Rational ligand design for the arylation of hindered primary amines guided by reaction progress kinetic analysis.
Ruiz-Castillo, Paula; Blackmond, Donna G.; Buchwald, Stephen L.; Journal of the American Chemical Society 137 (2015) 3085–3092; doi:10.1021/ja512903g

data_4123463
_publ_section_title
;
 Rational ligand design for the arylation of hindered primary amines
 guided by reaction progress kinetic analysis.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3085
_journal_page_last               3092
_journal_paper_doi               10.1021/ja512903g
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C35 H33 Br N3 P Pd'
_chemical_formula_weight         712.92
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2012
_cell_angle_alpha                97.5770(10)
_cell_angle_beta                 109.4170(10)
_cell_angle_gamma                113.6010(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1917(7)
_cell_length_b                   11.9481(8)
_cell_length_c                   14.9831(10)
_cell_measurement_reflns_used    9566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.62
_cell_measurement_theta_min      2.41
_cell_volume                     1500.88(18)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            66034
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_min         1.514
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         9570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0180
_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^)+(0.0222P)^2^+0.8526P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9148
_reflns_number_total             9570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja512903g_si_001.cif
_cod_data_source_block           x14001
_cod_depositor_comments
'Adding full bibliography for 4123462--4123463.cif.'
_cod_database_code               4123463
_shelx_estimated_absorpt_t_min   0.554
_shelx_estimated_absorpt_t_max   0.675
_shelxl_version_number           2012-9
_shelx_res_checksum              92831
_shelx_hkl_checksum              65192