Rearrangement of an aniline linked perylene bisimide under acidic conditions and visible to near-infrared emission from intramolecular charge-transfer state of its fused derivatives
Kojima, Mitsuru; Tamoto, Akira; Aratani, Naoki; Yamada, Hiroko; Chem. Commun.  (2017) –; doi:10.1039/C7CC01520H

data_7119975
_publ_section_title
;
 Rearrangement of an aniline linked perylene bisimide under acidic
 conditions and visible to near-infrared emission from intramolecular
 charge-transfer state of its fused derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC01520H
_journal_year                    2017
_chemical_formula_moiety         'C72 H52 N4 O4 S2'
_chemical_formula_sum            'C72 H52 N4 O4 S2'
_chemical_formula_weight         1101.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-23 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                82.196(6)
_cell_angle_beta                 72.123(5)
_cell_angle_gamma                64.915(5)
_cell_formula_units_Z            1
_cell_length_a                   10.5479(11)
_cell_length_b                   12.3384(13)
_cell_length_c                   16.2391(17)
_cell_measurement_reflns_used    6778
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      3.20
_cell_volume                     1821.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1433
_diffrn_reflns_av_unetI/netI     0.1502
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20855
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        23.500
_diffrn_reflns_theta_max         23.500
_diffrn_reflns_theta_min         3.195
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9140
_exptl_absorpt_correction_T_min  0.3370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.259
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_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.2158
_refine_ls_R_factor_gt           0.0911
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2043
_reflns_number_total             5349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01520h2.cif
_cod_data_source_block           shelxl
_cod_database_code               7119975
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              80255
_platon_squeeze_void_probe_radius 1.20