Thiourea-Quaternary Ammonium Salt Catalyzed Asymmetric 1, 3-Dipolar Cycloaddition of Imino Esters To Construct Spiro[pyrrolidin-3,3'-oxindoles].
Zhang, Jia-Xing; Wang, Hong-Yu; Jin, Qiao-Wen; Zheng, Chang-Wu; Zhao, Gang; Shang, Yong-Jia; Organic letters 18 (2016) 4774–4777; doi:10.1021/acs.orglett.6b02098

data_1555693
_publ_section_title
;
 Thiourea-Quaternary Ammonium Salt Catalyzed Asymmetric 1, 3-Dipolar
 Cycloaddition of Imino Esters To Construct
 Spiro[pyrrolidin-3,3'-oxindoles].
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4774
_journal_page_last               4777
_journal_paper_doi               10.1021/acs.orglett.6b02098
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H36 N2 O3'
_chemical_formula_sum            'C36 H36 N2 O3'
_chemical_formula_weight         544.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.3650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3376(3)
_cell_length_b                   9.2055(2)
_cell_length_c                   14.8038(4)
_cell_measurement_reflns_used    8498
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      6.50
_cell_volume                     1482.45(7)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10745
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         6.499
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0458P)^2^+0.1850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4976
_reflns_number_total             5145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02098_si_001.cif
_cod_data_source_block           P
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555693
_shelxl_version_number           2014-3
_shelx_res_checksum              38543
_shelx_hkl_checksum              73708