Dynamic kinetic resolution of γ,γ-disubstituted indole 2-carboxaldehydes <i>via</i> NHC-Lewis acid cooperative catalysis for the synthesis of tetracyclic ε-lactones.
Balanna, Kuruva; Barik, Soumen; Shee, Sayan; Gonnade, Rajesh G.; Biju, Akkattu T.; Chemical science 13 (2022) 11513–11518; doi:10.1039/d2sc03745a

data_1567538
_publ_section_title
;
 Dynamic kinetic resolution of \g,\g-disubstituted indole
 2-carboxaldehydes <i>via</i> NHC-Lewis acid cooperative catalysis for the
 synthesis of tetracyclic \e-lactones.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11513
_journal_page_last               11518
_journal_paper_doi               10.1039/d2sc03745a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H33 N O3, CH3 CH2 OH'
_chemical_formula_sum            'C33 H39 N O4'
_chemical_formula_weight         513.65
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-01 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.351(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2800(10)
_cell_length_b                   17.0143(19)
_cell_length_c                   10.0461(10)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.20
_cell_measurement_theta_min      2.60
_cell_volume                     1433.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28158
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.240
_diffrn_reflns_theta_min         4.871
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0121(15)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0408P)^2^+0.6926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                5497
_reflns_number_total             5575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03745a2.cif
_cod_data_source_block           dh_hme_050821
_cod_depositor_comments          'Adding full bibliography for 1567538.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567538
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              67400