Palladium-Catalyzed Amination of Aromatic C-H Bonds with Oxime Esters
Yichen Tan; John F. Hartwig; Journal of the American Chemical Society 132 (2010) 3676–3677; doi:10.1021/ja100676r

data_4102097
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       dgray@illinois.edu
_publ_contact_author_fax         '1  217 244 8068'
_publ_contact_author_phone       '1  217 244 1708'
_publ_section_title
;
 Palladium-Catalyzed Amination of Aromatic C-H Bonds with Oxime Esters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3676
_journal_page_last               3677
_journal_paper_doi               10.1021/ja100676r
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C58 H80 F5 N O2 P2 Pd'
_chemical_formula_sum            'C58 H80 F5 N O2 P2 Pd'
_chemical_formula_weight         1086.57
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                85.975(3)
_cell_angle_beta                 73.270(2)
_cell_angle_gamma                84.930(2)
_cell_formula_units_Z            2
_cell_length_a                   13.5197(17)
_cell_length_b                   14.6840(18)
_cell_length_c                   17.417(2)
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      19.51
_cell_measurement_theta_min      2.18
_cell_volume                     3294.7(7)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  b33ff_2as_sqz
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32193
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.8743
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_id                b33ff_2as_sqz
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research). 
;
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_platon_squeeze_details
; 
Absorption correction was performed on the data prior to the squeeze 
routine using the formula C68H104F5NO2P2Pd, 2(C5H12) to calculate a Mu 
of 0.39mm-1.  The 187 e- squeezed from the model is approximately 
equivalent to two pentane molecules in the solvent accessible void, 
which is consistent with the initial dissordered model. 
;
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         12039
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                6145
_reflns_number_total             12039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100676r_si_002.cif
_cod_data_source_block           b32ff_2as_sqz
_cod_original_cell_volume        3294.8(7)
_cod_database_code               4102097