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_7718982
_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         'C37 H28 Cl2 O8 P Re, 1(C H Cl3)'
_chemical_formula_sum            'C38 H29 Cl5 O8 P Re'
_chemical_formula_weight         1008.03
_chemical_name_systematic
(triphenylphosphine)-[7-acetoxy-5-oxido-2-(4-acetoxyphenyl)-4H-1-benzopyran-4-onato]-dichlorido-oxido-rhenium(V)
_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             2024-11-29
_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                109.1600(10)
_cell_angle_beta                 91.3940(10)
_cell_angle_gamma                101.3280(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4722(4)
_cell_length_b                   21.1056(10)
_cell_length_c                   21.4236(10)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      63.240
_cell_measurement_theta_min      3.179
_cell_volume                     3948.6(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            162484
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.289
_diffrn_reflns_theta_min         1.908
_diffrn_source                   MetalJet
_diffrn_source_current           3.57
_diffrn_source_power             0.24979289999999998
_diffrn_source_voltage           69.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.518
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1473 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.7341.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1071
_refine_ls_number_reflns         19509
_refine_ls_number_restraints     202
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0237P)^2^+6.5379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19054
_reflns_number_total             19509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01095k2.cif
_cod_data_source_block           snk35-4
_cod_depositor_comments
'Adding full bibliography for 7718978--7718982.cif.'
_cod_database_code               7718982
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.441
_shelx_estimated_absorpt_t_min   0.282
_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
 C81-Cl11 = C81-Cl12 = C81-Cl13
 1.78 with sigma of 0.02
 C84-Cl21 = C84-Cl22 = C84-Cl20
 1.78 with sigma of 0.02
 C83-Cl17 = C83-Cl18 = C83-Cl19
 1.78 with sigma of 0.02
 C81-Cl11 \\sim C81-Cl12 \\sim C81-Cl13
 with sigma of 0.02
 Cl11-Cl12 \\sim Cl12-Cl13 \\sim Cl13-Cl11
 with sigma of 0.04
 C84-Cl21 \\sim C84-Cl22 \\sim C84-Cl20
 with sigma of 0.02
 Cl21-Cl22 \\sim Cl21-Cl20 \\sim Cl22-Cl20
 with sigma of 0.04
 C83-Cl17 \\sim C84-Cl18 \\sim C84-Cl19
 with sigma of 0.02
 Cl17-Cl18 \\sim Cl17-Cl19 \\sim Cl18-Cl19
 with sigma of 0.04
 C81-Cl11 \\sim C82-Cl15
 with sigma of 0.02
 C81-Cl12 \\sim C82-Cl16
 with sigma of 0.02
 C81-Cl13 \\sim C82-Cl14
 with sigma of 0.02
 Cl11-Cl12 \\sim Cl15-Cl16
 with sigma of 0.04
 Cl11-Cl13 \\sim Cl15-Cl14
 with sigma of 0.04
 Cl12-Cl13 \\sim Cl16-Cl14
 with sigma of 0.04
 C84-Cl21 \\sim C85-Cl23
 with sigma of 0.02
 C84-Cl22 \\sim C85-Cl24
 with sigma of 0.02
 C84-Cl20 \\sim C85-Cl25
 with sigma of 0.02
 Cl21-Cl22 \\sim Cl23-Cl24
 with sigma of 0.04
 Cl21-Cl20 \\sim Cl23-Cl25
 with sigma of 0.04
 Cl22-Cl20 \\sim Cl24-Cl25
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C81 \\sim Cl11 \\sim Cl12 \\sim Cl13: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C84 \\sim Cl21 \\sim Cl22 \\sim Cl20: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C83 \\sim Cl17 \\sim Cl18 \\sim Cl19: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C81, Cl11, Cl12, Cl13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C84, Cl21, Cl22, Cl20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C83, Cl17, Cl18, Cl19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C82, Cl16, Cl14, Cl15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl25, C85, Cl24, Cl23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(C83)+Sof(H83)+Sof(Cl17)+Sof(Cl19)+Sof(Cl18)]+1*[Sof(C84)+Sof(H84)+
 Sof(Cl21)+Sof(Cl22)+Sof(Cl20)]+1*[Sof(C85)+Sof(H85)+Sof(Cl25)+Sof(Cl24)+
 Sof(Cl23)]=1 with esd of 0
 Sof(C82)=Sof(H82)=Sof(Cl14)=Sof(Cl15)=Sof(Cl16)=1-FVAR(1)
 Sof(C81)=Sof(H81)=Sof(Cl11)=Sof(Cl12)=Sof(Cl13)=FVAR(1)
 Sof(C83)=Sof(H83)=Sof(Cl17)=Sof(Cl19)=Sof(Cl18)=FVAR(2)
 Sof(C84)=Sof(H84)=Sof(Cl21)=Sof(Cl22)=Sof(Cl20)=FVAR(3)
 Sof(C85)=Sof(H85)=Sof(Cl25)=Sof(Cl24)=Sof(Cl23)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C81(H81), C82(H82), C83(H83), C84(H84), C85(H85)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C71(H71),
 C73(H73), C42(H42), C44(H44), C48(H48), C51(H51), C52(H52), C54(H54), C55(H55),
  C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C67(H67), C68(H68),
 C69(H69), C70(H70), C76(H76), C77(H77), C74(H74), C75(H75)
6.c Idealised Me refined as rotating group:
 C17(H171,H172,H173), C19(H191,H192,H193), C57(H571,H572,H573), C59(H591,H592,
 H593)
;
_shelx_res_checksum              55386
_shelx_hkl_checksum              42636
_olex2_exptl_crystal_mounting_method 'The crystal was mounted on a nylon loop'
_olex2_submission_original_sample_id SNK35-4
_olex2_submission_special_instructions 'No special instructions were received'