Cooperative Aggregations of Nitrogen-Containing Perylene Diimides Driven by Rigid and Flexible Functional Groups
Kumagai, Shohei; Ishii, Hiroyuki; Watanabe, Go; Annaka, Tatsuro; Fukuzaki, Eiji; Tani, Yukio; Sugiura, Hiroki; Watanabe, Tetsuya; Kurosawa, Tadanori; Takeya, Jun; Okamoto, Toshihiro; Chemistry of Materials  (2020) –; doi:10.1021/acs.chemmater.0c01888

data_4003697
_publ_section_title
;
 Cooperative Aggregations of Nitrogen-Containing Perylene Diimides Driven
 by Rigid and Flexible Functional Groups
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01888
_journal_year                    2020
_chemical_formula_moiety         'C40 H28 N4 O4'
_chemical_formula_sum            'C40 H28 N4 O4'
_chemical_formula_weight         628.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 105.331(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7896(2)
_cell_length_b                   50.055(3)
_cell_length_c                   6.5050(4)
_cell_measurement_reflns_used    12352
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.53
_cell_volume                     1504.03(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17501
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.532
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1131P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.2017
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                2781
_reflns_number_total             5495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c01888_si_003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4003697
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.627
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              83789
_shelx_hkl_checksum              40058