[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_4133522
_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         'C16 H8 Br F5 N2 O Pd'
_chemical_formula_sum            'C16 H8 Br F5 N2 O Pd'
_chemical_formula_weight         525.57
_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'
_symmetry_Int_Tables_number      61
_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                   6.9050(2)
_cell_length_b                   20.1040(6)
_cell_length_c                   22.8460(6)
_cell_measurement_reflns_used    4681
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.6510
_cell_measurement_theta_min      2.7020
_cell_volume                     3171.44(16)
_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    '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 0.9996
_diffrn_measured_fraction_theta_max 0.8703
_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     45.00  79.00   1.00  107.41    --   -9.95 179.00 150.00   34
  2  \w     -7.00  91.00   1.00  107.41    --   11.82  19.00   0.00   98
  3  \w     50.00  77.00   1.00  107.41    --   11.82  19.00-150.00   27
;
_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      0.0067406000
_diffrn_orient_matrix_UB_12      0.0333628000
_diffrn_orient_matrix_UB_13      0.0098775000
_diffrn_orient_matrix_UB_21      -0.1015208000
_diffrn_orient_matrix_UB_22      0.0006441000
_diffrn_orient_matrix_UB_23      0.0046718000
_diffrn_orient_matrix_UB_31      0.0140291000
_diffrn_orient_matrix_UB_32      -0.0114456000
_diffrn_orient_matrix_UB_33      0.0290697000
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12947
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.77
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.753
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.635
_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    2.2013
_exptl_crystal_description       prism
_exptl_crystal_F_000             2007.1242
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.9010
_refine_diff_density_min         -0.7301
_refine_diff_density_rms         0.1762
_refine_ls_d_res_high            0.7157
_refine_ls_d_res_low             10.0520
_refine_ls_goodness_of_fit_ref   1.0365
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0365
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0380P)^2^+0.9294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2799
_reflns_number_total             3944
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja8b10680_si_002.cif
_cod_data_source_block           vs97_complex_1
_cod_database_code               4133522
_chemical_oxdiff_formula         'C16 H8 Br F5 N2 O Pd'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.814