AgSbF<sub>6</sub>-catalyzed C3 <i>aza</i>-Friedel-Crafts alkylation of <i>N</i>,<i>O</i>-acetals with indoles for the synthesis of <i>N-α</i> indole substituted pyrrolidine and piperidine derivatives.
Zhang, Yu; Yi, Zi-Juan; Yang, Ai-Mei; Guo, Jia-Ming; Li, Xin; Wei, Bang-Guo; Organic & biomolecular chemistry 21 (2023) 1303–1315; doi:10.1039/d2ob02213c

data_7159084
_publ_section_title
;
 AgSbF<sub>6</sub>-catalyzed C3 <i>aza</i>-Friedel-Crafts alkylation of
 <i>N</i>,<i>O</i>-acetals with indoles for the synthesis of
 <i>N-&#x3b1;</i> indole substituted pyrrolidine and piperidine
 derivatives.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1303
_journal_page_last               1315
_journal_paper_doi               10.1039/d2ob02213c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H44 N2 O3 Si'
_chemical_formula_weight         472.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-05-08 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.937(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2060(5)
_cell_length_b                   11.4624(6)
_cell_length_c                   12.4467(6)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.910
_cell_measurement_theta_min      4.560
_cell_volume                     1392.92(12)
_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 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22950
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 2235 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.025(10)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5418
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5084
_reflns_number_total             5418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02213c2.cif
_cod_data_source_block           mo_ddz21073_0m
_cod_depositor_comments
'Adding full bibliography for 7159083--7159084.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159084
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
_shelx_res_checksum              10950