research communications
N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine]dibromidomanganese(II) and its monophosphine oxide analogue
of the tetrahydrofuran disolvate of a 94:6 of [aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, A-1060 Vienna, Austria, and bX-Ray Centre, TU Wien, Getreidemarkt 9, A-1060 Vienna, Austria
*Correspondence e-mail: matthias.mastalir@tuwien.ac.at
The MnBr2 complex of N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine (1·MnBr2) co-crystallizes with 5.69% of the monophosphine oxide analogue (1O·MnBr2) and two tetrahydrofuran (THF) molecules, namely [N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine]dibromidomanganese(II)–[bis(di-tert-butylphosphanyl)({6-[(di-tert-butylphosphanyl)amino]pyridin-2-yl}amino)phosphine oxide]dibromidomanganese(II)–tetrahydrofuran (0.94/0.06/2), [MnBr2(C21H41N3P2)]0.94[MnBr2(C21H41N3OP2)]0.06·2C4H8O. The 1·MnBr2 and 1O·MnBr2 complexes are occupationally disordered about general positions. Both complexes feature square-pyramidal coordination of the MnII atoms. They are connected by weak N—H⋯Br hydrogen bonding into chains extending along [001]. The THF molecules are located between the layers formed by these chains. One THF molecule is involved in hydrogen bonding to an amine H atom.
Keywords: crystal structure; PNP; manganese; pincer complex; solid solution; phosphine oxide.
CCDC reference: 1565992
1. Chemical context
Pincer complexes of transition metals are versatile homogeneous catalysts (Dobereiner & Crabtree, 2010; Mastalir et al., 2017a). Traditionally, platinum-group metal complexes have been employed in these applications (Zell & Milstein, 2015; Bähn et al., 2011; Crabtree et al., 2011; Watson & Williams, 2010; Gunanathan et al., 2007; Zhang et al., 2005; Michlik & Kempe, 2010; Michlik et al., 2012). Our group is dedicated to the development of more cost-effective and environmentally friendly alternatives, such as PNP (pincer ligand coordinating via P, N and P) complexes of Fe (Glatz et al., 2015a,b; Mastalir et al., 2016a). Recently, we extended our research scope to MnI PNP complexes (Mastalir et al., 2016b,c, 2017b).
In this context, we attempted the synthesis of the MnBr2 complex with the PNP ligand N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine (1) as a precursor to MnI complexes. Inadvertently, on recrystallization of the crude product, a 94.31:5.69 (14)% of the expected 1·MnBr2 and its phosphine oxide analogue 1O·MnBr2 co-crystallized with two THF solvent molecules (see scheme), most likely as a result of an impure starting ligand. The crystal under investigation accordingly has the composition 0.9431(1·MnBr2)·0.0569(1O·MnBr2)·2THF.
2. Structural commentary
The title crystal possesses P21/c symmetry. A 94.31:5.69 (14) overlay of the 1·MnBr2 complex and the corresponding mono-oxidized 1O·MnBr2 complex is located on general positions. Two crystallographically independent THF solvent molecules are likewise located on general positions, one of which is positionally disordered.
The ligands of both the non-oxidized and the oxidized complexes occupy virtually the same space. They could therefore not be resolved into distinct sites and even the atomic displacement parameters (ADPs) are not significantly enlarged. The Mn and Br atoms, on the other hand, are clearly separated within the resolution of the experiment.
The MnII atom of the non-oxidized 1·MnBr2 complex features fivefold coordination with the PNP-ligand and two bromine atoms (Fig. 1) in a square-pyramidal conformation with a τ5 parameter (Addison et al., 1984) of 0.083. The ideal τ5 values for square-pyramidal and trigonal–bipyramidal coordinations are 0 and 1, respectively. The Mn atom is nearly equidistant [2.644 (9) and 2.639 (10) Å] to both P atoms.
The complex adopts a distinctly non-planar configuration with distances to the least-squares (LS) plane defined by the pryidine ring and amine-N atoms of 0.4391 (7) Å (Mn), 0.0700 (7) Å (P1) and 0.3100 (7) Å (P2), as is characteristic for this class of compounds.
In comparison, the recently structurally characterized MnCl2 complex of the isopropyl analogue of 1 (Mastalir et al., 2017a) features an even more ideal square-pyramidal conformation (τ5 = 0.041) and the MnII atom is likewise nearly equidistant to both P atoms [2.593 (5) and 2.579 (5) Å]. Likewise, the deviation from planarity is in the same range [distances to the LS plane described above: 0.4158 (2) Å (Mn), 0.3190 (4) Å (P1) and 0.0334 (4) Å (P2)].
In the monooxidized 1O·MnBr2 complex (Fig. 2), the coordination deviates more from the square-pyramidal mode than in 1·MnBr2 (τ5 = 0.196; Fig. 3). The O atom introduces an additional distortion, leading to an increased deviation from planarity, whereby the Mn′ and O atoms are located on opposite sides of the LS plane described above [0.712 (13) Å (Mn) and 0.12 (4) Å (O)]. The Mn′—P1 bond is distinctly shorter [2.453 (12) Å] than the corresponding bond in the non-oxidized complex.
3. Supramolecular features
The disordered THF molecule (O1/C22–C25) is connected to a complex molecule via a strong N1—H⋯O1 hydrogen bond (Table 1). The second THF molecule is not involved in hydrogen bonding (Fig. 4).
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The amine functionality that is not bonded to THF connects via a weak N2—H⋯Br1(Br1′) hydrogen bond, thus forming infinite chains of complex molecules extending along [001]. Adjacent complexes in this chain are related by the c glide reflection.
No further bonding intermolecular interactions are observed in the via van der Waals interactions, forming distinct layers parallel to (100). Between these layers are located the hydrogen-bonded and free THF molecules (Fig. 5).
The chains of complexes contact in the [001] direction4. Database survey
A search in the Cambridge Structural Database (Version 5.37; last update March 2016; Groom et al., 2016) for structures of fivefold-coordinated Mn/PNP complexes revealed no entries. Nevertheless, our group recently published the MnCl2 complex of the isopropyl analogue of 1 (see above). Moreover, three related Mn(PNP)(CO)3 complexes with octahedral coordination modes are known. One of these compounds is likewise pyridine-based (Flörke & Haupt, 1991), whereas the others are based on ditolylamines (Radosevich et al., 2009). No ligand mono-oxidized analogues of Mn/PNP complexes have been described up to now.
5. Synthesis and crystallization
The synthesis of 1 was performed as described previously (Deibl & Kempe, 2016). THF was dried over Na under an Ar atmosphere. All other reagents were obtained commercially and used as received. 1 and MnBr2 were stirred in dry THF for 18 h under an Ar atmosphere (see reaction scheme). The complex 1·MnBr2 was precipitated by addition of n-pentane. The microcrystalline powder was washed twice with n-pentane. Crystals were grown by slow vapour diffusion of diethyl ether into a room-temperature of 1·MnBr2 in THF.
6. Refinement
Crystal data, data collection and structure . H atoms bonded to C atoms were placed in calculated positions and refined as riding atoms, with fixed bond lengths in the range 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(CMe). The two amine H atoms were located in difference-Fourier maps and were refined freely.
details are summarized in Table 2Excessive electron density in difference-Fourier maps was attributed to alternative positions of the Mn and Br atoms. The Mn and Br atoms were therefore refined as positionally disordered (minor positions: Mn′ and Br′). The occupancies of the atoms of both orientations were constrained to the same value and the sum of the occupancies of both orientations were constrained to 1. The atoms in the minor (ca 6%) orientation were modelled with isotropic ADPs. The minor orientation featured an unreasonably long Mn—P distance (ca 3.18 Å). Inspection of the electron density in the difference-Fourier map close to the P atom revealed a faint positive peak that was attributed to an O atom that is bound to the P atom, forming an phosphine oxide. The occupancy of this atom was constrained to be equal to the occupancy of the minor positions. The position of the additional O atom was refined freely.
A C atom of a THF molecule featured excessively anisotropic ADPs. The position was therefore split and refined as positionally disordered with the sum of the occupancies of both positions constrained to 1; occupancy ratio 0.526 (14):0.474 (14). Both C atoms were refined with isotropic ADPs.
Supporting information
CCDC reference: 1565992
https://doi.org/10.1107/S2056989017011276/sj5533sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017011276/sj5533Isup2.hkl
Data collection: APEX2 (Bruker, 2015); cell
SAINT-Plus (Bruker, 2015); data reduction: SAINT-Plus (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: JANA20006 (Petříček et al., 2014); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[MnBr2(C21H41N3P2)]0.94[MnBr2(C21H41N3OP2)]0.06·2C4H8O | F(000) = 1574 |
Mr = 757.4 | Dx = 1.409 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ycb | Cell parameters from 9972 reflections |
a = 11.6496 (7) Å | θ = 2.5–27.9° |
b = 18.5016 (11) Å | µ = 2.73 mm−1 |
c = 17.1626 (9) Å | T = 100 K |
β = 105.1763 (16)° | Block, colourless |
V = 3570.2 (4) Å3 | 0.45 × 0.43 × 0.42 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 8452 independent reflections |
Radiation source: X-ray tube | 6175 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.031 |
ω– and φ–scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan SADABS | h = −15→12 |
Tmin = 0.29, Tmax = 0.32 | k = −24→24 |
29339 measured reflections | l = −22→21 |
Refinement on F | 250 constraints |
R[F > 3σ(F)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F) = 0.045 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 1.92 | (Δ/σ)max = 0.033 |
8452 reflections | Δρmax = 1.02 e Å−3 |
377 parameters | Δρmin = −0.70 e Å−3 |
0 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | −0.13106 (3) | 0.21675 (2) | 0.212868 (18) | 0.02007 (12) | 0.9431 (14) |
Br2 | 0.13368 (4) | 0.33931 (4) | 0.17703 (3) | 0.02331 (15) | 0.9431 (14) |
Mn1 | 0.01885 (5) | 0.22707 (4) | 0.12718 (3) | 0.01482 (17) | 0.9431 (14) |
P1 | −0.13202 (6) | 0.26779 (4) | −0.00936 (4) | 0.0159 (2) | |
P2 | 0.16177 (6) | 0.11993 (4) | 0.19188 (4) | 0.0181 (2) | |
N1 | 0.0909 (2) | 0.17720 (13) | 0.02291 (13) | 0.0176 (8) | |
N2 | −0.0580 (2) | 0.23660 (13) | −0.07467 (14) | 0.0162 (8) | |
N3 | 0.2335 (2) | 0.11176 (17) | 0.11855 (16) | 0.0304 (10) | |
C1 | 0.0446 (2) | 0.19576 (15) | −0.05555 (17) | 0.0171 (9) | |
C2 | 0.0954 (2) | 0.17562 (16) | −0.11712 (17) | 0.0196 (10) | |
C3 | 0.1999 (3) | 0.13664 (16) | −0.09629 (18) | 0.0230 (10) | |
C4 | 0.2492 (3) | 0.11602 (18) | −0.01763 (18) | 0.0270 (11) | |
C5 | 0.1901 (3) | 0.13566 (17) | 0.04007 (17) | 0.0221 (10) | |
C6 | −0.2769 (2) | 0.21863 (16) | −0.04271 (16) | 0.0194 (9) | |
C7 | −0.2484 (3) | 0.14164 (16) | −0.01047 (18) | 0.0246 (10) | |
C8 | −0.3270 (3) | 0.21438 (17) | −0.13518 (17) | 0.0239 (10) | |
C9 | −0.3688 (3) | 0.25190 (19) | −0.00383 (18) | 0.0285 (11) | |
C10 | −0.1495 (3) | 0.36663 (16) | −0.03135 (17) | 0.0222 (10) | |
C11 | −0.0270 (3) | 0.39435 (17) | −0.03689 (18) | 0.0312 (12) | |
C12 | −0.2398 (3) | 0.38786 (17) | −0.11023 (18) | 0.0312 (12) | |
C13 | −0.1813 (3) | 0.40295 (18) | 0.04066 (18) | 0.0306 (12) | |
C14 | 0.0926 (3) | 0.02904 (16) | 0.19525 (18) | 0.0225 (10) | |
C15 | −0.0099 (3) | 0.02794 (19) | 0.11757 (19) | 0.0360 (12) | |
C16 | 0.1749 (3) | −0.03522 (17) | 0.1940 (2) | 0.0352 (13) | |
C17 | 0.0398 (3) | 0.02424 (19) | 0.2676 (2) | 0.0385 (13) | |
C18 | 0.2845 (3) | 0.13803 (17) | 0.28446 (18) | 0.0270 (11) | |
C19 | 0.3647 (4) | 0.1961 (2) | 0.2623 (3) | 0.0712 (19) | |
C20 | 0.3635 (3) | 0.07417 (18) | 0.31918 (19) | 0.0335 (12) | |
C21 | 0.2270 (4) | 0.1694 (2) | 0.3455 (2) | 0.0595 (17) | |
O1 | 0.4581 (2) | 0.03040 (16) | 0.12665 (16) | 0.0561 (11) | |
C22 | 0.5077 (3) | −0.03355 (19) | 0.1672 (2) | 0.0361 (13) | |
C23 | 0.6257 (3) | −0.0110 (2) | 0.21980 (19) | 0.0353 (12) | |
C24 | 0.6682 (3) | 0.04216 (19) | 0.1660 (2) | 0.0376 (13) | |
C25 | 0.5443 (5) | 0.0679 (4) | 0.1037 (5) | 0.028 (2)* | 0.526 (14) |
C25' | 0.5681 (7) | 0.0877 (5) | 0.1459 (7) | 0.044 (3)* | 0.474 (14) |
O2 | 0.5419 (3) | 0.39891 (17) | 0.14239 (18) | 0.0699 (13) | |
C26 | 0.4652 (4) | 0.4329 (2) | 0.0740 (2) | 0.0598 (18) | |
C27 | 0.3497 (4) | 0.3968 (2) | 0.0567 (2) | 0.0526 (17) | |
C28 | 0.3868 (3) | 0.3206 (2) | 0.0795 (2) | 0.0366 (13) | |
C29 | 0.4875 (3) | 0.3300 (2) | 0.1544 (2) | 0.0425 (14) | |
H1c2 | 0.059049 | 0.188431 | −0.172261 | 0.0235* | |
H1c3 | 0.238693 | 0.123717 | −0.137222 | 0.0277* | |
H1c4 | 0.321964 | 0.088942 | −0.002941 | 0.0325* | |
H1c7 | −0.186839 | 0.121666 | −0.031736 | 0.0295* | |
H2c7 | −0.222058 | 0.142792 | 0.047401 | 0.0295* | |
H3c7 | −0.318525 | 0.11225 | −0.026886 | 0.0295* | |
H1c8 | −0.271293 | 0.189676 | −0.158223 | 0.0287* | |
H2c8 | −0.401014 | 0.188474 | −0.147807 | 0.0287* | |
H3c8 | −0.340002 | 0.262352 | −0.157041 | 0.0287* | |
H1c9 | −0.389071 | 0.299547 | −0.025156 | 0.0341* | |
H2c9 | −0.438911 | 0.222295 | −0.015517 | 0.0341* | |
H3c9 | −0.336027 | 0.254713 | 0.053552 | 0.0341* | |
H1c11 | −0.008889 | 0.374301 | −0.083898 | 0.0375* | |
H2c11 | −0.028618 | 0.446122 | −0.040693 | 0.0375* | |
H3c11 | 0.032869 | 0.379861 | 0.010465 | 0.0375* | |
H1c12 | −0.219226 | 0.364764 | −0.154818 | 0.0375* | |
H2c12 | −0.31787 | 0.372767 | −0.10837 | 0.0375* | |
H3c12 | −0.238838 | 0.439353 | −0.116916 | 0.0375* | |
H1c13 | −0.122777 | 0.390579 | 0.089545 | 0.0367* | |
H2c13 | −0.182949 | 0.454438 | 0.03357 | 0.0367* | |
H3c13 | −0.258094 | 0.386533 | 0.04391 | 0.0367* | |
H1c15 | 0.021899 | 0.031633 | 0.07147 | 0.0432* | |
H2c15 | −0.053403 | −0.016472 | 0.11484 | 0.0432* | |
H3c15 | −0.062181 | 0.06798 | 0.117963 | 0.0432* | |
H1c16 | 0.235551 | −0.037166 | 0.244141 | 0.0423* | |
H2c16 | 0.129566 | −0.079164 | 0.186929 | 0.0423* | |
H3c16 | 0.211316 | −0.029613 | 0.150251 | 0.0423* | |
H1c17 | 0.102692 | 0.024961 | 0.316543 | 0.0462* | |
H2c17 | −0.012172 | 0.064643 | 0.266956 | 0.0462* | |
H3c17 | −0.004476 | −0.019893 | 0.264691 | 0.0462* | |
H1c19 | 0.406858 | 0.175825 | 0.226307 | 0.0855* | |
H2c19 | 0.316768 | 0.235825 | 0.23631 | 0.0855* | |
H3c19 | 0.420678 | 0.212855 | 0.31042 | 0.0855* | |
H1c20 | 0.397018 | 0.054208 | 0.27842 | 0.0402* | |
H2c20 | 0.426309 | 0.090032 | 0.364147 | 0.0402* | |
H3c20 | 0.316983 | 0.037944 | 0.33691 | 0.0402* | |
H1c21 | 0.180491 | 0.2108 | 0.32283 | 0.0714* | |
H2c21 | 0.176437 | 0.133785 | 0.360104 | 0.0714* | |
H3c21 | 0.287371 | 0.183707 | 0.392693 | 0.0714* | |
H1c22 | 0.519189 | −0.068374 | 0.128432 | 0.0433* | |
H2c22 | 0.458372 | −0.050564 | 0.200205 | 0.0433* | |
H1c23 | 0.678176 | −0.051946 | 0.230347 | 0.0424* | |
H2c23 | 0.614582 | 0.013804 | 0.266395 | 0.0424* | |
H1c24 | 0.705351 | 0.082712 | 0.197661 | 0.0451* | 0.526 (14) |
H2c24 | 0.716077 | 0.017253 | 0.136788 | 0.0451* | 0.526 (14) |
H1c24' | 0.735268 | 0.068596 | 0.197649 | 0.0451* | 0.4744 |
H2c24' | 0.676461 | 0.017733 | 0.118449 | 0.0451* | 0.4744 |
H1c25 | 0.544358 | 0.054399 | 0.049694 | 0.0339* | 0.526 (14) |
H2c25 | 0.53318 | 0.118777 | 0.110279 | 0.0339* | 0.526 (14) |
H1c25' | 0.567881 | 0.114191 | 0.097713 | 0.0531* | 0.4744 |
H2c25' | 0.565383 | 0.116462 | 0.191882 | 0.0531* | 0.4744 |
H1c26 | 0.497915 | 0.428116 | 0.028376 | 0.0717* | |
H2c26 | 0.455711 | 0.482953 | 0.085831 | 0.0717* | |
H1c27 | 0.312275 | 0.399219 | −0.000187 | 0.0631* | |
H2c27 | 0.304979 | 0.415078 | 0.092141 | 0.0631* | |
H1c28 | 0.416345 | 0.298984 | 0.037768 | 0.044* | |
H2c28 | 0.32261 | 0.295283 | 0.092902 | 0.044* | |
H1c29 | 0.456057 | 0.333414 | 0.200692 | 0.051* | |
H2c29 | 0.544145 | 0.291762 | 0.157523 | 0.051* | |
Br1' | −0.1686 (6) | 0.2563 (4) | 0.2072 (4) | 0.025 (2)* | 0.0569 (14) |
Br2' | 0.1292 (11) | 0.3624 (6) | 0.1693 (8) | 0.047 (4)* | 0.0569 (14) |
Mn1' | −0.0068 (11) | 0.2547 (7) | 0.1291 (8) | 0.034 (4)* | 0.0569 (14) |
H1n2 | −0.080 (3) | 0.2446 (15) | −0.1241 (18) | 0.016 (8)* | |
H1n3 | 0.293 (3) | 0.0903 (18) | 0.126 (2) | 0.038 (11)* | |
O | 0.072 (3) | 0.167 (2) | 0.198 (2) | 0.029 (9)* | 0.0569 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01954 (18) | 0.0280 (3) | 0.01392 (16) | −0.00322 (16) | 0.00659 (12) | −0.00286 (15) |
Br2 | 0.0256 (2) | 0.0263 (3) | 0.0174 (2) | −0.0104 (2) | 0.00460 (14) | −0.0030 (2) |
Mn1 | 0.0145 (3) | 0.0199 (3) | 0.0096 (2) | −0.0017 (2) | 0.00218 (19) | 0.0000 (2) |
P1 | 0.0152 (4) | 0.0205 (4) | 0.0121 (4) | 0.0015 (3) | 0.0039 (3) | −0.0017 (3) |
P2 | 0.0156 (4) | 0.0239 (4) | 0.0147 (4) | 0.0000 (3) | 0.0037 (3) | 0.0019 (3) |
N1 | 0.0155 (12) | 0.0254 (14) | 0.0126 (12) | 0.0011 (10) | 0.0048 (10) | 0.0028 (11) |
N2 | 0.0168 (13) | 0.0258 (14) | 0.0063 (12) | 0.0056 (10) | 0.0036 (10) | 0.0022 (11) |
N3 | 0.0151 (14) | 0.055 (2) | 0.0223 (14) | 0.0153 (14) | 0.0074 (11) | 0.0184 (14) |
C1 | 0.0154 (14) | 0.0152 (15) | 0.0196 (15) | −0.0014 (12) | 0.0028 (12) | 0.0021 (13) |
C2 | 0.0194 (15) | 0.0230 (17) | 0.0161 (15) | 0.0029 (13) | 0.0044 (12) | 0.0025 (13) |
C3 | 0.0228 (16) | 0.0299 (18) | 0.0194 (15) | 0.0035 (14) | 0.0108 (13) | 0.0038 (15) |
C4 | 0.0179 (16) | 0.037 (2) | 0.0287 (17) | 0.0097 (14) | 0.0107 (13) | 0.0112 (16) |
C5 | 0.0171 (15) | 0.0278 (17) | 0.0227 (16) | 0.0029 (13) | 0.0073 (12) | 0.0094 (14) |
C6 | 0.0144 (14) | 0.0272 (17) | 0.0156 (14) | −0.0003 (13) | 0.0023 (11) | −0.0022 (14) |
C7 | 0.0197 (16) | 0.0281 (18) | 0.0246 (16) | −0.0085 (13) | 0.0033 (13) | −0.0034 (15) |
C8 | 0.0196 (16) | 0.0291 (18) | 0.0203 (15) | 0.0004 (14) | 0.0001 (12) | −0.0020 (15) |
C9 | 0.0194 (17) | 0.044 (2) | 0.0236 (17) | 0.0002 (15) | 0.0086 (14) | −0.0023 (16) |
C10 | 0.0296 (17) | 0.0209 (16) | 0.0171 (15) | 0.0021 (13) | 0.0079 (13) | −0.0027 (14) |
C11 | 0.043 (2) | 0.0215 (18) | 0.0297 (18) | −0.0028 (15) | 0.0111 (16) | 0.0029 (16) |
C12 | 0.039 (2) | 0.0241 (19) | 0.0276 (17) | 0.0087 (15) | 0.0031 (15) | 0.0012 (16) |
C13 | 0.039 (2) | 0.0277 (19) | 0.0238 (16) | 0.0080 (16) | 0.0049 (15) | −0.0078 (16) |
C14 | 0.0206 (16) | 0.0198 (16) | 0.0268 (16) | −0.0021 (13) | 0.0057 (13) | −0.0006 (14) |
C15 | 0.0286 (19) | 0.033 (2) | 0.042 (2) | −0.0101 (16) | 0.0004 (16) | −0.0034 (19) |
C16 | 0.0298 (19) | 0.0210 (18) | 0.054 (2) | 0.0031 (15) | 0.0094 (17) | −0.0070 (18) |
C17 | 0.037 (2) | 0.033 (2) | 0.053 (2) | 0.0011 (17) | 0.0253 (18) | 0.015 (2) |
C18 | 0.0270 (17) | 0.0264 (18) | 0.0201 (16) | 0.0010 (14) | −0.0072 (13) | 0.0036 (14) |
C19 | 0.050 (3) | 0.057 (3) | 0.074 (3) | −0.028 (2) | −0.043 (2) | 0.033 (3) |
C20 | 0.0285 (19) | 0.036 (2) | 0.0296 (18) | 0.0068 (16) | −0.0047 (14) | 0.0033 (17) |
C21 | 0.058 (3) | 0.067 (3) | 0.036 (2) | 0.032 (2) | −0.0183 (19) | −0.029 (2) |
O1 | 0.0181 (13) | 0.089 (2) | 0.0629 (17) | 0.0169 (14) | 0.0140 (12) | 0.0461 (17) |
C22 | 0.0283 (19) | 0.037 (2) | 0.044 (2) | −0.0058 (16) | 0.0101 (16) | −0.0047 (18) |
C23 | 0.0240 (18) | 0.051 (2) | 0.0291 (18) | 0.0091 (16) | 0.0042 (14) | −0.0006 (18) |
C24 | 0.0268 (18) | 0.039 (2) | 0.051 (2) | −0.0083 (16) | 0.0163 (17) | −0.0103 (19) |
O2 | 0.0551 (19) | 0.079 (2) | 0.068 (2) | −0.0295 (17) | 0.0026 (16) | −0.0065 (19) |
C26 | 0.089 (3) | 0.056 (3) | 0.034 (2) | −0.020 (3) | 0.015 (2) | 0.004 (2) |
C27 | 0.069 (3) | 0.051 (3) | 0.038 (2) | −0.006 (2) | 0.015 (2) | −0.009 (2) |
C28 | 0.035 (2) | 0.042 (2) | 0.0339 (19) | −0.0001 (17) | 0.0119 (16) | −0.0092 (18) |
C29 | 0.047 (2) | 0.053 (3) | 0.0293 (19) | −0.003 (2) | 0.0123 (17) | 0.0025 (19) |
Br1—Mn1 | 2.5677 (7) | C15—H1c15 | 0.96 |
Br1—N2i | 3.625 (2) | C15—H2c15 | 0.96 |
Br1—Br1' | 0.845 (8) | C15—H3c15 | 0.96 |
Br1—Mn1' | 2.398 (15) | C16—H1c16 | 0.96 |
Br2—Mn1 | 2.4968 (9) | C16—H2c16 | 0.96 |
Br2—Br2' | 0.446 (12) | C16—H3c16 | 0.96 |
Br2—Mn1' | 2.258 (12) | C17—H1c17 | 0.96 |
Mn1—P1 | 2.6443 (9) | C17—H2c17 | 0.96 |
Mn1—P2 | 2.6395 (10) | C17—H3c17 | 0.96 |
Mn1—N1 | 2.355 (3) | C18—C19 | 1.535 (6) |
Mn1—Br1' | 2.918 (7) | C18—C20 | 1.520 (4) |
Mn1—Br2' | 2.820 (12) | C18—C21 | 1.501 (5) |
Mn1—Mn1' | 0.597 (13) | C19—H1c19 | 0.96 |
Mn1—O | 1.65 (4) | C19—H2c19 | 0.96 |
P1—N2 | 1.685 (3) | C19—H3c19 | 0.96 |
P1—C6 | 1.870 (3) | C20—H1c20 | 0.96 |
P1—C10 | 1.867 (3) | C20—H2c20 | 0.96 |
P1—Mn1' | 2.453 (12) | C20—H3c20 | 0.96 |
P2—N3 | 1.690 (3) | C21—H1c21 | 0.96 |
P2—C14 | 1.872 (3) | C21—H2c21 | 0.96 |
P2—C18 | 1.869 (3) | C21—H3c21 | 0.96 |
P2—O | 1.38 (4) | O1—C22 | 1.417 (4) |
N1—C1 | 1.357 (3) | O1—C25 | 1.361 (8) |
N1—C5 | 1.355 (4) | O1—C25' | 1.629 (9) |
N2—C1 | 1.379 (4) | C22—C23 | 1.493 (4) |
N2—Br1'ii | 3.629 (6) | C22—H1c22 | 0.96 |
N2—H1n2 | 0.83 (3) | C22—H2c22 | 0.96 |
N3—C5 | 1.382 (4) | C23—C24 | 1.518 (5) |
N3—H1n3 | 0.78 (3) | C23—H1c23 | 0.96 |
C1—C2 | 1.391 (4) | C23—H2c23 | 0.96 |
C2—C3 | 1.378 (4) | C24—C25 | 1.628 (7) |
C2—H1c2 | 0.96 | C24—C25' | 1.407 (9) |
C3—C4 | 1.375 (4) | C24—H1c24 | 0.96 |
C3—H1c3 | 0.96 | C24—H2c24 | 0.96 |
C4—C5 | 1.394 (5) | C24—H1c24' | 0.96 |
C4—H1c4 | 0.96 | C24—H2c24' | 0.96 |
C6—C7 | 1.533 (4) | C25—C25' | 0.793 (13) |
C6—C8 | 1.543 (4) | C25—H1c25 | 0.96 |
C6—C9 | 1.531 (5) | C25—H2c25 | 0.96 |
C7—H1c7 | 0.96 | C25—H1c25' | 0.9125 |
C7—H2c7 | 0.96 | C25'—H2c25 | 0.8596 |
C7—H3c7 | 0.96 | C25'—H1c25' | 0.96 |
C8—H1c8 | 0.96 | C25'—H2c25' | 0.96 |
C8—H2c8 | 0.96 | O2—C26 | 1.423 (5) |
C8—H3c8 | 0.96 | O2—C29 | 1.462 (5) |
C9—H1c9 | 0.96 | C26—C27 | 1.462 (6) |
C9—H2c9 | 0.96 | C26—H1c26 | 0.96 |
C9—H3c9 | 0.96 | C26—H2c26 | 0.96 |
C10—C11 | 1.543 (5) | C27—C28 | 1.496 (5) |
C10—C12 | 1.532 (4) | C27—H1c27 | 0.96 |
C10—C13 | 1.535 (5) | C27—H2c27 | 0.96 |
C11—H1c11 | 0.96 | C28—C29 | 1.506 (4) |
C11—H2c11 | 0.96 | C28—H1c28 | 0.96 |
C11—H3c11 | 0.96 | C28—H2c28 | 0.96 |
C12—H1c12 | 0.96 | C29—H1c29 | 0.96 |
C12—H2c12 | 0.96 | C29—H2c29 | 0.96 |
C12—H3c12 | 0.96 | H1c24—H1c24' | 0.4356 |
C13—H1c13 | 0.96 | H2c24—H2c24' | 0.4859 |
C13—H2c13 | 0.96 | H2c25—H1c25' | 0.5126 |
C13—H3c13 | 0.96 | Br1'—Mn1' | 2.584 (17) |
C14—C15 | 1.540 (4) | Br2'—Mn1' | 2.526 (17) |
C14—C16 | 1.531 (4) | Mn1'—O | 2.08 (4) |
C14—C17 | 1.525 (5) | ||
Mn1—Br1—N2i | 122.86 (4) | C14—C17—H2c17 | 109.47 |
Mn1—Br1—Br1' | 106.2 (5) | C14—C17—H3c17 | 109.47 |
Mn1—Br1—Mn1' | 13.3 (3) | H1c17—C17—H2c17 | 109.47 |
N2i—Br1—Br1' | 83.6 (4) | H1c17—C17—H3c17 | 109.47 |
N2i—Br1—Mn1' | 120.9 (3) | H2c17—C17—H3c17 | 109.47 |
Br1'—Br1—Mn1' | 93.0 (6) | P2—C18—C19 | 107.1 (2) |
Mn1—Br2—Br2' | 133.1 (15) | P2—C18—C20 | 116.4 (2) |
Mn1—Br2—Mn1' | 13.2 (3) | P2—C18—C21 | 106.3 (2) |
Br2'—Br2—Mn1' | 122.5 (15) | C19—C18—C20 | 107.2 (3) |
Br1—Mn1—Br2 | 104.44 (3) | C19—C18—C21 | 108.3 (3) |
Br1—Mn1—P1 | 97.75 (3) | C20—C18—C21 | 111.2 (3) |
Br1—Mn1—P2 | 98.74 (3) | C18—C19—H1c19 | 109.47 |
Br1—Mn1—N1 | 146.86 (6) | C18—C19—H2c19 | 109.47 |
Br1—Mn1—Br1' | 16.14 (15) | C18—C19—H3c19 | 109.47 |
Br1—Mn1—Br2' | 104.6 (3) | H1c19—C19—H2c19 | 109.47 |
Br1—Mn1—Mn1' | 67.0 (14) | H1c19—C19—H3c19 | 109.47 |
Br1—Mn1—O | 73.0 (15) | H2c19—C19—H3c19 | 109.47 |
Br2—Mn1—P1 | 103.82 (3) | C18—C20—H1c20 | 109.47 |
Br2—Mn1—P2 | 104.95 (3) | C18—C20—H2c20 | 109.47 |
Br2—Mn1—N1 | 108.70 (6) | C18—C20—H3c20 | 109.47 |
Br2—Mn1—Br1' | 94.86 (14) | H1c20—C20—H2c20 | 109.47 |
Br2—Mn1—Br2' | 6.6 (2) | H1c20—C20—H3c20 | 109.47 |
Br2—Mn1—Mn1' | 60.0 (12) | H2c20—C20—H3c20 | 109.47 |
Br2—Mn1—O | 104.3 (12) | C18—C21—H1c21 | 109.47 |
P1—Mn1—P2 | 141.86 (3) | C18—C21—H2c21 | 109.47 |
P1—Mn1—N1 | 74.02 (5) | C18—C21—H3c21 | 109.47 |
P1—Mn1—Br1' | 87.62 (11) | H1c21—C21—H2c21 | 109.47 |
P1—Mn1—Br2' | 97.3 (2) | H1c21—C21—H3c21 | 109.47 |
P1—Mn1—Mn1' | 65.1 (12) | H2c21—C21—H3c21 | 109.47 |
P1—Mn1—O | 151.8 (12) | C22—O1—C25 | 109.4 (3) |
P2—Mn1—N1 | 73.40 (6) | C22—O1—C25' | 104.2 (4) |
P2—Mn1—Br1' | 114.11 (14) | C25—O1—C25' | 29.0 (5) |
P2—Mn1—Br2' | 111.3 (2) | O1—C22—C23 | 104.9 (3) |
P2—Mn1—Mn1' | 152.8 (12) | O1—C22—H1c22 | 109.47 |
P2—Mn1—O | 26.7 (15) | O1—C22—H2c22 | 109.47 |
N1—Mn1—Br1' | 152.83 (13) | C23—C22—H1c22 | 109.47 |
N1—Mn1—Br2' | 108.3 (3) | C23—C22—H2c22 | 109.47 |
N1—Mn1—Mn1' | 131.2 (13) | H1c22—C22—H2c22 | 113.73 |
N1—Mn1—O | 98.9 (14) | C22—C23—C24 | 102.0 (3) |
Br1'—Mn1—Br2' | 93.6 (3) | C22—C23—H1c23 | 109.47 |
Br1'—Mn1—Mn1' | 51.0 (14) | C22—C23—H2c23 | 109.47 |
Br1'—Mn1—O | 87.8 (15) | C24—C23—H1c23 | 109.47 |
Br2'—Mn1—Mn1' | 55.0 (12) | C24—C23—H2c23 | 109.47 |
Br2'—Mn1—O | 110.8 (12) | H1c23—C23—H2c23 | 116.01 |
Mn1'—Mn1—O | 129.6 (19) | C23—C24—C25 | 102.4 (4) |
Mn1—P1—N2 | 98.90 (8) | C23—C24—C25' | 99.0 (5) |
Mn1—P1—C6 | 118.03 (9) | C23—C24—H1c24 | 109.47 |
Mn1—P1—C10 | 118.04 (9) | C23—C24—H2c24 | 109.47 |
Mn1—P1—Mn1' | 12.8 (3) | C23—C24—H1c24' | 109.47 |
N2—P1—C6 | 102.01 (13) | C23—C24—H2c24' | 109.47 |
N2—P1—C10 | 104.40 (14) | C25—C24—C25' | 29.2 (5) |
N2—P1—Mn1' | 109.4 (3) | C25—C24—H1c24 | 109.47 |
C6—P1—C10 | 111.87 (13) | C25—C24—H2c24 | 109.47 |
C6—P1—Mn1' | 120.6 (3) | C25—C24—H1c24' | 132.27 |
C10—P1—Mn1' | 107.3 (3) | C25—C24—H2c24' | 81.22 |
Mn1—P2—N3 | 97.73 (10) | C25'—C24—H1c24 | 83.85 |
Mn1—P2—C14 | 117.28 (9) | C25'—C24—H2c24 | 135.73 |
Mn1—P2—C18 | 118.77 (10) | C25'—C24—H1c24' | 109.47 |
Mn1—P2—O | 32.5 (16) | C25'—C24—H2c24' | 109.47 |
N3—P2—C14 | 104.08 (15) | H1c24—C24—H2c24 | 115.69 |
N3—P2—C18 | 103.39 (14) | H1c24—C24—H1c24' | 26.22 |
N3—P2—O | 130.2 (16) | H1c24—C24—H2c24' | 135.91 |
C14—P2—C18 | 111.99 (13) | H2c24—C24—H1c24' | 92.42 |
C14—P2—O | 102.6 (16) | H2c24—C24—H2c24' | 29.32 |
C18—P2—O | 104.4 (14) | H1c24'—C24—H2c24' | 118.23 |
Mn1—N1—C1 | 121.76 (19) | O1—C25—C24 | 104.7 (5) |
Mn1—N1—C5 | 120.72 (18) | O1—C25—C25' | 94.5 (11) |
C1—N1—C5 | 117.0 (3) | O1—C25—H1c25 | 109.47 |
Br1ii—N2—P1 | 124.14 (10) | O1—C25—H2c25 | 109.47 |
Br1ii—N2—C1 | 109.31 (18) | O1—C25—H1c25' | 141.04 |
Br1ii—N2—Br1'ii | 13.37 (12) | C24—C25—C25' | 59.8 (7) |
Br1ii—N2—H1n2 | 6 (2) | C24—C25—H1c25 | 109.47 |
P1—N2—C1 | 126.3 (2) | C24—C25—H2c25 | 109.47 |
P1—N2—Br1'ii | 124.64 (15) | C24—C25—H1c25' | 96.15 |
P1—N2—H1n2 | 123 (2) | C25'—C25—H1c25 | 155.83 |
C1—N2—Br1'ii | 108.5 (2) | C25'—C25—H2c25 | 57.78 |
C1—N2—H1n2 | 111 (2) | C25'—C25—H1c25' | 68.08 |
Br1'ii—N2—H1n2 | 8.5 (19) | H1c25—C25—H2c25 | 113.82 |
P2—N3—C5 | 124.8 (2) | H1c25—C25—H1c25' | 93.45 |
P2—N3—H1n3 | 121 (3) | H2c25—C25—H1c25' | 31.65 |
C5—N3—H1n3 | 114 (3) | O1—C25'—C24 | 102.6 (6) |
N1—C1—N2 | 118.0 (3) | O1—C25'—C25 | 56.4 (8) |
N1—C1—C2 | 123.2 (3) | O1—C25'—H2c25 | 95.19 |
N2—C1—C2 | 118.7 (2) | O1—C25'—H1c25' | 109.47 |
C1—C2—C3 | 117.8 (3) | O1—C25'—H2c25' | 109.47 |
C1—C2—H1c2 | 121.12 | C24—C25'—C25 | 91.1 (9) |
C3—C2—H1c2 | 121.12 | C24—C25'—H2c25 | 141.59 |
C2—C3—C4 | 120.9 (3) | C24—C25'—H1c25' | 109.47 |
C2—C3—H1c3 | 119.57 | C24—C25'—H2c25' | 109.47 |
C4—C3—H1c3 | 119.57 | C25—C25'—H2c25 | 70.88 |
C3—C4—C5 | 117.9 (3) | C25—C25'—H1c25' | 61.87 |
C3—C4—H1c4 | 121.04 | C25—C25'—H2c25' | 157.99 |
C5—C4—H1c4 | 121.05 | H2c25—C25'—H1c25' | 32.13 |
N1—C5—N3 | 117.8 (3) | H2c25—C25'—H2c25' | 95.86 |
N1—C5—C4 | 123.0 (3) | H1c25'—C25'—H2c25' | 115.59 |
N3—C5—C4 | 119.1 (3) | C26—O2—C29 | 107.4 (3) |
P1—C6—C7 | 104.40 (17) | O2—C26—C27 | 108.1 (3) |
P1—C6—C8 | 114.1 (2) | O2—C26—H1c26 | 109.47 |
P1—C6—C9 | 110.4 (2) | O2—C26—H2c26 | 109.47 |
C7—C6—C8 | 108.2 (2) | C27—C26—H1c26 | 109.47 |
C7—C6—C9 | 109.0 (3) | C27—C26—H2c26 | 109.47 |
C8—C6—C9 | 110.4 (2) | H1c26—C26—H2c26 | 110.78 |
C6—C7—H1c7 | 109.47 | C26—C27—C28 | 101.0 (3) |
C6—C7—H2c7 | 109.47 | C26—C27—H1c27 | 109.47 |
C6—C7—H3c7 | 109.47 | C26—C27—H2c27 | 109.47 |
H1c7—C7—H2c7 | 109.47 | C28—C27—H1c27 | 109.47 |
H1c7—C7—H3c7 | 109.47 | C28—C27—H2c27 | 109.47 |
H2c7—C7—H3c7 | 109.47 | H1c27—C27—H2c27 | 116.82 |
C6—C8—H1c8 | 109.47 | C27—C28—C29 | 102.8 (3) |
C6—C8—H2c8 | 109.47 | C27—C28—H1c28 | 109.47 |
C6—C8—H3c8 | 109.47 | C27—C28—H2c28 | 109.47 |
H1c8—C8—H2c8 | 109.47 | C29—C28—H1c28 | 109.47 |
H1c8—C8—H3c8 | 109.47 | C29—C28—H2c28 | 109.47 |
H2c8—C8—H3c8 | 109.47 | H1c28—C28—H2c28 | 115.39 |
C6—C9—H1c9 | 109.47 | O2—C29—C28 | 104.5 (3) |
C6—C9—H2c9 | 109.47 | O2—C29—H1c29 | 109.47 |
C6—C9—H3c9 | 109.47 | O2—C29—H2c29 | 109.47 |
H1c9—C9—H2c9 | 109.47 | C28—C29—H1c29 | 109.47 |
H1c9—C9—H3c9 | 109.47 | C28—C29—H2c29 | 109.47 |
H2c9—C9—H3c9 | 109.47 | H1c29—C29—H2c29 | 114.04 |
P1—C10—C11 | 106.5 (2) | C24—H1c24—H1c24' | 76.89 |
P1—C10—C12 | 116.3 (2) | C24—H2c24—H2c24' | 75.34 |
P1—C10—C13 | 107.6 (2) | C24—H1c24'—H1c24 | 76.89 |
C11—C10—C12 | 107.0 (3) | C24—H2c24'—H2c24 | 75.34 |
C11—C10—C13 | 109.1 (2) | C25—H2c25—C25' | 51.33 |
C12—C10—C13 | 110.2 (2) | C25—H2c25—H1c25' | 69.07 |
C10—C11—H1c11 | 109.47 | C25'—H2c25—H1c25' | 84.79 |
C10—C11—H2c11 | 109.47 | C25—H1c25'—C25' | 50.05 |
C10—C11—H3c11 | 109.47 | C25—H1c25'—H2c25 | 79.29 |
H1c11—C11—H2c11 | 109.47 | C25'—H1c25'—H2c25 | 63.09 |
H1c11—C11—H3c11 | 109.47 | Br1—Br1'—Mn1 | 57.7 (4) |
H2c11—C11—H3c11 | 109.47 | Br1—Br1'—N2i | 83.0 (4) |
C10—C12—H1c12 | 109.47 | Br1—Br1'—Mn1' | 67.9 (5) |
C10—C12—H2c12 | 109.47 | Mn1—Br1'—N2i | 112.62 (18) |
C10—C12—H3c12 | 109.47 | Mn1—Br1'—Mn1' | 10.3 (3) |
H1c12—C12—H2c12 | 109.47 | N2i—Br1'—Mn1' | 115.2 (3) |
H1c12—C12—H3c12 | 109.47 | Br2—Br2'—Mn1 | 40.3 (13) |
H2c12—C12—H3c12 | 109.47 | Br2—Br2'—Mn1' | 48.9 (14) |
C10—C13—H1c13 | 109.47 | Mn1—Br2'—Mn1' | 11.2 (3) |
C10—C13—H2c13 | 109.47 | Br1—Mn1'—Br2 | 118.6 (6) |
C10—C13—H3c13 | 109.47 | Br1—Mn1'—Mn1 | 99.8 (15) |
H1c13—C13—H2c13 | 109.47 | Br1—Mn1'—P1 | 108.1 (5) |
H1c13—C13—H3c13 | 109.47 | Br1—Mn1'—Br1' | 19.1 (2) |
H2c13—C13—H3c13 | 109.47 | Br1—Mn1'—Br2' | 120.1 (6) |
P2—C14—C15 | 103.2 (2) | Br1—Mn1'—O | 71.0 (12) |
P2—C14—C16 | 114.9 (2) | Br2—Mn1'—Mn1 | 106.8 (13) |
P2—C14—C17 | 110.2 (2) | Br2—Mn1'—P1 | 118.4 (6) |
C15—C14—C16 | 108.9 (2) | Br2—Mn1'—Br1' | 111.1 (6) |
C15—C14—C17 | 108.5 (3) | Br2—Mn1'—Br2' | 8.6 (3) |
C16—C14—C17 | 110.7 (3) | Br2—Mn1'—O | 99.5 (11) |
C14—C15—H1c15 | 109.47 | Mn1—Mn1'—P1 | 102.2 (13) |
C14—C15—H2c15 | 109.47 | Mn1—Mn1'—Br1' | 118.7 (15) |
C14—C15—H3c15 | 109.47 | Mn1—Mn1'—Br2' | 113.8 (14) |
H1c15—C15—H2c15 | 109.47 | Mn1—Mn1'—O | 37.6 (15) |
H1c15—C15—H3c15 | 109.47 | P1—Mn1'—Br1' | 99.9 (5) |
H2c15—C15—H3c15 | 109.47 | P1—Mn1'—Br2' | 111.0 (6) |
C14—C16—H1c16 | 109.47 | P1—Mn1'—O | 133.6 (11) |
C14—C16—H2c16 | 109.47 | Br1'—Mn1'—Br2' | 109.9 (6) |
C14—C16—H3c16 | 109.47 | Br1'—Mn1'—O | 89.2 (13) |
H1c16—C16—H2c16 | 109.47 | Br2'—Mn1'—O | 108.1 (11) |
H1c16—C16—H3c16 | 109.47 | Mn1—O—P2 | 121 (3) |
H2c16—C16—H3c16 | 109.47 | Mn1—O—Mn1' | 12.7 (5) |
C14—C17—H1c17 | 109.47 | P2—O—Mn1' | 132 (3) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···Br1ii | 0.83 (3) | 2.80 (3) | 3.625 (2) | 173 (2) |
N2—H1N2···Br1′ii | 0.83 (3) | 2.81 (3) | 3.629 (7) | 169 (3) |
N3—H1N3···O1 | 0.78 (4) | 2.22 (4) | 2.990 (4) | 171 (3) |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
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