Synthesis and optical and electrochemical properties of core-fluorinated perylene bisimides.
Würthner, Frank; Osswald, Peter; Schmidt, Rüdiger; Kaiser, Theo E.; Mansikkamäki, Heidi; Könemann, Martin; Organic letters 8 (2006) 3765–3768; doi:10.1021/ol0613416

data_1506128
_publ_section_title
;
 Synthesis and optical and electrochemical properties of core-fluorinated
 perylene bisimides.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3765
_journal_page_last               3768
_journal_paper_doi               10.1021/ol0613416
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C48 H40 O4 N2 F2, 2(C7 H8)'
_chemical_formula_sum            'C62 H56 F2 N2 O4'
_chemical_formula_weight         931.09
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.135(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.040(2)
_cell_length_b                   11.320(1)
_cell_length_c                   25.137(2)
_cell_measurement_temperature    103(2)
_cell_volume                     4811.2(8)
_computing_molecular_graphics    'Mercury 1.4.1, ccdc'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker AXS CCD'
_diffrn_measurement_method       'rotation in phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28605
_diffrn_reflns_theta_full        57.44
_diffrn_reflns_theta_max         57.44
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.9352
_exptl_absorpt_correction_T_min  0.7729
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_recrystallization_method
'Cooling of toluene solution to -30\%C'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00376(18)
_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   1.035
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0516P)^2^+2.3971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                4828
_reflns_number_total             6387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0613416si1.cif
_cod_data_source_block           2a
_cod_original_cell_volume        4811.3(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1506128