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_1504282
_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            'C66 H48 F12 N4 O4'
_chemical_formula_weight         1189.08
_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                 103.6540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.3251(4)
_cell_length_b                   8.2876(2)
_cell_length_c                   18.7323(4)
_cell_measurement_reflns_used    8911
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.0
_cell_volume                     2764.50(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25460
_diffrn_reflns_theta_full        61.98
_diffrn_reflns_theta_max         61.98
_diffrn_reflns_theta_min         4.86
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0991
_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^)+(0.1600P)^2^+3.4531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2556
_refine_ls_wR_factor_ref         0.3364
_reflns_number_gt                2125
_reflns_number_total             4335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902271b_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2764.49(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504282