Synthesis, Photophysical and Electronic Properties of Tetra- Donor- or Acceptor-Substituted ortho-Perylenes Displaying Four Reversible Oxidations or Reductions
Merz, Julia; Steffen, Andreas; Nitsch, Jörn; Fink, Julian; Schürger, Claudia B.; Friedrich, Alexandra; Krummenacher, Ivo; Braunschweig, Holger; Moos, Michael; Mims, David; Lambert, Christoph; Marder, Todd B.; Chemical Science  (2019) –; doi:10.1039/C9SC02420D

data_1551893
_publ_section_title
;
 Synthesis, Photophysical and Electronic Properties of Tetra- Donor- or
 Acceptor-Substituted ortho-Perylenes Displaying Four Reversible
 Oxidations or Reductions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02420D
_journal_year                    2019
_chemical_formula_moiety         'C76 H64 N4 O8'
_chemical_formula_sum            'C76 H64 N4 O8'
_chemical_formula_weight         1161.31
_chemical_name_systematic
N2,N2,N5,N5,N8,N8,N11,N11-(4-methoxyphenyl)perylene-2,5,8,11-tetraamine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-11
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-28 deposited with the CCDC.    2019-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.45(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.025(7)
_cell_length_b                   11.576(7)
_cell_length_c                   18.285(9)
_cell_measurement_reflns_used    4322
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.60
_cell_volume                     2955(3)
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_collection       'APEX3 ver. 2016.1-0 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23828
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.511
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0520P)^2^+0.5086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4063
_reflns_number_total             6104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02420d2.cif
_cod_data_source_block           DPA-4-Per
_cod_database_code               1551893
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              6960