Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides
Qiao, Huijie; Sun, Suyan; Zhang, Yue; Zhu, Hongmei; Yu, Xiaomeng; Yang, Fan; Wu, Yusheng; Li, Zhongxian; Wu, Yangjie; Organic Chemistry Frontiers 4 (2017) 1981–; doi:10.1039/C7QO00305F

data_1553790
_publ_section_title
;
 Merging photoredox catalysis with transition metal catalysis:
 site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1981
_journal_paper_doi               10.1039/C7QO00305F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C29 H23 N2 O3 P'
_chemical_formula_sum            'C29 H23 N2 O3 P'
_chemical_formula_weight         478.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-02
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-05 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                103.110(8)
_cell_angle_beta                 94.035(8)
_cell_angle_gamma                114.371(8)
_cell_formula_units_Z            2
_cell_length_a                   9.5853(9)
_cell_length_b                   9.8739(8)
_cell_length_c                   14.7007(14)
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9490
_cell_measurement_theta_min      5.1250
_cell_volume                     1213.1(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -108.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  150.0000 76

  2 omega  -49.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -120.0000 86

  3 omega -102.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 87

  4 omega -104.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000   60.0000 93

  5 omega   -1.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   30.0000 110

  6 omega   57.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 53

  7 omega   -4.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 81

  8 omega   61.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 48

  9 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 26

 10 omega   -3.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 71

 11 omega   57.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 52

 12 omega   54.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 51

 13 omega   28.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -124.0000   58.0000 57

 14 omega   49.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 43

 15 omega   38.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 66

 16 omega   40.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 59

 17 omega   42.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 36

 18 omega   37.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 42

 19 omega   45.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 43

 20 omega   37.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 46

 21 omega   99.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 78

 22 omega   53.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 27

 23 omega   73.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 30

 24 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 26

 25 omega  128.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 25

 26 omega   39.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 60

 27 omega   94.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 74

 28 omega   64.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 43

 29 omega   40.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -148.0000 -105.0000 94

 30 omega  102.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1136452000
_diffrn_orient_matrix_UB_12      0.1717131000
_diffrn_orient_matrix_UB_13      0.0157059000
_diffrn_orient_matrix_UB_21      -0.0307724000
_diffrn_orient_matrix_UB_22      -0.0217059000
_diffrn_orient_matrix_UB_23      -0.1078005000
_diffrn_orient_matrix_UB_31      -0.1356213000
_diffrn_orient_matrix_UB_32      0.0444640000
_diffrn_orient_matrix_UB_33      0.0108153000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8680
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.003
_diffrn_reflns_theta_max         67.003
_diffrn_reflns_theta_min         5.125
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97307
_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    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0020(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   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0681P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3472
_reflns_number_total             4325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00305f2.cif
_cod_data_source_block           20170698
_cod_database_code               1553790
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O2P1
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'