polyoxometalates\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

Synthesis and characterization of hybrid Anderson hexa­molybdoaluminates(III) functionalized with indometacin or cinnamic acid

aUniversität Wien, Fakultät für Chemie, Institut für Biophysikalische Chemie, Althanstrasse 14, Wien 1090, Austria, bUniversität Wien, Facultät für Chemie, Zentrum für Röntgenstrukturanalyse, Währinger Strasse 42, Wien 1090, Austria, and cUniversität Wien, Institut für Mineralogie und Kristallographie, Althanstrasse 14, Wien 1090, Austria
*Correspondence e-mail: annette.rompel@univie.ac.at

Edited by J. R. Galán-Mascarós, Institute of Chemical Research of Catalonia (ICIQ), Spain (Received 12 June 2018; accepted 5 September 2018; online 24 October 2018)

The single-side Al-centred tris-functionalized hybrid organic–inorganic Anderson polyoxomolybdates (C16H36N)3[Al(OH)3Mo6O18(OCH2)3CNH(C10H8O)]·C9H7N·4CH3OH·5H2O (AlMo6-NH-Cin; Cin is cinnamic acid, C10H9O2) and (C16H36N)3[Al(OH)3Mo6O18(OCH2)3CNH(C19H15ClNO3)]·9H2O (AlMo6-NH-Indo; Indo is indometacin, C19H16ClNO4) have been prepared in a mild three-step synthesis and structurally characterized by single-crystal X-ray diffraction, 1H NMR and IR spectroscopies and elemental analysis. Both AlMo6-NH-Cin and AlMo6-NH-Indo crystallize in the ortho­rhom­bic space group Pbca. The anti­bacterial activities of AlMo6-NH-Cin and AlMo6-NH-Indo against the Gram-negative human mucosal pathogen Moraxella catarrhalis were investigated by determination of the minimum inhibitory concentration, which is 32 µg ml−1 for AlMo6-NH-Cin and 256 µg ml−1 for AlMo6-NH-Indo.

1. Introduction

Polyoxometalates (POMs), an exceptional class of metal–oxide clusters with various compositions, exhibit an oxygen-rich surface with strong coordination potential (Pope, 1983[Pope, M. (1983). In Heteropoly and Isopoly Oxometalates. Berlin: Springer.]). They have attracted much attention owing to their unique catalytic (Wang & Yang, 2015[Wang, S.-S. & Yang, G.-Y. (2015). Chem. Rev. 115, 4893-4962.]), redox (Gumerova & Rompel, 2018[Gumerova, N. I. & Rompel, A. (2018). Nat. Rev. Chem. 2, article No. 0112.]), magnetic (Clemente-Juan et al., 2012[Clemente-Juan, J. M., Coronado, E. & Gaita-Ariño, A. (2012). Chem. Soc. Rev. 41, 7464-7478.]) and bioactive properties (Bijelic & Rompel, 2015[Bijelic, A. & Rompel, A. (2015). Coord. Chem. Rev. 299, 22-38.], 2017[Bijelic, A. & Rompel, A. (2017). Acc. Chem. Res. 50, 1441-1448.]; Molitor et al., 2017[Molitor, C., Bijelic, A. & Rompel, A. (2017). IUCrJ, 4, 734-740.]; Fu et al., 2015[Fu, L., Gao, H., Yan, M., Shouzhu, L., Li, X., Dai, Z. & Liu, S. (2015). Small, 11, 2938-2945.]; Bijelic et al., 2018a[Bijelic, A., Aureliano, M. & Rompel, A. (2018a). Angew. Chem. Int. Ed. In the press. doi:10.1002/anie.201803868.],b[Bijelic, A., Aureliano, M. & Rompel, A. (2018b). Chem. Commun. 54, 1153-1169.]) and constitute promising building blocks for advanced materials. Recently, increasing effort has been devoted to the introduction of organic and metal–organic units into the metal oxide frameworks in order to functionalize POM materials (Dolbecq et al., 2010[Dolbecq, A., Dumas, E., Mayer, C. R. & Mialane, P. (2010). Chem. Rev. 110, 6009-6048.]). Among the various synthetic strategies for the organic functionalization of POMs, alk­oxy­lation has gained much attention due to the diversity and tunability of alkoxyl ligands, especially when using the disk-shaped Anderson-type anions [Xn+HmM6O24](12–nm)– (M = Mo6+ and W6+; X = heteroatom, e.g. Te6+ and I7+ for A-type with m = 0, or Al3+ and Ni2+ for B-type with m = 6), with a wide spectrum of central heteroatoms (Blazevic & Rompel, 2016[Blazevic, A. & Rompel, A. (2016). Coord. Chem. Rev. 307, 42-64.]; Zhang et al., 2018[Zhang, J., Huang, Y., Li, G. & Wei, Y. (2018). Coord. Chem. Rev. In the press. doi: 10.1016/j.ccr.2017.10.025.]). In particular, after Hasenknopf et al. (2002[Hasenknopf, B., Delmont, R., Herson, P. & Gouzerh, P. (2002). Eur. J. Inorg. Chem. pp. 1081-1087]) had pioneered and established the synthesis of tris-derivatives of Anderson polyoxomolybdates (POMos), this archetype has been widely used as starting materials for the attachment of various tris [tris­(hy­droxy­meth­yl)methane]-based organic ligands [RC(CH2OH)3, de­noted R-Tris]. If the R group itself is reactive (–NH2, –CH2OH etc.), post-functionalization with a variety of organic mol­ecules, including ligands containing aromatic units (Al-Sayed et al., 2015[Al-Sayed, E., Blazevic, A., Roller, A. & Rompel, A. (2015). Chem. Eur. J. 21, 17800-17807.]) or alkyl chains (Rosnes et al., 2013[Rosnes, M. H., Musumeci, C., Yvon, C., Macdonell, A., Pradeep, C. P., Sartorio, C., Long, D.-L., Pignataro, B. & Cronin, L. (2013). Small, 9, 2316-2324.]) via imine, amide or ester-bond formation, is possible. The resulting hybrid materials were used in supra­molecular self-assembly (Macdonell et al., 2015[Macdonell, A., Johnson, N. A. B., Surman, A. J. & Cronin, L. (2015). J. Am. Chem. Soc. 137, 5662-5665.]) or for the formation of metal–organic frameworks (MOFs; Li et al., 2016[Li, X.-X., Wang, Y.-X., Wang, R.-H., Cui, C.-Y., Tian, C.-B. & Yang, G.-Y. (2016). Angew. Chem. Int. Ed. 55, 6462-6466.]). Major application fields are bio-inorganic (Yvon et al., 2014[Yvon, C., Surman, A. J., Hutin, M., Alex, J., Smith, B. O., Long, D.-L. & Cronin, L. (2014). Angew. Chem. Int. Ed. 53, 3336-3341.]), nano-structured (Song et al., 2009[Song, Y.-F., McMillan, N., Long, D.-L., Kane, S., Malm, J., Riehle, M. O., Pradeep, C. P., Gadegaard, N. & Cronin, L. (2009). J. Am. Chem. Soc. 131, 1340-1341.]), energy storage (Ji et al., 2015[Ji, Y., Hu, J., Huang, L., Chen, W., Streb, C. & Song, Y.-F. (2015). Chem. Eur. J. 21, 6469-6474.]), optical (Boulmier et al., 2018[Boulmier, A., Vacher, A., Zang, D., Yang, S., Saad, A., Marrot, J., Oms, O., Mialane, P., Ledoux, I., Ruhlmann, L., Lorcy, D. & Dolbecq, A. (2018). Inorg. Chem. 57, 3742-3752.]) and photochemical (Schaming et al., 2010[Schaming, D., Allain, C., Farha, R., Goldmann, M., Lobstein, S., Giraudeau, A., Hasenknopf, B. & Ruhlmann, L. (2010). Langmuir, 26, 5101-5109.]) materials.

Herein, two biologically active mol­ecules, namely indometacin and cinnamic acid, were used to post-functionalize the Al-centred Anderson anion [Al(OH)3Mo6O18(OCH2)3CNH2]3− (Wu et al., 2011[Wu, P., Yin, P., Zhang, J., Hao, J., Xiao, Z. & Wei, Y. (2011). Chem. Eur. J. 17, 12002-12005.]) via amidation reaction, resulting in two novel single-side grafted hybrid organic–inorganic Anderson-type POMos, namely (TBA)3[Al(OH)3Mo6O18(OCH2)3CNH(C10H8O)]·C9H7N·4CH3OH·5H2O (AlMo6-NH-Cin; Cin is cinnamic acid and TBA is tetra­butyl­ammonium) and (TBA)3[Al(OH)3Mo6O18(OCH2)3CNH(C19H15ClNO3)]·9H2O (AlMo6-NH-Indo; Indo is indometacin). Both com­pounds were structurally characterized by single-crystal X-ray diffraction, IR spectroscopy and elemental analysis. Their anti­bacterial activity against Moraxella catarrhalis was investigated by determination of the minimum inhibitory concentration (MIC).

2. Experimental

2.1. Synthesis and crystallization

2.1.1. Synthesis of AlMo6-NH-Indo

Na3(H2O)6[Al(OH)6Mo6O18]·2H2O (AlMo6) was prepared according to a published procedure (Shivaiah & Das, 2005[Shivaiah, V. & Das, S. (2005). J. Chem. Sci. 117, 227-233.]). The single-side attachment of Tris-NH2 to AlMo6 was achieved through a modified published procedure (Wu et al., 2011[Wu, P., Yin, P., Zhang, J., Hao, J., Xiao, Z. & Wei, Y. (2011). Chem. Eur. J. 17, 12002-12005.]). AlMo6 (3.84 g, 3.28 mmol) was dissolved in water (20.5 ml) and heated to reflux, when Tris-NH2 (0.735 g, 6.02 mmol) was added. After refluxing for 3 h, the solvent was removed by vacuum. The white powder obtained was redissolved with deionized H2O and then centrifuged to remove unreacted educts. Tetra­butyl­ammonium bromide (TBABr) (4.12 g, 12.8 mmol) was added to the solution and a white precipitate appeared. In order to functionalize AlMo6-NH2 with indometacin, a mixture of indometacin (0.172 g, 0.500 mmol), AlMo6-NH2 (1.05 g, 0.519 mmol) and EEDQ (N-eth­oxy­carbonyl-2-eth­oxy-1,2-di­hydro­quinoline; 0.143 g, 0.570 mmol) in CH3CN (9.00 ml) was stirred at 323 K for 24 h. The solvent was collected and removed by vacuum. The remaining yellow solid was redissolved in an MeOH–H2O mixture (2:1 v/v), followed by the addition of TBABr (0.5 g). After several weeks, crystals suitable for single-crystal X-ray diffraction were obtained [yield 2.3 g, 32% (based on Mo)]. FT–IR (cm−1): 324 (s), 368 (s), 395 (m), 442 (s), 484 (s), 505 (m), 534 (m, sh), 567 (m), 611 (m), 650 (s), 736 (m), 754 (m), 796 (m), 833 (w), 850 (m), 897 (s), 918 (s), 939 (s), 1012 (w, sh), 1027 (m), 1053 (m), 1072 (m), 1091 (m), 1122 (m), 1151 (m), 1174 (w), 1224 (m), 1290 (w), 1315 (m), 1336 (w, sh), 1361 (m), 1369 (m), 1396 (sh), 1458 (m), 1479 (m), 1552 (m), 1564 (m), 1610 (m), 1677 (m), 2871 (m), 2933 (m), 2960 (m), 3081 (w), 3322 (m, br). Elemental analysis for C71H145AlClMo6N5O36 (calculated) (%): C 38.38 (37.27), H 6.75 (6.61), N 3.06 (3.06), Cl 1.29 (1.55), O 22.3 (25.17). 1H NMR (500.32 MHz, CD3CN, 298 K): δ 0.96 (t, 36H), 1.34 (m, 24H), 1.59 (m, 24H), 3.53 (m, 24H), 3.62 (s, 2H), 3.81 (s, 3H), 2.15 (s, 3H), 6.66 (dd, 1H), 6.85 (d, 1H), 6.96 (d, 1H), 7.02 (d, 1H), 7.55 (d, 2H), 7.64 (d, 2H), 64 (s, 6H in CH2μ3-O groups).

2.1.2. Synthesis of AlMo6-NH-Cin

The preparation of AlMo6-NH-Cin was similar to that of AlMo6-NH-Indo, except that cinnamic acid (0.074 g, 0.500 mmol) was used instead of indometacin [yield 1.9 g, 27% (based on Mo)]. FT–IR (cm−1): 324 (s), 368 (s), 441 (s), 482 (s), 503 (m), 518 (m), 534 (m), 565 (m), 578 (m), 607 (m), 649 (s), 832 (w), 898 (s), 916 (s), 939 (s), 983 (w), 1035 (m), 1060 (m), 1112 (w), 1118 (m), 1153 (m), 1193 (w), 1228 (m), 1284 (w), 1323 (w), 1348 (m), 1380 (m), 1458 (m), 1479 (m), 1548 (m, br), 1575 (w), 1627 (m), 1668 (m), 1720 (w), 1731 (w, sh), 2874 (m), 2933 (m), 2960 (m), 3062 (w), 3290 (m, br), 3404 (m, br). Elemental analysis for C73H154AlMo6N5O32.6 (calculated) (%): C 36.48 (36.92), H 6.50 (7.00), N 2.92 (3.16), O 22.16 (23.10). 1H NMR (500.32 MHz, CD3CN, 298 K): δ 0.98 (t, 36H), 1.37 (m, 24H in TBA), 1.61 (m, 24H), 3.11 (d, 12H), 3.51 (m, 24H), 5.12 (q, 4H), 6.46 (d, 1H), 7.37 (d, 1H), 7.47–7.91 (m, 5H), 64 (s, 6H in CH2μ3-O groups).

2.2. IR spectroscopy

Both compounds were identified by IR measurements on a Bruker Vertex70 IR Spectrometer equipped with a single-reflection diamond-ATR (attenuated total reflectance) unit in the range 4000–300 cm−1.

2.3. 1H NMR

NMR spectra were recorded on a Bruker FT–NMR Avance III 500 MHz instrument at 500.32 (1H) MHz in CD3CN at ambient temperature. Chemical shifts were referenced relative to the solvent signal for 1H nucleus.

2.4. Elemental analysis

The determination of C/H/N/O/Cl was carried out using an `EA 1108 CHNS-O' elemental analyzer by Carlo Erba Instruments at the Mikroanalytisches Laboratorium, University of Vienna.

2.5. MIC determination

Minimum inhibitory concentrations (MICs) were determined by the broth microdilution method according to guidelines of the Clinical Laboratory Standards Institute (Wikler, 2009[Wikler, M. A. (2009). Approved Standard M7-A8. https://clsi.org/standards/products/microbiology/documents/m07/.]). Double dilutions of tested compounds in 96-well microtiter plates were prepared in the concentration range 1–256 µg ml−1. M. catarrhalis (ATCC 23246) was grown on Columbia agar with 5% defibrinated sheep blood. Inocula were prepared by the direct colony suspension method and plates were inoculated with 5 × 10−4 CFU per well. Results were determined by visual inspection after 20–22 h of incubation at 310 K in ambient air. Testing was performed by the standard broth microdilution method with azithromycin (Lode et al., 1996[Lode, H., Borner, K., Koeppe, P. & Schaberg, T. (1996). J. Antimicrob. Chemother. 37, 1-8.]) as the reference anti­biotic to assess test validity. MIC determinatiom was performed at the School of Medicine, University of Zagreb, Croatia.

2.6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The positions of the independent H atoms were obtained by difference Fourier techniques and were refined with free isotropic displacement parameters. Fixed isotropic displacement parameters for all H atoms with a value equal to 1.5Ueq of the corresponding OH or H2O group atom were assigned. Restrained distances for D—H bonds were applied to avoid short D—H⋯H—D inter­actions. In the case of disordered groups, some bonds were added to or deleted from the connectivity array.

Table 1
Experimental details

  AlMo6-NH-Cin AlMo6-NH-Indo
Crystal data
Chemical formula (C16H36N)3[Al(OH)3Mo6O18(OCH2)3CNH(C10H8O)]·C9H7N·4CH3OH·5H2O (C16H36N)3[Al(OH)3Mo6O18(OCH2)3CNH(C19H15ClNO3)]·9H2O
Mr 2227.19 2288.02
Crystal system, space group Orthorhombic, Pbca Orthorhombic, Pbca
Temperature (K) 100 200
a, b, c (Å) 16.1062 (17), 26.512 (3), 45.569 (5) 21.8904 (6), 23.9848 (6), 37.719 (1)
V3) 19458 (3) 19803.9 (9)
Z 8 8
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.84 0.85
Crystal size (mm) 0.23 × 0.15 × 0.03 0.15 × 0.12 × 0.05
 
Data collection
Diffractometer Bruker APEXII CCD Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.666, 0.746 0.678, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 293657, 17800, 15423 374956, 18115, 15743
Rint 0.066 0.050
(sin θ/λ)max−1) 0.602 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.144, 1.24 0.029, 0.075, 1.06
No. of reflections 17800 18115
No. of parameters 1129 1166
No. of restraints 39 53
H-atom treatment H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.27, −1.04 1.18, −0.64
Computer programs: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

3. Results and discussion

AlMo6-NH-Cin and AlMo6-NH-Indo were prepared via post-functionalization by pre-forming the hybrid cluster AlMo6-NH2 which was modified by amidation reactions (Fig. 1[link]). The fact that single-side grafted anions were obtained supports an earlier theory claiming that the aqueous solvent is a key factor for the formation of single-sided Anderson derivatives (Wu et al., 2011[Wu, P., Yin, P., Zhang, J., Hao, J., Xiao, Z. & Wei, Y. (2011). Chem. Eur. J. 17, 12002-12005.]; Blazevic et al., 2015[Blazevic, A., Al-Sayed, E., Roller, A., Giester, G. & Rompel, A. (2015). Chem. Eur. J. 21, 17800-17807.]; Gumerova et al., 2016[Gumerova, N. I., Roller, A. & Rompel, A. (2016). Eur. J. Inorg. Chem. pp. 5507-5511.]).

[Figure 1]
Figure 1
Functionalization of [Al(OH)6Mo6O18]3− (AlMo6) with the Tris-NH2 ligand, followed by further post-functionalization of [Al(OH)3Mo6O18(OCH2)3CNH2]3− (AlMo6-NH2) with indometacin or cinnamic acid, respectively. EEDQ is N-eth­oxy­carbonyl-2-eth­oxy-1,2-di­hydro­quinoline. Colour code: {MoO6} octa­hedra orange and {AlO6} octa­hedra yellow, with C atoms black, N blue, Cl green, H grey and O red.

X-ray crystallographic analysis shows that the asymmetric units in AlMo6-NH-Cin and AlMo6-NH-Indo consist of the hybrid Anderson anion, three TBA counter-cations, solvent mol­ecules and, in the case of AlMo6-NH-Cin, one mol­ecule of quinoline as a by-product from EEDQ decomposition. The structural analysis revealed that both compounds crystallize in the ortho­rhom­bic space group Pbca. AlMo6-NH-Cin and AlMo6-NH-Indo both show the characteristic Anderson-type structure, with a central {AlO6} octa­hedron surrounded by six edge-shared {MoO6} octa­hedra that form a planar array of distorted octa­hedra (Fig. 1[link]). Three different coordination modes of O atoms are found in the structure: six triple-bridged O atoms (denoted μ3-O) connect the heteroatom and two Mo atoms, six double-bridged O atoms (denoted μ2-O) connect two Mo atoms and two terminal O atoms (denoted Ot) are connected to each of the six Mo atoms. The bond lengths of the three different binding modes are summarized in Table 2[link] and are in good agreement with other tris-functionalized Anderson POMos (Wu et al., 2011[Wu, P., Yin, P., Zhang, J., Hao, J., Xiao, Z. & Wei, Y. (2011). Chem. Eur. J. 17, 12002-12005.]; Al-Sayed et al., 2015[Al-Sayed, E., Blazevic, A., Roller, A. & Rompel, A. (2015). Chem. Eur. J. 21, 17800-17807.]; Blazevic et al., 2015[Blazevic, A., Al-Sayed, E., Roller, A., Giester, G. & Rompel, A. (2015). Chem. Eur. J. 21, 17800-17807.]).

Table 2
Selected bond lengths (Å) in AlMo6—NH-Cin and AlMo6—NH-Indo

  AlMo6—NH-Cin AlMo6—NH-Indo
Mo—μ3-O 2.291 (4)–2.391 (4) 2.3068 (19)–2.3632 (18)
Mo—μ2-O 1.910 (4)–1.941 (5) 1.912 (2)–1.944 (2)
Mo—Ot 1.694 (5)–1.722 (5) 1.696 (2)–1.711 (2)
Al—μ3-O 1.864 (5)–1.923 (4) 1.863 (2)–1.927 (2)

The tris-ligand caps one side of the planar hexa­gon by binding to three μ3-O atoms of the {AlO6} fragment, whereas on the other side of AlMo6-NH-Cin and AlMo6-NH-Indo, the respective μ3-O atoms according to BVS calculations [−1.16 (O2), −1.20 (O4) and −1.19 (O6) for AlMo6-NH-Indo, and −1.15 (O1), −1.16 (O3) and −1.18 (O5) for AlMo6-NH-Indo, calculated according to (Brown & Altermatt, 1985[Brown, I. D. & Altermatt, D. (1985). Acta Cryst. B41, 244-247.])] are protonated.

The crystal packing of AlMo6-NH-Cin can be described as alternate layers of POMo anions and TBA counter-cations, which are repeated along the c axis (Fig. 2[link]). The orientations of the hybrid polyanions along the c and b axes also alternate with an angle of approximately 85° between the planes of the inorganic Anderson `disks' (Fig. 2[link]a). The attached ligands are turned towards each other along the bc plane. The distances between the inorganic POMo skeletons along the a axis are around 9.5 Å, and around 14 Å along the b axis. All four lattice water mol­ecules are situated in front of the undecorated side of the anion and form strong inter­molecular hydrogen bonds with μ3-O—H fragments, with short distances in the region 1.85–1.94 Å.

[Figure 2]
Figure 2
The crystal packing of AlMo6-NH-Cin, viewed along (a) the c axis and (b) the a axis. The TBA counter-cations and the solvent mol­ecules have been omitted for clarity. Colour code: {MoO6} octa­hedra orange and {AlO6} octa­hedra yellow, with C atoms black, N blue, H grey and O red.

The crystal packing of AlMo6-NH-Indo is similar to that of AlMo6-NH-Cin and can be described as alternate layers of POMo anions and TBA counter-cations, which are repeated along the a axis (Fig. 3[link]). The orientation of the hybrid polyanions along the c and b axes is the same, with the grafted sides turned in different directions (Fig. 3[link]b). The distances between inorganic POMos along the a axis are around 12 Å, around 11 Å along the b axis and approximately 5 Å along the c axis. Six of nine lattice water mol­ecules are situated in front of the unfunctionalized side and form strong inter­molecular hydrogen bonds with μ3-O—H fragments and Ot atoms, with distances in the range 1.86–2.08 Å. The crystallographic refinement results for both AlMo6-NH-Cin and AlMo6-NH-Indo suggest no ππ inter­actions between the aromatic ring and the C=C double bond based on geometry and separation.

[Figure 3]
Figure 3
The crystal packing of AlMo6-NH-Indo, viewed along (a) the a axis and (b) the b axis. The TBA counter-cations and the solvent mol­ecules have been omitted for clarity. Colour code: {MoO6} octa­hedra orange and {AlO6} octa­hedra yellow, with C atoms black, N blue, H grey and O red.

The IR spectra of AlMo6-NH-Cin and AlMo6-NH-Indo (Fig. 4[link]) are typical for Anderson-type POMos and the characteristic peaks of the core structure are all in agreement with the peaks observed in the spectrum of Na3(H2O)6[Al(OH)6Mo6O18]·2H2O (Shivaiah & Das, 2005[Shivaiah, V. & Das, S. (2005). J. Chem. Sci. 117, 227-233.]). The stretching vibrations of the terminal Mo=O units appear at 939 cm−1, whereas the peaks in the region from 300 to 920 cm−1 correspond to the anti­symmetric and symmetric deformation vibrations of the Mo—O—Mo and Mo—O—Al bridging fragments. The peaks appearing in the region 1030–1125 cm−1 could be assigned to C—O stretching vibrations, indicating the successful grafting of the tris ligands.

[Figure 4]
Figure 4
The IR spectra of AlMo6-NH-Cin and AlMo6-NH-Indo in the region from 4000 to 300 cm−1.

The anti­bacterial activities of AlMo6-NH-Cin and AlMo6-NH-Indo against the Gram-negative human mucosal pathogen Moraxella catarrhalis (Karalus & Campagnari, 2000[Karalus, R. & Campagnari, A. (2000). Microbes Infect. 2, 547-559.]) were investigated by determination of the minimum inhibitory concentration (MIC). AlMo6-NH-Cin shows a higher activity, with MIC values of 32 µg ml−1, while AlMo6-NH-Indo shows an MIC value of 256 µg ml−1. The MIC values for both compounds are much higher than for the clinically applied drug azithromycin, which has an MIC value of 0.06 µg ml−1. Taking into account that AlMo6-NH-Cin and AlMo6-NH-Indo have the same inorganic POMo part, counter-cations and net charge, it can be assumed that their anti­bacterial activities differs only due to the organic ligands attached. It is known that cinnamic acid and its derivatives exhibit anti­microbial activity against pathogenic and spoilage bacteria (Sova, 2012[Sova, M. (2012). Mini Rev. Med. Chem. 12, 749-767.]), indometacin in its turn, as a nonsteroidal anti-inflammatory drug (Lucas, 2016[Lucas, S. (2016). Headache: J. Head Face Pain, 56, 436-446.]), showed bacteriostatic activity against Helicobacter pylori (Shirin et al., 2006[Shirin, H., Moss, S. F., Kancherla, S., Kancherla, K., Holt, P. R., Weinstein, I. B. & Sordillo, E. M. (2006). J. Gastroenterol. Hepatol. 21, 1388-1393.]), whereas pure inorganic Ni- and Te-centred Anderson-type POMos and POTs are inactive (MIC > 256 µg ml−1) against M. catarrhalis (Gumerova et al., 2018[Gumerova, N. I., Al-Sayed, E., Krivosudský, L., Čipčić-Paljetak, H., Verbanac, D. & Rompel, A. (2018). Front. Chem. 6, article No. 336.]). Thereby, the activity of AlMo6-NH-Cin is caused by the synergistic effect of AlMo6 and cinnamic acid, which is not the case for AlMo6-NH-Indo. The preliminary results obtained here show that not only does the activity of the attached ligand play a role, but also synergism with POMs strongly influences the properties of the hybrid compounds.

4. Conclusion

The success in synthesizing AlMo6-NH-Cin and AlMo6-NH-Indo shows the versatility and reproducibility of the post-functionalization protocol for the alk­oxy­lation of Anderson POMs. The attachment of bioactive ligands makes the hybrid Anderson POMos reported herein potentially superior to pure inorganic structures for anti­bacterial applications.

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2013) for mo_ambl235_pbca; 'APEX2 (Bruker, 2013) for taco104_0m. For both structures, cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(mo_ambl235_pbca) top
Crystal data top
C13H17AlMo6NO25·4.73(H2O)·3(CH4O)·2(C16H36N)·C16H35.5N·C9H7NDx = 1.521 Mg m3
Mr = 2227.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9772 reflections
a = 16.1062 (17) Åθ = 2.3–29.5°
b = 26.512 (3) ŵ = 0.84 mm1
c = 45.569 (5) ÅT = 100 K
V = 19458 (3) Å3Plate, clear colourless
Z = 80.23 × 0.15 × 0.03 mm
F(000) = 9222
Data collection top
Bruker APEXII CCD
diffractometer
15423 reflections with I > 2σ(I)
φ and ω scansRint = 0.066
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
θmax = 25.4°, θmin = 2.3°
Tmin = 0.666, Tmax = 0.746h = 1919
293657 measured reflectionsk = 3131
17800 independent reflectionsl = 5454
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.0201P)2 + 204.0739P]
where P = (Fo2 + 2Fc2)/3
S = 1.24(Δ/σ)max = 0.001
17800 reflectionsΔρmax = 1.27 e Å3
1129 parametersΔρmin = 1.04 e Å3
39 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. _olex2_refinement_description

1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2. Restrained distances O6-H6 = O2-H2 0.88 with sigma of 0.02 O4-H4 0.88 with sigma of 0.02 H1BB-H6 = H1BB-H1DB = H1AA-H4 2.2 with sigma of 0.04 H29S-O16_$1 1.9 with sigma of 0.08 O1C-H1DB 1.85 with sigma of 0.015 H2-H1CB 2.1 with sigma of 0.015 H1CB-O30S 1.95 with sigma of 0.03 O1A-H1CA 1.95 with sigma of 0.03 H73B-H1CB_$1 2.1 with sigma of 0.02 O30S-C74S ~ O27S-C72S ~ O29S-C73S with sigma of 0.02 C61-C60 ~ C49-C48 ~ C53-C52 ~ C57-C56 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C59) ~ Ueq, Uanis(C60) ~ Ueq, Uanis(C61) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Others Sof(O30S)=Sof(H30S)=Sof(C74S)=Sof(H74A)=Sof(H74B)=Sof(H74C)=1-FVAR(1) Sof(O29S)=Sof(H29S)=Sof(C73S)=Sof(H73A)=Sof(H73B)=Sof(H73C)=FVAR(1) Sof(O28S)=Sof(H28C)=Sof(H28D)=FVAR(2) Fixed Sof: H58A(0.75) H58B(0.75) 5.a Free rotating group: O1A(H1AA,H1AB), O1B(H1BA,H1BB), O1C(H1CA,H1CB), O1D(H1DA,H1DB), O28S(H28C,H28D) 5.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A, H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C46(H46A,H46B), C47(H47A, H47B), C48(H48A,H48B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B) 5.c Aromatic/amide H refined with riding coordinates: N1(H1), C6(H6A), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C62(H62), C63(H63), C64(H64), C66(H66), C67(H67), C68(H68), C69(H69) 5.d Tetrahedral OH refined with riding coordinates: O27S(H27S) 5.e Idealised Me refined as rotating group: C71S(H71A,H71B,H71C), C72S(H72A,H72B,H72C), C73S(H73A,H73B,H73C), C17(H17A, H17B,H17C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C45(H45A,H45B, H45C), C49(H49A,H49B,H49C), C53(H53A,H53B,H53C), C57(H57A,H57B,H57C), C61(H61A, H61B,H61C), C74S(H74A,H74B,H74C) 5.f Idealised tetrahedral OH refined as rotating group: O26S(H26S), O29S(H29S), O30S(H30S)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Mo10.28978 (3)0.12375 (2)0.15448 (2)0.02046 (13)
Mo20.26650 (4)0.12931 (2)0.08205 (2)0.02403 (14)
Mo30.14206 (4)0.21510 (2)0.05222 (2)0.02528 (14)
Mo40.03843 (3)0.29405 (2)0.09578 (2)0.02120 (13)
Mo50.05897 (3)0.28718 (2)0.16801 (2)0.01787 (13)
Mo60.19091 (3)0.20442 (2)0.19676 (2)0.01845 (13)
Al10.16091 (11)0.20713 (7)0.12491 (4)0.0157 (4)
O10.2752 (2)0.18828 (16)0.11964 (9)0.0180 (9)
O20.1387 (3)0.16351 (17)0.09338 (10)0.0218 (10)
H20.097 (3)0.144 (2)0.0881 (13)0.012 (16)*
O30.1719 (3)0.25809 (16)0.09537 (9)0.0184 (9)
O40.0525 (3)0.23026 (17)0.12979 (10)0.0197 (9)
H40.008 (3)0.212 (3)0.1280 (18)0.04 (2)*
O50.1917 (2)0.25372 (16)0.15493 (9)0.0157 (9)
O60.1597 (3)0.15885 (16)0.15511 (9)0.0174 (9)
H60.118 (3)0.1382 (19)0.1566 (14)0.017 (18)*
O70.2477 (3)0.09393 (17)0.11854 (10)0.0245 (10)
O80.2519 (3)0.18994 (18)0.05924 (9)0.0240 (10)
O90.0397 (3)0.23830 (18)0.06851 (10)0.0258 (11)
O100.0778 (3)0.32261 (16)0.13199 (9)0.0196 (9)
O110.0791 (3)0.22767 (16)0.19056 (9)0.0185 (9)
O120.2936 (3)0.18129 (17)0.18001 (10)0.0207 (10)
O130.2642 (3)0.07662 (18)0.17817 (11)0.0292 (11)
O140.3934 (3)0.11791 (18)0.14810 (10)0.0273 (11)
O150.3719 (3)0.1254 (2)0.07897 (11)0.0331 (12)
O160.2271 (3)0.0845 (2)0.05880 (11)0.0381 (13)
O170.1043 (3)0.1703 (2)0.02849 (11)0.0400 (14)
O180.1693 (3)0.2650 (2)0.03089 (11)0.0353 (13)
O190.0692 (3)0.34262 (19)0.07379 (10)0.0301 (11)
O200.0660 (3)0.30034 (19)0.09925 (11)0.0303 (11)
O210.0460 (3)0.29147 (19)0.17170 (11)0.0290 (11)
O220.0991 (3)0.33269 (17)0.19056 (10)0.0247 (10)
O230.2301 (3)0.25227 (18)0.21712 (10)0.0251 (10)
O240.1690 (3)0.15656 (18)0.22111 (10)0.0256 (10)
O250.4523 (3)0.29582 (19)0.15522 (11)0.0295 (11)
N10.3683 (3)0.3169 (2)0.11673 (12)0.0227 (12)
H10.36470.33680.10130.027*
C10.3020 (4)0.2795 (2)0.12057 (13)0.0173 (13)
C20.3386 (4)0.2264 (3)0.11847 (14)0.0226 (14)
H2A0.36970.22310.09980.027*
H2B0.37810.22110.13480.027*
C30.2426 (4)0.2908 (3)0.09541 (14)0.0218 (14)
H3A0.22350.32620.09700.026*
H3B0.27260.28720.07660.026*
C40.2593 (4)0.2878 (3)0.15033 (13)0.0195 (14)
H4A0.30050.28340.16620.023*
H4B0.23830.32290.15130.023*
C50.4350 (4)0.3237 (3)0.13473 (15)0.0243 (15)
C60.4829 (4)0.3685 (3)0.12725 (16)0.0257 (15)
H6A0.47410.38550.10920.031*
C70.5408 (5)0.3856 (3)0.14672 (18)0.0345 (18)
H70.55120.36450.16320.041*
C80.5883 (5)0.4321 (4)0.1454 (2)0.047 (2)
C90.5936 (6)0.4596 (4)0.1207 (2)0.056 (3)
H90.56750.44830.10320.067*
C100.6382 (7)0.5054 (4)0.1209 (3)0.068 (3)
H100.64080.52520.10350.082*
C110.6775 (8)0.5215 (4)0.1456 (3)0.075 (3)
H110.70700.55260.14550.090*
C120.6745 (9)0.4930 (5)0.1707 (3)0.096 (5)
H120.70270.50370.18790.115*
C130.6298 (7)0.4485 (5)0.1704 (2)0.075 (4)
H130.62730.42860.18780.090*
O1A0.0631 (3)0.1555 (2)0.12810 (13)0.0389 (13)
H1AA0.10940.17240.12890.058*
H1AB0.05680.13810.14410.058*
O1B0.0314 (3)0.0941 (2)0.16390 (12)0.0348 (12)
H1BA0.03420.08750.18250.052*
H1BB0.04790.06780.15390.052*
O1C0.0080 (4)0.0977 (2)0.08468 (14)0.0544 (17)
H1CA0.03620.10780.09390.082*
H1CB0.00250.10430.06600.082*
O1D0.1030 (4)0.0368 (2)0.11923 (15)0.0524 (16)
H1DA0.15360.04810.12060.079*
H1DB0.07410.05670.10800.079*
O26S0.0689 (4)0.0732 (2)0.22182 (15)0.0498 (16)
H26S0.10190.09750.22380.075*
C71S0.1139 (7)0.0279 (4)0.2216 (3)0.069 (3)
H71A0.07950.00100.21320.103*
H71B0.12930.01880.24170.103*
H71C0.16420.03210.20980.103*
O27S0.3490 (4)0.3846 (3)0.06798 (15)0.071 (2)
H27S0.37480.41190.06980.106*
O28S0.4326 (6)0.4679 (3)0.0745 (2)0.058 (3)0.726 (18)
H28C0.43990.48150.09170.087*0.726 (18)
H28D0.39810.48800.06560.087*0.726 (18)
O29S0.3705 (9)0.5161 (5)0.0291 (3)0.033 (4)0.395 (11)
H29S0.32810.52850.03700.049*0.395 (11)
C72S0.2841 (9)0.3912 (7)0.0500 (4)0.150 (9)
H72A0.29970.38130.03000.225*
H72B0.26770.42680.05010.225*
H72C0.23750.37040.05670.225*
C73S0.4340 (15)0.5502 (9)0.0303 (6)0.090 (14)0.395 (11)
H73A0.45580.55590.01050.134*0.395 (11)
H73B0.47830.53690.04290.134*0.395 (11)
H73C0.41350.58210.03840.134*0.395 (11)
N20.0810 (5)0.3123 (3)0.00127 (15)0.0482 (19)
C140.1458 (6)0.3528 (4)0.0044 (2)0.051 (2)
H14A0.12350.37650.01930.061*
H14B0.19560.33660.01300.061*
C150.1723 (7)0.3829 (4)0.0223 (2)0.064 (3)
H15A0.12410.40180.03010.077*
H15B0.19220.35970.03780.077*
C160.2419 (8)0.4202 (4)0.0142 (2)0.066 (3)
H16A0.22050.44370.00090.079*
H16B0.28820.40100.00520.079*
C170.2762 (8)0.4511 (4)0.0399 (2)0.075 (3)
H17A0.29250.42830.05580.113*
H17B0.32470.47040.03330.113*
H17C0.23330.47430.04690.113*
C180.0016 (6)0.3362 (4)0.01053 (19)0.050 (2)
H18A0.00770.35620.02860.059*
H18B0.04120.30890.01540.059*
C190.0413 (7)0.3702 (4)0.0125 (2)0.062 (3)
H19A0.04390.35260.03160.075*
H19B0.00800.40130.01490.075*
C200.1284 (7)0.3834 (4)0.0020 (2)0.063 (3)
H20A0.12510.39790.01790.076*
H20B0.16190.35210.00090.076*
C210.1713 (8)0.4207 (5)0.0222 (3)0.082 (4)
H21A0.14370.45350.02090.122*
H21B0.16840.40840.04250.122*
H21C0.22960.42420.01640.122*
C220.0701 (6)0.2825 (3)0.02684 (18)0.046 (2)
H22A0.12300.26520.03140.055*
H22B0.05870.30640.04300.055*
C230.0022 (7)0.2441 (4)0.0260 (2)0.065 (3)
H23A0.01360.21990.01000.079*
H23B0.05090.26120.02160.079*
C240.0066 (7)0.2156 (4)0.0545 (2)0.060 (3)
H24A0.04530.19670.05810.072*
H24B0.01340.24020.07060.072*
C250.0783 (8)0.1792 (4)0.0553 (2)0.074 (3)
H25A0.08170.16380.07480.110*
H25B0.06970.15280.04050.110*
H25C0.13000.19730.05110.110*
C260.1065 (6)0.2782 (4)0.0263 (2)0.054 (3)
H26A0.10770.29830.04460.065*
H26B0.06350.25180.02870.065*
C270.1914 (6)0.2521 (4)0.0226 (2)0.058 (3)
H27A0.23570.27790.02150.070*
H27B0.19190.23250.00420.070*
C280.2079 (6)0.2179 (5)0.0479 (2)0.070 (3)
H28A0.26590.20580.04660.084*
H28B0.20250.23740.06630.084*
C290.1502 (7)0.1722 (5)0.0495 (3)0.087 (4)
H29A0.15330.15330.03100.130*
H29B0.16730.15030.06570.130*
H29C0.09300.18360.05270.130*
N30.4974 (4)0.2232 (2)0.22640 (13)0.0315 (14)
C300.4703 (5)0.1913 (3)0.25231 (17)0.0361 (18)
H30A0.51070.16350.25480.043*
H30B0.47260.21240.27020.043*
C310.3843 (5)0.1688 (3)0.24991 (18)0.0368 (18)
H31A0.38120.14760.23210.044*
H31B0.34310.19630.24790.044*
C320.3622 (6)0.1366 (3)0.27686 (18)0.043 (2)
H32A0.31070.11750.27280.051*
H32B0.40730.11190.28050.051*
C330.3500 (7)0.1686 (4)0.3039 (2)0.064 (3)
H33A0.40330.18320.30980.096*
H33B0.32830.14760.31990.096*
H33C0.31050.19570.29960.096*
C340.4381 (4)0.2667 (3)0.22307 (16)0.0285 (16)
H34A0.38290.25310.21780.034*
H34B0.45720.28780.20650.034*
C350.4282 (5)0.3001 (3)0.2497 (2)0.047 (2)
H35A0.39370.28240.26450.057*
H35B0.48350.30620.25850.057*
C360.3889 (6)0.3494 (3)0.2424 (2)0.056 (3)
H36A0.33240.34330.23460.067*
H36B0.42170.36610.22680.067*
C370.3831 (7)0.3852 (4)0.2695 (3)0.077 (4)
H37A0.43900.39170.27710.116*
H37B0.34940.36920.28480.116*
H37C0.35730.41710.26360.116*
C380.5846 (4)0.2430 (3)0.23305 (16)0.0318 (17)
H38A0.58160.26570.25030.038*
H38B0.62050.21410.23840.038*
C390.6246 (5)0.2713 (3)0.20769 (17)0.0375 (19)
H39A0.58140.29080.19720.045*
H39B0.64850.24670.19370.045*
C400.6927 (5)0.3071 (3)0.21802 (17)0.0363 (18)
H40A0.72230.32070.20070.044*
H40B0.73320.28810.23000.044*
C410.6581 (6)0.3513 (3)0.2363 (2)0.049 (2)
H41A0.70180.37650.23920.074*
H41B0.63940.33870.25540.074*
H41C0.61130.36660.22590.074*
C420.4946 (5)0.1935 (3)0.19805 (19)0.0392 (19)
H42A0.43560.18880.19260.047*
H42B0.52040.21440.18250.047*
C430.5360 (7)0.1423 (4)0.1975 (3)0.067 (3)
H43A0.51430.12360.21470.080*
H43B0.51490.12480.17990.080*
C440.6231 (7)0.1355 (4)0.1976 (2)0.065 (3)
H44A0.64500.14510.21710.078*
H44B0.64810.15860.18300.078*
C450.6508 (6)0.0804 (4)0.1905 (2)0.056 (3)
H45A0.63240.07130.17080.084*
H45B0.62600.05720.20480.084*
H45C0.71150.07800.19160.084*
N40.4373 (5)0.0337 (3)0.14557 (19)0.052 (2)
C460.5074 (6)0.0727 (3)0.1469 (2)0.048 (2)
H46A0.49460.09670.16290.057*
H46B0.50710.09200.12830.057*
C470.5948 (6)0.0526 (3)0.1518 (3)0.059 (3)
H47A0.60200.04310.17270.071*
H47B0.60380.02220.13960.071*
C480.6581 (7)0.0935 (4)0.1435 (3)0.068 (3)
H48A0.71120.08660.15370.082*
H48B0.63760.12670.15020.082*
C490.6731 (9)0.0953 (5)0.1110 (3)0.104 (5)
H49A0.69400.06260.10430.156*
H49B0.62100.10310.10090.156*
H49C0.71420.12150.10660.156*
C500.4381 (5)0.0003 (3)0.1722 (2)0.044 (2)
H50A0.49350.01560.17360.053*
H50B0.39710.02700.16910.053*
C510.4196 (6)0.0252 (3)0.2009 (2)0.049 (2)
H51A0.45940.05300.20420.059*
H51B0.36300.03960.20040.059*
C520.4259 (7)0.0129 (4)0.2260 (2)0.058 (3)
H52A0.48380.02510.22740.070*
H52B0.39000.04220.22160.070*
C530.4009 (8)0.0088 (4)0.2547 (2)0.080 (4)
H53A0.43310.03950.25840.120*
H53B0.34160.01710.25420.120*
H53C0.41160.01580.27030.120*
C540.3575 (6)0.0644 (3)0.1442 (2)0.053 (3)
H54A0.35930.08610.12650.064*
H54B0.35510.08680.16150.064*
C550.2790 (6)0.0332 (3)0.1432 (3)0.074 (4)
H55A0.27560.01520.12420.089*
H55B0.28020.00770.15910.089*
C560.2033 (6)0.0667 (3)0.1469 (3)0.064 (3)
H56A0.15310.04730.14150.077*
H56B0.20780.09550.13320.077*
C570.1931 (7)0.0864 (4)0.1772 (3)0.074 (4)
H57A0.18400.05820.19070.111*
H57B0.24330.10480.18300.111*
H57C0.14520.10920.17790.111*
C580.4474 (8)0.0003 (3)0.1190 (2)0.065 (3)
H58A0.40420.02680.12000.077*0.75
H58B0.50190.01730.12060.077*0.75
C590.4426 (11)0.0235 (5)0.0896 (3)0.101 (4)
H59A0.48050.05290.08920.121*
H59B0.38550.03630.08660.121*
C600.4634 (10)0.0092 (5)0.0652 (3)0.090 (4)
H60A0.43690.04230.06870.108*
H60B0.52420.01450.06530.108*
C610.4400 (14)0.0078 (7)0.0365 (4)0.161 (8)
H61A0.37970.01280.03580.242*
H61B0.46800.03980.03220.242*
H61C0.45630.01750.02190.242*
N50.7865 (4)0.2020 (3)0.12613 (16)0.0459 (18)
C620.7838 (6)0.2503 (4)0.13404 (19)0.049 (2)
H620.83430.26610.13970.059*
C630.7122 (6)0.2788 (4)0.1345 (2)0.055 (3)
H630.71430.31360.13950.066*
C640.6383 (6)0.2566 (4)0.1278 (2)0.055 (3)
H640.58840.27560.12830.066*
C650.6365 (5)0.2050 (4)0.12010 (18)0.042 (2)
C660.5626 (5)0.1773 (4)0.1129 (2)0.059 (3)
H660.51050.19410.11320.071*
C670.5655 (6)0.1293 (4)0.1057 (2)0.062 (3)
H670.51530.11190.10140.075*
C680.6415 (6)0.1031 (4)0.1043 (2)0.060 (3)
H680.64240.06850.09870.072*
C690.7135 (5)0.1273 (4)0.1109 (2)0.053 (2)
H690.76480.10970.10980.064*
C700.7124 (5)0.1789 (3)0.11928 (18)0.040 (2)
O30S0.0141 (8)0.0886 (5)0.0218 (3)0.065 (4)0.605 (11)
H30S0.05020.11130.01990.098*0.605 (11)
C74S0.0257 (18)0.0828 (10)0.0032 (5)0.167 (18)0.605 (11)
H74A0.00080.10450.01820.251*0.605 (11)
H74B0.08420.09200.00060.251*0.605 (11)
H74C0.02190.04750.00940.251*0.605 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.0161 (3)0.0229 (3)0.0223 (3)0.0046 (2)0.0010 (2)0.0003 (2)
Mo20.0211 (3)0.0289 (3)0.0221 (3)0.0041 (2)0.0010 (2)0.0086 (3)
Mo30.0227 (3)0.0367 (4)0.0165 (3)0.0047 (3)0.0047 (2)0.0081 (3)
Mo40.0172 (3)0.0278 (3)0.0185 (3)0.0034 (2)0.0051 (2)0.0031 (2)
Mo50.0149 (3)0.0217 (3)0.0170 (3)0.0027 (2)0.0008 (2)0.0024 (2)
Mo60.0148 (3)0.0246 (3)0.0160 (3)0.0024 (2)0.0013 (2)0.0003 (2)
Al10.0111 (9)0.0198 (9)0.0162 (9)0.0002 (7)0.0014 (7)0.0033 (7)
O10.011 (2)0.024 (2)0.019 (2)0.0010 (18)0.0003 (17)0.0041 (18)
O20.015 (2)0.025 (2)0.025 (2)0.0002 (19)0.0025 (19)0.009 (2)
O30.011 (2)0.026 (2)0.018 (2)0.0008 (18)0.0026 (18)0.0009 (18)
O40.013 (2)0.023 (2)0.023 (2)0.0012 (19)0.0014 (18)0.0048 (19)
O50.010 (2)0.023 (2)0.014 (2)0.0003 (17)0.0003 (17)0.0024 (17)
O60.013 (2)0.018 (2)0.022 (2)0.0017 (18)0.0004 (18)0.0039 (18)
O70.022 (2)0.022 (2)0.030 (3)0.0038 (19)0.002 (2)0.005 (2)
O80.023 (2)0.036 (3)0.013 (2)0.003 (2)0.0029 (19)0.0043 (19)
O90.021 (2)0.034 (3)0.023 (2)0.003 (2)0.009 (2)0.011 (2)
O100.021 (2)0.022 (2)0.015 (2)0.0015 (19)0.0009 (18)0.0030 (18)
O110.014 (2)0.025 (2)0.017 (2)0.0004 (18)0.0037 (17)0.0014 (18)
O120.012 (2)0.027 (2)0.023 (2)0.0006 (18)0.0023 (18)0.0005 (19)
O130.028 (3)0.028 (3)0.031 (3)0.004 (2)0.007 (2)0.001 (2)
O140.020 (2)0.034 (3)0.028 (3)0.009 (2)0.000 (2)0.006 (2)
O150.025 (3)0.043 (3)0.031 (3)0.008 (2)0.005 (2)0.004 (2)
O160.042 (3)0.038 (3)0.034 (3)0.005 (3)0.002 (2)0.011 (2)
O170.035 (3)0.055 (4)0.030 (3)0.010 (3)0.013 (2)0.015 (3)
O180.031 (3)0.053 (3)0.021 (3)0.011 (3)0.002 (2)0.001 (2)
O190.034 (3)0.035 (3)0.021 (2)0.008 (2)0.007 (2)0.001 (2)
O200.021 (2)0.038 (3)0.032 (3)0.003 (2)0.008 (2)0.005 (2)
O210.018 (2)0.037 (3)0.032 (3)0.002 (2)0.004 (2)0.000 (2)
O220.026 (3)0.026 (3)0.022 (2)0.003 (2)0.000 (2)0.003 (2)
O230.019 (2)0.034 (3)0.022 (2)0.005 (2)0.0000 (19)0.002 (2)
O240.025 (3)0.031 (3)0.020 (2)0.006 (2)0.003 (2)0.002 (2)
O250.021 (2)0.038 (3)0.030 (3)0.004 (2)0.003 (2)0.002 (2)
N10.018 (3)0.035 (3)0.015 (3)0.004 (2)0.001 (2)0.003 (2)
C10.011 (3)0.026 (3)0.015 (3)0.007 (3)0.000 (2)0.004 (3)
C20.013 (3)0.036 (4)0.019 (3)0.003 (3)0.004 (3)0.003 (3)
C30.017 (3)0.029 (4)0.020 (3)0.006 (3)0.003 (3)0.002 (3)
C40.010 (3)0.030 (4)0.019 (3)0.010 (3)0.000 (2)0.008 (3)
C50.013 (3)0.032 (4)0.029 (4)0.001 (3)0.005 (3)0.007 (3)
C60.016 (3)0.027 (4)0.035 (4)0.000 (3)0.003 (3)0.000 (3)
C70.027 (4)0.033 (4)0.044 (5)0.008 (3)0.008 (3)0.003 (3)
C80.035 (5)0.055 (6)0.050 (5)0.006 (4)0.001 (4)0.004 (4)
C90.049 (6)0.063 (6)0.056 (6)0.018 (5)0.005 (5)0.002 (5)
C100.076 (8)0.055 (6)0.073 (7)0.020 (6)0.015 (6)0.011 (6)
C110.087 (9)0.068 (7)0.070 (7)0.042 (7)0.002 (7)0.003 (6)
C120.123 (12)0.099 (10)0.066 (8)0.073 (9)0.020 (8)0.001 (7)
C130.082 (8)0.092 (9)0.052 (6)0.049 (7)0.021 (6)0.005 (6)
O1A0.026 (3)0.039 (3)0.052 (4)0.004 (2)0.004 (3)0.006 (3)
O1B0.030 (3)0.035 (3)0.039 (3)0.001 (2)0.003 (3)0.002 (2)
O1C0.038 (3)0.064 (4)0.061 (4)0.010 (3)0.005 (3)0.016 (3)
O1D0.041 (4)0.049 (4)0.067 (4)0.004 (3)0.012 (3)0.002 (3)
O26S0.059 (4)0.035 (3)0.055 (4)0.003 (3)0.010 (3)0.002 (3)
C71S0.071 (7)0.044 (6)0.091 (8)0.014 (5)0.034 (6)0.003 (6)
O27S0.064 (5)0.089 (5)0.059 (4)0.027 (4)0.024 (4)0.025 (4)
O28S0.067 (7)0.041 (5)0.065 (7)0.010 (4)0.001 (5)0.010 (5)
O29S0.043 (9)0.026 (7)0.029 (8)0.011 (6)0.005 (6)0.000 (6)
C72S0.096 (11)0.195 (19)0.158 (16)0.062 (12)0.073 (11)0.123 (15)
C73S0.12 (3)0.10 (3)0.050 (17)0.10 (3)0.010 (18)0.005 (17)
N20.057 (5)0.056 (5)0.032 (4)0.001 (4)0.027 (3)0.000 (3)
C140.057 (6)0.053 (6)0.042 (5)0.003 (5)0.026 (4)0.003 (4)
C150.083 (8)0.076 (7)0.034 (5)0.000 (6)0.019 (5)0.011 (5)
C160.088 (8)0.059 (7)0.051 (6)0.018 (6)0.016 (6)0.011 (5)
C170.101 (10)0.071 (8)0.055 (6)0.005 (7)0.007 (6)0.011 (6)
C180.061 (6)0.052 (5)0.035 (5)0.009 (5)0.028 (4)0.005 (4)
C190.082 (8)0.063 (6)0.043 (5)0.018 (6)0.029 (5)0.011 (5)
C200.065 (7)0.060 (6)0.065 (7)0.017 (5)0.026 (5)0.011 (5)
C210.088 (9)0.086 (9)0.070 (8)0.012 (7)0.012 (7)0.029 (7)
C220.052 (5)0.054 (5)0.032 (4)0.001 (4)0.023 (4)0.001 (4)
C230.075 (7)0.066 (7)0.056 (6)0.020 (6)0.037 (6)0.015 (5)
C240.070 (7)0.048 (6)0.063 (6)0.005 (5)0.031 (5)0.002 (5)
C250.092 (9)0.071 (7)0.058 (7)0.022 (7)0.023 (6)0.015 (6)
C260.050 (6)0.070 (7)0.043 (5)0.005 (5)0.025 (4)0.009 (5)
C270.042 (5)0.078 (7)0.055 (6)0.003 (5)0.020 (5)0.006 (5)
C280.042 (6)0.106 (9)0.063 (7)0.016 (6)0.007 (5)0.008 (7)
C290.063 (8)0.106 (10)0.091 (9)0.024 (7)0.016 (7)0.037 (8)
N30.020 (3)0.044 (4)0.031 (3)0.003 (3)0.012 (3)0.009 (3)
C300.034 (4)0.046 (5)0.028 (4)0.006 (4)0.009 (3)0.013 (4)
C310.030 (4)0.048 (5)0.032 (4)0.005 (4)0.007 (3)0.006 (4)
C320.043 (5)0.043 (5)0.041 (5)0.008 (4)0.002 (4)0.010 (4)
C330.066 (7)0.085 (8)0.042 (5)0.024 (6)0.004 (5)0.003 (5)
C340.023 (4)0.035 (4)0.027 (4)0.001 (3)0.004 (3)0.004 (3)
C350.030 (4)0.055 (5)0.056 (5)0.003 (4)0.006 (4)0.010 (5)
C360.048 (6)0.044 (5)0.076 (7)0.002 (4)0.023 (5)0.002 (5)
C370.062 (7)0.066 (7)0.103 (9)0.021 (6)0.021 (7)0.024 (7)
C380.023 (4)0.044 (5)0.028 (4)0.006 (3)0.009 (3)0.009 (3)
C390.028 (4)0.054 (5)0.030 (4)0.008 (4)0.009 (3)0.005 (4)
C400.033 (4)0.041 (5)0.034 (4)0.004 (4)0.005 (3)0.009 (4)
C410.056 (6)0.041 (5)0.051 (5)0.007 (4)0.009 (5)0.004 (4)
C420.022 (4)0.046 (5)0.050 (5)0.003 (3)0.008 (4)0.001 (4)
C430.059 (7)0.062 (7)0.079 (8)0.008 (5)0.007 (6)0.013 (6)
C440.070 (7)0.066 (7)0.060 (7)0.001 (6)0.011 (6)0.006 (5)
C450.046 (5)0.061 (6)0.061 (6)0.004 (5)0.002 (5)0.009 (5)
N40.054 (5)0.029 (4)0.072 (6)0.005 (3)0.004 (4)0.007 (4)
C460.056 (6)0.022 (4)0.066 (6)0.001 (4)0.006 (5)0.003 (4)
C470.055 (6)0.034 (5)0.089 (8)0.006 (4)0.010 (6)0.002 (5)
C480.053 (6)0.046 (6)0.106 (9)0.004 (5)0.027 (6)0.003 (6)
C490.108 (11)0.074 (9)0.131 (13)0.025 (8)0.062 (10)0.010 (8)
C500.037 (5)0.024 (4)0.072 (6)0.002 (3)0.010 (4)0.004 (4)
C510.040 (5)0.028 (4)0.080 (7)0.000 (4)0.000 (5)0.004 (4)
C520.059 (6)0.042 (5)0.073 (7)0.004 (5)0.002 (5)0.005 (5)
C530.097 (9)0.064 (7)0.080 (9)0.025 (7)0.012 (7)0.007 (6)
C540.052 (6)0.020 (4)0.088 (7)0.000 (4)0.018 (5)0.002 (4)
C550.060 (7)0.028 (5)0.134 (11)0.005 (5)0.031 (7)0.006 (6)
C560.058 (6)0.031 (5)0.103 (9)0.007 (4)0.031 (6)0.006 (5)
C570.053 (6)0.072 (8)0.098 (9)0.010 (6)0.003 (6)0.041 (7)
C580.094 (8)0.030 (5)0.070 (7)0.007 (5)0.002 (6)0.005 (5)
C590.146 (9)0.063 (6)0.093 (8)0.005 (7)0.002 (7)0.003 (6)
C600.114 (8)0.078 (7)0.079 (7)0.018 (6)0.003 (6)0.013 (6)
C610.217 (17)0.123 (13)0.143 (14)0.039 (13)0.012 (13)0.004 (11)
N50.023 (3)0.067 (5)0.048 (4)0.001 (3)0.002 (3)0.011 (4)
C620.041 (5)0.067 (7)0.040 (5)0.009 (5)0.002 (4)0.001 (4)
C630.047 (6)0.073 (7)0.045 (5)0.009 (5)0.007 (4)0.005 (5)
C640.035 (5)0.074 (7)0.056 (6)0.019 (5)0.006 (4)0.000 (5)
C650.027 (4)0.060 (6)0.039 (5)0.006 (4)0.002 (3)0.009 (4)
C660.018 (4)0.089 (8)0.071 (7)0.007 (5)0.002 (4)0.027 (6)
C670.035 (5)0.071 (7)0.081 (8)0.009 (5)0.012 (5)0.023 (6)
C680.047 (6)0.061 (6)0.072 (7)0.018 (5)0.005 (5)0.007 (5)
C690.032 (5)0.048 (5)0.079 (7)0.001 (4)0.009 (5)0.018 (5)
C700.021 (4)0.059 (6)0.040 (5)0.001 (4)0.002 (3)0.006 (4)
O30S0.068 (9)0.071 (9)0.058 (8)0.031 (7)0.011 (6)0.003 (6)
C74S0.19 (3)0.16 (3)0.15 (3)0.13 (3)0.07 (2)0.11 (2)
Geometric parameters (Å, º) top
Mo1—O12.346 (4)O29S—C73S1.37 (2)
Mo1—O62.293 (4)N2—C141.520 (11)
Mo1—O71.941 (5)N2—C181.533 (11)
Mo1—O121.920 (4)N2—C221.515 (11)
Mo1—O131.702 (5)N2—C261.513 (12)
Mo1—O141.702 (5)C14—C151.518 (13)
Mo2—O12.324 (4)C15—C161.539 (14)
Mo2—O22.307 (4)C16—C171.532 (14)
Mo2—O71.933 (5)C18—C191.523 (13)
Mo2—O81.929 (5)C19—C201.522 (13)
Mo2—O151.707 (5)C20—C211.518 (14)
Mo2—O161.713 (5)C22—C231.494 (13)
Mo3—O22.322 (5)C23—C241.507 (13)
Mo3—O32.323 (4)C24—C251.504 (14)
Mo3—O81.917 (5)C26—C271.540 (12)
Mo3—O91.910 (5)C27—C281.489 (14)
Mo3—O171.718 (5)C28—C291.528 (16)
Mo3—O181.699 (5)N3—C301.516 (9)
Mo4—O32.352 (4)N3—C341.505 (9)
Mo4—O42.305 (5)N3—C381.530 (9)
Mo4—O91.931 (4)N3—C421.513 (10)
Mo4—O101.923 (4)C30—C311.513 (10)
Mo4—O191.705 (5)C31—C321.537 (11)
Mo4—O201.697 (5)C32—C331.509 (13)
Mo5—O42.307 (4)C34—C351.510 (11)
Mo5—O52.390 (4)C35—C361.490 (12)
Mo5—O101.915 (4)C36—C371.562 (14)
Mo5—O111.911 (4)C38—C391.521 (10)
Mo5—O211.703 (5)C39—C401.526 (10)
Mo5—O221.711 (5)C40—C411.540 (12)
Mo6—O52.311 (4)C42—C431.512 (13)
Mo6—O62.305 (4)C43—C441.415 (14)
Mo6—O111.924 (4)C44—C451.562 (14)
Mo6—O121.922 (4)N4—C461.532 (11)
Mo6—O231.694 (5)N4—C501.501 (12)
Mo6—O241.722 (5)N4—C541.522 (11)
Al1—O11.923 (4)N4—C581.519 (12)
Al1—O21.879 (5)C46—C471.521 (13)
Al1—O31.915 (5)C47—C481.535 (13)
Al1—O41.865 (5)C48—C491.503 (13)
Al1—O51.909 (4)C50—C511.494 (12)
Al1—O61.880 (5)C51—C521.528 (13)
O1—C21.437 (8)C52—C531.482 (12)
O3—C31.432 (7)C54—C551.511 (13)
O5—C41.431 (7)C55—C561.518 (14)
O25—C51.223 (8)C56—C571.485 (12)
N1—C11.469 (8)C58—C591.484 (16)
N1—C51.363 (8)C59—C601.447 (17)
C1—C21.529 (9)C60—C611.432 (14)
C1—C31.523 (8)N5—C621.331 (12)
C1—C41.537 (8)N5—C701.377 (10)
C5—C61.458 (9)C62—C631.379 (13)
C6—C71.364 (10)C63—C641.363 (14)
C7—C81.452 (11)C64—C651.412 (14)
C8—C91.345 (13)C65—C661.436 (13)
C8—C131.391 (13)C65—C701.405 (11)
C9—C101.410 (13)C66—C671.316 (15)
C10—C111.364 (15)C67—C681.409 (14)
C11—C121.369 (16)C68—C691.361 (13)
C12—C131.384 (14)C69—C701.422 (13)
O26S—C71S1.403 (11)O30S—C74S1.315 (19)
O27S—C72S1.340 (12)
O6—Mo1—O167.73 (15)Al1—O3—Mo3103.28 (19)
O7—Mo1—O172.00 (17)Al1—O3—Mo4101.29 (18)
O7—Mo1—O681.74 (17)C3—O3—Mo3117.6 (4)
O12—Mo1—O180.43 (17)C3—O3—Mo4118.8 (4)
O12—Mo1—O672.48 (16)C3—O3—Al1120.0 (4)
O12—Mo1—O7147.80 (19)Mo4—O4—Mo591.85 (16)
O13—Mo1—O1160.16 (19)Al1—O4—Mo4104.7 (2)
O13—Mo1—O694.0 (2)Al1—O4—Mo5105.2 (2)
O13—Mo1—O798.7 (2)Mo6—O5—Mo589.97 (14)
O13—Mo1—O12101.9 (2)Al1—O5—Mo5100.75 (17)
O14—Mo1—O192.80 (19)Al1—O5—Mo6102.93 (19)
O14—Mo1—O6159.3 (2)C4—O5—Mo5118.8 (4)
O14—Mo1—O799.3 (2)C4—O5—Mo6118.9 (3)
O14—Mo1—O1298.3 (2)C4—O5—Al1120.1 (3)
O14—Mo1—O13106.2 (2)Mo1—O6—Mo691.36 (15)
O2—Mo2—O167.94 (15)Al1—O6—Mo1104.94 (19)
O7—Mo2—O172.65 (17)Al1—O6—Mo6104.10 (19)
O7—Mo2—O281.84 (18)Mo2—O7—Mo1118.2 (2)
O8—Mo2—O181.02 (17)Mo3—O8—Mo2119.5 (2)
O8—Mo2—O271.58 (18)Mo3—O9—Mo4120.4 (2)
O8—Mo2—O7148.07 (18)Mo5—O10—Mo4119.3 (2)
O15—Mo2—O192.3 (2)Mo5—O11—Mo6120.2 (2)
O15—Mo2—O2158.3 (2)Mo1—O12—Mo6117.8 (2)
O15—Mo2—O7101.4 (2)C5—N1—C1126.2 (6)
O15—Mo2—O897.3 (2)N1—C1—C2109.5 (5)
O15—Mo2—O16106.0 (3)N1—C1—C3103.5 (5)
O16—Mo2—O1160.9 (2)N1—C1—C4109.5 (5)
O16—Mo2—O294.6 (2)C2—C1—C4111.2 (5)
O16—Mo2—O797.9 (2)C3—C1—C2112.2 (5)
O16—Mo2—O8101.5 (2)C3—C1—C4110.8 (5)
O2—Mo3—O367.05 (15)O1—C2—C1111.7 (5)
O8—Mo3—O271.43 (17)O3—C3—C1112.3 (5)
O8—Mo3—O380.71 (16)O5—C4—C1112.2 (5)
O9—Mo3—O281.71 (18)O25—C5—N1124.0 (6)
O9—Mo3—O372.05 (16)O25—C5—C6123.4 (6)
O9—Mo3—O8147.53 (19)N1—C5—C6112.6 (6)
O17—Mo3—O295.3 (2)C7—C6—C5118.7 (7)
O17—Mo3—O3161.0 (2)C6—C7—C8128.0 (8)
O17—Mo3—O8101.0 (2)C9—C8—C7121.9 (9)
O17—Mo3—O999.3 (2)C9—C8—C13119.1 (9)
O18—Mo3—O2157.9 (2)C13—C8—C7119.0 (9)
O18—Mo3—O392.8 (2)C8—C9—C10119.7 (10)
O18—Mo3—O897.4 (2)C11—C10—C9120.8 (10)
O18—Mo3—O9101.2 (2)C10—C11—C12120.0 (10)
O18—Mo3—O17105.6 (3)C11—C12—C13118.9 (11)
O4—Mo4—O367.56 (15)C12—C13—C8121.5 (11)
O9—Mo4—O371.04 (17)C14—N2—C18110.6 (7)
O9—Mo4—O482.54 (18)C22—N2—C14107.6 (6)
O10—Mo4—O382.24 (17)C22—N2—C18110.4 (7)
O10—Mo4—O471.32 (17)C26—N2—C14111.4 (8)
O10—Mo4—O9148.23 (19)C26—N2—C18106.0 (6)
O19—Mo4—O392.1 (2)C26—N2—C22110.9 (7)
O19—Mo4—O4157.0 (2)C15—C14—N2115.3 (7)
O19—Mo4—O9101.4 (2)C14—C15—C16110.4 (7)
O19—Mo4—O1096.4 (2)C17—C16—C15115.0 (9)
O20—Mo4—O3161.1 (2)C19—C18—N2114.8 (7)
O20—Mo4—O496.1 (2)C20—C19—C18107.9 (7)
O20—Mo4—O998.4 (2)C21—C20—C19112.3 (9)
O20—Mo4—O10102.0 (2)C23—C22—N2114.8 (7)
O20—Mo4—O19105.6 (2)C22—C23—C24113.0 (8)
O4—Mo5—O567.02 (14)C25—C24—C23114.6 (8)
O10—Mo5—O471.39 (17)N2—C26—C27115.4 (7)
O10—Mo5—O580.02 (16)C28—C27—C26110.4 (8)
O11—Mo5—O482.74 (17)C27—C28—C29114.3 (10)
O11—Mo5—O571.07 (16)C30—N3—C38107.5 (5)
O11—Mo5—O10147.03 (18)C34—N3—C30108.9 (6)
O21—Mo5—O494.2 (2)C34—N3—C38109.9 (6)
O21—Mo5—O5159.6 (2)C34—N3—C42107.1 (5)
O21—Mo5—O10102.1 (2)C42—N3—C30111.5 (6)
O21—Mo5—O1199.8 (2)C42—N3—C38112.0 (6)
O21—Mo5—O22105.6 (2)C31—C30—N3115.3 (6)
O22—Mo5—O4158.70 (19)C30—C31—C32111.9 (6)
O22—Mo5—O594.24 (18)C33—C32—C31111.7 (7)
O22—Mo5—O1096.3 (2)N3—C34—C35115.8 (6)
O22—Mo5—O11101.3 (2)C36—C35—C34112.2 (8)
O6—Mo6—O567.59 (15)C35—C36—C37112.4 (9)
O11—Mo6—O572.71 (16)C39—C38—N3114.0 (6)
O11—Mo6—O680.97 (16)C38—C39—C40112.2 (6)
O12—Mo6—O581.27 (16)C39—C40—C41112.4 (7)
O12—Mo6—O672.15 (16)C43—C42—N3117.9 (7)
O12—Mo6—O11148.13 (18)C44—C43—C42123.5 (10)
O23—Mo6—O591.50 (19)C43—C44—C45113.7 (10)
O23—Mo6—O6157.64 (19)C50—N4—C46111.0 (7)
O23—Mo6—O11100.9 (2)C50—N4—C54110.9 (7)
O23—Mo6—O1297.8 (2)C50—N4—C58107.1 (7)
O23—Mo6—O24106.0 (2)C54—N4—C46105.3 (6)
O24—Mo6—O5161.67 (19)C58—N4—C46110.7 (8)
O24—Mo6—O695.72 (19)C58—N4—C54111.9 (8)
O24—Mo6—O1198.0 (2)C47—C46—N4116.9 (7)
O24—Mo6—O12101.3 (2)C46—C47—C48109.4 (8)
O2—Al1—O185.8 (2)C49—C48—C47111.9 (10)
O2—Al1—O385.1 (2)C51—C50—N4116.5 (7)
O2—Al1—O5174.8 (2)C50—C51—C52110.6 (7)
O2—Al1—O698.0 (2)C53—C52—C51112.7 (8)
O3—Al1—O190.41 (19)C55—C54—N4114.5 (7)
O4—Al1—O1175.9 (2)C54—C55—C56110.4 (8)
O4—Al1—O296.6 (2)C57—C56—C55113.4 (10)
O4—Al1—O386.5 (2)C59—C58—N4117.6 (8)
O4—Al1—O586.85 (19)C60—C59—C58115.2 (11)
O4—Al1—O697.3 (2)C61—C60—C59116.8 (13)
O5—Al1—O190.51 (19)C62—N5—C70117.4 (8)
O5—Al1—O391.3 (2)N5—C62—C63123.9 (9)
O6—Al1—O185.7 (2)C64—C63—C62119.3 (10)
O6—Al1—O3174.8 (2)C63—C64—C65119.5 (9)
O6—Al1—O585.33 (19)C64—C65—C66124.6 (8)
Mo2—O1—Mo190.82 (15)C70—C65—C64117.7 (8)
Al1—O1—Mo1101.59 (19)C70—C65—C66117.7 (9)
Al1—O1—Mo2102.06 (18)C67—C66—C65121.5 (9)
C2—O1—Mo1117.8 (4)C66—C67—C68121.3 (9)
C2—O1—Mo2119.2 (3)C69—C68—C67119.9 (10)
C2—O1—Al1120.1 (4)C68—C69—C70120.2 (9)
Mo2—O2—Mo391.73 (16)N5—C70—C65122.0 (8)
Al1—O2—Mo2104.1 (2)N5—C70—C69118.5 (8)
Al1—O2—Mo3104.5 (2)C65—C70—C69119.5 (8)
Mo3—O3—Mo490.94 (14)
Mo1—O1—C2—C1127.0 (4)C18—N2—C22—C2353.5 (11)
Mo2—O1—C2—C1124.7 (4)C18—N2—C26—C27176.6 (9)
Mo3—O3—C3—C1127.1 (4)C18—C19—C20—C21175.5 (10)
Mo4—O3—C3—C1125.0 (5)C22—N2—C14—C15173.4 (8)
Mo5—O5—C4—C1127.3 (4)C22—N2—C18—C1956.7 (10)
Mo6—O5—C4—C1125.1 (4)C22—N2—C26—C2763.6 (11)
Al1—O1—C2—C12.3 (7)C22—C23—C24—C25175.8 (10)
Al1—O3—C3—C10.1 (7)C26—N2—C14—C1551.6 (11)
Al1—O5—C4—C12.9 (7)C26—N2—C18—C19176.9 (9)
O1—Al1—O2—Mo22.7 (2)C26—N2—C22—C2363.6 (11)
O1—Al1—O2—Mo392.9 (2)C26—C27—C28—C2967.1 (13)
O1—Al1—O6—Mo12.42 (19)N3—C30—C31—C32179.4 (7)
O1—Al1—O6—Mo692.89 (19)N3—C34—C35—C36163.6 (7)
O2—Al1—O4—Mo483.4 (2)N3—C38—C39—C40157.5 (7)
O2—Al1—O4—Mo5179.5 (2)N3—C42—C43—C4472.4 (14)
O2—Al1—O6—Mo182.7 (2)C30—N3—C34—C3556.5 (8)
O2—Al1—O6—Mo6178.01 (19)C30—N3—C38—C39173.8 (7)
O3—Al1—O2—Mo293.5 (2)C30—N3—C42—C4349.6 (9)
O3—Al1—O2—Mo32.11 (19)C30—C31—C32—C3369.6 (10)
O3—Al1—O4—Mo41.2 (2)C34—N3—C30—C3160.3 (9)
O3—Al1—O4—Mo594.8 (2)C34—N3—C38—C3967.8 (8)
O4—Al1—O2—Mo2179.3 (2)C34—N3—C42—C43168.7 (7)
O4—Al1—O2—Mo383.7 (2)C34—C35—C36—C37176.8 (7)
O4—Al1—O6—Mo1179.50 (19)C38—N3—C30—C31179.3 (7)
O4—Al1—O6—Mo684.2 (2)C38—N3—C34—C3561.0 (8)
O5—Al1—O4—Mo492.8 (2)C38—N3—C42—C4370.9 (9)
O5—Al1—O4—Mo53.3 (2)C38—C39—C40—C4167.2 (9)
O5—Al1—O6—Mo193.29 (19)C42—N3—C30—C3157.7 (9)
O5—Al1—O6—Mo62.02 (19)C42—N3—C34—C35177.2 (7)
O6—Al1—O2—Mo282.3 (2)C42—N3—C38—C3951.1 (9)
O6—Al1—O2—Mo3177.89 (19)C42—C43—C44—C45168.2 (9)
O6—Al1—O4—Mo4177.64 (19)N4—C46—C47—C48163.2 (9)
O6—Al1—O4—Mo581.6 (2)N4—C50—C51—C52177.9 (8)
O25—C5—C6—C712.0 (10)N4—C54—C55—C56170.7 (10)
N1—C1—C2—O1175.2 (5)N4—C58—C59—C60172.3 (12)
N1—C1—C3—O3179.5 (5)C46—N4—C50—C5165.6 (10)
N1—C1—C4—O5177.7 (5)C46—N4—C54—C55179.0 (10)
N1—C5—C6—C7166.9 (6)C46—N4—C58—C5963.1 (14)
C1—N1—C5—O257.2 (11)C46—C47—C48—C4981.4 (11)
C1—N1—C5—C6171.7 (6)C50—N4—C46—C4753.6 (11)
C2—C1—C3—O362.6 (7)C50—N4—C54—C5558.8 (11)
C2—C1—C4—O561.2 (7)C50—N4—C58—C59175.8 (11)
C3—C1—C2—O160.9 (7)C50—C51—C52—C53175.0 (9)
C3—C1—C4—O564.2 (7)C54—N4—C46—C47173.6 (9)
C4—C1—C2—O163.8 (6)C54—N4—C50—C5151.1 (10)
C4—C1—C3—O362.3 (7)C54—N4—C58—C5954.0 (14)
C5—N1—C1—C263.3 (8)C54—C55—C56—C5772.1 (13)
C5—N1—C1—C3176.9 (6)C58—N4—C46—C4765.2 (11)
C5—N1—C1—C458.8 (8)C58—N4—C50—C51173.5 (8)
C5—C6—C7—C8172.3 (8)C58—N4—C54—C5560.7 (12)
C6—C7—C8—C915.1 (15)C58—C59—C60—C61164.9 (16)
C6—C7—C8—C13165.2 (10)N5—C62—C63—C643.0 (15)
C7—C8—C9—C10177.8 (9)C62—N5—C70—C650.8 (12)
C7—C8—C13—C12178.6 (12)C62—N5—C70—C69179.8 (8)
C8—C9—C10—C111.5 (18)C62—C63—C64—C650.8 (15)
C9—C8—C13—C121.7 (19)C63—C64—C65—C66179.4 (9)
C9—C10—C11—C120 (2)C63—C64—C65—C701.0 (14)
C10—C11—C12—C131 (2)C64—C65—C66—C67179.6 (10)
C11—C12—C13—C80 (2)C64—C65—C70—N51.0 (13)
C13—C8—C9—C102.5 (16)C64—C65—C70—C69178.3 (8)
N2—C14—C15—C16176.3 (9)C65—C66—C67—C681.3 (17)
N2—C18—C19—C20170.5 (9)C66—C65—C70—N5179.4 (8)
N2—C22—C23—C24179.7 (9)C66—C65—C70—C691.3 (13)
N2—C26—C27—C28177.4 (9)C66—C67—C68—C691.2 (17)
C14—N2—C18—C1962.2 (11)C67—C68—C69—C700.3 (16)
C14—N2—C22—C23174.3 (9)C68—C69—C70—N5179.2 (9)
C14—N2—C26—C2756.2 (11)C68—C69—C70—C651.5 (14)
C14—C15—C16—C17177.5 (10)C70—N5—C62—C632.9 (14)
C18—N2—C14—C1566.0 (11)C70—C65—C66—C670.1 (14)
(taco104_0m) top
Crystal data top
C23H25AlClMo6N2O27·9(H2O)·2(C16H36N)·C16H35NDx = 1.535 Mg m3
Mr = 2288.02Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9039 reflections
a = 21.8904 (6) Åθ = 2.5–29.1°
b = 23.9848 (6) ŵ = 0.85 mm1
c = 37.719 (1) ÅT = 200 K
V = 19803.9 (9) Å3Plate, clear dark green
Z = 80.15 × 0.12 × 0.05 mm
F(000) = 9448
Data collection top
Bruker APEX-II CCD
diffractometer
15743 reflections with I > 2σ(I)
φ and ω scansRint = 0.050
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
θmax = 25.4°, θmin = 2.2°
Tmin = 0.678, Tmax = 0.746h = 2626
374956 measured reflectionsk = 2828
18115 independent reflectionsl = 4545
Refinement top
Refinement on F253 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0307P)2 + 38.9537P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.005
18115 reflectionsΔρmax = 1.18 e Å3
1166 parametersΔρmin = 0.63 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. _olex2_refinement_description 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H,H) groups 2. Restrained distances H32C-H36E 2.1 with sigma of 0.02 H34D-H33D 2.1 with sigma of 0.02 H37D-H29B 2.1 with sigma of 0.02 H29B-H37C 2.1 with sigma of 0.02 H28C-H35E_$1 2.1 with sigma of 0.02 C38-C37 ~ C37-C36 ~ C36-C37A ~ C37A-C38A ~ C38A-C39A ~ C39-C38 with sigma of 0.02 O3-H3 ~ O5-H5 ~ O1-H1 with sigma of 0.01 C31A-C30 ~ C31-C30 ~ C30-C29 ~ C28-C29 with sigma of 0.02 3. Rigid bond restraints C36, C37, C38, C37A, C38A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Uiso/Uaniso restraints and constraints C37 ~ C37A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(C37A) ~ Ueq, Uanis(C37) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 5. Others Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(C38A)=Sof(H38C)=Sof(H38D)=Sof(C39A)= Sof(H39D)=Sof(H39E)=Sof(H39F)=1-FVAR(1) Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)= Sof(H39B)=Sof(H39C)=FVAR(1) Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(2) Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(2) Fixed Sof: H36A(0.5) H36B(0.5) H36C(0.5) H36D(0.5) 6.a Free rotating group: O28(H28C,H28D), O29(H29C,H29D), O30(H30E,H30F), O31(H31G,H31H), O32(H32C, H32D), O33(H33C,H33D), O34(H34C,H34D), O35(H35D,H35E), O36(H36E,H36F) 6.b Secondary CH2 refined with riding coordinates: C1(H1B,H1C), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C56(H56A,H56B), C57(H57A, H57B), C58(H58A,H58B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B), C40(H40A,H40B), C41(H41A,H41B), C44(H44A,H44B), C45(H45A, H45B), C46(H46A,H46B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C30(H30C, H30D), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B), C36(H36C,H36D), C37(H37A,H37B), C38(H38A,H38B), C37A(H37C,H37D), C38A(H38C, H38D) 6.c Aromatic/amide H refined with riding coordinates: N1(H1A), C11(H11), C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), C42(H42) 6.d Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C59(H59A,H59B,H59C), C63(H63A,H63B, H63C), C67(H67A,H67B,H67C), C71(H71A,H71B,H71C), C43(H43A,H43B,H43C), C47(H47A, H47B,H47C), C51(H51A,H51B,H51C), C55(H55A,H55B,H55C), C27(H27A,H27B,H27C), C35(H35A,H35B,H35C), C31(H31A,H31B,H31C), C39(H39A,H39B,H39C), C31A(H31D,H31E, H31F), C39A(H39D,H39E,H39F)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Mo10.38344 (2)0.54750 (2)0.56120 (2)0.01876 (6)
Mo20.38949 (2)0.41213 (2)0.54338 (2)0.01851 (6)
Mo30.46290 (2)0.32597 (2)0.59697 (2)0.01923 (6)
Mo40.52407 (2)0.37445 (2)0.67227 (2)0.01915 (6)
Mo50.51712 (2)0.50938 (2)0.69045 (2)0.01967 (6)
Mo60.45106 (2)0.59683 (2)0.63343 (2)0.01943 (6)
Cl11.13904 (6)0.59166 (7)0.61924 (4)0.0835 (4)
Al10.45154 (3)0.46060 (3)0.61741 (2)0.01350 (16)
O10.39852 (8)0.40276 (8)0.60405 (5)0.0177 (4)
O20.45671 (8)0.47740 (7)0.56841 (4)0.0143 (4)
O30.39356 (8)0.51857 (8)0.61928 (5)0.0173 (4)
O40.51078 (8)0.51710 (7)0.62810 (5)0.0152 (4)
O50.45153 (8)0.44436 (8)0.66574 (5)0.0169 (4)
O60.51547 (8)0.40570 (7)0.61360 (5)0.0150 (4)
O70.44728 (9)0.59114 (8)0.58283 (5)0.0218 (4)
O80.32102 (10)0.58856 (9)0.56881 (6)0.0320 (5)
O90.40337 (10)0.55811 (8)0.51813 (5)0.0266 (5)
O100.34218 (9)0.47671 (8)0.55733 (5)0.0220 (4)
O110.33243 (10)0.36470 (9)0.53945 (6)0.0342 (5)
O120.40874 (10)0.43100 (9)0.50130 (5)0.0286 (5)
O130.45839 (9)0.36411 (8)0.55234 (5)0.0196 (4)
O140.40467 (10)0.27903 (9)0.59318 (6)0.0322 (5)
O150.52805 (10)0.28995 (9)0.58878 (6)0.0312 (5)
O160.46295 (9)0.33037 (8)0.64844 (5)0.0219 (4)
O170.50269 (11)0.35904 (9)0.71477 (5)0.0325 (5)
O180.58728 (10)0.33537 (9)0.66424 (6)0.0322 (5)
O190.49588 (11)0.49390 (10)0.73261 (5)0.0349 (5)
O200.56449 (9)0.44463 (8)0.67753 (5)0.0204 (4)
O210.57620 (10)0.55541 (9)0.69410 (6)0.0317 (5)
O220.45133 (9)0.56024 (8)0.67924 (5)0.0217 (4)
O230.51442 (10)0.63746 (8)0.63623 (5)0.0298 (5)
O240.39050 (10)0.63988 (9)0.64191 (6)0.0330 (5)
O250.69976 (10)0.47434 (11)0.59651 (5)0.0362 (6)
O260.93869 (12)0.38839 (11)0.58143 (9)0.0575 (8)
O270.86240 (12)0.64512 (12)0.46946 (8)0.0553 (8)
N10.62325 (10)0.48441 (10)0.55628 (6)0.0191 (5)
H1A0.61670.49370.53400.023*
N20.88830 (11)0.46349 (11)0.55840 (7)0.0314 (6)
C10.51561 (12)0.48452 (12)0.55214 (7)0.0180 (6)
H1B0.51790.52220.54160.022*
H1C0.52010.45710.53270.022*
C20.56650 (12)0.52145 (11)0.60751 (7)0.0185 (6)
H2A0.60220.51690.62340.022*
H2B0.56890.55890.59660.022*
C30.57029 (12)0.41818 (11)0.59373 (7)0.0192 (6)
H3A0.57470.39100.57410.023*
H3B0.60630.41430.60940.023*
C40.56869 (11)0.47718 (11)0.57842 (7)0.0158 (5)
C50.68201 (13)0.47852 (12)0.56591 (7)0.0214 (6)
C60.72449 (13)0.47496 (14)0.53373 (8)0.0275 (7)
H6A0.71730.43870.52190.033*
H6B0.71260.50460.51680.033*
C70.79175 (13)0.48032 (13)0.54075 (8)0.0270 (7)
C80.82712 (14)0.44402 (13)0.55882 (8)0.0286 (7)
C90.80915 (15)0.39129 (14)0.57705 (9)0.0351 (8)
H9A0.76460.38770.57680.053*
H9B0.82370.39210.60160.053*
H9C0.82740.35950.56470.053*
C100.83021 (14)0.52331 (14)0.52617 (9)0.0315 (7)
C110.81826 (15)0.56815 (15)0.50339 (9)0.0367 (8)
H110.77770.57640.49620.044*
C120.86663 (16)0.59999 (16)0.49172 (10)0.0415 (8)
C130.92668 (16)0.58762 (17)0.50235 (10)0.0446 (9)
H130.95930.61030.49420.054*
C140.93910 (16)0.54318 (16)0.52437 (10)0.0424 (9)
H140.97990.53410.53070.051*
C150.89037 (14)0.51210 (15)0.53705 (9)0.0348 (8)
C160.93806 (15)0.43818 (15)0.57565 (10)0.0364 (8)
C170.98805 (15)0.47540 (15)0.58653 (9)0.0351 (8)
C180.97462 (16)0.52781 (16)0.60125 (10)0.0430 (9)
H180.93330.53910.60390.052*
C191.02114 (18)0.56307 (19)0.61185 (11)0.0515 (10)
H191.01240.59850.62200.062*
C201.08094 (18)0.5453 (2)0.60731 (10)0.0537 (11)
C211.09508 (17)0.49361 (19)0.59434 (11)0.0524 (10)
H211.13640.48180.59240.063*
C221.04770 (17)0.45893 (18)0.58412 (11)0.0484 (10)
H221.05680.42280.57520.058*
C230.80267 (18)0.65923 (19)0.45721 (13)0.0606 (12)
H23A0.80520.69140.44120.091*
H23B0.77670.66860.47750.091*
H23C0.78510.62740.44450.091*
O280.72919 (13)0.34330 (13)0.37814 (8)0.0554 (7)
H28C0.70990.31890.39010.083*
H28D0.73380.37050.39230.083*
O290.71747 (12)0.46184 (11)0.34943 (7)0.0434 (6)
H29C0.72790.42890.35500.065*
H29D0.70610.45930.32790.065*
O300.65908 (11)0.57515 (10)0.30301 (6)0.0368 (5)
H30E0.64770.60130.28930.055*
H30F0.67960.59130.31910.055*
O310.34120 (12)0.53722 (11)0.71708 (7)0.0461 (6)
H31G0.34370.50210.71440.069*
H31H0.37400.54990.70810.069*
O320.38081 (14)0.34181 (13)0.73972 (7)0.0538 (7)
H32C0.37840.31700.72370.081*
H32D0.41770.35280.73890.081*
O330.24067 (12)0.45998 (13)0.60128 (7)0.0529 (7)
H33C0.26850.47000.58690.079*
H33D0.21670.43990.58900.079*
O340.29073 (11)0.37358 (11)0.63812 (7)0.0427 (6)
H34C0.28270.33970.63350.064*
H34D0.26500.39200.62590.064*
O350.29529 (13)0.25727 (12)0.62754 (8)0.0576 (8)
H35D0.33060.26890.62200.086*
H35E0.28920.22930.61420.086*
O360.38207 (12)0.26705 (11)0.68514 (7)0.0463 (6)
H36E0.40890.28620.67440.070*
H36F0.35310.25940.67100.070*
N30.47841 (12)0.68789 (11)0.76002 (7)0.0323 (6)
C560.51693 (16)0.63516 (14)0.76153 (10)0.0387 (8)
H56A0.49530.60740.77630.046*
H56B0.52000.61960.73730.046*
C570.58083 (17)0.64259 (17)0.77610 (12)0.0504 (10)
H57A0.60540.66510.75930.060*
H57B0.57890.66290.79890.060*
C580.61104 (17)0.58654 (18)0.78167 (11)0.0500 (10)
H58A0.60630.56370.76000.060*
H58B0.59050.56680.80140.060*
C590.67895 (19)0.5929 (2)0.79017 (12)0.0646 (13)
H59A0.70000.60930.76980.097*
H59B0.69650.55620.79540.097*
H59C0.68390.61730.81080.097*
C600.46558 (16)0.71026 (14)0.79697 (8)0.0329 (7)
H60A0.50520.71760.80870.039*
H60B0.44420.74650.79460.039*
C610.42781 (18)0.67314 (15)0.82113 (10)0.0415 (8)
H61A0.44570.63530.82170.050*
H61B0.38570.67020.81180.050*
C620.4264 (2)0.69740 (16)0.85848 (10)0.0535 (11)
H62A0.46840.69740.86820.064*
H62B0.41250.73660.85720.064*
C630.3855 (3)0.6660 (2)0.88324 (13)0.0811 (17)
H63A0.34310.66880.87500.122*
H63B0.38870.68200.90710.122*
H63C0.39780.62680.88390.122*
C640.41939 (15)0.67164 (14)0.74125 (9)0.0345 (8)
H64A0.42990.65700.71750.041*
H64B0.40020.64080.75470.041*
C650.37283 (17)0.71747 (16)0.73678 (10)0.0419 (9)
H65A0.39000.74760.72190.050*
H65B0.36240.73350.76020.050*
C660.31578 (17)0.69402 (18)0.71944 (11)0.0516 (10)
H66A0.32690.67810.69610.062*
H66B0.29970.66340.73430.062*
C670.2661 (2)0.7370 (2)0.71425 (13)0.0716 (14)
H67A0.28230.76840.70040.107*
H67B0.25220.75050.73740.107*
H67C0.23180.72010.70150.107*
C680.51168 (17)0.73400 (15)0.74029 (9)0.0391 (8)*
H68A0.48510.76740.74000.047*
H68B0.54880.74370.75390.047*
C690.53056 (19)0.72149 (19)0.70252 (10)0.0526 (10)
H69A0.49430.71030.68850.063*
H69B0.56010.69020.70230.063*
C700.5606 (3)0.7747 (3)0.68556 (12)0.0858 (19)
H70A0.52960.80470.68430.103*
H70B0.59390.78780.70120.103*
C710.5856 (3)0.7650 (2)0.64974 (14)0.0824 (16)
H71A0.61730.73620.65090.124*
H71B0.60340.79960.64060.124*
H71C0.55280.75270.63390.124*
N40.74296 (12)0.43812 (12)0.70443 (7)0.0327 (6)
C400.71554 (16)0.48719 (15)0.68431 (9)0.0389 (8)
H40A0.73080.48590.65960.047*
H40B0.67070.48200.68340.047*
C410.7282 (2)0.54375 (17)0.69883 (11)0.0530 (10)
H41A0.77150.54660.70610.064*
H41B0.70230.55060.71990.064*
C420.7141 (2)0.58707 (19)0.67008 (15)0.0698 (14)
H420.70390.57750.64640.084*
C430.7178 (4)0.6430 (3)0.6824 (2)0.122 (3)
H43A0.70790.66860.66300.183*
H43B0.75940.65060.69080.183*
H43C0.68890.64850.70190.183*
C440.81231 (14)0.44254 (16)0.70681 (9)0.0354 (8)
H44A0.82260.47760.71930.042*
H44B0.82740.41130.72160.042*
C450.84656 (16)0.44170 (17)0.67194 (9)0.0431 (9)
H45A0.83030.47090.65600.052*
H45B0.84110.40510.66020.052*
C460.91481 (17)0.45219 (17)0.67907 (10)0.0456 (9)
H46A0.92870.42700.69820.055*
H46B0.93840.44300.65740.055*
C470.9282 (2)0.51121 (19)0.68954 (11)0.0562 (11)
H47A0.91090.53660.67190.084*
H47B0.97250.51670.69080.084*
H47C0.90990.51890.71280.084*
C480.72107 (15)0.43645 (16)0.74266 (8)0.0371 (8)
H48A0.74430.40700.75520.044*
H48B0.73170.47240.75390.044*
C490.65392 (16)0.42599 (18)0.74872 (9)0.0447 (9)
H49A0.64160.39090.73690.054*
H49B0.62970.45680.73840.054*
C500.64140 (18)0.4219 (2)0.78812 (10)0.0536 (11)
H50A0.66700.39190.79830.064*
H50B0.65340.45740.79960.064*
C510.5753 (2)0.4101 (2)0.79644 (13)0.0756 (16)
H51A0.56400.37350.78680.113*
H51B0.54950.43890.78570.113*
H51C0.56930.41010.82220.113*
C520.72437 (16)0.38665 (15)0.68374 (9)0.0390 (8)
H52A0.67920.38440.68360.047*
H52B0.73800.39120.65890.047*
C530.7494 (2)0.33229 (17)0.69768 (12)0.0555 (11)
H53A0.73930.32870.72320.067*
H53B0.79440.33220.69530.067*
C540.7232 (2)0.28321 (18)0.67774 (12)0.0573 (11)
H54A0.74190.24860.68710.069*
H54B0.67880.28130.68250.069*
C550.7328 (2)0.2850 (2)0.63830 (14)0.0755 (15)
H55A0.72130.24910.62790.113*
H55B0.77590.29260.63320.113*
H55C0.70750.31460.62800.113*
N50.48691 (14)0.27269 (12)0.47164 (7)0.0367 (7)
C240.51075 (17)0.22825 (14)0.44666 (9)0.0351 (8)
H24A0.47530.20910.43580.042*
H24B0.53340.20030.46080.042*
C250.55219 (17)0.24845 (14)0.41711 (9)0.0380 (8)
H25A0.53060.27680.40270.046*
H25B0.58910.26610.42740.046*
C260.57075 (18)0.19998 (15)0.39381 (10)0.0427 (9)
H26A0.53360.18350.38310.051*
H26B0.59020.17100.40870.051*
C270.6145 (2)0.21623 (18)0.36452 (11)0.0591 (12)
H27A0.62320.18360.34970.089*
H27B0.65260.23000.37490.089*
H27C0.59610.24560.35000.089*
C280.45485 (18)0.24536 (16)0.50351 (10)0.0449 (9)
H28A0.48670.23410.52070.054*
H28B0.42940.27420.51520.054*
C290.4153 (2)0.19582 (17)0.49664 (10)0.0535 (11)
H29A0.44060.16510.48710.064*
H29B0.38420.20550.47860.064*
C300.3834 (3)0.1764 (2)0.53010 (12)0.0849 (19)
H30A0.37810.13550.52970.102*0.126 (11)
H30B0.40790.18650.55120.102*0.126 (11)
H30C0.41480.16650.54790.102*0.874 (11)
H30D0.35920.20780.53980.102*0.874 (11)
C320.53868 (18)0.30782 (14)0.48615 (10)0.0420 (9)
H32A0.55610.33000.46640.050*
H32B0.52160.33440.50360.050*
C330.5899 (2)0.27594 (17)0.50367 (10)0.0533 (11)
H33A0.57440.25800.52550.064*
H33B0.60410.24610.48750.064*
C340.6431 (2)0.3132 (2)0.51296 (14)0.0690 (13)
H34A0.66010.32930.49090.083*
H34B0.62810.34450.52780.083*
C350.6928 (3)0.2834 (3)0.53243 (17)0.115 (3)
H35A0.70910.25340.51750.172*
H35B0.67640.26750.55440.172*
H35C0.72560.30970.53810.172*
C360.44488 (18)0.31485 (16)0.45387 (12)0.0513 (10)
H36A0.44620.34910.46850.062*0.5
H36B0.46360.32430.43080.062*0.5
H36C0.43410.34390.47140.062*0.5
H36D0.46760.33320.43440.062*0.5
C310.3223 (14)0.205 (2)0.5313 (12)0.10 (2)0.126 (11)
H31A0.30450.20050.55500.156*0.126 (11)
H31B0.29510.18820.51360.156*0.126 (11)
H31C0.32750.24470.52620.156*0.126 (11)
C370.3822 (5)0.3033 (6)0.4472 (4)0.056 (4)0.413 (15)
H37A0.36130.29480.46980.068*0.413 (15)
H37B0.37880.27020.43170.068*0.413 (15)
C380.3522 (4)0.3517 (4)0.4299 (3)0.033 (3)0.413 (15)
H38A0.37050.35800.40630.040*0.413 (15)
H38B0.35860.38560.44440.040*0.413 (15)
C390.2842 (4)0.3406 (6)0.4261 (4)0.058 (4)0.413 (15)
H39A0.27780.30940.40980.087*0.413 (15)
H39B0.26410.37400.41670.087*0.413 (15)
H39C0.26680.33140.44930.087*0.413 (15)
C31A0.3421 (4)0.1275 (3)0.52492 (15)0.113 (4)0.874 (11)
H31D0.30850.13790.50910.169*0.874 (11)
H31E0.32540.11590.54790.169*0.874 (11)
H31F0.36520.09660.51440.169*0.874 (11)
H10.370 (3)0.395 (3)0.6145 (19)0.169*
H30.367 (3)0.516 (3)0.6318 (18)0.169*
H50.421 (2)0.436 (3)0.6739 (19)0.169*
C37A0.3872 (5)0.2911 (5)0.4390 (4)0.100 (5)0.587 (15)
H37C0.36240.27690.45910.120*0.587 (15)
H37D0.39820.25860.42410.120*0.587 (15)
C38A0.3468 (5)0.3299 (5)0.4169 (3)0.076 (3)0.587 (15)
H38C0.37310.35300.40140.091*0.587 (15)
H38D0.32020.30710.40140.091*0.587 (15)
C39A0.3079 (8)0.3671 (6)0.4389 (3)0.100 (5)0.587 (15)
H39D0.27830.38620.42370.149*0.587 (15)
H39E0.33370.39470.45080.149*0.587 (15)
H39F0.28620.34480.45660.149*0.587 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.01950 (12)0.02207 (13)0.01470 (11)0.00500 (10)0.00147 (9)0.00069 (9)
Mo20.01694 (12)0.02293 (13)0.01566 (12)0.00276 (9)0.00218 (9)0.00190 (9)
Mo30.02231 (13)0.01587 (12)0.01950 (12)0.00241 (9)0.00034 (10)0.00050 (9)
Mo40.02074 (13)0.01765 (12)0.01906 (12)0.00023 (9)0.00347 (9)0.00331 (9)
Mo50.02338 (13)0.02119 (13)0.01444 (11)0.00208 (10)0.00390 (9)0.00292 (9)
Mo60.02484 (13)0.01597 (12)0.01748 (12)0.00340 (10)0.00096 (9)0.00195 (9)
Cl10.0554 (7)0.1203 (12)0.0748 (8)0.0373 (7)0.0177 (6)0.0061 (8)
Al10.0129 (4)0.0155 (4)0.0121 (4)0.0001 (3)0.0007 (3)0.0001 (3)
O10.0144 (9)0.0216 (10)0.0172 (9)0.0034 (8)0.0012 (7)0.0003 (8)
O20.0113 (9)0.0187 (9)0.0129 (9)0.0003 (7)0.0017 (7)0.0006 (7)
O30.0168 (10)0.0207 (10)0.0146 (9)0.0023 (8)0.0015 (7)0.0006 (8)
O40.0151 (9)0.0168 (9)0.0138 (9)0.0005 (7)0.0006 (7)0.0015 (7)
O50.0181 (10)0.0199 (10)0.0127 (9)0.0002 (8)0.0006 (7)0.0023 (7)
O60.0136 (9)0.0164 (9)0.0149 (9)0.0008 (7)0.0017 (7)0.0007 (7)
O70.0274 (11)0.0186 (10)0.0193 (10)0.0014 (8)0.0007 (8)0.0022 (8)
O80.0284 (12)0.0374 (13)0.0304 (12)0.0137 (10)0.0032 (9)0.0035 (10)
O90.0333 (12)0.0282 (11)0.0183 (10)0.0009 (9)0.0015 (9)0.0016 (8)
O100.0162 (10)0.0300 (11)0.0199 (10)0.0007 (8)0.0018 (8)0.0002 (8)
O110.0259 (12)0.0374 (13)0.0394 (13)0.0099 (10)0.0066 (10)0.0029 (10)
O120.0341 (12)0.0342 (12)0.0177 (10)0.0011 (10)0.0009 (9)0.0014 (9)
O130.0212 (10)0.0210 (10)0.0166 (9)0.0011 (8)0.0023 (8)0.0029 (8)
O140.0386 (13)0.0264 (11)0.0317 (12)0.0127 (10)0.0004 (10)0.0014 (9)
O150.0368 (13)0.0251 (11)0.0316 (12)0.0083 (10)0.0026 (10)0.0000 (9)
O160.0258 (11)0.0193 (10)0.0207 (10)0.0055 (8)0.0007 (8)0.0039 (8)
O170.0433 (13)0.0318 (12)0.0223 (11)0.0066 (10)0.0040 (10)0.0074 (9)
O180.0274 (12)0.0214 (11)0.0480 (14)0.0031 (9)0.0071 (10)0.0008 (10)
O190.0456 (14)0.0420 (14)0.0170 (10)0.0093 (11)0.0006 (10)0.0006 (9)
O200.0190 (10)0.0211 (10)0.0211 (10)0.0012 (8)0.0044 (8)0.0005 (8)
O210.0308 (12)0.0287 (12)0.0355 (12)0.0007 (9)0.0101 (10)0.0098 (10)
O220.0257 (11)0.0237 (10)0.0156 (9)0.0048 (8)0.0003 (8)0.0030 (8)
O230.0403 (13)0.0223 (11)0.0269 (11)0.0045 (9)0.0024 (10)0.0033 (9)
O240.0386 (13)0.0295 (12)0.0310 (12)0.0125 (10)0.0007 (10)0.0037 (9)
O250.0191 (11)0.0684 (17)0.0210 (11)0.0004 (11)0.0012 (9)0.0013 (11)
O260.0437 (16)0.0367 (16)0.092 (2)0.0063 (12)0.0173 (15)0.0000 (15)
O270.0347 (14)0.0613 (18)0.0700 (19)0.0108 (13)0.0082 (13)0.0301 (15)
N10.0136 (11)0.0282 (13)0.0155 (11)0.0016 (10)0.0018 (9)0.0046 (10)
N20.0154 (13)0.0341 (15)0.0447 (16)0.0010 (11)0.0015 (11)0.0029 (12)
C10.0136 (13)0.0267 (15)0.0137 (13)0.0018 (11)0.0018 (10)0.0022 (11)
C20.0140 (13)0.0219 (14)0.0197 (13)0.0042 (11)0.0036 (11)0.0016 (11)
C30.0139 (13)0.0208 (14)0.0229 (14)0.0006 (11)0.0064 (11)0.0007 (11)
C40.0114 (12)0.0213 (14)0.0147 (12)0.0011 (10)0.0036 (10)0.0013 (11)
C50.0168 (14)0.0251 (15)0.0222 (15)0.0047 (11)0.0012 (11)0.0008 (12)
C60.0168 (15)0.0442 (19)0.0215 (15)0.0047 (13)0.0032 (12)0.0012 (13)
C70.0174 (15)0.0351 (17)0.0285 (16)0.0030 (13)0.0054 (12)0.0035 (13)
C80.0205 (15)0.0342 (17)0.0310 (16)0.0029 (13)0.0037 (13)0.0047 (14)
C90.0301 (18)0.0369 (19)0.0384 (19)0.0035 (14)0.0013 (15)0.0010 (15)
C100.0187 (15)0.0377 (18)0.0382 (18)0.0012 (13)0.0019 (13)0.0003 (15)
C110.0197 (16)0.046 (2)0.045 (2)0.0002 (14)0.0001 (14)0.0068 (16)
C120.0315 (19)0.049 (2)0.044 (2)0.0056 (16)0.0024 (16)0.0085 (17)
C130.0237 (17)0.058 (2)0.052 (2)0.0135 (16)0.0010 (16)0.0096 (19)
C140.0219 (17)0.055 (2)0.050 (2)0.0046 (16)0.0032 (15)0.0091 (18)
C150.0219 (16)0.0409 (19)0.0417 (19)0.0025 (14)0.0006 (14)0.0031 (15)
C160.0258 (17)0.040 (2)0.044 (2)0.0066 (15)0.0003 (15)0.0056 (16)
C170.0253 (17)0.047 (2)0.0334 (18)0.0015 (15)0.0057 (14)0.0047 (15)
C180.0294 (19)0.053 (2)0.047 (2)0.0037 (16)0.0020 (16)0.0115 (18)
C190.045 (2)0.062 (3)0.047 (2)0.003 (2)0.0016 (18)0.013 (2)
C200.038 (2)0.082 (3)0.041 (2)0.015 (2)0.0067 (17)0.002 (2)
C210.0215 (18)0.073 (3)0.062 (3)0.0067 (18)0.0075 (17)0.001 (2)
C220.034 (2)0.057 (2)0.055 (2)0.0104 (18)0.0048 (18)0.003 (2)
C230.036 (2)0.065 (3)0.081 (3)0.006 (2)0.014 (2)0.030 (2)
O280.0456 (17)0.0564 (18)0.0642 (18)0.0168 (14)0.0026 (14)0.0194 (15)
O290.0352 (14)0.0543 (16)0.0408 (14)0.0130 (12)0.0089 (12)0.0034 (12)
O300.0332 (13)0.0448 (14)0.0325 (13)0.0012 (11)0.0066 (10)0.0043 (11)
O310.0462 (16)0.0498 (16)0.0424 (14)0.0070 (13)0.0147 (12)0.0002 (13)
O320.0570 (18)0.0613 (19)0.0432 (16)0.0130 (15)0.0113 (14)0.0132 (13)
O330.0294 (14)0.0673 (19)0.0619 (17)0.0017 (13)0.0063 (13)0.0007 (15)
O340.0338 (14)0.0498 (15)0.0445 (15)0.0052 (12)0.0011 (11)0.0027 (12)
O350.0497 (17)0.0565 (18)0.0666 (19)0.0248 (14)0.0159 (15)0.0166 (15)
O360.0396 (15)0.0506 (16)0.0489 (15)0.0131 (12)0.0062 (12)0.0208 (13)
N30.0312 (15)0.0295 (15)0.0360 (15)0.0020 (12)0.0051 (12)0.0153 (12)
C560.0354 (19)0.0304 (18)0.050 (2)0.0061 (15)0.0058 (16)0.0188 (16)
C570.038 (2)0.047 (2)0.066 (3)0.0032 (18)0.0128 (19)0.016 (2)
C580.042 (2)0.058 (3)0.050 (2)0.0125 (19)0.0120 (18)0.0142 (19)
C590.047 (2)0.092 (4)0.055 (3)0.017 (2)0.016 (2)0.015 (2)
C600.0390 (19)0.0280 (17)0.0317 (17)0.0023 (14)0.0062 (14)0.0122 (14)
C610.051 (2)0.0313 (19)0.042 (2)0.0018 (16)0.0018 (17)0.0082 (16)
C620.085 (3)0.037 (2)0.039 (2)0.013 (2)0.003 (2)0.0036 (17)
C630.121 (5)0.059 (3)0.064 (3)0.033 (3)0.031 (3)0.015 (2)
C640.0294 (18)0.0362 (18)0.0379 (18)0.0007 (14)0.0058 (14)0.0161 (15)
C650.042 (2)0.043 (2)0.040 (2)0.0092 (17)0.0086 (16)0.0101 (16)
C660.039 (2)0.068 (3)0.048 (2)0.010 (2)0.0102 (18)0.013 (2)
C670.056 (3)0.094 (4)0.065 (3)0.024 (3)0.023 (2)0.011 (3)
C690.050 (2)0.067 (3)0.041 (2)0.001 (2)0.0001 (18)0.013 (2)
C700.081 (4)0.129 (5)0.048 (3)0.053 (4)0.010 (2)0.027 (3)
C710.085 (4)0.094 (4)0.068 (3)0.019 (3)0.003 (3)0.001 (3)
N40.0243 (14)0.0468 (17)0.0270 (14)0.0042 (12)0.0065 (11)0.0073 (12)
C400.0317 (18)0.053 (2)0.0325 (18)0.0006 (16)0.0054 (15)0.0146 (16)
C410.057 (3)0.050 (2)0.052 (2)0.000 (2)0.007 (2)0.0052 (19)
C420.071 (3)0.052 (3)0.087 (4)0.012 (2)0.018 (3)0.016 (3)
C430.138 (6)0.082 (5)0.145 (7)0.005 (4)0.035 (5)0.008 (4)
C440.0240 (17)0.050 (2)0.0321 (17)0.0031 (15)0.0069 (14)0.0018 (15)
C450.036 (2)0.056 (2)0.0367 (19)0.0070 (17)0.0003 (16)0.0043 (17)
C460.033 (2)0.058 (2)0.046 (2)0.0041 (17)0.0021 (17)0.0051 (19)
C470.048 (2)0.071 (3)0.050 (2)0.019 (2)0.0023 (19)0.006 (2)
C480.0327 (18)0.054 (2)0.0248 (16)0.0000 (16)0.0055 (14)0.0076 (15)
C490.0332 (19)0.068 (3)0.0334 (18)0.0007 (18)0.0028 (15)0.0175 (18)
C500.043 (2)0.079 (3)0.039 (2)0.002 (2)0.0006 (17)0.020 (2)
C510.048 (3)0.120 (5)0.059 (3)0.009 (3)0.017 (2)0.037 (3)
C520.0327 (18)0.049 (2)0.0354 (18)0.0070 (16)0.0087 (15)0.0002 (16)
C530.052 (2)0.053 (2)0.062 (3)0.000 (2)0.015 (2)0.006 (2)
C540.047 (2)0.048 (2)0.077 (3)0.0021 (19)0.007 (2)0.006 (2)
C550.081 (4)0.062 (3)0.083 (4)0.016 (3)0.012 (3)0.017 (3)
N50.0461 (17)0.0298 (15)0.0343 (15)0.0003 (13)0.0116 (13)0.0032 (12)
C240.047 (2)0.0279 (17)0.0299 (17)0.0041 (15)0.0003 (15)0.0010 (14)
C250.049 (2)0.0325 (18)0.0322 (18)0.0042 (16)0.0031 (16)0.0021 (14)
C260.053 (2)0.035 (2)0.040 (2)0.0020 (17)0.0025 (17)0.0048 (16)
C270.078 (3)0.052 (3)0.047 (2)0.004 (2)0.019 (2)0.011 (2)
C280.057 (2)0.044 (2)0.0336 (19)0.0107 (18)0.0117 (17)0.0011 (16)
C290.075 (3)0.047 (2)0.038 (2)0.018 (2)0.012 (2)0.0029 (18)
C300.126 (5)0.084 (4)0.045 (3)0.062 (4)0.022 (3)0.007 (2)
C320.059 (2)0.0246 (17)0.043 (2)0.0065 (16)0.0166 (18)0.0089 (15)
C330.079 (3)0.044 (2)0.037 (2)0.019 (2)0.008 (2)0.0011 (17)
C340.071 (3)0.059 (3)0.076 (3)0.019 (2)0.002 (3)0.019 (2)
C350.129 (6)0.110 (5)0.105 (5)0.049 (4)0.072 (4)0.017 (4)
C360.054 (2)0.039 (2)0.061 (3)0.0075 (18)0.018 (2)0.0090 (19)
C310.09 (4)0.16 (6)0.07 (3)0.02 (4)0.00 (3)0.02 (3)
C370.042 (5)0.070 (7)0.056 (6)0.011 (5)0.029 (4)0.031 (5)
C380.040 (5)0.019 (5)0.040 (6)0.005 (4)0.009 (4)0.006 (4)
C390.039 (6)0.063 (8)0.072 (9)0.012 (5)0.005 (5)0.007 (6)
C31A0.174 (8)0.117 (6)0.047 (3)0.099 (6)0.015 (4)0.003 (3)
C37A0.080 (7)0.083 (7)0.137 (9)0.003 (5)0.021 (6)0.040 (6)
C38A0.078 (7)0.041 (6)0.109 (9)0.001 (5)0.026 (6)0.006 (6)
C39A0.111 (12)0.111 (10)0.077 (7)0.015 (9)0.004 (7)0.007 (7)
Geometric parameters (Å, º) top
Mo1—O22.3395 (18)C10—C151.405 (4)
Mo1—O32.3087 (18)C11—C121.378 (5)
Mo1—O71.927 (2)C12—C131.406 (5)
Mo1—O81.708 (2)C13—C141.378 (5)
Mo1—O91.7014 (19)C14—C151.387 (5)
Mo1—O101.929 (2)C16—C171.471 (5)
Mo2—O12.3078 (19)C17—C181.405 (5)
Mo2—O22.3467 (18)C17—C221.367 (5)
Mo2—O101.936 (2)C18—C191.383 (5)
Mo2—O111.696 (2)C19—C201.387 (6)
Mo2—O121.703 (2)C20—C211.368 (6)
Mo2—O131.9275 (19)C21—C221.384 (6)
Mo3—O12.3343 (19)N3—C561.521 (4)
Mo3—O62.3183 (18)N3—C601.520 (4)
Mo3—O131.9182 (19)N3—C641.524 (4)
Mo3—O141.707 (2)N3—C681.519 (4)
Mo3—O151.696 (2)C56—C571.513 (5)
Mo3—O161.9442 (19)C57—C581.513 (5)
Mo4—O52.3224 (19)C58—C591.528 (5)
Mo4—O62.3440 (17)C60—C611.519 (5)
Mo4—O161.9276 (19)C61—C621.525 (5)
Mo4—O171.711 (2)C62—C631.497 (6)
Mo4—O181.698 (2)C64—C651.509 (5)
Mo4—O201.9119 (19)C65—C661.518 (5)
Mo5—O42.3633 (17)C66—C671.511 (6)
Mo5—O52.3156 (19)C68—C691.514 (5)
Mo5—O191.698 (2)C69—C701.572 (7)
Mo5—O201.9299 (19)C70—C711.476 (7)
Mo5—O211.706 (2)N4—C401.524 (4)
Mo5—O221.9341 (19)N4—C441.525 (4)
Mo6—O32.3222 (19)N4—C481.520 (4)
Mo6—O42.3251 (18)N4—C521.516 (4)
Mo6—O71.9152 (19)C40—C411.489 (5)
Mo6—O221.9380 (19)C41—C421.533 (6)
Mo6—O231.698 (2)C42—C431.423 (8)
Mo6—O241.711 (2)C44—C451.514 (5)
Cl1—C201.749 (4)C45—C461.539 (5)
Al1—O11.878 (2)C46—C471.498 (6)
Al1—O21.8950 (19)C48—C491.509 (5)
Al1—O31.884 (2)C49—C501.514 (5)
Al1—O41.9183 (19)C50—C511.508 (6)
Al1—O51.8639 (19)C52—C531.509 (5)
Al1—O61.9269 (19)C53—C541.510 (6)
O2—C11.438 (3)C54—C551.503 (6)
O4—C21.450 (3)N5—C241.515 (4)
O6—C31.446 (3)N5—C281.539 (4)
O25—C51.222 (3)N5—C321.515 (5)
O26—C161.214 (4)N5—C361.523 (5)
O27—C121.373 (4)C24—C251.517 (5)
O27—C231.427 (4)C25—C261.513 (5)
N1—C41.468 (3)C26—C271.513 (5)
N1—C51.344 (4)C28—C291.493 (5)
N2—C81.418 (4)C29—C301.514 (5)
N2—C151.418 (4)C30—C311.504 (16)
N2—C161.407 (4)C30—C31A1.495 (6)
C1—C41.538 (4)C32—C331.510 (6)
C2—C41.528 (4)C33—C341.509 (6)
C3—C41.529 (4)C34—C351.496 (8)
C5—C61.531 (4)C36—C371.422 (11)
C6—C71.502 (4)C36—C37A1.494 (11)
C7—C81.350 (4)C37—C381.484 (11)
C7—C101.440 (4)C38—C391.518 (11)
C8—C91.493 (4)C37A—C38A1.533 (10)
C10—C111.401 (5)C38A—C39A1.485 (12)
O3—Mo1—O266.92 (6)Mo5—O5—Mo491.12 (7)
O7—Mo1—O281.02 (7)Al1—O5—Mo4104.75 (8)
O7—Mo1—O372.06 (7)Al1—O5—Mo5104.65 (8)
O7—Mo1—O10148.18 (8)Mo3—O6—Mo491.80 (6)
O8—Mo1—O2160.56 (9)Al1—O6—Mo3102.91 (8)
O8—Mo1—O395.20 (9)Al1—O6—Mo4101.91 (8)
O8—Mo1—O7101.29 (10)C3—O6—Mo3116.26 (15)
O8—Mo1—O1098.37 (10)C3—O6—Mo4119.26 (15)
O9—Mo1—O292.45 (8)C3—O6—Al1120.00 (15)
O9—Mo1—O3157.90 (9)Mo6—O7—Mo1119.47 (10)
O9—Mo1—O797.88 (9)Mo1—O10—Mo2118.32 (10)
O9—Mo1—O8106.21 (10)Mo3—O13—Mo2118.63 (9)
O9—Mo1—O10100.34 (9)Mo4—O16—Mo3119.71 (9)
O10—Mo1—O272.37 (7)Mo4—O20—Mo5119.08 (10)
O10—Mo1—O381.50 (7)Mo5—O22—Mo6118.87 (10)
O1—Mo2—O267.19 (6)C12—O27—C23116.5 (3)
O10—Mo2—O181.62 (7)C5—N1—C4127.8 (2)
O10—Mo2—O272.08 (7)C15—N2—C8107.9 (2)
O11—Mo2—O194.85 (9)C16—N2—C8125.7 (3)
O11—Mo2—O2160.81 (9)C16—N2—C15126.4 (3)
O11—Mo2—O1099.58 (10)O2—C1—C4112.9 (2)
O11—Mo2—O12106.20 (11)O4—C2—C4111.2 (2)
O11—Mo2—O13101.00 (10)O6—C3—C4111.6 (2)
O12—Mo2—O1158.22 (9)N1—C4—C1103.6 (2)
O12—Mo2—O292.44 (8)N1—C4—C2110.6 (2)
O12—Mo2—O1099.96 (9)N1—C4—C3107.8 (2)
O12—Mo2—O1397.39 (9)C2—C4—C1111.1 (2)
O13—Mo2—O172.59 (7)C2—C4—C3111.9 (2)
O13—Mo2—O280.65 (7)C3—C4—C1111.5 (2)
O13—Mo2—O10148.09 (8)O25—C5—N1124.6 (3)
O6—Mo3—O167.54 (6)O25—C5—C6123.4 (3)
O13—Mo3—O172.13 (7)N1—C5—C6111.9 (2)
O13—Mo3—O682.51 (7)C7—C6—C5116.8 (2)
O13—Mo3—O16148.25 (8)C8—C7—C6126.6 (3)
O14—Mo3—O194.54 (9)C8—C7—C10108.6 (3)
O14—Mo3—O6159.64 (9)C10—C7—C6124.5 (3)
O14—Mo3—O13101.68 (9)N2—C8—C9122.2 (3)
O14—Mo3—O1696.88 (9)C7—C8—N2108.9 (3)
O15—Mo3—O1158.52 (9)C7—C8—C9128.9 (3)
O15—Mo3—O692.99 (9)C11—C10—C7132.4 (3)
O15—Mo3—O1397.27 (9)C11—C10—C15120.1 (3)
O15—Mo3—O14106.06 (11)C15—C10—C7107.4 (3)
O15—Mo3—O16102.07 (9)C12—C11—C10118.5 (3)
O16—Mo3—O180.98 (7)O27—C12—C11125.5 (3)
O16—Mo3—O671.63 (7)O27—C12—C13113.8 (3)
O5—Mo4—O667.30 (6)C11—C12—C13120.7 (3)
O16—Mo4—O582.64 (8)C14—C13—C12121.3 (3)
O16—Mo4—O671.31 (7)C13—C14—C15118.2 (3)
O17—Mo4—O593.91 (9)C10—C15—N2107.0 (3)
O17—Mo4—O6158.74 (9)C14—C15—N2131.5 (3)
O17—Mo4—O1697.38 (9)C14—C15—C10121.2 (3)
O17—Mo4—O20102.68 (9)O26—C16—N2121.1 (3)
O18—Mo4—O5159.49 (9)O26—C16—C17122.6 (3)
O18—Mo4—O694.23 (9)N2—C16—C17116.3 (3)
O18—Mo4—O16100.35 (9)C18—C17—C16119.8 (3)
O18—Mo4—O17105.71 (11)C22—C17—C16121.1 (3)
O18—Mo4—O2097.32 (9)C22—C17—C18119.0 (3)
O20—Mo4—O572.05 (7)C19—C18—C17120.5 (3)
O20—Mo4—O681.59 (7)C18—C19—C20118.1 (4)
O20—Mo4—O16148.49 (8)C19—C20—Cl1117.3 (4)
O5—Mo5—O467.40 (6)C21—C20—Cl1120.3 (3)
O19—Mo5—O4158.93 (9)C21—C20—C19122.4 (4)
O19—Mo5—O593.44 (9)C20—C21—C22118.3 (4)
O19—Mo5—O20101.99 (10)C17—C22—C21121.6 (4)
O19—Mo5—O21105.88 (11)C56—N3—C64105.9 (2)
O19—Mo5—O2297.98 (10)C60—N3—C56111.2 (3)
O20—Mo5—O480.99 (7)C60—N3—C64111.1 (2)
O20—Mo5—O571.91 (7)C68—N3—C56111.0 (3)
O20—Mo5—O22148.48 (8)C68—N3—C60106.3 (2)
O21—Mo5—O494.25 (9)C68—N3—C64111.4 (3)
O21—Mo5—O5159.77 (9)C57—C56—N3115.3 (3)
O21—Mo5—O2097.69 (9)C58—C57—C56110.5 (3)
O21—Mo5—O22100.01 (9)C57—C58—C59111.4 (4)
O22—Mo5—O471.90 (7)C61—C60—N3116.3 (3)
O22—Mo5—O582.83 (8)C60—C61—C62110.0 (3)
O3—Mo6—O467.67 (6)C63—C62—C61113.4 (4)
O7—Mo6—O371.94 (7)C65—C64—N3116.0 (3)
O7—Mo6—O483.07 (7)C64—C65—C66109.5 (3)
O7—Mo6—O22148.91 (8)C67—C66—C65113.2 (4)
O22—Mo6—O380.82 (7)C69—C68—N3116.6 (3)
O22—Mo6—O472.72 (7)C68—C69—C70109.6 (3)
O23—Mo6—O3157.03 (9)C71—C70—C69113.5 (4)
O23—Mo6—O491.04 (8)C40—N4—C44111.6 (3)
O23—Mo6—O797.93 (9)C48—N4—C40111.6 (3)
O23—Mo6—O22101.66 (9)C48—N4—C44105.1 (2)
O23—Mo6—O24105.97 (11)C52—N4—C40105.5 (2)
O24—Mo6—O396.35 (9)C52—N4—C44110.7 (3)
O24—Mo6—O4161.50 (9)C52—N4—C48112.5 (3)
O24—Mo6—O7101.30 (9)C41—C40—N4116.6 (3)
O24—Mo6—O2296.25 (9)C40—C41—C42108.7 (3)
O1—Al1—O286.11 (8)C43—C42—C41113.4 (5)
O1—Al1—O397.99 (9)C45—C44—N4116.2 (3)
O1—Al1—O4174.93 (9)C44—C45—C46109.1 (3)
O1—Al1—O685.64 (8)C47—C46—C45113.0 (3)
O2—Al1—O490.82 (8)C49—C48—N4117.1 (3)
O2—Al1—O691.67 (8)C48—C49—C50109.6 (3)
O3—Al1—O285.40 (8)C51—C50—C49113.0 (4)
O3—Al1—O485.77 (8)C53—C52—N4115.3 (3)
O3—Al1—O6175.16 (9)C52—C53—C54111.2 (3)
O4—Al1—O690.43 (8)C55—C54—C53114.7 (4)
O5—Al1—O196.20 (9)C24—N5—C28110.1 (3)
O5—Al1—O2176.58 (9)C24—N5—C36113.7 (3)
O5—Al1—O396.75 (9)C32—N5—C24111.0 (3)
O5—Al1—O486.69 (8)C32—N5—C28107.2 (3)
O5—Al1—O686.00 (8)C32—N5—C36104.0 (3)
Mo2—O1—Mo390.87 (7)C36—N5—C28110.6 (3)
Al1—O1—Mo2104.31 (8)N5—C24—C25116.0 (3)
Al1—O1—Mo3103.91 (8)C26—C25—C24110.0 (3)
Mo1—O2—Mo290.16 (6)C25—C26—C27113.3 (3)
Al1—O2—Mo1103.02 (8)C29—C28—N5117.9 (3)
Al1—O2—Mo2102.31 (8)C28—C29—C30111.5 (3)
C1—O2—Mo1118.66 (15)C31—C30—C29107 (2)
C1—O2—Mo2118.01 (15)C31A—C30—C29114.2 (4)
C1—O2—Al1119.67 (15)C33—C32—N5115.6 (3)
Mo1—O3—Mo691.56 (7)C34—C33—C32112.0 (3)
Al1—O3—Mo1104.53 (8)C35—C34—C33113.1 (4)
Al1—O3—Mo6103.88 (8)C37—C36—N5122.1 (6)
Mo6—O4—Mo590.65 (6)C37A—C36—N5114.9 (5)
Al1—O4—Mo5101.15 (8)C36—C37—C38110.7 (9)
Al1—O4—Mo6102.66 (8)C37—C38—C39109.9 (9)
C2—O4—Mo5119.28 (15)C36—C37A—C38A117.4 (9)
C2—O4—Mo6117.40 (15)C39A—C38A—C37A113.0 (11)
C2—O4—Al1120.47 (15)
Selected bond lengths (Å) and angles (°) in AlMo6-NH-Cin and AlMo6-NH-Indo top
AlMo6-NH-CinAlMo6-NH-Indo
Mo—µ3-O2.291 (4)–2.391 (4)2.3068 (19)–2.3632 (18)
Mo—µ2-O1.910 (4)–1.941 (5)1.912 (2)–1.944 (2)
Mo—Ot1.694 (5)–1.722 (5)1.696 (2)–1.711 (2)
Al—µ3-O1.864 (5)–1.923 (4)1.863 (2)–1.927 (2)
 

Acknowledgements

We are grateful to Dr Hana Čipčić-Paljetak and Professor Dr Donatella Verbanac for the anti­bacterial investigations at the Center for Translational and Clinical Research, Croatian Center of Excellence for Reproductive and Regenerative Medicine, School of Medicine, University of Zagreb, Croatia. We thank Ricarda Bugl for the support with NMR spectroscopy measurements at the NMR Centre, Core facilities service of University of Vienna, and Elias Tanuhadi, MSc, for proofreading the manuscript.

Funding information

Funding for this research was provided by the Austrian Science Fund (FWF) (award No. M2203 to Nadiia I. Gumerova; award No. P27534 to Annette Rompel).

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