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_1572772
_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         'C23 H35 B Br N'
_chemical_formula_sum            'C23 H35 B Br N'
_chemical_formula_weight         416.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1571(5)
_cell_length_b                   13.5618(7)
_cell_length_c                   25.8390(13)
_cell_measurement_reflns_used    9433
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.962
_cell_measurement_theta_min      2.300
_cell_volume                     4260.1(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            217441
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.576
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0932 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8600.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.023
_refine_diff_density_max         1.874
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0350P)^2^+11.4584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3590
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05524a3.cif
_cod_data_source_block           5Br
_cod_depositor_comments
'Adding full bibliography for 1572763--1572772.cif.'
_cod_database_code               1572772
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1-B1 \\sim Br2-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br2)
4. Others
 Sof(H1BB)=Sof(Br1)=1-FVAR(1)
 Sof(Br2)=Sof(H1AA)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), B1(H1AA), B1(H1BB)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              28715
_shelx_hkl_checksum              47404
_olex2_submission_special_instructions 'No special instructions were received'