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_7129450
_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         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.24
_chemical_name_systematic        3b-9
_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     dual
_audit_creation_date             2021-07-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.547(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4761(3)
_cell_length_b                   18.2940(7)
_cell_length_c                   8.6517(4)
_cell_measurement_reflns_used    8194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4040
_cell_measurement_theta_min      3.8280
_cell_volume                     1115.08(9)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (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 0.998
_diffrn_measured_fraction_theta_max 0.940
_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    -81.00   3.00   1.00   10.07    --  -13.49 -57.00 -30.00   84
  2  \w    -83.00   5.00   1.00   10.07    --  -13.49 -38.00-120.00   88
  3  \w    -81.00   3.00   1.00   10.07    --  -13.49 -57.00-180.00   84
  4  \w    -20.00  25.00   1.00   10.07    --  -13.49 -99.00  90.00   45
  5  \w     -4.00  84.00   1.00   10.07    --   14.89  38.00 120.00   88
  6  \w    -20.00  54.00   1.00   10.07    --   14.89 -99.00-180.00   74
  7  \w    -54.00  84.00   1.00   10.07    --   14.89   0.00-120.00  138
  8  \w    -20.00  54.00   1.00   10.07    --   14.89 -99.00  60.00   74
  9  \w     -7.00  62.00   1.00   10.07    --   14.89-114.00 -64.62   69
 10  \w    -64.00 -18.00   1.00   10.07    --  -13.49 119.00 175.20   46
 11  \w    -86.00 -35.00   1.00   10.07    --  -13.49-178.00  30.00   51
 12  \w    -20.00  25.00   1.00   10.07    --  -13.49 -99.00-180.00   45
 13  \w     35.00  87.00   1.00   10.07    --   14.89 178.00 -30.00   52
 14  \w    -20.00  54.00   1.00   10.07    --   14.89 -99.00 120.00   74
 15  \w     -1.00  67.00   1.00   10.07    --   14.89-122.00  47.56   68
;
_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      -0.0453169000
_diffrn_orient_matrix_UB_12      0.0335599000
_diffrn_orient_matrix_UB_13      0.0048390000
_diffrn_orient_matrix_UB_21      0.0716810000
_diffrn_orient_matrix_UB_22      0.0077680000
_diffrn_orient_matrix_UB_23      0.0759119000
_diffrn_orient_matrix_UB_31      0.0542343000
_diffrn_orient_matrix_UB_32      0.0177834000
_diffrn_orient_matrix_UB_33      -0.0422653000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70889
_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 blackish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       needle
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0363P)^2^+0.4329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2168
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06110k2.cif
_cod_data_source_block           lzq20210731-1
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.8(C13 H10 N2 O2)'
_cod_original_formula_units_Z            5
_cod_database_code               7129450
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.992
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C2(H2), C1(H1A), C12(H12), C10(H10), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              34043
_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.651