Atroposelective synthesis of sterically hindered stereochemically complex BINOL derivatives <i>via</i> central-to-axial chirality induction.
Yang, Yang; Bai, Guishun; Qin, Mengmeng; Wang, Juelian; Yang, Yihuan; Wang, Hong; Bonne, Damien; Rodriguez, Jean; Bao, Xiaoze; Chemical science 16 (2025) 19342–19349; doi:10.1039/d5sc05212b

data_1575845
_publ_section_title
;
 Atroposelective synthesis of sterically hindered stereochemically complex
 BINOL derivatives <i>via</i> central-to-axial chirality induction.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              19342
_journal_page_last               19349
_journal_paper_doi               10.1039/d5sc05212b
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C36 H21 N O6), C H Cl3'
_chemical_formula_sum            'C73 H43 Cl3 N2 O12'
_chemical_formula_weight         1246.44
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.418(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8612(9)
_cell_length_b                   34.138(3)
_cell_length_c                   9.8708(9)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      65.11
_cell_measurement_theta_min      2.59
_cell_volume                     2949.7(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32173
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.680
_diffrn_reflns_theta_max         66.680
_diffrn_reflns_theta_min         2.589
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.987
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1727 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.4772.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.100(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     811
_refine_ls_number_reflns         10272
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0721
_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^)+(0.1545P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                8581
_reflns_number_total             10272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05212b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1575843--1575846.cif.'
_cod_original_cell_volume        2949.6(5)
_cod_database_code               1575845
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.716
_shelx_estimated_absorpt_t_min   0.669
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00R(H00R), C012(H012), C01V(H01V), C02I(H02I)
2.b Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00X(H00X), C016(H016), C017(H017), C019(H019), C01A(H01A),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01Q(H01Q), C01T(H01T), C01U(H01U), C01W(H01W),
 C01X(H01X), C01Y(H01Y), C01Z(H01Z), C021(H021), C022(H022), C023(H023),
 C024(H024), C025(H025), C026(H026), C027(H027), C028(H028), C029(H029),
 C02A(H02A), C02B(H02B), C02C(H02C), C02D(H02D), C02E(H02E), C02F(H02F),
 C02G(H02G), C02H(H02H)
;
_shelx_res_checksum              25338
_olex2_submission_special_instructions 'No special instructions were received'