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_4127865
_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            'C28 H22 B2 N4'
_chemical_formula_weight         436.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0959(7)
_cell_length_b                   16.8166(18)
_cell_length_c                   21.650(2)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.24
_cell_volume                     2219.4(4)
_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 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12281
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         1.533
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0365P)^2^+0.3539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4358
_reflns_number_total             4932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06910_si_002.cif
_cod_data_source_block           KYBdan2
_cod_original_cell_volume        2219.3(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4127865
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              96457
_shelx_hkl_checksum              34919