Ambient stable solution-processed organic field effect transistors from electron deficient planar aromatics: effect of end-groups on ambient stability
Giri, Indrajit; Biswas, Sagar; Chhetri, Shant; Choudhuri, Anwesha; Mondal, Indrajit; Senanayak, Satyaprasad P.; Iyer, Parameswar Krishnan; Chaudhuri, Debangshu; Vijayaraghavan, Ratheesh K.; RSC Advances 14 (2024) 7915–7923; doi:10.1039/D4RA01499E

data_7248287
_publ_section_title
;
 Ambient stable solution-processed organic field effect transistors from
 electron deficient planar aromatics: effect of end-groups on ambient
 stability
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              7915
_journal_page_last               7923
_journal_paper_doi               10.1039/D4RA01499E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C32.01 H34 N4 O4'
_chemical_formula_sum            'C32.01 H34 N4 O4'
_chemical_formula_weight         538.75
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                99.995(6)
_cell_angle_beta                 93.825(7)
_cell_angle_gamma                95.201(8)
_cell_formula_units_Z            1
_cell_length_a                   5.3597(6)
_cell_length_b                   8.2900(8)
_cell_length_c                   15.7629(8)
_cell_measurement_reflns_used    3749
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      68.0810
_cell_measurement_theta_min      2.8580
_cell_volume                     684.48(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.967
_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     26.00 107.00   0.50    0.91    --   40.96  38.00 -30.00  162
  2  \w     99.00 164.00   0.50    3.64    --   96.67 117.00  30.00  130
  3  \w    128.00 157.00   0.50    3.64    --   96.67 145.00 120.00   58
  4  \w     99.00 164.00   0.50    3.64    --   96.67 117.00 150.00  130
  5  \w    100.00 164.00   0.50    3.64    --   96.67 117.00 120.00  128
  6  \w     80.00 163.00   0.50    3.64    --   96.67  42.00   0.00  166
  7  \w    120.00 163.00   0.50    3.64    --   96.67 145.00-120.00   86
  8  \w    105.00 168.00   0.50    3.64    --   96.67 103.00-168.00  126
  9  \w     93.00 119.00   0.50    3.64    --   96.67 145.00-120.00   52
 10  \w     70.00 165.00   0.50    3.64    --   96.67  77.00-120.00  190
 11  \w     80.00 163.00   0.50    3.64    --   96.67  42.00 -60.00  166
 12  \w     83.00 154.00   0.50    3.64    --   96.67  33.00-180.00  142
 13  \w     75.00 164.00   0.50    3.64    --   96.67  59.00  30.00  178
 14  \w     82.00 167.00   0.50    3.64    --   96.67  25.00 120.00  170
 15  \w     44.00 127.00   0.50    3.64    --   96.67-145.00   0.00  166
 16  \w     42.00  68.00   0.50    3.64    --   96.67 -59.00-150.00   52
 17  \w     27.00 127.00   0.50    3.64    --   96.67 -87.00-180.00  200
 18  \w     41.00 100.00   0.50    0.91    --   40.96-138.00-180.00  118
 19  \w     30.00 109.00   0.50    3.64    --   96.67-117.00-150.00  158
 20  \w     30.00 109.00   0.50    3.64    --   96.67-117.00-180.00  158
 21  \w     29.00  68.00   0.50    3.64    --   96.67 -59.00-180.00   78
 22  \w     30.00 109.00   0.50    3.64    --   96.67-117.00   0.00  158
 23  \w     30.00 109.00   0.50    3.64    --   96.67-117.00  90.00  158
 24  \w     30.00  57.00   0.50    3.64    --   96.67 -50.00  60.00   54
 25  \w     29.00  83.00   0.50    3.64    --   96.67 -68.00  90.00  108
 26  \w     29.00  68.00   0.50    3.64    --   96.67 -59.00  60.00   78
 27  \w     30.00  57.00   0.50    3.64    --   96.67 -50.00 120.00   54
 28  \w     25.00 107.00   0.50    3.64    --   96.67-103.00  90.00  164
 29  \w     14.00  79.00   0.50    0.91    --   40.96-103.00  90.00  130
 30  \w    -24.00  35.00   0.50    0.91    --  -40.96  12.00 120.00  118
 31  \w    -25.00  43.00   0.50    0.91    --   40.96 -38.00 -30.00  136
 32  \w    -26.00  64.00   0.50    0.91    --   40.96 -64.00 -90.00  180
 33  \w    -34.00  24.00   0.50    0.91    --   40.96 -12.00 -90.00  116
 34  \w    -57.00  26.00   0.50    0.91    --  -40.96  50.00-180.00  166
 35  \w    -47.00 -15.00   0.50    3.64    --  -82.50  42.00-150.00   64
 36  \w    -47.00 -15.00   0.50    3.64    --  -82.50  42.00-180.00   64
 37  \w    -47.00 -15.00   0.50    3.64    --  -82.50  42.00-120.00   64
 38  \w    -68.00  28.00   0.50    0.91    --  -40.96  77.00 -60.00  192
 39  \w    -47.00 -15.00   0.50    3.64    --  -82.50  42.00   0.00   64
 40  \w    -47.00 -15.00   0.50    3.64    --  -82.50  42.00 150.00   64
 41  \w   -108.00 -18.00   0.50    0.91    --  -40.96 -64.00  30.00  180
 42  \w    -82.00 -11.00   0.50    3.64    --  -82.50 103.00-168.00  142
 43  \w    -79.00   8.00   0.50    0.91    --  -40.96 103.00-168.00  174
 44  \w   -154.00 -83.00   0.50    3.64    --  -82.50-103.00  90.00  142
 45  \w   -156.00 -58.00   0.50    3.64    --  -82.50 -17.00  30.00  196
 46  \w   -157.00 -83.00   0.50    3.64    --  -82.50 -96.00-150.00  148
;
_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      0.0234871000
_diffrn_orient_matrix_UB_12      -0.0979391000
_diffrn_orient_matrix_UB_13      0.0742432000
_diffrn_orient_matrix_UB_21      0.1102874000
_diffrn_orient_matrix_UB_22      -0.1373516000
_diffrn_orient_matrix_UB_23      -0.0604068000
_diffrn_orient_matrix_UB_31      0.2667982000
_diffrn_orient_matrix_UB_32      0.0868268000
_diffrn_orient_matrix_UB_33      0.0275241000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6583
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.503
_diffrn_reflns_theta_min         2.857
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.456
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.456
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0986
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3060
_refine_ls_wR_factor_ref         0.3220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2030
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra01499e2.cif
_cod_data_source_block           trial1
_cod_database_code               7248287
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_diffrn_oxdiff_digest_frames
;
0104a20f3bac7ead4f04cb9157d3d29a6f059285034
;
_diffrn_oxdiff_digest_hkl
;
01c8ab07175da979d94a0037217bfd2dd7eba0
;
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H00J,H00K} of C00G, {H00L,H00M} of C00H
 At 1.5 times of:
  All C(H,H,H) groups, {H4A,H4B} of C4, {H00A,H00C} of C00D, All C(H,H,H,H,H,
  H) groups
2. Others
 Fixed Sof: H00G(0.5) H00H(0.5) H00I(0.5) H00D(0.5) H00E(0.5) H00F(0.5)
 C2(0.5) H2(0.5) C29(0.5) H29(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C29(H29)
3.b Secondary CH2 refined with riding coordinates:
 C00G(H00J,H00K), C00H(H00L,H00M)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00K(H00Q)
3.d Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I), C00E(H00D,H00E,H00F), C00J(H00N,H00O,H00P)
;
_shelx_res_checksum              66732
_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 4.364
_oxdiff_exptl_absorpt_empirical_full_min 0.446