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_4131548
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 N O3 S'
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.8777(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.63670(14)
_cell_length_b                   5.74782(3)
_cell_length_c                   17.80540(12)
_cell_measurement_reflns_used    45040
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.0380
_cell_measurement_theta_min      4.5980
_cell_volume                     1701.28(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -93.00  -8.00   0.50    1.00    --  -50.11 123.00-171.00  170
  2  \w    -94.00 -11.00   0.50    2.00    --  -82.50 123.00-171.00  166
  3  \w    -87.00 -11.00   0.50    2.00    --  -82.50  19.00   0.00  152
  4  \w   -121.00 -54.00   0.50    1.00    --  -50.11-148.00 -55.00  134
  5  \w   -121.00 -70.00   0.50    1.00    --  -50.11-125.00 -90.00  102
  6  \w   -121.00 -70.00   0.50    1.00    --  -50.11-125.00   0.00  102
  7  \w   -121.00 -72.00   0.50    1.00    --  -50.11-123.00 107.00   98
  8  \w   -121.00 -70.00   0.50    1.00    --  -50.11-125.00 150.00  102
  9  \w   -121.00 -38.00   0.50    1.00    --  -50.11 -57.00  30.00  166
 10  \w     30.00  94.00   0.50    1.00    --   50.11-123.00 107.00  128
 11  \w     32.00 120.00   0.50    2.00    --  104.00-123.00 107.00  176
 12  \w     44.00 133.00   0.50    2.00    --  104.00-148.00 -55.00  178
 13  \w     33.00 116.00   0.50    2.00    --  104.00 -57.00  90.00  166
 14  \w     99.00 176.00   0.50    2.00    --  104.00  19.00 120.00  154
 15  \w     85.00 175.00   0.50    2.00    --  104.00  77.00 -30.00  180
 16  \w     92.00 176.00   0.50    2.00    --  104.00  57.00 -90.00  168
 17  \w     99.00 176.00   0.50    2.00    --  104.00  37.00-180.00  154
 18  \w     76.00 172.00   0.50    2.00    --  104.00 148.00  -8.00  192
 19  \w     56.00 111.00   0.50    2.00    --  104.00   0.00-180.00  110
 20  \w     31.00 121.00   0.50    1.00    --   50.11  77.00-150.00  180
 21  \w     56.00 111.00   0.50    2.00    --  104.00   0.00   0.00  110
 22  \w     45.00 122.00   0.50    1.00    --   50.11  37.00  30.00  154
 23  \w     39.00 122.00   0.50    1.00    --   50.11  57.00 -90.00  166
 24  \w     32.00 110.00   0.50    2.00    --  104.00 -37.00  60.00  156
 25  \w     33.00 124.00   0.50    2.00    --  104.00 -77.00 -60.00  182
 26  \w     33.00 124.00   0.50    2.00    --  104.00 -77.00  90.00  182
 27  \w     33.00 116.00   0.50    2.00    --  104.00 -57.00 -90.00  166
 28  \w     32.00 110.00   0.50    2.00    --  104.00 -99.00 -90.00  156
 29  \w     32.00 110.00   0.50    2.00    --  104.00 -37.00-120.00  156
 30  \w     31.00 121.00   0.50    1.00    --   50.11  77.00-180.00  180
 31  \w     31.00 121.00   0.50    1.00    --   50.11  77.00 -60.00  180
 32  \w     31.00 121.00   0.50    1.00    --   50.11  77.00 120.00  180
 33  \w     31.00 121.00   0.50    1.00    --   50.11  77.00  60.00  180
 34  \w     31.00 121.00   0.50    1.00    --   50.11  77.00  30.00  180
 35  \w    -20.00  56.00   0.50    1.00    --   50.11 -37.00  60.00  152
 36  \w   -121.00 -70.00   0.50    1.00    --  -50.11-125.00-180.00  102
 37  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00 -30.00  180
 38  \w   -154.00 -54.00   0.50    2.00    --  -82.50-148.00 -55.00  200
 39  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00 120.00  180
 40  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00  60.00  180
 41  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00-120.00  180
 42  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00-180.00  180
 43  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00 -60.00  180
 44  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00  30.00  180
 45  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00 150.00  180
 46  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00  90.00  180
 47  \w   -153.00 -63.00   0.50    2.00    --  -82.50 -77.00-150.00  180
;
_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      -0.0012353000
_diffrn_orient_matrix_UB_12      0.2256229000
_diffrn_orient_matrix_UB_13      -0.0472470000
_diffrn_orient_matrix_UB_21      -0.0170780000
_diffrn_orient_matrix_UB_22      -0.1427221000
_diffrn_orient_matrix_UB_23      -0.0795786000
_diffrn_orient_matrix_UB_31      -0.0910744000
_diffrn_orient_matrix_UB_32      0.0237064000
_diffrn_orient_matrix_UB_33      -0.0290414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47108
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.698
_diffrn_reflns_theta_min         4.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (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    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(3)
_refine_ls_extinction_coef       0.0027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5775
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0197
_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^)+(0.0325P)^2^+0.3667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0529
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                5768
_reflns_number_total             5775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06723_si_003.cif
_cod_data_source_block           rwh1_abs
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H21 N O3 S)'
_cod_original_formula_sum        'C38 H42 N2 O6 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     686.85
_cod_database_code               4131548
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C38H42N2O6S2
_chemical_oxdiff_usercomment     'Crystallized from acetone'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C111(H111), C211(H211)
2.b Secondary CH2 refined with riding coordinates:
 C108(H10A,H10B), C110(H11A,H11B), C208(H20A,H20B), C210(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105), C113(H113),
 C114(H114), C115(H115), C116(H116), C117(H117), C201(H201), C202(H202),
 C203(H203), C204(H204), C205(H205), C213(H213), C214(H214), C215(H215),
 C216(H216), C217(H217)
2.d Idealised Me refined as rotating group:
 C118(H11C,H11D,H11E), C119(H11F,H11G,H11H), C218(H21C,H21D,H21E), C219(H21F,
 H21G,H21H)
;
_shelx_res_checksum              75989
_shelx_hkl_checksum              84221
_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 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.740