Functionalization of Alkenes through Telescoped Continuous Flow Aziridination Processes.
Hsueh, Nathanael; Clarkson, Guy J.; Shipman, Michael; Organic letters 18 (2016) 4908–4911; doi:10.1021/acs.orglett.6b02349

data_1555753
_publ_section_title
;
 Functionalization of Alkenes through Telescoped Continuous Flow
 Aziridination Processes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4908
_journal_page_last               4911
_journal_paper_doi               10.1021/acs.orglett.6b02349
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C18 H17 Cl N2 O2 S'
_chemical_formula_sum            'C18 H17 Cl N2 O2 S'
_chemical_formula_weight         360.84
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0333(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.48668(7)
_cell_length_b                   7.37203(6)
_cell_length_c                   20.25344(15)
_cell_measurement_reflns_used    18908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7740
_cell_measurement_theta_min      3.9980
_cell_volume                     1648.35(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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_environment      N~2~
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -115.00 -16.00   1.00    2.50    --  -41.46 -41.00  -9.00   99
  2  \w   -114.00 -13.00   1.00    2.50    --  -41.46 -57.00-120.00  101
  3  \w    -70.00  32.00   1.00    2.50    --  -41.46  57.00 150.00  102
  4  \w     13.00 114.00   1.00    2.50    --   41.46  57.00-120.00  101
  5  \w     -4.00  82.00   1.00    2.50    --   41.46 -99.00   0.00   86
  6  \w     18.00  97.00   1.00    2.50    --   41.46-125.00 -30.00   79
  7  \w     17.00 116.00   1.00    2.50    --   41.46  38.00 -30.00   99
  8  \w     57.00 151.00   1.00   10.00    --  114.00 178.00   0.00   94
  9  \w     81.00 178.00   1.00   10.00    --  114.00  77.00-180.00   97
 10  \w     81.00 178.00   1.00   10.00    --  114.00  77.00 -90.00   97
 11  \w    100.00 178.00   1.00   10.00    --  114.00 111.00  60.00   78
 12  \w     85.00 178.00   1.00   10.00    --  114.00  61.00-180.00   93
 13  \w     81.00 178.00   1.00   10.00    --  114.00  77.00 150.00   97
 14  \w     85.00 178.00   1.00   10.00    --  114.00  61.00-120.00   93
 15  \w     42.00 143.00   1.00   10.00    --  114.00 -61.00 -30.00  101
 16  \w     85.00 178.00   1.00   10.00    --  114.00  61.00 -90.00   93
 17  \w     61.00 178.00   1.00   10.00    --  114.00  15.00 -60.00  117
 18  \w     85.00 178.00   1.00   10.00    --  114.00  61.00 -60.00   93
 19  \w     81.00 178.00   1.00   10.00    --  114.00  77.00-120.00   97
 20  \w     85.00 178.00   1.00   10.00    --  114.00  61.00-150.00   93
 21  \w     32.00 109.00   1.00   10.00    --  114.00 -95.00   0.00   77
 22  \w     88.00 178.00   1.00   10.00    --  114.00  45.00 -90.00   90
 23  \w     61.00 178.00   1.00   10.00    --  114.00  15.00  60.00  117
 24  \w     88.00 178.00   1.00   10.00    --  114.00  45.00-150.00   90
 25  \w     86.00 178.00   1.00   10.00    --  114.00  30.00 -60.00   92
 26  \w     81.00 178.00   1.00   10.00    --  114.00  77.00-150.00   97
 27  \w     88.00 178.00   1.00   10.00    --  114.00  45.00 -60.00   90
 28  \w     88.00 178.00   1.00   10.00    --  114.00  45.00-120.00   90
 29  \w     33.00 110.00   1.00   10.00    --  114.00 -98.00 140.00   77
 30  \w     86.00 178.00   1.00   10.00    --  114.00  30.00-150.00   92
 31  \w     86.00 178.00   1.00   10.00    --  114.00  30.00-120.00   92
 32  \w     81.00 178.00   1.00   10.00    --  114.00  77.00 -60.00   97
 33  \w     41.00 140.00   1.00   10.00    --  114.00 -45.00 120.00   99
 34  \w   -116.00 -17.00   1.00    2.50    --  -41.46 -38.00  90.00   99
 35  \w      2.00  30.00   1.00    2.50    --   41.46  95.00 166.58   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135676000
_diffrn_orient_matrix_UB_12      -0.0422219000
_diffrn_orient_matrix_UB_13      0.0719935000
_diffrn_orient_matrix_UB_21      0.1230372000
_diffrn_orient_matrix_UB_22      -0.0985901000
_diffrn_orient_matrix_UB_23      0.0185540000
_diffrn_orient_matrix_UB_31      0.0644020000
_diffrn_orient_matrix_UB_32      0.1793879000
_diffrn_orient_matrix_UB_33      0.0271436000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32278
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.077
_diffrn_reflns_theta_min         4.004
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.5284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3327
_reflns_number_total             3520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02349_si_003.cif
_cod_data_source_block           nh6
_cod_database_code               1555753
_chemical_oxdiff_formula         '|C20 H20 N2 O2 S Cl'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
The NH was located in a difference map and allowed to refine freely

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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              56181
_shelx_hkl_checksum              39544
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.697
_oxdiff_exptl_absorpt_empirical_full_min 0.808