Pd-Catalyzed Asymmetric Dearomative Cycloaddition for Construction of Optically Active Pyrroloindoline and Cyclopentaindoline Derivatives: Access to 3a-Aminopyrroloindolines.
Zhang, Jun-Qi; Tong, Feifei; Sun, Bing-Bing; Fan, Wei-Tai; Chen, Jun-Bo; Hu, Dandan; Wang, Xing-Wang; The Journal of organic chemistry 83 (2018) 2882–2891; doi:10.1021/acs.joc.8b00046

data_4033515
_publ_section_title
;
 Pd-Catalyzed Asymmetric Dearomative Cycloaddition for Construction of
 Optically Active Pyrroloindoline and Cyclopentaindoline Derivatives:
 Access to 3a-Aminopyrroloindolines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2882
_journal_page_last               2891
_journal_paper_doi               10.1021/acs.joc.8b00046
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H21 Br N3 O6 S'
_chemical_formula_sum            'C21 H21 Br N3 O6 S'
_chemical_formula_weight         522.86
_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   geom
_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                   7.0520(5)
_cell_length_b                   22.3291(13)
_cell_length_c                   27.6452(17)
_cell_measurement_reflns_used    4154
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.34
_cell_volume                     4353.1(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20431
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.366
_diffrn_reflns_theta_min         1.733
_exptl_absorpt_coefficient_mu    2.029
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       rodlike
_exptl_crystal_F_000             2132
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 1961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         7968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0444P)^2^+0.7034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6157
_reflns_number_total             7999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00046_si_002.cif
_cod_data_source_block           aa_a
_cod_depositor_comments
;
       Adding full bibliography for 4033515.cif.

2020-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H41 Br2 N6 O12 S2'
_cod_original_formula_weight         1045.73
_cod_original_formula_moiety         'C21 H21 Br N3 O6 S, C21 H20 Br N3 O6 S'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4353.2(5)
_cod_database_code               4033515
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              19726
_shelx_hkl_checksum              38217