α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines
Grellepois, Fabienne; Ben Jamaa, Abdelkhalek; Saraiva Rosa, Nathalie; Organic & Biomolecular Chemistry  (2017) –; doi:10.1039/C7OB02506H

data_7155974
_publ_section_title
;
 \a-Trifluoromethylated tertiary homoallylic amines: diastereoselective
 synthesis and conversion into \b-aminoesters, \g- and \d-aminoalcohols,
 azetidines and pyrrolidines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02506H
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H22 F3 N O S'
_chemical_formula_weight         273.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   9.071(5)
_cell_length_b                   16.862(5)
_cell_length_c                   19.003(5)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      3.50
_cell_volume                     2907(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48644
_diffrn_reflns_theta_full        72.44
_diffrn_reflns_theta_max         72.44
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.2711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0601
_reflns_number_gt                5551
_reflns_number_total             5748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02506h2.cif
_cod_data_source_block           cu_15fg015_0m
_cod_depositor_comments
;

2018-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C22 H44 F6 N2 O2 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     546.71
_cod_database_code               7155974