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_7129452
_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         'C18 H12 Cl N O'
_chemical_formula_sum            'C18 H12 Cl N O'
_chemical_formula_weight         293.75
_chemical_name_systematic        3j-1
_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 1.2
(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                90
_cell_angle_beta                 115.115(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7326(5)
_cell_length_b                   16.1644(7)
_cell_length_c                   9.2583(5)
_cell_measurement_reflns_used    5622
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2230
_cell_measurement_theta_min      4.0120
_cell_volume                     1454.33(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.891
_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    -20.00  25.00   1.00    5.03    --  -13.49 -99.00 120.00   45
  2  \w    -20.00  25.00   1.00    5.03    --  -13.49 -99.00 -60.00   45
  3  \w    -30.00  54.00   1.00    5.03    --  -13.49  57.00 150.00   84
  4  \w    -20.00  54.00   1.00    5.03    --   14.89 -99.00 -90.00   74
  5  \w     -4.00  84.00   1.00    5.03    --   14.89  38.00 120.00   88
  6  \w    -57.00  44.00   1.00    5.03    --   14.89 -19.00 -60.00  101
  7  \w    -81.00 -56.00   1.00    5.03    --  -13.49 -77.00 -30.00   25
  8  \w    -30.00  54.00   1.00    5.03    --  -13.49  53.00  90.00   84
;
_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      -0.0447720000
_diffrn_orient_matrix_UB_12      0.0239996000
_diffrn_orient_matrix_UB_13      -0.0657129000
_diffrn_orient_matrix_UB_21      -0.0136162000
_diffrn_orient_matrix_UB_22      0.0263478000
_diffrn_orient_matrix_UB_23      0.0528727000
_diffrn_orient_matrix_UB_31      0.0560340000
_diffrn_orient_matrix_UB_32      0.0255545000
_diffrn_orient_matrix_UB_33      0.0071563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_min         3.278
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83386
_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 whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    2.596
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0461P)^2^+0.3883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2403
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06110k2.cif
_cod_data_source_block           lzq20210731-2
_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 Cl0.08 N O'
_cod_original_formula_weight         174.93
_cod_original_formula_moiety         '0.31(C18 H12 Cl N O)'
_cod_original_formula_units_Z            13
_cod_database_code               7129452
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C6(H6), C13(H13), C15(H15), C2(H2), C1(H1), C12(H12),
 C11(H11), C16(H16), C17(H17)
;
_shelx_res_checksum              53262
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.787