Non-fullerene acceptors with direct and indirect hexa-fluorination afford >17% efficiency in polymer solar cells
Li, Guoping; Feng, Liang-Wen; Mukherjee, Subhrangsu; Jones, Leighton O.; Jacobberger, Robert M.; Huang, Wei; Young, Ryan M.; Pankow, Robert M.; Zhu, Weigang; Lu, Norman; Kohlstedt, Kevin L.; Sangwan, Vinod K.; Wasielewski, Michael R.; Hersam, Mark C.; Schatz, George C.; DeLongchamp, Dean M.; Facchetti, Antonio; Marks, Tobin J.; Energy & Environmental Science 15 (2022) 645–659; doi:10.1039/D1EE03225A

data_1565981
_publ_section_title
;
 Non-fullerene acceptors with direct and indirect hexa-fluorination afford
 &gt;17% efficiency in polymer solar cells
;
_journal_issue                   2
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              645
_journal_page_last               659
_journal_paper_doi               10.1039/D1EE03225A
_journal_volume                  15
_journal_year                    2022
_chemical_formula_moiety         'C100 H108 F6 N8 O2 S5'
_chemical_formula_sum            'C100 H108 F6 N8 O2 S5'
_chemical_formula_weight         1728.24
_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             2020-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-13 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                111.025(6)
_cell_angle_beta                 94.188(7)
_cell_angle_gamma                96.672(8)
_cell_formula_units_Z            2
_cell_length_a                   16.0665(19)
_cell_length_b                   17.2536(10)
_cell_length_c                   17.4364(10)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      51.2380
_cell_measurement_theta_min      2.7710
_cell_volume                     4446.7(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     31.00  56.00   0.50   20.00    --   -0.08  17.00 147.00   50
  2  \w     96.00 131.00   0.50   70.00    --   55.50  17.00 147.00   70
  3  \w     59.00  90.00   0.50   70.00    --   55.50  17.00 147.00   62
  4  \w    -19.00  27.00   0.50   70.00    --   55.50 -17.00 -21.00   92
  5  \w    -22.00  19.00   0.50   70.00    --  -55.65  17.00 147.00   82
  6  \w   -125.00 -44.00   0.50   70.00    --  -55.65 -17.00 -21.00  162
  7  \w     -5.00  22.00   0.50   20.00    --   -0.08 -99.00 120.00   54
  8  \w     -5.00  21.00   0.50   20.00    --   -0.08 -99.00 -60.00   52
  9  \w    -37.00 -10.00   0.50   20.00    --   -0.08 -17.00 -21.00   54
 10  \w    -15.00  55.00   0.50   70.00    --   55.50 -57.00  90.00  140
 11  \w     49.00 101.00   0.50   70.00    --   55.50-125.00  90.00  104
 12  \w    -17.00  85.00   0.50   70.00    --   55.50 -99.00   0.00  204
 13  \w     42.00  68.00   0.50   70.00    --   55.50-125.00 150.00   52
 14  \w    -14.00  37.00   0.50   70.00    --   55.50 -77.00  60.00  102
 15  \w     48.00 108.00   0.50   70.00    --   55.50-134.00-131.32  120
 16  \w     70.00  97.00   0.50   70.00    --   55.50-125.00 150.00   54
 17  \w     22.00  82.00   0.50   70.00    --   55.50-125.00 -90.00  120
 18  \w     24.00 100.00   0.50   70.00    --   55.50-125.00   0.00  152
 19  \w    -63.00 -18.00   0.50   70.00    --  -55.65  57.00-150.00   90
 20  \w    -13.00  16.00   0.50   70.00    --  -55.65  37.00 -90.00   58
 21  \w    -31.00  15.00   0.50   70.00    --  -55.65  37.00-180.00   92
 22  \w    -61.00  15.00   0.50   70.00    --  -55.65  57.00 -90.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0375173000
_diffrn_orient_matrix_UB_12      0.0809168000
_diffrn_orient_matrix_UB_13      0.0105936000
_diffrn_orient_matrix_UB_21      0.0897394000
_diffrn_orient_matrix_UB_22      0.0502749000
_diffrn_orient_matrix_UB_23      0.0193631000
_diffrn_orient_matrix_UB_31      0.0020675000
_diffrn_orient_matrix_UB_32      -0.0171621000
_diffrn_orient_matrix_UB_33      -0.0927996000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20373
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        44.489
_diffrn_reflns_theta_max         44.489
_diffrn_reflns_theta_min         2.776
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.749
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.76a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             1828
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.369
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1290
_refine_ls_number_reflns         6978
_refine_ls_number_restraints     1297
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.1329
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3599
_refine_ls_wR_factor_ref         0.4050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             6978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee03225a2.cif
_cod_data_source_block           cx2002
_cod_depositor_comments
'Adding full bibliography for 1565981--1565982.cif.'
_cod_database_code               1565981
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C100H108F6O2S5N8
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.606
_diffrn_oxdiff_digest_frames
;
0181a43708b6ee9575d41c07f0c2567486021185f44
;
_diffrn_oxdiff_digest_hkl
;
01a88bf30255d994b764ae7d3386ca10705fba
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     44.45
_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. Restrained distances
 C87-C86 = C86-C85 = C85-C84 = C84-C83 = C83-C82 = C82-C81 = C81-C80 = C80-C79
 = C79-C78 = C78-C77 = C77-C14 = C95-C94 = C94-C93 = C93-C92 = C92-C91 = C91-
 C90 = C90-C89 = C96-C89 = C97-C96 = C98-C97 = C99-C98 = C89-C88 = C50-C49 =
 C51-C50 = C52-C51 = C53-C52 = C9EA-C53 = C9EA-C54 = C49-C48 = C55-C49 = C56-
 C55 = C57-C56 = C58-C57 = C5-C37 = C38-C37 = C39-C38 = C40-C39 = C41-C40 = C42-
 C41 = C43-C42 = C44-C43 = C45-C44 = C45-C46A = C47A-C46A = C46-C45 = C47-C46
 1.54 with sigma of 0.02
 C14-C78 = C77-C79 = C80-C82 = C81-C83 = C84-C86 = C85-C87 = C99-C97 = C98-C96
 = C90-C88 = C89-C91 = C92-C94 = C93-C95 = C58-C56 = C57-C55 = C54-C53 = C9EA-
 C52 = C51-C49 = C50-C48 = C47-C45 = C5-C38 = C37-C39 = C40-C42 = C41-C43 = C44-
 C46A
 2.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C95) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
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
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O2A)=Sof(N7A)=Sof(N8A)=Sof(C59A)=Sof(H59A)=
 Sof(C60A)=Sof(C61A)=Sof(C62A)=Sof(C63A)=Sof(H63A)=Sof(C69A)=Sof(C64A)=
 Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=Sof(C67A)=Sof(C68A)=Sof(H68A)=
 Sof(C70A)=Sof(H70A)=Sof(C71A)=Sof(C72A)=Sof(C73A)=Sof(C74A)=Sof(C75A)=
 Sof(C76A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(O2)=Sof(N7)=Sof(N8)=Sof(C59)=Sof(H59)=Sof(C60)=
 Sof(C61)=Sof(C62)=Sof(C63)=Sof(H63)=Sof(C64)=Sof(C69)=Sof(C70)=Sof(H70)=
 Sof(C71)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(C67)=Sof(H67)=Sof(C68)=Sof(H68)=
 Sof(C72)=Sof(C73)=Sof(C74)=Sof(C75)=Sof(C76)=FVAR(1)
 Sof(H45C)=Sof(H45D)=Sof(C46A)=Sof(H46A)=Sof(H46B)=Sof(C47A)=Sof(H47A)=
 Sof(H47B)=Sof(H47C)=1-FVAR(2)
 Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46C)=Sof(H46D)=Sof(C47)=Sof(H47D)=Sof(H47E)=
 Sof(H47F)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C49(H49), C89(H89)
6.b Secondary CH2 refined with riding coordinates:
 C9EA(H9EA,H9EB), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,
 H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B),
 C45(H45A,H45B), C45(H45C,H45D), C46(H46C,H46D), C46A(H46A,H46B), C48(H48A,
 H48B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B),
 C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C77(H77A,H77B), C78(H78A,H78B),
  C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,
 H83B), C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C88(H88A,H88B),
 C90(H90A,H90B), C91(H91A,H91B), C92(H92A,H92B), C93(H93A,H93B), C94(H94A,H94B),
  C96(H96A,H96B), C97(H97A,H97B), C98(H98A,H98B)
6.c Me refined with riding coordinates:
 C47(H47D,H47E,H47F), C47A(H47A,H47B,H47C), C54(H54A,H54B,H54C), C58(H58A,H58B,
 H58C), C87(H87A,H87B,H87C), C95(H95A,H95B,H95C), C99(H99A,H99B,H99C)
6.d Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C28(H28), C27(H27), C25(H25), C30(H30), C59(H59),
 C59A(H59A), C63(H63), C70(H70), C63A(H63A), C65(H65), C67(H67), C68(H68),
 C65A(H65A), C66A(H66A), C68A(H68A), C70A(H70A)
6.e Fitted hexagon refined as free rotating group:
 C24(C29,C28,C27,C26,C25), C62(C63,C64,C69,C70,C71), C69A(C64A,C65A,C66A,C67A,
 C68A)
;
_shelx_res_checksum              98596
_olex2_date_sample_data_collection 2020-09-10
_olex2_date_sample_submission    2020-08-23
_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 cx2002
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.556
_oxdiff_exptl_absorpt_empirical_full_min 0.537