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_1550684
_publ_section_title
;
 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
'C28 H28 Bi F3 N4 O3 S, 0.51(C5 H5 N), 0.49(C4 H10 O)'
_chemical_formula_sum            'C32.51 H35.44 Bi F3 N4.51 O3.49 S'
_chemical_formula_weight         843.26
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2019-01-17 deposited with the CCDC.    2019-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.991(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.527(3)
_cell_length_b                   27.102(11)
_cell_length_c                   11.870(4)
_cell_measurement_reflns_used    9632
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.28
_cell_volume                     3384(2)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            62337
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.190
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_min         1.874
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.328
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.7931.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6040
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+3.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5180
_reflns_number_total             6040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00278b2.cif
_cod_data_source_block           Compound_4
_cod_database_code               1550684
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.700
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C36
 1.5 with sigma of 0.02
 C36-C37
 1.54 with sigma of 0.04
 C34-C35
 1.54 with sigma of 0.04
 C35-O4
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C37, C36, O4, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30, C29, N5, C33, C32, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(O4)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(1)
 Sof(C30)=Sof(H30)=Sof(C29)=Sof(H29)=Sof(N5)=Sof(C33)=Sof(H33)=Sof(C32)=
 Sof(H32)=Sof(C31)=Sof(H31)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B)
5.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C8(H8), C23(H23), C5(H5), C27(H27), C22(H22), C21(H21),
 C6(H6), C24(H24), C9(H9), C20(H20), C4(H4), C12(H12), C10(H10), C11(H11),
 C26(H26), C19(H19), C25(H25), C30(H30), C29(H29), C33(H33), C32(H32), C31(H31)
5.c Fitted hexagon refined as free rotating group:
 C30(C29,N5,C33,C32,C31)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              56028
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'