Copper-catalyzed intramolecular dearomative aza-Wacker reaction of indole.
Wang, Bi; Liang, Ren-Xiao; Shen, Zhen-Lu; Jia, Yi-Xia; Chemical communications (Cambridge, England) 60 (2024) 3858–3861; doi:10.1039/d3cc06217a

data_7132808
_publ_section_title
;
 Copper-catalyzed intramolecular dearomative aza-Wacker reaction of
 indole.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3858
_journal_page_last               3861
_journal_paper_doi               10.1039/d3cc06217a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H23.63 Cl0.37 N2 O3 S'
_chemical_formula_sum            'C26 H23.62 Cl0.38 N2 O3 S'
_chemical_formula_weight         457.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-25 deposited with the CCDC.	2024-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.321(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.908(4)
_cell_length_b                   15.648(6)
_cell_length_c                   14.141(5)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.41
_cell_volume                     2232.8(14)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45570
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_min         2.027
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9178.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.041
_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     303
_refine_ls_number_reflns         4935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0502P)^2^+1.0856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4186
_reflns_number_total             4935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06217a2.cif
_cod_data_source_block           mo_211221_wb_2f_0m
_cod_depositor_comments          'Adding full bibliography for 7132808.cif.'
_cod_database_code               7132808
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.903
_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. Shared sites
{C26, C26A}
3. Uiso/Uaniso restraints and constraints
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(Cl1)=Sof(C26A)=Sof(H26C)=1-FVAR(1)
 Sof(C26)=Sof(H26A)=Sof(H26B)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14), C19(H19), C20(H20),
 C22(H22), C23(H23), C26A(H26C)
5.b X=CH2 refined with riding coordinates:
 C26(H26A,H26B)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              9334
_shelx_hkl_checksum              51102
_olex2_submission_special_instructions 'No special instructions were received'