Amination of N-Aryl Prolinol via Ring Expansion and Contraction: Application to the Chiral Ligand for the Catalytic Asymmetric Reaction
Mino, Takashi; Saito, Akio; Tanaka, Youichi; Hasegawa, Shintaro; Sato, Yutaka; Sakamoto, Masami; Fujita, Tsutomu; Journal of Organic Chemistry 70 (2005) 1937–1940; doi:10.1021/jo0479967

data_4020114
_publ_section_title
;
 Amination of N-Aryl Prolinol via Ring Expansion and Contraction:
 Application to the Chiral Ligand for the Catalytic Asymmetric Reaction
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   5
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1937
_journal_page_last               1940
_journal_paper_doi               10.1021/jo0479967
_journal_volume                  70
_journal_year                    2005
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C24 H25 Br N O2 P'
_chemical_formula_sum            'C24 H25 Br N O2 P'
_chemical_formula_weight         470.352
_chemical_name_common            3-Bromo-N-(2-diPhPO-6-MeOphenyl)piperidine
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.889(5)
_cell_length_b                   13.899(6)
_cell_length_c                   10.271(3)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    298
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     2235.4(14)
_diffrn_measurement_device       'Mac Science MXC18'
_diffrn_measurement_method       '\q \w scans'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.06173
_diffrn_orient_matrix_UB_12      0.00069
_diffrn_orient_matrix_UB_13      -0.00877
_diffrn_orient_matrix_UB_21      -0.01638
_diffrn_orient_matrix_UB_22      0.00256
_diffrn_orient_matrix_UB_23      -0.09834
_diffrn_orient_matrix_UB_31      0.00009
_diffrn_orient_matrix_UB_32      0.07190
_diffrn_orient_matrix_UB_33      0.00361
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' CuK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4664
_diffrn_reflns_theta_full        70.08
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    3.33
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             968
_refine_diff_density_max         0.81
_refine_diff_density_min         -0.82
_refine_diff_density_rms         0.10
_refine_ls_abs_structure_details
;
;
_refine_ls_abs_structure_Rogers  '_'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.779
_refine_ls_goodness_of_fit_gt    0.718
_refine_ls_goodness_of_fit_ref   0.718
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     568
_refine_ls_number_reflns         4216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.178
_refine_ls_wR_factor_gt          0.177
_refine_ls_wR_factor_ref         0.177
_reflns_d_resolution_high        0.64
_reflns_d_resolution_low         2.28
_reflns_limit_h_max              19
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                4216
_reflns_number_total             4433
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value
58 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 

 Updated bibliographic information and added the common chemical
 name extracted from the previous publication title.

 Antanas Vaitkus,
 2019-10-02
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020114