Synthesis of arylated perylene bisimides through C-H bond cleavage under ruthenium catalysis.
Nakazono, Satomi; Easwaramoorthi, Shanmugam; Kim, Dongho; Shinokubo, Hiroshi; Osuka, Atsuhiro; Organic letters 11 (2009) 5426–5429; doi:10.1021/ol902271b

data_1504284
_publ_section_title
;
 Synthesis of arylated perylene bisimides through C-H bond cleavage under
 ruthenium catalysis.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5426
_journal_page_last               5429
_journal_paper_doi               10.1021/ol902271b
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C76 H86 F12 N6 O18 S4'
_chemical_formula_weight         1727.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.543(19)
_cell_angle_beta                 80.424(18)
_cell_angle_gamma                84.60(2)
_cell_formula_units_Z            1
_cell_length_a                   6.815(4)
_cell_length_b                   14.674(10)
_cell_length_c                   20.572(10)
_cell_measurement_reflns_used    7477
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.1
_cell_volume                     1911(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_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  0.0886
_diffrn_reflns_av_sigmaI/netI    0.1317
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15951
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         7477
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.1990
_refine_ls_R_factor_gt           0.0956
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2600
_reflns_number_gt                3406
_reflns_number_total             7477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902271b_si_002.cif
_cod_data_source_block           8
_cod_original_cell_volume        1910.9(19)
_cod_database_code               1504284