Iron Catalyzed Highly Enantioselective Epoxidation of Cyclic Aliphatic Enones with Aqueous H2O2.
Cussó, Olaf; Cianfanelli, Marco; Ribas, Xavi; Klein Gebbink, Robertus J. M.; Costas, Miquel; Journal of the American Chemical Society 138 (2016) 2732–2738; doi:10.1021/jacs.5b12681

data_4124919
_publ_section_title
;
 Iron Catalyzed Highly Enantioselective Epoxidation of Cyclic Aliphatic
 Enones with Aqueous H2O2.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2732
_journal_page_last               2738
_journal_paper_doi               10.1021/jacs.5b12681
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H49 F6 Fe N5 O6 S2 Si, C H2 Cl2'
_chemical_formula_sum            'C35 H51 Cl2 F6 Fe N5 O6 S2 Si'
_chemical_formula_weight         970.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.337(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2394(19)
_cell_length_b                   15.092(3)
_cell_length_c                   16.250(3)
_cell_measurement_reflns_used    4216
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.41
_cell_volume                     2247.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_unetI/netI     0.1348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.480
_diffrn_reflns_theta_min         2.412
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.612768
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       needle
_exptl_crystal_F_000             1006
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.016(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         10964
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0527P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                7284
_reflns_number_total             10964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12681_si_002.cif
_cod_data_source_block           bztipspdpfe
_cod_depositor_comments          'Adding full bibliography for 4124919.cif.'
_cod_database_code               4124919
_shelxl_version_number           2013-3
_shelx_res_checksum              48811
_shelx_hkl_checksum              96133