Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki‒Miyaura Cross-Coupling
Bullough, Emma K.; Little, Marc A.; Willans, Charlotte E.; Organometallics 32 (2013) 570–; doi:10.1021/om301085s

data_4079959
_publ_section_title
;
 Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene
 Calix[4]arene and Its Transmetalation to Palladium: Activity of the
 Palladium Complex in Suzuki--Miyaura Cross-Coupling
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              570
_journal_paper_doi               10.1021/om301085s
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         '2(C88 H116 Br8 N12 O8 Pd4), 15(C2 H3 N)'
_chemical_formula_sum            'C206 H277 Br16 N39 O16 Pd8'
_chemical_formula_weight         5685.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 95.272(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   42.542(6)
_cell_length_b                   24.032(4)
_cell_length_c                   14.441(2)
_cell_measurement_reflns_used    7772
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.4505
_cell_measurement_theta_min      2.459
_cell_volume                     14702(4)
_computing_cell_refinement
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_collection
;
APEX 2 software, Bruker Nonius 2004 
;
_computing_data_reduction
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs. 
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, 
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M.     Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) 
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M.     Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean
; 
120 microns
;
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            88980
_diffrn_reflns_theta_full        24.44
_diffrn_reflns_theta_max         24.44
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  0.8767
_exptl_absorpt_correction_T_min  0.4783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
See Sheldrick, G. M. (2002). SADABS.
 University of Gottingen, Germany. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             5684
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
A calculated total of 38 additional MeCN 
solvent molecules per unit cell were removed by the 
SQUEEZE routine, this equates to 4.75 MeCN solvent molecules 
per asymmetric unit.    
;
_refine_diff_density_max         1.473
_refine_diff_density_min         -1.363
_refine_diff_density_rms         0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         12096
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+494.76P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2486
_refine_ls_wR_factor_ref         0.2566
_reflns_number_gt                9380
_reflns_number_total             12096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301085s_si_002.cif
_cod_data_source_block           complex_5
_cod_original_cell_volume        14701(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4079959