Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters
d’Aleman, Antoine; Gayraud, Oscar; Fressigné, Catherine; Petit, Emilie; Bailly, Laetitia; Maddaluno, Jacques; De Paolis, Michaël; Chemical Science 14 (2023) 2107–2113; doi:10.1039/D2SC06842G

data_1568331
_publ_section_title
;
 Organocatalyzed enantio- and diastereoselective isomerization of
 prochiral 1,3-cyclohexanediones into nonalactones bearing distant
 stereocenters
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              2107
_journal_page_last               2113
_journal_paper_doi               10.1039/D2SC06842G
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8529(12)
_cell_length_b                   20.5937(18)
_cell_length_c                   5.5853(5)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      39.44
_cell_measurement_theta_min      3.38
_cell_volume                     1708.4(3)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            19211
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         2.916
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2016/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   0.7477
_exptl_transmission_factor_min   0.6432
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0515P)^2^+0.2190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4581
_reflns_number_total             4754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06842g2.cif
_cod_data_source_block           depaolis1_a
_cod_depositor_comments          'Adding full bibliography for 1568331.cif.'
_cod_database_code               1568331
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              68345
_shelx_hkl_checksum              40754