Supramolecular Catalysis at Work: Diastereoselective Synthesis of a Molecular Bowl with Dynamic Inner Space
Zhiqing Yan; Troy McCracken; Shijing Xia; Veselin Maslak; Judith Gallucci; Christopher M. Hadad; Jovica D. Badjič; Journal of Organic Chemistry 73 (2008) 355–363; doi:10.1021/jo701538g

data_4023191
_publ_section_title
;
 Supramolecular Catalysis at Work: Diastereoselective Synthesis of
 a Molecular Bowl with Dynamic Inner Space
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              355
_journal_page_last               363
_journal_paper_doi               10.1021/jo701538g
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C39 H24 N6, 3(H2 O)'
_chemical_formula_sum            'C39 H30 N6 O3'
_chemical_formula_weight         630.69
_chemical_name_common            'Badjic 1579'
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      57
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-06-21T13:45:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6837(2)
_cell_length_b                   20.8217(2)
_cell_length_c                   19.9034(2)
_cell_measurement_reflns_used    9094
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     7328.53(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.90698E-2
_diffrn_orient_matrix_UB_12      0.54378E-1
_diffrn_orient_matrix_UB_13      -0.125933E-1
_diffrn_orient_matrix_UB_21      0.372299E-1
_diffrn_orient_matrix_UB_22      -0.1595E-2
_diffrn_orient_matrix_UB_23      -0.337004E-1
_diffrn_orient_matrix_UB_31      -0.313167E-1
_diffrn_orient_matrix_UB_32      -0.13092E-1
_diffrn_orient_matrix_UB_33      -0.33977E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            73462
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular rod'
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;The solvents used for recrystallization were ethyl acetate
and hexane, but neither of these molecules were recognized
in the disordered regions of electron density.  SQUEEZE
was used to account for the disordered solvent.
;
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         8642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.175
_reflns_number_gt                5143
_reflns_number_total             8642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701538g-File002.cif
_cod_data_source_block           Badjic1579
_cod_database_code               4023191