LED-induced Ru-photoredox Pd-catalyzed C–H arylation of (6-phenylpyridin-2-yl)pyrimidines and heteroaryl counterparts
Antoniou, Ioakeim M.; Ioannou, Natalia; Panagiotou, Nikos; Georgiades, Savvas N.; RSC Advances 14 (2024) 12179–12191; doi:10.1039/D4RA02173H

data_7248426
_publ_section_title
;
 LED-induced Ru-photoredox Pd-catalyzed C--H arylation of
 (6-phenylpyridin-2-yl)pyrimidines and heteroaryl counterparts
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              12179
_journal_page_last               12191
_journal_paper_doi               10.1039/D4RA02173H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C30 H23 F N4 O2'
_chemical_formula_sum            'C30 H23 F N4 O2'
_chemical_formula_weight         490.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-12 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1028(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.7627(4)
_cell_length_b                   9.05888(12)
_cell_length_c                   18.3792(2)
_cell_measurement_reflns_used    17452
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      77.6200
_cell_measurement_theta_min      2.9700
_cell_volume                     4952.00(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -83.00 -58.00   0.50    0.50    -- -105.51  77.00  60.00   50
  2  \w    -61.00 -36.00   0.50    0.50    -- -105.51  57.00  60.00   50
  3  \w    -42.00  21.00   0.50    0.10    --  -50.05  38.00  90.00  126
  4  \w    -17.00  21.00   0.50    0.10    --  -50.05  15.00  40.00   76
  5  \w    -62.00   4.00   0.50    0.10    --  -50.05  57.00-180.00  132
  6  \w   -133.00-103.00   0.50    0.50    -- -105.51   0.00 150.00   60
  7  \w   -154.00-102.00   0.50    0.50    -- -105.51   0.00 120.00  104
  8  \w   -108.00 -46.00   0.50    0.50    -- -105.51 108.00 168.06  124
  9  \w   -112.00 -37.00   0.50    0.50    -- -105.51 126.00  60.00  150
 10  \w   -109.00 -69.00   0.50    0.50    -- -105.51 126.00 -90.00   80
 11  \w    -70.00 -43.00   0.50    0.50    -- -105.51 113.00-143.24   54
 12  \w   -109.00 -84.00   0.50    0.50    -- -105.51 113.00-143.24   50
 13  \w   -100.00 -46.00   0.50    0.10    --  -50.05 -15.00-129.00  108
 14  \w   -172.00-101.00   0.50    0.50    -- -105.51 -15.00-129.00  142
 15  \w   -168.00-101.00   0.50    0.50    -- -105.51 -77.00 -60.00  134
 16  \w   -102.00 -77.00   0.50    0.10    --  -50.05-126.00-180.00   50
 17  \w    -21.00   6.00   0.50    0.10    --   50.05 -15.00-129.00   54
 18  \w     35.00  65.00   0.50    0.50    --  105.51 -57.00-120.00   60
 19  \w     34.00  59.00   0.50    0.50    --  105.51 -57.00-180.00   50
 20  \w     34.00 100.00   0.50    0.50    --  105.51 -77.00 -30.00  132
 21  \w     37.00  62.00   0.50    0.50    --  105.51 -57.00  60.00   50
 22  \w     34.00  65.00   0.50    0.50    --  105.51 -57.00  30.00   62
 23  \w     34.00  63.00   0.50    0.50    --  105.51 -57.00  90.00   58
 24  \w     34.00  64.00   0.50    0.50    --  105.51 -57.00 120.00   60
 25  \w     34.00  65.00   0.50    0.50    --  105.51 -57.00 150.00   62
 26  \w     74.00 107.00   0.50    0.10    --   50.05 126.00 150.00   66
 27  \w     59.00  84.00   0.50    0.50    --  105.51   0.00  90.00   50
 28  \w    101.00 170.00   0.50    0.50    --  105.51  15.00  40.00  138
 29  \w     93.00 118.00   0.50    0.10    --   50.05  15.00  40.00   50
 30  \w     47.00  81.00   0.50    0.10    --   50.05  15.00  40.00   68
 31  \w    104.00 146.00   0.50    0.50    --  105.51  38.00 -60.00   84
 32  \w     45.00  94.00   0.50    0.10    --   50.05  38.00-120.00   98
 33  \w     57.00  83.00   0.50    0.50    --  105.51   0.00   0.00   52
 34  \w     57.00 109.00   0.50    0.50    --  105.51   0.00  60.00  104
 35  \w     78.00 106.00   0.50    0.50    --  105.51 -99.00 -30.00   56
 36  \w     50.00 100.00   0.50    0.50    --  105.51-126.00 -90.00  100
 37  \w     52.00  84.00   0.50    0.50    --  105.51-126.00 -30.00   64
 38  \w     88.00 113.00   0.50    0.50    --  105.51-126.00 -30.00   50
 39  \w     36.00  81.00   0.50    0.50    --  105.51 -99.00  60.00   90
 40  \w     38.00  67.00   0.50    0.50    --  105.51 -99.00 -30.00   58
 41  \w     14.00  94.00   0.50    0.10    --   50.05-126.00 -60.00  160
 42  \w     56.00 109.00   0.50    0.50    --  105.51-126.00-180.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071214000
_diffrn_orient_matrix_UB_12      -0.1683144000
_diffrn_orient_matrix_UB_13      -0.0028964000
_diffrn_orient_matrix_UB_21      -0.0071278000
_diffrn_orient_matrix_UB_22      -0.0100101000
_diffrn_orient_matrix_UB_23      0.0824667000
_diffrn_orient_matrix_UB_31      -0.0508026000
_diffrn_orient_matrix_UB_32      -0.0220789000
_diffrn_orient_matrix_UB_33      -0.0151078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         2.972
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_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     336
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0483P)^2^+1.7069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3908
_reflns_number_total             4412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima-2f_auto
_cod_database_code               7248426
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'F O N C H'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.951
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              13524
_shelx_hkl_checksum              83842
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.815