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_7128836
_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 H32 O4 Zn4'
_chemical_formula_sum            'C28 H32 O4 Zn4'
_chemical_formula_weight         694.01
_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_update_record
;
2021-07-27 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1859(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.63748(12)
_cell_length_b                   16.05559(14)
_cell_length_c                   13.67121(12)
_cell_measurement_reflns_used    39317
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      79.053
_cell_measurement_theta_min      4.205
_cell_volume                     2993.40(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      173.01(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    -50.00  14.00   0.50    0.50    --  -21.00  91.00 -85.00  128
  2  \w     -6.00  20.00   0.50    0.50    --   47.91 -91.00 160.00   52
  3  \w     31.00  77.00   0.50    0.50    --   47.91 -91.00 160.00   92
  4  \w     78.00 103.00   0.50    2.50    --  113.25 -91.00 160.00   50
  5  \w    -87.00 -10.00   0.50    0.50    --  -21.00 -45.00  30.00  154
  6  \w    -25.00  51.00   0.50    0.50    --  -21.00  57.00  90.00  152
  7  \w      3.00  31.00   0.50    0.50    --   32.00  93.00 -92.83   56
  8  \w      8.00  40.00   0.50    0.50    --   32.00  79.00 171.24   64
  9  \w     13.00  38.00   0.50    0.50    --   40.00  87.00  -7.83   50
 10  \w     13.00  40.00   0.50    0.50    --   40.00  89.00  70.94   54
 11  \w     15.00  41.00   0.50    0.50    --   44.00  91.00  33.49   52
 12  \w     15.00  40.00   0.50    0.50    --   44.00  91.00-143.51   50
 13  \w     36.00  96.00   0.50    0.50    --   47.91-125.00-180.00  120
 14  \w     34.00  96.00   0.50    0.50    --   47.91-125.00  60.00  124
 15  \w     33.00  58.00   0.50    0.50    --   52.00  74.00-177.57   50
 16  \w     84.00 122.00   0.50    0.50    --   52.00  74.00-177.57   76
 17  \w     37.00  84.00   0.50    0.50    --   60.00  77.00 102.61   94
 18  \w     41.00  66.00   0.50    0.50    --   60.00  75.00 -97.46   50
 19  \w    105.00 131.00   0.50    0.50    --   60.00  77.00-179.83   52
 20  \w     38.00  83.00   0.50    0.50    --   60.00  76.00  52.41   90
 21  \w     37.00  67.00   0.50    0.50    --   60.00  77.00-179.83   60
 22  \w     42.00  74.00   0.50    0.50    --   64.00  77.00  94.56   64
 23  \w     41.00  91.00   0.50    0.50    --   64.00  77.00 129.89  100
 24  \w    111.00 137.00   0.50    0.50    --   64.00  77.00  94.56   52
 25  \w     45.00  77.00   0.50    0.50    --   64.00  75.00 -20.05   64
 26  \w     90.00 116.00   0.50    0.50    --   64.00  77.00-120.65   52
 27  \w     41.00  67.00   0.50    0.50    --   64.00  77.00-120.65   52
 28  \w     45.00 106.00   0.50    0.50    --   68.00  77.00 -55.06  122
 29  \w     46.00  77.00   0.50    0.50    --   68.00  76.00-177.57   62
 30  \w     45.00  80.00   0.50    0.50    --   68.00  77.00 -91.02   70
 31  \w     46.00  71.00   0.50    0.50    --   68.00  76.00   3.75   50
 32  \w     48.00  98.00   0.50    0.50    --   68.00  75.00  55.20  100
 33  \w     51.00  97.00   0.50    0.50    --   68.00  74.00  14.38   92
 34  \w    100.00 127.00   0.50    0.50    --   68.00  75.00  55.20   54
 35  \w     46.00  81.00   0.50    0.50    --   68.00  77.00-162.48   70
 36  \w     67.00 125.00   0.50    0.50    --   76.00  39.00 119.85  116
 37  \w     65.00  91.00   0.50    0.50    --   80.00  57.00-102.49   52
 38  \w     71.00  97.00   0.50    2.50    --   88.00  63.00-109.62   52
 39  \w     72.00  98.00   0.50    2.50    --   88.00  64.00 -37.51   52
 40  \w     77.00 115.00   0.50    2.50    --   92.00  56.00  -7.83   76
 41  \w     72.00 161.00   0.50    2.50    --   92.00  70.00 147.72  178
 42  \w     76.00 110.00   0.50    2.50    --   96.00  70.00 -76.41   68
 43  \w     86.00 139.00   0.50    2.50    --  100.00  53.00  42.15  106
 44  \w     97.00 152.00   0.50    2.50    --  113.25  61.00-150.00  110
 45  \w     56.00 105.00   0.50    2.50    --  113.25 -94.00  30.00   98
 46  \w     91.00 176.00   0.50    2.50    --  113.25  77.00-120.00  170
 47  \w     76.00 102.00   0.50    2.50    --  113.25 -94.00-150.00   52
 48  \w     42.00  67.00   0.50    2.50    --  113.25 -94.00-150.00   50
 49  \w    128.00 177.00   0.50    2.50    --  113.25  77.00-150.00   98
 50  \w     91.00 118.00   0.50    2.50    --  113.25  77.00-150.00   54
 51  \w     85.00 111.00   0.50    2.50    --  113.25-125.00 150.00   52
 52  \w     97.00 177.00   0.50    2.50    --  113.25  61.00  60.00  160
 53  \w     80.00 106.00   0.50    2.50    --  113.25 -94.00  60.00   52
 54  \w     42.00  74.00   0.50    2.50    --  113.25 -94.00  60.00   64
 55  \w    101.00 164.00   0.50    2.50    --  113.25  30.00 150.00  126
 56  \w     43.00  93.00   0.50    2.50    --  113.25 -77.00 -30.00  100
 57  \w     93.00 171.00   0.50    2.50    --  113.25  77.00 -60.00  156
 58  \w     98.00 130.00   0.50    2.50    --  113.25  61.00  90.00   64
 59  \w     46.00  74.00   0.50    2.50    --  113.25-125.00 150.00   56
 60  \w     91.00 143.00   0.50    2.50    --  113.25  77.00  60.00  104
 61  \w    101.00 132.00   0.50    2.50    --  113.25  45.00 150.00   62
 62  \w    142.00 171.00   0.50    2.50    --  113.25  77.00-180.00   58
 63  \w    147.00 174.00   0.50    2.50    --  113.25  77.00 150.00   54
 64  \w     92.00 130.00   0.50    2.50    --  113.25  77.00-180.00   76
 65  \w     42.00  67.00   0.50    2.50    --  113.25 -61.00-180.00   50
 66  \w     92.00 176.00   0.50    2.50    --  113.25  77.00  90.00  168
 67  \w    129.00 155.00   0.50    2.50    --  113.25  61.00-120.00   52
 68  \w     99.00 126.00   0.50    2.50    --  113.25  61.00-120.00   54
 69  \w    141.00 167.00   0.50    2.50    --  113.25  61.00 -60.00   52
 70  \w    100.00 128.00   0.50    2.50    --  113.25  61.00 -60.00   56
 71  \w     48.00 106.00   0.50    2.50    --  113.25 -99.00 142.03  116
 72  \w    118.00 177.00   0.50    2.50    --  113.25  45.00 -90.00  118
 73  \w    152.00 177.00   0.50    2.50    --  113.25  77.00  30.00   50
 74  \w     93.00 140.00   0.50    2.50    --  113.25  77.00  30.00   94
 75  \w     74.00 105.00   0.50    2.50    --  113.25 -94.00 -30.00   62
 76  \w     91.00 168.00   0.50    2.50    --  113.25  77.00 -30.00  154
 77  \w    130.00 174.00   0.50    2.50    --  113.25  73.00 143.10   88
 78  \w     95.00 122.00   0.50    2.50    --  113.25  73.00 143.10   54
 79  \w     46.00  97.00   0.50    2.50    --  113.25 -77.00  60.00  102
 80  \w    130.00 172.00   0.50    2.50    --  113.25  61.00  30.00   84
 81  \w     42.00  67.00   0.50    2.50    --  113.25 -61.00-150.00   50
 82  \w     44.00  71.00   0.50    2.50    --  113.25 -94.00 -30.00   54
 83  \w     76.00 105.00   0.50    2.50    --  113.25 -94.00-120.00   58
 84  \w     99.00 125.00   0.50    2.50    --  113.25  61.00  30.00   52
 85  \w     97.00 165.00   0.50    2.50    --  113.25  61.00-180.00  136
 86  \w     81.00 106.00   0.50    2.50    --  113.25 -94.00 -60.00   50
 87  \w     43.00  68.00   0.50    2.50    --  113.25 -94.00 -60.00   50
 88  \w    139.00 171.00   0.50    2.50    --  113.25  61.00 -30.00   64
 89  \w     97.00 171.00   0.50    2.50    --  113.25  61.00   0.00  148
 90  \w     92.00 118.00   0.50    2.50    --  113.25  77.00 150.00   52
 91  \w    102.00 132.00   0.50    2.50    --  113.25  61.00 -30.00   60
 92  \w     42.00  97.00   0.50    2.50    --  113.25 -77.00 150.00  110
 93  \w    115.00 141.00   0.50    2.50    --  113.25 125.00  60.00   52
 94  \w     48.00  99.00   0.50    2.50    --  113.25 -94.00 -90.00  102
 95  \w     42.00  68.00   0.50    2.50    --  113.25 -94.00-120.00   52
 96  \w    130.00 162.00   0.50    2.50    --  113.25  91.00 -85.00   64
;
_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      0.036442
_diffrn_orient_matrix_UB_12      0.0583224
_diffrn_orient_matrix_UB_13      0.0818846
_diffrn_orient_matrix_UB_21      -0.0893246
_diffrn_orient_matrix_UB_22      -0.0238177
_diffrn_orient_matrix_UB_23      0.062709
_diffrn_orient_matrix_UB_31      0.058735
_diffrn_orient_matrix_UB_32      -0.0723889
_diffrn_orient_matrix_UB_33      0.0454146
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            76825
_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         72.792
_diffrn_reflns_theta_min         3.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.864
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.45441
_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    1.54
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0476P)^2^+10.5293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0
_reflns_number_gt                5704
_reflns_number_total             5939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04137a2.cif
_cod_data_source_block           21EH057_AMB-394
_cod_depositor_comments
'Adding full bibliography for 7128836--7128839.cif.'
_cod_database_code               7128836
_shelx_estimated_absorpt_t_min   0.564
_shelx_estimated_absorpt_t_max   0.861
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.729
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
        1. Twinned data refinement
 Scales: 0.8222(16)
 0.1778(16)
        2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
        3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C21(H21), C6(H6), C19(H19), C24(H24), C25(H25), C18(H18),
 C26(H26), C13(H13), C27(H27), C3(H3), C11(H11), C28(H28), C5(H5), C4(H4),
 C14(H14), C10(H10), C20(H20), C12(H12)
        3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              273
_shelx_hkl_checksum              51075