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_1575860
_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_formula_moiety         'C22 H16 N2 O3 S'
_chemical_formula_sum            'C22 H16 N2 O3 S'
_chemical_formula_weight         388.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 100.9880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3478(2)
_cell_length_b                   11.1173(2)
_cell_length_c                   14.7905(3)
_cell_measurement_reflns_used    9684
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.31
_cell_volume                     1831.72(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18620
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, EtOAc'
_exptl_crystal_size_max          0.767
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.279
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0165(16)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0409P)^2^+0.6572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06841j2.cif
_cod_data_source_block           hqw031
_cod_depositor_comments
'Adding full bibliography for 1575859--1575862.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1575860
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.860
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              63803