Pyrazinoquinoxaline derivatives for flexible electronic devices: effect of the mechanical properties of the crystals on device durability.
Bezboruah, Jasmine; Khator, Kanha Ram; Gayen, Sayantan; Sanke, Devendra Mayurdhwaj; Mahapatra, Biplab; Sahoo, Anshuman; Nayak, Amlandeep; Reddy, C. Malla; Senanayak, Satyaprasad P.; Zade, Sanjio S.; Chemical science 15 (2024) 19000–19012; doi:10.1039/d4sc04157g

data_1572882
_publ_section_title
;
 Pyrazinoquinoxaline derivatives for flexible electronic devices: effect
 of the mechanical properties of the crystals on device durability.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              19000
_journal_page_last               19012
_journal_paper_doi               10.1039/d4sc04157g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C38 H22 N4 S4'
_chemical_formula_sum            'C38 H22 N4 S4'
_chemical_formula_weight         662.84
_chemical_name_systematic
5,10-diphenyl-2,3,7,8-tetra(thiophen-2-yl)pyrazino[2,3-g]quinoxaline
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-08 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.6590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.0664(2)
_cell_length_b                   18.6023(2)
_cell_length_c                   7.63310(10)
_cell_measurement_reflns_used    10201
_cell_measurement_temperature    273.00(10)
_cell_measurement_theta_max      68.0120
_cell_measurement_theta_min      3.1150
_cell_volume                     3097.57(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 97-2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -30.00  28.00   0.50    0.50    --   41.33 -21.00 -60.00  116
  2  \w    -26.00  65.00   0.50    0.50    --   41.33 -65.00 -30.00  182
  3  \w     32.00 110.00   0.50    4.50    --   96.67-122.00 -48.00  156
  4  \w     27.00 127.00   0.50    4.50    --   96.67 -87.00 120.00  200
  5  \w     47.00 109.00   0.50    0.50    --   41.33-151.00 150.00  124
  6  \w     47.00 130.00   0.50    4.50    --   96.67-151.00 150.00  166
  7  \w     29.00  68.00   0.50    4.50    --   96.67 -59.00 120.00   78
  8  \w     30.00  57.00   0.50    4.50    --   96.67 -50.00 150.00   54
  9  \w     30.00 109.00   0.50    4.50    --   96.67-117.00 150.00  158
 10  \w     30.00  57.00   0.50    4.50    --   96.67 -50.00  30.00   54
 11  \w     28.00 105.00   0.50    4.50    --   96.67 -77.00 -30.00  154
 12  \w     83.00 164.00   0.50    4.50    --   96.67  33.00 120.00  162
 13  \w    105.00 170.00   0.50    4.50    --   96.67  96.00  60.00  130
 14  \w     99.00 164.00   0.50    4.50    --   96.67 117.00   0.00  130
 15  \w     96.00 163.00   0.50    4.50    --   96.67 122.00  32.00  134
 16  \w     78.00 163.00   0.50    4.50    --   96.67  50.00-180.00  170
 17  \w     28.00 105.00   0.50    4.50    --   96.67 -77.00 -90.00  154
 18  \w     29.00  68.00   0.50    4.50    --   96.67 -59.00 -60.00   78
 19  \w     29.00  68.00   0.50    4.50    --   96.67 -59.00 -30.00   78
 20  \w     29.00  68.00   0.50    4.50    --   96.67 -59.00-180.00   78
 21  \w     15.00 110.00   0.50    0.50    --   41.33  77.00   0.00  190
 22  \w     15.00 110.00   0.50    0.50    --   41.33  77.00  60.00  190
 23  \w    -24.00  35.00   0.50    0.50    --  -41.33  11.00 120.00  118
 24  \w    -47.00 -15.00   0.50    4.50    --  -82.50  42.00  60.00   64
 25  \w    -85.00 -10.00   0.50    0.50    --  -41.33 122.00  32.00  150
 26  \w    -47.00 -15.00   0.50    4.50    --  -82.50  42.00 -90.00   64
 27  \w    -47.00 -15.00   0.50    4.50    --  -82.50  42.00-150.00   64
 28  \w    -47.00 -15.00   0.50    4.50    --  -82.50  42.00-180.00   64
 29  \w   -105.00 -25.00   0.50    0.50    --  -41.33 151.00-166.00  160
 30  \w   -109.00 -28.00   0.50    0.50    --  -41.33 -32.00  90.00  162
 31  \w   -110.00 -55.00   0.50    0.50    --  -41.33-151.00 150.00  110
 32  \w   -109.00 -18.00   0.50    0.50    --  -41.33 -65.00  60.00  182
 33  \w   -109.00 -18.00   0.50    0.50    --  -41.33 -65.00-120.00  182
 34  \w   -109.00 -18.00   0.50    0.50    --  -41.33 -65.00-180.00  182
 35  \w   -108.00 -21.00   0.50    0.50    --  -41.33 -54.00 -90.00  174
 36  \w   -117.00  -5.00   0.50    0.50    --  -41.33 -11.00 -90.00  224
 37  \w   -149.00 -75.00   0.50    4.50    --  -82.50-122.00 -48.00  148
 38  \w   -149.00 -55.00   0.50    4.50    --  -82.50-151.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0111237000
_diffrn_orient_matrix_UB_12      -0.0816616000
_diffrn_orient_matrix_UB_13      0.0153131000
_diffrn_orient_matrix_UB_21      0.0661484000
_diffrn_orient_matrix_UB_22      0.0109807000
_diffrn_orient_matrix_UB_23      -0.0367329000
_diffrn_orient_matrix_UB_31      0.0221221000
_diffrn_orient_matrix_UB_32      0.0082607000
_diffrn_orient_matrix_UB_33      0.2002160000
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            14057
_diffrn_reflns_theta_full        68.10
_diffrn_reflns_theta_max         68.10
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1368
_exptl_crystal_recrystallization_method 'Slow evaporation of solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+1.6178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                2548
_reflns_number_total             2809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc04157g4.cif
_cod_data_source_block           jb_j22
_cod_depositor_comments          'Adding full bibliography for 1572882.cif.'
_cod_database_code               1572882
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @RT
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: S1B(0.7995) S2B(0.2005)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2A(H2A), C4(H4), C2(H2), C3(H3), C3A(H3A), C4A(H4A), C4B(H4B)
;
_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 1.879
_oxdiff_exptl_absorpt_empirical_full_min 0.641