Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents
Kodama, Koichi; Takase, Fusato; Hirose, Takuji; RSC Advances 11 (2021) 18162–18170; doi:10.1039/D1RA03546K

data_7242887
_publ_section_title
;
 Direct enantioseparation of axially chiral
 1,1&#x2032;-biaryl-2,2&#x2032;-diols using amidine-based resolving agents
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              18162
_journal_page_last               18170
_journal_paper_doi               10.1039/D1RA03546K
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-01-20 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.928(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4244(13)
_cell_length_b                   5.0509(7)
_cell_length_c                   13.2982(18)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.44
_cell_volume                     621.54(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.968
_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  0.0852
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2944
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         1.560
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0518
_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^)+(0.1093P)^2^+0.0564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                1891
_reflns_number_total             1955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra03546k2.cif
_cod_data_source_block           benzamidine_nitrophenol
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242887
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
_shelx_res_checksum              10517