Organocatalytic enantioselective (4+3) cyclization for the synthesis of spiro-fused heterocyclic compounds containing isoindolinone, oxepine and indole moieties.
Rui, Kanghua; Huang, Shaoying; Wu, Yinong; Shen, Hanxiao; Lin, Xufeng; Chemical communications (Cambridge, England) 60 (2024) 9400–9403; doi:10.1039/d4cc03230f

data_7133483
_publ_section_title
;
 Organocatalytic enantioselective (4+3) cyclization for the synthesis of
 spiro-fused heterocyclic compounds containing isoindolinone, oxepine and
 indole moieties.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9400
_journal_page_last               9403
_journal_paper_doi               10.1039/d4cc03230f
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H25 I N2 O2, C H2 Cl2, C3 H7'
_chemical_formula_sum            'C41 H34 Cl2 I N2 O2'
_chemical_formula_weight         784.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-18 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.7760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.7116(11)
_cell_length_b                   10.1135(4)
_cell_length_c                   16.0912(6)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.470
_cell_measurement_theta_min      2.208
_cell_volume                     3654.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            57727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.208
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.060
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1313 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.8747.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 3148 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         8380
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0344P)^2^+4.8415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7592
_reflns_number_total             8380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03230f2.cif
_cod_data_source_block           mo_231204_rkh012_0m
_cod_depositor_comments          'Adding full bibliography for 7133483.cif.'
_cod_database_code               7133483
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.665
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C39-C40
 1.53 with sigma of 0.01
 C41-C41_$1
 1.53 with sigma of 0.01
 C40-C41
 1.53 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C38(H38A,H38B), C40(H40A,H40B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C18(H18), C16(H16), C22(H22), C33(H33), C15(H15), C31(H31),
 C34(H34), C4(H4), C3(H3), C19(H19), C23(H23), C37(H37), C2(H2A), C9(H9),
 C27(H27), C25(H25), C36(H36), C29(H29), C24(H24), C35(H35), C1(H1A), C28(H28),
 C30(H30)
3.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C)
;
_shelx_res_checksum              58535
_shelx_hkl_checksum              2811
_olex2_submission_special_instructions 'No special instructions were received'