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_7128839
_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         'C44 H56 O8 Zn7, C44 H54 O8 Zn7, 2(C7 H8)'
_chemical_formula_sum            'C102 H126 O16 Zn14'
_chemical_formula_weight         2523.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-10
_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                66.616(6)
_cell_angle_beta                 75.238(4)
_cell_angle_gamma                85.544(4)
_cell_formula_units_Z            1
_cell_length_a                   12.8055(5)
_cell_length_b                   14.5382(10)
_cell_length_c                   16.1933(10)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      21.9040
_cell_measurement_theta_min      1.8740
_cell_volume                     2674.8(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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_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    -28.00 109.00   1.00   35.00    --   27.84  38.00  30.00  137
  2  \w    -15.00  42.00   1.00   35.00    --   27.84  77.00 120.00   57
  3  \w     39.00 122.00   1.00   35.00    --   27.84 178.00 -30.00   83
  4  \w    -48.00  66.00   1.00   35.00    --   27.84 -57.00-150.00  114
  5  \w    -42.00  71.00   1.00   35.00    --   27.84 -77.00 -30.00  113
  6  \w    -54.00  83.00   1.00   35.00    --   27.84 -38.00  60.00  137
  7  \w    -15.00  30.00   1.00   35.00    --  -25.00 -99.00 -30.00   45
  8  \w    -15.00  67.00   1.00   35.00    --   27.84 -99.00  30.00   82
  9  \w    -15.00  42.00   1.00   35.00    --   27.84  77.00 -60.00   57
 10  \w    -10.00 104.00   1.00   35.00    --   27.84  57.00  90.00  114
 11  \w    -28.00 109.00   1.00   35.00    --   27.84  38.00-150.00  137
 12  \w    -15.00  42.00   1.00   35.00    --   27.84  77.00-120.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065545000
_diffrn_orient_matrix_UB_12      0.0267235000
_diffrn_orient_matrix_UB_13      0.0267650000
_diffrn_orient_matrix_UB_21      -0.0155706000
_diffrn_orient_matrix_UB_22      0.0446430000
_diffrn_orient_matrix_UB_23      -0.0327793000
_diffrn_orient_matrix_UB_31      -0.0547538000
_diffrn_orient_matrix_UB_32      -0.0109655000
_diffrn_orient_matrix_UB_33      0.0251318000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.5302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.170
_diffrn_reflns_theta_min         1.625
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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    1.566
_exptl_crystal_description       plate
_exptl_crystal_F_000             1286
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         19320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0001P)^2^+0.0020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5078
_reflns_number_total             19320
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9433\% 
 around [-0.00 1.00 -0.00] (reciprocal) or [0.03 0.94 -0.34] (direct)
;
_cod_data_source_file            d1cc04137a2.cif
_cod_data_source_block           19EH039_JMG037
_cod_depositor_comments
'Adding full bibliography for 7128836--7128839.cif.'
_cod_database_code               7128839
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C7H8O1Zn1
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.651
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6747(5)
 0.3253(5)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C22) = Uanis(C26) = Uanis(C23) = Uanis(C25) = Uanis(C24)
Uanis(C2) = Uanis(C4) = Uanis(C3) = Uanis(C1)
Uanis(C27) = Uanis(C32) = Uanis(C28) = Uanis(C30) = Uanis(C31) = Uanis(C29)
Uanis(C9) = Uanis(C10) = Uanis(C11) = Uanis(C14) = Uanis(C13) = Uanis(C12)
Uanis(C15) = Uanis(C20) = Uanis(C16) = Uanis(C18) = Uanis(C19) = Uanis(C17)
Uanis(C39) = Uanis(C015) = Uanis(C42) = Uanis(C40) = Uanis(C41) = Uanis(C43)
Uanis(C37) = Uanis(C33) = Uanis(C38) = Uanis(C34) = Uanis(C36) = Uanis(C35)
Uanis(O2) = Uanis(O4) = Uanis(O3) = Uanis(O1)
Uanis(C7) = Uanis(C5) = Uanis(C8) = Uanis(C6)
Uanis(O7) = Uanis(O5) = Uanis(O8) = Uanis(O6)
Uanis(C45) = Uanis(C46) = Uanis(C47) = Uanis(C44) = Uanis(C50) = Uanis(C48) =
Uanis(C49)
4.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B)
4.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C16(H16), C26(H26), C37(H37), C18(H18), C19(H19),
 C32(H32), C28(H28), C10(H10), C17(H17), C015(H015), C46(H46), C38(H38),
 C34(H34), C42(H42), C23(H23), C25(H25), C30(H30), C36(H36), C11(H11), C35(H35),
  C31(H31), C50(H50), C48(H48), C14(H14), C41(H41), C49(H49), C29(H29),
 C47(H47), C43(H43), C13(H13), C12(H12), C24(H24)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C4(H4A,H4B,H4C), C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C6(H6A,
 H6B,H6C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C44(H44A,H44B,
 H44C)
;
_shelx_res_checksum              63162
_shelx_hkl_checksum              78781
_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 1.525
_oxdiff_exptl_absorpt_empirical_full_min 0.630
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2