Anion and Carboxylic Acid Binding to Monotopic and Ditopic Amidopyridine Macrocycles
Ivan V. Korendovych; Mimi Cho; Olga V. Makhlynets; Phillip L. Butler; Richard J. Staples; Elena V. Rybak-Akimova; Journal of Organic Chemistry 73 (2008) 4771–4782; doi:10.1021/jo800128r

data_4023495
_publ_section_title
;
 Anion and Carboxylic Acid Binding to Monotopic and Ditopic
 Amidopyridine Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4771
_journal_page_last               4782
_journal_paper_doi               10.1021/jo800128r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H20 N5 O2, Cl O4 '
_chemical_formula_sum            'C13 H20 Cl N5 O6'
_chemical_formula_weight         377.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5718(16)
_cell_length_b                   15.192(2)
_cell_length_c                   9.5817(15)
_cell_measurement_temperature    293(2)
_cell_volume                     1684.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7316
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0864
_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^)+(0.1844P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2370
_refine_ls_wR_factor_ref         0.2800
_reflns_number_gt                905
_reflns_number_total             2220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800128r-File003.cif
_cod_data_source_block           623337
_cod_database_code               4023495