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_7158541
_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            'C21 H22 Cl2 N2 O3'
_chemical_formula_weight         421.30
_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                112.905(2)
_cell_angle_beta                 103.286(2)
_cell_angle_gamma                96.447(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2206(5)
_cell_length_b                   11.1857(6)
_cell_length_c                   11.8704(7)
_cell_measurement_reflns_used    8349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.185
_cell_measurement_theta_min      5.105
_cell_volume                     1069.43(11)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20962
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.127
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.4443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02383g2.cif
_cod_data_source_block           mo_dd21019_0m
_cod_original_cell_volume        1069.43(10)
_cod_database_code               7158541
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2013-4
_shelx_res_checksum              67169