Camphorsulfonic Acid-Mediated One-Pot Tandem Consecutive via the Ugi Four-Component Reaction for the Synthesis of Functionalized Indole and 2-Quinolone Derivatives by Switching Solvents.
Murugan, Sivan Perumal; Zhong, Hong-Jie; Wu, Chih-Yu; Pan, Hao-Wei; Chen, Chinpiao; Lee, Gene-Hsian; ACS omega 7 (2022) 5713–5729; doi:10.1021/acsomega.1c05460

data_4519356
_publ_section_title
;
 Camphorsulfonic Acid-Mediated One-Pot Tandem Consecutive via the Ugi
 Four-Component Reaction for the Synthesis of Functionalized Indole and
 2-Quinolone Derivatives by Switching Solvents.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              5713
_journal_page_last               5729
_journal_paper_doi               10.1021/acsomega.1c05460
_journal_volume                  7
_journal_year                    2022
_chemical_formula_sum            'C26 H21 N O4'
_chemical_formula_weight         411.44
_space_group_crystal_system      monoclinic
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_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
_cell_angle_alpha                90
_cell_angle_beta                 93.4435(5)
_cell_angle_gamma                90
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_cell_length_a                   8.79610(10)
_cell_length_b                   16.2533(3)
_cell_length_c                   14.8259(2)
_cell_measurement_reflns_used    17979
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.00
_cell_measurement_theta_min      4.04
_cell_volume                     2115.77(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.980
_diffrn_reflns_theta_min         4.040
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.7807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0644P)^2^+0.6504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3835
_reflns_number_total             4344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05460_si_001.cif
_cod_data_source_block           ic20371
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4519356
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              8152
_shelx_hkl_checksum              38527