Fluorination Effects on Indacenodithienothiophene Acceptor Packing and Electronic Structure, End-Group Redistribution, and Solar Cell Photovoltaic Response.
Aldrich, Thomas J.; Matta, Micaela; Zhu, Weigang; Swick, Steven M.; Stern, Charlotte L.; Schatz, George C.; Facchetti, Antonio; Melkonyan, Ferdinand S.; Marks, Tobin J.; Journal of the American Chemical Society 141 (2019) 3274–3287; doi:10.1021/jacs.8b13653

data_4128448
_publ_section_title
;
 Fluorination Effects on Indacenodithienothiophene Acceptor Packing and
 Electronic Structure, End-Group Redistribution, and Solar Cell
 Photovoltaic Response.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3274
_journal_page_last               3287
_journal_paper_doi               10.1021/jacs.8b13653
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C94 H76 F6 N4 O2 S4'
_chemical_formula_sum            'C94 H76 F6 N4 O2 S4'
_chemical_formula_weight         1535.82
_chemical_name_systematic        ITIC-6F
_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             2018-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-12-18 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                68.171(3)
_cell_angle_beta                 88.703(4)
_cell_angle_gamma                77.059(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3692(4)
_cell_length_b                   15.4456(7)
_cell_length_c                   18.9453(10)
_cell_measurement_reflns_used    6344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.050
_cell_measurement_theta_min      2.518
_cell_volume                     2210.7(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13387
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        65.206
_diffrn_reflns_theta_max         65.206
_diffrn_reflns_theta_min         2.518
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1168 before and 0.0482 after correction. The Ratio of minimum to maximum transmission is 0.8073. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       plate
_exptl_crystal_F_000             802
_exptl_crystal_recrystallization_method
'The material was obtained by vapor diffusion of n-heptane into a CH2Br2 solution.'
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.022
_refine_diff_density_max         1.338
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.1234
_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^)+(0.1030P)^2^+33.6617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3163
_refine_ls_wR_factor_ref         0.3243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5902
_reflns_number_total             7259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13653_si_004.cif
_cod_data_source_block           ITIC-6F
_cod_original_cell_volume        2210.69(19)
_cod_database_code               4128448
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=
 Sof(H34D)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C32(H32C,H32D), C33(H33A,
 H33B), C33A(H33C,H33D), C34(H34A,H34B), C34A(H34C,H34D), C42(H42A,H42B),
 C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C11(H11), C18(H18), C25(H25), C26(H26), C28(H28), C29(H29),
 C37(H37), C38(H38), C40(H40), C41(H41)
3.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C35A(H35D,H35E,H35F), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              35414
_shelx_hkl_checksum              95685
_shelx_fab_checksum              61763
_olex2_date_sample_data_collection 2018-05-04
_olex2_date_sample_submission    2018-03-30
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1245a
_olex2_submission_special_instructions 'No special instructions were received'