Dialkylated dibenzo[a,h]anthracenes for solution-processable organic thin-film transistors
Yang, Tengzhou; Zhang, Liang; Bao, Yucong; Wei, Haoming; RSC Advances 14 (2024) 36390–36397; doi:10.1039/D4RA07439D

data_7249592
_publ_section_title
;
 Dialkylated dibenzo[a,h]anthracenes for solution-processable organic
 thin-film transistors
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              36390
_journal_page_last               36397
_journal_paper_doi               10.1039/D4RA07439D
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         '2(C23 H31)'
_chemical_formula_sum            'C46 H62'
_chemical_formula_weight         614.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                88.781(4)
_cell_angle_beta                 89.088(3)
_cell_angle_gamma                89.979(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9582(3)
_cell_length_b                   7.7761(4)
_cell_length_c                   34.9263(15)
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74.7630
_cell_measurement_theta_min      2.5200
_cell_volume                     1889.11(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.953
_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     66.00 113.00   0.50    0.20    --   44.65 151.00 123.00   94
  2  \w     62.00  87.00   0.50    0.40    --  112.00 151.00 123.00   50
  3  \w    101.00 127.00   0.50    0.40    --  112.00 122.00 -37.00   52
  4  \w     48.00  94.00   0.50    0.40    --  112.00-125.00 120.00   92
  5  \w     68.00 118.00   0.50    0.40    --  112.00-151.00  78.00  100
  6  \w     77.00 106.00   0.50    0.40    --  112.00 -94.00 -90.00   58
  7  \w     40.00  66.00   0.50    0.40    --  112.00 -94.00 -90.00   52
  8  \w    -97.00 -72.00   0.50    0.20    --  -44.65 151.00 123.00   50
  9  \w    -90.00 -65.00   0.50    0.40    -- -100.00 151.00 123.00   50
 10  \w    -67.00 -42.00   0.50    0.20    --  -44.65 122.00 -37.00   50
 11  \w   -107.00 -80.00   0.50    0.40    -- -100.00 125.00-150.00   54
 12  \w   -112.00 -87.00   0.50    0.40    -- -100.00 125.00-180.00   50
 13  \w    -63.00 -31.00   0.50    0.40    -- -100.00 125.00-180.00   64
 14  \w    -73.00 -42.00   0.50    0.40    -- -100.00  61.00 -90.00   62
 15  \w    -54.00 -29.00   0.50    0.40    -- -100.00  45.00  90.00   50
 16  \w    -51.00 -25.00   0.50    0.40    -- -100.00  45.00 120.00   52
 17  \w   -129.00 -80.00   0.50    0.40    -- -100.00 -30.00 120.00   98
 18  \w   -170.00-132.00   0.50    0.40    -- -100.00 -30.00 120.00   76
 19  \w   -115.00 -90.00   0.50    0.20    --  -44.65-151.00  78.00   50
 20  \w   -139.00-114.00   0.50    0.40    -- -100.00-151.00  78.00   50
 21  \w   -104.00 -24.00   0.50    0.20    --  -44.65 -77.00 150.00  160
 22  \w   -108.00 -81.00   0.50    0.50    --  -45.28 -33.00 -55.00   54
 23  \w    -58.00 -24.00   0.50    0.50    --  -45.28 125.00-150.00   68
 24  \w    -52.00 -25.00   0.50    0.50    --  -45.28 -33.00 -55.00   54
 25  \w    -19.00  16.00   0.50    0.50    --  -45.28  19.00 -90.00   70
 26  \w     -9.00  22.00   0.50    0.50    --   45.28 -19.00  30.00   62
 27  \w    -73.00 -26.00   0.50    0.80    -- -100.00  61.00 -30.00   94
 28  \w   -126.00-101.00   0.50    0.80    -- -100.00 144.00 153.23   50
 29  \w   -111.00 -82.00   0.50    0.80    -- -100.00 125.00  60.00   58
 30  \w   -131.00 -82.00   0.50    0.80    -- -100.00-125.00-150.00   98
 31  \w    -74.00 -49.00   0.50    0.80    -- -100.00  61.00-180.00   50
 32  \w    -51.00 -26.00   0.50    0.80    -- -100.00 125.00  30.00   50
 33  \w   -103.00 -77.00   0.50    0.80    -- -100.00 125.00  90.00   52
 34  \w   -110.00 -84.00   0.50    0.80    -- -100.00 125.00  30.00   52
 35  \w    -54.00 -25.00   0.50    0.80    -- -100.00  45.00 -60.00   58
 36  \w    -54.00 -29.00   0.50    0.80    -- -100.00  45.00  30.00   50
 37  \w   -173.00-147.00   0.50    0.80    -- -100.00 -94.00  90.00   52
 38  \w    -54.00 -29.00   0.50    0.80    -- -100.00  45.00 150.00   50
 39  \w   -136.00-111.00   0.50    0.80    -- -100.00 -94.00  90.00   50
 40  \w   -174.00-146.00   0.50    0.80    -- -100.00-125.00-150.00   56
 41  \w    -51.00 -26.00   0.50    0.80    -- -100.00 125.00  90.00   50
 42  \w     66.00  92.00   0.50    0.80    --  112.00 -94.00   0.00   52
 43  \w     39.00  64.00   0.50    0.80    --  112.00 -61.00 120.00   50
 44  \w     77.00 103.00   0.50    0.80    --  112.00-125.00 -60.00   52
 45  \w     40.00  65.00   0.50    0.80    --  112.00 -61.00 150.00   50
 46  \w    149.00 175.00   0.50    0.80    --  112.00  61.00 -60.00   52
 47  \w     40.00  65.00   0.50    0.80    --  112.00 -61.00 -30.00   50
 48  \w     42.00 103.00   0.50    0.80    --  112.00 -94.00 120.00  122
 49  \w    131.00 166.00   0.50    0.80    --  112.00  30.00-120.00   70
 50  \w     99.00 140.00   0.50    0.80    --  112.00  61.00 -60.00   82
 51  \w    102.00 128.00   0.50    0.80    --  112.00  30.00-120.00   52
 52  \w     30.00  75.00   0.50    0.35    --   45.28 -96.00 133.00   90
 53  \w    -27.00  22.00   0.50    0.35    --   45.28 -19.00   0.00   98
 54  \w    -21.00  18.00   0.50    0.35    --   45.28 -19.00 150.00   78
 55  \w    -17.00  24.00   0.50    0.35    --   45.28 -19.00  60.00   82
 56  \w      1.00  35.00   0.50    0.35    --   45.28 -37.00 -90.00   68
 57  \w   -108.00 -82.00   0.50    0.64    -- -100.00 110.00-125.83   52
 58  \w    -54.00 -25.00   0.50    0.64    -- -100.00  45.00 -30.00   58
 59  \w   -126.00-100.00   0.50    0.64    -- -100.00 -30.00 150.00   52
 60  \w   -157.00-127.00   0.50    0.64    -- -100.00 -45.00  60.00   60
 61  \w   -166.00-118.00   0.50    0.64    -- -100.00 -61.00  30.00   96
 62  \w    -54.00 -29.00   0.50    0.64    -- -100.00  45.00-120.00   50
 63  \w   -172.00-145.00   0.50    0.64    -- -100.00 -30.00 150.00   54
 64  \w    -67.00 -32.00   0.50    0.64    -- -100.00 125.00 -60.00   70
 65  \w   -106.00 -80.00   0.50    0.64    -- -100.00 -45.00  60.00   52
 66  \w   -112.00 -87.00   0.50    0.64    -- -100.00 125.00 -60.00   50
 67  \w   -105.00 -80.00   0.50    0.64    -- -100.00 -61.00  30.00   50
 68  \w    -53.00 -30.50   0.50    0.64    -- -100.00  45.00  60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0435026000
_diffrn_orient_matrix_UB_12      -0.0700935000
_diffrn_orient_matrix_UB_13      0.0408080000
_diffrn_orient_matrix_UB_21      0.2159425000
_diffrn_orient_matrix_UB_22      -0.0331629000
_diffrn_orient_matrix_UB_23      0.0058586000
_diffrn_orient_matrix_UB_31      0.0225469000
_diffrn_orient_matrix_UB_32      0.1823562000
_diffrn_orient_matrix_UB_33      0.0157312000
_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  0.0993
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            23926
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         2.531
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1679
_refine_ls_R_factor_gt           0.1174
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3056
_refine_ls_wR_factor_ref         0.3415
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3993
_reflns_number_total             7098
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.8365\% 
around [0.00 -0.01 1.00] (reciprocal) or [-0.00 -0.30 0.95] (direct)
;
_cod_data_source_file            d4ra07439d2.cif
_cod_data_source_block           ytz-2
_cod_database_code               7249592
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_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:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
  C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,
 H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10), C11(H11), C25(H25), C26(H26),
 C29(H29), C31(H31), C33(H33), C34(H34)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              8446
_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 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.606
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2