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_7237299
_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         'C30 H16 F6 S2'
_chemical_formula_sum            'C30 H16 F6 S2'
_chemical_formula_weight         554.55
_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     direct
_audit_creation_date             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-25 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                103.52(2)
_cell_angle_beta                 91.36(2)
_cell_angle_gamma                101.337(15)
_cell_formula_units_Z            2
_cell_length_a                   8.951(5)
_cell_length_b                   9.552(5)
_cell_length_c                   14.344(9)
_cell_measurement_reflns_used    6712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.436
_cell_measurement_theta_min      2.664
_cell_volume                     1166.0(12)
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.02
_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 0.999
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.464
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1341 before and 0.0376 after correction. The Ratio of minimum to maximum transmission is 0.9353. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.052
_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     371
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0441P)^2^+0.7549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4034
_reflns_number_total             4758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc00970h2.cif
_cod_data_source_block           esser_mh_209_0m_a
_cod_original_cell_volume        1166.0(11)
_cod_database_code               7237299
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C23-F1A \\sim C23-F2A \\sim C23-F3A \\sim C23-F4A \\sim C23-F5A \\sim C23-F6A
 with sigma of 0.02
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.04
 C20-F1A \\sim C20-F2A \\sim C20-F3A \\sim C20-F4A \\sim C20-F5A \\sim C20-F6A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C20 \\sim C23 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C20, C23, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28), C29(H29)
;
_shelx_res_checksum              27675
_shelx_hkl_checksum              7205
_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_special_instructions 'No special instructions were received'