HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of 2-Aminoglycopyranoses.
Probst, Nicolas; Martin, Amélie; Désiré, Jérôme; Mingot, Agnès; Marrot, Jérôme; Blériot, Yves; Thibaudeau, Sébastien; Organic letters 19 (2017) 1040–1043; doi:10.1021/acs.orglett.7b00003

data_1545254
_publ_section_title
;
 HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of
 2-Aminoglycopyranoses.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1040
_journal_page_last               1043
_journal_paper_doi               10.1021/acs.orglett.7b00003
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H29 N O9 S'
_chemical_formula_weight         531.56
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.4340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8723(2)
_cell_length_b                   8.4197(2)
_cell_length_c                   14.4418(3)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.28
_cell_volume                     1319.65(5)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38133
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.002
_diffrn_reflns_theta_min         1.876
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012/1)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.7127
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 2182 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.4881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                5895
_reflns_number_total             7493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00003_si_001.cif
_cod_data_source_block           npr120
_cod_depositor_comments          'Adding full bibliography for 1545254.cif.'
_cod_database_code               1545254
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.969
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_shelx_res_checksum              48289
_shelx_hkl_checksum              4078