I2-induced cascade cyclization and dearomatization of indoles for the highly efficient synthesis of iodinated and vinylic spiroindolenines
Wei, Xiaohui; Liang, Xuewu; Li, Yazhou; Liu, Qi; Liu, Xuyi; Zhou, Yu; Liu, Hong; Green Chemistry 23 (2021) 9165–9171; doi:10.1039/D1GC02713A

data_7243844
_publ_section_title
;
 I2-induced cascade cyclization and dearomatization of indoles for the
 highly efficient synthesis of iodinated and vinylic spiroindolenines
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              9165
_journal_page_last               9171
_journal_paper_doi               10.1039/D1GC02713A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C23 H22 I N O4'
_chemical_formula_sum            'C23 H22 I N O4'
_chemical_formula_weight         503.31
_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             2020-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0055(2)
_cell_length_b                   15.3728(5)
_cell_length_c                   17.6184(4)
_cell_measurement_reflns_used    7436
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.326
_cell_measurement_theta_min      2.360
_cell_volume                     2124.18(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14703
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.360
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0690 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.8754. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.306
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+7.3199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3679
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02713a2.cif
_cod_data_source_block           mo_22020594_0m
_cod_depositor_comments
'Adding full bibliography for 7243842--7243844.cif.'
_cod_database_code               7243844
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.802
_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. Others
 Fixed Sof: O3(0.6) O2(0.4)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C15(H15A,H15B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C13(H13), C12(H12), C3(H3), C2(H2), C10(H10), C14(H14),
 C11(H11)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'