) | 0.54566 (9) | 0.0316 (4) | |
H50A | 0.1966 | 0.3888 | 0.5661 | 0.038* | |
C51 | 0.36826 (16) | 0.47229 (12) | 0.52272 (9) | 0.0268 (3) | |
C52 | 0.44457 (16) | 0.41122 (12) | 0.52806 (9) | 0.0290 (4) | |
H52A | 0.4069 | 0.3511 | 0.5468 | 0.035* | |
C53 | 0.57645 (16) | 0.43707 (12) | 0.50624 (9) | 0.0270 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.02942 (13) | 0.02400 (12) | 0.02744 (13) | 0.00157 (9) | 0.00143 (9) | 0.00138 (9) |
N1 | 0.0342 (8) | 0.0256 (7) | 0.0299 (8) | 0.0028 (6) | 0.0049 (6) | 0.0054 (6) |
N2 | 0.0357 (8) | 0.0218 (7) | 0.0281 (7) | 0.0018 (6) | 0.0021 (6) | 0.0060 (6) |
N3 | 0.0276 (7) | 0.0314 (8) | 0.0315 (8) | 0.0009 (6) | 0.0021 (6) | 0.0029 (6) |
N4 | 0.0266 (7) | 0.0300 (8) | 0.0329 (8) | −0.0002 (6) | 0.0048 (6) | 0.0014 (6) |
C1 | 0.0360 (10) | 0.0288 (9) | 0.0389 (10) | 0.0034 (8) | 0.0063 (8) | 0.0070 (8) |
C2 | 0.0432 (11) | 0.0374 (10) | 0.0478 (12) | 0.0114 (9) | 0.0144 (9) | 0.0108 (9) |
C3 | 0.0640 (14) | 0.0376 (11) | 0.0374 (11) | 0.0173 (10) | 0.0151 (10) | 0.0020 (9) |
C4 | 0.0582 (13) | 0.0340 (10) | 0.0285 (10) | 0.0092 (9) | 0.0048 (9) | 0.0027 (8) |
C5 | 0.0444 (11) | 0.0223 (8) | 0.0251 (9) | 0.0016 (8) | 0.0045 (8) | 0.0056 (7) |
C6 | 0.0428 (10) | 0.0230 (8) | 0.0274 (9) | 0.0031 (7) | 0.0012 (8) | 0.0079 (7) |
C7 | 0.0556 (12) | 0.0294 (9) | 0.0300 (10) | 0.0056 (9) | −0.0081 (9) | 0.0049 (8) |
C8 | 0.0472 (12) | 0.0368 (11) | 0.0485 (12) | 0.0045 (9) | −0.0170 (10) | 0.0093 (9) |
C9 | 0.0397 (11) | 0.0324 (10) | 0.0481 (11) | 0.0078 (8) | −0.0041 (9) | 0.0114 (9) |
C10 | 0.0360 (10) | 0.0250 (9) | 0.0375 (10) | 0.0045 (8) | 0.0021 (8) | 0.0097 (7) |
C11 | 0.0304 (9) | 0.0391 (10) | 0.0392 (10) | 0.0049 (8) | 0.0017 (8) | 0.0069 (8) |
C12 | 0.0344 (10) | 0.0600 (13) | 0.0470 (12) | 0.0109 (10) | 0.0012 (9) | 0.0178 (10) |
C13 | 0.0330 (10) | 0.0757 (15) | 0.0326 (11) | 0.0048 (10) | −0.0024 (8) | 0.0101 (10) |
C14 | 0.0303 (10) | 0.0563 (12) | 0.0322 (10) | −0.0008 (9) | 0.0034 (8) | 0.0007 (9) |
C15 | 0.0245 (9) | 0.0390 (10) | 0.0285 (9) | −0.0041 (8) | 0.0045 (7) | 0.0003 (8) |
C16 | 0.0280 (9) | 0.0331 (9) | 0.0334 (10) | −0.0021 (8) | 0.0057 (7) | −0.0020 (8) |
C17 | 0.0408 (11) | 0.0441 (12) | 0.0404 (11) | 0.0010 (9) | 0.0059 (9) | −0.0099 (9) |
C18 | 0.0484 (12) | 0.0348 (11) | 0.0628 (14) | 0.0062 (10) | 0.0110 (11) | −0.0124 (10) |
C19 | 0.0368 (11) | 0.0327 (10) | 0.0621 (13) | 0.0056 (8) | 0.0109 (10) | 0.0026 (9) |
C20 | 0.0303 (9) | 0.0272 (9) | 0.0451 (11) | 0.0023 (8) | 0.0073 (8) | 0.0045 (8) |
K1 | 0.02985 (19) | 0.02562 (18) | 0.0305 (2) | 0.00589 (15) | 0.00308 (15) | 0.00460 (15) |
N5 | 0.0424 (9) | 0.0246 (7) | 0.0333 (8) | 0.0051 (6) | 0.0013 (7) | 0.0069 (6) |
N6 | 0.0336 (8) | 0.0257 (7) | 0.0366 (8) | 0.0058 (6) | 0.0071 (6) | 0.0037 (6) |
O1 | 0.0425 (7) | 0.0369 (7) | 0.0332 (7) | 0.0092 (6) | −0.0060 (6) | 0.0074 (5) |
O2 | 0.0282 (6) | 0.0381 (7) | 0.0456 (8) | 0.0033 (5) | 0.0030 (6) | 0.0091 (6) |
O3 | 0.0352 (7) | 0.0303 (7) | 0.0475 (8) | 0.0027 (5) | 0.0100 (6) | 0.0057 (6) |
O4 | 0.0424 (7) | 0.0296 (6) | 0.0358 (7) | 0.0094 (6) | 0.0135 (6) | 0.0029 (5) |
O5 | 0.0465 (7) | 0.0302 (6) | 0.0311 (7) | 0.0127 (6) | 0.0060 (6) | 0.0059 (5) |
O6 | 0.0447 (7) | 0.0313 (7) | 0.0327 (7) | 0.0106 (6) | −0.0030 (6) | 0.0059 (5) |
C21 | 0.0590 (13) | 0.0278 (9) | 0.0415 (11) | 0.0154 (9) | 0.0008 (9) | 0.0102 (8) |
C22 | 0.0585 (13) | 0.0405 (11) | 0.0397 (11) | 0.0178 (10) | −0.0043 (9) | 0.0149 (9) |
C23 | 0.0460 (12) | 0.0491 (12) | 0.0421 (11) | 0.0129 (10) | −0.0117 (9) | 0.0064 (9) |
C24 | 0.0325 (10) | 0.0503 (12) | 0.0465 (12) | 0.0083 (9) | −0.0064 (9) | 0.0051 (9) |
C25 | 0.0305 (10) | 0.0386 (10) | 0.0432 (11) | −0.0019 (8) | 0.0044 (8) | 0.0077 (9) |
C26 | 0.0389 (11) | 0.0272 (9) | 0.0472 (11) | −0.0018 (8) | 0.0038 (9) | −0.0001 (8) |
C27 | 0.0524 (12) | 0.0278 (9) | 0.0402 (11) | 0.0006 (9) | 0.0073 (9) | 0.0121 (8) |
C28 | 0.0415 (11) | 0.0323 (10) | 0.0464 (11) | −0.0037 (8) | 0.0104 (9) | 0.0085 (8) |
C29 | 0.0384 (11) | 0.0434 (11) | 0.0491 (12) | 0.0092 (9) | 0.0177 (9) | 0.0089 (9) |
C30 | 0.0507 (12) | 0.0405 (11) | 0.0449 (11) | 0.0135 (9) | 0.0235 (10) | 0.0051 (9) |
C31 | 0.0437 (11) | 0.0294 (9) | 0.0423 (11) | 0.0118 (8) | 0.0104 (9) | −0.0024 (8) |
C32 | 0.0448 (11) | 0.0249 (9) | 0.0468 (11) | 0.0125 (8) | 0.0105 (9) | 0.0040 (8) |
C33 | 0.0483 (11) | 0.0237 (9) | 0.0404 (11) | 0.0024 (8) | −0.0029 (9) | 0.0027 (8) |
C34 | 0.0469 (11) | 0.0287 (9) | 0.0335 (10) | 0.0120 (8) | −0.0038 (8) | −0.0008 (8) |
C35 | 0.0385 (10) | 0.0385 (10) | 0.0273 (9) | 0.0095 (8) | 0.0007 (8) | 0.0027 (8) |
C36 | 0.0374 (10) | 0.0409 (10) | 0.0296 (9) | 0.0092 (8) | −0.0004 (8) | 0.0099 (8) |
C37 | 0.0487 (11) | 0.0353 (10) | 0.0365 (10) | 0.0170 (9) | 0.0100 (9) | 0.0152 (8) |
C38 | 0.0437 (11) | 0.0274 (9) | 0.0461 (11) | 0.0083 (8) | 0.0143 (9) | 0.0134 (8) |
O7 | 0.0459 (8) | 0.0471 (8) | 0.0723 (10) | 0.0155 (7) | 0.0048 (7) | 0.0263 (7) |
C39 | 0.0455 (12) | 0.0457 (12) | 0.0814 (17) | 0.0064 (10) | −0.0015 (11) | 0.0217 (12) |
C40 | 0.0538 (13) | 0.0462 (12) | 0.0670 (15) | 0.0093 (10) | 0.0034 (11) | 0.0226 (11) |
C41 | 0.0518 (13) | 0.0528 (13) | 0.0578 (14) | 0.0132 (11) | 0.0011 (11) | 0.0169 (11) |
C42 | 0.0409 (11) | 0.0364 (10) | 0.0591 (13) | 0.0100 (9) | 0.0045 (10) | 0.0107 (9) |
O8 | 0.142 (8) | 0.128 (7) | 0.086 (4) | 0.025 (7) | 0.049 (5) | 0.024 (4) |
C43 | 0.060 (4) | 0.094 (9) | 0.071 (5) | 0.019 (4) | 0.019 (4) | 0.017 (6) |
C44 | 0.050 (7) | 0.076 (8) | 0.114 (10) | 0.008 (6) | −0.005 (6) | −0.003 (7) |
C45 | 0.071 (5) | 0.060 (4) | 0.044 (4) | 0.031 (4) | 0.007 (4) | 0.007 (4) |
C46 | 0.113 (10) | 0.142 (12) | 0.064 (6) | 0.041 (8) | 0.038 (6) | 0.063 (6) |
O8' | 0.079 (5) | 0.129 (7) | 0.179 (9) | 0.042 (5) | 0.035 (5) | 0.012 (6) |
C43' | 0.079 (6) | 0.109 (7) | 0.102 (6) | 0.020 (6) | 0.053 (5) | 0.014 (5) |
C44' | 0.070 (5) | 0.095 (10) | 0.065 (5) | 0.005 (5) | 0.030 (4) | 0.018 (6) |
C45' | 0.105 (10) | 0.082 (7) | 0.150 (11) | −0.019 (8) | 0.036 (10) | 0.049 (8) |
C46' | 0.105 (7) | 0.147 (9) | 0.144 (10) | 0.012 (6) | 0.080 (7) | 0.029 (8) |
O8" | 0.105 (13) | 0.149 (15) | 0.132 (13) | 0.034 (11) | 0.009 (10) | −0.022 (12) |
C43" | 0.141 (17) | 0.117 (14) | 0.075 (11) | 0.073 (13) | 0.036 (11) | 0.002 (11) |
C44" | 0.106 (9) | 0.144 (12) | 0.142 (12) | 0.016 (9) | 0.087 (9) | 0.024 (10) |
C45" | 0.087 (12) | 0.084 (12) | 0.137 (16) | −0.014 (10) | 0.018 (12) | −0.014 (12) |
C46" | 0.074 (11) | 0.074 (11) | 0.061 (10) | −0.008 (9) | −0.001 (8) | 0.000 (9) |
C47 | 0.0324 (9) | 0.0273 (9) | 0.0308 (9) | 0.0084 (7) | 0.0009 (7) | 0.0051 (7) |
C48 | 0.0333 (10) | 0.0349 (10) | 0.0329 (9) | 0.0152 (8) | 0.0004 (8) | 0.0023 (8) |
C49 | 0.0243 (9) | 0.0411 (10) | 0.0325 (9) | 0.0091 (8) | 0.0053 (7) | 0.0034 (8) |
C50 | 0.0287 (9) | 0.0306 (9) | 0.0320 (9) | 0.0038 (7) | 0.0053 (7) | 0.0083 (7) |
C51 | 0.0261 (8) | 0.0268 (8) | 0.0247 (8) | 0.0049 (7) | 0.0021 (7) | 0.0048 (7) |
C52 | 0.0304 (9) | 0.0261 (8) | 0.0293 (9) | 0.0060 (7) | 0.0035 (7) | 0.0082 (7) |
C53 | 0.0276 (9) | 0.0262 (8) | 0.0252 (8) | 0.0062 (7) | 0.0012 (7) | 0.0046 (7) |
Co1—N3 | 1.8742 (14) | C29—C30 | 1.499 (3) |
Co1—N1 | 1.8764 (14) | C29—H29A | 0.9900 |
Co1—N2 | 1.8767 (14) | C29—H29B | 0.9900 |
Co1—N4 | 1.8794 (14) | C30—H30A | 0.9900 |
N1—C1 | 1.372 (2) | C30—H30B | 0.9900 |
N1—C5 | 1.411 (2) | C31—C32 | 1.508 (3) |
N2—C10 | 1.369 (2) | C31—H31A | 0.9900 |
N2—C6 | 1.408 (2) | C31—H31B | 0.9900 |
N3—C11 | 1.370 (2) | C32—H32A | 0.9900 |
N3—C15 | 1.405 (2) | C32—H32B | 0.9900 |
N4—C20 | 1.372 (2) | C33—C34 | 1.505 (3) |
N4—C16 | 1.401 (2) | C33—H33A | 0.9900 |
C1—C2 | 1.358 (3) | C33—H33B | 0.9900 |
C1—H1A | 0.9500 | C34—H34A | 0.9900 |
C2—C3 | 1.422 (3) | C34—H34B | 0.9900 |
C2—H2A | 0.9500 | C35—C36 | 1.491 (3) |
C3—C4 | 1.363 (3) | C35—H35A | 0.9900 |
C3—H3A | 0.9500 | C35—H35B | 0.9900 |
C4—C5 | 1.412 (2) | C36—H36A | 0.9900 |
C4—H4A | 0.9500 | C36—H36B | 0.9900 |
C5—C6 | 1.405 (3) | C37—C38 | 1.507 (3) |
C6—C7 | 1.415 (2) | C37—H37A | 0.9900 |
C7—C8 | 1.365 (3) | C37—H37B | 0.9900 |
C7—H7A | 0.9500 | C38—H38A | 0.9900 |
C8—C9 | 1.420 (3) | C38—H38B | 0.9900 |
C8—H8A | 0.9500 | O7—C42 | 1.426 (2) |
C9—C10 | 1.360 (2) | O7—C39 | 1.432 (2) |
C9—H9A | 0.9500 | C39—C40 | 1.503 (3) |
C10—H10A | 0.9500 | C39—H39A | 0.9900 |
C11—C12 | 1.365 (3) | C39—H39B | 0.9900 |
C11—H11A | 0.9500 | C40—C41 | 1.509 (3) |
C12—C13 | 1.413 (3) | C40—H40A | 0.9900 |
C12—H12A | 0.9500 | C40—H40B | 0.9900 |
C13—C14 | 1.363 (3) | C41—C42 | 1.501 (3) |
C13—H13A | 0.9500 | C41—H41A | 0.9900 |
C14—C15 | 1.409 (3) | C41—H41B | 0.9900 |
C14—H14A | 0.9500 | C42—H42A | 0.9900 |
C15—C16 | 1.405 (3) | C42—H42B | 0.9900 |
C16—C17 | 1.413 (3) | O8—C43 | 1.428 (9) |
C17—C18 | 1.360 (3) | O8—C46 | 1.446 (8) |
C17—H17A | 0.9500 | C43—C44 | 1.508 (9) |
C18—C19 | 1.409 (3) | C43—H43A | 0.9900 |
C18—H18A | 0.9500 | C43—H43B | 0.9900 |
C19—C20 | 1.366 (3) | C44—C45 | 1.509 (9) |
C19—H19A | 0.9500 | C44—H44A | 0.9900 |
C20—H20A | 0.9500 | C44—H44B | 0.9900 |
K1—O2 | 2.7993 (12) | C45—C46 | 1.501 (8) |
K1—O4 | 2.8300 (12) | C45—H45A | 0.9900 |
K1—O6 | 2.8377 (12) | C45—H45B | 0.9900 |
K1—O3 | 2.8499 (12) | C46—H46A | 0.9900 |
K1—O1 | 2.8536 (13) | C46—H46B | 0.9900 |
K1—O5 | 2.8968 (12) | O8'—C46' | 1.430 (9) |
K1—N5 | 3.0262 (14) | O8'—C43' | 1.453 (9) |
K1—N6 | 3.0618 (14) | C43'—C44' | 1.479 (9) |
N5—C21 | 1.469 (2) | C43'—H43C | 0.9900 |
N5—C27 | 1.477 (2) | C43'—H43D | 0.9900 |
N5—C33 | 1.478 (2) | C44'—C45' | 1.496 (8) |
N6—C32 | 1.468 (2) | C44'—H44C | 0.9900 |
N6—C26 | 1.470 (2) | C44'—H44D | 0.9900 |
N6—C38 | 1.473 (2) | C45'—C46' | 1.495 (9) |
O1—C23 | 1.425 (2) | C45'—H45C | 0.9900 |
O1—C22 | 1.428 (2) | C45'—H45D | 0.9900 |
O2—C24 | 1.415 (2) | C46'—H46C | 0.9900 |
O2—C25 | 1.433 (2) | C46'—H46D | 0.9900 |
O3—C29 | 1.413 (2) | O8"—C46" | 1.427 (9) |
O3—C28 | 1.434 (2) | O8"—C43" | 1.432 (9) |
O4—C30 | 1.426 (2) | C43"—C44" | 1.492 (10) |
O4—C31 | 1.435 (2) | C43"—H43E | 0.9900 |
O5—C34 | 1.427 (2) | C43"—H43F | 0.9900 |
O5—C35 | 1.428 (2) | C44"—C45" | 1.504 (9) |
O6—C37 | 1.426 (2) | C44"—H44E | 0.9900 |
O6—C36 | 1.428 (2) | C44"—H44F | 0.9900 |
C21—C22 | 1.508 (3) | C45"—C46" | 1.502 (9) |
C21—H21A | 0.9900 | C45"—H45E | 0.9900 |
C21—H21B | 0.9900 | C45"—H45F | 0.9900 |
C22—H22A | 0.9900 | C46"—H46E | 0.9900 |
C22—H22B | 0.9900 | C46"—H46F | 0.9900 |
C23—C24 | 1.497 (3) | C47—C48 | 1.362 (2) |
C23—H23A | 0.9900 | C47—C53i | 1.423 (2) |
C23—H23B | 0.9900 | C47—H47A | 0.9500 |
C24—H24A | 0.9900 | C48—C49 | 1.419 (2) |
C24—H24B | 0.9900 | C48—H48A | 0.9500 |
C25—C26 | 1.499 (3) | C49—C50 | 1.360 (2) |
C25—H25A | 0.9900 | C49—H49A | 0.9500 |
C25—H25B | 0.9900 | C50—C51 | 1.434 (2) |
C26—H26A | 0.9900 | C50—H50A | 0.9500 |
C26—H26B | 0.9900 | C51—C52 | 1.391 (2) |
C27—C28 | 1.496 (3) | C51—C53i | 1.438 (2) |
C27—H27A | 0.9900 | C52—C53 | 1.406 (2) |
C27—H27B | 0.9900 | C52—H52A | 0.9500 |
C28—H28A | 0.9900 | C53—C47i | 1.423 (2) |
C28—H28B | 0.9900 | C53—C51i | 1.438 (2) |
N3—Co1—N1 | 102.15 (6) | H28A—C28—H28B | 108.3 |
N3—Co1—N2 | 153.20 (6) | O3—C29—C30 | 109.21 (16) |
N1—Co1—N2 | 83.09 (6) | O3—C29—H29A | 109.8 |
N3—Co1—N4 | 83.16 (6) | C30—C29—H29A | 109.8 |
N1—Co1—N4 | 156.15 (6) | O3—C29—H29B | 109.8 |
N2—Co1—N4 | 102.73 (6) | C30—C29—H29B | 109.8 |
C1—N1—C5 | 116.32 (15) | H29A—C29—H29B | 108.3 |
C1—N1—Co1 | 127.86 (12) | O4—C30—C29 | 109.00 (15) |
C5—N1—Co1 | 115.81 (12) | O4—C30—H30A | 109.9 |
C10—N2—C6 | 116.46 (15) | C29—C30—H30A | 109.9 |
C10—N2—Co1 | 127.37 (12) | O4—C30—H30B | 109.9 |
C6—N2—Co1 | 115.85 (12) | C29—C30—H30B | 109.9 |
C11—N3—C15 | 116.26 (15) | H30A—C30—H30B | 108.3 |
C11—N3—Co1 | 128.00 (12) | O4—C31—C32 | 108.83 (14) |
C15—N3—Co1 | 115.56 (12) | O4—C31—H31A | 109.9 |
C20—N4—C16 | 116.13 (15) | C32—C31—H31A | 109.9 |
C20—N4—Co1 | 128.02 (12) | O4—C31—H31B | 109.9 |
C16—N4—Co1 | 115.76 (12) | C32—C31—H31B | 109.9 |
C2—C1—N1 | 124.48 (18) | H31A—C31—H31B | 108.3 |
C2—C1—H1A | 117.8 | N6—C32—C31 | 113.05 (15) |
N1—C1—H1A | 117.8 | N6—C32—H32A | 109.0 |
C1—C2—C3 | 119.28 (19) | C31—C32—H32A | 109.0 |
C1—C2—H2A | 120.4 | N6—C32—H32B | 109.0 |
C3—C2—H2A | 120.4 | C31—C32—H32B | 109.0 |
C4—C3—C2 | 118.26 (18) | H32A—C32—H32B | 107.8 |
C4—C3—H3A | 120.9 | N5—C33—C34 | 113.22 (14) |
C2—C3—H3A | 120.9 | N5—C33—H33A | 108.9 |
C3—C4—C5 | 121.29 (18) | C34—C33—H33A | 108.9 |
C3—C4—H4A | 119.4 | N5—C33—H33B | 108.9 |
C5—C4—H4A | 119.4 | C34—C33—H33B | 108.9 |
C6—C5—N1 | 112.55 (15) | H33A—C33—H33B | 107.7 |
C6—C5—C4 | 127.12 (17) | O5—C34—C33 | 108.46 (15) |
N1—C5—C4 | 120.31 (17) | O5—C34—H34A | 110.0 |
C5—C6—N2 | 112.67 (15) | C33—C34—H34A | 110.0 |
C5—C6—C7 | 126.90 (16) | O5—C34—H34B | 110.0 |
N2—C6—C7 | 120.28 (17) | C33—C34—H34B | 110.0 |
C8—C7—C6 | 121.15 (18) | H34A—C34—H34B | 108.4 |
C8—C7—H7A | 119.4 | O5—C35—C36 | 108.68 (14) |
C6—C7—H7A | 119.4 | O5—C35—H35A | 110.0 |
C7—C8—C9 | 118.33 (18) | C36—C35—H35A | 110.0 |
C7—C8—H8A | 120.8 | O5—C35—H35B | 110.0 |
C9—C8—H8A | 120.8 | C36—C35—H35B | 110.0 |
C10—C9—C8 | 119.21 (18) | H35A—C35—H35B | 108.3 |
C10—C9—H9A | 120.4 | O6—C36—C35 | 107.88 (14) |
C8—C9—H9A | 120.4 | O6—C36—H36A | 110.1 |
C9—C10—N2 | 124.56 (17) | C35—C36—H36A | 110.1 |
C9—C10—H10A | 117.7 | O6—C36—H36B | 110.1 |
N2—C10—H10A | 117.7 | C35—C36—H36B | 110.1 |
C12—C11—N3 | 124.14 (18) | H36A—C36—H36B | 108.4 |
C12—C11—H11A | 117.9 | O6—C37—C38 | 108.38 (15) |
N3—C11—H11A | 117.9 | O6—C37—H37A | 110.0 |
C11—C12—C13 | 119.5 (2) | C38—C37—H37A | 110.0 |
C11—C12—H12A | 120.3 | O6—C37—H37B | 110.0 |
C13—C12—H12A | 120.3 | C38—C37—H37B | 110.0 |
C14—C13—C12 | 118.16 (18) | H37A—C37—H37B | 108.4 |
C14—C13—H13A | 120.9 | N6—C38—C37 | 113.16 (14) |
C12—C13—H13A | 120.9 | N6—C38—H38A | 108.9 |
C13—C14—C15 | 121.31 (19) | C37—C38—H38A | 108.9 |
C13—C14—H14A | 119.3 | N6—C38—H38B | 108.9 |
C15—C14—H14A | 119.3 | C37—C38—H38B | 108.9 |
N3—C15—C16 | 112.94 (15) | H38A—C38—H38B | 107.8 |
N3—C15—C14 | 120.45 (18) | C42—O7—C39 | 108.73 (15) |
C16—C15—C14 | 126.61 (17) | O7—C39—C40 | 107.27 (17) |
N4—C16—C15 | 112.57 (15) | O7—C39—H39A | 110.3 |
N4—C16—C17 | 120.69 (18) | C40—C39—H39A | 110.3 |
C15—C16—C17 | 126.73 (18) | O7—C39—H39B | 110.3 |
C18—C17—C16 | 121.03 (19) | C40—C39—H39B | 110.3 |
C18—C17—H17A | 119.5 | H39A—C39—H39B | 108.5 |
C16—C17—H17A | 119.5 | C39—C40—C41 | 103.07 (17) |
C17—C18—C19 | 118.39 (18) | C39—C40—H40A | 111.1 |
C17—C18—H18A | 120.8 | C41—C40—H40A | 111.2 |
C19—C18—H18A | 120.8 | C39—C40—H40B | 111.1 |
C20—C19—C18 | 119.4 (2) | C41—C40—H40B | 111.1 |
C20—C19—H19A | 120.3 | H40A—C40—H40B | 109.1 |
C18—C19—H19A | 120.3 | C42—C41—C40 | 102.07 (17) |
C19—C20—N4 | 124.13 (19) | C42—C41—H41A | 111.4 |
C19—C20—H20A | 117.9 | C40—C41—H41A | 111.4 |
N4—C20—H20A | 117.9 | C42—C41—H41B | 111.4 |
O2—K1—O4 | 96.52 (4) | C40—C41—H41B | 111.4 |
O2—K1—O6 | 99.43 (4) | H41A—C41—H41B | 109.2 |
O4—K1—O6 | 95.87 (4) | O7—C42—C41 | 106.77 (16) |
O2—K1—O3 | 122.29 (4) | O7—C42—H42A | 110.4 |
O4—K1—O3 | 60.26 (3) | C41—C42—H42A | 110.4 |
O6—K1—O3 | 132.34 (4) | O7—C42—H42B | 110.4 |
O2—K1—O1 | 60.00 (4) | C41—C42—H42B | 110.4 |
O4—K1—O1 | 132.66 (4) | H42A—C42—H42B | 108.6 |
O6—K1—O1 | 126.36 (4) | C43—O8—C46 | 107.8 (8) |
O3—K1—O1 | 96.17 (4) | O8—C43—C44 | 103.3 (9) |
O2—K1—O5 | 135.91 (4) | O8—C43—H43A | 111.1 |
O4—K1—O5 | 122.06 (4) | C44—C43—H43A | 111.1 |
O6—K1—O5 | 59.44 (3) | O8—C43—H43B | 111.1 |
O3—K1—O5 | 96.87 (4) | C44—C43—H43B | 111.1 |
O1—K1—O5 | 99.64 (4) | H43A—C43—H43B | 109.1 |
O2—K1—N5 | 120.09 (4) | C43—C44—C45 | 100.2 (8) |
O4—K1—N5 | 120.23 (4) | C43—C44—H44A | 111.7 |
O6—K1—N5 | 119.44 (4) | C45—C44—H44A | 111.7 |
O3—K1—N5 | 60.34 (4) | C43—C44—H44B | 111.7 |
O1—K1—N5 | 60.32 (4) | C45—C44—H44B | 111.7 |
O5—K1—N5 | 60.25 (4) | H44A—C44—H44B | 109.5 |
O2—K1—N6 | 60.10 (4) | C46—C45—C44 | 103.3 (7) |
O4—K1—N6 | 59.95 (4) | C46—C45—H45A | 111.1 |
O6—K1—N6 | 60.19 (4) | C44—C45—H45A | 111.1 |
O3—K1—N6 | 119.89 (4) | C46—C45—H45B | 111.1 |
O1—K1—N6 | 119.84 (4) | C44—C45—H45B | 111.1 |
O5—K1—N6 | 119.39 (4) | H45A—C45—H45B | 109.1 |
N5—K1—N6 | 179.63 (4) | O8—C46—C45 | 106.3 (7) |
C21—N5—C27 | 109.62 (14) | O8—C46—H46A | 110.5 |
C21—N5—C33 | 109.29 (14) | C45—C46—H46A | 110.5 |
C27—N5—C33 | 109.38 (14) | O8—C46—H46B | 110.5 |
C21—N5—K1 | 109.31 (10) | C45—C46—H46B | 110.5 |
C27—N5—K1 | 109.60 (10) | H46A—C46—H46B | 108.7 |
C33—N5—K1 | 109.64 (10) | C46'—O8'—C43' | 107.9 (8) |
C32—N6—C26 | 109.79 (14) | O8'—C43'—C44' | 105.9 (9) |
C32—N6—C38 | 110.31 (14) | O8'—C43'—H43C | 110.6 |
C26—N6—C38 | 110.45 (14) | C44'—C43'—H43C | 110.6 |
C32—N6—K1 | 109.34 (10) | O8'—C43'—H43D | 110.6 |
C26—N6—K1 | 108.90 (10) | C44'—C43'—H43D | 110.6 |
C38—N6—K1 | 108.00 (10) | H43C—C43'—H43D | 108.7 |
C23—O1—C22 | 112.27 (14) | C43'—C44'—C45' | 105.5 (8) |
C23—O1—K1 | 112.18 (11) | C43'—C44'—H44C | 110.6 |
C22—O1—K1 | 115.34 (11) | C45'—C44'—H44C | 110.6 |
C24—O2—C25 | 111.23 (14) | C43'—C44'—H44D | 110.7 |
C24—O2—K1 | 116.38 (10) | C45'—C44'—H44D | 110.6 |
C25—O2—K1 | 116.16 (10) | H44C—C44'—H44D | 108.8 |
C29—O3—C28 | 112.06 (14) | C46'—C45'—C44' | 105.8 (7) |
C29—O3—K1 | 113.34 (10) | C46'—C45'—H45C | 110.6 |
C28—O3—K1 | 114.84 (10) | C44'—C45'—H45C | 110.6 |
C30—O4—C31 | 110.94 (13) | C46'—C45'—H45D | 110.6 |
C30—O4—K1 | 113.84 (10) | C44'—C45'—H45D | 110.6 |
C31—O4—K1 | 114.99 (10) | H45C—C45'—H45D | 108.7 |
C34—O5—C35 | 112.29 (13) | O8'—C46'—C45' | 107.7 (8) |
C34—O5—K1 | 112.03 (9) | O8'—C46'—H46C | 110.2 |
C35—O5—K1 | 111.76 (9) | C45'—C46'—H46C | 110.2 |
C37—O6—C36 | 112.19 (13) | O8'—C46'—H46D | 110.2 |
C37—O6—K1 | 115.01 (10) | C45'—C46'—H46D | 110.2 |
C36—O6—K1 | 115.52 (9) | H46C—C46'—H46D | 108.5 |
N5—C21—C22 | 113.55 (15) | C46"—O8"—C43" | 109.9 (8) |
N5—C21—H21A | 108.9 | O8"—C43"—C44" | 107.1 (9) |
C22—C21—H21A | 108.9 | O8"—C43"—H43E | 110.3 |
N5—C21—H21B | 108.9 | C44"—C43"—H43E | 110.3 |
C22—C21—H21B | 108.9 | O8"—C43"—H43F | 110.3 |
H21A—C21—H21B | 107.7 | C44"—C43"—H43F | 110.3 |
O1—C22—C21 | 108.92 (15) | H43E—C43"—H43F | 108.5 |
O1—C22—H22A | 109.9 | C43"—C44"—C45" | 103.6 (9) |
C21—C22—H22A | 109.9 | C43"—C44"—H44E | 111.0 |
O1—C22—H22B | 109.9 | C45"—C44"—H44E | 111.0 |
C21—C22—H22B | 109.9 | C43"—C44"—H44F | 111.0 |
H22A—C22—H22B | 108.3 | C45"—C44"—H44F | 111.0 |
O1—C23—C24 | 108.60 (15) | H44E—C44"—H44F | 109.0 |
O1—C23—H23A | 110.0 | C46"—C45"—C44" | 103.8 (10) |
C24—C23—H23A | 110.0 | C46"—C45"—H45E | 111.0 |
O1—C23—H23B | 110.0 | C44"—C45"—H45E | 111.0 |
C24—C23—H23B | 110.0 | C46"—C45"—H45F | 111.0 |
H23A—C23—H23B | 108.4 | C44"—C45"—H45F | 111.0 |
O2—C24—C23 | 109.00 (16) | H45E—C45"—H45F | 109.0 |
O2—C24—H24A | 109.9 | O8"—C46"—C45" | 106.2 (8) |
C23—C24—H24A | 109.9 | O8"—C46"—H46E | 110.5 |
O2—C24—H24B | 109.9 | C45"—C46"—H46E | 110.5 |
C23—C24—H24B | 109.9 | O8"—C46"—H46F | 110.5 |
H24A—C24—H24B | 108.3 | C45"—C46"—H46F | 110.5 |
O2—C25—C26 | 109.05 (14) | H46E—C46"—H46F | 108.7 |
O2—C25—H25A | 109.9 | C48—C47—C53i | 121.03 (16) |
C26—C25—H25A | 109.9 | C48—C47—H47A | 119.5 |
O2—C25—H25B | 109.9 | C53i—C47—H47A | 119.5 |
C26—C25—H25B | 109.9 | C47—C48—C49 | 120.25 (16) |
H25A—C25—H25B | 108.3 | C47—C48—H48A | 119.9 |
N6—C26—C25 | 114.18 (15) | C49—C48—H48A | 119.9 |
N6—C26—H26A | 108.7 | C50—C49—C48 | 120.93 (16) |
C25—C26—H26A | 108.7 | C50—C49—H49A | 119.5 |
N6—C26—H26B | 108.7 | C48—C49—H49A | 119.5 |
C25—C26—H26B | 108.7 | C49—C50—C51 | 120.57 (16) |
H26A—C26—H26B | 107.6 | C49—C50—H50A | 119.7 |
N5—C27—C28 | 113.94 (15) | C51—C50—H50A | 119.7 |
N5—C27—H27A | 108.8 | C52—C51—C50 | 121.63 (15) |
C28—C27—H27A | 108.8 | C52—C51—C53i | 120.00 (14) |
N5—C27—H27B | 108.8 | C50—C51—C53i | 118.37 (15) |
C28—C27—H27B | 108.8 | C51—C52—C53 | 121.06 (15) |
H27A—C27—H27B | 107.7 | C51—C52—H52A | 119.5 |
O3—C28—C27 | 109.10 (15) | C53—C52—H52A | 119.5 |
O3—C28—H28A | 109.9 | C52—C53—C47i | 122.24 (15) |
C27—C28—H28A | 109.9 | C52—C53—C51i | 118.94 (15) |
O3—C28—H28B | 109.9 | C47i—C53—C51i | 118.81 (14) |
C27—C28—H28B | 109.9 | ||
N3—Co1—N1—C1 | 27.24 (15) | K1—N5—C21—C22 | 42.36 (18) |
N2—Co1—N1—C1 | −179.42 (15) | C23—O1—C22—C21 | −175.37 (16) |
N4—Co1—N1—C1 | −73.5 (2) | K1—O1—C22—C21 | 54.44 (18) |
N3—Co1—N1—C5 | −152.02 (11) | N5—C21—C22—O1 | −66.8 (2) |
N2—Co1—N1—C5 | 1.32 (11) | C22—O1—C23—C24 | 175.29 (16) |
N4—Co1—N1—C5 | 107.28 (17) | K1—O1—C23—C24 | −52.92 (18) |
N3—Co1—N2—C10 | −71.4 (2) | C25—O2—C24—C23 | 178.00 (15) |
N1—Co1—N2—C10 | −174.72 (14) | K1—O2—C24—C23 | −45.88 (18) |
N4—Co1—N2—C10 | 28.77 (14) | O1—C23—C24—O2 | 66.5 (2) |
N3—Co1—N2—C6 | 101.88 (16) | C24—O2—C25—C26 | −166.36 (15) |
N1—Co1—N2—C6 | −1.45 (11) | K1—O2—C25—C26 | 57.42 (17) |
N4—Co1—N2—C6 | −157.96 (11) | C32—N6—C26—C25 | 157.10 (15) |
N1—Co1—N3—C11 | 29.96 (15) | C38—N6—C26—C25 | −81.03 (19) |
N2—Co1—N3—C11 | −68.9 (2) | K1—N6—C26—C25 | 37.41 (17) |
N4—Co1—N3—C11 | −173.63 (15) | O2—C25—C26—N6 | −64.4 (2) |
N1—Co1—N3—C15 | −155.13 (11) | C21—N5—C27—C28 | 159.76 (15) |
N2—Co1—N3—C15 | 106.04 (16) | C33—N5—C27—C28 | −80.43 (18) |
N4—Co1—N3—C15 | 1.28 (11) | K1—N5—C27—C28 | 39.79 (17) |
N3—Co1—N4—C20 | −176.92 (15) | C29—O3—C28—C27 | −172.82 (15) |
N1—Co1—N4—C20 | −72.3 (2) | K1—O3—C28—C27 | 55.98 (17) |
N2—Co1—N4—C20 | 29.63 (15) | N5—C27—C28—O3 | −65.9 (2) |
N3—Co1—N4—C16 | −0.66 (11) | C28—O3—C29—C30 | 178.01 (15) |
N1—Co1—N4—C16 | 104.00 (18) | K1—O3—C29—C30 | −50.03 (18) |
N2—Co1—N4—C16 | −154.11 (11) | C31—O4—C30—C29 | 178.76 (16) |
C5—N1—C1—C2 | 2.5 (2) | K1—O4—C30—C29 | −49.66 (19) |
Co1—N1—C1—C2 | −176.74 (14) | O3—C29—C30—O4 | 67.7 (2) |
N1—C1—C2—C3 | −0.8 (3) | C30—O4—C31—C32 | −170.51 (16) |
C1—C2—C3—C4 | −1.3 (3) | K1—O4—C31—C32 | 58.51 (17) |
C2—C3—C4—C5 | 1.6 (3) | C26—N6—C32—C31 | −80.24 (18) |
C1—N1—C5—C6 | 179.71 (14) | C38—N6—C32—C31 | 157.81 (15) |
Co1—N1—C5—C6 | −0.94 (18) | K1—N6—C32—C31 | 39.18 (17) |
C1—N1—C5—C4 | −2.1 (2) | O4—C31—C32—N6 | −66.8 (2) |
Co1—N1—C5—C4 | 177.21 (12) | C21—N5—C33—C34 | −79.84 (18) |
C3—C4—C5—C6 | 178.02 (17) | C27—N5—C33—C34 | 160.15 (16) |
C3—C4—C5—N1 | 0.2 (3) | K1—N5—C33—C34 | 39.95 (18) |
N1—C5—C6—N2 | −0.2 (2) | C35—O5—C34—C33 | −173.34 (14) |
C4—C5—C6—N2 | −178.23 (16) | K1—O5—C34—C33 | 59.93 (15) |
N1—C5—C6—C7 | 175.24 (16) | N5—C33—C34—O5 | −69.7 (2) |
C4—C5—C6—C7 | −2.8 (3) | C34—O5—C35—C36 | 179.68 (14) |
C10—N2—C6—C5 | 175.33 (14) | K1—O5—C35—C36 | −53.44 (15) |
Co1—N2—C6—C5 | 1.31 (17) | C37—O6—C36—C35 | 176.19 (14) |
C10—N2—C6—C7 | −0.5 (2) | K1—O6—C36—C35 | −49.33 (16) |
Co1—N2—C6—C7 | −174.50 (12) | O5—C35—C36—O6 | 69.47 (18) |
C5—C6—C7—C8 | −174.02 (17) | C36—O6—C37—C38 | −167.67 (14) |
N2—C6—C7—C8 | 1.1 (3) | K1—O6—C37—C38 | 57.60 (16) |
C6—C7—C8—C9 | −0.8 (3) | C32—N6—C38—C37 | −77.09 (18) |
C7—C8—C9—C10 | −0.2 (3) | C26—N6—C38—C37 | 161.35 (15) |
C8—C9—C10—N2 | 0.9 (3) | K1—N6—C38—C37 | 42.36 (17) |
C6—N2—C10—C9 | −0.5 (2) | O6—C37—C38—N6 | −69.15 (19) |
Co1—N2—C10—C9 | 172.69 (13) | C42—O7—C39—C40 | −4.9 (2) |
C15—N3—C11—C12 | 3.6 (2) | O7—C39—C40—C41 | 24.6 (3) |
Co1—N3—C11—C12 | 178.50 (14) | C39—C40—C41—C42 | −33.6 (2) |
N3—C11—C12—C13 | 0.3 (3) | C39—O7—C42—C41 | −17.3 (2) |
C11—C12—C13—C14 | −2.5 (3) | C40—C41—C42—O7 | 31.9 (2) |
C12—C13—C14—C15 | 0.6 (3) | C46—O8—C43—C44 | −33.0 (18) |
C11—N3—C15—C16 | 173.87 (15) | O8—C43—C44—C45 | 43.3 (14) |
Co1—N3—C15—C16 | −1.65 (18) | C43—C44—C45—C46 | −37.3 (13) |
C11—N3—C15—C14 | −5.4 (2) | C43—O8—C46—C45 | 8.8 (19) |
Co1—N3—C15—C14 | 179.04 (12) | C44—C45—C46—O8 | 18.8 (15) |
C13—C14—C15—N3 | 3.5 (3) | C46'—O8'—C43'—C44' | 26.7 (18) |
C13—C14—C15—C16 | −175.70 (18) | O8'—C43'—C44'—C45' | −25.9 (19) |
C20—N4—C16—C15 | 176.64 (14) | C43'—C44'—C45'—C46' | 16 (2) |
Co1—N4—C16—C15 | −0.08 (18) | C43'—O8'—C46'—C45' | −16.8 (19) |
C20—N4—C16—C17 | −4.6 (2) | C44'—C45'—C46'—O8' | 0 (2) |
Co1—N4—C16—C17 | 178.72 (13) | C46"—O8"—C43"—C44" | −7 (3) |
N3—C15—C16—N4 | 1.1 (2) | O8"—C43"—C44"—C45" | 24 (3) |
C14—C15—C16—N4 | −179.66 (16) | C43"—C44"—C45"—C46" | −30 (2) |
N3—C15—C16—C17 | −177.63 (16) | C43"—O8"—C46"—C45" | −12 (3) |
C14—C15—C16—C17 | 1.6 (3) | C44"—C45"—C46"—O8" | 27 (2) |
N4—C16—C17—C18 | 2.2 (3) | C53i—C47—C48—C49 | 0.8 (3) |
C15—C16—C17—C18 | −179.15 (18) | C47—C48—C49—C50 | −1.2 (3) |
C16—C17—C18—C19 | 1.6 (3) | C48—C49—C50—C51 | 0.0 (3) |
C17—C18—C19—C20 | −3.0 (3) | C49—C50—C51—C52 | −178.57 (16) |
C18—C19—C20—N4 | 0.5 (3) | C49—C50—C51—C53i | 1.6 (2) |
C16—N4—C20—C19 | 3.3 (2) | C50—C51—C52—C53 | −179.18 (15) |
Co1—N4—C20—C19 | 179.50 (13) | C53i—C51—C52—C53 | 0.7 (3) |
C27—N5—C21—C22 | −77.79 (19) | C51—C52—C53—C47i | 178.15 (15) |
C33—N5—C21—C22 | 162.34 (15) | C51—C52—C53—C51i | −0.7 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
(1) | (2) | |
Crystal data | ||
Chemical formula | [K(C18H36N2O6)2][Fe(C10H8N2)3](C14H10) | [K(C18H36N2O6)][Co(C10H8N2)2]·0.5C14H10·2C4H8O |
Mr | 1533.79 | 1020.20 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 |
Temperature (K) | 173 | 173 |
a, b, c (Å) | 23.049 (4), 17.067 (3), 21.543 (3) | 10.5981 (8), 14.4323 (11), 18.4886 (15) |
α, β, γ (°) | 90, 109.779 (3), 90 | 99.1054 (13), 90.8279 (14), 109.2433 (13) |
V (Å3) | 7975 (2) | 2629.5 (4) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.36 | 0.46 |
Crystal size (mm) | 0.42 × 0.16 × 0.06 | 0.40 × 0.18 × 0.12 |
Data collection | ||
Diffractometer | Siemens SMART CCD platform diffractometer | Siemens SMART CCD platform diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2012) | Multi-scan (SADABS; Sheldrick, 2012) |
Tmin, Tmax | 0.637, 0.745 | 0.684, 0.745 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22943, 7069, 4398 | 26404, 9299, 7616 |
Rint | 0.085 | 0.021 |
(sin θ/λ)max (Å−1) | 0.596 | 0.595 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.122, 1.02 | 0.031, 0.079, 1.03 |
No. of reflections | 7069 | 9299 |
No. of parameters | 474 | 715 |
No. of restraints | 0 | 257 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.39 | 0.31, −0.22 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SIR97 (Altomare et al., 1999), SHELXL2014 (Sheldrick, 2014), SHELXTL (Sheldrick, 2008).
Fe1—N1 | 1.959 (2) | C36—C37 | 1.380 (4) |
Fe1—N3 | 1.965 (2) | C37—C38 | 1.414 (4) |
Fe1—N2 | 1.969 (2) | C38—C39 | 1.406 (4) |
C5—C6 | 1.431 (4) | C38—C40ii | 1.451 (4) |
C15—C15i | 1.411 (6) | C39—C40 | 1.412 (4) |
C34—C40ii | 1.415 (4) | C40—C34ii | 1.415 (4) |
C35—C36 | 1.399 (5) |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+3/2, −y+1/2, −z+1. |
Co1—N3 | 1.8742 (14) | C48—C49 | 1.419 (2) |
Co1—N1 | 1.8764 (14) | C49—C50 | 1.360 (2) |
Co1—N2 | 1.8767 (14) | C50—C51 | 1.434 (2) |
Co1—N4 | 1.8794 (14) | C51—C52 | 1.391 (2) |
C5—C6 | 1.405 (3) | C51—C53i | 1.438 (2) |
C15—C16 | 1.405 (3) | C52—C53 | 1.406 (2) |
C47—C48 | 1.362 (2) | C53—C47i | 1.423 (2) |
C47—C53i | 1.423 (2) | ||
N3—Co1—N2 | 153.20 (6) | N3—Co1—N4 | 83.16 (6) |
N1—Co1—N2 | 83.09 (6) | N1—Co1—N4 | 156.15 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |