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_1572768
_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         'C35 H53 B Br N, C H2 Cl2'
_chemical_formula_sum            'C36 H55 B Br Cl2 N'
_chemical_formula_weight         663.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-26 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.539(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0779(6)
_cell_length_b                   12.7663(6)
_cell_length_c                   20.0966(10)
_cell_measurement_reflns_used    9787
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      32.044
_cell_measurement_theta_min      2.397
_cell_volume                     3610.5(3)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            283352
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_min         1.447
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8849.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.664
_refine_diff_density_min         -2.290
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         11523
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0617
_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^)+(0.1473P)^2^+6.5485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2129
_refine_ls_wR_factor_ref         0.2197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10368
_reflns_number_total             11523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05524a3.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 1572763--1572772.cif.'
_cod_database_code               1572768
_shelx_shelxl_version_number     2019/1
_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. Rigid bond restraints
 Br1, B1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
Br1 \\sim B1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4.a Ternary CH refined with riding coordinates:
 C36(H36), C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C24(H24A,H24B), C28(H28A,H28B), C6(H6A,H6B), C25(H25A,H25B),
 C27(H27A,H27B), C22(H22A,H22B), C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
4.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C21(H21A,H21B,H21C), C17(H17A,H17B,H17C), C34(H34A,H34B,
 H34C), C1(H1A,H1B,H1C), C32(H32A,H32B,H32C), C18(H18A,H18B,H18C), C20(H20A,
 H20B,H20C), C11(H11A,H11B,H11C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              73393
_shelx_hkl_checksum              12736
_olex2_submission_special_instructions 'No special instructions were received'