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_1571414
_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 Br2 I'
_chemical_formula_sum            'C12 H7 Br2 I'
_chemical_formula_weight         437.90
_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                82.325(4)
_cell_angle_beta                 74.766(4)
_cell_angle_gamma                65.240(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5376(9)
_cell_length_b                   7.9320(9)
_cell_length_c                   11.5935(12)
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.83
_cell_volume                     607.10(12)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_min         2.829
_exptl_absorpt_coefficient_mu    9.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.395
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0319P)^2^+0.1902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01234h2.cif
_cod_data_source_block           ejwddc230223
_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               1571414
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.321
_shelx_estimated_absorpt_t_max   0.460
_shelx_res_checksum              94201