Diastereoselective Synthesis of α-Quaternary Aziridine-2-carboxylates via Aza-Corey-Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino Esters.
Marsini, Maurice A.; Reeves, Jonathan T.; Desrosiers, Jean-Nicolas; Herbage, Melissa A.; Savoie, Jolaine; Li, Zhibin; Fandrick, Keith R.; Sader, C. Avery; McKibben, Bryan; Gao, Donghong A.; Cui, Jianwen; Gonnella, Nina C.; Lee, Heewon; Wei, Xudong; Roschangar, Frank; Lu, Bruce Z.; Senanayake, Chris H.; Organic letters 17 (2015) 5614–5617; doi:10.1021/acs.orglett.5b02838

data_1540606
_publ_section_title
;
 Diastereoselective Synthesis of \a-Quaternary Aziridine-2-carboxylates
 via Aza-Corey-Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino
 Esters.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5614
_journal_page_last               5617
_journal_paper_doi               10.1021/acs.orglett.5b02838
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C12 H17 N O3 S2'
_chemical_formula_weight         287.38
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7469(2)
_cell_length_b                   13.4624(3)
_cell_length_c                   24.6866(5)
_cell_measurement_temperature    100(2)
_cell_volume                     2906.95(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13540
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        66.612
_diffrn_reflns_theta_max         66.612
_diffrn_reflns_theta_min         3.581
_exptl_absorpt_coefficient_mu    3.334
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0237
_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^)+(0.0346P)^2^+0.2284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                4800
_reflns_number_total             4915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02838_si_001.cif
_cod_data_source_block           scan_0m_P212121
_cod_depositor_comments
;

2019-01-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C24 H34 N2 O6 S4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     574.77
_cod_database_code               1540606
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.635
_shelx_estimated_absorpt_t_max   0.851
_shelx_res_checksum              25368
_shelx_hkl_checksum              4123