Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye with Latent Bromo Groups for C‒C Cross Coupling
Frischmann, Peter D.; Würthner, Frank; Organic Letters 15 (2013) 4674–; doi:10.1021/ol401946g

data_1512293
_publ_section_title
;
 Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye
 with Latent Bromo Groups for C--C Cross Coupling
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4674
_journal_paper_doi               10.1021/ol401946g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety
'C48 H40 Br2 N2 O4, 1.5 (C7 H8), 0.3676 (C7 H8)'
_chemical_formula_sum            'C61.07 H54.94 Br2 N2 O4'
_chemical_formula_weight         1040.70
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 115.702(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3412(9)
_cell_length_b                   17.7644(10)
_cell_length_c                   17.8268(9)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.58
_cell_measurement_theta_min      3.71
_cell_volume                     4948.3(5)
_computing_cell_refinement       'Bruker SAINT V8.30C'
_computing_data_collection       'Bruker SAINT V8.30C'
_computing_data_reduction        'Bruker SAINT V8.30C'
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    Bruker-SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Cu-Microsource ImuSCu'
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35316
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         2.828
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  .7534
_exptl_absorpt_correction_T_min  .6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             2150
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.032
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     752
_refine_ls_number_reflns         8726
_refine_ls_number_restraints     536
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+6.4206P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7374
_reflns_number_total             8726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol401946g_si_002.cif
_cod_data_source_block           pfd21_ot
_cod_database_code               1512293
_shelx_estimated_absorpt_t_min   0.637
_shelx_estimated_absorpt_t_max   0.925
_shelxl_version_number           2013-2
_shelx_res_checksum              77163
_shelx_hkl_checksum              69425