Ruthenium-Catalyzed (<i>Z</i>)-Selective Hydroboration of Terminal Alkynes with Naphthalene-1,8-diaminatoborane.
Yamamoto, Kensuke; Mohara, Yusei; Mutoh, Yuichiro; Saito, Shinichi; Journal of the American Chemical Society 141 (2019) 17042–17047; doi:10.1021/jacs.9b06910

data_4127862
_publ_section_title
;
 Ruthenium-Catalyzed (<i>Z</i>)-Selective Hydroboration of Terminal
 Alkynes with Naphthalene-1,8-diaminatoborane.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17042
_journal_page_last               17047
_journal_paper_doi               10.1021/jacs.9b06910
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C48 H66 Cl N2 O P Ru'
_chemical_formula_weight         854.51
_space_group_crystal_system      monoclinic
_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   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 113.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8197(18)
_cell_length_b                   31.293(5)
_cell_length_c                   13.219(2)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.36
_cell_volume                     4496.5(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24189
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.797
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.193
_refine_diff_density_max         1.526
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         10085
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0162P)^2^+10.2941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8584
_reflns_number_total             10085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06910_si_002.cif
_cod_data_source_block           KY3511
_cod_original_cell_volume        4496.7(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4127862
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.914
_shelx_res_checksum              49058
_shelx_hkl_checksum              16629