Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes.
Takahashi, Masaki; Asaba, Kyohei; Lua, Trinh Thi; Inuzuka, Toshiyasu; Uemura, Naohiro; Sakamoto, Masami; Sengoku, Tetsuya; Yoda, Hidemi; The Journal of organic chemistry 83 (2018) 624–631; doi:10.1021/acs.joc.7b02540

data_4033333
_publ_section_title
;
 Controllable Monobromination of Perylene Ring System: Synthesis of
 Bay-Functionalized Perylene Dyes.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              624
_journal_page_last               631
_journal_paper_doi               10.1021/acs.joc.7b02540
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C58 H50 Cl6 N2 O6'
_chemical_formula_weight         1083.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 104.367(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6869(3)
_cell_length_b                   37.5546(12)
_cell_length_c                   11.2665(3)
_cell_measurement_reflns_used    7186
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2115
_cell_measurement_theta_min      3.7843
_cell_volume                     5200.1(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18278
_diffrn_reflns_theta_full        68.255
_diffrn_reflns_theta_max         68.255
_diffrn_reflns_theta_min         2.353
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    3.450
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.845
_refine_ls_abs_structure_details
;
Flack x determined using 2295 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.075(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         7508
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.322
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0947
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2709
_refine_ls_wR_factor_ref         0.2773
_reflns_number_gt                6996
_reflns_number_total             7508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02540_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4033333.cif.'
_cod_database_code               4033333