Synthesis of Quaternary 3,3-Disubstituted 2-Oxindoles from 2-Substituted Indole Using Selectfluor.
Jiang, Xiaojian; Yang, Junjie; Zhang, Feng; Yu, Pei; Yi, Peng; Sun, Yewei; Wang, Yuqiang; Organic letters 18 (2016) 3154–3157; doi:10.1021/acs.orglett.6b01367

data_1543438
_publ_section_title
;
 Synthesis of Quaternary 3,3-Disubstituted 2-Oxindoles from 2-Substituted
 Indole Using Selectfluor.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3154
_journal_page_last               3157
_journal_paper_doi               10.1021/acs.orglett.6b01367
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9339(2)
_cell_length_b                   12.3047(5)
_cell_length_c                   21.7128(9)
_cell_measurement_reflns_used    1782
_cell_measurement_temperature    199.16(10)
_cell_measurement_theta_max      62.9050
_cell_measurement_theta_min      4.1330
_cell_volume                     1585.36(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.16(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   26.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -60.0000 34

  2 omega  113.00  163.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   30.0000 50

  3 omega   83.00  111.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -18.0000   35.0000 28

  4 omega   56.00   82.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 26

  5 omega   35.00   61.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 26

  6 omega   25.00   50.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 25

  7 omega   45.00   83.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -150.0000 38

  8 omega   18.00   43.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -90.0000 25

  9 omega   17.00   60.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -18.0000   35.0000 43

 10 omega   24.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 53

 11 omega   57.00   82.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  120.0000 25

 12 omega   23.00   57.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 34

 13 omega  -39.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -19.0000 -120.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0363644000
_diffrn_orient_matrix_UB_12      -0.1210044000
_diffrn_orient_matrix_UB_13      -0.0153187000
_diffrn_orient_matrix_UB_21      -0.0537138000
_diffrn_orient_matrix_UB_22      0.0230908000
_diffrn_orient_matrix_UB_23      -0.0681537000
_diffrn_orient_matrix_UB_31      0.2513735000
_diffrn_orient_matrix_UB_32      0.0224782000
_diffrn_orient_matrix_UB_33      -0.0123835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3907
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        62.854
_diffrn_reflns_theta_max         62.854
_diffrn_reflns_theta_min         4.130
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0492P)^2^+0.0742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.512
_reflns_Friedel_fraction_full    0.738
_reflns_Friedel_fraction_max     0.738
_reflns_number_gt                2099
_reflns_number_total             2268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01367_si_002.cif
_cod_data_source_block           yangjunjie_20150309
_cod_depositor_comments          'Adding full bibliography for 1543438.cif.'
_cod_database_code               1543438
_reflns_odcompleteness_completeness 97.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C16(H16), C20(H20), C6(H6), C17(H17), C8(H8), C19(H19),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'