Dibismuthanes in catalysis: from synthesis and characterization to redox behavior towards oxidative cleavage of 1,2-diols.
Magre, Marc; Kuziola, Jennifer; Nöthling, Nils; Cornella, Josep; Organic & biomolecular chemistry 19 (2021) 4922–4929; doi:10.1039/d1ob00367d

data_7158068
_publ_section_title
;
 Dibismuthanes in catalysis: from synthesis and characterization to redox
 behavior towards oxidative cleavage of 1,2-diols.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4922
_journal_page_last               4929
_journal_paper_doi               10.1039/d1ob00367d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C39 H32 Bi2 Cl4 O, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C39.5 H33 Bi2 Cl5 O'
_chemical_formula_weight         1118.87
_chemical_name_systematic
;
(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dichlorodiphenyl-\l^5^-bismuthane)
;
_chemical_properties_physical    none
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                MBH-MA-077-01
_audit_creation_date             2020-07-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3959(6)
_cell_length_b                   13.9993(6)
_cell_length_c                   21.7582(10)
_cell_measurement_reflns_used    9637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.6319
_cell_measurement_theta_min      2.2165
_cell_volume                     3709.3(3)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         1\mS
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            144619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.672
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.867
_exptl_absorpt_correction_T_max  0.83591
_exptl_absorpt_correction_T_min  0.67911
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_description       prism
_exptl_crystal_F_000             2116
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  dichloromethane, hexane'
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.021
_refine_diff_density_max         2.264
_refine_diff_density_min         -2.609
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         8521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0160
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0071P)^2^+9.9351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0323
_refine_ls_wR_factor_ref         0.0339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7847
_reflns_number_total             8521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00367d2.cif
_cod_data_source_block           13220sadabs
_cod_depositor_comments
'Adding full bibliography for 7158061--7158068.cif.'
_cod_original_formula_sum        'C39.50 H33 Bi2 Cl5 O'
_cod_database_code               7158068
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.628
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H31,H31A} of C31
 At 1.5 times of:
  All C(H,H,H) groups, {H99A,H99B} of C99
2. Others
 Fixed Sof: C29A(0.6) H29A(0.6) C29B(0.4) H29B(0.4) C30A(0.6) H30A(0.6)
 C30B(0.4) H30B(0.4) H31(0.6) H31A(0.4) C34A(0.6) C34B(0.4) C35A(0.6) H35A(0.6)
 C35B(0.4) H35B(0.4) C36A(0.6) H36A(0.6) C36B(0.4) H36B(0.4) C37A(0.6)
 H37A(0.6) C37B(0.4) H37B(0.4) C38A(0.6) H38A(0.6) C38B(0.4) H38B(0.4)
 C39A(0.6) H39A(0.6) C39B(0.4) H39B(0.4) Cl5A(0.5) Cl5B(0.5) C99(0.5) H99A(0.5)
 H99B(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29A(H29A), C29B(H29B), C30A(H30A), C30B(H30B), C31(H31), C31(H31A), C32(H32),
  C33(H33), C35A(H35A), C35B(H35B), C36A(H36A), C36B(H36B), C37A(H37A),
 C37B(H37B), C38A(H38A), C38B(H38B), C39A(H39A), C39B(H39B)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              20011
_shelx_hkl_checksum              38608
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3