Regio- and Stereocontrolled Synthesis of 3-Substituted 1,2-Diazetidines by Asymmetric Allylic Amination of Vinyl Epoxide.
Rajkumar, Sundaram; Clarkson, Guy J.; Shipman, Michael; Organic letters 19 (2017) 2058–2061; doi:10.1021/acs.orglett.7b00653

data_1546617
_publ_section_title
;
 Regio- and Stereocontrolled Synthesis of 3-Substituted 1,2-Diazetidines
 by Asymmetric Allylic Amination of Vinyl Epoxide.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2058
_journal_page_last               2061
_journal_paper_doi               10.1021/acs.orglett.7b00653
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 N2 O4 S'
_chemical_formula_sum            'C19 H20 N2 O4 S'
_chemical_formula_weight         372.43
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.36858(10)
_cell_length_b                   17.0054(3)
_cell_length_c                   17.2914(3)
_cell_measurement_reflns_used    27492
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4160
_cell_measurement_theta_min      3.6290
_cell_volume                     1872.66(5)
_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 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -96.00  -2.00   1.00    5.00    --  -41.82 125.00 -90.00   94
  2  \w    -83.00  38.00   1.00    5.00    --  -41.82  19.00 -60.00  121
  3  \w     17.00 116.00   1.00    5.00    --   41.82  37.00  60.00   99
  4  \w     15.00 114.00   1.00    5.00    --   41.82  50.00-126.00   99
  5  \w     17.00 116.00   1.00    5.00    --   41.82  37.00 -30.00   99
  6  \w     31.00 140.00   1.00   20.00    --  107.00 -77.00 -90.00  109
  7  \w     74.00 178.00   1.00   20.00    --  107.00  77.00 -90.00  104
  8  \w     24.00 109.00   1.00   20.00    --  107.00 -94.00-150.00   85
  9  \w     94.00 178.00   1.00   20.00    --  107.00 125.00 -60.00   84
 10  \w     94.00 178.00   1.00   20.00    --  107.00 125.00 -90.00   84
 11  \w     34.00 121.00   1.00   20.00    --  107.00-125.00  90.00   87
 12  \w     24.00 109.00   1.00   20.00    --  107.00 -94.00-120.00   85
 13  \w     94.00 178.00   1.00   20.00    --  107.00 125.00-120.00   84
 14  \w     34.00 121.00   1.00   20.00    --  107.00-125.00-150.00   87
 15  \w     34.00 133.00   1.00   20.00    --  107.00 -45.00-150.00   99
 16  \w     94.00 178.00   1.00   20.00    --  107.00 125.00  30.00   84
 17  \w     34.00 121.00   1.00   20.00    --  107.00-125.00  30.00   87
 18  \w     25.00 160.00   1.00   20.00    --  107.00 -15.00 150.00  135
 19  \w     34.00 121.00   1.00   20.00    --  107.00-125.00 -30.00   87
 20  \w     54.00 178.00   1.00   20.00    --  107.00  15.00 -30.00  124
 21  \w     54.00 178.00   1.00   20.00    --  107.00  15.00 120.00  124
 22  \w    101.00 178.00   1.00   20.00    --  107.00 100.00 -32.00   77
 23  \w     34.00 133.00   1.00   20.00    --  107.00 -45.00 -60.00   99
 24  \w     28.00 145.00   1.00   20.00    --  107.00 -21.00-145.66  117
 25  \w   -118.00  -9.00   1.00    5.00    --  -41.82 -77.00  30.00  109
 26  \w   -118.00  -9.00   1.00    5.00    --  -41.82 -77.00 120.00  109
 27  \w   -118.00  -9.00   1.00    5.00    --  -41.82 -77.00-150.00  109
 28  \w   -118.00  -9.00   1.00    5.00    --  -41.82 -77.00 -60.00  109
 29  \w      1.00  83.00   1.00    5.00    --   41.82 -99.00  90.00   82
 30  \w      9.00 118.00   1.00    5.00    --   41.82  77.00 120.00  109
 31  \w      1.00  83.00   1.00    5.00    --   41.82 -99.00-180.00   82
 32  \w     78.00 178.00   1.00   20.00    --  107.00  61.00  60.00  100
 33  \w     78.00 178.00   1.00   20.00    --  107.00  61.00-120.00  100
 34  \w     78.00 178.00   1.00   20.00    --  107.00  61.00 120.00  100
 35  \w     78.00 178.00   1.00   20.00    --  107.00  61.00 -30.00  100
 36  \w     74.00 178.00   1.00   20.00    --  107.00  77.00   0.00  104
 37  \w     74.00 178.00   1.00   20.00    --  107.00  77.00 150.00  104
 38  \w     74.00 178.00   1.00   20.00    --  107.00  77.00-180.00  104
 39  \w     78.00 178.00   1.00   20.00    --  107.00  61.00 -60.00  100
 40  \w     78.00 178.00   1.00   20.00    --  107.00  61.00  90.00  100
 41  \w     24.00 109.00   1.00   20.00    --  107.00 -94.00  90.00   85
 42  \w     74.00 176.00   1.00   20.00    --  107.00  77.00 120.00  102
 43  \w     78.00 178.00   1.00   20.00    --  107.00  61.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0217946000
_diffrn_orient_matrix_UB_12      0.0740013000
_diffrn_orient_matrix_UB_13      0.0507468000
_diffrn_orient_matrix_UB_21      -0.2287724000
_diffrn_orient_matrix_UB_22      0.0226038000
_diffrn_orient_matrix_UB_23      -0.0185614000
_diffrn_orient_matrix_UB_31      -0.0758591000
_diffrn_orient_matrix_UB_32      -0.0471380000
_diffrn_orient_matrix_UB_33      0.0707842000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.106
_diffrn_reflns_theta_min         3.646
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09446
_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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Hooft y: -0.001(8) Olex2
Flack x: 0.008(10) Shelx2014
;
_refine_ls_abs_structure_Flack   0.008(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0521P)^2^+0.2502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3575
_reflns_number_total             3764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00653_si_003.cif
_cod_data_source_block           rs2
_cod_depositor_comments          'Adding full bibliography for 1546617.cif.'
_cod_original_cell_volume        1872.65(5)
_cod_database_code               1546617
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.08
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.e 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'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.692
_oxdiff_exptl_absorpt_empirical_full_min 0.454