Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.
Gentry, Emily C.; Rono, Lydia J.; Hale, Martina E.; Matsuura, Rei; Knowles, Robert R.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b13616

data_4127189
_publ_section_title
;
 Enantioselective Synthesis of Pyrroloindolines via Noncovalent
 Stabilization of Indole Radical Cations and Applications to the Synthesis
 of Alkaloid Natural Products.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b13616
_journal_year                    2018
_chemical_formula_sum            'C36 H34 N4 O4'
_chemical_formula_weight         586.67
_chemical_name_common            ECG1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                109.43(2)
_cell_angle_beta                 93.08(3)
_cell_angle_gamma                109.33(4)
_cell_formula_units_Z            2
_cell_length_a                   9.725(9)
_cell_length_b                   11.882(7)
_cell_length_c                   16.226(11)
_cell_measurement_reflns_used    76
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      37.8568
_cell_measurement_theta_min      5.2170
_cell_volume                     1640(2)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0313
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28668
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.407
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0380P)^2^+1.9059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                4792
_reflns_number_total             5700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b13616_si_002.cif
_cod_data_source_block           PDJECG1
_cod_original_cell_volume        1640.(2)
_cod_database_code               4127189
_shelx_res_checksum              58044
_shelx_hkl_checksum              54686
_shelx_fab_checksum              8879