Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.
Johnson, Rebecca E.; Ree, Hwisoo; Hartmann, Marco; Lang, Laura; Sawano, Shota; Sarpong, Richmond; Journal of the American Chemical Society 141 (2019) 2233–2237; doi:10.1021/jacs.8b13388

data_4128158
_publ_section_title
;
 Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole
 Functionalizations.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2233
_journal_page_last               2237
_journal_paper_doi               10.1021/jacs.8b13388
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C H2 Cl2, C26 H30 N2 O'
_chemical_formula_sum            'C27 H32 Cl2 N2 O'
_chemical_formula_weight         471.44
_chemical_name_common            PIDAsidepdt
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                99.7130(10)
_cell_angle_beta                 104.8560(10)
_cell_angle_gamma                110.2590(10)
_cell_formula_units_Z            2
_cell_length_a                   9.92760(10)
_cell_length_b                   10.75250(10)
_cell_length_c                   12.95480(10)
_cell_measurement_reflns_used    48794
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.4420
_cell_measurement_theta_min      3.6650
_cell_volume                     1202.35(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            58641
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         3.681
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0567P)^2^+0.5887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4845
_reflns_number_total             4913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13388_si_002.cif
_cod_data_source_block           PIDAsidepdt
_cod_original_cell_volume        1202.34(2)
_cod_database_code               4128158
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.599
_shelx_estimated_absorpt_t_max   0.639
_shelx_res_checksum              43893
_shelx_hkl_checksum              2073