Nickel-promoted C(2)‒H amidation of quinoline N-oxides with N-fluorobenzenesulfonimide
Han, Shuaijun; Gao, Xianying; Wu, Qingsong; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie; Organic Chemistry Frontiers 6 (2019) 830–; doi:10.1039/C8QO01281D

data_1554561
_publ_section_title
;
 Nickel-promoted C(2)--H amidation of quinoline N-oxides with
 N-fluorobenzenesulfonimide
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              830
_journal_paper_doi               10.1039/C8QO01281D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         '2(C15 H12 N2 O2 S), C Cl2'
_chemical_formula_sum            'C31 H26 Cl2 N4 O4 S2'
_chemical_formula_weight         653.58
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-17 deposited with the CCDC.
2019-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.373(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2400(4)
_cell_length_b                   10.3859(4)
_cell_length_c                   17.7438(8)
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5590
_cell_measurement_theta_min      4.2950
_cell_volume                     1511.84(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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -101.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 85

  2 omega  -81.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 53

  3 omega  -19.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 74

  4 omega    0.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   30.0000 57

  5 omega   60.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 45

  6 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  -60.0000 26

  7 omega  -35.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  -60.0000 82

  8 omega   77.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 32

  9 omega   37.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  126.0000 25

 10 omega   41.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 57

 11 omega   38.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 55

 12 omega   56.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 44

 13 omega  107.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 62

 14 omega   38.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 54

 15 omega   42.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 61

 16 omega   64.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0909197000
_diffrn_orient_matrix_UB_12      -0.0512890000
_diffrn_orient_matrix_UB_13      0.0658589000
_diffrn_orient_matrix_UB_21      -0.1499352000
_diffrn_orient_matrix_UB_22      -0.0296732000
_diffrn_orient_matrix_UB_23      -0.0557938000
_diffrn_orient_matrix_UB_31      0.0669991000
_diffrn_orient_matrix_UB_32      -0.1359788000
_diffrn_orient_matrix_UB_33      -0.0126668000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5575
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.054
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_min         4.940
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68398
_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    1.436
_exptl_crystal_description       prism
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.069
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0642
_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^)+(0.1024P)^2^+1.4400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.1981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2193
_reflns_number_total             2695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01281d2.cif
_cod_data_source_block           201803187
_cod_original_cell_volume        1511.85(12)
_cod_database_code               1554561
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H20N2O8P1
_shelx_estimated_absorpt_t_max   0.653
_shelx_estimated_absorpt_t_min   0.581
_reflns_odcompleteness_completeness 99.72
_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. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
 Cl1-C16
 1.98 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C16(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'