Diastereoselective synthesis of succinimide-fused polycycles <i>via</i> intermolecular interception of indanone-allene intermediates with maleimides.
Yu, Rongjing; Xia, Ting; Shen, Ruwei; Zhu, Shugao; Chemical communications (Cambridge, England) 61 (2025) 10335–10338; doi:10.1039/d5cc02315g

data_7134670
_publ_section_title
;
 Diastereoselective synthesis of succinimide-fused polycycles <i>via</i>
 intermolecular interception of indanone-allene intermediates with
 maleimides.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10335
_journal_page_last               10338
_journal_paper_doi               10.1039/d5cc02315g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C35 H25 N O4'
_chemical_formula_sum            'C35 H25 N O4'
_chemical_formula_weight         523.56
_chemical_name_systematic        1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-08 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.647(2)
_cell_angle_beta                 81.569(2)
_cell_angle_gamma                89.219(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6029(3)
_cell_length_b                   12.5447(5)
_cell_length_c                   12.7442(2)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0010
_cell_measurement_theta_min      3.6320
_cell_volume                     1317.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.964
_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    -47.00 -16.00   0.50    0.50    --   42.30   6.00-145.00   62
  2  \w      8.00  98.00   0.50    0.50    --   42.30   6.00-145.00  180
  3  \w     20.00  65.00   0.50    0.50    --   93.70  -6.00  37.00   90
  4  \w     93.00 177.00   0.50    0.50    --   93.70  -6.00  37.00  168
  5  \w    -47.00  11.00   0.50    0.50    --   42.30 -65.00 -90.00  116
  6  \w      2.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00  136
  7  \w     38.00  63.00   0.50    0.50    --   42.30 -65.00 -90.00   50
  8  \w    -45.00  44.00   0.50    0.50    --   42.30 -82.00  60.00  178
  9  \w    -47.00  -2.00   0.50    0.50    --   42.30 -82.00 -30.00   90
 10  \w     18.00  43.00   0.50    0.50    --   42.30  -6.00  37.00   50
 11  \w     19.00  70.00   0.50    0.50    --   42.30 -82.00-180.00  102
 12  \w    -40.00  53.00   0.50    0.50    --   42.30 -65.00 150.00  186
 13  \w     -4.00  69.00   0.50    0.50    --   42.30 -82.00  90.00  146
 14  \w    -45.00  22.00   0.50    0.50    --   42.30 -82.00-150.00  134
 15  \w    -26.00  72.00   0.50    0.50    --   42.30 -54.00  30.00  196
 16  \w     -6.00  67.00   0.50    0.50    --   42.30 -82.00 -90.00  146
 17  \w     23.00  48.00   0.50    0.50    --   42.30  65.00 -30.00   50
 18  \w      5.00  93.00   0.50    0.50    --   93.70 -82.00-120.00  176
 19  \w     27.00  65.00   0.50    0.50    --   93.70 -82.00   0.00   76
 20  \w     95.00 124.00   0.50    0.50    --   93.70 -42.00 150.00   58
 21  \w      5.00 120.00   0.50    0.50    --   93.70 -82.00 120.00  230
 22  \w     73.00 122.00   0.50    0.50    --   93.70 -42.00 -30.00   98
 23  \w      4.00 121.00   0.50    0.50    --   93.70 -82.00 -30.00  234
 24  \w     64.00 154.00   0.50    0.50    --   93.70  50.00  60.00  180
 25  \w      5.00  30.00   0.50    0.50    --   93.70 -42.00 -90.00   50
 26  \w      4.00 104.00   0.50    0.50    --   93.70 -82.00-180.00  200
 27  \w     64.00 183.00   0.50    0.50    --   93.70  50.00 -30.00  238
 28  \w      4.00  44.00   0.50    0.50    --   93.70 -42.00 -30.00   80
 29  \w     53.00  91.00   0.50    0.50    --   93.70 -82.00 -60.00   76
 30  \w     69.00  94.00   0.50    0.50    --   93.70 -82.00  30.00   50
 31  \w     13.00  57.00   0.50    0.50    --   93.70 -82.00  30.00   88
 32  \w      4.00  89.00   0.50    0.50    --   93.70 -82.00 -90.00  170
 33  \w     74.00 118.00   0.50    0.50    --   93.70 -82.00   0.00   88
 34  \w      9.00  96.00   0.50    0.50    --   93.70 -82.00  49.58  174
 35  \w     36.00  76.00   0.50    0.50    --   93.70 -82.00-150.00   80
 36  \w     71.00 142.00   0.50    0.50    --   93.70  68.00 120.00  142
 37  \w     47.00  95.00   0.50    0.50    --   93.70 -82.00  90.00   96
 38  \w     14.00  64.00   0.50    0.50    --   93.70 -77.00 150.00  100
 39  \w     69.00  94.00   0.50    0.50    --   93.70   6.00-145.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011253000
_diffrn_orient_matrix_UB_12      -0.1240462000
_diffrn_orient_matrix_UB_13      0.0054171000
_diffrn_orient_matrix_UB_21      0.1804139000
_diffrn_orient_matrix_UB_22      -0.0000135000
_diffrn_orient_matrix_UB_23      -0.0078880000
_diffrn_orient_matrix_UB_31      -0.0154932000
_diffrn_orient_matrix_UB_32      -0.0262728000
_diffrn_orient_matrix_UB_33      0.1258021000
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13219
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.354
_diffrn_reflns_theta_min         3.620
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0118(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0812P)^2^+0.1717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4029
_reflns_number_total             4670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02315g2.cif
_cod_data_source_block           n1_auto
_cod_depositor_comments
'Adding full bibliography for 7134670--7134671.cif.'
_cod_database_code               7134670
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              93034
_shelx_hkl_checksum              83287
_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 9.645
_oxdiff_exptl_absorpt_empirical_full_min 0.344