Matching the chirality of monodentate N-heterocyclic carbene ligands: a case study on well-defined palladium complexes for the asymmetric alpha-arylation of amides.
Luan, Xinjun; Mariz, Ronaldo; Robert, Carine; Gatti, Michele; Blumentritt, Sascha; Linden, Anthony; Dorta, Reto; Organic letters 10 (2008) 5569–5572; doi:10.1021/ol8021808

data_1504949
_publ_section_title
;
 Matching the chirality of monodentate N-heterocyclic carbene ligands: a
 case study on well-defined palladium complexes for the asymmetric
 alpha-arylation of amides.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5569
_journal_page_last               5572
_journal_paper_doi               10.1021/ol8021808
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C50 H47 Cl N2 Pd, C6 H14'
_chemical_formula_sum            'C56 H61 Cl N2 Pd'
_chemical_formula_weight         903.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             08-07-22
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.1693(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.3227(2)
_cell_length_b                   15.8780(3)
_cell_length_c                   13.5239(2)
_cell_measurement_reflns_used    60088
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     2432.67(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF94 (Beurskens et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            57893
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack & Bernardinelli (2000)'
_refine_ls_abs_structure_Flack   -0.039(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         11018
_refine_ls_number_restraints     331
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.4165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                9757
_reflns_number_total             11020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol8021808_si_001.cif
_cod_data_source_block           DT0816
_cod_database_code               1504949