Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes.
Hao, Wei; Wu, Xiangyu; Sun, James Z.; Siu, Juno C.; MacMillan, Samantha N.; Lin, Song; Journal of the American Chemical Society 139 (2017) 12141–12144; doi:10.1021/jacs.7b06723

data_4131549
_publ_section_title
;
 Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of
 N-Acylaziridines and Alkenes.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12141
_journal_page_last               12144
_journal_paper_doi               10.1021/jacs.7b06723
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C20 H18 Br Cl2 N O3'
_chemical_formula_sum            'C20 H18 Br Cl2 N O3'
_chemical_formula_weight         471.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-28
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                97.7480(10)
_cell_angle_beta                 93.0590(10)
_cell_angle_gamma                96.8100(10)
_cell_formula_units_Z            2
_cell_length_a                   8.04660(10)
_cell_length_b                   9.54360(10)
_cell_length_c                   13.3100(2)
_cell_measurement_reflns_used    25353
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.9400
_cell_measurement_theta_min      2.1580
_cell_volume                     1003.14(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -45.00  30.00   0.50    3.00    --    3.55 -87.00 -49.00  150
  2  \w    -26.00  27.00   0.50    3.00    --   -4.80 -99.00  30.00  106
  3  \w     10.00  50.00   0.50    3.00    --    3.55-125.00 146.31   80
  4  \w    -45.00  21.00   0.50    3.00    --   -4.80 -87.00 -49.00  132
  5  \w    -26.00  27.00   0.50    3.00    --   -4.80 -99.00-150.00  106
  6  \w    -26.00  27.00   0.50    3.00    --   -4.80 -99.00 -90.00  106
  7  \w    -16.00  70.00   0.50    3.00    --   -4.80  19.00-150.00  172
  8  \w    -16.00  68.00   0.50    3.00    --   -4.80  37.00 -30.00  168
  9  \w    -16.00  70.00   0.50    3.00    --   -4.80  19.00 120.00  172
 10  \w    -16.00  70.00   0.50    3.00    --   -4.80  19.00  60.00  172
 11  \w    -16.00  70.00   0.50    3.00    --   -4.80  19.00 -90.00  172
 12  \w    -16.00  19.00   0.50    3.00    --   -4.80  37.00  90.00   70
 13  \w    -31.00  24.00   0.50    3.00    --   -4.80  87.00  68.00  110
 14  \w    -69.00  15.00   0.50    3.00    --    3.55 -37.00 150.00  168
 15  \w    -71.00  15.00   0.50    3.00    --    3.55 -22.00  34.50  172
 16  \w    -69.00  15.00   0.50    3.00    --    3.55 -37.00  90.00  168
 17  \w    -71.00  15.00   0.50    3.00    --    3.55 -19.00   0.00  172
 18  \w    -71.00  15.00   0.50    3.00    --    3.55 -19.00-180.00  172
 19  \w    -71.00  15.00   0.50    3.00    --    3.55 -19.00-120.00  172
 20  \w    -71.00  15.00   0.50    3.00    --    3.55 -19.00 -60.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0431394000
_diffrn_orient_matrix_UB_12      0.0019187000
_diffrn_orient_matrix_UB_13      -0.0475828000
_diffrn_orient_matrix_UB_21      -0.0155157000
_diffrn_orient_matrix_UB_22      -0.0755342000
_diffrn_orient_matrix_UB_23      -0.0079159000
_diffrn_orient_matrix_UB_31      -0.0762807000
_diffrn_orient_matrix_UB_32      0.0030637000
_diffrn_orient_matrix_UB_33      0.0240859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51029
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_min         2.171
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0227
_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^)+(0.0229P)^2^+0.6004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4439
_reflns_number_total             4749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06723_si_004.cif
_cod_data_source_block           rwh3_abs
_cod_database_code               4131549
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C20H18BrCl2NO3
_chemical_oxdiff_usercomment     'Crystallized from Et2O'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C16(H16), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              35932
_shelx_hkl_checksum              19710
_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 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.955