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_1555122
_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         'C11 H14 N2 O2 S'
_chemical_formula_sum            'C11 H14 N2 O2 S'
_chemical_formula_weight         238.30
_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             2015-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.006(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2033(5)
_cell_length_b                   5.10542(13)
_cell_length_c                   15.6074(6)
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.2620
_cell_measurement_theta_min      3.5320
_cell_volume                     1152.10(7)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_details
;
  1 omega -101.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -47.0000  127.0000 85

  2 omega  -95.00  -59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000 -169.0000  -89.0000 36

  3 omega  -51.00   27.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   47.0000  -83.0000 78

  4 omega  -50.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000    0.0000 43

  5 omega   73.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3790   38.0000   90.0000 39

  6 omega   16.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3790   77.0000   30.0000 68

  7 omega   93.00  125.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   60.0000 32

  8 omega   52.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000   60.0000 44

  9 omega  153.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   47.0000  -83.0000 25

 10 omega  133.00  175.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000   30.0000 42

 11 omega   88.00  114.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000  -30.0000 26

 12 omega  122.00  176.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000  -30.0000 54

 13 omega  101.00  168.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000  150.0000 67

 14 omega   55.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 36

 15 omega   88.00  118.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000   30.0000 30

 16 omega   62.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -120.0000 29

 17 omega   92.00  121.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000    0.0000 29

 18 omega   84.00  110.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000   30.0000 26

 19 omega  140.00  166.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000    0.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0788327000
_diffrn_orient_matrix_UB_12      -0.1633228000
_diffrn_orient_matrix_UB_13      0.0157470000
_diffrn_orient_matrix_UB_21      -0.0354660000
_diffrn_orient_matrix_UB_22      -0.0669750000
_diffrn_orient_matrix_UB_23      -0.1011618000
_diffrn_orient_matrix_UB_31      0.0622816000
_diffrn_orient_matrix_UB_32      -0.2446449000
_diffrn_orient_matrix_UB_33      0.0171697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5511
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.484
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53701
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0649P)^2^+0.3253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2041
_reflns_number_total             2276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01777_si_004.cif
_cod_data_source_block           nh1
_cod_original_cell_volume        1152.11(7)
_cod_database_code               1555122
_chemical_oxdiff_formula         'C20 H20 N O2 S'
_reflns_odcompleteness_completeness 90.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_olex2_refinement_description
;
The crystals were very weakly diffracting and Cu radiation and long 
exposures were used to get the best data possible.
There is a B alert from the checkcif program for weak data.
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:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'