Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine.
Chen, Si-Kai; Ma, Wen-Qiang; Yan, Zhi-Bo; Zhang, Fu-Min; Wang, Shao-Hua; Tu, Yong-Qiang; Zhang, Xiao-Ming; Tian, Jin-Miao; Journal of the American Chemical Society 140 (2018) 10099–10103; doi:10.1021/jacs.8b05386

data_4132658
_publ_section_title
;
 Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of
 Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters
 and Total Synthesis of (-)-Chimonanthidine.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10099
_journal_page_last               10103
_journal_paper_doi               10.1021/jacs.8b05386
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H36 N2 O10'
_chemical_formula_sum            'C32 H36 N2 O10'
_chemical_formula_weight         608.63
_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
_audit_creation_date             2017-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                78.0860(10)
_cell_angle_beta                 76.3090(10)
_cell_angle_gamma                77.6630(10)
_cell_formula_units_Z            2
_cell_length_a                   11.4940(2)
_cell_length_b                   11.7725(2)
_cell_length_c                   12.7954(3)
_cell_measurement_reflns_used    8553
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.60
_cell_volume                     1621.03(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13381
_diffrn_reflns_point_group_measured_fraction_full 0.753
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.292
_diffrn_reflns_theta_min         3.604
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1532 before and 0.0799 after correction. The Ratio of minimum to maximum transmission is 0.7071. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     809
_refine_ls_number_reflns         8906
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0467P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.531
_reflns_Friedel_fraction_full    0.525
_reflns_Friedel_fraction_max     0.520
_reflns_number_gt                8275
_reflns_number_total             8906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05386_si_002.cif
_cod_data_source_block           20171017_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/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               4132658
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.747
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B), C55(H55A,H55B), C58(H58A,H58B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28),
 C29(H29), C50(H50), C51(H51), C52(H52), C53(H53), C61(H61), C62(H62), C63(H63),
  C64(H64)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C),
 C44(H44A,H44B,H44C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C57(H57A,H57B,
 H57C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              56965
_shelx_hkl_checksum              84627
_olex2_submission_special_instructions 'No special instructions were received'