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_7131635
_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         'C32 H39 N3 O2 S Zn'
_chemical_formula_sum            'C32 H39 N3 O2 S Zn'
_chemical_formula_weight         595.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.965(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.6033(8)
_cell_length_b                   9.8468(3)
_cell_length_c                   23.6134(5)
_cell_measurement_reflns_used    8255
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      74.5830
_cell_measurement_theta_min      4.6360
_cell_volume                     6625.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -33.00  55.00   0.50    1.00    --  -21.00  26.00  35.00  176
  2  \w    -96.00  -8.00   0.50    1.00    --  -21.00 -26.00-127.00  176
  3  \w    -27.00  28.00   0.50    1.00    --   46.89 -26.00-127.00  110
  4  \w     35.00 123.00   0.50    1.00    --   46.89  26.00  35.00  176
  5  \w    101.00 171.00   0.50    2.00    --  113.25  26.00  35.00  140
  6  \w    -68.00 -12.00   0.50    1.00    --  -21.00 125.00-180.00  112
  7  \w    -93.00   2.00   0.50    1.00    --  -21.00 -77.00   0.00  190
  8  \w    -27.00  23.00   0.50    1.00    --   46.89 -19.00-150.00  100
  9  \w    -27.00  23.00   0.50    1.00    --   46.89 -19.00  90.00  100
 10  \w     35.00  95.00   0.50    1.00    --   46.89-125.00  60.00  120
 11  \w     -1.00  81.00   0.50    1.00    --   46.89 -99.00 150.00  164
 12  \w    -26.00  40.00   0.50    1.00    --   46.89 -38.00-180.00  132
 13  \w     35.00  95.00   0.50    1.00    --   46.89-125.00-150.00  120
 14  \w     35.00  95.00   0.50    1.00    --   46.89-125.00 150.00  120
 15  \w     42.00 102.00   0.50    2.00    --  113.25 -77.00-180.00  120
 16  \w    101.00 171.00   0.50    2.00    --  113.25  30.00 120.00  140
 17  \w     42.00 102.00   0.50    2.00    --  113.25 -77.00  30.00  120
 18  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00  30.00  128
 19  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00 -30.00  128
 20  \w     42.00 102.00   0.50    2.00    --  113.25 -77.00 -30.00  120
 21  \w     95.00 171.00   0.50    2.00    --  113.25 125.00  60.00  152
 22  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00 -90.00  128
 23  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00  60.00  128
 24  \w     42.00 112.00   0.50    2.00    --  113.25-125.00 120.00  140
 25  \w    101.00 171.00   0.50    2.00    --  113.25  30.00   0.00  140
 26  \w    114.00 152.00   0.50    2.00    --  113.25  45.00 -60.00   76
 27  \w     43.00  92.00   0.50    2.00    --  113.25 -77.00 -90.00   98
 28  \w     43.00  95.00   0.50    2.00    --  113.25 -94.00 150.00  104
 29  \w    103.00 164.00   0.50    2.00    --  113.25  30.00 150.00  122
 30  \w     42.00  67.00   0.50    2.00    --  113.25 -61.00-180.00   50
 31  \w     42.00 105.00   0.50    2.00    --  113.25 -94.00-120.00  126
 32  \w    143.00 168.00   0.50    2.00    --  113.25  77.00 -60.00   50
 33  \w    102.00 130.00   0.50    2.00    --  113.25  30.00  90.00   56
 34  \w    141.00 171.00   0.50    2.00    --  113.25  30.00  90.00   60
 35  \w    112.00 167.00   0.50    2.00    --  113.25  37.00-161.52  110
 36  \w     77.00 106.00   0.50    2.00    --  113.25 -94.00 -60.00   58
 37  \w     42.00  68.00   0.50    2.00    --  113.25 -61.00-120.00   52
 38  \w     42.00  68.00   0.50    2.00    --  113.25 -61.00  90.00   52
 39  \w    106.00 166.00   0.50    2.00    --  113.25  38.00 168.66  120
 40  \w    103.00 132.00   0.50    2.00    --  113.25  78.00-165.94   58
 41  \w    144.00 171.00   0.50    2.00    --  113.25  78.00-165.94   54
 42  \w     79.00 106.00   0.50    2.00    --  113.25 -94.00-150.00   54
 43  \w     45.00 105.00   0.50    2.00    --  113.25 -94.00   0.00  120
 44  \w     51.00 106.00   0.50    2.00    --  113.25 -97.00 141.89  110
 45  \w     45.00 106.00   0.50    2.00    --  113.25 -94.00-180.00  122
 46  \w    105.00 165.00   0.50    2.00    --  113.25  51.00-113.46  120
 47  \w     91.00 127.00   0.50    2.00    --  113.25  77.00 -60.00   72
 48  \w     42.00  67.00   0.50    2.00    --  113.25 -61.00  60.00   50
 49  \w     42.00  68.00   0.50    2.00    --  113.25 -61.00 150.00   52
 50  \w     66.00 106.00   0.50    2.00    --  113.25 -94.00  90.00   80
 51  \w     84.00 109.00   0.50    2.00    --  113.25-125.00 150.00   50
 52  \w    101.00 169.00   0.50    2.00    --  113.25  45.00  30.00  136
 53  \w     72.00 107.00   0.50    2.00    --  113.25-102.00 -83.74   70
 54  \w    104.00 164.00   0.50    2.00    --  113.25  45.00-120.00  120
 55  \w     49.00  80.00   0.50    2.00    --  113.25-125.00 150.00   62
;
_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      0.0429824000
_diffrn_orient_matrix_UB_12      -0.0826465000
_diffrn_orient_matrix_UB_13      -0.0150754000
_diffrn_orient_matrix_UB_21      0.0319931000
_diffrn_orient_matrix_UB_22      0.1221868000
_diffrn_orient_matrix_UB_23      0.0161433000
_diffrn_orient_matrix_UB_31      0.0071804000
_diffrn_orient_matrix_UB_32      -0.0521714000
_diffrn_orient_matrix_UB_33      0.0616532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            56084
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.562
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.228
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       plate
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         7182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0678
_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^)+(0.0779P)^2^+29.0902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5595
_reflns_number_total             7182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01490h2.cif
_cod_data_source_block           20EH166_JN187
_cod_depositor_comments
'Adding full bibliography for 7131634--7131637.cif.'
_cod_database_code               7131635
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C256 H306 N24 O16 S8 Zn8 '
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.584
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C23(H23), C22(H22), C26(H26), C12(H12), C6(H6), C18(H18),
 C17(H17), C19(H19), C8(H8), C24(H24), C5(H5), C11(H11), C25(H25), C2(H2),
 C3(H3), C9(H9), C4(H4)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C27(H27A,H27B,H27C), C32(H32A,H32B,H32C), C28(H28A,H28B,
 H28C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              21460
_shelx_hkl_checksum              3609
_shelx_fab_checksum              49859
_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 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.510