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_4026813
_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         'C40 H30 N4 O2'
_chemical_formula_sum            'C40 H30 N4 O2'
_chemical_formula_weight         598.68
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 94.853(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3473(14)
_cell_length_b                   8.9927(8)
_cell_length_c                   23.966(2)
_cell_measurement_temperature    223(2)
_cell_volume                     3510.5(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16338
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 2001)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_platon_squeeze_details
;
Numerous peaks were identified in a disc-shaped region.  These peaks were 
likely caused by numerous overlapping fractionally occupied chloroform 
molecules.  Platon/Squeeze was used to correct the model for this disordered 
solvent.
;
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1304P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2200
_reflns_number_gt                2441
_reflns_number_total             4013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202107w_si_003.cif
_cod_data_source_block           LJB-III-14-6b
_cod_database_code               4026813