An Operationally Simple and Mild Oxidative Homocoupling of Aryl Boronic Esters To Access Conformationally Constrained Macrocycles.
Darzi, Evan R.; White, Brittany M.; Loventhal, Lance K.; Zakharov, Lev N.; Jasti, Ramesh; Journal of the American Chemical Society 139 (2017) 3106–3114; doi:10.1021/jacs.6b12658

data_4125486
_publ_section_title
;
 An Operationally Simple and Mild Oxidative Homocoupling of Aryl Boronic
 Esters To Access Conformationally Constrained Macrocycles.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3106
_journal_page_last               3114
_journal_paper_doi               10.1021/jacs.6b12658
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C34 H32 O4'
_chemical_formula_weight         504.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   36.9470(18)
_cell_length_b                   9.7771(5)
_cell_length_c                   38.2483(18)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.87
_cell_measurement_theta_min      4.16
_cell_volume                     12890.9(11)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0528
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            51624
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        66.918
_diffrn_reflns_theta_max         66.918
_diffrn_reflns_theta_min         2.476
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             5360
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 5045 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1711
_refine_ls_number_reflns         19979
_refine_ls_number_restraints     1637
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+6.2676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.748
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                14414
_reflns_number_total             19979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12658_si_001.cif
_cod_data_source_block           cu_jasti72_0m
_cod_depositor_comments
'Adding full bibliography for 4125484--4125486.cif.'
_cod_database_code               4125486
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              49159
_shelx_hkl_checksum              38483