Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.
Karmel, Caleb; Li, Bi-Jie; Hartwig, John F.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b11964

data_4127060
_publ_section_title
;
 Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the
 Synthesis of 1,4-Diols.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11964
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H25 N O5'
_chemical_formula_weight         335.39
_chemical_name_common            none
_chemical_name_systematic        Compound5t
_space_group.centring_type       primitive
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                88.767(2)
_cell_angle_beta                 87.077(2)
_cell_angle_gamma                88.171(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5555(3)
_cell_length_b                   7.2872(3)
_cell_length_c                   17.9836(7)
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      2.46
_cell_volume                     857.37(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5741
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.734
_diffrn_reflns_theta_min         2.461
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 2117 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5741
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.0464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                5196
_reflns_number_total             5741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11964_si_002.cif
_cod_data_source_block           Compound5t
_cod_database_code               4127060
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              9942
_shelx_hkl_checksum              20027