Mechanism of the Ullmann Biaryl Ether Synthesis Catalyzed by Complexes of Anionic Ligands. Evidence for the Reaction of Iodoarenes With Ligated Anionic CuI Intermediates.
Giri, Ramesh; Brusoe, Andrew; Troshin, Konstantin; Wang, Justin Y.; Font, Marc; Hartwig, John F.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b11853

data_4126977
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Mechanism of the Ullmann Biaryl Ether Synthesis Catalyzed by Complexes of
 Anionic Ligands. Evidence for the Reaction of Iodoarenes With Ligated
 Anionic CuI Intermediates.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11853
_journal_year                    2017
_chemical_compound_source        synthetic
_chemical_formula_analytical     'C18 H12 Cu K N2 O2'
_chemical_formula_iupac          'C18 H12 Cu K N2 O2'
_chemical_formula_moiety         'C18 H12 Cu K N2 O2'
_chemical_formula_sum            'C18 H12 Cu K N2 O2'
_chemical_formula_weight         390.94
_chemical_name_common            'potassium bis(quinolin-8-olate)copper(I)'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                72.568(3)
_cell_angle_beta                 71.515(3)
_cell_angle_gamma                81.227(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3084(4)
_cell_length_b                   10.3550(5)
_cell_length_c                   11.3185(6)
_cell_measurement_reflns_used    5933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.44
_cell_volume                     773.50(7)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba04nas
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16099
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.693
_exptl_absorpt_correction_T_max  0.8624
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_id                test
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 2 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.3250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                2491
_reflns_number_total             2842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b11853_si_002.cif
_cod_data_source_block           K[Cu(LX1)2]
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        773.49(7)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4126977