Chemo- and enantioselective intramolecular silver-catalyzed aziridinations of carbamimidates.
Trinh, Tuan Anh; Fu, Yue; Hu, Derek B.; Zappia, Soren A.; Guzei, Ilia A.; Liu, Peng; Schomaker, Jennifer M.; Chemical communications (Cambridge, England) 60 (2023) 224–227; doi:10.1039/d3cc05670h

data_7132421
_publ_section_title
;
 Chemo- and enantioselective intramolecular silver-catalyzed
 aziridinations of carbamimidates.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              224
_journal_page_last               227
_journal_paper_doi               10.1039/d3cc05670h
_journal_volume                  60
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H15 Cl3 N2 O4 S'
_chemical_formula_sum            'C14 H15 Cl3 N2 O4 S'
_chemical_formula_weight         413.69
_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             2022-10-24
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2022.10.14 svn.ra52d74a8 for OlexSys, GUI svn.r6611)
;
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.646(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.978(3)
_cell_length_b                   9.923(3)
_cell_length_c                   14.449(4)
_cell_measurement_reflns_used    9766
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.093
_cell_measurement_theta_min      2.346
_cell_volume                     1705.8(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX3 Ver. 2019.11-0. (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ver. 2019.1-0. (Bruker-AXS, 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54085
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.158
_diffrn_reflns_theta_min         1.419
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 5302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         11914
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0310P)^2^+0.2376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                11567
_reflns_number_total             11914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05670h2.cif
_cod_data_source_block           schomaker100
_cod_depositor_comments          'Adding full bibliography for 7132421.cif.'
_cod_database_code               7132421
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.865
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Same fragment restrains
{Cl1B, Cl2B, Cl3A, S1B, O1B, O2B, O3B, N1A, C1B, C2B} sigma for 1-2: 0.01, 1-3:
0.02
as in
{Cl1A, Cl2A, Cl3A, S1A, O1A, O2A, O3A, N1A, C1A, C2A}
3. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(S1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(C1B)=Sof(C2B)=
 Sof(H2BA)=Sof(H2BB)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(S1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C1A)=Sof(C2A)=
 Sof(H2AA)=Sof(H2AB)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C6A(H6A), C7A(H7A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C2A(H2AA,H2AB), C2B(H2BA,
 H2BB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C8A(H8AA,H8AB)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C10A(H10A), C11A(H11A),
 C12A(H12A), C13A(H13A), C14A(H14A)
;
_shelx_res_checksum              78315
_shelx_hkl_checksum              40745
_olex2_submission_special_instructions 'No special instructions were received'