Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.
Zhao, Jian; Jonker, Sybrand J. T.; Meyer, Denise N.; Schulz, Göran; Tran, C. Duc; Eriksson, Lars; Szabó, Kálmán J; Chemical science 9 (2018) 3305–3312; doi:10.1039/c7sc05123a

data_1548954
_publ_section_title
;
 Copper-catalyzed synthesis of allenylboronic acids. Access to sterically
 encumbered homopropargylic alcohols and amines by propargylboration.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              3305
_journal_page_last               3312
_journal_paper_doi               10.1039/c7sc05123a
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H34 O4 S'
_chemical_formula_sum            'C31 H34 O4 S'
_chemical_formula_weight         502.64
_chemical_name_systematic
'3,3-dimethyl-2-(4-(methylsulfonyl)phenyl)non-4-yn-2-yl [1,1'-biphenyl]-4-carboxylate'
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-15 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   21.2470(9)
_cell_length_b                   21.247
_cell_length_c                   11.2694(5)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.23
_cell_measurement_theta_min      2.21
_cell_volume                     4405.8(3)
_computing_cell_refinement       'Apex 3 (Bruker, 2016)'
_computing_data_collection       'Apex 3 (Bruker, 2016)'
_computing_data_reduction        'Apex 3 (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Advance'
_diffrn_measurement_method       '\w scan at different \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38447
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.328
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.142
_exptl_crystal_colour            colour_less
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prism
_exptl_crystal_F_000             1608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH, H2O'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     94
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1207P)^2^+0.2932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3799
_reflns_number_total             5347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc05123a2.cif
_cod_data_source_block           r
_cod_depositor_comments          'Adding full bibliography for 1548954.cif.'
_cod_original_cell_volume        4405.8(4)
_cod_database_code               1548954
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              82670