Green synthesis for diverse bioactive benzo-fused spiroindolines through DBU-catalysed post-Ugi double cyclization.
Zhao, Shuang; Chen, Mengxiao; Zhou, Wenlu; Ni, Dan; Li, Zhenghua; Nie, Shenyou; He, Yi; Chemical communications (Cambridge, England) 60 (2024) 5455–5458; doi:10.1039/d4cc00846d

data_7132975
_publ_section_title
;
 Green synthesis for diverse bioactive benzo-fused spiroindolines through
 DBU-catalysed post-Ugi double cyclization.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5455
_journal_page_last               5458
_journal_paper_doi               10.1039/d4cc00846d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H20 N2 O3'
_chemical_formula_sum            'C26 H20 N2 O3'
_chemical_formula_weight         408.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-02-01 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.7430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6096(3)
_cell_length_b                   16.4461(3)
_cell_length_c                   16.1674(3)
_cell_measurement_reflns_used    6786
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3990
_cell_measurement_theta_min      3.8530
_cell_volume                     4121.74(13)
_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 0.998
_diffrn_measured_fraction_theta_max 0.991
_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     11.00  39.00   1.00    1.00    --    0.00  57.00 150.00   28
  2  \w     -1.00  33.00   1.00    1.00    --    0.00  57.00   0.00   34
  3  \w     42.00  67.00   1.00    1.00    --    0.00  57.00   0.00   25
  4  \w    -19.00   6.00   1.00    1.00    --    0.00  57.00 150.00   25
  5  \w     26.00 121.00   1.00    1.00    --   54.00  77.00 -30.00   95
  6  \w     23.00  62.00   1.00    1.00    --   54.00-125.00-150.00   39
  7  \w     26.00 122.00   1.00    1.00    --   54.00  77.00  90.00   96
  8  \w     41.00  80.00   1.00    1.00    --   54.00 -38.00 -60.00   39
  9  \w    140.00 165.00   1.00    1.00    --  108.00  63.00   0.00   25
 10  \w    131.00 177.00   1.00    1.00    --  108.00  25.00 120.00   46
 11  \w     91.00 117.00   1.00    1.00    --  108.00  63.00   0.00   26
 12  \w     79.00 105.00   1.00    1.00    --  108.00 -63.00   0.00   26
 13  \w     81.00 107.00   1.00    1.00    --  108.00-111.00-150.00   26
 14  \w     72.00  98.00   1.00    1.00    --  108.00 -50.00 -90.00   26
 15  \w     58.00  88.00   1.00    1.00    --  108.00 -77.00-120.00   30
 16  \w     38.00  64.00   1.00    1.00    --  108.00 -38.00 120.00   26
 17  \w     55.00 101.00   1.00    1.00    --  108.00-111.00 -30.00   46
 18  \w     90.00 130.00   1.00    1.00    --  108.00 -50.00 150.00   40
 19  \w    126.00 157.00   1.00    1.00    --  108.00  25.00 150.00   31
 20  \w     75.00 107.00   1.00    1.00    --  108.00  25.00 150.00   32
 21  \w     43.00 128.00   1.00    1.00    --  108.00 -50.00  30.00   85
 22  \w    134.00 160.00   1.00    1.00    --  108.00  50.00-120.00   26
 23  \w     79.00 133.00   1.00    1.00    --  108.00 -38.00 120.00   54
 24  \w    120.00 145.00   1.00    1.00    --  108.00 111.00-150.00   25
 25  \w    149.00 175.00   1.00    1.00    --  108.00  38.00-180.00   26
 26  \w     96.00 177.00   1.00    1.00    --  108.00  38.00-150.00   81
 27  \w     86.00 124.00   1.00    1.00    --  108.00 -63.00  60.00   38
 28  \w     44.00  82.00   1.00    1.00    --  108.00-111.00  60.00   38
 29  \w    153.00 178.00   1.00    1.00    --  108.00 111.00  30.00   25
 30  \w     84.00 115.00   1.00    1.00    --  108.00 -63.00  30.00   31
 31  \w    108.00 138.00   1.00    1.00    --  108.00 -77.00-120.00   30
 32  \w     52.00  77.00   1.00    1.00    --  108.00 -25.00-150.00   25
 33  \w     56.00  81.00   1.00    1.00    --  108.00 -28.00  31.99   25
;
_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      0.0509098000
_diffrn_orient_matrix_UB_12      -0.0224931000
_diffrn_orient_matrix_UB_13      -0.0728091000
_diffrn_orient_matrix_UB_21      0.0585470000
_diffrn_orient_matrix_UB_22      0.0746851000
_diffrn_orient_matrix_UB_23      0.0193856000
_diffrn_orient_matrix_UB_31      0.0621413000
_diffrn_orient_matrix_UB_32      -0.0518914000
_diffrn_orient_matrix_UB_33      0.0593553000
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.491
_diffrn_reflns_theta_min         3.848
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44833
_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    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0761P)^2^+1.4006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3436
_reflns_number_total             3915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00846d2.cif
_cod_data_source_block           20230214-sz-02-07
_cod_depositor_comments          'Adding full bibliography for 7132975.cif.'
_cod_database_code               7132975
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H20 N2 O3'
_shelx_estimated_absorpt_t_max   0.839
_shelx_estimated_absorpt_t_min   0.823
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C2, C3, C1, C2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C1 \\sim C2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C20(H20), C10(H10), C4(H4), C1(H1), C3(H3), C13(H13), C2(H2),
 C11(H11), C23(H23), C21(H21), C12(H12), C22(H22)
;
_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 2.252
_oxdiff_exptl_absorpt_empirical_full_min 0.739