Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction.
Farndon, Joshua J.; Young, Tom A.; Bower, John F.; Journal of the American Chemical Society 140 (2018) 17846–17850; doi:10.1021/jacs.8b10485

data_4133505
_publ_section_title
;
 Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent:
 An Aza-Prilezhaev Reaction.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17846
_journal_page_last               17850
_journal_paper_doi               10.1021/jacs.8b10485
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C26 H27 N3 O7 S'
_chemical_formula_sum            'C26 H27 N3 O7 S'
_chemical_formula_weight         525.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.747(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7778(3)
_cell_length_b                   10.9762(3)
_cell_length_c                   23.2290(6)
_cell_measurement_reflns_used    8172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      2.555
_cell_volume                     2487.68(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            44706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.983
_diffrn_reflns_theta_min         1.757
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0684 before and 0.0542 after correction. The Ratio of minimum to maximum transmission is 0.8706. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.244
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6002
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0373P)^2^+1.0715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4786
_reflns_number_total             6002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10485_si_004.cif
_cod_data_source_block           testm1
_cod_database_code               4133505
_shelx_shelxl_version_number     2017/1
_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. Restrained distances
 O1-C9 \\sim O1-C9A
 with sigma of 0.01
 C9A-C10A \\sim C9-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C11A \\sim C12A
\\sim C13A \\sim C14A \\sim C15A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9A) = Uanis(C9)
Uanis(C10A) = Uanis(C10)
4. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C23(H23), C25(H25), C26(H26), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C15A(H15A)
5.d Fitted hexagon refined as free rotating group:
 C10(C11,C12,C13,C14,C15), C10A(C11A,C12A,C13A,C14A,C15A)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              85066
_shelx_hkl_checksum              7261
_olex2_submission_special_instructions 'No special instructions were received'