Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions.
Tao, Mengna; Tu, Youshao; Liu, Yu; Wu, Haihong; Liu, Lu; Zhang, Junliang; Chemical science 11 (2020) 6283–6288; doi:10.1039/d0sc01391a

data_1558153
_publ_section_title
;
 Pd/Xiang-Phos-catalyzed enantioselective intermolecular
 carboheterofunctionalization under mild conditions.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6283
_journal_page_last               6288
_journal_paper_doi               10.1039/d0sc01391a
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H23 N O5 S'
_chemical_formula_sum            'C25 H23 N O5 S'
_chemical_formula_weight         449.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-10
_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.	2020-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.91430(10)
_cell_length_b                   12.5172(3)
_cell_length_c                   14.5829(3)
_cell_measurement_reflns_used    13639
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2160
_cell_measurement_theta_min      4.6380
_cell_volume                     1070.54(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      100.00(10)
_diffrn_detector                 'CCD plate'
_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     -7.00  88.00   1.00    1.00    --    0.00  57.00  30.00   95
  2  \w    -20.00  16.00   1.00    1.00    --    0.00  57.00-150.00   36
  3  \w     38.00  64.00   1.00    1.00    --    0.00  38.00  30.00   26
  4  \w     16.00  89.00   1.00    1.00    --    0.00  57.00 -90.00   73
  5  \w    -23.00  12.00   1.00    1.00    --    0.00  57.00 -90.00   35
  6  \w    -23.00  53.00   1.00    1.00    --    0.00  19.00  90.00   76
  7  \w     23.00  59.00   1.00    1.00    --    0.00  57.00-150.00   36
  8  \w    -18.00  18.00   1.00    1.00    --    0.00  38.00  30.00   36
  9  \w      5.00  71.00   1.00    1.00    --    0.00  38.00 -30.00   66
 10  \w    -19.00  57.00   1.00    1.00    --    0.00  57.00 150.00   76
 11  \w    125.00 185.00   1.00    1.00    --   95.80  68.00 -31.97   60
 12  \w     65.00  91.00   1.00    1.00    --   95.80  78.00  25.77   26
 13  \w    121.00 172.00   1.00    1.00    --   95.80  78.00  25.77   51
 14  \w     75.00 143.00   1.00    1.00    --   95.80  45.00-180.00   68
 15  \w    110.00 185.00   1.00    1.00    --   95.80  80.00 138.88   75
 16  \w     70.00  96.00   1.00    1.00    --   95.80  68.00 -31.97   26
 17  \w     67.00  93.00   1.00    1.00    --   95.80  71.00  86.65   26
 18  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 138.88   26
 19  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 20  \w     79.00 127.00   1.00    1.00    --   95.80 -82.00 150.00   48
 21  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-180.00   26
 22  \w     65.00  97.00   1.00    1.00    --   95.80  77.00 120.00   32
 23  \w     75.00 185.00   1.00    1.00    --   95.80  45.00-120.00  110
 24  \w     15.00 126.00   1.00    1.00    --   95.80 -82.00  30.00  111
 25  \w     64.00  90.00   1.00    1.00    --   95.80  82.00   0.00   26
 26  \w    136.00 162.00   1.00    1.00    --   95.80  82.00   0.00   26
 27  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 28  \w     43.00  68.00   1.00    1.00    --   95.80 -82.00-150.00   25
 29  \w     86.00 127.00   1.00    1.00    --   95.80 -82.00-150.00   41
 30  \w    137.00 164.00   1.00    1.00    --   95.80  76.00  51.51   27
 31  \w     65.00  91.00   1.00    1.00    --   95.80  76.00 133.57   26
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  \w     75.00 118.00   1.00    1.00    --   95.80  45.00 -30.00   43
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 35  \w     65.00 106.00   1.00    1.00    --   95.80  76.00  51.51   41
 36  \w     94.00 185.00   1.00    1.00    --   95.80  82.00  90.00   91
 37  \w    155.00 185.00   1.00    1.00    --   95.80  45.00 -30.00   30
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 39  \w     39.00 125.00   1.00    1.00    --   95.80 -82.00 -60.00   86
 40  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 41  \w     75.00 185.00   1.00    1.00    --   95.80  45.00  60.00  110
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 43  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 150.00   26
 44  \w     75.00 183.00   1.00    1.00    --   95.80  45.00-150.00  108
 45  \w     75.00 103.00   1.00    1.00    --   95.80  45.00  30.00   28
 46  \w     64.00 126.00   1.00    1.00    --   95.80 -77.00  60.00   62
 47  \w     71.00 105.00   1.00    1.00    --   95.80  61.00 -90.00   34
 48  \w    125.00 183.00   1.00    1.00    --   95.80  61.00 -90.00   58
 49  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 50  \w     65.00 128.00   1.00    1.00    --   95.80  77.00 -30.00   63
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 52  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 53  \w     34.00  59.00   1.00    1.00    --   95.80 -77.00  60.00   25
 54  \w     38.00 127.00   1.00    1.00    --   95.80 -82.00 120.00   89
 55  \w     68.00  94.00   1.00    1.00    --   95.80  69.00   4.23   26
 56  \w    131.00 157.00   1.00    1.00    --   95.80  71.00  86.65   26
 57  \w    134.00 177.00   1.00    1.00    --   95.80  51.00 -58.52   43
 58  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-120.00   26
 59  \w     71.00 123.00   1.00    1.00    --   95.80  61.00  90.00   52
 60  \w     66.00 116.00   1.00    1.00    --   95.80  77.00  60.00   50
 61  \w     74.00 108.00   1.00    1.00    --   95.80  51.00 -58.52   34
;
_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      0.2612602000
_diffrn_orient_matrix_UB_12      0.0004696000
_diffrn_orient_matrix_UB_13      0.0247260000
_diffrn_orient_matrix_UB_21      0.0247815000
_diffrn_orient_matrix_UB_22      0.0513311000
_diffrn_orient_matrix_UB_23      -0.0941722000
_diffrn_orient_matrix_UB_31      -0.0124098000
_diffrn_orient_matrix_UB_32      0.1119236000
_diffrn_orient_matrix_UB_33      0.0430371000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20571
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.050
_diffrn_reflns_theta_max         67.050
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13267
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0523
_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^)+(0.1164P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3642
_reflns_number_total             3747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01391a2.cif
_cod_data_source_block           exp_1114
_cod_depositor_comments
;Adding full bibliography for 1558153--1558154.cif.

 Adding full bibliography for 1558153--1558154.cif.
;
_cod_database_code               1558153
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.776
_shelx_estimated_absorpt_t_min   0.671
_reflns_odcompleteness_completeness 100.00
_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:
 C13(H13), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18),
 C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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 3.234
_oxdiff_exptl_absorpt_empirical_full_min 0.352