Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups.
Chen, Xiao-Yang; Sorensen, Erik J.; Journal of the American Chemical Society 140 (2018) 2789–2792; doi:10.1021/jacs.8b00048

data_4132005
_publ_section_title
;
 Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes
 Using Orthanilic Acids as Transient Directing Groups.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2789
_journal_page_last               2792
_journal_paper_doi               10.1021/jacs.8b00048
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C32 H25 Cl2 F N O3 P Pd S'
_chemical_formula_weight         730.86
_chemical_name_common            XC4
_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
_cell_angle_alpha                90
_cell_angle_beta                 98.6077(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7112(5)
_cell_length_b                   14.8397(6)
_cell_length_c                   15.9385(6)
_cell_measurement_reflns_used    9747
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      40.3171
_cell_measurement_theta_min      2.8382
_cell_volume                     2972.6(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            118216
_diffrn_reflns_theta_full        39.38
_diffrn_reflns_theta_max         39.38
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'translucent pale yellow'
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.192
_refine_diff_density_max         1.480
_refine_diff_density_min         -0.619
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         17723
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+2.5718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                15393
_reflns_number_total             17723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b00048_si_002.cif
_cod_data_source_block           PDJXC4
_cod_database_code               4132005
_shelx_res_checksum              73669
_shelx_hkl_checksum              33130