Copper/ruthenium relay catalysis enables 1,6-double chiral inductions with stereodivergence
Yang, Hao-Ran; Cheng, Xiang; Chang, Xin; Wang, Zuo-Fei; Dong, Xiu-Qin; Wang, Chun-Jiang; Chemical Science 15 (2024) 10135–10145; doi:10.1039/D4SC01804D

data_1571654
_publ_section_title
;
 Copper/ruthenium relay catalysis enables 1,6-double chiral inductions
 with stereodivergence
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              10135
_journal_page_last               10145
_journal_paper_doi               10.1039/D4SC01804D
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H31 N O5 S'
_chemical_formula_sum            'C24 H31 N O5 S'
_chemical_formula_weight         445.55
_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             2023-07-03
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-01-28 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.9320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8686(2)
_cell_length_b                   5.43670(10)
_cell_length_c                   22.9849(2)
_cell_measurement_reflns_used    29464
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.1410
_cell_measurement_theta_min      1.9110
_cell_volume                     2349.13(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_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     27.00  52.00   0.50    0.05    --    8.00  41.00  71.52   50
  2  \w     31.00  56.00   0.50    0.05    --   12.00  41.00  27.93   50
  3  \w     35.00  60.00   0.50    0.05    --   16.00  41.00  64.10   50
  4  \w     35.00  60.00   0.50    0.05    --   16.00  41.00  76.37   50
  5  \w     39.00  64.00   0.50    0.05    --   20.00  41.00  84.56   50
  6  \w     39.00  64.00   0.50    0.05    --   20.00  41.00  81.80   50
  7  \w     35.00  60.00   0.50    0.05    --   16.00  41.00 113.78   50
  8  \w     39.00  64.00   0.50    0.05    --   20.00  41.00 123.75   50
  9  \w     43.00  68.00   0.50    0.05    --   24.00  41.00 141.07   50
 10  \w     31.00  56.00   0.50    0.05    --   12.00  40.00 151.38   50
 11  \w     55.00  80.00   0.50    0.05    --   36.00  41.00 120.72   50
 12  \w     31.00  56.00   0.50    0.05    --   12.00  40.00 103.92   50
 13  \w     47.00  72.00   0.50    0.05    --   28.00  40.00  46.31   50
 14  \w     43.00  68.00   0.50    0.05    --   24.00  37.00 120.73   50
 15  \w     43.00  68.00   0.50    0.05    --   24.00  41.00  31.32   50
 16  \w     55.00  80.00   0.50    0.05    --   36.00  41.00  -5.19   50
 17  \w     55.00  80.00   0.50    0.05    --   36.00  40.00   4.38   50
 18  \w     69.00  94.00   0.50    0.05    --   62.88  14.00 -70.00   50
 19  \w     91.00 116.00   0.50    0.05    --   76.80  14.00 -70.00   50
 20  \w     62.00  88.00   0.50    0.05    --   72.82  14.00 -70.00   52
 21  \w     34.00  60.00   0.50    0.05    --   72.82-125.00   0.00   52
 22  \w     32.00  58.00   0.50    0.05    --   72.82-125.00 -30.00   52
 23  \w     36.00  96.00   0.50    0.05    --   76.80-125.00 -60.00  120
 24  \w     39.00  89.00   0.50    0.05    --   72.82-125.00-120.00  100
 25  \w     22.00  74.00   0.50    0.05    --   62.88-125.00-180.00  104
 26  \w      7.00  32.00   0.50    0.05    --   16.00-120.00-116.14   50
 27  \w    -97.00 -72.00   0.50    0.05    --  -52.00 -41.00 -73.24   50
 28  \w   -105.00 -80.00   0.50    0.05    --  -60.00 -41.00 -78.38   50
 29  \w   -109.00 -84.00   0.50    0.05    --  -64.00 -41.00 -70.24   50
 30  \w   -109.00 -83.00   0.50    0.05    --  -64.00 -41.00 -52.57   52
 31  \w    -93.00 -67.00   0.50    0.05    --  -48.00 -40.00  32.72   52
 32  \w   -105.00 -80.00   0.50    0.05    --  -60.00 -41.00  61.54   50
 33  \w   -109.00 -84.00   0.50    0.05    --  -64.00 -41.00  58.82   50
 34  \w   -113.00 -87.00   0.50    0.05    --  -68.00 -41.00  52.49   52
 35  \w   -113.00 -88.00   0.50    0.05    --  -68.00 -39.00 -34.91   50
 36  \w   -113.00 -88.00   0.50    0.05    --  -68.00 -38.00 -16.75   50
 37  \w   -117.00 -91.00   0.50    0.05    --  -72.00 -38.00 -18.26   52
 38  \w   -101.00 -76.00   0.50    0.05    --  -56.00 -37.00 -40.37   50
 39  \w    -97.00 -72.00   0.50    0.05    --  -52.00 -36.00 -19.68   50
 40  \w   -112.00 -87.00   0.50    0.05    --  -68.00 -33.00  66.68   50
 41  \w   -120.00 -94.00   0.50    0.05    --  -76.60 -33.00  68.90   52
 42  \w   -100.00 -74.00   0.50    0.05    --  -56.00 -36.00   9.95   52
 43  \w   -100.00 -74.00   0.50    0.05    --  -56.00 -31.00  47.18   52
 44  \w    -99.00 -74.00   0.50    0.05    --  -56.00 -32.00  54.69   50
 45  \w   -123.00 -94.00   0.50    0.05    --  -76.60 -31.00  60.98   58
 46  \w   -106.00 -81.00   0.50    0.05    --  -60.00 -35.00  -2.60   50
 47  \w   -119.00 -88.00   0.50    0.05    --  -76.60 -22.00   9.64   62
 48  \w   -122.00 -97.00   0.50    0.05    --  -76.60 -30.00 -78.55   50
 49  \w   -120.00 -94.00   0.50    0.05    --  -76.60 -32.00 -87.05   52
 50  \w   -121.00 -76.00   0.50    0.05    --  -81.50 -15.00-120.00   90
 51  \w    -90.00 -62.00   0.50    0.05    --  -63.33 -15.00-180.00   56
 52  \w   -125.00 -75.00   0.50    0.05    --  -81.50 -15.00-180.00  100
 53  \w   -113.00 -88.00   0.50    0.05    --  -81.50 -15.00 -30.00   50
 54  \w   -125.00 -80.00   0.50    0.05    --  -81.50 -14.00 118.00   90
 55  \w    -98.00 -64.00   0.50    0.05    --  -76.34 -14.00 118.00   68
 56  \w   -103.00 -78.00   0.50    0.05    --  -63.33 -14.00 118.00   50
 57  \w    -89.00 -63.00   0.50    0.05    --  -71.69 -14.00 118.00   52
 58  \w    -53.00 -27.00   0.50    0.05    --  -63.33 125.00-120.00   52
 59  \w    -95.00 -38.00   0.50    0.05    --  -76.34 125.00 -90.00  114
 60  \w   -101.00 -53.00   0.50    0.05    --  -81.50 125.00-120.00   96
 61  \w    -78.00 -44.00   0.50    0.05    --  -81.50 125.00-180.00   68
 62  \w    -95.00 -45.00   0.50    0.05    --  -81.50 125.00 -60.00  100
 63  \w    -93.00 -58.00   0.50    0.05    --  -76.34 125.00 -30.00   70
 64  \w   -101.00 -56.00   0.50    0.05    --  -81.50 125.00   0.00   90
 65  \w    -65.00 -39.00   0.50    0.05    --  -76.34 125.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0787399000
_diffrn_orient_matrix_UB_12      0.0476639000
_diffrn_orient_matrix_UB_13      0.0202896000
_diffrn_orient_matrix_UB_21      0.0172096000
_diffrn_orient_matrix_UB_22      0.0209062000
_diffrn_orient_matrix_UB_23      -0.0641377000
_diffrn_orient_matrix_UB_31      -0.0147245000
_diffrn_orient_matrix_UB_32      0.2785590000
_diffrn_orient_matrix_UB_33      0.0013550000
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37596
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.776
_diffrn_reflns_theta_min         1.929
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(13)
_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     569
_refine_ls_number_reflns         8532
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0655P)^2^+0.7750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                8325
_reflns_number_total             8532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01804d2.cif
_cod_data_source_block           20230703-yhr-rrrp_r_auto
_cod_depositor_comments
;
Adding full bibliography for 1571654--1571655.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H62 N2 O10 S2'
_cod_original_formula_weight         891.11
_cod_original_formula_moiety         '2(C24 H31 N O5 S)'
_cod_original_formula_units_Z            2
_cod_database_code               1571654
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNOHS
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00L), C00Y(H00Y), C013(H013), C019(H019)
2.b Secondary CH2 refined with riding coordinates:
 C01C(H01A,H01C), C01E(H01G,H01H), C01J(H01X,H01Y), C01Q(H3,HF)
2.c Aromatic/amide H refined with riding coordinates:
 N00C(H00C), N00D(H00D), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C010(H010), C011(H011), C014(H014), C015(H015), C016(H016), C017(H017),
 C018(H018), C01A(H01R), C01B(H01B), C01F(H01S), C01I(H01W), C01P(H2)
2.d Idealised Me refined as rotating group:
 C01D(H01D,H01E,H01F), C01G(H01I,H01J,H01K), C01H(H01T,H01U,H01V), C01K(H01Z,H,
 HA), C01L(H01L,H01M,H01N), C01M(H01O,H01P,H01Q), C01N(H01,HB,HC), C01O(H1,HD,
 HE)
2.e Idealised tetrahedral OH refined as rotating group:
 O00B(H00B), O00E(H00E)
;
_shelx_res_checksum              66309
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.665