Unveiling the migration reactivity of bicyclic diaziridines: enantioselective synthesis of chiral pyrazolines.
Liu, Zhili; Ning, Lichao; Yang, Bingqian; Wang, Kaixuan; Lin, Lili; Feng, Xiaoming; Chemical science 16 (2025) 16584–16589; doi:10.1039/d5sc04846j

data_1575369
_publ_section_title
;
 Unveiling the migration reactivity of bicyclic diaziridines:
 enantioselective synthesis of chiral pyrazolines.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              16584
_journal_page_last               16589
_journal_paper_doi               10.1039/d5sc04846j
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H29 Cl N2 O2'
_chemical_formula_sum            'C33 H29 Cl N2 O2'
_chemical_formula_weight         521.03
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2025-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.12930(10)
_cell_length_b                   9.12930(10)
_cell_length_c                   29.9464(8)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.95
_cell_volume                     2161.47(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18181
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         4.429
_exptl_absorpt_coefficient_mu    1.413
_exptl_absorpt_correction_T_max  0.7561
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       rod
_exptl_crystal_F_000             822
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: iPrOH, Hexane'
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.252
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 2179 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.060(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0365P)^2^+0.1488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                4818
_reflns_number_total             4900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04846j2.cif
_cod_data_source_block           lxb026
_cod_depositor_comments          'Adding full bibliography for 1575369.cif.'
_cod_database_code               1575369
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.519
_shelx_estimated_absorpt_t_max   0.717
_shelx_res_checksum              65543