Iron(III)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of beta-keto esters and N-Boc oxindoles
Xin Gu; Yan Zhang; Zhen-Jiang Xu; Chi-Ming Che; Chem.Commun. 50 (2014) 7870–; doi:10.1039/C4CC01631A

data_7115268
_publ_section_title
;
 Iron(III)-salan complexes catalysed highly enantioselective fluorination
 and hydroxylation of beta-keto esters and N-Boc oxindoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              7870
_journal_paper_doi               10.1039/C4CC01631A
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H40 Br2 Cl Fe N2 O2'
_chemical_formula_weight         711.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9311(11)
_cell_length_b                   14.3912(16)
_cell_length_c                   22.008(2)
_cell_measurement_reflns_used    3333
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.234
_cell_measurement_theta_min      4.500
_cell_volume                     3145.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_sigmaI/netI    0.1156
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19032
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    3.134
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3306
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1452
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(10)
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         7117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0434
_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 
 [0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0338P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                4060
_reflns_number_total             7117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc01631a2.cif
_cod_data_source_block           cd201302
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7115268