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_1553791
_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         'C28 H21 N2 O2 P'
_chemical_formula_sum            'C28 H21 N2 O2 P'
_chemical_formula_weight         448.44
_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             2017-04-07
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-11 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.014(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9961(5)
_cell_length_b                   8.6310(3)
_cell_length_c                   21.6563(7)
_cell_measurement_reflns_used    3472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5200
_cell_measurement_theta_min      4.1000
_cell_volume                     2233.68(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -103.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 66

  2 omega   66.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

  3 omega   63.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 47

  4 omega   18.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 27

  5 omega   61.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 27

  6 omega   58.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

  7 omega  -30.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 78

  8 omega   58.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 29

  9 omega   14.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 92

 10 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 26

 11 omega   42.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 46

 12 omega   40.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

 13 omega   40.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 41

 14 omega   39.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 60

 15 omega   78.00  114.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 36

 16 omega   38.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 51

 17 omega  118.00  146.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 28

 18 omega   51.00  125.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 74

 19 omega   50.00  163.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1172872000
_diffrn_orient_matrix_UB_12      -0.0218074000
_diffrn_orient_matrix_UB_13      0.0339732000
_diffrn_orient_matrix_UB_21      -0.0536532000
_diffrn_orient_matrix_UB_22      -0.0609586000
_diffrn_orient_matrix_UB_23      0.0574224000
_diffrn_orient_matrix_UB_31      0.0042792000
_diffrn_orient_matrix_UB_32      -0.1662412000
_diffrn_orient_matrix_UB_33      -0.0254576000
_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     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8345
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.087
_diffrn_reflns_theta_max         67.087
_diffrn_reflns_theta_min         3.699
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96053
_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    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0015(2)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0535P)^2^+0.5200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3377
_reflns_number_total             3994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00305f2.cif
_cod_data_source_block           20170442
_cod_original_cell_volume        2233.68(15)
_cod_database_code               1553791
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2OS1F2
_reflns_odcompleteness_completeness 99.98
_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 N(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), C21(H21), C22(H22), C25(H25),
  C26(H26), C27(H27), C28(H28), N1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'