[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_4133524
_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         'C22 H16 F3 N3 O Pd'
_chemical_formula_sum            'C22 H16 F3 N3 O Pd'
_chemical_formula_weight         501.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8072(3)
_cell_length_b                   15.7255(6)
_cell_length_c                   32.2864(16)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.2700
_cell_measurement_theta_min      3.5930
_cell_volume                     3963.9(3)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 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 0.994
_diffrn_measured_fraction_theta_max 0.803
_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    -18.00  82.00   1.00   50.00    --   10.16  57.00 -90.00  100
;
_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      0.0033302000
_diffrn_orient_matrix_UB_12      -0.0437205000
_diffrn_orient_matrix_UB_13      -0.0054398000
_diffrn_orient_matrix_UB_21      -0.0120361000
_diffrn_orient_matrix_UB_22      -0.0111888000
_diffrn_orient_matrix_UB_23      0.0210745000
_diffrn_orient_matrix_UB_31      -0.0899086000
_diffrn_orient_matrix_UB_32      -0.0001062000
_diffrn_orient_matrix_UB_33      -0.0030393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9904
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.902
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.867
_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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       plate
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0281P)^2^+1.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2666
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10680_si_002.cif
_cod_data_source_block           vs944x_complex_10
_cod_database_code               4133524
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H16 F3 N3 O Pd'
_chemical_oxdiff_usercomment     'yellow plate'
_reflns_odcompleteness_completeness 98.79
_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 Aromatic/amide H refined with riding coordinates:
 C16(H16)
;
_shelx_res_checksum              50682
_shelx_hkl_checksum              46992
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.929