Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes.
Hsueh, Nathanael; Clarkson, Guy J.; Shipman, Michael; Organic letters 17 (2015) 3632–3635; doi:10.1021/acs.orglett.5b01777

data_1555124
_publ_section_title
;
 Generation and Ring Opening of Aziridines in Telescoped Continuous Flow
 Processes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3632
_journal_page_last               3635
_journal_paper_doi               10.1021/acs.orglett.5b01777
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H16 N2 O2 S'
_chemical_formula_sum            'C16 H16 N2 O2 S'
_chemical_formula_weight         300.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.856(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2360(2)
_cell_length_b                   21.1919(5)
_cell_length_c                   8.4904(2)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      78.4490
_cell_measurement_theta_min      4.1780
_cell_volume                     1438.76(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -64.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 93

  2 omega  -67.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000 -180.0000 99

  3 omega  -66.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000   60.0000 98

  4 omega   38.00  109.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 71

  5 omega   93.00  171.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000  -90.0000 78

  6 omega   37.00  109.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   90.0000 72

  7 omega   44.00   98.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000   90.0000 54

  8 omega  114.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000   90.0000 64

  9 omega   51.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 40

 10 omega  107.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 70

 11 omega   92.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -150.0000 85

 12 omega   64.00  109.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  150.0000 45

 13 omega   47.00  138.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -180.0000 91

 14 omega   41.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -30.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1000027000
_diffrn_orient_matrix_UB_12      0.0025334000
_diffrn_orient_matrix_UB_13      -0.1317454000
_diffrn_orient_matrix_UB_21      -0.0025432000
_diffrn_orient_matrix_UB_22      -0.0725847000
_diffrn_orient_matrix_UB_23      -0.0094948000
_diffrn_orient_matrix_UB_31      -0.1646892000
_diffrn_orient_matrix_UB_32      0.0026887000
_diffrn_orient_matrix_UB_33      -0.1322270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.761
_diffrn_reflns_theta_min         4.172
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0613P)^2^+0.2324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01777_si_005.cif
_cod_data_source_block           nh3
_cod_original_cell_volume        1438.78(6)
_cod_database_code               1555124
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'