Electron-donating arene-substituted pentacenedione derivatives: a study of structural, electronic, and electrochemical properties
Younes, Eyad A.; Hammad, Yamen J.; Salami, Fatemeh; Rasras, Anas J.; Al-Qawasmeh, Raed A.; Zhao, Yuming; RSC Advances 14 (2024) 5331–5339; doi:10.1039/D3RA05173K

data_7248119
_publ_section_title
;
 Electron-donating arene-substituted pentacenedione derivatives: a study
 of structural, electronic, and electrochemical properties
;
_journal_issue                   8
_journal_name_full               'RSC Advances'
_journal_page_first              5331
_journal_page_last               5339
_journal_paper_doi               10.1039/D3RA05173K
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C52 H38 O6'
_chemical_formula_sum            'C52 H38 O6'
_chemical_formula_weight         758.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-08
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-07-25 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.32520(10)
_cell_length_b                   22.6642(2)
_cell_length_c                   23.2798(2)
_cell_measurement_reflns_used    24625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.7090
_cell_measurement_theta_min      2.7040
_cell_volume                     3861.37(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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   -119.00 -37.00   0.50    2.70    --  -48.29 -46.00-146.00  164
  2  \w    -44.00  24.00   0.50    2.00    --  -48.29  46.00   2.00  136
  3  \w    -23.00  58.00   0.50    2.00    --   48.29 -46.00-146.00  162
  4  \w     37.00 120.00   0.50    2.00    --   48.29  46.00   2.00  166
  5  \w   -161.00 -79.00   0.50   10.00    --  -90.00 -46.00-146.00  164
  6  \w    -44.00 -18.00   0.50   10.00    --  -90.00  46.00   2.00   52
  7  \w    100.00 178.00   0.50   10.00    --  111.50  46.00   2.00  156
  8  \w    -59.00  24.00   0.50    2.00    --  -48.29  57.00-150.00  166
  9  \w    -16.00  26.00   0.50    2.00    --  -48.29  19.00 150.00   84
 10  \w    -16.00  26.00   0.50    2.00    --  -48.29  19.00 -60.00   84
 11  \w   -161.00 -68.00   0.50   10.00    --  -90.00 -77.00 -60.00  186
 12  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00-150.00   78
 13  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00  60.00   78
 14  \w     40.00 105.00   0.50   10.00    --  111.50 -94.00-120.00  130
 15  \w     40.00 133.00   0.50   10.00    --  111.50 -77.00 -30.00  186
 16  \w    101.00 178.00   0.50   10.00    --  111.50  30.00 120.00  154
 17  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00 120.00   78
 18  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00-180.00   78
 19  \w    101.00 178.00   0.50   10.00    --  111.50  30.00 150.00  154
 20  \w     40.00 105.00   0.50   10.00    --  111.50 -94.00 -60.00  130
 21  \w     40.00 105.00   0.50   10.00    --  111.50 -94.00  90.00  130
 22  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00 150.00   78
 23  \w    101.00 178.00   0.50   10.00    --  111.50  15.00  60.00  154
 24  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00 -60.00   78
 25  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00-120.00   78
 26  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00   0.00   78
 27  \w     40.00  79.00   0.50   10.00    --  111.50 -61.00  90.00   78
 28  \w   -119.00 -34.00   0.50    2.00    --  -48.29 -57.00 150.00  170
 29  \w   -119.00 -88.00   0.50    2.00    --  -48.29 -77.00 -30.00   62
 30  \w     27.00 120.00   0.50    2.00    --   48.29  77.00  60.00  186
 31  \w     -6.00  21.00   0.50    2.00    --    0.94  77.00-150.00   54
 32  \w    -12.00  14.00   0.50    2.00    --  -48.89  19.00 -30.00   52
 33  \w     40.00  86.00   0.50    2.00    --   50.77  57.00 120.00   92
 34  \w     63.00  90.00   0.50    2.00    --   50.77-125.00  30.00   54
 35  \w     91.00 123.00   0.50    2.00    --   50.77  37.00 150.00   64
 36  \w     44.00  81.00   0.50    2.00    --   50.77  37.00 150.00   74
 37  \w   -102.00 -77.00   0.50    2.00    --  -48.29 -46.00-146.00   50
 38  \w    -74.00 -48.00   0.50    2.00    --  -48.29 125.00-180.00   52
 39  \w   -102.00 -73.00   0.50   10.00    --  -90.00 -70.00  64.61   58
 40  \w    -96.00 -71.00   0.50   10.00    --  -90.00 -77.00 150.00   50
 41  \w    -94.00 -68.00   0.50   10.00    --  -90.00 -77.00  90.00   52
 42  \w    -97.00 -71.00   0.50   10.00    --  -90.00 -73.00 124.13   52
 43  \w    -94.00 -68.00   0.50   10.00    --  -90.00 -77.00 120.00   52
 44  \w    -94.00 -69.00   0.50   10.00    --  -90.00 -74.00 107.70   50
 45  \w   -102.00 -77.00   0.50   10.00    --  -90.00 -61.00 150.00   50
 46  \w   -101.00 -76.00   0.50   10.00    --  -90.00 -61.00 120.00   50
 47  \w    -96.00 -71.00   0.50   10.00    --  -90.00 -70.00 124.17   50
 48  \w     95.00 120.00   0.50   10.00    --  111.50  77.00  30.00   50
 49  \w    125.00 165.00   0.50   10.00    --  111.50  61.00  60.00   80
 50  \w    111.00 150.00   0.50   10.00    --  111.50  61.00-120.00   78
 51  \w     91.00 116.00   0.50   10.00    --  111.50  77.00 120.00   50
 52  \w    143.00 178.00   0.50   10.00    --  111.50  45.00  40.61   70
 53  \w     45.00  86.00   0.50   10.00    --  111.50-125.00-120.00   82
 54  \w     96.00 122.00   0.50   10.00    --  111.50  61.00 150.00   52
 55  \w    137.00 163.00   0.50   10.00    --  111.50  77.00  90.00   52
 56  \w    148.00 174.00   0.50   10.00    --  111.50  77.00 150.00   52
 57  \w     56.00  90.00   0.50   10.00    --  111.50-125.00  90.00   68
 58  \w     97.00 122.00   0.50   10.00    --  111.50  61.00  90.00   50
 59  \w    134.00 170.00   0.50   10.00    --  111.50  61.00  90.00   72
 60  \w     49.00  92.00   0.50   10.00    --  111.50-125.00 -90.00   86
 61  \w     99.00 161.00   0.50   10.00    --  111.50  77.00 -30.00  124
 62  \w    117.00 143.00   0.50   10.00    --  111.50 125.00-120.00   52
 63  \w    101.00 150.00   0.50   10.00    --  111.50  45.00 150.00   98
 64  \w     71.00 103.00   0.50   10.00    --  111.50 -94.00-180.00   64
 65  \w     44.00  93.00   0.50   10.00    --  111.50 -94.00 150.00   98
 66  \w     40.00  65.00   0.50   10.00    --  111.50 -54.00  -6.95   50
 67  \w     52.00  97.00   0.50   10.00    --  111.50 -94.00 120.00   90
 68  \w     91.00 128.00   0.50   10.00    --  111.50  77.00 150.00   74
 69  \w     90.00 115.00   0.50   10.00    --  111.50  77.00  90.00   50
 70  \w    116.00 149.00   0.50   10.00    --  111.50 125.00 -30.00   66
 71  \w    111.00 142.00   0.50   10.00    --  111.50 125.00  30.00   62
 72  \w    106.00 132.00   0.50   10.00    --  111.50 125.00 -60.00   52
 73  \w    101.00 127.00   0.50   10.00    --  111.50  45.00 120.00   52
 74  \w     98.00 138.00   0.50   10.00    --  111.50   0.00 -90.00   80
 75  \w     41.00  89.00   0.50   10.00    --  111.50 -94.00  30.00   96
 76  \w    113.00 176.00   0.50   10.00    --  111.50  61.00 -90.00  126
 77  \w    120.00 147.00   0.50   10.00    --  111.50 125.00  60.00   54
 78  \w    114.00 140.00   0.50   10.00    --  111.50 125.00-150.00   52
 79  \w    148.00 176.00   0.50   10.00    --  111.50  61.00-150.00   56
 80  \w    126.00 177.00   0.50   10.00    --  111.50  77.00-120.00  102
 81  \w     63.00  89.00   0.50   10.00    --  111.50 -77.00   0.00   52
 82  \w    101.00 130.00   0.50   10.00    --  111.50 -77.00   0.00   58
 83  \w     40.00  66.00   0.50   10.00    --  111.50 -94.00 -30.00   52
 84  \w     91.00 116.00   0.50   10.00    --  111.50  77.00  60.00   50
 85  \w     42.00  67.00   0.50   10.00    --  111.50-125.00 -30.00   50
 86  \w     98.00 135.00   0.50   10.00    --  111.50  61.00-180.00   74
 87  \w    152.00 177.00   0.50   10.00    --  111.50  15.00  30.00   50
 88  \w    102.00 117.00   0.50   10.00    --  111.50 125.00   0.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1789773000
_diffrn_orient_matrix_UB_12      0.0124837000
_diffrn_orient_matrix_UB_13      0.0350137000
_diffrn_orient_matrix_UB_21      -0.0700751000
_diffrn_orient_matrix_UB_22      -0.0365868000
_diffrn_orient_matrix_UB_23      0.0503000000
_diffrn_orient_matrix_UB_31      0.0856930000
_diffrn_orient_matrix_UB_32      -0.0559220000
_diffrn_orient_matrix_UB_33      -0.0251428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49012
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.218
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.76a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       prism
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3361 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7972
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0554P)^2^+2.5809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                7750
_reflns_number_total             7972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra05173k2.cif
_cod_data_source_block           ey-mome
_cod_database_code               7248119
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C52H38O6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29), C32(H32), C33(H33),
  C35(H35), C36(H36), C40(H40), C41(H41), C43(H43), C44(H44), C47(H47),
 C48(H48), C50(H50), C51(H51)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C37(H37A,H37B,H37C), C45(H45A,H45B,H45C), C52(H52A,H52B,
 H52C)
;
_shelx_res_checksum              26496
_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 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.488