1-Mono- and 1,7-Disubstituted Perylene Bisimide Dyes with Voluminous Groups at Bay Positions: In Search for Highly Effective Solid-State Fluorescence Materials
Stolte, Matthias; Schembri, Tim; Süß, Jasmin; Schmidt, David; Krause, Ana-Maria; Vysotsky, Myroslav O.; Würthner, Frank; Chemistry of Materials  (2020) –; doi:10.1021/acs.chemmater.0c02115

data_4003623
_publ_section_title
;
 1-Mono- and 1,7-Disubstituted Perylene Bisimide Dyes with Voluminous
 Groups at Bay Positions: In Search for Highly Effective Solid-State
 Fluorescence Materials
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c02115
_journal_year                    2020
_chemical_formula_moiety         'C108 H110 N2 O6, 3 (C H2 Cl2)'
_chemical_formula_sum            'C111 H116 Cl6 N2 O6'
_chemical_formula_weight         1786.75
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.624(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.9195(4)
_cell_length_b                   22.9952(7)
_cell_length_c                   15.6794(5)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      3.59
_cell_volume                     4665.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_Photon100
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34238
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.188
_diffrn_reflns_theta_min         3.590
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1892
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.106
_refine_diff_density_min         -1.266
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         9106
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0831
_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^)+(0.1224P)^2^+10.3306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6482
_reflns_number_total             9106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c02115_si_006.cif
_cod_data_source_block           294_JSBA07_fertig_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4003623
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              58725
_shelx_hkl_checksum              22334