Oxidorhenium(V) complexes of apigenin: a rare example of catalysis with <i>O</i>,<i>O</i>-bidentate ligands obtained from a naturally renewable resource.
Milovanović, Milan R; Nikolić, Stefan R; Dupé, Antoine; Schachner, Jörg A; Mihajlović, Ljiljana E; Dalton transactions (Cambridge, England : 2003) 54 (2025) 11047–11055; doi:10.1039/d5dt01095k

data_7718981
_publ_section_title
;
 Oxidorhenium(V) complexes of apigenin: a rare example of catalysis with
 <i>O</i>,<i>O</i>-bidentate ligands obtained from a naturally renewable
 resource.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11047
_journal_page_last               11055
_journal_paper_doi               10.1039/d5dt01095k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C45 H52 Cl2 O6 P Re Si2, 0.5(C3 H6 O)'
_chemical_formula_sum            'C46.5 H55 Cl2 O6.5 P Re Si2'
_chemical_formula_weight         1062.15
_chemical_name_systematic
'(triphenylphosphine)-[7-{[t-butyl(dimethyl)silyl]oxy}-5-oxido-2-(4-{[t-butyl(dimethyl)silyl]oxy}phenyl)-4H-1-benzopyran-4-onato]-dichlorido-oxido-rhenium(V) acetone solvate 2:1'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-03
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2024-12-04 deposited with the CCDC.	2025-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                74.2060(10)
_cell_angle_beta                 79.4460(10)
_cell_angle_gamma                66.5190(10)
_cell_formula_units_Z            2
_cell_length_a                   10.52860(10)
_cell_length_b                   13.15930(10)
_cell_length_c                   19.46270(10)
_cell_measurement_reflns_used    35635
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.7630
_cell_measurement_theta_min      3.7620
_cell_volume                     2371.33(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.113a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.106a 64-bit (release 01-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.113a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  27.00   0.50    0.20    --   24.00  75.00  97.23   52
  2  \w      9.00  40.00   0.50    0.20    --   28.00  65.00  49.31   62
  3  \w     13.00  40.00   0.50    0.20    --   32.00  65.00 -38.81   54
  4  \w      2.00  28.00   0.50    0.20    --   24.00  74.00 -98.45   52
  5  \w     34.00  60.00   0.50    0.60    --  106.72 -61.00 -30.00   52
  6  \w     47.00  73.00   0.50    0.60    --  110.00 -80.00  13.29   52
  7  \w    110.00 135.00   0.50    0.60    --  110.00 -79.00  97.09   50
  8  \w     52.00  84.00   0.50    0.60    --  110.00 -79.00  97.09   64
  9  \w     43.00  69.00   0.50    0.60    --  110.00 -80.00 -80.38   52
 10  \w     44.00  85.00   0.50    0.60    --  110.00 -79.00-101.39   82
 11  \w     40.00 105.00   0.50    0.60    --  106.72 -77.00-150.00  130
 12  \w    110.00 136.00   0.50    0.60    --  110.00 -79.00-101.39   52
 13  \w     39.00  70.00   0.50    0.60    --  110.00-133.00 -14.94   62
 14  \w     73.00 111.00   0.50    0.60    --  106.72-125.00  90.00   76
 15  \w     86.00 112.00   0.50    0.60    --  106.72-125.00  60.00   52
 16  \w     52.00  78.00   0.50    0.60    --  106.72-111.00 -24.00   52
 17  \w     91.00 116.00   0.50    0.60    --  110.00-133.00 -14.94   50
 18  \w     86.00 112.00   0.50    0.60    --  106.72-125.00-150.00   52
 19  \w     77.00 112.00   0.50    0.60    --  106.72-125.00-120.00   70
 20  \w     48.00  73.00   0.50    0.60    --  106.72 -95.00-120.00   50
 21  \w     61.00 112.00   0.50    0.60    --  106.72-125.00 -60.00  102
 22  \w     82.00 108.00   0.50    0.60    --  106.72-111.00 -24.00   52
 23  \w    111.00 137.00   0.50    0.60    --  110.00 -88.00  73.05   52
 24  \w    108.00 134.00   0.50    0.60    --  110.00 -88.00 -60.07   52
 25  \w     88.00 125.00   0.50    0.60    --  110.00 -88.00 -16.22   74
 26  \w     46.00  72.00   0.50    0.60    --  110.00 -88.00 -38.25   52
 27  \w     54.00  84.00   0.50    0.60    --  110.00 -88.00  32.46   60
 28  \w     60.00 107.00   0.50    0.60    --  110.00-103.00 113.83   94
 29  \w     43.00  80.00   0.50    0.60    --  110.00 -88.00  73.05   74
 30  \w     44.00  70.00   0.50    0.60    --  110.00 -88.00  36.03   52
 31  \w     85.00 111.00   0.50    0.60    --  110.00 -88.00  36.03   52
 32  \w     44.00  70.00   0.50    0.60    --  110.00 -88.00 -60.07   52
 33  \w     44.00 104.00   0.50    0.60    --  110.00 -87.00-116.45  120
 34  \w     46.00  76.00   0.50    0.60    --  110.00 -88.00 -16.22   60
 35  \w     48.00  74.00   0.50    0.60    --  110.00 -87.00  10.90   52
 36  \w     77.00 105.00   0.50    0.60    --  110.00 -86.00  42.38   56
 37  \w     46.00  72.00   0.50    0.60    --  110.00 -86.00  42.38   52
 38  \w     45.00  71.00   0.50    0.60    --  110.00 -86.00  96.17   52
 39  \w     47.00  73.00   0.50    0.60    --  110.00 -87.00 145.09   52
 40  \w     44.00  80.00   0.50    0.60    --  110.00 -84.00 174.42   72
 41  \w     45.00 107.00   0.50    0.60    --  110.00 -87.00 139.46  124
 42  \w    100.00 126.00   0.50    0.60    --  110.00 -84.00 174.42   52
 43  \w     44.00  69.00   0.50    0.60    --  110.00 -83.00 119.09   50
 44  \w     44.00  77.00   0.50    0.60    --  110.00 -81.00 149.34   66
 45  \w     53.00 110.00   0.50    0.60    --  110.00 -81.00  84.43  114
 46  \w     43.00  71.00   0.50    0.60    --  110.00 -82.00  57.72   56
 47  \w     50.00  75.00   0.50    0.60    --  110.00 -82.00 -35.64   50
 48  \w     44.00  94.00   0.50    0.60    --  110.00 -81.00-159.05  100
 49  \w    139.00 165.00   0.50    0.60    --  110.00  10.00-150.87   52
 50  \w     98.00 127.00   0.50    0.60    --  106.72  45.00-150.00   58
 51  \w    137.00 163.00   0.50    0.60    --  106.72  77.00  60.00   52
 52  \w    142.00 167.00   0.50    0.60    --  106.72  77.00  90.00   50
 53  \w    107.00 136.00   0.50    0.60    --  106.72  77.00  90.00   58
 54  \w     91.00 122.00   0.50    0.60    --  106.72  30.00 120.00   62
 55  \w     72.00 110.00   0.50    0.60    --  110.00  19.00  35.33   76
 56  \w     64.00 144.00   0.50    0.60    --  110.00  17.00  77.60  160
 57  \w     90.00 134.00   0.50    0.60    --  110.00  19.00 -59.76   88
 58  \w     70.00 118.00   0.50    0.60    --  110.00  18.00-128.55   96
 59  \w     73.00 148.00   0.50    0.60    --  110.00  19.00-176.47  150
 60  \w     69.00 124.00   0.50    0.60    --  110.00  18.00 -69.96  110
 61  \w    131.00 158.00   0.50    0.60    --  110.00  15.00 104.29   54
 62  \w    121.00 154.00   0.50    0.60    --  110.00  14.00 159.38   66
 63  \w     73.00  99.00   0.50    0.60    --  110.00  15.00 104.29   52
 64  \w     57.00  86.00   0.50    0.60    --  110.00  11.00  70.64   58
 65  \w     62.00  88.00   0.50    0.60    --  110.00  14.00 159.38   52
 66  \w    136.00 173.00   0.50    0.60    --  110.00  11.00  70.64   74
 67  \w    123.00 149.00   0.50    0.60    --  110.00  13.00 -19.74   52
 68  \w    136.00 162.00   0.50    0.60    --  106.72 125.00  30.00   52
 69  \w   -142.00 -51.00   0.50    0.20    --  -68.00 -56.00 117.34  182
 70  \w   -143.00 -51.00   0.50    0.20    --  -68.00 -55.00   4.53  184
 71  \w    -29.00   3.00   0.50    0.20    --   12.00 105.00  23.29   64
 72  \w    -39.00  -7.00   0.50    0.20    --    8.00 117.00 171.99   64
 73  \w    -86.00 -13.00   0.50    0.20    --  -80.24 125.00 150.00  146
 74  \w   -105.00 -13.00   0.50    0.20    --  -80.24  77.00 120.00  184
 75  \w    -35.00  -2.00   0.50    0.20    --  -80.24  30.00  90.00   66
 76  \w    -35.00  -2.00   0.50    0.20    --  -80.24  30.00 120.00   66
 77  \w    -71.00  -7.00   0.50    0.20    --  -80.24  61.00 -30.00  128
 78  \w    -51.00  -4.00   0.50    0.20    --  -80.24  45.00 -90.00   94
 79  \w    -35.00  -2.00   0.50    0.20    --  -80.24  30.00-120.00   66
 80  \w    -26.00  25.00   0.50    0.20    --  -51.95  19.00-180.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0210826000
_diffrn_orient_matrix_UB_12      -0.0804026000
_diffrn_orient_matrix_UB_13      0.0746398000
_diffrn_orient_matrix_UB_21      -0.1337240000
_diffrn_orient_matrix_UB_22      0.0837138000
_diffrn_orient_matrix_UB_23      0.0309539000
_diffrn_orient_matrix_UB_31      -0.0854836000
_diffrn_orient_matrix_UB_32      -0.0604582000
_diffrn_orient_matrix_UB_33      -0.0169225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51866
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.371
_diffrn_reflns_theta_min         3.755
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.227
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.113a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method
'crystallized by slow evaporation from an acetone solution'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         10041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+2.3282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9662
_reflns_number_total             10041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01095k2.cif
_cod_data_source_block           ad38
_cod_depositor_comments
'Adding full bibliography for 7718978--7718982.cif.'
_cod_original_formula_sum        'C46.50 H55 Cl2 O6.50 P Re Si2'
_cod_database_code               7718981
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C46.50 H55 Cl2 O6.50 P Re Si2'
_chemical_oxdiff_usercomment     MRM66-8
_shelx_estimated_absorpt_t_max   0.632
_shelx_estimated_absorpt_t_min   0.532
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41),
  C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C16(H161,H162,H163), C17(H171,H172,H173), C19(H191,H192,H193), C20(H201,H202,
 H203), C21(H211,H212,H213), C22(H221,H222,H223), C23(H231,H232,H233), C25(H251,
 H252,H253), C26(H261,H262,H263), C27(H271,H272,H273)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 32 electrons were 
found in a volume of 222\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C3H6O] per Asymmetric Unit 
which account for 32 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              42780
_shelx_hkl_checksum              13278
_shelx_fab_checksum              24142
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_original_sample_id MRM66-8
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.716