High-efficiency organic solar cells from low-cost pentacyclic fused-ring electron acceptors via crystal engineering
Wei, Wenkui; Yuan, Xiyue; Zhong, Jianbin; Wang, Zhiqiang; Zhou, Xia; Zhao, Feixiang; Feng, Dinglong; Zhang, Yue; Chen, Weidi; Yang, Mingqun; Zhang, Wei; Ma, Zaifei; Tang, Zheng; Lu, Xinhui; Huang, Fei; Cao, Yong; Duan, Chunhui; Energy & Environmental Science 17 (2024) 6627–6639; doi:10.1039/D4EE02296C

data_1572791
_publ_section_title
;
 High-efficiency organic solar cells from low-cost pentacyclic fused-ring
 electron acceptors via crystal engineering
;
_journal_issue                   18
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              6627
_journal_page_last               6639
_journal_paper_doi               10.1039/D4EE02296C
_journal_volume                  17
_journal_year                    2024
_chemical_formula_moiety         'C76 H78 F4 N9 O2 S2'
_chemical_formula_sum            'C76 H78 F4 N9 O2 S2'
_chemical_formula_weight         1289.59
_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             2022-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-26 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                85.291(4)
_cell_angle_beta                 68.991(5)
_cell_angle_gamma                81.688(4)
_cell_formula_units_Z            2
_cell_length_a                   14.9787(7)
_cell_length_b                   15.6453(7)
_cell_length_c                   15.6646(11)
_cell_measurement_reflns_used    9390
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2700
_cell_measurement_theta_min      3.1400
_cell_volume                     3389.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.944
_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    -69.00  10.00   0.50    1.95    --   -2.20 -72.00  30.00  158
  2  \w    -80.00   7.00   0.50    1.95    --   -2.20 -57.00 120.00  174
  3  \w    -11.00  69.00   0.50    1.95    --    2.20  57.00 -30.00  160
  4  \w    -57.00  16.00   0.50    7.80    --    5.00 -19.00 150.00  146
  5  \w     47.00  92.00   0.50    7.80    --    5.00  19.00  90.00   90
  6  \w      9.00  38.00   0.50    7.80    --    5.00  72.00-120.00   58
  7  \w    -99.00 -51.00   0.50    7.80    -- -101.30  72.00   0.00   96
  8  \w    -94.00 -62.00   0.50    7.80    -- -101.30  72.00-180.00   64
  9  \w    -43.00 -15.00   0.50    7.80    -- -101.30  72.00  90.00   56
 10  \w   -115.00 -18.00   0.50    7.80    -- -101.30  72.00 150.00  194
 11  \w   -100.00 -19.00   0.50    7.80    -- -101.30  72.00 -30.00  162
 12  \w   -184.00-157.00   0.50    7.80    -- -101.30 -72.00-180.00   54
 13  \w   -112.00 -13.00   0.50    7.80    -- -101.30  57.00 -90.00  198
 14  \w   -115.00 -13.00   0.50    7.80    -- -101.30  57.00 120.00  204
 15  \w   -113.00 -12.00   0.50    7.80    -- -101.30  19.00  90.00  202
 16  \w   -115.00 -26.00   0.50    7.80    -- -101.30  72.00-150.00  178
 17  \w   -109.00 -13.00   0.50    7.80    -- -101.30  19.00   0.00  192
 18  \w   -115.00 -20.00   0.50    7.80    -- -101.30  72.00  30.00  190
 19  \w   -111.00 -13.00   0.50    7.80    -- -101.30  72.00 -90.00  196
 20  \w   -126.00 -93.00   0.50    7.80    -- -101.30 -72.00-180.00   66
 21  \w    -99.00 -74.00   0.50    7.80    -- -101.30  72.00  90.00   50
 22  \w    -95.00 -64.00   0.50    7.80    -- -101.30  72.00 -60.00   62
 23  \w    -88.00 -61.00   0.50    7.80    -- -101.30  72.00 120.00   54
 24  \w    -92.00 -67.00   0.50    7.80    -- -101.30  72.00  60.00   50
 25  \w   -177.00 -12.00   0.50    7.80    -- -101.30   0.00 120.00  330
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0418490000
_diffrn_orient_matrix_UB_12      -0.0580379000
_diffrn_orient_matrix_UB_13      -0.0835740000
_diffrn_orient_matrix_UB_21      0.0128869000
_diffrn_orient_matrix_UB_22      0.0808946000
_diffrn_orient_matrix_UB_23      -0.0642087000
_diffrn_orient_matrix_UB_31      0.1020311000
_diffrn_orient_matrix_UB_32      0.0001803000
_diffrn_orient_matrix_UB_33      0.0020637000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33559
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.530
_diffrn_reflns_theta_min         2.856
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       needle
_exptl_crystal_F_000             1362
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.861
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     844
_refine_ls_number_reflns         13113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.2217
_refine_ls_R_factor_gt           0.1982
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.7000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6373
_refine_ls_wR_factor_ref         0.6754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9503
_reflns_number_total             13113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee02296c2.cif
_cod_data_source_block           1
_cod_database_code               1572791
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C01N(H01N), C028(H028)
2.b Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C00X(H00C,H00D), C00Z(H00E,H00F), C013(H01A,H01B), C017(H01C,
 H01D), C01L(H01F,H01G), C01P(H01H,H01I), C01Q(H01K,H01L), C01V(H01T,H01V),
 C01W(H01W,H01X), C01Y(H01Z,HB), C01Z(H01,HC), C020(H02A,H02B), C021(H02C,H02D),
  C023(H02E,H02F), C024(H02G,H02H), C026(H02I,H02J), C027(H02K,H02L), C02B(H02S,
 H02T), C02C(H02U,H02V), C02D(H02W,H02X), C02E(H02Y,HD), C02F(H02Z,HE),
 C02G(H02,HF), C02H(H0AA,HG), C02I(H1AA,HH)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C011(H011), C015(H015), C01A(H01E), C01J(H01J), C01U(H01U)
2.d Idealised Me refined as rotating group:
 C01S(H01M,H01O,H01P), C01T(H01Q,H01R,H01S), C01X(H01Y,H,HA), C029(H02M,H02N,
 H02O), C02A(H02P,H02Q,H02R), C02K(H2AA,HI,HJ)
;
_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 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.786