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_4133507
_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_absolute_configuration unk
_chemical_formula_moiety         'C11 H12 Cl N'
_chemical_formula_sum            'C11 H12 Cl N'
_chemical_formula_weight         193.67
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7714(2)
_cell_length_b                   7.3205(2)
_cell_length_c                   22.5971(7)
_cell_measurement_reflns_used    2851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.92
_cell_volume                     954.72(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 0.999
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.934
_diffrn_reflns_theta_min         2.925
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0545 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.8610. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.1066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2090
_reflns_number_total             2296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10485_si_002.cif
_cod_data_source_block           testo1
_cod_database_code               4133507
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Shared sites
{C8, N1A}
{C8A, N1}
3. Uiso/Uaniso restraints and constraints
N1 \\sim C8A \\sim C11 \\sim C10 \\sim C9 \\sim N1A \\sim C8: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8A) = Uanis(N1)
Uanis(C8) = Uanis(N1A)
4. Others
 Sof(H7B)=Sof(H11C)=Sof(H11D)=Sof(H9BC)=Sof(H9BD)=Sof(N1A)=Sof(C8A)=Sof(H8A)=1-
 FVAR(1)
 Sof(N1)=Sof(C8)=Sof(H8)=Sof(H7A)=Sof(H11A)=Sof(H11B)=Sof(H9AA)=Sof(H9AB)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7A), C7(H7B), C8A(H8A)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C10(H10A,H10B), C9(H9AA,H9AB), C9(H9BC,H9BD)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_shelx_res_checksum              53573
_shelx_hkl_checksum              63428
_olex2_submission_special_instructions 'No special instructions were received'