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_7158919
_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         'C39 H37 Br N2 O5 S2'
_chemical_formula_sum            'C39 H37 Br N2 O5 S2'
_chemical_formula_weight         757.73
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-25 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                92.9000(10)
_cell_angle_beta                 107.4510(10)
_cell_angle_gamma                105.810(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1834(2)
_cell_length_b                   12.1739(2)
_cell_length_c                   15.8758(2)
_cell_measurement_reflns_used    13112
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.5850
_cell_measurement_theta_min      2.9260
_cell_volume                     1787.67(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_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     82.00 109.00   0.50    2.00    --   46.62  21.00  63.00   54
  2  \w     91.00 176.00   0.50    8.00    --  105.44  21.00  63.00  170
  3  \w     90.00 177.00   0.50    8.00    --  105.44  30.00 150.00  174
  4  \w     68.00 110.00   0.50    8.00    --  105.44-125.00   0.00   84
  5  \w     69.00 110.00   0.50    8.00    --  105.44-125.00 -60.00   82
  6  \w     77.00 110.00   0.50    8.00    --  105.44-125.00-120.00   66
  7  \w     82.00 107.00   0.50    8.00    --  105.44 -77.00-180.00   50
  8  \w     42.00  68.00   0.50    8.00    --  105.44 -77.00-180.00   52
  9  \w     35.00  61.00   0.50    8.00    --  105.44 -61.00-120.00   52
 10  \w     33.00  72.00   0.50    8.00    --  105.44 -61.00 -90.00   78
 11  \w     34.00  73.00   0.50    8.00    --  105.44 -61.00-150.00   78
 12  \w     33.00  70.00   0.50    8.00    --  105.44 -61.00-180.00   74
 13  \w     66.00 120.00   0.50    2.00    --   46.62  38.00-120.00  108
 14  \w     89.00 164.00   0.50    8.00    --  105.44  77.00-180.00  150
 15  \w     34.00  64.00   0.50    2.00    --   46.62  21.00  63.00   60
 16  \w     37.00  72.00   0.50    8.00    --  105.44 -61.00  60.00   70
 17  \w     41.00  71.00   0.50    8.00    --  105.44 -61.00  30.00   60
 18  \w     34.00 102.00   0.50    8.00    --  105.44 -94.00   0.00  136
 19  \w     33.00  64.00   0.50    8.00    --  105.44-125.00   0.00   62
 20  \w     19.00  70.00   0.50    2.00    --   46.62-125.00 120.00  102
 21  \w     52.00 111.00   0.50    8.00    --  105.44-125.00 120.00  118
 22  \w    -24.00   6.00   0.50    2.00    --   46.62 -21.00-102.00   60
 23  \w    -63.00 -21.00   0.50    2.00    --  -46.62  57.00 -60.00   84
 24  \w    -16.00  25.00   0.50    2.00    --  -46.62  57.00 -60.00   82
 25  \w    -24.00  25.00   0.50    2.00    --  -46.62  19.00-150.00   98
 26  \w    -59.00 -30.00   0.50    8.00    -- -100.00 125.00 -60.00   58
 27  \w    -66.00 -41.00   0.50    8.00    -- -100.00 108.00  12.74   50
 28  \w    -67.00 -36.00   0.50    8.00    -- -100.00  61.00 -30.00   62
 29  \w    -26.00  30.00   0.50    2.00    --  -46.62  21.00  63.00  112
 30  \w    -69.00 -28.00   0.50    8.00    -- -100.00  61.00-120.00   82
 31  \w    -96.00 -40.00   0.50    2.00    --  -46.62 -21.00-102.00  112
 32  \w    -89.00 -14.00   0.50    2.00    --  -46.62 125.00 150.00  150
 33  \w    -94.00 -41.00   0.50    8.00    -- -100.00 125.00 150.00  106
 34  \w   -105.00 -49.00   0.50    8.00    -- -100.00 125.00  60.00  112
 35  \w   -103.00 -44.00   0.50    8.00    -- -100.00 125.00 120.00  118
 36  \w   -106.00 -46.00   0.50    8.00    -- -100.00 125.00  90.00  120
 37  \w   -107.00 -74.00   0.50    8.00    -- -100.00 108.00  12.74   66
 38  \w   -107.00 -75.00   0.50    8.00    -- -100.00 105.00 -11.63   64
 39  \w   -167.00-117.00   0.50    8.00    -- -100.00 -21.00-102.00  100
 40  \w   -172.00-121.00   0.50    8.00    -- -100.00 -61.00 -30.00  102
 41  \w   -173.00 -84.00   0.50    8.00    -- -100.00 -61.00  30.00  178
 42  \w   -167.00-105.00   0.50    8.00    -- -100.00 -61.00 150.00  124
;
_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      0.1198662000
_diffrn_orient_matrix_UB_12      -0.0308876000
_diffrn_orient_matrix_UB_13      -0.0274289000
_diffrn_orient_matrix_UB_21      0.0811466000
_diffrn_orient_matrix_UB_22      0.1292636000
_diffrn_orient_matrix_UB_23      0.0097285000
_diffrn_orient_matrix_UB_31      0.0819568000
_diffrn_orient_matrix_UB_32      -0.0013742000
_diffrn_orient_matrix_UB_33      0.0985879000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.094
_diffrn_reflns_theta_min         2.949
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0253P)^2^+1.0907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6403
_reflns_number_total             7135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01679f2.cif
_cod_data_source_block           shhk_210520
_cod_original_cell_volume        1787.67(5)
_cod_database_code               7158919
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOBr
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.863
_reflns_odcompleteness_completeness 99.80
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N009(H009), C00G(H00G), C00L(H00L), C00Q(H00Q), C00R(H00R), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011),
 C012(H012), C014(H014), C017(H017), C018(H018), C019(H019), C01A(H01J),
 C01C(H01N), C01D(H01O)
2.c Idealised Me refined as rotating group:
 C00Z(H00C,H00D,H00E), C013(H01A,H01B,H01C), C015(H01D,H01E,H01F), C016(H01G,
 H01H,H01I), C01B(H01K,H01L,H01M)
;
_shelx_res_checksum              1445
_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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.724