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_7248424
_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         'C38 H28 N4 O3'
_chemical_formula_sum            'C38 H28 N4 O3'
_chemical_formula_weight         588.64
_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     iterative
_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                 98.5987(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.57556(11)
_cell_length_b                   33.1193(3)
_cell_length_c                   9.47501(10)
_cell_measurement_reflns_used    15012
_cell_measurement_temperature    149.98(16)
_cell_measurement_theta_max      77.2910
_cell_measurement_theta_min      2.6660
_cell_volume                     3281.37(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     36.00  79.00   0.50    0.75    --  105.35 -99.00  60.00   86
  2  \w     45.00  70.00   0.50    0.15    --   49.97-114.00-113.00   50
  3  \w     52.00 108.00   0.50    0.75    --  105.35-114.00-113.00  112
  4  \w     48.00 101.00   0.50    0.75    --  105.35 -99.00 -60.00  106
  5  \w     35.00  64.00   0.50    0.75    --  105.35 -57.00-120.00   58
  6  \w     34.00  61.00   0.50    0.75    --  105.35 -57.00 -90.00   54
  7  \w     41.00  66.00   0.50    0.75    --  105.35 -57.00-150.00   50
  8  \w    -20.00  25.00   0.50    0.15    --   49.97 -19.00-150.00   90
  9  \w     34.00  66.00   0.50    0.75    --  105.35 -57.00  90.00   64
 10  \w     35.00  60.00   0.50    0.75    --  105.35 -57.00 120.00   50
 11  \w     73.00 102.00   0.50    0.75    --  105.35   0.00 120.00   58
 12  \w    103.00 171.00   0.50    0.75    --  105.35  19.00  90.00  136
 13  \w     74.00 107.00   0.50    0.15    --   49.97 125.00 -90.00   66
 14  \w     74.00 117.00   0.50    0.15    --   49.97 125.00-180.00   86
 15  \w     98.00 125.00   0.50    0.75    --  105.35 114.00 -22.00   54
 16  \w     78.00 118.00   0.50    0.15    --   49.97 125.00  90.00   80
 17  \w    -73.00 -38.00   0.50    0.75    -- -105.35 125.00 150.00   70
 18  \w   -110.00 -84.00   0.50    0.75    -- -105.35 125.00 150.00   52
 19  \w    -86.00 -45.00   0.50    0.15    --  -49.97 114.00 -22.00   82
 20  \w   -104.00 -38.00   0.50    0.75    -- -105.35 114.00 -22.00  132
 21  \w    -96.00 -70.00   0.50    0.75    -- -105.35  77.00 -30.00   52
 22  \w    -26.00  20.00   0.50    0.15    --  -49.97  19.00  60.00   92
 23  \w    -62.00 -37.00   0.50    0.75    -- -105.35  77.00 -30.00   50
 24  \w    -66.00 -40.00   0.50    0.75    -- -105.35  57.00 -90.00   52
 25  \w    -64.00 -38.00   0.50    0.75    -- -105.35  57.00-180.00   52
 26  \w   -154.00-123.00   0.50    0.75    -- -105.35   0.00 -60.00   62
 27  \w   -130.00 -81.00   0.50    0.75    -- -105.35-114.00-113.00   98
 28  \w   -119.00 -74.00   0.50    0.15    --  -49.97-125.00  90.00   90
;
_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      0.0641069000
_diffrn_orient_matrix_UB_12      -0.0173671000
_diffrn_orient_matrix_UB_13      -0.1225287000
_diffrn_orient_matrix_UB_21      0.0001399000
_diffrn_orient_matrix_UB_22      0.0423405000
_diffrn_orient_matrix_UB_23      -0.0672970000
_diffrn_orient_matrix_UB_31      0.1326544000
_diffrn_orient_matrix_UB_32      0.0083264000
_diffrn_orient_matrix_UB_33      0.0865856000
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.996
_diffrn_reflns_theta_max         66.996
_diffrn_reflns_theta_min         2.668
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0777P)^2^+1.0790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5286
_reflns_number_total             5857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima_3bf_white_auto
_cod_database_code               7248424
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O N C H'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.930
_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:
 N11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22),
 C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49376
_shelx_hkl_checksum              65536
_shelx_fab_checksum              72696
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.777