Stereochemical Requirements of Oxidative Cyclizations in Extended Iterative Organoiron-Mediated Routes to Alkaloids
G. Richard Stephenson; Caroline Roe; Christopher E. Anson; Journal of Organic Chemistry 77 (2012) 9684–9692; doi:10.1021/jo301617f

data_4027633
_publ_section_title
;
 Stereochemical Requirements of Oxidative Cyclizations in Extended
 Iterative Organoiron-Mediated Routes to Alkaloids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9684
_journal_page_last               9692
_journal_paper_doi               10.1021/jo301617f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C36.5 H41.5 Fe O7 Si'
_chemical_formula_weight         676.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.923(4)
_cell_angle_beta                 84.618(4)
_cell_angle_gamma                78.411(4)
_cell_formula_units_Z            4
_cell_length_a                   12.145(3)
_cell_length_b                   16.906(4)
_cell_length_c                   18.104(4)
_cell_measurement_reflns_used    4453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.38
_cell_volume                     3396.8(14)
_computing_cell_refinement       'SMART-NT 5.6 (Bruker AXS Inc., 2005)'
_computing_data_collection       'SMART-NT 5.6 (Bruker AXS Inc., 2005)'
_computing_data_reduction        'SAINT+ 6.45 (Bruker AXS Inc., 2003)'
_computing_molecular_graphics    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_publication_material  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_refinement  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_solution    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18747
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2005)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1426
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_refine_diff_density_max         2.804
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     838
_refine_ls_number_reflns         12286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0734P)^2^+5.0734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                9176
_reflns_number_total             12286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301617f_si_002.cif
_cod_data_source_block           crc329
_cod_original_cell_volume        3396.9(12)
_cod_original_formula_sum        'C36.50 H41.50 Fe O7 Si'
_cod_database_code               4027633