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_7248428
_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         'C31 H26 N4 O2'
_chemical_formula_sum            'C31 H26 N4 O2'
_chemical_formula_weight         486.56
_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                 94.5518(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.8184(4)
_cell_length_b                   8.96166(12)
_cell_length_c                   18.6116(2)
_cell_measurement_reflns_used    12195
_cell_measurement_temperature    179.98(10)
_cell_measurement_theta_max      76.1980
_cell_measurement_theta_min      4.7370
_cell_volume                     5124.01(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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.98(10)
_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   -120.00 -40.00   0.50    0.50    --  -47.44 -70.00  94.00  160
  2  \w    -44.00  12.00   0.50    0.50    --  -47.44  70.00-134.00  112
  3  \w     84.00 120.00   0.50    0.50    --   47.44  70.00-134.00   72
  4  \w     14.00  65.00   0.50    0.50    --   47.44 -70.00  94.00  102
  5  \w   -158.00 -86.00   0.50    2.00    -- -106.00 -70.00  94.00  144
  6  \w    -80.00 -37.00   0.50    2.00    -- -106.00  70.00-134.00   86
  7  \w     34.00  71.00   0.50    2.00    --  106.24 -70.00  94.00   74
  8  \w     89.00 149.00   0.50    2.00    --  106.24  70.00-134.00  120
  9  \w    -28.00  23.00   0.50    0.50    --  -47.44  19.00-150.00  102
 10  \w     18.00  91.00   0.50    0.50    --   47.44-126.00  90.00  146
 11  \w     -3.00  25.00   0.50    0.50    --   47.44 -19.00  90.00   56
 12  \w    -15.00  29.00   0.50    0.50    --   47.44 -19.00-120.00   88
 13  \w     81.00 117.00   0.50    0.50    --   47.44 126.00  90.00   72
 14  \w     85.00 118.00   0.50    0.50    --   47.44 126.00 -30.00   66
 15  \w    -70.00 -45.00   0.50    2.00    -- -106.00  61.00 -90.00   50
 16  \w   -176.00 -93.00   0.50    2.00    -- -106.00 -45.00 -30.00  166
 17  \w   -108.00 -78.00   0.50    2.00    -- -106.00 111.00  46.63   60
 18  \w   -112.00 -37.00   0.50    2.00    -- -106.00 126.00-120.00  150
 19  \w    -97.00 -35.00   0.50    2.00    -- -106.00  77.00 -90.00  124
 20  \w   -175.00-127.00   0.50    2.00    -- -106.00 -45.00 150.00   96
 21  \w     39.00  64.00   0.50    2.00    --  106.24-126.00-120.00   50
 22  \w     34.00  59.00   0.50    2.00    --  106.24 -61.00   0.00   50
 23  \w     40.00  66.00   0.50    2.00    --  106.24 -61.00 -30.00   52
 24  \w     37.00  99.00   0.50    2.00    --  106.24 -95.00 120.00  124
 25  \w     48.00 111.00   0.50    2.00    --  106.24-126.00   0.00  126
 26  \w    126.00 170.00   0.50    2.00    --  106.24  30.00 -90.00   88
 27  \w     55.00 104.00   0.50    2.00    --  106.24 -95.00 150.00   98
 28  \w     36.00 101.00   0.50    2.00    --  106.24-126.00  90.00  130
 29  \w     95.00 170.00   0.50    2.00    --  106.24  45.00-180.00  150
 30  \w     36.00 109.00   0.50    2.00    --  106.24-126.00  60.00  146
 31  \w     88.00 113.00   0.50    2.00    --  106.24-126.00-120.00   50
 32  \w     34.00  60.00   0.50    2.00    --  106.24 -61.00  60.00   52
 33  \w     98.00 176.00   0.50    2.00    --  106.24  45.00 150.00  156
 34  \w     40.00  65.00   0.50    2.00    --  106.24 -61.00-120.00   50
;
_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      0.0371510000
_diffrn_orient_matrix_UB_12      0.0329357000
_diffrn_orient_matrix_UB_13      -0.0484179000
_diffrn_orient_matrix_UB_21      -0.0134002000
_diffrn_orient_matrix_UB_22      0.1655965000
_diffrn_orient_matrix_UB_23      -0.0034626000
_diffrn_orient_matrix_UB_31      0.0309031000
_diffrn_orient_matrix_UB_32      0.0321550000
_diffrn_orient_matrix_UB_33      0.0673846000
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.997
_diffrn_reflns_theta_max         66.997
_diffrn_reflns_theta_min         2.877
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98929
_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    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0488P)^2^+2.0156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3876
_reflns_number_total             4572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima_2me_auto
_cod_original_cell_volume        5124.01(12)
_cod_database_code               7248428
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O N C H'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.969
_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), C18(H18), C33(H33), C37(H37), C14(H14), C34(H34), C35(H35),
 C22(H22), C24(H24), C17(H17), C15(H15), C29(H29), C36(H36), C23(H23), C16(H16),
  C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              62063
_shelx_hkl_checksum              91977
_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 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.949