Brønsted acid-catalyzed two-component tandem condensation and cycloisomerization to 6(2H)-isoquinolinones
Yang, Fang; Wang, Lin-Lin; Liu, Yu-Hua; Wu, Ke-Xin; Chen, Zi-Sheng; Ji, Kegong; RSC Advances 15 (2025) 8913–8917; doi:10.1039/D5RA01267H

data_7250173
_publ_section_title
;
 Br\/onsted acid-catalyzed two-component tandem condensation and
 cycloisomerization to 6(2H)-isoquinolinones
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              8913
_journal_page_last               8917
_journal_paper_doi               10.1039/D5RA01267H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-05-04 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5288(5)
_cell_length_b                   14.6591(5)
_cell_length_c                   16.0719(6)
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.9680
_cell_measurement_theta_min      5.3820
_cell_volume                     2951.78(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -33.00  62.00   1.00    1.50    --   40.98 -38.00  60.00   95
  2  \w     41.00 115.00   1.00    2.00    --  106.95-125.00  90.00   74
  3  \w     82.00 109.00   1.00    2.00    --  106.95 -95.00 -60.00   27
  4  \w     62.00  92.00   1.00    1.50    --   40.98-125.00-120.00   30
  5  \w     61.00  88.00   1.00    1.50    --   40.98-125.00-180.00   27
  6  \w     28.00 106.00   1.00    2.00    --  106.95 -95.00-150.00   78
  7  \w     78.00 178.00   1.00    2.00    --  106.95  77.00-150.00  100
  8  \w    123.00 169.00   1.00    2.00    --  106.95 125.00 -90.00   46
  9  \w    107.00 157.00   1.00    2.00    --  106.95 123.00  23.00   50
 10  \w     78.00 170.00   1.00    2.00    --  106.95  61.00 120.00   92
 11  \w   -112.00 -16.00   1.00    1.50    --  -40.98 -38.00 -90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1174549000
_diffrn_orient_matrix_UB_12      -0.0313976000
_diffrn_orient_matrix_UB_13      -0.0039118000
_diffrn_orient_matrix_UB_21      0.0354809000
_diffrn_orient_matrix_UB_22      -0.0913833000
_diffrn_orient_matrix_UB_23      -0.0382997000
_diffrn_orient_matrix_UB_31      0.0105311000
_diffrn_orient_matrix_UB_32      -0.0414261000
_diffrn_orient_matrix_UB_33      0.0875855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.833
_diffrn_reflns_theta_min         5.399
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0725P)^2^+1.6857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2299
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra01267h2.cif
_cod_data_source_block           71-1
_cod_database_code               7250173
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C2(H2), C21(H21), C3(H3), C11(H11), C20(H20), C5(H5),
 C17(H17), C19(H19), C15(H15), C18(H18), C12(H12), C13(H13), C14(H14)
;
_shelx_res_checksum              82211
_olex2_date_sample_data_collection 2020-06-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.801
_oxdiff_exptl_absorpt_empirical_full_min 0.207