An efficient nickel/silver co-catalyzed remote C–H amination of 8-aminoquinolines with azodicarboxylates at room temperature
Zhao, Ruinan; Yang, Yaocheng; Wang, Xia; Ren, Peng; Zhang, Qian; Li, Dong; RSC Advances 8 (2018) 37064–; doi:10.1039/C8RA07647B

data_7231763
_publ_section_title
;
 An efficient nickel/silver co-catalyzed remote C--H amination of
 8-aminoquinolines with azodicarboxylates at room temperature
;
_journal_issue                   65
_journal_name_full               'RSC Advances'
_journal_page_first              37064
_journal_paper_doi               10.1039/C8RA07647B
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C17 H20 N4 O5'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.591(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3537(5)
_cell_length_b                   22.3285(17)
_cell_length_c                   8.8584(6)
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8500
_cell_measurement_theta_min      3.9460
_cell_volume                     1782.0(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -103.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 95

  2 omega  -35.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 26

  3 omega   69.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 37

  4 omega -103.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 51

  5 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -60.0000 87

  6 omega   19.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 38

  7 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 27

  8 omega   66.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 31

  9 omega   12.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 34

 10 omega   53.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 54

 11 omega   89.00  159.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 70

 12 omega   56.00   82.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 26

 13 omega   39.00  133.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 94

 14 omega   44.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 37

 15 omega   64.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 35

 16 omega   53.00   98.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 45

 17 omega   48.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 59

 18 omega   94.00  151.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 57

 19 omega  -48.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   90.0000 33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1103681000
_diffrn_orient_matrix_UB_12      -0.0513337000
_diffrn_orient_matrix_UB_13      0.0002303000
_diffrn_orient_matrix_UB_21      0.0147489000
_diffrn_orient_matrix_UB_22      0.0209966000
_diffrn_orient_matrix_UB_23      -0.1608891000
_diffrn_orient_matrix_UB_31      0.1298230000
_diffrn_orient_matrix_UB_32      0.0411761000
_diffrn_orient_matrix_UB_33      0.0818795000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6810
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.124
_diffrn_reflns_theta_max         67.124
_diffrn_reflns_theta_min         3.960
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94499
_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    1.343
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0044(4)
_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   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0552P)^2^+0.3850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2496
_reflns_number_total             3166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07647b2.cif
_cod_data_source_block           201806304
_cod_database_code               7231763
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1Zn
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'