Non-fullerene acceptors with hetero-dihalogenated terminals induce significant difference in single crystallography and enable binary organic solar cells with 17.5% efficiency
Wang, Lai; An, Qiaoshi; Yan, Lu; Bai, Hai-Rui; Jiang, Mengyun; Mahmood, Asif; Yang, Can; Zhi, Hongfu; Wang, Jin-Liang; Energy & Environmental Science 15 (2022) 320–333; doi:10.1039/D1EE01832A

data_1564845
_publ_section_title
;
 Non-fullerene acceptors with hetero-dihalogenated terminals induce
 significant difference in single crystallography and enable binary
 organic solar cells with 17.5% efficiency
;
_journal_issue                   1
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              320
_journal_page_last               333
_journal_paper_doi               10.1039/D1EE01832A
_journal_volume                  15
_journal_year                    2022
_chemical_formula_moiety         'C90 H102 Cl2 F2 N8 O2 S5'
_chemical_formula_sum            'C90 H102 Cl2 F2 N8 O2 S5'
_chemical_formula_weight         1596.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-08-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.646(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.5046(10)
_cell_length_b                   23.0448(11)
_cell_length_c                   31.2654(18)
_cell_measurement_reflns_used    7654
_cell_measurement_temperature    99.97(12)
_cell_measurement_theta_max      68.2340
_cell_measurement_theta_min      2.5660
_cell_volume                     18198.1(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.948
_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    -23.00  26.00   0.50    1.00    --  -46.95  38.00  60.00   98
  2  \w    -67.00 -35.00   0.50    6.00    --  -99.00  61.00-120.00   64
  3  \w    -77.00 -42.00   0.50    6.00    --  -99.00  77.00 -60.00   70
  4  \w    -79.00  20.00   0.50    1.00    --  -46.95  99.00 -59.00  198
  5  \w    -63.00 -27.00   0.50    6.00    --  -99.00  61.00 150.00   72
  6  \w    -60.00 -33.00   0.50    6.00    --  -99.00  61.00  90.00   54
  7  \w    -90.00 -53.00   0.50    6.00    --  -99.00  99.00 -59.00   74
  8  \w    -20.00  27.00   0.50    1.00    --  -46.95  19.00-150.00   94
  9  \w     31.00  59.00   0.50    1.00    --   46.95 -99.00-165.00   56
 10  \w     31.00 104.00   0.50    6.00    --  103.25 -99.00-165.00  146
 11  \w     48.00 104.00   0.50    6.00    --  103.25 -94.00-120.00  112
 12  \w     41.00  70.00   0.50    6.00    --  103.25 -61.00-120.00   58
 13  \w     32.00  74.00   0.50    6.00    --  103.25 -61.00-150.00   84
 14  \w     32.00  71.00   0.50    6.00    --  103.25 -61.00 -30.00   78
 15  \w     36.00  75.00   0.50    6.00    --  103.25 -61.00   0.00   78
 16  \w     32.00  75.00   0.50    6.00    --  103.25 -61.00  60.00   86
 17  \w     31.00  68.00   0.50    6.00    --  103.25 -61.00  90.00   74
 18  \w    111.00 161.00   0.50    6.00    --  103.25  15.00 120.00  100
 19  \w     99.00 141.00   0.50    6.00    --  103.25  99.00 -59.00   84
 20  \w     92.00 165.00   0.50    6.00    --  103.25  45.00-120.00  146
 21  \w   -101.00 -76.00   0.50    6.00    --  -99.00 -77.00 150.00   50
 22  \w   -118.00 -75.00   0.50    1.00    --  -46.95-125.00   0.00   86
 23  \w   -115.00 -78.00   0.50    1.00    --  -46.95-125.00 -30.00   74
 24  \w   -161.00-106.00   0.50    6.00    --  -99.00 -99.00-165.00  110
 25  \w   -167.00-138.00   0.50    6.00    --  -99.00 -77.00 150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0204756000
_diffrn_orient_matrix_UB_12      -0.0242042000
_diffrn_orient_matrix_UB_13      0.0376524000
_diffrn_orient_matrix_UB_21      -0.0119129000
_diffrn_orient_matrix_UB_22      -0.0585957000
_diffrn_orient_matrix_UB_23      -0.0246017000
_diffrn_orient_matrix_UB_31      0.0562087000
_diffrn_orient_matrix_UB_32      -0.0211497000
_diffrn_orient_matrix_UB_33      0.0255545000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            64918
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.565
_diffrn_reflns_theta_min         2.596
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             6768
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1024
_refine_ls_number_reflns         17918
_refine_ls_number_restraints     389
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.2140
_refine_ls_R_factor_gt           0.1481
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1900P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3777
_refine_ls_wR_factor_ref         0.4448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6567
_reflns_number_total             17918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee01832a2.cif
_cod_data_source_block           tx4020a
_cod_depositor_comments
'Adding full bibliography for 1564845--1564847.cif.'
_cod_database_code               1564845
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHNOFSCl
_shelx_estimated_absorpt_t_max   0.663
_shelx_estimated_absorpt_t_min   0.338
_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
 C012-C022
 1.54 with sigma of 0.001
 C022-C02A
 1.54 with sigma of 0.001
 C02A-C024
 1.54 with sigma of 0.001
 C024-C029
 1.54 with sigma of 0.001
 C029-C21
 1.54 with sigma of 0.001
 C21-C23
 1.54 with sigma of 0.001
 C23-C68
 1.54 with sigma of 0.001
 C00F-C00R
 1.54 with sigma of 0.001
 C00F-N10
 1.34 with sigma of 0.02
 C1-C010
 1.54 with sigma of 0.001
 C89-C59
 1.54 with sigma of 0.001
 C59-C58
 1.54 with sigma of 0.001
 C58-C02D
 1.54 with sigma of 0.001
 C02D-C01O
 1.54 with sigma of 0.001
 C01O-C017
 1.54 with sigma of 0.001
 C026-C49
 2.8 with sigma of 0.02
 C49-C83
 1.54 with sigma of 0.001
 C49-C20
 1.54 with sigma of 0.001
 C20-C026
 1.54 with sigma of 0.001
 C026-C020
 1.54 with sigma of 0.001
 C02E-C37
 1.54 with sigma of 0.001
 C37-C30
 1.54 with sigma of 0.001
 C02E-C02B
 1.54 with sigma of 0.001
 C02B-C021
 1.54 with sigma of 0.001
 C021-C027
 1.54 with sigma of 0.001
 C027-C01V
 1.54 with sigma of 0.001
 C01V-C01Y
 1.54 with sigma of 0.001
 C01Y-C025
 1.54 with sigma of 0.001
 C025-C02C
 1.54 with sigma of 0.001
 C02C-C02J
 1.54 with sigma of 0.001
 C01W-C01Q
 1.54 with sigma of 0.001
 C01W-C028
 1.54 with sigma of 0.001
 C028-C02G
 1.54 with sigma of 0.001
 C02G-C29
 1.54 with sigma of 0.001
 C17-C89
 1.54 with sigma of 0.001
 C3-C17
 1.54 with sigma of 0.001
 C0AA-C3
 1.54 with sigma of 0.001
 C16-C94
 1.54 with sigma of 0.001
 C13-C19
 1.54 with sigma of 0.001
 C97-C13
 1.54 with sigma of 0.001
 C19-C97
 2.8 with sigma of 0.02
 C0AA-C16
 1.54 with sigma of 0.001
 C94-C1AA
 1.54 with sigma of 0.001
 C0AA_$1-C3
 3.5 with sigma of 0.02
 C01B-C019
 3.4 with sigma of 0.02
 C01B-C83_$2
 3.5 with sigma of 0.02
 C89-C3
 2.5 with sigma of 0.02
 C30_$2-C29
 3.8 with sigma of 0.01
 C20-C83
 2.5 with sigma of 0.02
 F6A-Cl
 2.8 with sigma of 0.01
 F6A-C01T
 1.7 with sigma of 0.01
 C17-C0AA
 2.5 with sigma of 0.01
 C29-C00N
 3.7 with sigma of 0.001
 C29-C30_$2
 3.9 with sigma of 0.001
 Cl-C01P \\sim F1-C01P
 with sigma of 0.02
 F009-C01L \\sim Cl0-C01L
 with sigma of 0.02
 F-C01U \\sim Cl1-C01U
 with sigma of 0.02
3. Rigid bond restraints
 C1AA, C94, C16, C0AA, C3, C17, C89, C59, C58, C02D, C01O
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C012, C022, C02A, C024, C029, C21, C23, C68, C19, C13, C97
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C83, C49, C20, C026, C020, C01Z, C01W, C028, C02G, C29
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C30, C37, C02E, C02B, C021, C027, C01V, C019, C01Y, C025, C02C, C02J
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F6A, Cl6, Cl, F1
 with sigma for 1-2 distances of 0.0013 and sigma for 1-3 distances of 0.0013
 Cl1, F, F009, Cl0
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Uiso/Uaniso restraints and constraints
C1AA \\sim C94 \\sim C16 \\sim C0AA \\sim C3 \\sim C17 \\sim C89 \\sim C59
\\sim C58 \\sim C02D \\sim C01O: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C012 \\sim C022 \\sim C02A \\sim C024 \\sim C029 \\sim C21 \\sim C23 \\sim C68
\\sim C19 \\sim C13 \\sim C97: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
C83 \\sim C49 \\sim C20 \\sim C026 \\sim C020 \\sim C01Z \\sim C01W \\sim C028
\\sim C02G \\sim C29: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
C30 \\sim C37 \\sim C02E \\sim C02B \\sim C021 \\sim C027 \\sim C01V \\sim C019
\\sim C01Y \\sim C025 \\sim C02C \\sim C02J: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
F6A \\sim Cl6 \\sim Cl \\sim F1: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
Cl1 \\sim F \\sim F009 \\sim Cl0: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
Cl0 \\sim F009 \\sim Cl1 \\sim F: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
5. Others
 Fixed Sof: Cl(0.75) F(0.5) F009(0.5) Cl6(0.25) F1(0.75) F6A(0.25) Cl0(0.5)
 Cl1(0.5)
6.a Ternary CH refined with riding coordinates:
 C01Q(H01Q), C01V(H01V)
6.b Secondary CH2 refined with riding coordinates:
 C012(H01A,H01B), C019(H01C,H01D), C01B(H01E,H01F), C01O(H01G,H01H), C01W(H01K,
 H01L), C01Y(H01M,H01O), C01Z(H01P,H01S), C020(H02A,H02B), C021(H02C,H02D),
 C022(H02E,H02F), C024(H02G,H02H), C025(H02I,H02J), C026(H02K,H02L), C027(H02M,
 H02N), C028(H02O,H02P), C029(H02Q,H02R), C02A(H02S,H02T), C02B(H02U,H02V),
 C02C(H02W,H02X), C02D(H02Y,H), C02E(H02Z,HA), C02G(H02,HB), C20(H20A,H20B),
 C21(H21A,H21B), C23(H23A,H23B), C37(H37A,H37B), C49(H49A,H49B), C58(H58A,H58B),
  C68(H68A,H68B), C19(H19A,H19B), C13(H13A,H13B), C59(H59A,H59B), C89(H89A,
 H89B), C17(H17A,H17B), C3(H3A,H3B), C0AA(H0AA,H0AB), C16(H16A,H16B), C94(H94A,
 H94B)
6.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C014(H014), C01I(H01I), C01J(H01J), C01N(H01N), C01R(H01R)
6.d Idealised Me refined as rotating group:
 C02J(H1,HC,HD), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C83(H83A,H83B,H83C),
  C97(H97A,H97B,H97C), C1AA(H1AA,H1AB,H1AC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              99563
_shelx_fab_checksum              27778
_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 2.258
_oxdiff_exptl_absorpt_empirical_full_min 0.553