Ring Expansion of Cyclic β-Amino Alcohols Induced by Diethylaminosulfur Trifluoride: Synthesis of Cyclic Amines with a Tertiary Fluorine at C3
Bruno Anxionnat; Benoit Robert; Pascal George; Gino Ricci; Marc-Antoine Perrin; Domingo Gomez Pardo; Janine Cossy; Journal of Organic Chemistry 77 (2012) 6087–6099; doi:10.1021/jo300887u

data_4027303
_publ_section_title
;
 Ring Expansion of Cyclic \b-Amino Alcohols Induced by Diethylaminosulfur
 Trifluoride: Synthesis of Cyclic Amines with a Tertiary Fluorine at C3
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6087
_journal_page_last               6099
_journal_paper_doi               10.1021/jo300887u
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'Cl, C19 H23 F N, O'
_chemical_formula_sum            'C19 H25 Cl F N O'
_chemical_formula_weight         337.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8205(5)
_cell_length_b                   12.3343(11)
_cell_length_c                   27.224(3)
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.741
_cell_measurement_theta_min      2.228
_cell_volume                     1954.5(3)
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            16105
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.648048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1325 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.6480.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             720
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.035(5)
_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   1.137
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          4.260
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.0909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                3895
_reflns_number_total             4643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300887u_si_001.cif
_cod_data_source_block           amp251d
_cod_original_cell_volume        1954.4(3)
_cod_database_code               4027303