Molecular "backbone surgery" of electron-deficient heteroarenes based on dithienopyrrolobenzothiadiazole: conformation-dependent crystal structures and charge transport properties.
Chen, Yuzhong; Wu, Zeng; Chen, Zekun; Zhang, Shuixin; Li, Wenhao; Zhao, Yan; Wang, Yang; Liu, Yunqi; Chemical science 15 (2024) 11761–11774; doi:10.1039/d4sc02794a

data_1571938
_publ_section_title
;
 Molecular "backbone surgery" of electron-deficient heteroarenes based on
 dithienopyrrolobenzothiadiazole: conformation-dependent crystal
 structures and charge transport properties.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              11761
_journal_page_last               11774
_journal_paper_doi               10.1039/d4sc02794a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C82 H86 F4 N8 O4 S5'
_chemical_formula_sum            'C82 H86 F4 N8 O4 S5'
_chemical_formula_weight         1483.88
_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             2023-04-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.535(2)
_cell_angle_beta                 98.131(2)
_cell_angle_gamma                105.597(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9852(10)
_cell_length_b                   14.5835(12)
_cell_length_c                   26.719(3)
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.89
_cell_measurement_theta_min      2.18
_cell_volume                     4002.6(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 PILATUS3-S_2M
_diffrn_detector_type            HPAD
_diffrn_measured_fraction_theta_full 0.686
_diffrn_measured_fraction_theta_max 0.686
_diffrn_measurement_device       SSRF
_diffrn_measurement_device_type  'synchrotron radiation'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'synchrotron radiation'
_diffrn_radiation_wavelength     0.68878
_diffrn_reflns_av_R_equivalents  0.1878
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_Laue_measured_fraction_full 0.686
_diffrn_reflns_Laue_measured_fraction_max 0.686
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24697
_diffrn_reflns_point_group_measured_fraction_full 0.686
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        21.396
_diffrn_reflns_theta_max         21.396
_diffrn_reflns_theta_min         0.761
_diffrn_source                   'synchrotron radiation'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_type              'synchrotron radiation'
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.099
_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     1066
_refine_ls_number_reflns         6844
_refine_ls_number_restraints     421
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0903
_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^)+(0.1602P)^2^+9.7121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2466
_refine_ls_wR_factor_ref         0.2774
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5126
_reflns_number_total             6844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02794a2.cif
_cod_data_source_block           11_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571936--1571938.cif.
;
_cod_original_cell_volume        4002.7(6)
_cod_database_code               1571938
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Restrained distances
 C77-C77A = C77-C76 = C79-C76 = C80-C79 = C81-C80 = C82-C81
 1.5 with sigma of 0.01
 C70-C69 = C69-C68 = C71-C68 = C71-C72 = C73-C72 = C73-C74
 1.5 with sigma of 0.01
 C69-C71
 2.5 with sigma of 0.01
 C80-C82
 2.5 with sigma of 0.01
 C77A-C76
 2.5 with sigma of 0.01
 C77-C79
 2.5 with sigma of 0.01
 C71-C73
 2.5 with sigma of 0.01
 C76-C80
 2.5 with sigma of 0.01
 C79-C81
 2.5 with sigma of 0.01
 C68-C70
 2.5 with sigma of 0.01
 C68-C72
 2.5 with sigma of 0.01
 C72-C74
 2.5 with sigma of 0.01
 C68-C67 \\sim C68A-C67
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C75A \\sim C76A \\sim C77A \\sim C78A \\sim C79A \\sim C80A \\sim C81A \\sim
C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C75:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C68 \\sim C69 \\sim C70 \\sim C71 \\sim C68A \\sim C69A \\sim C70A \\sim C67
\\sim C72 \\sim C73 \\sim C74 \\sim C71A \\sim C72A \\sim C73A \\sim C74A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{C75A, C76A, C77A, C78A, C79A, C80A, C81A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C76, C77, C78, C79, C80, C81, C82}
{C68A, C69A, C70A, C71A, C72A, C73A, C74A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C68, C69, C70, C71, C72, C73, C74}
4. Others
 Sof(H75C)=Sof(H75D)=Sof(C75A)=Sof(H75E)=Sof(C76A)=Sof(H76A)=Sof(H76B)=
 Sof(C77A)=Sof(H77A)=Sof(H77B)=Sof(H77C)=Sof(C78A)=Sof(H78A)=Sof(H78B)=
 Sof(C79A)=Sof(H79A)=Sof(H79B)=Sof(C80A)=Sof(H80A)=Sof(H80B)=Sof(C81A)=
 Sof(H81A)=Sof(H81B)=Sof(H81C)=1-FVAR(1)
 Sof(H75A)=Sof(H75B)=Sof(C76)=Sof(H76)=Sof(C77)=Sof(H77D)=Sof(H77E)=Sof(C78)=
 Sof(H78C)=Sof(H78D)=Sof(H78E)=Sof(C79)=Sof(H79C)=Sof(H79D)=Sof(C80)=Sof(H80C)=
 Sof(H80D)=Sof(C81)=Sof(H81D)=Sof(H81E)=Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(H82C)=
 FVAR(1)
 Sof(H67C)=Sof(H67D)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69C)=Sof(H69D)=
 Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(C71A)=Sof(H71C)=Sof(H71D)=
 Sof(C72A)=Sof(H72C)=Sof(H72D)=Sof(C73A)=Sof(H73C)=Sof(H73D)=Sof(C74A)=
 Sof(H74D)=Sof(H74E)=Sof(H74F)=1-FVAR(2)
 Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=
 Sof(H70A)=Sof(H70B)=Sof(H70C)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(C72)=Sof(H72A)=
 Sof(H72B)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=
 FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C75A(H75E), C76(H76), C68(H68), C68A(H68A)
5.b Secondary CH2 refined with riding coordinates:
 C58(H58A,H58B), C61(H61A,H61B), C75(H75C,H75D), C75(H75A,H75B), C57(H57A,
 H57B), C56(H56A,H56B), C64(H64A,H64B), C62(H62A,H62B), C59(H59A,H59B),
 C63(H63A,H63B), C60(H60A,H60B), C67(H67A,H67B), C67(H67C,H67D), C45(H45A,H45B),
  C65(H65A,H65B), C46(H46A,H46B), C76A(H76A,H76B), C78A(H78A,H78B), C79A(H79A,
 H79B), C80A(H80A,H80B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,H51B),
 C48(H48A,H48B), C49(H49A,H49B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B),
  C77(H77D,H77E), C79(H79C,H79D), C80(H80C,H80D), C81(H81D,H81E), C69(H69A,
 H69B), C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C69A(H69C,H69D),
 C71A(H71C,H71D), C72A(H72C,H72D), C73A(H73C,H73D)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C3(H3), C32(H32), C36(H36), C39(H39)
5.d Idealised Me refined as rotating group:
 C77A(H77A,H77B,H77C), C81A(H81A,H81B,H81C), C66(H66A,H66B,H66C), C78(H78C,
 H78D,H78E), C82(H82A,H82B,H82C), C70(H70A,H70B,H70C), C74(H74A,H74B,H74C),
 C55(H55A,H55B,H55C), C70A(H70D,H70E,H70F), C74A(H74D,H74E,H74F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              18849
_shelx_fab_checksum              90933
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU