Asymmetric synthesis of quinolinone-based polycyclic indoles through [1,3]-rearrangement/cyclization reaction
Xu, Fuxing; Xiong, Zongli; Qin, Wenling; Yao, Weijun; Wang, Zhen; Chemical Communications 61 (2025) 8403–8406; doi:10.1039/D5CC00612K

data_7134485
_publ_section_title
;
 Asymmetric synthesis of quinolinone-based polycyclic indoles through
 [1,3]-rearrangement/cyclization reaction
;
_journal_issue                   46
_journal_name_full               'Chemical Communications'
_journal_page_first              8403
_journal_page_last               8406
_journal_paper_doi               10.1039/D5CC00612K
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C42 H36 N2 O5 S2'
_chemical_formula_sum            'C42 H36 N2 O5 S2'
_chemical_formula_weight         712.85
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-07 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7401(2)
_cell_length_b                   18.2838(3)
_cell_length_c                   18.5074(3)
_cell_measurement_reflns_used    10737
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8830
_cell_measurement_theta_min      3.3970
_cell_volume                     3630.08(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -67.00  10.00   1.00    1.00    --    0.00 -57.00 -60.00   77
  2  \w    -11.00  16.00   1.00    1.00    --    0.00  57.00  60.00   27
  3  \w     79.00 123.00   1.00    1.52    --   54.00  57.00 120.00   44
  4  \w     79.00 116.00   1.00    1.52    --   54.00  19.00 -90.00   37
  5  \w    -15.00  73.00   1.00    1.52    --   54.00 -57.00 -30.00   88
  6  \w     24.00 102.00   1.00    1.52    --   54.00-125.00 -60.00   78
  7  \w     10.00  41.00   1.00    1.52    --   54.00  19.00 -90.00   31
  8  \w     26.00  68.00   1.00    1.52    --   54.00-125.00-180.00   42
  9  \w     96.00 130.00   1.00    1.52    --  108.00 -50.00  30.00   34
 10  \w     90.00 172.00   1.00    1.52    --  108.00  38.00-120.00   82
 11  \w     81.00 110.00   1.00    1.52    --  108.00-111.00 -60.00   29
 12  \w     83.00 110.00   1.00    1.52    --  108.00-111.00-120.00   27
 13  \w     89.00 121.00   1.00    1.52    --  108.00  77.00 -60.00   32
 14  \w    110.00 178.00   1.00    1.52    --  108.00  50.00-150.00   68
 15  \w     40.00  80.00   1.00    1.52    --  108.00 -50.00  30.00   40
 16  \w     58.00  83.00   1.00    1.52    --  108.00 -63.00  60.00   25
 17  \w     89.00 175.00   1.00    1.52    --  108.00  63.00 120.00   86
 18  \w     93.00 119.00   1.00    1.52    --  108.00  63.00-180.00   26
 19  \w     94.00 119.00   1.00    1.52    --  108.00 -38.00 -30.00   25
 20  \w     36.00  67.00   1.00    1.52    --  108.00 -38.00 -30.00   31
 21  \w     86.00 175.00   1.00    1.52    --  108.00  63.00 -90.00   89
 22  \w     97.00 129.00   1.00    1.52    --  108.00 -63.00  60.00   32
 23  \w    138.00 163.00   1.00    1.52    --  108.00  63.00  60.00   25
 24  \w     79.00 147.00   1.00    1.52    --  108.00  77.00 150.00   68
 25  \w     36.00 111.00   1.00    1.52    --  108.00-111.00  30.00   75
 26  \w     68.00  94.00   1.00    1.52    --  108.00 -50.00 -90.00   26
 27  \w    100.00 147.00   1.00    1.52    --  108.00  38.00 -60.00   47
 28  \w     66.00  92.00   1.00    1.52    --  108.00 -25.00  30.00   26
 29  \w     98.00 123.00   1.00    1.52    --  108.00 -25.00  30.00   25
 30  \w    130.00 158.00   1.00    1.52    --  108.00  38.00 150.00   28
 31  \w     94.00 129.00   1.00    1.52    --  108.00 -91.00  30.00   35
 32  \w     50.00  88.00   1.00    1.52    --  108.00 -91.00  30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283144000
_diffrn_orient_matrix_UB_12      0.0086901000
_diffrn_orient_matrix_UB_13      0.0803731000
_diffrn_orient_matrix_UB_21      0.0581627000
_diffrn_orient_matrix_UB_22      -0.0755784000
_diffrn_orient_matrix_UB_23      0.0163415000
_diffrn_orient_matrix_UB_31      0.1281578000
_diffrn_orient_matrix_UB_32      0.0362611000
_diffrn_orient_matrix_UB_33      0.0148253000
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23365
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.128
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0661P)^2^+0.7858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5804
_reflns_number_total             6887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00612k2.cif
_cod_data_source_block           20250407-yanhl-qwl-2_auto
_cod_depositor_comments
'Adding full bibliography for 7134484--7134485.cif.'
_cod_database_code               7134485
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C011(H01A,H01B), C012(H01C,H01D)
2.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C013(H013), C014(H014), C017(H017), C018(H018), C019(H019), C01A(H01H),
 C01B(H01I), C01C(H01J), C01F(H01Q)
2.c Idealised Me refined as rotating group:
 C016(H01E,H01F,H01G), C01D(H01K,H01L,H01M), C01E(H01N,H01O,H01P)
;
_shelx_res_checksum              13175
_shelx_hkl_checksum              94905
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.761