Silver-Catalyzed Difluoroamidation of Activated Alkenes for the Construction of Difluorinated 3,3-Disubstituted Oxindoles.
Wang, Chao; Chen, Qiao; Guo, Quanping; Liu, Hong; Xu, Zhaoqing; Liu, Yubing; Wang, Mengran; Wang, Rui; The Journal of organic chemistry 81 (2016) 5782–5788; doi:10.1021/acs.joc.6b01013

data_4031999
_publ_section_title
;
 Silver-Catalyzed Difluoroamidation of Activated Alkenes for the
 Construction of Difluorinated 3,3-Disubstituted Oxindoles.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5782
_journal_page_last               5788
_journal_paper_doi               10.1021/acs.joc.6b01013
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H26 F2 N2 O2'
_chemical_formula_sum            'C23 H26 F2 N2 O2'
_chemical_formula_weight         400.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3541(8)
_cell_length_b                   12.9841(9)
_cell_length_c                   23.2417(13)
_cell_measurement_reflns_used    1192
_cell_measurement_temperature    295.06(10)
_cell_measurement_theta_max      20.1010
_cell_measurement_theta_min      3.6750
_cell_volume                     4331.7(5)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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      air
_diffrn_ambient_temperature      295.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -15.00   22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.8354  -99.0000 -120.0000 37

  2 omega   24.00   72.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541   57.0000  -30.0000 48

  3 omega  -45.00   39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541  -38.0000   30.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0058189000
_diffrn_orient_matrix_UB_12      0.0430422000
_diffrn_orient_matrix_UB_13      -0.0184689000
_diffrn_orient_matrix_UB_21      -0.0078036000
_diffrn_orient_matrix_UB_22      -0.0320462000
_diffrn_orient_matrix_UB_23      -0.0242254000
_diffrn_orient_matrix_UB_31      -0.0484447000
_diffrn_orient_matrix_UB_32      0.0103201000
_diffrn_orient_matrix_UB_33      0.0017013000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12075
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30440
_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    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.2101
_refine_ls_R_factor_gt           0.0951
_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^)+(0.1429P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2415
_refine_ls_wR_factor_ref         0.3318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1623
_reflns_number_total             4255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01013_si_002.cif
_cod_data_source_block           wangchao1208
_cod_depositor_comments          'Adding full bibliography for 4031999.cif.'
_cod_original_cell_volume        4331.7(4)
_cod_database_code               4031999
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B), C20(H20A,H20B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'