Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael-Michael Cascade Reactions.
Chaudhari, Prakash D.; Hong, Bor-Cherng; Wen, Chao-Lin; Lee, Gene-Hsiang; ACS omega 4 (2019) 655–667; doi:10.1021/acsomega.8b03049

data_4514959
_publ_section_title
;
 Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four
 Consecutive Stereocenters and Quaternary \a-Nitro Esters via
 Organocatalytic Enantioselective Michael-Michael Cascade Reactions.
;
_journal_issue                   1
_journal_name_full               'ACS omega'
_journal_page_first              655
_journal_page_last               667
_journal_paper_doi               10.1021/acsomega.8b03049
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C48 H48 Br2 N6 O16'
_chemical_formula_weight         1124.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                105.2163(11)
_cell_angle_beta                 96.8216(12)
_cell_angle_gamma                109.1621(12)
_cell_formula_units_Z            2
_cell_length_a                   11.3435(4)
_cell_length_b                   14.1708(5)
_cell_length_c                   17.3486(6)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.19
_cell_measurement_theta_min      3.49
_cell_volume                     2476.78(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0151
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19447
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.996
_diffrn_reflns_theta_min         2.709
_exptl_absorpt_coefficient_mu    2.733
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.058
_refine_diff_density_max         1.119
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         10155
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.540
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0688P)^2^+3.0699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9238
_reflns_number_total             10155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03049_si_003.cif
_cod_data_source_block           ic19210
_cod_database_code               4514959
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.709
_shelx_estimated_absorpt_t_max   0.858
_shelx_res_checksum              37157
_shelx_hkl_checksum              93884