Highly Active Chiral Dilithium(I) Binaphthyldisulfonate Catalysts for Enantio- and Chemoselective Strecker-Type Reactions
Hatano, Manabu; Nishio, Kosuke; Mochizuki, Takuya; Nishikawa, Keisuke; Ishihara, Kazuaki; ACS Catalysis 9 (2019) 8178–; doi:10.1021/acscatal.9b02739

data_4514857
_publ_section_title
;
 Highly Active Chiral Dilithium(I) Binaphthyldisulfonate Catalysts for
 Enantio- and Chemoselective Strecker-Type Reactions
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8178
_journal_paper_doi               10.1021/acscatal.9b02739
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration R
_chemical_formula_sum            'C23 H17 Br N2'
_chemical_formula_weight         401.29
_chemical_name_common
;
(R)-2-((Anthracen-9-ylmethyl)amino)-2-(4-bromophenyl)acetonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 92.925(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.030(4)
_cell_length_b                   5.7133(18)
_cell_length_c                   14.591(5)
_cell_measurement_reflns_used    3213
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.272
_cell_volume                     918.3(5)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_unetI/netI     0.1520
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7811
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.399
_diffrn_reflns_theta_min         3.273
_exptl_absorpt_coefficient_mu    2.246
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         1.841
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details
;
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.809
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.809
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.140
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                2214
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02739_si_002.cif
_cod_data_source_block           CrystalClear
_cod_database_code               4514857
_shelx_estimated_absorpt_t_min   0.662
_shelx_estimated_absorpt_t_max   0.807
_shelxl_version_number           2014/6
_shelx_res_checksum              8460
_shelx_hkl_checksum              57923