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_7131634
_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         'C104 H92 N4 O8 S4 Zn4'
_chemical_formula_sum            'C104 H92 N4 O8 S4 Zn4'
_chemical_formula_weight         1915.53
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-20T12:42:03-00:00
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                70.109(2)
_cell_angle_beta                 81.732(2)
_cell_angle_gamma                72.621(2)
_cell_formula_units_Z            1
_cell_length_a                   13.5602(3)
_cell_length_b                   13.8377(3)
_cell_length_c                   14.8499(2)
_cell_measurement_reflns_used    49088
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.991
_cell_measurement_theta_min      3.139
_cell_volume                     2497.85(9)
_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 0.997
_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    -66.00  -9.00   0.50    1.20    --  -23.00 121.00 -54.00  114
  2  \w    -86.00 -26.00   0.50    1.20    --  -23.00 152.00 106.00  120
  3  \w    -94.00  -8.00   0.50    1.20    --  -23.00 -57.00-180.00  172
  4  \w    -96.00 -10.00   0.50    1.20    --  -23.00 -38.00 -90.00  172
  5  \w    -68.00 -12.00   0.50    1.20    --  -23.00 125.00 -90.00  112
  6  \w    -94.00  -8.00   0.50    1.20    --  -23.00 -57.00  60.00  172
  7  \w      1.00  43.00   0.50    1.20    --   30.00  90.00 -82.71   84
  8  \w     -1.00  29.00   0.50    1.20    --   30.00  96.00 129.05   60
  9  \w     15.00  43.00   0.50    1.20    --   42.00  87.00 -68.54   56
 10  \w     17.00  43.00   0.50    1.20    --   46.00  90.00 176.29   52
 11  \w     17.00  43.00   0.50    1.20    --   46.00  90.00   6.88   52
 12  \w     17.00  43.00   0.50    1.20    --   46.00  90.00 134.67   52
 13  \w    -24.00  71.00   0.50    1.20    --   47.92 -77.00 -60.00  190
 14  \w    -24.00  71.00   0.50    1.20    --   47.92 -77.00 120.00  190
 15  \w     28.00 122.00   0.50    1.20    --   50.00  76.00-103.45  188
 16  \w     27.00 122.00   0.50    1.20    --   50.00  77.00 -41.11  190
 17  \w     32.00 126.00   0.50    1.20    --   54.00  76.00  72.18  188
 18  \w     40.00 135.00   0.50    1.20    --   62.00  75.00  29.37  190
 19  \w     40.00 135.00   0.50    1.20    --   62.00  75.00 138.45  190
 20  \w     39.00 135.00   0.50    1.20    --   62.00  77.00  73.75  192
 21  \w     40.00 135.00   0.50    1.20    --   62.00  75.00 -90.74  190
 22  \w     39.00 135.00   0.50    1.20    --   62.00  77.00-176.72  192
 23  \w     45.00 139.00   0.50    1.20    --   66.00  73.00  36.21  188
 24  \w     43.00 139.00   0.50    1.20    --   66.00  77.00 105.26  192
 25  \w     43.00 139.00   0.50    1.20    --   66.00  77.00 -17.33  192
 26  \w     44.00 139.00   0.50    1.20    --   66.00  75.00  -0.29  190
 27  \w     48.00 143.00   0.50    1.20    --   70.00  76.00 141.43  190
 28  \w     48.00 143.00   0.50    1.20    --   70.00  76.00 -46.94  190
 29  \w     48.00 143.00   0.50    1.20    --   70.00  75.00-127.35  190
 30  \w     48.00 143.00   0.50    1.20    --   70.00  75.00 -76.27  190
 31  \w     51.00 146.00   0.50    1.20    --   74.00  77.00-157.71  190
 32  \w     59.00 151.00   0.50    1.20    --   78.00  67.00 -52.96  184
 33  \w     67.00 159.00   0.50    6.00    --   86.00  67.00 -26.40  184
 34  \w     74.00 162.00   0.50    6.00    --   90.00  59.00 115.32  176
 35  \w     85.00 175.00   0.50    6.00    --  102.00  63.00 -78.20  180
 36  \w     86.00 175.00   0.50    6.00    --  102.00  59.00-173.43  178
 37  \w     91.00 177.00   0.50    6.00    --  110.00  69.00 178.84  172
 38  \w     97.00 177.00   0.50    6.00    --  113.25  61.00 -60.00  160
 39  \w     91.00 177.00   0.50    6.00    --  113.25  77.00  90.00  172
 40  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00 -30.00  128
 41  \w     91.00 177.00   0.50    6.00    --  113.25  77.00-150.00  172
 42  \w     97.00 177.00   0.50    6.00    --  113.25  61.00 120.00  160
 43  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00 120.00  120
 44  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00 150.00  120
 45  \w     97.00 177.00   0.50    6.00    --  113.25  61.00  30.00  160
 46  \w     91.00 177.00   0.50    6.00    --  113.25  77.00  30.00  172
 47  \w     97.00 177.00   0.50    6.00    --  113.25  61.00  60.00  160
 48  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00-120.00  120
 49  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00-180.00  120
 50  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00   0.00  120
 51  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00 -90.00  120
 52  \w     97.00 177.00   0.50    6.00    --  113.25  61.00-120.00  160
 53  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00  90.00  128
 54  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00  90.00  120
 55  \w     97.00 177.00   0.50    6.00    --  113.25  61.00 -30.00  160
 56  \w     91.00 177.00   0.50    6.00    --  113.25  77.00 -60.00  172
 57  \w     97.00 177.00   0.50    6.00    --  113.25  61.00 150.00  160
 58  \w     91.00 177.00   0.50    6.00    --  113.25  77.00 150.00  172
 59  \w     91.00 177.00   0.50    6.00    --  113.25  77.00-120.00  172
 60  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00-150.00  128
 61  \w     42.00 102.00   0.50    6.00    --  113.25 -77.00  60.00  120
 62  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00-120.00  128
 63  \w     97.00 177.00   0.50    6.00    --  113.25  61.00-150.00  160
 64  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00 150.00  128
 65  \w     42.00 106.00   0.50    6.00    --  113.25 -94.00 -90.00  128
 66  \w     91.00 177.00   0.50    6.00    --  113.25  77.00 -90.00  172
 67  \w     97.00 177.00   0.50    6.00    --  113.25  61.00  90.00  160
 68  \w     97.00 177.00   0.50    6.00    --  113.25  61.00   0.00  160
 69  \w     91.00 174.00   0.50    6.00    --  113.25  77.00  60.00  166
 70  \w    141.00 175.00   0.50    6.00    --  113.25  77.00 120.00   68
 71  \w    134.00 177.00   0.50    6.00    --  113.25  77.00   0.00   86
 72  \w     91.00 129.00   0.50    6.00    --  113.25  77.00 120.00   76
 73  \w    136.00 177.00   0.50    6.00    --  113.25  77.00 -30.00   82
 74  \w     91.00 118.00   0.50    6.00    --  113.25  77.00   0.00   54
 75  \w     79.00 106.00   0.50    6.00    --  113.25 -94.00  30.00   54
 76  \w     42.00  95.00   0.50    6.00    --  113.25 -77.00 -30.00  106
 77  \w     91.00 123.00   0.50    6.00    --  113.25  77.00 -30.00   64
 78  \w    151.00 177.00   0.50    6.00    --  113.25  77.00-180.00   52
 79  \w     91.00 126.00   0.50    6.00    --  113.25  77.00-180.00   70
 80  \w     42.00  69.00   0.50    6.00    --  113.25 -94.00  30.00   54
;
_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      -0.0743493
_diffrn_orient_matrix_UB_12      0.1114341
_diffrn_orient_matrix_UB_13      -0.0102158
_diffrn_orient_matrix_UB_21      0.0220046
_diffrn_orient_matrix_UB_22      0.0328248
_diffrn_orient_matrix_UB_23      -0.1093839
_diffrn_orient_matrix_UB_31      -0.0905018
_diffrn_orient_matrix_UB_32      -0.0401278
_diffrn_orient_matrix_UB_33      -0.0113668
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.024
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            96707
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         3.168
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.42.86a (Rigaku Oxford Diffraction, 2023)
        Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.00046(11)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         10200
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0799P)^2^+1.9201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0
_reflns_number_gt                9000
_reflns_number_total             10200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01490h2.cif
_cod_data_source_block           22EH167_TK-137
_cod_depositor_comments
'Adding full bibliography for 7131634--7131637.cif.'
_cod_database_code               7131634
_shelx_estimated_absorpt_t_min   0.714
_shelx_estimated_absorpt_t_max   0.928
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.101
_oxdiff_exptl_absorpt_empirical_full_min 0.686
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C40A, C45A, C44A, C43A, C42A, C41A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C40, C45, C44, C43, C42, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C41A) \\sim Ueq, Uanis(C40A) \\sim Ueq, Uanis(C45A) \\sim Ueq,
Uanis(C44A) \\sim Ueq, Uanis(C43A) \\sim Ueq, Uanis(C42A) \\sim Ueq, Uanis(C40)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C42)
\\sim Ueq, Uanis(C41) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H33A)=Sof(C45A)=Sof(H45A)=Sof(C44A)=Sof(H44A)=Sof(C43A)=Sof(H43A)=
 Sof(C42A)=Sof(H42A)=Sof(C41A)=Sof(H41A)=Sof(C40A)=1-FVAR(1)
 Sof(H33)=Sof(C40)=Sof(C41)=Sof(H41)=Sof(C45)=Sof(H45)=Sof(C44)=Sof(H44)=
 Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C33(H33), C33(H33A)
5.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C25(H25), C21(H21), C19(H19), C28(H28), C39(H39), C47(H47),
 C51(H51), C24(H24), C15(H15), C22(H22), C38(H38), C35(H35), C29(H29), C18(H18),
  C48(H48), C37(H37), C9(H9), C50(H50), C16(H16), C36(H36), C13(H13), C11(H11),
 C17(H17), C31(H31), C6(H6), C30(H30), C12(H12), C41(H41), C10(H10), C2(H2),
 C45(H45), C4(H4), C3(H3), C44(H44), C5(H5), C42(H42), C43(H43), C45A(H45A),
 C44A(H44A), C43A(H43A), C42A(H42A), C41A(H41A)
5.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C52(H52A,H52B,H52C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              81132
_shelx_hkl_checksum              31595
_shelx_fab_checksum              97519