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_4079958
_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
'4(C80 H108 N8 O8), 11(C2 H6 O S), 16(Br), 2(H2O)'
_chemical_formula_sum            'C342 H502 Br16 N32 O44 S11'
_chemical_formula_weight         7392.92
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                99.003(4)
_cell_angle_beta                 98.530(4)
_cell_angle_gamma                96.578(4)
_cell_formula_units_Z            1
_cell_length_a                   18.4774(16)
_cell_length_b                   22.3850(19)
_cell_length_c                   27.557(2)
_cell_measurement_reflns_used    8100
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.105
_cell_measurement_theta_min      2.501
_cell_volume                     11021.8(16)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_detector       'ApexII camera'
_diffrn_radiation_monochromator
;
graphite model mounted in "parallel" mode
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            108088
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  0.8856
_exptl_absorpt_correction_T_min  0.8001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
See Sheldrick, G. M. (2002). SADABS.
 University of Gottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             3862.0
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
A calculated total of 12 additional DMSO solvent molecules  
were removed by the SQUEEZE routine, this equates to 6 DMSO 
solvent molecules per asymmetric unit.    
;
_refine_diff_density_max         2.783
_refine_diff_density_min         -1.457
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1959
_refine_ls_number_reflns         28737
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0949
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2802
_refine_ls_wR_factor_ref         0.3059
_reflns_number_gt                18742
_reflns_number_total             28814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301085s_si_002.cif
_cod_data_source_block           compound_3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4079958