Regioselective synthesis of ortho-iodobiphenylboronic acid derivatives: a superior catalyst for carboxylic acid activation
Al-Zoubi, Raed M.; Al-Jammal, Walid K.; McDonald, Robert; New Journal of Chemistry 44 (2020) 3612–3623; doi:10.1039/C9NJ05708K

data_7059266
_publ_section_title
;
 Regioselective synthesis of ortho-iodobiphenylboronic acid derivatives: a
 superior catalyst for carboxylic acid activation
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3612
_journal_page_last               3623
_journal_paper_doi               10.1039/C9NJ05708K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C19 H16 B I O4'
_chemical_formula_sum            'C19 H16 B I O4'
_chemical_formula_weight         446.03
_chemical_name_common            (21A)
_chemical_name_systematic
'(2-iodo-5-methoxy-4'-phenoxybiphenyl-3-yl)boronic acid'
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                114.1398(17)
_cell_angle_beta                 94.4519(16)
_cell_angle_gamma                93.3392(16)
_cell_formula_units_Z            2
_cell_length_a                   5.1433(2)
_cell_length_b                   13.2175(4)
_cell_length_c                   14.1071(4)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.67
_cell_measurement_theta_min      3.45
_cell_volume                     868.24(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6177
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_min         3.455
_exptl_absorpt_coefficient_mu    14.668
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_correction_T_min  0.2320
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes'
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0309P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             3396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05708k2.cif
_cod_data_source_block           jus1509
_cod_depositor_comments
;Adding full bibliography for 7059263--7059266.cif.

 Adding full bibliography for 7059263--7059266.cif.
;
_cod_database_code               7059266
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.145
_shelx_estimated_absorpt_t_max   0.748
_shelx_res_checksum              8837