Diastereoselective Construction of Indole-Bridged Chroman Spirooxindoles through a TfOH-Catalyzed Michael Addition-Inspired Cascade Reaction.
Guo, Jiaomei; Bai, Xuguan; Wang, Qilin; Bu, Zhanwei; The Journal of organic chemistry 83 (2018) 3679–3687; doi:10.1021/acs.joc.8b00035

data_4035470
_publ_section_title
;
 Diastereoselective Construction of Indole-Bridged Chroman Spirooxindoles
 through a TfOH-Catalyzed Michael Addition-Inspired Cascade Reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3679
_journal_page_last               3687
_journal_paper_doi               10.1021/acs.joc.8b00035
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C32 H24 N2 O2, 0.5(C2 H6 O), 0.5(H2 O)'
_chemical_formula_sum            'C33 H28 N2 O3'
_chemical_formula_weight         500.57
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                70.8640(10)
_cell_angle_beta                 81.8930(10)
_cell_angle_gamma                62.4650(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8978(6)
_cell_length_b                   10.2382(7)
_cell_length_c                   14.8927(10)
_cell_measurement_reflns_used    7580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.35
_cell_volume                     1264.17(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18991
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.720
_diffrn_reflns_theta_min         1.447
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.4936
_exptl_transmission_factor_min   0.4460
_refine_diff_density_max         1.372
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 5434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         14101
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0822P)^2^+0.6154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                12773
_reflns_number_total             14101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00035_si_002.cif
_cod_data_source_block           mo_hd_wql15_0m
_cod_depositor_comments
;

2020-05-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C66 H56 N4 O6'
_cod_original_formula_weight         1001.14
_cod_original_formula_moiety         '2(C32 H24 N2 O2), C2 H6 O, H2 O'
_cod_original_formula_units_Z            1
_cod_database_code               4035470
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              37027
_shelx_hkl_checksum              19193