A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
Hien-Quang Do; Rana M. Kashif Khan; Olafs Daugulis; Journal of the American Chemical Society 130 (2008) 15185–15192; doi:10.1021/ja805688p

data_4108640
_publ_section_title
;
 A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15185
_journal_page_last               15192
_journal_paper_doi               10.1021/ja805688p
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C38 H22 Cu2 F8 N4 O2'
_chemical_formula_weight         845.68
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.516(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3839(6)
_cell_length_b                   17.3423(11)
_cell_length_c                   10.0786(6)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.34
_cell_volume                     1637.09(18)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8401
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.389
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'Bright red'
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       column
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.0356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                2082
_reflns_number_total             3001
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            ja805688p_si_001.cif
_cod_data_source_block           k1123
_cod_database_code               4108640