Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively.
Xiong, Cheng; Cheng, Kunpeng; Wang, Jiahua; Yang, Fulai; Lu, Jinrong; Zhou, Qingfa; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00652

data_4038524
_publ_section_title
;
 Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to
 Form Spiro-1,2-dioxolanes Diastereoselectively.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00652
_journal_year                    2020
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4100(11)
_cell_length_b                   12.802(3)
_cell_length_c                   22.803(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      7
_cell_volume                     1579.3(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.847
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.2910
_diffrn_reflns_Laue_measured_fraction_full 0.847
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2132
_diffrn_reflns_point_group_measured_fraction_full 0.661
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.511
_diffrn_reflns_theta_min         1.786
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       Block/needle/plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 98 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.3239
_refine_ls_R_factor_gt           0.0885
_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^)+(0.0700P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.2670
_reflns_Friedel_coverage         0.316
_reflns_Friedel_fraction_full    0.392
_reflns_Friedel_fraction_max     0.378
_reflns_number_gt                535
_reflns_number_total             1907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00652_si_002.cif
_cod_data_source_block           Q
_cod_database_code               4038524
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              98711
_shelx_hkl_checksum              79287