trans-Hydroboration vs. 1,2-reduction: divergent reactivity of ynones and ynoates in Lewis-base-catalyzed reactions with pinacolborane.
Zi, You; Schömberg, Fritz; Seifert, Fabian; Görls, Helmar; Vilotijevic, Ivan; Organic & biomolecular chemistry 16 (2018) 6341–6349; doi:10.1039/c8ob01343h

data_7156373
_publ_section_title
;
 trans-Hydroboration vs. 1,2-reduction: divergent reactivity of ynones and
 ynoates in Lewis-base-catalyzed reactions with pinacolborane.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6341
_journal_page_last               6349
_journal_paper_doi               10.1039/c8ob01343h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C16 H20 B Br O4'
_chemical_formula_sum            'C16 H20 B Br O4'
_chemical_formula_weight         367.04
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-05-25 deposited with the CCDC.
2018-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.091(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2446(3)
_cell_length_b                   10.9482(5)
_cell_length_c                   21.3662(9)
_cell_measurement_reflns_used    19180
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.68
_cell_volume                     1677.80(13)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19180
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+3.2536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                3241
_reflns_number_total             3834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob01343h2.cif
_cod_data_source_block           FO6598
_cod_depositor_comments          'Adding full bibliography for 7156373.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7156373