Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization of norbornene and norbornadiene.
Tao, Mengna; Li, Wenbo; Zhang, Junliang; Chemical communications (Cambridge, England) 56 (2020) 13125–13128; doi:10.1039/d0cc04996d

data_7127292
_publ_section_title
;
 Pd/Xiang-Phos-catalyzed enantioselective intermolecular
 carboheterofunctionalization of norbornene and norbornadiene.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13125
_journal_page_last               13128
_journal_paper_doi               10.1039/d0cc04996d
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 N O2 S'
_chemical_formula_sum            'C20 H21 N O2 S'
_chemical_formula_weight         339.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2019-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-02 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                107.436(5)
_cell_angle_beta                 107.421(7)
_cell_angle_gamma                90.517(6)
_cell_formula_units_Z            1
_cell_length_a                   6.0451(5)
_cell_length_b                   8.3029(4)
_cell_length_c                   9.2867(5)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9950
_cell_measurement_theta_min      5.5960
_cell_volume                     421.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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     -1.00  29.00   1.00    1.00    --    0.00  38.00  60.00   30
  2  \w     23.00  69.00   1.00    1.00    --    0.00  38.00 -60.00   46
  3  \w     56.00  84.00   1.00    1.00    --    0.00  77.00 -60.00   28
  4  \w    -22.00  88.00   1.00    1.00    --    0.00  19.00-150.00  110
  5  \w    -22.00  37.00   1.00    1.00    --    0.00  57.00  90.00   59
  6  \w    -27.00   3.00   1.00    1.00    --    0.00  77.00 -60.00   30
  7  \w      9.00  56.00   1.00    1.00    --    0.00  77.00 -30.00   47
  8  \w    -29.00   2.00   1.00    1.00    --    0.00  77.00 -30.00   31
  9  \w    -18.00   7.00   1.00    1.00    --    0.00  38.00 -60.00   25
 10  \w     49.00  87.00   1.00    1.00    --    0.00  57.00  90.00   38
 11  \w     52.00 123.00   1.00    1.00    --   95.80 -82.00-120.00   71
 12  \w    129.00 178.00   1.00    1.00    --   95.80  45.00  90.00   49
 13  \w     64.00  92.00   1.00    1.00    --   95.80  82.00 -90.00   28
 14  \w     65.00 108.00   1.00    1.00    --   95.80  77.00-150.00   43
 15  \w     77.00 105.00   1.00    1.00    --   95.80  45.00  90.00   28
 16  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -30.00   26
 17  \w     63.00  91.00   1.00    1.00    --   95.80  82.00  30.00   28
 18  \w    123.00 177.00   1.00    1.00    --   95.80  61.00   0.00   54
 19  \w      9.00  53.00   1.00    1.00    --   95.80 -82.00  90.00   44
 20  \w     63.00 105.00   1.00    1.00    --   95.80  82.00-180.00   42
 21  \w     67.00 126.00   1.00    1.00    --   95.80 -82.00  90.00   59
 22  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 23  \w    115.00 184.00   1.00    1.00    --   95.80  77.00 -30.00   69
 24  \w     71.00 140.00   1.00    1.00    --   95.80  61.00 150.00   69
 25  \w     63.00  99.00   1.00    1.00    --   95.80  82.00  60.00   36
 26  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 150.00   26
 27  \w    100.00 184.00   1.00    1.00    --   95.80  82.00 -90.00   84
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 30  \w     72.00 108.00   1.00    1.00    --   95.80  61.00 120.00   36
 31  \w     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 32  \w      7.00 100.00   1.00    1.00    --   95.80 -82.00  60.00   93
 33  \w     76.00 146.00   1.00    1.00    --   95.80  45.00-150.00   70
 34  \w     74.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   54
 35  \w     40.00  66.00   1.00    1.00    --   95.80 -82.00-180.00   26
 36  \w    112.00 185.00   1.00    1.00    --   95.80  77.00 120.00   73
 37  \w     64.00  91.00   1.00    1.00    --   95.80  82.00 150.00   27
 38  \w     75.00 107.00   1.00    1.00    --   95.80  45.00 -90.00   32
 39  \w    119.00 180.00   1.00    1.00    --   95.80  45.00 -90.00   61
 40  \w     75.00 118.00   1.00    1.00    --   95.80  45.00 -30.00   43
 41  \w     76.00 111.00   1.00    1.00    --   95.80  45.00   0.00   35
 42  \w     75.00 108.00   1.00    1.00    --   95.80  45.00  60.00   33
 43  \w    136.00 185.00   1.00    1.00    --   95.80  45.00  60.00   49
 44  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -90.00   26
 45  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  60.00   26
 46  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  90.00   26
 47  \w     66.00  91.00   1.00    1.00    --   95.80  82.00-150.00   25
 48  \w     82.00 107.00   1.00    1.00    --   95.80  30.00 -60.00   25
 49  \w    138.00 163.00   1.00    1.00    --   95.80  30.00 -60.00   25
 50  \w     75.00 104.00   1.00    1.00    --   95.80  45.00  30.00   29
 51  \w    141.00 180.00   1.00    1.00    --   95.80  45.00  30.00   39
 52  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 53  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 54  \w    125.00 179.00   1.00    1.00    --   95.80  77.00 150.00   54
 55  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 56  \w    136.00 162.00   1.00    1.00    --   95.80  77.00-150.00   26
 57  \w     79.00 116.00   1.00    1.00    --   95.80 -82.00 -30.00   37
 58  \w    156.00 181.00   1.00    1.00    --   95.80  82.00  30.00   25
;
_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      -0.1044239000
_diffrn_orient_matrix_UB_12      0.1334403000
_diffrn_orient_matrix_UB_13      -0.0781817000
_diffrn_orient_matrix_UB_21      -0.0914335000
_diffrn_orient_matrix_UB_22      -0.1399386000
_diffrn_orient_matrix_UB_23      -0.1626203000
_diffrn_orient_matrix_UB_31      -0.2300545000
_diffrn_orient_matrix_UB_32      -0.0297218000
_diffrn_orient_matrix_UB_33      0.0323288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5537
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         5.263
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0645
_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^)+(0.1441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                2458
_reflns_number_total             2596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04996d2.cif
_cod_data_source_block           exp_623
_cod_depositor_comments
'Adding full bibliography for 7127292--7127293.cif.'
_cod_database_code               7127292
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 98.67
_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:
 C1(H1), C2(H2), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              41754
_shelx_hkl_checksum              22581
_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 7.101
_oxdiff_exptl_absorpt_empirical_full_min 0.187