Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products
Robert J. Comito; Fernanda G. Finelli; David W. C. MacMillan; Journal of the American Chemical Society 135 (2013) 9358–9361; doi:10.1021/ja4047312

data_4119999
_publ_section_title
;
 Enantioselective Intramolecular Aldehyde \a-Alkylation with Simple
 Olefins: Direct Access to Homo-Ene Products
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9358
_journal_page_last               9361
_journal_paper_doi               10.1021/ja4047312
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C36 H24 Fe N6, 3(C2 F6 N O4 S2), 2(C2 H3 N)'
_chemical_formula_sum            'C46 H30 F18 Fe N11 O12 S6'
_chemical_formula_weight         1519.02
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 104.2570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3520(5)
_cell_length_b                   15.4353(4)
_cell_length_c                   19.6446(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      59.80
_cell_measurement_theta_min      3.64
_cell_volume                     5981.1(2)
_computing_cell_refinement       'BRUKER, APEX II SOFTWARE SUITE'
_computing_data_collection       'BRUKER, APEX II SOFTWARE SUITE'
_computing_data_reduction        'BRUKER, APEX II SOFTWARE SUITE'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Giacovazzo, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28724
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.39
_diffrn_reflns_theta_min         3.64
_diffrn_standards_interval_count 0
_exptl_absorpt_coefficient_mu    5.115
_exptl_absorpt_correction_T_max  0.6287
_exptl_absorpt_correction_T_min  0.4949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       block
_exptl_crystal_F_000             3052
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
The data was treated with the platon/squeeze
routine to account for a further 3 molecules
of acet0nitrile present within the unit cell.
;
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.752
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.758
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0498
_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 w=1/[\s^2^(Fo^2^)+(0.1225P)^2^+44.4362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                4562
_reflns_number_total             5145
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja4047312_si_001.cif
_cod_data_source_block           rco1
_cod_database_code               4119999