Thioether- and sulfone-functionalized dibenzopentalenes as n-channel semiconductors for organic field-effect transistors
Hermann, Mathias; Wu, Ruihan; Grenz, David C.; Kratzert, Daniel; Li, Hanying; Esser, Birgit; Journal of Materials Chemistry C 6 (2018) 5420–; doi:10.1039/C8TC00970H

data_7237298
_publ_section_title
;
 Thioether- and sulfone-functionalized dibenzopentalenes as n-channel
 semiconductors for organic field-effect transistors
;
_journal_issue                   20
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5420
_journal_paper_doi               10.1039/C8TC00970H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C28 H18 S2'
_chemical_formula_sum            'C28 H18 S2'
_chemical_formula_weight         418.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_audit_update_record
;
2017-02-15 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.214(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.307(3)
_cell_length_b                   5.5294(14)
_cell_length_c                   15.071(5)
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.40
_cell_volume                     1002.4(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.108
_diffrn_reflns_theta_min         1.946
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1156 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.9453. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0335P)^2^+1.0946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2027
_reflns_number_total             2191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc00970h2.cif
_cod_data_source_block           esser_mh_192_0m
_cod_database_code               7237298
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              55224
_shelx_hkl_checksum              69137
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id MH_192
_olex2_submission_special_instructions 'No special instructions were received'