Arene extrusion as an approach to reductive elimination at boron: implication of carbene-ligated haloborylene as a transient reactive intermediate.
Zhang, Chonghe; Gilliard, Jr, Robert J; Cummins, Christopher C.; Chemical science 15 (2024) 17873–17880; doi:10.1039/d4sc05524a

data_1572770
_publ_section_title
;
 Arene extrusion as an approach to reductive elimination at boron:
 implication of carbene-ligated haloborylene as a transient reactive
 intermediate.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              17873
_journal_page_last               17880
_journal_paper_doi               10.1039/d4sc05524a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'Cl, 3(C H2 Cl2), C33 H42 B N2'
_chemical_formula_sum            'C36 H48 B Cl7 N2'
_chemical_formula_weight         767.72
_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
_audit_creation_date             2023-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-26 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                108.946(3)
_cell_angle_beta                 93.723(2)
_cell_angle_gamma                95.092(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7206(8)
_cell_length_b                   12.0045(8)
_cell_length_c                   15.0853(10)
_cell_measurement_reflns_used    28584
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      61.557
_cell_measurement_theta_min      15.598
_cell_volume                     1989.7(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28466
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.070
_diffrn_reflns_theta_min         1.434
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.9142.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.023
_refine_diff_density_max         1.699
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         12481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0413P)^2^+1.4508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11008
_reflns_number_total             12481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05524a3.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1572763--1572772.cif.'
_cod_database_code               1572770
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.939
_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.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C34(H34A,H34B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C20(H20), C29(H29), C27(H27), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C31(H31A,H31B,H31C),
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C33(H33A,H33B,H33C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              92704
_shelx_hkl_checksum              66661
_olex2_submission_special_instructions 'No special instructions were received'