Mechanistic and Synthetic Implications of the Diol-Ritter Reaction: Unexpected Yet Reversible Pathways in the Regioselective Synthesis of Vicinal-Aminoalcohols.
Ondari, Mark E.; Klosin, Jerzy; Froese, Robert D. J.; Kruper, William R.; MacDonald, Jason; Arriola, Dan J.; Bell, Bruce M.; Briggs, John R.; Kruper, William J.; The Journal of organic chemistry 84 (2019) 4715–4722; doi:10.1021/acs.joc.8b02320

data_4035932
_publ_section_title
;
 Mechanistic and Synthetic Implications of the Diol-Ritter Reaction:
 Unexpected Yet Reversible Pathways in the Regioselective Synthesis of
 Vicinal-Aminoalcohols.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4715
_journal_page_last               4722
_journal_paper_doi               10.1021/acs.joc.8b02320
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C9 H9 Cl6 O2 Sb'
_chemical_formula_weight         483.61
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.9760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4833(2)
_cell_length_b                   18.1783(6)
_cell_length_c                   13.2669(4)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.74
_cell_volume                     1529.54(8)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13414
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.656
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.00619(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0165
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0076P)^2^+1.3237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0373
_reflns_number_gt                3429
_reflns_number_total             3510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02320_si_001.cif
_cod_data_source_block           final
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4035932