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_1575843
_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         'C36 H22 Br2 N2 O8, C H Cl3'
_chemical_formula_sum            'C37 H23 Br2 Cl3 N2 O8'
_chemical_formula_weight         889.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8643(3)
_cell_length_b                   15.3347(3)
_cell_length_c                   23.6263(5)
_cell_measurement_reflns_used    6872
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      58.73
_cell_measurement_theta_min      3.25
_cell_volume                     3573.86(15)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12158
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.302
_diffrn_reflns_theta_min         3.255
_diffrn_source                   MetalJet
_diffrn_source_current           2.23
_diffrn_source_power             0.15540869999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.588
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8055.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+5.0240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3316
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05212b2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575843--1575846.cif.
;
_cod_database_code               1575843
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.715
_shelx_estimated_absorpt_t_min   0.653
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C19-Cl2 = C19-Cl1 = C19-Cl3
 1.78 with sigma of 0.02
 C19-Cl2 \\sim C19-Cl1 \\sim C19-Cl3
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl1-Cl3 \\sim Cl3-Cl2
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C19 \\sim Cl2 \\sim Cl1 \\sim Cl3: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C19, Cl2, Cl1, Cl3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C19(0.5) H19(0.5) Cl2(0.5) Cl1(0.5) Cl3(0.5)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C11(H11), C19(H19)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C18(H18), C14(H14), C4(H4), C17(H17), C15(H15)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              40036
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU