Ugi multicomponent reactions of optically active aldehydes and chiral aminoindanols: diastereoselective synthesis of bisamides relevant to SARS-CoV-2 Mpro inhibitors.
Ghosh, Arun K.; Bhattacharjee, Amlan; Jayashankar, Uttara; Bogan, Sydney N.; Mesecar, Andrew D.; Organic & biomolecular chemistry 24 (2026) 2542–2558; doi:10.1039/d5ob01897h

data_7161053
_publ_section_title
;
 Ugi multicomponent reactions of optically active aldehydes and chiral
 aminoindanols: diastereoselective synthesis of bisamides relevant to
 SARS-CoV-2 Mpro inhibitors.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2542
_journal_page_last               2558
_journal_paper_doi               10.1039/d5ob01897h
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_sum            'C32 H41 N5 O6'
_chemical_formula_weight         591.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-11-07 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.949(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6747(5)
_cell_length_b                   10.7211(4)
_cell_length_c                   15.9751(6)
_cell_measurement_reflns_used    6298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8011
_cell_measurement_theta_min      4.5765
_cell_volume                     1654.80(12)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2020)'
_computing_data_collection       'Apex6 v2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2020)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27249
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.484
_diffrn_reflns_theta_min         4.576
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_current           '1.1 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(18)
_refine_ls_extinction_coef       0.0091(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         7037
_refine_ls_number_restraints     470
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0311P)^2^+0.0972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                4961
_reflns_number_total             7037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01897h2.cif
_cod_data_source_block           AB_03_065_0m
_cod_depositor_comments
'Adding full bibliography for 7161052--7161055.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7161053
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.759
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              55096