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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2018 Sep 14;74(Pt 10):1433–1438. doi: 10.1107/S2056989018012859

[Bis(2,6-diiso­propyl­phen­yl) phosphato-κO]pentakis­(methanol-κO)manganese bis­(2,6-diiso­propyl­phen­yl) phosphate methanol tris­olvate

Mikhail E Minyaev a,*, Alexander N Tavtorkin a,b, Sof’ya A Korchagina a,b, Ilya E Nifant’ev a,b, Andrei V Churakov c, Artem O Dmitrienko d, Konstantin A Lyssenko d
PMCID: PMC6176441  PMID: 30319795

The crystal structure of the complex [Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+[OOP(O-2,6-iPr2C6H3)2]−·(CH3OH)3 exhibits O—H⋯O bonds between the cations, anions and non-coordinating methanol mol­ecules, forming infinite one-dimensional associates. The complex demonstrates inhibition of thermal oxidation of polydi­methyl­siloxane.

Keywords: manganese, organophosphate, hydrogen bonding, coordination compound, polydi­methyl­siloxane, thermal oxidation, crystal structure

Abstract

The title compound, [Mn(C24H34O4P)(CH3OH)5](C24H34O4P)·3CH3OH, was formed in the reaction between a hydrate of a manganese(II) salt [either Mn(NO3)2(H2O)6 or MnCl2(H2O)4] with a methanol solvate of lithium bis­(2,6-diiso­propyl­phen­yl) phosphate, {Li[OOP(O-2,6-iPr2C6H3)2]·(CH4O)3}·CH4O, in methanol. The structure has monoclinic (Cc) symmetry at 150 K. The complex consists of an [Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+ cation, an [OOP(O-2,6-iPr2C6H3)2]− anion and three non-coordinating methanol mol­ecules. The anion demonstrates disorder of an isopropyl group [occupancy ratio is 0.57 (4):0.43 (4)]. The di­aryl­phosphate ligand in the cation exhibits a κ1 O terminal coordination mode. The Mn atom is in a nearly unperturbed octa­hedral environment. The [Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+ cation exhibits one intra­molecular O—H⋯O bond, and is coordinated via two inter­molecular O—H⋯O hydrogen bonds to the [OOP(O-2,6-iPr2C6H3)2]− anion. The cations, anions and non-coordinating methanol mol­ecules are linked into infinite chains along the c-axis direction via 0—H⋯O hydrogen bonding. The complex is of inter­est as a possible inhibitor for the thermal decomposition of polydi­methyl­siloxane. The crystal studied was refined as an inversion twin with a domain ratio of 0.47 (3):0.53 (3).

Chemical context  

Polydi­methyl­siloxane (PDMS) liquids are widely applied in many devices as shock-absorbing, hydraulic and damping liquids, as bases for greases and as heat-transfer agents for many industrial processes carried out at elevated temperatures. Various lipophilic derivatives of metals with variable valency, such as Mn, Fe, Ni, Ce, etc., are used for the inhibition of thermo-oxidative decomposition of polyorganosiloxane heat carriers (Swihart & Jones, 1985 ▸; Nielsen, 1961 ▸; Halm, 1980 ▸; Kobzova et al., 1966 ▸; Kishimoto et al., 1976 ▸; Rozanova et al., 1995 ▸; Minyaev et al., 2018a ▸) in order to increase their operating time and temperature (usually up to ca 550 K). As manganese-based inhibitors, cymantrene and its derivatives have shown promising results (Sobolevskiy et al., 1970 ▸). However, these Mn compounds are not available on an industrial scale. Easily accessible disubstituted organophosphate ligands are usually regarded as being lipophilic. For example, rare-earth complexes with such disubstituted organophosphate ligands are highly soluble in hydro­carbon media (Nifant’ev et al., 2013 ▸, 2014 ▸). Therefore, the obtained manganese derivative with the organophosphate ligand might be a readily available alternative to cymantrene and to its derivatives.

Herein we report on the crystal structure of the Mn organo­phosphate complex [Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+[OOP(O-2,6-iPr2C6H3)2]−·3CH3OH, which contains a lipophilic diaryl-substituted organophosphate ligand, and on its properties regarding inhibition of the thermal oxidation of polydi­methyl­siloxane.graphic file with name e-74-01433-scheme1.jpg

The title compound can be synthesized (Fig. 1 ▸) by the reaction of either manganese(II) nitrate hexa­hydrate, Mn(NO3)2(H2O)6, or manganese(II) chloride tetra­hydrate, MnCl2(H2O)4, with lithium bis­(2,6-diiso­propyl­phen­yl) phosphate methanol solvate, {Li[OOP(O-2,6-iPr2C6H3)2](CH3OH)3}·CH3OH (for its structure, see Minyaev et al., 2015 ▸). Performing the reaction in a methanol medium provided the ionic complex instead of the expected neutral complex.

Figure 1.

Figure 1

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Synthesis of [Mn{(2,6-iPr2C6H3-O)2PO2}(CH3OH)5][(2,6-iPr2C6H3-O)2PO2]·(CH3OH)3.

Analysis of thermal decomposition inhibition properties  

We tested the title Mn compound as a possible inhibitor for the thermal decomposition of the heat-transfer agent PDMS in air at a temperature of 573 K, and compared the obtained results with control experiments and with experiments, where the Ce complex [Ce{O2P(O-2,6-iPr2C6H3)2}2(CH3OH)5]·CH3OH bearing the same ligand was used (Minyaev et al., 2018a ▸). All experiments were carried out under the same conditions (Table 1 ▸).

Table 1. Weight loss (%) versus time and gel time (h) in the thermal destruction of PDMS.

The starting mass of PDMS-50 was 2.000 g. The thermal destruction experiments were carried out at T = 573 K. The Mn complex is [Mn{O2P(O-2,6-iPr2C6H3)2}(CH3OH)5]+[O2P(O-2,6-iPr2C6H3)2]−·3CH3OH and the Ce complex is [Ce{O2P(O-2,6-iPr2C6H3)2}2(CH3OH)5]·CH3OH.

Entry Additive Weight loss Gel timea
    1 h 2 h 3 h 5 h 9 h  
1 None (control) 1.5% 3.5% 5.5% 9% 13.5% 5 h
2 0.1% Mn 1% 2% 3% 6% 8.5% 9 h
3 0.5% Mn 1% 2% 2.5% 3.5% 6% –b
4 0.1% Ce 1% 1.5% 2% 3% 4.5% –b
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Notes: (a) After this time, the PDMS liquid becomes fully solidified. (b) No precipitate, low viscosity, clear liquid at the end of the experiment (9 h).

The results indicate that the manganese derivative inhibits the thermal decomposition of the silicone heat carrier, although to a much lesser extent than the cerium derivative at the same loads (each 0.1% by mass, entries 2 and 4). Moreover, the PDMS liquid containing 0.1% of the Mn complex became solidified at the end of the experiment. However, with an increase of the manganese derivative load of up to 0.5% (entry 3), the PDMS decomposition decreases to the level displayed by the cerium additive at 0.1%. Thus, the lipophilic manganese derivative may be used as an accessible alternative to cerium and organometallic manganese derivatives.

Structural commentary  

The mol­ecular components of the title compound comprise an [Mn{O2P(O-2,6-iPr2C6H3)2}(CH3OH)5]+ cation (Fig. 2 ▸, left), an [O2P(O-2,6-iPr2C6H3)2]− anion (Fig. 2 ▸, right) and three non-coordinating methanol mol­ecules (Fig. 3 ▸). The bis­(2,6-diiso­propyl­phen­yl)phosphate ligand in the cation exhibits a κ1 O terminal coordination mode. The Mn2+ cation is also coordinated by five methanol mol­ecules, providing a nearly unperturbed octa­hedral environment. The Mn—Omethanol bond distances range from 2.146 (3) to 2.236 (4) Å, whereas the Mn—Ophosphate bond length is shorter, with a value of 2.116 (3) Å (Table 2 ▸). The shortest Mn—OMethanol bond (Mn—O1) is at the trans-position to the Mn—Ophosphate bond. The O—Mn—O bond angles between two neighboring ligands (at the cis-positions) are very close to 90° and vary between 86.88 (14)° [O1—Mn—O4] and 93.86 (13)° [O2—Mn—O9]. The O—Mn—O angles between trans-ligands range from 175.26 (14)° [O2—Mn—O4] to 178.62 (16)° [O3—Mn—O5].

Figure 2.

Figure 2

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The structures of the [Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+ cation (left) and [OOP(O-2,6-iPr2C6H3)2]− anion (right). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.

Figure 3.

Figure 3

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The asymmetric unit and hydrogen bonding within it. Displacement ellipsoids are drawn at the 50% probability level. Only hy­droxy H atoms and only Cipso atoms (C9, C21, C33 and C45) of aryl groups are shown for clarity.

Table 2. Selected bond lengths (Å).

Mn1—O1 2.146 (3) P1—O10 1.488 (3)
Mn1—O2 2.236 (4) P1—O11 1.600 (3)
Mn1—O3 2.158 (4) P1—O12 1.597 (3)
Mn1—O4 2.213 (4) P2—O13 1.496 (4)
Mn1—O5 2.220 (4) P2—O14 1.488 (3)
Mn1—O9 2.116 (3) P2—O15 1.607 (3)
P1—O9 1.503 (3) P2—O16 1.600 (3)
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The O—Cipso bond distances [which range from 1.403 (5) Å for O12–C21 to 1.409 (5) Å for O16—C45] correspond to those of a slightly shortened regular single O—C bond (1.43 Å), indicating no significant charge redistribution between the PO4 and aryl fragments. Both phospho­rous atoms adopt distorted tetra­hedral environments. The value of the P—OMn distance [P1—O9 = 1.503 (3) Å] is very close to the P—O distances for O atoms that are not connected to any other non-H atoms in both phosphate groups [1.488 (3)–1.496 (4) Å for the P1—O10, P2—O13 and P2—O14 bonds; see Table 2 ▸]. This indicates a mainly ionic character of the Mn—phosphate bond. The P—OC bond lengths are considerably higher [1.597 (3)–1.607 (3) Å]. Regardless of aryl steric hindrance, the OC—P—OC bond angles are the smallest [100.3 (2)° for O11—P1—O12 and 99.3 (2)° for O15—P2—O16] among all of the O—P—O angles, which range from 105.8 (2)° for O10—P1—O12 to 117.1 (2)° for O13—P2—O14.

All of these facts point not only to an approximately equal negative charge redistribution on atoms O9, O10 and O13, O14, but also to more pronounced double-bond character for the corresponding P—O bonds compared to the P—OC bonds. These results are in good agreement with data obtained for rare-earth phosphates bearing the same ligand: [Ln{O2P(O-2,6-iPr2C6H3)2}2Cl(CH3OH)4]·2CH3OH (Ln = Nd, Lu, Y; Minyaev et al., 2017 ▸), [Ln{O2P(O-2,6-iPr2C6H3)2}3(CH3OH)5]·CH3OH (Ln = La, Ce, Nd; Minyaev et al., 2018a ▸), {La2[(2,6-iPr2C6H3-O)2POO]5(H2O)2(OH)}·2(hexa­ne) and {Nd2[(2,6-iPr2C6H3-O)2POO]4(H2O)4(OH)}+[(2,6-iPr2C6H3-O)2POO]−·2(hepta­ne) (Minyaev et al., 2018b ▸).

Supra­molecular features  

The [Mn{O2P(O-2,6-iPr2C6H3)2}(CH3OH)5]+ cation exhibits one intra­molecular hydrogen bond (O5—H5⋯O10, Table 3 ▸). The [OOP(O-2,6-iPr2C6H3)2]− anion and the cation are connected via two hydrogen bonds: O1—H1⋯O13 and O2—H2⋯O14. The cation is also connected to the non-coordin­ating methanol mol­ecules via O3—H3⋯O7 and O4—-H4⋯O6 hydrogen bonds, and further linked to the third mol­ecule by the O7—H7⋯O8 hydrogen bond, forming the supramolecular moiety shown in Fig. 3 ▸. These moieties are linked by O6—H6⋯O14i and O8—H8⋯O10ii bonds [symmetry codes: (i) x, −y + 1, z − Inline graphic; (ii) x, −y + 1, z + Inline graphic; see Table 3 ▸], forming infinite chains along the c-axis direction (Fig. 4 ▸).

Table 3. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O13 0.85 1.79 2.537 (5) 145
O2—H2⋯O14 0.82 1.99 2.724 (5) 148
O3—H3⋯O7 0.86 1.79 2.644 (6) 170
O4—H4⋯O6 0.85 1.95 2.700 (7) 147
O5—H5⋯O10 0.85 1.84 2.661 (5) 163
O6—H6⋯O14i 0.86 1.89 2.708 (6) 157
O7—H7⋯O8 0.85 1.88 2.697 (8) 159
O8—H8⋯O10ii 0.85 1.86 2.708 (7) 174
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Figure 4.

Figure 4

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An infinite one-dimensional supramolecular chain {[Mn{OOP(O-2,6-iPr2C6H3)2}(CH3OH)5]+[OOP(O-2,6-iPr2C6H3)2]−·3CH3OH3}∞ formed by O—H⋯O bonds (blue dashed lines). Displacement ellipsoids are drawn at the 50% probability level. Disorder is not shown.

The presence of two separate ions in the crystal lattice can be explained by the relatively large solvation energy obtained from the formation of many O—H⋯O bonds within a one-dimensional hydrogen-bond network. This might be one of the driving forces for crystal formation.

Database survey  

The crystal structures of manganese complexes with various di-substituted organophosphate ligands have not yet been studied well. Thus, the number of structures in the Cambridge Structural Database (CSD version 5.38, latest update May 2017; Groom et al., 2016 ▸) is limited to 20 (after the exclusion of duplicated structures). These comprise: one mononuclear complex (MOKCEU; Murugavel & Sathiyendiran, 2001 ▸); four binuclear complexes [DAVFEM (Shiraishi et al., 2005 ▸), ENIMUJ (Yashiro et al., 2003 ▸), YIWYUA and YIWZAH (Pothi­raja et al., 2014 ▸)]; three tetra­nuclear complexes (YOSPIH, YOSPON and YOSPUT; Van Allsburg et al., 2015 ▸); two trinuclear heterometallic complexes [ENEHAI (Nakajima et al., 2016 ▸) and RITKIO (Dean et al., 1997 ▸)]; two dodeca­nuclear complexes [DAGJEB/DAGJEB01 (Bian et al., 2004 ▸; Kuroda-Sowa et al., 2005 ▸) and XUBXOH/XUBXOH01 (Kuroda-Sowa et al., 2002 ▸, 2005 ▸)]; eight coordination polymers [KOZZAC and KOZZUW (Rajakannu et al., 2015 ▸), LULGEE (Sathiyendiran & Murugavel, 2002 ▸), ODEWOK (Rafizadeh et al., 2007 ▸), SAMNEA/SAMNEA01 (Pothiraja et al., 2004 ▸, 2005 ▸), TEKQOR and TEKQUX (Dey et al., 2013 ▸) and WENSUE (Rafizadeh et al., 2006 ▸)]. All of the above are heteroleptic complexes containing the following di-substituted organophosphate ligands: PO2(OPh)2, PO2(OC6H4-4-NO2)2, PO2(OMe)2, PO2(OtBu)2 and PO2(OCMe2CMe2O). The ligands mainly display a μ2-κ1 O:κ1 O′ bridging coordination mode, and occasionally a κ1 O terminal mode. The Mn complexes, especially mononuclear ones, with other disubstituted organophosphate anions are yet to be synthesized. It is worth mentioning that the tile complex is mononuclear, incorporates a novel organo­phosphate ligand, and is the first Mn–phosphate complex with a phosphate anion separated from the Mn complex cation in the crystal lattice.

Synthesis and crystallization  

General experimental remarks  

The synthesis of the title complex was carried out under an argon atmosphere. Lithium bis­(2,6-diiso­propyl­phen­yl) phosphate methanol tetra­solvate, [Li{OOP(O-2,6-iPr2C6H3)2}(CH3OH)3]·CH3OH, was synthesized according to the literature procedure (Minyaev et al., 2015 ▸). C/H elemental analysis was performed with a Perkin–Elmer 2400 Series II elemental analyzer. Methanol was distilled over a Ca/Mg alloy and stored over mol­ecular sieves (4 Å). Polydi­methyl­siloxane (PDMS-50, viscosity 50 mm2 s−1) was used as purchased (Sofex–Silicone). XRF studies were performed with an ARL ADVANTIX instrument. Powder patterns (supplementary Figs. S1–S5) were recorded on a Bruker D8 Advance Vario diffractometer, using Cu Kα1 radiation [Ge(111) monochromator] and a LynxEye 1D position-sensitive detector in transmission mode at room temperature. The 2θ range was 2–90° with a 0.01° step for all samples. The Rietveld analysis was carried out with Topas software (Bruker, 2015 ▸).

Synthesis and crystallization of the complex  

A solution of Mn(NO3)2(H2O)6 (159 mg, 0.55 mmol) in 5 ml of methanol was carefully added to a solution of [Li{OOP(O-2,6-iPr2C6H3)2}(CH3OH)3]·CH3OH (580 mg, 1.05 mmol) in 5 ml of methanol at room temperature. The mixture was stirred for 10 s. Crystals started to precipitate out after 20 min.. The following day, some crystals were taken from the mother liquor for X-ray studies. The remaining crystals were filtered off, washed with methanol (2 × 10 ml) and dried briefly under dynamic vacuum [yield 485 mg (0.42 mmol, 81%) as colourless prismatic crystals. Analysis found (calculated for C56H100MnO16P2): C 58.75 (58.68), H 8.72% (8.79%). The same com­pound was prepared in 80% yield from MnCl2(H2O)4 under similar reaction conditions. The crystal shapes varied from needles to blocks, depending on the synthesis and crystal growth conditions. The formed high-spin Mn complex cannot be studied by NMR techniques because of its paramagnetic behaviour.

Thermal oxidation of polydi­methyl­siloxane  

A mixture (2.000 g) of the Mn complex (either 2 mg or 10 mg) and PDMS was placed in a glass beaker. No additive was used in the control experiments. The beaker was placed into a muffle furnace with a preset temperature of 573 K. The beaker was periodically taken out from the furnace and weighed to determine the weight loss.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. The positions of most hydrogen atoms were found from the difference electron-density map, but they were positioned geometrically (C—H = 0.95 Å for aromatic, 0.98 Å for methyl and 0.99 Å for methyl­ene H atoms) and refined as riding atoms with relative isotropic displacement parameters U iso(H) = 1.5Ueq(C) for methyl H atoms and 1.2U eq(C) otherwise. The positions of the hy­droxy H atoms were refined with restrained O—H distances of 0.85 (2) Å with U iso(H)= 1.2U eq(O). A rotating group model was applied for methyl groups. Two reflections (Inline graphic 0 0 and 2 0 0) were affected by the beam stop, and were therefore omitted from the refinement. Two reflections (Inline graphic 2 10 and 4 0 4) were also omitted from the final cycles of the refinement as their (I obs − I calcd)/σ(w) values were over 10.

Table 4. Experimental details.

Crystal data
Chemical formula [Mn(C24H34O4P)(CH4O)5](C24H34O4P)·3CH4O
M r 1146.23
Crystal system, space group Monoclinic, C c
Temperature (K) 150
a, b, c (Å) 31.872 (6), 12.640 (2), 16.881 (3)
β (°) 109.990 (2)
V (Å3) 6391 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.32
Crystal size (mm) 0.40 × 0.40 × 0.25
 
Data collection
Diffractometer Bruker SMART APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2008 ▸)
T min, T max 0.724, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections 36871, 18839, 16119
R int 0.031
(sin θ/λ)max (Å−1) 0.714
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.072, 0.197, 1.07
No. of reflections 18839
No. of parameters 730
No. of restraints 52
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 3.11, −0.74
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.47 (2)
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Computer programs: APEX2 and SAINT (Bruker, 2008 ▸), SHELXS2013 and SHELXTL (Sheldrick, 2008 ▸), SHELXL2017 (Sheldrick, 2015 ▸), publCIF (Westrip, 2010 ▸) and Mercury (Macrae et al.,2006 ▸).

One of the isopropyl groups is disordered over two sets of sites with an occupancy ratio of 0.57 (4):0.43 (4) for atoms C40A/C41A and C40B/C41B, respectively. Four HC—CH3 distances in the disordered fragment were restrained to be equal within an estimated standard deviation of 0.01 Å. Similarity restraints for thermal displacement ellipsoids were also applied. The crystal studied was refined as an inversion twin with a domain ratio of 0.47 (3):0.53 (3).

The final crystallographic model exhibits some problems, including two relatively high remaining Q peaks of residual electron density, which could not be reasonably handled, and a rather high Δρmax/Δρmin ratio.

The problems might have been caused by (1) incomplete substitution of NO3 − in crystals initially made from Mn(NO3)2(H2O)6, (2) some content of other metal impurities, (3) crystal decomposition during data collection, (4) twinning or (5) disorder. Several attempts to prepare crystal batches were made, starting from Mn(NO3)2(H2O)6 and from MnCl2(H2O)4 by varying the crystal-growth conditions slightly. Several attempts to reestablish the crystal structure were made using different diffractometers and software (see Table S1 in the supporting information for details). Crystallographic models of the studied crystals demonstrated the same problems regardless of differences in the preparation and the instrument used. Modelling disorder and applying various twinning laws (using CELL_NOW) were unsuccessful. The X-ray fluorescence (XRF) analysis demonstrated the presence of only the elements P and Mn and the absence of a noticeable qu­antity of any other heavy element (heavier than Ne). Several C/H analyses undertaken immediately after the crystal preparation showed very similar results that were nearly identical to calculated values.

Inter­esting results were obtained by using the powder X-ray diffraction (pXRD) method (see the supporting information). After several days without being in the solvent, the sample became non-single-phased. Moreover, the sample demonstrated dramatic changes in its phase composition during the pXRD measurements (see Figs. S2–S5). Such a phase change might be attributed to the facile loss of non-coordinating methanol mol­ecules.

Therefore, the inherent problems of the presented crystallographic model can only be the result of slow crystal decomposition during the X-ray measurements or/and, more likely, from some subtle unrevealed twinning.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018012859/pj2055sup1.cif

e-74-01433-sup1.cif (1.1MB, cif)
Click here for additional data file. (9.1KB, cdx)

Supporting information file. DOI: 10.1107/S2056989018012859/pj2055Isup3.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018012859/pj2055Isup4.hkl

e-74-01433-Isup4.hkl (1.5MB, hkl)

Powder XRD data and single crystal X-ray diffraction studies. DOI: 10.1107/S2056989018012859/pj2055sup5.pdf

e-74-01433-sup5.pdf (276.2KB, pdf)

CCDC reference: 1867164

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

Equipment from the collective exploitation center ‘New petrochemical processes, polymer composites and adhesives’ of the TIPS RAS was used.

supplementary crystallographic information

Crystal data

[Mn(C24H34O4P)(CH4O)5](C24H34O4P)·3CH4O F(000) = 2476
Mr = 1146.23 Dx = 1.191 Mg m−3
Monoclinic, Cc Mo Kα radiation, λ = 0.71073 Å
a = 31.872 (6) Å Cell parameters from 9949 reflections
b = 12.640 (2) Å θ = 2.3–30.5°
c = 16.881 (3) Å µ = 0.32 mm−1
β = 109.990 (2)° T = 150 K
V = 6391 (2) Å3 Prism, colourless
Z = 4 0.40 × 0.40 × 0.25 mm
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Data collection

Bruker SMART APEXII diffractometer 18839 independent reflections
Radiation source: fine-focus sealed tube 16119 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.031
ω scans θmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008) h = −45→45
Tmin = 0.724, Tmax = 0.923 k = −17→17
36871 measured reflections l = −24→24
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.072 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.197 w = 1/[σ2(Fo2) + (0.1189P)2 + 8.5165P] where P = (Fo2 + 2Fc2)/3
S = 1.07 (Δ/σ)max = 0.002
18839 reflections Δρmax = 3.11 e Å−3
730 parameters Δρmin = −0.74 e Å−3
52 restraints Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods Absolute structure parameter: 0.47 (2)
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Special details

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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Refined as a 2-component inversion twin.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
Mn1 0.51624 (2) 0.56670 (5) 0.44955 (4) 0.02200 (15)
O1 0.45043 (11) 0.5084 (3) 0.4319 (2) 0.0317 (8)
H1 0.4396 (4) 0.5541 (15) 0.4563 (8) 0.048*
C1 0.41774 (19) 0.4808 (7) 0.3527 (4) 0.0469 (16)
H1A 0.404356 0.412417 0.357752 0.070*
H1B 0.432005 0.475751 0.309781 0.070*
H1C 0.394447 0.535174 0.336204 0.070*
O2 0.51222 (12) 0.6630 (3) 0.5578 (2) 0.0324 (8)
H2 0.4873 (9) 0.6797 (7) 0.5578 (2) 0.049*
C2 0.54381 (19) 0.7447 (5) 0.5988 (4) 0.0374 (12)
H2A 0.528752 0.799432 0.620322 0.056*
H2B 0.555995 0.776127 0.558241 0.056*
H2C 0.568134 0.713868 0.645766 0.056*
O3 0.54723 (14) 0.4397 (4) 0.5350 (3) 0.0419 (10)
H3 0.5324 (5) 0.3856 (18) 0.5417 (4) 0.063*
C3 0.5834 (2) 0.4602 (7) 0.6116 (4) 0.0498 (16)
H3A 0.582758 0.408705 0.654509 0.075*
H3B 0.580468 0.531835 0.631333 0.075*
H3C 0.611784 0.454225 0.601316 0.075*
O4 0.51420 (13) 0.4692 (3) 0.3394 (3) 0.0336 (8)
H4 0.51595 (14) 0.402 (2) 0.3393 (3) 0.050*
C4 0.5057 (2) 0.5088 (6) 0.2549 (4) 0.0444 (14)
H4A 0.514894 0.455615 0.221773 0.067*
H4B 0.522807 0.573981 0.257462 0.067*
H4C 0.473811 0.523579 0.228182 0.067*
O5 0.48595 (12) 0.6992 (3) 0.3625 (3) 0.0335 (8)
H5 0.5086 (8) 0.7311 (11) 0.3584 (3) 0.050*
C5 0.4553 (2) 0.7743 (6) 0.3730 (5) 0.0472 (15)
H5A 0.442418 0.814878 0.320784 0.071*
H5B 0.470828 0.822452 0.419211 0.071*
H5C 0.431422 0.737556 0.386175 0.071*
O6 0.48720 (19) 0.2694 (4) 0.2918 (3) 0.0506 (12)
H6 0.4699 (6) 0.2887 (8) 0.2426 (17) 0.076*
C6 0.4648 (3) 0.1958 (8) 0.3256 (7) 0.071 (3)
H6A 0.455252 0.135345 0.287273 0.107*
H6B 0.438547 0.229462 0.332550 0.107*
H6C 0.484905 0.171313 0.380533 0.107*
O7 0.5105 (2) 0.2605 (4) 0.5589 (4) 0.0547 (13)
H7 0.5293 (7) 0.2376 (9) 0.6050 (16) 0.082*
C7 0.4701 (4) 0.2874 (8) 0.5717 (10) 0.087 (3)
H7A 0.447395 0.233779 0.545471 0.130*
H7B 0.459763 0.356567 0.546185 0.130*
H7C 0.475196 0.290601 0.632291 0.130*
O8 0.5566 (3) 0.1457 (5) 0.6957 (4) 0.0733 (19)
H8 0.5582 (3) 0.1795 (12) 0.7402 (15) 0.110*
C8 0.5546 (4) 0.0388 (7) 0.7096 (6) 0.071 (3)
H8A 0.582879 0.015402 0.751309 0.107*
H8B 0.549415 0.000387 0.656664 0.107*
H8C 0.530132 0.024446 0.730777 0.107*
P1 0.59610 (3) 0.69092 (9) 0.40155 (6) 0.0186 (2)
O9 0.58012 (10) 0.6249 (3) 0.4596 (2) 0.0206 (6)
O10 0.56168 (12) 0.7604 (3) 0.3429 (2) 0.0274 (7)
O11 0.63971 (10) 0.7556 (3) 0.4553 (2) 0.0229 (6)
O12 0.61596 (10) 0.6216 (3) 0.3435 (2) 0.0207 (6)
C9 0.64458 (15) 0.8004 (4) 0.5344 (3) 0.0250 (9)
C10 0.62856 (17) 0.9022 (4) 0.5377 (4) 0.0325 (11)
C11 0.6356 (2) 0.9445 (5) 0.6181 (5) 0.0437 (14)
H11 0.625280 1.013925 0.622988 0.052*
C12 0.6572 (2) 0.8867 (6) 0.6907 (4) 0.0446 (14)
H12 0.660979 0.916022 0.744462 0.053*
C13 0.67350 (19) 0.7859 (5) 0.6847 (3) 0.0361 (11)
H13 0.688395 0.747236 0.734672 0.043*
C14 0.66832 (16) 0.7409 (4) 0.6069 (3) 0.0255 (9)
C15 0.6067 (2) 0.9678 (5) 0.4592 (4) 0.0424 (13)
H15 0.602164 0.919607 0.409978 0.051*
C16 0.6377 (4) 1.0557 (8) 0.4513 (7) 0.088 (4)
H16A 0.663790 1.024608 0.441984 0.132*
H16B 0.647472 1.097612 0.503294 0.132*
H16C 0.621809 1.101472 0.403628 0.132*
C17 0.5615 (4) 1.0072 (12) 0.4531 (8) 0.100 (4)
H17A 0.539894 0.949104 0.436031 0.149*
H17B 0.552412 1.064061 0.411173 0.149*
H17C 0.562474 1.034393 0.508085 0.149*
C18 0.68866 (16) 0.6365 (4) 0.6000 (3) 0.0288 (10)
H18 0.666495 0.596753 0.552851 0.035*
C19 0.73069 (17) 0.6506 (5) 0.5770 (4) 0.0349 (11)
H19A 0.723064 0.687691 0.522881 0.052*
H19B 0.743288 0.581107 0.572412 0.052*
H19C 0.752679 0.692168 0.620832 0.052*
C20 0.6993 (2) 0.5684 (6) 0.6793 (4) 0.0432 (14)
H20A 0.672884 0.564327 0.696477 0.065*
H20B 0.724067 0.600105 0.724787 0.065*
H20C 0.707638 0.497050 0.667457 0.065*
C21 0.65996 (15) 0.5850 (4) 0.3640 (3) 0.0229 (8)
C22 0.69048 (16) 0.6485 (4) 0.3443 (3) 0.0270 (9)
C23 0.73334 (17) 0.6070 (6) 0.3618 (4) 0.0380 (12)
H23 0.755256 0.648890 0.350039 0.046*
C24 0.74489 (19) 0.5081 (6) 0.3953 (4) 0.0432 (14)
H24 0.774325 0.482028 0.406709 0.052*
C25 0.7130 (2) 0.4466 (5) 0.4124 (4) 0.0394 (13)
H25 0.720828 0.377781 0.435336 0.047*
C26 0.66984 (17) 0.4836 (4) 0.3968 (3) 0.0279 (9)
C27 0.67872 (18) 0.7571 (5) 0.3055 (3) 0.0321 (10)
H27 0.647754 0.774791 0.303253 0.038*
C28 0.7104 (3) 0.8409 (6) 0.3582 (5) 0.0548 (18)
H28A 0.712653 0.833643 0.417308 0.082*
H28B 0.698883 0.911374 0.337689 0.082*
H28C 0.739952 0.831668 0.353447 0.082*
C29 0.6796 (3) 0.7569 (6) 0.2156 (4) 0.0478 (15)
H29A 0.659885 0.700978 0.183023 0.072*
H29B 0.710112 0.744111 0.216873 0.072*
H29C 0.669238 0.825632 0.189213 0.072*
C30 0.6346 (2) 0.4124 (4) 0.4107 (3) 0.0316 (10)
H30 0.610950 0.458936 0.418554 0.038*
C31 0.6530 (3) 0.3440 (6) 0.4892 (4) 0.0498 (16)
H31A 0.666722 0.389301 0.538407 0.075*
H31B 0.675575 0.295508 0.482408 0.075*
H31C 0.628722 0.303066 0.497385 0.075*
C32 0.6127 (2) 0.3442 (6) 0.3331 (4) 0.0435 (14)
H32A 0.587165 0.306581 0.339576 0.065*
H32B 0.634398 0.292885 0.326952 0.065*
H32C 0.602394 0.389357 0.282955 0.065*
P2 0.40310 (3) 0.65637 (9) 0.57832 (6) 0.0196 (2)
O13 0.40161 (12) 0.5762 (3) 0.5122 (2) 0.0271 (7)
O14 0.44699 (11) 0.7068 (3) 0.6233 (2) 0.0277 (7)
O15 0.36432 (11) 0.7424 (3) 0.5400 (2) 0.0268 (7)
O16 0.38666 (10) 0.6071 (3) 0.6500 (2) 0.0207 (6)
C33 0.35548 (16) 0.7897 (4) 0.4612 (3) 0.0262 (9)
C34 0.37518 (19) 0.8881 (4) 0.4574 (4) 0.0374 (12)
C35 0.3646 (2) 0.9357 (5) 0.3782 (5) 0.0500 (17)
H35 0.377233 1.002428 0.373348 0.060*
C36 0.3366 (3) 0.8874 (6) 0.3081 (5) 0.058 (2)
H36 0.330423 0.920113 0.254656 0.070*
C37 0.3166 (3) 0.7909 (6) 0.3135 (4) 0.0518 (17)
H37 0.296772 0.759342 0.263690 0.062*
C38 0.32544 (18) 0.7394 (4) 0.3912 (3) 0.0334 (11)
C39 0.4047 (2) 0.9445 (5) 0.5350 (6) 0.058 (2)
H39A 0.422484 0.887536 0.572793 0.070* 0.57 (4)
H39B 0.407375 0.893641 0.581821 0.070* 0.43 (4)
C40A 0.3824 (9) 1.002 (2) 0.586 (2) 0.082 (6) 0.57 (4)
H40A 0.404196 1.018163 0.641604 0.123* 0.57 (4)
H40B 0.358483 0.958016 0.592595 0.123* 0.57 (4)
H40C 0.369636 1.068167 0.557448 0.123* 0.57 (4)
C41A 0.4384 (8) 1.0114 (19) 0.5135 (17) 0.080 (6) 0.57 (4)
H41A 0.460891 0.965505 0.503487 0.121* 0.57 (4)
H41B 0.452990 1.059465 0.560364 0.121* 0.57 (4)
H41C 0.423300 1.052677 0.462546 0.121* 0.57 (4)
C40B 0.3777 (10) 1.034 (2) 0.551 (3) 0.080 (8) 0.43 (4)
H40D 0.350731 1.006181 0.558900 0.121* 0.43 (4)
H40E 0.369220 1.082706 0.502804 0.121* 0.43 (4)
H40F 0.395541 1.072513 0.601940 0.121* 0.43 (4)
C41B 0.4512 (6) 0.975 (3) 0.548 (3) 0.085 (8) 0.43 (4)
H41D 0.469580 0.910790 0.555035 0.128* 0.43 (4)
H41E 0.462694 1.019171 0.598049 0.128* 0.43 (4)
H41F 0.452287 1.014068 0.498424 0.128* 0.43 (4)
C42 0.30163 (18) 0.6380 (4) 0.3977 (4) 0.0359 (12)
H42 0.321929 0.595733 0.445600 0.043*
C43 0.2902 (2) 0.5700 (5) 0.3168 (5) 0.0513 (18)
H43A 0.276166 0.503786 0.324824 0.077*
H43B 0.317642 0.554119 0.305213 0.077*
H43C 0.269586 0.609055 0.269214 0.077*
C44 0.2597 (2) 0.6629 (5) 0.4174 (4) 0.0413 (13)
H44A 0.267737 0.701560 0.470804 0.062*
H44B 0.244612 0.596832 0.421899 0.062*
H44C 0.239707 0.706440 0.372085 0.062*
C45 0.34258 (14) 0.5721 (4) 0.6342 (3) 0.0233 (8)
C46 0.33076 (16) 0.4681 (4) 0.6054 (3) 0.0279 (9)
C47 0.28661 (19) 0.4370 (5) 0.5914 (4) 0.0365 (12)
H47 0.277268 0.368134 0.570252 0.044*
C48 0.25617 (17) 0.5045 (5) 0.6078 (4) 0.0390 (13)
H48 0.226544 0.481295 0.598748 0.047*
C49 0.26909 (16) 0.6054 (5) 0.6374 (4) 0.0354 (12)
H49 0.247931 0.651035 0.648040 0.042*
C50 0.31255 (15) 0.6426 (4) 0.6521 (3) 0.0252 (9)
C51 0.3635 (2) 0.3893 (4) 0.5925 (4) 0.0349 (11)
H51 0.392547 0.426363 0.602465 0.042*
C52 0.3713 (3) 0.2997 (5) 0.6566 (5) 0.0515 (17)
H52A 0.375328 0.329392 0.712378 0.077*
H52B 0.398046 0.260064 0.658719 0.077*
H52C 0.345406 0.252199 0.639885 0.077*
C53 0.3473 (2) 0.3454 (5) 0.5018 (4) 0.0441 (14)
H53A 0.339329 0.404357 0.461655 0.066*
H53B 0.321086 0.300420 0.493272 0.066*
H53C 0.371194 0.303714 0.492801 0.066*
C54 0.32659 (17) 0.7519 (4) 0.6884 (3) 0.0286 (9)
H54 0.357329 0.765947 0.687678 0.034*
C55 0.3285 (2) 0.7536 (6) 0.7818 (4) 0.0422 (13)
H55A 0.349082 0.698622 0.813622 0.063*
H55B 0.298639 0.740184 0.783963 0.063*
H55C 0.339020 0.822963 0.806553 0.063*
C56 0.2958 (2) 0.8386 (5) 0.6375 (5) 0.0445 (14)
H56A 0.296648 0.839253 0.580044 0.067*
H56B 0.305648 0.907309 0.664184 0.067*
H56C 0.265159 0.824765 0.635536 0.067*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Mn1 0.0168 (3) 0.0254 (3) 0.0250 (3) −0.0019 (2) 0.0087 (2) −0.0027 (3)
O1 0.0203 (15) 0.046 (2) 0.0307 (18) −0.0062 (15) 0.0115 (14) −0.0132 (16)
C1 0.023 (2) 0.075 (5) 0.040 (3) −0.013 (3) 0.007 (2) −0.029 (3)
O2 0.0208 (15) 0.044 (2) 0.037 (2) −0.0079 (14) 0.0156 (14) −0.0157 (16)
C2 0.028 (2) 0.044 (3) 0.041 (3) −0.012 (2) 0.013 (2) −0.017 (2)
O3 0.0301 (19) 0.043 (2) 0.048 (2) −0.0038 (17) 0.0073 (17) 0.0173 (19)
C3 0.034 (3) 0.070 (5) 0.040 (3) 0.011 (3) 0.005 (2) 0.019 (3)
O4 0.0324 (18) 0.0347 (19) 0.036 (2) −0.0044 (15) 0.0143 (15) −0.0090 (15)
C4 0.048 (3) 0.052 (4) 0.038 (3) −0.018 (3) 0.020 (3) −0.015 (3)
O5 0.0211 (15) 0.0308 (19) 0.047 (2) 0.0036 (13) 0.0093 (15) 0.0033 (16)
C5 0.025 (2) 0.053 (4) 0.057 (4) 0.012 (2) 0.005 (2) −0.006 (3)
O6 0.061 (3) 0.047 (3) 0.037 (2) −0.008 (2) 0.007 (2) 0.0022 (19)
C6 0.067 (5) 0.064 (5) 0.076 (6) 0.001 (4) 0.016 (4) 0.028 (5)
O7 0.073 (4) 0.034 (2) 0.059 (3) −0.003 (2) 0.024 (3) 0.006 (2)
C7 0.079 (7) 0.049 (5) 0.150 (11) −0.008 (4) 0.061 (7) 0.009 (6)
O8 0.119 (6) 0.057 (3) 0.039 (3) −0.001 (3) 0.020 (3) −0.014 (2)
C8 0.094 (7) 0.052 (4) 0.058 (5) 0.017 (4) 0.013 (5) −0.019 (4)
P1 0.0157 (4) 0.0217 (5) 0.0178 (4) −0.0022 (4) 0.0048 (4) 0.0031 (4)
O9 0.0177 (13) 0.0232 (15) 0.0213 (14) −0.0026 (11) 0.0072 (11) 0.0031 (11)
O10 0.0245 (15) 0.0229 (16) 0.0292 (17) 0.0019 (12) 0.0019 (13) 0.0036 (13)
O11 0.0186 (13) 0.0254 (16) 0.0239 (15) −0.0050 (11) 0.0061 (11) 0.0035 (12)
O12 0.0161 (13) 0.0243 (15) 0.0227 (14) −0.0013 (11) 0.0078 (11) −0.0006 (12)
C9 0.0180 (18) 0.028 (2) 0.029 (2) −0.0085 (16) 0.0077 (16) −0.0026 (17)
C10 0.024 (2) 0.027 (2) 0.045 (3) −0.0078 (18) 0.010 (2) 0.001 (2)
C11 0.042 (3) 0.032 (3) 0.057 (4) −0.008 (2) 0.016 (3) −0.012 (3)
C12 0.044 (3) 0.050 (4) 0.037 (3) −0.014 (3) 0.010 (2) −0.019 (3)
C13 0.036 (3) 0.042 (3) 0.026 (2) −0.011 (2) 0.005 (2) −0.006 (2)
C14 0.0219 (19) 0.029 (2) 0.022 (2) −0.0104 (17) 0.0038 (16) −0.0028 (17)
C15 0.048 (3) 0.022 (2) 0.052 (4) −0.002 (2) 0.011 (3) 0.002 (2)
C16 0.092 (7) 0.066 (6) 0.084 (7) −0.045 (5) 0.001 (5) 0.027 (5)
C17 0.069 (6) 0.139 (11) 0.085 (7) 0.066 (7) 0.020 (6) 0.029 (7)
C18 0.024 (2) 0.031 (2) 0.022 (2) −0.0055 (18) −0.0037 (17) 0.0023 (17)
C19 0.024 (2) 0.043 (3) 0.032 (3) −0.003 (2) 0.0016 (19) 0.000 (2)
C20 0.035 (3) 0.051 (4) 0.033 (3) −0.002 (2) −0.001 (2) 0.012 (2)
C21 0.0209 (19) 0.026 (2) 0.0222 (19) −0.0022 (16) 0.0078 (16) 0.0014 (16)
C22 0.023 (2) 0.033 (2) 0.027 (2) −0.0052 (17) 0.0107 (17) 0.0023 (18)
C23 0.022 (2) 0.060 (4) 0.037 (3) −0.003 (2) 0.016 (2) −0.001 (3)
C24 0.024 (2) 0.070 (4) 0.037 (3) 0.012 (3) 0.012 (2) 0.001 (3)
C25 0.035 (3) 0.047 (3) 0.035 (3) 0.016 (2) 0.012 (2) 0.004 (2)
C26 0.030 (2) 0.029 (2) 0.026 (2) 0.0059 (18) 0.0110 (18) 0.0014 (17)
C27 0.030 (2) 0.038 (3) 0.033 (2) −0.010 (2) 0.016 (2) 0.003 (2)
C28 0.062 (4) 0.041 (4) 0.055 (4) −0.021 (3) 0.012 (3) −0.002 (3)
C29 0.058 (4) 0.057 (4) 0.033 (3) −0.011 (3) 0.022 (3) 0.011 (3)
C30 0.043 (3) 0.022 (2) 0.035 (3) 0.004 (2) 0.021 (2) 0.0016 (18)
C31 0.072 (5) 0.040 (3) 0.037 (3) −0.006 (3) 0.019 (3) 0.007 (3)
C32 0.046 (3) 0.046 (3) 0.036 (3) −0.014 (3) 0.012 (3) −0.004 (2)
P2 0.0128 (4) 0.0282 (5) 0.0168 (4) 0.0042 (4) 0.0039 (3) −0.0041 (4)
O13 0.0234 (15) 0.0327 (18) 0.0260 (16) 0.0015 (13) 0.0094 (13) −0.0055 (13)
O14 0.0175 (14) 0.0394 (19) 0.0254 (16) −0.0052 (13) 0.0064 (12) 0.0007 (14)
O15 0.0237 (15) 0.0281 (17) 0.0286 (17) 0.0090 (13) 0.0090 (13) −0.0023 (13)
O16 0.0135 (12) 0.0206 (14) 0.0271 (15) 0.0021 (11) 0.0058 (11) −0.0010 (12)
C33 0.024 (2) 0.018 (2) 0.034 (2) 0.0052 (16) 0.0073 (18) 0.0037 (17)
C34 0.029 (2) 0.017 (2) 0.061 (4) 0.0064 (18) 0.009 (2) 0.001 (2)
C35 0.045 (3) 0.025 (3) 0.079 (5) 0.008 (2) 0.019 (3) 0.019 (3)
C36 0.069 (5) 0.043 (4) 0.061 (5) 0.019 (3) 0.019 (4) 0.029 (3)
C37 0.059 (4) 0.042 (3) 0.035 (3) 0.011 (3) −0.008 (3) 0.012 (3)
C38 0.030 (2) 0.028 (2) 0.033 (3) 0.0063 (19) −0.001 (2) 0.007 (2)
C39 0.053 (4) 0.022 (3) 0.085 (5) −0.006 (3) 0.005 (4) −0.017 (3)
C40A 0.090 (11) 0.083 (13) 0.086 (13) −0.035 (10) 0.046 (10) −0.033 (10)
C41A 0.045 (9) 0.074 (11) 0.114 (14) −0.013 (8) 0.016 (9) −0.040 (10)
C40B 0.077 (12) 0.058 (13) 0.109 (17) −0.018 (10) 0.035 (13) −0.049 (12)
C41B 0.032 (9) 0.080 (14) 0.126 (18) 0.016 (9) 0.004 (10) −0.032 (13)
C42 0.026 (2) 0.027 (2) 0.038 (3) −0.0010 (18) −0.010 (2) 0.007 (2)
C43 0.030 (3) 0.043 (3) 0.069 (5) 0.002 (2) 0.002 (3) −0.021 (3)
C44 0.040 (3) 0.040 (3) 0.035 (3) −0.005 (2) 0.001 (2) −0.002 (2)
C45 0.0149 (17) 0.022 (2) 0.032 (2) −0.0008 (15) 0.0068 (16) −0.0058 (17)
C46 0.024 (2) 0.021 (2) 0.039 (3) −0.0026 (16) 0.0108 (19) −0.0031 (18)
C47 0.028 (2) 0.035 (3) 0.044 (3) −0.012 (2) 0.009 (2) −0.003 (2)
C48 0.018 (2) 0.047 (3) 0.052 (3) −0.009 (2) 0.012 (2) 0.004 (3)
C49 0.019 (2) 0.041 (3) 0.050 (3) 0.0006 (19) 0.018 (2) −0.003 (2)
C50 0.0165 (18) 0.027 (2) 0.033 (2) 0.0000 (16) 0.0099 (16) −0.0028 (18)
C51 0.039 (3) 0.022 (2) 0.041 (3) 0.005 (2) 0.010 (2) −0.003 (2)
C52 0.067 (5) 0.033 (3) 0.057 (4) 0.016 (3) 0.025 (3) 0.013 (3)
C53 0.053 (4) 0.031 (3) 0.047 (3) 0.003 (3) 0.014 (3) −0.003 (2)
C54 0.030 (2) 0.025 (2) 0.032 (2) 0.0048 (18) 0.0130 (19) −0.0057 (18)
C55 0.047 (3) 0.045 (3) 0.040 (3) 0.004 (3) 0.023 (3) −0.008 (3)
C56 0.048 (3) 0.027 (3) 0.053 (4) 0.011 (2) 0.010 (3) −0.005 (2)
Open in a new tab

Geometric parameters (Å, º)

Mn1—O1 2.146 (3) C27—C28 1.522 (9)
Mn1—O2 2.236 (4) C27—C29 1.527 (8)
Mn1—O3 2.158 (4) C27—H27 1.0000
Mn1—O4 2.213 (4) C28—H28A 0.9800
Mn1—O5 2.220 (4) C28—H28B 0.9800
Mn1—O9 2.116 (3) C28—H28C 0.9800
O1—C1 1.430 (6) C29—H29A 0.9800
O1—H1 0.85 (3) C29—H29B 0.9800
C1—H1A 0.9800 C29—H29C 0.9800
C1—H1B 0.9800 C30—C32 1.522 (8)
C1—H1C 0.9800 C30—C31 1.523 (8)
O2—C2 1.443 (6) C30—H30 1.0000
O2—H2 0.82 (3) C31—H31A 0.9800
C2—H2A 0.9800 C31—H31B 0.9800
C2—H2B 0.9800 C31—H31C 0.9800
C2—H2C 0.9800 C32—H32A 0.9800
O3—C3 1.432 (8) C32—H32B 0.9800
O3—H3 0.86 (3) C32—H32C 0.9800
C3—H3A 0.9800 P2—O13 1.496 (4)
C3—H3B 0.9800 P2—O14 1.488 (3)
C3—H3C 0.9800 P2—O15 1.607 (3)
O4—C4 1.448 (8) P2—O16 1.600 (3)
O4—H4 0.85 (3) O15—C33 1.397 (6)
C4—H4A 0.9800 O16—C45 1.409 (5)
C4—H4B 0.9800 C33—C38 1.394 (7)
C4—H4C 0.9800 C33—C34 1.405 (7)
O5—C5 1.416 (7) C34—C35 1.397 (10)
O5—H5 0.85 (3) C34—C39 1.506 (10)
C5—H5A 0.9800 C35—C36 1.360 (12)
C5—H5B 0.9800 C35—H35 0.9500
C5—H5C 0.9800 C36—C37 1.392 (11)
O6—C6 1.408 (10) C36—H36 0.9500
O6—H6 0.86 (3) C37—C38 1.405 (8)
C6—H6A 0.9800 C37—H37 0.9500
C6—H6B 0.9800 C38—C42 1.513 (8)
C6—H6C 0.9800 C39—C41B 1.473 (13)
O7—C7 1.419 (11) C39—C40A 1.482 (13)
O7—H7 0.85 (3) C39—C40B 1.504 (13)
C7—H7A 0.9800 C39—C41A 1.505 (13)
C7—H7B 0.9800 C39—H39A 1.0000
C7—H7C 0.9800 C39—H39B 1.0000
O8—C8 1.377 (11) C40A—H40A 0.9800
O8—H8 0.85 (3) C40A—H40B 0.9800
C8—H8A 0.9800 C40A—H40C 0.9800
C8—H8B 0.9800 C41A—H41A 0.9800
C8—H8C 0.9800 C41A—H41B 0.9800
P1—O9 1.503 (3) C41A—H41C 0.9800
P1—O10 1.488 (3) C40B—H40D 0.9800
P1—O11 1.600 (3) C40B—H40E 0.9800
P1—O12 1.597 (3) C40B—H40F 0.9800
O11—C9 1.410 (6) C41B—H41D 0.9800
O12—C21 1.403 (5) C41B—H41E 0.9800
C9—C10 1.392 (8) C41B—H41F 0.9800
C9—C14 1.415 (7) C42—C44 1.515 (9)
C10—C11 1.404 (9) C42—C43 1.547 (9)
C10—C15 1.517 (9) C42—H42 1.0000
C11—C12 1.391 (10) C43—H43A 0.9800
C11—H11 0.9500 C43—H43B 0.9800
C12—C13 1.392 (10) C43—H43C 0.9800
C12—H12 0.9500 C44—H44A 0.9800
C13—C14 1.387 (7) C44—H44B 0.9800
C13—H13 0.9500 C44—H44C 0.9800
C14—C18 1.493 (8) C45—C46 1.408 (6)
C15—C17 1.494 (12) C45—C50 1.414 (6)
C15—C16 1.523 (10) C46—C47 1.401 (7)
C15—H15 1.0000 C46—C51 1.511 (7)
C16—H16A 0.9800 C47—C48 1.389 (9)
C16—H16B 0.9800 C47—H47 0.9500
C16—H16C 0.9800 C48—C49 1.380 (9)
C17—H17A 0.9800 C48—H48 0.9500
C17—H17B 0.9800 C49—C50 1.402 (6)
C17—H17C 0.9800 C49—H49 0.9500
C18—C19 1.528 (8) C50—C54 1.517 (7)
C18—C20 1.529 (8) C51—C52 1.527 (9)
C18—H18 1.0000 C51—C53 1.542 (9)
C19—H19A 0.9800 C51—H51 1.0000
C19—H19B 0.9800 C52—H52A 0.9800
C19—H19C 0.9800 C52—H52B 0.9800
C20—H20A 0.9800 C52—H52C 0.9800
C20—H20B 0.9800 C53—H53A 0.9800
C20—H20C 0.9800 C53—H53B 0.9800
C21—C22 1.387 (6) C53—H53C 0.9800
C21—C26 1.389 (7) C54—C56 1.525 (8)
C22—C23 1.397 (7) C54—C55 1.556 (8)
C22—C27 1.512 (8) C54—H54 1.0000
C23—C24 1.370 (10) C55—H55A 0.9800
C23—H23 0.9500 C55—H55B 0.9800
C24—C25 1.385 (10) C55—H55C 0.9800
C24—H24 0.9500 C56—H56A 0.9800
C25—C26 1.390 (7) C56—H56B 0.9800
C25—H25 0.9500 C56—H56C 0.9800
C26—C30 1.519 (8)
O9—Mn1—O1 176.85 (14) C28—C27—H27 108.4
O9—Mn1—O3 89.81 (14) C29—C27—H27 108.4
O1—Mn1—O3 92.26 (16) C27—C28—H28A 109.5
O9—Mn1—O4 90.71 (14) C27—C28—H28B 109.5
O1—Mn1—O4 86.88 (14) H28A—C28—H28B 109.5
O3—Mn1—O4 91.29 (18) C27—C28—H28C 109.5
O9—Mn1—O5 88.84 (13) H28A—C28—H28C 109.5
O1—Mn1—O5 89.09 (15) H28B—C28—H28C 109.5
O3—Mn1—O5 178.62 (16) C27—C29—H29A 109.5
O4—Mn1—O5 89.03 (16) C27—C29—H29B 109.5
O9—Mn1—O2 93.86 (13) H29A—C29—H29B 109.5
O1—Mn1—O2 88.51 (13) C27—C29—H29C 109.5
O3—Mn1—O2 89.98 (18) H29A—C29—H29C 109.5
O4—Mn1—O2 175.26 (14) H29B—C29—H29C 109.5
O5—Mn1—O2 89.81 (16) C26—C30—C32 110.4 (4)
C1—O1—Mn1 125.4 (3) C26—C30—C31 112.6 (5)
C1—O1—H1 109.5 C32—C30—C31 110.8 (5)
Mn1—O1—H1 103.8 C26—C30—H30 107.6
O1—C1—H1A 109.5 C32—C30—H30 107.6
O1—C1—H1B 109.5 C31—C30—H30 107.6
H1A—C1—H1B 109.5 C30—C31—H31A 109.5
O1—C1—H1C 109.5 C30—C31—H31B 109.5
H1A—C1—H1C 109.5 H31A—C31—H31B 109.5
H1B—C1—H1C 109.5 C30—C31—H31C 109.5
C2—O2—Mn1 123.8 (3) H31A—C31—H31C 109.5
C2—O2—H2 109.5 H31B—C31—H31C 109.5
Mn1—O2—H2 117.6 C30—C32—H32A 109.5
O2—C2—H2A 109.5 C30—C32—H32B 109.5
O2—C2—H2B 109.5 H32A—C32—H32B 109.5
H2A—C2—H2B 109.5 C30—C32—H32C 109.5
O2—C2—H2C 109.5 H32A—C32—H32C 109.5
H2A—C2—H2C 109.5 H32B—C32—H32C 109.5
H2B—C2—H2C 109.5 O14—P2—O13 117.1 (2)
C3—O3—Mn1 120.8 (4) O14—P2—O16 105.98 (18)
C3—O3—H3 109.5 O13—P2—O16 111.4 (2)
Mn1—O3—H3 122.2 O14—P2—O15 112.0 (2)
O3—C3—H3A 109.5 O13—P2—O15 109.5 (2)
O3—C3—H3B 109.5 O16—P2—O15 99.33 (18)
H3A—C3—H3B 109.5 C33—O15—P2 123.4 (3)
O3—C3—H3C 109.5 C45—O16—P2 122.9 (3)
H3A—C3—H3C 109.5 C38—C33—O15 117.9 (4)
H3B—C3—H3C 109.5 C38—C33—C34 123.6 (5)
C4—O4—Mn1 125.3 (4) O15—C33—C34 118.4 (5)
C4—O4—H4 109.5 C35—C34—C33 117.4 (6)
Mn1—O4—H4 125.0 C35—C34—C39 120.2 (6)
O4—C4—H4A 109.5 C33—C34—C39 122.4 (6)
O4—C4—H4B 109.5 C36—C35—C34 120.7 (6)
H4A—C4—H4B 109.5 C36—C35—H35 119.6
O4—C4—H4C 109.5 C34—C35—H35 119.6
H4A—C4—H4C 109.5 C35—C36—C37 121.0 (7)
H4B—C4—H4C 109.5 C35—C36—H36 119.5
C5—O5—Mn1 125.9 (4) C37—C36—H36 119.5
C5—O5—H5 109.5 C36—C37—C38 121.1 (7)
Mn1—O5—H5 102.9 C36—C37—H37 119.4
O5—C5—H5A 109.5 C38—C37—H37 119.4
O5—C5—H5B 109.5 C33—C38—C37 116.1 (5)
H5A—C5—H5B 109.5 C33—C38—C42 122.8 (5)
O5—C5—H5C 109.5 C37—C38—C42 121.0 (5)
H5A—C5—H5C 109.5 C41B—C39—C40B 112.9 (17)
H5B—C5—H5C 109.5 C40A—C39—C41A 112.9 (13)
C6—O6—H6 109.5 C41B—C39—C34 123.2 (16)
O6—C6—H6A 109.5 C40A—C39—C34 117.1 (13)
O6—C6—H6B 109.5 C40B—C39—C34 106.7 (15)
H6A—C6—H6B 109.5 C41A—C39—C34 109.9 (11)
O6—C6—H6C 109.5 C40A—C39—H39A 105.3
H6A—C6—H6C 109.5 C41A—C39—H39A 105.3
H6B—C6—H6C 109.5 C34—C39—H39A 105.3
C7—O7—H7 109.5 C41B—C39—H39B 104.0
O7—C7—H7A 109.5 C40B—C39—H39B 104.0
O7—C7—H7B 109.5 C34—C39—H39B 104.0
H7A—C7—H7B 109.5 C39—C40A—H40A 109.5
O7—C7—H7C 109.5 C39—C40A—H40B 109.5
H7A—C7—H7C 109.5 H40A—C40A—H40B 109.5
H7B—C7—H7C 109.5 C39—C40A—H40C 109.5
C8—O8—H8 109.5 H40A—C40A—H40C 109.5
O8—C8—H8A 109.5 H40B—C40A—H40C 109.5
O8—C8—H8B 109.5 C39—C41A—H41A 109.5
H8A—C8—H8B 109.5 C39—C41A—H41B 109.5
O8—C8—H8C 109.5 H41A—C41A—H41B 109.5
H8A—C8—H8C 109.5 C39—C41A—H41C 109.5
H8B—C8—H8C 109.5 H41A—C41A—H41C 109.5
O10—P1—O9 115.2 (2) H41B—C41A—H41C 109.5
O10—P1—O12 105.8 (2) C39—C40B—H40D 109.5
O9—P1—O12 112.90 (18) C39—C40B—H40E 109.5
O10—P1—O11 112.08 (19) H40D—C40B—H40E 109.5
O9—P1—O11 109.62 (18) C39—C40B—H40F 109.5
O12—P1—O11 100.29 (18) H40D—C40B—H40F 109.5
P1—O9—Mn1 132.20 (19) H40E—C40B—H40F 109.5
C9—O11—P1 122.4 (3) C39—C41B—H41D 109.5
C21—O12—P1 127.0 (3) C39—C41B—H41E 109.5
C10—C9—O11 119.1 (5) H41D—C41B—H41E 109.5
C10—C9—C14 123.5 (5) C39—C41B—H41F 109.5
O11—C9—C14 117.3 (4) H41D—C41B—H41F 109.5
C9—C10—C11 116.8 (5) H41E—C41B—H41F 109.5
C9—C10—C15 122.4 (5) C38—C42—C44 109.9 (5)
C11—C10—C15 120.7 (5) C38—C42—C43 112.3 (6)
C12—C11—C10 121.2 (6) C44—C42—C43 110.5 (5)
C12—C11—H11 119.4 C38—C42—H42 108.0
C10—C11—H11 119.4 C44—C42—H42 108.0
C11—C12—C13 120.1 (6) C43—C42—H42 108.0
C11—C12—H12 119.9 C42—C43—H43A 109.5
C13—C12—H12 119.9 C42—C43—H43B 109.5
C14—C13—C12 121.1 (6) H43A—C43—H43B 109.5
C14—C13—H13 119.4 C42—C43—H43C 109.5
C12—C13—H13 119.4 H43A—C43—H43C 109.5
C13—C14—C9 117.1 (5) H43B—C43—H43C 109.5
C13—C14—C18 121.5 (5) C42—C44—H44A 109.5
C9—C14—C18 121.3 (4) C42—C44—H44B 109.5
C17—C15—C10 112.8 (7) H44A—C44—H44B 109.5
C17—C15—C16 113.0 (9) C42—C44—H44C 109.5
C10—C15—C16 110.9 (6) H44A—C44—H44C 109.5
C17—C15—H15 106.6 H44B—C44—H44C 109.5
C10—C15—H15 106.6 C46—C45—O16 119.3 (4)
C16—C15—H15 106.6 C46—C45—C50 122.8 (4)
C15—C16—H16A 109.5 O16—C45—C50 117.8 (4)
C15—C16—H16B 109.5 C47—C46—C45 117.0 (5)
H16A—C16—H16B 109.5 C47—C46—C51 119.6 (5)
C15—C16—H16C 109.5 C45—C46—C51 123.3 (4)
H16A—C16—H16C 109.5 C48—C47—C46 121.6 (5)
H16B—C16—H16C 109.5 C48—C47—H47 119.2
C15—C17—H17A 109.5 C46—C47—H47 119.2
C15—C17—H17B 109.5 C49—C48—C47 119.8 (5)
H17A—C17—H17B 109.5 C49—C48—H48 120.1
C15—C17—H17C 109.5 C47—C48—H48 120.1
H17A—C17—H17C 109.5 C48—C49—C50 121.9 (5)
H17B—C17—H17C 109.5 C48—C49—H49 119.1
C14—C18—C19 111.0 (4) C50—C49—H49 119.1
C14—C18—C20 113.6 (5) C49—C50—C45 116.8 (5)
C19—C18—C20 109.8 (5) C49—C50—C54 120.9 (4)
C14—C18—H18 107.4 C45—C50—C54 122.2 (4)
C19—C18—H18 107.4 C46—C51—C52 109.9 (5)
C20—C18—H18 107.4 C46—C51—C53 111.5 (5)
C18—C19—H19A 109.5 C52—C51—C53 110.8 (5)
C18—C19—H19B 109.5 C46—C51—H51 108.2
H19A—C19—H19B 109.5 C52—C51—H51 108.2
C18—C19—H19C 109.5 C53—C51—H51 108.2
H19A—C19—H19C 109.5 C51—C52—H52A 109.5
H19B—C19—H19C 109.5 C51—C52—H52B 109.5
C18—C20—H20A 109.5 H52A—C52—H52B 109.5
C18—C20—H20B 109.5 C51—C52—H52C 109.5
H20A—C20—H20B 109.5 H52A—C52—H52C 109.5
C18—C20—H20C 109.5 H52B—C52—H52C 109.5
H20A—C20—H20C 109.5 C51—C53—H53A 109.5
H20B—C20—H20C 109.5 C51—C53—H53B 109.5
C22—C21—C26 123.2 (5) H53A—C53—H53B 109.5
C22—C21—O12 118.3 (4) C51—C53—H53C 109.5
C26—C21—O12 118.3 (4) H53A—C53—H53C 109.5
C21—C22—C23 116.6 (5) H53B—C53—H53C 109.5
C21—C22—C27 122.6 (4) C50—C54—C56 112.5 (5)
C23—C22—C27 120.8 (5) C50—C54—C55 109.0 (5)
C24—C23—C22 122.4 (5) C56—C54—C55 110.9 (5)
C24—C23—H23 118.8 C50—C54—H54 108.1
C22—C23—H23 118.8 C56—C54—H54 108.1
C23—C24—C25 119.0 (5) C55—C54—H54 108.1
C23—C24—H24 120.5 C54—C55—H55A 109.5
C25—C24—H24 120.5 C54—C55—H55B 109.5
C24—C25—C26 121.4 (6) H55A—C55—H55B 109.5
C24—C25—H25 119.3 C54—C55—H55C 109.5
C26—C25—H25 119.3 H55A—C55—H55C 109.5
C21—C26—C25 117.4 (5) H55B—C55—H55C 109.5
C21—C26—C30 121.9 (4) C54—C56—H56A 109.5
C25—C26—C30 120.5 (5) C54—C56—H56B 109.5
C22—C27—C28 111.2 (5) H56A—C56—H56B 109.5
C22—C27—C29 110.1 (5) C54—C56—H56C 109.5
C28—C27—C29 110.4 (5) H56A—C56—H56C 109.5
C22—C27—H27 108.4 H56B—C56—H56C 109.5
O10—P1—O9—Mn1 25.7 (3) O13—P2—O15—C33 −45.8 (4)
O12—P1—O9—Mn1 −95.9 (3) O16—P2—O15—C33 −162.6 (4)
O11—P1—O9—Mn1 153.2 (2) O14—P2—O16—C45 166.3 (3)
O10—P1—O11—C9 90.7 (4) O13—P2—O16—C45 −65.3 (4)
O9—P1—O11—C9 −38.5 (4) O15—P2—O16—C45 50.1 (4)
O12—P1—O11—C9 −157.5 (3) P2—O15—C33—C38 88.9 (5)
O10—P1—O12—C21 146.7 (4) P2—O15—C33—C34 −94.9 (5)
O9—P1—O12—C21 −86.5 (4) C38—C33—C34—C35 −1.8 (8)
O11—P1—O12—C21 30.1 (4) O15—C33—C34—C35 −177.8 (5)
P1—O11—C9—C10 −88.0 (5) C38—C33—C34—C39 175.1 (5)
P1—O11—C9—C14 95.9 (4) O15—C33—C34—C39 −1.0 (8)
O11—C9—C10—C11 −177.9 (4) C33—C34—C35—C36 −0.4 (10)
C14—C9—C10—C11 −2.2 (7) C39—C34—C35—C36 −177.3 (7)
O11—C9—C10—C15 −1.1 (7) C34—C35—C36—C37 1.7 (12)
C14—C9—C10—C15 174.7 (5) C35—C36—C37—C38 −1.0 (12)
C9—C10—C11—C12 −0.4 (8) O15—C33—C38—C37 178.5 (5)
C15—C10—C11—C12 −177.3 (6) C34—C33—C38—C37 2.4 (8)
C10—C11—C12—C13 1.6 (10) O15—C33—C38—C42 1.3 (8)
C11—C12—C13—C14 −0.3 (9) C34—C33—C38—C42 −174.8 (5)
C12—C13—C14—C9 −2.1 (8) C36—C37—C38—C33 −1.0 (10)
C12—C13—C14—C18 175.2 (5) C36—C37—C38—C42 176.2 (7)
C10—C9—C14—C13 3.4 (7) C35—C34—C39—C41B −61 (2)
O11—C9—C14—C13 179.2 (4) C33—C34—C39—C41B 122 (2)
C10—C9—C14—C18 −173.9 (4) C35—C34—C39—C40A 98.1 (18)
O11—C9—C14—C18 1.9 (6) C33—C34—C39—C40A −78.7 (17)
C9—C10—C15—C17 125.9 (8) C35—C34—C39—C40B 72 (2)
C11—C10—C15—C17 −57.4 (10) C33—C34—C39—C40B −105 (2)
C9—C10—C15—C16 −106.3 (8) C35—C34—C39—C41A −32.5 (15)
C11—C10—C15—C16 70.4 (9) C33—C34—C39—C41A 150.7 (14)
C13—C14—C18—C19 −102.7 (5) C33—C38—C42—C44 85.4 (6)
C9—C14—C18—C19 74.5 (5) C37—C38—C42—C44 −91.7 (7)
C13—C14—C18—C20 21.6 (7) C33—C38—C42—C43 −151.2 (5)
C9—C14—C18—C20 −161.2 (4) C37—C38—C42—C43 31.8 (8)
P1—O12—C21—C22 −90.2 (5) P2—O16—C45—C46 86.4 (5)
P1—O12—C21—C26 94.9 (5) P2—O16—C45—C50 −96.5 (5)
C26—C21—C22—C23 −2.2 (8) O16—C45—C46—C47 179.4 (5)
O12—C21—C22—C23 −176.9 (4) C50—C45—C46—C47 2.5 (8)
C26—C21—C22—C27 177.6 (5) O16—C45—C46—C51 1.9 (8)
O12—C21—C22—C27 2.9 (7) C50—C45—C46—C51 −175.0 (5)
C21—C22—C23—C24 1.1 (8) C45—C46—C47—C48 −2.0 (9)
C27—C22—C23—C24 −178.7 (6) C51—C46—C47—C48 175.6 (6)
C22—C23—C24—C25 0.1 (9) C46—C47—C48—C49 1.0 (10)
C23—C24—C25—C26 −0.4 (9) C47—C48—C49—C50 −0.4 (10)
C22—C21—C26—C25 2.0 (8) C48—C49—C50—C45 0.8 (9)
O12—C21—C26—C25 176.6 (5) C48—C49—C50—C54 −177.1 (6)
C22—C21—C26—C30 −174.6 (5) C46—C45—C50—C49 −1.9 (8)
O12—C21—C26—C30 0.1 (7) O16—C45—C50—C49 −178.9 (5)
C24—C25—C26—C21 −0.6 (8) C46—C45—C50—C54 176.0 (5)
C24—C25—C26—C30 176.0 (5) O16—C45—C50—C54 −1.0 (7)
C21—C22—C27—C28 124.6 (6) C47—C46—C51—C52 −64.9 (7)
C23—C22—C27—C28 −55.6 (7) C45—C46—C51—C52 112.5 (6)
C21—C22—C27—C29 −112.7 (6) C47—C46—C51—C53 58.4 (7)
C23—C22—C27—C29 67.1 (7) C45—C46—C51—C53 −124.2 (6)
C21—C26—C30—C32 91.5 (6) C49—C50—C54—C56 −54.2 (7)
C25—C26—C30—C32 −85.0 (7) C45—C50—C54—C56 127.9 (6)
C21—C26—C30—C31 −144.2 (5) C49—C50—C54—C55 69.1 (6)
C25—C26—C30—C31 39.4 (7) C45—C50—C54—C55 −108.7 (6)
O14—P2—O15—C33 85.9 (4)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O1—H1···O13 0.85 1.79 2.537 (5) 145
O2—H2···O14 0.82 1.99 2.724 (5) 148
O3—H3···O7 0.86 1.79 2.644 (6) 170
O4—H4···O6 0.85 1.95 2.700 (7) 147
O5—H5···O10 0.85 1.84 2.661 (5) 163
O6—H6···O14i 0.86 1.89 2.708 (6) 157
O7—H7···O8 0.85 1.88 2.697 (8) 159
O8—H8···O10ii 0.85 1.86 2.708 (7) 174
C1—H1B···O4 0.98 2.49 3.162 (7) 125
C7—H7B···O1 0.98 2.66 3.570 (13) 154
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Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2.

Funding Statement

This work was funded by Russian Academy of Sciences grant .

References

  1. Bian, G.-Q., Kuroda-Sowa, T., Konaka, H., Hatano, M., Maekawa, M., Munakata, M., Miyasaka, H. & Yamashita, M. (2004). Inorg. Chem. 43, 4790–4792. [DOI] [PubMed]
  2. Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc.,Madison, Wisconsin, USA.
  3. Bruker (2015). TOPAS. Bruker AXS, Karlsruhe, Germany.
  4. Dean, N. S., Mokry, L. M., Bond, M. R., Mohan, M., Otieno, T., O’Connor, C. J., Spartalian, K. & Carrano, C. J. (1997). Inorg. Chem. 36, 1424–1430. [DOI] [PubMed]
  5. Dey, R., Bhattacharya, B., Colacio, E. & Ghoshal, D. (2013). Dalton Trans. 42, 2094–2106. [DOI] [PubMed]
  6. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
  7. Halm, R. L. (1980). Patent US4193885 (to Dow Corning Corporation).
  8. Kishimoto, K., Koda, Y. & Sasaki, Sh. (1976). Patent US4070343 (to Toray Silicone Company).
  9. Kobzova, R. I., Tubyanskaya, G. S., Oparina, E. M., Zaitsev, V. A. & Egorova, A. A. (1966). Chem. Technol. Fuels Oils, 2, 270–271.
  10. Kuroda-Sowa, T., Bian, G.-Q., Hatano, M., Konaka, H., Fukuda, S., Miyoshi, S., Maekawa, M., Munakata, M., Miyasaka, H. & Yamashita, M. (2005). Polyhedron, 24, 2680–2690.
  11. Kuroda-Sowa, T., Fukuda, S., Miyoshi, S., Maekawa, M., Munakata, M., Miyasaka, H. & Yamashita, M. (2002). Chem. Lett. 31, 682–683.
  12. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
  13. Minyaev, M. E., Korchagina, S. A., Tavtorkin, A. N., Churakov, A. V. & Nifant’ev, I. E. (2018b). Acta Cryst. C74, 673–682. [DOI] [PubMed]
  14. Minyaev, M. E., Nifant’ev, I. E., Tavtorkin, A. N., Korchagina, S. A., Zeynalova, S. S., Ananyev, I. V. & Churakov, A. V. (2017). Acta Cryst. C73, 820–827. [DOI] [PubMed]
  15. Minyaev, M. E., Nifant’ev, I. E., Tavtorkin, A. N., Korchagina, S. A. & Zeynalova, S. S. (2015). Acta Cryst. E71, 443–446. [DOI] [PMC free article] [PubMed]
  16. Minyaev, M. E., Tavtorkin, A. N., Korchagina, S. A., Bondarenko, G. N., Churakov, A. V. & Nifant’ev, I. E. (2018a). Acta Cryst. C74, 590–598. [DOI] [PubMed]
  17. Murugavel, R. & Sathiyendiran, M. (2001). Chem. Lett. 30, 84–85.
  18. Nakajima, T., Yamashiro, C., Taya, M., Kure, B. & Tanase, T. (2016). Eur. J. Inorg. Chem. pp. 2764–2773.
  19. Nielsen, J. M. (1961). Patent US3009876 (to General Electric Company).
  20. Nifant’ev, I. E., Tavtorkin, A. N., Korchagina, S. A., Gavrilenko, I. F., Glebova, N. N., Kostitsyna, N. N., Yakovlev, V. A., Bondarenko, G. N. & Filatova, M. P. (2014). Appl. Catal. Gen. 478, 219–227.
  21. Nifant’ev, I. E., Tavtorkin, A. N., Shlyahtin, A. V., Korchagina, S. A., Gavrilenko, I. F., Glebova, N. N. & Churakov, A. V. (2013). Dalton Trans. 42, 1223–1230. [DOI] [PubMed]
  22. Pothiraja, R., Rajakannu, P., Vishnoi, P., Butcher, R. J. & Murugavel, R. (2014). Inorg. Chim. Acta, 414, 264–273.
  23. Pothiraja, R., Sathiyendiran, M., Butcher, R. J. & Murugavel, R. (2004). Inorg. Chem. 43, 7585–7587. [DOI] [PubMed]
  24. Pothiraja, R., Sathiyendiran, M., Butcher, R. J. & Murugavel, R. (2005). Inorg. Chem. 44, 6314–6323. [DOI] [PubMed]
  25. Rafizadeh, M., Amani, V. & Aghayan, H. (2006). Acta Cryst. E62, m2450–m2452.
  26. Rafizadeh, M., Amani, V. & Farajian, H. (2007). Z. Anorg. Allg. Chem. 633, 1143–1145.
  27. Rajakannu, P., Howlader, R., Kalita, A. Ch., Butcher, R. J. & Murugavel, R. (2015). Inorg. Chem. Front. 2, 55–66.
  28. Rozanova, N. L., Klimov, A. K., Zverev, O. V., Mukhanova, E. E., Gusev, V. K., Raskin, Ju. E., Markina, E. B. & Minsker, M. Z. (1995). Patent RU2034868 (to the All-Russian Research Institute for Oil Refining).
  29. Sathiyendiran, M. & Murugavel, R. (2002). Inorg. Chem. 41, 6404–6411. [DOI] [PubMed]
  30. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  31. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
  32. Shiraishi, H., Jikido, R., Matsufuji, K., Nakanishi, T., Shiga, T., Ohba, M., Sakai, K., Kitagawa, H. & Okawa, H. (2005). Bull. Chem. Soc. Jpn, 78, 1072–1076.
  33. Sobolevskiy, M. B., Skorokhodov, I. I., Ditsent, V. E. & Sobolevskaya, L. V. (1970). Proceedings of the USSR conference ‘Synthesis and study of the efficiency of chemicals for polymer materials’ ,Tambov, pp. 194–208. (In Russian.)
  34. Swihart, T. J. & Jones, J. E. (1985). Patent US 4528313 (to Dow Corning Corporation).
  35. Van Allsburg, K. M., Anzenberg, E., Drisdell, W. S., Yano, J. & Tilley, T. D. (2015). Chem. Eur. J. 21, 4646–4654. [DOI] [PubMed]
  36. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
  37. Yashiro, M., Higuchi, M., Komiyama, M. & Ishii, Y. (2003). Bull. Chem. Soc. Jpn, 76, 1813–1817.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018012859/pj2055sup1.cif

e-74-01433-sup1.cif (1.1MB, cif)
Click here for additional data file. (9.1KB, cdx)

Supporting information file. DOI: 10.1107/S2056989018012859/pj2055Isup3.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018012859/pj2055Isup4.hkl

e-74-01433-Isup4.hkl (1.5MB, hkl)

Powder XRD data and single crystal X-ray diffraction studies. DOI: 10.1107/S2056989018012859/pj2055sup5.pdf

e-74-01433-sup5.pdf (276.2KB, pdf)

CCDC reference: 1867164

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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