1-Aminopyridinium Ylides as Monodentate Directing Groups for sp<sup>3</sup> C-H Bond Functionalization.
Le, Ky Khac Anh; Nguyen, Hanh; Daugulis, Olafs; Journal of the American Chemical Society 141 (2019) 14728–14735; doi:10.1021/jacs.9b06643

data_4127619
_publ_section_title
;
 1-Aminopyridinium Ylides as Monodentate Directing Groups for
 sp<sup>3</sup> C-H Bond Functionalization.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14728
_journal_page_last               14735
_journal_paper_doi               10.1021/jacs.9b06643
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C67 H104 N12 O16 Pd4'
_chemical_formula_weight         1759.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.0110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.7232(4)
_cell_length_b                   16.4364(4)
_cell_length_c                   15.5875(4)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      2.87
_cell_volume                     3978.60(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.611
_diffrn_reflns_theta_max         66.611
_diffrn_reflns_theta_min         3.916
_exptl_absorpt_coefficient_mu    7.733
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5370
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1804
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+5.3450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3379
_reflns_number_total             3520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06643_si_001.cif
_cod_data_source_block           XW81
_cod_database_code               4127619
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.411
_shelx_estimated_absorpt_t_max   0.801
_shelx_res_checksum              21454
_shelx_hkl_checksum              2561