Convergent, asymmetric synthesis of vicinal amino alcohols via Rh-catalyzed addition of α-amido trifluoroborates to carbonyls
Buesking, Andrew W.; Ellman, Jonathan A.; Chemical Science 5 (2014) 1983–; doi:10.1039/c4sc00084f

data_1514294
_publ_section_title
;
 Convergent, asymmetric synthesis of vicinal amino alcohols via
 Rh-catalyzed addition of \a-amido trifluoroborates to carbonyls
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1983
_journal_paper_doi               10.1039/c4sc00084f
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 F3 N O2 S'
_chemical_formula_sum            'C19 H22 F3 N O2 S'
_chemical_formula_weight         385.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-26
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.621(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7359(2)
_cell_length_b                   17.0050(4)
_cell_length_c                   9.7453(7)
_cell_measurement_reflns_used    11853
_cell_measurement_temperature    93
_cell_measurement_theta_max      65.0
_cell_measurement_theta_min      2.6
_cell_volume                     927.58(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 180.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 180.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 220.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 50.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 125.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 55.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 225.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 300.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 250.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 320.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 110.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 150.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 75.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 350.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 0.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 275.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 25.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 175.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 0.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 325.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: -48.0000 - 132.0000
         Image width: 2.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 165.0000
                 XTD: 42.0000
              2theta: 42.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 275.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 100.0000
                 XTD: 42.0000
              2theta: 90.0000
scan:
    Number of images: 90
               Slice: 0.0000 - 180.0000
         Image width: 2.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: 200.0000
                 XTD: 42.0000
              2theta: 90.0000
;
_diffrn_measurement_device
;
AFC11 (Left): Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_measurement_specimen_support Unknown
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.075889
_diffrn_orient_matrix_UB_12      -0.021793
_diffrn_orient_matrix_UB_13      -0.094516
_diffrn_orient_matrix_UB_21      -0.160790
_diffrn_orient_matrix_UB_22      0.004369
_diffrn_orient_matrix_UB_23      0.023396
_diffrn_orient_matrix_UB_31      -0.017474
_diffrn_orient_matrix_UB_32      0.054444
_diffrn_orient_matrix_UB_33      -0.039710
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26893
_diffrn_reflns_theta_full        65.02
_diffrn_reflns_theta_max         65.02
_diffrn_reflns_theta_min         4.65
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R (1998) Private Communication'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(16)
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0492P)^2^+0.0314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                2923
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00084f2.cif
_cod_data_source_block           00713074
_cod_database_code               1514294
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 N1-H1A
 0.89 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C13(H13), C5(H5), C11(H11), C14(H14), C2(H2), C15(H15),
 C4(H4), C1(H1B)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;