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_1558154
_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 ad
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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             2019-05-13
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.90430(10)
_cell_length_b                   10.79480(10)
_cell_length_c                   31.6319(2)
_cell_measurement_reflns_used    39460
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      74.2070
_cell_measurement_theta_min      4.3100
_cell_volume                     3040.46(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_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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     30.00  74.00   1.00    1.00    --    0.00  38.00  60.00   44
  2  \w    -19.00  82.00   1.00    1.00    --    0.00  38.00-150.00  101
  3  \w     60.00  88.00   1.00    1.00    --    0.00  77.00 -30.00   28
  4  \w    -26.00  20.00   1.00    1.00    --    0.00 -19.00 -60.00   46
  5  \w    -71.00 -45.00   1.00    1.00    --    0.00 -19.00 -60.00   26
  6  \w    -14.00  26.00   1.00    1.00    --    0.00  38.00  60.00   40
  7  \w    -17.00  56.00   1.00    1.00    --    0.00  38.00 -30.00   73
  8  \w    -28.00  -3.00   1.00    1.00    --    0.00  77.00 -30.00   25
  9  \w    -30.00  87.00   1.00    1.00    --    0.00  82.00 -90.00  117
 10  \w    -73.00 -33.00   1.00    1.00    --    0.00 -57.00 -60.00   40
 11  \w    -16.00  21.00   1.00    1.00    --    0.00 -57.00 -60.00   37
 12  \w    -13.00  79.00   1.00    1.00    --    0.00  38.00 120.00   92
 13  \w     24.00  49.00   1.00    1.00    --    0.00  77.00 -30.00   25
 14  \w     63.00  88.00   1.00    1.00    --   95.80  81.00 136.93   25
 15  \w     72.00 180.00   1.00    1.00    --   95.80  57.00 -44.20  108
 16  \w    152.00 178.00   1.00    1.00    --   95.80  78.00  52.49   26
 17  \w     71.00 163.00   1.00    1.00    --   95.80  58.00-103.70   92
 18  \w    132.00 185.00   1.00    1.00    --   95.80  79.00-156.68   53
 19  \w     65.00  96.00   1.00    1.00    --   95.80  78.00  52.49   31
 20  \w     75.00 121.00   1.00    1.00    --   95.80  45.00 170.13   46
 21  \w     31.00 107.00   1.00    1.00    --   95.80 -82.00  60.00   76
 22  \w     64.00  89.00   1.00    1.00    --   95.80  79.00-156.68   25
 23  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 24  \w     63.00  98.00   1.00    1.00    --   95.80  82.00  30.00   35
 25  \w    102.00 128.00   1.00    1.00    --   95.80  82.00  30.00   26
 26  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 27  \w    118.00 185.00   1.00    1.00    --   95.80  77.00   0.00   67
 28  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 29  \w    105.00 184.00   1.00    1.00    --   95.80  82.00  60.00   79
 30  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 31  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 120.00  122
 32  \w     64.00 127.00   1.00    1.00    --   95.80 -82.00 -90.00   63
 33  \w    146.00 172.00   1.00    1.00    --   95.80  79.00 -40.56   26
 34  \w    153.00 184.00   1.00    1.00    --   95.80  70.00  90.93   31
 35  \w    117.00 183.00   1.00    1.00    --   95.80  82.00 150.00   66
 36  \w     63.00  93.00   1.00    1.00    --   95.80  82.00 150.00   30
 37  \w     11.00  58.00   1.00    1.00    --   95.80 -82.00 -90.00   47
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 39  \w     71.00 108.00   1.00    1.00    --   95.80  61.00-150.00   37
 40  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 41  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 42  \w     65.00 167.00   1.00    1.00    --   95.80  77.00 -30.00  102
 43  \w     52.00  78.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 44  \w     18.00 120.00   1.00    1.00    --   95.80 -61.00 120.00  102
 45  \w     64.00 113.00   1.00    1.00    --   95.80  79.00 -40.56   49
 46  \w     71.00 123.00   1.00    1.00    --   95.80  61.00-120.00   52
 47  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 49  \w     75.00 156.00   1.00    1.00    --   95.80  45.00-150.00   81
 50  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 51  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 52  \w    119.00 144.00   1.00    1.00    --   95.80  82.00   0.00   25
 53  \w     75.00 101.00   1.00    1.00    --   95.80  61.00  90.00   26
 54  \w    114.00 181.00   1.00    1.00    --   95.80  61.00  90.00   67
 55  \w    113.00 138.00   1.00    1.00    --   95.80  77.00 120.00   25
 56  \w     75.00 100.00   1.00    1.00    --   95.80  45.00  30.00   25
 57  \w     75.00 103.00   1.00    1.00    --   95.80  45.00  90.00   28
 58  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 59  \w     63.00  89.00   1.00    1.00    --   95.80  81.00 -57.09   26
 60  \w     71.00  97.00   1.00    1.00    --   95.80  59.00 134.30   26
 61  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 62  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 63  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 64  \w    140.00 174.00   1.00    1.00    --   95.80  45.00 120.00   34
 65  \w     76.00 103.00   1.00    1.00    --   95.80  45.00 120.00   27
 66  \w    103.00 128.00   1.00    1.00    --   95.80  82.00-120.00   25
 67  \w    120.00 185.00   1.00    1.00    --   95.80  81.00 136.93   65
 68  \w     93.00 119.00   1.00    1.00    --   95.80 -82.00-180.00   26
 69  \w     75.00 114.00   1.00    1.00    --   95.80  45.00 -60.00   39
 70  \w     68.00 167.00   1.00    1.00    --   95.80  69.00  25.48   99
 71  \w     68.00  93.00   1.00    1.00    --   95.80  70.00  90.93   25
 72  \w    130.00 165.00   1.00    1.00    --   95.80  44.00-163.69   35
 73  \w     82.00 111.00   1.00    1.00    --   95.80 -82.00 -30.00   29
 74  \w     76.00 102.00   1.00    1.00    --   95.80  44.00-163.69   26
;
_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      -0.0112666000
_diffrn_orient_matrix_UB_12      0.0916480000
_diffrn_orient_matrix_UB_13      0.0371948000
_diffrn_orient_matrix_UB_21      0.0000644000
_diffrn_orient_matrix_UB_22      -0.1092103000
_diffrn_orient_matrix_UB_23      0.0313264000
_diffrn_orient_matrix_UB_31      0.1727098000
_diffrn_orient_matrix_UB_32      0.0060697000
_diffrn_orient_matrix_UB_33      0.0024052000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            75990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.528
_diffrn_reflns_theta_min         4.328
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23950
_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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.9283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6061
_reflns_number_total             6165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01391a2.cif
_cod_data_source_block           exp_815
_cod_depositor_comments
;
 Adding full bibliography for 1558153--1558154.cif.

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H17 N O3 S)'
_cod_original_formula_sum        'C34 H34 N2 O6 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     630.75
_cod_database_code               1558154
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.81
_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:
 C7(H7), C8(H8), C24(H24), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22), C29(H29), C30(H30), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              92400
_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 6.536
_oxdiff_exptl_absorpt_empirical_full_min 0.306