Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization
Gui, Yang; Liang, Xinping; Li, Yanan; Li, Kuiliang; Zha, Zhenggen; Wang, Zhiyong; Organic Chemistry Frontiers 6 (2019) 942–; doi:10.1039/C8QO01397G

data_1554582
_publ_section_title
;
 Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic
 dehydration/aminalization/aza-Michael desymmetrization
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              942
_journal_paper_doi               10.1039/C8QO01397G
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H14 F3 N O4 S'
_chemical_formula_weight         373.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc21bmrs
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_audit_update_record
;
2018-12-23 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_reflns_used    5287
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.9610
_cell_measurement_theta_min      5.3450
_cell_volume                     2008.08(4)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6685
_diffrn_reflns_point_group_measured_fraction_full 0.994
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.101
_diffrn_reflns_theta_min         3.931
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       blcok
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_platon_squeeze_details
;
;
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.001(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0796P)^2^+0.0962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3655
_reflns_number_total             3761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01397g2.cif
_cod_data_source_block           shelxl
_cod_database_code               1554582
_shelx_estimated_absorpt_t_min   0.654
_shelx_estimated_absorpt_t_max   0.697
_shelxl_version_number           2013-4
_shelx_res_checksum              44426
_shelx_hkl_checksum              9409