Enantioselective synthesis of C-C and C-N axially chiral pyrazole-based heterobiaryls.
He, Jun; Yang, Zun; Lin, Lili; Feng, Xiaoming; Chemical science 16 (2025) 20021–20029; doi:10.1039/d5sc06841j

data_1575861
_publ_section_title
;
 Enantioselective synthesis of C-C and C-N axially chiral pyrazole-based
 heterobiaryls.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              20021
_journal_page_last               20029
_journal_paper_doi               10.1039/d5sc06841j
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H24 N4 O3'
_chemical_formula_sum            'C32 H24 N4 O3'
_chemical_formula_weight         512.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3004(6)
_cell_length_b                   12.8214(7)
_cell_length_c                   20.1111(11)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.09
_cell_volume                     2656.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX5'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16456
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_min         4.089
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9366
_exptl_absorpt_correction_T_min  0.7759
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone, MeOH, DCM, Hexane'
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 2012 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0321P)^2^+0.2853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4753
_reflns_number_total             4857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06841j2.cif
_cod_data_source_block           hqw030
_cod_depositor_comments
'Adding full bibliography for 1575859--1575862.cif.'
_cod_database_code               1575861
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.789
_shelx_estimated_absorpt_t_max   0.890
_shelx_res_checksum              51214