Synthesis of Mono- and 1,3-Diaminocalix[4]arenes via Ullmann-Type Amination and Amidation of 1,3-Bistriflate Esters of Calix[4]arenes
Yuka Nakamura; Shinya Tanaka; Ryuichi Serizawa; Naoya Morohashi; Tetsutaro Hattori; Journal of Organic Chemistry 76 (2011) 2168–2179; doi:10.1021/jo102566e

data_4026168
_publ_section_title
;
 Synthesis of Mono- and 1,3-Diaminocalix[4]arenes via Ullmann-Type
 Amination and Amidation of 1,3-Bistriflate Esters of Calix[4]arenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2168
_journal_page_last               2179
_journal_paper_doi               10.1021/jo102566e
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C60 H76 N2 O6 S6'
_chemical_formula_weight         1113.59
_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                 106.207(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.710(3)
_cell_length_b                   23.366(3)
_cell_length_c                   18.063(4)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.35
_cell_volume                     5962(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33189
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.785900
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       prism
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0579P)^2^+8.1502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                5945
_reflns_number_total             6800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102566e_si_004.cif
_cod_data_source_block           1-3-BisNHTs
_cod_original_cell_volume        5962.0(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4026168