Highly Enantioselective Transfer Hydrogenation of Polar Double Bonds by Macrocyclic Iron(II)/(NH)2P2Catalysts
Bigler, Raphael; Mezzetti, Antonio; Organic Process Research & Development 20 (2016) 253–; doi:10.1021/acs.oprd.5b00391

data_1542333
_publ_section_title
;
 Highly Enantioselective Transfer Hydrogenation of Polar Double Bonds by
 Macrocyclic Iron(II)/(NH)2P2Catalysts
;
_journal_issue                   2
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              253
_journal_paper_doi               10.1021/acs.oprd.5b00391
_journal_volume                  20
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C32 H32 O6 P2'
_chemical_formula_sum            'C32 H32 O6 P2'
_chemical_formula_weight         574.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.212(3)
_cell_angle_beta                 98.226(3)
_cell_angle_gamma                96.026(3)
_cell_formula_units_Z            1
_cell_length_a                   8.4358(4)
_cell_length_b                   8.6021(4)
_cell_length_c                   9.8323(4)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.47
_cell_volume                     677.20(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31764
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         2.170
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 2574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7614
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0577P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6277
_reflns_number_total             7614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op5b00391_si_002.cif
_cod_data_source_block           Compound4
_cod_depositor_comments
'Adding full bibliography for 1542332--1542333.cif.'
_cod_database_code               1542333
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.957
_shelx_res_checksum              55122
_shelx_hkl_checksum              61209