Palladium- and Brønsted acid-catalyzed enantio-, site- and E/Z-selective addition of alkylidenecyclopropanes with imines
Liu, Xin-Lian; Lin, Han-Ze; Tan, Lu-Qi; Peng, Jin-Bao; Chemical Science 14 (2023) 2348–2352; doi:10.1039/D2SC05674G

data_1568446
_publ_section_title
;
 Palladium- and Br\/onsted acid-catalyzed enantio-, site- and
 E/Z-selective addition of alkylidenecyclopropanes with imines
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2348
_journal_page_last               2352
_journal_paper_doi               10.1039/D2SC05674G
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 N O2 S'
_chemical_formula_sum            'C24 H23 N O2 S'
_chemical_formula_weight         389.49
_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
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2czbvk
_audit_creation_date             2022-08-28
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-29 deposited with the CCDC.	2023-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3434(2)
_cell_length_b                   9.5869(3)
_cell_length_c                   25.2570(6)
_cell_measurement_reflns_used    4436
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5780
_cell_measurement_theta_min      4.9360
_cell_volume                     2020.24(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_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      8.00  81.00   0.50    0.50    --   42.30 -82.00-150.00  146
  2  \w     83.00 131.00   0.50    0.50    --   42.30  77.00 -60.00   96
  3  \w     92.00 132.00   0.50    0.50    --   42.30  77.00-180.00   80
  4  \w     81.00 125.00   0.50    0.50    --   42.30  77.00 120.00   88
  5  \w    136.00 185.00   0.50    0.56    --  102.30  50.00   0.00   98
  6  \w     92.00 118.00   0.50    0.56    --  102.30  82.00 150.00   52
  7  \w     92.00 122.00   0.50    0.56    --  102.30  82.00-120.00   60
  8  \w    146.00 192.00   0.50    0.56    --  102.30  82.00 150.00   92
  9  \w     48.00 118.00   0.50    0.56    --  102.30 -64.00 150.00  140
 10  \w    132.00 175.00   0.50    0.56    --  102.30  82.00-120.00   86
 11  \w     74.00 131.00   0.50    0.56    --  102.30  50.00   0.00  114
 12  \w    142.00 191.00   0.50    0.56    --  102.30  82.00 -90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1437661000
_diffrn_orient_matrix_UB_12      0.0072857000
_diffrn_orient_matrix_UB_13      -0.0382248000
_diffrn_orient_matrix_UB_21      0.0775880000
_diffrn_orient_matrix_UB_22      0.1126656000
_diffrn_orient_matrix_UB_23      0.0350415000
_diffrn_orient_matrix_UB_31      0.0860340000
_diffrn_orient_matrix_UB_32      -0.1143782000
_diffrn_orient_matrix_UB_33      0.0321073000
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6222
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.987
_diffrn_reflns_theta_min         3.500
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.063(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0393P)^2^+0.8673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.724
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                3280
_reflns_number_total             3382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05674g2.cif
_cod_data_source_block           04-0817
_cod_depositor_comments          'Adding full bibliography for 1568446.cif.'
_cod_database_code               1568446
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23),
  C24(H24)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              16060
_shelx_hkl_checksum              54527
_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 2.576
_oxdiff_exptl_absorpt_empirical_full_min 0.557