P(NMe2)3-Mediated Aziridination of Imines with α-Ketoesters for Synthesis of Aziridine-2-carboxylates.
Jiang, Jin; Liu, Hui; Lu, Chong-Dao; Xu, Yan-Jun; The Journal of organic chemistry 82 (2017) 811–818; doi:10.1021/acs.joc.6b02669

data_4032100
_publ_section_title
;
 P(NMe2)3-Mediated Aziridination of Imines with \a-Ketoesters for
 Synthesis of Aziridine-2-carboxylates.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              811
_journal_page_last               818
_journal_paper_doi               10.1021/acs.joc.6b02669
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H25 N O5 S'
_chemical_formula_sum            'C25 H25 N O5 S'
_chemical_formula_weight         451.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.143(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.751(7)
_cell_length_b                   16.267(9)
_cell_length_c                   12.438(7)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.369
_cell_measurement_theta_min      2.215
_cell_volume                     2347(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13670
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.078
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.9020.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0585P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2618
_reflns_number_total             5352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02669_si_002.cif
_cod_data_source_block           4c
_cod_depositor_comments          'Adding full bibliography for 4032100.cif.'
_cod_database_code               4032100
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 S1, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C7(H7), C20(H20), C24(H24), C21(H21), C23(H23), C11(H11), C16(H16),
 C8(H8), C13(H13), C10(H10), C9(H9), C14(H14)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C5(H5A,H5B,H5C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              75460
_shelx_hkl_checksum              48022
_olex2_submission_special_instructions 'No special instructions were received'