Synthesis and characterization of chlorotriarylbismuthonium salts.
Kuziola, Jennifer; Nöthling, Nils; Leutzsch, Markus; Cornella, Josep; Chemical communications (Cambridge, England) 60 (2024) 10532–10535; doi:10.1039/d4cc03364g

data_7133588
_publ_section_title
;
 Synthesis and characterization of chlorotriarylbismuthonium salts.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10532
_journal_page_last               10535
_journal_paper_doi               10.1039/d4cc03364g
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H12 B F24, C32 H38 Bi Cl N O'
_chemical_formula_sum            'C64 H50 B Bi Cl F24 N O'
_chemical_formula_weight         1560.29
_chemical_name_systematic
'((chloromesityl-\l^5^-bismut)oxy)pyridinium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate'
_chemical_properties_physical    none
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                15552
_audit_creation_date             2024-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                91.274(2)
_cell_angle_beta                 104.828(2)
_cell_angle_gamma                99.677(2)
_cell_formula_units_Z            1
_cell_length_a                   10.8125(4)
_cell_length_b                   12.0526(4)
_cell_length_c                   13.0336(5)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.28
_cell_volume                     1614.80(10)
_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 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45758
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         1.620
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_T_max  0.81139
_exptl_absorpt_correction_T_min  0.60986
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       prism
_exptl_crystal_F_000             770
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  dichloromethane, hexane'
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.119
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 6059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1007
_refine_ls_number_reflns         17115
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0333P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                15711
_reflns_number_total             17115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03364g2.cif
_cod_data_source_block           15552sadabs
_cod_depositor_comments
'Adding full bibliography for 7133586--7133592.cif.'
_cod_database_code               7133588
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.725
_shelx_estimated_absorpt_t_min   0.495
_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
 C56-F18A = F17A-F17B
 1.38 with sigma of 0.1
 C63B-F19B
 1.29 with sigma of 0.02
 C63B-F21B
 1.36 with sigma of 0.02
 C63B-F20B
 1.27 with sigma of 0.02
 F19A-F21A \\sim F21A-F20A \\sim F20A-F19A
 with sigma of 0.03
 C63B-F19B \\sim C63B-F21B \\sim C63B-F20B
 with sigma of 0.02
 F19B-F21B \\sim F21B-F20B \\sim F20B-F19B
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(F9A) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F18A)
\\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F3A) \\sim Ueq,
Uanis(F24A) \\sim Ueq, Uanis(F22A) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F23A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F17A) \\sim Ueq, Uanis(F13A) \\sim Ueq,
Uanis(F5A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F20A) \\sim Ueq, Uanis(F21A) \\sim Ueq, Uanis(F19A) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(F17A) \\sim Ueq, Uanis(F18A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(F16A) \\sim Ueq, Uanis(F17A) \\sim Ueq, Uanis(F18A) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(F10A) \\sim Ueq, Uanis(F12A) \\sim Ueq, Uanis(F11A) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: F1A(0.45) F2A(0.45) F3A(0.45) F4A(0.45) F5A(0.45) F6A(0.45)
 F7A(0.45) F8A(0.45) F9A(0.45) F10A(0.7) F11A(0.7) F12A(0.7) F13A(0.45)
 F14A(0.45) F15A(0.45) F16A(0.6) F17A(0.6) F18A(0.6) F19A(0.7) F20A(0.7)
 F21A(0.7) F22A(0.45) F23A(0.45) F24A(0.45) C63A(0.7) F1B(0.3) F2B(0.3)
 F3B(0.3) F4B(0.3) F5B(0.3) F6B(0.3) F7B(0.3) F8B(0.3) F9B(0.3) F10B(0.3)
 F11B(0.3) F12B(0.3) F13B(0.3) F14B(0.25) F15B(0.25) F16B(0.4) F17B(0.4)
 F18B(0.4) F19B(0.3) F20B(0.3) F21B(0.3) F22B(0.3) F23B(0.3) F24B(0.3)
 C63B(0.3) F1C(0.25) F2C(0.25) F3C(0.25) F4C(0.25) F5C(0.25) F6C(0.25)
 F7C(0.25) F8C(0.25) F9C(0.25) F13C(0.25) F14C(0.3) F15C(0.3) F22C(0.25)
 F23C(0.25) F24C(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C14(H14), C21(H21), C23(H23), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C34(H34), C36(H36), C38(H38), C42(H42), C44(H44),
  C46(H46), C50(H50), C52(H52), C54(H54), C58(H58), C60(H60), C62(H62)
5.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              29327
_shelx_hkl_checksum              18593
_olex2_submission_special_instructions 'No special instructions were received'