The structure of a pincer ligand consists of a backbone and two `arms' which typically contain a P or N atom. They are tridentate ligands that coordinate to a metal center in a meridional configuration. A series of three iron complexes containing the pyrrole-based PNP pincer ligand 2,5-bis[(diisopropylphosphanyl)methyl]pyrrolide (PNpyrP) has been synthesized. These complexes are possible precursors to new iron catalysts. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3P,N,P′}carbonylchlorido(trimethylphosphane-κP)iron(II), [Fe(C18H34NP2)Cl(C3H9P)(CO)] or [Fe(PNpyrP)Cl(PMe3)(CO)], (I), has a slightly distorted octahedral geometry, with the Cl and CO ligands occupying the apical positions. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3P,N,P′}chlorido(pyridine-κN)iron(II), [Fe(C18H34NP2)Cl(C5H5N)] or [Fe(PNpyrP)Cl(py)] (py is pyridine), (II), is a five-coordinate square-pyramidal complex, with the pyridine ligand in the apical position. {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-κ3P,N,P′}dicarbonylchloridoiron(II), [Fe(C18H34NP2)Cl(CO)2] or [Fe(PNpyrP)Cl(CO)2], (III), is structurally similar to (I), but with the PMe3 ligand replaced by a second carbonyl ligand from the reaction of (II) with CO. The two carbonyl ligands are in a cis configuration, and there is positional disorder of the chloride and trans carbonyl ligands.
Supporting information
CCDC references: 1557265; 1557264; 1557263
For all compounds, data collection: SAINT (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (I), (III); olex2.solve (Bourhis et al., 2015) for (II). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (I), (III); SHELXL2016 (Sheldrick, 2015b) for (II). For all compounds, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
(I) {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-
κ3P,
N,
P'}carbonylchlorido(trimethylphosphane-
κP)iron(II)
top
Crystal data top
[Fe(C18H34NP2)Cl(C3H9P)(CO)] | F(000) = 1112 |
Mr = 521.78 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.0243 (16) Å | Cell parameters from 9059 reflections |
b = 10.494 (1) Å | θ = 2.3–27.9° |
c = 15.1374 (14) Å | µ = 0.90 mm−1 |
β = 109.090 (3)° | T = 120 K |
V = 2555.6 (4) Å3 | Rod, orange |
Z = 4 | 0.44 × 0.15 × 0.09 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6421 independent reflections |
Radiation source: fine-focus sealed tube | 5417 reflections with I > 2σ(I) |
Detector resolution: 8.33 pixels mm-1 | Rint = 0.049 |
φ and ω scans | θmax = 28.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −22→22 |
Tmin = 0.664, Tmax = 0.746 | k = −14→13 |
65628 measured reflections | l = −19→20 |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.030P)2 + 2.290P] where P = (Fo2 + 2Fc2)/3 |
6421 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.74275 (2) | 0.48764 (2) | 0.87576 (2) | 0.01299 (6) | |
Cl1 | 0.66509 (3) | 0.37458 (4) | 0.73868 (3) | 0.02033 (10) | |
P1 | 0.82669 (3) | 0.59346 (4) | 0.80510 (3) | 0.01412 (9) | |
P2 | 0.70737 (3) | 0.32606 (4) | 0.95927 (3) | 0.01529 (10) | |
P3 | 0.62985 (3) | 0.61581 (4) | 0.83773 (3) | 0.01965 (10) | |
O1 | 0.82605 (9) | 0.62872 (13) | 1.04304 (9) | 0.0256 (3) | |
N1 | 0.83671 (9) | 0.36830 (13) | 0.89447 (10) | 0.0145 (3) | |
C1 | 0.91419 (11) | 0.39862 (17) | 0.89198 (12) | 0.0162 (3) | |
C2 | 0.83528 (11) | 0.24005 (16) | 0.91080 (12) | 0.0174 (3) | |
C3 | 0.91175 (12) | 0.18785 (17) | 0.91757 (13) | 0.0201 (4) | |
H3 | 0.9275 | 0.1009 | 0.9286 | 0.024* | |
C4 | 0.96197 (11) | 0.28952 (17) | 0.90484 (12) | 0.0191 (4) | |
H4 | 1.0177 | 0.2837 | 0.9051 | 0.023* | |
C5 | 0.92901 (11) | 0.53630 (17) | 0.87792 (13) | 0.0182 (3) | |
H5A | 0.9706 | 0.5468 | 0.8456 | 0.022* | |
H5B | 0.9483 | 0.5822 | 0.9383 | 0.022* | |
C6 | 0.75766 (11) | 0.18961 (16) | 0.92251 (13) | 0.0189 (4) | |
H6A | 0.7706 | 0.1218 | 0.9706 | 0.023* | |
H6B | 0.7207 | 0.1539 | 0.8629 | 0.023* | |
C7 | 0.81768 (12) | 0.53001 (17) | 0.68775 (12) | 0.0197 (4) | |
H7 | 0.7996 | 0.4393 | 0.6877 | 0.024* | |
C8 | 0.89772 (15) | 0.5257 (2) | 0.66308 (17) | 0.0379 (6) | |
H8A | 0.9186 | 0.6125 | 0.6620 | 0.057* | |
H8B | 0.8865 | 0.4865 | 0.6014 | 0.057* | |
H8C | 0.9395 | 0.4753 | 0.7100 | 0.057* | |
C9 | 0.74841 (15) | 0.5959 (2) | 0.61168 (14) | 0.0322 (5) | |
H9A | 0.6962 | 0.5878 | 0.6253 | 0.048* | |
H9B | 0.7423 | 0.5561 | 0.5512 | 0.048* | |
H9C | 0.7620 | 0.6863 | 0.6094 | 0.048* | |
C10 | 0.83630 (12) | 0.76974 (16) | 0.79928 (13) | 0.0198 (4) | |
H10 | 0.7894 | 0.7996 | 0.7440 | 0.024* | |
C11 | 0.91649 (14) | 0.81490 (19) | 0.78530 (16) | 0.0309 (5) | |
H11A | 0.9642 | 0.7858 | 0.8377 | 0.046* | |
H11B | 0.9167 | 0.9082 | 0.7824 | 0.046* | |
H11C | 0.9202 | 0.7797 | 0.7268 | 0.046* | |
C12 | 0.82722 (13) | 0.83620 (17) | 0.88490 (14) | 0.0254 (4) | |
H12A | 0.7758 | 0.8079 | 0.8946 | 0.038* | |
H12B | 0.8252 | 0.9286 | 0.8752 | 0.038* | |
H12C | 0.8748 | 0.8148 | 0.9400 | 0.038* | |
C13 | 0.59921 (11) | 0.26886 (17) | 0.93367 (13) | 0.0197 (4) | |
H13 | 0.5707 | 0.2789 | 0.8649 | 0.024* | |
C14 | 0.59263 (14) | 0.1279 (2) | 0.95694 (16) | 0.0326 (5) | |
H14A | 0.6187 | 0.0754 | 0.9207 | 0.049* | |
H14B | 0.5339 | 0.1042 | 0.9412 | 0.049* | |
H14C | 0.6210 | 0.1139 | 1.0238 | 0.049* | |
C15 | 0.54999 (13) | 0.3469 (2) | 0.98283 (16) | 0.0344 (5) | |
H15A | 0.5656 | 0.3207 | 1.0484 | 0.052* | |
H15B | 0.4904 | 0.3325 | 0.9521 | 0.052* | |
H15C | 0.5624 | 0.4376 | 0.9795 | 0.052* | |
C16 | 0.75262 (12) | 0.32256 (18) | 1.08894 (13) | 0.0213 (4) | |
H16 | 0.7329 | 0.2417 | 1.1096 | 0.026* | |
C17 | 0.84810 (13) | 0.3160 (2) | 1.12313 (14) | 0.0281 (4) | |
H17A | 0.8660 | 0.2450 | 1.0922 | 0.042* | |
H17B | 0.8686 | 0.3028 | 1.1909 | 0.042* | |
H17C | 0.8706 | 0.3960 | 1.1080 | 0.042* | |
C18 | 0.72538 (14) | 0.4310 (2) | 1.14050 (14) | 0.0288 (4) | |
H18A | 0.7404 | 0.5131 | 1.1196 | 0.043* | |
H18B | 0.7533 | 0.4219 | 1.2080 | 0.043* | |
H18C | 0.6650 | 0.4273 | 1.1268 | 0.043* | |
C19 | 0.61832 (13) | 0.7339 (2) | 0.74540 (16) | 0.0319 (5) | |
H19A | 0.6657 | 0.7925 | 0.7640 | 0.048* | |
H19B | 0.5668 | 0.7820 | 0.7354 | 0.048* | |
H19C | 0.6163 | 0.6905 | 0.6874 | 0.048* | |
C20 | 0.61926 (13) | 0.7175 (2) | 0.93058 (16) | 0.0304 (5) | |
H20A | 0.6197 | 0.6649 | 0.9842 | 0.046* | |
H20B | 0.5667 | 0.7645 | 0.9079 | 0.046* | |
H20C | 0.6656 | 0.7780 | 0.9497 | 0.046* | |
C21 | 0.52587 (12) | 0.5462 (2) | 0.79256 (15) | 0.0280 (4) | |
H21A | 0.5198 | 0.5013 | 0.7340 | 0.042* | |
H21B | 0.4841 | 0.6140 | 0.7811 | 0.042* | |
H21C | 0.5179 | 0.4861 | 0.8384 | 0.042* | |
C22 | 0.79219 (11) | 0.57246 (16) | 0.97588 (13) | 0.0180 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01322 (12) | 0.01225 (12) | 0.01398 (12) | −0.00068 (9) | 0.00509 (9) | −0.00120 (9) |
Cl1 | 0.0194 (2) | 0.0220 (2) | 0.0187 (2) | −0.00379 (17) | 0.00517 (17) | −0.00460 (16) |
P1 | 0.0146 (2) | 0.01292 (19) | 0.0147 (2) | −0.00178 (16) | 0.00475 (17) | −0.00015 (16) |
P2 | 0.0159 (2) | 0.0147 (2) | 0.0168 (2) | −0.00039 (16) | 0.00738 (17) | 0.00058 (16) |
P3 | 0.0166 (2) | 0.0187 (2) | 0.0223 (2) | 0.00013 (17) | 0.00443 (19) | −0.00075 (18) |
O1 | 0.0305 (8) | 0.0256 (7) | 0.0200 (7) | −0.0071 (6) | 0.0074 (6) | −0.0067 (6) |
N1 | 0.0141 (7) | 0.0149 (7) | 0.0151 (7) | 0.0006 (5) | 0.0055 (6) | −0.0004 (5) |
C1 | 0.0142 (8) | 0.0193 (8) | 0.0142 (8) | −0.0007 (6) | 0.0034 (6) | −0.0005 (6) |
C2 | 0.0194 (9) | 0.0148 (8) | 0.0187 (9) | 0.0005 (7) | 0.0072 (7) | −0.0011 (6) |
C3 | 0.0217 (9) | 0.0168 (8) | 0.0210 (9) | 0.0042 (7) | 0.0060 (7) | −0.0013 (7) |
C4 | 0.0144 (8) | 0.0237 (9) | 0.0187 (9) | 0.0019 (7) | 0.0050 (7) | −0.0022 (7) |
C5 | 0.0132 (8) | 0.0210 (9) | 0.0191 (9) | −0.0017 (7) | 0.0035 (7) | 0.0008 (7) |
C6 | 0.0215 (9) | 0.0131 (8) | 0.0241 (9) | −0.0001 (7) | 0.0101 (7) | 0.0009 (7) |
C7 | 0.0248 (9) | 0.0181 (8) | 0.0172 (9) | −0.0052 (7) | 0.0084 (7) | −0.0013 (7) |
C8 | 0.0405 (13) | 0.0449 (13) | 0.0389 (13) | −0.0155 (11) | 0.0272 (11) | −0.0180 (10) |
C9 | 0.0469 (13) | 0.0274 (10) | 0.0182 (10) | 0.0007 (9) | 0.0051 (9) | 0.0008 (8) |
C10 | 0.0216 (9) | 0.0140 (8) | 0.0230 (9) | −0.0028 (7) | 0.0061 (7) | 0.0012 (7) |
C11 | 0.0354 (12) | 0.0208 (9) | 0.0429 (12) | −0.0093 (9) | 0.0215 (10) | −0.0023 (9) |
C12 | 0.0314 (11) | 0.0158 (8) | 0.0308 (11) | −0.0030 (8) | 0.0125 (9) | −0.0035 (8) |
C13 | 0.0163 (8) | 0.0228 (9) | 0.0206 (9) | −0.0031 (7) | 0.0068 (7) | 0.0015 (7) |
C14 | 0.0262 (11) | 0.0322 (11) | 0.0346 (12) | −0.0111 (9) | 0.0032 (9) | 0.0092 (9) |
C15 | 0.0204 (10) | 0.0501 (14) | 0.0359 (12) | −0.0028 (9) | 0.0138 (9) | −0.0070 (10) |
C16 | 0.0251 (10) | 0.0216 (9) | 0.0170 (9) | −0.0023 (7) | 0.0067 (7) | 0.0030 (7) |
C17 | 0.0265 (10) | 0.0297 (10) | 0.0225 (10) | 0.0011 (8) | 0.0004 (8) | 0.0014 (8) |
C18 | 0.0349 (11) | 0.0349 (11) | 0.0196 (9) | −0.0047 (9) | 0.0129 (9) | −0.0049 (8) |
C19 | 0.0232 (10) | 0.0308 (11) | 0.0384 (12) | 0.0068 (9) | 0.0056 (9) | 0.0130 (9) |
C20 | 0.0225 (10) | 0.0318 (11) | 0.0387 (12) | 0.0014 (8) | 0.0125 (9) | −0.0101 (9) |
C21 | 0.0176 (9) | 0.0291 (10) | 0.0332 (11) | −0.0018 (8) | 0.0029 (8) | 0.0006 (9) |
C22 | 0.0186 (9) | 0.0160 (8) | 0.0225 (9) | 0.0001 (7) | 0.0108 (7) | 0.0014 (7) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.3806 (5) | C9—H9C | 0.9800 |
Fe1—P1 | 2.3280 (5) | C10—H10 | 1.0000 |
Fe1—P2 | 2.3094 (5) | C10—C11 | 1.524 (3) |
Fe1—P3 | 2.2607 (5) | C10—C12 | 1.524 (3) |
Fe1—N1 | 1.9776 (14) | C11—H11A | 0.9800 |
Fe1—C22 | 1.7214 (19) | C11—H11B | 0.9800 |
P1—C5 | 1.8312 (18) | C11—H11C | 0.9800 |
P1—C7 | 1.8558 (18) | C12—H12A | 0.9800 |
P1—C10 | 1.8618 (18) | C12—H12B | 0.9800 |
P2—C6 | 1.8452 (18) | C12—H12C | 0.9800 |
P2—C13 | 1.8533 (18) | C13—H13 | 1.0000 |
P2—C16 | 1.8597 (19) | C13—C14 | 1.534 (3) |
P3—C19 | 1.830 (2) | C13—C15 | 1.528 (3) |
P3—C20 | 1.820 (2) | C14—H14A | 0.9800 |
P3—C21 | 1.828 (2) | C14—H14B | 0.9800 |
O1—C22 | 1.154 (2) | C14—H14C | 0.9800 |
N1—C1 | 1.369 (2) | C15—H15A | 0.9800 |
N1—C2 | 1.370 (2) | C15—H15B | 0.9800 |
C1—C4 | 1.381 (2) | C15—H15C | 0.9800 |
C1—C5 | 1.494 (2) | C16—H16 | 1.0000 |
C2—C3 | 1.385 (2) | C16—C17 | 1.538 (3) |
C2—C6 | 1.487 (2) | C16—C18 | 1.535 (3) |
C3—H3 | 0.9500 | C17—H17A | 0.9800 |
C3—C4 | 1.419 (3) | C17—H17B | 0.9800 |
C4—H4 | 0.9500 | C17—H17C | 0.9800 |
C5—H5A | 0.9900 | C18—H18A | 0.9800 |
C5—H5B | 0.9900 | C18—H18B | 0.9800 |
C6—H6A | 0.9900 | C18—H18C | 0.9800 |
C6—H6B | 0.9900 | C19—H19A | 0.9800 |
C7—H7 | 1.0000 | C19—H19B | 0.9800 |
C7—C8 | 1.527 (3) | C19—H19C | 0.9800 |
C7—C9 | 1.519 (3) | C20—H20A | 0.9800 |
C8—H8A | 0.9800 | C20—H20B | 0.9800 |
C8—H8B | 0.9800 | C20—H20C | 0.9800 |
C8—H8C | 0.9800 | C21—H21A | 0.9800 |
C9—H9A | 0.9800 | C21—H21B | 0.9800 |
C9—H9B | 0.9800 | C21—H21C | 0.9800 |
| | | |
P1—Fe1—Cl1 | 94.968 (19) | H9A—C9—H9C | 109.5 |
P2—Fe1—Cl1 | 86.636 (19) | H9B—C9—H9C | 109.5 |
P2—Fe1—P1 | 155.63 (2) | P1—C10—H10 | 107.0 |
P3—Fe1—Cl1 | 83.741 (19) | C11—C10—P1 | 114.34 (13) |
P3—Fe1—P1 | 101.40 (2) | C11—C10—H10 | 107.0 |
P3—Fe1—P2 | 102.95 (2) | C12—C10—P1 | 112.31 (13) |
N1—Fe1—Cl1 | 90.11 (4) | C12—C10—H10 | 107.0 |
N1—Fe1—P1 | 77.20 (4) | C12—C10—C11 | 108.70 (16) |
N1—Fe1—P2 | 78.48 (4) | C10—C11—H11A | 109.5 |
N1—Fe1—P3 | 173.57 (4) | C10—C11—H11B | 109.5 |
C22—Fe1—Cl1 | 175.86 (6) | C10—C11—H11C | 109.5 |
C22—Fe1—P1 | 87.76 (6) | H11A—C11—H11B | 109.5 |
C22—Fe1—P2 | 92.16 (6) | H11A—C11—H11C | 109.5 |
C22—Fe1—P3 | 92.68 (6) | H11B—C11—H11C | 109.5 |
C22—Fe1—N1 | 93.54 (7) | C10—C12—H12A | 109.5 |
C5—P1—Fe1 | 99.97 (6) | C10—C12—H12B | 109.5 |
C5—P1—C7 | 102.90 (9) | C10—C12—H12C | 109.5 |
C5—P1—C10 | 105.84 (8) | H12A—C12—H12B | 109.5 |
C7—P1—Fe1 | 113.43 (6) | H12A—C12—H12C | 109.5 |
C7—P1—C10 | 106.99 (8) | H12B—C12—H12C | 109.5 |
C10—P1—Fe1 | 124.92 (6) | P2—C13—H13 | 107.1 |
C6—P2—Fe1 | 100.07 (6) | C14—C13—P2 | 114.00 (14) |
C6—P2—C13 | 102.29 (8) | C14—C13—H13 | 107.1 |
C6—P2—C16 | 103.30 (9) | C15—C13—P2 | 112.97 (14) |
C13—P2—Fe1 | 122.86 (6) | C15—C13—H13 | 107.1 |
C13—P2—C16 | 104.75 (8) | C15—C13—C14 | 108.20 (17) |
C16—P2—Fe1 | 120.00 (6) | C13—C14—H14A | 109.5 |
C19—P3—Fe1 | 117.86 (7) | C13—C14—H14B | 109.5 |
C20—P3—Fe1 | 116.29 (7) | C13—C14—H14C | 109.5 |
C20—P3—C19 | 100.34 (11) | H14A—C14—H14B | 109.5 |
C20—P3—C21 | 101.23 (10) | H14A—C14—H14C | 109.5 |
C21—P3—Fe1 | 119.75 (7) | H14B—C14—H14C | 109.5 |
C21—P3—C19 | 97.82 (10) | C13—C15—H15A | 109.5 |
C1—N1—Fe1 | 126.17 (12) | C13—C15—H15B | 109.5 |
C1—N1—C2 | 107.90 (14) | C13—C15—H15C | 109.5 |
C2—N1—Fe1 | 125.92 (12) | H15A—C15—H15B | 109.5 |
N1—C1—C4 | 109.38 (15) | H15A—C15—H15C | 109.5 |
N1—C1—C5 | 115.96 (15) | H15B—C15—H15C | 109.5 |
C4—C1—C5 | 134.66 (16) | P2—C16—H16 | 106.4 |
N1—C2—C3 | 109.28 (16) | C17—C16—P2 | 112.55 (13) |
N1—C2—C6 | 116.10 (15) | C17—C16—H16 | 106.4 |
C3—C2—C6 | 134.50 (16) | C18—C16—P2 | 115.61 (13) |
C2—C3—H3 | 126.7 | C18—C16—H16 | 106.4 |
C2—C3—C4 | 106.62 (16) | C18—C16—C17 | 108.91 (16) |
C4—C3—H3 | 126.7 | C16—C17—H17A | 109.5 |
C1—C4—C3 | 106.81 (15) | C16—C17—H17B | 109.5 |
C1—C4—H4 | 126.6 | C16—C17—H17C | 109.5 |
C3—C4—H4 | 126.6 | H17A—C17—H17B | 109.5 |
P1—C5—H5A | 111.1 | H17A—C17—H17C | 109.5 |
P1—C5—H5B | 111.1 | H17B—C17—H17C | 109.5 |
C1—C5—P1 | 103.35 (12) | C16—C18—H18A | 109.5 |
C1—C5—H5A | 111.1 | C16—C18—H18B | 109.5 |
C1—C5—H5B | 111.1 | C16—C18—H18C | 109.5 |
H5A—C5—H5B | 109.1 | H18A—C18—H18B | 109.5 |
P2—C6—H6A | 110.5 | H18A—C18—H18C | 109.5 |
P2—C6—H6B | 110.5 | H18B—C18—H18C | 109.5 |
C2—C6—P2 | 106.13 (12) | P3—C19—H19A | 109.5 |
C2—C6—H6A | 110.5 | P3—C19—H19B | 109.5 |
C2—C6—H6B | 110.5 | P3—C19—H19C | 109.5 |
H6A—C6—H6B | 108.7 | H19A—C19—H19B | 109.5 |
P1—C7—H7 | 105.7 | H19A—C19—H19C | 109.5 |
C8—C7—P1 | 116.35 (14) | H19B—C19—H19C | 109.5 |
C8—C7—H7 | 105.7 | P3—C20—H20A | 109.5 |
C9—C7—P1 | 111.28 (14) | P3—C20—H20B | 109.5 |
C9—C7—H7 | 105.7 | P3—C20—H20C | 109.5 |
C9—C7—C8 | 111.21 (18) | H20A—C20—H20B | 109.5 |
C7—C8—H8A | 109.5 | H20A—C20—H20C | 109.5 |
C7—C8—H8B | 109.5 | H20B—C20—H20C | 109.5 |
C7—C8—H8C | 109.5 | P3—C21—H21A | 109.5 |
H8A—C8—H8B | 109.5 | P3—C21—H21B | 109.5 |
H8A—C8—H8C | 109.5 | P3—C21—H21C | 109.5 |
H8B—C8—H8C | 109.5 | H21A—C21—H21B | 109.5 |
C7—C9—H9A | 109.5 | H21A—C21—H21C | 109.5 |
C7—C9—H9B | 109.5 | H21B—C21—H21C | 109.5 |
C7—C9—H9C | 109.5 | O1—C22—Fe1 | 179.33 (17) |
H9A—C9—H9B | 109.5 | | |
| | | |
Fe1—P1—C5—C1 | 40.89 (12) | C4—C1—C5—P1 | 149.24 (19) |
Fe1—P1—C7—C8 | −142.56 (14) | C5—P1—C7—C8 | −35.53 (17) |
Fe1—P1—C7—C9 | 88.66 (14) | C5—P1—C7—C9 | −164.30 (14) |
Fe1—P1—C10—C11 | 157.20 (12) | C5—P1—C10—C11 | 42.51 (16) |
Fe1—P1—C10—C12 | 32.73 (16) | C5—P1—C10—C12 | −81.96 (15) |
Fe1—P2—C6—C2 | 34.85 (13) | C5—C1—C4—C3 | 177.90 (19) |
Fe1—P2—C13—C14 | 150.08 (12) | C6—P2—C13—C14 | 39.36 (16) |
Fe1—P2—C13—C15 | −85.85 (15) | C6—P2—C13—C15 | 163.43 (15) |
Fe1—P2—C16—C17 | −59.10 (15) | C6—P2—C16—C17 | 51.02 (15) |
Fe1—P2—C16—C18 | 66.94 (16) | C6—P2—C16—C18 | 177.06 (14) |
Fe1—N1—C1—C4 | −177.89 (12) | C6—C2—C3—C4 | −175.79 (19) |
Fe1—N1—C1—C5 | 2.9 (2) | C7—P1—C5—C1 | −76.14 (13) |
Fe1—N1—C2—C3 | 178.30 (12) | C7—P1—C10—C11 | −66.71 (16) |
Fe1—N1—C2—C6 | −5.0 (2) | C7—P1—C10—C12 | 168.82 (13) |
N1—C1—C4—C3 | −1.1 (2) | C10—P1—C5—C1 | 171.74 (12) |
N1—C1—C5—P1 | −31.79 (18) | C10—P1—C7—C8 | 75.74 (17) |
N1—C2—C3—C4 | 0.1 (2) | C10—P1—C7—C9 | −53.03 (16) |
N1—C2—C6—P2 | −23.20 (19) | C13—P2—C6—C2 | 161.91 (12) |
C1—N1—C2—C3 | −0.8 (2) | C13—P2—C16—C17 | 157.79 (14) |
C1—N1—C2—C6 | 175.95 (15) | C13—P2—C16—C18 | −76.18 (16) |
C2—N1—C1—C4 | 1.2 (2) | C16—P2—C6—C2 | −89.47 (13) |
C2—N1—C1—C5 | −178.04 (15) | C16—P2—C13—C14 | −68.15 (16) |
C2—C3—C4—C1 | 0.6 (2) | C16—P2—C13—C15 | 55.92 (16) |
C3—C2—C6—P2 | 152.46 (19) | | |
(II) {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-
κ3P,
N,
P'}chlorido(pyridine-
κN)iron(II)
top
Crystal data top
[Fe(C18H34NP2)Cl(C5H5N)] | F(000) = 1056 |
Mr = 496.80 | Dx = 1.244 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6074 (6) Å | Cell parameters from 9997 reflections |
b = 18.2229 (15) Å | θ = 2.2–26.4° |
c = 19.1442 (16) Å | µ = 0.80 mm−1 |
β = 92.3658 (13)° | T = 296 K |
V = 2651.7 (4) Å3 | Block, yellow |
Z = 4 | 0.60 × 0.36 × 0.36 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 5423 independent reflections |
Radiation source: fine-focus sealed-tube | 5174 reflections with I > 2σ(I) |
Detector resolution: 8.33 pixels mm-1 | Rint = 0.023 |
φ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→9 |
Tmin = 0.639, Tmax = 0.745 | k = −22→22 |
44868 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.021 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.025P)2 + 1.182P] where P = (Fo2 + 2Fc2)/3 |
5423 reflections | (Δ/σ)max = 0.001 |
270 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.42549 (2) | 0.28801 (2) | 0.43529 (2) | 0.01567 (5) | |
Cl1 | 0.15367 (4) | 0.33264 (2) | 0.46273 (2) | 0.02582 (7) | |
P1 | 0.33422 (4) | 0.15339 (2) | 0.45019 (2) | 0.02159 (7) | |
P2 | 0.52956 (4) | 0.40115 (2) | 0.36887 (2) | 0.01918 (7) | |
N1 | 0.57357 (13) | 0.23834 (6) | 0.36254 (5) | 0.0212 (2) | |
N2 | 0.57605 (12) | 0.29532 (5) | 0.53036 (5) | 0.01751 (19) | |
C1 | 0.55480 (16) | 0.16632 (7) | 0.34046 (7) | 0.0246 (3) | |
C2 | 0.65300 (15) | 0.27547 (7) | 0.30945 (6) | 0.0232 (2) | |
C3 | 0.67976 (16) | 0.22858 (8) | 0.25453 (7) | 0.0301 (3) | |
H3 | 0.7292 | 0.2405 | 0.2124 | 0.036* | |
C4 | 0.61773 (16) | 0.15886 (8) | 0.27451 (7) | 0.0310 (3) | |
H4 | 0.6192 | 0.1161 | 0.2481 | 0.037* | |
C5 | 0.48060 (18) | 0.10983 (7) | 0.38790 (7) | 0.0303 (3) | |
H5A | 0.5758 | 0.0849 | 0.4134 | 0.036* | |
H5B | 0.4151 | 0.0736 | 0.3603 | 0.036* | |
C6 | 0.70037 (16) | 0.35472 (7) | 0.31915 (6) | 0.0260 (3) | |
H6A | 0.7097 | 0.3781 | 0.2739 | 0.031* | |
H6B | 0.8134 | 0.3588 | 0.3442 | 0.031* | |
C7 | 0.3528 (3) | 0.09513 (7) | 0.52955 (7) | 0.0434 (4) | |
H7 | 0.3318 | 0.0440 | 0.5158 | 0.052* | |
C8 | 0.5372 (3) | 0.10094 (9) | 0.56399 (10) | 0.0642 (6) | |
H8A | 0.6231 | 0.0893 | 0.5304 | 0.096* | |
H8B | 0.5478 | 0.0672 | 0.6024 | 0.096* | |
H8C | 0.5563 | 0.1500 | 0.5808 | 0.096* | |
C9 | 0.2137 (3) | 0.11766 (10) | 0.58046 (8) | 0.0611 (6) | |
H9A | 0.2286 | 0.1685 | 0.5924 | 0.092* | |
H9B | 0.2261 | 0.0884 | 0.6221 | 0.092* | |
H9C | 0.0987 | 0.1103 | 0.5590 | 0.092* | |
C10 | 0.11042 (17) | 0.13506 (7) | 0.41300 (7) | 0.0281 (3) | |
H10 | 0.0275 | 0.1596 | 0.4431 | 0.034* | |
C11 | 0.0562 (2) | 0.05443 (9) | 0.40821 (8) | 0.0437 (4) | |
H11A | 0.1338 | 0.0287 | 0.3784 | 0.065* | |
H11B | −0.0623 | 0.0510 | 0.3892 | 0.065* | |
H11C | 0.0630 | 0.0329 | 0.4540 | 0.065* | |
C12 | 0.0912 (2) | 0.17101 (9) | 0.34094 (8) | 0.0380 (3) | |
H12A | 0.1233 | 0.2219 | 0.3446 | 0.057* | |
H12B | −0.0286 | 0.1670 | 0.3236 | 0.057* | |
H12C | 0.1669 | 0.1467 | 0.3094 | 0.057* | |
C13 | 0.63846 (15) | 0.48419 (7) | 0.40586 (7) | 0.0239 (2) | |
H13 | 0.5458 | 0.5153 | 0.4240 | 0.029* | |
C14 | 0.76244 (17) | 0.46424 (7) | 0.46777 (7) | 0.0302 (3) | |
H14A | 0.6986 | 0.4376 | 0.5018 | 0.045* | |
H14B | 0.8100 | 0.5083 | 0.4886 | 0.045* | |
H14C | 0.8566 | 0.4343 | 0.4518 | 0.045* | |
C15 | 0.73362 (19) | 0.52982 (8) | 0.35199 (8) | 0.0357 (3) | |
H15A | 0.8214 | 0.5002 | 0.3310 | 0.054* | |
H15B | 0.7889 | 0.5713 | 0.3747 | 0.054* | |
H15C | 0.6503 | 0.5466 | 0.3165 | 0.054* | |
C16 | 0.37789 (17) | 0.43727 (8) | 0.29881 (7) | 0.0295 (3) | |
H16 | 0.4477 | 0.4648 | 0.2658 | 0.035* | |
C17 | 0.2876 (2) | 0.37410 (10) | 0.25928 (9) | 0.0470 (4) | |
H17A | 0.3750 | 0.3423 | 0.2408 | 0.070* | |
H17B | 0.2143 | 0.3933 | 0.2216 | 0.070* | |
H17C | 0.2167 | 0.3469 | 0.2906 | 0.070* | |
C18 | 0.24214 (19) | 0.48941 (8) | 0.32810 (8) | 0.0383 (3) | |
H18A | 0.1765 | 0.4642 | 0.3625 | 0.057* | |
H18B | 0.1634 | 0.5059 | 0.2909 | 0.057* | |
H18C | 0.3011 | 0.5309 | 0.3493 | 0.057* | |
C19 | 0.75073 (16) | 0.28459 (7) | 0.53339 (7) | 0.0242 (2) | |
H19 | 0.8076 | 0.2769 | 0.4919 | 0.029* | |
C20 | 0.84954 (17) | 0.28449 (8) | 0.59556 (7) | 0.0299 (3) | |
H20 | 0.9705 | 0.2771 | 0.5957 | 0.036* | |
C21 | 0.76672 (18) | 0.29547 (8) | 0.65766 (7) | 0.0307 (3) | |
H21 | 0.8303 | 0.2952 | 0.7002 | 0.037* | |
C22 | 0.58713 (17) | 0.30679 (8) | 0.65485 (6) | 0.0290 (3) | |
H22 | 0.5276 | 0.3145 | 0.6957 | 0.035* | |
C23 | 0.49691 (15) | 0.30662 (7) | 0.59080 (6) | 0.0220 (2) | |
H23 | 0.3761 | 0.3147 | 0.5895 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01572 (8) | 0.01647 (9) | 0.01488 (8) | 0.00190 (6) | 0.00138 (6) | −0.00042 (6) |
Cl1 | 0.01695 (13) | 0.02615 (15) | 0.03487 (16) | 0.00341 (11) | 0.00717 (11) | 0.00372 (12) |
P1 | 0.02903 (16) | 0.01517 (14) | 0.02005 (15) | −0.00129 (11) | −0.00541 (12) | 0.00120 (11) |
P2 | 0.01712 (14) | 0.02107 (15) | 0.01962 (14) | 0.00171 (11) | 0.00411 (11) | 0.00427 (11) |
N1 | 0.0211 (5) | 0.0226 (5) | 0.0198 (5) | 0.0035 (4) | 0.0003 (4) | −0.0039 (4) |
N2 | 0.0178 (5) | 0.0163 (4) | 0.0183 (5) | −0.0014 (3) | 0.0004 (4) | 0.0007 (4) |
C1 | 0.0195 (6) | 0.0247 (6) | 0.0291 (6) | 0.0060 (5) | −0.0050 (5) | −0.0098 (5) |
C2 | 0.0181 (5) | 0.0325 (7) | 0.0192 (5) | 0.0066 (5) | 0.0021 (4) | −0.0011 (5) |
C3 | 0.0216 (6) | 0.0485 (8) | 0.0202 (6) | 0.0101 (6) | 0.0012 (5) | −0.0079 (6) |
C4 | 0.0221 (6) | 0.0404 (8) | 0.0301 (7) | 0.0102 (5) | −0.0050 (5) | −0.0185 (6) |
C5 | 0.0311 (7) | 0.0196 (6) | 0.0398 (7) | 0.0038 (5) | −0.0037 (6) | −0.0080 (5) |
C6 | 0.0234 (6) | 0.0322 (7) | 0.0232 (6) | 0.0029 (5) | 0.0095 (5) | 0.0035 (5) |
C7 | 0.0867 (12) | 0.0153 (6) | 0.0264 (7) | −0.0076 (7) | −0.0193 (7) | 0.0042 (5) |
C8 | 0.1120 (17) | 0.0235 (8) | 0.0525 (10) | 0.0075 (9) | −0.0532 (11) | 0.0014 (7) |
C9 | 0.1220 (18) | 0.0393 (9) | 0.0222 (7) | −0.0290 (10) | 0.0061 (9) | 0.0026 (6) |
C10 | 0.0265 (6) | 0.0301 (7) | 0.0275 (6) | −0.0088 (5) | −0.0003 (5) | 0.0006 (5) |
C11 | 0.0524 (9) | 0.0391 (8) | 0.0391 (8) | −0.0245 (7) | −0.0028 (7) | 0.0012 (7) |
C12 | 0.0328 (7) | 0.0438 (8) | 0.0360 (8) | −0.0075 (6) | −0.0149 (6) | 0.0094 (6) |
C13 | 0.0200 (6) | 0.0202 (6) | 0.0320 (6) | 0.0010 (4) | 0.0072 (5) | 0.0030 (5) |
C14 | 0.0271 (6) | 0.0255 (6) | 0.0378 (7) | −0.0023 (5) | −0.0012 (5) | −0.0031 (5) |
C15 | 0.0321 (7) | 0.0285 (7) | 0.0477 (8) | −0.0041 (6) | 0.0139 (6) | 0.0089 (6) |
C16 | 0.0279 (6) | 0.0346 (7) | 0.0260 (6) | 0.0032 (5) | −0.0002 (5) | 0.0116 (5) |
C17 | 0.0499 (9) | 0.0492 (9) | 0.0399 (8) | 0.0082 (8) | −0.0212 (7) | −0.0003 (7) |
C18 | 0.0299 (7) | 0.0384 (8) | 0.0462 (8) | 0.0101 (6) | −0.0041 (6) | 0.0106 (7) |
C19 | 0.0193 (6) | 0.0292 (6) | 0.0243 (6) | 0.0010 (5) | 0.0030 (5) | 0.0018 (5) |
C20 | 0.0184 (6) | 0.0389 (8) | 0.0321 (7) | −0.0001 (5) | −0.0033 (5) | 0.0050 (6) |
C21 | 0.0305 (7) | 0.0373 (7) | 0.0234 (6) | −0.0057 (5) | −0.0081 (5) | 0.0025 (5) |
C22 | 0.0295 (7) | 0.0391 (7) | 0.0185 (6) | −0.0047 (6) | 0.0016 (5) | −0.0036 (5) |
C23 | 0.0189 (5) | 0.0254 (6) | 0.0217 (6) | −0.0018 (5) | 0.0017 (4) | −0.0024 (5) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.3028 (3) | C10—C11 | 1.5280 (19) |
Fe1—P1 | 2.5688 (4) | C10—C12 | 1.5287 (18) |
Fe1—P2 | 2.5646 (4) | C11—H11A | 0.9600 |
Fe1—N1 | 2.0391 (10) | C11—H11B | 0.9600 |
Fe1—N2 | 2.1143 (10) | C11—H11C | 0.9600 |
P1—C5 | 1.8444 (14) | C12—H12A | 0.9600 |
P1—C7 | 1.8540 (14) | C12—H12B | 0.9600 |
P1—C10 | 1.8485 (13) | C12—H12C | 0.9600 |
P2—C6 | 1.8473 (12) | C13—H13 | 0.9800 |
P2—C13 | 1.8519 (13) | C13—C14 | 1.5278 (18) |
P2—C16 | 1.8535 (13) | C13—C15 | 1.5297 (17) |
N1—C1 | 1.3843 (16) | C14—H14A | 0.9600 |
N1—C2 | 1.3808 (16) | C14—H14B | 0.9600 |
N2—C19 | 1.3420 (15) | C14—H14C | 0.9600 |
N2—C23 | 1.3420 (15) | C15—H15A | 0.9600 |
C1—C4 | 1.3752 (18) | C15—H15B | 0.9600 |
C1—C5 | 1.4986 (19) | C15—H15C | 0.9600 |
C2—C3 | 1.3765 (17) | C16—H16 | 0.9800 |
C2—C6 | 1.4981 (18) | C16—C17 | 1.525 (2) |
C3—H3 | 0.9300 | C16—C18 | 1.5269 (19) |
C3—C4 | 1.413 (2) | C17—H17A | 0.9600 |
C4—H4 | 0.9300 | C17—H17B | 0.9600 |
C5—H5A | 0.9700 | C17—H17C | 0.9600 |
C5—H5B | 0.9700 | C18—H18A | 0.9600 |
C6—H6A | 0.9700 | C18—H18B | 0.9600 |
C6—H6B | 0.9700 | C18—H18C | 0.9600 |
C7—H7 | 0.9800 | C19—H19 | 0.9300 |
C7—C8 | 1.529 (2) | C19—C20 | 1.3813 (18) |
C7—C9 | 1.524 (3) | C20—H20 | 0.9300 |
C8—H8A | 0.9600 | C20—C21 | 1.3828 (19) |
C8—H8B | 0.9600 | C21—H21 | 0.9300 |
C8—H8C | 0.9600 | C21—C22 | 1.3805 (19) |
C9—H9A | 0.9600 | C22—H22 | 0.9300 |
C9—H9B | 0.9600 | C22—C23 | 1.3803 (17) |
C9—H9C | 0.9600 | C23—H23 | 0.9300 |
C10—H10 | 0.9800 | | |
| | | |
Cl1—Fe1—P1 | 93.588 (12) | P1—C10—H10 | 107.2 |
Cl1—Fe1—P2 | 97.336 (12) | C11—C10—P1 | 116.05 (11) |
P2—Fe1—P1 | 155.950 (12) | C11—C10—H10 | 107.2 |
N1—Fe1—Cl1 | 147.06 (3) | C11—C10—C12 | 110.02 (12) |
N1—Fe1—P1 | 79.13 (3) | C12—C10—P1 | 108.80 (9) |
N1—Fe1—P2 | 80.08 (3) | C12—C10—H10 | 107.2 |
N1—Fe1—N2 | 108.72 (4) | C10—C11—H11A | 109.5 |
N2—Fe1—Cl1 | 103.95 (3) | C10—C11—H11B | 109.5 |
N2—Fe1—P1 | 95.96 (3) | C10—C11—H11C | 109.5 |
N2—Fe1—P2 | 102.06 (3) | H11A—C11—H11B | 109.5 |
C5—P1—Fe1 | 99.56 (4) | H11A—C11—H11C | 109.5 |
C5—P1—C7 | 104.82 (7) | H11B—C11—H11C | 109.5 |
C5—P1—C10 | 104.14 (6) | C10—C12—H12A | 109.5 |
C7—P1—Fe1 | 128.76 (4) | C10—C12—H12B | 109.5 |
C10—P1—Fe1 | 112.25 (4) | C10—C12—H12C | 109.5 |
C10—P1—C7 | 104.48 (7) | H12A—C12—H12B | 109.5 |
C6—P2—Fe1 | 97.21 (4) | H12A—C12—H12C | 109.5 |
C6—P2—C13 | 104.96 (6) | H12B—C12—H12C | 109.5 |
C6—P2—C16 | 102.70 (6) | P2—C13—H13 | 107.0 |
C13—P2—Fe1 | 127.57 (4) | C14—C13—P2 | 110.75 (8) |
C13—P2—C16 | 103.99 (6) | C14—C13—H13 | 107.0 |
C16—P2—Fe1 | 116.65 (4) | C14—C13—C15 | 110.98 (11) |
C1—N1—Fe1 | 125.21 (8) | C15—C13—P2 | 113.77 (9) |
C2—N1—Fe1 | 123.78 (8) | C15—C13—H13 | 107.0 |
C2—N1—C1 | 106.41 (10) | C13—C14—H14A | 109.5 |
C19—N2—Fe1 | 121.89 (8) | C13—C14—H14B | 109.5 |
C19—N2—C23 | 117.64 (10) | C13—C14—H14C | 109.5 |
C23—N2—Fe1 | 120.36 (8) | H14A—C14—H14B | 109.5 |
N1—C1—C5 | 120.19 (11) | H14A—C14—H14C | 109.5 |
C4—C1—N1 | 109.79 (12) | H14B—C14—H14C | 109.5 |
C4—C1—C5 | 129.99 (12) | C13—C15—H15A | 109.5 |
N1—C2—C6 | 119.44 (10) | C13—C15—H15B | 109.5 |
C3—C2—N1 | 109.94 (12) | C13—C15—H15C | 109.5 |
C3—C2—C6 | 130.59 (12) | H15A—C15—H15B | 109.5 |
C2—C3—H3 | 126.6 | H15A—C15—H15C | 109.5 |
C2—C3—C4 | 106.84 (11) | H15B—C15—H15C | 109.5 |
C4—C3—H3 | 126.6 | P2—C16—H16 | 108.1 |
C1—C4—C3 | 107.00 (11) | C17—C16—P2 | 110.19 (10) |
C1—C4—H4 | 126.5 | C17—C16—H16 | 108.1 |
C3—C4—H4 | 126.5 | C17—C16—C18 | 110.75 (12) |
P1—C5—H5A | 109.6 | C18—C16—P2 | 111.44 (10) |
P1—C5—H5B | 109.6 | C18—C16—H16 | 108.1 |
C1—C5—P1 | 110.42 (8) | C16—C17—H17A | 109.5 |
C1—C5—H5A | 109.6 | C16—C17—H17B | 109.5 |
C1—C5—H5B | 109.6 | C16—C17—H17C | 109.5 |
H5A—C5—H5B | 108.1 | H17A—C17—H17B | 109.5 |
P2—C6—H6A | 109.8 | H17A—C17—H17C | 109.5 |
P2—C6—H6B | 109.8 | H17B—C17—H17C | 109.5 |
C2—C6—P2 | 109.55 (8) | C16—C18—H18A | 109.5 |
C2—C6—H6A | 109.8 | C16—C18—H18B | 109.5 |
C2—C6—H6B | 109.8 | C16—C18—H18C | 109.5 |
H6A—C6—H6B | 108.2 | H18A—C18—H18B | 109.5 |
P1—C7—H7 | 108.6 | H18A—C18—H18C | 109.5 |
C8—C7—P1 | 110.56 (12) | H18B—C18—H18C | 109.5 |
C8—C7—H7 | 108.6 | N2—C19—H19 | 118.7 |
C9—C7—P1 | 109.77 (11) | N2—C19—C20 | 122.68 (11) |
C9—C7—H7 | 108.6 | C20—C19—H19 | 118.7 |
C9—C7—C8 | 110.76 (14) | C19—C20—H20 | 120.3 |
C7—C8—H8A | 109.5 | C19—C20—C21 | 119.31 (12) |
C7—C8—H8B | 109.5 | C21—C20—H20 | 120.3 |
C7—C8—H8C | 109.5 | C20—C21—H21 | 120.9 |
H8A—C8—H8B | 109.5 | C22—C21—C20 | 118.26 (12) |
H8A—C8—H8C | 109.5 | C22—C21—H21 | 120.9 |
H8B—C8—H8C | 109.5 | C21—C22—H22 | 120.4 |
C7—C9—H9A | 109.5 | C23—C22—C21 | 119.30 (12) |
C7—C9—H9B | 109.5 | C23—C22—H22 | 120.4 |
C7—C9—H9C | 109.5 | N2—C23—C22 | 122.81 (11) |
H9A—C9—H9B | 109.5 | N2—C23—H23 | 118.6 |
H9A—C9—H9C | 109.5 | C22—C23—H23 | 118.6 |
H9B—C9—H9C | 109.5 | | |
| | | |
Fe1—P1—C5—C1 | −15.25 (9) | C5—P1—C7—C8 | 67.33 (12) |
Fe1—P1—C7—C8 | −48.31 (15) | C5—P1—C7—C9 | −170.18 (11) |
Fe1—P1—C7—C9 | 74.18 (13) | C5—P1—C10—C11 | 63.33 (12) |
Fe1—P1—C10—C11 | 170.07 (9) | C5—P1—C10—C12 | −61.35 (11) |
Fe1—P1—C10—C12 | 45.39 (11) | C5—C1—C4—C3 | −177.30 (12) |
Fe1—P2—C6—C2 | 27.00 (9) | C6—P2—C13—C14 | −75.54 (10) |
Fe1—P2—C13—C14 | 36.14 (10) | C6—P2—C13—C15 | 50.28 (10) |
Fe1—P2—C13—C15 | 161.96 (7) | C6—P2—C16—C17 | 66.49 (11) |
Fe1—P2—C16—C17 | −38.40 (12) | C6—P2—C16—C18 | −170.15 (10) |
Fe1—P2—C16—C18 | 84.96 (10) | C6—C2—C3—C4 | 176.81 (12) |
Fe1—N1—C1—C4 | 155.35 (8) | C7—P1—C5—C1 | −149.78 (9) |
Fe1—N1—C1—C5 | −26.61 (15) | C7—P1—C10—C11 | −46.40 (12) |
Fe1—N1—C2—C3 | −155.50 (8) | C7—P1—C10—C12 | −171.08 (10) |
Fe1—N1—C2—C6 | 26.26 (15) | C10—P1—C5—C1 | 100.75 (10) |
Fe1—N2—C19—C20 | −175.74 (10) | C10—P1—C7—C8 | 176.56 (11) |
Fe1—N2—C23—C22 | 175.39 (10) | C10—P1—C7—C9 | −60.95 (12) |
N1—C1—C4—C3 | 0.49 (14) | C13—P2—C6—C2 | 159.06 (9) |
N1—C1—C5—P1 | 26.75 (14) | C13—P2—C16—C17 | 175.70 (10) |
N1—C2—C3—C4 | −1.16 (14) | C13—P2—C16—C18 | −60.95 (11) |
N1—C2—C6—P2 | −36.72 (14) | C16—P2—C6—C2 | −92.47 (9) |
N2—C19—C20—C21 | 0.3 (2) | C16—P2—C13—C14 | 176.93 (9) |
C1—N1—C2—C3 | 1.45 (13) | C16—P2—C13—C15 | −57.25 (10) |
C1—N1—C2—C6 | −176.78 (10) | C19—N2—C23—C22 | −0.72 (18) |
C2—N1—C1—C4 | −1.19 (13) | C19—C20—C21—C22 | −0.5 (2) |
C2—N1—C1—C5 | 176.85 (10) | C20—C21—C22—C23 | 0.1 (2) |
C2—C3—C4—C1 | 0.41 (14) | C21—C22—C23—N2 | 0.5 (2) |
C3—C2—C6—P2 | 145.46 (12) | C23—N2—C19—C20 | 0.30 (18) |
C4—C1—C5—P1 | −155.66 (11) | | |
(III) {2,5-Bis[(diisopropylphosphanyl)methyl]pyrrolido-
κ3P,
N,
P'}dicarbonylchloridoiron(II)
top
Crystal data top
[Fe(C18H34NP2)Cl(CO)2] | F(000) = 1000 |
Mr = 473.72 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.7917 (17) Å | Cell parameters from 9904 reflections |
b = 14.6349 (18) Å | θ = 2.3–28.1° |
c = 11.2225 (13) Å | µ = 0.94 mm−1 |
β = 90.729 (2)° | T = 120 K |
V = 2265.0 (5) Å3 | Block, orange |
Z = 4 | 0.23 × 0.20 × 0.17 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5626 independent reflections |
Radiation source: fine-focus sealed-tube | 5123 reflections with I > 2σ(I) |
Detector resolution: 8.33 pixels mm-1 | Rint = 0.041 |
φ and ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −18→18 |
Tmin = 0.678, Tmax = 0.746 | k = −19→19 |
44037 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.31 | w = 1/[σ2(Fo2) + 4.0807P] where P = (Fo2 + 2Fc2)/3 |
5626 reflections | (Δ/σ)max = 0.001 |
279 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.73290 (2) | 0.49021 (2) | 0.34183 (3) | 0.01150 (8) | |
Cl1A | 0.6184 (2) | 0.5939 (2) | 0.2657 (3) | 0.0220 (6) | 0.3333 |
Cl1 | 0.84319 (11) | 0.38085 (11) | 0.41377 (12) | 0.0209 (3) | 0.6667 |
P1 | 0.79901 (4) | 0.58295 (4) | 0.48640 (5) | 0.01294 (12) | |
P2 | 0.70826 (4) | 0.41814 (4) | 0.16232 (5) | 0.01386 (12) | |
O2 | 0.5846 (3) | 0.6156 (3) | 0.2662 (4) | 0.0321 (11) | 0.6667 |
O2A | 0.8652 (7) | 0.3494 (5) | 0.4333 (9) | 0.028 (2) | 0.3333 |
O1 | 0.58964 (19) | 0.3980 (2) | 0.4889 (2) | 0.0574 (8) | |
N1 | 0.83295 (14) | 0.55086 (13) | 0.24775 (17) | 0.0147 (4) | |
C7 | 0.74777 (19) | 0.69742 (16) | 0.5135 (2) | 0.0189 (5) | |
H7 | 0.7860 | 0.7251 | 0.5807 | 0.023* | |
C10 | 0.82660 (19) | 0.53324 (17) | 0.6343 (2) | 0.0181 (5) | |
H10 | 0.8547 | 0.4714 | 0.6190 | 0.022* | |
C5 | 0.91928 (17) | 0.60593 (18) | 0.4245 (2) | 0.0179 (5) | |
H5A | 0.9422 | 0.6673 | 0.4490 | 0.022* | |
H5B | 0.9667 | 0.5600 | 0.4534 | 0.022* | |
C16 | 0.77215 (18) | 0.31139 (17) | 0.1253 (2) | 0.0200 (5) | |
H16 | 0.7514 | 0.2949 | 0.0423 | 0.024* | |
C11 | 0.7372 (2) | 0.51773 (19) | 0.7113 (2) | 0.0260 (6) | |
H11A | 0.7158 | 0.5762 | 0.7445 | 0.039* | |
H11B | 0.7536 | 0.4756 | 0.7764 | 0.039* | |
H11C | 0.6849 | 0.4914 | 0.6623 | 0.039* | |
C4 | 0.96296 (19) | 0.63374 (19) | 0.1981 (2) | 0.0226 (5) | |
H4 | 1.0197 | 0.6704 | 0.2038 | 0.027* | |
C13 | 0.58283 (19) | 0.40506 (19) | 0.1043 (2) | 0.0237 (5) | |
H13 | 0.5552 | 0.4682 | 0.1009 | 0.028* | |
C3 | 0.9176 (2) | 0.60232 (19) | 0.0924 (2) | 0.0245 (6) | |
H3 | 0.9382 | 0.6136 | 0.0133 | 0.029* | |
C6 | 0.7599 (2) | 0.50214 (18) | 0.0593 (2) | 0.0235 (5) | |
H6A | 0.7870 | 0.4709 | −0.0110 | 0.028* | |
H6B | 0.7091 | 0.5453 | 0.0317 | 0.028* | |
C8 | 0.7601 (2) | 0.75983 (18) | 0.4055 (2) | 0.0264 (6) | |
H8A | 0.8289 | 0.7632 | 0.3850 | 0.040* | |
H8B | 0.7363 | 0.8212 | 0.4244 | 0.040* | |
H8C | 0.7231 | 0.7352 | 0.3377 | 0.040* | |
C12 | 0.9043 (2) | 0.5865 (2) | 0.7040 (2) | 0.0251 (6) | |
H12A | 0.9636 | 0.5899 | 0.6570 | 0.038* | |
H12B | 0.9183 | 0.5553 | 0.7796 | 0.038* | |
H12C | 0.8807 | 0.6484 | 0.7201 | 0.038* | |
C19 | 0.6449 (2) | 0.4343 (2) | 0.4308 (2) | 0.0276 (6) | |
C9 | 0.6418 (2) | 0.6957 (2) | 0.5517 (3) | 0.0302 (6) | |
H9A | 0.6008 | 0.6762 | 0.4845 | 0.045* | |
H9B | 0.6223 | 0.7571 | 0.5771 | 0.045* | |
H9C | 0.6344 | 0.6529 | 0.6181 | 0.045* | |
C15 | 0.5780 (2) | 0.3690 (2) | −0.0230 (3) | 0.0306 (6) | |
H15A | 0.6234 | 0.4032 | −0.0724 | 0.046* | |
H15B | 0.5120 | 0.3766 | −0.0549 | 0.046* | |
H15C | 0.5953 | 0.3041 | −0.0235 | 0.046* | |
C17 | 0.7435 (2) | 0.23123 (19) | 0.2043 (3) | 0.0325 (7) | |
H17A | 0.7622 | 0.2444 | 0.2871 | 0.049* | |
H17B | 0.7768 | 0.1758 | 0.1777 | 0.049* | |
H17C | 0.6733 | 0.2219 | 0.1989 | 0.049* | |
C18 | 0.8820 (2) | 0.3239 (2) | 0.1225 (3) | 0.0302 (6) | |
H18A | 0.8978 | 0.3765 | 0.0722 | 0.045* | |
H18B | 0.9121 | 0.2688 | 0.0900 | 0.045* | |
H18C | 0.9067 | 0.3346 | 0.2036 | 0.045* | |
C14 | 0.5165 (2) | 0.3511 (3) | 0.1851 (3) | 0.0527 (11) | |
H14A | 0.5387 | 0.2875 | 0.1893 | 0.079* | |
H14B | 0.4501 | 0.3529 | 0.1529 | 0.079* | |
H14C | 0.5179 | 0.3779 | 0.2651 | 0.079* | |
C20 | 0.6421 (4) | 0.5689 (4) | 0.2971 (5) | 0.0198 (11) | 0.6667 |
C20A | 0.8107 (8) | 0.4104 (8) | 0.3908 (9) | 0.0185 (19) | 0.3333 |
C1 | 0.90896 (17) | 0.60093 (17) | 0.2917 (2) | 0.0158 (5) | |
C2 | 0.83779 (19) | 0.55196 (17) | 0.1258 (2) | 0.0184 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.01164 (15) | 0.01116 (15) | 0.01167 (15) | −0.00031 (12) | −0.00145 (11) | 0.00019 (12) |
Cl1A | 0.0203 (17) | 0.0172 (17) | 0.0281 (15) | 0.0109 (11) | −0.0154 (13) | −0.0062 (11) |
Cl1 | 0.0247 (9) | 0.0195 (9) | 0.0183 (7) | 0.0029 (6) | −0.0020 (6) | −0.0022 (6) |
P1 | 0.0128 (3) | 0.0138 (3) | 0.0122 (3) | 0.0000 (2) | −0.0003 (2) | −0.0021 (2) |
P2 | 0.0144 (3) | 0.0141 (3) | 0.0131 (3) | −0.0017 (2) | −0.0021 (2) | −0.0014 (2) |
O2 | 0.034 (3) | 0.028 (3) | 0.034 (2) | 0.0077 (18) | −0.016 (2) | −0.0050 (18) |
O2A | 0.036 (5) | 0.015 (4) | 0.033 (4) | 0.010 (3) | −0.009 (3) | 0.004 (3) |
O1 | 0.0497 (15) | 0.094 (2) | 0.0290 (12) | −0.0478 (15) | 0.0139 (11) | −0.0091 (13) |
N1 | 0.0172 (10) | 0.0153 (9) | 0.0116 (9) | −0.0038 (8) | 0.0001 (7) | −0.0007 (7) |
C7 | 0.0242 (13) | 0.0143 (11) | 0.0182 (12) | 0.0025 (9) | −0.0014 (10) | −0.0031 (9) |
C10 | 0.0251 (13) | 0.0157 (11) | 0.0134 (11) | 0.0021 (9) | −0.0031 (9) | −0.0013 (9) |
C5 | 0.0112 (10) | 0.0250 (12) | 0.0175 (12) | −0.0013 (9) | −0.0001 (9) | −0.0038 (10) |
C16 | 0.0205 (12) | 0.0207 (12) | 0.0186 (12) | 0.0024 (10) | −0.0023 (10) | −0.0077 (10) |
C11 | 0.0361 (15) | 0.0266 (13) | 0.0155 (12) | −0.0062 (12) | 0.0018 (11) | 0.0027 (10) |
C4 | 0.0191 (12) | 0.0263 (13) | 0.0225 (13) | −0.0056 (10) | 0.0016 (10) | −0.0009 (10) |
C13 | 0.0185 (12) | 0.0273 (14) | 0.0250 (13) | 0.0010 (10) | −0.0083 (10) | −0.0074 (11) |
C3 | 0.0276 (14) | 0.0294 (14) | 0.0165 (12) | −0.0073 (11) | 0.0042 (10) | 0.0032 (10) |
C6 | 0.0328 (14) | 0.0236 (13) | 0.0139 (11) | −0.0100 (11) | −0.0063 (10) | 0.0040 (10) |
C8 | 0.0357 (15) | 0.0166 (12) | 0.0267 (14) | −0.0010 (11) | −0.0050 (12) | 0.0031 (10) |
C12 | 0.0243 (13) | 0.0340 (15) | 0.0169 (12) | 0.0019 (11) | −0.0051 (10) | −0.0066 (11) |
C19 | 0.0245 (14) | 0.0382 (16) | 0.0202 (13) | −0.0108 (12) | −0.0002 (11) | −0.0068 (12) |
C9 | 0.0297 (15) | 0.0313 (15) | 0.0297 (15) | 0.0131 (12) | 0.0076 (12) | −0.0008 (12) |
C15 | 0.0272 (14) | 0.0398 (17) | 0.0245 (14) | −0.0078 (13) | −0.0104 (11) | −0.0029 (12) |
C17 | 0.0426 (18) | 0.0163 (13) | 0.0383 (17) | −0.0015 (12) | −0.0046 (14) | −0.0036 (12) |
C18 | 0.0208 (13) | 0.0374 (16) | 0.0323 (16) | 0.0063 (12) | 0.0020 (11) | −0.0107 (13) |
C14 | 0.0236 (16) | 0.105 (3) | 0.0301 (17) | −0.0275 (19) | 0.0019 (13) | −0.0096 (19) |
C20 | 0.021 (3) | 0.022 (3) | 0.016 (3) | −0.007 (2) | −0.001 (2) | −0.0051 (19) |
C20A | 0.019 (5) | 0.019 (5) | 0.017 (5) | −0.001 (4) | 0.001 (4) | 0.002 (4) |
C1 | 0.0130 (11) | 0.0193 (11) | 0.0150 (11) | −0.0032 (9) | −0.0015 (9) | −0.0016 (9) |
C2 | 0.0246 (13) | 0.0186 (11) | 0.0119 (11) | −0.0050 (10) | −0.0017 (9) | 0.0014 (9) |
Geometric parameters (Å, º) top
Fe1—Cl1A | 2.343 (3) | C11—H11C | 0.9800 |
Fe1—Cl1 | 2.3444 (19) | C4—H4 | 0.9500 |
Fe1—P1 | 2.2953 (7) | C4—C3 | 1.410 (4) |
Fe1—P2 | 2.2954 (7) | C4—C1 | 1.382 (3) |
Fe1—N1 | 1.960 (2) | C13—H13 | 1.0000 |
Fe1—C19 | 1.781 (3) | C13—C15 | 1.523 (4) |
Fe1—C20 | 1.770 (6) | C13—C14 | 1.518 (4) |
Fe1—C20A | 1.674 (12) | C3—H3 | 0.9500 |
P1—C7 | 1.845 (2) | C3—C2 | 1.381 (4) |
P1—C10 | 1.847 (2) | C6—H6A | 0.9900 |
P1—C5 | 1.838 (2) | C6—H6B | 0.9900 |
P2—C16 | 1.844 (3) | C6—C2 | 1.491 (3) |
P2—C13 | 1.850 (3) | C8—H8A | 0.9800 |
P2—C6 | 1.837 (3) | C8—H8B | 0.9800 |
O2—C20 | 1.100 (6) | C8—H8C | 0.9800 |
O2A—C20A | 1.258 (11) | C12—H12A | 0.9800 |
O1—C19 | 1.140 (3) | C12—H12B | 0.9800 |
N1—C1 | 1.366 (3) | C12—H12C | 0.9800 |
N1—C2 | 1.372 (3) | C9—H9A | 0.9800 |
C7—H7 | 1.0000 | C9—H9B | 0.9800 |
C7—C8 | 1.530 (4) | C9—H9C | 0.9800 |
C7—C9 | 1.528 (4) | C15—H15A | 0.9800 |
C10—H10 | 1.0000 | C15—H15B | 0.9800 |
C10—C11 | 1.532 (4) | C15—H15C | 0.9800 |
C10—C12 | 1.533 (3) | C17—H17A | 0.9800 |
C5—H5A | 0.9900 | C17—H17B | 0.9800 |
C5—H5B | 0.9900 | C17—H17C | 0.9800 |
C5—C1 | 1.497 (3) | C18—H18A | 0.9800 |
C16—H16 | 1.0000 | C18—H18B | 0.9800 |
C16—C17 | 1.526 (4) | C18—H18C | 0.9800 |
C16—C18 | 1.527 (4) | C14—H14A | 0.9800 |
C11—H11A | 0.9800 | C14—H14B | 0.9800 |
C11—H11B | 0.9800 | C14—H14C | 0.9800 |
| | | |
P1—Fe1—Cl1A | 97.74 (8) | C3—C4—H4 | 126.6 |
P1—Fe1—Cl1 | 84.84 (4) | C1—C4—H4 | 126.6 |
P1—Fe1—P2 | 160.93 (3) | C1—C4—C3 | 106.8 (2) |
P2—Fe1—Cl1A | 83.45 (8) | P2—C13—H13 | 105.8 |
P2—Fe1—Cl1 | 94.40 (4) | C15—C13—P2 | 113.30 (19) |
N1—Fe1—Cl1A | 89.19 (11) | C15—C13—H13 | 105.8 |
N1—Fe1—Cl1 | 92.09 (7) | C14—C13—P2 | 114.3 (2) |
N1—Fe1—P1 | 80.62 (6) | C14—C13—H13 | 105.8 |
N1—Fe1—P2 | 80.37 (6) | C14—C13—C15 | 111.1 (2) |
C19—Fe1—Cl1A | 92.38 (14) | C4—C3—H3 | 126.5 |
C19—Fe1—Cl1 | 86.38 (11) | C2—C3—C4 | 107.0 (2) |
C19—Fe1—P1 | 98.22 (9) | C2—C3—H3 | 126.5 |
C19—Fe1—P2 | 100.75 (9) | P2—C6—H6A | 110.3 |
C19—Fe1—N1 | 178.17 (11) | P2—C6—H6B | 110.3 |
C20—Fe1—Cl1 | 174.79 (17) | H6A—C6—H6B | 108.5 |
C20—Fe1—P1 | 95.12 (17) | C2—C6—P2 | 107.17 (17) |
C20—Fe1—P2 | 87.34 (17) | C2—C6—H6A | 110.3 |
C20—Fe1—N1 | 93.04 (18) | C2—C6—H6B | 110.3 |
C20—Fe1—C19 | 88.5 (2) | C7—C8—H8A | 109.5 |
C20A—Fe1—Cl1A | 176.0 (4) | C7—C8—H8B | 109.5 |
C20A—Fe1—P1 | 86.2 (3) | C7—C8—H8C | 109.5 |
C20A—Fe1—P2 | 93.1 (3) | H8A—C8—H8B | 109.5 |
C20A—Fe1—N1 | 92.3 (3) | H8A—C8—H8C | 109.5 |
C20A—Fe1—C19 | 86.2 (3) | H8B—C8—H8C | 109.5 |
C7—P1—Fe1 | 120.27 (8) | C10—C12—H12A | 109.5 |
C7—P1—C10 | 106.52 (11) | C10—C12—H12B | 109.5 |
C10—P1—Fe1 | 118.53 (8) | C10—C12—H12C | 109.5 |
C5—P1—Fe1 | 101.15 (8) | H12A—C12—H12B | 109.5 |
C5—P1—C7 | 104.22 (12) | H12A—C12—H12C | 109.5 |
C5—P1—C10 | 103.59 (12) | H12B—C12—H12C | 109.5 |
C16—P2—Fe1 | 121.43 (8) | O1—C19—Fe1 | 179.0 (3) |
C16—P2—C13 | 106.28 (12) | C7—C9—H9A | 109.5 |
C13—P2—Fe1 | 118.91 (9) | C7—C9—H9B | 109.5 |
C6—P2—Fe1 | 100.98 (8) | C7—C9—H9C | 109.5 |
C6—P2—C16 | 103.60 (13) | H9A—C9—H9B | 109.5 |
C6—P2—C13 | 102.47 (13) | H9A—C9—H9C | 109.5 |
C1—N1—Fe1 | 126.21 (16) | H9B—C9—H9C | 109.5 |
C1—N1—C2 | 107.9 (2) | C13—C15—H15A | 109.5 |
C2—N1—Fe1 | 125.90 (16) | C13—C15—H15B | 109.5 |
P1—C7—H7 | 107.0 | C13—C15—H15C | 109.5 |
C8—C7—P1 | 111.37 (18) | H15A—C15—H15B | 109.5 |
C8—C7—H7 | 107.0 | H15A—C15—H15C | 109.5 |
C9—C7—P1 | 113.66 (18) | H15B—C15—H15C | 109.5 |
C9—C7—H7 | 107.0 | C16—C17—H17A | 109.5 |
C9—C7—C8 | 110.4 (2) | C16—C17—H17B | 109.5 |
P1—C10—H10 | 106.2 | C16—C17—H17C | 109.5 |
C11—C10—P1 | 114.02 (18) | H17A—C17—H17B | 109.5 |
C11—C10—H10 | 106.2 | H17A—C17—H17C | 109.5 |
C11—C10—C12 | 110.5 (2) | H17B—C17—H17C | 109.5 |
C12—C10—P1 | 113.15 (18) | C16—C18—H18A | 109.5 |
C12—C10—H10 | 106.2 | C16—C18—H18B | 109.5 |
P1—C5—H5A | 110.3 | C16—C18—H18C | 109.5 |
P1—C5—H5B | 110.3 | H18A—C18—H18B | 109.5 |
H5A—C5—H5B | 108.6 | H18A—C18—H18C | 109.5 |
C1—C5—P1 | 107.01 (16) | H18B—C18—H18C | 109.5 |
C1—C5—H5A | 110.3 | C13—C14—H14A | 109.5 |
C1—C5—H5B | 110.3 | C13—C14—H14B | 109.5 |
P2—C16—H16 | 106.4 | C13—C14—H14C | 109.5 |
C17—C16—P2 | 113.11 (19) | H14A—C14—H14B | 109.5 |
C17—C16—H16 | 106.4 | H14A—C14—H14C | 109.5 |
C17—C16—C18 | 111.6 (2) | H14B—C14—H14C | 109.5 |
C18—C16—P2 | 112.32 (18) | O2—C20—Fe1 | 177.5 (6) |
C18—C16—H16 | 106.4 | O2A—C20A—Fe1 | 176.0 (11) |
C10—C11—H11A | 109.5 | N1—C1—C5 | 116.6 (2) |
C10—C11—H11B | 109.5 | N1—C1—C4 | 109.3 (2) |
C10—C11—H11C | 109.5 | C4—C1—C5 | 134.0 (2) |
H11A—C11—H11B | 109.5 | N1—C2—C3 | 109.0 (2) |
H11A—C11—H11C | 109.5 | N1—C2—C6 | 116.7 (2) |
H11B—C11—H11C | 109.5 | C3—C2—C6 | 134.3 (2) |
| | | |
Fe1—P1—C7—C8 | −64.7 (2) | C5—P1—C7—C8 | 47.6 (2) |
Fe1—P1—C7—C9 | 60.8 (2) | C5—P1—C7—C9 | 173.05 (19) |
Fe1—P1—C10—C11 | −75.67 (19) | C5—P1—C10—C11 | 173.36 (18) |
Fe1—P1—C10—C12 | 156.94 (15) | C5—P1—C10—C12 | 46.0 (2) |
Fe1—P1—C5—C1 | 28.94 (18) | C16—P2—C13—C15 | −47.1 (2) |
Fe1—P2—C16—C17 | 65.5 (2) | C16—P2—C13—C14 | 81.5 (3) |
Fe1—P2—C16—C18 | −61.9 (2) | C16—P2—C6—C2 | −97.1 (2) |
Fe1—P2—C13—C15 | 171.46 (17) | C4—C3—C2—N1 | −0.4 (3) |
Fe1—P2—C13—C14 | −59.9 (3) | C4—C3—C2—C6 | 179.0 (3) |
Fe1—P2—C6—C2 | 29.3 (2) | C13—P2—C16—C17 | −74.7 (2) |
Fe1—N1—C1—C5 | 3.2 (3) | C13—P2—C16—C18 | 157.84 (19) |
Fe1—N1—C1—C4 | −179.17 (17) | C13—P2—C6—C2 | 152.52 (19) |
Fe1—N1—C2—C3 | 179.30 (18) | C3—C4—C1—N1 | 0.1 (3) |
Fe1—N1—C2—C6 | −0.2 (3) | C3—C4—C1—C5 | 177.1 (3) |
P1—C5—C1—N1 | −23.3 (3) | C6—P2—C16—C17 | 177.70 (19) |
P1—C5—C1—C4 | 159.9 (3) | C6—P2—C16—C18 | 50.3 (2) |
P2—C6—C2—N1 | −21.7 (3) | C6—P2—C13—C15 | 61.3 (2) |
P2—C6—C2—C3 | 158.9 (3) | C6—P2—C13—C14 | −170.1 (2) |
C7—P1—C10—C11 | 63.8 (2) | C1—N1—C2—C3 | 0.5 (3) |
C7—P1—C10—C12 | −63.6 (2) | C1—N1—C2—C6 | −179.0 (2) |
C7—P1—C5—C1 | −96.51 (18) | C1—C4—C3—C2 | 0.2 (3) |
C10—P1—C7—C8 | 156.73 (18) | C2—N1—C1—C5 | −178.0 (2) |
C10—P1—C7—C9 | −77.8 (2) | C2—N1—C1—C4 | −0.4 (3) |
C10—P1—C5—C1 | 152.21 (17) | | |