metal-organic compounds
Di-μ-tricyanido-tetracyanidobis[hydrotris(pyrazoylborato)]tetramethanoldiiron(III)iron(II) dimethanol disolvate
aInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koen, Fukuoka 816-0811, Japan
*Correspondence e-mail: sato@cm.kyushu-u.ac.jp
In the title complex, [FeIIFeIII2(C9H10BN6)2(CN)6(CH3OH)4]·2CH3OH, two [FeIII(Tp)(CN)3]− anions [Tp is hydrotris(pyrazoylborate)] are bridged by an [FeII(MeOH)4]2+ cation, forming a centrosymmetric trinuclear unit. These units are connected via O—H⋯O and O—H⋯N hydrogen bonds involving the uncoordinated methanol solvent molecules, forming a three-dimensional network.
CCDC reference: 981575
Related literature
For the synthesis of bis{tricyano[hydrotris(pyrazoylborate)]ferrate(III)}, see Lescouëzec et al. (2002). For a related structure, see Kim et al. (2004).
Experimental
Crystal data
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Data collection: CrystalClear (Rigaku, 2008); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 981575
10.1107/S1600536814001019/pk2510sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001019/pk2510Isup2.hkl
A trinuclear cyanide bridged complex was synthesized by slow evaporation. In this compound, the central iron(II) ion is coordinated by two nitrogen atoms from cyanide bridging of [FeIII(Tp)(CN)3]- (Tp = hydrotris(pyrazoylborate) with trans geometry, and four oxygen atoms from coordinated methanol molecules. While, the FeIII in the [FeIII(Tp)(CN)3]- part is coordinated by three nitrogen atoms from Tp- and three carbon atoms from cyanide. The Fe1—N—C—Fe2 structure unit is almost linear with Fe1—C—N and Fe2—N—C angles of 176.1 (3)° and 168.2 (3)°, respectively. Two types of hydrogen bonds O1—H10···O3 and O3—H30···N9 are present between the uncoordinated methanol molecules and [FeIII(Tp)(CN)3]2[FeII(MeOH)4] units, linking the trinuclear units into a three-dimensional supra-molecule. The carbon atom of the uncoordinated methanol molecules is probably disordered. An isostructural compound [FeIII(Tp)(CN)3]2[MnII(MeOH)4] and two methanol molecules was reported previously (Kim et al., 2004).
Tetra-n-butylammonium bis-[tricyano-hydrotris(pyrazoylborate)-ferrate(III)] (0.589g,0.1mmol) and ferrous perchlorate hydrated (0.018g. 0.05 mmol) in 10 ml methanol were reacted for 30 min at room temperature. Slow evaporation of the filtrate gave red crystals.
Carbon-bound H-atoms of pyrazole were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The carbon-bound H-atoms of methanol, O-bound H-atoms and B-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraints of C—H, O—H and B—H 0.98±0.01 Å, 0.82±0.1 Å, 1.12 Å, respectively; with Uiso(H) set to 1.2Ueq(N).Crystal data, data collection and structure
details are summarized in Table 1.A trinuclear cyanide bridged complex was synthesized by slow evaporation. In this compound, the central iron(II) ion is coordinated by two nitrogen atoms from cyanide bridging of [FeIII(Tp)(CN)3]- (Tp = hydrotris(pyrazoylborate) with trans geometry, and four oxygen atoms from coordinated methanol molecules. While, the FeIII in the [FeIII(Tp)(CN)3]- part is coordinated by three nitrogen atoms from Tp- and three carbon atoms from cyanide. The Fe1—N—C—Fe2 structure unit is almost linear with Fe1—C—N and Fe2—N—C angles of 176.1 (3)° and 168.2 (3)°, respectively. Two types of hydrogen bonds O1—H10···O3 and O3—H30···N9 are present between the uncoordinated methanol molecules and [FeIII(Tp)(CN)3]2[FeII(MeOH)4] units, linking the trinuclear units into a three-dimensional supra-molecule. The carbon atom of the uncoordinated methanol molecules is probably disordered. An isostructural compound [FeIII(Tp)(CN)3]2[MnII(MeOH)4] and two methanol molecules was reported previously (Kim et al., 2004).
Tetra-n-butylammonium bis-[tricyano-hydrotris(pyrazoylborate)-ferrate(III)] (0.589g,0.1mmol) and ferrous perchlorate hydrated (0.018g. 0.05 mmol) in 10 ml methanol were reacted for 30 min at room temperature. Slow evaporation of the filtrate gave red crystals.
For the synthesis of bis[tricyano[hydrotris(pyrazoylborate)]ferrate(III)], see Lescouëzec et al. (2002). For a related structure, see Kim et al. (2004).
detailsCarbon-bound H-atoms of pyrazole were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The carbon-bound H-atoms of methanol, O-bound H-atoms and B-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraints of C—H, O—H and B—H 0.98±0.01 Å, 0.82±0.1 Å, 1.12 Å, respectively; with Uiso(H) set to 1.2Ueq(N).Crystal data, data collection and structure
details are summarized in Table 1.Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The displacement ellipsoid plot (50% probability level) of the title compound. Unlabelled atoms are related to their labelled counterparts by the symmetry operation (–x + 1, -y + 1, -z + 1). | |
Fig. 2. The packing diagram of the title compound viewed along the crystallographic a–axis. H atoms are omitted to enhance clarity. |
[Fe3(C9H10BN6)2(CN)6(CH4O)4]·2CH4O | F(000) = 972 |
Mr = 942.00 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 4554 reflections |
a = 9.261 (4) Å | θ = 3.1–27.5° |
b = 16.405 (7) Å | µ = 1.05 mm−1 |
c = 14.331 (6) Å | T = 123 K |
β = 94.671 (2)° | Block, red |
V = 2169.9 (16) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 2 |
Rigaku Saturn70 diffractometer | 4922 independent reflections |
Radiation source: fine-focus sealed tube | 4557 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
Detector resolution: 7.314 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −21→21 |
Tmin = 0.743, Tmax = 0.902 | l = −18→16 |
16575 measured 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0721P)2 + 4.4189P] where P = (Fo2 + 2Fc2)/3 |
4922 reflections | (Δ/σ)max = 0.001 |
269 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.82 e Å−3 |
[Fe3(C9H10BN6)2(CN)6(CH4O)4]·2CH4O | V = 2169.9 (16) Å3 |
Mr = 942.00 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.261 (4) Å | µ = 1.05 mm−1 |
b = 16.405 (7) Å | T = 123 K |
c = 14.331 (6) Å | 0.30 × 0.20 × 0.10 mm |
β = 94.671 (2)° |
Rigaku Saturn70 diffractometer | 4922 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4557 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.902 | Rint = 0.097 |
16575 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.95 e Å−3 |
4922 reflections | Δρmin = −0.82 e Å−3 |
269 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.16211 (4) | 0.53724 (3) | 0.76431 (3) | 0.01108 (15) | |
Fe2 | 0.5000 | 0.5000 | 0.5000 | 0.01447 (18) | |
O1 | 0.6195 (3) | 0.61004 (16) | 0.52139 (18) | 0.0259 (6) | |
H1O | 0.5856 | 0.6453 | 0.5654 | 0.031* | |
O2 | 0.3481 (3) | 0.57099 (18) | 0.41549 (19) | 0.0295 (6) | |
H2O | 0.2586 | 0.5732 | 0.4119 | 0.035* | |
O3 | 0.5843 (4) | 0.71803 (18) | 0.6547 (2) | 0.0424 (8) | |
H3O | 0.6238 | 0.7647 | 0.6527 | 0.051* | |
N1 | 0.1053 (3) | 0.64652 (16) | 0.71911 (18) | 0.0132 (5) | |
N2 | 0.0729 (3) | 0.70462 (16) | 0.78192 (18) | 0.0139 (5) | |
N3 | 0.0040 (3) | 0.54145 (16) | 0.84969 (18) | 0.0136 (5) | |
N4 | −0.0165 (3) | 0.61102 (16) | 0.89905 (18) | 0.0146 (5) | |
N5 | 0.2907 (3) | 0.58953 (16) | 0.86392 (18) | 0.0133 (5) | |
N6 | 0.2409 (3) | 0.65368 (16) | 0.91250 (18) | 0.0151 (5) | |
N7 | −0.0531 (3) | 0.45434 (18) | 0.6197 (2) | 0.0223 (6) | |
N8 | 0.3854 (3) | 0.52601 (18) | 0.6178 (2) | 0.0192 (6) | |
N9 | 0.2724 (3) | 0.36947 (17) | 0.8348 (2) | 0.0210 (6) | |
C1 | 0.0913 (4) | 0.6807 (2) | 0.6342 (2) | 0.0180 (6) | |
H1 | 0.1081 | 0.6539 | 0.5774 | 0.022* | |
C2 | 0.0484 (4) | 0.7615 (2) | 0.6417 (2) | 0.0218 (7) | |
H2 | 0.0302 | 0.7998 | 0.5924 | 0.026* | |
C3 | 0.0379 (4) | 0.77434 (19) | 0.7362 (2) | 0.0191 (7) | |
H3 | 0.0107 | 0.8239 | 0.7642 | 0.023* | |
C4 | −0.0966 (4) | 0.4884 (2) | 0.8710 (2) | 0.0169 (6) | |
H4 | −0.1068 | 0.4348 | 0.8462 | 0.020* | |
C5 | −0.1852 (4) | 0.5225 (2) | 0.9348 (2) | 0.0199 (7) | |
H5 | −0.2653 | 0.4978 | 0.9612 | 0.024* | |
C6 | −0.1310 (3) | 0.5999 (2) | 0.9513 (2) | 0.0180 (6) | |
H6 | −0.1676 | 0.6390 | 0.9922 | 0.022* | |
C7 | 0.4266 (3) | 0.5739 (2) | 0.9010 (2) | 0.0179 (6) | |
H7 | 0.4877 | 0.5322 | 0.8805 | 0.021* | |
C8 | 0.4640 (4) | 0.6281 (2) | 0.9736 (2) | 0.0225 (7) | |
H8 | 0.5528 | 0.6307 | 1.0116 | 0.027* | |
C9 | 0.3438 (4) | 0.6775 (2) | 0.9786 (2) | 0.0197 (7) | |
H9 | 0.3353 | 0.7210 | 1.0216 | 0.024* | |
C10 | 0.2287 (3) | 0.4314 (2) | 0.8080 (2) | 0.0150 (6) | |
C11 | 0.3056 (3) | 0.53102 (18) | 0.6750 (2) | 0.0138 (6) | |
C12 | 0.0301 (3) | 0.48514 (19) | 0.6716 (2) | 0.0149 (6) | |
C13 | 0.7555 (5) | 0.6320 (3) | 0.4880 (4) | 0.0401 (11) | |
H13A | 0.7890 | 0.6835 | 0.5168 | 0.048* | |
H13B | 0.7438 | 0.6384 | 0.4198 | 0.048* | |
H13C | 0.8267 | 0.5891 | 0.5043 | 0.048* | |
C14 | 0.3792 (5) | 0.6167 (3) | 0.3344 (3) | 0.0386 (10) | |
H14A | 0.3525 | 0.5845 | 0.2780 | 0.046* | |
H14B | 0.4830 | 0.6293 | 0.3376 | 0.046* | |
H14C | 0.3235 | 0.6676 | 0.3321 | 0.046* | |
C15 | 0.6291 (13) | 0.6822 (4) | 0.7417 (4) | 0.123 (5) | |
H15A | 0.7292 | 0.6981 | 0.7604 | 0.148* | |
H15B | 0.6232 | 0.6227 | 0.7362 | 0.148* | |
H15C | 0.5658 | 0.7007 | 0.7891 | 0.148* | |
B1 | 0.0838 (4) | 0.6841 (2) | 0.8869 (2) | 0.0150 (7) | |
H10 | 0.0501 | 0.7378 | 0.9281 | 0.018* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0115 (2) | 0.0095 (2) | 0.0126 (2) | 0.00115 (15) | 0.00292 (16) | 0.00043 (15) |
Fe2 | 0.0125 (3) | 0.0171 (3) | 0.0143 (3) | −0.0025 (2) | 0.0040 (2) | −0.0033 (2) |
O1 | 0.0240 (13) | 0.0255 (13) | 0.0297 (14) | −0.0087 (11) | 0.0112 (10) | −0.0113 (11) |
O2 | 0.0152 (12) | 0.0420 (16) | 0.0312 (14) | 0.0014 (11) | 0.0002 (10) | 0.0111 (12) |
O3 | 0.065 (2) | 0.0274 (15) | 0.0368 (16) | −0.0274 (15) | 0.0179 (15) | −0.0142 (12) |
N1 | 0.0154 (12) | 0.0117 (12) | 0.0127 (12) | 0.0005 (10) | 0.0030 (9) | 0.0004 (9) |
N2 | 0.0175 (12) | 0.0117 (12) | 0.0126 (12) | 0.0018 (10) | 0.0022 (9) | −0.0003 (10) |
N3 | 0.0144 (13) | 0.0112 (12) | 0.0156 (13) | 0.0019 (10) | 0.0033 (10) | −0.0001 (9) |
N4 | 0.0146 (12) | 0.0141 (13) | 0.0154 (12) | 0.0045 (10) | 0.0028 (10) | −0.0012 (10) |
N5 | 0.0126 (12) | 0.0145 (12) | 0.0131 (12) | 0.0008 (10) | 0.0028 (9) | −0.0008 (10) |
N6 | 0.0177 (13) | 0.0135 (12) | 0.0146 (12) | −0.0001 (10) | 0.0043 (10) | −0.0017 (10) |
N7 | 0.0203 (14) | 0.0233 (15) | 0.0231 (15) | −0.0024 (12) | 0.0006 (12) | 0.0013 (12) |
N8 | 0.0192 (14) | 0.0198 (14) | 0.0194 (14) | −0.0016 (11) | 0.0059 (11) | −0.0040 (11) |
N9 | 0.0241 (15) | 0.0135 (13) | 0.0252 (15) | 0.0025 (11) | 0.0001 (11) | 0.0003 (11) |
C1 | 0.0218 (16) | 0.0173 (15) | 0.0151 (15) | 0.0010 (13) | 0.0018 (12) | 0.0008 (12) |
C2 | 0.0341 (19) | 0.0143 (15) | 0.0167 (15) | 0.0032 (14) | −0.0004 (14) | 0.0049 (12) |
C3 | 0.0255 (17) | 0.0099 (14) | 0.0217 (16) | 0.0019 (13) | 0.0001 (13) | 0.0013 (12) |
C4 | 0.0156 (15) | 0.0158 (15) | 0.0195 (15) | −0.0003 (12) | 0.0033 (12) | 0.0024 (12) |
C5 | 0.0157 (15) | 0.0239 (17) | 0.0210 (16) | 0.0028 (13) | 0.0068 (12) | 0.0039 (13) |
C6 | 0.0158 (15) | 0.0235 (16) | 0.0154 (14) | 0.0034 (13) | 0.0052 (11) | 0.0015 (12) |
C7 | 0.0132 (14) | 0.0202 (16) | 0.0202 (15) | 0.0011 (12) | 0.0010 (12) | 0.0011 (13) |
C8 | 0.0169 (15) | 0.0267 (18) | 0.0234 (17) | −0.0024 (14) | −0.0011 (13) | −0.0015 (14) |
C9 | 0.0225 (16) | 0.0202 (16) | 0.0162 (15) | −0.0027 (13) | 0.0009 (12) | −0.0025 (12) |
C10 | 0.0140 (14) | 0.0170 (15) | 0.0140 (14) | 0.0013 (12) | 0.0012 (11) | −0.0017 (11) |
C11 | 0.0148 (14) | 0.0107 (14) | 0.0160 (15) | 0.0002 (11) | 0.0019 (11) | 0.0001 (11) |
C12 | 0.0139 (14) | 0.0136 (14) | 0.0175 (15) | 0.0023 (12) | 0.0040 (11) | 0.0008 (12) |
C13 | 0.027 (2) | 0.037 (2) | 0.057 (3) | −0.0175 (18) | 0.0123 (19) | −0.009 (2) |
C14 | 0.027 (2) | 0.049 (3) | 0.041 (2) | 0.0047 (19) | 0.0040 (17) | 0.018 (2) |
C15 | 0.272 (13) | 0.069 (4) | 0.027 (3) | −0.107 (7) | 0.007 (5) | 0.001 (3) |
B1 | 0.0174 (16) | 0.0145 (16) | 0.0134 (15) | 0.0013 (13) | 0.0030 (12) | −0.0008 (12) |
Fe1—C11 | 1.922 (3) | N6—B1 | 1.554 (4) |
Fe1—C10 | 1.930 (3) | N7—C12 | 1.144 (5) |
Fe1—C12 | 1.930 (3) | N8—C11 | 1.150 (4) |
Fe1—N1 | 1.963 (3) | N9—C10 | 1.148 (4) |
Fe1—N5 | 1.979 (3) | C1—C2 | 1.391 (5) |
Fe1—N3 | 1.984 (3) | C1—H1 | 0.9500 |
Fe2—N8i | 2.109 (3) | C2—C3 | 1.382 (5) |
Fe2—N8 | 2.109 (3) | C2—H2 | 0.9500 |
Fe2—O1i | 2.127 (3) | C3—H3 | 0.9500 |
Fe2—O1 | 2.127 (3) | C4—C5 | 1.395 (5) |
Fe2—O2 | 2.127 (3) | C4—H4 | 0.9500 |
Fe2—O2i | 2.127 (3) | C5—C6 | 1.379 (5) |
O1—C13 | 1.429 (5) | C5—H5 | 0.9500 |
O1—H1O | 0.9286 | C6—H6 | 0.9500 |
O2—C14 | 1.432 (5) | C7—C8 | 1.390 (5) |
O2—H2O | 0.8267 | C7—H7 | 0.9500 |
O3—C15 | 1.410 (8) | C8—C9 | 1.383 (5) |
O3—H3O | 0.8500 | C8—H8 | 0.9500 |
N1—C1 | 1.336 (4) | C9—H9 | 0.9500 |
N1—N2 | 1.361 (4) | C13—H13A | 0.9800 |
N2—C3 | 1.344 (4) | C13—H13B | 0.9800 |
N2—B1 | 1.537 (4) | C13—H13C | 0.9800 |
N3—C4 | 1.329 (4) | C14—H14A | 0.9800 |
N3—N4 | 1.364 (4) | C14—H14B | 0.9800 |
N4—C6 | 1.359 (4) | C14—H14C | 0.9800 |
N4—B1 | 1.535 (5) | C15—H15A | 0.9800 |
N5—C7 | 1.350 (4) | C15—H15B | 0.9800 |
N5—N6 | 1.363 (4) | C15—H15C | 0.9800 |
N6—C9 | 1.345 (4) | B1—H10 | 1.1191 |
C11—Fe1—C10 | 87.03 (13) | C11—N8—Fe2 | 168.2 (3) |
C11—Fe1—C12 | 87.23 (14) | N1—C1—C2 | 109.7 (3) |
C10—Fe1—C12 | 89.59 (13) | N1—C1—H1 | 125.1 |
C11—Fe1—N1 | 90.58 (12) | C2—C1—H1 | 125.1 |
C10—Fe1—N1 | 176.91 (12) | C3—C2—C1 | 105.3 (3) |
C12—Fe1—N1 | 92.27 (12) | C3—C2—H2 | 127.4 |
C11—Fe1—N5 | 95.46 (12) | C1—C2—H2 | 127.4 |
C10—Fe1—N5 | 89.89 (12) | N2—C3—C2 | 108.3 (3) |
C12—Fe1—N5 | 177.23 (12) | N2—C3—H3 | 125.8 |
N1—Fe1—N5 | 88.37 (11) | C2—C3—H3 | 125.8 |
C11—Fe1—N3 | 176.14 (12) | N3—C4—C5 | 110.4 (3) |
C10—Fe1—N3 | 93.65 (12) | N3—C4—H4 | 124.8 |
C12—Fe1—N3 | 88.97 (13) | C5—C4—H4 | 124.8 |
N1—Fe1—N3 | 88.87 (11) | C6—C5—C4 | 104.9 (3) |
N5—Fe1—N3 | 88.34 (11) | C6—C5—H5 | 127.6 |
N8i—Fe2—N8 | 179.999 (1) | C4—C5—H5 | 127.6 |
N8i—Fe2—O1i | 90.17 (10) | N4—C6—C5 | 108.6 (3) |
N8—Fe2—O1i | 89.83 (10) | N4—C6—H6 | 125.7 |
N8i—Fe2—O1 | 89.83 (10) | C5—C6—H6 | 125.7 |
N8—Fe2—O1 | 90.17 (10) | N5—C7—C8 | 109.9 (3) |
O1i—Fe2—O1 | 179.998 (1) | N5—C7—H7 | 125.0 |
N8i—Fe2—O2 | 90.45 (11) | C8—C7—H7 | 125.0 |
N8—Fe2—O2 | 89.55 (11) | C9—C8—C7 | 105.1 (3) |
O1i—Fe2—O2 | 94.03 (11) | C9—C8—H8 | 127.4 |
O1—Fe2—O2 | 85.97 (11) | C7—C8—H8 | 127.4 |
N8i—Fe2—O2i | 89.55 (11) | N6—C9—C8 | 108.7 (3) |
N8—Fe2—O2i | 90.45 (11) | N6—C9—H9 | 125.7 |
O1i—Fe2—O2i | 85.97 (11) | C8—C9—H9 | 125.7 |
O1—Fe2—O2i | 94.03 (11) | N9—C10—Fe1 | 177.9 (3) |
O2—Fe2—O2i | 180.000 (1) | N8—C11—Fe1 | 176.1 (3) |
C13—O1—Fe2 | 128.9 (2) | N7—C12—Fe1 | 176.7 (3) |
C13—O1—H1O | 115.3 | O1—C13—H13A | 109.5 |
Fe2—O1—H1O | 115.2 | O1—C13—H13B | 109.5 |
C14—O2—Fe2 | 125.5 (2) | H13A—C13—H13B | 109.5 |
C14—O2—H2O | 101.2 | O1—C13—H13C | 109.5 |
Fe2—O2—H2O | 132.2 | H13A—C13—H13C | 109.5 |
C15—O3—H3O | 108.1 | H13B—C13—H13C | 109.5 |
C1—N1—N2 | 107.3 (3) | O2—C14—H14A | 109.5 |
C1—N1—Fe1 | 133.4 (2) | O2—C14—H14B | 109.5 |
N2—N1—Fe1 | 119.27 (19) | H14A—C14—H14B | 109.5 |
C3—N2—N1 | 109.3 (3) | O2—C14—H14C | 109.5 |
C3—N2—B1 | 131.1 (3) | H14A—C14—H14C | 109.5 |
N1—N2—B1 | 119.6 (2) | H14B—C14—H14C | 109.5 |
C4—N3—N4 | 107.4 (3) | O3—C15—H15A | 109.5 |
C4—N3—Fe1 | 133.3 (2) | O3—C15—H15B | 109.5 |
N4—N3—Fe1 | 119.4 (2) | H15A—C15—H15B | 109.5 |
C6—N4—N3 | 108.8 (3) | O3—C15—H15C | 109.5 |
C6—N4—B1 | 132.3 (3) | H15A—C15—H15C | 109.5 |
N3—N4—B1 | 118.9 (3) | H15B—C15—H15C | 109.5 |
C7—N5—N6 | 106.8 (3) | N4—B1—N2 | 106.8 (3) |
C7—N5—Fe1 | 133.6 (2) | N4—B1—N6 | 106.7 (3) |
N6—N5—Fe1 | 119.6 (2) | N2—B1—N6 | 106.7 (2) |
C9—N6—N5 | 109.5 (3) | N4—B1—H10 | 111.0 |
C9—N6—B1 | 132.0 (3) | N2—B1—H10 | 110.1 |
N5—N6—B1 | 118.5 (2) | N6—B1—H10 | 115.1 |
N8i—Fe2—O1—C13 | −20.3 (4) | N8i—Fe2—N8—C11 | 164 (4) |
N8—Fe2—O1—C13 | 159.7 (4) | O1i—Fe2—N8—C11 | −20.8 (14) |
O1i—Fe2—O1—C13 | −88 (7) | O1—Fe2—N8—C11 | 159.2 (14) |
O2—Fe2—O1—C13 | −110.8 (4) | O2—Fe2—N8—C11 | 73.2 (14) |
O2i—Fe2—O1—C13 | 69.2 (4) | O2i—Fe2—N8—C11 | −106.8 (14) |
N8i—Fe2—O2—C14 | −31.2 (3) | N2—N1—C1—C2 | −0.4 (4) |
N8—Fe2—O2—C14 | 148.8 (3) | Fe1—N1—C1—C2 | −179.5 (2) |
O1i—Fe2—O2—C14 | −121.4 (3) | N1—C1—C2—C3 | 0.3 (4) |
O1—Fe2—O2—C14 | 58.5 (3) | N1—N2—C3—C2 | −0.3 (4) |
O2i—Fe2—O2—C14 | 12 (53) | B1—N2—C3—C2 | 178.1 (3) |
C11—Fe1—N1—C1 | 38.3 (3) | C1—C2—C3—N2 | 0.0 (4) |
C10—Fe1—N1—C1 | 78 (2) | N4—N3—C4—C5 | 0.0 (4) |
C12—Fe1—N1—C1 | −48.9 (3) | Fe1—N3—C4—C5 | −178.8 (2) |
N5—Fe1—N1—C1 | 133.8 (3) | N3—C4—C5—C6 | −0.3 (4) |
N3—Fe1—N1—C1 | −137.9 (3) | N3—N4—C6—C5 | −0.4 (4) |
C11—Fe1—N1—N2 | −140.6 (2) | B1—N4—C6—C5 | 178.7 (3) |
C10—Fe1—N1—N2 | −101 (2) | C4—C5—C6—N4 | 0.4 (4) |
C12—Fe1—N1—N2 | 132.1 (2) | N6—N5—C7—C8 | 0.1 (4) |
N5—Fe1—N1—N2 | −45.2 (2) | Fe1—N5—C7—C8 | −177.2 (2) |
N3—Fe1—N1—N2 | 43.2 (2) | N5—C7—C8—C9 | −0.1 (4) |
C1—N1—N2—C3 | 0.4 (4) | N5—N6—C9—C8 | 0.0 (4) |
Fe1—N1—N2—C3 | 179.6 (2) | B1—N6—C9—C8 | 177.9 (3) |
C1—N1—N2—B1 | −178.2 (3) | C7—C8—C9—N6 | 0.0 (4) |
Fe1—N1—N2—B1 | 1.0 (4) | C11—Fe1—C10—N9 | 63 (8) |
C11—Fe1—N3—C4 | 53.1 (19) | C12—Fe1—C10—N9 | 150 (8) |
C10—Fe1—N3—C4 | −47.0 (3) | N1—Fe1—C10—N9 | 23 (10) |
C12—Fe1—N3—C4 | 42.5 (3) | N5—Fe1—C10—N9 | −33 (8) |
N1—Fe1—N3—C4 | 134.8 (3) | N3—Fe1—C10—N9 | −121 (8) |
N5—Fe1—N3—C4 | −136.8 (3) | Fe2—N8—C11—Fe1 | −25 (6) |
C11—Fe1—N3—N4 | −125.6 (17) | C10—Fe1—C11—N8 | 100 (4) |
C10—Fe1—N3—N4 | 134.3 (2) | C12—Fe1—C11—N8 | 10 (4) |
C12—Fe1—N3—N4 | −136.2 (2) | N1—Fe1—C11—N8 | −82 (4) |
N1—Fe1—N3—N4 | −43.9 (2) | N5—Fe1—C11—N8 | −170 (4) |
N5—Fe1—N3—N4 | 44.5 (2) | N3—Fe1—C11—N8 | 0 (6) |
C4—N3—N4—C6 | 0.2 (3) | C11—Fe1—C12—N7 | 179 (100) |
Fe1—N3—N4—C6 | 179.2 (2) | C10—Fe1—C12—N7 | 92 (5) |
C4—N3—N4—B1 | −179.1 (3) | N1—Fe1—C12—N7 | −91 (5) |
Fe1—N3—N4—B1 | −0.1 (4) | N5—Fe1—C12—N7 | 12 (7) |
C11—Fe1—N5—C7 | −47.6 (3) | N3—Fe1—C12—N7 | −2 (5) |
C10—Fe1—N5—C7 | 39.4 (3) | C6—N4—B1—N2 | −122.6 (3) |
C12—Fe1—N5—C7 | 119 (2) | N3—N4—B1—N2 | 56.4 (3) |
N1—Fe1—N5—C7 | −138.0 (3) | C6—N4—B1—N6 | 123.6 (3) |
N3—Fe1—N5—C7 | 133.0 (3) | N3—N4—B1—N6 | −57.4 (3) |
C11—Fe1—N5—N6 | 135.3 (2) | C3—N2—B1—N4 | 124.2 (4) |
C10—Fe1—N5—N6 | −137.6 (2) | N1—N2—B1—N4 | −57.6 (3) |
C12—Fe1—N5—N6 | −58 (3) | C3—N2—B1—N6 | −122.0 (4) |
N1—Fe1—N5—N6 | 44.9 (2) | N1—N2—B1—N6 | 56.2 (3) |
N3—Fe1—N5—N6 | −44.0 (2) | C9—N6—B1—N4 | −119.9 (4) |
C7—N5—N6—C9 | −0.1 (3) | N5—N6—B1—N4 | 57.8 (3) |
Fe1—N5—N6—C9 | 177.7 (2) | C9—N6—B1—N2 | 126.1 (3) |
C7—N5—N6—B1 | −178.3 (3) | N5—N6—B1—N2 | −56.1 (3) |
Fe1—N5—N6—B1 | −0.5 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3 | 0.93 | 1.75 | 2.645 (4) | 161 |
O2—H2O···N7ii | 0.83 | 1.97 | 2.769 (4) | 161 |
O3—H3O···N9iii | 0.85 | 1.97 | 2.815 (4) | 172 |
O1—H1O···O3 | 0.93 | 1.75 | 2.645 (4) | 161 |
O2—H2O···N7ii | 0.83 | 1.97 | 2.769 (4) | 161 |
C8—H8···N9iv | 0.95 | 2.62 | 3.523 (5) | 158 |
O3—H3O···N9iii | 0.85 | 1.97 | 2.815 (4) | 172 |
Symmetry codes: (ii) −x, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3 | 0.93 | 1.75 | 2.645 (4) | 160.6 |
O2—H2O···N7i | 0.83 | 1.97 | 2.769 (4) | 161.4 |
O3—H3O···N9ii | 0.85 | 1.97 | 2.815 (4) | 172.1 |
O1—H1O···O3 | 0.93 | 1.75 | 2.645 (4) | 160.6 |
O2—H2O···N7i | 0.83 | 1.97 | 2.769 (4) | 161.4 |
C8—H8···N9iii | 0.95 | 2.62 | 3.523 (5) | 158.0 |
O3—H3O···N9ii | 0.85 | 1.97 | 2.815 (4) | 172.1 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2. |
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