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_4128452
_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         '2(C47 H40 F N2 O S2)'
_chemical_formula_sum            'C94 H80 F2 N4 O2 S4'
_chemical_formula_weight         1463.86
_chemical_name_systematic        ITIC-2F
_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             2018-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-18 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                72.141(8)
_cell_angle_beta                 68.454(6)
_cell_angle_gamma                80.226(7)
_cell_formula_units_Z            2
_cell_length_a                   15.5206(9)
_cell_length_b                   17.8326(16)
_cell_length_c                   20.9600(19)
_cell_measurement_reflns_used    5534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.076
_cell_measurement_theta_min      3.177
_cell_volume                     5125.1(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.1431
_diffrn_reflns_av_unetI/netI     0.2274
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26604
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        61.532
_diffrn_reflns_theta_max         61.532
_diffrn_reflns_theta_min         2.351
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1446 before and 0.0710 after correction. The Ratio of minimum to maximum transmission is 0.6583. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    0.949
_exptl_crystal_description       needle
_exptl_crystal_F_000             1540
_exptl_crystal_recrystallization_method
'The material was obtained by vapor diffusion of n-heptane into a CH2Br2 solution.'
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.614
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         15232
_refine_ls_number_restraints     1873
_refine_ls_restrained_S_all      1.570
_refine_ls_R_factor_all          0.2814
_refine_ls_R_factor_gt           0.2316
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5059
_refine_ls_wR_factor_ref         0.5329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8638
_reflns_number_total             15232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13653_si_005.cif
_cod_data_source_block           ITIC-2F
_cod_database_code               4128452
_shelx_shelxl_version_number     2017/1
_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
 C45-C43 \\sim C42-C40
 with sigma of 0.001
 C39-C42 \\sim C43-C42 \\sim C43-C44 \\sim C45-C44 \\sim C45-C46 \\sim C47-C46
\\sim C89-C86 \\sim C89-C90
 \\sim C91-C90 \\sim C91-C92 \\sim C93-C92 \\sim C94-C93 \\sim C30-C27 \\sim
C30-C31 \\sim C31-C32 \\sim C33-
 C32 \\sim C33-C34 \\sim C35-C34 \\sim C77-C74 \\sim C78-C77 \\sim C79-C78
\\sim C79-C80 \\sim C81-C80 ~
 C81-C82
 with sigma of 0.01
 C82-C80 \\sim C81-C79 \\sim C78-C74 \\sim C27-C31 \\sim C30-C32 \\sim C33-C35
\\sim C90-C86 \\sim C89-C91
 \\sim C92-C94 \\sim C47-C45 \\sim C46-C44 \\sim C43-C39
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: F1(0.5) F2(0.5) H5(0.5) H6(0.5) F3(0.5) F4(0.5) H52(0.5) H53(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,
 H34B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B),
 C46(H46A,H46B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B),
  C81(H81A,H81B), C89(H89A,H89B), C90(H90A,H90B), C91(H91A,H91B), C92(H92A,
 H92B), C93(H93A,H93B)
6.b Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C47(H47A,H47B,H47C), C82(H82A,H82B,H82C), C94(H94A,H94B,
 H94C)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C15(H15), C23(H23), C25(H25),
 C26(H26), C28(H28), C29(H29), C37(H37), C38(H38), C40(H40), C41(H41), C51(H51),
  C52(H52), C53(H53), C54(H54), C60(H60), C62(H62), C70(H70), C72(H72),
 C73(H73), C75(H75), C76(H76), C84(H84), C85(H85), C87(H87), C88(H88)
;
_shelx_res_checksum              5795
_shelx_hkl_checksum              69136
_shelx_fab_checksum              34541
_olex2_date_sample_data_collection 2018-06-07
_olex2_date_sample_submission    2018-06-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with Paratone oil'
_olex2_submission_original_sample_id cx1302
_olex2_submission_special_instructions 'No special instructions were received'