Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles.
Chaudhari, Prakash D.; Hong, Bor-Cherng; Lee, Gene-Hsiang; Organic letters 19 (2017) 6112–6115; doi:10.1021/acs.orglett.7b02962

data_1547860
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Michael-Michael-Aldol
 Condensation Reactions: Control of Six Stereocenters in a
 Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic
 Oxindoles.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6112
_journal_page_last               6115
_journal_paper_doi               10.1021/acs.orglett.7b02962
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30.16 H25.33 Cl0.33 N O2'
_chemical_formula_weight         891.33
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 90
_cell_angle_gamma                120
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_cell_length_a                   26.4511(4)
_cell_length_b                   26.4511(4)
_cell_length_c                   11.7055(2)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.86
_cell_volume                     7092.64(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            41560
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         3.342
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       needle
_exptl_crystal_F_000             2820
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.114
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_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 3998 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8975
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0757P)^2^+0.4331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8679
_reflns_number_total             8975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02962_si_002.cif
_cod_data_source_block           ic17986
_cod_depositor_comments
;
Adding full bibliography for 1547860--1547863.cif.

2019-08-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C60.33 H50.67 Cl0.67 N2 O4'
_cod_original_formula_weight         891.33
_cod_original_formula_units_Z            6
_cod_original_cell_volume        7092.6(2)
_cod_database_code               1547860
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.794
_shelx_estimated_absorpt_t_max   0.900
_shelx_res_checksum              79991
_shelx_hkl_checksum              46408