Cu(OTf)2-catalyzed C3 aza-Friedel–Crafts alkylation of indoles with N,O-acetals
Yi, Zi-Juan; Sun, Jian-Ting; Yang, Tian-Yu; Yu, Xian-Yong; Han, Xiao-Li; Wei, Bang-Guo; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02383G

data_7158542
_publ_section_title
;
 Cu(OTf)2-catalyzed C3 aza-Friedel--Crafts alkylation of indoles with
 N,O-acetals
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02383G
_journal_year                    2022
_chemical_formula_sum            'C20 H21 Br N2 O'
_chemical_formula_weight         385.30
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-10-26 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                91.317(2)
_cell_angle_beta                 95.348(2)
_cell_angle_gamma                108.325(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7774(6)
_cell_length_b                   10.6374(7)
_cell_length_c                   18.9895(14)
_cell_measurement_reflns_used    7988
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      48.718
_cell_measurement_theta_min      4.473
_cell_volume                     1863.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.342
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0453P)^2^+1.4689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4819
_reflns_number_total             7312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02383g2.cif
_cod_data_source_block           mo_dd21044_0m
_cod_database_code               7158542
_shelx_estimated_absorpt_t_min   0.718
_shelx_estimated_absorpt_t_max   0.809
_shelxl_version_number           2013-4
_shelx_res_checksum              68560