Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent
Ester Böeß; Devarajulu Sureshkumar; Abhishek Sud; Cornelia Wirtz; Christophe Farès; Martin Klußmann; Journal of the American Chemical Society 133 (2011) 8106–8109; doi:10.1021/ja201610c

data_4106183
_publ_section_title
;
 Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction
 with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the
 Role of Methanol As a Solvent
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8106
_journal_page_last               8109
_journal_paper_doi               10.1021/ja201610c
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        methanole
_chemical_formula_moiety         'C15 H14 N, 0.5(Br4 Cu2)'
_chemical_formula_sum            'C15 H14 Br2 Cu N'
_chemical_formula_weight         431.63
_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'
_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     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                BSR-BD-061-02
_audit_creation_date             2011-02-04
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.01.21 svn.r1625, GUI svn.r3464)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.803(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0417(12)
_cell_length_b                   10.888(2)
_cell_length_c                   13.8614(17)
_cell_measurement_reflns_used    28322
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.798
_cell_measurement_theta_min      2.6042
_cell_volume                     1510.2(4)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26070
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.90
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.723
_exptl_absorpt_correction_T_max  0.99793
_exptl_absorpt_correction_T_min  0.99270
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.131
_refine_diff_density_min         -1.402
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         5631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+3.7452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                3310
_reflns_number_total             5631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201610c_si_003_2.cif
_cod_data_source_block           7239sadabs
_cod_original_cell_volume        1510.1(4)
_cod_original_sg_symbol_Hall     '-p 2yn)'
_cod_database_code               4106183