Palladium-catalyzed intramolecular enantioselective C(sp3)–H insertion of donor/donor carbenes
Li, Wendeng; Zhang, He; Chen, Kai; Jiang, Huanfeng; Sun, Jianwei; Zhu, Shifa; Chemical Science 13 (2022) 12396–12402; doi:10.1039/D2SC03524C

data_1567702
_publ_section_title
;
 Palladium-catalyzed intramolecular enantioselective C(sp3)--H insertion
 of donor/donor carbenes
;
_journal_issue                   42
_journal_name_full               'Chemical Science'
_journal_page_first              12396
_journal_page_last               12402
_journal_paper_doi               10.1039/D2SC03524C
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-04-06 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.94940(10)
_cell_length_b                   10.28380(10)
_cell_length_c                   24.4594(3)
_cell_measurement_reflns_used    15388
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9010
_cell_measurement_theta_min      3.7130
_cell_volume                     1999.56(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      150.00(10)
_diffrn_detector                 'CCD plate'
_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    -89.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  240
  2  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00   0.00  212
  3  \w      6.00 119.00   0.50    0.50    --   95.20 -61.00-150.00  226
  4  \w     76.00 185.00   0.50    0.50    --   95.20  45.00 120.00  218
  5  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00-150.00  242
  6  \w     66.00 185.00   0.50    0.50    --   95.20  77.00 -60.00  238
  7  \w     79.00 185.00   0.50    0.50    --   95.20  30.00 -30.00  212
  8  \w      6.00 112.00   0.50    0.50    --   95.20 -30.00-150.00  212
  9  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00  90.00  212
 10  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00-180.00  212
 11  \w     64.00 185.00   0.50    0.50    --   95.20  82.00-150.00  242
 12  \w     64.00 179.00   0.50    0.50    --   95.20  82.00-180.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0830936000
_diffrn_orient_matrix_UB_12      0.0761389000
_diffrn_orient_matrix_UB_13      -0.0470881000
_diffrn_orient_matrix_UB_21      0.0455000000
_diffrn_orient_matrix_UB_22      -0.1101128000
_diffrn_orient_matrix_UB_23      -0.0399802000
_diffrn_orient_matrix_UB_31      -0.1691927000
_diffrn_orient_matrix_UB_32      -0.0669908000
_diffrn_orient_matrix_UB_33      0.0123416000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.184
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0578P)^2^+0.4597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3861
_reflns_number_total             3985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03524c2.cif
_cod_data_source_block           53-1
_cod_depositor_comments
'Adding full bibliography for 1567702--1567704.cif.'
_cod_database_code               1567702
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C6(H6), C17(H17), C3(H3), C14(H14), C12(H12), C4(H4),
 C13(H13)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C20(H20A,H20B,
 H20C)
;
_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 15.887
_oxdiff_exptl_absorpt_empirical_full_min 0.660