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_4031831
_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         'C33 H29 Br F I N2 O4'
_chemical_formula_sum            'C33 H29 Br F I N2 O4'
_chemical_formula_weight         743.39
_chemical_name_systematic
; 
(S)-3-((2R,5S)-2-((S)-(4-bromophenyl)((4-iodophenyl)amino)methyl)
-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one 
;
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.5700(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.3461(12)
_cell_length_b                   5.8463(2)
_cell_length_c                   34.0783(13)
_cell_measurement_reflns_used    9331
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.87
_cell_measurement_theta_min      2.84
_cell_volume                     6006.2(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            71975
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.952
_diffrn_reflns_theta_min         1.305
_diffrn_source                   'sealed-tube X-ray generator'
_exptl_absorpt_coefficient_mu    10.329
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2960
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
; 
 Flack x determined using 8341 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1600
_refine_ls_number_reflns         21405
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0170P)^2^+28.3814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                20127
_reflns_number_total             21405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02452_si_003.cif
_cod_data_source_block           mdk099
_cod_database_code               4031831
_shelx_estimated_absorpt_t_min   0.306
_shelx_estimated_absorpt_t_max   0.820
_shelxl_version_number           2014-3
_shelx_res_checksum              1930
_shelx_hkl_checksum              15240