Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines.
Maji, Modhu Sudan; Fröhlich, Roland; Studer, Armido; Organic letters 10 (2008) 1847–1850; doi:10.1021/ol800478q

data_1504641
_publ_section_title
;
 Desymmetrization of metallated cyclohexadienes with chiral
 N-tert-butanesulfinyl imines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1847
_journal_page_last               1850
_journal_paper_doi               10.1021/ol800478q
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H23 N O S'
_chemical_formula_weight         289.42
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   'at N3 from difmap, others geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.377(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5120(1)
_cell_length_b                   5.5194(1)
_cell_length_c                   14.7817(1)
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1588.15(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f 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  0.050
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11405
_diffrn_reflns_theta_full        68.40
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_min         4.54
_exptl_absorpt_coefficient_mu    1.761
_exptl_absorpt_correction_T_max  0.8867
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+1.0762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                2122
_reflns_number_total             2232
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800478q-file004.cif
_cod_data_source_block           stu4200
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1504641