Organocatalytic cyclization-rearrangement cascade reaction: asymmetric construction of γ-lactams.
Wu, Sheng-Feng; Wang, Zhi-Yuan; Sun, Xing-Wen; Organic & biomolecular chemistry 23 (2025) 4197–4205; doi:10.1039/d5ob00010f

data_7160466
_publ_section_title
;
 Organocatalytic cyclization-rearrangement cascade reaction: asymmetric
 construction of &#x3b3;-lactams.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4197
_journal_page_last               4205
_journal_paper_doi               10.1039/d5ob00010f
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H37 Cl N2 O8 S'
_chemical_formula_weight         669.16
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.2905(2)
_cell_length_b                   19.2905(2)
_cell_length_c                   21.2551(5)
_cell_measurement_reflns_used    8206
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      42.4881
_cell_measurement_theta_min      3.0937
_cell_volume                     7909.5(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'd8 venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2242
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            112269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        65.165
_diffrn_reflns_theta_max         65.165
_diffrn_reflns_theta_min         3.094
_exptl_absorpt_coefficient_mu    1.726
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0847P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3891
_reflns_number_total             6760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00010f2.cif
_cod_data_source_block           cu_20240201wsf_2_6_cl_0m_sq
_cod_depositor_comments          'Adding full bibliography for 7160466.cif.'
_cod_database_code               7160466
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              72043
_shelx_fab_checksum              42529