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_7718978
_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         'C19 H14 O7'
_chemical_formula_sum            'C19 H14 O7'
_chemical_formula_weight         354.30
_chemical_name_systematic
5-hydroxy-7-acetoxy-2-(4-[acetoxy]phenyl)-4H-1-benzopyran-4-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-29
_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                90
_cell_angle_beta                 105.164(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3307(3)
_cell_length_b                   4.99390(10)
_cell_length_c                   19.0125(3)
_cell_measurement_reflns_used    7897
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      77.4550
_cell_measurement_theta_min      3.0670
_cell_volume                     1588.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.106a 64-bit (release 01-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.123a (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      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -41.00  -9.00   0.50    0.70    --    8.00 120.00-153.19   64
  2  \w    -29.00   3.00   0.50    0.70    --   12.00 105.00 109.03   64
  3  \w      9.00  39.00   0.50    0.70    --   28.00  66.00  57.57   60
  4  \w   -143.00 -51.00   0.50    0.70    --  -68.00 -53.00-157.85  184
  5  \w    -85.00 -13.00   0.50    0.70    --  -80.27 125.00  90.00  144
  6  \w    -35.00  -3.00   0.50    0.70    --  -80.27  30.00-120.00   64
  7  \w    -71.00  -7.00   0.50    0.70    --  -80.27  61.00  60.00  128
  8  \w    -35.00  -3.00   0.50    0.70    --  -80.27  30.00 -60.00   64
  9  \w   -160.00 -68.00   0.50    3.50    --  -84.00 -47.00 138.27  184
 10  \w     40.00 105.00   0.50    3.50    --  106.75 -77.00 120.00  130
 11  \w    101.00 174.00   0.50    3.50    --  106.75  91.00-175.00  146
 12  \w     34.00  71.00   0.50    3.50    --  106.75 -61.00-180.00   74
 13  \w     34.00  71.00   0.50    3.50    --  106.75 -61.00  60.00   74
 14  \w     90.00 178.00   0.50    3.50    --  106.75  30.00   0.00  176
 15  \w     34.00  71.00   0.50    3.50    --  106.75 -61.00   0.00   74
 16  \w    148.00 177.00   0.50    3.50    --  110.00  -5.00 150.96   58
 17  \w     66.00 163.00   0.50    3.50    --  110.00  18.00  70.89  194
 18  \w     81.00 133.00   0.50    3.50    --  110.00 -88.00 -94.67  104
 19  \w     44.00  70.00   0.50    3.50    --  110.00 -87.00  40.32   52
 20  \w    106.00 132.00   0.50    3.50    --  110.00 -82.00 131.62   52
 21  \w     45.00  71.00   0.50    3.50    --  110.00 -82.00 131.62   52
 22  \w     52.00  89.00   0.50    3.50    --  110.00 -78.00  -3.58   74
 23  \w    153.00 178.00   0.50    3.50    --  110.00  14.00  18.38   50
 24  \w     67.00 105.00   0.50    3.50    --  110.00  14.00  18.38   76
 25  \w    137.00 171.00   0.50    3.50    --  110.00  11.00 -80.42   68
 26  \w    106.00 134.00   0.50    3.50    --  110.00 -81.00  89.16   56
 27  \w     45.00  85.00   0.50    3.50    --  110.00  11.00 -80.42   80
 28  \w     80.00 113.00   0.50    3.50    --  110.00 -88.00 -29.20   66
 29  \w    121.00 146.00   0.50    3.50    --  110.00  18.00  70.89   50
 30  \w     61.00  86.00   0.50    3.50    --  110.00   4.00 -99.41   50
 31  \w     50.00  86.00   0.50    3.50    --  110.00 -85.00 144.63   72
 32  \w    130.00 156.00   0.50    3.50    --  110.00   4.00 -99.41   52
 33  \w     43.00 125.00   0.50    3.50    --  110.00 -87.00  54.85  164
 34  \w     71.00  97.00   0.50    3.50    --  110.00 -81.00  89.16   52
 35  \w     49.00 103.00   0.50    3.50    --  110.00 -87.00-130.02  108
 36  \w    153.00 178.00   0.50    3.50    --  110.00  19.00 177.29   50
 37  \w     55.00 100.00   0.50    3.50    --  110.00 -88.00-158.65   90
;
_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      0.0221854000
_diffrn_orient_matrix_UB_12      -0.1723895000
_diffrn_orient_matrix_UB_13      0.0695762000
_diffrn_orient_matrix_UB_21      -0.0298359000
_diffrn_orient_matrix_UB_22      0.2234940000
_diffrn_orient_matrix_UB_23      0.0421818000
_diffrn_orient_matrix_UB_31      -0.0842823000
_diffrn_orient_matrix_UB_32      -0.1244773000
_diffrn_orient_matrix_UB_33      -0.0206115000
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17848
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.367
_diffrn_reflns_theta_min         3.074
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.123a (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    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'The material was recrystallised from THF by slow evaporation'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.4467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2952
_reflns_number_total             3369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01095k2.cif
_cod_data_source_block           ad67
_cod_depositor_comments
'Adding full bibliography for 7718978--7718982.cif.'
_cod_database_code               7718978
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C19 H14 O7'
_chemical_oxdiff_usercomment     AKME28
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.876
_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. Restrained distances
 O1-H1
 0.88 with sigma of 0.001
3. Others
 Sof(O8)=1-FVAR(1)
 Sof(O7)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C2(H2), C15(H15), C11(H11), C14(H14), C12(H12)
4.b Idealised Me refined as rotating group:
 C19(H191,H192,H193), C17(H171,H172,H173)
;
_shelx_res_checksum              28899
_shelx_hkl_checksum              33279
_olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MiTeGen loop'
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.875