Diketopyrrolopyrrole-based small molecules for solution-processed n-channel organic thin film transistors
Zhou, Qian; Jiang, Yu; Du, Tian; Wang, Zhongli; Liang, Ziqi; Han, Yang; Deng, Yunfeng; Tian, Hongkun; Geng, Yanhou; Journal of Materials Chemistry C 7 (2019) 13939–; doi:10.1039/C9TC05038H

data_7238032
_publ_section_title
;
 Diketopyrrolopyrrole-based small molecules for solution-processed
 n-channel organic thin film transistors
;
_journal_issue                   44
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              13939
_journal_paper_doi               10.1039/C9TC05038H
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C72 H76 F4 N6 O4 S2'
_chemical_formula_sum            'C72 H76 F4 N6 O4 S2'
_chemical_formula_weight         1229.50
_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             2019-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-11 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                96.078(4)
_cell_angle_beta                 95.431(5)
_cell_angle_gamma                102.535(4)
_cell_formula_units_Z            1
_cell_length_a                   6.6078(7)
_cell_length_b                   14.9482(15)
_cell_length_c                   16.8745(18)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.78
_cell_measurement_theta_min      7.82
_cell_volume                     1606.0(3)
_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      170.01
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15682
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.959
_diffrn_reflns_theta_min         3.741
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0937 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.7270. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             650
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6045
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1487P)^2^+0.5470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2127
_refine_ls_wR_factor_ref         0.2450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4055
_reflns_number_total             6045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc05038h2.cif
_cod_data_source_block           mj19390_0m
_cod_database_code               7238032
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.921
_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. Restrained distances
 C34-C33 = C35-C34 = C35-C36 = C33-C32
 1.53 with sigma of 0.02
 C27-C26 = C28-C27 = C26-C25
 1.53 with sigma of 0.02
 H28A-H36A_$1
 2.1 with sigma of 0.01
3. Rigid bond restraints
 C33, C34, C34, C35, C35, C36
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C28) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5.a Ternary CH refined with riding coordinates:
 C22(H22)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C12(H12), C15(H15)
5.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              29228
_olex2_submission_special_instructions 'No special instructions were received'