Diastereoselective Formation of Glycoluril Dimers: Isomerization Mechanism and Implications for Cucurbit[n]uril Synthesis
Arindam Chakraborty; Anxin Wu; Dariusz Witt; Jason Lagona; James C. Fettinger; Lyle Isaacs; Journal of the American Chemical Society 124 (2002) 8297–8306; doi:10.1021/ja025876f

data_4114945
_publ_contact_author
;
Lyle Isaacs
University of Maryland
Department of Chemistry and Biochemistry
College Park, MD 20742
;
_publ_contact_author_email       LI8@umail.umd.edu
_publ_section_title
;
 Diastereoselective Formation of Glycoluril Dimers: Isomerization
 Mechanism and Implications for Cucurbit[n]uril Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8297
_journal_page_last               8306
_journal_paper_doi               10.1021/ja025876f
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C45 H40 F8 N8 O12'
_chemical_formula_weight         1036.85
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c 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                   16.1489(10)
_cell_length_b                   11.4856(7)
_cell_length_c                   24.0250(15)
_cell_measurement_temperature    193(2)
_cell_volume                     4456.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            67824
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   'empirical, SADABS'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_coef       0.00047(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     819
_refine_ls_number_reflns         10247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0467P)^2^+1.0238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                8968
_reflns_number_total             10247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja025876f_s2.cif
_cod_data_source_block           18c
_cod_database_code               4114945