Solution-Processable Organic Semiconductors Featuring S-Shaped Dinaphthothienothiophene (S-DNTT): Effects of Alkyl Chain Length on Self-Organization and Carrier Transport Properties
Yamaguchi, Yuji; Kojiguchi, Yuka; Kawata, So; Mori, Tatsuya; Okamoto, Kazuo; Tsutsui, Masanori; Koganezawa, Tomoyuki; Katagiri, Hiroshi; Yasuda, Takuma; Chemistry of Materials  (2020) –; doi:10.1021/acs.chemmater.0c01740

data_4003571
_publ_section_title
;
 Solution-Processable Organic Semiconductors Featuring S-Shaped
 Dinaphthothienothiophene (S-DNTT): Effects of Alkyl Chain Length on
 Self-Organization and Carrier Transport Properties
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01740
_journal_year                    2020
_chemical_formula_moiety         'C15 H14 S'
_chemical_formula_sum            'C15 H14 S'
_chemical_formula_weight         226.32
_chemical_name_common            S-DNTT-4
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.494(3)
_cell_angle_beta                 90.898(4)
_cell_angle_gamma                101.587(4)
_cell_formula_units_Z            2
_cell_length_a                   4.8135(2)
_cell_length_b                   7.9484(3)
_cell_length_c                   14.8781(6)
_cell_measurement_reflns_used    6358
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.5470
_cell_measurement_theta_min      2.5840
_cell_volume                     553.62(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -84.00  94.00   0.50    5.00    --    5.00  45.00  60.00  356
  2  \w    -99.00  79.00   0.50    5.00    --  -10.30  45.00   0.00  356
  3  \w    -99.00  79.00   0.50    5.00    --  -10.30  45.00  90.00  356
  4  \w    -99.00  79.00   0.50    5.00    --  -10.30  45.00 150.00  356
  5  \w    -84.00 -59.00   0.50    5.00    --    5.00  45.00 120.00   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002975000
_diffrn_orient_matrix_UB_12      0.0208789000
_diffrn_orient_matrix_UB_13      0.0476354000
_diffrn_orient_matrix_UB_21      -0.0552139000
_diffrn_orient_matrix_UB_22      -0.0881217000
_diffrn_orient_matrix_UB_23      0.0047215000
_diffrn_orient_matrix_UB_31      0.1400462000
_diffrn_orient_matrix_UB_32      -0.0146729000
_diffrn_orient_matrix_UB_33      0.0037963000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.634
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0406P)^2^+0.2355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2252
_reflns_number_total             2539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c01740_si_002.cif
_cod_data_source_block           S-DNTT-4
_cod_database_code               4003571
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C9(H9), C4(H4)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.844