Flexible C2-Symmetric Bis-Sulfoxides as Ligands in Enantioselective 1,4-Addition of Boronic Acids to Electron-Deficient Alkenes
Noureddine Khiar; Álvaro Salvador; Victoria Valdivia; Ahmed Chelouan; Ana Alcudia; Eleuterio Álvarez; Inmaculada Fernández; Journal of Organic Chemistry 78 (2013) 6510–6521; doi:10.1021/jo400700m

data_4028393
_publ_section_title
;
 Flexible C2-Symmetric Bis-Sulfoxides as Ligands in Enantioselective
 1,4-Addition of Boronic Acids to Electron-Deficient Alkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6510
_journal_page_last               6521
_journal_paper_doi               10.1021/jo400700m
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 Fe2 O2 S2'
_chemical_formula_sum            'C22 H22 Fe2 O2 S2'
_chemical_formula_weight         494.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   5.8114(5)
_cell_length_b                   10.6834(9)
_cell_length_c                   32.091(3)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.29
_cell_volume                     1992.4(3)
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            39414
_diffrn_reflns_theta_full        30.46
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         1.27
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.682
_exptl_absorpt_correction_T_max  0.9058
_exptl_absorpt_correction_T_min  0.5183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
program SADABS, Bruker (2001).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0305P)^2^+0.3423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0584
_reflns_number_gt                5673
_reflns_number_total             6058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400700m_si_002.cif
_cod_data_source_block           11
_cod_database_code               4028393