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_1555119
_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         'C12 H15 F N2 O4 S'
_chemical_formula_sum            'C12 H15 F N2 O4 S'
_chemical_formula_weight         302.32
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7362(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.70613(9)
_cell_length_b                   8.92562(11)
_cell_length_c                   21.9646(3)
_cell_measurement_reflns_used    3911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.4980
_cell_measurement_theta_min      4.0180
_cell_volume                     1314.12(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega -106.00  -38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  -30.0000 68

  2 omega  -34.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  -30.0000 27

  3 omega  -50.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -30.0000 82

  4 omega   50.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3790 -125.0000  -30.0000 47

  5 omega   95.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000   90.0000 75

  6 omega   63.00  124.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -135.0000 -147.0000 61

  7 omega   94.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000    0.0000 84

  8 omega  113.00  143.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000 -150.0000 30

  9 omega   52.00  102.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -60.0000 50

 10 omega   47.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000 -150.0000 51

 11 omega   35.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 68

 12 omega  129.00  158.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -60.0000 29

 13 omega   62.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2040424000
_diffrn_orient_matrix_UB_12      -0.0234265000
_diffrn_orient_matrix_UB_13      -0.0289346000
_diffrn_orient_matrix_UB_21      -0.0999989000
_diffrn_orient_matrix_UB_22      0.0108304000
_diffrn_orient_matrix_UB_23      -0.0639093000
_diffrn_orient_matrix_UB_31      0.0343670000
_diffrn_orient_matrix_UB_32      0.1706358000
_diffrn_orient_matrix_UB_33      0.0000673000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5727
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.780
_diffrn_reflns_theta_min         4.027
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83156
_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    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0550P)^2^+0.6169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2680
_reflns_number_total             2782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01777_si_003.cif
_cod_data_source_block           nh4
_cod_database_code               1555119
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_reflns_odcompleteness_completeness 98.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.17
_olex2_refinement_description
;
The molecule has disorder of the fluoride position. 
The disorder occurs at the equatorial position of C1 and C5.
The occupancy of the F1-C1 to F5-C5 position was linked to a 
free variable and refined to an occupancy of 81:19.

The sulphonamide NH was located in a difference map and refined with a 
DFIX restraint and given thermal parameters Uiso 1.5 times Uequiv of 
the parent nitrogen.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All F(H) groups
2. Restrained distances
 N7-H7
 0.88 with sigma of 0.02
3. Others
 Sof(H1BA)=Sof(H1BB)=Sof(H5B)=Sof(F5)=1-FVAR(1)
 Sof(H1A)=Sof(F1)=Sof(H5AA)=Sof(H5AB)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5B), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1BA,H1BB), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5AA,H5AB)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'