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_7128837
_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         'C29 H26 F10 N2 Zn'
_chemical_formula_sum            'C29 H26 F10 N2 Zn'
_chemical_formula_weight         657.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.154(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4666(4)
_cell_length_b                   17.7242(7)
_cell_length_c                   16.3037(5)
_cell_measurement_reflns_used    10339
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.0410
_cell_measurement_theta_min      5.0060
_cell_volume                     2719.80(18)
_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      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_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     26.00 122.00   0.50    1.40    --   48.53  77.00  90.00  192
  2  \w     97.00 174.00   0.50    5.45    --  107.16 118.00  36.00  154
  3  \w     93.00 174.00   0.50    5.45    --  107.16  57.00 120.00  162
  4  \w     27.00  93.00   0.50    1.40    --   48.53-118.00 -50.00  132
  5  \w     35.00 113.00   0.50    5.45    --  107.16-118.00 -50.00  156
  6  \w     35.00 110.00   0.50    5.45    --  107.16 -99.00   0.00  150
  7  \w     35.00  62.00   0.50    5.45    --  107.16 -57.00 -90.00   54
  8  \w     35.00 110.00   0.50    5.45    --  107.16 -99.00 -60.00  150
  9  \w     35.00 102.00   0.50    5.45    --  107.16 -77.00   0.00  134
 10  \w     35.00  62.00   0.50    5.45    --  107.16 -57.00  60.00   54
 11  \w     35.00 102.00   0.50    5.45    --  107.16 -77.00  60.00  134
 12  \w     35.00  62.00   0.50    5.45    --  107.16 -57.00 150.00   54
 13  \w     35.00  62.00   0.50    5.45    --  107.16 -57.00  30.00   54
 14  \w     35.00  62.00   0.50    5.45    --  107.16 -57.00 -30.00   54
 15  \w     35.00 102.00   0.50    5.45    --  107.16 -77.00  30.00  134
 16  \w     93.00 174.00   0.50    5.45    --  107.16  57.00-150.00  162
 17  \w     93.00 174.00   0.50    5.45    --  107.16  57.00-180.00  162
 18  \w     35.00 102.00   0.50    5.45    --  107.16 -77.00-180.00  134
 19  \w     26.00  99.00   0.50    1.40    --   48.53  77.00 -30.00  146
 20  \w    -24.00  40.00   0.50    1.40    --   48.53 -38.00-150.00  128
 21  \w    -25.00  23.00   0.50    1.40    --   48.53 -19.00 -30.00   96
 22  \w    -25.00  23.00   0.50    1.40    --   48.53 -19.00 -60.00   96
 23  \w    -63.00  -4.00   0.50    1.40    --  -18.75 118.00  36.00  118
 24  \w    -66.00  -9.00   0.50    1.40    --  -18.75 125.00 -60.00  114
 25  \w    -88.00 -27.00   0.50    1.40    --  -18.75 160.00-171.00  122
;
_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      -0.0234982000
_diffrn_orient_matrix_UB_12      -0.0854426000
_diffrn_orient_matrix_UB_13      -0.0116806000
_diffrn_orient_matrix_UB_21      -0.1576657000
_diffrn_orient_matrix_UB_22      0.0095671000
_diffrn_orient_matrix_UB_23      0.0134092000
_diffrn_orient_matrix_UB_31      -0.0375319000
_diffrn_orient_matrix_UB_32      0.0121838000
_diffrn_orient_matrix_UB_33      -0.0934011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23035
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.423
_diffrn_reflns_theta_min         3.695
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.275
_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    1.607
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.102
_refine_diff_density_max         4.502
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.419
_refine_ls_R_factor_all          0.1983
_refine_ls_R_factor_gt           0.1933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5125
_refine_ls_wR_factor_ref         0.5157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4996
_reflns_number_total             5586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04137a2.cif
_cod_data_source_block           19EH014_JMG012
_cod_depositor_comments
'Adding full bibliography for 7128836--7128839.cif.'
_cod_database_code               7128837
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C80 H80 N16 O32 F16 Zn8 '
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C2(H2A,H2B), C15(H15A,H15B), C5(H5A,H5B), C16(H16A,
 H16B), C4(H4A,H4B), C19(H19A,H19B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C10(H10), C9(H9)
;
_shelx_res_checksum              76531
_shelx_hkl_checksum              39425
_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 3.433
_oxdiff_exptl_absorpt_empirical_full_min 0.376