Nitrofluorene-based A-D-A electron acceptors for organic photovoltaics
Yuxuan Che; Muhammad Rizwan Niazi; Ting Yu; Thierry Maris; Cheng-Hao Liu; Dongling Ma; Ricardo Izquierdo; Igor F. Perepichka; Dmytro F. Perepichka; Journal of Material Chemistry C 11 (2023) 8186–8195; doi:10.1039/d2tc05127c

data_7247677
_publ_section_title
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 Nitrofluorene-based A-D-A electron acceptors for organic photovoltaics
;
_journal_name_full               'Journal of Material Chemistry C'
_journal_page_first              8186
_journal_page_last               8195
_journal_paper_doi               10.1039/d2tc05127c
_journal_volume                  11
_journal_year                    2023
_chemical_formula_moiety         '2(C88 H86 N12 O16 S4), 4(C3 H6 O), C H Cl3'
_chemical_formula_sum            'C189 H197 Cl3 N24 O36 S8'
_chemical_formula_weight         3743.52
_chemical_name_systematic
;
4,4'-(4,4,9,9-tetraoctyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']bisthiophene 
2,7-diyl)bis{7-[(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)methyl]-2,1,3-
benzothiadiazole} acetone chloroform solvate
;
_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
_cell_angle_alpha                72.040(1)
_cell_angle_beta                 79.167(1)
_cell_angle_gamma                82.071(2)
_cell_formula_units_Z            1
_cell_length_a                   11.3383(3)
_cell_length_b                   17.6646(5)
_cell_length_c                   25.5872(7)
_cell_measurement_reflns_used    9818
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.902
_cell_measurement_theta_min      2.387
_cell_volume                     4770.6(2)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support cryoloop
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            161417
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.926
_diffrn_reflns_theta_min         2.386
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.2536
_exptl_absorpt_correction_T_min  0.1680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.6625.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1966
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone, chloroform'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.901
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1247
_refine_ls_number_reflns         18059
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0866
_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^)+(0.1659P)^2^+6.4141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2496
_refine_ls_wR_factor_ref         0.2525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16967
_reflns_number_total             18059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            per1311.cif
_cod_data_source_block           per1311
_cod_database_code               7247677
_cod_database_fobs_code 7247677