Coordination Effect Enabled Palladium-Catalyzed Regioselective O-Alkylation of 2-Pyridones
Lu, Zhiqiang; li, yanzhi; ru, yi; yang, shujian; hao, chu; zuo, mengke; jiao, rongkai; Wu, Weilong; Zhou, Yan; Yao, Hui; huang, nianyu; Fu, Yuqin; Chemical Communications  (2022) –; doi:10.1039/D1CC06110K

data_7129451
_publ_section_title
;
 Coordination Effect Enabled Palladium-Catalyzed Regioselective
 O-Alkylation of 2-Pyridones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06110K
_journal_year                    2022
_chemical_formula_moiety         'C21 H18 N2 O'
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_name_systematic        zqlu3i-7
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.494(3)
_cell_angle_beta                 94.001(3)
_cell_angle_gamma                110.869(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2919(3)
_cell_length_b                   8.7725(4)
_cell_length_c                   13.1099(5)
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9360
_cell_measurement_theta_min      4.1710
_cell_volume                     862.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_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    -68.00  -3.00   1.00    8.66    --  -13.64 126.00  86.76   65
  2  \w    -52.00  32.00   1.00    8.66    --   15.05 -57.00-120.00   84
  3  \w     -2.00  82.00   1.00    8.66    --   15.05  57.00  60.00   84
  4  \w    -54.00  34.00   1.00    8.66    --   15.05 -38.00 150.00   88
  5  \w     -4.00  65.00   1.00    8.66    --   15.05-118.00 -31.00   69
  6  \w    -12.00  83.00   1.00    8.66    --   15.05  77.00 150.00   95
  7  \w     -4.00  84.00   1.00    8.66    --   15.05  38.00 -30.00   88
  8  \w    -20.00  54.00   1.00    8.66    --   15.05 -99.00  60.00   74
  9  \w    -54.00  84.00   1.00    8.66    --   15.05   0.00 -90.00  138
 10  \w    -20.00  25.00   1.00    8.66    --  -13.64 -99.00-180.00   45
 11  \w    -64.00   3.00   1.00    8.66    --  -13.64 119.00 139.12   67
 12  \w    -20.00  25.00   1.00    8.66    --  -13.64 -99.00 -90.00   45
 13  \w    -20.00  52.00   1.00    8.66    --   15.05 -99.00-120.00   72
 14  \w      5.00  71.00   1.00    8.66    --   15.05-129.00  37.36   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0227378000
_diffrn_orient_matrix_UB_12      0.0108222000
_diffrn_orient_matrix_UB_13      0.0548694000
_diffrn_orient_matrix_UB_21      -0.0657463000
_diffrn_orient_matrix_UB_22      0.0327013000
_diffrn_orient_matrix_UB_23      0.0100045000
_diffrn_orient_matrix_UB_31      -0.0611901000
_diffrn_orient_matrix_UB_32      -0.0822231000
_diffrn_orient_matrix_UB_33      -0.0033652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20397
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.466
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_preparation
'obtained by slow evaporation of their ether acetate/PE mixed solutions'
_exptl_crystal_recrystallization_method
'A crystal with approximate dimensions of 0.18*0.18*0.18mm^3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0614P)^2^+0.1932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3113
_reflns_number_total             3916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06110k2.cif
_cod_data_source_block           lzq20210801-1
_cod_original_cell_volume        862.81(6)
_cod_database_code               7129451
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              92271
_olex2_date_sample_data_collection 2021-08-01
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.624