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_1568788
_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         'C28 H34 N2 O4'
_chemical_formula_sum            'C28 H34 N2 O4'
_chemical_formula_weight         462.57
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.025(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8730(2)
_cell_length_b                   4.84356(13)
_cell_length_c                   33.0246(9)
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.2370
_cell_measurement_theta_min      2.6020
_cell_volume                     1254.50(6)
_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      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0593
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.914
_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    -51.00  53.00   1.00   65.00    --   22.18 -57.00 -90.00  104
  2  \w    -55.00 104.00   1.00   65.00    --   22.18  19.00 -90.00  159
  3  \w   -111.00 -34.00   1.00   65.00    --  -23.36 178.00 -60.00   77
  4  \w     -9.00  96.00   1.00   65.00    --   22.18  57.00  30.00  105
  5  \w    -56.00  39.00   1.00   65.00    --   22.18 -38.00  90.00   95
  6  \w     35.00 110.00   1.00   65.00    --   22.18 178.00 -90.00   75
  7  \w    -20.00  27.00   1.00   65.00    --  -23.36 -99.00-120.00   47
  8  \w    -20.00  27.00   1.00   65.00    --  -23.36 -99.00  60.00   47
;
_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      0.0241610000
_diffrn_orient_matrix_UB_12      0.0864585000
_diffrn_orient_matrix_UB_13      -0.0158531000
_diffrn_orient_matrix_UB_21      0.0830713000
_diffrn_orient_matrix_UB_22      0.0122962000
_diffrn_orient_matrix_UB_23      0.0100442000
_diffrn_orient_matrix_UB_31      0.0264577000
_diffrn_orient_matrix_UB_32      -0.1175147000
_diffrn_orient_matrix_UB_33      -0.0106094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            12647
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96353
_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_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0471P)^2^+0.3826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2210
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            NDI_C7.cif
_cod_data_source_block           ndi_c7
_cod_database_code               1568788
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_date_sample_data_collection 2020-02-07
_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 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.923