Optically active bis(aminophenols) and their metal complexes
Carbonel, Halen; Mikulski, Timothy D.; Nugraha, Kahargyan; Johnston, James; Wang, Yichun; Brown, Seth N.; Dalton Transactions  (2023) –; doi:10.1039/D3DT02436A

data_7713819
_publ_section_title
;
 Optically active bis(aminophenols) and their metal complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02436A
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C48 H56 N2 O2, C7 H8, C H4 O'
_chemical_formula_sum            'C56 H68 N2 O3'
_chemical_formula_weight         817.12
_chemical_name_common            '(R)-BiniqH4 . CH3OH . PhCH3'
_chemical_name_systematic
'(R)-2,2'-bis-N-(2-hydroxy-3,5-di-tert-butylphenyl)amino-1,1'-binaphthyl methanol toluene solvate'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-07-14 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.041(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.1059(14)
_cell_length_b                   9.4304(9)
_cell_length_c                   17.6428(16)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.341
_cell_measurement_theta_min      2.360
_cell_volume                     2458.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0687
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            82110
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             884
_exptl_crystal_recrystallization_method
'Crystals formed on diffusion of methanol into a toluene solution of the compound.'
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         9921
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0502P)^2^+5.0527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2183
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7691
_reflns_number_total             9921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02436a2.cif
_cod_data_source_block           biniqh4
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7713819
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
_shelx_res_checksum              32134