Diastereoselective Addition of Enantiopure Lithium tert-Butylsulfinylferrocene to Imines
Guillaume Grach; Jana Sopkova-de Oliveira Santos; Jean-François Lohier; Ljubica Mojovic; Nelly Plé; Alain Turck; Vincent Reboul; Patrick Metzner; Journal of Organic Chemistry 71 (2006) 9572–9579; doi:10.1021/jo061360t

data_4022172
_publ_contact_author_address
;     Centre d'\'Etudes et la Recherche sur le Medicament de Normandie (CERMN)
      Universit\'e de Caen
      5 rue Vaub\'enard
      14032 Caen
      France
;
_publ_contact_author_email       jana.sopkova@unicaen.fr
_publ_contact_author_fax         '332 31 93 11 88'
_publ_contact_author_name        'Sopkov\'a-de Oliveira Santos, Jana'
_publ_contact_author_phone       '332 31 56 59 10'
_publ_section_title
;
 Diastereoselective Addition of Enantiopure Lithium
 tert-Butylsulfinylferrocene to Imines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9572
_journal_page_last               9579
_journal_paper_doi               10.1021/jo061360t
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        synthetised
_chemical_formula_moiety         'C28 H37 Fe N O3 S2'
_chemical_formula_sum            'C28 H37 Fe N O3 S2'
_chemical_formula_weight         555.56
_chemical_melting_point          426.15
_chemical_name_systematic
;
 (S~Fc~,S~S~)-2-(N-tosyl-1-amino-2-cyclohexyl)-1-tert-butylsulfinylferrocene
;
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                   11.8067(4)
_cell_length_b                   11.8067(4)
_cell_length_c                   19.3721(7)
_cell_measurement_reflns_used    18377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      43.05
_cell_measurement_theta_min      1.72
_cell_volume                     2700.43(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            115827
_diffrn_reflns_theta_full        43.05
_diffrn_reflns_theta_max         43.05
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack (1983), 8160 Friedel pairs'
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         18377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.0026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0616
_reflns_number_gt                15879
_reflns_number_total             18377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061360tsi20060630_084035.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '153\%C' was changed to '426.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022172