A copper-catalyzed three-component reaction of dithioacetals with diazo ketones and ketimines
Sha, Hong-Kai; Qian, Yu; Yang, Xiangji; Dong, Kuiyong; Xu, Xinfang; Hu, Wenhao; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01679F

data_7158921
_publ_section_title
;
 A copper-catalyzed three-component reaction of dithioacetals with diazo
 ketones and ketimines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01679F
_journal_year                    2022
_chemical_formula_moiety         'C27 H22 O3 S2'
_chemical_formula_sum            'C27 H22 O3 S2'
_chemical_formula_weight         458.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-16 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                103.079(2)
_cell_angle_beta                 97.132(2)
_cell_angle_gamma                100.779(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2253(2)
_cell_length_b                   11.0686(2)
_cell_length_c                   22.4374(5)
_cell_measurement_reflns_used    17895
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9910
_cell_measurement_theta_min      4.0740
_cell_volume                     2392.88(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.947
_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     90.00 151.00   0.50    0.10    --  105.51 105.00 -33.00  122
  2  \w    106.00 162.00   0.50    0.10    --  105.51  30.00 -60.00  112
  3  \w    138.00 173.00   0.50    0.10    --  105.51  61.00  60.00   70
  4  \w    105.00 176.00   0.50    0.10    --  105.51  45.00 120.00  142
  5  \w     87.00 115.00   0.50    0.10    --  105.51  61.00  60.00   56
  6  \w    -27.00  16.00   0.50    0.05    --   45.43 -19.00 -60.00   86
  7  \w      6.00  70.00   0.50    0.05    --   45.43 -77.00   0.00  128
  8  \w     34.00 103.00   0.50    0.10    --  105.51 -77.00-150.00  138
  9  \w     32.00  69.00   0.50    0.10    --  105.51 -61.00-150.00   74
 10  \w     36.00  62.00   0.50    0.10    --  105.51 -77.00  90.00   52
 11  \w     76.00 107.00   0.50    0.10    --  105.51 -77.00  90.00   62
 12  \w     66.00  91.00   0.50    0.10    --  105.51 -94.00 120.00   50
 13  \w     36.00  78.00   0.50    0.10    --  105.51 -94.00  30.00   84
 14  \w     35.00 107.00   0.50    0.10    --  105.51-105.00  -2.91  144
 15  \w     65.00  90.00   0.50    0.05    --   45.43-125.00 -90.00   50
 16  \w      6.00  51.00   0.50    0.05    --   45.43-105.00-133.00   90
 17  \w     74.00 107.00   0.50    0.10    --  105.51-105.00-133.00   66
 18  \w    -12.00  24.00   0.50    0.05    --  -45.43  19.00-150.00   72
 19  \w    -65.00 -27.00   0.50    0.10    -- -100.00  61.00-180.00   76
 20  \w    -24.00  29.00   0.50    0.05    --  -45.43  19.00 150.00  106
 21  \w    -69.00 -28.00   0.50    0.10    -- -100.00  61.00  90.00   82
 22  \w   -120.00 -30.00   0.50    0.10    -- -100.00 136.00  40.37  180
 23  \w    -99.00 -31.00   0.50    0.10    -- -100.00 125.00 150.00  136
 24  \w   -112.00 -28.00   0.50    0.10    -- -100.00 125.00  90.00  168
 25  \w   -108.00 -60.00   0.50    0.10    -- -100.00 111.00  54.65   96
 26  \w    -57.00 -11.00   0.50    0.05    --  -45.43 105.00 -33.00   92
 27  \w    -92.00 -54.00   0.50    0.10    -- -100.00 105.00 -33.00   76
 28  \w   -112.00 -42.00   0.50    0.10    -- -100.00 125.00 -90.00  140
 29  \w   -112.00 -71.00   0.50    0.10    -- -100.00 125.00-180.00   82
 30  \w   -175.00 -83.00   0.50    0.10    -- -100.00 -30.00-120.00  184
 31  \w   -173.00-118.00   0.50    0.10    -- -100.00 -61.00 -90.00  110
 32  \w   -113.00 -81.00   0.50    0.10    -- -100.00 -61.00 -90.00   64
 33  \w   -163.00 -85.00   0.50    0.10    -- -100.00 -45.00 -60.00  156
 34  \w   -168.00-142.00   0.50    0.10    -- -100.00 -77.00  30.00   52
 35  \w   -123.00 -76.00   0.50    0.10    -- -100.00 -77.00  30.00   94
 36  \w   -117.00 -29.00   0.50    0.05    --  -45.43 -57.00-120.00  176
 37  \w   -117.00 -35.00   0.50    0.05    --  -45.43 -77.00-180.00  164
 38  \w   -124.00 -86.00   0.50    0.10    -- -100.00-105.00-133.00   76
 39  \w   -153.00-127.00   0.50    0.10    -- -100.00-105.00-133.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1101302000
_diffrn_orient_matrix_UB_12      0.0756817000
_diffrn_orient_matrix_UB_13      -0.0080522000
_diffrn_orient_matrix_UB_21      -0.0136291000
_diffrn_orient_matrix_UB_22      0.0149168000
_diffrn_orient_matrix_UB_23      0.0687559000
_diffrn_orient_matrix_UB_31      0.1092784000
_diffrn_orient_matrix_UB_32      0.1246253000
_diffrn_orient_matrix_UB_33      0.0182099000
_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  0.0449
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30182
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.502
_diffrn_reflns_theta_min         4.108
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         9400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0681P)^2^+2.5567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8056
_reflns_number_total             9400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01679f2.cif
_cod_data_source_block           shhk_210812_auto
_cod_database_code               7158921
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.555
_reflns_odcompleteness_completeness 99.86
_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
2.a Ternary CH refined with riding coordinates:
 C00W(H00W), C01A(H01C)
2.b Secondary CH2 refined with riding coordinates:
 C015(H01H,H01J), C017(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00T(H00T), C010(H010), C013(H013),
 C018(H018), C01B(H01L), C01D(H01D), C01E(H01M), C01F(H01F), C01G(H01N),
 C01H(H01Q), C01I(H01I), C01J(H01R), C01K(H01K), C01L(H01S), C01M(H01W),
 C01N(H01X), C01O(H01O), C01P(H01P), C01Q(H01Y), C01R(H01Z), C01T(H01T),
 C01U(H01U), C01V(H01V)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              94897
_shelx_fab_checksum              722
_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 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.657