Copper-Mediated C-H Amination of Imidazopyridines with N-Fluorobenzenesulfonimide.
Lu, Shuai; Tian, Lu-Lu; Cui, Tian-Wei; Zhu, Yu-Shen; Zhu, Xinju; Hao, Xin-Qi; Song, Mao-Ping; The Journal of organic chemistry 83 (2018) 13991–14000; doi:10.1021/acs.joc.8b02348

data_4034865
_publ_section_title
;
 Copper-Mediated C-H Amination of Imidazopyridines with
 N-Fluorobenzenesulfonimide.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13991
_journal_page_last               14000
_journal_paper_doi               10.1021/acs.joc.8b02348
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C25 H19 N3 O4 S2'
_chemical_formula_sum            'C25 H19 N3 O4 S2'
_chemical_formula_weight         489.55
_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
_audit_creation_date             2018-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 128.667(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4751(4)
_cell_length_b                   19.2998(3)
_cell_length_c                   24.0776(7)
_cell_measurement_reflns_used    7230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8080
_cell_measurement_theta_min      3.9910
_cell_volume                     4526.3(4)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00  -80.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 28

  2 omega  -92.00  -57.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 35

  3 omega  -36.00   -7.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 29

  4 omega  -76.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 44

  5 omega   67.00   97.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 30

  6 omega   20.00   49.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 29

  7 omega   44.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 27

  8 omega  -30.00   -4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 26

  9 omega   62.00   97.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 35

 10 omega    2.00   35.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 33

 11 omega   71.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 38

 12 omega   39.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 32

 13 omega   72.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 33

 14 omega   26.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 74

 15 omega   79.00  106.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 27

 16 omega   39.00  137.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 98

 17 omega   68.00  108.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 40

 18 omega   38.00  106.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 68

 19 omega  127.00  171.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 44

 20 omega   62.00   90.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 28

 21 omega   88.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 90

 22 omega  104.00  169.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 65

 23 omega   43.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

 24 omega  125.00  151.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 26

 25 omega   80.00  159.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1498475000
_diffrn_orient_matrix_UB_12      0.0132432000
_diffrn_orient_matrix_UB_13      0.0309843000
_diffrn_orient_matrix_UB_21      -0.0302022000
_diffrn_orient_matrix_UB_22      0.0781592000
_diffrn_orient_matrix_UB_23      -0.0142784000
_diffrn_orient_matrix_UB_31      0.0405950000
_diffrn_orient_matrix_UB_32      0.0094687000
_diffrn_orient_matrix_UB_33      0.0745021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19890
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.005
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94375
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         8072
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6591
_reflns_number_total             8072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02348_si_001.cif
_cod_data_source_block           201803197
_cod_original_cell_volume        4526.3(3)
_cod_database_code               4034865
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2S1
_shelx_estimated_absorpt_t_max   0.724
_shelx_estimated_absorpt_t_min   0.639
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C13', C8'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13', C12'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2', C5'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C7', C8'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C4', C5'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C5') \\sim Ueq, Uanis(N2') \\sim Ueq, Uanis(C4') \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C12') \\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C7')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'),
 C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'), C13'(H13'), C15'(H15'),
 C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19'), C21'(H21'), C22'(H22'),
 C23'(H23'), C24'(H24'), C25'(H25')
;
_olex2_submission_special_instructions 'No special instructions were received'