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_7248425
_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 O3, C H2 Cl2'
_chemical_formula_sum            'C32 H28 Cl2 N4 O3'
_chemical_formula_weight         587.48
_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
_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                 91.4501(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.20645(12)
_cell_length_b                   9.47536(7)
_cell_length_c                   21.65599(18)
_cell_measurement_reflns_used    27491
_cell_measurement_temperature    180.00(16)
_cell_measurement_theta_max      77.4490
_cell_measurement_theta_min      3.0900
_cell_volume                     2914.21(4)
_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      180.00(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     67.00 106.00   0.50    0.25    --   50.05-147.00 116.00   78
  2  \w    100.00 125.00   0.50    1.00    --  105.51-147.00 116.00   50
  3  \w     74.00 107.00   0.50    1.00    --  105.51-126.00   0.00   66
  4  \w     28.00  90.00   0.50    0.25    --   50.05-125.00 -77.00  124
  5  \w     50.00  75.00   0.50    1.00    --  105.51-125.00 -77.00   50
  6  \w     39.00  81.00   0.50    1.00    --  105.51 -99.00 -60.00   84
  7  \w     36.00  66.00   0.50    1.00    --  105.51-126.00   0.00   60
  8  \w     60.00 105.00   0.50    1.00    --  105.51 -99.00 150.00   90
  9  \w     76.00 102.00   0.50    1.00    --  105.51 -99.00 120.00   52
 10  \w     37.00  62.00   0.50    1.00    --  105.51 -57.00 -30.00   50
 11  \w     34.00  60.00   0.50    1.00    --  105.51 -57.00-180.00   52
 12  \w     35.00  65.00   0.50    1.00    --  105.51 -57.00-120.00   60
 13  \w     39.00  65.00   0.50    1.00    --  105.51 -57.00 -60.00   52
 14  \w     38.00  65.00   0.50    1.00    --  105.51 -57.00 120.00   54
 15  \w     34.00  63.00   0.50    1.00    --  105.51 -57.00 150.00   58
 16  \w     61.00 112.00   0.50    1.00    --  105.51   0.00   0.00  102
 17  \w     64.00 111.00   0.50    1.00    --  105.51   0.00  60.00   94
 18  \w     59.00 108.00   0.50    1.00    --  105.51   0.00 150.00   98
 19  \w    135.00 161.00   0.50    1.00    --  105.51  57.00 -90.00   52
 20  \w     96.00 121.00   0.50    1.00    --  105.51  57.00 -90.00   50
 21  \w    123.00 156.00   0.50    1.00    --  105.51 125.00  -0.00   66
 22  \w     75.00 120.00   0.50    0.25    --   50.05 126.00-120.00   90
 23  \w    108.00 141.00   0.50    1.00    --  105.51 147.00 165.00   66
 24  \w     69.00  98.00   0.50    1.00    --  105.51 147.00 165.00   58
 25  \w     58.00  90.00   0.50    0.25    --   50.05 147.00 165.00   64
 26  \w     94.00 120.00   0.50    0.25    --   50.05 147.00 165.00   52
 27  \w    -62.00 -37.00   0.50    1.00    -- -105.51  57.00  30.00   50
 28  \w    -64.00 -38.00   0.50    1.00    -- -105.51  57.00  60.00   52
 29  \w    -63.00 -34.00   0.50    1.00    -- -105.51  57.00 120.00   58
 30  \w    -97.00 -45.00   0.50    0.25    --  -50.05   0.00-150.00  104
 31  \w    -63.00 -35.00   0.50    1.00    -- -105.51  57.00-120.00   56
 32  \w    -60.00 -34.00   0.50    1.00    -- -105.51  57.00 -30.00   52
 33  \w   -154.00-102.00   0.50    1.00    -- -105.51   0.00 150.00  104
 34  \w   -108.00 -38.00   0.50    1.00    -- -105.51 108.00  76.52  140
 35  \w   -109.00 -83.00   0.50    1.00    -- -105.51 125.00  -0.00   52
 36  \w    -78.00 -42.00   0.50    1.00    -- -105.51 125.00  -0.00   72
 37  \w   -107.00 -65.00   0.50    1.00    -- -105.51 108.00 -25.10   84
 38  \w   -109.00 -77.00   0.50    1.00    -- -105.51 115.00 -94.72   64
 39  \w    -81.00 -20.00   0.50    0.25    --  -50.05 125.00  -0.00  122
 40  \w   -127.00 -65.00   0.50    1.00    -- -105.51 147.00 165.00  124
 41  \w   -108.00 -49.00   0.50    1.00    -- -105.51 108.00 163.15  118
 42  \w    -67.00 -41.00   0.50    0.25    --  -50.05 147.00 165.00   52
 43  \w   -174.00-100.00   0.50    1.00    -- -105.51 -38.00-120.00  148
 44  \w   -175.00-143.00   0.50    1.00    -- -105.51 -57.00   0.00   64
 45  \w   -128.00 -96.00   0.50    1.00    -- -105.51 -57.00   0.00   64
 46  \w   -121.00 -33.00   0.50    0.25    --  -50.05 -77.00   0.00  176
 47  \w    -80.00 -45.00   0.50    0.25    --  -50.05 -38.00-150.00   70
 48  \w   -120.00 -87.00   0.50    0.25    --  -50.05 -38.00-150.00   66
 49  \w   -119.00 -94.00   0.50    0.25    --  -50.05-125.00 -77.00   50
 50  \w   -102.00 -76.00   0.50    0.25    --  -50.05-126.00-150.00   52
 51  \w   -124.00 -95.00   0.50    1.00    -- -105.51-125.00 -77.00   58
 52  \w   -165.00 -96.00   0.50    1.00    -- -105.51-126.00   0.00  138
 53  \w   -137.00-112.00   0.50    1.00    -- -105.51-147.00 116.00   50
 54  \w    -92.00 -64.00   0.50    0.25    --  -50.05-147.00 116.00   56
;
_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      -0.0652665000
_diffrn_orient_matrix_UB_12      -0.0191157000
_diffrn_orient_matrix_UB_13      0.0551342000
_diffrn_orient_matrix_UB_21      -0.0860613000
_diffrn_orient_matrix_UB_22      -0.0042196000
_diffrn_orient_matrix_UB_23      -0.0446791000
_diffrn_orient_matrix_UB_31      0.0100183000
_diffrn_orient_matrix_UB_32      -0.1613900000
_diffrn_orient_matrix_UB_33      -0.0053590000
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40637
_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         3.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59932
_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    1.339
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.044
_refine_diff_density_max         1.518
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0788P)^2^+3.1531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4888
_reflns_number_total             5191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima_2ome_auto
_cod_database_code               7248425
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O N C H'
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.693
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22),
 C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              99376
_shelx_hkl_checksum              90029
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.568