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_4023870
_publ_contact_author             'Gibson, H. W.'
_publ_contact_author_email       hwgibson@vt.edu
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C37 H45 N O14'
_chemical_formula_sum            'C37 H45 N O14'
_chemical_formula_weight         727.74
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             2008-06-23T16:24:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                73.219(6)
_cell_angle_beta                 87.759(5)
_cell_angle_gamma                64.149(7)
_cell_formula_units_Z            2
_cell_length_a                   11.3377(8)
_cell_length_b                   12.6716(8)
_cell_length_c                   14.0225(9)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      135
_cell_measurement_theta_min      1
_cell_measurement_wavelength     0.71073
_cell_volume                     1726.9(2)
_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, 1997)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8591
_diffrn_reflns_theta_full        62.5
_diffrn_reflns_theta_max         62.55
_diffrn_reflns_theta_min         4.07
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.4
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.79
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.79
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                3353
_reflns_number_total             5205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801886x_si_002.cif
_cod_data_source_block           amp007
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023870