High-Yielding, Regiospecific Synthesis of cis(4,4')-Di(carbomethoxybenzo)-30-crown-10, Its Conversion to a Pyridyl Cryptand and Strong Complexation of 2,2'- and 4,4'-Bipyridinium Derivatives
Adam M.-P. Pederson; Elizabeth M. Ward; Daniel V. Schoonover; Carla Slebodnick; Harry W. Gibson; Journal of Organic Chemistry 73 (2008) 9094–9101; doi:10.1021/jo801886x

data_4023873
_publ_section_title
;
 High-Yielding, Regiospecific Synthesis of
 cis(4,4')-Di(carbomethoxybenzo)-30-crown-10, Its Conversion
 to a Pyridyl Cryptand and Strong Complexation
 of 2,2'- and 4,4'-Bipyridinium Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9094
_journal_page_last               9101
_journal_paper_doi               10.1021/jo801886x
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety
'2(C37 H45 N O14), 2(C14 H18 N2 O2), 4(F6 P), C3 H6 O, 2(H2 O)'
_chemical_formula_sum            'C105 H136 F24 N6 O35 P4'
_chemical_formula_weight         2622.08
_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                89.867(2)
_cell_angle_beta                 81.082(2)
_cell_angle_gamma                85.426(2)
_cell_formula_units_Z            2
_cell_length_a                   13.9741(4)
_cell_length_b                   16.8936(5)
_cell_length_c                   26.4827(5)
_cell_measurement_reflns_used    9490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9999
_cell_measurement_theta_min      3.7067
_cell_volume                     6156.3(3)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_publication_material
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_type            'Oxford Diffraction Sapphire 3 CCD'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41900
_diffrn_reflns_theta_full        26.11
_diffrn_reflns_theta_max         26.11
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2728
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_platon_squeeze_details
;
 A region of weak residual electron density peaks(1-2 e/A^3^)
 could not be modeled as anything chemically reasonable.  Presumably
 the peaks were from partially evaporated solvent (acetone and
 pentane) molecules.  An electron count of "8" in the void space
 also suggests partially evaporated solvent.
;
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1646
_refine_ls_number_reflns         24087
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1694
_reflns_number_gt                9612
_reflns_number_total             24087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801886x_si_005.cif
_cod_data_source_block           gibson1b
_cod_database_code               4023873