Asymmetric synthesis of CF<sub>2</sub>-functionalized aziridines by combined strong Brønsted acid catalysis.
Tan, Xing-Fa; Zhang, Fa-Guang; Ma, Jun-An; Beilstein journal of organic chemistry 16 (2020) 638–644; doi:10.3762/bjoc.16.60

data_4038240
_publ_section_title
;
 Asymmetric synthesis of CF<sub>2</sub>-functionalized aziridines by
 combined strong Br\/onsted acid catalysis.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              638
_journal_page_last               644
_journal_paper_doi               10.3762/bjoc.16.60
_journal_volume                  16
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H20 Cl F2 N O4 S'
_chemical_formula_sum            'C23 H20 Cl F2 N O4 S'
_chemical_formula_weight         479.91
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.12(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5826(8)
_cell_length_b                   16.132(2)
_cell_length_c                   11.8958(13)
_cell_measurement_reflns_used    4059
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.505
_cell_measurement_theta_min      2.525
_cell_volume                     1071.3(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12417
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.564
_diffrn_reflns_theta_min         2.525
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0905 before and 0.0580 after correction. The Ratio of minimum to maximum transmission is 0.9292. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                3351
_reflns_number_total             4273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-60-S3.cif
_cod_data_source_block           ds
_cod_depositor_comments
'Adding full bibliography for 4038239--4038240.cif.'
_cod_database_code               4038240
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C16(H16), C19(H19), C21(H21), C12(H12), C18(H18), C13(H13),
 C14(H14), C15(H15), C1(H1A), C4(H4), C5(H5), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'