Palladium(0)-catalyzed asymmetric C(sp(3))-H arylation using a chiral binol-derived phosphate and an achiral ligand.
Yang, Lei; Melot, Romain; Neuburger, Markus; Baudoin, Olivier; Chemical science 8 (2017) 1344–1349; doi:10.1039/c6sc04006c

data_1544316
_publ_section_title
;
 Palladium(0)-catalyzed asymmetric C(sp(3))-H arylation using a chiral
 binol-derived phosphate and an achiral ligand.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              1344
_journal_page_last               1349
_journal_paper_doi               10.1039/c6sc04006c
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 Fe1 N1 O3'
_chemical_formula_sum            'C22 H21 Fe N O3'
_chemical_formula_weight         403.26
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2016-06-20 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.7138(5)
_cell_length_b                   9.7138(5)
_cell_length_c                   33.882(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    123
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2768.7(3)
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_collection       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie 1996)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            17736
_diffrn_reflns_theta_full        52.800
_diffrn_reflns_theta_max         57.346
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_source_voltage           70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.640
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1259.993
_exptl_crystal_recrystallization_method
; 
 
;
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.39
_refine_ls_abs_structure_details 'Flack (1983), 1492 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.024(6)
_refine_ls_extinction_coef       21.1(17)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0750
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.0003095
_refine_ls_shift/su_mean         0.0000331
_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: 
 0.455 0.276 0.108 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0444
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0402
_reflns_limit_h_max              5
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              -41
_reflns_number_gt                4478
_reflns_number_total             5109
_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   0.0369
_oxford_refine_ls_scale          0.3426(5)
_oxford_reflns_number_all        5109
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_cod_data_source_file            c6sc04006c2.cif
_cod_data_source_block           1
_cod_depositor_comments
;Adding full bibliography for 1544315--1544316.cif.

 Adding full bibliography for 1544315--1544316.cif.
;
_cod_original_formula_sum        'C22 H21 Fe1 N1 O3'
_cod_database_code               1544316