Oxidative Fragmentations and Skeletal Rearrangements of Oxindole Derivatives.
Klare, Hendrik F. T.; Goldberg, Alexander F. G.; Duquette, Douglas C.; Stoltz, Brian M.; Organic letters 19 (2017) 988–991; doi:10.1021/acs.orglett.6b03789

data_1545435
_publ_section_title
;
 Oxidative Fragmentations and Skeletal Rearrangements of Oxindole
 Derivatives.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              988
_journal_page_last               991
_journal_paper_doi               10.1021/acs.orglett.6b03789
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4713),
 SHELXL-2013,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.7256(10)
_cell_length_b                   12.4161(7)
_cell_length_c                   25.1262(14)
_cell_measurement_reflns_used    9616
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.20
_cell_volume                     5217.9(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_collection
'APEX2 2011.2-3, APEX2 2013.2-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics
'DIAMOND 3 (Crystal Impact, 1999),Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013/2 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41655
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.485
_diffrn_reflns_theta_min         2.043
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.8792.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       blade
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 3159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         10988
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0367P)^2^+0.2379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.665
_reflns_number_gt                8290
_reflns_number_total             10988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03789_si_001.cif
_cod_data_source_block           hkl01
_cod_database_code               1545435
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), N1B(H1B), C4B(H4B), C5B(H5B),
 C6B(H6B), C7B(H7B), N1C(H1C), C4C(H4C), C5C(H5C), C6C(H6C), C7C(H7C), N1D(H1D),
  C4D(H4D), C5D(H5D), C6D(H6D), C7D(H7D)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C9B(H9D,H9E,H9F), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F), C13B(H13D,
 H13E,H13F), C9C(H9G,H9H,H9I), C11C(H11G,H11H,H11I), C12C(H12G,H12H,H12I),
 C13C(H13G,H13H,H13I), C9D(H9J,H9K,H9L), C11D(H11J,H11K,H11L), C12D(H12J,H12K,
 H12L), C13D(H13J,H13K,H13L)
;