Atom-efficient arylation of <i>N</i>-tosylimines mediated by cooperative ZnAr<sub>2</sub>/Zn(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> combinations.
Borys, Andryj M.; Kunzmann, Tim; Gil-Negrete, Jose M; Hevia, Eva; Chemical communications (Cambridge, England) 59 (2023) 7583–7586; doi:10.1039/d3cc01490h

data_7131637
_publ_section_title
;
 Atom-efficient arylation of <i>N</i>-tosylimines mediated by cooperative
 ZnAr<sub>2</sub>/Zn(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> combinations.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7583
_journal_page_last               7586
_journal_paper_doi               10.1039/d3cc01490h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C76 H46 F20 N2 O4 S2 Zn4'
_chemical_formula_sum            'C76 H46 F20 N2 O4 S2 Zn4'
_chemical_formula_weight         1756.75
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-20T11:59:21-00:00
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2751(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.61445(7)
_cell_length_b                   17.36835(10)
_cell_length_c                   15.87255(9)
_cell_measurement_reflns_used    59759
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      79.834
_cell_measurement_theta_min      2.529
_cell_volume                     3471.87(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_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    -59.00   1.00   0.50    0.15    --  -23.00 107.00 150.00  120
  2  \w     20.00  84.00   0.50    0.15    --   47.92-107.00  52.00  128
  3  \w     44.00 107.00   0.50    0.60    --  113.25-107.00  52.00  126
  4  \w    105.00 177.00   0.50    0.60    --  113.25 107.00 150.00  144
  5  \w    -36.00  49.00   0.50    0.15    --  -23.00  45.00 -90.00  170
  6  \w    -94.00  -8.00   0.50    0.15    --  -23.00 -57.00  90.00  172
  7  \w    -97.00 -10.00   0.50    0.15    --  -23.00 -30.00 -60.00  174
  8  \w    -68.00 -12.00   0.50    0.15    --  -23.00 125.00 -60.00  112
  9  \w     -1.00  80.00   0.50    0.15    --   47.92 -99.00  60.00  162
 10  \w     -1.00  80.00   0.50    0.15    --   47.92 -99.00-150.00  162
 11  \w    -26.00  23.00   0.50    0.15    --   47.92 -19.00 150.00   98
 12  \w    -26.00  23.00   0.50    0.15    --   47.92 -19.00 -30.00   98
 13  \w     33.00 120.00   0.50    0.15    --   47.92  57.00 -90.00  174
 14  \w    -26.00  23.00   0.50    0.15    --   47.92 -19.00-120.00   98
 15  \w     97.00 177.00   0.50    0.60    --  113.25  61.00-180.00  160
 16  \w    100.00 177.00   0.50    0.60    --  113.25  15.00  60.00  154
 17  \w     97.00 177.00   0.50    0.60    --  113.25  61.00-120.00  160
 18  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  90.00  128
 19  \w    101.00 177.00   0.50    0.60    --  113.25  30.00 150.00  152
 20  \w    101.00 177.00   0.50    0.60    --  113.25  30.00-120.00  152
 21  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00-150.00   52
 22  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 120.00  128
 23  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -60.00  128
 24  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  60.00  128
 25  \w     97.00 177.00   0.50    0.60    --  113.25  61.00  90.00  160
 26  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00  30.00  120
 27  \w     91.00 177.00   0.50    0.60    --  113.25  77.00-120.00  172
 28  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00-150.00  128
 29  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  30.00  128
 30  \w     91.00 177.00   0.50    0.60    --  113.25  77.00-150.00  172
 31  \w    101.00 177.00   0.50    0.60    --  113.25  45.00-150.00  152
 32  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00  60.00  120
 33  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -30.00  128
 34  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 150.00  128
 35  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -90.00  128
 36  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00 -30.00   52
 37  \w     97.00 177.00   0.50    0.60    --  113.25  61.00 -90.00  160
 38  \w    100.00 177.00   0.50    0.60    --  113.25  15.00  90.00  154
 39  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00  90.00  120
 40  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00   0.00  128
 41  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00-120.00  128
 42  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00 120.00  120
 43  \w    110.00 174.00   0.50    0.60    --  113.25  30.00-180.00  128
 44  \w    102.00 171.00   0.50    0.60    --  113.25  30.00  30.00  138
 45  \w     44.00 105.00   0.50    0.60    --  113.25 -94.00-180.00  122
 46  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00 120.00   52
 47  \w    142.00 167.00   0.50    0.60    --  113.25  54.00 -42.00   50
 48  \w     42.00  67.00   0.50    0.60    --  113.25 -61.00 150.00   50
 49  \w     42.00  67.00   0.50    0.60    --  113.25 -61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0808502
_diffrn_orient_matrix_UB_12      -0.0167637
_diffrn_orient_matrix_UB_13      -0.0668188
_diffrn_orient_matrix_UB_21      0.0372846
_diffrn_orient_matrix_UB_22      0.0844266
_diffrn_orient_matrix_UB_23      0.0044828
_diffrn_orient_matrix_UB_31      0.0836902
_diffrn_orient_matrix_UB_32      -0.0213128
_diffrn_orient_matrix_UB_33      0.0706571
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            69714
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.494
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.081
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.19
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.42.86a (Rigaku Oxford Diffraction, 2023)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.68
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.34
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00107(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+2.3893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0
_reflns_number_gt                7079
_reflns_number_total             7101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01490h2.cif
_cod_data_source_block           22EH166_TK-138
_cod_depositor_comments
'Adding full bibliography for 7131634--7131637.cif.'
_cod_database_code               7131637
_shelx_estimated_absorpt_t_min   0.367
_shelx_estimated_absorpt_t_max   0.642
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.834
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C12(H12), C15(H15), C32(H32), C8(H8), C26(H26), C17(H17),
 C28(H28), C29(H29), C11(H11), C31(H31), C30(H30), C22(H22), C9(H9), C25(H25),
 C10(H10), C24(H24), C23(H23)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              10735
_shelx_hkl_checksum              26043