Organocatalytic Enantioselective Friedel–Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
Montesinos-Magraner, Marc; Vila, Carlos; Rendón-Patiño, Alejandra; Blay, Gonzalo; Fernández, Isabel; Muñoz, M. Carmen; Pedro, José R.; ACS Catalysis 6 (2016) 2689–; doi:10.1021/acscatal.6b00260

data_4513856
_publ_section_title
;
 Organocatalytic Enantioselective Friedel--Crafts Aminoalkylation of
 Indoles in the Carbocyclic Ring
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2689
_journal_paper_doi               10.1021/acscatal.6b00260
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H29 N3 O6 S'
_chemical_formula_weight         547.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5920(2)
_cell_length_b                   11.3280(3)
_cell_length_c                   27.7780(5)
_cell_measurement_reflns_used    6400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2703.64(11)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12178
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.976
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.744
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         6176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.744
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0440
_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^)+(0.1243P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3463
_reflns_number_total             6176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00260_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4513855--4513857.cif.'
_cod_database_code               4513856
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014-1
_shelx_res_checksum              11923
_shelx_hkl_checksum              17822