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_4127332
_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 O2'
_chemical_formula_sum            'C33 H36 N8 O2'
_chemical_formula_weight         576.71
_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
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                88.66(3)
_cell_angle_beta                 89.03(3)
_cell_angle_gamma                78.79(3)
_cell_formula_units_Z            2
_cell_length_a                   9.875(2)
_cell_length_b                   12.094(2)
_cell_length_c                   12.985(3)
_cell_measurement_reflns_used    4536
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4709
_cell_measurement_theta_min      1.5688
_cell_volume                     1520.7(6)
_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      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.0839
              2theta: -20.0234
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.0839
              2theta: -20.0234
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.0839
              2theta: -20.0234
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0355
_diffrn_orient_matrix_UB_12      -0.0683
_diffrn_orient_matrix_UB_13      0.0688
_diffrn_orient_matrix_UB_21      -0.0340
_diffrn_orient_matrix_UB_22      -0.0511
_diffrn_orient_matrix_UB_23      -0.0578
_diffrn_orient_matrix_UB_31      0.0676
_diffrn_orient_matrix_UB_32      -0.0006
_diffrn_orient_matrix_UB_33      -0.0370
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19256
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.443
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6912
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0759
_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^)+(0.0567P)^2^+0.8047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1739
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6251
_reflns_number_total             6912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10226_si_002.cif
_cod_data_source_block           sa4411
_cod_original_cell_volume        1520.8(6)
_cod_database_code               4127332
_diffrn_number_total             6925
_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. Rigid bond restraints
 C19, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Others
 Sof(H7)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H7A)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(O1A)=Sof(C8A)=Sof(O2A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=1-FVAR(2)
 Sof(O2)=Sof(C8)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(O1)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C7(H7A), C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11A(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C26(H26), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C9A(H9AA,H9AB,H9AC)
;
_shelx_res_checksum              61806
_shelx_hkl_checksum              64244
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'