Weak-coordination-auxiliary aminocatalysis enables directed [3 + 2] cyclization for 2-acylindolizines
Zeng, Kui; Pandit, Neeraj Kumar; Oliveira, João C. A.; Dechert, Sebastian; Ackermann, Lutz; Zhang, Kai; Green Chemistry 26 (2024) 5253–5259; doi:10.1039/D3GC03552B

data_7247856
_publ_section_title
;
 Weak-coordination-auxiliary aminocatalysis enables directed [3 + 2]
 cyclization for 2-acylindolizines
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              5253
_journal_page_last               5259
_journal_paper_doi               10.1039/D3GC03552B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.317(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5190(13)
_cell_length_b                   12.050(2)
_cell_length_c                   11.678(2)
_cell_measurement_reflns_used    155
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.1858
_cell_measurement_theta_min      2.4498
_cell_volume                     1041.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1020
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31200
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0516P)^2^+0.5691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1762
_reflns_number_total             2483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03552b2.cif
_cod_data_source_block           kui1366_21
_cod_depositor_comments
'Adding full bibliography for 7247855--7247856.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247856
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              50727