Atom-efficient transition-metal-free arylation of <i>N</i>,<i>O</i>-acetals using diarylzinc reagents through Zn/Zn cooperativity.
Borys, Andryj M.; Gil-Negrete, Jose M; Hevia, Eva; Chemical communications (Cambridge, England) 57 (2021) 8905–8908; doi:10.1039/d1cc04137a

data_7128838
_publ_section_title
;
 Atom-efficient transition-metal-free arylation of
 <i>N</i>,<i>O</i>-acetals using diarylzinc reagents through Zn/Zn
 cooperativity.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8905
_journal_page_last               8908
_journal_paper_doi               10.1039/d1cc04137a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C28 H12 F20 O4 Zn4, C7 H8'
_chemical_formula_sum            'C35 H20 F20 O4 Zn4'
_chemical_formula_weight         1145.99
_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_update_record
;
2021-07-27 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                85.6520(10)
_cell_angle_beta                 82.5450(10)
_cell_angle_gamma                84.9310(10)
_cell_formula_units_Z            2
_cell_length_a                   10.17870(10)
_cell_length_b                   10.3481(2)
_cell_length_c                   19.0323(3)
_cell_measurement_reflns_used    33961
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.935
_cell_measurement_theta_min      2.34
_cell_volume                     1975.75(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -31.00  50.00   0.50    0.50    --  -21.00  55.00 141.00  162
  2  \w     76.00 118.00   0.50    0.50    --   47.91  55.00 141.00   84
  3  \w    -23.00  60.00   0.50    0.50    --   47.91 -55.00  -1.00  166
  4  \w    148.00 176.00   0.50    1.80    --  113.25  55.00 141.00   56
  5  \w    100.00 139.00   0.50    1.80    --  113.25  55.00 141.00   78
  6  \w    -93.00  -5.00   0.50    0.50    --  -21.00 -61.00 150.00  176
  7  \w    -87.00 -17.00   0.50    0.50    --  -21.00 -55.00  -1.00  140
  8  \w     -4.00  21.00   0.50    0.50    --   28.00  97.00 175.17   50
  9  \w      0.00  26.00   0.50    0.50    --   32.00  97.00 -17.71   52
 10  \w     10.00  41.00   0.50    0.50    --   40.00  92.00-116.69   62
 11  \w     12.00  37.00   0.50    0.50    --   40.00  88.00 121.16   50
 12  \w     14.00  39.00   0.50    0.50    --   44.00  92.00-102.52   50
 13  \w     17.00  43.00   0.50    0.50    --   44.00  89.00  21.97   52
 14  \w     36.00  95.00   0.50    0.50    --   47.91-125.00 -60.00  118
 15  \w     26.00  52.00   0.50    0.50    --   47.91  77.00   0.00   52
 16  \w     34.00  96.00   0.50    0.50    --   47.91-125.00-150.00  124
 17  \w     31.00  57.00   0.50    0.50    --   52.00  75.00 170.28   52
 18  \w     37.00  68.00   0.50    0.50    --   60.00  77.00-166.46   62
 19  \w     37.00  65.00   0.50    0.50    --   60.00  77.00-117.99   56
 20  \w     41.00  76.00   0.50    0.50    --   64.00  77.00-154.97   70
 21  \w     41.00  67.00   0.50    0.50    --   64.00  77.00  19.00   52
 22  \w     43.00  79.00   0.50    0.50    --   64.00  77.00 141.27   72
 23  \w     41.00  71.00   0.50    0.50    --   64.00  77.00-104.88   60
 24  \w    107.00 137.00   0.50    0.50    --   64.00  77.00-154.97   60
 25  \w    111.00 136.00   0.50    0.50    --   64.00  77.00-104.88   50
 26  \w     88.00 120.00   0.50    0.50    --   68.00  77.00 -57.95   64
 27  \w     45.00  80.00   0.50    0.50    --   68.00  77.00 114.21   70
 28  \w    105.00 131.00   0.50    0.50    --   68.00  77.00  78.27   52
 29  \w     46.00  76.00   0.50    0.50    --   68.00  75.00 -13.72   60
 30  \w     45.00  70.00   0.50    0.50    --   68.00  77.00 -57.95   50
 31  \w     47.00  78.00   0.50    0.50    --   68.00  75.00  45.83   62
 32  \w    104.00 130.00   0.50    0.50    --   68.00  76.00 -87.59   52
 33  \w    112.00 139.00   0.50    0.50    --   68.00  77.00 114.21   54
 34  \w     46.00  77.00   0.50    0.50    --   68.00  76.00 -87.59   62
 35  \w     45.00  88.00   0.50    0.50    --   68.00  77.00  78.27   86
 36  \w     50.00 109.00   0.50    0.50    --   72.00  75.00   8.77  118
 37  \w    118.00 143.00   0.50    0.50    --   80.00  67.00 132.81   50
 38  \w     61.00  97.00   0.50    0.50    --   80.00  67.00 132.81   72
 39  \w     68.00  96.00   0.50    1.80    --   84.00  60.00 -45.98   56
 40  \w     71.00 156.00   0.50    1.80    --   84.00  55.00  35.02  170
 41  \w     69.00  97.00   0.50    1.80    --   84.00  60.00   5.91   56
 42  \w     75.00 165.00   0.50    1.80    --   92.00  62.00  64.83  180
 43  \w    130.00 172.00   0.50    1.80    --  113.25  77.00  60.00   84
 44  \w     91.00 117.00   0.50    1.80    --  113.25  77.00  60.00   52
 45  \w     42.00  67.00   0.50    1.80    --  113.25 -61.00  90.00   50
 46  \w     97.00 177.00   0.50    1.80    --  113.25  61.00-180.00  160
 47  \w     74.00 106.00   0.50    1.80    --  113.25 -94.00  90.00   64
 48  \w     97.00 168.00   0.50    1.80    --  113.25  61.00  30.00  142
 49  \w     46.00 106.00   0.50    1.80    --  113.25 -94.00 -30.00  120
 50  \w    131.00 157.00   0.50    1.80    --  113.25  61.00 120.00   52
 51  \w    133.00 175.00   0.50    1.80    --  113.25  77.00  90.00   84
 52  \w     97.00 127.00   0.50    1.80    --  113.25  61.00 120.00   60
 53  \w     91.00 122.00   0.50    1.80    --  113.25  77.00  90.00   62
 54  \w    136.00 162.00   0.50    1.80    --  113.25  77.00 -60.00   52
 55  \w     97.00 174.00   0.50    1.80    --  113.25  61.00 -30.00  154
 56  \w     91.00 117.00   0.50    1.80    --  113.25  77.00 -60.00   52
 57  \w     97.00 177.00   0.50    1.80    --  113.25  61.00-120.00  160
 58  \w    151.00 176.00   0.50    1.80    --  113.25  77.00 150.00   50
 59  \w     43.00  68.00   0.50    1.80    --  113.25 -94.00  90.00   50
 60  \w    126.00 177.00   0.50    1.80    --  113.25  77.00-150.00  102
 61  \w     97.00 146.00   0.50    1.80    --  113.25  61.00-150.00   98
 62  \w     91.00 120.00   0.50    1.80    --  113.25  77.00 -30.00   58
 63  \w    103.00 162.00   0.50    1.80    --  113.25  61.00  60.00  118
 64  \w     98.00 136.00   0.50    1.80    --  113.25  61.00 150.00   76
 65  \w    139.00 165.00   0.50    1.80    --  113.25  61.00 150.00   52
 66  \w     45.00  71.00   0.50    1.80    --  113.25 -94.00  60.00   52
 67  \w     97.00 142.00   0.50    1.80    --  113.25  61.00 -90.00   90
 68  \w     91.00 131.00   0.50    1.80    --  113.25  77.00 150.00   80
 69  \w     92.00 118.00   0.50    1.80    --  113.25  77.00-150.00   52
 70  \w     77.00 106.00   0.50    1.80    --  113.25 -98.00-139.04   58
 71  \w     55.00 104.00   0.50    1.80    --  113.25 -94.00 -60.00   98
 72  \w     98.00 156.00   0.50    1.80    --  113.25  61.00   0.00  116
 73  \w     43.00  69.00   0.50    1.80    --  113.25 -98.00-139.04   52
 74  \w    107.00 174.00   0.50    1.80    --  113.25 125.00 -60.00  134
 75  \w    126.00 152.00   0.50    1.80    --  113.25  77.00-180.00   52
 76  \w     54.00 111.00   0.50    1.80    --  113.25-125.00-180.00  114
 77  \w     42.00 103.00   0.50    1.80    --  113.25 -94.00 -90.00  122
 78  \w     91.00 116.00   0.50    1.80    --  113.25  77.00-180.00   50
 79  \w     97.00 139.00   0.50    1.80    --  113.25  61.00  90.00   84
 80  \w     98.00 149.00   0.50    1.80    --  113.25  61.00 -60.00  102
 81  \w    113.00 144.00   0.50    1.80    --  113.25 125.00-180.00   62
 82  \w    132.00 177.00   0.50    1.80    --  113.25  77.00 -90.00   90
 83  \w    138.00 176.00   0.50    1.80    --  113.25  77.00 120.00   76
 84  \w     46.00 104.00   0.50    1.80    --  113.25 -94.00  30.00  116
 85  \w     92.00 118.00   0.50    1.80    --  113.25  77.00 -90.00   52
 86  \w    105.00 158.00   0.50    1.80    --  113.25 125.00  60.00  106
 87  \w     92.00 118.00   0.50    1.80    --  113.25  77.00 120.00   52
 88  \w     91.00 140.00   0.50    1.80    --  113.25  77.00-120.00   98
 89  \w     91.00 175.00   0.50    1.80    --  113.25  77.00   0.00  168
 90  \w     48.00  97.00   0.50    1.80    --  113.25 -77.00 -30.00   98
 91  \w     46.00  96.00   0.50    1.80    --  113.25 -77.00  90.00  100
 92  \w     43.00  74.00   0.50    1.80    --  113.25 -94.00-180.00   62
 93  \w     80.00 105.00   0.50    1.80    --  113.25 -94.00-180.00   50
 94  \w     78.00 105.00   0.50    1.80    --  113.25 -94.00  60.00   54
 95  \w    121.00 170.00   0.50    1.80    --  113.25 125.00   0.00   98
;
_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      -0.0812653
_diffrn_orient_matrix_UB_12      -0.1193459
_diffrn_orient_matrix_UB_13      0.018653
_diffrn_orient_matrix_UB_21      -0.100591
_diffrn_orient_matrix_UB_22      0.0799318
_diffrn_orient_matrix_UB_23      0.0505458
_diffrn_orient_matrix_UB_31      -0.0820044
_diffrn_orient_matrix_UB_32      0.0424335
_diffrn_orient_matrix_UB_33      -0.0615614
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49800
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.998
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.62722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_description       plate
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         7249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0441P)^2^+1.3094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0
_reflns_number_gt                6804
_reflns_number_total             7249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04137a2.cif
_cod_data_source_block           21EH056_AMB-398
_cod_depositor_comments
'Adding full bibliography for 7128836--7128839.cif.'
_cod_database_code               7128838
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.819
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.997
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_shelx_shelxl_version_number     2018/3
_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 Aromatic/amide H refined with riding coordinates:
 C30(H30), C34(H34), C32(H32), C33(H33), C31(H31)
        2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              94590
_shelx_hkl_checksum              62229