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_4125484
_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            'C55 H60 O5'
_chemical_formula_weight         801.03
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   25.4957(12)
_cell_length_b                   25.4957(12)
_cell_length_c                   6.2727(3)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      49.27
_cell_measurement_theta_min      3.47
_cell_volume                     3531.2(3)
_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 0.565
_diffrn_measured_fraction_theta_max 0.988
_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  0.1121
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.565
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13892
_diffrn_reflns_point_group_measured_fraction_full 0.548
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         49.927
_diffrn_reflns_theta_min         2.001
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       needle
_exptl_crystal_F_000             1290
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_platon_squeeze_details
;
In the structure there two channels. A disordered THF molecule
fills out one of the and difordered pentane molecule fill out
the second one. The correction of the X-ray data after SQUEEZE
is 312 electron/cell; the requred value is 246 electron/cell.
;
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1027P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.528
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                1943
_reflns_number_total             2348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12658_si_002.cif
_cod_data_source_block           cu_jasti54_0m_sqd
_cod_depositor_comments
'Adding full bibliography for 4125484--4125486.cif.'
_cod_original_cell_volume        3531.2(4)
_cod_database_code               4125484
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.978
_platon_squeeze_void_probe_radius 1.20
_shelxl_version_number           2013-4
_shelx_res_checksum              6653
_shelx_hkl_checksum              11163