Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel cocatalysis.
Wang, Rui; Wang, Chuan; Chemical science 14 (2023) 6449–6456; doi:10.1039/d3sc01945d

data_1569197
_publ_section_title
;
 Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel
 cocatalysis.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              6449
_journal_page_last               6456
_journal_paper_doi               10.1039/d3sc01945d
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H31 N3 O2 S'
_chemical_formula_sum            'C24 H31 N3 O2 S'
_chemical_formula_weight         425.58
_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'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2fdjn1
_audit_creation_date             2023-03-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-05 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.26014(12)
_cell_length_b                   11.7541(2)
_cell_length_c                   21.9162(3)
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6450
_cell_measurement_theta_min      5.1860
_cell_volume                     2385.46(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -66.00  30.00   1.00    2.00    --  -41.76  38.00-120.00   96
  2  \w    -82.00 -47.00   1.00    2.00    --  -41.76 125.00 120.00   35
  3  \w    -83.00 -33.00   1.00    2.00    --  -41.76 -38.00  30.00   50
  4  \w     33.00 102.00   1.00    6.00    --  106.05 -45.00   0.00   69
  5  \w     81.00 166.00   1.00    6.00    --  106.05  45.00-180.00   85
  6  \w    107.00 174.00   1.00    6.00    --  106.05  96.00  14.00   67
  7  \w     94.00 178.00   1.00    6.00    --  106.05  45.00 120.00   84
  8  \w     47.00  84.00   1.00    6.00    --  106.05-125.00   0.00   37
  9  \w    113.00 178.00   1.00    6.00    --  106.05  77.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294008000
_diffrn_orient_matrix_UB_12      0.0949289000
_diffrn_orient_matrix_UB_13      0.0468692000
_diffrn_orient_matrix_UB_21      -0.1079070000
_diffrn_orient_matrix_UB_22      -0.0780293000
_diffrn_orient_matrix_UB_23      0.0333711000
_diffrn_orient_matrix_UB_31      0.1231332000
_diffrn_orient_matrix_UB_32      -0.0455947000
_diffrn_orient_matrix_UB_33      0.0403966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8750
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.870
_diffrn_reflns_theta_min         4.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_coef       0.0052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0771P)^2^+0.2115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                4341
_reflns_number_total             4615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01945d2.cif
_cod_data_source_block           wr-nnhts_auto
_cod_depositor_comments          'Adding full bibliography for 1569197.cif.'
_cod_database_code               1569197
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C202H20N2O2S1
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.750
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
1.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C8(H8), C7(H7), C19(H19), C9(H9), C23(H23), C20(H20),
 C22(H22)
1.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              94473
_shelx_hkl_checksum              80097
_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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.798