Easy access to polyhalogenated biaryls: regioselective (di)halogenation of hypervalent bromines and chlorines.
Carter Martos, Daniel; de Abreu, Maxime; Hauk, Pascal; Fackler, Philipp; Wencel-Delord, Joanna; Chemical science 15 (2024) 6770–6776; doi:10.1039/d4sc01234h

data_1571417
_publ_section_title
;
 Easy access to polyhalogenated biaryls: regioselective (di)halogenation
 of hypervalent bromines and chlorines.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              6770
_journal_page_last               6776
_journal_paper_doi               10.1039/d4sc01234h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C12 H7 Br3'
_chemical_formula_sum            'C12 H7 Br3'
_chemical_formula_weight         390.91
_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_method           SHELXL-2018/3
_audit_update_record
;
2023-12-28 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                83.9920(10)
_cell_angle_beta                 76.4460(10)
_cell_angle_gamma                65.0730(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4022(3)
_cell_length_b                   7.8572(3)
_cell_length_c                   11.3380(4)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.86
_cell_volume                     581.33(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       '\f and \w shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24581
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_min         2.859
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    10.370
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0244P)^2^+0.8713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2485
_reflns_number_total             2772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01234h2.cif
_cod_data_source_block           ejwddc230712
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571414--1571417.cif.
;
_cod_database_code               1571417
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.288
_shelx_estimated_absorpt_t_max   0.424
_shelx_res_checksum              52955