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_4127059
_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_formula_moiety         'C78 H64 O2 P4 Rh'
_chemical_formula_sum            'C78 H64 O2 P4 Rh'
_chemical_formula_weight         1260.18
_chemical_name_common            compound9
_chemical_name_systematic        compound9
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.862(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6304(6)
_cell_length_b                   18.1797(6)
_cell_length_c                   18.7127(6)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.49
_cell_volume                     5954.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.9811
_diffrn_measured_fraction_theta_max 0.9696
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26276
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4055
_exptl_crystal_description       prism
_exptl_crystal_F_000             2610.0971
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.3854
_refine_diff_density_min         -0.8013
_refine_diff_density_rms         0.1288
_refine_ls_d_res_high            0.8290
_refine_ls_d_res_low             12.6094
_refine_ls_goodness_of_fit_ref   1.0342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0342
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+11.7921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3986
_reflns_number_total             5321
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja7b11964_si_004.cif
_cod_data_source_block           compound9
_cod_database_code               4127059
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C27(H27a,H27b,H27c)
;
_olex2_submission_special_instructions 'No special instructions were received'