[2,2'-Bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine.
Salamanca, Vanesa; Toledo, Alberto; Albéniz, Ana C; Journal of the American Chemical Society 140 (2018) 17851–17856; doi:10.1021/jacs.8b10680

data_4133523
_publ_section_title
;
 [2,2'-Bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the
 Palladium-Mediated C-H Activation Step: Experimental Evidence in the
 Direct C-3 Arylation of Pyridine.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17851
_journal_page_last               17856
_journal_paper_doi               10.1021/jacs.8b10680
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C21 H12 F5 N3 O Pd, 2(H2 O)'
_chemical_formula_sum            'C21 H16 F5 N3 O3 Pd'
_chemical_formula_weight         559.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                71.425(5)
_cell_angle_beta                 83.843(4)
_cell_angle_gamma                75.990(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4795(4)
_cell_length_b                   12.5387(7)
_cell_length_c                   12.6596(6)
_cell_measurement_reflns_used    3625
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.3140
_cell_measurement_theta_min      3.6050
_cell_volume                     1091.35(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.8433
_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      9.00  35.00   1.00    5.44    --  -10.64  37.00  30.00   26
  2  \w    -75.00  12.00   1.00    5.44    --  -10.64 -57.00 150.00   87
  3  \w      1.00  27.00   1.00    5.44    --  -10.64 -99.00 -60.00   26
  4  \w    -39.00  63.00   1.00    5.44    --  -10.64  57.00 -60.00  102
  5  \w     63.00  89.00   1.00    5.44    --   12.20-178.00-150.00   26
  6  \w     34.00  99.00   1.00    5.44    --   12.20-178.00 150.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0246332000
_diffrn_orient_matrix_UB_12      0.0082169000
_diffrn_orient_matrix_UB_13      0.0530017000
_diffrn_orient_matrix_UB_21      -0.0205739000
_diffrn_orient_matrix_UB_22      -0.0554802000
_diffrn_orient_matrix_UB_23      0.0203114000
_diffrn_orient_matrix_UB_31      0.0923751000
_diffrn_orient_matrix_UB_32      -0.0244560000
_diffrn_orient_matrix_UB_33      0.0166056000
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9863
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.47
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.7034
_exptl_crystal_description       prism
_exptl_crystal_F_000             554.3847
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.135
_refine_diff_density_max         1.0119
_refine_diff_density_min         -0.7277
_refine_diff_density_rms         0.1447
_refine_ls_d_res_high            0.7224
_refine_ls_d_res_low             6.1404
_refine_ls_goodness_of_fit_ref   0.9654
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9654
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3947
_reflns_number_total             5123
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja8b10680_si_002.cif
_cod_data_source_block           vs984t_complex_7
_cod_database_code               4133523
_chemical_oxdiff_formula         'C21 H12 N3 F5 O Pd'
_chemical_oxdiff_usercomment     yellow
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H22,H23), O3(H24,H25)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C9(H9), C7(H7), C8(H8), C3(H3), C2(H2), C21(H21), C17(H17),
 C20(H20), C19(H19), C18(H18)
;
_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.671