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_1571655
_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         445.56
_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             2023-07-05
_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                 116.175(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6662(4)
_cell_length_b                   5.60080(10)
_cell_length_c                   36.6350(11)
_cell_measurement_reflns_used    4817
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.2180
_cell_measurement_theta_min      2.6830
_cell_volume                     2332.40(14)
_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 2018/2 (Sheldrick, 2018)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.959
_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   -106.00 -53.00   0.50    0.30    --  -63.03 -15.00 120.00  106
  2  \w   -104.00 -68.00   0.50    0.30    --  -71.69 -15.00 120.00   72
  3  \w   -116.00 -84.00   0.50    0.30    --  -76.15 -15.00 -30.00   64
  4  \w    -98.00 -72.00   0.50    0.30    --  -76.15 -15.00 -90.00   52
  5  \w   -106.00 -53.00   0.50    0.30    --  -63.03 -15.00-120.00  106
  6  \w   -100.00 -70.00   0.50    0.30    --  -71.69 -15.00-120.00   60
  7  \w   -121.00 -91.00   0.50    0.30    --  -81.50 -15.00  30.00   60
  8  \w   -125.00 -73.00   0.50    0.30    --  -81.50 -15.00  90.00  104
  9  \w    -74.00 -41.00   0.50    0.30    --  -81.50 125.00-120.00   66
 10  \w   -100.00 -50.00   0.50    0.30    --  -81.50 125.00-180.00  100
 11  \w    -95.00 -41.00   0.50    0.30    --  -81.50 125.00 -60.00  108
 12  \w    -54.00 -25.00   0.50    0.30    --  -63.03 125.00  60.00   58
 13  \w    -88.00 -49.00   0.50    0.30    --  -81.50 125.00 120.00   78
 14  \w     66.00 118.00   0.50    0.30    --   76.61  15.00 -90.00  104
 15  \w     37.00  83.00   0.50    0.30    --   76.61-125.00-120.00   92
 16  \w     45.00  87.00   0.50    0.30    --   76.61-125.00-180.00   84
 17  \w     42.00  75.00   0.50    0.30    --   76.61-125.00 -60.00   66
 18  \w     26.00  66.00   0.50    0.30    --   62.57-125.00  30.00   80
 19  \w     38.00  64.00   0.50    0.30    --   76.61-125.00  60.00   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      0.0794661000
_diffrn_orient_matrix_UB_12      -0.2173721000
_diffrn_orient_matrix_UB_13      0.0196095000
_diffrn_orient_matrix_UB_21      -0.0743533000
_diffrn_orient_matrix_UB_22      -0.0620946000
_diffrn_orient_matrix_UB_23      0.0225219000
_diffrn_orient_matrix_UB_31      -0.0807182000
_diffrn_orient_matrix_UB_32      -0.1566136000
_diffrn_orient_matrix_UB_33      -0.0361224000
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15118
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.793
_diffrn_reflns_theta_min         2.688
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  0.98116
_exptl_absorpt_correction_T_min  0.98116
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.051
_refine_diff_density_max         1.587
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1219P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.431
_reflns_Friedel_fraction_full    0.571
_reflns_Friedel_fraction_max     0.511
_reflns_number_gt                5635
_reflns_number_total             7349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01804d2.cif
_cod_data_source_block           20230705-yhr-rrrp_s_4
_cod_depositor_comments
'Adding full bibliography for 1571654--1571655.cif.'
_cod_original_cell_volume        2332.40(13)
_cod_database_code               1571655
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNSO
_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:
 C00H(H00H), C00J(H00J), C00T(H00T), C012(H012)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01T,H01U), C01G(H2,HB), C01L(H01I,H01J), C01M(H01K,H01L)
2.c Aromatic/amide H refined with riding coordinates:
 N00D(H00D), N00E(H00E), C00F(H00F), C00I(H00I), C00L(H00L), C00M(H00M),
 C00P(H00P), C00S(H00S), C00V(H00V), C00W(H00W), C00Z(H00Z), C010(H010),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C01A(H01A),
 C01C(H01C), C01D(H01Z), C01E(H01), C01F(H1), C01J(H4), C01P(H01P)
2.d Idealised Me refined as rotating group:
 C019(H01V,H01W,H01X), C01B(H01Y,H,HA), C01H(H3,HC,HD), C01I(H01B,H01D,H01E),
 C01K(H01F,H01G,H01H), C01N(H01M,H01N,H01O), C01O(H5,HE,HF), C01Q(H01Q,H01R,
 H01S)
2.e Idealised tetrahedral OH refined as rotating group:
 O006(H006), O008(H008)
;
_shelx_res_checksum              37322
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.632