Photoredox catalytic intramolecular imine C–H bond functionalization using ligand free Cu(ii) salts
Ren, Xuhong; Wang, Qiyang; Yu, Wenjia; Zhan, Xiaoyu; Yao, Yishan; Qin, Bingjie; Dong, Mingxin; He, Xinhua; Organic Chemistry Frontiers 4 (2017) 2022–; doi:10.1039/C7QO00348J

data_1553797
_publ_section_title
;
 Photoredox catalytic intramolecular imine C--H bond functionalization
 using ligand free Cu(ii) salts
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2022
_journal_paper_doi               10.1039/C7QO00348J
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C20 H13 F N2 O'
_chemical_formula_sum            'C20 H13 F N2 O'
_chemical_formula_weight         316.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-03-25 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3556(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.17425(19)
_cell_length_b                   7.88736(13)
_cell_length_c                   21.7312(4)
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.9820
_cell_measurement_theta_min      4.8640
_cell_volume                     1551.57(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -67.00  32.00   1.00    1.00    --  -41.49  57.00  60.00   99
  2  \w    -51.00  31.00   1.00    1.00    --  -41.49  37.00-150.00   82
  3  \w     47.00  77.00   1.00    1.00    --   41.49 -99.00-180.00   30
  4  \w     79.00 131.00   1.00    1.00    --  107.19 -77.00-120.00   52
  5  \w     91.00 130.00   1.00    1.00    --  107.19 -77.00 -60.00   39
  6  \w     85.00 134.00   1.00    1.00    --  107.19 -61.00  60.00   49
  7  \w     72.00  98.00   1.00    1.00    --   41.49-125.00 120.00   26
  8  \w     44.00 121.00   1.00    1.00    --  107.19-125.00 120.00   77
  9  \w     58.00 105.00   1.00    1.00    --  107.19 -94.00 -90.00   47
 10  \w     54.00 111.00   1.00    1.00    --  107.19-125.00-120.00   57
 11  \w     44.00  71.00   1.00    1.00    --  107.19 -77.00-120.00   27
 12  \w     91.00 165.00   1.00    1.00    --  107.19  45.00  60.00   74
 13  \w    134.00 166.00   1.00    1.00    --  107.19  45.00 -60.00   32
 14  \w     94.00 174.00   1.00    1.00    --  107.19 125.00-120.00   80
 15  \w     84.00 178.00   1.00    1.00    --  107.19  45.00 -30.00   94
 16  \w     83.00 119.00   1.00    1.00    --  107.19  45.00 -60.00   36
 17  \w     76.00 178.00   1.00    1.00    --  107.19  77.00   0.00  102
 18  \w      5.00  48.00   1.00    1.00    --   41.49 -99.00 120.00   43
 19  \w   -108.00 -20.00   1.00    1.00    --  -41.49 -57.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288165000
_diffrn_orient_matrix_UB_12      0.1437766000
_diffrn_orient_matrix_UB_13      0.0484703000
_diffrn_orient_matrix_UB_21      -0.1563940000
_diffrn_orient_matrix_UB_22      -0.0242474000
_diffrn_orient_matrix_UB_23      0.0157920000
_diffrn_orient_matrix_UB_31      0.0606273000
_diffrn_orient_matrix_UB_32      -0.1298779000
_diffrn_orient_matrix_UB_33      0.0506701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.186
_diffrn_reflns_theta_min         4.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0542P)^2^+0.3970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2833
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00348j5.cif
_cod_data_source_block           20161101b
_cod_original_cell_volume        1551.56(5)
_cod_database_code               1553797
_chemical_oxdiff_formula         c1h1n1o1f1
_reflns_odcompleteness_completeness 99.97
_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. Others
 Sof(H11)=Sof(F1B)=1-FVAR(1)
 Sof(H13)=Sof(F1A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              51535
_shelx_hkl_checksum              40797
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.703