Sn-Catalyzed Criegee-Type Rearrangement of Peroxyoxindoles Enabled by Catalytic Dual Activation of Esters and Peroxides.
Chaudhari, Moreshwar Bhagwan; Jayan, Krishna; Gnanaprakasam, Boopathy; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03160

data_4037927
_publ_section_title
;
 Sn-Catalyzed Criegee-Type Rearrangement of Peroxyoxindoles Enabled by
 Catalytic Dual Activation of Esters and Peroxides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03160
_journal_year                    2020
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                89.11(2)
_cell_angle_beta                 89.82(3)
_cell_angle_gamma                89.99(3)
_cell_formula_units_Z            4
_cell_length_a                   5.449(5)
_cell_length_b                   13.428(12)
_cell_length_c                   18.080(17)
_cell_measurement_reflns_used    750
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.89
_cell_measurement_theta_min      2.26
_cell_volume                     1323(2)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2170
_diffrn_reflns_av_unetI/netI     0.3456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20036
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.868
_diffrn_reflns_theta_min         1.126
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       rod
_exptl_crystal_F_000             572
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.2965
_refine_ls_R_factor_gt           0.0828
_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^)+(0.0586P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.2277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2038
_reflns_number_total             6768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03160_si_002.cif
_cod_data_source_block           MBC_a
_cod_database_code               4037927
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              90939
_shelx_hkl_checksum              10369