Radical Reactivity, Catalysis and Reaction Mechanism of Arylcopper(II) Compounds: The Missing Link in Organocopper Chemistry.
Zhang, Qian; Wang, Ting; Zhang, Xinhao; Tong, Shuo; Wu, Yun-Dong; Wang, Mei-Xiang; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10226

data_4127335
_publ_section_title
;
 Radical Reactivity, Catalysis and Reaction Mechanism of Arylcopper(II)
 Compounds: The Missing Link in Organocopper Chemistry.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10226
_journal_year                    2019
_chemical_formula_moiety         'C33 H36 N8 O'
_chemical_formula_sum            'C33 H36 N8 O'
_chemical_formula_weight         560.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                87.306(7)
_cell_angle_beta                 88.844(8)
_cell_angle_gamma                80.607(9)
_cell_formula_units_Z            2
_cell_length_a                   9.994(3)
_cell_length_b                   12.000(3)
_cell_length_c                   13.119(4)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    296.1500
_cell_measurement_theta_max      27.4779
_cell_measurement_theta_min      1.5541
_cell_volume                     1550.4(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      296.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.0045
              2theta: -19.8981
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.0045
              2theta: -19.8981
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0045
              2theta: -19.8981
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0141
_diffrn_orient_matrix_UB_12      0.0252
_diffrn_orient_matrix_UB_13      0.0972
_diffrn_orient_matrix_UB_21      0.0695
_diffrn_orient_matrix_UB_22      0.0454
_diffrn_orient_matrix_UB_23      -0.0160
_diffrn_orient_matrix_UB_31      -0.0462
_diffrn_orient_matrix_UB_32      0.0565
_diffrn_orient_matrix_UB_33      -0.0223
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16068
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.200
_diffrn_reflns_theta_max         25.200
_diffrn_reflns_theta_min         1.554
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      2.292
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.1099
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2991
_refine_ls_wR_factor_ref         0.3097
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4425
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10226_si_005.cif
_cod_data_source_block           mx4807a
_cod_original_cell_volume        1550.4(7)
_cod_database_code               4127335
_diffrn_number_total             7056
_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. Restrained distances
 O32-C31 = O32A-C31
 1.2 with sigma of 0.01
 C31-C25 = C31-C1
 1.54 with sigma of 0.01
 C1-O32A
 2.4 with sigma of 0.02
 C25-O32A
 2.4 with sigma of 0.02
3. Rigid bond restraints
 C10, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O32 \\sim C31 \\sim O32A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(O32) \\sim Ueq, Uanis(O32A) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(N8A) \\sim Ueq, Uanis(N8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(O32A)=1-FVAR(1)
 Sof(O32)=FVAR(1)
 Sof(H25A)=Sof(C30A)=Sof(N8A)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=
 Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(C28A)=Sof(H28D)=Sof(H28E)=
 Sof(H28F)=1-FVAR(2)
 Sof(N8)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30)=FVAR(2)
 Fixed Z: C25(0.206629)
6.a Ternary CH refined with riding coordinates:
 C25(H25), C25(H25A)
6.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C26A(H26C,H26D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22)
6.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C1(H1A,H1B,H1C), C29A(H29D,
 H29E,H29F), C28A(H28D,H28E,H28F)
;
_shelx_res_checksum              41151
_shelx_hkl_checksum              85032
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'