Highly efficient enantioselective synthesis of bispiro[benzofuran-oxindole-pyrrolidine]s through organocatalytic cycloaddition
Li, Boyu; Gao, Fengyun; Feng, Xing; Sun, Mengmeng; Guo, Yifei; Wen, Dongwa; Deng, Yabo; Huang, Jinqi; Wang, Kairong; Yan, Wenjin; Organic Chemistry Frontiers 6 (2019) 1567–; doi:10.1039/C9QO00241C

data_1554795
_publ_section_title
;
 Highly efficient enantioselective synthesis of
 bispiro[benzofuran-oxindole-pyrrolidine]s through organocatalytic
 cycloaddition
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1567
_journal_paper_doi               10.1039/C9QO00241C
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C36 H23 Br F3 N2 O3'
_chemical_formula_weight         668.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-25 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6434(5)
_cell_length_b                   14.1860(5)
_cell_length_c                   17.6525(6)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      4.00
_cell_volume                     2915.72(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16960
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.998
_exptl_absorpt_coefficient_mu    2.442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.3820
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0001P)^2^+3.6220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5017
_reflns_number_total             5106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00241c2.cif
_cod_data_source_block           20180308_Liby_C36HO3NF3Br_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1554795
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.528
_shelx_estimated_absorpt_t_max   0.641
_shelx_res_checksum              72544
_shelx_hkl_checksum              33432