Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics
Chlebosz, Dorota; Goldeman, Waldemar; Janus, Krzysztof; Szuster, Michał; Kiersnowski, Adam; Molecules 28 (2023) 2940–; doi:10.3390/molecules28072940

data_1568789
_publ_section_title
;
 Synthesis, Solution, and Solid State Properties of Homological
 Dialkylated Naphthalene Diimides---A Systematic Review of Molecules for
 Next-Generation Organic Electronics
;
_journal_issue                   7
_journal_name_full               Molecules
_journal_page_first              2940
_journal_paper_doi               10.3390/molecules28072940
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'C32 H42 N2 O4'
_chemical_formula_sum            'C32 H42 N2 O4'
_chemical_formula_weight         518.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.026(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8486(5)
_cell_length_b                   4.8383(5)
_cell_length_c                   37.741(2)
_cell_measurement_reflns_used    1266
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8420
_cell_measurement_theta_min      3.8410
_cell_volume                     1427.66(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0593
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     28.00  68.20   0.30   60.00    --   18.63 -99.00-180.00  134
  2  \w     43.00  71.20   0.30   60.00    --  -19.25 178.00  60.00   94
  3  \w    -72.00  53.10   0.30   60.00    --  -19.25  38.00-150.00  417
  4  \w    -39.00  11.10   0.30   60.00    --  -19.25 -77.00 -30.00  167
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124750000
_diffrn_orient_matrix_UB_12      0.0147475000
_diffrn_orient_matrix_UB_13      0.0147011000
_diffrn_orient_matrix_UB_21      -0.0395502000
_diffrn_orient_matrix_UB_22      -0.0934396000
_diffrn_orient_matrix_UB_23      0.0022895000
_diffrn_orient_matrix_UB_31      0.0583488000
_diffrn_orient_matrix_UB_32      -0.0663986000
_diffrn_orient_matrix_UB_33      0.0000078000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            4992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         22.184
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Ag) X-ray Source'
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0531P)^2^+0.1312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2168
_reflns_number_total             3040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            NDI_C9.cif
_cod_data_source_block           ndi_c9
_cod_database_code               1568789
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     19.94
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C4(H4A,H4B), C5(H5A,H5B),
 C6(H6A,H6B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2020-02-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.850