Carbon Monoxide Insertion at a Heavy p-Block Element: Unprecedented Formation of a Cationic Bismuth Carbamoyl
Ramler, Jacqueline; Poater, Jordi; Hrisch, Florian; Ritschel, Benedikt; Fischer, Ingo; Bickelhaupt, F. Matthias; Lichtenberg, Crispin; Chemical Science  (2019) –; doi:10.1039/C9SC00278B

data_1550683
_publ_section_title
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 Carbon Monoxide Insertion at a Heavy p-Block Element: Unprecedented
 Formation of a Cationic Bismuth Carbamoyl
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00278B
_journal_year                    2019
_chemical_formula_moiety         'C25 H22 Bi F3 N4 O3 S, 0.5(C5 H5 N)'
_chemical_formula_sum            'C27.5 H24.5 Bi F3 N4.5 O3 S'
_chemical_formula_weight         764.05
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2019-01-17 deposited with the CCDC.    2019-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1963(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7873(9)
_cell_length_b                   19.5468(10)
_cell_length_c                   17.0940(8)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.42
_cell_volume                     5646.1(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            84157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.771
_diffrn_reflns_theta_min         1.630
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.377
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.6289.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_description       needle
_exptl_crystal_F_000             2968
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     736
_refine_ls_number_reflns         12009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0090P)^2^+8.2200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10659
_reflns_number_total             12009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00278b2.cif
_cod_data_source_block           Compound_3
_cod_depositor_comments
;

2019-07-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C55 H49 Bi2 F6 N9 O6 S2'
_cod_original_formula_weight         1528.11
_cod_original_formula_moiety         '2(C25 H22 Bi F3 N4 O3 S), C5 H5 N'
_cod_original_formula_units_Z            4
_cod_database_code               1550683
_shelx_estimated_absorpt_t_max   0.709
_shelx_estimated_absorpt_t_min   0.124
_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. Uiso/Uaniso restraints and constraints
Uanis(C55A) = Uanis(C54A) = Uanis(C53A) = Uanis(C52A) = Uanis(C51A)
Uanis(N9) = Uanis(N9A)
3. Others
 Sof(C54A)=Sof(H54A)=Sof(C53A)=Sof(H53A)=Sof(C52A)=Sof(H52A)=Sof(C51A)=
 Sof(H51A)=Sof(N9A)=Sof(C55A)=Sof(H55A)=1-FVAR(1)
 Sof(C54)=Sof(H54)=Sof(N9)=Sof(C53)=Sof(H53)=Sof(C55)=Sof(H55)=Sof(C52)=
 Sof(H52)=Sof(C51)=Sof(H51)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C43(H43), C30(H30), C12(H12), C18(H18), C16(H16), C4(H4),
 C17(H17), C15(H15), C24(H24), C48(H48), C23(H23), C46(H46), C8(H8), C32(H32),
 C33(H33), C20(H20), C28(H28), C5(H5), C42(H42), C47(H47), C6(H6), C29(H29),
 C11(H11), C44(H44), C9(H9), C39(H39), C27(H27), C21(H21), C54(H54), C41(H41),
 C45(H45), C40(H40), C36(H36), C10(H10), C35(H35), C34(H34), C53(H53), C55(H55),
  C52(H52), C51(H51), C22(H22), C54A(H54A), C53A(H53A), C52A(H52A), C51A(H51A),
 C55A(H55A)
4.b Fitted hexagon refined as free rotating group:
 C54A(C53A,C52A,C51A,N9A,C55A)
4.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C14(H14A,H14B,H14C)
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_shelx_res_checksum              63025
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'