Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis.
Wang, Xia; Wang, Shao-Jie; Xin, Xiaolan; An, Hao; Tu, Zhifeng; Yang, Hui; Wong, Ming Wah; Lu, Shenci; Chemical science 15 (2024) 13240–13249; doi:10.1039/d4sc03190c

data_1572009
_publ_section_title
;
 Enantioconvergent and diastereoselective synthesis of atropisomeric
 hydrazides bearing a cyclic quaternary stereocenter through ternary
 catalysis.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              13240
_journal_page_last               13249
_journal_paper_doi               10.1039/d4sc03190c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H33 N3 O7'
_chemical_formula_sum            'C24 H33 N3 O7'
_chemical_formula_weight         475.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-06 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                97.915(6)
_cell_angle_beta                 92.615(6)
_cell_angle_gamma                118.101(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4813(16)
_cell_length_b                   10.5048(16)
_cell_length_c                   13.991(2)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      51.694
_cell_measurement_theta_min      2.80
_cell_volume                     1335.1(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45082
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         65.108
_diffrn_reflns_theta_min         2.797
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8759.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 3410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         12815
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1066P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                8482
_reflns_number_total             12815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03190c2.cif
_cod_data_source_block           20220728bl_0m
_cod_depositor_comments
'Adding full bibliography for 1572009--1572010.cif.'
_cod_original_cell_volume        1335.2(4)
_cod_database_code               1572009
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C36(H36), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C40(H40A,H40B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4A), C6(H6), C2(H2), C3(H3A), C4(H4), C5(H5), C31(H31), C27(H27),
 C33(H33), C8(H8), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C37(H37A,H37B,
 H37C), C01H(H01A,H01B,H01C), C23(H23A,H23B,H23C), C01J(H01D,H01E,H01F),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C01N(H01G,H01H,H01I), C41(H41A,H41B,
 H41C), C17(H17A,H17B,H17C), C44(H44A,H44B,H44C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              74527
_olex2_submission_special_instructions 'No special instructions were received'