Efficient Pd0-Catalyzed Asymmetric Activation of Primary and Secondary C–H Bonds Enabled by Modular Binepine Ligands and Carbonate Bases
Holstein, Philipp M.; Vogler, Maria; Larini, Paolo; Pilet, Guillaume; Clot, Eric; Baudoin, Olivier; ACS Catalysis 5 (2015) 4300–; doi:10.1021/acscatal.5b00898

data_4513219
_publ_section_title
;
 Efficient Pd0-Catalyzed Asymmetric Activation of Primary and Secondary
 C--H Bonds Enabled by Modular Binepine Ligands and Carbonate Bases
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4300
_journal_paper_doi               10.1021/acscatal.5b00898
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C43 H38 N1 O3.50 P1 Pd1 S1'
_chemical_formula_sum            'C43 H38 N O3.5 P Pd S'
_chemical_formula_weight         794.22
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   14.5165(2)
_cell_length_b                   14.5165(2)
_cell_length_c                   37.1387(10)
_cell_measurement_reflns_used    13517
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     7826.2(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            40357
_diffrn_reflns_theta_full        25.305
_diffrn_reflns_theta_max         29.425
_diffrn_reflns_theta_min         2.806
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.67
_refine_ls_abs_structure_details 'Flack (1983), 3891 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0811
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7582
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.0023044
_refine_ls_shift/su_mean         0.0000686
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 7.26 4.34 6.52 2.37 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0505
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0442
_reflns_limit_h_max              14
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              50
_reflns_limit_l_min              0
_reflns_number_gt                8295
_reflns_number_total             9712
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0465
_oxford_refine_ls_scale          0.6869(10)
_oxford_reflns_number_all        9690
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            cs5b00898_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4513215--4513219.cif.'
_cod_original_sg_symbol_H-M      'P 41 21 2 '
_cod_original_formula_sum        'C43 H38 N1 O3.50 P1 Pd1 S1'
_cod_database_code               4513219
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = O(49) TO C(53) 
END                                                                             
;