Benzobisoxazole Cruciforms: Heterocyclic Fluorophores with Spatially Separated Frontier Molecular Orbitals
Jaebum Lim; Thomas A. Albright; Benjamin R. Martin; Ognjen Š. Miljanić; Journal of Organic Chemistry 76 (2011) 10207–10219; doi:10.1021/jo202107w

data_4026812
_publ_contact_author_email       miljanic@uh.edu
_publ_contact_author_name        'Ognjen S. Miljanic'
_publ_section_title
;
 Benzobisoxazole Cruciforms: Heterocyclic Fluorophores with Spatially
 Separated Frontier Molecular Orbitals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10207
_journal_page_last               10219
_journal_paper_doi               10.1021/jo202107w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C36 H20 N2 O2'
_chemical_formula_sum            'C36 H20 N2 O2'
_chemical_formula_weight         512.54
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   40.531(3)
_cell_length_b                   40.531(3)
_cell_length_c                   4.3751(4)
_cell_measurement_reflns_used    87
_cell_measurement_temperature    223(2)
_cell_volume                     6224.3(9)
_computing_cell_refinement       'Process-Auto (Rigaku, 2006)'
_computing_data_collection       'SCXmini (Rigaku, 2006)'
_computing_data_reduction        'Process-Auto (Rigaku, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            21017
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 2001)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2394
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_platon_squeeze_details
;
The structure was initially refined with dummy atoms in the cylidrical void 
spaces.  No reasonable electron density peaks could be identified in the 
vicinity of these atoms, and the positions could be split indefinitely.  
Following the Squeeze procedure, the electron density in these regions was 
suppressed and a reasonable structure solution was found with minimal 
residual peaks.
;
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.727
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.727
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                1946
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202107w_si_002.cif
_cod_data_source_block           LJB-12
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4026812