Copper-Catalyzed Radical-Promoted Aminocyclization of Acrylamides with N-Fluorobenzenesulfonimide.
Xia, Xiao-Feng; Zhu, Su-Li; Liu, Jian-Biao; Wang, Dawei; Liang, Yong-Min; The Journal of organic chemistry 81 (2016) 12482–12488; doi:10.1021/acs.joc.6b02337

data_4037441
_publ_section_title
;
 Copper-Catalyzed Radical-Promoted Aminocyclization of Acrylamides with
 N-Fluorobenzenesulfonimide.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12482
_journal_page_last               12488
_journal_paper_doi               10.1021/acs.joc.6b02337
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H22 N2 O6 S2'
_chemical_formula_sum            'C24 H22 N2 O6 S2'
_chemical_formula_weight         498.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.193(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1594(5)
_cell_length_b                   9.5200(3)
_cell_length_c                   13.9945(4)
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      28.4050
_cell_measurement_theta_min      3.8650
_cell_volume                     2279.99(12)
_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      air
_diffrn_ambient_temperature      294.06(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   62.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000 -120.0000 34

  2 omega  -30.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 115

  3 omega   -6.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  -90.0000 74
;
_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      0.0237242000
_diffrn_orient_matrix_UB_12      -0.0603238000
_diffrn_orient_matrix_UB_13      0.0086362000
_diffrn_orient_matrix_UB_21      0.0092170000
_diffrn_orient_matrix_UB_22      0.0226534000
_diffrn_orient_matrix_UB_23      0.0477782000
_diffrn_orient_matrix_UB_31      -0.0327034000
_diffrn_orient_matrix_UB_32      -0.0374007000
_diffrn_orient_matrix_UB_33      0.0150391000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8912
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80793
_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    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                3385
_reflns_number_total             4480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02337_si_003.cif
_cod_data_source_block           yanxb_1203
_cod_database_code               4037441
_reflns_odcompleteness_completeness 99.68
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2015-12-04
_olex2_submission_special_instructions 'No special instructions were received'