Promotion of a Ti-Mediated Mannich Reaction by a Proton Source.
Limanto, John; Yoshikawa, Naoki; Reamer, Robert A.; Tan, Lushi; Brunskill, Andrew; Reibarkh, Mikhail; The Journal of organic chemistry 81 (2016) 723–728; doi:10.1021/acs.joc.5b02452

data_4031832
_publ_section_title
;
 Promotion of a Ti-Mediated Mannich Reaction by a Proton Source.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              723
_journal_page_last               728
_journal_paper_doi               10.1021/acs.joc.5b02452
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H46 F I N2 O5 Si2'
_chemical_formula_sum            'C39 H46 F I N2 O5 Si2'
_chemical_formula_weight         824.86
_chemical_name_systematic
; 
(S)-3-((2R,5S)-5-(4-fluorophenyl)-2-((S)-((4-iodophenyl)amino)
(4-((trimethylsilyl)oxy) phenyl)methyl)-5-((trimethylsilyl)oxy)
pentanoyl)-4-phenyloxazolidin-2-one 
;
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                81.5151(14)
_cell_angle_beta                 89.5040(16)
_cell_angle_gamma                89.5445(14)
_cell_formula_units_Z            2
_cell_length_a                   5.7152(3)
_cell_length_b                   15.4683(7)
_cell_length_c                   22.7213(10)
_cell_measurement_reflns_used    9323
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      5.22
_cell_volume                     1986.56(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37418
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.692
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    7.303
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.7528
_exptl_transmission_factor_min   0.5563
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.006(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     944
_refine_ls_number_reflns         13490
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+4.8700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                13261
_reflns_number_total             13490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02452_si_002.cif
_cod_data_source_block           mdk097
_cod_database_code               4031832
_shelx_estimated_absorpt_t_min   0.474
_shelx_estimated_absorpt_t_max   0.759
_shelxl_version_number           2014-3
_shelx_res_checksum              63164
_shelx_hkl_checksum              39972