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research communications
N-diphenylphosphanyl-N,N′-diisopropyl-P-phenylphosphonous diamide-κ2P,P′)cobalt(I) tetracarbonylcobaltate(−I) toluene 0.25-solvate
of tricarbonyl(aLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: torsten.beweries@catalysis.de
The 24H30N2P2)(CO)3][Co(CO)4]·0.25C7H8, consists of two crystallographically independent cations with similar conformations, two anions, and one-half of a toluene molecule disordered about an inversion centre. In the cations, a Co/P/N/P four-membered slightly bent metallacycle is the key structural element. The pendant NH group is not coordinated to the CoI atom, which displays a distorted trigonal–bipyramidal coordination geometry. Weak interionic hydrogen bonds are observed between the NH groups and a carbonyl group of the tetrahedral [Co(CO)4]− anions.
of the title compound, [Co(CKeywords: crystal structure; cobalt; phosphine ligand; metallacycle.
CCDC reference: 1033917
1. Chemical context
Reaction of the PNPNH ligand N-(diphenylphosphanyl)-N,N′-diisopropyl-diaminophenylphosphine, Ph2PN(i-Pr)P(Ph)N(H)i-Pr, with the cobalt precursor Co2(CO)8 was performed to prepare a noble-metal-free catalyst for light-driven water reduction to produce hydrogen. These compounds are attractive in terms of environmental acceptability as well as for economic reasons. Several very active intermolecular water-reduction systems using 3d metal complexes as catalytically active centres are known, examples include work on iron (e.g. Mejía et al., 2013), nickel (e.g. Zhang et al., 2011
) and cobalt (e.g. Tong et al., 2014
) complexes. It is likely that the NH group of the ligand and the Co atom cooperate in the proton-reduction process as has been reported for other water-reduction complexes (Han et al., 2012
). We found that, apart from the previously described catalytically active dinuclear CO-bridged product Co2(CO)6(PNPNH) (Hansen et al., 2013
), an ionic complex is also formed in this reaction. Both complexes can be separated by fractionated crystallization from toluene. It should be noted that in solution, the title compound is rapidly converted into the neutral dinuclear species Co2(CO)6(PNPNH) and therefore the IR and NMR spectra were measured only from freshly prepared samples.
2. Structural commentary
The title compound crystallizes in the monoclinic P21/n with eight cations, eight anions as well as two molecules of toluene in the The toluene solvent molecules are found to be disordered about inversion centres. The is shown in Fig. 1. In the cation, the CoI atom is fivefold coordinated by three carbonyl ligands and the PNPNH ligand, which is bound via both P atoms (Fig. 2
). Thus, the bidentate ligand forms a four-membered metallacycle at the CoI atom with the central N atom being tilted out of the plane formed by the Co and the two P atoms [the dihedral angles between the CoP2 and NP2 planes are 15.73 (10) and 14.44 (9)°]. The terminal secondary amine is not involved in complexation with the CoI atom and acts as a spectator group. In the cyclic units the following bond lengths are observed: Co1—P1 2.1948 (7), P1—N2 1.698 (2), N2—P2 1.695 (2), P2—Co1 2.1800 (7), Co2—P3 2.1884 (7), P3—N4 1.695 (2), N4—P4 1.702 (2), P4—Co2 2.1971 (7) Å. A similar coordination mode was previously found for this ligand in a variety of transition metal complexes (Aluri et al., 2010
). In the cationic parts, one of the Co—C distances [Co1—C3 1.821 (3) and Co2—C30 1.832 (3) Å] is slightly longer than the other two values. In the anion, the geometry at the cobalt atom is found to be distorted tetrahedral; all C—Co—C angles are found to be between 105.75 (13) and 111.89 (14)°, thus indicating a minor deviation from ideal Td symmetry. The Co—C bond lengths in the anions vary from 1.754 (4)–1.770 (3) Å and are comparable to those observed for a range of complexes displaying tetracarbonylcobaltate anions (vide supra), including ionic salts of tetracarbonylcobaltate with alkali (Klüfers, 1984a
,b
) and ammonium cations (Brammer et al. 1992
; Brammer & Zhao, 1995
).
![]() | Figure 1 The asymmetric unit of the title compound. Hydrogen atoms are omitted for clarity. Displacement ellipsoids correspond to the 30% probability level. Only one orientation of the disordered toluene molecule is shown. |
![]() | Figure 2 Interionic N—H⋯O hydrogen bond (dashed line) connecting an ion-pair in the title compound. Hydrogen atoms not involved in hydrogen bonding, the co-crystallized toluene molecule and the second ion-pair of the asymmetric unit are omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level. |
3. Supramolecular features
A weak hydrogen-bonding interaction is observed between the NH group of the cation and one of the O atoms of the tetracarbonylcobaltate(−I) anions (Table 1). Other than in the literature-known compound [Et3NH][Co(CO)4] (Brammer et al., 1992
), no 3c–4e hydrogen-bond-like N—H⋯Co interaction has been found.
|
4. Database survey
For a similar, carbonyl-bridged dinuclear cobalt complex with this PNPNH ligand, see: Hansen et al. (2013). Examples for structural reports of other CoI–Co−I ion-pair complexes can be found in Fellmann et al. (1983
), Bockman & Kochi (1989
), Zhang et al. (1994
), Uehara et al. (2005
), van Rensburg et al. (2007
) and Azhakar et al. (2012
). Other transition metal complexes with this ligand are described in Aluri et al. (2010
) and Dulai et al. (2011
).
5. Synthesis and crystallization
General: N-(diphenylphosphanyl)-N,N′-diisopropyl-diaminophenylphosphine was synthesized by a literature method (Peitz et al., 2010). Co2(CO)8 was purchased from Strem and used without further purification. Toluene was dried over CaH2 and distilled prior to use. Synthesis: A solution of Co2(CO)8 (0.30 g, 0.88 mmol) in toluene (10 ml) was added to N-(diphenylphosphanyl)-N,N′-diisopropyl-diaminophenylphosphine, Ph2PN(i-Pr)P(Ph)N(H)i-Pr (0.36 g, 0.88 mmol) in a After gas evolution subsided, the 50 ml Schlenk flask was closed and heated to 383 K for 35 min without stirring to preserve the two-phase system. After crystallization from toluene at room temperature for three days, two crystal fractions were separated from the solvent and washed with n-hexane (2 × 5 ml). The fraction of cubic brown crystals showed space-group and lattice parameters identical to X-ray diffraction data published previously (Hansen et al., 2013
). The second fraction contained yellow needles with the presented here. Further isolation of this new complex was not possible as it inevitably forms the known dinuclear product when dissolved in organic solvents. Manual picking of the crystals was difficult as the material proved too delicate. Analytics: 31P NMR (297 K, THF-d8, 162 Hz): δ (p.p.m) 61.8 (d, J = 150 Hz), 59.9 (d, J = 150 Hz); IR (ATR, THF): ν−1 [cm−1] 3335 (w), 3191 (w), 3058 (w), 2975 (m), 2869 (m), 2081 [s, Co(CO)3+], 2021 [s, Co(CO)3+], 1979 (w), 1872 [s, Co(CO)4−], 1586 (w), 1462 (w), 1436 (m), 1390 (w), 1369 (w), 1311(w), 1165 (w), 1125 (m), 1097 (m), 1064 (m), 999 (w), 896 (m), 869 (m), 747 (m), 716 (w), 694 (m), 631 (w), 612 (w), 550 (s), 501 (m), 426 (m).
6. Refinement
Crystal data, data collection and structure . Atoms H1 and H3 were located in a difference Fourier map and their coordinates were refined with the restraint N—H = 0.87 (1) Å. All other H atoms were placed in idealized positions with d(C—H) = 0.95–1.00 (CH) and 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) for CH and 1.5 Ueq(C) for CH3. The ring of the half-occupied toluene molecule was constrained to resemble an ideal hexagon with C—C distances of 1.39 Å. SADI instructions were used to improve the geometry of one phenyl ring (C24–C25, C25–C26) and one i-propyl group (C13–C14, C13–C15).
|
Supporting information
CCDC reference: 1033917
10.1107/S1600536814024908/rz5139sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814024908/rz5139Isup2.hkl
The reaction of the PNPNH ligand N-(diphenylphosphino)-N,N'-diisopropyl- diaminophenylphosphine, Ph2PN(i-Pr)P(Ph)N(H)i-Pr, with the cobalt precursor Co2(CO)8 was performed to prepare a noble-metal-free catalyst for light-driven water reduction to produce hydrogen. These compounds are attractive in terms of environmental acceptability as well as for economic reasons. Several very active intermolecular water-reduction systems using 3d metal complexes as catalytically active centres are known, examples include work on iron (e.g. Mejía et al., 2013), nickel (e.g. Zhang et al., 2011) and cobalt (e.g. Tong et al., 2014) complexes. It is likely that the NH group of the ligand and the Co centre cooperate in the proton-reduction process as has been reported for other water-reduction complexes (Han et al., 2012). We found that, apart from the previously described catalytically active dinuclear CO-bridged product Co2(CO)6(PNPNH) (Hansen et al., 2013), an ionic complex is also formed in this reaction. Both complexes can be separated by fractionated crystallization from toluene. It should be noted that in solution, the title compound is rapidly converted into the neutral dinuclear species Co2(CO)6(PNPNH) and therefore the IR and NMR spectra were measured only from freshly prepared samples.
The title compound crystallizes in the monoclinic
P21/n with eight cations, eight anions as well as two molecules of toluene in the The toluene solvent molecules are found to be disordered about inversion centres. The is shown in Fig. 1. In the cation, the CoI atom is fivefold coordinated by three carbonyl ligands and the PNPNH ligand, which is bound via both P atoms (Fig. 2). Thus, the bidentate ligand forms a four-membered metallacycle at the CoI atom with the central N atom being tilted out of the plane formed by the Co and the two P atoms [the dihedral angles between the CoP2 and NP2 planes are 15.73 (10) and 14.44 (9)°]. The terminal secondary amine is not involved in complexation with the CoI atom and acts as a spectator group. In the cyclic units the following bond lengths are observed: Co1—P1 2.1948 (7), P1—N2 1.698 (2), N2—P2 1.695 (2), P2—Co1 2.1800 (7), Co2—P3 2.1884 (7), P3—N4 1.695 (2), N4—P4 1.702 (2), P4—Co2 2.1971 (7) Å. A similar coordination mode was previously found for this ligand in a variety of transition metal complexes (Aluri et al., 2010). In the cationic parts, one of the Co—C distances [Co1—C3 1.821 (3) and Co2—C30 1.832 (3) Å] is slightly longer than the other two values. In the anion, the geometry at the cobalt centre is found to be distorted tetrahedral; all C—Co—C angles are found to be between 105.75 (13) and 111.89 (14)°, thus indicating a minor deviation from ideal Td symmetry. The Co—C bond lengths in the anions vary from 1.754 (4)–1.770 (3) Å and are comparable to those observed for a range of complexes displaying tetracarbonylcobalt anions (vide supra), including ionic salts of tetracarbonylcobaltate with alkali (Klüfers, 1984a,b) and ammonium cations (Brammer et al. 1992; Brammer & Zhao, 1995).A weak hydrogen-bonding interaction is observed between the NH group of the cation and one of the O atoms of the tetracarbonylcobalt(-I) anions (Table 1). Other than in the literature-known compound [Et3NH][Co(CO)4] (Brammer et al., 1992), no 3c--4e hydrogen-bond-like N—H···Co interaction has been found.
For a similar, carbonyl-bridged dinuclear cobalt complex with this PNP ligand, see: Hansen et al. (2013). Examples for structural reports of other CoI–Co—I ion-pair complexes can be found in Fellmann et al. (1983), Bockman & Kochi (1989), Zhang et al. (1994), Uehara et al. (2005), van Rensburg et al. (2007) and Azhakar et al. (2012). Other transition metal complexes with this ligand are described in Aluri et al. (2010) and Dulai et al. (2011).
\ Generale: N-(diphenylphosphino)-N,N'-diisopropyl-\ diaminophenylphosphine was synthesized as published before (Peitz et al., 2010). Co2(CO)8 was purchased from Strem and used without further purification. Toluene was dried over CaH2 and distilled prior to use. Synthesis: A solution of Co2(CO)8 (0.30g, 0.88mmol) in toluene (10 mL) was added to N-(diphenylphosphino)-N,N'-diisopropyl-\ diaminophenylphosphine, Ph2PN(i-Pr)P(Ph)N(H)i-Pr (0.36 g, 0.88 mmol) in a δ (p.p.m) 61.8 (d, J = 150 Hz), 59.9 (d, J = 150 Hz); IR (ATR, THF): ν-1 [cm-1] 3335 (w), 3191 (w), 3058 (w), 2975 (m), 2869 (m), 2081 [s, Co(CO)3+], 2021 [s, Co(CO)3+], 1979 (w), 1872 [s, Co(CO)4-], 1586 (w), 1462 (w), 1436 (m), 1390 (w), 1369 (w), 1311(w), 1165 (w), 1125 (m), 1097 (m), 1064 (m), 999 (w), 896 (m), 869 (m), 747 (m), 716 (w), 694 (m), 631 (w), 612 (w), 550 (s), 501 (m), 426 (m).
After gas evolution subsided, the 50 mL Schlenk flask was closed and heated to 383 K for 35 min without stirring to preserve the two-phase system. After crystallization from toluene at room temperature for three days, two crystal fractions were separated from the solvent and washed with n-hexane (2 × 5 mL). The fraction of cubic brown crystals showed space-group and lattice parameters identical to X-ray diffraction data published previously (Hansen et al., 2013). The second fraction contained yellow needles with the presented here. Further isolation of this new complex was not possible as it inevitably forms the known dinuclear product when dissolved in organic solvents. Manual picking of the crystals was difficult as the material proved too delicate. Analytics: 31P NMR (297 K, THF-d8, 162 Hz):Crystal data, data collection and structure
details are summarized in Table 2. Atoms H1 and H3 were located in a difference Fourier map and their coordinates were refined with the restraint N—H = 0.87 (1) Å. All other H atoms were placed in idealized positions with d(C—H) = 0.95–1.00 (CH) and 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) for CH and 1.5 Ueq(C) for CH3. The ring of the half-occupied toluene molecule was constrained to resemble an ideal hexagon with C—C distances of 1.39 Å. SADI instructions were used to improve the geometry of one phenyl ring (C24–C25, C25–C26) and one i-propyl group (C13–C14, C13–C15).Data collection: APEX2 (Bruker, 2011); cell
SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Figure 1. The asymmetric unit of the title compound. Hydrogen atoms are omitted for clarity. Displacement ellipsoids correspond to 30% probability. Only one orientation of the disordered toluene molecule is shown. Figure 2. Interionic N—H···O hydrogen bond (dashed line) connecting an ion-pair in the title compound. Hydrogen atoms not involved in hydrogen bonding, the co-crystallized toluene molecule and the second ion-pair of the are omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level. |
[Co(C24H30N2P2)(CO)3][Co(CO)4]·0.25C7H8 | F(000) = 3060 |
Mr = 745.40 | Dx = 1.432 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 22.1602 (6) Å | Cell parameters from 9777 reflections |
b = 12.9730 (3) Å | θ = 3.7–66.7° |
c = 24.7883 (6) Å | µ = 8.79 mm−1 |
β = 103.9330 (12)° | T = 150 K |
V = 6916.6 (3) Å3 | Needle, yellow |
Z = 8 | 0.43 × 0.11 × 0.05 mm |
Bruker Kappa APEXII DUO diffractometer | 12171 independent reflections |
Radiation source: microfocus | 11080 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.044 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 66.5°, θmin = 2.4° |
ϕ and ω scans | h = −26→25 |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | k = −15→14 |
Tmin = 0.12, Tmax = 0.65 | l = −23→29 |
89837 measured reflections |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0494P)2 + 7.7784P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
12171 reflections | Δρmax = 0.93 e Å−3 |
825 parameters | Δρmin = −0.57 e Å−3 |
[Co(C24H30N2P2)(CO)3][Co(CO)4]·0.25C7H8 | V = 6916.6 (3) Å3 |
Mr = 745.40 | Z = 8 |
Monoclinic, P21/n | Cu Kα radiation |
a = 22.1602 (6) Å | µ = 8.79 mm−1 |
b = 12.9730 (3) Å | T = 150 K |
c = 24.7883 (6) Å | 0.43 × 0.11 × 0.05 mm |
β = 103.9330 (12)° |
Bruker Kappa APEXII DUO diffractometer | 12171 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | 11080 reflections with I > 2σ(I) |
Tmin = 0.12, Tmax = 0.65 | Rint = 0.044 |
89837 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 4 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.93 e Å−3 |
12171 reflections | Δρmin = −0.57 e Å−3 |
825 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.26645 (13) | 0.8434 (2) | 0.15492 (12) | 0.0349 (6) | |
C2 | 0.25541 (13) | 0.7575 (2) | 0.05615 (13) | 0.0368 (7) | |
C3 | 0.25514 (13) | 0.6280 (2) | 0.15325 (14) | 0.0384 (7) | |
C4 | 0.12520 (16) | 0.9773 (2) | 0.10407 (12) | 0.0387 (7) | |
H4 | 0.1533 | 0.9488 | 0.0816 | 0.046* | |
C5 | 0.1505 (2) | 1.0822 (3) | 0.12626 (17) | 0.0603 (11) | |
H5A | 0.1226 | 1.1132 | 0.1470 | 0.090* | |
H5B | 0.1531 | 1.1271 | 0.0951 | 0.090* | |
H5C | 0.1919 | 1.0737 | 0.1510 | 0.090* | |
C6 | 0.06036 (18) | 0.9842 (3) | 0.06670 (15) | 0.0571 (10) | |
H6A | 0.0472 | 0.9159 | 0.0514 | 0.086* | |
H6B | 0.0603 | 1.0324 | 0.0363 | 0.086* | |
H6C | 0.0315 | 1.0087 | 0.0883 | 0.086* | |
C7 | 0.15272 (13) | 0.7513 (2) | 0.22363 (11) | 0.0292 (6) | |
C8 | 0.13489 (14) | 0.6542 (2) | 0.23867 (12) | 0.0348 (6) | |
H8 | 0.1163 | 0.6062 | 0.2107 | 0.042* | |
C9 | 0.14415 (16) | 0.6277 (3) | 0.29406 (13) | 0.0446 (8) | |
H9 | 0.1315 | 0.5619 | 0.3040 | 0.053* | |
C10 | 0.17175 (17) | 0.6966 (3) | 0.33486 (13) | 0.0503 (9) | |
H10 | 0.1781 | 0.6782 | 0.3729 | 0.060* | |
C11 | 0.19017 (17) | 0.7918 (3) | 0.32061 (13) | 0.0480 (8) | |
H11 | 0.2094 | 0.8390 | 0.3489 | 0.058* | |
C12 | 0.18085 (14) | 0.8195 (2) | 0.26511 (12) | 0.0374 (7) | |
H12 | 0.1938 | 0.8854 | 0.2555 | 0.045* | |
C13 | 0.02566 (11) | 0.70193 (17) | 0.10262 (9) | 0.0246 (5) | |
H13 | 0.0072 | 0.7400 | 0.0674 | 0.029* | |
C14 | 0.00085 (14) | 0.7512 (3) | 0.14945 (13) | 0.0432 (8) | |
H14A | 0.0192 | 0.7164 | 0.1847 | 0.065* | |
H14B | −0.0445 | 0.7442 | 0.1409 | 0.065* | |
H14C | 0.0120 | 0.8244 | 0.1526 | 0.065* | |
C15 | 0.00114 (14) | 0.5900 (2) | 0.09563 (15) | 0.0422 (7) | |
H15A | 0.0162 | 0.5560 | 0.0661 | 0.063* | |
H15B | −0.0444 | 0.5906 | 0.0858 | 0.063* | |
H15C | 0.0161 | 0.5524 | 0.1306 | 0.063* | |
C16 | 0.09747 (12) | 0.72904 (19) | −0.00255 (10) | 0.0247 (5) | |
C17 | 0.11839 (13) | 0.8191 (2) | −0.02320 (11) | 0.0283 (6) | |
H17 | 0.1535 | 0.8546 | −0.0017 | 0.034* | |
C18 | 0.08784 (14) | 0.8567 (2) | −0.07507 (11) | 0.0337 (6) | |
H18 | 0.1026 | 0.9173 | −0.0891 | 0.040* | |
C19 | 0.03626 (14) | 0.8065 (2) | −0.10626 (12) | 0.0368 (7) | |
H19 | 0.0155 | 0.8326 | −0.1417 | 0.044* | |
C20 | 0.01487 (14) | 0.7183 (3) | −0.08597 (12) | 0.0392 (7) | |
H20 | −0.0209 | 0.6842 | −0.1073 | 0.047* | |
C21 | 0.04531 (13) | 0.6793 (2) | −0.03476 (11) | 0.0329 (6) | |
H21 | 0.0306 | 0.6180 | −0.0213 | 0.039* | |
C22 | 0.14085 (12) | 0.54130 (19) | 0.05436 (10) | 0.0237 (5) | |
C23 | 0.15779 (14) | 0.5072 (2) | 0.00688 (11) | 0.0329 (6) | |
H23 | 0.1593 | 0.5542 | −0.0221 | 0.039* | |
C24 | 0.17251 (16) | 0.4042 (2) | 0.00199 (12) | 0.0411 (7) | |
H24 | 0.1841 | 0.3808 | −0.0304 | 0.049* | |
C25 | 0.17039 (15) | 0.3355 (2) | 0.04412 (10) | 0.0421 (7) | |
H25 | 0.1805 | 0.2651 | 0.0407 | 0.050* | |
C26 | 0.15350 (15) | 0.3695 (2) | 0.09130 (12) | 0.0379 (7) | |
H26 | 0.1517 | 0.3220 | 0.1200 | 0.046* | |
C27 | 0.13923 (13) | 0.4717 (2) | 0.09699 (11) | 0.0299 (6) | |
H27 | 0.1283 | 0.4947 | 0.1298 | 0.036* | |
C28 | 0.58062 (13) | 0.4567 (2) | 0.27082 (11) | 0.0308 (6) | |
C29 | 0.67739 (12) | 0.5553 (2) | 0.25305 (10) | 0.0277 (6) | |
C30 | 0.69210 (14) | 0.3421 (2) | 0.26735 (11) | 0.0335 (6) | |
C31 | 0.58671 (12) | 0.6413 (2) | 0.12397 (11) | 0.0259 (5) | |
H31 | 0.5690 | 0.6143 | 0.1547 | 0.031* | |
C32 | 0.53701 (14) | 0.6327 (3) | 0.06988 (12) | 0.0399 (7) | |
H32A | 0.5535 | 0.6585 | 0.0392 | 0.060* | |
H32B | 0.5007 | 0.6737 | 0.0725 | 0.060* | |
H32C | 0.5248 | 0.5604 | 0.0631 | 0.060* | |
C33 | 0.60641 (15) | 0.7521 (2) | 0.13732 (13) | 0.0380 (7) | |
H33A | 0.6385 | 0.7545 | 0.1723 | 0.057* | |
H33B | 0.5704 | 0.7928 | 0.1410 | 0.057* | |
H33C | 0.6231 | 0.7806 | 0.1073 | 0.057* | |
C34 | 0.73787 (11) | 0.4484 (2) | 0.14454 (10) | 0.0238 (5) | |
C35 | 0.76054 (13) | 0.3498 (2) | 0.13827 (11) | 0.0320 (6) | |
H35 | 0.7337 | 0.2918 | 0.1348 | 0.038* | |
C36 | 0.82267 (14) | 0.3365 (3) | 0.13713 (12) | 0.0399 (7) | |
H36 | 0.8381 | 0.2694 | 0.1328 | 0.048* | |
C37 | 0.86170 (13) | 0.4201 (3) | 0.14227 (12) | 0.0406 (7) | |
H37 | 0.9039 | 0.4107 | 0.1412 | 0.049* | |
C38 | 0.83978 (13) | 0.5175 (3) | 0.14893 (12) | 0.0382 (7) | |
H38 | 0.8671 | 0.5750 | 0.1526 | 0.046* | |
C39 | 0.77817 (13) | 0.5323 (2) | 0.15025 (11) | 0.0296 (6) | |
H39 | 0.7634 | 0.5996 | 0.1550 | 0.036* | |
C40 | 0.59574 (12) | 0.3382 (2) | 0.05627 (10) | 0.0267 (5) | |
H40 | 0.5505 | 0.3551 | 0.0435 | 0.032* | |
C41 | 0.60339 (16) | 0.2242 (2) | 0.04650 (12) | 0.0372 (7) | |
H41A | 0.6474 | 0.2055 | 0.0587 | 0.056* | |
H41B | 0.5883 | 0.2089 | 0.0068 | 0.056* | |
H41C | 0.5794 | 0.1843 | 0.0677 | 0.056* | |
C42 | 0.63040 (15) | 0.4023 (2) | 0.02205 (11) | 0.0345 (6) | |
H42A | 0.6215 | 0.4755 | 0.0260 | 0.052* | |
H42B | 0.6168 | 0.3824 | −0.0172 | 0.052* | |
H42C | 0.6752 | 0.3902 | 0.0352 | 0.052* | |
C43 | 0.58053 (13) | 0.2016 (2) | 0.18317 (10) | 0.0276 (6) | |
C44 | 0.53245 (15) | 0.1575 (2) | 0.20273 (12) | 0.0364 (7) | |
H44 | 0.4973 | 0.1977 | 0.2051 | 0.044* | |
C45 | 0.53624 (17) | 0.0543 (3) | 0.21875 (13) | 0.0458 (8) | |
H45 | 0.5037 | 0.0240 | 0.2322 | 0.055* | |
C46 | 0.58709 (18) | −0.0042 (2) | 0.21511 (12) | 0.0458 (8) | |
H46 | 0.5892 | −0.0747 | 0.2257 | 0.055* | |
C47 | 0.63477 (16) | 0.0394 (2) | 0.19621 (12) | 0.0405 (7) | |
H47 | 0.6697 | −0.0013 | 0.1938 | 0.049* | |
C48 | 0.63226 (14) | 0.1421 (2) | 0.18073 (11) | 0.0332 (6) | |
H48 | 0.6657 | 0.1720 | 0.1685 | 0.040* | |
C49 | 0.49608 (12) | 0.3638 (2) | 0.13700 (10) | 0.0263 (5) | |
C50 | 0.46769 (12) | 0.4538 (2) | 0.14867 (11) | 0.0296 (6) | |
H50 | 0.4899 | 0.5005 | 0.1758 | 0.036* | |
C51 | 0.40676 (13) | 0.4755 (2) | 0.12067 (12) | 0.0367 (7) | |
H51 | 0.3875 | 0.5371 | 0.1286 | 0.044* | |
C52 | 0.37425 (14) | 0.4077 (3) | 0.08138 (13) | 0.0404 (7) | |
H52 | 0.3327 | 0.4230 | 0.0623 | 0.049* | |
C53 | 0.40198 (14) | 0.3178 (3) | 0.06969 (12) | 0.0397 (7) | |
H53 | 0.3794 | 0.2716 | 0.0425 | 0.048* | |
C54 | 0.46254 (13) | 0.2946 (2) | 0.09748 (11) | 0.0331 (6) | |
H54 | 0.4812 | 0.2322 | 0.0898 | 0.040* | |
C55 | 0.42419 (15) | 0.8392 (3) | 0.26588 (12) | 0.0401 (7) | |
C56 | 0.52940 (14) | 0.7284 (2) | 0.24900 (11) | 0.0316 (6) | |
C57 | 0.42198 (14) | 0.7594 (2) | 0.15653 (12) | 0.0349 (6) | |
C58 | 0.41993 (13) | 0.6173 (2) | 0.24610 (11) | 0.0338 (6) | |
C59 | 0.14719 (16) | 0.1170 (3) | 0.95283 (15) | 0.0474 (8) | |
C60 | 0.25789 (16) | 0.0432 (2) | 1.02628 (14) | 0.0439 (8) | |
C61 | 0.26473 (15) | 0.2103 (3) | 0.95163 (13) | 0.0412 (7) | |
C62 | 0.23996 (18) | 0.0006 (3) | 0.91221 (15) | 0.0587 (10) | |
Co1 | 0.22216 (2) | 0.74279 (3) | 0.11504 (2) | 0.02425 (10) | |
Co2 | 0.63667 (2) | 0.43778 (3) | 0.23007 (2) | 0.02064 (10) | |
Co3 | 0.44772 (2) | 0.73693 (3) | 0.22886 (2) | 0.02648 (11) | |
Co4 | 0.22726 (2) | 0.09426 (4) | 0.95973 (2) | 0.03635 (12) | |
N1 | 0.12681 (11) | 0.90667 (17) | 0.15071 (10) | 0.0306 (5) | |
N2 | 0.09256 (10) | 0.70471 (16) | 0.11124 (9) | 0.0243 (4) | |
N3 | 0.64182 (10) | 0.57857 (16) | 0.12197 (9) | 0.0234 (4) | |
N4 | 0.61636 (10) | 0.36438 (16) | 0.11707 (8) | 0.0218 (4) | |
O1 | 0.29238 (11) | 0.90745 (18) | 0.18266 (10) | 0.0517 (6) | |
O2 | 0.27494 (12) | 0.7675 (2) | 0.01802 (11) | 0.0610 (7) | |
O3 | 0.27388 (12) | 0.5557 (2) | 0.17721 (13) | 0.0676 (8) | |
O4 | 0.54660 (11) | 0.46924 (18) | 0.29796 (9) | 0.0458 (5) | |
O5 | 0.70530 (9) | 0.62862 (16) | 0.26537 (8) | 0.0380 (5) | |
O6 | 0.72663 (12) | 0.28503 (19) | 0.29185 (10) | 0.0553 (6) | |
O7 | 0.41050 (14) | 0.9060 (2) | 0.29101 (10) | 0.0648 (8) | |
O8 | 0.58259 (10) | 0.72001 (18) | 0.26369 (9) | 0.0455 (5) | |
O9 | 0.40486 (12) | 0.7722 (2) | 0.10943 (9) | 0.0554 (6) | |
O10 | 0.40428 (11) | 0.53707 (18) | 0.25765 (10) | 0.0492 (6) | |
O11 | 0.09514 (12) | 0.1332 (2) | 0.95002 (13) | 0.0701 (8) | |
O12 | 0.27831 (15) | 0.0082 (2) | 1.06974 (11) | 0.0703 (8) | |
O13 | 0.28943 (12) | 0.2881 (2) | 0.94823 (11) | 0.0555 (6) | |
O14 | 0.24920 (18) | −0.0636 (3) | 0.88265 (13) | 0.0971 (12) | |
P1 | 0.14487 (3) | 0.78514 (5) | 0.15180 (3) | 0.02196 (13) | |
P2 | 0.13585 (3) | 0.67810 (5) | 0.06516 (2) | 0.02233 (14) | |
P3 | 0.65869 (3) | 0.46497 (5) | 0.14979 (2) | 0.01982 (13) | |
P4 | 0.57780 (3) | 0.33814 (5) | 0.16712 (2) | 0.02187 (13) | |
H1 | 0.1107 (15) | 0.931 (3) | 0.1765 (11) | 0.046 (10)* | |
H3 | 0.6629 (13) | 0.603 (2) | 0.0999 (11) | 0.040 (9)* | |
C63 | 0.46917 (16) | 0.0090 (4) | 0.02383 (17) | 0.0476 (16)* | 0.5 |
C64 | 0.52811 (19) | −0.0277 (3) | 0.04918 (13) | 0.0308 (12)* | 0.5 |
H64 | 0.5381 | −0.0448 | 0.0876 | 0.037* | 0.5 |
C65 | 0.57243 (14) | −0.0394 (4) | 0.0184 (2) | 0.0521 (17)* | 0.5 |
H65 | 0.6127 | −0.0644 | 0.0357 | 0.062* | 0.5 |
C66 | 0.55781 (19) | −0.0143 (4) | −0.03781 (19) | 0.0560 (19)* | 0.5 |
H66 | 0.5881 | −0.0223 | −0.0589 | 0.067* | 0.5 |
C67 | 0.4989 (2) | 0.0223 (4) | −0.06317 (13) | 0.0567 (18)* | 0.5 |
H67 | 0.4889 | 0.0394 | −0.1016 | 0.068* | 0.5 |
C68 | 0.45455 (15) | 0.0340 (4) | −0.03235 (17) | 0.0410 (14)* | 0.5 |
H68 | 0.4143 | 0.0591 | −0.0497 | 0.049* | 0.5 |
C69 | 0.4213 (4) | 0.0175 (8) | 0.0563 (4) | 0.073 (2)* | 0.5 |
H69A | 0.3827 | 0.0444 | 0.0325 | 0.110* | 0.5 |
H69B | 0.4136 | −0.0507 | 0.0703 | 0.110* | 0.5 |
H69C | 0.4361 | 0.0644 | 0.0877 | 0.110* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0331 (15) | 0.0352 (16) | 0.0358 (15) | −0.0044 (13) | 0.0071 (12) | −0.0001 (13) |
C2 | 0.0273 (14) | 0.0455 (18) | 0.0386 (16) | −0.0011 (13) | 0.0099 (13) | −0.0077 (14) |
C3 | 0.0261 (14) | 0.0319 (16) | 0.0515 (18) | 0.0030 (12) | −0.0016 (13) | −0.0017 (14) |
C4 | 0.0578 (19) | 0.0275 (15) | 0.0358 (15) | 0.0094 (14) | 0.0211 (14) | 0.0036 (12) |
C5 | 0.103 (3) | 0.0238 (17) | 0.064 (2) | −0.0030 (18) | 0.040 (2) | 0.0042 (16) |
C6 | 0.062 (2) | 0.063 (2) | 0.0479 (19) | 0.0244 (19) | 0.0146 (17) | 0.0098 (18) |
C7 | 0.0313 (14) | 0.0300 (15) | 0.0259 (13) | 0.0053 (11) | 0.0062 (11) | −0.0057 (11) |
C8 | 0.0430 (16) | 0.0257 (15) | 0.0365 (15) | 0.0071 (12) | 0.0114 (13) | 0.0033 (12) |
C9 | 0.059 (2) | 0.0366 (17) | 0.0432 (18) | 0.0176 (15) | 0.0215 (15) | 0.0124 (14) |
C10 | 0.068 (2) | 0.054 (2) | 0.0285 (16) | 0.0254 (18) | 0.0115 (15) | 0.0094 (15) |
C11 | 0.060 (2) | 0.052 (2) | 0.0280 (15) | 0.0149 (17) | 0.0038 (14) | −0.0061 (14) |
C12 | 0.0458 (17) | 0.0331 (16) | 0.0315 (15) | 0.0026 (13) | 0.0056 (13) | −0.0034 (12) |
C13 | 0.0241 (12) | 0.0321 (14) | 0.0225 (12) | 0.0157 (11) | 0.0152 (10) | 0.0105 (11) |
C14 | 0.0346 (16) | 0.0487 (19) | 0.0525 (19) | 0.0037 (14) | 0.0228 (14) | −0.0057 (15) |
C15 | 0.0276 (15) | 0.0387 (17) | 0.061 (2) | −0.0103 (13) | 0.0125 (14) | −0.0064 (15) |
C16 | 0.0299 (13) | 0.0203 (13) | 0.0244 (13) | 0.0029 (10) | 0.0074 (10) | −0.0026 (10) |
C17 | 0.0325 (14) | 0.0262 (14) | 0.0280 (13) | 0.0012 (11) | 0.0107 (11) | −0.0032 (11) |
C18 | 0.0467 (17) | 0.0284 (15) | 0.0294 (14) | 0.0079 (12) | 0.0156 (13) | 0.0052 (12) |
C19 | 0.0421 (16) | 0.0413 (17) | 0.0254 (14) | 0.0169 (14) | 0.0051 (12) | −0.0010 (13) |
C20 | 0.0347 (15) | 0.0440 (18) | 0.0341 (15) | 0.0054 (13) | −0.0013 (12) | −0.0081 (13) |
C21 | 0.0358 (15) | 0.0302 (15) | 0.0305 (14) | −0.0014 (12) | 0.0038 (12) | −0.0034 (12) |
C22 | 0.0263 (12) | 0.0168 (12) | 0.0266 (13) | −0.0023 (10) | 0.0035 (10) | −0.0057 (10) |
C23 | 0.0431 (16) | 0.0297 (15) | 0.0260 (13) | 0.0050 (12) | 0.0086 (12) | −0.0016 (11) |
C24 | 0.058 (2) | 0.0323 (16) | 0.0341 (16) | 0.0108 (14) | 0.0126 (14) | −0.0070 (13) |
C25 | 0.0562 (19) | 0.0223 (15) | 0.0483 (18) | 0.0065 (13) | 0.0137 (15) | −0.0055 (13) |
C26 | 0.0497 (18) | 0.0220 (14) | 0.0435 (17) | 0.0017 (13) | 0.0141 (14) | 0.0037 (12) |
C27 | 0.0370 (15) | 0.0225 (14) | 0.0316 (14) | −0.0025 (11) | 0.0111 (11) | −0.0017 (11) |
C28 | 0.0402 (16) | 0.0252 (14) | 0.0274 (13) | −0.0006 (12) | 0.0088 (12) | 0.0016 (11) |
C29 | 0.0309 (14) | 0.0301 (15) | 0.0217 (12) | 0.0052 (12) | 0.0057 (10) | 0.0010 (11) |
C30 | 0.0425 (16) | 0.0292 (15) | 0.0267 (14) | 0.0040 (13) | 0.0045 (12) | −0.0010 (12) |
C31 | 0.0271 (13) | 0.0229 (13) | 0.0284 (13) | 0.0072 (10) | 0.0085 (10) | 0.0048 (11) |
C32 | 0.0358 (16) | 0.0500 (19) | 0.0314 (15) | 0.0119 (14) | 0.0035 (12) | 0.0052 (14) |
C33 | 0.0496 (18) | 0.0221 (14) | 0.0458 (17) | 0.0091 (13) | 0.0182 (14) | 0.0039 (13) |
C34 | 0.0259 (13) | 0.0280 (14) | 0.0174 (11) | 0.0044 (10) | 0.0050 (10) | 0.0019 (10) |
C35 | 0.0336 (14) | 0.0312 (15) | 0.0309 (14) | 0.0070 (12) | 0.0074 (11) | 0.0018 (12) |
C36 | 0.0386 (16) | 0.0489 (19) | 0.0332 (15) | 0.0211 (15) | 0.0102 (12) | 0.0004 (14) |
C37 | 0.0260 (14) | 0.065 (2) | 0.0319 (15) | 0.0107 (14) | 0.0091 (12) | 0.0035 (14) |
C38 | 0.0265 (14) | 0.055 (2) | 0.0332 (15) | −0.0051 (13) | 0.0074 (11) | 0.0022 (14) |
C39 | 0.0317 (14) | 0.0311 (15) | 0.0262 (13) | 0.0006 (11) | 0.0073 (11) | 0.0001 (11) |
C40 | 0.0323 (14) | 0.0279 (14) | 0.0193 (12) | −0.0003 (11) | 0.0047 (10) | −0.0017 (10) |
C41 | 0.0565 (19) | 0.0288 (15) | 0.0279 (14) | −0.0056 (13) | 0.0134 (13) | −0.0059 (12) |
C42 | 0.0522 (18) | 0.0325 (16) | 0.0209 (13) | −0.0021 (13) | 0.0126 (12) | 0.0000 (11) |
C43 | 0.0389 (15) | 0.0214 (13) | 0.0212 (12) | −0.0057 (11) | 0.0046 (11) | 0.0000 (10) |
C44 | 0.0478 (17) | 0.0311 (16) | 0.0316 (14) | −0.0071 (13) | 0.0121 (13) | 0.0026 (12) |
C45 | 0.065 (2) | 0.0358 (18) | 0.0384 (17) | −0.0171 (16) | 0.0149 (15) | 0.0074 (14) |
C46 | 0.080 (2) | 0.0210 (15) | 0.0310 (15) | −0.0076 (16) | 0.0035 (15) | 0.0036 (12) |
C47 | 0.060 (2) | 0.0227 (15) | 0.0348 (15) | 0.0058 (14) | 0.0037 (14) | 0.0009 (12) |
C48 | 0.0438 (16) | 0.0224 (14) | 0.0315 (14) | −0.0005 (12) | 0.0052 (12) | 0.0007 (11) |
C49 | 0.0276 (13) | 0.0278 (14) | 0.0244 (12) | −0.0022 (11) | 0.0083 (10) | 0.0028 (11) |
C50 | 0.0294 (14) | 0.0310 (15) | 0.0299 (14) | −0.0017 (11) | 0.0098 (11) | 0.0022 (12) |
C51 | 0.0325 (15) | 0.0393 (17) | 0.0399 (16) | 0.0047 (13) | 0.0120 (12) | 0.0091 (13) |
C52 | 0.0286 (14) | 0.054 (2) | 0.0374 (16) | 0.0003 (14) | 0.0063 (12) | 0.0116 (14) |
C53 | 0.0371 (16) | 0.0511 (19) | 0.0285 (14) | −0.0126 (14) | 0.0034 (12) | 0.0005 (14) |
C54 | 0.0337 (15) | 0.0361 (16) | 0.0295 (14) | −0.0038 (12) | 0.0074 (11) | −0.0001 (12) |
C55 | 0.0498 (18) | 0.0395 (18) | 0.0292 (15) | 0.0122 (14) | 0.0060 (13) | 0.0030 (14) |
C56 | 0.0402 (17) | 0.0268 (14) | 0.0284 (14) | −0.0024 (12) | 0.0094 (12) | −0.0023 (11) |
C57 | 0.0342 (15) | 0.0372 (16) | 0.0335 (16) | 0.0019 (12) | 0.0084 (12) | 0.0022 (13) |
C58 | 0.0326 (14) | 0.0422 (18) | 0.0272 (14) | −0.0020 (13) | 0.0085 (11) | 0.0028 (13) |
C59 | 0.046 (2) | 0.0408 (19) | 0.054 (2) | 0.0012 (15) | 0.0078 (15) | −0.0026 (15) |
C60 | 0.057 (2) | 0.0323 (17) | 0.0434 (19) | −0.0089 (15) | 0.0130 (15) | −0.0044 (14) |
C61 | 0.0395 (16) | 0.052 (2) | 0.0347 (16) | 0.0096 (15) | 0.0146 (13) | 0.0109 (15) |
C62 | 0.058 (2) | 0.072 (3) | 0.0418 (19) | 0.015 (2) | 0.0039 (16) | −0.0135 (19) |
Co1 | 0.0222 (2) | 0.0224 (2) | 0.0275 (2) | −0.00050 (16) | 0.00468 (17) | −0.00343 (17) |
Co2 | 0.0264 (2) | 0.0172 (2) | 0.01802 (19) | 0.00094 (16) | 0.00476 (15) | 0.00057 (15) |
Co3 | 0.0298 (2) | 0.0261 (2) | 0.0237 (2) | 0.00174 (17) | 0.00678 (17) | 0.00064 (17) |
Co4 | 0.0363 (3) | 0.0368 (3) | 0.0357 (3) | 0.0031 (2) | 0.0083 (2) | −0.0046 (2) |
N1 | 0.0434 (13) | 0.0199 (12) | 0.0313 (12) | 0.0052 (10) | 0.0147 (10) | −0.0033 (9) |
N2 | 0.0260 (11) | 0.0217 (11) | 0.0251 (11) | 0.0002 (9) | 0.0061 (9) | −0.0036 (9) |
N3 | 0.0268 (11) | 0.0207 (11) | 0.0249 (11) | 0.0044 (9) | 0.0105 (9) | 0.0044 (9) |
N4 | 0.0285 (11) | 0.0184 (10) | 0.0191 (10) | −0.0001 (8) | 0.0067 (8) | −0.0001 (8) |
O1 | 0.0507 (14) | 0.0445 (14) | 0.0541 (14) | −0.0169 (11) | 0.0014 (11) | −0.0130 (11) |
O2 | 0.0473 (14) | 0.094 (2) | 0.0504 (14) | −0.0018 (13) | 0.0283 (12) | −0.0065 (14) |
O3 | 0.0497 (14) | 0.0401 (14) | 0.097 (2) | 0.0078 (12) | −0.0137 (14) | 0.0197 (14) |
O4 | 0.0544 (13) | 0.0510 (14) | 0.0409 (12) | 0.0026 (11) | 0.0290 (11) | 0.0010 (10) |
O5 | 0.0402 (11) | 0.0326 (11) | 0.0392 (11) | −0.0102 (9) | 0.0055 (9) | −0.0072 (9) |
O6 | 0.0651 (16) | 0.0451 (14) | 0.0465 (13) | 0.0258 (12) | −0.0048 (12) | 0.0053 (11) |
O7 | 0.093 (2) | 0.0541 (16) | 0.0451 (14) | 0.0320 (15) | 0.0130 (13) | −0.0114 (12) |
O8 | 0.0317 (12) | 0.0534 (14) | 0.0494 (13) | −0.0013 (10) | 0.0058 (10) | −0.0061 (11) |
O9 | 0.0607 (15) | 0.0723 (18) | 0.0299 (12) | 0.0053 (13) | 0.0044 (11) | 0.0079 (11) |
O10 | 0.0568 (14) | 0.0454 (14) | 0.0480 (13) | −0.0147 (11) | 0.0176 (11) | 0.0109 (11) |
O11 | 0.0411 (15) | 0.0700 (19) | 0.097 (2) | 0.0080 (13) | 0.0119 (14) | 0.0024 (16) |
O12 | 0.105 (2) | 0.0587 (17) | 0.0426 (15) | −0.0054 (16) | 0.0096 (14) | 0.0110 (13) |
O13 | 0.0536 (14) | 0.0556 (16) | 0.0618 (16) | −0.0015 (12) | 0.0226 (12) | 0.0213 (13) |
O14 | 0.112 (3) | 0.112 (3) | 0.0626 (19) | 0.035 (2) | 0.0114 (18) | −0.043 (2) |
P1 | 0.0280 (3) | 0.0161 (3) | 0.0218 (3) | −0.0006 (2) | 0.0061 (2) | −0.0033 (2) |
P2 | 0.0286 (3) | 0.0172 (3) | 0.0208 (3) | −0.0005 (2) | 0.0051 (2) | −0.0027 (2) |
P3 | 0.0231 (3) | 0.0169 (3) | 0.0196 (3) | 0.0016 (2) | 0.0055 (2) | 0.0007 (2) |
P4 | 0.0270 (3) | 0.0187 (3) | 0.0202 (3) | −0.0010 (2) | 0.0062 (2) | 0.0004 (2) |
C1—O1 | 1.142 (4) | C37—C38 | 1.378 (5) |
C1—Co1 | 1.782 (3) | C37—H37 | 0.9500 |
C2—O2 | 1.138 (4) | C38—C39 | 1.387 (4) |
C2—Co1 | 1.797 (3) | C38—H38 | 0.9500 |
C3—O3 | 1.134 (4) | C39—H39 | 0.9500 |
C3—Co1 | 1.821 (3) | C40—N4 | 1.505 (3) |
C4—N1 | 1.469 (4) | C40—C41 | 1.515 (4) |
C4—C6 | 1.513 (5) | C40—C42 | 1.521 (4) |
C4—C5 | 1.523 (5) | C40—H40 | 1.0000 |
C4—H4 | 1.0000 | C41—H41A | 0.9800 |
C5—H5A | 0.9800 | C41—H41B | 0.9800 |
C5—H5B | 0.9800 | C41—H41C | 0.9800 |
C5—H5C | 0.9800 | C42—H42A | 0.9800 |
C6—H6A | 0.9800 | C42—H42B | 0.9800 |
C6—H6B | 0.9800 | C42—H42C | 0.9800 |
C6—H6C | 0.9800 | C43—C44 | 1.395 (4) |
C7—C12 | 1.386 (4) | C43—C48 | 1.396 (4) |
C7—C8 | 1.397 (4) | C43—P4 | 1.813 (3) |
C7—P1 | 1.801 (3) | C44—C45 | 1.394 (4) |
C8—C9 | 1.382 (4) | C44—H44 | 0.9500 |
C8—H8 | 0.9500 | C45—C46 | 1.379 (5) |
C9—C10 | 1.377 (5) | C45—H45 | 0.9500 |
C9—H9 | 0.9500 | C46—C47 | 1.376 (5) |
C10—C11 | 1.374 (5) | C46—H46 | 0.9500 |
C10—H10 | 0.9500 | C47—C48 | 1.384 (4) |
C11—C12 | 1.388 (4) | C47—H47 | 0.9500 |
C11—H11 | 0.9500 | C48—H48 | 0.9500 |
C12—H12 | 0.9500 | C49—C50 | 1.389 (4) |
C13—N2 | 1.446 (3) | C49—C54 | 1.402 (4) |
C13—C14 | 1.538 (3) | C49—P4 | 1.816 (3) |
C13—C15 | 1.546 (3) | C50—C51 | 1.390 (4) |
C13—H13 | 1.0000 | C50—H50 | 0.9500 |
C14—H14A | 0.9800 | C51—C52 | 1.379 (5) |
C14—H14B | 0.9800 | C51—H51 | 0.9500 |
C14—H14C | 0.9800 | C52—C53 | 1.382 (5) |
C15—H15A | 0.9800 | C52—H52 | 0.9500 |
C15—H15B | 0.9800 | C53—C54 | 1.386 (4) |
C15—H15C | 0.9800 | C53—H53 | 0.9500 |
C16—C21 | 1.395 (4) | C54—H54 | 0.9500 |
C16—C17 | 1.398 (4) | C55—O7 | 1.149 (4) |
C16—P2 | 1.814 (3) | C55—Co3 | 1.762 (3) |
C17—C18 | 1.389 (4) | C56—O8 | 1.152 (4) |
C17—H17 | 0.9500 | C56—Co3 | 1.761 (3) |
C18—C19 | 1.379 (4) | C57—O9 | 1.149 (4) |
C18—H18 | 0.9500 | C57—Co3 | 1.770 (3) |
C19—C20 | 1.379 (5) | C58—O10 | 1.155 (4) |
C19—H19 | 0.9500 | C58—Co3 | 1.760 (3) |
C20—C21 | 1.382 (4) | C59—O11 | 1.158 (4) |
C20—H20 | 0.9500 | C59—Co4 | 1.766 (4) |
C21—H21 | 0.9500 | C60—O12 | 1.156 (4) |
C22—C23 | 1.391 (4) | C60—Co4 | 1.755 (3) |
C22—C27 | 1.397 (4) | C61—O13 | 1.161 (4) |
C22—P2 | 1.802 (3) | C61—Co4 | 1.754 (4) |
C23—C24 | 1.387 (4) | C62—O14 | 1.159 (5) |
C23—H23 | 0.9500 | C62—Co4 | 1.761 (4) |
C24—C25 | 1.382 (3) | Co1—P2 | 2.1800 (7) |
C24—H24 | 0.9500 | Co1—P1 | 2.1948 (7) |
C25—C26 | 1.383 (3) | Co2—P3 | 2.1884 (7) |
C25—H25 | 0.9500 | Co2—P4 | 2.1971 (7) |
C26—C27 | 1.377 (4) | N1—P1 | 1.625 (2) |
C26—H26 | 0.9500 | N1—H1 | 0.865 (10) |
C27—H27 | 0.9500 | N2—P2 | 1.695 (2) |
C28—O4 | 1.137 (3) | N2—P1 | 1.698 (2) |
C28—Co2 | 1.797 (3) | N3—P3 | 1.632 (2) |
C29—O5 | 1.136 (3) | N3—H3 | 0.862 (10) |
C29—Co2 | 1.793 (3) | N4—P3 | 1.695 (2) |
C30—O6 | 1.131 (4) | N4—P4 | 1.702 (2) |
C30—Co2 | 1.832 (3) | P1—P2 | 2.5246 (8) |
C31—N3 | 1.478 (3) | P3—P4 | 2.5445 (9) |
C31—C33 | 1.515 (4) | C63—C64 | 1.3900 |
C31—C32 | 1.521 (4) | C63—C68 | 1.3900 |
C31—H31 | 1.0000 | C63—C69 | 1.482 (10) |
C32—H32A | 0.9800 | C64—C65 | 1.3900 |
C32—H32B | 0.9800 | C64—H64 | 0.9500 |
C32—H32C | 0.9800 | C65—C66 | 1.3900 |
C33—H33A | 0.9800 | C65—H65 | 0.9500 |
C33—H33B | 0.9800 | C66—C67 | 1.3900 |
C33—H33C | 0.9800 | C66—H66 | 0.9500 |
C34—C39 | 1.394 (4) | C67—C68 | 1.3900 |
C34—C35 | 1.396 (4) | C67—H67 | 0.9500 |
C34—P3 | 1.804 (3) | C68—H68 | 0.9500 |
C35—C36 | 1.394 (4) | C69—H69A | 0.9800 |
C35—H35 | 0.9500 | C69—H69B | 0.9800 |
C36—C37 | 1.374 (5) | C69—H69C | 0.9800 |
C36—H36 | 0.9500 | ||
O1—C1—Co1 | 175.7 (3) | C44—C43—C48 | 119.5 (3) |
O2—C2—Co1 | 178.2 (3) | C44—C43—P4 | 119.3 (2) |
O3—C3—Co1 | 177.9 (3) | C48—C43—P4 | 121.0 (2) |
N1—C4—C6 | 111.0 (3) | C45—C44—C43 | 119.6 (3) |
N1—C4—C5 | 109.6 (3) | C45—C44—H44 | 120.2 |
C6—C4—C5 | 112.4 (3) | C43—C44—H44 | 120.2 |
N1—C4—H4 | 107.9 | C46—C45—C44 | 120.2 (3) |
C6—C4—H4 | 107.9 | C46—C45—H45 | 119.9 |
C5—C4—H4 | 107.9 | C44—C45—H45 | 119.9 |
C4—C5—H5A | 109.5 | C47—C46—C45 | 120.2 (3) |
C4—C5—H5B | 109.5 | C47—C46—H46 | 119.9 |
H5A—C5—H5B | 109.5 | C45—C46—H46 | 119.9 |
C4—C5—H5C | 109.5 | C46—C47—C48 | 120.5 (3) |
H5A—C5—H5C | 109.5 | C46—C47—H47 | 119.8 |
H5B—C5—H5C | 109.5 | C48—C47—H47 | 119.8 |
C4—C6—H6A | 109.5 | C47—C48—C43 | 120.0 (3) |
C4—C6—H6B | 109.5 | C47—C48—H48 | 120.0 |
H6A—C6—H6B | 109.5 | C43—C48—H48 | 120.0 |
C4—C6—H6C | 109.5 | C50—C49—C54 | 119.5 (3) |
H6A—C6—H6C | 109.5 | C50—C49—P4 | 121.7 (2) |
H6B—C6—H6C | 109.5 | C54—C49—P4 | 118.6 (2) |
C12—C7—C8 | 118.9 (3) | C49—C50—C51 | 120.0 (3) |
C12—C7—P1 | 119.8 (2) | C49—C50—H50 | 120.0 |
C8—C7—P1 | 121.2 (2) | C51—C50—H50 | 120.0 |
C9—C8—C7 | 120.4 (3) | C52—C51—C50 | 120.2 (3) |
C9—C8—H8 | 119.8 | C52—C51—H51 | 119.9 |
C7—C8—H8 | 119.8 | C50—C51—H51 | 119.9 |
C10—C9—C8 | 120.1 (3) | C51—C52—C53 | 120.2 (3) |
C10—C9—H9 | 120.0 | C51—C52—H52 | 119.9 |
C8—C9—H9 | 120.0 | C53—C52—H52 | 119.9 |
C11—C10—C9 | 120.1 (3) | C52—C53—C54 | 120.3 (3) |
C11—C10—H10 | 119.9 | C52—C53—H53 | 119.8 |
C9—C10—H10 | 119.9 | C54—C53—H53 | 119.8 |
C10—C11—C12 | 120.3 (3) | C53—C54—C49 | 119.7 (3) |
C10—C11—H11 | 119.8 | C53—C54—H54 | 120.1 |
C12—C11—H11 | 119.8 | C49—C54—H54 | 120.1 |
C7—C12—C11 | 120.2 (3) | O7—C55—Co3 | 178.1 (3) |
C7—C12—H12 | 119.9 | O8—C56—Co3 | 177.4 (3) |
C11—C12—H12 | 119.9 | O9—C57—Co3 | 178.7 (3) |
N2—C13—C14 | 114.7 (2) | O10—C58—Co3 | 177.0 (3) |
N2—C13—C15 | 111.11 (19) | O11—C59—Co4 | 177.8 (3) |
C14—C13—C15 | 107.2 (2) | O12—C60—Co4 | 178.9 (3) |
N2—C13—H13 | 107.9 | O13—C61—Co4 | 177.5 (3) |
C14—C13—H13 | 107.9 | O14—C62—Co4 | 177.3 (4) |
C15—C13—H13 | 107.9 | C1—Co1—C2 | 95.41 (14) |
C13—C14—H14A | 109.5 | C1—Co1—C3 | 102.23 (14) |
C13—C14—H14B | 109.5 | C2—Co1—C3 | 108.51 (15) |
H14A—C14—H14B | 109.5 | C1—Co1—P2 | 152.54 (10) |
C13—C14—H14C | 109.5 | C2—Co1—P2 | 93.17 (10) |
H14A—C14—H14C | 109.5 | C3—Co1—P2 | 99.65 (9) |
H14B—C14—H14C | 109.5 | C1—Co1—P1 | 88.11 (10) |
C13—C15—H15A | 109.5 | C2—Co1—P1 | 145.53 (10) |
C13—C15—H15B | 109.5 | C3—Co1—P1 | 104.15 (10) |
H15A—C15—H15B | 109.5 | P2—Co1—P1 | 70.49 (3) |
C13—C15—H15C | 109.5 | C29—Co2—C28 | 93.93 (12) |
H15A—C15—H15C | 109.5 | C29—Co2—C30 | 101.01 (12) |
H15B—C15—H15C | 109.5 | C28—Co2—C30 | 106.21 (13) |
C21—C16—C17 | 118.6 (2) | C29—Co2—P3 | 86.94 (8) |
C21—C16—P2 | 120.0 (2) | C28—Co2—P3 | 145.58 (9) |
C17—C16—P2 | 121.3 (2) | C30—Co2—P3 | 107.38 (9) |
C18—C17—C16 | 120.1 (3) | C29—Co2—P4 | 153.27 (9) |
C18—C17—H17 | 120.0 | C28—Co2—P4 | 96.14 (9) |
C16—C17—H17 | 120.0 | C30—Co2—P4 | 99.84 (9) |
C19—C18—C17 | 120.4 (3) | P3—Co2—P4 | 70.93 (2) |
C19—C18—H18 | 119.8 | C58—Co3—C56 | 105.75 (13) |
C17—C18—H18 | 119.8 | C58—Co3—C55 | 111.89 (14) |
C20—C19—C18 | 119.9 (3) | C56—Co3—C55 | 108.22 (14) |
C20—C19—H19 | 120.1 | C58—Co3—C57 | 110.19 (14) |
C18—C19—H19 | 120.1 | C56—Co3—C57 | 110.86 (13) |
C19—C20—C21 | 120.3 (3) | C55—Co3—C57 | 109.85 (14) |
C19—C20—H20 | 119.9 | C61—Co4—C60 | 110.15 (15) |
C21—C20—H20 | 119.9 | C61—Co4—C62 | 111.04 (18) |
C20—C21—C16 | 120.7 (3) | C60—Co4—C62 | 106.30 (17) |
C20—C21—H21 | 119.7 | C61—Co4—C59 | 109.74 (15) |
C16—C21—H21 | 119.7 | C60—Co4—C59 | 107.83 (17) |
C23—C22—C27 | 119.7 (2) | C62—Co4—C59 | 111.68 (17) |
C23—C22—P2 | 118.6 (2) | C4—N1—P1 | 125.26 (19) |
C27—C22—P2 | 120.70 (19) | C4—N1—H1 | 114 (2) |
C24—C23—C22 | 119.8 (3) | P1—N1—H1 | 119 (2) |
C24—C23—H23 | 120.1 | C13—N2—P2 | 128.44 (16) |
C22—C23—H23 | 120.1 | C13—N2—P1 | 129.22 (16) |
C25—C24—C23 | 120.2 (3) | P2—N2—P1 | 96.18 (11) |
C25—C24—H24 | 119.9 | C31—N3—P3 | 126.15 (17) |
C23—C24—H24 | 119.9 | C31—N3—H3 | 113 (2) |
C24—C25—C26 | 119.9 (3) | P3—N3—H3 | 120 (2) |
C24—C25—H25 | 120.0 | C40—N4—P3 | 130.76 (17) |
C26—C25—H25 | 120.0 | C40—N4—P4 | 126.89 (17) |
C27—C26—C25 | 120.6 (3) | P3—N4—P4 | 97.02 (10) |
C27—C26—H26 | 119.7 | N1—P1—N2 | 117.14 (12) |
C25—C26—H26 | 119.7 | N1—P1—C7 | 102.57 (12) |
C26—C27—C22 | 119.7 (3) | N2—P1—C7 | 108.97 (12) |
C26—C27—H27 | 120.1 | N1—P1—Co1 | 116.72 (9) |
C22—C27—H27 | 120.1 | N2—P1—Co1 | 95.18 (8) |
O4—C28—Co2 | 177.9 (3) | C7—P1—Co1 | 116.75 (9) |
O5—C29—Co2 | 175.8 (2) | N1—P1—P2 | 123.42 (9) |
O6—C30—Co2 | 177.8 (3) | C7—P1—P2 | 132.52 (9) |
N3—C31—C33 | 109.4 (2) | Co1—P1—P2 | 54.48 (2) |
N3—C31—C32 | 111.0 (2) | N2—P2—C22 | 111.46 (11) |
C33—C31—C32 | 111.8 (2) | N2—P2—C16 | 109.52 (11) |
N3—C31—H31 | 108.2 | C22—P2—C16 | 104.67 (12) |
C33—C31—H31 | 108.2 | N2—P2—Co1 | 95.80 (8) |
C32—C31—H31 | 108.2 | C22—P2—Co1 | 112.73 (8) |
C31—C32—H32A | 109.5 | C16—P2—Co1 | 122.45 (9) |
C31—C32—H32B | 109.5 | N2—P2—P1 | 41.95 (7) |
H32A—C32—H32B | 109.5 | C22—P2—P1 | 132.29 (9) |
C31—C32—H32C | 109.5 | C16—P2—P1 | 120.68 (8) |
H32A—C32—H32C | 109.5 | Co1—P2—P1 | 55.03 (2) |
H32B—C32—H32C | 109.5 | N3—P3—N4 | 116.68 (11) |
C31—C33—H33A | 109.5 | N3—P3—C34 | 101.84 (11) |
C31—C33—H33B | 109.5 | N4—P3—C34 | 108.01 (11) |
H33A—C33—H33B | 109.5 | N3—P3—Co2 | 116.83 (8) |
C31—C33—H33C | 109.5 | N4—P3—Co2 | 95.29 (7) |
H33A—C33—H33C | 109.5 | C34—P3—Co2 | 118.70 (8) |
H33B—C33—H33C | 109.5 | N3—P3—P4 | 123.80 (8) |
C39—C34—C35 | 119.2 (2) | C34—P3—P4 | 132.22 (9) |
C39—C34—P3 | 120.7 (2) | Co2—P3—P4 | 54.69 (2) |
C35—C34—P3 | 120.0 (2) | N4—P4—C43 | 111.06 (11) |
C36—C35—C34 | 119.9 (3) | N4—P4—C49 | 106.85 (11) |
C36—C35—H35 | 120.0 | C43—P4—C49 | 104.25 (12) |
C34—C35—H35 | 120.0 | N4—P4—Co2 | 94.80 (7) |
C37—C36—C35 | 120.2 (3) | C43—P4—Co2 | 115.86 (9) |
C37—C36—H36 | 119.9 | C49—P4—Co2 | 123.18 (9) |
C35—C36—H36 | 119.9 | C43—P4—P3 | 132.93 (9) |
C36—C37—C38 | 120.2 (3) | C49—P4—P3 | 119.05 (9) |
C36—C37—H37 | 119.9 | Co2—P4—P3 | 54.38 (2) |
C38—C37—H37 | 119.9 | C64—C63—C68 | 120.0 |
C37—C38—C39 | 120.5 (3) | C64—C63—C69 | 119.8 (5) |
C37—C38—H38 | 119.8 | C68—C63—C69 | 120.2 (5) |
C39—C38—H38 | 119.8 | C65—C64—C63 | 120.0 |
C38—C39—C34 | 120.0 (3) | C65—C64—H64 | 120.0 |
C38—C39—H39 | 120.0 | C63—C64—H64 | 120.0 |
C34—C39—H39 | 120.0 | C64—C65—C66 | 120.0 |
N4—C40—C41 | 111.2 (2) | C64—C65—H65 | 120.0 |
N4—C40—C42 | 111.3 (2) | C66—C65—H65 | 120.0 |
C41—C40—C42 | 110.7 (2) | C67—C66—C65 | 120.0 |
N4—C40—H40 | 107.8 | C67—C66—H66 | 120.0 |
C41—C40—H40 | 107.8 | C65—C66—H66 | 120.0 |
C42—C40—H40 | 107.8 | C68—C67—C66 | 120.0 |
C40—C41—H41A | 109.5 | C68—C67—H67 | 120.0 |
C40—C41—H41B | 109.5 | C66—C67—H67 | 120.0 |
H41A—C41—H41B | 109.5 | C67—C68—C63 | 120.0 |
C40—C41—H41C | 109.5 | C67—C68—H68 | 120.0 |
H41A—C41—H41C | 109.5 | C63—C68—H68 | 120.0 |
H41B—C41—H41C | 109.5 | C63—C69—H69A | 109.5 |
C40—C42—H42A | 109.5 | C63—C69—H69B | 109.5 |
C40—C42—H42B | 109.5 | H69A—C69—H69B | 109.5 |
H42A—C42—H42B | 109.5 | C63—C69—H69C | 109.5 |
C40—C42—H42C | 109.5 | H69A—C69—H69C | 109.5 |
H42A—C42—H42C | 109.5 | H69B—C69—H69C | 109.5 |
H42B—C42—H42C | 109.5 | ||
C12—C7—C8—C9 | 1.2 (4) | C8—C7—P1—Co1 | −86.4 (2) |
P1—C7—C8—C9 | 176.7 (2) | C12—C7—P1—P2 | 154.23 (19) |
C7—C8—C9—C10 | −0.8 (5) | C8—C7—P1—P2 | −21.2 (3) |
C8—C9—C10—C11 | 0.0 (5) | C13—N2—P2—C22 | −76.0 (2) |
C9—C10—C11—C12 | 0.3 (5) | P1—N2—P2—C22 | 130.11 (11) |
C8—C7—C12—C11 | −0.9 (4) | C13—N2—P2—C16 | 39.3 (2) |
P1—C7—C12—C11 | −176.5 (2) | P1—N2—P2—C16 | −114.55 (12) |
C10—C11—C12—C7 | 0.1 (5) | C13—N2—P2—Co1 | 166.8 (2) |
C21—C16—C17—C18 | −0.8 (4) | P1—N2—P2—Co1 | 12.91 (9) |
P2—C16—C17—C18 | −179.6 (2) | C13—N2—P2—P1 | 153.9 (3) |
C16—C17—C18—C19 | 0.9 (4) | C23—C22—P2—N2 | 160.8 (2) |
C17—C18—C19—C20 | −0.2 (4) | C27—C22—P2—N2 | −30.9 (2) |
C18—C19—C20—C21 | −0.7 (4) | C23—C22—P2—C16 | 42.6 (2) |
C19—C20—C21—C16 | 0.8 (4) | C27—C22—P2—C16 | −149.2 (2) |
C17—C16—C21—C20 | −0.1 (4) | C23—C22—P2—Co1 | −92.8 (2) |
P2—C16—C21—C20 | 178.8 (2) | C27—C22—P2—Co1 | 75.5 (2) |
C27—C22—C23—C24 | 0.5 (4) | C23—C22—P2—P1 | −155.44 (17) |
P2—C22—C23—C24 | 168.8 (2) | C27—C22—P2—P1 | 12.8 (3) |
C22—C23—C24—C25 | 0.0 (5) | C21—C16—P2—N2 | −74.9 (2) |
C23—C24—C25—C26 | 0.0 (5) | C17—C16—P2—N2 | 104.0 (2) |
C24—C25—C26—C27 | −0.6 (5) | C21—C16—P2—C22 | 44.7 (2) |
C25—C26—C27—C22 | 1.0 (5) | C17—C16—P2—C22 | −136.5 (2) |
C23—C22—C27—C26 | −1.0 (4) | C21—C16—P2—Co1 | 174.48 (18) |
P2—C22—C27—C26 | −169.1 (2) | C17—C16—P2—Co1 | −6.7 (3) |
C39—C34—C35—C36 | −0.8 (4) | C21—C16—P2—P1 | −119.9 (2) |
P3—C34—C35—C36 | −176.6 (2) | C17—C16—P2—P1 | 59.0 (2) |
C34—C35—C36—C37 | 0.1 (4) | C31—N3—P3—N4 | 74.6 (2) |
C35—C36—C37—C38 | 0.4 (4) | C31—N3—P3—C34 | −168.1 (2) |
C36—C37—C38—C39 | −0.3 (4) | C31—N3—P3—Co2 | −37.1 (2) |
C37—C38—C39—C34 | −0.3 (4) | C31—N3—P3—P4 | 26.8 (2) |
C35—C34—C39—C38 | 0.9 (4) | C40—N4—P3—N3 | 42.9 (3) |
P3—C34—C39—C38 | 176.7 (2) | P4—N4—P3—N3 | −111.83 (11) |
C48—C43—C44—C45 | −1.0 (4) | C40—N4—P3—C34 | −71.0 (2) |
P4—C43—C44—C45 | −175.6 (2) | P4—N4—P3—C34 | 134.29 (11) |
C43—C44—C45—C46 | −0.2 (5) | C40—N4—P3—Co2 | 166.5 (2) |
C44—C45—C46—C47 | 0.7 (5) | P4—N4—P3—Co2 | 11.80 (9) |
C45—C46—C47—C48 | 0.0 (5) | C40—N4—P3—P4 | 154.8 (3) |
C46—C47—C48—C43 | −1.3 (4) | C39—C34—P3—N3 | 34.8 (2) |
C44—C43—C48—C47 | 1.8 (4) | C35—C34—P3—N3 | −149.4 (2) |
P4—C43—C48—C47 | 176.3 (2) | C39—C34—P3—N4 | 158.2 (2) |
C54—C49—C50—C51 | −0.9 (4) | C35—C34—P3—N4 | −26.0 (2) |
P4—C49—C50—C51 | 173.6 (2) | C39—C34—P3—Co2 | −95.0 (2) |
C49—C50—C51—C52 | 0.2 (4) | C35—C34—P3—Co2 | 80.8 (2) |
C50—C51—C52—C53 | 0.2 (4) | C39—C34—P3—P4 | −161.90 (16) |
C51—C52—C53—C54 | 0.3 (4) | C35—C34—P3—P4 | 13.9 (3) |
C52—C53—C54—C49 | −1.0 (4) | C40—N4—P4—C43 | 72.0 (2) |
C50—C49—C54—C53 | 1.4 (4) | P3—N4—P4—C43 | −131.83 (11) |
P4—C49—C54—C53 | −173.4 (2) | C40—N4—P4—C49 | −41.1 (2) |
C6—C4—N1—P1 | 94.1 (3) | P3—N4—P4—C49 | 115.07 (12) |
C5—C4—N1—P1 | −141.2 (3) | C40—N4—P4—Co2 | −167.91 (19) |
C14—C13—N2—P2 | −168.3 (2) | P3—N4—P4—Co2 | −11.74 (9) |
C15—C13—N2—P2 | 70.0 (3) | C40—N4—P4—P3 | −156.2 (3) |
C14—C13—N2—P1 | −22.7 (3) | C44—C43—P4—N4 | −152.1 (2) |
C15—C13—N2—P1 | −144.4 (2) | C48—C43—P4—N4 | 33.4 (2) |
C33—C31—N3—P3 | 135.5 (2) | C44—C43—P4—C49 | −37.4 (2) |
C32—C31—N3—P3 | −100.6 (3) | C48—C43—P4—C49 | 148.1 (2) |
C41—C40—N4—P3 | 137.6 (2) | C44—C43—P4—Co2 | 101.3 (2) |
C42—C40—N4—P3 | 13.7 (3) | C48—C43—P4—Co2 | −73.3 (2) |
C41—C40—N4—P4 | −74.4 (3) | C44—C43—P4—P3 | 165.62 (17) |
C42—C40—N4—P4 | 161.70 (19) | C48—C43—P4—P3 | −8.9 (3) |
C4—N1—P1—N2 | −71.6 (3) | C50—C49—P4—N4 | −101.6 (2) |
C4—N1—P1—C7 | 169.2 (2) | C54—C49—P4—N4 | 73.0 (2) |
C4—N1—P1—Co1 | 40.2 (3) | C50—C49—P4—C43 | 140.7 (2) |
C4—N1—P1—P2 | −23.2 (3) | C54—C49—P4—C43 | −44.6 (2) |
C13—N2—P1—N1 | −42.8 (3) | C50—C49—P4—Co2 | 6.0 (3) |
P2—N2—P1—N1 | 110.82 (13) | C54—C49—P4—Co2 | −179.38 (17) |
C13—N2—P1—C7 | 73.0 (2) | C50—C49—P4—P3 | −58.3 (2) |
P2—N2—P1—C7 | −133.40 (12) | C54—C49—P4—P3 | 116.3 (2) |
C13—N2—P1—Co1 | −166.4 (2) | C68—C63—C64—C65 | 0.0 |
P2—N2—P1—Co1 | −12.81 (9) | C69—C63—C64—C65 | 177.7 (6) |
C13—N2—P1—P2 | −153.6 (3) | C63—C64—C65—C66 | 0.0 |
C12—C7—P1—N1 | −39.8 (3) | C64—C65—C66—C67 | 0.0 |
C8—C7—P1—N1 | 144.7 (2) | C65—C66—C67—C68 | 0.0 |
C12—C7—P1—N2 | −164.6 (2) | C66—C67—C68—C63 | 0.0 |
C8—C7—P1—N2 | 19.9 (3) | C64—C63—C68—C67 | 0.0 |
C12—C7—P1—Co1 | 89.1 (2) | C69—C63—C68—C67 | −177.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O10i | 0.87 (1) | 2.22 (2) | 3.041 (3) | 159 (3) |
N3—H3···O13ii | 0.86 (1) | 2.27 (1) | 3.101 (3) | 163 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O10i | 0.865 (10) | 2.218 (16) | 3.041 (3) | 159 (3) |
N3—H3···O13ii | 0.862 (10) | 2.265 (14) | 3.101 (3) | 163 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co(C24H30N2P2)(CO)3][Co(CO)4]·0.25C7H8 |
Mr | 745.40 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 22.1602 (6), 12.9730 (3), 24.7883 (6) |
β (°) | 103.9330 (12) |
V (Å3) | 6916.6 (3) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 8.79 |
Crystal size (mm) | 0.43 × 0.11 × 0.05 |
Data collection | |
Diffractometer | Bruker Kappa APEXII DUO diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2011) |
Tmin, Tmax | 0.12, 0.65 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 89837, 12171, 11080 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 1.03 |
No. of reflections | 12171 |
No. of parameters | 825 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.93, −0.57 |
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
Financial support by the BMBF (project `Light2Hydrogen') is gratefully acknowledged. TB would like to thank Professor Uwe Rosenthal for support.
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