Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst
Chen, Jiean; Meng, Sixuan; Wang, Leming; Tang, Hongmei; Huang, Yong; Chem. Sci. 6 (2015) 4184–; doi:10.1039/C5SC00878F

data_1519439
_publ_section_title
;
 Highly enantioselective sulfa-Michael addition reactions using
 N-heterocyclic carbene as a non-covalent organocatalyst
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4184
_journal_paper_doi               10.1039/C5SC00878F
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 F3 N S'
_chemical_formula_sum            'C17 H18 F3 N S'
_chemical_formula_weight         325.38
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-02-05 deposited with the CCDC.
2015-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.727(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.11670(10)
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_cell_length_c                   11.3854(8)
_cell_measurement_reflns_used    9396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      6.90
_cell_volume                     792.25(6)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10973
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.255
_diffrn_reflns_theta_min         6.892
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
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_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0693P)^2^+0.0749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2403
_reflns_number_total             2783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00878f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1519439.cif.'
_cod_database_code               1519439
_shelxl_version_number           2014-3
_shelx_res_checksum              56780
_shelx_hkl_checksum              42277