Lewis Acid-Catalyzed Nucleophilic Addition of Indoles to in Situ-Generated 2-Amidoallyl Cations.
Schlegel, Marcel; Schneider, Christoph; The Journal of organic chemistry 82 (2017) 5986–5992; doi:10.1021/acs.joc.7b00791

data_4032555
_publ_section_title
;
 Lewis Acid-Catalyzed Nucleophilic Addition of Indoles to in
 Situ-Generated 2-Amidoallyl Cations.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5986
_journal_page_last               5992
_journal_paper_doi               10.1021/acs.joc.7b00791
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.44
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7868(3)
_cell_length_b                   19.7868(3)
_cell_length_c                   10.0428(3)
_cell_measurement_reflns_used    5909
_cell_measurement_temperature    130
_cell_measurement_theta_max      21.3400
_cell_measurement_theta_min      3.0430
_cell_volume                     3931.93(14)
_computing_cell_refinement
; 
'Sun Jun 05 12:58:46 2016' 
;
_computing_data_collection
; 
'Sun Jun 05 12:58:46 2016' 
;
_computing_data_reduction
; 
'Sun Jun 05 12:58:46 2016' 
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35938
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.274
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'Sun Jun 05 12:58:46 2016' 
;
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description
; 
'Sun Jun 05 12:58:46 2016' 
;
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3012
_reflns_number_total             3595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00791_si_002.cif
_cod_data_source_block           try1
_cod_original_cell_volume        3931.93(17)
_cod_database_code               4032555
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              48492
_shelx_hkl_checksum              52468